# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jonathan Steed' _publ_contact_author_address ; Department of Chemistry University of Durham University Science Laboratories South Road Durham DH1 3LE ; _publ_contact_author_email JON.STEED@DUR.AC.UK _publ_section_title ; Polyaza Metacyclophanes as Ditopic Anion Receptors ; loop_ _publ_author_name 'Jonathan Steed' 'Christos A. Ilioudis' data_PBCAREF.CIF _database_code_depnum_ccdc_archive 'CCDC 272024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 N3' _chemical_formula_weight 205.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.805(2) _cell_length_b 10.863(2) _cell_length_c 19.502(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2289.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10982 _diffrn_reflns_av_R_equivalents 0.2017 _diffrn_reflns_av_sigmaI/netI 0.1520 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2012 _reflns_number_gt 1457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0089P)^2^+6.6855P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2012 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1854 _refine_ls_R_factor_gt 0.1280 _refine_ls_wR_factor_ref 0.2049 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 1.259 _refine_ls_restrained_S_all 1.259 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.2059(3) -0.2259(3) 0.06796(19) 0.0210(10) Uani 1 1 d . . . N2 N 0.0705(3) -0.1987(3) 0.02683(18) 0.0208(10) Uani 1 1 d . . . N3 N 0.1258(3) 0.0580(3) 0.06262(18) 0.0193(9) Uani 1 1 d . . . C1 C -0.2673(4) -0.1729(4) 0.1282(2) 0.0253(12) Uani 1 1 d . . . H1A H -0.2990 -0.2399 0.1579 0.030 Uiso 1 1 calc R . . H1B H -0.3386 -0.1223 0.1134 0.030 Uiso 1 1 calc R . . C2 C -0.1063(4) -0.3125(4) 0.0863(2) 0.0245(12) Uani 1 1 d . . . H2A H -0.1412 -0.3965 0.0900 0.029 Uiso 1 1 calc R . . H2B H -0.0724 -0.2897 0.1317 0.029 Uiso 1 1 calc R . . C3 C -0.0017(4) -0.3132(4) 0.0339(3) 0.0271(12) Uani 1 1 d . . . H3A H 0.0561 -0.3804 0.0461 0.033 Uiso 1 1 calc R . . H3B H -0.0375 -0.3334 -0.0114 0.033 Uiso 1 1 calc R . . C4 C 0.1466(4) -0.1678(4) 0.0859(2) 0.0241(12) Uani 1 1 d . . . H4A H 0.2090 -0.2331 0.0935 0.029 Uiso 1 1 calc R . . H4B H 0.0941 -0.1621 0.1274 0.029 Uiso 1 1 calc R . . C5 C 0.2110(4) -0.0454(4) 0.0734(2) 0.0246(12) Uani 1 1 d . . . H5A H 0.2646 -0.0267 0.1132 0.030 Uiso 1 1 calc R . . H5B H 0.2650 -0.0534 0.0326 0.030 Uiso 1 1 calc R . . C6 C 0.0879(5) 0.1224(4) 0.1247(2) 0.0272(12) Uani 1 1 d . . . H6A H 0.0502 0.2022 0.1121 0.033 Uiso 1 1 calc R . . H6B H 0.1619 0.1395 0.1531 0.033 Uiso 1 1 calc R . . C7 C -0.0045(4) 0.0480(4) 0.1666(2) 0.0227(12) Uani 1 1 d . . . C8 C -0.1008(4) -0.0116(4) 0.1343(2) 0.0198(11) Uani 1 1 d . . . H8 H -0.1152 0.0039 0.0870 0.024 Uiso 1 1 calc R . . C9 C -0.1773(4) -0.0938(4) 0.1686(2) 0.0207(12) Uani 1 1 d . . . C10 C -0.1605(4) -0.1088(5) 0.2384(3) 0.0305(13) Uani 1 1 d . . . H10 H -0.2137 -0.1624 0.2632 0.037 Uiso 1 1 calc R . . C11 C -0.0673(5) -0.0469(5) 0.2725(3) 0.0387(15) Uani 1 1 d . . . H11 H -0.0576 -0.0574 0.3206 0.046 Uiso 1 1 calc R . . C12 C 0.0124(5) 0.0306(5) 0.2369(2) 0.0302(13) Uani 1 1 d . . . H12 H 0.0777 0.0714 0.2603 0.036 Uiso 1 1 calc R . . H1N H -0.2753 -0.2694 0.0401 0.036 Uiso 1 1 d R . . H3N H 0.1732 0.1220 0.0347 0.036 Uiso 1 1 d R . . H2N H 0.0336 -0.1767 -0.0193 0.036 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.021(2) 0.019(2) 0.023(2) -0.0013(19) 0.0041(18) -0.0022(18) N2 0.022(2) 0.021(2) 0.019(2) 0.0028(18) -0.0034(17) -0.0047(19) N3 0.021(2) 0.020(2) 0.017(2) -0.0002(18) -0.0004(17) -0.0049(18) C1 0.016(3) 0.027(3) 0.033(3) 0.007(2) 0.002(2) 0.000(2) C2 0.027(3) 0.018(3) 0.029(3) 0.002(2) 0.002(2) -0.002(2) C3 0.025(3) 0.022(3) 0.035(3) 0.003(2) 0.001(2) 0.005(2) C4 0.017(3) 0.025(3) 0.030(3) 0.007(2) 0.000(2) 0.007(2) C5 0.018(3) 0.034(3) 0.022(3) -0.006(2) -0.003(2) 0.003(2) C6 0.028(3) 0.026(3) 0.028(3) 0.000(2) -0.002(2) -0.009(2) C7 0.017(3) 0.023(3) 0.028(3) -0.009(2) 0.003(2) -0.001(2) C8 0.025(3) 0.018(2) 0.016(2) 0.003(2) -0.002(2) 0.006(2) C9 0.017(3) 0.021(3) 0.024(3) 0.002(2) 0.005(2) 0.005(2) C10 0.020(3) 0.044(3) 0.028(3) 0.009(3) 0.008(2) -0.003(3) C11 0.030(3) 0.071(4) 0.015(3) 0.001(3) 0.007(2) 0.002(3) C12 0.028(3) 0.045(3) 0.018(3) -0.012(3) 0.000(2) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.468(6) . ? N1 C2 1.474(6) . ? N2 C4 1.454(6) . ? N2 C3 1.475(6) . ? N3 C6 1.457(6) . ? N3 C5 1.468(6) . ? C1 C9 1.518(6) . ? C2 C3 1.523(6) . ? C4 C5 1.521(6) . ? C6 C7 1.522(6) . ? C7 C8 1.379(6) . ? C7 C12 1.396(6) . ? C8 C9 1.389(6) . ? C9 C10 1.382(6) . ? C10 C11 1.382(7) . ? C11 C12 1.390(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 112.7(4) . . ? C4 N2 C3 114.8(4) . . ? C6 N3 C5 115.1(4) . . ? N1 C1 C9 110.4(4) . . ? N1 C2 C3 112.5(4) . . ? N2 C3 C2 116.9(4) . . ? N2 C4 C5 109.4(4) . . ? N3 C5 C4 113.9(4) . . ? N3 C6 C7 112.1(4) . . ? C8 C7 C12 118.9(4) . . ? C8 C7 C6 119.9(4) . . ? C12 C7 C6 120.9(4) . . ? C7 C8 C9 122.0(4) . . ? C10 C9 C8 118.2(4) . . ? C10 C9 C1 121.9(4) . . ? C8 C9 C1 119.7(4) . . ? C11 C10 C9 120.8(5) . . ? C10 C11 C12 120.4(4) . . ? C11 C12 C7 119.5(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.558 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.083 data_L1-TS3.CIF _database_code_depnum_ccdc_archive 'CCDC 272025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Revised CIF' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33.33 H37.33 Cl N3 O6 S3' _chemical_formula_weight 707.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0306(11) _cell_length_b 13.5130(13) _cell_length_c 14.3379(15) _cell_angle_alpha 108.817(5) _cell_angle_beta 104.119(15) _cell_angle_gamma 103.132(6) _cell_volume 1682.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 743 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min 0.9026 _exptl_absorpt_correction_T_max 0.9659 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '2o phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8530 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.1111 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4608 _reflns_number_gt 3143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo-SMN _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.6240P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4608 _refine_ls_number_parameters 445 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1598 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91122(13) 0.04756(9) 0.32595(9) 0.0299(3) Uani 1 1 d . . . S2 S 0.45703(12) 0.19233(8) 0.13343(8) 0.0258(3) Uani 1 1 d . . . S3 S 0.68462(13) 0.32838(9) -0.15713(9) 0.0292(3) Uani 1 1 d . . . O1 O 1.0609(4) 0.1069(3) 0.3913(3) 0.0432(8) Uani 1 1 d . . . O2 O 0.7981(4) 0.0671(3) 0.3671(2) 0.0395(8) Uani 1 1 d . . . O3 O 0.4201(3) 0.1072(2) 0.1702(2) 0.0358(8) Uani 1 1 d . . . O4 O 0.3573(3) 0.1903(3) 0.0417(2) 0.0390(8) Uani 1 1 d . . . O5 O 0.5798(4) 0.3659(2) -0.1169(2) 0.0363(8) Uani 1 1 d . . . O6 O 0.8192(3) 0.4058(2) -0.1425(3) 0.0401(8) Uani 1 1 d . . . N1 N 0.8806(4) 0.0738(3) 0.2217(3) 0.0307(9) Uani 1 1 d . . . N2 N 0.6065(4) 0.1894(3) 0.1082(3) 0.0272(8) Uani 1 1 d . . . N3 N 0.7241(4) 0.2445(3) -0.1042(3) 0.0287(9) Uani 1 1 d . . . C1 C 1.1271(5) 0.3420(4) 0.1552(4) 0.0407(12) Uani 1 1 d . . . H1 H 1.1956 0.4134 0.2007 0.049 Uiso 1 1 calc R . . C2 C 1.0443(5) 0.3232(4) 0.0551(4) 0.0327(10) Uani 1 1 d . . . H2 H 1.0555 0.3825 0.0326 0.039 Uiso 1 1 calc R . . C3 C 0.9448(5) 0.2192(3) -0.0132(3) 0.0270(10) Uani 1 1 d . . . C4 C 0.9310(5) 0.1324(3) 0.0217(3) 0.0267(9) Uani 1 1 d . . . H4 H 0.8655 0.0602 -0.0247 0.032 Uiso 1 1 calc R . . C5 C 1.0121(5) 0.1511(4) 0.1231(3) 0.0293(10) Uani 1 1 d . . . C6 C 1.1103(5) 0.2562(4) 0.1893(4) 0.0388(12) Uani 1 1 d . . . H6 H 1.1665 0.2695 0.2586 0.047 Uiso 1 1 calc R . . C7 C 0.8445(5) 0.2009(4) -0.1184(4) 0.0332(11) Uani 1 1 d . . . H7A H 0.8993 0.2395 -0.1526 0.040 Uiso 1 1 calc R . . H7B H 0.8038 0.1207 -0.1640 0.040 Uiso 1 1 calc R . . C8 C 0.6221(5) 0.1876(3) -0.0644(3) 0.0267(9) Uani 1 1 d . . . H8A H 0.6325 0.1145 -0.0720 0.032 Uiso 1 1 calc R . . H8B H 0.5206 0.1751 -0.1058 0.032 Uiso 1 1 calc R . . C9 C 0.6540(5) 0.2579(3) 0.0511(4) 0.0337(11) Uani 1 1 d . . . H9A H 0.7600 0.2987 0.0854 0.040 Uiso 1 1 calc R . . H9B H 0.6032 0.3132 0.0559 0.040 Uiso 1 1 calc R . . C10 C 0.7257(5) 0.1844(4) 0.1904(4) 0.0335(10) Uani 1 1 d . . . H10A H 0.7093 0.2099 0.2583 0.040 Uiso 1 1 calc R . . H10B H 0.8200 0.2354 0.1987 0.040 Uiso 1 1 calc R . . C11 C 0.7340(5) 0.0674(3) 0.1634(4) 0.0297(10) Uani 1 1 d . . . H11A H 0.6601 0.0231 0.1822 0.036 Uiso 1 1 calc R . . H11B H 0.7132 0.0305 0.0870 0.036 Uiso 1 1 calc R . . C12 C 0.9823(5) 0.0600(4) 0.1617(4) 0.0351(12) Uani 1 1 d . . . H12A H 0.9388 -0.0128 0.1011 0.042 Uiso 1 1 calc R . . H12B H 1.0751 0.0615 0.2073 0.042 Uiso 1 1 calc R . . C13 C 0.8896(5) -0.0953(3) 0.2841(3) 0.0265(10) Uani 1 1 d . . . C14 C 0.8062(5) -0.1689(4) 0.1821(4) 0.0335(11) Uani 1 1 d . . . H14 H 0.7600 -0.1426 0.1335 0.040 Uiso 1 1 calc R . . C15 C 0.7898(5) -0.2799(4) 0.1505(4) 0.0405(12) Uani 1 1 d . . . H15 H 0.7318 -0.3295 0.0803 0.049 Uiso 1 1 calc R . . C16 C 0.8559(6) -0.3198(4) 0.2189(5) 0.0447(14) Uani 1 1 d . . . C17 C 0.9378(6) -0.2464(4) 0.3219(5) 0.0451(13) Uani 1 1 d . . . H17 H 0.9807 -0.2741 0.3704 0.054 Uiso 1 1 calc R . . C18 C 0.9589(5) -0.1325(4) 0.3563(4) 0.0325(10) Uani 1 1 d . . . H18 H 1.0181 -0.0825 0.4261 0.039 Uiso 1 1 calc R . . C19 C 0.8440(7) -0.4410(4) 0.1817(6) 0.071(2) Uani 1 1 d . . . H19A H 0.7629 -0.4836 0.1149 0.106 Uiso 1 1 calc R . . H19B H 0.8262 -0.4691 0.2341 0.106 Uiso 1 1 calc R . . H19C H 0.9350 -0.4487 0.1718 0.106 Uiso 1 1 calc R . . C20 C 0.5021(4) 0.3217(3) 0.2370(3) 0.0256(9) Uani 1 1 d . . . C21 C 0.5017(5) 0.4150(3) 0.2149(4) 0.0317(10) Uani 1 1 d . . . H21 H 0.4647 0.4072 0.1444 0.038 Uiso 1 1 calc R . . C22 C 0.5549(5) 0.5176(4) 0.2953(4) 0.0387(12) Uani 1 1 d . . . H22 H 0.5554 0.5807 0.2793 0.046 Uiso 1 1 calc R . . C23 C 0.6087(6) 0.5326(4) 0.4002(4) 0.0434(12) Uani 1 1 d . . . C24 C 0.6035(6) 0.4371(4) 0.4202(4) 0.0472(13) Uani 1 1 d . . . H24 H 0.6374 0.4443 0.4908 0.057 Uiso 1 1 calc R . . C25 C 0.5503(5) 0.3326(4) 0.3398(3) 0.0322(10) Uani 1 1 d . . . H25 H 0.5470 0.2689 0.3552 0.039 Uiso 1 1 calc R . . C26 C 0.6730(8) 0.6457(5) 0.4866(5) 0.0702(18) Uani 1 1 d . . . H26A H 0.6934 0.6394 0.5544 0.105 Uiso 1 1 calc R . . H26B H 0.6040 0.6862 0.4803 0.105 Uiso 1 1 calc R . . H26C H 0.7639 0.6858 0.4817 0.105 Uiso 1 1 calc R . . C27 C 0.5997(5) 0.2505(3) -0.2928(3) 0.0263(9) Uani 1 1 d . . . C28 C 0.6803(5) 0.2485(4) -0.3598(4) 0.0320(10) Uani 1 1 d . . . H28 H 0.7805 0.2924 -0.3326 0.038 Uiso 1 1 calc R . . C29 C 0.6142(5) 0.1824(4) -0.4657(4) 0.0346(11) Uani 1 1 d . . . H29 H 0.6701 0.1810 -0.5107 0.042 Uiso 1 1 calc R . . C30 C 0.4675(6) 0.1179(4) -0.5079(4) 0.0364(11) Uani 1 1 d . . . C31 C 0.3895(5) 0.1212(4) -0.4397(4) 0.0387(12) Uani 1 1 d . . . H31 H 0.2894 0.0772 -0.4670 0.046 Uiso 1 1 calc R . . C32 C 0.4531(5) 0.1868(4) -0.3335(4) 0.0342(11) Uani 1 1 d . . . H32 H 0.3970 0.1881 -0.2887 0.041 Uiso 1 1 calc R . . C33 C 0.3947(6) 0.0491(4) -0.6230(4) 0.0458(13) Uani 1 1 d . . . H33A H 0.3326 -0.0240 -0.6342 0.069 Uiso 1 1 calc R . . H33B H 0.4689 0.0405 -0.6556 0.069 Uiso 1 1 calc R . . H33C H 0.3349 0.0859 -0.6547 0.069 Uiso 1 1 calc R . . Cl2S Cl 1.0479(8) -0.3527(4) 0.5298(4) 0.0648(16) Uani 0.33 1 d P . . Cl1S Cl 1.0417(5) -0.5307(4) 0.3571(4) 0.0671(12) Uani 0.33 1 d P . . Cl3S Cl 0.9591(9) -0.5860(10) 0.5080(13) 0.194(7) Uani 0.33 1 d P . . C1S C 0.9754(19) -0.4859(14) 0.4519(13) 0.042(4) Uani 0.33 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0389(7) 0.0280(6) 0.0231(6) 0.0093(5) 0.0126(5) 0.0112(5) S2 0.0269(6) 0.0255(6) 0.0225(6) 0.0064(5) 0.0097(5) 0.0077(5) S3 0.0342(7) 0.0268(6) 0.0245(6) 0.0103(5) 0.0088(5) 0.0078(5) O1 0.041(2) 0.0344(19) 0.034(2) 0.0086(17) -0.0027(17) -0.0018(15) O2 0.052(2) 0.0396(19) 0.039(2) 0.0155(17) 0.0294(19) 0.0217(17) O3 0.044(2) 0.0250(16) 0.0356(19) 0.0097(16) 0.0208(17) 0.0030(14) O4 0.0309(19) 0.049(2) 0.0282(19) 0.0079(17) 0.0025(16) 0.0161(16) O5 0.046(2) 0.0371(18) 0.0241(18) 0.0067(16) 0.0108(17) 0.0207(16) O6 0.041(2) 0.0321(18) 0.035(2) 0.0130(16) 0.0059(17) -0.0017(14) N1 0.034(2) 0.039(2) 0.036(2) 0.022(2) 0.020(2) 0.0231(19) N2 0.031(2) 0.0256(19) 0.030(2) 0.0106(18) 0.0163(18) 0.0128(16) N3 0.033(2) 0.035(2) 0.027(2) 0.0174(19) 0.0151(19) 0.0148(18) C1 0.026(3) 0.043(3) 0.042(3) 0.014(3) 0.006(2) 0.001(2) C2 0.030(3) 0.034(3) 0.036(3) 0.016(2) 0.013(2) 0.009(2) C3 0.029(3) 0.033(2) 0.026(2) 0.013(2) 0.015(2) 0.012(2) C4 0.028(2) 0.026(2) 0.026(2) 0.007(2) 0.015(2) 0.0097(19) C5 0.031(3) 0.042(3) 0.028(3) 0.019(2) 0.018(2) 0.021(2) C6 0.024(3) 0.061(3) 0.026(3) 0.016(3) 0.006(2) 0.009(2) C7 0.033(3) 0.046(3) 0.026(3) 0.017(2) 0.013(2) 0.015(2) C8 0.026(2) 0.028(2) 0.029(2) 0.014(2) 0.010(2) 0.0079(19) C9 0.044(3) 0.026(2) 0.035(3) 0.011(2) 0.023(2) 0.009(2) C10 0.029(3) 0.034(3) 0.031(3) 0.006(2) 0.007(2) 0.014(2) C11 0.032(3) 0.026(2) 0.033(3) 0.010(2) 0.015(2) 0.013(2) C12 0.041(3) 0.047(3) 0.039(3) 0.025(3) 0.025(3) 0.028(2) C13 0.025(3) 0.031(2) 0.026(2) 0.011(2) 0.012(2) 0.010(2) C14 0.027(3) 0.040(3) 0.026(3) 0.009(2) 0.007(2) 0.008(2) C15 0.035(3) 0.035(3) 0.042(3) 0.006(3) 0.018(3) 0.004(2) C16 0.040(3) 0.027(3) 0.071(4) 0.013(3) 0.038(3) 0.006(2) C17 0.049(3) 0.044(3) 0.060(4) 0.031(3) 0.026(3) 0.024(3) C18 0.030(3) 0.035(3) 0.032(3) 0.016(2) 0.009(2) 0.009(2) C19 0.071(4) 0.032(3) 0.121(6) 0.026(4) 0.059(5) 0.016(3) C20 0.017(2) 0.025(2) 0.029(3) 0.004(2) 0.008(2) 0.0056(18) C21 0.028(3) 0.030(3) 0.036(3) 0.009(2) 0.011(2) 0.013(2) C22 0.038(3) 0.031(3) 0.048(3) 0.014(3) 0.016(3) 0.014(2) C23 0.046(3) 0.027(3) 0.047(3) 0.003(3) 0.013(3) 0.014(2) C24 0.062(4) 0.044(3) 0.028(3) 0.006(3) 0.013(3) 0.019(3) C25 0.039(3) 0.028(3) 0.024(3) 0.005(2) 0.009(2) 0.011(2) C26 0.084(5) 0.038(3) 0.064(4) 0.002(3) 0.017(4) 0.012(3) C27 0.032(3) 0.026(2) 0.022(2) 0.011(2) 0.009(2) 0.0100(19) C28 0.030(3) 0.033(2) 0.033(3) 0.013(2) 0.013(2) 0.009(2) C29 0.040(3) 0.043(3) 0.030(3) 0.018(2) 0.019(2) 0.019(2) C30 0.054(3) 0.029(2) 0.028(3) 0.013(2) 0.012(2) 0.016(2) C31 0.039(3) 0.039(3) 0.027(3) 0.012(3) 0.007(2) 0.002(2) C32 0.035(3) 0.039(3) 0.027(3) 0.013(2) 0.014(2) 0.007(2) C33 0.063(4) 0.038(3) 0.029(3) 0.012(3) 0.009(3) 0.013(3) Cl2S 0.092(4) 0.044(3) 0.042(3) 0.012(3) -0.005(3) 0.033(3) Cl1S 0.048(3) 0.063(3) 0.065(3) -0.003(3) 0.005(2) 0.030(2) Cl3S 0.078(5) 0.157(9) 0.354(18) 0.219(12) -0.035(9) -0.002(7) C1S 0.037(5) 0.039(5) 0.047(6) 0.005(4) 0.014(4) 0.027(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.434(3) . ? S1 O2 1.438(3) . ? S1 N1 1.619(3) . ? S1 C13 1.769(4) . ? S2 O3 1.425(3) . ? S2 O4 1.433(3) . ? S2 N2 1.631(3) . ? S2 C20 1.762(4) . ? S3 O6 1.428(3) . ? S3 O5 1.430(3) . ? S3 N3 1.621(3) . ? S3 C27 1.756(4) . ? N1 C11 1.472(5) . ? N1 C12 1.493(5) . ? N2 C10 1.492(6) . ? N2 C9 1.494(4) . ? N3 C8 1.476(4) . ? N3 C7 1.487(5) . ? C1 C2 1.379(7) . ? C1 C6 1.389(6) . ? C2 C3 1.389(6) . ? C3 C4 1.408(5) . ? C3 C7 1.501(6) . ? C4 C5 1.390(6) . ? C5 C6 1.388(7) . ? C5 C12 1.505(5) . ? C8 C9 1.528(6) . ? C10 C11 1.528(6) . ? C13 C14 1.383(6) . ? C13 C18 1.397(6) . ? C14 C15 1.377(6) . ? C15 C16 1.372(7) . ? C16 C17 1.390(8) . ? C16 C19 1.515(7) . ? C17 C18 1.403(6) . ? C20 C25 1.381(6) . ? C20 C21 1.397(5) . ? C21 C22 1.367(7) . ? C22 C23 1.397(7) . ? C23 C24 1.403(6) . ? C23 C26 1.492(8) . ? C24 C25 1.384(7) . ? C27 C32 1.388(6) . ? C27 C28 1.396(5) . ? C28 C29 1.381(7) . ? C29 C30 1.391(7) . ? C30 C31 1.389(6) . ? C30 C33 1.494(7) . ? C31 C32 1.383(7) . ? Cl2S Cl3S 0.806(15) 2_746 ? Cl2S C1S 1.651(17) . ? Cl2S C1S 2.247(17) 2_746 ? Cl1S C1S 1.659(14) . ? Cl1S Cl3S 2.068(19) 2_746 ? Cl3S Cl2S 0.806(15) 2_746 ? Cl3S C1S 0.934(19) 2_746 ? Cl3S C1S 1.780(16) . ? Cl3S Cl1S 2.068(19) 2_746 ? Cl3S Cl3S 2.387(12) 2_746 ? C1S Cl3S 0.934(19) 2_746 ? C1S C1S 1.54(3) 2_746 ? C1S Cl2S 2.247(17) 2_746 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.4(2) . . ? O1 S1 N1 108.71(18) . . ? O2 S1 N1 105.96(17) . . ? O1 S1 C13 106.70(19) . . ? O2 S1 C13 108.77(18) . . ? N1 S1 C13 106.70(19) . . ? O3 S2 O4 120.2(2) . . ? O3 S2 N2 106.64(17) . . ? O4 S2 N2 106.15(17) . . ? O3 S2 C20 108.59(18) . . ? O4 S2 C20 108.26(19) . . ? N2 S2 C20 106.16(19) . . ? O6 S3 O5 120.6(2) . . ? O6 S3 N3 107.28(18) . . ? O5 S3 N3 106.12(15) . . ? O6 S3 C27 106.70(18) . . ? O5 S3 C27 108.07(19) . . ? N3 S3 C27 107.47(18) . . ? C11 N1 C12 116.6(3) . . ? C11 N1 S1 121.3(2) . . ? C12 N1 S1 117.8(2) . . ? C10 N2 C9 115.8(4) . . ? C10 N2 S2 116.5(3) . . ? C9 N2 S2 116.9(3) . . ? C8 N3 C7 116.7(3) . . ? C8 N3 S3 121.1(3) . . ? C7 N3 S3 120.5(2) . . ? C2 C1 C6 119.8(5) . . ? C1 C2 C3 121.1(4) . . ? C2 C3 C4 118.4(4) . . ? C2 C3 C7 121.3(4) . . ? C4 C3 C7 120.1(4) . . ? C5 C4 C3 120.8(4) . . ? C6 C5 C4 119.2(4) . . ? C6 C5 C12 121.3(4) . . ? C4 C5 C12 119.3(4) . . ? C5 C6 C1 120.6(4) . . ? N3 C7 C3 109.3(3) . . ? N3 C8 C9 109.9(3) . . ? N2 C9 C8 112.3(3) . . ? N2 C10 C11 112.2(4) . . ? N1 C11 C10 109.4(4) . . ? N1 C12 C5 110.5(3) . . ? C14 C13 C18 120.4(4) . . ? C14 C13 S1 121.0(3) . . ? C18 C13 S1 118.6(4) . . ? C15 C14 C13 120.5(4) . . ? C16 C15 C14 120.9(5) . . ? C15 C16 C17 118.7(4) . . ? C15 C16 C19 120.4(6) . . ? C17 C16 C19 120.8(5) . . ? C16 C17 C18 121.8(4) . . ? C13 C18 C17 117.6(5) . . ? C25 C20 C21 120.1(4) . . ? C25 C20 S2 120.1(3) . . ? C21 C20 S2 119.6(3) . . ? C22 C21 C20 119.7(4) . . ? C21 C22 C23 122.0(4) . . ? C22 C23 C24 117.1(5) . . ? C22 C23 C26 121.2(4) . . ? C24 C23 C26 121.7(5) . . ? C25 C24 C23 121.7(5) . . ? C20 C25 C24 119.4(4) . . ? C32 C27 C28 119.7(4) . . ? C32 C27 S3 119.9(3) . . ? C28 C27 S3 120.4(3) . . ? C29 C28 C27 119.9(4) . . ? C28 C29 C30 121.3(4) . . ? C31 C30 C29 117.7(5) . . ? C31 C30 C33 120.9(5) . . ? C29 C30 C33 121.4(4) . . ? C32 C31 C30 122.1(4) . . ? C31 C32 C27 119.3(4) . . ? Cl3S Cl2S C1S 19.7(11) 2_746 . ? Cl3S Cl2S C1S 45.7(10) 2_746 2_746 ? C1S Cl2S C1S 43.4(9) . 2_746 ? C1S Cl1S Cl3S 26.2(7) . 2_746 ? Cl2S Cl3S C1S 143(2) 2_746 2_746 ? Cl2S Cl3S C1S 115.4(17) 2_746 . ? C1S Cl3S C1S 60.1(14) 2_746 . ? Cl2S Cl3S Cl1S 154.5(12) 2_746 2_746 ? C1S Cl3S Cl1S 51.7(14) 2_746 2_746 ? C1S Cl3S Cl1S 89.9(7) . 2_746 ? Cl2S Cl3S Cl3S 129(2) 2_746 2_746 ? C1S Cl3S Cl3S 40.3(10) 2_746 2_746 ? C1S Cl3S Cl3S 19.8(6) . 2_746 ? Cl1S Cl3S Cl3S 75.9(8) 2_746 2_746 ? Cl3S C1S C1S 88.3(19) 2_746 2_746 ? Cl3S C1S Cl2S 16.9(11) 2_746 . ? C1S C1S Cl2S 89.3(15) 2_746 . ? Cl3S C1S Cl1S 102.2(18) 2_746 . ? C1S C1S Cl1S 116.6(12) 2_746 . ? Cl2S C1S Cl1S 116.6(10) . . ? Cl3S C1S Cl3S 119.9(14) 2_746 . ? C1S C1S Cl3S 31.6(8) 2_746 . ? Cl2S C1S Cl3S 119.4(11) . . ? Cl1S C1S Cl3S 106.1(10) . . ? Cl3S C1S Cl2S 133.0(15) 2_746 2_746 ? C1S C1S Cl2S 47.3(10) 2_746 2_746 ? Cl2S C1S Cl2S 136.6(9) . 2_746 ? Cl1S C1S Cl2S 88.8(6) . 2_746 ? Cl3S C1S Cl2S 18.9(7) . 2_746 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C11 -153.4(3) . . . . ? O2 S1 N1 C11 -23.9(4) . . . . ? C13 S1 N1 C11 91.9(3) . . . . ? O1 S1 N1 C12 50.7(4) . . . . ? O2 S1 N1 C12 -179.8(3) . . . . ? C13 S1 N1 C12 -64.0(4) . . . . ? O3 S2 N2 C10 -47.4(3) . . . . ? O4 S2 N2 C10 -176.6(3) . . . . ? C20 S2 N2 C10 68.3(3) . . . . ? O3 S2 N2 C9 169.8(3) . . . . ? O4 S2 N2 C9 40.5(4) . . . . ? C20 S2 N2 C9 -74.6(3) . . . . ? O6 S3 N3 C8 153.4(3) . . . . ? O5 S3 N3 C8 23.3(4) . . . . ? C27 S3 N3 C8 -92.1(3) . . . . ? O6 S3 N3 C7 -42.1(4) . . . . ? O5 S3 N3 C7 -172.2(4) . . . . ? C27 S3 N3 C7 72.4(4) . . . . ? C6 C1 C2 C3 -0.8(6) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C1 C2 C3 C7 174.2(4) . . . . ? C2 C3 C4 C5 1.8(6) . . . . ? C7 C3 C4 C5 -173.0(3) . . . . ? C3 C4 C5 C6 -1.7(6) . . . . ? C3 C4 C5 C12 173.1(3) . . . . ? C4 C5 C6 C1 0.3(6) . . . . ? C12 C5 C6 C1 -174.3(4) . . . . ? C2 C1 C6 C5 0.9(7) . . . . ? C8 N3 C7 C3 -65.7(5) . . . . ? S3 N3 C7 C3 129.2(3) . . . . ? C2 C3 C7 N3 -76.5(5) . . . . ? C4 C3 C7 N3 98.2(4) . . . . ? C7 N3 C8 C9 104.4(4) . . . . ? S3 N3 C8 C9 -90.6(4) . . . . ? C10 N2 C9 C8 113.0(4) . . . . ? S2 N2 C9 C8 -103.9(4) . . . . ? N3 C8 C9 N2 -154.4(3) . . . . ? C9 N2 C10 C11 -115.4(4) . . . . ? S2 N2 C10 C11 101.3(3) . . . . ? C12 N1 C11 C10 -101.9(4) . . . . ? S1 N1 C11 C10 102.0(3) . . . . ? N2 C10 C11 N1 158.3(3) . . . . ? C11 N1 C12 C5 62.4(5) . . . . ? S1 N1 C12 C5 -140.6(3) . . . . ? C6 C5 C12 N1 78.8(5) . . . . ? C4 C5 C12 N1 -95.8(4) . . . . ? O1 S1 C13 C14 -139.1(3) . . . . ? O2 S1 C13 C14 90.9(3) . . . . ? N1 S1 C13 C14 -23.0(4) . . . . ? O1 S1 C13 C18 40.8(3) . . . . ? O2 S1 C13 C18 -89.2(4) . . . . ? N1 S1 C13 C18 156.9(3) . . . . ? C18 C13 C14 C15 0.3(6) . . . . ? S1 C13 C14 C15 -179.8(3) . . . . ? C13 C14 C15 C16 -0.3(6) . . . . ? C14 C15 C16 C17 1.4(6) . . . . ? C14 C15 C16 C19 -176.6(4) . . . . ? C15 C16 C17 C18 -2.5(7) . . . . ? C19 C16 C17 C18 175.5(4) . . . . ? C14 C13 C18 C17 -1.3(6) . . . . ? S1 C13 C18 C17 178.8(3) . . . . ? C16 C17 C18 C13 2.4(6) . . . . ? O3 S2 C20 C25 24.1(4) . . . . ? O4 S2 C20 C25 156.2(3) . . . . ? N2 S2 C20 C25 -90.2(4) . . . . ? O3 S2 C20 C21 -161.8(3) . . . . ? O4 S2 C20 C21 -29.7(4) . . . . ? N2 S2 C20 C21 83.9(3) . . . . ? C25 C20 C21 C22 2.7(6) . . . . ? S2 C20 C21 C22 -171.4(3) . . . . ? C20 C21 C22 C23 -0.8(6) . . . . ? C21 C22 C23 C24 -1.1(7) . . . . ? C21 C22 C23 C26 177.0(5) . . . . ? C22 C23 C24 C25 1.2(7) . . . . ? C26 C23 C24 C25 -176.9(5) . . . . ? C21 C20 C25 C24 -2.6(6) . . . . ? S2 C20 C25 C24 171.5(4) . . . . ? C23 C24 C25 C20 0.6(7) . . . . ? O6 S3 C27 C32 -164.9(3) . . . . ? O5 S3 C27 C32 -33.9(4) . . . . ? N3 S3 C27 C32 80.3(3) . . . . ? O6 S3 C27 C28 17.9(4) . . . . ? O5 S3 C27 C28 149.0(3) . . . . ? N3 S3 C27 C28 -96.9(3) . . . . ? C32 C27 C28 C29 -0.6(6) . . . . ? S3 C27 C28 C29 176.6(3) . . . . ? C27 C28 C29 C30 0.5(6) . . . . ? C28 C29 C30 C31 -0.6(6) . . . . ? C28 C29 C30 C33 178.0(4) . . . . ? C29 C30 C31 C32 0.6(6) . . . . ? C33 C30 C31 C32 -178.0(4) . . . . ? C30 C31 C32 C27 -0.7(6) . . . . ? C28 C27 C32 C31 0.6(6) . . . . ? S3 C27 C32 C31 -176.5(3) . . . . ? C1S Cl2S C1S Cl3S -86(3) 2_746 . . 2_746 ? Cl3S Cl2S C1S C1S 86(3) 2_746 . . 2_746 ? Cl3S Cl2S C1S Cl1S -33(3) 2_746 . . . ? C1S Cl2S C1S Cl1S -119.6(17) 2_746 . . . ? Cl3S Cl2S C1S Cl3S 96(4) 2_746 . . . ? C1S Cl2S C1S Cl3S 10.1(6) 2_746 . . . ? Cl3S Cl2S C1S Cl2S 86(3) 2_746 . . 2_746 ? C1S Cl2S C1S Cl2S 0.000(1) 2_746 . . 2_746 ? Cl3S Cl1S C1S C1S -94(2) 2_746 . . 2_746 ? Cl3S Cl1S C1S Cl2S 9.4(7) 2_746 . . . ? Cl3S Cl1S C1S Cl3S -126.4(17) 2_746 . . . ? Cl3S Cl1S C1S Cl2S -133.9(16) 2_746 . . 2_746 ? Cl2S Cl3S C1S Cl3S -139(2) 2_746 . . 2_746 ? C1S Cl3S C1S Cl3S 0.000(3) 2_746 . . 2_746 ? Cl1S Cl3S C1S Cl3S 44.4(15) 2_746 . . 2_746 ? Cl2S Cl3S C1S C1S -139(2) 2_746 . . 2_746 ? Cl1S Cl3S C1S C1S 44.4(15) 2_746 . . 2_746 ? Cl3S Cl3S C1S C1S 0.000(7) 2_746 . . 2_746 ? Cl2S Cl3S C1S Cl2S -158.2(11) 2_746 . . . ? C1S Cl3S C1S Cl2S -19.5(13) 2_746 . . . ? Cl1S Cl3S C1S Cl2S 24.9(9) 2_746 . . . ? Cl3S Cl3S C1S Cl2S -19.5(13) 2_746 . . . ? Cl2S Cl3S C1S Cl1S -23.9(16) 2_746 . . . ? C1S Cl3S C1S Cl1S 115(2) 2_746 . . . ? Cl1S Cl3S C1S Cl1S 159.2(9) 2_746 . . . ? Cl3S Cl3S C1S Cl1S 115(2) 2_746 . . . ? C1S Cl3S C1S Cl2S 139(2) 2_746 . . 2_746 ? Cl1S Cl3S C1S Cl2S -176.9(14) 2_746 . . 2_746 ? Cl3S Cl3S C1S Cl2S 139(2) 2_746 . . 2_746 ? _diffrn_measured_fraction_theta_max 0.696 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.696 _refine_diff_density_max 0.496 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.062 data_c:\structs\chris\a3clo4b\a3clo4b _database_code_depnum_ccdc_archive 'CCDC 272026' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H28 Cl3 N3 O13' _chemical_formula_weight 552.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7647(4) _cell_length_b 11.2725(6) _cell_length_c 12.7812(8) _cell_angle_alpha 82.1469(24) _cell_angle_beta 71.7511(23) _cell_angle_gamma 69.0389(32) _cell_volume 1119.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3311 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2214 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.8525P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2214 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1489 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.5332(2) 0.41086(16) 0.21234(14) 0.0232(6) Uani 1 1 d . . . O1 O 0.7163(6) 0.3554(4) 0.1839(4) 0.0290(13) Uani 1 1 d . . . O2 O 0.4815(6) 0.4335(5) 0.1137(4) 0.0430(16) Uani 1 1 d . . . O4 O 0.4850(7) 0.5310(5) 0.2613(5) 0.0565(18) Uani 1 1 d . . . O3 O 0.4570(7) 0.3292(5) 0.2856(4) 0.0498(17) Uani 1 1 d . . . Cl2 Cl 0.2577(2) 0.20764(17) 0.04442(15) 0.0259(6) Uani 1 1 d . . . Cl3 Cl 1.0587(2) -0.25960(16) -0.46012(14) 0.0246(6) Uani 1 1 d . . . O10 O 1.1995(6) -0.2943(5) -0.4125(4) 0.0348(14) Uani 1 1 d . . . N3 N 1.1777(6) -0.0966(5) -0.2750(4) 0.0168(14) Uani 1 1 d . . . H3A H 1.2192 -0.0990 -0.2167 0.020 Uiso 1 1 calc R . . H3B H 1.1730 -0.1760 -0.2792 0.020 Uiso 1 1 calc R . . O9 O 0.9684(8) -0.1243(5) -0.4511(5) 0.0568(18) Uani 1 1 d . . . O11 O 0.9484(7) -0.3287(6) -0.4036(4) 0.0476(16) Uani 1 1 d . . . C1 C 1.2818(9) 0.1608(7) -0.3878(5) 0.0199(18) Uani 1 1 d . . . H1 H 1.1773 0.1844 -0.4057 0.024 Uiso 1 1 calc R . . C3 C 1.5227(9) -0.0011(7) -0.3430(5) 0.0232(19) Uani 1 1 d . . . H3 H 1.5825 -0.0875 -0.3286 0.028 Uiso 1 1 calc R . . C12 C 0.9605(8) 0.0954(6) -0.1681(5) 0.0185(17) Uani 1 1 d . . . H12A H 1.0492 0.1363 -0.1901 0.022 Uiso 1 1 calc R . . H12B H 0.9590 0.0544 -0.0944 0.022 Uiso 1 1 calc R . . O6 O 0.1173(7) 0.3122(6) 0.0924(6) 0.078(2) Uani 1 1 d . . . N1 N 1.1946(7) 0.4671(5) -0.2984(4) 0.0249(15) Uani 1 1 d . . . H1A H 1.2903 0.4757 -0.2896 0.030 Uiso 1 1 calc R . . H1B H 1.1236 0.5473 -0.3105 0.030 Uiso 1 1 calc R . . O8 O 0.1977(7) 0.1369(5) -0.0086(5) 0.0444(16) Uani 1 1 d . . . N2 N 0.7303(7) 0.2948(5) -0.0824(4) 0.0205(15) Uani 1 1 d . . . H2A H 0.6962 0.2600 -0.0133 0.025 Uiso 1 1 calc R . . H2B H 0.6360 0.3584 -0.0946 0.025 Uiso 1 1 calc R . . C11 C 0.7872(8) 0.1939(6) -0.1651(5) 0.0212(18) Uani 1 1 d . . . H11A H 0.7919 0.2347 -0.2392 0.025 Uiso 1 1 calc R . . H11B H 0.7016 0.1504 -0.1475 0.025 Uiso 1 1 calc R . . O7 O 0.3326(6) 0.1277(6) 0.1257(4) 0.0472(17) Uani 1 1 d . . . C8 C 1.1064(9) 0.4142(7) -0.1935(5) 0.0229(19) Uani 1 1 d . . . H8B H 1.0865 0.4678 -0.1322 0.028 Uiso 1 1 calc R . . H8A H 1.1815 0.3278 -0.1797 0.028 Uiso 1 1 calc R . . O12 O 1.1224(6) -0.2901(6) -0.5737(4) 0.0474(17) Uani 1 1 d . . . C2 C 1.3664(9) 0.0326(6) -0.3688(5) 0.0151(17) Uani 1 1 d . . . C14 C 1.3016(8) -0.0698(7) -0.3789(5) 0.0204(18) Uani 1 1 d . . . H14A H 1.3997 -0.1488 -0.4007 0.024 Uiso 1 1 calc R . . H14B H 1.2453 -0.0452 -0.4385 0.024 Uiso 1 1 calc R . . C13 C 0.9979(8) -0.0019(6) -0.2507(5) 0.0222(18) Uani 1 1 d . . . H13A H 0.9794 0.0426 -0.3203 0.027 Uiso 1 1 calc R . . H13B H 0.9161 -0.0488 -0.2225 0.027 Uiso 1 1 calc R . . O5 O 0.3834(8) 0.2492(6) -0.0351(5) 0.062(2) Uani 1 1 d . . . C5 C 1.5025(9) 0.2187(7) -0.3576(5) 0.0255(19) Uani 1 1 d . . . H5 H 1.5501 0.2812 -0.3542 0.031 Uiso 1 1 calc R . . C6 C 1.3461(9) 0.2554(7) -0.3814(5) 0.0213(19) Uani 1 1 d . . . C9 C 0.9379(9) 0.4070(7) -0.1943(5) 0.0245(19) Uani 1 1 d . . . H9A H 0.9559 0.3506 -0.2532 0.029 Uiso 1 1 calc R . . H9B H 0.8611 0.4926 -0.2085 0.029 Uiso 1 1 calc R . . C10 C 0.8585(8) 0.3544(7) -0.0817(5) 0.0212(19) Uani 1 1 d . . . H10A H 0.9507 0.2901 -0.0551 0.025 Uiso 1 1 calc R . . H10B H 0.8022 0.4244 -0.0289 0.025 Uiso 1 1 calc R . . C4 C 1.5872(9) 0.0933(7) -0.3391(5) 0.0230(19) Uani 1 1 d . . . H4 H 1.6931 0.0704 -0.3231 0.028 Uiso 1 1 calc R . . C7 C 1.2478(9) 0.3912(6) -0.4001(5) 0.0236(19) Uani 1 1 d . . . H7A H 1.1452 0.3961 -0.4200 0.028 Uiso 1 1 calc R . . H7B H 1.3190 0.4281 -0.4624 0.028 Uiso 1 1 calc R . . O13 O 1.3226(9) -0.1091(7) -0.0970(5) 0.0229(15) Uani 1 1 d . . . H131 H 1.300(9) -0.049(7) -0.076(6) 0.01(3) Uiso 1 1 d . . . H132 H 1.427(10) -0.124(6) -0.120(5) 0.02(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0283(13) 0.0161(11) 0.0245(11) -0.0011(8) -0.0099(9) -0.0045(9) O1 0.023(3) 0.022(3) 0.035(3) 0.003(2) -0.010(2) 0.001(2) O2 0.036(3) 0.059(4) 0.026(3) -0.005(3) -0.026(3) 0.009(3) O4 0.045(4) 0.038(4) 0.090(5) -0.042(4) -0.015(3) -0.007(3) O3 0.050(4) 0.051(4) 0.055(4) 0.026(3) -0.018(3) -0.032(3) Cl2 0.0248(12) 0.0226(11) 0.0311(11) 0.0012(9) -0.0160(10) -0.0026(9) Cl3 0.0379(13) 0.0161(11) 0.0247(11) 0.0029(8) -0.0189(9) -0.0075(9) O10 0.055(4) 0.025(3) 0.046(3) 0.006(2) -0.043(3) -0.016(3) N3 0.026(4) 0.008(3) 0.019(3) -0.001(2) -0.013(3) -0.004(3) O9 0.083(5) 0.011(3) 0.090(5) -0.005(3) -0.066(4) 0.004(3) O11 0.042(4) 0.062(4) 0.046(3) 0.030(3) -0.018(3) -0.031(3) C1 0.017(4) 0.027(5) 0.016(4) -0.001(3) -0.005(3) -0.007(4) C3 0.026(5) 0.027(5) 0.016(4) -0.004(3) -0.011(4) -0.003(4) C12 0.022(4) 0.012(4) 0.022(4) 0.005(3) -0.010(3) -0.005(3) O6 0.049(4) 0.077(5) 0.103(5) -0.061(4) -0.048(4) 0.029(4) N1 0.037(4) 0.019(3) 0.026(3) 0.004(3) -0.016(3) -0.014(3) O8 0.049(4) 0.023(3) 0.077(4) -0.013(3) -0.044(3) -0.003(3) N2 0.021(4) 0.013(3) 0.022(3) 0.001(3) -0.008(3) 0.001(3) C11 0.025(4) 0.016(4) 0.021(4) 0.002(3) -0.010(3) -0.004(3) O7 0.034(3) 0.065(4) 0.045(3) 0.034(3) -0.025(3) -0.020(3) C8 0.028(5) 0.020(4) 0.019(4) 0.000(3) -0.006(3) -0.006(4) O12 0.039(4) 0.078(5) 0.019(3) -0.006(3) -0.008(3) -0.010(3) C2 0.023(4) 0.014(4) 0.010(4) 0.001(3) -0.009(3) -0.007(3) C14 0.016(4) 0.025(4) 0.016(4) -0.006(3) 0.000(3) -0.003(4) C13 0.020(4) 0.018(4) 0.024(4) 0.001(3) -0.006(3) -0.003(3) O5 0.057(4) 0.094(5) 0.059(4) 0.047(4) -0.035(3) -0.056(4) C5 0.025(5) 0.033(5) 0.023(4) -0.004(3) -0.004(4) -0.016(4) C6 0.026(5) 0.022(5) 0.016(4) 0.001(3) -0.002(3) -0.012(4) C9 0.031(5) 0.014(4) 0.024(4) 0.004(3) -0.011(4) -0.002(3) C10 0.018(4) 0.025(4) 0.017(4) -0.002(3) -0.002(3) -0.004(4) C4 0.024(5) 0.029(5) 0.023(4) -0.003(3) -0.015(4) -0.010(4) C7 0.038(5) 0.020(4) 0.016(4) 0.007(3) -0.011(4) -0.014(4) O13 0.020(4) 0.024(4) 0.026(3) 0.002(3) -0.011(3) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O3 1.408(5) . ? Cl1 O2 1.431(5) . ? Cl1 O4 1.435(5) . ? Cl1 O1 1.441(5) . ? Cl2 O6 1.402(6) . ? Cl2 O5 1.416(6) . ? Cl2 O8 1.429(5) . ? Cl2 O7 1.439(5) . ? Cl3 O11 1.418(5) . ? Cl3 O12 1.424(5) . ? Cl3 O9 1.447(5) . ? Cl3 O10 1.451(5) . ? N3 C14 1.502(8) . ? N3 C13 1.517(8) . ? C1 C6 1.394(10) . ? C1 C2 1.396(9) . ? C3 C4 1.385(10) . ? C3 C2 1.416(9) . ? C12 C13 1.506(9) . ? C12 C11 1.520(9) . ? N1 C8 1.488(8) . ? N1 C7 1.509(8) . ? N2 C11 1.501(8) . ? N2 C10 1.505(9) . ? C8 C9 1.511(10) . ? C2 C14 1.493(10) . ? C5 C4 1.368(10) . ? C5 C6 1.402(10) . ? C6 C7 1.493(9) . ? C9 C10 1.531(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cl1 O2 110.4(4) . . ? O3 Cl1 O4 110.9(4) . . ? O2 Cl1 O4 108.3(4) . . ? O3 Cl1 O1 110.3(3) . . ? O2 Cl1 O1 108.9(3) . . ? O4 Cl1 O1 108.0(3) . . ? O6 Cl2 O5 110.3(5) . . ? O6 Cl2 O8 107.3(3) . . ? O5 Cl2 O8 109.2(4) . . ? O6 Cl2 O7 111.6(4) . . ? O5 Cl2 O7 108.9(3) . . ? O8 Cl2 O7 109.5(3) . . ? O11 Cl3 O12 109.4(4) . . ? O11 Cl3 O9 110.6(4) . . ? O12 Cl3 O9 108.7(4) . . ? O11 Cl3 O10 108.9(3) . . ? O12 Cl3 O10 109.7(3) . . ? O9 Cl3 O10 109.6(3) . . ? C14 N3 C13 115.4(5) . . ? C6 C1 C2 122.0(6) . . ? C4 C3 C2 119.2(7) . . ? C13 C12 C11 107.5(6) . . ? C8 N1 C7 116.3(5) . . ? C11 N2 C10 116.9(5) . . ? N2 C11 C12 113.3(6) . . ? N1 C8 C9 113.1(6) . . ? C1 C2 C3 118.4(6) . . ? C1 C2 C14 122.4(6) . . ? C3 C2 C14 119.1(6) . . ? C2 C14 N3 113.9(5) . . ? C12 C13 N3 113.7(6) . . ? C4 C5 C6 120.4(7) . . ? C1 C6 C5 118.2(7) . . ? C1 C6 C7 119.5(6) . . ? C5 C6 C7 122.3(7) . . ? C8 C9 C10 108.0(6) . . ? N2 C10 C9 114.0(5) . . ? C5 C4 C3 121.8(7) . . ? C6 C7 N1 111.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N2 C11 C12 47.1(7) . . . . ? C13 C12 C11 N2 177.8(5) . . . . ? C7 N1 C8 C9 -63.3(8) . . . . ? C6 C1 C2 C3 -0.4(9) . . . . ? C6 C1 C2 C14 -178.1(6) . . . . ? C4 C3 C2 C1 -0.9(9) . . . . ? C4 C3 C2 C14 176.8(6) . . . . ? C1 C2 C14 N3 -87.6(7) . . . . ? C3 C2 C14 N3 94.7(7) . . . . ? C13 N3 C14 C2 77.8(7) . . . . ? C11 C12 C13 N3 171.8(5) . . . . ? C14 N3 C13 C12 -99.4(6) . . . . ? C2 C1 C6 C5 1.5(10) . . . . ? C2 C1 C6 C7 -178.7(6) . . . . ? C4 C5 C6 C1 -1.3(10) . . . . ? C4 C5 C6 C7 178.9(6) . . . . ? N1 C8 C9 C10 -178.6(5) . . . . ? C11 N2 C10 C9 53.2(7) . . . . ? C8 C9 C10 N2 -157.5(6) . . . . ? C6 C5 C4 C3 0.0(10) . . . . ? C2 C3 C4 C5 1.2(10) . . . . ? C1 C6 C7 N1 117.7(7) . . . . ? C5 C6 C7 N1 -62.5(8) . . . . ? C8 N1 C7 C6 -51.1(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A O13 0.92 1.98 2.900(8) 176.5 . N3 H3B O10 0.92 2.21 2.940(7) 135.8 . N3 H3B O1 0.92 2.28 2.922(7) 126.9 2_755 N1 H1A O4 0.92 2.09 2.999(8) 172.0 2_765 N1 H1A O1 0.92 2.46 3.065(8) 123.8 2_765 N1 H1A Cl1 0.92 2.78 3.634(6) 155.0 2_765 N1 H1B O11 0.92 2.21 3.029(8) 147.9 1_565 N1 H1B O10 0.92 2.24 2.887(7) 127.1 1_565 N1 H1B Cl3 0.92 2.72 3.515(6) 145.7 1_565 N2 H2A O13 0.92 2.08 2.927(8) 153.4 2_755 N2 H2B O2 0.92 2.21 3.008(7) 144.2 2_665 N2 H2B O4 0.92 2.64 3.386(8) 138.9 2_665 N2 H2B Cl1 0.92 2.97 3.809(6) 153.1 2_665 O13 H131 O8 0.70(7) 2.15(7) 2.841(9) 173(8) 1_655 O13 H132 O7 0.83(7) 2.07(8) 2.861(8) 159(7) 2_755 _diffrn_measured_fraction_theta_max 0.431 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.431 _refine_diff_density_max 0.525 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.099 data_c:\structs\chris\t22\t22 _database_code_depnum_ccdc_archive 'CCDC 272027' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H41 N3 O6 S3' _chemical_formula_weight 695.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.6393(8) _cell_length_b 12.0999(7) _cell_length_c 18.0854(11) _cell_angle_alpha 90.00 _cell_angle_beta 115.5684(28) _cell_angle_gamma 90.00 _cell_volume 3284.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 26070 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.0972 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7513 _reflns_number_gt 4971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+2.1369P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7513 _refine_ls_number_parameters 427 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.43162(4) -0.01821(6) 0.25553(4) 0.02417(16) Uani 1 1 d . . . S2 S -0.24291(4) 0.28040(6) 0.06165(4) 0.02375(16) Uani 1 1 d . . . S3 S 0.07595(4) 0.31985(6) 0.41823(4) 0.02464(16) Uani 1 1 d . . . O1 O -0.39545(12) -0.12578(15) 0.28414(12) 0.0309(5) Uani 1 1 d . . . O2 O -0.48537(12) -0.00082(17) 0.16976(11) 0.0335(5) Uani 1 1 d . . . O3 O -0.33738(11) 0.29599(16) 0.03016(12) 0.0313(5) Uani 1 1 d . . . O4 O -0.18696(11) 0.37197(15) 0.06440(11) 0.0281(4) Uani 1 1 d . . . O5 O 0.03024(12) 0.40000(15) 0.35557(12) 0.0320(5) Uani 1 1 d . . . O6 O 0.06793(12) 0.32118(16) 0.49409(12) 0.0308(4) Uani 1 1 d . . . N1 N -0.34746(13) 0.06694(17) 0.28223(12) 0.0202(5) Uani 1 1 d . . . N2 N -0.20771(14) 0.23486(19) 0.15423(13) 0.0265(5) Uani 1 1 d . . . N3 N 0.03984(13) 0.19871(18) 0.37732(13) 0.0231(5) Uani 1 1 d . . . C1 C -0.11162(16) 0.0733(2) 0.39673(15) 0.0212(5) Uani 1 1 d . . . H1 H -0.1129 0.1463 0.4155 0.025 Uiso 1 1 calc R . . C2 C -0.18895(16) 0.0102(2) 0.36704(15) 0.0208(5) Uani 1 1 d . . . C3 C -0.18586(17) -0.0974(2) 0.34020(15) 0.0229(6) Uani 1 1 d . . . H3 H -0.2384 -0.1412 0.3185 0.027 Uiso 1 1 calc R . . C4 C -0.10689(17) -0.1404(2) 0.34498(16) 0.0261(6) Uani 1 1 d . . . H4 H -0.1048 -0.2144 0.3284 0.031 Uiso 1 1 calc R . . C5 C -0.03053(17) -0.0755(2) 0.37405(16) 0.0252(6) Uani 1 1 d . . . H5 H 0.0233 -0.1054 0.3764 0.030 Uiso 1 1 calc R . . C6 C -0.03196(16) 0.0315(2) 0.39952(15) 0.0215(5) Uani 1 1 d . . . C7 C -0.27469(16) 0.0550(2) 0.36638(15) 0.0227(6) Uani 1 1 d . . . H7A H -0.2947 0.0047 0.3983 0.027 Uiso 1 1 calc R . . H7B H -0.2625 0.1280 0.3938 0.027 Uiso 1 1 calc R . . C8 C -0.36784(17) 0.1819(2) 0.25144(17) 0.0252(6) Uani 1 1 d . . . H8A H -0.3800 0.2269 0.2912 0.030 Uiso 1 1 calc R . . H8B H -0.4223 0.1820 0.1989 0.030 Uiso 1 1 calc R . . C9 C -0.29194(17) 0.2342(2) 0.23844(17) 0.0252(6) Uani 1 1 d . . . H9A H -0.2390 0.2396 0.2919 0.030 Uiso 1 1 calc R . . H9B H -0.3093 0.3102 0.2172 0.030 Uiso 1 1 calc R . . C10 C -0.26687(17) 0.1698(2) 0.17905(16) 0.0261(6) Uani 1 1 d . . . H10A H -0.2366 0.1004 0.2054 0.031 Uiso 1 1 calc R . . H10B H -0.3217 0.1501 0.1298 0.031 Uiso 1 1 calc R . . C11 C -0.11567(16) 0.2527(2) 0.21585(16) 0.0261(6) Uani 1 1 d . . . H11A H -0.1167 0.2718 0.2687 0.031 Uiso 1 1 calc R . . H11B H -0.0906 0.3167 0.1988 0.031 Uiso 1 1 calc R . . C12 C -0.05464(18) 0.1542(2) 0.22910(16) 0.0283(6) Uani 1 1 d . . . H12A H -0.0507 0.1371 0.1772 0.034 Uiso 1 1 calc R . . H12B H -0.0805 0.0891 0.2441 0.034 Uiso 1 1 calc R . . C13 C 0.03883(17) 0.1752(2) 0.29636(16) 0.0261(6) Uani 1 1 d . . . H13A H 0.0764 0.1096 0.3014 0.031 Uiso 1 1 calc R . . H13B H 0.0653 0.2387 0.2803 0.031 Uiso 1 1 calc R . . C14 C 0.05162(16) 0.1022(2) 0.43117(16) 0.0248(6) Uani 1 1 d . . . H14A H 0.0654 0.1280 0.4873 0.030 Uiso 1 1 calc R . . H14B H 0.1025 0.0573 0.4338 0.030 Uiso 1 1 calc R . . C15 C 0.19057(16) 0.3312(2) 0.44214(16) 0.0233(6) Uani 1 1 d . . . C16 C 0.21678(17) 0.3784(2) 0.38629(17) 0.0279(6) Uani 1 1 d . . . H16 H 0.1733 0.4050 0.3352 0.033 Uiso 1 1 calc R . . C17 C 0.30732(16) 0.3867(2) 0.40520(16) 0.0239(6) Uani 1 1 d . . . H17 H 0.3253 0.4195 0.3670 0.029 Uiso 1 1 calc R . . C18 C 0.37149(17) 0.3473(2) 0.47985(18) 0.0282(6) Uani 1 1 d . . . C19 C 0.34293(16) 0.3039(2) 0.53743(17) 0.0269(6) Uani 1 1 d . . . H19 H 0.3858 0.2812 0.5900 0.032 Uiso 1 1 calc R . . C20 C 0.25371(17) 0.2943(2) 0.51777(17) 0.0273(6) Uani 1 1 d . . . H20 H 0.2351 0.2625 0.5559 0.033 Uiso 1 1 calc R . . C21 C 0.46986(17) 0.3470(3) 0.49890(18) 0.0332(7) Uani 1 1 d . . . H21A H 0.4776 0.3767 0.4519 0.050 Uiso 1 1 calc R . . H21B H 0.4927 0.2712 0.5098 0.050 Uiso 1 1 calc R . . H21C H 0.5028 0.3930 0.5472 0.050 Uiso 1 1 calc R . . C22 C -0.22637(16) 0.1800(2) -0.00106(15) 0.0230(6) Uani 1 1 d . . . C23 C -0.14183(17) 0.1652(2) 0.00183(16) 0.0251(6) Uani 1 1 d . . . H23 H -0.0926 0.2061 0.0398 0.030 Uiso 1 1 calc R . . C24 C -0.13020(18) 0.0914(2) -0.05046(16) 0.0281(6) Uani 1 1 d . . . H24 H -0.0722 0.0805 -0.0473 0.034 Uiso 1 1 calc R . . C25 C -0.20119(18) 0.0323(2) -0.10781(17) 0.0298(6) Uani 1 1 d . . . C26 C -0.28497(18) 0.0474(2) -0.10994(17) 0.0304(6) Uani 1 1 d . . . H26 H -0.3343 0.0076 -0.1489 0.036 Uiso 1 1 calc R . . C27 C -0.29808(17) 0.1194(2) -0.05629(16) 0.0274(6) Uani 1 1 d . . . H27 H -0.3554 0.1271 -0.0574 0.033 Uiso 1 1 calc R . . C28 C -0.1866(2) -0.0439(3) -0.1668(2) 0.0421(8) Uani 1 1 d . . . H28A H -0.1229 -0.0603 -0.1462 0.063 Uiso 1 1 calc R . . H28B H -0.2078 -0.0083 -0.2206 0.063 Uiso 1 1 calc R . . H28C H -0.2195 -0.1128 -0.1719 0.063 Uiso 1 1 calc R . . C29 C -0.49724(16) 0.0189(2) 0.30706(16) 0.0240(6) Uani 1 1 d . . . C30 C -0.54482(17) 0.1179(2) 0.28891(16) 0.0276(6) Uani 1 1 d . . . H30 H -0.5376 0.1705 0.2532 0.033 Uiso 1 1 calc R . . C31 C -0.60258(18) 0.1379(2) 0.32385(18) 0.0306(6) Uani 1 1 d . . . H31 H -0.6352 0.2051 0.3119 0.037 Uiso 1 1 calc R . . C32 C -0.61417(18) 0.0616(2) 0.37619(18) 0.0299(6) Uani 1 1 d . . . C33 C -0.56189(18) -0.0324(2) 0.39664(17) 0.0308(6) Uani 1 1 d . . . H33 H -0.5662 -0.0831 0.4349 0.037 Uiso 1 1 calc R . . C34 C -0.50380(18) -0.0543(2) 0.36288(17) 0.0303(6) Uani 1 1 d . . . H34 H -0.4684 -0.1194 0.3778 0.036 Uiso 1 1 calc R . . C35 C -0.6837(2) 0.0789(3) 0.4084(2) 0.0402(8) Uani 1 1 d . . . H35A H -0.7297 0.0217 0.3862 0.060 Uiso 1 1 calc R . . H35B H -0.7111 0.1519 0.3915 0.060 Uiso 1 1 calc R . . H35C H -0.6553 0.0744 0.4684 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0201(3) 0.0267(4) 0.0262(4) -0.0053(3) 0.0105(3) -0.0039(3) S2 0.0197(3) 0.0290(4) 0.0212(3) 0.0009(3) 0.0075(3) -0.0015(3) S3 0.0183(3) 0.0268(4) 0.0265(4) 0.0002(3) 0.0075(3) -0.0008(3) O1 0.0285(10) 0.0214(10) 0.0465(13) -0.0078(9) 0.0195(10) -0.0035(8) O2 0.0261(10) 0.0499(13) 0.0209(11) -0.0073(9) 0.0067(9) -0.0081(9) O3 0.0191(9) 0.0420(12) 0.0282(11) -0.0026(9) 0.0058(8) 0.0021(8) O4 0.0278(10) 0.0290(11) 0.0248(10) 0.0015(8) 0.0088(9) -0.0054(8) O5 0.0237(9) 0.0292(11) 0.0358(12) 0.0082(9) 0.0061(9) 0.0016(8) O6 0.0265(10) 0.0372(12) 0.0300(11) -0.0067(9) 0.0134(9) -0.0021(8) N1 0.0168(10) 0.0216(11) 0.0209(11) 0.0008(9) 0.0069(9) -0.0004(9) N2 0.0212(11) 0.0398(14) 0.0140(11) -0.0002(10) 0.0034(9) -0.0112(10) N3 0.0217(11) 0.0259(12) 0.0208(12) -0.0001(9) 0.0083(10) -0.0030(9) C1 0.0217(12) 0.0214(13) 0.0175(13) -0.0002(11) 0.0055(11) 0.0003(10) C2 0.0215(12) 0.0251(14) 0.0153(13) 0.0048(10) 0.0073(11) 0.0025(10) C3 0.0230(13) 0.0252(14) 0.0205(14) -0.0004(11) 0.0094(11) -0.0024(11) C4 0.0315(14) 0.0218(14) 0.0255(15) 0.0003(11) 0.0128(13) 0.0031(11) C5 0.0222(13) 0.0286(15) 0.0254(15) 0.0043(12) 0.0108(12) 0.0031(11) C6 0.0225(12) 0.0232(14) 0.0163(13) 0.0030(11) 0.0062(11) -0.0004(11) C7 0.0222(13) 0.0268(14) 0.0190(14) -0.0018(11) 0.0088(11) -0.0014(11) C8 0.0239(13) 0.0267(15) 0.0258(15) 0.0020(12) 0.0114(12) 0.0024(11) C9 0.0266(13) 0.0228(14) 0.0278(15) 0.0024(12) 0.0133(12) 0.0006(11) C10 0.0238(13) 0.0322(15) 0.0218(14) -0.0020(12) 0.0094(12) -0.0084(11) C11 0.0222(13) 0.0328(16) 0.0207(14) -0.0007(12) 0.0067(12) -0.0075(11) C12 0.0313(14) 0.0316(16) 0.0216(15) -0.0020(12) 0.0108(13) -0.0041(12) C13 0.0249(13) 0.0331(15) 0.0214(14) 0.0019(12) 0.0109(12) 0.0009(12) C14 0.0203(12) 0.0266(14) 0.0246(14) 0.0048(12) 0.0071(12) 0.0001(11) C15 0.0206(12) 0.0207(13) 0.0266(15) 0.0006(11) 0.0081(12) 0.0007(10) C16 0.0229(13) 0.0282(15) 0.0269(15) 0.0059(12) 0.0054(12) 0.0009(11) C17 0.0176(12) 0.0256(14) 0.0259(14) 0.0075(12) 0.0071(11) -0.0009(11) C18 0.0239(13) 0.0229(14) 0.0364(17) -0.0002(12) 0.0116(13) 0.0003(11) C19 0.0189(13) 0.0235(14) 0.0291(16) 0.0013(12) 0.0016(12) 0.0046(11) C20 0.0277(14) 0.0285(15) 0.0244(15) 0.0011(12) 0.0098(12) 0.0004(12) C21 0.0173(13) 0.0483(19) 0.0294(16) -0.0044(14) 0.0057(12) -0.0057(12) C22 0.0231(13) 0.0261(14) 0.0174(13) 0.0047(11) 0.0063(11) -0.0008(11) C23 0.0194(12) 0.0293(15) 0.0235(14) 0.0048(12) 0.0062(11) -0.0011(11) C24 0.0262(14) 0.0318(16) 0.0283(16) 0.0040(13) 0.0134(13) 0.0004(12) C25 0.0333(15) 0.0280(15) 0.0264(16) 0.0042(12) 0.0111(13) 0.0034(12) C26 0.0273(14) 0.0312(16) 0.0266(16) -0.0066(12) 0.0058(13) -0.0059(12) C27 0.0197(13) 0.0315(15) 0.0274(15) 0.0018(12) 0.0068(12) -0.0028(12) C28 0.0468(19) 0.0416(19) 0.0392(19) -0.0077(15) 0.0198(16) 0.0025(15) C29 0.0201(12) 0.0246(14) 0.0286(15) -0.0028(12) 0.0116(12) -0.0047(11) C30 0.0279(14) 0.0286(15) 0.0254(15) 0.0050(12) 0.0105(12) 0.0045(12) C31 0.0304(15) 0.0257(15) 0.0377(17) -0.0022(13) 0.0166(14) 0.0019(12) C32 0.0291(14) 0.0290(15) 0.0354(17) -0.0055(13) 0.0175(13) -0.0065(12) C33 0.0326(15) 0.0310(16) 0.0312(16) 0.0023(13) 0.0161(14) -0.0036(13) C34 0.0267(14) 0.0263(15) 0.0365(17) 0.0057(13) 0.0125(13) 0.0018(12) C35 0.0481(18) 0.0351(18) 0.049(2) -0.0043(15) 0.0320(17) -0.0005(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.433(2) . ? S1 O1 1.434(2) . ? S1 N1 1.635(2) . ? S1 C29 1.772(3) . ? S2 O4 1.4342(19) . ? S2 O3 1.4346(18) . ? S2 N2 1.614(2) . ? S2 C22 1.763(3) . ? S3 O6 1.4347(19) . ? S3 O5 1.435(2) . ? S3 N3 1.635(2) . ? S3 C15 1.770(2) . ? N1 C8 1.482(3) . ? N1 C7 1.487(3) . ? N2 C11 1.470(3) . ? N2 C10 1.473(3) . ? N3 C14 1.478(3) . ? N3 C13 1.484(3) . ? C1 C2 1.390(3) . ? C1 C6 1.399(3) . ? C2 C3 1.398(4) . ? C2 C7 1.522(3) . ? C3 C4 1.381(3) . ? C4 C5 1.389(4) . ? C5 C6 1.379(4) . ? C6 C14 1.519(3) . ? C8 C9 1.519(3) . ? C9 C10 1.523(4) . ? C11 C12 1.516(4) . ? C12 C13 1.527(4) . ? C15 C16 1.384(4) . ? C15 C20 1.391(4) . ? C16 C17 1.397(3) . ? C17 C18 1.395(4) . ? C18 C19 1.419(4) . ? C18 C21 1.520(3) . ? C19 C20 1.374(4) . ? C22 C27 1.389(4) . ? C22 C23 1.396(3) . ? C23 C24 1.374(4) . ? C24 C25 1.387(4) . ? C25 C26 1.390(4) . ? C25 C28 1.507(4) . ? C26 C27 1.389(4) . ? C29 C34 1.383(4) . ? C29 C30 1.394(4) . ? C30 C31 1.381(4) . ? C31 C32 1.394(4) . ? C32 C33 1.382(4) . ? C32 C35 1.519(4) . ? C33 C34 1.374(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.52(12) . . ? O2 S1 N1 106.39(11) . . ? O1 S1 N1 107.03(11) . . ? O2 S1 C29 107.07(12) . . ? O1 S1 C29 107.36(12) . . ? N1 S1 C29 109.17(11) . . ? O4 S2 O3 119.72(12) . . ? O4 S2 N2 106.76(11) . . ? O3 S2 N2 107.55(12) . . ? O4 S2 C22 106.00(11) . . ? O3 S2 C22 106.48(12) . . ? N2 S2 C22 110.16(12) . . ? O6 S3 O5 120.75(12) . . ? O6 S3 N3 105.97(11) . . ? O5 S3 N3 106.41(12) . . ? O6 S3 C15 107.50(12) . . ? O5 S3 C15 106.76(12) . . ? N3 S3 C15 109.10(11) . . ? C8 N1 C7 115.4(2) . . ? C8 N1 S1 116.91(16) . . ? C7 N1 S1 117.16(16) . . ? C11 N2 C10 117.5(2) . . ? C11 N2 S2 121.97(17) . . ? C10 N2 S2 120.50(17) . . ? C14 N3 C13 116.2(2) . . ? C14 N3 S3 119.44(17) . . ? C13 N3 S3 117.60(17) . . ? C2 C1 C6 121.4(2) . . ? C1 C2 C3 118.6(2) . . ? C1 C2 C7 121.0(2) . . ? C3 C2 C7 120.3(2) . . ? C4 C3 C2 120.4(2) . . ? C3 C4 C5 120.1(2) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C1 118.7(2) . . ? C5 C6 C14 120.7(2) . . ? C1 C6 C14 120.6(2) . . ? N1 C7 C2 112.90(19) . . ? N1 C8 C9 112.2(2) . . ? C8 C9 C10 113.3(2) . . ? N2 C10 C9 111.4(2) . . ? N2 C11 C12 114.4(2) . . ? C11 C12 C13 112.2(2) . . ? N3 C13 C12 113.1(2) . . ? N3 C14 C6 110.9(2) . . ? C16 C15 C20 120.5(2) . . ? C16 C15 S3 120.0(2) . . ? C20 C15 S3 119.5(2) . . ? C15 C16 C17 119.8(2) . . ? C18 C17 C16 120.4(2) . . ? C17 C18 C19 118.6(2) . . ? C17 C18 C21 121.3(2) . . ? C19 C18 C21 120.1(2) . . ? C20 C19 C18 120.5(3) . . ? C19 C20 C15 120.1(2) . . ? C27 C22 C23 119.9(2) . . ? C27 C22 S2 120.15(19) . . ? C23 C22 S2 119.9(2) . . ? C24 C23 C22 119.7(2) . . ? C23 C24 C25 121.5(2) . . ? C24 C25 C26 118.2(3) . . ? C24 C25 C28 119.9(3) . . ? C26 C25 C28 121.8(3) . . ? C27 C26 C25 121.4(3) . . ? C22 C27 C26 119.2(2) . . ? C34 C29 C30 120.4(2) . . ? C34 C29 S1 118.8(2) . . ? C30 C29 S1 120.7(2) . . ? C31 C30 C29 118.7(2) . . ? C30 C31 C32 121.5(3) . . ? C33 C32 C31 118.1(2) . . ? C33 C32 C35 120.5(3) . . ? C31 C32 C35 121.4(3) . . ? C34 C33 C32 121.5(3) . . ? C33 C34 C29 119.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C8 44.8(2) . . . . ? O1 S1 N1 C8 173.66(17) . . . . ? C29 S1 N1 C8 -70.4(2) . . . . ? O2 S1 N1 C7 -172.01(17) . . . . ? O1 S1 N1 C7 -43.2(2) . . . . ? C29 S1 N1 C7 72.75(19) . . . . ? O4 S2 N2 C11 -24.3(2) . . . . ? O3 S2 N2 C11 -153.9(2) . . . . ? C22 S2 N2 C11 90.4(2) . . . . ? O4 S2 N2 C10 157.9(2) . . . . ? O3 S2 N2 C10 28.3(2) . . . . ? C22 S2 N2 C10 -87.4(2) . . . . ? O6 S3 N3 C14 -31.2(2) . . . . ? O5 S3 N3 C14 -160.94(17) . . . . ? C15 S3 N3 C14 84.2(2) . . . . ? O6 S3 N3 C13 178.75(17) . . . . ? O5 S3 N3 C13 49.1(2) . . . . ? C15 S3 N3 C13 -65.8(2) . . . . ? C6 C1 C2 C3 0.5(4) . . . . ? C6 C1 C2 C7 178.3(2) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? C7 C2 C3 C4 -176.4(2) . . . . ? C2 C3 C4 C5 -2.1(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C4 C5 C6 C1 1.0(4) . . . . ? C4 C5 C6 C14 -179.9(2) . . . . ? C2 C1 C6 C5 -1.7(4) . . . . ? C2 C1 C6 C14 179.2(2) . . . . ? C8 N1 C7 C2 -106.2(2) . . . . ? S1 N1 C7 C2 110.0(2) . . . . ? C1 C2 C7 N1 116.4(3) . . . . ? C3 C2 C7 N1 -65.8(3) . . . . ? C7 N1 C8 C9 67.0(3) . . . . ? S1 N1 C8 C9 -149.21(18) . . . . ? N1 C8 C9 C10 57.9(3) . . . . ? C11 N2 C10 C9 71.3(3) . . . . ? S2 N2 C10 C9 -110.8(2) . . . . ? C8 C9 C10 N2 167.5(2) . . . . ? C10 N2 C11 C12 78.0(3) . . . . ? S2 N2 C11 C12 -99.9(3) . . . . ? N2 C11 C12 C13 -177.4(2) . . . . ? C14 N3 C13 C12 91.4(3) . . . . ? S3 N3 C13 C12 -117.6(2) . . . . ? C11 C12 C13 N3 60.4(3) . . . . ? C13 N3 C14 C6 -72.3(3) . . . . ? S3 N3 C14 C6 137.32(19) . . . . ? C5 C6 C14 N3 116.3(3) . . . . ? C1 C6 C14 N3 -64.6(3) . . . . ? O6 S3 C15 C16 -152.3(2) . . . . ? O5 S3 C15 C16 -21.4(3) . . . . ? N3 S3 C15 C16 93.2(2) . . . . ? O6 S3 C15 C20 26.6(2) . . . . ? O5 S3 C15 C20 157.5(2) . . . . ? N3 S3 C15 C20 -87.9(2) . . . . ? C20 C15 C16 C17 1.4(4) . . . . ? S3 C15 C16 C17 -179.7(2) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C16 C17 C18 C19 -3.1(4) . . . . ? C16 C17 C18 C21 175.0(3) . . . . ? C17 C18 C19 C20 4.2(4) . . . . ? C21 C18 C19 C20 -173.9(3) . . . . ? C18 C19 C20 C15 -2.5(4) . . . . ? C16 C15 C20 C19 -0.4(4) . . . . ? S3 C15 C20 C19 -179.2(2) . . . . ? O4 S2 C22 C27 -140.1(2) . . . . ? O3 S2 C22 C27 -11.6(2) . . . . ? N2 S2 C22 C27 104.8(2) . . . . ? O4 S2 C22 C23 36.7(2) . . . . ? O3 S2 C22 C23 165.2(2) . . . . ? N2 S2 C22 C23 -78.5(2) . . . . ? C27 C22 C23 C24 0.5(4) . . . . ? S2 C22 C23 C24 -176.3(2) . . . . ? C22 C23 C24 C25 1.5(4) . . . . ? C23 C24 C25 C26 -1.7(4) . . . . ? C23 C24 C25 C28 177.1(3) . . . . ? C24 C25 C26 C27 -0.1(4) . . . . ? C28 C25 C26 C27 -178.8(3) . . . . ? C23 C22 C27 C26 -2.1(4) . . . . ? S2 C22 C27 C26 174.6(2) . . . . ? C25 C26 C27 C22 2.0(4) . . . . ? O2 S1 C29 C34 129.6(2) . . . . ? O1 S1 C29 C34 0.1(3) . . . . ? N1 S1 C29 C34 -115.6(2) . . . . ? O2 S1 C29 C30 -47.4(2) . . . . ? O1 S1 C29 C30 -176.9(2) . . . . ? N1 S1 C29 C30 67.4(2) . . . . ? C34 C29 C30 C31 -3.9(4) . . . . ? S1 C29 C30 C31 173.0(2) . . . . ? C29 C30 C31 C32 -0.2(4) . . . . ? C30 C31 C32 C33 4.0(4) . . . . ? C30 C31 C32 C35 -174.4(3) . . . . ? C31 C32 C33 C34 -3.9(4) . . . . ? C35 C32 C33 C34 174.5(3) . . . . ? C32 C33 C34 C29 -0.1(4) . . . . ? C30 C29 C34 C33 4.1(4) . . . . ? S1 C29 C34 C33 -172.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.376 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.089 data_c:\structs\chris\a2br\a2br _database_code_depnum_ccdc_archive 'CCDC 272028' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H26 Br3 N3' _chemical_formula_weight 476.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0558(5) _cell_length_b 11.6209(5) _cell_length_c 15.1984(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.8422(26) _cell_angle_gamma 90.00 _cell_volume 1858.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 6.507 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10798 _diffrn_reflns_av_R_equivalents 0.0996 _diffrn_reflns_av_sigmaI/netI 0.1003 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4242 _reflns_number_gt 3202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+1.2521P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4242 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.28728(5) -0.09780(4) 0.02648(3) 0.01854(16) Uani 1 1 d . . . Br2 Br 0.96556(5) 0.41253(5) 0.12631(4) 0.02418(17) Uani 1 1 d . . . Br3 Br 0.49543(5) 0.49373(4) 0.24887(3) 0.01846(16) Uani 1 1 d . . . N2 N 0.4114(4) 0.0746(4) 0.1974(3) 0.0168(9) Uani 1 1 d . . . C1 C 0.7387(4) 0.3006(4) 0.4112(3) 0.0156(10) Uani 1 1 d . . . H1 H 0.7125 0.3727 0.3821 0.019 Uiso 1 1 calc R . . C13 C 0.6982(5) 0.2459(4) 0.1828(3) 0.0172(11) Uani 1 1 d . . . H13A H 0.6797 0.2596 0.1157 0.021 Uiso 1 1 calc R . . H13B H 0.6692 0.3141 0.2098 0.021 Uiso 1 1 calc R . . C4 C 0.8191(5) 0.0929(5) 0.5003(4) 0.0226(12) Uani 1 1 d . . . H4 H 0.8474 0.0225 0.5316 0.027 Uiso 1 1 calc R . . C12 C 0.6243(5) 0.1402(4) 0.1974(3) 0.0168(10) Uani 1 1 d . . . H12A H 0.6418 0.0744 0.1617 0.020 Uiso 1 1 calc R . . H12B H 0.6519 0.1188 0.2636 0.020 Uiso 1 1 calc R . . C2 C 0.8355(4) 0.2387(4) 0.3908(3) 0.0173(10) Uani 1 1 d . . . C11 C 0.4831(5) 0.1664(5) 0.1659(3) 0.0185(11) Uani 1 1 d . . . H11A H 0.4680 0.2415 0.1914 0.022 Uiso 1 1 calc R . . H11B H 0.4522 0.1717 0.0976 0.022 Uiso 1 1 calc R . . C6 C 0.6803(4) 0.2576(4) 0.4736(3) 0.0166(10) Uani 1 1 d . . . C10 C 0.2913(5) 0.1084(5) 0.2178(4) 0.0219(12) Uani 1 1 d . . . H10A H 0.2629 0.0429 0.2482 0.026 Uiso 1 1 calc R . . H10B H 0.2243 0.1235 0.1586 0.026 Uiso 1 1 calc R . . C5 C 0.7210(5) 0.1543(5) 0.5185(3) 0.0208(11) Uani 1 1 d . . . H5 H 0.6821 0.1253 0.5616 0.025 Uiso 1 1 calc R . . C3 C 0.8754(5) 0.1345(5) 0.4364(3) 0.0221(11) Uani 1 1 d . . . H3 H 0.9414 0.0918 0.4237 0.026 Uiso 1 1 calc R . . C14 C 0.8932(5) 0.2834(5) 0.3205(3) 0.0196(11) Uani 1 1 d . . . H14A H 0.9856 0.2677 0.3422 0.024 Uiso 1 1 calc R . . H14B H 0.8817 0.3679 0.3159 0.024 Uiso 1 1 calc R . . N3 N 0.8380(4) 0.2321(4) 0.2258(3) 0.0179(9) Uani 1 1 d . . . N1 N 0.4528(4) 0.3203(4) 0.4087(3) 0.0164(9) Uani 1 1 d . . . C7 C 0.5699(4) 0.3208(4) 0.4907(3) 0.0171(10) Uani 1 1 d . . . H7A H 0.5501 0.2846 0.5437 0.020 Uiso 1 1 calc R . . H7B H 0.5953 0.4014 0.5078 0.020 Uiso 1 1 calc R . . C9 C 0.3050(5) 0.2134(5) 0.2788(3) 0.0210(11) Uani 1 1 d . . . H9A H 0.2246 0.2256 0.2933 0.025 Uiso 1 1 calc R . . H9B H 0.3196 0.2817 0.2444 0.025 Uiso 1 1 calc R . . C8 C 0.4141(5) 0.2031(4) 0.3691(3) 0.0186(11) Uani 1 1 d . . . H8A H 0.3867 0.1560 0.4138 0.022 Uiso 1 1 calc R . . H8B H 0.4873 0.1643 0.3573 0.022 Uiso 1 1 calc R . . H3B H 0.877(6) 0.257(5) 0.190(4) 0.021(16) Uiso 1 1 d . . . H2B H 0.379(5) 0.023(5) 0.157(4) 0.011(13) Uiso 1 1 d . . . H1A H 0.373(10) 0.320(9) 0.434(6) 0.10(3) Uiso 1 1 d . . . H3A H 0.862(5) 0.150(6) 0.230(4) 0.025(15) Uiso 1 1 d . . . H1B H 0.468(8) 0.356(8) 0.373(6) 0.06(3) Uiso 1 1 d . . . H2A H 0.481(7) 0.019(6) 0.264(5) 0.05(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0198(3) 0.0219(3) 0.0139(3) -0.00335(19) 0.0050(2) -0.00402(19) Br2 0.0341(3) 0.0209(3) 0.0213(3) -0.0032(2) 0.0141(2) -0.0060(2) Br3 0.0183(3) 0.0171(3) 0.0190(3) 0.00246(19) 0.0042(2) -0.00110(19) N2 0.018(2) 0.018(2) 0.013(2) -0.0048(18) 0.0022(18) -0.0049(17) C1 0.013(2) 0.015(2) 0.014(2) -0.0027(19) -0.0020(19) -0.0025(19) C13 0.019(3) 0.019(3) 0.015(2) 0.000(2) 0.008(2) 0.002(2) C4 0.023(3) 0.024(3) 0.019(3) 0.004(2) 0.002(2) 0.004(2) C12 0.017(2) 0.016(3) 0.016(2) 0.000(2) 0.0030(19) -0.002(2) C2 0.012(2) 0.022(3) 0.014(2) -0.004(2) -0.0020(19) -0.004(2) C11 0.020(3) 0.021(3) 0.014(2) -0.001(2) 0.004(2) 0.000(2) C6 0.012(2) 0.022(3) 0.011(2) -0.0013(19) -0.0029(18) -0.003(2) C10 0.017(3) 0.025(3) 0.022(3) -0.005(2) 0.003(2) -0.003(2) C5 0.019(3) 0.027(3) 0.014(2) 0.000(2) 0.002(2) -0.001(2) C3 0.015(2) 0.031(3) 0.017(3) 0.002(2) 0.000(2) 0.007(2) C14 0.016(2) 0.022(3) 0.020(3) -0.001(2) 0.005(2) -0.004(2) N3 0.021(2) 0.018(2) 0.018(2) 0.0010(18) 0.0104(19) 0.0012(18) N1 0.017(2) 0.018(2) 0.012(2) 0.0014(18) 0.0022(17) 0.0013(18) C7 0.013(2) 0.020(3) 0.015(2) -0.002(2) -0.0001(19) -0.0027(19) C9 0.011(2) 0.031(3) 0.016(2) -0.002(2) -0.004(2) 0.002(2) C8 0.018(3) 0.021(3) 0.014(2) -0.004(2) 0.000(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C11 1.492(7) . ? N2 C10 1.505(7) . ? C1 C6 1.393(7) . ? C1 C2 1.401(7) . ? C13 N3 1.491(6) . ? C13 C12 1.529(7) . ? C4 C3 1.390(8) . ? C4 C5 1.394(8) . ? C12 C11 1.517(7) . ? C2 C3 1.398(7) . ? C2 C14 1.495(7) . ? C6 C5 1.386(7) . ? C6 C7 1.514(7) . ? C10 C9 1.511(7) . ? C14 N3 1.504(6) . ? N1 C7 1.497(6) . ? N1 C8 1.497(6) . ? C9 C8 1.529(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N2 C10 117.9(4) . . ? C6 C1 C2 120.7(5) . . ? N3 C13 C12 112.2(4) . . ? C3 C4 C5 120.1(5) . . ? C11 C12 C13 109.7(4) . . ? C3 C2 C1 118.7(5) . . ? C3 C2 C14 121.2(5) . . ? C1 C2 C14 120.1(5) . . ? N2 C11 C12 110.6(4) . . ? C5 C6 C1 119.8(5) . . ? C5 C6 C7 119.5(4) . . ? C1 C6 C7 120.6(4) . . ? N2 C10 C9 114.1(4) . . ? C6 C5 C4 120.0(5) . . ? C4 C3 C2 120.5(5) . . ? C2 C14 N3 114.2(4) . . ? C13 N3 C14 116.0(4) . . ? C7 N1 C8 114.0(4) . . ? N1 C7 C6 113.1(4) . . ? C10 C9 C8 113.0(4) . . ? N1 C8 C9 109.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C13 C12 C11 171.0(4) . . . . ? C6 C1 C2 C3 -2.0(7) . . . . ? C6 C1 C2 C14 177.2(4) . . . . ? C10 N2 C11 C12 149.1(4) . . . . ? C13 C12 C11 N2 -168.1(4) . . . . ? C2 C1 C6 C5 2.1(7) . . . . ? C2 C1 C6 C7 -175.9(4) . . . . ? C11 N2 C10 C9 -48.5(6) . . . . ? C1 C6 C5 C4 -0.8(7) . . . . ? C7 C6 C5 C4 177.3(4) . . . . ? C3 C4 C5 C6 -0.6(8) . . . . ? C5 C4 C3 C2 0.8(8) . . . . ? C1 C2 C3 C4 0.5(7) . . . . ? C14 C2 C3 C4 -178.7(5) . . . . ? C3 C2 C14 N3 82.2(6) . . . . ? C1 C2 C14 N3 -97.0(5) . . . . ? C12 C13 N3 C14 -96.3(5) . . . . ? C2 C14 N3 C13 57.5(6) . . . . ? C8 N1 C7 C6 51.6(6) . . . . ? C5 C6 C7 N1 -110.5(5) . . . . ? C1 C6 C7 N1 67.5(6) . . . . ? N2 C10 C9 C8 -53.7(6) . . . . ? C7 N1 C8 C9 -172.5(4) . . . . ? C10 C9 C8 N1 159.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3B Br2 0.84(6) 2.39(6) 3.159(5) 151(5) . N2 H2B Br1 0.85(6) 2.39(6) 3.234(4) 171(5) . N1 H1A Br1 1.06(10) 2.25(10) 3.245(5) 155(8) 2 N3 H3A Br3 0.98(6) 2.36(6) 3.283(5) 155(5) 2_645 N1 H1B Br3 0.75(9) 2.56(9) 3.299(5) 173(8) . N2 H2A Br2 1.25(7) 2.01(7) 3.216(4) 160(5) 2_645 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.291 _refine_diff_density_min -1.568 _refine_diff_density_rms 0.192 data_c:\structs\chris\a2cl\a2cl _database_code_depnum_ccdc_archive 'CCDC 272029' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H26 Cl3 N3' _chemical_formula_weight 342.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5996(3) _cell_length_b 10.1003(4) _cell_length_c 17.1572(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.8496(20) _cell_angle_gamma 90.00 _cell_volume 1659.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.547 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10814 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3784 _reflns_number_gt 3164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.5686P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3784 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.07432(3) 0.31889(4) 0.03601(2) 0.01451(10) Uani 1 1 d . . . Cl2 Cl 0.35118(3) 0.57200(4) 0.12123(2) 0.01486(10) Uani 1 1 d . . . Cl3 Cl 0.21556(4) 0.49685(4) 0.44706(2) 0.01611(10) Uani 1 1 d . . . N1 N 0.49103(13) 0.37477(13) 0.39910(7) 0.0131(3) Uani 1 1 d . . . N3 N 0.77413(13) 0.42137(12) 0.05104(7) 0.0127(3) Uani 1 1 d . . . N2 N 0.35144(12) 0.25837(14) 0.13959(7) 0.0129(3) Uani 1 1 d . . . C3 C 0.89293(15) 0.42075(15) 0.22089(9) 0.0156(3) Uani 1 1 d . . . H3 H 0.9647 0.4039 0.1866 0.019 Uiso 1 1 calc R . . C9 C 0.33578(15) 0.32749(15) 0.28008(8) 0.0139(3) Uani 1 1 d . . . H9A H 0.3677 0.4100 0.2557 0.017 Uiso 1 1 calc R . . H9B H 0.2539 0.3497 0.3097 0.017 Uiso 1 1 calc R . . C5 C 0.80573(15) 0.40526(15) 0.34972(9) 0.0151(3) Uani 1 1 d . . . H5 H 0.8177 0.3774 0.4026 0.018 Uiso 1 1 calc R . . C13 C 0.71536(14) 0.28606(14) 0.06186(9) 0.0139(3) Uani 1 1 d . . . H13A H 0.7542 0.2504 0.1125 0.017 Uiso 1 1 calc R . . H13B H 0.7470 0.2277 0.0202 0.017 Uiso 1 1 calc R . . C14 C 0.74129(15) 0.52619(15) 0.10873(8) 0.0146(3) Uani 1 1 d . . . H14A H 0.6414 0.5501 0.1005 0.017 Uiso 1 1 calc R . . H14B H 0.7968 0.6063 0.0986 0.017 Uiso 1 1 calc R . . C2 C 0.77102(14) 0.48500(14) 0.19313(8) 0.0122(3) Uani 1 1 d . . . C8 C 0.45213(14) 0.27537(15) 0.33664(8) 0.0137(3) Uani 1 1 d . . . H8A H 0.4211 0.1925 0.3610 0.016 Uiso 1 1 calc R . . H8B H 0.5351 0.2546 0.3076 0.016 Uiso 1 1 calc R . . C6 C 0.68386(14) 0.47049(14) 0.32274(8) 0.0127(3) Uani 1 1 d . . . C11 C 0.50598(14) 0.24842(15) 0.14020(8) 0.0136(3) Uani 1 1 d . . . H11A H 0.5356 0.1577 0.1556 0.016 Uiso 1 1 calc R . . H11B H 0.5491 0.3109 0.1792 0.016 Uiso 1 1 calc R . . C10 C 0.29110(15) 0.22816(16) 0.21554(8) 0.0154(3) Uani 1 1 d . . . H10A H 0.3207 0.1382 0.2326 0.018 Uiso 1 1 calc R . . H10B H 0.1880 0.2282 0.2078 0.018 Uiso 1 1 calc R . . C12 C 0.55600(14) 0.28002(15) 0.06023(8) 0.0151(3) Uani 1 1 d . . . H12A H 0.5167 0.3662 0.0422 0.018 Uiso 1 1 calc R . . H12B H 0.5215 0.2113 0.0226 0.018 Uiso 1 1 calc R . . C4 C 0.90992(15) 0.38108(16) 0.29876(9) 0.0174(3) Uani 1 1 d . . . H4 H 0.9932 0.3372 0.3172 0.021 Uiso 1 1 calc R . . C1 C 0.66801(15) 0.51070(14) 0.24512(9) 0.0123(3) Uani 1 1 d . . . H1 H 0.5856 0.5565 0.2270 0.015 Uiso 1 1 calc R . . C7 C 0.56649(15) 0.49739(14) 0.37526(9) 0.0138(3) Uani 1 1 d . . . H7A H 0.6052 0.5433 0.4229 0.017 Uiso 1 1 calc R . . H7B H 0.4984 0.5578 0.3478 0.017 Uiso 1 1 calc R . . H2A H 0.3148(18) 0.201(2) 0.1068(11) 0.025(5) Uiso 1 1 d . . . H2B H 0.3239(18) 0.342(2) 0.1247(11) 0.026(5) Uiso 1 1 d . . . H3A H 0.870(2) 0.4097(18) 0.0496(10) 0.025(5) Uiso 1 1 d . . . H3B H 0.7430(18) 0.4470(18) 0.0031(12) 0.025(5) Uiso 1 1 d . . . H1B H 0.408(2) 0.4037(18) 0.4188(11) 0.026(5) Uiso 1 1 d . . . H1A H 0.5372(18) 0.3328(18) 0.4394(11) 0.023(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01132(17) 0.0172(2) 0.01483(19) -0.00157(14) -0.00041(13) 0.00054(13) Cl2 0.01660(18) 0.01430(19) 0.01338(18) -0.00003(14) -0.00122(13) 0.00185(13) Cl3 0.01908(19) 0.01418(19) 0.01540(19) 0.00313(14) 0.00362(14) 0.00383(14) N1 0.0132(6) 0.0166(7) 0.0094(6) 0.0013(5) 0.0011(5) 0.0019(5) N3 0.0121(6) 0.0156(7) 0.0104(7) -0.0004(5) 0.0005(5) 0.0005(5) N2 0.0118(6) 0.0138(7) 0.0129(6) -0.0014(5) -0.0005(5) -0.0018(5) C3 0.0134(7) 0.0186(8) 0.0152(8) -0.0036(6) 0.0032(6) -0.0008(6) C9 0.0140(7) 0.0151(8) 0.0128(7) -0.0005(6) 0.0022(6) -0.0005(5) C5 0.0162(7) 0.0171(8) 0.0117(7) 0.0001(6) -0.0018(6) -0.0014(6) C13 0.0148(7) 0.0113(7) 0.0156(7) -0.0018(6) 0.0016(6) 0.0002(6) C14 0.0180(7) 0.0134(8) 0.0125(8) -0.0016(6) 0.0022(6) 0.0007(6) C2 0.0143(7) 0.0101(7) 0.0122(7) -0.0024(6) 0.0014(5) -0.0039(5) C8 0.0152(7) 0.0131(8) 0.0130(7) -0.0008(6) 0.0015(6) -0.0004(6) C6 0.0137(7) 0.0108(7) 0.0137(7) -0.0038(6) 0.0010(6) -0.0035(5) C11 0.0112(7) 0.0143(8) 0.0152(7) -0.0008(6) 0.0008(5) 0.0000(6) C10 0.0142(7) 0.0191(8) 0.0131(8) -0.0010(6) 0.0020(6) -0.0043(6) C12 0.0139(7) 0.0177(8) 0.0135(7) -0.0018(6) 0.0004(6) -0.0012(6) C4 0.0124(7) 0.0206(8) 0.0186(8) -0.0022(7) -0.0023(6) 0.0021(6) C1 0.0127(7) 0.0094(7) 0.0144(7) -0.0021(6) -0.0019(5) -0.0010(5) C7 0.0149(7) 0.0135(7) 0.0130(8) -0.0015(6) 0.0016(6) -0.0021(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.4974(19) . ? N1 C7 1.5051(19) . ? N3 C13 1.4947(19) . ? N3 C14 1.4973(19) . ? N2 C11 1.4863(18) . ? N2 C10 1.4926(19) . ? C3 C2 1.394(2) . ? C3 C4 1.394(2) . ? C9 C8 1.524(2) . ? C9 C10 1.534(2) . ? C5 C4 1.394(2) . ? C5 C6 1.394(2) . ? C13 C12 1.529(2) . ? C14 C2 1.515(2) . ? C2 C1 1.400(2) . ? C6 C1 1.391(2) . ? C6 C7 1.514(2) . ? C11 C12 1.518(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C7 117.29(11) . . ? C13 N3 C14 117.80(11) . . ? C11 N2 C10 115.19(12) . . ? C2 C3 C4 120.19(14) . . ? C8 C9 C10 113.04(12) . . ? C4 C5 C6 119.74(14) . . ? N3 C13 C12 114.81(12) . . ? N3 C14 C2 113.78(12) . . ? C3 C2 C1 118.78(14) . . ? C3 C2 C14 123.67(13) . . ? C1 C2 C14 117.54(13) . . ? N1 C8 C9 111.18(12) . . ? C1 C6 C5 119.42(13) . . ? C1 C6 C7 118.66(13) . . ? C5 C6 C7 121.91(13) . . ? N2 C11 C12 110.83(12) . . ? N2 C10 C9 112.98(12) . . ? C11 C12 C13 111.63(12) . . ? C5 C4 C3 120.55(14) . . ? C6 C1 C2 121.30(14) . . ? N1 C7 C6 113.90(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N3 C13 C12 59.29(17) . . . . ? C13 N3 C14 C2 51.01(17) . . . . ? C4 C3 C2 C1 1.1(2) . . . . ? C4 C3 C2 C14 -177.28(14) . . . . ? N3 C14 C2 C3 45.28(19) . . . . ? N3 C14 C2 C1 -133.16(13) . . . . ? C7 N1 C8 C9 -70.44(16) . . . . ? C10 C9 C8 N1 -179.28(11) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C4 C5 C6 C7 179.03(13) . . . . ? C10 N2 C11 C12 179.59(12) . . . . ? C11 N2 C10 C9 64.57(17) . . . . ? C8 C9 C10 N2 -101.10(15) . . . . ? N2 C11 C12 C13 173.41(12) . . . . ? N3 C13 C12 C11 -110.45(14) . . . . ? C6 C5 C4 C3 -0.4(2) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C5 C6 C1 C2 1.1(2) . . . . ? C7 C6 C1 C2 -178.01(13) . . . . ? C3 C2 C1 C6 -1.6(2) . . . . ? C14 C2 C1 C6 176.88(13) . . . . ? C8 N1 C7 C6 -45.22(17) . . . . ? C1 C6 C7 N1 110.61(15) . . . . ? C5 C6 C7 N1 -68.47(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A Cl3 0.86(2) 2.27(2) 3.0777(15) 155.0(17) 2_545 N2 H2B Cl2 0.92(2) 2.34(2) 3.1832(16) 153.1(15) . N3 H3A Cl1 0.929(19) 2.192(19) 3.0889(14) 161.9(16) 1_655 N3 H3B Cl2 0.89(2) 2.27(2) 3.1163(15) 158.1(16) 3_665 N1 H1B Cl3 0.935(19) 2.155(19) 3.0793(14) 169.4(16) . N1 H1A Cl1 0.902(19) 2.268(19) 3.1194(14) 157.4(15) 4_666 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.316 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.055 data_L2-HF-2H[HF2]-H2O.CIF _database_code_depnum_ccdc_archive 'CCDC 272030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H30 F5 N3 O' _chemical_formula_weight 351.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.4382(3) _cell_length_b 16.5549(9) _cell_length_c 19.6525(13) _cell_angle_alpha 90.00 _cell_angle_beta 91.581(2) _cell_angle_gamma 90.00 _cell_volume 1768.62(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min 0.9537 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9562 _diffrn_reflns_av_R_equivalents 0.2443 _diffrn_reflns_av_sigmaI/netI 0.3965 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3628 _reflns_number_gt 1178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo-SMN _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3628 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2775 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.886 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.0949(4) 0.70965(13) 0.09336(12) 0.0395(8) Uani 1 1 d . . . O1 O -0.2033(7) 0.98340(18) 0.29738(17) 0.0429(10) Uani 1 1 d . . . N1 N 0.7877(6) 0.6753(2) -0.00804(18) 0.0371(11) Uani 1 1 d . . . H1A H 0.8742 0.6904 0.0308 0.045 Uiso 1 1 calc R . . H1B H 0.8804 0.6377 -0.0303 0.045 Uiso 1 1 calc R . . C1 C 0.6867(8) 0.8409(2) 0.0465(2) 0.0341(12) Uani 1 1 d . . . H1 H 0.8320 0.8195 0.0675 0.041 Uiso 1 1 calc R . . H1F H 0.0920 1.0794 0.1772 0.095(19) Uiso 1 1 d R . . F2 F 0.0343(5) 1.14791(15) 0.16744(14) 0.0608(9) Uani 1 1 d . . . N2 N 0.4096(6) 0.6333(2) 0.16910(17) 0.0345(11) Uani 1 1 d . . . H2A H 0.3074 0.5901 0.1766 0.041 Uiso 1 1 calc R . . H2B H 0.3295 0.6676 0.1391 0.041 Uiso 1 1 calc R . . C2 C 0.5495(9) 0.8998(3) 0.0807(2) 0.0343(13) Uani 1 1 d . . . F3 F 0.1213(5) 1.01689(14) 0.20355(13) 0.0501(9) Uani 1 1 d . . . N3 N 0.4615(7) 0.9064(2) 0.20476(18) 0.0382(11) Uani 1 1 d . . . H3A H 0.3297 0.9411 0.2005 0.046 Uiso 1 1 calc R . . H3B H 0.5376 0.9165 0.2463 0.046 Uiso 1 1 calc R . . C3 C 0.3403(9) 0.9313(3) 0.0486(3) 0.0388(13) Uani 1 1 d . . . H3 H 0.2478 0.9717 0.0709 0.047 Uiso 1 1 calc R . . F4 F 0.0106(5) 0.92186(15) 0.40578(14) 0.0481(8) Uani 1 1 d . . . C4 C 0.2647(9) 0.9048(3) -0.0151(3) 0.0407(13) Uani 1 1 d . . . H4 H 0.1203 0.9265 -0.0363 0.049 Uiso 1 1 calc R . . H2F H 0.149(16) 0.895(4) 0.378(4) 0.16(3) Uiso 1 1 d . . . F5 F 0.3590(6) 0.88099(18) 0.34929(14) 0.0642(9) Uani 1 1 d . . . C5 C 0.4009(9) 0.8460(3) -0.0483(2) 0.0378(13) Uani 1 1 d . . . H5 H 0.3489 0.8278 -0.0922 0.045 Uiso 1 1 calc R . . C6 C 0.6115(9) 0.8139(2) -0.0175(2) 0.0294(12) Uani 1 1 d . . . C7 C 0.7530(9) 0.7476(2) -0.0527(2) 0.0396(13) Uani 1 1 d . . . H7A H 0.6627 0.7316 -0.0950 0.047 Uiso 1 1 calc R . . H7B H 0.9159 0.7686 -0.0655 0.047 Uiso 1 1 calc R . . C8 C 0.5496(8) 0.6370(3) 0.0117(2) 0.0373(13) Uani 1 1 d . . . H8A H 0.4683 0.6130 -0.0292 0.045 Uiso 1 1 calc R . . H8B H 0.4393 0.6792 0.0294 0.045 Uiso 1 1 calc R . . C9 C 0.5870(8) 0.5721(2) 0.0652(2) 0.0366(13) Uani 1 1 d . . . H9A H 0.7257 0.5373 0.0518 0.044 Uiso 1 1 calc R . . H9B H 0.4377 0.5379 0.0656 0.044 Uiso 1 1 calc R . . C10 C 0.6398(8) 0.6034(3) 0.1376(2) 0.0374(13) Uani 1 1 d . . . H10A H 0.7116 0.5594 0.1658 0.045 Uiso 1 1 calc R . . H10B H 0.7613 0.6478 0.1361 0.045 Uiso 1 1 calc R . . C11 C 0.4577(9) 0.6767(3) 0.2350(2) 0.0410(14) Uani 1 1 d . . . H11A H 0.5747 0.6445 0.2634 0.049 Uiso 1 1 calc R . . H11B H 0.3018 0.6804 0.2597 0.049 Uiso 1 1 calc R . . C12 C 0.5619(9) 0.7615(3) 0.2267(2) 0.0409(13) Uani 1 1 d . . . H12A H 0.6401 0.7791 0.2703 0.049 Uiso 1 1 calc R . . H12B H 0.6903 0.7604 0.1920 0.049 Uiso 1 1 calc R . . C13 C 0.3649(8) 0.8218(3) 0.2054(2) 0.0391(13) Uani 1 1 d . . . H13A H 0.2997 0.8077 0.1594 0.047 Uiso 1 1 calc R . . H13B H 0.2275 0.8184 0.2373 0.047 Uiso 1 1 calc R . . C14 C 0.6383(9) 0.9265(3) 0.1503(2) 0.0395(13) Uani 1 1 d . . . H14A H 0.7982 0.9003 0.1613 0.047 Uiso 1 1 calc R . . H14B H 0.6654 0.9856 0.1499 0.047 Uiso 1 1 calc R . . H1O H -0.085(10) 0.993(3) 0.279(3) 0.07(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0379(17) 0.0427(15) 0.0377(17) -0.0011(12) -0.0006(14) -0.0015(12) O1 0.040(2) 0.045(2) 0.044(2) -0.0060(16) 0.007(2) -0.0037(17) N1 0.041(3) 0.037(2) 0.034(3) -0.0046(18) 0.005(2) 0.0031(19) C1 0.027(3) 0.037(3) 0.039(3) 0.003(3) -0.001(3) -0.001(2) F2 0.064(2) 0.056(2) 0.063(2) 0.0178(15) 0.0056(17) 0.0040(15) N2 0.038(3) 0.033(2) 0.032(3) 0.0025(18) 0.005(2) -0.0062(18) C2 0.031(3) 0.035(3) 0.037(4) 0.005(2) 0.000(3) -0.001(2) F3 0.0491(19) 0.0463(17) 0.055(2) 0.0015(14) 0.0088(15) 0.0040(13) N3 0.042(3) 0.037(2) 0.036(3) -0.0018(17) 0.005(2) 0.0018(19) C3 0.035(3) 0.034(3) 0.047(4) 0.004(3) 0.007(3) 0.002(2) F4 0.0476(18) 0.0530(17) 0.0440(18) 0.0084(13) 0.0056(15) -0.0031(14) C4 0.040(3) 0.049(3) 0.032(3) 0.009(3) -0.011(3) -0.002(3) F5 0.064(2) 0.087(2) 0.0410(19) -0.0050(16) 0.0051(16) 0.0099(17) C5 0.038(3) 0.042(3) 0.034(3) 0.000(2) 0.003(3) 0.000(3) C6 0.029(3) 0.029(3) 0.030(3) 0.002(2) -0.005(3) -0.002(2) C7 0.044(3) 0.040(3) 0.035(3) 0.005(2) 0.003(3) 0.006(2) C8 0.038(3) 0.039(3) 0.035(3) -0.005(2) 0.000(3) -0.002(2) C9 0.034(3) 0.032(3) 0.044(3) -0.002(2) 0.005(3) 0.002(2) C10 0.033(3) 0.037(3) 0.042(3) 0.001(2) -0.001(3) 0.006(2) C11 0.047(3) 0.043(3) 0.033(3) 0.001(2) -0.005(3) -0.001(3) C12 0.037(3) 0.043(3) 0.042(3) -0.007(2) -0.001(3) -0.001(3) C13 0.039(3) 0.036(3) 0.042(3) 0.000(2) 0.002(3) -0.006(2) C14 0.042(3) 0.038(3) 0.039(3) -0.002(2) 0.002(3) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.494(5) . ? N1 C8 1.503(5) . ? C1 C6 1.386(6) . ? C1 C2 1.410(5) . ? N2 C10 1.496(5) . ? N2 C11 1.499(5) . ? C2 C3 1.387(6) . ? C2 C14 1.506(6) . ? N3 C14 1.495(5) . ? N3 C13 1.497(5) . ? C3 C4 1.378(6) . ? C4 C5 1.396(6) . ? C5 C6 1.386(6) . ? C6 C7 1.519(5) . ? C8 C9 1.513(6) . ? C9 C10 1.534(6) . ? C11 C12 1.525(6) . ? C12 C13 1.514(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C8 113.2(3) . . ? C6 C1 C2 120.5(4) . . ? C10 N2 C11 112.9(4) . . ? C3 C2 C1 118.8(5) . . ? C3 C2 C14 122.7(4) . . ? C1 C2 C14 118.4(4) . . ? C14 N3 C13 116.6(3) . . ? C4 C3 C2 120.8(4) . . ? C3 C4 C5 119.9(5) . . ? C6 C5 C4 120.3(5) . . ? C1 C6 C5 119.6(4) . . ? C1 C6 C7 120.4(4) . . ? C5 C6 C7 120.0(4) . . ? N1 C7 C6 111.6(3) . . ? N1 C8 C9 112.3(4) . . ? C8 C9 C10 115.0(4) . . ? N2 C10 C9 111.0(4) . . ? N2 C11 C12 113.9(4) . . ? C13 C12 C11 112.0(4) . . ? N3 C13 C12 111.9(4) . . ? N3 C14 C2 112.9(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(6) . . . . ? C6 C1 C2 C14 179.5(4) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? C14 C2 C3 C4 -179.6(4) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C2 C1 C6 C5 0.7(6) . . . . ? C2 C1 C6 C7 -177.1(3) . . . . ? C4 C5 C6 C1 -0.2(6) . . . . ? C4 C5 C6 C7 177.6(4) . . . . ? C8 N1 C7 C6 61.4(5) . . . . ? C1 C6 C7 N1 52.2(5) . . . . ? C5 C6 C7 N1 -125.6(4) . . . . ? C7 N1 C8 C9 -171.4(4) . . . . ? N1 C8 C9 C10 75.9(4) . . . . ? C11 N2 C10 C9 -170.6(3) . . . . ? C8 C9 C10 N2 76.6(5) . . . . ? C10 N2 C11 C12 75.2(5) . . . . ? N2 C11 C12 C13 77.8(5) . . . . ? C14 N3 C13 C12 69.7(5) . . . . ? C11 C12 C13 N3 173.6(3) . . . . ? C13 N3 C14 C2 48.6(5) . . . . ? C3 C2 C14 N3 64.2(5) . . . . ? C1 C2 C14 N3 -116.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F1 0.92 1.72 2.627(4) 166.4 1_655 N1 H1B F4 0.92 1.76 2.653(4) 162.9 4_675 F3 H1F F2 1.17 1.19 2.327(4) 161.5 . N2 H2A O1 0.92 1.93 2.809(4) 159.6 2_545 N2 H2B F1 0.92 1.69 2.570(4) 158.8 . N3 H3A F3 0.92 1.69 2.601(4) 168.4 . N3 H3B O1 0.92 2.04 2.842(5) 145.6 1_655 N3 H3B F5 0.92 2.34 2.940(4) 122.2 . F4 H2F F5 1.04(8) 1.31(8) 2.323(3) 163(7) . _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 0.423 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.116 data_a5 _database_code_depnum_ccdc_archive 'CCDC 272031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H28 N4' _chemical_formula_weight 276.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.5482(8) _cell_length_b 14.9721(11) _cell_length_c 17.2980(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.7346(29) _cell_angle_gamma 90.00 _cell_volume 3248.3(11) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5174 _diffrn_reflns_av_R_equivalents 0.0927 _diffrn_reflns_av_sigmaI/netI 0.1422 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 29.00 _reflns_number_total 2494 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0101(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2494 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1595 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3462(3) 0.2359(2) 0.39108(16) 0.0531(9) Uani 1 1 d . . . N3 N 0.4275(4) 0.4563(2) 0.5964(2) 0.0583(9) Uani 1 1 d . . . N4 N 0.3250(3) 0.5612(2) 0.45892(18) 0.0537(8) Uani 1 1 d . . . N2 N 0.4017(2) 0.25279(19) 0.56232(17) 0.0554(9) Uani 1 1 d . . . C6 C 0.2803(3) 0.3486(2) 0.30024(16) 0.0486(9) Uani 1 1 d . . . C1 C 0.2934(3) 0.4214(2) 0.34898(18) 0.0494(9) Uani 1 1 d . . . C8 C 0.3981(4) 0.1500(2) 0.40187(19) 0.0641(11) Uani 1 1 d . . . C2 C 0.2310(3) 0.4969(2) 0.34350(17) 0.0518(9) Uani 1 1 d . . . C7 C 0.3472(3) 0.2673(2) 0.31099(17) 0.0574(10) Uani 1 1 d . . . C14 C 0.4106(3) 0.6215(2) 0.5779(2) 0.0656(11) Uani 1 1 d . . . C11 C 0.4581(4) 0.2970(3) 0.6269(2) 0.0655(11) Uani 1 1 d . . . C13 C 0.4002(4) 0.5420(3) 0.6306(2) 0.0711(11) Uani 1 1 d . . . C5 C 0.2002(3) 0.3534(3) 0.24245(18) 0.0618(10) Uani 1 1 d . . . C3 C 0.1523(3) 0.5003(3) 0.2847(2) 0.0615(10) Uani 1 1 d . . . C16 C 0.2414(3) 0.5737(2) 0.3995(2) 0.0639(10) Uani 1 1 d . . . C9 C 0.3851(4) 0.1144(3) 0.4831(2) 0.0646(11) Uani 1 1 d . . . C4 C 0.1383(3) 0.4288(3) 0.2351(2) 0.0668(11) Uani 1 1 d . . . C12 C 0.4113(4) 0.3833(3) 0.6503(2) 0.0690(11) Uani 1 1 d . . . C10 C 0.4445(4) 0.1652(2) 0.5469(2) 0.0653(11) Uani 1 1 d . . . C15 C 0.3228(4) 0.6329(3) 0.5169(2) 0.0689(11) Uani 1 1 d . . . H8B H 0.470(3) 0.1586(19) 0.3929(14) 0.054(10) Uiso 1 1 d . . . H7B H 0.422(3) 0.2829(17) 0.2978(14) 0.049(9) Uiso 1 1 d . . . H10B H 0.517(3) 0.1648(18) 0.5338(13) 0.048(9) Uiso 1 1 d . . . H9B H 0.407(3) 0.052(3) 0.4821(16) 0.080(11) Uiso 1 1 d . . . H8A H 0.370(4) 0.094(3) 0.365(2) 0.133(15) Uiso 1 1 d . . . H14B H 0.482(3) 0.6175(19) 0.5534(15) 0.063(9) Uiso 1 1 d . . . H15A H 0.254(3) 0.6297(19) 0.5421(15) 0.060(9) Uiso 1 1 d . . . H14A H 0.407(3) 0.676(2) 0.6114(17) 0.085(10) Uiso 1 1 d . . . H16B H 0.254(2) 0.630(2) 0.3671(16) 0.075(9) Uiso 1 1 d . . . H16A H 0.170(3) 0.5831(19) 0.4258(15) 0.066(9) Uiso 1 1 d . . . H7A H 0.322(2) 0.2178(17) 0.2762(14) 0.051(8) Uiso 1 1 d . . . H10A H 0.443(2) 0.131(2) 0.5950(16) 0.063(9) Uiso 1 1 d . . . H9A H 0.312(3) 0.112(2) 0.4939(17) 0.074(12) Uiso 1 1 d . . . H15B H 0.327(3) 0.686(2) 0.4887(16) 0.072(10) Uiso 1 1 d . . . H3 H 0.106(3) 0.554(2) 0.2812(15) 0.061(10) Uiso 1 1 d . . . H5 H 0.186(3) 0.303(2) 0.2099(17) 0.071(10) Uiso 1 1 d . . . H4 H 0.081(3) 0.430(2) 0.1961(19) 0.078(12) Uiso 1 1 d . . . H1 H 0.351(3) 0.4164(16) 0.3877(15) 0.056(9) Uiso 1 1 d . . . H11B H 0.529(3) 0.3004(19) 0.6124(15) 0.054(10) Uiso 1 1 d . . . H11A H 0.458(2) 0.2608(19) 0.6719(18) 0.065(9) Uiso 1 1 d . . . H11 H 0.299(3) 0.237(3) 0.406(2) 0.085(19) Uiso 1 1 d . . . H21 H 0.404(3) 0.285(2) 0.5302(18) 0.077(14) Uiso 1 1 d . . . H13A H 0.331(3) 0.532(2) 0.6483(15) 0.064(10) Uiso 1 1 d . . . H12A H 0.339(3) 0.378(2) 0.6604(16) 0.067(11) Uiso 1 1 d . . . H12B H 0.440(2) 0.4020(18) 0.7011(18) 0.064(9) Uiso 1 1 d . . . H13B H 0.441(3) 0.548(2) 0.6760(19) 0.074(12) Uiso 1 1 d . . . H41A H 0.306(4) 0.515(3) 0.478(2) 0.021(15) Uiso 0.50 1 d P A 2 H41B H 0.391(6) 0.561(4) 0.442(3) 0.06(2) Uiso 0.50 1 d P B 1 H31A H 0.392(4) 0.457(3) 0.559(2) 0.008(16) Uiso 0.50 1 d P C 1 H31B H 0.480(5) 0.459(3) 0.576(3) 0.03(2) Uiso 0.50 1 d P D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.054(2) 0.0562(19) 0.0500(17) 0.0033(12) 0.0066(16) 0.0086(17) N3 0.059(3) 0.069(2) 0.048(2) -0.0071(16) 0.004(2) -0.0105(18) N4 0.038(2) 0.0473(19) 0.076(2) -0.0035(16) 0.0011(18) 0.0021(17) N2 0.058(2) 0.0562(18) 0.0513(17) 0.0145(15) -0.0112(14) -0.0038(16) C6 0.048(2) 0.060(2) 0.0386(17) 0.0048(15) 0.0023(16) -0.0045(18) C1 0.042(2) 0.058(2) 0.0485(19) 0.0067(16) -0.0067(17) -0.0034(19) C8 0.055(3) 0.061(2) 0.077(2) 0.0013(18) 0.011(2) 0.007(2) C2 0.039(2) 0.057(2) 0.0590(19) 0.0161(16) -0.0030(17) -0.0017(19) C7 0.062(3) 0.065(2) 0.045(2) -0.0077(16) 0.0099(18) -0.005(2) C14 0.053(3) 0.060(2) 0.084(3) -0.026(2) 0.010(2) -0.003(2) C11 0.061(3) 0.082(3) 0.053(2) 0.018(2) -0.011(2) -0.011(2) C13 0.068(3) 0.080(3) 0.067(3) -0.022(2) 0.014(2) -0.009(2) C5 0.069(3) 0.074(3) 0.0424(19) 0.0044(19) 0.0033(19) -0.016(2) C3 0.043(3) 0.075(3) 0.066(2) 0.028(2) -0.0016(19) -0.001(2) C16 0.050(3) 0.054(2) 0.087(3) 0.008(2) -0.007(2) 0.010(2) C9 0.064(3) 0.048(2) 0.081(3) 0.0069(18) 0.000(2) -0.003(2) C4 0.050(3) 0.095(3) 0.055(2) 0.019(2) -0.007(2) -0.012(3) C12 0.072(3) 0.090(3) 0.044(2) -0.0007(19) 0.001(2) -0.020(3) C10 0.054(3) 0.063(3) 0.078(3) 0.021(2) -0.002(2) 0.008(2) C15 0.060(3) 0.054(2) 0.092(3) -0.009(2) 0.011(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.450(4) . ? N1 C7 1.464(4) . ? N3 C12 1.455(5) . ? N3 C13 1.459(4) . ? N4 C16 1.459(4) . ? N4 C15 1.470(4) . ? N2 C10 1.446(4) . ? N2 C11 1.462(4) . ? C6 C1 1.386(4) . ? C6 C5 1.398(5) . ? C6 C7 1.487(4) . ? C1 C2 1.376(4) . ? C8 C9 1.516(5) . ? C2 C3 1.397(4) . ? C2 C16 1.506(5) . ? C14 C13 1.507(5) . ? C14 C15 1.512(5) . ? C11 C12 1.482(5) . ? C5 C4 1.375(5) . ? C3 C4 1.380(5) . ? C9 C10 1.517(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C7 113.0(3) . . ? C12 N3 C13 111.2(3) . . ? C16 N4 C15 111.0(3) . . ? C10 N2 C11 112.1(3) . . ? C1 C6 C5 117.7(3) . . ? C1 C6 C7 120.8(3) . . ? C5 C6 C7 121.5(3) . . ? C2 C1 C6 123.2(3) . . ? N1 C8 C9 111.7(3) . . ? C1 C2 C3 118.0(3) . . ? C1 C2 C16 123.0(3) . . ? C3 C2 C16 119.0(3) . . ? N1 C7 C6 111.1(3) . . ? C13 C14 C15 115.8(4) . . ? N2 C11 C12 114.6(3) . . ? N3 C13 C14 115.1(3) . . ? C4 C5 C6 120.0(4) . . ? C4 C3 C2 119.8(4) . . ? N4 C16 C2 113.7(3) . . ? C8 C9 C10 115.7(3) . . ? C5 C4 C3 121.3(4) . . ? N3 C12 C11 114.5(3) . . ? N2 C10 C9 114.3(3) . . ? N4 C15 C14 111.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C6 C1 C2 0.7(4) . . . . ? C7 C6 C1 C2 -177.5(3) . . . . ? C7 N1 C8 C9 -173.7(4) . . . . ? C6 C1 C2 C3 -1.4(4) . . . . ? C6 C1 C2 C16 176.3(3) . . . . ? C8 N1 C7 C6 171.9(3) . . . . ? C1 C6 C7 N1 51.1(4) . . . . ? C5 C6 C7 N1 -127.0(3) . . . . ? C10 N2 C11 C12 -174.4(3) . . . . ? C12 N3 C13 C14 -177.9(4) . . . . ? C15 C14 C13 N3 76.3(5) . . . . ? C1 C6 C5 C4 0.5(5) . . . . ? C7 C6 C5 C4 178.7(3) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C16 C2 C3 C4 -177.0(3) . . . . ? C15 N4 C16 C2 -173.3(3) . . . . ? C1 C2 C16 N4 1.1(5) . . . . ? C3 C2 C16 N4 178.8(3) . . . . ? N1 C8 C9 C10 -68.8(5) . . . . ? C6 C5 C4 C3 -1.0(5) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C13 N3 C12 C11 -167.7(4) . . . . ? N2 C11 C12 N3 -72.4(5) . . . . ? C11 N2 C10 C9 177.0(3) . . . . ? C8 C9 C10 N2 70.4(5) . . . . ? C16 N4 C15 C14 -178.9(3) . . . . ? C13 C14 C15 N4 -67.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H11 N2 0.66(4) 2.60(4) 3.241(5) 169(5) 7_556 N2 H21 N1 0.74(3) 2.60(3) 3.033(4) 119(3) . N4 H41A N3 0.81(5) 2.67(5) 3.096(5) 115(4) . N4 H41B N3 0.88(7) 2.41(7) 3.287(6) 173(5) 5_666 N3 H31A N4 0.77(4) 2.46(4) 3.096(5) 141(4) . N3 H31B N4 0.75(6) 2.56(6) 3.287(6) 164(5) 5_666 _diffrn_measured_fraction_theta_max 0.577 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.577 _refine_diff_density_max 0.209 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.064 data_c:\structs\chris\a5clo4\pna21 _database_code_depnum_ccdc_archive 'CCDC 272032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H34 Br Cl3 N4 O13' _chemical_formula_weight 676.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 14.8930(4) _cell_length_b 18.0550(6) _cell_length_c 10.0567(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2704.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 1.884 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15138 _diffrn_reflns_av_R_equivalents 0.1006 _diffrn_reflns_av_sigmaI/netI 0.0976 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5068 _reflns_number_gt 4064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+33.9735P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 5068 _refine_ls_number_parameters 363 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1153 _refine_ls_R_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.2047 _refine_ls_wR_factor_gt 0.1944 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.29513(8) 0.77039(6) 0.63061(13) 0.0367(3) Uani 1 1 d . . . Cl1 Cl 0.57439(19) 0.81005(15) 0.9638(3) 0.0302(6) Uani 1 1 d . . . O1 O 0.6106(6) 0.7372(5) 0.9735(12) 0.052(3) Uani 1 1 d . . . N1 N 0.3099(5) 0.9514(5) 0.6930(9) 0.024(2) Uani 1 1 d . . . H1D H 0.2557 0.9756 0.6981 0.028 Uiso 1 1 calc R . . H1C H 0.3000 0.9062 0.6534 0.028 Uiso 1 1 calc R . . C1 C 0.3445(8) 0.9389(6) 0.8307(11) 0.031(3) Uani 1 1 d . . . H1A H 0.3684 0.9860 0.8665 0.037 Uiso 1 1 calc R . . H1B H 0.3944 0.9027 0.8277 0.037 Uiso 1 1 calc R . . Cl2 Cl 0.1945(2) 0.92557(16) 0.3298(3) 0.0410(8) Uani 1 1 d . . . O2 O 0.6448(6) 0.8610(5) 0.9250(8) 0.044(2) Uani 1 1 d . . . N2 N 0.3018(8) 0.7756(5) 0.9459(9) 0.044(3) Uani 1 1 d . . . H2D H 0.2441 0.7623 0.9231 0.052 Uiso 1 1 calc R . . H2C H 0.3336 0.7816 0.8683 0.052 Uiso 1 1 calc R . . C2 C 0.2682(9) 0.9088(6) 0.9266(13) 0.031(3) Uani 1 1 d . . . H2A H 0.2454 0.9505 0.9810 0.037 Uiso 1 1 calc R . . H2B H 0.2177 0.8903 0.8719 0.037 Uiso 1 1 calc R . . Cl3 Cl 0.14345(19) 1.08585(15) 0.8174(3) 0.0301(6) Uani 1 1 d . . . O3 O 0.5034(5) 0.8100(4) 0.8657(8) 0.0301(19) Uani 1 1 d . . . N3 N 0.4456(6) 0.6548(5) 0.8579(10) 0.033(2) Uani 1 1 d . . . H3C H 0.4526 0.7042 0.8379 0.039 Uiso 1 1 calc R . . H3D H 0.4920 0.6414 0.9133 0.039 Uiso 1 1 calc R . . C3 C 0.2985(10) 0.8484(6) 1.0172(11) 0.039(3) Uani 1 1 d . . . H3A H 0.2568 0.8448 1.0935 0.047 Uiso 1 1 calc R . . H3B H 0.3590 0.8604 1.0521 0.047 Uiso 1 1 calc R . . O4 O 0.5387(6) 0.8318(5) 1.0894(8) 0.044(2) Uani 1 1 d . . . N4 N 0.5847(11) 0.7250(7) 0.4822(15) 0.026(3) Uani 0.60 1 d P A 1 H4A H 0.5903 0.6862 0.4235 0.031 Uiso 0.60 1 calc PR A 1 H4B H 0.6388 0.7304 0.5255 0.031 Uiso 0.60 1 calc PR A 1 C4 C 0.3428(9) 0.7139(6) 1.0229(11) 0.032(3) Uani 1 1 d . . . H1 H 0.3030 0.7004 1.0980 0.039 Uiso 1 1 calc R . . H2 H 0.4011 0.7302 1.0600 0.039 Uiso 1 1 calc R . . O5 O 0.2926(7) 0.9091(8) 0.3180(12) 0.073(4) Uani 1 1 d . . . C5 C 0.3575(7) 0.6447(6) 0.9318(12) 0.029(3) Uani 1 1 d . . . H5A H 0.3597 0.5991 0.9865 0.035 Uiso 1 1 calc R . . H5B H 0.3074 0.6400 0.8678 0.035 Uiso 1 1 calc R . . O6 O 0.1843(7) 0.9847(6) 0.2408(10) 0.063(3) Uani 1 1 d . . . C6 C 0.4526(9) 0.6108(7) 0.7317(13) 0.039(3) Uani 1 1 d . . . H6A H 0.3991 0.6202 0.6757 0.047 Uiso 1 1 calc R . . H6B H 0.4543 0.5573 0.7531 0.047 Uiso 1 1 calc R . . O7 O 0.1412(12) 0.8682(8) 0.2910(14) 0.123(6) Uani 1 1 d . . . C7 C 0.5365(8) 0.6319(6) 0.6558(11) 0.034(3) Uani 1 1 d . . . H7A H 0.5526 0.5919 0.5927 0.040 Uiso 1 1 calc R B 1 H7B H 0.5872 0.6387 0.7183 0.040 Uiso 1 1 calc R B 1 O8 O 0.1815(7) 0.9479(6) 0.4630(9) 0.058(3) Uani 1 1 d . . . C8 C 0.5179(16) 0.7079(11) 0.576(2) 0.028(5) Uani 0.60 1 d PU A 1 H8A H 0.4595 0.7039 0.5292 0.033 Uiso 0.60 1 calc PR A 1 H8B H 0.5134 0.7491 0.6403 0.033 Uiso 0.60 1 calc PR A 1 O9 O 0.2329(5) 1.1098(5) 0.7888(10) 0.046(2) Uani 1 1 d . . . C9 C 0.5644(16) 0.7966(12) 0.403(2) 0.024(5) Uani 0.60 1 d PU A 1 H9A H 0.6150 0.8068 0.3424 0.028 Uiso 0.60 1 calc PR A 1 H9B H 0.5100 0.7886 0.3486 0.028 Uiso 0.60 1 calc PR A 1 O10 O 0.1295(6) 1.0191(5) 0.7441(9) 0.045(2) Uani 1 1 d . . . C10 C 0.5504(9) 0.8601(6) 0.4874(12) 0.037(3) Uani 1 1 d . . . O11 O 0.0820(6) 1.1430(5) 0.7766(9) 0.044(2) Uani 1 1 d . . . C11 C 0.6237(10) 0.8856(8) 0.5538(14) 0.048(4) Uani 1 1 d . A . H11 H 0.6794 0.8605 0.5445 0.058 Uiso 1 1 calc R . . O12 O 0.1360(6) 1.0729(4) 0.9553(9) 0.043(2) Uani 1 1 d . . . C12 C 0.6186(8) 0.9474(7) 0.6346(16) 0.044(3) Uani 1 1 d . . . H12 H 0.6712 0.9655 0.6768 0.053 Uiso 1 1 calc R A . O13 O 0.5501(7) 0.5727(5) 1.0246(9) 0.049(2) Uani 1 1 d . . . C13 C 0.5382(8) 0.9828(6) 0.6543(11) 0.030(3) Uani 1 1 d . A . H13 H 0.5349 1.0243 0.7123 0.036 Uiso 1 1 calc R . . C14 C 0.4617(8) 0.9579(5) 0.5891(10) 0.026(3) Uani 1 1 d . . . C15 C 0.4656(9) 0.8959(6) 0.5049(11) 0.031(3) Uani 1 1 d . A . H15 H 0.4133 0.8782 0.4609 0.037 Uiso 1 1 calc R . . C16 C 0.3724(9) 0.9959(6) 0.6066(10) 0.035(3) Uani 1 1 d . A . H16A H 0.3444 1.0034 0.5184 0.042 Uiso 1 1 calc R . . H16B H 0.3820 1.0452 0.6473 0.042 Uiso 1 1 calc R . . N4A N 0.5007(14) 0.7198(11) 0.486(2) 0.018(4) Uani 0.40 1 d PU A 2 H4A1 H 0.4436 0.7311 0.5144 0.021 Uiso 0.40 1 calc PR A 2 H4A2 H 0.4964 0.6783 0.4331 0.021 Uiso 0.40 1 calc PR A 2 C8A C 0.556(2) 0.6999(16) 0.606(3) 0.026(7) Uani 0.40 1 d PU A 2 H8A1 H 0.6205 0.7015 0.5821 0.031 Uiso 0.40 1 calc PR A 2 H8A2 H 0.5458 0.7375 0.6765 0.031 Uiso 0.40 1 calc PR A 2 C9A C 0.533(2) 0.7830(15) 0.400(3) 0.015(7) Uani 0.40 1 d PU A 2 H9A1 H 0.4886 0.7929 0.3296 0.018 Uiso 0.40 1 calc PR A 2 H9A2 H 0.5903 0.7683 0.3563 0.018 Uiso 0.40 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0542(7) 0.0283(5) 0.0277(5) -0.0006(6) 0.0027(7) -0.0019(6) Cl1 0.0338(15) 0.0286(14) 0.0282(13) -0.0018(12) -0.0032(12) -0.0076(13) O1 0.021(5) 0.032(5) 0.103(8) 0.003(5) -0.021(5) 0.003(4) N1 0.009(4) 0.024(5) 0.038(5) -0.002(4) -0.002(4) 0.002(4) C1 0.043(7) 0.027(6) 0.023(5) -0.001(5) -0.001(5) 0.003(5) Cl2 0.060(2) 0.0349(16) 0.0277(14) -0.0041(13) -0.0091(15) 0.0074(15) O2 0.065(6) 0.038(5) 0.029(4) -0.006(4) 0.000(4) -0.038(5) N2 0.085(9) 0.033(5) 0.014(4) 0.004(4) -0.012(5) 0.010(5) C2 0.035(7) 0.023(6) 0.036(7) 0.003(5) -0.011(5) -0.011(5) Cl3 0.0383(16) 0.0288(14) 0.0230(13) 0.0018(12) 0.0014(12) 0.0059(12) O3 0.022(4) 0.037(5) 0.031(4) 0.001(4) -0.009(3) 0.003(4) N3 0.034(6) 0.031(5) 0.033(6) -0.003(4) 0.003(4) 0.010(5) C3 0.070(10) 0.024(6) 0.023(6) 0.002(5) 0.012(6) -0.009(6) O4 0.044(5) 0.056(5) 0.031(5) -0.006(4) 0.001(4) -0.021(4) N4 0.037(10) 0.011(7) 0.031(8) -0.003(6) 0.000(7) 0.005(6) C4 0.052(8) 0.023(6) 0.022(6) 0.001(5) -0.003(5) 0.004(6) O5 0.059(7) 0.103(9) 0.058(7) -0.003(7) -0.031(6) 0.013(7) C5 0.012(5) 0.030(6) 0.044(7) -0.005(5) 0.010(5) 0.000(5) O6 0.058(7) 0.077(8) 0.055(6) 0.021(6) 0.002(5) 0.003(6) C6 0.063(9) 0.025(6) 0.028(6) -0.001(5) -0.005(6) -0.007(6) O7 0.189(16) 0.089(10) 0.090(10) 0.029(9) -0.058(11) -0.096(11) C7 0.051(7) 0.032(6) 0.018(6) 0.000(5) 0.012(5) -0.003(5) O8 0.072(7) 0.072(7) 0.029(5) -0.006(5) 0.001(5) -0.011(6) C8 0.032(6) 0.027(6) 0.025(6) 0.005(4) 0.005(5) -0.001(5) O9 0.017(4) 0.065(6) 0.057(6) -0.009(5) 0.000(4) -0.006(4) C9 0.024(6) 0.024(6) 0.023(6) 0.001(4) -0.002(5) 0.000(5) O10 0.036(5) 0.048(5) 0.050(5) -0.016(4) -0.001(4) 0.009(4) C10 0.064(9) 0.022(6) 0.026(6) 0.010(5) 0.015(6) 0.019(6) O11 0.048(6) 0.035(5) 0.048(5) 0.010(4) -0.013(5) 0.012(4) C11 0.034(8) 0.060(9) 0.050(8) 0.024(7) 0.004(6) 0.009(7) O12 0.063(6) 0.032(5) 0.034(5) 0.006(4) 0.006(5) 0.009(4) C12 0.043(7) 0.046(7) 0.043(7) 0.019(8) -0.013(8) 0.006(6) O13 0.057(7) 0.052(6) 0.037(5) -0.004(5) -0.014(4) 0.006(5) C13 0.046(7) 0.022(5) 0.021(6) 0.007(5) -0.001(5) -0.005(5) C14 0.052(8) 0.010(5) 0.017(5) 0.003(4) 0.000(5) 0.000(5) C15 0.054(8) 0.017(5) 0.023(6) 0.010(5) 0.008(5) 0.001(5) C16 0.069(9) 0.020(5) 0.015(6) 0.012(5) -0.001(5) 0.001(6) N4A 0.019(6) 0.018(6) 0.016(6) -0.002(4) 0.000(4) -0.001(4) C8A 0.025(8) 0.027(8) 0.025(8) -0.001(5) -0.002(5) 0.001(5) C9A 0.014(8) 0.013(8) 0.017(8) -0.001(5) 0.002(5) 0.000(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O1 1.425(9) . ? Cl1 O4 1.425(9) . ? Cl1 O3 1.446(8) . ? Cl1 O2 1.449(8) . ? N1 C1 1.494(14) . ? N1 C16 1.506(14) . ? C1 C2 1.586(17) . ? Cl2 O7 1.362(12) . ? Cl2 O6 1.401(10) . ? Cl2 O8 1.412(10) . ? Cl2 O5 1.496(11) . ? N2 C4 1.488(14) . ? N2 C3 1.499(14) . ? C2 C3 1.491(16) . ? Cl3 O12 1.412(9) . ? Cl3 O10 1.428(9) . ? Cl3 O9 1.430(9) . ? Cl3 O11 1.439(9) . ? N3 C6 1.501(15) . ? N3 C5 1.519(14) . ? N4 C8 1.40(2) . ? N4 C9 1.55(2) . ? C4 C5 1.564(15) . ? C6 C7 1.512(17) . ? C7 C8A 1.36(3) . ? C7 C8 1.62(2) . ? C9 C10 1.44(2) . ? C10 C11 1.36(2) . ? C10 C15 1.430(17) . ? C10 C9A 1.67(3) . ? C11 C12 1.38(2) . ? C12 C13 1.372(16) . ? C13 C14 1.390(16) . ? C14 C15 1.405(15) . ? C14 C16 1.506(16) . ? N4A C8A 1.51(3) . ? N4A C9A 1.51(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cl1 O4 109.5(6) . . ? O1 Cl1 O3 108.8(5) . . ? O4 Cl1 O3 109.4(5) . . ? O1 Cl1 O2 109.3(6) . . ? O4 Cl1 O2 109.5(5) . . ? O3 Cl1 O2 110.2(5) . . ? C1 N1 C16 113.7(8) . . ? N1 C1 C2 111.6(9) . . ? O7 Cl2 O6 109.4(8) . . ? O7 Cl2 O8 114.2(9) . . ? O6 Cl2 O8 111.9(7) . . ? O7 Cl2 O5 113.3(10) . . ? O6 Cl2 O5 101.9(7) . . ? O8 Cl2 O5 105.4(7) . . ? C4 N2 C3 114.9(9) . . ? C3 C2 C1 113.8(11) . . ? O12 Cl3 O10 110.9(6) . . ? O12 Cl3 O9 108.7(6) . . ? O10 Cl3 O9 106.7(6) . . ? O12 Cl3 O11 110.5(6) . . ? O10 Cl3 O11 111.4(6) . . ? O9 Cl3 O11 108.6(6) . . ? C6 N3 C5 114.2(10) . . ? C2 C3 N2 111.1(9) . . ? C8 N4 C9 112.8(16) . . ? N2 C4 C5 110.5(9) . . ? N3 C5 C4 108.1(9) . . ? N3 C6 C7 110.5(10) . . ? C8A C7 C6 126.2(16) . . ? C8A C7 C8 23.8(13) . . ? C6 C7 C8 108.9(12) . . ? N4 C8 C7 113.6(16) . . ? C10 C9 N4 113.2(15) . . ? C11 C10 C15 119.7(12) . . ? C11 C10 C9 116.2(14) . . ? C15 C10 C9 124.0(15) . . ? C11 C10 C9A 131.6(15) . . ? C15 C10 C9A 108.0(15) . . ? C9 C10 C9A 17.5(12) . . ? C10 C11 C12 121.2(13) . . ? C13 C12 C11 120.7(12) . . ? C12 C13 C14 119.7(11) . . ? C13 C14 C15 120.6(11) . . ? C13 C14 C16 121.4(9) . . ? C15 C14 C16 118.0(11) . . ? C14 C15 C10 118.1(12) . . ? C14 C16 N1 111.8(8) . . ? C8A N4A C9A 117(2) . . ? C7 C8A N4A 113(2) . . ? N4A C9A C10 112(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N1 C1 C2 166.7(9) . . . . ? N1 C1 C2 C3 138.0(10) . . . . ? C1 C2 C3 N2 -79.3(14) . . . . ? C4 N2 C3 C2 172.2(11) . . . . ? C3 N2 C4 C5 -170.4(11) . . . . ? C6 N3 C5 C4 -157.3(9) . . . . ? N2 C4 C5 N3 83.6(12) . . . . ? C5 N3 C6 C7 172.5(10) . . . . ? N3 C6 C7 C8A -61(2) . . . . ? N3 C6 C7 C8 -80.0(14) . . . . ? C9 N4 C8 C7 178.2(15) . . . . ? C8A C7 C8 N4 51(4) . . . . ? C6 C7 C8 N4 -168.4(15) . . . . ? C8 N4 C9 C10 56(2) . . . . ? N4 C9 C10 C11 69(2) . . . . ? N4 C9 C10 C15 -110.5(17) . . . . ? N4 C9 C10 C9A -85(5) . . . . ? C15 C10 C11 C12 -2.5(18) . . . . ? C9 C10 C11 C12 178.4(14) . . . . ? C9A C10 C11 C12 -171.4(16) . . . . ? C10 C11 C12 C13 3(2) . . . . ? C11 C12 C13 C14 -2.1(18) . . . . ? C12 C13 C14 C15 1.1(16) . . . . ? C12 C13 C14 C16 -179.2(10) . . . . ? C13 C14 C15 C10 -0.8(15) . . . . ? C16 C14 C15 C10 179.5(9) . . . . ? C11 C10 C15 C14 1.4(16) . . . . ? C9 C10 C15 C14 -179.5(14) . . . . ? C9A C10 C15 C14 172.7(13) . . . . ? C13 C14 C16 N1 -105.7(11) . . . . ? C15 C14 C16 N1 74.0(11) . . . . ? C1 N1 C16 C14 60.9(11) . . . . ? C6 C7 C8A N4A -73(3) . . . . ? C8 C7 C8A N4A -25(3) . . . . ? C9A N4A C8A C7 -163(2) . . . . ? C8A N4A C9A C10 -54(3) . . . . ? C11 C10 C9A N4A 89(3) . . . . ? C15 C10 C9A N4A -81(2) . . . . ? C9 C10 C9A N4A 120(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D O10 0.92 2.09 2.997(12) 168.9 . N1 H1D O9 0.92 2.61 3.229(13) 125.0 . N1 H1D Cl3 0.92 2.86 3.688(9) 150.0 . N1 H1C Br1 0.92 2.46 3.335(9) 158.0 . N2 H2D O1 0.92 2.05 2.870(15) 147.3 4_465 N2 H2D Cl1 0.92 2.87 3.727(13) 154.6 4_465 N2 H2C Br1 0.92 2.47 3.173(9) 133.8 . N2 H2C O3 0.92 2.58 3.172(15) 122.6 . N3 H3C O3 0.92 2.07 2.932(13) 154.7 . N3 H3C Cl1 0.92 2.92 3.559(10) 127.5 . N3 H3D O13 0.92 1.88 2.726(14) 151.5 . N3 H3D O1 0.92 2.54 3.098(13) 119.1 . N4 H4A O7 0.92 1.82 2.69(2) 156.7 4_565 N4 H4A Cl2 0.92 2.71 3.523(14) 147.2 4_565 N4 H4B Br1 0.92 2.56 3.472(16) 172.4 4_565 N4A H4A1 Br1 0.92 2.60 3.51(2) 170.6 . N4A H4A2 O11 0.92 2.06 2.81(2) 137.0 3_544 N4A H4A2 Cl3 0.92 2.91 3.65(2) 138.4 3_544 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.964 _refine_diff_density_min -1.026 _refine_diff_density_rms 0.147 data_c:\structs\chris\t5\t5 _database_code_depnum_ccdc_archive 'CCDC 272033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H52 N4 O8 S4' _chemical_formula_weight 893.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.8732(12) _cell_length_b 13.1219(10) _cell_length_c 15.1537(11) _cell_angle_alpha 88.4512(67) _cell_angle_beta 86.6823(59) _cell_angle_gamma 68.4241(61) _cell_volume 2191.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14657 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.1932 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.57 _reflns_number_total 9826 _reflns_number_gt 5921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.8380P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0050(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9826 _refine_ls_number_parameters 546 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1759 _refine_ls_R_factor_gt 0.0988 _refine_ls_wR_factor_ref 0.1583 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S2 S 0.44314(8) 0.22471(8) 0.04593(6) 0.0183(2) Uani 1 1 d . . . S1 S 1.06001(8) -0.05759(8) -0.19135(6) 0.0194(2) Uani 1 1 d . . . S3 S 0.47078(8) -0.09476(8) 0.27839(6) 0.0182(2) Uani 1 1 d . . . S4 S 0.95181(9) -0.51244(8) 0.27971(7) 0.0255(3) Uani 1 1 d . . . O3 O 0.4351(2) 0.2598(2) -0.04417(16) 0.0228(6) Uani 1 1 d . . . O1 O 1.1647(2) -0.1566(2) -0.19672(17) 0.0243(6) Uani 1 1 d . . . O6 O 0.5056(2) -0.1754(2) 0.34797(16) 0.0234(6) Uani 1 1 d . . . O4 O 0.3531(2) 0.1874(2) 0.08671(17) 0.0235(6) Uani 1 1 d . . . N2 N 0.5723(2) 0.1233(2) 0.05441(19) 0.0161(7) Uani 1 1 d . . . O2 O 1.0735(2) 0.0434(2) -0.17073(18) 0.0276(7) Uani 1 1 d . . . N3 N 0.5956(2) -0.0977(2) 0.22613(19) 0.0160(7) Uani 1 1 d . . . N1 N 0.9648(3) -0.0762(2) -0.11540(19) 0.0176(7) Uani 1 1 d . . . O5 O 0.3904(2) -0.1018(2) 0.21412(17) 0.0245(6) Uani 1 1 d . . . O8 O 1.0390(2) -0.5990(2) 0.22847(18) 0.0298(7) Uani 1 1 d . . . O7 O 0.9932(3) -0.4616(2) 0.34637(18) 0.0347(7) Uani 1 1 d . . . C12 C 0.5890(3) -0.0439(3) 0.1388(2) 0.0164(8) Uani 1 1 d . . . H12A H 0.5128 -0.0388 0.1123 0.020 Uiso 1 1 calc R . . H12B H 0.6574 -0.0901 0.0996 0.020 Uiso 1 1 calc R . . N4 N 0.8754(3) -0.4214(3) 0.2109(2) 0.0266(8) Uani 1 1 d . . . C8 C 0.8571(3) 0.0244(3) -0.0951(3) 0.0234(9) Uani 1 1 d . . . H8B H 0.8129 0.0496 -0.1498 0.028 Uiso 1 1 calc R . . H8A H 0.8854 0.0826 -0.0772 0.028 Uiso 1 1 calc R . . C10 C 0.6796(3) 0.1256(3) 0.0014(2) 0.0206(9) Uani 1 1 d . . . H10B H 0.7213 0.1635 0.0353 0.025 Uiso 1 1 calc R . . H10A H 0.6527 0.1683 -0.0534 0.025 Uiso 1 1 calc R . . C7 C 0.9444(3) -0.1820(3) -0.1223(2) 0.0186(8) Uani 1 1 d . . . H7A H 0.9831 -0.2180 -0.1786 0.022 Uiso 1 1 calc R . . H7B H 0.8562 -0.1659 -0.1236 0.022 Uiso 1 1 calc R . . C24 C 0.4423(3) 0.3366(3) 0.1098(2) 0.0173(8) Uani 1 1 d . . . C11 C 0.5934(3) 0.0707(3) 0.1429(2) 0.0176(8) Uani 1 1 d . . . H11A H 0.5305 0.1154 0.1865 0.021 Uiso 1 1 calc R . . H11B H 0.6736 0.0657 0.1621 0.021 Uiso 1 1 calc R . . C38 C 0.8472(3) -0.5628(3) 0.3337(3) 0.0248(9) Uani 1 1 d . . . C6 C 0.9948(3) -0.2601(3) -0.0466(2) 0.0180(8) Uani 1 1 d . . . C1 C 0.9220(3) -0.3073(3) 0.0005(2) 0.0200(9) Uani 1 1 d . . . H1 H 0.8393 -0.2861 -0.0130 0.024 Uiso 1 1 calc R . . C25 C 0.5180(3) 0.3927(3) 0.0831(3) 0.0237(9) Uani 1 1 d . . . H25 H 0.5732 0.3686 0.0333 0.028 Uiso 1 1 calc R . . C36 C 0.4576(3) 0.0583(3) 0.4002(2) 0.0212(9) Uani 1 1 d . . . H36 H 0.5311 0.0060 0.4202 0.025 Uiso 1 1 calc R . . C13 C 0.7061(3) -0.1209(3) 0.2750(2) 0.0182(8) Uani 1 1 d . . . H13A H 0.6888 -0.1342 0.3380 0.022 Uiso 1 1 calc R . . H13B H 0.7304 -0.0563 0.2714 0.022 Uiso 1 1 calc R . . C31 C 0.4037(3) 0.0347(3) 0.3288(2) 0.0168(8) Uani 1 1 d . . . C16 C 0.8874(3) -0.4382(3) 0.1147(2) 0.0239(9) Uani 1 1 d . . . H16B H 0.8057 -0.4083 0.0907 0.029 Uiso 1 1 calc R . . H16A H 0.9217 -0.5179 0.1028 0.029 Uiso 1 1 calc R . . C19 C 0.9563(4) -0.1141(4) -0.4272(3) 0.0282(10) Uani 1 1 d . . . H19 H 0.9747 -0.1744 -0.4660 0.034 Uiso 1 1 calc R . . C2 C 0.9668(3) -0.3848(3) 0.0668(2) 0.0213(9) Uani 1 1 d . . . C18 C 1.0164(3) -0.1284(3) -0.3490(3) 0.0235(9) Uani 1 1 d . . . H18 H 1.0747 -0.1978 -0.3341 0.028 Uiso 1 1 calc R . . C32 C 0.2994(3) 0.1115(3) 0.2974(3) 0.0225(9) Uani 1 1 d . . . H32 H 0.2641 0.0960 0.2473 0.027 Uiso 1 1 calc R . . C34 C 0.2970(3) 0.2360(3) 0.4129(3) 0.0251(9) Uani 1 1 d . . . C35 C 0.4041(4) 0.1583(3) 0.4422(3) 0.0250(9) Uani 1 1 d . . . H35 H 0.4408 0.1742 0.4914 0.030 Uiso 1 1 calc R . . C9 C 0.7693(3) 0.0109(3) -0.0231(2) 0.0205(9) Uani 1 1 d . . . H9B H 0.8137 -0.0260 0.0292 0.025 Uiso 1 1 calc R . . H9A H 0.7256 -0.0341 -0.0447 0.025 Uiso 1 1 calc R . . C15 C 0.7786(4) -0.3227(3) 0.2460(3) 0.0273(10) Uani 1 1 d . . . H15A H 0.7608 -0.3350 0.3092 0.033 Uiso 1 1 calc R . . H15B H 0.7041 -0.3102 0.2141 0.033 Uiso 1 1 calc R . . C4 C 1.1604(3) -0.3670(4) 0.0417(3) 0.0311(10) Uani 1 1 d . . . H4 H 1.2423 -0.3865 0.0566 0.037 Uiso 1 1 calc R . . C14 C 0.8102(3) -0.2208(3) 0.2377(3) 0.0239(9) Uani 1 1 d . . . H14B H 0.8277 -0.2076 0.1746 0.029 Uiso 1 1 calc R . . H14A H 0.8840 -0.2322 0.2700 0.029 Uiso 1 1 calc R . . C22 C 0.9068(3) 0.0631(3) -0.3154(3) 0.0240(9) Uani 1 1 d . . . H22 H 0.8916 0.1244 -0.2782 0.029 Uiso 1 1 calc R . . C20 C 0.8695(4) -0.0132(4) -0.4497(3) 0.0312(11) Uani 1 1 d . . . C39 C 0.8455(4) -0.5759(3) 0.4252(3) 0.0312(10) Uani 1 1 d . . . H39 H 0.9016 -0.5592 0.4587 0.037 Uiso 1 1 calc R . . C40 C 0.7609(4) -0.6135(3) 0.4672(3) 0.0383(12) Uani 1 1 d . . . H40 H 0.7598 -0.6229 0.5295 0.046 Uiso 1 1 calc R . . C17 C 0.9897(3) -0.0394(3) -0.2932(2) 0.0189(8) Uani 1 1 d . . . C26 C 0.5122(4) 0.4836(3) 0.1296(3) 0.0286(10) Uani 1 1 d . . . H26 H 0.5645 0.5212 0.1117 0.034 Uiso 1 1 calc R . . C29 C 0.3630(3) 0.3710(3) 0.1831(3) 0.0249(9) Uani 1 1 d . . . H28 H 0.3122 0.3323 0.2022 0.030 Uiso 1 1 calc R . . C28 C 0.3589(4) 0.4627(3) 0.2279(3) 0.0300(10) Uani 1 1 d . . . H27 H 0.3045 0.4865 0.2782 0.036 Uiso 1 1 calc R . . C5 C 1.1144(3) -0.2918(3) -0.0259(3) 0.0267(10) Uani 1 1 d . . . H5 H 1.1662 -0.2619 -0.0581 0.032 Uiso 1 1 calc R . . C27 C 0.4318(4) 0.5209(3) 0.2017(3) 0.0303(10) Uani 1 1 d . . . C3 C 1.0867(3) -0.4135(3) 0.0872(3) 0.0265(10) Uani 1 1 d . . . H3 H 1.1187 -0.4655 0.1328 0.032 Uiso 1 1 calc R . . C21 C 0.8470(4) 0.0743(4) -0.3927(3) 0.0317(11) Uani 1 1 d . . . H21 H 0.7888 0.1438 -0.4074 0.038 Uiso 1 1 calc R . . C42 C 0.6828(4) -0.6268(4) 0.3282(3) 0.0391(12) Uani 1 1 d . . . H42 H 0.6278 -0.6453 0.2948 0.047 Uiso 1 1 calc R . . C33 C 0.2464(3) 0.2118(3) 0.3398(3) 0.0245(9) Uani 1 1 d . . . H33 H 0.1743 0.2646 0.3184 0.029 Uiso 1 1 calc R . . C41 C 0.6785(4) -0.6374(3) 0.4194(3) 0.0383(12) Uani 1 1 d . . . C37 C 0.2363(4) 0.3428(4) 0.4616(3) 0.0407(12) Uani 1 1 d . . . H37C H 0.1810 0.3335 0.5089 0.061 Uiso 1 1 calc R . . H37A H 0.1904 0.3997 0.4204 0.061 Uiso 1 1 calc R . . H37B H 0.2981 0.3644 0.4871 0.061 Uiso 1 1 calc R . . C43 C 0.7667(4) -0.5894(3) 0.2852(3) 0.0344(11) Uani 1 1 d . . . H43 H 0.7688 -0.5820 0.2227 0.041 Uiso 1 1 calc R . . C23 C 0.8006(4) -0.0011(4) -0.5318(3) 0.0445(13) Uani 1 1 d . . . H23A H 0.7250 -0.0133 -0.5172 0.067 Uiso 1 1 calc R . . H23C H 0.8501 -0.0551 -0.5755 0.067 Uiso 1 1 calc R . . H23B H 0.7819 0.0728 -0.5562 0.067 Uiso 1 1 calc R . . C30 C 0.4255(5) 0.6213(4) 0.2507(3) 0.0521(14) Uani 1 1 d . . . H30C H 0.4885 0.6007 0.2939 0.078 Uiso 1 1 calc R . . H30B H 0.3456 0.6540 0.2813 0.078 Uiso 1 1 calc R . . H30A H 0.4383 0.6745 0.2086 0.078 Uiso 1 1 calc R . . C44 C 0.5799(5) -0.6717(4) 0.4651(4) 0.0620(17) Uani 1 1 d . . . H44B H 0.6048 -0.7013 0.5239 0.093 Uiso 1 1 calc R . . H44C H 0.5676 -0.7279 0.4299 0.093 Uiso 1 1 calc R . . H44A H 0.5041 -0.6079 0.4709 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S2 0.0163(5) 0.0167(5) 0.0220(5) -0.0015(4) -0.0022(4) -0.0060(4) S1 0.0159(5) 0.0221(6) 0.0225(5) 0.0009(4) 0.0007(4) -0.0101(4) S3 0.0187(5) 0.0187(5) 0.0187(5) -0.0008(4) 0.0007(4) -0.0091(4) S4 0.0270(5) 0.0194(6) 0.0259(6) 0.0042(4) 0.0019(5) -0.0044(4) O3 0.0277(14) 0.0197(15) 0.0203(14) 0.0011(11) -0.0052(12) -0.0075(12) O1 0.0143(13) 0.0274(16) 0.0284(15) 0.0016(12) 0.0019(11) -0.0049(11) O6 0.0307(15) 0.0199(15) 0.0221(15) 0.0026(12) 0.0007(12) -0.0126(12) O4 0.0174(13) 0.0220(16) 0.0352(16) -0.0015(12) -0.0012(12) -0.0120(11) N2 0.0142(15) 0.0175(17) 0.0180(16) -0.0002(13) 0.0021(13) -0.0079(13) O2 0.0283(15) 0.0264(17) 0.0362(17) -0.0012(13) 0.0039(13) -0.0203(13) N3 0.0138(15) 0.0187(17) 0.0152(16) 0.0005(13) 0.0009(13) -0.0059(13) N1 0.0162(16) 0.0155(17) 0.0208(17) -0.0027(13) 0.0025(13) -0.0059(13) O5 0.0239(14) 0.0312(17) 0.0237(15) -0.0038(12) -0.0015(12) -0.0161(12) O8 0.0257(15) 0.0198(16) 0.0331(17) 0.0062(13) 0.0022(13) 0.0035(12) O7 0.0408(17) 0.0347(18) 0.0316(17) 0.0042(14) -0.0048(14) -0.0171(14) C12 0.0194(19) 0.014(2) 0.0143(19) 0.0020(15) 0.0004(16) -0.0044(15) N4 0.0297(18) 0.0141(18) 0.0241(19) 0.0067(14) 0.0069(15) 0.0044(14) C8 0.021(2) 0.019(2) 0.030(2) -0.0019(17) 0.0064(18) -0.0078(17) C10 0.0204(19) 0.020(2) 0.023(2) -0.0020(17) 0.0046(17) -0.0101(16) C7 0.0173(18) 0.019(2) 0.023(2) -0.0013(16) -0.0014(16) -0.0103(16) C24 0.0161(18) 0.011(2) 0.024(2) -0.0008(15) -0.0038(16) -0.0028(15) C11 0.0205(19) 0.021(2) 0.0116(19) 0.0020(15) -0.0023(15) -0.0085(16) C38 0.025(2) 0.015(2) 0.030(2) 0.0059(17) 0.0016(19) -0.0028(17) C6 0.0189(19) 0.016(2) 0.020(2) -0.0010(16) -0.0018(16) -0.0076(16) C1 0.0170(19) 0.015(2) 0.025(2) -0.0013(17) -0.0011(17) -0.0027(16) C25 0.024(2) 0.022(2) 0.026(2) 0.0007(18) -0.0003(18) -0.0103(17) C36 0.0185(19) 0.018(2) 0.023(2) -0.0002(17) 0.0010(17) -0.0025(16) C13 0.0189(19) 0.015(2) 0.022(2) 0.0009(16) -0.0023(16) -0.0066(16) C31 0.0144(18) 0.021(2) 0.017(2) 0.0015(16) 0.0012(16) -0.0089(16) C16 0.022(2) 0.019(2) 0.028(2) 0.0061(17) 0.0055(17) -0.0053(17) C19 0.029(2) 0.037(3) 0.025(2) -0.0028(19) -0.0001(19) -0.020(2) C2 0.0193(19) 0.018(2) 0.023(2) 0.0001(17) 0.0042(17) -0.0041(16) C18 0.020(2) 0.027(2) 0.027(2) -0.0016(18) 0.0043(18) -0.0139(17) C32 0.020(2) 0.026(2) 0.022(2) 0.0035(17) -0.0042(17) -0.0086(18) C34 0.027(2) 0.019(2) 0.027(2) -0.0015(18) 0.0060(19) -0.0074(18) C35 0.031(2) 0.022(2) 0.023(2) -0.0011(17) -0.0020(18) -0.0123(18) C9 0.0184(19) 0.021(2) 0.023(2) -0.0015(17) 0.0024(16) -0.0086(17) C15 0.025(2) 0.014(2) 0.035(2) 0.0044(18) 0.0100(19) -0.0006(17) C4 0.0141(19) 0.040(3) 0.041(3) 0.014(2) -0.0123(19) -0.0117(19) C14 0.019(2) 0.018(2) 0.032(2) 0.0031(17) 0.0006(18) -0.0033(16) C22 0.022(2) 0.025(2) 0.023(2) 0.0029(18) 0.0051(18) -0.0069(17) C20 0.022(2) 0.054(3) 0.023(2) 0.012(2) -0.0013(19) -0.021(2) C39 0.040(3) 0.019(2) 0.033(3) -0.0017(18) 0.004(2) -0.0096(19) C40 0.050(3) 0.023(3) 0.036(3) 0.002(2) 0.015(2) -0.009(2) C17 0.0178(19) 0.023(2) 0.018(2) 0.0015(16) 0.0015(16) -0.0102(17) C26 0.031(2) 0.023(2) 0.038(3) 0.0015(19) -0.009(2) -0.0167(19) C29 0.024(2) 0.025(2) 0.026(2) -0.0013(18) 0.0019(18) -0.0098(18) C28 0.040(2) 0.025(2) 0.024(2) -0.0061(18) 0.004(2) -0.010(2) C5 0.020(2) 0.031(2) 0.033(2) 0.0092(19) -0.0047(18) -0.0135(18) C27 0.042(2) 0.019(2) 0.030(2) -0.0019(18) -0.015(2) -0.0091(19) C3 0.022(2) 0.027(2) 0.029(2) 0.0115(18) -0.0057(18) -0.0068(18) C21 0.026(2) 0.034(3) 0.030(3) 0.012(2) 0.003(2) -0.0064(19) C42 0.031(2) 0.030(3) 0.055(3) 0.011(2) -0.007(2) -0.010(2) C33 0.0169(19) 0.019(2) 0.033(2) 0.0081(18) -0.0037(18) -0.0011(17) C41 0.032(2) 0.023(3) 0.055(3) 0.011(2) 0.005(2) -0.007(2) C37 0.039(3) 0.030(3) 0.044(3) -0.005(2) 0.001(2) -0.002(2) C43 0.033(2) 0.027(3) 0.036(3) 0.010(2) -0.004(2) -0.004(2) C23 0.037(3) 0.069(4) 0.035(3) 0.016(2) -0.006(2) -0.030(3) C30 0.078(4) 0.025(3) 0.054(3) -0.011(2) -0.012(3) -0.019(3) C44 0.054(3) 0.049(4) 0.084(4) 0.018(3) 0.016(3) -0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S2 O3 1.426(3) . ? S2 O4 1.434(2) . ? S2 N2 1.629(3) . ? S2 C24 1.778(4) . ? S1 O1 1.430(3) . ? S1 O2 1.436(3) . ? S1 N1 1.643(3) . ? S1 C17 1.766(4) . ? S3 O5 1.430(3) . ? S3 O6 1.439(3) . ? S3 N3 1.627(3) . ? S3 C31 1.763(4) . ? S4 O7 1.429(3) . ? S4 O8 1.433(3) . ? S4 N4 1.607(3) . ? S4 C38 1.762(4) . ? N2 C10 1.474(4) . ? N2 C11 1.484(4) . ? N3 C13 1.473(5) . ? N3 C12 1.475(4) . ? N1 C8 1.486(5) . ? N1 C7 1.502(5) . ? C12 C11 1.527(5) . ? N4 C15 1.468(5) . ? N4 C16 1.471(5) . ? C8 C9 1.518(5) . ? C10 C9 1.531(5) . ? C7 C6 1.513(5) . ? C24 C29 1.385(5) . ? C24 C25 1.394(5) . ? C38 C43 1.384(6) . ? C38 C39 1.394(5) . ? C6 C5 1.378(5) . ? C6 C1 1.394(5) . ? C1 C2 1.391(5) . ? C25 C26 1.378(6) . ? C36 C35 1.384(5) . ? C36 C31 1.386(5) . ? C13 C14 1.528(5) . ? C31 C32 1.378(5) . ? C16 C2 1.512(5) . ? C19 C18 1.391(6) . ? C19 C20 1.394(6) . ? C2 C3 1.384(5) . ? C18 C17 1.390(5) . ? C32 C33 1.389(5) . ? C34 C33 1.387(6) . ? C34 C35 1.394(5) . ? C34 C37 1.509(6) . ? C15 C14 1.516(5) . ? C4 C3 1.382(5) . ? C4 C5 1.391(5) . ? C22 C21 1.381(6) . ? C22 C17 1.390(5) . ? C20 C21 1.392(6) . ? C20 C23 1.501(6) . ? C39 C40 1.389(6) . ? C40 C41 1.377(7) . ? C26 C27 1.382(5) . ? C29 C28 1.381(6) . ? C28 C27 1.386(6) . ? C27 C30 1.506(6) . ? C42 C41 1.385(6) . ? C42 C43 1.387(6) . ? C41 C44 1.527(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S2 O4 120.05(17) . . ? O3 S2 N2 107.52(15) . . ? O4 S2 N2 105.92(15) . . ? O3 S2 C24 107.08(17) . . ? O4 S2 C24 106.73(16) . . ? N2 S2 C24 109.24(17) . . ? O1 S1 O2 119.47(17) . . ? O1 S1 N1 107.46(16) . . ? O2 S1 N1 106.75(15) . . ? O1 S1 C17 107.69(17) . . ? O2 S1 C17 107.78(18) . . ? N1 S1 C17 107.10(16) . . ? O5 S3 O6 119.79(16) . . ? O5 S3 N3 107.85(15) . . ? O6 S3 N3 106.65(15) . . ? O5 S3 C31 107.41(17) . . ? O6 S3 C31 107.36(16) . . ? N3 S3 C31 107.20(16) . . ? O7 S4 O8 118.92(18) . . ? O7 S4 N4 109.83(18) . . ? O8 S4 N4 106.82(16) . . ? O7 S4 C38 106.19(18) . . ? O8 S4 C38 108.70(18) . . ? N4 S4 C38 105.64(18) . . ? C10 N2 C11 117.1(3) . . ? C10 N2 S2 119.2(2) . . ? C11 N2 S2 115.3(2) . . ? C13 N3 C12 118.2(3) . . ? C13 N3 S3 119.9(2) . . ? C12 N3 S3 119.1(2) . . ? C8 N1 C7 117.5(3) . . ? C8 N1 S1 113.6(2) . . ? C7 N1 S1 114.9(2) . . ? N3 C12 C11 113.2(3) . . ? C15 N4 C16 118.1(3) . . ? C15 N4 S4 118.3(3) . . ? C16 N4 S4 123.1(3) . . ? N1 C8 C9 114.9(3) . . ? N2 C10 C9 112.7(3) . . ? N1 C7 C6 112.9(3) . . ? C29 C24 C25 120.3(4) . . ? C29 C24 S2 120.2(3) . . ? C25 C24 S2 119.4(3) . . ? N2 C11 C12 109.6(3) . . ? C43 C38 C39 119.9(4) . . ? C43 C38 S4 120.1(3) . . ? C39 C38 S4 120.0(3) . . ? C5 C6 C1 118.2(4) . . ? C5 C6 C7 121.7(3) . . ? C1 C6 C7 120.0(3) . . ? C2 C1 C6 121.9(3) . . ? C26 C25 C24 119.4(3) . . ? C35 C36 C31 119.8(4) . . ? N3 C13 C14 111.4(3) . . ? C32 C31 C36 120.5(4) . . ? C32 C31 S3 120.5(3) . . ? C36 C31 S3 119.1(3) . . ? N4 C16 C2 113.6(3) . . ? C18 C19 C20 121.4(4) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 C16 120.5(3) . . ? C1 C2 C16 121.0(3) . . ? C17 C18 C19 118.8(4) . . ? C31 C32 C33 119.4(4) . . ? C33 C34 C35 118.6(4) . . ? C33 C34 C37 121.2(4) . . ? C35 C34 C37 120.2(4) . . ? C36 C35 C34 120.6(4) . . ? C8 C9 C10 107.4(3) . . ? N4 C15 C14 113.3(3) . . ? C3 C4 C5 120.0(4) . . ? C15 C14 C13 110.9(3) . . ? C21 C22 C17 118.7(4) . . ? C21 C20 C19 118.0(4) . . ? C21 C20 C23 121.5(4) . . ? C19 C20 C23 120.5(4) . . ? C40 C39 C38 119.4(4) . . ? C41 C40 C39 120.8(4) . . ? C18 C17 C22 121.1(4) . . ? C18 C17 S1 119.4(3) . . ? C22 C17 S1 119.5(3) . . ? C25 C26 C27 121.3(4) . . ? C28 C29 C24 118.8(4) . . ? C29 C28 C27 121.9(4) . . ? C6 C5 C4 120.9(3) . . ? C26 C27 C28 118.2(4) . . ? C26 C27 C30 120.4(4) . . ? C28 C27 C30 121.3(4) . . ? C4 C3 C2 120.5(4) . . ? C22 C21 C20 122.0(4) . . ? C41 C42 C43 120.6(5) . . ? C34 C33 C32 121.1(4) . . ? C40 C41 C42 119.4(4) . . ? C40 C41 C44 121.4(5) . . ? C42 C41 C44 119.2(5) . . ? C38 C43 C42 119.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S2 N2 C10 36.6(3) . . . . ? O4 S2 N2 C10 166.1(3) . . . . ? C24 S2 N2 C10 -79.2(3) . . . . ? O3 S2 N2 C11 -176.0(2) . . . . ? O4 S2 N2 C11 -46.5(3) . . . . ? C24 S2 N2 C11 68.1(3) . . . . ? O5 S3 N3 C13 -163.9(3) . . . . ? O6 S3 N3 C13 -34.0(3) . . . . ? C31 S3 N3 C13 80.7(3) . . . . ? O5 S3 N3 C12 35.4(3) . . . . ? O6 S3 N3 C12 165.3(3) . . . . ? C31 S3 N3 C12 -80.0(3) . . . . ? O1 S1 N1 C8 173.5(3) . . . . ? O2 S1 N1 C8 44.2(3) . . . . ? C17 S1 N1 C8 -71.0(3) . . . . ? O1 S1 N1 C7 -47.1(3) . . . . ? O2 S1 N1 C7 -176.4(3) . . . . ? C17 S1 N1 C7 68.3(3) . . . . ? C13 N3 C12 C11 -62.8(4) . . . . ? S3 N3 C12 C11 98.2(3) . . . . ? O7 S4 N4 C15 -49.9(3) . . . . ? O8 S4 N4 C15 179.9(3) . . . . ? C38 S4 N4 C15 64.3(3) . . . . ? O7 S4 N4 C16 138.0(3) . . . . ? O8 S4 N4 C16 7.8(4) . . . . ? C38 S4 N4 C16 -107.9(3) . . . . ? C7 N1 C8 C9 43.6(5) . . . . ? S1 N1 C8 C9 -178.1(3) . . . . ? C11 N2 C10 C9 63.6(4) . . . . ? S2 N2 C10 C9 -149.6(3) . . . . ? C8 N1 C7 C6 -110.1(3) . . . . ? S1 N1 C7 C6 112.2(3) . . . . ? O3 S2 C24 C29 129.4(3) . . . . ? O4 S2 C24 C29 -0.3(4) . . . . ? N2 S2 C24 C29 -114.4(3) . . . . ? O3 S2 C24 C25 -47.5(3) . . . . ? O4 S2 C24 C25 -177.2(3) . . . . ? N2 S2 C24 C25 68.7(3) . . . . ? C10 N2 C11 C12 -102.0(4) . . . . ? S2 N2 C11 C12 110.0(3) . . . . ? N3 C12 C11 N2 -173.6(3) . . . . ? O7 S4 C38 C43 162.3(3) . . . . ? O8 S4 C38 C43 -68.7(4) . . . . ? N4 S4 C38 C43 45.6(4) . . . . ? O7 S4 C38 C39 -17.7(4) . . . . ? O8 S4 C38 C39 111.3(3) . . . . ? N4 S4 C38 C39 -134.4(3) . . . . ? N1 C7 C6 C5 -54.9(5) . . . . ? N1 C7 C6 C1 129.2(3) . . . . ? C5 C6 C1 C2 -0.1(6) . . . . ? C7 C6 C1 C2 175.8(3) . . . . ? C29 C24 C25 C26 -0.8(6) . . . . ? S2 C24 C25 C26 176.1(3) . . . . ? C12 N3 C13 C14 -76.9(4) . . . . ? S3 N3 C13 C14 122.2(3) . . . . ? C35 C36 C31 C32 2.2(5) . . . . ? C35 C36 C31 S3 -178.1(3) . . . . ? O5 S3 C31 C32 -6.7(3) . . . . ? O6 S3 C31 C32 -136.8(3) . . . . ? N3 S3 C31 C32 108.9(3) . . . . ? O5 S3 C31 C36 173.5(3) . . . . ? O6 S3 C31 C36 43.5(3) . . . . ? N3 S3 C31 C36 -70.8(3) . . . . ? C15 N4 C16 C2 87.8(4) . . . . ? S4 N4 C16 C2 -100.1(4) . . . . ? C6 C1 C2 C3 1.3(6) . . . . ? C6 C1 C2 C16 -177.7(3) . . . . ? N4 C16 C2 C3 59.4(5) . . . . ? N4 C16 C2 C1 -121.6(4) . . . . ? C20 C19 C18 C17 -0.7(5) . . . . ? C36 C31 C32 C33 -2.1(5) . . . . ? S3 C31 C32 C33 178.2(3) . . . . ? C31 C36 C35 C34 -0.6(5) . . . . ? C33 C34 C35 C36 -1.2(5) . . . . ? C37 C34 C35 C36 177.2(4) . . . . ? N1 C8 C9 C10 168.9(3) . . . . ? N2 C10 C9 C8 166.0(3) . . . . ? C16 N4 C15 C14 -80.0(5) . . . . ? S4 N4 C15 C14 107.5(4) . . . . ? N4 C15 C14 C13 179.8(3) . . . . ? N3 C13 C14 C15 -61.7(4) . . . . ? C18 C19 C20 C21 1.8(5) . . . . ? C18 C19 C20 C23 -176.6(3) . . . . ? C43 C38 C39 C40 -1.3(6) . . . . ? S4 C38 C39 C40 178.7(3) . . . . ? C38 C39 C40 C41 -0.4(6) . . . . ? C19 C18 C17 C22 -1.6(5) . . . . ? C19 C18 C17 S1 177.1(3) . . . . ? C21 C22 C17 C18 2.7(5) . . . . ? C21 C22 C17 S1 -175.9(3) . . . . ? O1 S1 C17 C18 18.8(3) . . . . ? O2 S1 C17 C18 149.0(3) . . . . ? N1 S1 C17 C18 -96.5(3) . . . . ? O1 S1 C17 C22 -162.5(3) . . . . ? O2 S1 C17 C22 -32.3(3) . . . . ? N1 S1 C17 C22 82.2(3) . . . . ? C24 C25 C26 C27 -0.7(6) . . . . ? C25 C24 C29 C28 1.1(6) . . . . ? S2 C24 C29 C28 -175.7(3) . . . . ? C24 C29 C28 C27 0.0(6) . . . . ? C1 C6 C5 C4 -1.5(6) . . . . ? C7 C6 C5 C4 -177.4(4) . . . . ? C3 C4 C5 C6 2.0(7) . . . . ? C25 C26 C27 C28 1.8(6) . . . . ? C25 C26 C27 C30 -179.0(4) . . . . ? C29 C28 C27 C26 -1.4(7) . . . . ? C29 C28 C27 C30 179.4(4) . . . . ? C5 C4 C3 C2 -0.8(7) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C16 C2 C3 C4 178.2(4) . . . . ? C17 C22 C21 C20 -1.6(5) . . . . ? C19 C20 C21 C22 -0.7(6) . . . . ? C23 C20 C21 C22 177.7(3) . . . . ? C35 C34 C33 C32 1.3(5) . . . . ? C37 C34 C33 C32 -177.0(4) . . . . ? C31 C32 C33 C34 0.3(5) . . . . ? C39 C40 C41 C42 2.0(6) . . . . ? C39 C40 C41 C44 -176.0(4) . . . . ? C43 C42 C41 C40 -1.9(6) . . . . ? C43 C42 C41 C44 176.1(4) . . . . ? C39 C38 C43 C42 1.4(6) . . . . ? S4 C38 C43 C42 -178.6(3) . . . . ? C41 C42 C43 C38 0.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.531 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.084 data_L3-HF\L3-HF.CIF _database_code_depnum_ccdc_archive 'CCDC 272034' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common L3-HF _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H39 F5 N4 O3' _chemical_formula_weight 430.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.1345(8) _cell_length_b 11.3695(5) _cell_length_c 19.3298(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.385(4) _cell_angle_gamma 90.00 _cell_volume 4324.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colourless _exptl_crystal_colour plate _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min 0.9430 _exptl_absorpt_correction_T_max 0.9766 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8370 _diffrn_reflns_av_R_equivalents 0.1190 _diffrn_reflns_av_sigmaI/netI 0.1756 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3449 _reflns_number_gt 1693 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3449 _refine_ls_number_parameters 309 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1535 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.03530(8) 0.56038(17) 0.07196(9) 0.0238(5) Uani 1 1 d . . . O1 O 0.27221(15) 0.4423(3) 0.02412(15) 0.0352(7) Uani 1 1 d . . . N1 N 0.35567(12) 1.0268(2) -0.18720(14) 0.0184(7) Uani 1 1 d . . . H1A H 0.3455 1.0476 -0.1464 0.022 Uiso 1 1 calc R . . H1B H 0.3960 0.9860 -0.1705 0.022 Uiso 1 1 calc R . . C1 C 0.33589(15) 0.7418(3) -0.19476(18) 0.0205(9) Uani 1 1 d . . . H1 H 0.3601 0.7403 -0.2277 0.025 Uiso 1 1 calc R . . F2 F 0.04781(9) 0.59684(18) 0.23660(10) 0.0362(6) Uani 1 1 d . . . O2 O 0.21428(14) 0.1583(3) 0.10394(18) 0.0402(8) Uani 1 1 d . . . N2 N 0.52613(14) 1.1387(3) -0.07634(18) 0.0214(8) Uani 1 1 d . . . C2 C 0.33974(15) 0.6460(3) -0.14892(18) 0.0172(9) Uani 1 1 d . . . H2 H 0.3891(17) 0.409(4) -0.366(2) 0.027(15) Uiso 1 1 d . . . F3 F 0.17616(8) 0.38796(17) 0.07939(9) 0.0273(5) Uani 1 1 d . . . O3 O 0.37122(14) 0.3891(3) -0.4047(2) 0.0336(8) Uani 1 1 d . . . N3 N 0.58780(16) 0.8875(3) -0.05846(17) 0.0185(7) Uani 1 1 d . . . C3 C 0.30233(15) 0.6485(3) -0.10255(18) 0.0218(9) Uani 1 1 d . . . H3 H 0.3048 0.5841 -0.0704 0.026 Uiso 1 1 calc R . . F4 F 0.53001(8) 1.36866(16) -0.04002(9) 0.0236(5) Uani 1 1 d . . . N4 N 0.45734(14) 0.5672(3) -0.09546(18) 0.0198(8) Uani 1 1 d . . . C4 C 0.26169(15) 0.7440(3) -0.10306(19) 0.0245(9) Uani 1 1 d . . . H4 H 0.2353 0.7436 -0.0725 0.029 Uiso 1 1 calc R . . F5 F 0.44218(15) 0.4564(3) -0.26876(17) 0.0347(11) Uani 0.58 1 d P A 1 C5 C 0.25929(15) 0.8393(3) -0.14745(18) 0.0220(9) Uani 1 1 d . . . H5 H 0.2317 0.9051 -0.1470 0.026 Uiso 1 1 calc R . . C6 C 0.29716(15) 0.8400(3) -0.19323(18) 0.0179(9) Uani 1 1 d . . . C7 C 0.30113(15) 0.9484(3) -0.23572(18) 0.0217(9) Uani 1 1 d . . . H7A H 0.3111 0.9262 -0.2802 0.026 Uiso 1 1 calc R . . H7B H 0.2570 0.9902 -0.2524 0.026 Uiso 1 1 calc R . . C8 C 0.36446(16) 1.1355(3) -0.22566(19) 0.0237(9) Uani 1 1 d . . . H8B H 0.3213 1.1802 -0.2429 0.028 Uiso 1 1 calc R . . H8A H 0.3747 1.1133 -0.2700 0.028 Uiso 1 1 calc R . . C9 C 0.42100(15) 1.2139(3) -0.17590(19) 0.0251(9) Uani 1 1 d . . . H9A H 0.4134 1.2275 -0.1289 0.030 Uiso 1 1 calc R . . H9B H 0.4181 1.2911 -0.2006 0.030 Uiso 1 1 calc R . . C10 C 0.49290(15) 1.1645(3) -0.15722(18) 0.0233(9) Uani 1 1 d . . . H10A H 0.4905 1.0915 -0.1860 0.028 Uiso 1 1 calc R . . H10B H 0.5207 1.2222 -0.1720 0.028 Uiso 1 1 calc R . . C11 C 0.59964(14) 1.1059(3) -0.05313(18) 0.0206(9) Uani 1 1 d . . . H11A H 0.6189 1.0973 0.0016 0.025 Uiso 1 1 calc R . . H11B H 0.6242 1.1707 -0.0666 0.025 Uiso 1 1 calc R . . C12 C 0.61157(16) 0.9936(3) -0.08793(19) 0.0207(9) Uani 1 1 d . . . H12A H 0.5873 0.9979 -0.1424 0.025 Uiso 1 1 calc R . . H12B H 0.6607 0.9856 -0.0782 0.025 Uiso 1 1 calc R . . C13 C 0.60175(15) 0.7752(3) -0.09013(19) 0.0211(9) Uani 1 1 d . . . H13B H 0.6513 0.7607 -0.0711 0.025 Uiso 1 1 calc R . . H13A H 0.5859 0.7821 -0.1449 0.025 Uiso 1 1 calc R . . C14 C 0.56644(14) 0.6728(3) -0.06991(18) 0.0239(9) Uani 1 1 d . . . H14A H 0.5695 0.6819 -0.0179 0.029 Uiso 1 1 calc R . . H14B H 0.5901 0.5991 -0.0732 0.029 Uiso 1 1 calc R . . C15 C 0.49238(14) 0.6633(3) -0.12014(17) 0.0202(9) Uani 1 1 d . . . H15A H 0.4693 0.7389 -0.1199 0.024 Uiso 1 1 calc R . . H15B H 0.4893 0.6476 -0.1717 0.024 Uiso 1 1 calc R . . C16 C 0.38573(15) 0.5433(3) -0.14682(18) 0.0204(9) Uani 1 1 d . . . H16A H 0.3686 0.4721 -0.1300 0.024 Uiso 1 1 calc R . . H16B H 0.3851 0.5282 -0.1975 0.024 Uiso 1 1 calc R . . H101 H 0.246(2) 0.425(4) 0.049(2) 0.064(16) Uiso 1 1 d . . . H102 H 0.303(2) 0.504(5) 0.047(3) 0.11(2) Uiso 1 1 d . . . H201 H 0.207(2) 0.237(6) 0.095(3) 0.11(2) Uiso 1 1 d . . . H202 H 0.218(3) 0.130(5) 0.063(3) 0.12(3) Uiso 1 1 d . . . H301 H 0.407(3) 0.375(5) -0.433(3) 0.12(2) Uiso 1 1 d . . . H2A H 0.5237(15) 1.195(3) -0.0559(18) 0.012(11) Uiso 1 1 d . . . H3A H 0.6110(16) 0.879(3) -0.005(2) 0.045(12) Uiso 1 1 d . . . H4A H 0.4843(15) 0.491(3) -0.0889(17) 0.030(10) Uiso 1 1 d . . . F5A F 0.5000 0.4500(5) -0.2500 0.0297(18) Uani 0.42 2 d SPU B 2 H2B H 0.505(2) 1.059(4) -0.055(2) 0.088(15) Uiso 1 1 d . . . H3B H 0.540(2) 0.896(3) -0.065(2) 0.054(13) Uiso 1 1 d . . . H4B H 0.4550(16) 0.587(3) -0.054(2) 0.032(12) Uiso 1 1 d . . . H2F H 0.0000 0.598(5) 0.2500 0.068(19) Uiso 1 2 d S . . H5F H 0.5000 0.4500(5) -0.2500 0.030 Uiso 0.58 2 d SP C 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0210(10) 0.0191(13) 0.0304(12) 0.0006(10) 0.0082(8) -0.0010(9) O1 0.0339(16) 0.038(2) 0.0386(17) -0.0064(16) 0.0185(15) -0.0065(15) N1 0.0164(15) 0.016(2) 0.0199(16) 0.0013(14) 0.0035(13) 0.0020(13) C1 0.0170(19) 0.021(3) 0.021(2) -0.0013(19) 0.0033(16) 0.0014(17) F2 0.0363(12) 0.0354(16) 0.0396(13) -0.0010(11) 0.0169(10) 0.0028(11) O2 0.0545(18) 0.025(2) 0.039(2) 0.0044(17) 0.0139(14) 0.0001(15) N2 0.0297(19) 0.012(2) 0.024(2) -0.0039(18) 0.0109(15) 0.0044(16) C2 0.0174(19) 0.011(2) 0.020(2) -0.0003(17) 0.0027(16) -0.0040(16) F3 0.0317(11) 0.0231(14) 0.0266(11) -0.0015(10) 0.0100(9) 0.0004(10) O3 0.0336(17) 0.028(2) 0.042(2) -0.0008(17) 0.0173(17) 0.0029(14) N3 0.0199(18) 0.014(2) 0.0215(19) 0.0041(16) 0.0078(14) 0.0005(14) C3 0.0227(19) 0.016(3) 0.022(2) 0.0025(17) 0.0030(17) -0.0025(17) F4 0.0282(10) 0.0166(13) 0.0266(11) -0.0007(9) 0.0109(9) 0.0029(9) N4 0.0237(19) 0.013(2) 0.022(2) -0.0043(16) 0.0077(16) 0.0023(15) C4 0.022(2) 0.024(3) 0.029(2) -0.003(2) 0.0106(17) -0.0017(19) F5 0.0126(18) 0.075(3) 0.019(2) -0.0111(19) 0.0087(17) -0.0045(17) C5 0.021(2) 0.014(2) 0.028(2) -0.005(2) 0.0061(17) 0.0018(17) C6 0.0172(19) 0.013(2) 0.019(2) 0.0006(17) 0.0009(16) -0.0012(17) C7 0.0202(19) 0.017(2) 0.022(2) -0.0050(19) 0.0003(16) -0.0031(17) C8 0.023(2) 0.018(3) 0.029(2) 0.0050(19) 0.0074(16) 0.0019(17) C9 0.028(2) 0.012(2) 0.037(2) 0.0022(19) 0.0138(18) 0.0000(17) C10 0.028(2) 0.019(2) 0.022(2) -0.0007(18) 0.0083(17) -0.0042(17) C11 0.019(2) 0.015(2) 0.026(2) 0.0034(18) 0.0057(16) -0.0010(16) C12 0.0246(19) 0.014(2) 0.023(2) 0.0035(18) 0.0079(16) 0.0000(17) C13 0.025(2) 0.007(2) 0.032(2) -0.0024(18) 0.0112(17) 0.0009(16) C14 0.018(2) 0.019(2) 0.031(2) 0.0008(19) 0.0045(17) 0.0059(17) C15 0.025(2) 0.015(2) 0.021(2) 0.0015(17) 0.0088(17) -0.0014(17) C16 0.021(2) 0.016(2) 0.021(2) -0.0031(18) 0.0041(17) -0.0031(17) F5A 0.071(4) 0.014(4) 0.004(3) 0.000 0.013(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.488(4) . ? N1 C7 1.488(4) . ? C1 C2 1.388(4) . ? C1 C6 1.391(4) . ? N2 C10 1.491(4) . ? N2 C11 1.499(4) . ? C2 C3 1.395(4) . ? C2 C16 1.510(4) . ? N3 C13 1.491(4) . ? N3 C12 1.497(4) . ? C3 C4 1.382(4) . ? N4 C15 1.492(4) . ? N4 C16 1.501(4) . ? C4 C5 1.372(5) . ? C5 C6 1.393(4) . ? C6 C7 1.500(4) . ? C8 C9 1.520(4) . ? C9 C10 1.535(4) . ? C11 C12 1.506(4) . ? C13 C14 1.510(4) . ? C14 C15 1.515(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C7 113.1(2) . . ? C2 C1 C6 121.0(3) . . ? C10 N2 C11 113.8(3) . . ? C1 C2 C3 118.6(3) . . ? C1 C2 C16 120.7(3) . . ? C3 C2 C16 120.6(3) . . ? C13 N3 C12 112.9(3) . . ? C4 C3 C2 120.5(3) . . ? C15 N4 C16 114.8(3) . . ? C5 C4 C3 120.4(3) . . ? C4 C5 C6 120.2(3) . . ? C1 C6 C5 119.2(3) . . ? C1 C6 C7 119.8(3) . . ? C5 C6 C7 120.8(3) . . ? N1 C7 C6 109.4(3) . . ? N1 C8 C9 112.6(3) . . ? C8 C9 C10 114.6(3) . . ? N2 C10 C9 111.5(3) . . ? N2 C11 C12 113.6(3) . . ? N3 C12 C11 112.3(3) . . ? N3 C13 C14 111.3(3) . . ? C13 C14 C15 112.4(3) . . ? N4 C15 C14 111.4(3) . . ? N4 C16 C2 111.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.8(5) . . . . ? C6 C1 C2 C16 -175.6(3) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C16 C2 C3 C4 178.2(3) . . . . ? C2 C3 C4 C5 -2.1(5) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? C2 C1 C6 C5 -3.0(5) . . . . ? C2 C1 C6 C7 171.9(3) . . . . ? C4 C5 C6 C1 1.7(5) . . . . ? C4 C5 C6 C7 -173.3(3) . . . . ? C8 N1 C7 C6 178.5(3) . . . . ? C1 C6 C7 N1 -90.2(3) . . . . ? C5 C6 C7 N1 84.7(3) . . . . ? C7 N1 C8 C9 -179.1(3) . . . . ? N1 C8 C9 C10 69.9(4) . . . . ? C11 N2 C10 C9 -172.1(3) . . . . ? C8 C9 C10 N2 -114.9(3) . . . . ? C10 N2 C11 C12 -63.7(4) . . . . ? C13 N3 C12 C11 -177.7(3) . . . . ? N2 C11 C12 N3 -69.8(4) . . . . ? C12 N3 C13 C14 -170.0(3) . . . . ? N3 C13 C14 C15 81.5(4) . . . . ? C16 N4 C15 C14 -173.8(3) . . . . ? C13 C14 C15 N4 -175.6(3) . . . . ? C15 N4 C16 C2 -66.6(4) . . . . ? C1 C2 C16 N4 83.2(4) . . . . ? C3 C2 C16 N4 -94.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F3 0.92 1.69 2.599(3) 168.8 7_565 N1 H1B F1 0.92 2.00 2.741(3) 136.5 7_565 N1 H1B F2 0.92 2.24 2.910(3) 128.9 7_565 N3 H3B F1 0.98(4) 1.62(4) 2.587(3) 167(3) 7_565 N4 H4A F4 1.02(4) 1.76(4) 2.721(4) 156(3) 1_545 O3 H301 F4 1.09(6) 1.60(6) 2.680(3) 168(5) 2_644 N2 H2A F4 0.76(3) 2.00(4) 2.701(4) 154(3) . N4 H4B F4 0.84(4) 1.81(4) 2.636(4) 167(3) 5_675 N2 H2B F1 1.16(5) 1.57(5) 2.626(4) 148(4) 7_565 N3 H3A F3 0.98(4) 1.71(4) 2.638(4) 157(3) 3 O1 H101 F3 0.88(5) 1.82(5) 2.688(4) 166(4) . O2 H202 O1 0.88(6) 1.95(7) 2.834(5) 176(6) 7 O2 H201 F3 0.92(7) 1.82(7) 2.723(4) 169(4) . O1 H102 O3 0.95(6) 1.86(6) 2.801(4) 173(4) 6_566 O3 H2 F5 0.75(3) 1.88(4) 2.620(5) 174(4) . _diffrn_measured_fraction_theta_max 0.698 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.698 _refine_diff_density_max 0.415 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.094 data_c:\structs\chris\a5br\a5br _database_code_depnum_ccdc_archive 'CCDC 272035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 Br4 N4' _chemical_formula_weight 600.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4815(8) _cell_length_b 11.0386(10) _cell_length_c 11.4504(10) _cell_angle_alpha 88.5738(23) _cell_angle_beta 68.2659(19) _cell_angle_gamma 86.0713(22) _cell_volume 1110.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 7.254 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7106 _diffrn_reflns_av_R_equivalents 0.1726 _diffrn_reflns_av_sigmaI/netI 0.2479 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4839 _reflns_number_gt 2996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+31.8853P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4839 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2350 _refine_ls_R_factor_gt 0.1621 _refine_ls_wR_factor_ref 0.3011 _refine_ls_wR_factor_gt 0.2677 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.5071(2) 0.71460(16) 0.44611(16) 0.0275(5) Uani 1 1 d . . . Br2 Br 0.9834(2) 0.21089(16) -0.02624(17) 0.0285(5) Uani 1 1 d . . . Br3 Br 0.5166(2) 0.72256(17) -0.18533(18) 0.0331(5) Uani 1 1 d . . . Br4 Br 0.7933(2) 0.99154(19) 0.75197(17) 0.0354(5) Uani 1 1 d . . . N2 N 0.7876(18) 1.0146(13) 0.1922(13) 0.029(4) Uani 1 1 d . . . H21 H 0.8178 1.0686 0.1264 0.035 Uiso 1 1 calc R . . H22 H 0.8573 0.9489 0.1728 0.035 Uiso 1 1 calc R . . C15 C 0.738(2) 0.5390(16) 0.1194(16) 0.029(4) Uani 1 1 d . . . H15A H 0.7999 0.4745 0.0605 0.035 Uiso 1 1 calc R . . H15B H 0.8071 0.6018 0.1210 0.035 Uiso 1 1 calc R . . N1 N 0.7867(17) 0.8119(14) 0.5383(14) 0.031(4) Uani 1 1 d . . . H11 H 0.7021 0.7752 0.5393 0.037 Uiso 1 1 calc R . . H12 H 0.7574 0.8621 0.6073 0.037 Uiso 1 1 calc R . . C9 C 0.7331(19) 0.9924(15) 0.4291(15) 0.025(4) Uani 1 1 d . . . H9A H 0.7174 1.0412 0.5047 0.030 Uiso 1 1 calc R . . H9B H 0.6342 0.9610 0.4384 0.030 Uiso 1 1 calc R . . N4 N 0.6719(14) 0.4868(12) 0.2454(13) 0.025(3) Uani 1 1 d . . . H41 H 0.5943 0.4398 0.2481 0.030 Uiso 1 1 calc R . . H42 H 0.6305 0.5488 0.3027 0.030 Uiso 1 1 calc R . . N3 N 0.6658(18) 0.8187(14) 0.0366(15) 0.033(4) Uani 1 1 d . . . H31 H 0.7613 0.7983 0.0371 0.039 Uiso 1 1 calc R . . H32 H 0.6717 0.8146 -0.0453 0.039 Uiso 1 1 calc R . . C14 C 0.6150(17) 0.5979(15) 0.0688(16) 0.023(4) Uani 1 1 d . . . H14A H 0.6586 0.5967 -0.0242 0.027 Uiso 1 1 calc R . . H14B H 0.5263 0.5472 0.0964 0.027 Uiso 1 1 calc R . . C8 C 0.8462(19) 0.8862(15) 0.4219(16) 0.026(4) Uani 1 1 d . . . H8A H 0.8615 0.8357 0.3474 0.031 Uiso 1 1 calc R . . H8B H 0.9454 0.9164 0.4135 0.031 Uiso 1 1 calc R . . C6 C 1.101(2) 0.6395(15) 0.3396(17) 0.029(4) Uani 1 1 d . . . H6 H 1.1698 0.6927 0.3505 0.035 Uiso 1 1 calc R . . C12 C 0.620(2) 0.9451(17) 0.0817(16) 0.028(4) Uani 1 1 d . . . H12A H 0.5130 0.9632 0.0910 0.034 Uiso 1 1 calc R . . H12B H 0.6830 1.0004 0.0165 0.034 Uiso 1 1 calc R . . C7 C 0.903(2) 0.7153(15) 0.5482(16) 0.025(4) Uani 1 1 d . . . H7B H 0.8574 0.6663 0.6250 0.030 Uiso 1 1 calc R . . H7A H 0.9910 0.7543 0.5546 0.030 Uiso 1 1 calc R . . C3 C 0.9017(19) 0.4882(14) 0.3047(16) 0.023(4) Uani 1 1 d . . . C2 C 1.045(2) 0.4949(16) 0.2134(17) 0.031(4) Uani 1 1 d . . . H2 H 1.0754 0.4484 0.1384 0.037 Uiso 1 1 calc R . . C11 C 0.6360(18) 0.9735(16) 0.2072(15) 0.023(4) Uani 1 1 d . . . H11A H 0.5571 1.0374 0.2518 0.028 Uiso 1 1 calc R . . H11B H 0.6169 0.8997 0.2604 0.028 Uiso 1 1 calc R . . C13 C 0.5600(18) 0.7284(14) 0.1127(16) 0.022(4) Uani 1 1 d . . . H13A H 0.4587 0.7467 0.1077 0.026 Uiso 1 1 calc R . . H13B H 0.5486 0.7358 0.2018 0.026 Uiso 1 1 calc R . . C10 C 0.786(2) 1.0756(15) 0.3115(16) 0.030(4) Uani 1 1 d . . . H10A H 0.7170 1.1501 0.3280 0.036 Uiso 1 1 calc R . . H10B H 0.8893 1.1002 0.2973 0.036 Uiso 1 1 calc R . . C16 C 0.7863(19) 0.4100(15) 0.2834(16) 0.026(4) Uani 1 1 d . . . H16A H 0.8406 0.3496 0.2168 0.031 Uiso 1 1 calc R . . H16B H 0.7323 0.3654 0.3617 0.031 Uiso 1 1 calc R . . C5 C 0.957(2) 0.6334(18) 0.4331(17) 0.033(5) Uani 1 1 d . . . C4 C 0.857(2) 0.5552(16) 0.4163(15) 0.025(4) Uani 1 1 d . . . H4 H 0.7590 0.5474 0.4797 0.030 Uiso 1 1 calc R . . C1 C 1.146(2) 0.5714(18) 0.2336(17) 0.030(4) Uani 1 1 d . . . H1 H 1.2456 0.5758 0.1726 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0244(9) 0.0287(10) 0.0256(9) -0.0021(7) -0.0047(7) -0.0017(7) Br2 0.0248(10) 0.0253(10) 0.0322(10) 0.0013(7) -0.0072(8) 0.0009(7) Br3 0.0400(11) 0.0298(10) 0.0354(10) 0.0047(8) -0.0194(9) -0.0120(8) Br4 0.0315(11) 0.0466(12) 0.0269(10) -0.0051(8) -0.0070(8) -0.0133(9) N2 0.039(9) 0.025(8) 0.021(8) 0.003(6) -0.007(7) -0.001(7) C15 0.036(11) 0.021(9) 0.024(9) -0.004(7) -0.006(8) 0.005(8) N1 0.028(8) 0.031(9) 0.028(8) 0.001(7) -0.004(7) 0.005(7) C9 0.021(9) 0.026(9) 0.019(8) 0.000(7) 0.003(7) -0.002(7) N4 0.007(6) 0.023(8) 0.033(8) -0.013(6) 0.008(6) -0.007(5) N3 0.038(9) 0.033(9) 0.039(9) -0.006(7) -0.028(8) 0.009(7) C14 0.011(8) 0.024(9) 0.029(9) 0.002(7) -0.002(7) -0.003(7) C8 0.018(8) 0.028(10) 0.021(9) 0.011(7) 0.006(7) -0.010(7) C6 0.038(11) 0.016(9) 0.044(11) 0.016(8) -0.027(9) -0.012(8) C12 0.019(9) 0.036(11) 0.029(10) 0.011(8) -0.009(7) 0.000(8) C7 0.028(10) 0.024(9) 0.027(9) 0.007(7) -0.014(8) 0.000(7) C3 0.028(9) 0.013(8) 0.031(9) 0.002(7) -0.014(8) -0.006(7) C2 0.020(9) 0.025(10) 0.028(9) -0.010(7) 0.014(7) 0.001(7) C11 0.020(9) 0.031(10) 0.017(8) 0.011(7) -0.007(7) 0.002(7) C13 0.013(8) 0.019(9) 0.027(9) 0.006(7) 0.000(7) 0.001(6) C10 0.029(10) 0.018(9) 0.031(10) 0.005(7) 0.000(8) 0.011(7) C16 0.018(9) 0.024(9) 0.021(9) 0.000(7) 0.009(7) 0.000(7) C5 0.026(10) 0.047(12) 0.029(10) 0.006(9) -0.017(8) 0.006(9) C4 0.025(9) 0.028(10) 0.016(8) 0.002(7) -0.004(7) 0.004(8) C1 0.017(9) 0.044(12) 0.029(10) -0.001(9) -0.008(8) 0.005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C11 1.48(2) . ? N2 C10 1.53(2) . ? C15 N4 1.46(2) . ? C15 C14 1.58(2) . ? N1 C8 1.49(2) . ? N1 C7 1.51(2) . ? C9 C8 1.52(2) . ? C9 C10 1.55(2) . ? N4 C16 1.51(2) . ? N3 C12 1.48(2) . ? N3 C13 1.49(2) . ? C14 C13 1.53(2) . ? C6 C1 1.36(3) . ? C6 C5 1.40(3) . ? C12 C11 1.54(2) . ? C7 C5 1.52(3) . ? C3 C2 1.38(2) . ? C3 C4 1.40(2) . ? C3 C16 1.53(3) . ? C2 C1 1.40(3) . ? C5 C4 1.39(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N2 C10 112.0(13) . . ? N4 C15 C14 113.3(14) . . ? C8 N1 C7 112.6(13) . . ? C8 C9 C10 112.9(13) . . ? C15 N4 C16 113.1(12) . . ? C12 N3 C13 113.9(13) . . ? C13 C14 C15 114.4(15) . . ? N1 C8 C9 109.2(12) . . ? C1 C6 C5 121.7(18) . . ? N3 C12 C11 115.3(13) . . ? N1 C7 C5 110.0(14) . . ? C2 C3 C4 121.2(17) . . ? C2 C3 C16 120.2(16) . . ? C4 C3 C16 118.6(15) . . ? C3 C2 C1 118.7(17) . . ? N2 C11 C12 113.6(13) . . ? N3 C13 C14 112.7(13) . . ? N2 C10 C9 113.2(15) . . ? N4 C16 C3 111.3(13) . . ? C4 C5 C6 118.7(18) . . ? C4 C5 C7 119.4(16) . . ? C6 C5 C7 121.8(18) . . ? C5 C4 C3 119.2(16) . . ? C6 C1 C2 120.4(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C15 N4 C16 169.0(14) . . . . ? N4 C15 C14 C13 84.0(18) . . . . ? C7 N1 C8 C9 -171.1(15) . . . . ? C10 C9 C8 N1 179.8(16) . . . . ? C13 N3 C12 C11 70.2(19) . . . . ? C8 N1 C7 C5 -57(2) . . . . ? C4 C3 C2 C1 -1(3) . . . . ? C16 C3 C2 C1 177.2(16) . . . . ? C10 N2 C11 C12 163.8(13) . . . . ? N3 C12 C11 N2 89.3(18) . . . . ? C12 N3 C13 C14 -176.5(14) . . . . ? C15 C14 C13 N3 81.5(18) . . . . ? C11 N2 C10 C9 57.8(18) . . . . ? C8 C9 C10 N2 68(2) . . . . ? C15 N4 C16 C3 69.3(18) . . . . ? C2 C3 C16 N4 -101.2(18) . . . . ? C4 C3 C16 N4 76.8(18) . . . . ? C1 C6 C5 C4 0(3) . . . . ? C1 C6 C5 C7 -176.1(16) . . . . ? N1 C7 C5 C4 -69(2) . . . . ? N1 C7 C5 C6 106.9(18) . . . . ? C6 C5 C4 C3 -2(2) . . . . ? C7 C5 C4 C3 174.1(15) . . . . ? C2 C3 C4 C5 2(3) . . . . ? C16 C3 C4 C5 -175.5(15) . . . . ? C5 C6 C1 C2 2(3) . . . . ? C3 C2 C1 C6 -1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H21 Br2 0.92 2.48 3.352(14) 158.2 1_565 N2 H22 Br2 0.92 2.47 3.311(15) 151.6 2_765 N1 H11 Br1 0.92 2.58 3.437(17) 154.9 . N1 H12 Br4 0.92 2.35 3.208(17) 156.0 . N4 H41 Br3 0.92 2.39 3.250(14) 155.5 2_665 N4 H42 Br1 0.92 2.42 3.337(13) 175.6 . N3 H31 Br2 0.92 2.37 3.279(16) 167.9 2_765 N3 H32 Br3 0.92 2.79 3.547(16) 140.1 . N3 H32 Br4 0.92 2.94 3.579(16) 128.0 1_554 _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 1.545 _refine_diff_density_min -1.569 _refine_diff_density_rms 0.288 data_L4-4HCl-1.5H2O.CIF _database_code_depnum_ccdc_archive 'CCDC 272036' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Revised CIF' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H30 Cl4 N4 O1.50' _chemical_formula_weight 420.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.725(3) _cell_length_b 6.3480(7) _cell_length_c 22.054(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.999(4) _cell_angle_gamma 90.00 _cell_volume 4151.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.582 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min 0.8006 _exptl_absorpt_correction_T_max 0.9441 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2156 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.1390 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.08 _reflns_number_total 1599 _reflns_number_gt 990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0003(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1599 _refine_ls_number_parameters 221 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.13654(6) 0.6467(3) 0.13726(8) 0.0360(8) Uani 1 1 d . . . O1 O 0.0000 -0.2824(16) 0.2500 0.035(3) Uani 1 2 d S . . N1 N 0.05517(19) -0.0784(10) 0.1722(3) 0.0290(18) Uani 1 1 d . . . H1A H 0.0417 -0.1526 0.2019 0.035 Uiso 1 1 calc R . . H1B H 0.0793 -0.1566 0.1609 0.035 Uiso 1 1 calc R . . C1 C 0.0512(2) 0.3428(12) 0.0000(4) 0.027(2) Uani 1 1 d . . . H1 H 0.0444 0.4852 -0.0103 0.032 Uiso 1 1 calc R . . Cl2 Cl 0.27685(6) 0.6007(3) 0.16296(8) 0.0333(7) Uani 1 1 d . . . O2 O 0.1371(3) -0.3406(17) 0.3126(4) 0.067(3) Uani 1 1 d . . . N2 N 0.15320(18) 0.0210(8) 0.2299(2) 0.0278(17) Uani 1 1 d . . . H2A H 0.1717 -0.0127 0.2637 0.033 Uiso 1 1 calc R . . H2B H 0.1491 -0.0992 0.2068 0.033 Uiso 1 1 calc R . . C2 C 0.0798(2) 0.2247(14) -0.0349(3) 0.022(2) Uani 1 1 d . . . H2 H 0.0922 0.2868 -0.0691 0.026 Uiso 1 1 calc R . . Cl3 Cl 0.04586(6) -0.5907(3) 0.33820(8) 0.0366(7) Uani 1 1 d . . . N3 N 0.21455(18) -0.0267(9) 0.1156(3) 0.0275(18) Uani 1 1 d . . . H3A H 0.2002 -0.1483 0.1264 0.033 Uiso 1 1 calc R . . H3B H 0.2427 -0.0638 0.1046 0.033 Uiso 1 1 calc R . . C3 C 0.0899(2) 0.0164(14) -0.0195(3) 0.020(2) Uani 1 1 d U . . Cl4 Cl 0.19304(6) 0.5590(3) 0.43812(8) 0.0338(7) Uani 1 1 d . . . N4 N 0.16924(18) -0.0286(9) -0.0492(3) 0.0298(18) Uani 1 1 d . . . H4A H 0.1691 0.1160 -0.0523 0.036 Uiso 1 1 calc R . . H4B H 0.1849 -0.0805 -0.0805 0.036 Uiso 1 1 calc R . . C4 C 0.0704(2) -0.0716(12) 0.0294(3) 0.023(2) Uani 1 1 d . . . H4 H 0.0761 -0.2153 0.0392 0.028 Uiso 1 1 calc R . . C5 C 0.0428(2) 0.0449(15) 0.0647(3) 0.022(2) Uani 1 1 d . . . C6 C 0.0330(2) 0.2508(15) 0.0495(3) 0.027(2) Uani 1 1 d . . . H6 H 0.0135 0.3302 0.0731 0.032 Uiso 1 1 calc R . . C7 C 0.0218(2) -0.0537(11) 0.1180(3) 0.030(2) Uani 1 1 d U . . H7A H 0.0096 -0.1938 0.1060 0.036 Uiso 1 1 calc R . . H7B H -0.0036 0.0351 0.1295 0.036 Uiso 1 1 calc R . . C8 C 0.0723(2) 0.1246(13) 0.1984(4) 0.034(2) Uani 1 1 d . . . H8A H 0.0469 0.2046 0.2138 0.041 Uiso 1 1 calc R . . H8B H 0.0850 0.2094 0.1661 0.041 Uiso 1 1 calc R . . C9 C 0.1083(2) 0.0911(11) 0.2500(3) 0.037(2) Uani 1 1 d . . . H9A H 0.1126 0.2245 0.2729 0.044 Uiso 1 1 calc R . . H9B H 0.0974 -0.0158 0.2781 0.044 Uiso 1 1 calc R . . C10 C 0.1763(3) 0.1829(11) 0.1936(3) 0.032(2) Uani 1 1 d . . . H10A H 0.1824 0.3086 0.2194 0.038 Uiso 1 1 calc R . . H10B H 0.1554 0.2261 0.1588 0.038 Uiso 1 1 calc R . . C11 C 0.2200(2) 0.1101(12) 0.1696(3) 0.031(2) Uani 1 1 d . . . H11A H 0.2377 0.2356 0.1593 0.037 Uiso 1 1 calc R . . H11B H 0.2376 0.0330 0.2023 0.037 Uiso 1 1 calc R . . C12 C 0.1886(2) 0.0662(12) 0.0611(3) 0.028(2) Uani 1 1 d . . . H12A H 0.2009 0.2061 0.0511 0.034 Uiso 1 1 calc R . . H12B H 0.1563 0.0819 0.0687 0.034 Uiso 1 1 calc R . . C13 C 0.1945(2) -0.0884(12) 0.0102(3) 0.032(2) Uani 1 1 d . . . H13A H 0.1840 -0.2288 0.0227 0.038 Uiso 1 1 calc R . . H13B H 0.2270 -0.0999 0.0036 0.038 Uiso 1 1 calc R . . C14 C 0.1212(2) -0.1054(11) -0.0576(3) 0.029(2) Uani 1 1 d . . . H15A H 0.1105 -0.0924 -0.1010 0.035 Uiso 1 1 calc R . . H15B H 0.1201 -0.2564 -0.0465 0.035 Uiso 1 1 calc R . . H101 H -0.013(2) -0.368(11) 0.224(3) 0.03(3) Uiso 1 1 d . . . H201 H 0.123(3) -0.371(19) 0.320(5) 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0350(14) 0.0322(18) 0.0399(15) 0.0006(12) -0.0035(11) 0.0022(11) O1 0.038(6) 0.042(8) 0.026(7) 0.000 0.002(5) 0.000 N1 0.019(4) 0.044(6) 0.024(4) 0.009(4) 0.002(4) 0.000(4) C1 0.018(5) 0.024(6) 0.038(6) 0.002(5) -0.007(5) 0.003(5) Cl2 0.0275(13) 0.0446(17) 0.0278(14) 0.0016(11) 0.0022(11) 0.0067(11) O2 0.056(6) 0.093(6) 0.053(5) 0.025(4) 0.001(4) -0.029(5) N2 0.027(4) 0.032(5) 0.023(4) -0.005(4) -0.010(3) 0.005(4) C2 0.011(5) 0.037(7) 0.015(5) 0.001(5) -0.010(4) 0.000(5) Cl3 0.0308(13) 0.0479(18) 0.0311(14) -0.0002(12) 0.0024(11) -0.0014(12) N3 0.011(4) 0.046(5) 0.024(4) 0.004(4) -0.003(4) 0.000(4) C3 0.013(4) 0.024(4) 0.022(4) -0.006(4) -0.006(4) 0.006(4) Cl4 0.0271(13) 0.0423(18) 0.0324(14) 0.0026(11) 0.0035(11) -0.0009(11) N4 0.023(4) 0.040(5) 0.027(5) -0.006(4) 0.006(4) 0.004(3) C4 0.018(5) 0.025(6) 0.025(5) 0.002(5) -0.010(5) -0.005(5) C5 0.010(5) 0.041(8) 0.013(5) 0.007(5) -0.006(4) 0.007(5) C6 0.011(5) 0.042(8) 0.025(6) 0.012(5) -0.007(4) 0.006(5) C7 0.023(4) 0.036(4) 0.030(4) -0.005(4) -0.007(4) -0.002(3) C8 0.022(5) 0.033(7) 0.047(6) -0.010(6) -0.003(5) -0.001(5) C9 0.025(5) 0.058(7) 0.029(6) -0.009(5) 0.007(5) 0.011(5) C10 0.054(6) 0.013(6) 0.028(5) 0.008(5) -0.001(5) -0.007(5) C11 0.019(5) 0.048(7) 0.024(6) -0.003(5) 0.000(5) 0.002(5) C12 0.026(5) 0.042(7) 0.016(5) -0.004(5) -0.011(5) 0.002(5) C13 0.020(5) 0.047(7) 0.028(6) 0.000(5) -0.007(5) 0.006(5) C14 0.021(5) 0.034(6) 0.033(5) 0.001(5) -0.004(5) -0.001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.487(7) . ? N1 C7 1.508(7) . ? C1 C6 1.381(8) . ? C1 C2 1.402(8) . ? N2 C10 1.497(7) . ? N2 C9 1.502(7) . ? C2 C3 1.393(8) . ? N3 C11 1.472(7) . ? N3 C12 1.503(7) . ? C3 C4 1.377(9) . ? C3 C14 1.509(8) . ? N4 C14 1.509(8) . ? N4 C13 1.511(7) . ? C4 C5 1.385(8) . ? C5 C6 1.376(9) . ? C5 C7 1.504(9) . ? C8 C9 1.522(8) . ? C10 C11 1.510(8) . ? C12 C13 1.511(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C7 113.9(6) . . ? C6 C1 C2 119.5(7) . . ? C10 N2 C9 113.8(5) . . ? C3 C2 C1 120.2(7) . . ? C11 N3 C12 115.9(6) . . ? C4 C3 C2 118.7(7) . . ? C4 C3 C14 122.5(8) . . ? C2 C3 C14 118.8(8) . . ? C14 N4 C13 115.7(5) . . ? C3 C4 C5 121.5(7) . . ? C6 C5 C4 119.6(7) . . ? C6 C5 C7 119.6(7) . . ? C4 C5 C7 120.8(8) . . ? C5 C6 C1 120.5(7) . . ? C5 C7 N1 112.2(5) . . ? N1 C8 C9 111.9(6) . . ? N2 C9 C8 114.5(5) . . ? N2 C10 C11 114.5(6) . . ? N3 C11 C10 114.5(6) . . ? N3 C12 C13 105.1(6) . . ? C12 C13 N4 113.9(6) . . ? C3 C14 N4 112.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(10) . . . . ? C1 C2 C3 C4 1.6(10) . . . . ? C1 C2 C3 C14 -179.3(6) . . . . ? C2 C3 C4 C5 -2.7(11) . . . . ? C14 C3 C4 C5 178.3(6) . . . . ? C3 C4 C5 C6 2.6(11) . . . . ? C3 C4 C5 C7 -180.0(7) . . . . ? C4 C5 C6 C1 -1.3(11) . . . . ? C7 C5 C6 C1 -178.8(6) . . . . ? C2 C1 C6 C5 0.2(10) . . . . ? C6 C5 C7 N1 -106.1(8) . . . . ? C4 C5 C7 N1 76.5(8) . . . . ? C8 N1 C7 C5 64.9(7) . . . . ? C7 N1 C8 C9 -175.8(5) . . . . ? C10 N2 C9 C8 66.1(8) . . . . ? N1 C8 C9 N2 73.6(7) . . . . ? C9 N2 C10 C11 -176.2(6) . . . . ? C12 N3 C11 C10 58.6(8) . . . . ? N2 C10 C11 N3 77.8(8) . . . . ? C11 N3 C12 C13 171.0(5) . . . . ? N3 C12 C13 N4 177.8(5) . . . . ? C14 N4 C13 C12 -87.8(7) . . . . ? C4 C3 C14 N4 -110.7(8) . . . . ? C2 C3 C14 N4 70.2(8) . . . . ? C13 N4 C14 C3 73.9(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B Cl2 0.92 2.22 3.104(5) 162.2 7 N4 H4A Cl4 0.92 2.20 3.081(6) 160.8 6_565 N2 H2A Cl2 0.92 2.27 3.079(6) 147.2 4_545 N2 H2B Cl1 0.92 2.24 3.150(6) 170.1 1_545 N1 H1A O1 0.92 1.88 2.775(7) 164.6 . N1 H1B Cl1 0.92 2.20 3.122(6) 177.4 1_545 N3 H3A Cl1 0.92 2.32 3.171(6) 153.0 1_545 N3 H3B Cl4 0.92 2.32 3.115(5) 144.3 4_545 N3 H3B Cl2 0.92 2.65 3.138(6) 113.7 1_545 O2 H201 Cl3 0.50(9) 2.74(9) 3.228(6) 166(17) . O1 H101 Cl3 0.85(5) 2.16(6) 3.017(7) 178(7) 2 _diffrn_measured_fraction_theta_max 0.350 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.350 _refine_diff_density_max 0.369 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.088 data_t4c _database_code_depnum_ccdc_archive 'CCDC 272037' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H50 Cl4 N4 O8 S4' _chemical_formula_weight 1032.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0881(10) _cell_length_b 30.6387(9) _cell_length_c 15.8038(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.292(3) _cell_angle_gamma 90.00 _cell_volume 4870.9(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 0.469 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17287 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.1099 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8547 _reflns_number_gt 5823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+2.1222P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8547 _refine_ls_number_parameters 636 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.12807(13) -0.22004(3) 1.01660(6) 0.0662(3) Uani 1 1 d . . . S1 S -0.26739(8) 0.06536(2) 0.98860(5) 0.0245(2) Uani 1 1 d . . . O1 O -0.3450(2) 0.04692(7) 1.05170(12) 0.0326(5) Uani 1 1 d . . . N1 N -0.2573(2) 0.02879(7) 0.91477(14) 0.0219(6) Uani 1 1 d . . . C1 C -0.1667(3) 0.03755(9) 0.84790(18) 0.0214(7) Uani 1 1 d . . . H1A H -0.1583 0.0695 0.8402 0.026 Uiso 1 1 calc R . . H1B H -0.2044 0.0250 0.7936 0.026 Uiso 1 1 calc R . . Cl2 Cl 0.0605(3) -0.19690(10) 0.8943(2) 0.0776(8) Uani 0.50 1 d P A 1 S2 S 0.15194(7) 0.05528(2) 0.77729(5) 0.0238(2) Uani 1 1 d . . . O2 O -0.1344(2) 0.07980(7) 1.01114(13) 0.0319(5) Uani 1 1 d . . . N2 N 0.0500(2) 0.01617(7) 0.79603(14) 0.0217(6) Uani 1 1 d . . . C2 C -0.0289(3) 0.01796(9) 0.87018(18) 0.0224(7) Uani 1 1 d . . . H2A H 0.0185 0.0358 0.9150 0.027 Uiso 1 1 calc R . . H2B H -0.0389 -0.0119 0.8928 0.027 Uiso 1 1 calc R . . Cl3 Cl 0.6085(8) -0.04554(17) 0.5243(4) 0.068(2) Uani 0.33 1 d P B 1 S3 S 0.23513(7) -0.11083(2) 0.64692(4) 0.0224(2) Uani 1 1 d . . . O3 O 0.2217(2) 0.06725(7) 0.85572(13) 0.0315(5) Uani 1 1 d . . . N3 N 0.1034(2) -0.09094(7) 0.68781(14) 0.0199(6) Uani 1 1 d . . . C3 C 0.0243(3) -0.01910(9) 0.73385(18) 0.0228(7) Uani 1 1 d . . . H3A H 0.0314 -0.0076 0.6758 0.027 Uiso 1 1 calc R . . H3B H -0.0670 -0.0304 0.7376 0.027 Uiso 1 1 calc R . . Cl4 Cl 0.7766(3) 0.02822(10) 0.5678(2) 0.0541(8) Uani 0.33 1 d P B 1 S4 S -0.25320(8) -0.18867(2) 0.59646(5) 0.0258(2) Uani 1 1 d . . . O4 O 0.2243(2) 0.04136(7) 0.70776(13) 0.0338(5) Uani 1 1 d . . . N4 N -0.2283(2) -0.14862(7) 0.66443(14) 0.0212(6) Uani 1 1 d . . . C4 C 0.1241(3) -0.05581(9) 0.75115(18) 0.0227(7) Uani 1 1 d . . . H4A H 0.2154 -0.0441 0.7496 0.027 Uiso 1 1 calc R . . H4B H 0.1148 -0.0678 0.8086 0.027 Uiso 1 1 calc R . . O5 O 0.3258(2) -0.07553(7) 0.63873(13) 0.0297(5) Uani 1 1 d . . . C5 C -0.0009(3) -0.12310(10) 0.70252(18) 0.0227(7) Uani 1 1 d . . . H5A H -0.0233 -0.1211 0.7623 0.027 Uiso 1 1 calc R . . H5B H 0.0338 -0.1528 0.6932 0.027 Uiso 1 1 calc R . . O6 O 0.1888(2) -0.13527(7) 0.57351(12) 0.0312(5) Uani 1 1 d . . . C6 C -0.1264(3) -0.11622(9) 0.64474(18) 0.0233(7) Uani 1 1 d . . . H6A H -0.1609 -0.0864 0.6527 0.028 Uiso 1 1 calc R . . H6B H -0.1057 -0.1193 0.5848 0.028 Uiso 1 1 calc R . . O7 O -0.1253(2) -0.20152(7) 0.57198(13) 0.0338(5) Uani 1 1 d . . . C7 C -0.3474(3) -0.13119(10) 0.70160(18) 0.0232(7) Uani 1 1 d . . . H7A H -0.4100 -0.1554 0.7103 0.028 Uiso 1 1 calc R . . H7B H -0.3925 -0.1101 0.6616 0.028 Uiso 1 1 calc R . . O8 O -0.3366(2) -0.21998(6) 0.63436(13) 0.0311(5) Uani 1 1 d . . . C8 C -0.3120(3) -0.10881(9) 0.78512(17) 0.0192(6) Uani 1 1 d . . . C9 C -0.2417(3) -0.13030(10) 0.85146(18) 0.0253(7) Uani 1 1 d . . . H9 H -0.2130 -0.1595 0.8441 0.030 Uiso 1 1 calc R . . C10 C -0.2133(3) -0.10957(10) 0.92792(19) 0.0279(7) Uani 1 1 d . . . H10 H -0.1645 -0.1244 0.9729 0.033 Uiso 1 1 calc R . . C11 C -0.2556(3) -0.06723(10) 0.93961(18) 0.0267(7) Uani 1 1 d . . . H11 H -0.2348 -0.0531 0.9925 0.032 Uiso 1 1 calc R . . C12 C -0.3278(3) -0.04512(9) 0.87511(18) 0.0212(7) Uani 1 1 d . . . C13 C -0.3545(3) -0.06592(9) 0.79744(17) 0.0202(7) Uani 1 1 d . . . H13 H -0.4021 -0.0509 0.7522 0.024 Uiso 1 1 calc R . . C14 C -0.3732(3) 0.00088(9) 0.8900(2) 0.0261(7) Uani 1 1 d . . . H14A H -0.4206 0.0124 0.8377 0.031 Uiso 1 1 calc R . . H14B H -0.4355 0.0011 0.9356 0.031 Uiso 1 1 calc R . . C15 C -0.3557(3) 0.10997(9) 0.94225(18) 0.0225(7) Uani 1 1 d . . . C16 C -0.4929(3) 0.10764(10) 0.92878(19) 0.0273(7) Uani 1 1 d . . . H16 H -0.5391 0.0821 0.9439 0.033 Uiso 1 1 calc R . . C17 C -0.5616(3) 0.14292(11) 0.8932(2) 0.0348(8) Uani 1 1 d . . . H17 H -0.6557 0.1416 0.8847 0.042 Uiso 1 1 calc R . . C18 C -0.4959(4) 0.18040(11) 0.8694(2) 0.0385(9) Uani 1 1 d . . . C19 C -0.3585(3) 0.18186(11) 0.8829(2) 0.0392(9) Uani 1 1 d . . . H19 H -0.3118 0.2072 0.8672 0.047 Uiso 1 1 calc R . . C20 C -0.2887(3) 0.14677(10) 0.9191(2) 0.0333(8) Uani 1 1 d . . . H20 H -0.1946 0.1481 0.9279 0.040 Uiso 1 1 calc R . . C21 C -0.5726(4) 0.21850(12) 0.8300(3) 0.0592(12) Uani 1 1 d . . . H21A H -0.6672 0.2152 0.8390 0.089 Uiso 1 1 calc R . . H21B H -0.5612 0.2194 0.7689 0.089 Uiso 1 1 calc R . . H21C H -0.5393 0.2457 0.8563 0.089 Uiso 1 1 calc R . . C22 C 0.0546(3) 0.10086(9) 0.74454(18) 0.0222(7) Uani 1 1 d . . . C23 C -0.0051(3) 0.10262(10) 0.66206(19) 0.0294(7) Uani 1 1 d . . . H23 H 0.0108 0.0803 0.6224 0.035 Uiso 1 1 calc R . . C24 C -0.0881(3) 0.13737(11) 0.6385(2) 0.0329(8) Uani 1 1 d . . . H24 H -0.1283 0.1387 0.5823 0.040 Uiso 1 1 calc R . . C25 C -0.1137(3) 0.17030(10) 0.6957(2) 0.0320(8) Uani 1 1 d . . . C26 C -0.0487(3) 0.16891(10) 0.7761(2) 0.0315(8) Uani 1 1 d . . . H26 H -0.0614 0.1920 0.8149 0.038 Uiso 1 1 calc R . . C27 C 0.0340(3) 0.13463(10) 0.80090(19) 0.0265(7) Uani 1 1 d . . . H27 H 0.0770 0.1341 0.8565 0.032 Uiso 1 1 calc R . . C28 C -0.2129(4) 0.20609(12) 0.6722(3) 0.0492(10) Uani 1 1 d . . . H28A H -0.2999 0.1980 0.6911 0.074 Uiso 1 1 calc R . . H28B H -0.2202 0.2101 0.6105 0.074 Uiso 1 1 calc R . . H28C H -0.1830 0.2334 0.6997 0.074 Uiso 1 1 calc R . . C29 C 0.3065(3) -0.14798(9) 0.72219(17) 0.0188(6) Uani 1 1 d . . . C30 C 0.3598(3) -0.13214(10) 0.80063(18) 0.0224(7) Uani 1 1 d . . . H30 H 0.3603 -0.1017 0.8121 0.027 Uiso 1 1 calc R . . C31 C 0.4113(3) -0.16110(10) 0.86102(18) 0.0252(7) Uani 1 1 d . . . H31 H 0.4482 -0.1503 0.9140 0.030 Uiso 1 1 calc R . . C32 C 0.4104(3) -0.20591(10) 0.84612(19) 0.0272(7) Uani 1 1 d . . . C33 C 0.3598(3) -0.22076(10) 0.7676(2) 0.0299(8) Uani 1 1 d . . . H33 H 0.3610 -0.2512 0.7559 0.036 Uiso 1 1 calc R . . C34 C 0.3070(3) -0.19219(9) 0.70525(19) 0.0249(7) Uani 1 1 d . . . H34 H 0.2717 -0.2030 0.6519 0.030 Uiso 1 1 calc R . . C35 C 0.4604(4) -0.23658(12) 0.9156(2) 0.0464(10) Uani 1 1 d . . . H35A H 0.5484 -0.2271 0.9388 0.070 Uiso 1 1 calc R . . H35B H 0.4666 -0.2661 0.8925 0.070 Uiso 1 1 calc R . . H35C H 0.3988 -0.2365 0.9606 0.070 Uiso 1 1 calc R . . C36 C -0.3442(3) -0.16613(10) 0.50706(18) 0.0258(7) Uani 1 1 d . . . C37 C -0.4768(3) -0.15626(12) 0.5121(2) 0.0355(8) Uani 1 1 d . . . H37 H -0.5208 -0.1647 0.5606 0.043 Uiso 1 1 calc R . . C38 C -0.5455(3) -0.13405(12) 0.4465(2) 0.0403(9) Uani 1 1 d . . . H38 H -0.6362 -0.1267 0.4508 0.048 Uiso 1 1 calc R . . C39 C -0.4834(3) -0.12240(11) 0.3741(2) 0.0345(8) Uani 1 1 d . . . C40 C -0.3519(3) -0.13411(11) 0.3689(2) 0.0354(8) Uani 1 1 d . . . H40 H -0.3094 -0.1274 0.3188 0.042 Uiso 1 1 calc R . . C41 C -0.2808(3) -0.15542(10) 0.4351(2) 0.0313(8) Uani 1 1 d . . . H41 H -0.1899 -0.1626 0.4311 0.038 Uiso 1 1 calc R . . C42 C -0.5572(4) -0.09661(13) 0.3038(2) 0.0478(10) Uani 1 1 d . . . H42A H -0.4937 -0.0794 0.2737 0.072 Uiso 1 1 calc R . . H42B H -0.6209 -0.0770 0.3282 0.072 Uiso 1 1 calc R . . H42C H -0.6049 -0.1167 0.2640 0.072 Uiso 1 1 calc R . . C43 C 0.0297(12) -0.2097(4) 0.9709(9) 0.092(5) Uani 0.50 1 d P A 1 H43A H 0.0747 -0.1882 1.0099 0.110 Uiso 0.50 1 calc PR A 1 H43B H 0.0799 -0.2373 0.9807 0.110 Uiso 0.50 1 calc PR A 1 C44 C 0.7078(5) -0.01000(15) 0.4821(3) 0.0670(13) Uani 1 1 d . . . Cl2A Cl 0.0265(3) -0.22833(11) 0.86853(17) 0.0770(7) Uani 0.50 1 d P A 2 Cl3A Cl 0.6627(6) -0.0127(2) 0.5861(4) 0.084(2) Uani 0.33 1 d P B 2 Cl4A Cl 0.8925(9) -0.0122(3) 0.4986(4) 0.0628(16) Uani 0.33 1 d P . 2 C43A C 0.0041(10) -0.2361(3) 0.9618(6) 0.057(2) Uani 0.50 1 d P A 2 H43C H 0.0835 -0.2238 0.9939 0.068 Uiso 0.50 1 calc PR A 2 H43D H 0.0099 -0.2681 0.9696 0.068 Uiso 0.50 1 calc PR A 2 Cl3B Cl 0.5978(11) -0.0299(3) 0.5599(5) 0.096(4) Uani 0.33 1 d P B 3 Cl4B Cl 0.8589(14) -0.0007(4) 0.5058(7) 0.185(6) Uani 0.33 1 d P B 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1003(10) 0.0496(6) 0.0485(6) 0.0051(5) 0.0049(6) 0.0012(6) S1 0.0246(5) 0.0281(4) 0.0211(4) -0.0067(3) 0.0039(3) -0.0009(3) O1 0.0371(14) 0.0385(13) 0.0236(12) -0.0024(10) 0.0123(10) 0.0007(11) N1 0.0205(14) 0.0219(13) 0.0246(14) -0.0080(11) 0.0092(11) -0.0042(11) C1 0.0235(17) 0.0204(15) 0.0210(16) -0.0022(12) 0.0066(13) -0.0019(13) Cl2 0.0506(16) 0.079(2) 0.105(2) 0.0281(19) 0.0162(14) 0.0106(14) S2 0.0190(4) 0.0274(4) 0.0253(4) 0.0028(3) 0.0031(3) -0.0035(3) O2 0.0236(13) 0.0386(13) 0.0326(13) -0.0106(10) -0.0034(9) -0.0007(10) N2 0.0218(14) 0.0227(13) 0.0213(14) -0.0029(10) 0.0074(11) -0.0047(11) C2 0.0223(17) 0.0243(16) 0.0212(16) 0.0013(13) 0.0056(13) -0.0001(13) Cl3 0.069(4) 0.036(2) 0.095(5) 0.027(2) -0.025(4) -0.020(2) S3 0.0195(4) 0.0285(4) 0.0198(4) 0.0002(3) 0.0055(3) 0.0007(3) O3 0.0272(13) 0.0342(13) 0.0313(12) 0.0057(10) -0.0081(10) -0.0081(10) N3 0.0144(13) 0.0243(13) 0.0211(13) -0.0025(10) 0.0026(10) -0.0024(11) C3 0.0179(17) 0.0277(17) 0.0227(17) -0.0030(13) 0.0011(13) -0.0004(13) Cl4 0.0482(19) 0.0466(17) 0.063(2) -0.0128(15) -0.0236(16) -0.0058(14) S4 0.0240(5) 0.0274(4) 0.0260(4) -0.0079(3) 0.0018(3) -0.0006(4) O4 0.0309(13) 0.0363(13) 0.0370(13) 0.0027(10) 0.0207(10) -0.0006(10) N4 0.0143(13) 0.0240(13) 0.0253(14) -0.0077(11) 0.0013(10) -0.0025(11) C4 0.0192(17) 0.0284(17) 0.0203(16) -0.0015(13) -0.0008(12) -0.0009(13) O5 0.0212(12) 0.0329(12) 0.0362(13) 0.0092(10) 0.0107(9) -0.0030(10) C5 0.0154(16) 0.0281(16) 0.0248(17) 0.0011(13) 0.0034(13) -0.0011(13) O6 0.0315(13) 0.0429(13) 0.0194(11) -0.0063(10) 0.0026(9) 0.0041(11) C6 0.0226(17) 0.0260(16) 0.0210(16) -0.0019(13) 0.0002(13) -0.0028(13) O7 0.0252(13) 0.0368(13) 0.0400(14) -0.0115(10) 0.0062(10) 0.0085(10) C7 0.0177(16) 0.0265(16) 0.0257(17) -0.0067(13) 0.0022(13) -0.0017(13) O8 0.0361(14) 0.0246(11) 0.0328(13) -0.0037(9) 0.0029(10) -0.0083(10) C8 0.0142(15) 0.0207(15) 0.0233(16) -0.0018(12) 0.0053(12) -0.0026(12) C9 0.0262(18) 0.0223(16) 0.0279(18) 0.0006(14) 0.0054(14) -0.0006(14) C10 0.0280(19) 0.0316(18) 0.0237(18) 0.0051(14) 0.0004(14) -0.0001(15) C11 0.0304(19) 0.0339(18) 0.0164(16) -0.0053(13) 0.0049(13) -0.0058(15) C12 0.0191(16) 0.0235(16) 0.0221(17) -0.0015(13) 0.0092(13) -0.0049(13) C13 0.0156(16) 0.0269(16) 0.0181(16) 0.0006(13) 0.0019(12) -0.0031(13) C14 0.0225(17) 0.0280(17) 0.0287(18) -0.0070(14) 0.0070(14) -0.0043(14) C15 0.0232(17) 0.0238(16) 0.0208(16) -0.0084(13) 0.0033(13) -0.0033(14) C16 0.0261(19) 0.0266(17) 0.0291(18) -0.0048(14) 0.0019(14) -0.0052(15) C17 0.0228(18) 0.0344(19) 0.047(2) -0.0081(16) -0.0014(15) -0.0019(16) C18 0.038(2) 0.0271(18) 0.050(2) -0.0073(16) -0.0002(17) 0.0053(16) C19 0.035(2) 0.0223(18) 0.062(2) -0.0025(16) 0.0151(18) -0.0046(16) C20 0.0271(19) 0.0230(17) 0.051(2) -0.0089(15) 0.0087(16) -0.0021(15) C21 0.056(3) 0.038(2) 0.081(3) 0.004(2) -0.010(2) 0.010(2) C22 0.0198(16) 0.0242(16) 0.0227(17) 0.0039(13) 0.0022(13) -0.0066(13) C23 0.0289(19) 0.0357(18) 0.0238(18) 0.0013(14) 0.0038(14) -0.0014(15) C24 0.0275(19) 0.045(2) 0.0254(18) 0.0094(16) -0.0019(14) -0.0079(16) C25 0.0211(18) 0.0313(18) 0.043(2) 0.0100(16) 0.0016(15) -0.0035(15) C26 0.0283(19) 0.0271(18) 0.039(2) 0.0010(15) 0.0011(15) -0.0046(15) C27 0.0252(18) 0.0295(18) 0.0247(17) -0.0006(14) 0.0016(13) -0.0074(14) C28 0.038(2) 0.045(2) 0.064(3) 0.0174(19) 0.0007(19) 0.0020(18) C29 0.0134(15) 0.0237(16) 0.0201(16) -0.0019(12) 0.0060(12) -0.0014(13) C30 0.0182(16) 0.0232(16) 0.0266(17) -0.0053(13) 0.0072(13) -0.0001(13) C31 0.0196(17) 0.0354(19) 0.0209(17) -0.0011(14) 0.0024(13) 0.0036(14) C32 0.0240(18) 0.0299(18) 0.0286(19) 0.0041(14) 0.0077(14) 0.0032(14) C33 0.0296(19) 0.0212(16) 0.040(2) -0.0021(14) 0.0079(15) -0.0007(14) C34 0.0208(17) 0.0272(17) 0.0266(17) -0.0082(14) 0.0022(13) -0.0029(14) C35 0.055(3) 0.044(2) 0.040(2) 0.0125(17) 0.0078(18) 0.0106(19) C36 0.0218(18) 0.0330(17) 0.0228(17) -0.0079(14) 0.0042(13) -0.0063(14) C37 0.0224(19) 0.063(2) 0.0213(18) -0.0011(16) 0.0030(14) -0.0075(17) C38 0.0225(19) 0.072(3) 0.0267(19) -0.0026(18) 0.0010(15) -0.0014(18) C39 0.030(2) 0.047(2) 0.0254(19) -0.0007(15) -0.0008(15) -0.0062(16) C40 0.033(2) 0.044(2) 0.0305(19) -0.0001(16) 0.0097(15) -0.0095(17) C41 0.0215(18) 0.0369(19) 0.036(2) -0.0059(15) 0.0076(15) -0.0059(15) C42 0.043(2) 0.065(3) 0.035(2) 0.0074(19) -0.0001(17) 0.003(2) C43 0.079(8) 0.053(7) 0.129(12) 0.017(8) -0.082(8) -0.017(7) C44 0.086(4) 0.079(3) 0.038(2) 0.010(2) 0.017(2) -0.009(3) Cl2A 0.0665(18) 0.086(2) 0.080(2) -0.0100(15) 0.0171(13) -0.0018(15) Cl3A 0.084(4) 0.122(5) 0.049(3) 0.030(3) 0.033(3) 0.045(4) Cl4A 0.090(4) 0.082(3) 0.017(2) -0.005(2) 0.007(2) 0.003(3) C43A 0.062(7) 0.050(6) 0.057(6) 0.005(5) 0.001(5) 0.015(5) Cl3B 0.077(5) 0.156(10) 0.059(6) 0.070(6) 0.026(5) 0.015(7) Cl4B 0.179(12) 0.243(15) 0.119(9) 0.086(8) -0.086(8) -0.097(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C43A 1.715(9) . ? Cl1 C43 1.824(15) . ? S1 O1 1.430(2) . ? S1 O2 1.432(2) . ? S1 N1 1.626(2) . ? S1 C15 1.761(3) . ? N1 C1 1.473(4) . ? N1 C14 1.477(4) . ? C1 C2 1.530(4) . ? Cl2 C43 1.332(15) . ? S2 O3 1.427(2) . ? S2 O4 1.429(2) . ? S2 N2 1.621(2) . ? S2 C22 1.762(3) . ? N2 C2 1.466(4) . ? N2 C3 1.470(3) . ? Cl3 C44 1.654(8) . ? S3 O5 1.429(2) . ? S3 O6 1.430(2) . ? S3 N3 1.638(2) . ? S3 C29 1.761(3) . ? N3 C5 1.473(3) . ? N3 C4 1.474(3) . ? C3 C4 1.521(4) . ? Cl4 C44 1.883(5) . ? S4 O7 1.430(2) . ? S4 O8 1.436(2) . ? S4 N4 1.638(2) . ? S4 C36 1.767(3) . ? N4 C7 1.476(4) . ? N4 C6 1.479(4) . ? C5 C6 1.519(4) . ? C7 C8 1.506(4) . ? C8 C9 1.387(4) . ? C8 C13 1.400(4) . ? C9 C10 1.376(4) . ? C10 C11 1.382(4) . ? C11 C12 1.385(4) . ? C12 C13 1.391(4) . ? C12 C14 1.506(4) . ? C15 C20 1.378(4) . ? C15 C16 1.386(4) . ? C16 C17 1.381(4) . ? C17 C18 1.391(5) . ? C18 C19 1.388(5) . ? C18 C21 1.509(5) . ? C19 C20 1.385(4) . ? C22 C27 1.391(4) . ? C22 C23 1.396(4) . ? C23 C24 1.388(4) . ? C24 C25 1.391(5) . ? C25 C26 1.386(4) . ? C25 C28 1.512(4) . ? C26 C27 1.380(4) . ? C29 C34 1.381(4) . ? C29 C30 1.400(4) . ? C30 C31 1.376(4) . ? C31 C32 1.393(4) . ? C32 C33 1.383(4) . ? C32 C35 1.503(4) . ? C33 C34 1.393(4) . ? C36 C37 1.380(4) . ? C36 C41 1.385(4) . ? C37 C38 1.383(5) . ? C38 C39 1.391(5) . ? C39 C40 1.383(4) . ? C39 C42 1.513(5) . ? C40 C41 1.387(5) . ? C44 Cl4B 1.568(14) . ? C44 Cl3A 1.739(7) . ? C44 Cl3B 1.821(9) . ? C44 Cl4A 1.863(10) . ? Cl2A C43A 1.527(10) . ? Cl4A Cl4A 2.292(19) 3_756 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C43A Cl1 C43 27.8(4) . . ? O1 S1 O2 120.03(13) . . ? O1 S1 N1 107.16(13) . . ? O2 S1 N1 106.48(13) . . ? O1 S1 C15 108.08(14) . . ? O2 S1 C15 107.41(14) . . ? N1 S1 C15 107.04(13) . . ? C1 N1 C14 115.9(2) . . ? C1 N1 S1 117.68(18) . . ? C14 N1 S1 119.87(19) . . ? N1 C1 C2 111.4(2) . . ? O3 S2 O4 119.86(14) . . ? O3 S2 N2 108.04(13) . . ? O4 S2 N2 106.69(12) . . ? O3 S2 C22 106.21(13) . . ? O4 S2 C22 108.42(13) . . ? N2 S2 C22 107.00(13) . . ? C2 N2 C3 118.8(2) . . ? C2 N2 S2 120.55(19) . . ? C3 N2 S2 120.26(19) . . ? N2 C2 C1 111.7(2) . . ? O5 S3 O6 119.72(13) . . ? O5 S3 N3 107.33(12) . . ? O6 S3 N3 106.81(12) . . ? O5 S3 C29 108.55(13) . . ? O6 S3 C29 107.58(13) . . ? N3 S3 C29 106.08(12) . . ? C5 N3 C4 116.6(2) . . ? C5 N3 S3 115.07(18) . . ? C4 N3 S3 117.48(18) . . ? N2 C3 C4 110.0(2) . . ? O7 S4 O8 119.86(13) . . ? O7 S4 N4 106.66(12) . . ? O8 S4 N4 107.01(12) . . ? O7 S4 C36 108.46(14) . . ? O8 S4 C36 107.99(14) . . ? N4 S4 C36 106.06(13) . . ? C7 N4 C6 116.1(2) . . ? C7 N4 S4 116.30(18) . . ? C6 N4 S4 116.08(19) . . ? N3 C4 C3 111.1(2) . . ? N3 C5 C6 112.7(2) . . ? N4 C6 C5 110.0(2) . . ? N4 C7 C8 111.5(2) . . ? C9 C8 C13 119.0(3) . . ? C9 C8 C7 121.3(3) . . ? C13 C8 C7 119.6(2) . . ? C10 C9 C8 120.4(3) . . ? C9 C10 C11 120.3(3) . . ? C10 C11 C12 120.8(3) . . ? C11 C12 C13 118.8(3) . . ? C11 C12 C14 119.5(3) . . ? C13 C12 C14 121.7(3) . . ? C12 C13 C8 120.8(3) . . ? N1 C14 C12 109.8(2) . . ? C20 C15 C16 120.3(3) . . ? C20 C15 S1 120.2(2) . . ? C16 C15 S1 119.5(2) . . ? C17 C16 C15 119.1(3) . . ? C16 C17 C18 121.4(3) . . ? C19 C18 C17 118.4(3) . . ? C19 C18 C21 120.9(3) . . ? C17 C18 C21 120.7(3) . . ? C20 C19 C18 120.6(3) . . ? C15 C20 C19 120.0(3) . . ? C27 C22 C23 119.7(3) . . ? C27 C22 S2 120.5(2) . . ? C23 C22 S2 119.8(2) . . ? C24 C23 C22 119.3(3) . . ? C23 C24 C25 121.3(3) . . ? C26 C25 C24 118.4(3) . . ? C26 C25 C28 120.4(3) . . ? C24 C25 C28 121.2(3) . . ? C27 C26 C25 121.2(3) . . ? C26 C27 C22 120.0(3) . . ? C34 C29 C30 120.3(3) . . ? C34 C29 S3 120.7(2) . . ? C30 C29 S3 119.0(2) . . ? C31 C30 C29 119.4(3) . . ? C30 C31 C32 121.4(3) . . ? C33 C32 C31 118.2(3) . . ? C33 C32 C35 122.1(3) . . ? C31 C32 C35 119.7(3) . . ? C32 C33 C34 121.6(3) . . ? C29 C34 C33 119.1(3) . . ? C37 C36 C41 120.3(3) . . ? C37 C36 S4 119.2(2) . . ? C41 C36 S4 120.3(2) . . ? C36 C37 C38 119.9(3) . . ? C37 C38 C39 120.8(3) . . ? C40 C39 C38 118.4(3) . . ? C40 C39 C42 120.9(3) . . ? C38 C39 C42 120.7(3) . . ? C39 C40 C41 121.4(3) . . ? C36 C41 C40 119.1(3) . . ? Cl2 C43 Cl1 132.9(6) . . ? Cl4B C44 Cl3 129.1(6) . . ? Cl4B C44 Cl3A 95.8(5) . . ? Cl3 C44 Cl3A 51.6(4) . . ? Cl4B C44 Cl3B 122.0(6) . . ? Cl3 C44 Cl3B 24.4(3) . . ? Cl3A C44 Cl3B 29.7(3) . . ? Cl4B C44 Cl4A 13.9(6) . . ? Cl3 C44 Cl4A 123.3(5) . . ? Cl3A C44 Cl4A 101.3(3) . . ? Cl3B C44 Cl4A 123.2(5) . . ? Cl4B C44 Cl4 54.3(5) . . ? Cl3 C44 Cl4 108.8(3) . . ? Cl3A C44 Cl4 57.2(3) . . ? Cl3B C44 Cl4 86.2(4) . . ? Cl4A C44 Cl4 67.1(3) . . ? C44 Cl4A Cl4A 157.8(7) . 3_756 ? Cl2A C43A Cl1 128.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C1 -171.7(2) . . . . ? O2 S1 N1 C1 -42.1(2) . . . . ? C15 S1 N1 C1 72.6(2) . . . . ? O1 S1 N1 C14 37.7(2) . . . . ? O2 S1 N1 C14 167.3(2) . . . . ? C15 S1 N1 C14 -78.0(2) . . . . ? C14 N1 C1 C2 -115.5(3) . . . . ? S1 N1 C1 C2 92.7(3) . . . . ? O3 S2 N2 C2 43.0(2) . . . . ? O4 S2 N2 C2 173.1(2) . . . . ? C22 S2 N2 C2 -71.0(2) . . . . ? O3 S2 N2 C3 -144.0(2) . . . . ? O4 S2 N2 C3 -13.9(2) . . . . ? C22 S2 N2 C3 102.0(2) . . . . ? C3 N2 C2 C1 -79.0(3) . . . . ? S2 N2 C2 C1 94.2(3) . . . . ? N1 C1 C2 N2 164.9(2) . . . . ? O5 S3 N3 C5 -178.88(19) . . . . ? O6 S3 N3 C5 51.6(2) . . . . ? C29 S3 N3 C5 -63.0(2) . . . . ? O5 S3 N3 C4 -35.7(2) . . . . ? O6 S3 N3 C4 -165.22(19) . . . . ? C29 S3 N3 C4 80.2(2) . . . . ? C2 N2 C3 C4 -97.8(3) . . . . ? S2 N2 C3 C4 89.1(3) . . . . ? O7 S4 N4 C7 -177.4(2) . . . . ? O8 S4 N4 C7 -48.0(2) . . . . ? C36 S4 N4 C7 67.1(2) . . . . ? O7 S4 N4 C6 40.5(2) . . . . ? O8 S4 N4 C6 169.97(19) . . . . ? C36 S4 N4 C6 -74.9(2) . . . . ? C5 N3 C4 C3 -82.5(3) . . . . ? S3 N3 C4 C3 134.9(2) . . . . ? N2 C3 C4 N3 -178.0(2) . . . . ? C4 N3 C5 C6 104.3(3) . . . . ? S3 N3 C5 C6 -112.2(2) . . . . ? C7 N4 C6 C5 112.8(3) . . . . ? S4 N4 C6 C5 -105.1(2) . . . . ? N3 C5 C6 N4 -178.3(2) . . . . ? C6 N4 C7 C8 -61.0(3) . . . . ? S4 N4 C7 C8 157.03(19) . . . . ? N4 C7 C8 C9 -55.7(4) . . . . ? N4 C7 C8 C13 126.4(3) . . . . ? C13 C8 C9 C10 -0.5(4) . . . . ? C7 C8 C9 C10 -178.4(3) . . . . ? C8 C9 C10 C11 0.5(5) . . . . ? C9 C10 C11 C12 0.5(5) . . . . ? C10 C11 C12 C13 -1.5(4) . . . . ? C10 C11 C12 C14 179.6(3) . . . . ? C11 C12 C13 C8 1.5(4) . . . . ? C14 C12 C13 C8 -179.6(3) . . . . ? C9 C8 C13 C12 -0.5(4) . . . . ? C7 C8 C13 C12 177.4(3) . . . . ? C1 N1 C14 C12 69.0(3) . . . . ? S1 N1 C14 C12 -139.9(2) . . . . ? C11 C12 C14 N1 57.5(4) . . . . ? C13 C12 C14 N1 -121.4(3) . . . . ? O1 S1 C15 C20 143.2(2) . . . . ? O2 S1 C15 C20 12.3(3) . . . . ? N1 S1 C15 C20 -101.7(3) . . . . ? O1 S1 C15 C16 -37.2(3) . . . . ? O2 S1 C15 C16 -168.1(2) . . . . ? N1 S1 C15 C16 77.9(3) . . . . ? C20 C15 C16 C17 -1.0(4) . . . . ? S1 C15 C16 C17 179.4(2) . . . . ? C15 C16 C17 C18 0.9(5) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C16 C17 C18 C21 179.5(3) . . . . ? C17 C18 C19 C20 0.0(5) . . . . ? C21 C18 C19 C20 -179.9(3) . . . . ? C16 C15 C20 C19 0.7(5) . . . . ? S1 C15 C20 C19 -179.8(2) . . . . ? C18 C19 C20 C15 -0.1(5) . . . . ? O3 S2 C22 C27 -14.2(3) . . . . ? O4 S2 C22 C27 -144.3(2) . . . . ? N2 S2 C22 C27 101.0(2) . . . . ? O3 S2 C22 C23 167.4(2) . . . . ? O4 S2 C22 C23 37.4(3) . . . . ? N2 S2 C22 C23 -77.3(3) . . . . ? C27 C22 C23 C24 -2.3(4) . . . . ? S2 C22 C23 C24 176.1(2) . . . . ? C22 C23 C24 C25 -0.5(5) . . . . ? C23 C24 C25 C26 3.3(5) . . . . ? C23 C24 C25 C28 -174.8(3) . . . . ? C24 C25 C26 C27 -3.4(5) . . . . ? C28 C25 C26 C27 174.8(3) . . . . ? C25 C26 C27 C22 0.7(5) . . . . ? C23 C22 C27 C26 2.2(4) . . . . ? S2 C22 C27 C26 -176.1(2) . . . . ? O5 S3 C29 C34 -132.6(2) . . . . ? O6 S3 C29 C34 -1.7(3) . . . . ? N3 S3 C29 C34 112.4(2) . . . . ? O5 S3 C29 C30 49.2(3) . . . . ? O6 S3 C29 C30 -179.9(2) . . . . ? N3 S3 C29 C30 -65.9(2) . . . . ? C34 C29 C30 C31 -0.7(4) . . . . ? S3 C29 C30 C31 177.6(2) . . . . ? C29 C30 C31 C32 -0.7(4) . . . . ? C30 C31 C32 C33 1.9(4) . . . . ? C30 C31 C32 C35 -176.5(3) . . . . ? C31 C32 C33 C34 -1.9(5) . . . . ? C35 C32 C33 C34 176.4(3) . . . . ? C30 C29 C34 C33 0.7(4) . . . . ? S3 C29 C34 C33 -177.6(2) . . . . ? C32 C33 C34 C29 0.7(4) . . . . ? O7 S4 C36 C37 172.1(2) . . . . ? O8 S4 C36 C37 40.7(3) . . . . ? N4 S4 C36 C37 -73.7(3) . . . . ? O7 S4 C36 C41 -12.8(3) . . . . ? O8 S4 C36 C41 -144.2(2) . . . . ? N4 S4 C36 C41 101.4(3) . . . . ? C41 C36 C37 C38 -2.5(5) . . . . ? S4 C36 C37 C38 172.6(3) . . . . ? C36 C37 C38 C39 1.6(5) . . . . ? C37 C38 C39 C40 0.9(5) . . . . ? C37 C38 C39 C42 -177.7(3) . . . . ? C38 C39 C40 C41 -2.6(5) . . . . ? C42 C39 C40 C41 176.0(3) . . . . ? C37 C36 C41 C40 0.9(5) . . . . ? S4 C36 C41 C40 -174.1(2) . . . . ? C39 C40 C41 C36 1.7(5) . . . . ? C43A Cl1 C43 Cl2 87.5(15) . . . . ? Cl4B C44 Cl4A Cl4A -43(2) . . . 3_756 ? Cl3 C44 Cl4A Cl4A -161.7(11) . . . 3_756 ? Cl3A C44 Cl4A Cl4A -110.6(12) . . . 3_756 ? Cl3B C44 Cl4A Cl4A -132.5(12) . . . 3_756 ? Cl4 C44 Cl4A Cl4A -63.7(11) . . . 3_756 ? C43 Cl1 C43A Cl2A -80.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.532 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.121 data_c:\structs\chris\a6i\a6i _database_code_depnum_ccdc_archive 'CCDC 272038' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H34 I7 N5' _chemical_formula_weight 1184.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.7945(18) _cell_length_b 11.5702(8) _cell_length_c 15.8028(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.8594(50) _cell_angle_gamma 90.00 _cell_volume 5999(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4288 _exptl_absorpt_coefficient_mu 7.256 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type scalepack _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12929 _diffrn_reflns_av_R_equivalents 0.0937 _diffrn_reflns_av_sigmaI/netI 0.1296 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5536 _reflns_number_gt 3068 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+42.1498P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5536 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1330 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I4 I 0.03552(3) 0.36886(7) 0.45942(6) 0.0351(3) Uani 1 1 d . . . I5 I -0.04006(3) 0.38430(7) 0.33444(6) 0.0411(3) Uani 1 1 d . . . I3 I 0.11286(3) 0.35065(8) 0.60601(6) 0.0450(3) Uani 1 1 d . . . I1 I -0.10734(3) 0.08597(8) 0.38950(6) 0.0400(3) Uani 1 1 d . . . I6 I -0.14833(3) 0.39603(7) 0.18502(6) 0.0412(3) Uani 1 1 d . . . I7 I -0.26312(4) 0.14385(9) 0.12484(8) 0.0660(4) Uani 1 1 d . . . I2 I -0.17416(3) 0.13655(8) 0.65833(6) 0.0412(3) Uani 1 1 d . . . N5 N -0.1064(4) -0.1196(9) 0.6603(7) 0.049(4) Uani 1 1 d . . . H5A H -0.1148 -0.1873 0.6812 0.059 Uiso 1 1 calc R . . H5B H -0.1194 -0.0596 0.6809 0.059 Uiso 1 1 calc R . . N2 N -0.1575(4) 0.3528(9) 0.4050(6) 0.040(3) Uani 1 1 d . . . H2A H -0.1417 0.2910 0.3968 0.048 Uiso 1 1 calc R . . H2B H -0.1489 0.4163 0.3793 0.048 Uiso 1 1 calc R . . C8 C -0.1070(4) 0.3569(10) 0.5436(8) 0.035(3) Uani 1 1 d . . . H8A H -0.0968 0.2848 0.5224 0.042 Uiso 1 1 calc R . . H8B H -0.0906 0.4222 0.5302 0.042 Uiso 1 1 calc R . . C2 C -0.0455(4) 0.0042(10) 0.6668(8) 0.032(3) Uani 1 1 d . . . N1 N -0.1028(4) 0.3495(9) 0.6387(7) 0.040(3) Uani 1 1 d . . . H1A H -0.1190 0.2904 0.6500 0.048 Uiso 1 1 calc R . . H1B H -0.1121 0.4172 0.6576 0.048 Uiso 1 1 calc R . . N3 N -0.2112(4) 0.1136(11) 0.3341(9) 0.065(4) Uani 1 1 d . . . H3A H -0.2192 0.1309 0.2756 0.078 Uiso 1 1 calc R . . H3B H -0.1834 0.1027 0.3471 0.078 Uiso 1 1 calc R . . C6 C -0.0432(4) 0.2124(10) 0.6671(8) 0.030(3) Uani 1 1 d . . . C16 C -0.0601(5) -0.1067(10) 0.6966(9) 0.040(4) Uani 1 1 d . . . H16A H -0.0537 -0.1084 0.7611 0.048 Uiso 1 1 calc R . . H16B H -0.0459 -0.1722 0.6765 0.048 Uiso 1 1 calc R . . C1 C -0.0587(4) 0.1127(10) 0.6919(8) 0.032(3) Uani 1 1 d . . . H1 H -0.0783 0.1157 0.7260 0.038 Uiso 1 1 calc R . . N4 N -0.1773(4) -0.1155(9) 0.4374(8) 0.050(3) Uani 1 1 d . . . H4A H -0.1580 -0.0707 0.4205 0.060 Uiso 1 1 calc R . . H4B H -0.1816 -0.1808 0.4031 0.060 Uiso 1 1 calc R . . C4 C -0.0020(5) 0.1055(12) 0.5907(9) 0.044(4) Uani 1 1 d . . . H4 H 0.0171 0.1034 0.5552 0.053 Uiso 1 1 calc R . . C3 C -0.0171(4) 0.0005(13) 0.6172(8) 0.038(4) Uani 1 1 d . . . H3 H -0.0077 -0.0716 0.6010 0.046 Uiso 1 1 calc R . . C5 C -0.0146(5) 0.2088(12) 0.6157(8) 0.042(4) Uani 1 1 d . . . H5 H -0.0040 0.2787 0.5984 0.050 Uiso 1 1 calc R . . C15 C -0.1190(5) -0.1207(12) 0.5663(9) 0.045(4) Uani 1 1 d . . . H15A H -0.1023 -0.1777 0.5435 0.054 Uiso 1 1 calc R . . H15B H -0.1139 -0.0437 0.5439 0.054 Uiso 1 1 calc R . . C11 C -0.2199(6) 0.2174(14) 0.3844(12) 0.072(5) Uani 1 1 d . . . H11A H -0.2089 0.2032 0.4474 0.086 Uiso 1 1 calc R . . H11B H -0.2497 0.2272 0.3742 0.086 Uiso 1 1 calc R . . C9 C -0.1509(5) 0.3744(12) 0.4988(9) 0.052(4) Uani 1 1 d . . . H9A H -0.1680 0.3211 0.5238 0.063 Uiso 1 1 calc R . . H9B H -0.1591 0.4545 0.5084 0.063 Uiso 1 1 calc R . . C7 C -0.0593(4) 0.3286(10) 0.6896(9) 0.038(4) Uani 1 1 d . . . H7A H -0.0581 0.3311 0.7527 0.046 Uiso 1 1 calc R . . H7B H -0.0416 0.3911 0.6766 0.046 Uiso 1 1 calc R . . C10 C -0.2016(5) 0.3277(14) 0.3594(11) 0.058(5) Uani 1 1 d . . . H10A H -0.2185 0.3932 0.3707 0.070 Uiso 1 1 calc R . . H10B H -0.2037 0.3256 0.2958 0.070 Uiso 1 1 calc R . . C12 C -0.2307(6) 0.0010(17) 0.3487(16) 0.122(11) Uani 1 1 d . . . H12A H -0.2603 0.0141 0.3401 0.147 Uiso 1 1 calc R . . H12B H -0.2270 -0.0542 0.3033 0.147 Uiso 1 1 calc R . . C14 C -0.1621(5) -0.1496(14) 0.5335(9) 0.056(4) Uani 1 1 d . . . H14A H -0.1784 -0.1088 0.5685 0.067 Uiso 1 1 calc R . . H14B H -0.1660 -0.2338 0.5398 0.067 Uiso 1 1 calc R . . C13 C -0.2169(6) -0.0482(16) 0.4257(16) 0.097(8) Uani 1 1 d . . . H13A H -0.2382 -0.1014 0.4363 0.117 Uiso 1 1 calc R . . H13B H -0.2129 0.0127 0.4709 0.117 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I4 0.0377(6) 0.0250(4) 0.0474(6) -0.0015(4) 0.0195(5) -0.0017(4) I5 0.0411(6) 0.0328(5) 0.0501(6) -0.0058(4) 0.0126(5) -0.0028(4) I3 0.0411(7) 0.0446(6) 0.0490(6) -0.0036(4) 0.0104(5) 0.0104(5) I1 0.0374(6) 0.0404(5) 0.0431(6) 0.0044(4) 0.0112(5) -0.0017(4) I6 0.0491(7) 0.0289(5) 0.0479(6) 0.0013(4) 0.0161(5) -0.0028(4) I7 0.0421(7) 0.0572(7) 0.0987(9) 0.0147(6) 0.0169(7) 0.0113(6) I2 0.0302(6) 0.0459(5) 0.0477(6) -0.0016(4) 0.0098(5) -0.0005(5) N5 0.078(11) 0.032(6) 0.049(8) 0.000(5) 0.038(7) -0.011(6) N2 0.051(9) 0.043(7) 0.032(7) 0.019(5) 0.021(6) 0.023(6) C8 0.043(10) 0.023(6) 0.040(9) 0.009(6) 0.011(7) -0.004(6) C2 0.045(10) 0.021(6) 0.029(8) -0.001(5) 0.009(7) -0.002(6) N1 0.047(9) 0.031(6) 0.042(7) -0.007(5) 0.008(6) 0.016(6) N3 0.029(8) 0.070(10) 0.085(10) 0.030(8) -0.007(7) -0.008(7) C6 0.024(9) 0.030(7) 0.035(8) -0.003(6) 0.007(7) 0.001(6) C16 0.050(11) 0.024(7) 0.051(9) 0.002(6) 0.021(8) 0.009(7) C1 0.027(9) 0.039(8) 0.032(8) -0.001(6) 0.012(7) 0.008(6) N4 0.027(8) 0.037(7) 0.081(10) 0.003(6) 0.003(7) -0.008(6) C4 0.040(10) 0.058(10) 0.033(9) 0.000(7) 0.009(7) 0.004(8) C3 0.026(9) 0.070(10) 0.019(8) -0.008(7) 0.007(7) 0.018(8) C5 0.056(12) 0.049(9) 0.025(8) 0.002(7) 0.020(8) -0.005(8) C15 0.049(11) 0.039(8) 0.047(10) 0.001(7) 0.013(8) 0.005(7) C11 0.045(12) 0.070(12) 0.092(14) 0.034(11) 0.003(10) 0.024(10) C9 0.071(13) 0.037(8) 0.044(9) 0.006(7) 0.004(9) 0.025(8) C7 0.043(11) 0.028(7) 0.050(9) -0.011(6) 0.026(8) -0.002(7) C10 0.031(11) 0.069(11) 0.077(12) 0.017(9) 0.018(9) 0.010(9) C12 0.026(12) 0.103(16) 0.21(3) 0.114(17) -0.032(14) -0.026(11) C14 0.058(13) 0.071(11) 0.038(9) -0.015(8) 0.013(9) -0.012(10) C13 0.061(15) 0.063(12) 0.17(2) 0.041(13) 0.021(15) -0.012(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I4 I5 2.8356(17) . ? I4 I3 3.0563(18) . ? N5 C15 1.445(17) . ? N5 C16 1.539(18) . ? N2 C9 1.467(17) . ? N2 C10 1.519(19) . ? C8 N1 1.478(15) . ? C8 C9 1.50(2) . ? C2 C3 1.376(18) . ? C2 C1 1.420(16) . ? C2 C16 1.492(16) . ? N1 C7 1.518(17) . ? N3 C12 1.502(19) . ? N3 C11 1.51(2) . ? C6 C1 1.363(17) . ? C6 C5 1.405(18) . ? C6 C7 1.525(16) . ? N4 C13 1.52(2) . ? N4 C14 1.534(18) . ? C4 C5 1.359(18) . ? C4 C3 1.419(19) . ? C15 C14 1.46(2) . ? C11 C10 1.51(2) . ? C12 C13 1.32(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I5 I4 I3 175.12(4) . . ? C15 N5 C16 114.0(11) . . ? C9 N2 C10 114.0(12) . . ? N1 C8 C9 109.3(11) . . ? C3 C2 C1 119.7(12) . . ? C3 C2 C16 118.8(12) . . ? C1 C2 C16 121.4(12) . . ? C8 N1 C7 113.1(10) . . ? C12 N3 C11 117.5(16) . . ? C1 C6 C5 120.5(11) . . ? C1 C6 C7 119.8(11) . . ? C5 C6 C7 119.6(11) . . ? C2 C16 N5 110.5(11) . . ? C6 C1 C2 119.9(12) . . ? C13 N4 C14 109.1(14) . . ? C5 C4 C3 120.5(13) . . ? C2 C3 C4 119.4(12) . . ? C4 C5 C6 120.0(13) . . ? N5 C15 C14 113.0(12) . . ? N3 C11 C10 113.0(15) . . ? N2 C9 C8 110.4(12) . . ? N1 C7 C6 111.8(10) . . ? C11 C10 N2 117.0(13) . . ? C13 C12 N3 116.4(19) . . ? C15 C14 N4 111.1(12) . . ? C12 C13 N4 116(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C8 N1 C7 178.5(10) . . . . ? C3 C2 C16 N5 -119.3(13) . . . . ? C1 C2 C16 N5 63.8(16) . . . . ? C15 N5 C16 C2 60.5(14) . . . . ? C5 C6 C1 C2 0.9(19) . . . . ? C7 C6 C1 C2 176.3(12) . . . . ? C3 C2 C1 C6 -0.1(19) . . . . ? C16 C2 C1 C6 176.7(13) . . . . ? C1 C2 C3 C4 -1.1(19) . . . . ? C16 C2 C3 C4 -178.1(12) . . . . ? C5 C4 C3 C2 2(2) . . . . ? C3 C4 C5 C6 -1(2) . . . . ? C1 C6 C5 C4 0(2) . . . . ? C7 C6 C5 C4 -175.8(13) . . . . ? C16 N5 C15 C14 171.7(11) . . . . ? C12 N3 C11 C10 -175.3(14) . . . . ? C10 N2 C9 C8 160.0(11) . . . . ? N1 C8 C9 N2 -165.7(10) . . . . ? C8 N1 C7 C6 -63.6(13) . . . . ? C1 C6 C7 N1 -69.0(15) . . . . ? C5 C6 C7 N1 106.5(14) . . . . ? N3 C11 C10 N2 -85.3(18) . . . . ? C9 N2 C10 C11 -65.9(17) . . . . ? C11 N3 C12 C13 -70(2) . . . . ? N5 C15 C14 N4 163.2(11) . . . . ? C13 N4 C14 C15 -131.2(14) . . . . ? N3 C12 C13 N4 -80(3) . . . . ? C14 N4 C13 C12 170.8(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A I6 0.92 2.67 3.557(11) 160.8 6_556 N5 H5B I2 0.92 2.90 3.740(12) 153.1 . N2 H2A I1 0.92 2.66 3.559(10) 167.1 . N2 H2B I3 0.92 2.94 3.769(11) 150.0 5_566 N2 H2B I6 0.92 3.08 3.598(10) 117.1 . N1 H1A I2 0.92 2.60 3.512(12) 170.0 . N1 H1B I6 0.92 2.57 3.480(10) 169.5 6_566 N3 H3A I7 0.92 2.49 3.370(13) 159.7 . N3 H3B I1 0.92 2.50 3.422(13) 175.8 . N4 H4A I1 0.92 2.62 3.529(12) 169.7 . N4 H4B I7 0.92 2.72 3.438(11) 135.4 4_445 N4 H4B I3 0.92 3.07 3.651(12) 122.6 5_556 _diffrn_measured_fraction_theta_max 0.800 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.800 _refine_diff_density_max 1.899 _refine_diff_density_min -2.118 _refine_diff_density_rms 0.246 data_c:\structs\chris\a6br\a6br _database_code_depnum_ccdc_archive 'CCDC 272039' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H38 Br5 N5 O2' _chemical_formula_weight 732.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4897(9) _cell_length_b 11.1914(11) _cell_length_c 14.9026(10) _cell_angle_alpha 82.7077(64) _cell_angle_beta 81.8566(54) _cell_angle_gamma 69.5010(58) _cell_volume 1308.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 7.700 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method scalepack _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9218 _diffrn_reflns_av_R_equivalents 0.1127 _diffrn_reflns_av_sigmaI/netI 0.1375 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5930 _reflns_number_gt 4573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+5.7630P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5930 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.1597 _refine_ls_wR_factor_gt 0.1473 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br3 Br 0.40206(9) 0.82187(7) 0.48762(5) 0.0190(2) Uani 1 1 d . . . Br2 Br 0.94112(9) 0.73528(8) 0.81658(5) 0.0210(2) Uani 1 1 d . . . Br1 Br 0.71720(9) 0.53129(7) 0.60733(5) 0.0187(2) Uani 1 1 d . . . Br5 Br 1.07733(9) 0.03070(7) 0.70175(5) 0.0225(2) Uani 1 1 d . . . N5 N 0.9326(7) 0.3224(6) 0.7563(4) 0.0188(13) Uani 1 1 d . . . H5A H 0.9707 0.2436 0.7332 0.023 Uiso 1 1 calc R . . H5B H 0.8467 0.3755 0.7235 0.023 Uiso 1 1 calc R . . N2 N 0.6958(7) 0.9374(6) 0.6653(4) 0.0178(13) Uani 1 1 d . . . H2A H 0.6967 1.0190 0.6479 0.021 Uiso 1 1 calc R . . H2B H 0.7598 0.9054 0.7135 0.021 Uiso 1 1 calc R . . N4 N 1.3038(7) 0.4073(6) 0.6268(4) 0.0207(13) Uani 1 1 d . . . H4A H 1.3893 0.3573 0.6608 0.025 Uiso 1 1 calc R . . H4B H 1.3448 0.3986 0.5665 0.025 Uiso 1 1 calc R . . N3 N 1.0866(7) 0.7660(6) 0.6062(4) 0.0168(13) Uani 1 1 d . . . H3A H 1.1849 0.7840 0.5887 0.020 Uiso 1 1 calc R . . H3B H 1.0580 0.7774 0.6672 0.020 Uiso 1 1 calc R . . N1 N 0.3794(7) 0.8369(6) 0.8208(4) 0.0178(13) Uani 1 1 d . . . H1A H 0.2772 0.8854 0.8001 0.021 Uiso 1 1 calc R . . H1B H 0.4033 0.8832 0.8606 0.021 Uiso 1 1 calc R . . C8 C 0.5133(9) 0.8144(7) 0.7419(5) 0.0205(15) Uani 1 1 d . . . H8A H 0.4886 0.7654 0.6981 0.025 Uiso 1 1 calc R . . H8B H 0.6245 0.7636 0.7633 0.025 Uiso 1 1 calc R . . C10 C 0.7727(9) 0.8560(8) 0.5882(5) 0.0188(15) Uani 1 1 d . . . H10A H 0.6996 0.8865 0.5380 0.023 Uiso 1 1 calc R . . H10B H 0.7798 0.7666 0.6083 0.023 Uiso 1 1 calc R . . C1 C 0.7303(9) 0.5718(8) 1.0144(5) 0.0219(16) Uani 1 1 d . . . H1 H 0.7684 0.5914 1.0658 0.026 Uiso 1 1 calc R . . C2 C 0.8250(9) 0.4601(7) 0.9722(5) 0.0165(14) Uani 1 1 d . . . H2 H 0.9256 0.4031 0.9954 0.020 Uiso 1 1 calc R . . C14 C 1.1605(9) 0.3550(8) 0.6467(5) 0.0209(16) Uani 1 1 d . . . H14A H 1.2046 0.2622 0.6384 0.025 Uiso 1 1 calc R . . H14B H 1.0765 0.3974 0.6027 0.025 Uiso 1 1 calc R . . C11 C 0.9482(9) 0.8595(7) 0.5539(5) 0.0188(15) Uani 1 1 d . . . H11A H 0.9729 0.8410 0.4891 0.023 Uiso 1 1 calc R . . H11B H 0.9491 0.9471 0.5570 0.023 Uiso 1 1 calc R . . C9 C 0.5188(9) 0.9424(7) 0.6952(5) 0.0191(15) Uani 1 1 d . . . H9A H 0.4537 0.9650 0.6417 0.023 Uiso 1 1 calc R . . H9B H 0.4649 1.0099 0.7378 0.023 Uiso 1 1 calc R . . C12 C 1.1182(9) 0.6313(8) 0.5926(5) 0.0213(16) Uani 1 1 d . . . H12A H 1.1457 0.6184 0.5270 0.026 Uiso 1 1 calc R . . H12B H 1.0151 0.6095 0.6143 0.026 Uiso 1 1 calc R . . C6 C 0.5816(10) 0.6541(8) 0.9821(5) 0.0203(16) Uani 1 1 d . . . H6 H 0.5166 0.7279 1.0128 0.024 Uiso 1 1 calc R . . C16 C 0.8630(9) 0.3081(8) 0.8541(5) 0.0209(16) Uani 1 1 d . . . H16A H 0.9575 0.2581 0.8903 0.025 Uiso 1 1 calc R . . H16B H 0.7852 0.2587 0.8585 0.025 Uiso 1 1 calc R . . C7 C 0.3635(8) 0.7159(7) 0.8713(5) 0.0150(14) Uani 1 1 d . . . H7A H 0.2763 0.7380 0.9239 0.018 Uiso 1 1 calc R . . H7B H 0.3256 0.6702 0.8306 0.018 Uiso 1 1 calc R . . C15 C 1.0730(9) 0.3751(7) 0.7435(5) 0.0202(16) Uani 1 1 d . . . H15A H 1.1549 0.3309 0.7883 0.024 Uiso 1 1 calc R . . H15B H 1.0282 0.4676 0.7528 0.024 Uiso 1 1 calc R . . C3 C 0.7698(9) 0.4332(7) 0.8953(5) 0.0174(15) Uani 1 1 d . . . C13 C 1.2645(9) 0.5436(7) 0.6445(5) 0.0188(15) Uani 1 1 d . . . H13A H 1.3658 0.5688 0.6253 0.023 Uiso 1 1 calc R . . H13B H 1.2343 0.5530 0.7105 0.023 Uiso 1 1 calc R . . C4 C 0.6209(9) 0.5164(7) 0.8635(5) 0.0182(15) Uani 1 1 d . . . H4 H 0.5819 0.4961 0.8126 0.022 Uiso 1 1 calc R . . C5 C 0.5265(8) 0.6293(7) 0.9043(5) 0.0162(14) Uani 1 1 d . . . Br4 Br 0.48066(10) 0.77272(8) 0.21428(5) 0.0247(2) Uani 1 1 d . . . O1 O 0.4039(8) 1.0187(7) 0.9292(4) 0.0370(15) Uani 1 1 d . . . O2 O 0.9219(8) 0.9130(7) 0.9883(5) 0.0451(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br3 0.0128(3) 0.0182(4) 0.0229(4) 0.0011(3) -0.0006(3) -0.0027(3) Br2 0.0174(4) 0.0263(4) 0.0187(4) 0.0008(3) -0.0036(3) -0.0068(3) Br1 0.0131(3) 0.0202(4) 0.0212(4) -0.0020(3) -0.0043(3) -0.0028(3) Br5 0.0172(4) 0.0160(4) 0.0335(4) -0.0047(3) -0.0085(3) -0.0013(3) N5 0.010(3) 0.018(3) 0.029(3) -0.003(3) -0.008(2) -0.003(3) N2 0.016(3) 0.015(3) 0.022(3) -0.002(2) 0.000(2) -0.005(3) N4 0.013(3) 0.019(4) 0.027(3) -0.002(3) -0.001(2) -0.002(3) N3 0.013(3) 0.020(3) 0.021(3) -0.007(2) -0.001(2) -0.008(3) N1 0.009(3) 0.022(4) 0.021(3) -0.004(3) -0.005(2) -0.001(3) C8 0.012(3) 0.019(4) 0.026(4) -0.001(3) -0.001(3) 0.000(3) C10 0.017(4) 0.022(4) 0.018(3) -0.002(3) -0.004(3) -0.006(3) C1 0.014(4) 0.032(5) 0.019(4) -0.003(3) -0.007(3) -0.005(3) C2 0.010(3) 0.015(4) 0.022(3) 0.007(3) -0.005(3) -0.003(3) C14 0.016(4) 0.021(4) 0.028(4) 0.000(3) -0.001(3) -0.010(3) C11 0.014(3) 0.018(4) 0.022(4) 0.002(3) -0.007(3) -0.003(3) C9 0.014(3) 0.017(4) 0.024(4) 0.002(3) 0.000(3) -0.003(3) C12 0.013(4) 0.024(4) 0.025(4) -0.002(3) -0.004(3) -0.003(3) C6 0.023(4) 0.021(4) 0.019(3) -0.004(3) 0.002(3) -0.011(3) C16 0.012(3) 0.021(4) 0.028(4) 0.001(3) -0.004(3) -0.002(3) C7 0.008(3) 0.014(4) 0.019(3) 0.003(3) -0.004(3) 0.001(3) C15 0.016(4) 0.017(4) 0.030(4) -0.003(3) -0.001(3) -0.008(3) C3 0.015(3) 0.018(4) 0.022(4) 0.000(3) -0.002(3) -0.008(3) C13 0.011(3) 0.023(4) 0.022(4) -0.004(3) -0.003(3) -0.005(3) C4 0.010(3) 0.020(4) 0.025(4) -0.002(3) -0.001(3) -0.007(3) C5 0.008(3) 0.013(4) 0.026(4) 0.005(3) -0.004(3) -0.002(3) Br4 0.0223(4) 0.0251(5) 0.0272(4) -0.0020(3) -0.0095(3) -0.0062(4) O1 0.046(4) 0.045(4) 0.028(3) -0.006(3) -0.007(3) -0.023(3) O2 0.041(4) 0.042(4) 0.050(4) -0.016(3) -0.014(3) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N5 C15 1.485(9) . ? N5 C16 1.505(9) . ? N2 C10 1.488(9) . ? N2 C9 1.489(9) . ? N4 C13 1.492(10) . ? N4 C14 1.505(9) . ? N3 C12 1.472(10) . ? N3 C11 1.508(9) . ? N1 C8 1.495(9) . ? N1 C7 1.503(9) . ? C8 C9 1.524(11) . ? C10 C11 1.518(10) . ? C1 C6 1.385(10) . ? C1 C2 1.399(10) . ? C2 C3 1.401(10) . ? C14 C15 1.531(10) . ? C12 C13 1.526(10) . ? C6 C5 1.402(10) . ? C16 C3 1.506(10) . ? C7 C5 1.493(9) . ? C3 C4 1.386(10) . ? C4 C5 1.399(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N5 C16 113.5(5) . . ? C10 N2 C9 111.9(5) . . ? C13 N4 C14 116.8(6) . . ? C12 N3 C11 113.7(5) . . ? C8 N1 C7 113.7(6) . . ? N1 C8 C9 109.6(6) . . ? N2 C10 C11 111.4(6) . . ? C6 C1 C2 120.7(6) . . ? C1 C2 C3 119.3(7) . . ? N4 C14 C15 112.4(6) . . ? N3 C11 C10 114.0(6) . . ? N2 C9 C8 111.3(6) . . ? N3 C12 C13 110.3(6) . . ? C1 C6 C5 120.5(7) . . ? N5 C16 C3 114.1(6) . . ? C5 C7 N1 112.1(5) . . ? N5 C15 C14 108.5(6) . . ? C4 C3 C2 119.5(7) . . ? C4 C3 C16 120.7(6) . . ? C2 C3 C16 119.5(7) . . ? N4 C13 C12 110.6(6) . . ? C3 C4 C5 121.8(6) . . ? C4 C5 C6 118.2(7) . . ? C4 C5 C7 121.2(6) . . ? C6 C5 C7 120.4(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C8 C9 179.7(6) . . . . ? C9 N2 C10 C11 175.8(6) . . . . ? C6 C1 C2 C3 1.3(11) . . . . ? C13 N4 C14 C15 -53.1(9) . . . . ? C12 N3 C11 C10 69.0(7) . . . . ? N2 C10 C11 N3 84.6(8) . . . . ? C10 N2 C9 C8 70.0(8) . . . . ? N1 C8 C9 N2 141.1(6) . . . . ? C11 N3 C12 C13 177.6(5) . . . . ? C2 C1 C6 C5 -2.3(11) . . . . ? C15 N5 C16 C3 68.5(8) . . . . ? C8 N1 C7 C5 56.5(7) . . . . ? C16 N5 C15 C14 166.4(6) . . . . ? N4 C14 C15 N5 179.2(6) . . . . ? C1 C2 C3 C4 -1.2(10) . . . . ? C1 C2 C3 C16 -175.0(6) . . . . ? N5 C16 C3 C4 65.1(8) . . . . ? N5 C16 C3 C2 -121.2(7) . . . . ? C14 N4 C13 C12 -55.6(8) . . . . ? N3 C12 C13 N4 -176.8(5) . . . . ? C2 C3 C4 C5 2.2(10) . . . . ? C16 C3 C4 C5 176.0(7) . . . . ? C3 C4 C5 C6 -3.2(10) . . . . ? C3 C4 C5 C7 -177.9(6) . . . . ? C1 C6 C5 C4 3.3(10) . . . . ? C1 C6 C5 C7 178.0(6) . . . . ? N1 C7 C5 C4 -107.4(7) . . . . ? N1 C7 C5 C6 78.1(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A Br5 0.92 2.32 3.226(6) 169.6 . N5 H5B Br1 0.92 2.38 3.252(7) 157.5 . N2 H2A Br3 0.92 2.54 3.249(7) 133.7 2_676 N2 H2A Br4 0.92 3.13 3.647(6) 117.5 2_676 N2 H2B Br2 0.92 2.50 3.357(7) 155.9 . N4 H4A Br4 0.92 2.36 3.233(7) 158.5 2_766 N4 H4B Br1 0.92 2.68 3.486(6) 146.7 2_766 N4 H4B Br3 0.92 2.77 3.338(6) 121.2 2_766 N3 H3A Br3 0.92 2.33 3.199(6) 156.5 1_655 N3 H3B Br2 0.92 2.37 3.225(6) 155.2 . N1 H1A Br5 0.92 2.42 3.294(6) 159.4 1_465 N1 H1B O1 0.92 1.94 2.832(8) 164.1 . _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 1.188 _refine_diff_density_min -1.484 _refine_diff_density_rms 0.217 data_L5-5HCl-2-5H2O.CIF _database_code_depnum_ccdc_archive 'CCDC 272040' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CIF _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H39 Cl5 N5 O2.5' _chemical_formula_weight 518.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5378(8) _cell_length_b 11.8423(6) _cell_length_c 20.8415(12) _cell_angle_alpha 81.0248(41) _cell_angle_beta 78.1161(36) _cell_angle_gamma 87.7689(35) _cell_volume 2513.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAPPA CCD' _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 22586 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.1627 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.51 _reflns_number_total 10628 _reflns_number_gt 6512 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+12.7757P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10628 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1771 _refine_ls_R_factor_gt 0.1078 _refine_ls_wR_factor_ref 0.2058 _refine_ls_wR_factor_gt 0.1783 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.96407(13) 0.62779(11) 0.20232(7) 0.0174(3) Uani 1 1 d . . . Cl3 Cl 1.01200(13) 0.86470(11) 0.30800(7) 0.0173(3) Uani 1 1 d . . . Cl2 Cl 0.85626(13) 0.34599(11) 0.25887(7) 0.0174(3) Uani 1 1 d . . . Cl5 Cl 1.30149(14) 0.68109(12) 0.32001(8) 0.0242(4) Uani 1 1 d . . . Cl6 Cl 0.67474(15) 0.80615(12) 0.19324(8) 0.0275(4) Uani 1 1 d . . . Cl7 Cl 1.45896(14) 1.26225(12) 0.33902(8) 0.0279(4) Uani 1 1 d . . . Cl8 Cl 1.34656(18) 1.17233(14) 0.59290(9) 0.0380(4) Uani 1 1 d . . . N1 N 1.1590(4) 0.4060(4) 0.1878(2) 0.0150(10) Uani 1 1 d . . . N2 N 1.0922(5) 0.5113(4) 0.3168(2) 0.0161(10) Uani 1 1 d . . . N7 N 1.3153(4) 0.9334(4) 0.2499(2) 0.0176(11) Uani 1 1 d . . . N10 N 0.8239(4) 1.0875(4) 0.3173(2) 0.0159(10) Uani 1 1 d . . . N9 N 0.8891(4) 0.9733(4) 0.1903(2) 0.0164(10) Uani 1 1 d . . . N8 N 1.1632(5) 0.8583(4) 0.1548(2) 0.0182(11) Uani 1 1 d . . . N5 N 0.7171(4) 0.4323(4) 0.1308(2) 0.0159(10) Uani 1 1 d . . . N6 N 1.2661(5) 1.0690(4) 0.3704(2) 0.0175(10) Uani 1 1 d . . . N3 N 0.8136(4) 0.6278(4) 0.3542(2) 0.0163(10) Uani 1 1 d . . . N4 N 0.6653(4) 0.5525(4) 0.2566(2) 0.0169(10) Uani 1 1 d . . . C30 C 0.8087(6) 1.0779(5) 0.2013(3) 0.0185(13) Uani 1 1 d . . . H30A H 0.7465 1.0879 0.1712 0.022 Uiso 1 1 calc R . . H30B H 0.8659 1.1455 0.1901 0.022 Uiso 1 1 calc R . . C3 C 1.1256(5) 0.3463(4) 0.0844(3) 0.0155(12) Uani 1 1 d . . . C21 C 0.8555(6) 1.1480(5) 0.4207(3) 0.0179(13) Uani 1 1 d . . . C11 C 0.9159(6) 0.6014(5) 0.3952(3) 0.0187(13) Uani 1 1 d . . . H11A H 0.8732 0.5910 0.4427 0.022 Uiso 1 1 calc R . . H11B H 0.9742 0.6680 0.3868 0.022 Uiso 1 1 calc R . . C9 C 1.1690(6) 0.4053(5) 0.3056(3) 0.0187(13) Uani 1 1 d . . . H9A H 1.1093 0.3395 0.3153 0.022 Uiso 1 1 calc R . . H9B H 1.2290 0.3918 0.3369 0.022 Uiso 1 1 calc R . . C8 C 1.2466(5) 0.4115(5) 0.2353(3) 0.0164(12) Uani 1 1 d . . . H8B H 1.2960 0.4837 0.2227 0.020 Uiso 1 1 calc R . . H8A H 1.3094 0.3471 0.2329 0.020 Uiso 1 1 calc R . . C12 C 0.7079(6) 0.5401(5) 0.3708(3) 0.0195(13) Uani 1 1 d . . . H12A H 0.6643 0.5380 0.4179 0.023 Uiso 1 1 calc R . . H12B H 0.7473 0.4640 0.3658 0.023 Uiso 1 1 calc R . . C25 C 1.4128(5) 0.9675(5) 0.2865(3) 0.0190(13) Uani 1 1 d . . . H25A H 1.4459 1.0447 0.2662 0.023 Uiso 1 1 calc R . . H25B H 1.4870 0.9133 0.2826 0.023 Uiso 1 1 calc R . . C26 C 1.3717(6) 0.9189(5) 0.1801(3) 0.0209(13) Uani 1 1 d . . . H26A H 1.4064 0.8402 0.1790 0.025 Uiso 1 1 calc R . . H26B H 1.4447 0.9725 0.1624 0.025 Uiso 1 1 calc R . . C14 C 0.5682(5) 0.5217(5) 0.2191(3) 0.0169(12) Uani 1 1 d . . . H14A H 0.4928 0.5743 0.2253 0.020 Uiso 1 1 calc R . . H14B H 0.5370 0.4431 0.2371 0.020 Uiso 1 1 calc R . . C2 C 1.1502(6) 0.2619(5) 0.0434(3) 0.0202(13) Uani 1 1 d . . . H2 H 1.2292 0.2198 0.0403 0.024 Uiso 1 1 calc R . . C1 C 1.0600(6) 0.2394(5) 0.0074(3) 0.0253(14) Uani 1 1 d . . . H1 H 1.0785 0.1827 -0.0208 0.030 Uiso 1 1 calc R . . C23 C 1.1981(6) 1.0630(5) 0.4414(3) 0.0205(13) Uani 1 1 d . . . H23A H 1.2537 1.0977 0.4659 0.025 Uiso 1 1 calc R . . H23B H 1.1850 0.9818 0.4616 0.025 Uiso 1 1 calc R . . C13 C 0.6069(6) 0.5634(5) 0.3277(3) 0.0203(13) Uani 1 1 d . . . H13A H 0.5349 0.5084 0.3446 0.024 Uiso 1 1 calc R . . H13B H 0.5709 0.6414 0.3301 0.024 Uiso 1 1 calc R . . C22 C 0.8251(6) 1.2284(5) 0.4637(3) 0.0220(14) Uani 1 1 d . . . H22A H 0.7434 1.2664 0.4677 0.026 Uiso 1 1 calc R . . C20 C 0.9778(6) 1.0949(5) 0.4147(3) 0.0159(12) Uani 1 1 d . . . H20 H 0.9988 1.0381 0.3866 0.019 Uiso 1 1 calc R . . C15 C 0.6257(6) 0.5287(5) 0.1459(3) 0.0196(13) Uani 1 1 d . . . H15A H 0.5547 0.5283 0.1214 0.024 Uiso 1 1 calc R . . H15B H 0.6725 0.6020 0.1301 0.024 Uiso 1 1 calc R . . C29 C 0.9830(5) 0.9914(5) 0.1253(3) 0.0171(12) Uani 1 1 d . . . H29A H 1.0415 1.0551 0.1248 0.021 Uiso 1 1 calc R . . H29B H 0.9346 1.0136 0.0892 0.021 Uiso 1 1 calc R . . C4 C 1.0096(6) 0.4069(5) 0.0877(3) 0.0172(12) Uani 1 1 d . . . H4 H 0.9930 0.4664 0.1141 0.021 Uiso 1 1 calc R . . C7 C 1.2238(6) 0.3696(5) 0.1237(3) 0.0193(13) Uani 1 1 d . . . H7A H 1.2760 0.2997 0.1325 0.023 Uiso 1 1 calc R . . H7B H 1.2833 0.4305 0.0976 0.023 Uiso 1 1 calc R . . C17 C 0.9125(7) 1.2535(5) 0.5006(3) 0.0267(15) Uani 1 1 d . . . H17 H 0.8886 1.3052 0.5317 0.032 Uiso 1 1 calc R . . C10 C 0.9973(6) 0.4957(4) 0.3815(3) 0.0169(12) Uani 1 1 d . . . H10B H 1.0453 0.4735 0.4178 0.020 Uiso 1 1 calc R . . H33B H 0.9386 0.4321 0.3822 0.020 Uiso 1 1 calc R . . C32 C 0.7572(6) 1.1173(5) 0.3835(3) 0.0212(13) Uani 1 1 d . . . H32A H 0.6973 1.1826 0.3770 0.025 Uiso 1 1 calc R . . H32B H 0.7056 1.0513 0.4096 0.025 Uiso 1 1 calc R . . C24 C 1.3537(6) 0.9679(5) 0.3587(3) 0.0198(13) Uani 1 1 d . . . H24A H 1.3035 0.8968 0.3761 0.024 Uiso 1 1 calc R . . H24B H 1.4241 0.9681 0.3836 0.024 Uiso 1 1 calc R . . C27 C 1.2722(6) 0.9406(5) 0.1362(3) 0.0210(13) Uani 1 1 d . . . H27A H 1.2365 1.0189 0.1382 0.025 Uiso 1 1 calc R . . H27B H 1.3162 0.9371 0.0897 0.025 Uiso 1 1 calc R . . C28 C 1.0631(5) 0.8861(5) 0.1124(3) 0.0167(12) Uani 1 1 d . . . H28A H 1.0042 0.8201 0.1199 0.020 Uiso 1 1 calc R . . H28B H 1.1077 0.8966 0.0652 0.020 Uiso 1 1 calc R . . C31 C 0.7345(6) 1.0720(5) 0.2722(3) 0.0206(13) Uani 1 1 d . . . H31A H 0.6669 1.1325 0.2745 0.025 Uiso 1 1 calc R . . H31B H 0.6911 0.9971 0.2867 0.025 Uiso 1 1 calc R . . C16 C 0.7917(6) 0.4496(5) 0.0597(3) 0.0235(14) Uani 1 1 d . . . H16A H 0.7378 0.4252 0.0307 0.028 Uiso 1 1 calc R . . H16B H 0.8109 0.5319 0.0450 0.028 Uiso 1 1 calc R . . C18 C 1.0364(6) 1.2030(5) 0.4924(3) 0.0254(14) Uani 1 1 d . . . H18 H 1.0976 1.2229 0.5163 0.030 Uiso 1 1 calc R . . C19 C 1.0690(6) 1.1235(5) 0.4488(3) 0.0182(13) Uani 1 1 d . . . C5 C 0.9171(6) 0.3822(5) 0.0529(3) 0.0197(13) Uani 1 1 d . . . C6 C 0.9432(6) 0.2982(5) 0.0121(3) 0.0246(14) Uani 1 1 d . . . H6 H 0.8815 0.2815 -0.0124 0.030 Uiso 1 1 calc R . . Cl4 Cl 0.12796(13) 0.14219(11) 0.24320(7) 0.0169(3) Uani 1 1 d . . . Cl9 Cl 0.30986(17) 0.64874(14) 0.11061(8) 0.0350(4) Uani 1 1 d . . . Cl10 Cl 0.54579(16) 0.22511(13) 0.14251(9) 0.0366(4) Uani 1 1 d . . . O5 O 1.2585(5) 0.4935(5) 0.4553(2) 0.0459(14) Uani 1 1 d . . . O2 O 1.2558(5) 0.9318(5) -0.0359(2) 0.0526(15) Uani 1 1 d . . . O1 O 1.4804(5) 1.3533(4) 0.4672(3) 0.0505(14) Uani 1 1 d . . . O4 O 0.5410(6) 0.6957(6) -0.0042(3) 0.0624(17) Uani 1 1 d . . . O3 O 0.5966(6) 0.8786(5) 0.0543(3) 0.0727(19) Uani 1 1 d . . . H201 H 1.2641 1.0153 -0.0411 0.087 Uiso 1 1 d R . . H501 H 1.2385 0.4104 0.4619 0.087 Uiso 1 1 d R . . H92 H 0.8402 0.9177 0.1920 0.087 Uiso 1 1 d R . . H71 H 1.2625 0.9869 0.2490 0.087 Uiso 1 1 d R . . H82 H 1.1910 0.7968 0.1482 0.087 Uiso 1 1 d R . . H21 H 1.0523 0.5368 0.2861 0.087 Uiso 1 1 d R . . H102 H 0.8731 1.0331 0.3204 0.087 Uiso 1 1 d R . . H11 H 1.1231 0.4691 0.1794 0.087 Uiso 1 1 d R . . H101 H 0.8899 1.1276 0.2976 0.087 Uiso 1 1 d R . . H61 H 1.3328 1.1350 0.3581 0.087 Uiso 1 1 d R . . H42 H 0.6961 0.6223 0.2389 0.087 Uiso 1 1 d R . . H81 H 1.1162 0.8567 0.1930 0.087 Uiso 1 1 d R . . H52 H 0.6763 0.3650 0.1370 0.087 Uiso 1 1 d R . . H41 H 0.7377 0.4867 0.2596 0.087 Uiso 1 1 d R . . H51 H 0.7675 0.4214 0.1577 0.087 Uiso 1 1 d R . . H91 H 0.9325 0.9409 0.2232 0.087 Uiso 1 1 d R . . H22 H 1.1632 0.5775 0.3102 0.087 Uiso 1 1 d R . . H62 H 1.2106 1.0855 0.3444 0.087 Uiso 1 1 d R . . H32 H 0.7775 0.6937 0.3556 0.087 Uiso 1 1 d R . . H31 H 0.8394 0.6379 0.3082 0.087 Uiso 1 1 d R . . H72 H 1.2995 0.8701 0.2805 0.087 Uiso 1 1 d R . . H12 H 1.0974 0.3581 0.2112 0.087 Uiso 1 1 d R . . H502 H 1.3583 0.4866 0.4465 0.087 Uiso 1 1 d R . . H301 H 0.5855 0.8061 0.0391 0.087 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0179(7) 0.0130(6) 0.0216(7) 0.0006(6) -0.0076(6) 0.0015(5) Cl3 0.0196(7) 0.0118(6) 0.0215(7) -0.0012(5) -0.0077(6) 0.0024(5) Cl2 0.0163(7) 0.0116(6) 0.0235(7) -0.0003(6) -0.0042(6) 0.0025(5) Cl5 0.0202(8) 0.0153(7) 0.0392(9) -0.0031(6) -0.0120(7) 0.0011(6) Cl6 0.0201(8) 0.0149(7) 0.0512(10) -0.0053(7) -0.0158(7) 0.0029(6) Cl7 0.0189(8) 0.0209(7) 0.0425(9) 0.0033(7) -0.0089(7) 0.0003(6) Cl8 0.0466(11) 0.0246(8) 0.0446(10) -0.0123(8) -0.0111(9) 0.0153(7) N1 0.018(3) 0.015(2) 0.015(2) -0.0046(19) -0.007(2) -0.0014(19) N2 0.021(3) 0.013(2) 0.016(2) -0.0003(19) -0.007(2) 0.0027(19) N7 0.015(3) 0.017(2) 0.022(3) -0.003(2) -0.009(2) 0.0030(19) N10 0.016(3) 0.017(2) 0.018(2) -0.006(2) -0.008(2) 0.0029(19) N9 0.015(3) 0.014(2) 0.021(2) -0.004(2) -0.007(2) 0.0030(19) N8 0.019(3) 0.014(2) 0.023(3) -0.004(2) -0.006(2) 0.0056(19) N5 0.018(3) 0.017(2) 0.014(2) -0.0020(19) -0.007(2) 0.0018(19) N6 0.019(3) 0.015(2) 0.019(2) -0.003(2) -0.005(2) 0.0037(19) N3 0.017(3) 0.009(2) 0.024(3) -0.002(2) -0.009(2) 0.0037(19) N4 0.013(2) 0.016(2) 0.023(3) -0.005(2) -0.006(2) 0.0041(19) C30 0.020(3) 0.018(3) 0.021(3) -0.008(2) -0.010(3) 0.010(2) C3 0.018(3) 0.015(3) 0.015(3) -0.003(2) -0.003(2) -0.002(2) C21 0.019(3) 0.019(3) 0.015(3) 0.002(2) -0.005(2) 0.000(2) C11 0.025(3) 0.016(3) 0.017(3) -0.006(2) -0.006(3) 0.004(2) C9 0.024(3) 0.017(3) 0.020(3) -0.007(2) -0.014(3) 0.007(2) C8 0.010(3) 0.020(3) 0.023(3) -0.004(2) -0.010(2) 0.003(2) C12 0.020(3) 0.017(3) 0.022(3) -0.004(2) -0.004(3) 0.001(2) C25 0.014(3) 0.022(3) 0.024(3) -0.005(3) -0.009(3) 0.002(2) C26 0.017(3) 0.028(3) 0.020(3) -0.008(3) -0.005(3) 0.005(3) C14 0.010(3) 0.018(3) 0.026(3) -0.008(2) -0.008(2) 0.000(2) C2 0.025(3) 0.017(3) 0.019(3) -0.003(2) -0.005(3) 0.006(2) C1 0.037(4) 0.023(3) 0.021(3) -0.010(3) -0.014(3) 0.003(3) C23 0.025(3) 0.024(3) 0.013(3) -0.003(2) -0.005(3) 0.003(3) C13 0.018(3) 0.026(3) 0.018(3) -0.005(3) -0.004(3) 0.006(2) C22 0.025(3) 0.015(3) 0.027(3) -0.003(3) -0.006(3) 0.004(2) C20 0.022(3) 0.014(3) 0.013(3) -0.006(2) -0.004(2) -0.003(2) C15 0.021(3) 0.018(3) 0.021(3) -0.002(2) -0.011(3) 0.002(2) C29 0.016(3) 0.020(3) 0.018(3) -0.004(2) -0.008(2) 0.002(2) C4 0.024(3) 0.018(3) 0.012(3) -0.006(2) -0.004(2) -0.004(2) C7 0.017(3) 0.027(3) 0.014(3) -0.008(2) 0.001(2) -0.003(2) C17 0.047(4) 0.018(3) 0.019(3) -0.011(3) -0.012(3) 0.006(3) C10 0.022(3) 0.015(3) 0.017(3) -0.004(2) -0.010(3) -0.003(2) C32 0.020(3) 0.023(3) 0.020(3) -0.007(3) -0.001(3) 0.003(2) C24 0.023(3) 0.014(3) 0.028(3) -0.004(2) -0.016(3) 0.005(2) C27 0.017(3) 0.027(3) 0.018(3) -0.006(3) -0.001(3) 0.005(2) C28 0.017(3) 0.016(3) 0.020(3) -0.005(2) -0.012(2) 0.002(2) C31 0.020(3) 0.018(3) 0.028(3) -0.011(3) -0.009(3) 0.005(2) C16 0.028(4) 0.025(3) 0.019(3) -0.001(3) -0.012(3) 0.005(3) C18 0.031(4) 0.023(3) 0.026(3) -0.009(3) -0.012(3) 0.003(3) C19 0.018(3) 0.017(3) 0.017(3) 0.002(2) -0.002(2) 0.001(2) C5 0.028(3) 0.021(3) 0.011(3) -0.001(2) -0.007(3) -0.003(3) C6 0.036(4) 0.024(3) 0.017(3) -0.004(3) -0.012(3) -0.002(3) Cl4 0.0161(7) 0.0123(6) 0.0219(7) -0.0004(5) -0.0053(6) 0.0027(5) Cl9 0.0373(10) 0.0289(9) 0.0385(9) -0.0097(7) -0.0062(8) 0.0153(7) Cl10 0.0290(9) 0.0220(8) 0.0601(12) 0.0036(8) -0.0190(8) -0.0021(7) O5 0.030(3) 0.066(4) 0.036(3) 0.002(3) -0.002(2) 0.005(3) O2 0.031(3) 0.094(4) 0.029(3) -0.003(3) -0.002(2) 0.000(3) O1 0.055(4) 0.044(3) 0.051(3) 0.001(3) -0.013(3) 0.000(3) O4 0.048(4) 0.088(5) 0.053(3) -0.016(3) -0.008(3) -0.007(3) O3 0.078(5) 0.076(4) 0.064(4) -0.019(3) -0.003(4) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.489(7) . ? N1 C8 1.496(7) . ? N2 C9 1.490(7) . ? N2 C10 1.495(7) . ? N7 C26 1.488(7) . ? N7 C25 1.501(7) . ? N10 C31 1.496(7) . ? N10 C32 1.502(7) . ? N9 C30 1.494(7) . ? N9 C29 1.496(7) . ? N8 C27 1.485(7) . ? N8 C28 1.506(7) . ? N5 C15 1.494(7) . ? N5 C16 1.514(7) . ? N6 C23 1.499(7) . ? N6 C24 1.503(7) . ? N3 C12 1.502(7) . ? N3 C11 1.503(7) . ? N4 C14 1.496(7) . ? N4 C13 1.507(7) . ? C30 C31 1.514(8) . ? C3 C4 1.388(8) . ? C3 C2 1.396(8) . ? C3 C7 1.504(8) . ? C21 C22 1.391(8) . ? C21 C20 1.403(8) . ? C21 C32 1.501(8) . ? C11 C10 1.520(8) . ? C9 C8 1.517(8) . ? C12 C13 1.520(8) . ? C25 C24 1.506(8) . ? C26 C27 1.518(8) . ? C14 C15 1.512(8) . ? C2 C1 1.383(9) . ? C1 C6 1.383(9) . ? C23 C19 1.504(8) . ? C22 C17 1.384(9) . ? C20 C19 1.388(8) . ? C29 C28 1.506(8) . ? C4 C5 1.393(8) . ? C17 C18 1.404(9) . ? C16 C5 1.510(8) . ? C18 C19 1.393(8) . ? C5 C6 1.391(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C8 114.6(4) . . ? C9 N2 C10 112.0(4) . . ? C26 N7 C25 113.5(4) . . ? C31 N10 C32 114.5(4) . . ? C30 N9 C29 111.4(4) . . ? C27 N8 C28 112.4(4) . . ? C15 N5 C16 112.6(4) . . ? C23 N6 C24 112.5(4) . . ? C12 N3 C11 113.0(4) . . ? C14 N4 C13 113.1(4) . . ? N9 C30 C31 112.6(4) . . ? C4 C3 C2 118.5(5) . . ? C4 C3 C7 121.5(5) . . ? C2 C3 C7 119.9(5) . . ? C22 C21 C20 118.4(5) . . ? C22 C21 C32 120.1(5) . . ? C20 C21 C32 121.4(5) . . ? N3 C11 C10 114.4(5) . . ? N2 C9 C8 112.8(4) . . ? N1 C8 C9 110.7(4) . . ? N3 C12 C13 113.5(5) . . ? N7 C25 C24 111.1(5) . . ? N7 C26 C27 112.0(5) . . ? N4 C14 C15 111.5(5) . . ? C1 C2 C3 120.3(6) . . ? C2 C1 C6 120.9(6) . . ? N6 C23 C19 112.5(4) . . ? N4 C13 C12 111.0(5) . . ? C17 C22 C21 120.7(6) . . ? C19 C20 C21 121.5(5) . . ? N5 C15 C14 112.7(4) . . ? N9 C29 C28 112.3(4) . . ? C3 C4 C5 121.2(5) . . ? N1 C7 C3 110.9(5) . . ? C22 C17 C18 120.4(6) . . ? N2 C10 C11 114.1(4) . . ? C21 C32 N10 110.2(5) . . ? N6 C24 C25 112.9(4) . . ? N8 C27 C26 113.9(5) . . ? N8 C28 C29 114.5(5) . . ? N10 C31 C30 110.6(5) . . ? C5 C16 N5 111.1(4) . . ? C19 C18 C17 119.6(6) . . ? C20 C19 C18 119.4(6) . . ? C20 C19 C23 119.4(5) . . ? C18 C19 C23 121.1(5) . . ? C6 C5 C4 119.5(6) . . ? C6 C5 C16 121.8(5) . . ? C4 C5 C16 118.7(5) . . ? C1 C6 C5 119.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C29 N9 C30 C31 -167.3(5) . . . . ? C12 N3 C11 C10 67.3(6) . . . . ? C10 N2 C9 C8 168.9(4) . . . . ? C7 N1 C8 C9 -159.0(4) . . . . ? N2 C9 C8 N1 -71.1(6) . . . . ? C11 N3 C12 C13 -177.6(5) . . . . ? C26 N7 C25 C24 -173.6(4) . . . . ? C25 N7 C26 C27 -152.8(5) . . . . ? C13 N4 C14 C15 171.5(4) . . . . ? C4 C3 C2 C1 -0.4(8) . . . . ? C7 C3 C2 C1 179.6(5) . . . . ? C3 C2 C1 C6 -1.1(9) . . . . ? C24 N6 C23 C19 -151.2(5) . . . . ? C14 N4 C13 C12 154.0(5) . . . . ? N3 C12 C13 N4 65.9(6) . . . . ? C20 C21 C22 C17 -1.3(8) . . . . ? C32 C21 C22 C17 176.9(5) . . . . ? C22 C21 C20 C19 -2.0(8) . . . . ? C32 C21 C20 C19 179.8(5) . . . . ? C16 N5 C15 C14 -170.3(5) . . . . ? N4 C14 C15 N5 73.6(6) . . . . ? C30 N9 C29 C28 -178.7(4) . . . . ? C2 C3 C4 C5 2.2(8) . . . . ? C7 C3 C4 C5 -177.7(5) . . . . ? C8 N1 C7 C3 169.9(4) . . . . ? C4 C3 C7 N1 32.4(7) . . . . ? C2 C3 C7 N1 -147.6(5) . . . . ? C21 C22 C17 C18 3.7(9) . . . . ? C9 N2 C10 C11 -179.7(5) . . . . ? N3 C11 C10 N2 72.9(6) . . . . ? C22 C21 C32 N10 148.0(5) . . . . ? C20 C21 C32 N10 -33.8(7) . . . . ? C31 N10 C32 C21 -171.5(4) . . . . ? C23 N6 C24 C25 174.6(5) . . . . ? N7 C25 C24 N6 -75.1(6) . . . . ? C28 N8 C27 C26 177.1(5) . . . . ? N7 C26 C27 N8 -63.8(6) . . . . ? C27 N8 C28 C29 -70.9(6) . . . . ? N9 C29 C28 N8 -71.6(6) . . . . ? C32 N10 C31 C30 163.0(4) . . . . ? N9 C30 C31 N10 73.5(6) . . . . ? C15 N5 C16 C5 156.3(5) . . . . ? C22 C17 C18 C19 -2.8(9) . . . . ? C21 C20 C19 C18 2.9(8) . . . . ? C21 C20 C19 C23 179.2(5) . . . . ? C17 C18 C19 C20 -0.5(8) . . . . ? C17 C18 C19 C23 -176.7(5) . . . . ? N6 C23 C19 C20 54.2(7) . . . . ? N6 C23 C19 C18 -129.6(6) . . . . ? C3 C4 C5 C6 -2.6(8) . . . . ? C3 C4 C5 C16 178.8(5) . . . . ? N5 C16 C5 C6 119.7(6) . . . . ? N5 C16 C5 C4 -61.7(7) . . . . ? C2 C1 C6 C5 0.8(9) . . . . ? C4 C5 C6 C1 1.0(8) . . . . ? C16 C5 C6 C1 179.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H92 Cl6 0.84 2.22 3.046(5) 165.5 . N7 H71 Cl4 0.83 2.28 3.108(5) 176.3 1_665 N8 H82 Cl9 0.80 2.26 3.037(5) 165.2 1_655 N2 H21 Cl1 0.85 2.25 3.095(5) 171.5 . N10 H102 Cl3 0.81 2.44 3.244(5) 168.3 . N1 H11 Cl1 0.83 2.51 3.283(5) 155.7 . N1 H11 Cl9 0.83 2.94 3.352(5) 112.4 1_655 N10 H101 Cl4 0.85 2.53 3.299(5) 150.4 1_665 N10 H101 Cl2 0.85 2.62 3.118(5) 118.5 1_565 N6 H61 Cl7 1.04 1.99 3.024(5) 177.3 . N4 H42 Cl6 0.90 2.26 3.084(5) 153.1 . N4 H42 Cl1 0.90 2.77 3.229(5) 113.2 . N8 H81 Cl3 0.85 2.44 3.273(5) 170.5 . N5 H52 Cl10 0.90 2.17 3.052(5) 167.4 . N4 H41 Cl2 1.07 2.04 3.107(5) 170.5 . N5 H51 Cl2 0.84 2.51 3.311(5) 160.7 . N9 H91 Cl3 0.93 2.17 3.089(5) 173.2 . N2 H22 Cl5 1.08 2.00 3.059(5) 165.8 . N6 H62 Cl4 0.87 2.43 3.266(5) 159.6 1_665 N3 H32 Cl8 0.86 2.27 3.067(5) 153.9 2_776 N3 H31 Cl1 0.93 2.34 3.235(5) 160.7 . N7 H72 Cl5 0.90 2.26 3.109(5) 156.5 . N1 H12 Cl2 0.89 2.53 3.283(5) 142.4 . N1 H12 Cl4 0.89 2.56 3.162(5) 125.1 1_655 O5 H502 O1 1.03 2.05 2.845(7) 132.1 1_545 O3 H301 O4 0.98 1.83 2.782(9) 164.4 . _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 1.374 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.110 data_L5-5HCl-H2O.CIF _database_code_depnum_ccdc_archive 'CCDC 272041' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5,8,11,14-pentazaz[15]metacyclophane pentahydrochloride monohydrate ; _chemical_name_common ;2,5,8,11,14-pentazaz(15)metacyclophane pentahydrochloride monohydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H38 Cl5 N5 O' _chemical_formula_weight 493.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.862(2) _cell_length_b 10.525(2) _cell_length_c 12.113(2) _cell_angle_alpha 97.654(2) _cell_angle_beta 100.990(2) _cell_angle_gamma 103.968(3) _cell_volume 1176.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3085 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2352 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement 'DENZO SMN' _computing_data_reduction 'DENZO SMN' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+1.4390P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2352 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl5 Cl 0.36041(12) 0.75839(10) 0.43780(10) 0.0256(4) Uani 1 1 d . . . Cl1 Cl 0.09175(11) 0.06359(10) 0.40003(10) 0.0235(4) Uani 1 1 d . . . Cl2 Cl 0.07093(12) -0.10987(11) -0.09808(10) 0.0263(4) Uani 1 1 d . . . N2 N -0.1737(4) -0.1607(3) 0.2573(3) 0.0191(9) Uani 1 1 d . . . H2A H -0.1756 -0.2203 0.3064 0.023 Uiso 1 1 calc R . . H2B H -0.0996 -0.0858 0.2915 0.023 Uiso 1 1 calc R . . N1 N 0.1085(3) -0.0922(3) 0.1625(3) 0.0176(9) Uani 1 1 d . . . H1A H 0.0855 -0.0736 0.0903 0.021 Uiso 1 1 calc R . . H1B H 0.0925 -0.0272 0.2131 0.021 Uiso 1 1 calc R . . N5 N 0.3536(4) 0.4827(4) 0.3021(4) 0.0374(12) Uani 1 1 d . A 1 H5A H 0.3568 0.5478 0.3620 0.045 Uiso 1 1 calc R A 1 H5B H 0.3958 0.5262 0.2510 0.045 Uiso 1 1 calc R A 1 N3 N -0.2284(4) 0.0814(3) 0.4011(3) 0.0193(10) Uani 1 1 d . . . H3A H -0.2492 0.1151 0.4680 0.023 Uiso 1 1 calc R . . H3B H -0.1376 0.0703 0.4195 0.023 Uiso 1 1 calc R . . C10 C -0.3118(5) -0.1227(4) 0.2412(4) 0.0227(12) Uani 1 1 d . . . H10A H -0.3927 -0.2040 0.2100 0.027 Uiso 1 1 calc R . . H10B H -0.3132 -0.0631 0.1845 0.027 Uiso 1 1 calc R . . C2 C 0.4447(4) 0.2875(4) 0.2611(4) 0.0187(12) Uani 1 1 d . A . C1 C 0.3718(4) 0.1608(4) 0.2705(4) 0.0214(12) Uani 1 1 d . . . H1 H 0.3339 0.1485 0.3360 0.026 Uiso 1 1 calc R . . C5 C 0.4123(5) 0.0696(4) 0.0916(4) 0.0208(12) Uani 1 1 d . . . H5 H 0.3986 -0.0040 0.0320 0.025 Uiso 1 1 calc R . . C6 C 0.3530(4) 0.0503(4) 0.1846(4) 0.0182(12) Uani 1 1 d . . . C4 C 0.4917(5) 0.1952(4) 0.0840(4) 0.0218(12) Uani 1 1 d . . . H4 H 0.5356 0.2070 0.0214 0.026 Uiso 1 1 calc R . . C11 C -0.3331(5) -0.0529(4) 0.3518(4) 0.0213(12) Uani 1 1 d . . . H11A H -0.4315 -0.0420 0.3378 0.026 Uiso 1 1 calc R . . H11B H -0.3259 -0.1109 0.4093 0.026 Uiso 1 1 calc R . . C12 C -0.2274(4) 0.1812(4) 0.3247(4) 0.0217(12) Uani 1 1 d . . . H12A H -0.3176 0.2084 0.3173 0.026 Uiso 1 1 calc R . . H12B H -0.2227 0.1404 0.2475 0.026 Uiso 1 1 calc R . . C3 C 0.5062(5) 0.3036(4) 0.1693(4) 0.0221(12) Uani 1 1 d . . . H3 H 0.5593 0.3899 0.1639 0.026 Uiso 1 1 calc R . . C16 C 0.4526(5) 0.4065(4) 0.3491(4) 0.0236(12) Uani 1 1 d . . . H16A H 0.4263 0.3761 0.4180 0.028 Uiso 1 1 calc R A 1 H16B H 0.5521 0.4652 0.3721 0.028 Uiso 1 1 calc R A 1 C13 C -0.1003(5) 0.3029(4) 0.3717(4) 0.0248(13) Uani 1 1 d . . . H13A H -0.1306 0.3726 0.4163 0.030 Uiso 1 1 calc R B 1 H13B H -0.0243 0.2789 0.4240 0.030 Uiso 1 1 calc R B 1 C8 C 0.0114(5) -0.2236(4) 0.1660(4) 0.0239(12) Uani 1 1 d . . . H8A H 0.0421 -0.2486 0.2409 0.029 Uiso 1 1 calc R . . H8B H 0.0201 -0.2923 0.1056 0.029 Uiso 1 1 calc R . . C7 C 0.2638(4) -0.0862(4) 0.1914(4) 0.0229(12) Uani 1 1 d . . . H7A H 0.2829 -0.1553 0.1373 0.027 Uiso 1 1 calc R . . H7B H 0.2907 -0.1040 0.2697 0.027 Uiso 1 1 calc R . . C9 C -0.1435(5) -0.2214(4) 0.1488(4) 0.0226(12) Uani 1 1 d . . . H9A H -0.1655 -0.1695 0.0886 0.027 Uiso 1 1 calc R . . H9B H -0.2065 -0.3136 0.1226 0.027 Uiso 1 1 calc R . . N4 N -0.0433(5) 0.3550(4) 0.2805(4) 0.0758(19) Uani 1 1 d . A 1 H4A H -0.0859 0.4184 0.2565 0.091 Uiso 1 1 calc R A 1 H4B H -0.0568 0.2880 0.2190 0.091 Uiso 1 1 calc R A 1 C14 C 0.1340(10) 0.4231(10) 0.3417(9) 0.024(2) Uiso 0.50 1 d P A 1 H14A H 0.1493 0.5132 0.3867 0.029 Uiso 0.50 1 calc PR A 1 H14B H 0.1687 0.3672 0.3941 0.029 Uiso 0.50 1 calc PR A 1 C15 C 0.2144(9) 0.4317(9) 0.2497(9) 0.020(2) Uiso 0.50 1 d P A 1 H15A H 0.1981 0.3422 0.2034 0.024 Uiso 0.50 1 calc PR A 1 H15B H 0.1827 0.4901 0.1985 0.024 Uiso 0.50 1 calc PR A 1 Cl3 Cl 0.19590(14) 0.40068(11) 0.63042(12) 0.0382(4) Uani 1 1 d . . . Cl4 Cl 0.3762(3) 0.5708(4) 1.0782(3) 0.0317(9) Uani 0.50 1 d P C 1 Cl4A Cl 0.1551(3) 0.5574(2) 0.9730(3) 0.0265(7) Uani 0.50 1 d P D 2 O1 O 0.0914(8) 0.5463(7) 0.8975(8) 0.043(2) Uani 0.50 1 d P E 1 O1A O 0.4591(9) 0.5748(8) 1.1021(7) 0.028(2) Uani 0.50 1 d P F 2 C15A C 0.1901(10) 0.3830(9) 0.3092(9) 0.019(2) Uiso 0.50 1 d P G 2 C14A C 0.0794(10) 0.4652(8) 0.2927(9) 0.021(2) Uiso 0.50 1 d P G 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl5 0.0322(8) 0.0175(6) 0.0285(8) 0.0011(6) 0.0103(6) 0.0086(6) Cl1 0.0222(7) 0.0253(7) 0.0210(8) -0.0009(6) 0.0067(5) 0.0041(5) Cl2 0.0350(8) 0.0254(7) 0.0215(8) 0.0020(6) 0.0069(6) 0.0149(6) N2 0.022(2) 0.0128(19) 0.025(3) 0.0057(18) 0.0066(18) 0.0057(17) N1 0.023(2) 0.0136(19) 0.020(2) 0.0038(18) 0.0086(18) 0.0081(18) N5 0.056(3) 0.021(2) 0.030(3) -0.007(2) -0.005(2) 0.019(2) N3 0.021(2) 0.018(2) 0.019(2) -0.0011(19) 0.0057(18) 0.0072(18) C10 0.024(3) 0.015(2) 0.027(3) 0.004(2) 0.005(2) 0.003(2) C2 0.016(3) 0.022(3) 0.017(3) -0.002(2) 0.003(2) 0.007(2) C1 0.017(3) 0.031(3) 0.018(3) 0.005(3) 0.006(2) 0.010(2) C5 0.023(3) 0.022(3) 0.018(3) 0.001(2) 0.005(2) 0.009(2) C6 0.015(3) 0.019(3) 0.024(3) 0.007(2) 0.006(2) 0.009(2) C4 0.021(3) 0.027(3) 0.021(3) 0.004(3) 0.009(2) 0.009(2) C11 0.018(3) 0.020(3) 0.024(3) 0.003(2) 0.006(2) 0.003(2) C12 0.022(3) 0.027(3) 0.019(3) 0.010(2) 0.004(2) 0.008(2) C3 0.024(3) 0.021(3) 0.024(3) 0.006(2) 0.007(2) 0.009(2) C16 0.015(3) 0.028(3) 0.024(3) -0.003(2) 0.000(2) 0.006(2) C13 0.022(3) 0.021(3) 0.032(3) 0.006(3) 0.005(2) 0.005(2) C8 0.030(3) 0.012(2) 0.031(3) 0.004(2) 0.011(2) 0.005(2) C7 0.019(3) 0.026(3) 0.029(3) 0.004(2) 0.009(2) 0.013(2) C9 0.030(3) 0.014(2) 0.021(3) -0.002(2) 0.007(2) 0.004(2) N4 0.107(4) 0.044(3) 0.047(4) -0.026(3) 0.055(3) -0.046(3) Cl3 0.0517(9) 0.0220(7) 0.0360(9) 0.0067(6) 0.0077(7) 0.0023(6) Cl4 0.037(2) 0.0318(16) 0.029(2) 0.0137(15) 0.0057(18) 0.011(2) Cl4A 0.0275(17) 0.0254(14) 0.0283(18) 0.0039(14) 0.0051(13) 0.0119(13) O1 0.037(5) 0.032(4) 0.052(6) 0.013(4) -0.016(4) 0.010(4) O1A 0.038(6) 0.018(4) 0.021(5) 0.002(3) -0.001(5) 0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C10 1.495(5) . ? N2 C9 1.497(5) . ? N1 C7 1.488(5) . ? N1 C8 1.490(5) . ? N5 C15 1.341(9) . ? N5 C16 1.485(5) . ? N3 C12 1.490(5) . ? N3 C11 1.502(5) . ? C10 C11 1.516(6) . ? C2 C3 1.376(6) . ? C2 C1 1.385(6) . ? C2 C16 1.509(6) . ? C1 C6 1.404(6) . ? C5 C6 1.380(6) . ? C5 C4 1.389(6) . ? C6 C7 1.514(6) . ? C4 C3 1.392(6) . ? C12 C13 1.515(6) . ? C13 N4 1.444(6) . ? C8 C9 1.509(6) . ? N4 C14 1.697(10) . ? C14 C15 1.487(13) . ? C15A C14A 1.549(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N2 C9 114.3(3) . . ? C7 N1 C8 113.9(3) . . ? C15 N5 C16 126.0(5) . . ? C12 N3 C11 115.1(3) . . ? N2 C10 C11 112.5(4) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 C16 120.7(4) . . ? C1 C2 C16 120.1(4) . . ? C2 C1 C6 121.0(4) . . ? C6 C5 C4 120.9(4) . . ? C5 C6 C1 118.7(4) . . ? C5 C6 C7 120.7(4) . . ? C1 C6 C7 120.5(4) . . ? C5 C4 C3 119.2(4) . . ? N3 C11 C10 115.0(3) . . ? N3 C12 C13 111.0(4) . . ? C2 C3 C4 121.0(4) . . ? N5 C16 C2 110.6(4) . . ? N4 C13 C12 111.1(4) . . ? N1 C8 C9 112.3(3) . . ? N1 C7 C6 109.8(3) . . ? N2 C9 C8 111.2(4) . . ? C13 N4 C14 103.4(5) . . ? C15 C14 N4 108.6(7) . . ? N5 C15 C14 106.5(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N2 C10 C11 -176.0(3) . . . . ? C3 C2 C1 C6 -3.6(6) . . . . ? C16 C2 C1 C6 174.6(4) . . . . ? C4 C5 C6 C1 1.4(6) . . . . ? C4 C5 C6 C7 178.7(4) . . . . ? C2 C1 C6 C5 1.8(6) . . . . ? C2 C1 C6 C7 -175.5(4) . . . . ? C6 C5 C4 C3 -2.7(6) . . . . ? C12 N3 C11 C10 58.9(5) . . . . ? N2 C10 C11 N3 66.2(5) . . . . ? C11 N3 C12 C13 -169.0(3) . . . . ? C1 C2 C3 C4 2.3(6) . . . . ? C16 C2 C3 C4 -176.0(4) . . . . ? C5 C4 C3 C2 0.8(6) . . . . ? C15 N5 C16 C2 50.4(8) . . . . ? C3 C2 C16 N5 73.8(5) . . . . ? C1 C2 C16 N5 -104.4(5) . . . . ? N3 C12 C13 N4 143.5(4) . . . . ? C7 N1 C8 C9 173.9(4) . . . . ? C8 N1 C7 C6 179.6(4) . . . . ? C5 C6 C7 N1 -102.6(4) . . . . ? C1 C6 C7 N1 74.6(5) . . . . ? C10 N2 C9 C8 165.0(3) . . . . ? N1 C8 C9 N2 -80.4(5) . . . . ? C12 C13 N4 C14 -149.6(5) . . . . ? C13 N4 C14 C15 157.8(7) . . . . ? C16 N5 C15 C14 84.1(9) . . . . ? N4 C14 C15 N5 -178.5(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A Cl3 0.92 2.12 3.007(4) 161.7 2_556 N2 H2B Cl1 0.92 2.20 3.101(4) 166.9 . N1 H1B Cl1 0.92 2.34 3.170(4) 150.0 . N1 H1B Cl2 0.92 2.72 3.162(4) 110.2 2 N1 H1A Cl2 0.92 2.23 3.083(4) 153.1 . N5 H5A Cl5 0.92 2.27 3.118(4) 152.5 . N5 H5B Cl4 0.92 2.19 3.010(6) 148.2 1_554 N3 H3A Cl5 0.92 2.25 3.082(4) 150.4 2_566 N3 H3B Cl1 0.92 2.33 3.210(4) 158.8 . N3 H3B Cl1 0.92 2.78 3.268(4) 114.4 2_556 N4 H4A Cl3 0.92 2.75 3.434(6) 132.2 2_566 N4 H4B Cl2 0.92 2.18 3.086(5) 169.0 2 _diffrn_measured_fraction_theta_max 0.436 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.436 _refine_diff_density_max 0.337 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.074 data_114MON.CIF _database_code_depnum_ccdc_archive 'CCDC 272042' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common l5-tS5 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H59 N5 O10 S5' _chemical_formula_weight 1062.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.925(2) _cell_length_b 16.012(2) _cell_length_c 22.880(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.651(8) _cell_angle_gamma 90.00 _cell_volume 5043.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 21828 _diffrn_reflns_av_R_equivalents 0.2058 _diffrn_reflns_av_sigmaI/netI 0.1881 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8431 _reflns_number_gt 5667 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+66.9513P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8431 _refine_ls_number_parameters 645 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2499 _refine_ls_R_factor_gt 0.1870 _refine_ls_wR_factor_ref 0.3184 _refine_ls_wR_factor_gt 0.2940 _refine_ls_goodness_of_fit_ref 1.319 _refine_ls_restrained_S_all 1.319 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S4 S 0.2571(2) -0.09252(19) 0.83894(12) 0.0266(7) Uani 1 1 d . . . S3 S -0.0466(2) 0.1501(2) 0.71273(12) 0.0293(7) Uani 1 1 d . . . S1 S -0.1109(2) 0.2651(2) 0.96754(12) 0.0289(7) Uani 1 1 d . . . S5 S -0.0416(3) -0.1857(2) 0.72895(13) 0.0400(9) Uani 1 1 d . . . S2 S 0.2505(2) 0.2570(2) 0.89659(13) 0.0303(7) Uani 1 1 d . . . O7 O 0.2681(6) -0.1802(5) 0.8345(3) 0.034(2) Uani 1 1 d . . . O5 O -0.1213(6) 0.0906(6) 0.7203(3) 0.037(2) Uani 1 1 d . . . O6 O -0.0620(6) 0.2350(5) 0.7266(3) 0.040(2) Uani 1 1 d . . . O3 O 0.2377(6) 0.2263(5) 0.9538(3) 0.033(2) Uani 1 1 d . . . O4 O 0.3316(6) 0.2291(5) 0.8699(4) 0.038(2) Uani 1 1 d . . . O1 O -0.0366(6) 0.2704(5) 1.0173(3) 0.036(2) Uani 1 1 d . . . N4 N 0.1426(7) -0.0729(6) 0.8396(4) 0.028(2) Uani 1 1 d . . . O8 O 0.2861(5) -0.0380(5) 0.7946(3) 0.033(2) Uani 1 1 d . . . N3 N 0.0535(7) 0.1190(6) 0.7544(4) 0.029(2) Uani 1 1 d . . . N2 N 0.1532(7) 0.2319(6) 0.8502(4) 0.029(2) Uani 1 1 d . . . C11 C 0.1431(8) 0.1670(7) 0.7500(5) 0.025(3) Uani 1 1 d . . . H11A H 0.1432 0.1818 0.7080 0.030 Uiso 1 1 calc R . . H11B H 0.1996 0.1301 0.7622 0.030 Uiso 1 1 calc R . . C9 C 0.0576(8) 0.2529(7) 0.8688(5) 0.029(3) Uani 1 1 d . . . H9B H 0.0064 0.2497 0.8339 0.034 Uiso 1 1 calc R . . H9A H 0.0600 0.3112 0.8833 0.034 Uiso 1 1 calc R . . O2 O -0.2064(6) 0.2381(5) 0.9750(4) 0.041(2) Uani 1 1 d . . . N1 N -0.0727(7) 0.2001(6) 0.9218(4) 0.029(2) Uani 1 1 d . . . O10 O 0.0534(8) -0.1654(6) 0.7170(4) 0.053(3) Uani 1 1 d . . . C26 C -0.2204(10) 0.4745(9) 0.8867(5) 0.041(3) Uani 1 1 d . . . H26A H -0.2821 0.4931 0.8677 0.050 Uiso 1 1 calc R . . C33 C 0.2140(9) 0.4928(8) 0.9509(5) 0.037(3) Uani 1 1 d . . . H33A H 0.1972 0.5201 0.9848 0.044 Uiso 1 1 calc R . . C14 C 0.0912(9) -0.1265(7) 0.8775(5) 0.029(3) Uani 1 1 d . . . H14A H 0.0490 -0.0911 0.8984 0.035 Uiso 1 1 calc R . . H14B H 0.1395 -0.1538 0.9077 0.035 Uiso 1 1 calc R . . C12 C 0.0684(8) 0.0293(7) 0.7637(5) 0.025(3) Uani 1 1 d . . . H12B H 0.1148 0.0083 0.7383 0.031 Uiso 1 1 calc R . . H12A H 0.0061 -0.0007 0.7528 0.031 Uiso 1 1 calc R . . C7 C -0.1413(9) 0.1511(7) 0.8805(5) 0.031(3) Uani 1 1 d . . . H7B H -0.1257 0.1582 0.8400 0.037 Uiso 1 1 calc R . . H7A H -0.2079 0.1726 0.8809 0.037 Uiso 1 1 calc R . . O9 O -0.1247(9) -0.1522(7) 0.6932(4) 0.071(3) Uani 1 1 d . . . C4 C -0.1402(7) -0.0033(7) 0.8526(5) 0.026(3) Uani 1 1 d . . . H4 H -0.1372 0.0135 0.8131 0.031 Uiso 1 1 calc R . . C28 C -0.0570(9) 0.5022(9) 0.9247(5) 0.039(3) Uani 1 1 d . . . H28A H -0.0039 0.5401 0.9315 0.046 Uiso 1 1 calc R . . C40 C 0.0277(11) 0.0783(10) 0.5569(5) 0.055(4) Uani 1 1 d . . . H40A H 0.0514 0.0291 0.5407 0.067 Uiso 1 1 calc R . . N5 N -0.0465(7) -0.1566(6) 0.7980(4) 0.030(2) Uani 1 1 d . . . C2 C -0.1484(8) -0.1116(8) 0.9229(6) 0.032(3) Uani 1 1 d . . . H2 H -0.1515 -0.1690 0.9330 0.038 Uiso 1 1 calc R . . C49 C 0.3654(8) -0.0879(10) 1.0113(5) 0.038(3) Uani 1 1 d . . . H49 H 0.3755 -0.1264 1.0432 0.045 Uiso 1 1 calc R . . C32 C 0.2253(8) 0.4065(8) 0.9511(5) 0.031(3) Uani 1 1 d . . . H32A H 0.2165 0.3745 0.9848 0.038 Uiso 1 1 calc R . . C8 C 0.0295(8) 0.1957(7) 0.9172(5) 0.029(3) Uani 1 1 d . . . H8B H 0.0464 0.1373 0.9086 0.035 Uiso 1 1 calc R . . H8A H 0.0677 0.2115 0.9556 0.035 Uiso 1 1 calc R . . C21 C 0.0218(10) -0.4309(9) 0.7364(6) 0.047(4) Uani 1 1 d . . . H21A H 0.0782 -0.4645 0.7370 0.056 Uiso 1 1 calc R . . C6 C -0.1405(8) 0.0335(8) 0.9542(5) 0.030(3) Uani 1 1 d . . . H6 H -0.1379 0.0737 0.9849 0.036 Uiso 1 1 calc R . . C15 C 0.0294(8) -0.1934(7) 0.8425(4) 0.024(3) Uani 1 1 d . . . H15B H 0.0717 -0.2299 0.8225 0.029 Uiso 1 1 calc R . . H15A H -0.0016 -0.2284 0.8701 0.029 Uiso 1 1 calc R . . C50 C 0.3316(7) -0.1178(8) 0.9551(5) 0.028(3) Uani 1 1 d . . . H50 H 0.3190 -0.1756 0.9484 0.033 Uiso 1 1 calc R . . C38 C -0.0261(8) 0.1487(8) 0.6378(5) 0.033(3) Uani 1 1 d . . . C5 C -0.1385(8) 0.0588(8) 0.8959(5) 0.029(3) Uani 1 1 d . . . C47 C 0.3711(9) 0.0506(9) 0.9753(6) 0.040(3) Uani 1 1 d . . . H47 H 0.3849 0.1082 0.9821 0.048 Uiso 1 1 calc R . . C25 C -0.2092(8) 0.3904(7) 0.9043(5) 0.024(3) Uani 1 1 d . . . H25A H -0.2608 0.3516 0.8950 0.029 Uiso 1 1 calc R . . C3 C -0.1458(8) -0.0869(7) 0.8642(5) 0.027(3) Uani 1 1 d . . . C44 C 0.0427(11) 0.1505(11) 0.4610(6) 0.064(5) Uani 1 1 d . . . H44B H -0.0164 0.1579 0.4323 0.097 Uiso 1 1 calc R . . H44C H 0.0736 0.0974 0.4534 0.097 Uiso 1 1 calc R . . H44A H 0.0877 0.1966 0.4571 0.097 Uiso 1 1 calc R . . C35 C 0.2522(8) 0.4989(8) 0.8530(5) 0.034(3) Uani 1 1 d . . . H35A H 0.2608 0.5309 0.8192 0.041 Uiso 1 1 calc R . . C19 C -0.1485(9) -0.4185(10) 0.7382(5) 0.046(4) Uani 1 1 d . . . H19A H -0.2094 -0.4441 0.7406 0.055 Uiso 1 1 calc R . . C24 C -0.1231(8) 0.3666(7) 0.9348(5) 0.025(3) Uani 1 1 d . . . C17 C -0.0545(9) -0.2951(8) 0.7287(5) 0.035(3) Uani 1 1 d . . . C43 C -0.0323(11) 0.2223(8) 0.6070(6) 0.050(4) Uani 1 1 d . . . H43A H -0.0482 0.2731 0.6248 0.060 Uiso 1 1 calc R . . C13 C 0.1086(8) 0.0130(8) 0.8290(5) 0.030(3) Uani 1 1 d . . . H13B H 0.1631 0.0518 0.8416 0.036 Uiso 1 1 calc R . . H13A H 0.0571 0.0247 0.8533 0.036 Uiso 1 1 calc R . . C45 C 0.3167(7) -0.0614(8) 0.9092(5) 0.028(3) Uani 1 1 d . . . C18 C -0.1430(9) -0.3327(9) 0.7309(5) 0.038(3) Uani 1 1 d . . . H18A H -0.2003 -0.2998 0.7274 0.045 Uiso 1 1 calc R . . C30 C -0.1575(12) 0.6223(9) 0.8824(6) 0.055(4) Uani 1 1 d . . . H30B H -0.2135 0.6310 0.8515 0.082 Uiso 1 1 calc R . . H30A H -0.0986 0.6431 0.8687 0.082 Uiso 1 1 calc R . . H30C H -0.1676 0.6525 0.9182 0.082 Uiso 1 1 calc R . . C31 C 0.2502(8) 0.3675(8) 0.9002(5) 0.034(3) Uani 1 1 d . . . C29 C -0.0442(10) 0.4186(8) 0.9439(5) 0.035(3) Uani 1 1 d . . . H29A H 0.0173 0.3990 0.9626 0.041 Uiso 1 1 calc R . . C34 C 0.2269(9) 0.5392(8) 0.9021(5) 0.031(3) Uani 1 1 d . . . C51 C 0.4146(9) 0.0256(10) 1.0849(6) 0.050(4) Uani 1 1 d . . . H51C H 0.3574 0.0468 1.1004 0.075 Uiso 1 1 calc R . . H51A H 0.4625 0.0705 1.0853 0.075 Uiso 1 1 calc R . . H51B H 0.4431 -0.0207 1.1097 0.075 Uiso 1 1 calc R . . C10 C 0.1573(9) 0.2469(8) 0.7866(5) 0.035(3) Uani 1 1 d . . . H10B H 0.2210 0.2718 0.7824 0.042 Uiso 1 1 calc R . . H10A H 0.1062 0.2876 0.7711 0.042 Uiso 1 1 calc R . . C27 C -0.1463(10) 0.5295(8) 0.8961(5) 0.036(3) Uani 1 1 d . . . C39 C 0.0046(11) 0.0769(10) 0.6141(5) 0.052(4) Uani 1 1 d . . . H39A H 0.0101 0.0266 0.6364 0.062 Uiso 1 1 calc R . . C46 C 0.3377(8) 0.0234(8) 0.9184(5) 0.034(3) Uani 1 1 d . . . H46 H 0.3291 0.0616 0.8863 0.041 Uiso 1 1 calc R . . C36 C 0.2649(9) 0.4156(8) 0.8520(5) 0.032(3) Uani 1 1 d . . . H36A H 0.2840 0.3897 0.8182 0.038 Uiso 1 1 calc R . . C37 C 0.2142(10) 0.6323(8) 0.9017(6) 0.044(3) Uani 1 1 d . . . H37C H 0.1448 0.6459 0.8953 0.066 Uiso 1 1 calc R . . H37A H 0.2451 0.6566 0.8698 0.066 Uiso 1 1 calc R . . H37B H 0.2446 0.6553 0.9397 0.066 Uiso 1 1 calc R . . C1 C -0.1461(8) -0.0490(7) 0.9664(5) 0.027(3) Uani 1 1 d . . . H1 H -0.1487 -0.0654 1.0061 0.033 Uiso 1 1 calc R . . C48 C 0.3850(8) -0.0048(9) 1.0226(5) 0.039(4) Uani 1 1 d . . . C20 C -0.0650(9) -0.4673(8) 0.7419(5) 0.034(3) Uani 1 1 d . . . C23 C -0.0707(11) -0.5613(9) 0.7498(7) 0.057(4) Uani 1 1 d . . . H23A H -0.1143 -0.5740 0.7785 0.086 Uiso 1 1 calc R . . H23C H -0.0057 -0.5833 0.7643 0.086 Uiso 1 1 calc R . . H23B H -0.0957 -0.5873 0.7118 0.086 Uiso 1 1 calc R . . C41 C 0.0165(10) 0.1500(10) 0.5238(5) 0.044(4) Uani 1 1 d . . . C16 C -0.1438(9) -0.1517(8) 0.8162(5) 0.038(3) Uani 1 1 d . . . H16B H -0.1614 -0.2069 0.8309 0.046 Uiso 1 1 calc R . . H16A H -0.1924 -0.1370 0.7815 0.046 Uiso 1 1 calc R . . C42 C -0.0144(11) 0.2199(9) 0.5481(6) 0.053(4) Uani 1 1 d . . . H42A H -0.0244 0.2691 0.5246 0.064 Uiso 1 1 calc R . . C22 C 0.0282(10) -0.3443(9) 0.7298(5) 0.042(4) Uani 1 1 d . . . H22A H 0.0887 -0.3192 0.7260 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S4 0.0305(17) 0.0265(18) 0.0257(15) -0.0017(14) 0.0137(13) -0.0018(14) S3 0.0394(18) 0.0271(18) 0.0224(15) 0.0031(13) 0.0076(13) 0.0026(15) S1 0.0352(18) 0.0273(18) 0.0268(15) 0.0004(14) 0.0135(14) 0.0016(14) S5 0.070(3) 0.032(2) 0.0191(15) -0.0008(14) 0.0098(16) 0.0028(18) S2 0.0320(17) 0.0306(19) 0.0304(16) 0.0017(14) 0.0118(13) -0.0001(15) O7 0.032(5) 0.037(5) 0.035(5) -0.007(4) 0.013(4) 0.009(4) O5 0.036(5) 0.047(6) 0.029(4) 0.000(4) 0.010(4) -0.005(4) O6 0.042(5) 0.037(6) 0.037(5) 0.006(4) 0.000(4) 0.016(4) O3 0.034(5) 0.040(5) 0.025(4) 0.007(4) 0.006(4) 0.000(4) O4 0.041(5) 0.031(5) 0.046(5) 0.002(4) 0.017(4) 0.007(4) O1 0.050(5) 0.031(5) 0.028(4) 0.003(4) 0.011(4) 0.006(4) N4 0.037(6) 0.022(6) 0.027(5) 0.000(4) 0.010(4) 0.004(5) O8 0.032(5) 0.034(5) 0.039(5) 0.003(4) 0.022(4) -0.006(4) N3 0.035(6) 0.026(6) 0.029(5) -0.003(5) 0.011(5) -0.010(5) N2 0.049(6) 0.027(6) 0.017(5) 0.011(4) 0.026(4) 0.004(5) C11 0.035(7) 0.022(7) 0.022(6) -0.001(5) 0.014(5) 0.001(5) C9 0.037(7) 0.025(7) 0.023(6) 0.002(5) 0.003(5) -0.013(6) O2 0.052(6) 0.033(5) 0.043(5) -0.001(4) 0.030(4) 0.006(4) N1 0.030(6) 0.025(6) 0.032(5) -0.011(5) 0.007(5) -0.006(5) O10 0.097(8) 0.037(6) 0.035(5) -0.008(4) 0.040(5) -0.008(6) C26 0.035(8) 0.049(10) 0.040(7) -0.011(7) 0.006(6) -0.010(7) C33 0.048(8) 0.039(9) 0.027(7) -0.003(6) 0.017(6) 0.008(7) C14 0.044(7) 0.024(7) 0.022(6) 0.014(5) 0.012(5) 0.015(6) C12 0.020(6) 0.018(7) 0.041(7) -0.009(5) 0.014(5) -0.001(5) C7 0.041(7) 0.028(7) 0.027(6) 0.005(6) 0.017(6) 0.015(6) O9 0.116(9) 0.064(8) 0.026(5) -0.007(5) -0.017(6) 0.015(7) C4 0.017(6) 0.032(8) 0.028(6) -0.018(6) 0.004(5) -0.008(5) C28 0.033(8) 0.049(10) 0.037(7) -0.010(7) 0.014(6) -0.014(7) C40 0.079(11) 0.061(11) 0.028(7) 0.006(7) 0.012(7) 0.023(9) N5 0.038(6) 0.025(6) 0.026(5) -0.001(5) 0.006(4) 0.009(5) C2 0.017(6) 0.023(7) 0.060(8) 0.002(6) 0.016(6) -0.004(5) C49 0.020(6) 0.073(11) 0.019(6) 0.004(7) 0.000(5) -0.008(7) C32 0.037(7) 0.042(9) 0.016(6) 0.002(6) 0.009(5) 0.000(6) C8 0.044(8) 0.014(6) 0.032(6) 0.005(5) 0.010(6) 0.003(6) C21 0.039(8) 0.049(10) 0.055(9) -0.012(7) 0.015(7) 0.014(7) C6 0.029(7) 0.033(8) 0.029(6) -0.004(6) 0.011(5) 0.002(6) C15 0.036(7) 0.018(6) 0.021(6) -0.003(5) 0.011(5) 0.004(5) C50 0.008(5) 0.036(8) 0.040(7) 0.010(6) 0.009(5) -0.008(5) C38 0.030(7) 0.035(8) 0.035(7) -0.002(6) 0.007(6) 0.001(6) C5 0.013(6) 0.044(8) 0.031(7) 0.001(6) 0.003(5) 0.002(6) C47 0.034(8) 0.034(8) 0.055(9) 0.012(7) 0.013(7) 0.002(6) C25 0.030(7) 0.014(6) 0.029(6) -0.004(5) 0.010(5) -0.014(5) C3 0.019(6) 0.025(7) 0.040(7) -0.012(6) 0.011(5) 0.000(5) C44 0.075(11) 0.082(13) 0.045(8) 0.001(9) 0.038(8) -0.005(10) C35 0.035(7) 0.036(8) 0.036(7) -0.010(6) 0.021(6) -0.015(6) C19 0.017(7) 0.078(12) 0.039(8) -0.014(8) -0.004(6) -0.009(7) C24 0.032(7) 0.022(7) 0.021(6) -0.011(5) 0.007(5) 0.002(6) C17 0.041(8) 0.040(8) 0.028(7) -0.009(6) 0.016(6) 0.017(7) C43 0.096(12) 0.012(7) 0.048(8) 0.002(6) 0.028(8) -0.004(7) C13 0.028(7) 0.037(8) 0.027(6) -0.009(6) 0.013(5) -0.004(6) C45 0.012(6) 0.040(8) 0.036(7) 0.002(6) 0.018(5) 0.001(5) C18 0.027(7) 0.049(10) 0.035(7) -0.024(7) -0.004(6) 0.004(7) C30 0.090(12) 0.038(9) 0.037(8) -0.003(7) 0.008(8) 0.000(8) C31 0.028(7) 0.052(9) 0.024(6) 0.000(6) 0.011(5) -0.001(6) C29 0.047(8) 0.024(7) 0.033(7) -0.006(6) 0.007(6) 0.013(6) C34 0.034(7) 0.028(7) 0.030(7) -0.003(6) 0.006(6) -0.010(6) C51 0.029(8) 0.067(11) 0.054(9) -0.007(8) 0.008(7) 0.013(7) C10 0.043(7) 0.036(8) 0.032(6) 0.005(6) 0.026(6) -0.007(6) C27 0.052(9) 0.034(8) 0.027(7) -0.004(6) 0.018(6) -0.005(7) C39 0.073(11) 0.059(11) 0.024(7) 0.005(7) 0.008(7) 0.004(8) C46 0.033(7) 0.042(9) 0.027(7) 0.010(6) 0.006(6) 0.010(6) C36 0.041(8) 0.033(8) 0.024(6) -0.010(6) 0.014(6) -0.002(6) C37 0.048(9) 0.034(8) 0.052(8) -0.005(7) 0.014(7) -0.008(7) C1 0.034(7) 0.025(7) 0.027(6) 0.004(5) 0.017(5) 0.001(6) C48 0.012(6) 0.066(11) 0.041(8) -0.026(8) 0.007(5) -0.017(6) C20 0.046(8) 0.024(7) 0.035(7) -0.012(6) 0.013(6) -0.023(6) C23 0.059(10) 0.048(10) 0.066(10) -0.015(8) 0.015(8) -0.012(8) C41 0.043(8) 0.060(11) 0.031(7) 0.013(7) 0.009(6) 0.004(8) C16 0.034(7) 0.036(8) 0.044(7) 0.003(7) 0.006(6) 0.001(6) C42 0.083(12) 0.035(9) 0.044(8) 0.029(7) 0.017(8) 0.007(8) C22 0.052(9) 0.038(9) 0.044(8) -0.019(7) 0.029(7) -0.025(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S4 O7 1.418(9) . ? S4 O8 1.441(8) . ? S4 N4 1.627(10) . ? S4 C45 1.766(12) . ? S3 O6 1.420(9) . ? S3 O5 1.440(9) . ? S3 N3 1.642(10) . ? S3 C38 1.781(12) . ? S1 O1 1.421(8) . ? S1 O2 1.432(9) . ? S1 N1 1.621(9) . ? S1 C24 1.787(12) . ? S5 O9 1.418(11) . ? S5 O10 1.428(10) . ? S5 N5 1.659(9) . ? S5 C17 1.762(14) . ? S2 O4 1.433(8) . ? S2 O3 1.433(8) . ? S2 N2 1.642(10) . ? S2 C31 1.771(14) . ? N4 C13 1.462(15) . ? N4 C14 1.479(14) . ? N3 C12 1.463(14) . ? N3 C11 1.482(14) . ? N2 C10 1.483(13) . ? N2 C9 1.496(14) . ? C11 C10 1.526(16) . ? C9 C8 1.532(14) . ? N1 C8 1.445(14) . ? N1 C7 1.466(15) . ? C26 C27 1.349(17) . ? C26 C25 1.408(17) . ? C33 C34 1.375(16) . ? C33 C32 1.391(17) . ? C14 C15 1.524(16) . ? C12 C13 1.537(15) . ? C7 C5 1.518(17) . ? C4 C3 1.369(16) . ? C4 C5 1.401(15) . ? C28 C27 1.386(18) . ? C28 C29 1.411(18) . ? C40 C41 1.371(19) . ? C40 C39 1.394(17) . ? N5 C15 1.476(14) . ? N5 C16 1.478(14) . ? C2 C3 1.407(16) . ? C2 C1 1.409(16) . ? C49 C48 1.375(19) . ? C49 C50 1.387(16) . ? C32 C31 1.410(15) . ? C21 C20 1.365(17) . ? C21 C22 1.399(19) . ? C6 C1 1.354(16) . ? C6 C5 1.400(15) . ? C50 C45 1.376(16) . ? C38 C39 1.365(18) . ? C38 C43 1.369(17) . ? C47 C46 1.384(17) . ? C47 C48 1.390(18) . ? C25 C24 1.348(15) . ? C3 C16 1.514(16) . ? C44 C41 1.536(17) . ? C35 C36 1.347(17) . ? C35 C34 1.385(16) . ? C19 C18 1.39(2) . ? C19 C20 1.392(18) . ? C24 C29 1.370(17) . ? C17 C18 1.379(17) . ? C17 C22 1.392(18) . ? C43 C42 1.410(18) . ? C45 C46 1.399(17) . ? C30 C27 1.522(18) . ? C31 C36 1.384(16) . ? C34 C37 1.501(17) . ? C51 C48 1.505(17) . ? C20 C23 1.521(19) . ? C41 C42 1.348(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 S4 O8 120.4(5) . . ? O7 S4 N4 108.0(5) . . ? O8 S4 N4 105.6(5) . . ? O7 S4 C45 107.6(6) . . ? O8 S4 C45 109.1(5) . . ? N4 S4 C45 105.3(5) . . ? O6 S3 O5 118.1(5) . . ? O6 S3 N3 107.7(5) . . ? O5 S3 N3 107.2(5) . . ? O6 S3 C38 106.2(6) . . ? O5 S3 C38 109.3(5) . . ? N3 S3 C38 108.0(5) . . ? O1 S1 O2 120.0(5) . . ? O1 S1 N1 106.6(5) . . ? O2 S1 N1 106.5(5) . . ? O1 S1 C24 107.1(5) . . ? O2 S1 C24 107.0(5) . . ? N1 S1 C24 109.4(5) . . ? O9 S5 O10 120.2(7) . . ? O9 S5 N5 107.2(6) . . ? O10 S5 N5 106.9(5) . . ? O9 S5 C17 107.5(7) . . ? O10 S5 C17 108.9(6) . . ? N5 S5 C17 105.3(5) . . ? O4 S2 O3 119.8(5) . . ? O4 S2 N2 105.9(5) . . ? O3 S2 N2 107.7(5) . . ? O4 S2 C31 109.8(5) . . ? O3 S2 C31 107.4(5) . . ? N2 S2 C31 105.5(5) . . ? C13 N4 C14 118.0(9) . . ? C13 N4 S4 118.3(8) . . ? C14 N4 S4 117.0(7) . . ? C12 N3 C11 114.6(9) . . ? C12 N3 S3 118.1(8) . . ? C11 N3 S3 117.0(8) . . ? C10 N2 C9 114.3(9) . . ? C10 N2 S2 116.4(7) . . ? C9 N2 S2 116.3(7) . . ? N3 C11 C10 116.0(9) . . ? N2 C9 C8 114.0(9) . . ? C8 N1 C7 118.7(9) . . ? C8 N1 S1 120.0(8) . . ? C7 N1 S1 121.0(7) . . ? C27 C26 C25 122.0(13) . . ? C34 C33 C32 120.8(11) . . ? N4 C14 C15 112.7(9) . . ? N3 C12 C13 109.3(9) . . ? N1 C7 C5 112.3(9) . . ? C3 C4 C5 123.6(11) . . ? C27 C28 C29 120.6(12) . . ? C41 C40 C39 120.5(14) . . ? C15 N5 C16 114.8(9) . . ? C15 N5 S5 114.7(7) . . ? C16 N5 S5 117.0(8) . . ? C3 C2 C1 118.3(11) . . ? C48 C49 C50 122.6(12) . . ? C33 C32 C31 118.6(11) . . ? N1 C8 C9 112.6(9) . . ? C20 C21 C22 120.3(13) . . ? C1 C6 C5 119.3(11) . . ? N5 C15 C14 111.8(9) . . ? C45 C50 C49 118.2(12) . . ? C39 C38 C43 121.4(11) . . ? C39 C38 S3 119.8(10) . . ? C43 C38 S3 118.4(10) . . ? C6 C5 C4 117.9(12) . . ? C6 C5 C7 120.0(11) . . ? C4 C5 C7 122.0(10) . . ? C46 C47 C48 121.2(13) . . ? C24 C25 C26 118.1(11) . . ? C4 C3 C2 118.1(10) . . ? C4 C3 C16 121.4(11) . . ? C2 C3 C16 120.4(11) . . ? C36 C35 C34 121.7(12) . . ? C18 C19 C20 120.1(12) . . ? C25 C24 C29 122.5(11) . . ? C25 C24 S1 119.7(9) . . ? C29 C24 S1 117.7(9) . . ? C18 C17 C22 119.6(13) . . ? C18 C17 S5 121.7(10) . . ? C22 C17 S5 118.6(10) . . ? C38 C43 C42 117.5(12) . . ? N4 C13 C12 112.5(9) . . ? C50 C45 C46 121.2(11) . . ? C50 C45 S4 120.4(10) . . ? C46 C45 S4 118.0(9) . . ? C17 C18 C19 120.2(12) . . ? C36 C31 C32 119.7(12) . . ? C36 C31 S2 121.1(9) . . ? C32 C31 S2 118.9(9) . . ? C24 C29 C28 117.9(12) . . ? C33 C34 C35 119.1(12) . . ? C33 C34 C37 120.8(11) . . ? C35 C34 C37 120.1(11) . . ? N2 C10 C11 112.4(9) . . ? C26 C27 C28 118.7(13) . . ? C26 C27 C30 123.5(14) . . ? C28 C27 C30 117.5(13) . . ? C38 C39 C40 119.3(14) . . ? C47 C46 C45 118.7(12) . . ? C35 C36 C31 120.1(11) . . ? C6 C1 C2 122.9(11) . . ? C49 C48 C47 118.1(11) . . ? C49 C48 C51 120.6(13) . . ? C47 C48 C51 121.2(13) . . ? C21 C20 C19 119.9(13) . . ? C21 C20 C23 119.7(13) . . ? C19 C20 C23 120.3(12) . . ? C42 C41 C40 119.0(12) . . ? C42 C41 C44 121.1(13) . . ? C40 C41 C44 119.9(14) . . ? N5 C16 C3 111.0(10) . . ? C41 C42 C43 122.0(12) . . ? C17 C22 C21 119.8(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 S4 N4 C13 -164.9(8) . . . . ? O8 S4 N4 C13 -34.9(9) . . . . ? C45 S4 N4 C13 80.4(9) . . . . ? O7 S4 N4 C14 44.3(9) . . . . ? O8 S4 N4 C14 174.2(8) . . . . ? C45 S4 N4 C14 -70.5(9) . . . . ? O6 S3 N3 C12 159.7(8) . . . . ? O5 S3 N3 C12 31.7(9) . . . . ? C38 S3 N3 C12 -86.0(9) . . . . ? O6 S3 N3 C11 -57.0(9) . . . . ? O5 S3 N3 C11 175.0(7) . . . . ? C38 S3 N3 C11 57.3(9) . . . . ? O4 S2 N2 C10 -42.1(9) . . . . ? O3 S2 N2 C10 -171.4(8) . . . . ? C31 S2 N2 C10 74.3(9) . . . . ? O4 S2 N2 C9 178.6(8) . . . . ? O3 S2 N2 C9 49.3(9) . . . . ? C31 S2 N2 C9 -65.1(8) . . . . ? C12 N3 C11 C10 -133.0(10) . . . . ? S3 N3 C11 C10 82.4(11) . . . . ? C10 N2 C9 C8 145.9(10) . . . . ? S2 N2 C9 C8 -74.0(11) . . . . ? O1 S1 N1 C8 -33.9(10) . . . . ? O2 S1 N1 C8 -163.1(8) . . . . ? C24 S1 N1 C8 81.6(9) . . . . ? O1 S1 N1 C7 152.1(8) . . . . ? O2 S1 N1 C7 22.9(10) . . . . ? C24 S1 N1 C7 -92.4(9) . . . . ? C13 N4 C14 C15 107.8(11) . . . . ? S4 N4 C14 C15 -101.2(10) . . . . ? C11 N3 C12 C13 78.5(11) . . . . ? S3 N3 C12 C13 -137.4(8) . . . . ? C8 N1 C7 C5 75.4(12) . . . . ? S1 N1 C7 C5 -110.6(10) . . . . ? O9 S5 N5 C15 173.9(9) . . . . ? O10 S5 N5 C15 -56.0(9) . . . . ? C17 S5 N5 C15 59.6(9) . . . . ? O9 S5 N5 C16 35.2(11) . . . . ? O10 S5 N5 C16 165.3(9) . . . . ? C17 S5 N5 C16 -79.0(10) . . . . ? C34 C33 C32 C31 -0.1(19) . . . . ? C7 N1 C8 C9 81.7(13) . . . . ? S1 N1 C8 C9 -92.5(11) . . . . ? N2 C9 C8 N1 -162.4(9) . . . . ? C16 N5 C15 C14 -98.8(11) . . . . ? S5 N5 C15 C14 121.6(8) . . . . ? N4 C14 C15 N5 -60.7(12) . . . . ? C48 C49 C50 C45 -0.4(17) . . . . ? O6 S3 C38 C39 170.8(11) . . . . ? O5 S3 C38 C39 -60.8(12) . . . . ? N3 S3 C38 C39 55.5(12) . . . . ? O6 S3 C38 C43 -2.8(13) . . . . ? O5 S3 C38 C43 125.6(11) . . . . ? N3 S3 C38 C43 -118.1(11) . . . . ? C1 C6 C5 C4 -1.5(17) . . . . ? C1 C6 C5 C7 174.5(11) . . . . ? C3 C4 C5 C6 1.5(17) . . . . ? C3 C4 C5 C7 -174.4(11) . . . . ? N1 C7 C5 C6 47.1(14) . . . . ? N1 C7 C5 C4 -137.0(10) . . . . ? C27 C26 C25 C24 4.4(17) . . . . ? C5 C4 C3 C2 -1.1(17) . . . . ? C5 C4 C3 C16 -177.8(10) . . . . ? C1 C2 C3 C4 0.7(16) . . . . ? C1 C2 C3 C16 177.4(10) . . . . ? C26 C25 C24 C29 -6.6(16) . . . . ? C26 C25 C24 S1 170.7(8) . . . . ? O1 S1 C24 C25 -152.4(8) . . . . ? O2 S1 C24 C25 -22.6(10) . . . . ? N1 S1 C24 C25 92.5(9) . . . . ? O1 S1 C24 C29 25.2(10) . . . . ? O2 S1 C24 C29 154.9(8) . . . . ? N1 S1 C24 C29 -90.0(9) . . . . ? O9 S5 C17 C18 -39.3(12) . . . . ? O10 S5 C17 C18 -170.9(10) . . . . ? N5 S5 C17 C18 74.8(11) . . . . ? O9 S5 C17 C22 144.5(10) . . . . ? O10 S5 C17 C22 12.8(12) . . . . ? N5 S5 C17 C22 -101.5(10) . . . . ? C39 C38 C43 C42 6(2) . . . . ? S3 C38 C43 C42 179.1(11) . . . . ? C14 N4 C13 C12 -115.5(10) . . . . ? S4 N4 C13 C12 93.9(10) . . . . ? N3 C12 C13 N4 -169.2(9) . . . . ? C49 C50 C45 C46 1.8(16) . . . . ? C49 C50 C45 S4 -170.6(8) . . . . ? O7 S4 C45 C50 -23.5(10) . . . . ? O8 S4 C45 C50 -155.6(8) . . . . ? N4 S4 C45 C50 91.5(9) . . . . ? O7 S4 C45 C46 163.8(8) . . . . ? O8 S4 C45 C46 31.7(10) . . . . ? N4 S4 C45 C46 -81.2(9) . . . . ? C22 C17 C18 C19 4.4(18) . . . . ? S5 C17 C18 C19 -171.9(9) . . . . ? C20 C19 C18 C17 -1.5(19) . . . . ? C33 C32 C31 C36 1.5(18) . . . . ? C33 C32 C31 S2 -172.5(10) . . . . ? O4 S2 C31 C36 45.8(12) . . . . ? O3 S2 C31 C36 177.5(10) . . . . ? N2 S2 C31 C36 -67.9(11) . . . . ? O4 S2 C31 C32 -140.3(9) . . . . ? O3 S2 C31 C32 -8.6(11) . . . . ? N2 S2 C31 C32 106.0(10) . . . . ? C25 C24 C29 C28 5.4(16) . . . . ? S1 C24 C29 C28 -172.0(8) . . . . ? C27 C28 C29 C24 -1.8(17) . . . . ? C32 C33 C34 C35 -0.5(19) . . . . ? C32 C33 C34 C37 179.7(12) . . . . ? C36 C35 C34 C33 -0.3(19) . . . . ? C36 C35 C34 C37 179.4(12) . . . . ? C9 N2 C10 C11 -99.6(11) . . . . ? S2 N2 C10 C11 120.2(9) . . . . ? N3 C11 C10 N2 55.2(14) . . . . ? C25 C26 C27 C28 -1.0(18) . . . . ? C25 C26 C27 C30 -174.7(11) . . . . ? C29 C28 C27 C26 -0.3(17) . . . . ? C29 C28 C27 C30 173.8(11) . . . . ? C43 C38 C39 C40 -2(2) . . . . ? S3 C38 C39 C40 -175.0(11) . . . . ? C41 C40 C39 C38 -2(2) . . . . ? C48 C47 C46 C45 0.7(18) . . . . ? C50 C45 C46 C47 -2.0(17) . . . . ? S4 C45 C46 C47 170.6(8) . . . . ? C34 C35 C36 C31 1.8(19) . . . . ? C32 C31 C36 C35 -2.3(19) . . . . ? S2 C31 C36 C35 171.5(10) . . . . ? C5 C6 C1 C2 1.2(18) . . . . ? C3 C2 C1 C6 -0.8(17) . . . . ? C50 C49 C48 C47 -0.8(18) . . . . ? C50 C49 C48 C51 175.4(10) . . . . ? C46 C47 C48 C49 0.6(18) . . . . ? C46 C47 C48 C51 -175.6(11) . . . . ? C22 C21 C20 C19 3(2) . . . . ? C22 C21 C20 C23 -179.3(12) . . . . ? C18 C19 C20 C21 -2.3(19) . . . . ? C18 C19 C20 C23 -179.9(12) . . . . ? C39 C40 C41 C42 2(2) . . . . ? C39 C40 C41 C44 179.7(14) . . . . ? C15 N5 C16 C3 70.2(13) . . . . ? S5 N5 C16 C3 -151.2(9) . . . . ? C4 C3 C16 N5 70.1(14) . . . . ? C2 C3 C16 N5 -106.5(12) . . . . ? C40 C41 C42 C43 2(2) . . . . ? C44 C41 C42 C43 -175.5(14) . . . . ? C38 C43 C42 C41 -6(2) . . . . ? C18 C17 C22 C21 -3.6(19) . . . . ? S5 C17 C22 C21 172.7(10) . . . . ? C20 C21 C22 C17 0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.627 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.139