# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge ? loop_ _publ_author_name 'Alexander von Zelewsky' 'Chrisophe Bonte' 'Sarah Richard Ducotterd' 'Mathias Duggeli' 'Catherine Goujon-Ginglinger' 'David Mauron' 'Antonia Neels' 'Helen Stoeckli-Evans' _publ_contact_author_name 'Prof Alexander von Zelewsky' _publ_contact_author_address ; Department opf Chemistry UNIFR Perolles Fribourg CH-1700 SWITZERLAND ; _publ_contact_author_email 'ALEXANDER.VONZELEWSKY@UNIFR.CH' _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthetic routes for a new family of chiral tetradentate ligands containing pyridine rings. ; data_cpd1 _database_code_CSD 179702 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 N2 O' _chemical_formula_weight 356.45 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.1016(9) _cell_length_b 9.3289(7) _cell_length_c 11.1653(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.651(13) _cell_angle_gamma 90.00 _cell_volume 941.64(15) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6755 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.94 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.077 _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 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7352 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.94 _reflns_number_total 3477 _reflns_number_gt 2978 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0396P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(12) _refine_ls_number_reflns 3477 _refine_ls_number_parameters 340 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0664 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.10348(13) 0.25330(13) 0.61130(10) 0.0276(3) Uani 1 1 d . . . N2 N 0.29171(13) 0.10671(14) 0.88597(10) 0.0330(3) Uani 1 1 d . . . O1 O 1.10937(12) 0.09711(13) 1.18097(10) 0.0420(3) Uani 1 1 d . . . C1 C 0.11940(15) 0.18789(15) 0.71982(12) 0.0260(3) Uani 1 1 d . . . C2 C 0.00035(16) 0.12436(15) 0.76800(12) 0.0279(3) Uani 1 1 d . . . H2 H 0.0177(15) 0.0789(18) 0.8451(14) 0.029(4) Uiso 1 1 d . . . C3 C -0.13769(16) 0.12700(15) 0.70165(12) 0.0279(3) Uani 1 1 d . . . H3 H -0.2211(16) 0.0832(17) 0.7356(12) 0.025(4) Uiso 1 1 d . . . C4 C -0.15567(15) 0.19087(15) 0.58921(12) 0.0264(3) Uani 1 1 d . . . C5 C -0.29603(16) 0.19560(16) 0.50393(13) 0.0304(3) Uani 1 1 d . . . H5 H -0.3785(19) 0.1514(19) 0.5405(15) 0.037(4) Uiso 1 1 d . . . C6 C -0.32255(16) 0.35123(16) 0.45187(13) 0.0292(3) Uani 1 1 d . . . C7 C -0.20617(17) 0.31016(17) 0.36528(13) 0.0330(3) Uani 1 1 d . . . H7 H -0.2195(17) 0.3510(17) 0.2855(15) 0.025(4) Uiso 1 1 d . . . C8 C -0.04888(17) 0.32731(19) 0.42697(13) 0.0339(4) Uani 1 1 d . . . H8A H 0.0198(18) 0.287(2) 0.3772(15) 0.041(5) Uiso 1 1 d . . . H8B H -0.0244(19) 0.427(2) 0.4384(15) 0.045(5) Uiso 1 1 d . . . C9 C -0.03018(15) 0.25448(15) 0.54866(12) 0.0271(3) Uani 1 1 d . . . C10 C -0.2545(2) 0.15154(18) 0.37798(14) 0.0374(4) Uani 1 1 d . . . H10A H -0.1776(18) 0.079(2) 0.3778(14) 0.038(4) Uiso 1 1 d . . . H10B H -0.3425(17) 0.1300(18) 0.3169(14) 0.030(4) Uiso 1 1 d . . . C11 C -0.29329(18) 0.47732(17) 0.53756(14) 0.0332(3) Uani 1 1 d . . . H11A H -0.375(2) 0.486(2) 0.5939(17) 0.051(5) Uiso 1 1 d . . . H11B H -0.1969(19) 0.4702(19) 0.5902(15) 0.035(4) Uiso 1 1 d . . . H11C H -0.2957(18) 0.569(2) 0.4918(15) 0.042(4) Uiso 1 1 d . . . C12 C -0.47638(19) 0.36822(19) 0.38242(16) 0.0393(4) Uani 1 1 d . . . H12A H -0.552(2) 0.367(2) 0.4378(17) 0.041(5) Uiso 1 1 d . . . H12B H -0.4845(18) 0.457(2) 0.3338(15) 0.040(5) Uiso 1 1 d . . . H12C H -0.499(2) 0.284(3) 0.3209(19) 0.062(6) Uiso 1 1 d . . . C13 C 0.27096(15) 0.18678(15) 0.78541(12) 0.0267(3) Uani 1 1 d . . . C14 C 0.38610(16) 0.26566(16) 0.74509(13) 0.0297(3) Uani 1 1 d . . . H14 H 0.3647(18) 0.3245(19) 0.6684(16) 0.036(4) Uiso 1 1 d . . . C15 C 0.52491(17) 0.25930(16) 0.80844(13) 0.0299(3) Uani 1 1 d . . . H15 H 0.6036(18) 0.3109(18) 0.7799(14) 0.030(4) Uiso 1 1 d . . . C16 C 0.55045(16) 0.17443(16) 0.91215(12) 0.0282(3) Uani 1 1 d . . . C17 C 0.42722(16) 0.10228(18) 0.94552(13) 0.0327(3) Uani 1 1 d . . . H17 H 0.4411(16) 0.0420(18) 1.0178(15) 0.033(4) Uiso 1 1 d . . . C18 C 0.69768(16) 0.15925(15) 0.98326(12) 0.0286(3) Uani 1 1 d . . . C19 C 0.73967(17) 0.02907(17) 1.03957(14) 0.0324(3) Uani 1 1 d . . . H19 H 0.6717(18) -0.054(2) 1.0282(15) 0.038(4) Uiso 1 1 d . . . C20 C 0.87714(19) 0.01246(18) 1.10476(13) 0.0346(4) Uani 1 1 d . . . H20 H 0.908(2) -0.077(2) 1.1357(16) 0.044(5) Uiso 1 1 d . . . C21 C 0.97611(17) 0.12556(17) 1.11554(12) 0.0307(3) Uani 1 1 d . . . C22 C 0.93716(17) 0.25574(18) 1.06214(13) 0.0325(3) Uani 1 1 d . . . H22 H 1.0046(18) 0.335(2) 1.0707(14) 0.033(4) Uiso 1 1 d . . . C23 C 0.79844(17) 0.27092(17) 0.99641(13) 0.0317(3) Uani 1 1 d . . . H23 H 0.7723(18) 0.361(2) 0.9571(15) 0.036(4) Uiso 1 1 d . . . C24 C 1.2191(2) 0.2062(2) 1.18631(17) 0.0419(4) Uani 1 1 d . . . H24A H 1.2348(18) 0.235(2) 1.1042(17) 0.041(5) Uiso 1 1 d . . . H24B H 1.305(2) 0.164(2) 1.2315(16) 0.042(5) Uiso 1 1 d . . . H24C H 1.193(2) 0.292(3) 1.2321(19) 0.061(6) 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 N1 0.0297(6) 0.0252(6) 0.0286(6) 0.0006(5) 0.0071(5) 0.0038(5) N2 0.0322(7) 0.0352(8) 0.0319(6) 0.0059(5) 0.0051(5) 0.0008(6) O1 0.0382(6) 0.0422(7) 0.0425(6) 0.0052(5) -0.0092(5) -0.0047(6) C1 0.0315(7) 0.0197(7) 0.0276(7) -0.0020(6) 0.0069(6) 0.0049(7) C2 0.0363(8) 0.0221(7) 0.0267(7) -0.0002(6) 0.0089(6) 0.0037(6) C3 0.0311(7) 0.0207(7) 0.0337(7) 0.0003(6) 0.0112(6) -0.0004(6) C4 0.0292(7) 0.0200(7) 0.0309(7) -0.0040(6) 0.0073(6) 0.0016(6) C5 0.0311(7) 0.0242(8) 0.0359(8) 0.0000(6) 0.0038(6) -0.0050(7) C6 0.0305(7) 0.0254(8) 0.0310(7) 0.0011(6) 0.0005(6) -0.0008(6) C7 0.0390(8) 0.0337(8) 0.0262(7) 0.0006(6) 0.0031(6) 0.0013(7) C8 0.0325(8) 0.0405(10) 0.0296(8) 0.0060(7) 0.0079(6) 0.0019(7) C9 0.0315(7) 0.0235(7) 0.0269(7) 0.0009(6) 0.0068(6) 0.0022(6) C10 0.0449(9) 0.0313(9) 0.0349(8) -0.0061(6) 0.0002(7) 0.0020(7) C11 0.0380(9) 0.0264(8) 0.0350(8) 0.0004(6) 0.0027(7) 0.0018(7) C12 0.0354(9) 0.0375(10) 0.0434(9) 0.0012(8) -0.0018(8) -0.0001(8) C13 0.0325(7) 0.0226(7) 0.0259(7) -0.0018(6) 0.0074(5) 0.0040(7) C14 0.0339(8) 0.0264(7) 0.0293(7) 0.0050(6) 0.0053(6) 0.0044(7) C15 0.0314(7) 0.0244(7) 0.0356(8) 0.0015(6) 0.0108(6) 0.0017(7) C16 0.0307(7) 0.0254(7) 0.0290(7) -0.0011(6) 0.0061(6) 0.0046(6) C17 0.0348(8) 0.0353(9) 0.0285(7) 0.0075(6) 0.0057(6) 0.0033(7) C18 0.0330(8) 0.0277(8) 0.0262(7) -0.0024(6) 0.0078(6) 0.0030(7) C19 0.0344(8) 0.0281(8) 0.0340(8) 0.0004(6) 0.0014(6) -0.0038(7) C20 0.0399(9) 0.0303(9) 0.0329(8) 0.0064(6) 0.0008(7) 0.0008(7) C21 0.0338(8) 0.0330(8) 0.0244(6) -0.0028(6) -0.0001(5) -0.0001(7) C22 0.0358(8) 0.0265(8) 0.0358(8) -0.0065(6) 0.0070(6) -0.0028(7) C23 0.0366(8) 0.0232(8) 0.0361(8) -0.0003(6) 0.0074(6) 0.0032(7) C24 0.0359(9) 0.0463(10) 0.0421(10) -0.0034(8) -0.0008(7) -0.0067(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 N1 C9 1.3312(18) . ? N1 C1 1.3494(18) . ? N2 C17 1.332(2) . ? N2 C13 1.3436(18) . ? O1 C21 1.3674(18) . ? O1 C24 1.422(2) . ? C1 C2 1.396(2) . ? C1 C13 1.4850(19) . ? C2 C3 1.383(2) . ? C2 H2 0.956(16) . ? C3 C4 1.382(2) . ? C3 H3 0.977(15) . ? C4 C9 1.4076(19) . ? C4 C5 1.5029(19) . ? C5 C10 1.553(2) . ? C5 C6 1.572(2) . ? C5 H5 0.986(18) . ? C6 C11 1.520(2) . ? C6 C12 1.528(2) . ? C6 C7 1.562(2) . ? C7 C8 1.523(2) . ? C7 C10 1.555(2) . ? C7 H7 0.963(16) . ? C8 C9 1.5110(19) . ? C8 H8A 0.961(18) . ? C8 H8B 0.96(2) . ? C10 H10A 0.973(18) . ? C10 H10B 1.010(15) . ? C11 H11A 1.03(2) . ? C11 H11B 1.000(17) . ? C11 H11C 1.00(2) . ? C12 H12A 0.98(2) . ? C12 H12B 0.99(2) . ? C12 H12C 1.05(2) . ? C13 C14 1.397(2) . ? C14 C15 1.376(2) . ? C14 H14 1.016(18) . ? C15 C16 1.400(2) . ? C15 H15 0.948(17) . ? C16 C17 1.395(2) . ? C16 C18 1.483(2) . ? C17 H17 0.980(17) . ? C18 C23 1.384(2) . ? C18 C19 1.400(2) . ? C19 C20 1.381(2) . ? C19 H19 0.989(19) . ? C20 C21 1.384(2) . ? C20 H20 0.94(2) . ? C21 C22 1.381(2) . ? C22 C23 1.392(2) . ? C22 H22 0.960(18) . ? C23 H23 0.964(19) . ? C24 H24A 0.982(19) . ? C24 H24B 0.964(19) . ? C24 H24C 1.00(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 C9 N1 C1 118.17(12) . . ? C17 N2 C13 117.82(13) . . ? C21 O1 C24 117.29(13) . . ? N1 C1 C2 122.04(13) . . ? N1 C1 C13 116.29(12) . . ? C2 C1 C13 121.67(12) . . ? C3 C2 C1 118.91(13) . . ? C3 C2 H2 122.4(9) . . ? C1 C2 H2 118.7(9) . . ? C4 C3 C2 119.93(13) . . ? C4 C3 H3 121.1(8) . . ? C2 C3 H3 118.9(8) . . ? C3 C4 C9 117.30(12) . . ? C3 C4 C5 126.20(13) . . ? C9 C4 C5 116.47(12) . . ? C4 C5 C10 106.71(12) . . ? C4 C5 C6 110.13(12) . . ? C10 C5 C6 87.29(11) . . ? C4 C5 H5 110.9(9) . . ? C10 C5 H5 122.8(10) . . ? C6 C5 H5 116.6(10) . . ? C11 C6 C12 108.82(13) . . ? C11 C6 C7 119.82(13) . . ? C12 C6 C7 111.00(13) . . ? C11 C6 C5 118.28(12) . . ? C12 C6 C5 112.08(13) . . ? C7 C6 C5 85.20(11) . . ? C8 C7 C10 108.64(13) . . ? C8 C7 C6 111.31(12) . . ? C10 C7 C6 87.59(11) . . ? C8 C7 H7 112.8(9) . . ? C10 C7 H7 117.0(9) . . ? C6 C7 H7 116.9(9) . . ? C9 C8 C7 111.19(13) . . ? C9 C8 H8A 109.3(10) . . ? C7 C8 H8A 109.8(10) . . ? C9 C8 H8B 108.4(10) . . ? C7 C8 H8B 110.7(10) . . ? H8A C8 H8B 107.4(16) . . ? N1 C9 C4 123.63(12) . . ? N1 C9 C8 118.49(12) . . ? C4 C9 C8 117.88(13) . . ? C5 C10 C7 86.08(11) . . ? C5 C10 H10A 115.9(9) . . ? C7 C10 H10A 116.8(10) . . ? C5 C10 H10B 113.9(9) . . ? C7 C10 H10B 109.8(9) . . ? H10A C10 H10B 112.0(13) . . ? C6 C11 H11A 110.9(11) . . ? C6 C11 H11B 113.3(10) . . ? H11A C11 H11B 106.9(13) . . ? C6 C11 H11C 110.6(10) . . ? H11A C11 H11C 105.9(15) . . ? H11B C11 H11C 108.9(14) . . ? C6 C12 H12A 110.6(10) . . ? C6 C12 H12B 111.8(9) . . ? H12A C12 H12B 109.8(15) . . ? C6 C12 H12C 110.8(11) . . ? H12A C12 H12C 107.8(16) . . ? H12B C12 H12C 105.8(16) . . ? N2 C13 C14 121.60(13) . . ? N2 C13 C1 116.65(12) . . ? C14 C13 C1 121.74(12) . . ? C15 C14 C13 119.35(13) . . ? C15 C14 H14 122.1(10) . . ? C13 C14 H14 118.6(10) . . ? C14 C15 C16 120.28(14) . . ? C14 C15 H15 119.3(9) . . ? C16 C15 H15 120.4(9) . . ? C17 C16 C15 115.61(13) . . ? C17 C16 C18 121.02(13) . . ? C15 C16 C18 123.37(13) . . ? N2 C17 C16 125.32(14) . . ? N2 C17 H17 116.9(9) . . ? C16 C17 H17 117.8(9) . . ? C23 C18 C19 117.52(13) . . ? C23 C18 C16 122.09(13) . . ? C19 C18 C16 120.39(14) . . ? C20 C19 C18 121.16(15) . . ? C20 C19 H19 119.6(10) . . ? C18 C19 H19 119.1(10) . . ? C19 C20 C21 120.08(15) . . ? C19 C20 H20 120.8(11) . . ? C21 C20 H20 118.9(11) . . ? O1 C21 C22 124.66(14) . . ? O1 C21 C20 115.26(14) . . ? C22 C21 C20 120.07(14) . . ? C21 C22 C23 119.27(15) . . ? C21 C22 H22 120.4(10) . . ? C23 C22 H22 120.3(10) . . ? C18 C23 C22 121.91(14) . . ? C18 C23 H23 118.7(10) . . ? C22 C23 H23 119.3(10) . . ? O1 C24 H24A 109.5(10) . . ? O1 C24 H24B 104.3(12) . . ? H24A C24 H24B 113.9(15) . . ? O1 C24 H24C 112.8(12) . . ? H24A C24 H24C 109.2(16) . . ? H24B C24 H24C 107.1(15) . . ? 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 N1 C1 C2 -1.0(2) . . . . ? C9 N1 C1 C13 178.86(12) . . . . ? N1 C1 C2 C3 0.9(2) . . . . ? C13 C1 C2 C3 -178.99(12) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C2 C3 C4 C9 -1.6(2) . . . . ? C2 C3 C4 C5 176.59(13) . . . . ? C3 C4 C5 C10 -132.56(15) . . . . ? C9 C4 C5 C10 45.64(17) . . . . ? C3 C4 C5 C6 134.14(14) . . . . ? C9 C4 C5 C6 -47.66(16) . . . . ? C4 C5 C6 C11 -42.14(17) . . . . ? C10 C5 C6 C11 -148.95(14) . . . . ? C4 C5 C6 C12 -169.97(13) . . . . ? C10 C5 C6 C12 83.22(14) . . . . ? C4 C5 C6 C7 79.29(12) . . . . ? C10 C5 C6 C7 -27.52(11) . . . . ? C11 C6 C7 C8 38.39(18) . . . . ? C12 C6 C7 C8 166.58(14) . . . . ? C5 C6 C7 C8 -81.59(14) . . . . ? C11 C6 C7 C10 147.47(13) . . . . ? C12 C6 C7 C10 -84.34(14) . . . . ? C5 C6 C7 C10 27.49(10) . . . . ? C10 C7 C8 C9 -45.27(17) . . . . ? C6 C7 C8 C9 49.54(18) . . . . ? C1 N1 C9 C4 -0.2(2) . . . . ? C1 N1 C9 C8 -179.91(13) . . . . ? C3 C4 C9 N1 1.5(2) . . . . ? C5 C4 C9 N1 -176.86(13) . . . . ? C3 C4 C9 C8 -178.80(13) . . . . ? C5 C4 C9 C8 2.84(19) . . . . ? C7 C8 C9 N1 176.50(13) . . . . ? C7 C8 C9 C4 -3.2(2) . . . . ? C4 C5 C10 C7 -82.59(13) . . . . ? C6 C5 C10 C7 27.63(11) . . . . ? C8 C7 C10 C5 83.89(13) . . . . ? C6 C7 C10 C5 -27.81(11) . . . . ? C17 N2 C13 C14 -1.3(2) . . . . ? C17 N2 C13 C1 179.06(13) . . . . ? N1 C1 C13 N2 -171.85(13) . . . . ? C2 C1 C13 N2 8.01(19) . . . . ? N1 C1 C13 C14 8.52(19) . . . . ? C2 C1 C13 C14 -171.61(14) . . . . ? N2 C13 C14 C15 1.2(2) . . . . ? C1 C13 C14 C15 -179.15(13) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C17 -1.2(2) . . . . ? C14 C15 C16 C18 178.37(14) . . . . ? C13 N2 C17 C16 0.1(2) . . . . ? C15 C16 C17 N2 1.2(2) . . . . ? C18 C16 C17 N2 -178.41(15) . . . . ? C17 C16 C18 C23 -146.30(15) . . . . ? C15 C16 C18 C23 34.2(2) . . . . ? C17 C16 C18 C19 34.0(2) . . . . ? C15 C16 C18 C19 -145.58(15) . . . . ? C23 C18 C19 C20 -0.6(2) . . . . ? C16 C18 C19 C20 179.10(15) . . . . ? C18 C19 C20 C21 0.1(2) . . . . ? C24 O1 C21 C22 -5.0(2) . . . . ? C24 O1 C21 C20 175.00(14) . . . . ? C19 C20 C21 O1 -179.39(14) . . . . ? C19 C20 C21 C22 0.6(2) . . . . ? O1 C21 C22 C23 179.22(14) . . . . ? C20 C21 C22 C23 -0.8(2) . . . . ? C19 C18 C23 C22 0.5(2) . . . . ? C16 C18 C23 C22 -179.28(13) . . . . ? C21 C22 C23 C18 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.133 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.025 #=========================================================================== #========================================= data_cpd2 _database_code_CSD 179703 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 N2' _chemical_formula_weight 326.43 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8641(16) _cell_length_b 6.3600(8) _cell_length_c 13.0544(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.312(10) _cell_angle_gamma 90.00 _cell_volume 902.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used '17 + equivalents' _cell_measurement_theta_min 12.55 _cell_measurement_theta_max 18.60 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'STOE AED2 4-circle diffractometer' _diffrn_measurement_method 2\q/\w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 4520 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2260 _reflns_number_gt 1520 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie GmbH, Darmstadt, 1997)' _computing_cell_refinement 'STADI4 (Stoe & Cie GmbH, Darmstadt, 1997)' _computing_data_reduction 'X-RED (Stoe & Cie GmbH, Darmstadt, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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 w==1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.1223P] 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 0.026(4) _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(6) _refine_ls_number_reflns 2260 _refine_ls_number_parameters 315 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1616(2) 0.9458(4) 0.61076(18) 0.0482(7) Uani 1 d . . . N2 N 0.3415(2) 0.8267(5) 0.38677(19) 0.0507(7) Uani 1 d . . . C1 C 0.2074(3) 0.8360(6) 0.5317(2) 0.0458(8) Uani 1 d . . . C2 C 0.1700(3) 0.6303(6) 0.5124(2) 0.0488(8) Uani 1 d . . . H2 H 0.205(3) 0.559(6) 0.456(2) 0.053(9) Uiso 1 d . . . C3 C 0.0814(3) 0.5372(6) 0.5735(2) 0.0492(8) Uani 1 d . . . H3 H 0.054(3) 0.394(6) 0.556(2) 0.051(9) Uiso 1 d . . . C4 C 0.0329(3) 0.6508(5) 0.6530(2) 0.0438(8) Uani 1 d . . . C5 C -0.0640(3) 0.5737(6) 0.7255(2) 0.0487(8) Uani 1 d . . . H5 H -0.092(3) 0.429(6) 0.710(2) 0.043(8) Uiso 1 d . . . C6 C -0.0210(3) 0.6159(6) 0.8389(2) 0.0511(8) Uani 1 d . . . C7 C -0.0659(3) 0.8457(6) 0.8186(3) 0.0544(9) Uani 1 d . . . H7 H -0.100(3) 0.917(5) 0.875(2) 0.047(9) Uiso 1 d . . . C8 C 0.0302(4) 0.9741(6) 0.7618(3) 0.0583(10) Uani 1 d . . . H8A H -0.004(3) 1.095(8) 0.738(3) 0.070(12) Uiso 1 d . . . H8B H 0.114(3) 1.014(7) 0.807(3) 0.078(12) Uiso 1 d . . . C9 C 0.0773(3) 0.8540(5) 0.6695(2) 0.0462(8) Uani 1 d . . . C10 C -0.1580(3) 0.7544(6) 0.7406(3) 0.0562(9) Uani 1 d . . . H10A H -0.236(3) 0.704(6) 0.776(2) 0.072(11) Uiso 1 d . . . H10B H -0.175(3) 0.840(6) 0.678(3) 0.069(11) Uiso 1 d . . . C11 C 0.1131(4) 0.5755(8) 0.8652(3) 0.0669(11) Uani 1 d . . . H11A H 0.133(3) 0.636(7) 0.933(3) 0.078(11) Uiso 1 d . . . H11B H 0.129(5) 0.405(10) 0.863(4) 0.130(19) Uiso 1 d . . . H11C H 0.172(3) 0.655(7) 0.821(3) 0.081(13) Uiso 1 d . . . C12 C -0.1019(5) 0.5027(8) 0.9157(3) 0.0718(12) Uani 1 d . . . H12A H -0.083(4) 0.349(9) 0.922(3) 0.101(16) Uiso 1 d . . . H12B H -0.079(3) 0.559(7) 0.988(3) 0.076(11) Uiso 1 d . . . H12C H -0.191(3) 0.529(7) 0.901(3) 0.080(13) Uiso 1 d . . . C13 C 0.3007(3) 0.9389(6) 0.4667(2) 0.0471(8) Uani 1 d . . . C14 C 0.3443(3) 1.1393(6) 0.4887(3) 0.0539(9) Uani 1 d . . . H14 H 0.307(3) 1.219(6) 0.547(3) 0.072(11) Uiso 1 d . . . C15 C 0.4309(3) 1.2258(7) 0.4259(3) 0.0629(10) Uani 1 d . . . H15 H 0.465(3) 1.372(7) 0.437(2) 0.064(10) Uiso 1 d . . . C16 C 0.4759(3) 1.1112(8) 0.3447(3) 0.0658(11) Uani 1 d . . . H16 H 0.533(3) 1.161(6) 0.297(2) 0.071(11) Uiso 1 d . . . C17 C 0.4293(3) 0.9113(6) 0.3267(3) 0.0534(10) Uani 1 d . . . C18 C 0.4699(3) 0.7760(7) 0.2399(2) 0.0582(10) Uani 1 d . . . C19 C 0.5888(4) 0.7813(10) 0.2037(3) 0.0847(14) Uani 1 d . . . H19 H 0.646(4) 0.884(8) 0.233(3) 0.112(17) Uiso 1 d . . . C20 C 0.6238(4) 0.6555(11) 0.1232(4) 0.0953(17) Uani 1 d . . . H20 H 0.704(4) 0.656(8) 0.098(3) 0.100(14) Uiso 1 d . . . C21 C 0.5425(5) 0.5206(10) 0.0782(4) 0.0909(16) Uani 1 d . . . H21 H 0.572(4) 0.432(9) 0.026(4) 0.118(18) Uiso 1 d . . . C22 C 0.4229(5) 0.5130(9) 0.1137(4) 0.0940(16) Uani 1 d . . . H22 H 0.372(4) 0.428(9) 0.083(3) 0.113(19) Uiso 1 d . . . C23 C 0.3884(4) 0.6401(8) 0.1936(3) 0.0740(12) Uani 1 d . . . H23 H 0.306(3) 0.624(6) 0.219(2) 0.070(10) Uiso 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 N1 0.0608(16) 0.0374(16) 0.0466(14) -0.0067(13) 0.0006(13) -0.0002(14) N2 0.0487(15) 0.0527(18) 0.0508(15) 0.0028(14) 0.0027(12) -0.0035(14) C1 0.0491(18) 0.043(2) 0.0451(17) -0.0003(15) -0.0045(14) 0.0033(16) C2 0.0545(19) 0.047(2) 0.0449(17) -0.0100(17) 0.0068(15) 0.0001(18) C3 0.064(2) 0.039(2) 0.0450(17) -0.0063(15) 0.0005(15) -0.0036(17) C4 0.0522(17) 0.0404(19) 0.0388(15) -0.0033(15) -0.0044(13) 0.0054(17) C5 0.0551(19) 0.045(2) 0.0458(17) -0.0001(15) 0.0034(14) -0.0012(16) C6 0.0621(19) 0.051(2) 0.0402(15) -0.0018(16) 0.0000(13) 0.0084(18) C7 0.068(2) 0.051(2) 0.0443(17) -0.0095(16) 0.0079(16) 0.0141(18) C8 0.083(3) 0.038(2) 0.054(2) -0.0113(18) 0.0090(19) 0.007(2) C9 0.0585(19) 0.0380(19) 0.0420(16) -0.0044(15) 0.0025(15) 0.0041(17) C10 0.053(2) 0.062(2) 0.0533(19) 0.0060(19) -0.0016(16) 0.0127(19) C11 0.074(3) 0.074(3) 0.052(2) -0.002(2) -0.0091(18) 0.018(2) C12 0.096(3) 0.072(3) 0.048(2) 0.007(2) 0.012(2) 0.009(3) C13 0.0450(17) 0.047(2) 0.0495(18) 0.0007(16) -0.0067(15) -0.0008(17) C14 0.054(2) 0.049(2) 0.059(2) 0.0021(19) -0.0085(17) -0.0012(19) C15 0.058(2) 0.053(3) 0.077(3) 0.001(2) -0.0071(19) -0.012(2) C16 0.055(2) 0.072(3) 0.070(2) 0.011(2) 0.0004(18) -0.017(2) C17 0.0429(18) 0.060(2) 0.057(2) 0.0049(19) -0.0019(15) -0.0030(18) C18 0.0540(19) 0.069(3) 0.0519(19) 0.0065(19) 0.0080(15) -0.006(2) C19 0.062(2) 0.115(4) 0.077(3) -0.017(3) 0.015(2) -0.017(3) C20 0.064(3) 0.134(5) 0.088(3) -0.013(3) 0.026(2) -0.004(3) C21 0.095(3) 0.097(4) 0.081(3) -0.013(3) 0.038(3) -0.002(3) C22 0.103(4) 0.093(4) 0.086(3) -0.024(3) 0.035(3) -0.032(3) C23 0.072(2) 0.073(3) 0.077(2) -0.010(2) 0.031(2) -0.019(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 C9 1.332(4) . ? N1 C1 1.344(4) . ? N2 C13 1.342(4) . ? N2 C17 1.350(4) . ? C1 C2 1.392(5) . ? C1 C13 1.478(4) . ? C2 C3 1.386(5) . ? C3 C4 1.372(4) . ? C4 C9 1.396(5) . ? C4 C5 1.503(4) . ? C5 C10 1.550(5) . ? C5 C6 1.572(4) . ? C6 C11 1.517(5) . ? C6 C12 1.519(5) . ? C6 C7 1.563(5) . ? C7 C8 1.522(5) . ? C7 C10 1.537(5) . ? C8 C9 1.517(4) . ? C13 C14 1.389(5) . ? C14 C15 1.367(5) . ? C15 C16 1.378(6) . ? C16 C17 1.389(6) . ? C17 C18 1.491(5) . ? C18 C23 1.375(5) . ? C18 C19 1.379(5) . ? C19 C20 1.375(6) . ? C20 C21 1.363(7) . ? C21 C22 1.382(6) . ? C22 C23 1.373(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 C9 N1 C1 118.2(3) . . ? C13 N2 C17 118.5(3) . . ? N1 C1 C2 121.2(3) . . ? N1 C1 C13 117.9(3) . . ? C2 C1 C13 120.8(3) . . ? C3 C2 C1 120.0(3) . . ? C4 C3 C2 118.7(3) . . ? C3 C4 C9 118.1(3) . . ? C3 C4 C5 125.3(3) . . ? C9 C4 C5 116.6(3) . . ? C4 C5 C10 107.6(3) . . ? C4 C5 C6 109.3(3) . . ? C10 C5 C6 86.9(2) . . ? C11 C6 C12 109.2(3) . . ? C11 C6 C7 119.7(3) . . ? C12 C6 C7 111.9(3) . . ? C11 C6 C5 117.7(3) . . ? C12 C6 C5 111.7(3) . . ? C7 C6 C5 84.8(2) . . ? C8 C7 C10 109.0(3) . . ? C8 C7 C6 111.7(3) . . ? C10 C7 C6 87.7(3) . . ? C9 C8 C7 110.6(3) . . ? N1 C9 C4 123.7(3) . . ? N1 C9 C8 118.2(3) . . ? C4 C9 C8 118.1(3) . . ? C7 C10 C5 86.4(2) . . ? N2 C13 C14 122.4(3) . . ? N2 C13 C1 116.2(3) . . ? C14 C13 C1 121.5(3) . . ? C15 C14 C13 118.7(4) . . ? C14 C15 C16 119.8(4) . . ? C15 C16 C17 118.9(4) . . ? N2 C17 C16 121.7(4) . . ? N2 C17 C18 115.1(3) . . ? C16 C17 C18 123.2(3) . . ? C23 C18 C19 117.8(4) . . ? C23 C18 C17 120.3(3) . . ? C19 C18 C17 121.9(4) . . ? C20 C19 C18 120.7(5) . . ? C21 C20 C19 121.0(4) . . ? C20 C21 C22 119.1(5) . . ? C23 C22 C21 119.6(5) . . ? C22 C23 C18 121.8(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 C9 N1 C1 C2 -1.2(4) . . . . ? C9 N1 C1 C13 179.9(3) . . . . ? N1 C1 C2 C3 1.8(5) . . . . ? C13 C1 C2 C3 -179.3(3) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C9 -1.2(5) . . . . ? C2 C3 C4 C5 179.5(3) . . . . ? C3 C4 C5 C10 -136.8(3) . . . . ? C9 C4 C5 C10 43.9(4) . . . . ? C3 C4 C5 C6 130.2(3) . . . . ? C9 C4 C5 C6 -49.1(4) . . . . ? C4 C5 C6 C11 -40.9(4) . . . . ? C10 C5 C6 C11 -148.5(4) . . . . ? C4 C5 C6 C12 -168.4(3) . . . . ? C10 C5 C6 C12 84.0(3) . . . . ? C4 C5 C6 C7 80.1(3) . . . . ? C10 C5 C6 C7 -27.6(2) . . . . ? C11 C6 C7 C8 37.3(4) . . . . ? C12 C6 C7 C8 166.9(3) . . . . ? C5 C6 C7 C8 -81.8(3) . . . . ? C11 C6 C7 C10 146.9(3) . . . . ? C12 C6 C7 C10 -83.6(3) . . . . ? C5 C6 C7 C10 27.8(2) . . . . ? C10 C7 C8 C9 -46.6(4) . . . . ? C6 C7 C8 C9 48.7(4) . . . . ? C1 N1 C9 C4 -0.7(5) . . . . ? C1 N1 C9 C8 177.1(3) . . . . ? C3 C4 C9 N1 1.9(5) . . . . ? C5 C4 C9 N1 -178.7(3) . . . . ? C3 C4 C9 C8 -175.9(3) . . . . ? C5 C4 C9 C8 3.4(4) . . . . ? C7 C8 C9 N1 179.4(3) . . . . ? C7 C8 C9 C4 -2.6(5) . . . . ? C8 C7 C10 C5 84.1(3) . . . . ? C6 C7 C10 C5 -28.2(2) . . . . ? C4 C5 C10 C7 -81.4(3) . . . . ? C6 C5 C10 C7 28.0(2) . . . . ? C17 N2 C13 C14 0.9(5) . . . . ? C17 N2 C13 C1 -178.2(3) . . . . ? N1 C1 C13 N2 -178.1(3) . . . . ? C2 C1 C13 N2 3.0(4) . . . . ? N1 C1 C13 C14 2.9(4) . . . . ? C2 C1 C13 C14 -176.1(3) . . . . ? N2 C13 C14 C15 0.8(5) . . . . ? C1 C13 C14 C15 179.8(3) . . . . ? C13 C14 C15 C16 -2.2(5) . . . . ? C14 C15 C16 C17 1.9(6) . . . . ? C13 N2 C17 C16 -1.2(5) . . . . ? C13 N2 C17 C18 179.8(3) . . . . ? C15 C16 C17 N2 -0.2(6) . . . . ? C15 C16 C17 C18 178.8(3) . . . . ? N2 C17 C18 C23 31.8(5) . . . . ? C16 C17 C18 C23 -147.2(4) . . . . ? N2 C17 C18 C19 -147.9(4) . . . . ? C16 C17 C18 C19 33.0(6) . . . . ? C23 C18 C19 C20 0.5(7) . . . . ? C17 C18 C19 C20 -179.7(4) . . . . ? C18 C19 C20 C21 -0.9(8) . . . . ? C19 C20 C21 C22 0.8(9) . . . . ? C20 C21 C22 C23 -0.4(8) . . . . ? C21 C22 C23 C18 0.0(8) . . . . ? C19 C18 C23 C22 0.0(7) . . . . ? C17 C18 C23 C22 -179.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.136 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.030 #=========================================================================== #=============================================== data_cpd3 _database_code_CSD 179704 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 Cl3 N2 O' _chemical_formula_weight 475.82 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.6825(5) _cell_length_b 7.4085(4) _cell_length_c 23.4403(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.080(10) _cell_angle_gamma 90.00 _cell_volume 1157.52(14) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 7989 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 25.92 _exptl_crystal_description plate _exptl_crystal_colour colurless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.416 _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 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9156 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.92 _reflns_number_total 4208 _reflns_number_gt 3435 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0375P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(5) _refine_ls_number_reflns 4208 _refine_ls_number_parameters 380 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0684 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.923 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5308(2) 0.1637(2) 0.61866(5) 0.0290(4) Uani 1 1 d . . . N1 N -0.0290(2) 0.2664(3) 0.21480(6) 0.0221(4) Uani 1 1 d . . . N2 N 0.1077(2) 0.2287(2) 0.36601(6) 0.0201(4) Uani 1 1 d . . . C1 C 0.0848(3) 0.2885(3) 0.26429(7) 0.0198(4) Uani 1 1 d . . . C2 C 0.2822(3) 0.3480(3) 0.26526(8) 0.0239(5) Uani 1 1 d . . . H2 H 0.358(3) 0.369(3) 0.3034(10) 0.036(6) Uiso 1 1 d . . . C3 C 0.3649(3) 0.3857(3) 0.21409(8) 0.0245(5) Uani 1 1 d . . . H3 H 0.499(3) 0.424(3) 0.2133(8) 0.014(5) Uiso 1 1 d . . . C4 C 0.2496(3) 0.3651(3) 0.16304(8) 0.0217(5) Uani 1 1 d . . . C5 C 0.3166(3) 0.4031(3) 0.10437(9) 0.0253(5) Uani 1 1 d . . . H5 H 0.454(3) 0.443(3) 0.1062(9) 0.021(6) Uiso 1 1 d . . . C6 C 0.2557(3) 0.2425(3) 0.06308(7) 0.0275(5) Uani 1 1 d . . . C7 C 0.0445(3) 0.3315(4) 0.05950(9) 0.0303(6) Uani 1 1 d . . . H7 H -0.029(3) 0.315(4) 0.0248(9) 0.035(6) Uiso 1 1 d . . . C8 C -0.0748(3) 0.2774(4) 0.11030(8) 0.0310(5) Uani 1 1 d . . . H8A H -0.204(4) 0.349(3) 0.1106(9) 0.029(6) Uiso 1 1 d . . . H8B H -0.114(4) 0.153(4) 0.1079(10) 0.041(8) Uiso 1 1 d . . . C9 C 0.0519(3) 0.3046(3) 0.16595(7) 0.0210(5) Uani 1 1 d . . . C10 C 0.1471(4) 0.5138(4) 0.07198(10) 0.0303(5) Uani 1 1 d . . . H10A H 0.193(4) 0.577(4) 0.0374(11) 0.032(7) Uiso 1 1 d . . . H10B H 0.081(4) 0.598(4) 0.0920(11) 0.038(7) Uiso 1 1 d . . . C11 C 0.2812(5) 0.0525(4) 0.08559(12) 0.0417(7) Uani 1 1 d . . . H11A H 0.229(5) -0.047(6) 0.0581(16) 0.082(12) Uiso 1 1 d . . . H11B H 0.417(6) 0.025(5) 0.0874(14) 0.073(11) Uiso 1 1 d . . . H11C H 0.220(4) 0.030(4) 0.1207(12) 0.044(7) Uiso 1 1 d . . . C12 C 0.3550(4) 0.2566(5) 0.00649(9) 0.0386(6) Uani 1 1 d . . . H12A H 0.301(4) 0.169(4) -0.0198(11) 0.040(7) Uiso 1 1 d . . . H12B H 0.342(3) 0.374(4) -0.0089(10) 0.028(7) Uiso 1 1 d . . . H12C H 0.484(5) 0.220(5) 0.0095(11) 0.053(8) Uiso 1 1 d . . . C13 C -0.0124(3) 0.2381(3) 0.31742(7) 0.0197(4) Uani 1 1 d . . . C14 C -0.2157(3) 0.1987(3) 0.31567(8) 0.0235(5) Uani 1 1 d . . . H14 H -0.288(3) 0.212(3) 0.2827(9) 0.025(6) Uiso 1 1 d . . . C15 C -0.2966(3) 0.1407(3) 0.36467(9) 0.0261(5) Uani 1 1 d . . . H15 H -0.441(3) 0.109(3) 0.3645(9) 0.022(6) Uiso 1 1 d . . . C16 C -0.1756(3) 0.1258(3) 0.41429(9) 0.0243(5) Uani 1 1 d . . . H16 H -0.220(3) 0.089(3) 0.4482(10) 0.021(6) Uiso 1 1 d . . . C17 C 0.0270(3) 0.1748(3) 0.41413(8) 0.0207(4) Uani 1 1 d . . . C18 C 0.1628(3) 0.1732(3) 0.46722(8) 0.0197(4) Uani 1 1 d . . . C19 C 0.1087(3) 0.0860(3) 0.51685(9) 0.0237(5) Uani 1 1 d . . . H19 H -0.016(4) 0.022(3) 0.5179(8) 0.024(6) Uiso 1 1 d . . . C20 C 0.2332(3) 0.0875(3) 0.56643(9) 0.0244(5) Uani 1 1 d . . . H20 H 0.196(3) 0.028(4) 0.5988(10) 0.024(6) Uiso 1 1 d . . . C21 C 0.4167(3) 0.1762(3) 0.56797(8) 0.0231(5) Uani 1 1 d . . . C22 C 0.4735(3) 0.2650(3) 0.51942(7) 0.0219(4) Uani 1 1 d . . . H22 H 0.595(3) 0.327(3) 0.5214(8) 0.023(6) Uiso 1 1 d . . . C23 C 0.3461(3) 0.2623(3) 0.46981(8) 0.0215(4) Uani 1 1 d . . . H23 H 0.385(3) 0.325(3) 0.4375(8) 0.014(5) Uiso 1 1 d . . . C24 C 0.7242(3) 0.2460(5) 0.62212(10) 0.0386(6) Uani 1 1 d . . . H24A H 0.797(3) 0.198(3) 0.5931(9) 0.023(6) Uiso 1 1 d . . . H24B H 0.774(3) 0.215(4) 0.6592(10) 0.034(6) Uiso 1 1 d . . . H24C H 0.714(4) 0.386(5) 0.6188(11) 0.053(9) Uiso 1 1 d . . . Cl1 Cl 0.72633(13) 0.73699(11) 0.27713(3) 0.0628(2) Uani 1 1 d . . . Cl2 Cl 1.09053(11) 0.79162(11) 0.21974(3) 0.0559(2) Uani 1 1 d . . . Cl3 Cl 0.71095(11) 0.77259(12) 0.15372(2) 0.0574(2) Uani 1 1 d . . . C25 C 0.8336(4) 0.8405(4) 0.21953(10) 0.0402(6) Uani 1 1 d . . . H25 H 0.822(3) 0.966(4) 0.2219(9) 0.022(6) 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 O1 0.0291(8) 0.0373(11) 0.0203(7) 0.0024(6) 0.0001(6) -0.0015(7) N1 0.0206(8) 0.0238(11) 0.0219(7) -0.0010(8) 0.0009(6) 0.0013(8) N2 0.0220(8) 0.0193(11) 0.0194(7) 0.0008(7) 0.0040(6) 0.0015(7) C1 0.0203(9) 0.0187(13) 0.0204(9) 0.0000(9) 0.0015(7) 0.0030(8) C2 0.0231(10) 0.0278(15) 0.0205(10) 0.0022(8) -0.0016(8) 0.0014(9) C3 0.0192(11) 0.0304(15) 0.0238(10) 0.0019(9) 0.0003(8) -0.0024(9) C4 0.0207(10) 0.0203(14) 0.0243(10) 0.0019(8) 0.0022(8) 0.0012(8) C5 0.0219(12) 0.0298(16) 0.0243(11) 0.0042(9) 0.0027(9) -0.0024(9) C6 0.0332(11) 0.0294(16) 0.0202(9) 0.0006(10) 0.0044(8) 0.0008(10) C7 0.0299(11) 0.0423(18) 0.0177(10) 0.0023(9) -0.0050(9) 0.0006(10) C8 0.0260(11) 0.0453(19) 0.0212(10) -0.0012(11) -0.0016(8) -0.0025(12) C9 0.0215(9) 0.0211(14) 0.0201(9) -0.0005(8) 0.0008(7) 0.0033(9) C10 0.0371(13) 0.0285(16) 0.0251(12) 0.0078(10) 0.0013(10) 0.0062(10) C11 0.061(2) 0.036(2) 0.0298(14) -0.0004(11) 0.0117(13) 0.0066(13) C12 0.0465(15) 0.045(2) 0.0254(11) -0.0011(13) 0.0102(10) 0.0018(14) C13 0.0214(9) 0.0167(13) 0.0210(9) -0.0027(8) 0.0022(7) 0.0029(8) C14 0.0215(10) 0.0253(15) 0.0236(10) -0.0047(8) 0.0014(8) 0.0019(8) C15 0.0200(11) 0.0295(15) 0.0293(11) -0.0058(9) 0.0053(8) -0.0018(9) C16 0.0245(11) 0.0267(16) 0.0226(10) -0.0010(9) 0.0082(8) -0.0012(9) C17 0.0219(10) 0.0180(13) 0.0225(9) -0.0023(8) 0.0043(8) 0.0025(8) C18 0.0212(10) 0.0175(13) 0.0211(9) -0.0025(8) 0.0051(7) 0.0031(8) C19 0.0245(11) 0.0226(14) 0.0247(11) 0.0021(9) 0.0062(9) -0.0024(9) C20 0.0306(12) 0.0224(14) 0.0209(10) 0.0045(9) 0.0063(9) -0.0004(9) C21 0.0249(10) 0.0247(14) 0.0197(9) -0.0020(8) 0.0019(8) 0.0044(9) C22 0.0210(9) 0.0222(13) 0.0231(9) -0.0020(10) 0.0052(7) 0.0000(9) C23 0.0247(10) 0.0205(13) 0.0200(9) 0.0013(9) 0.0077(7) -0.0011(9) C24 0.0319(12) 0.056(2) 0.0271(11) 0.0005(13) -0.0051(9) -0.0065(13) Cl1 0.1050(6) 0.0485(6) 0.0369(3) -0.0033(3) 0.0182(3) -0.0309(4) Cl2 0.0685(4) 0.0533(6) 0.0455(3) 0.0048(3) 0.0011(3) 0.0191(4) Cl3 0.0806(5) 0.0533(5) 0.0364(3) -0.0006(3) -0.0103(3) -0.0036(4) C25 0.0612(17) 0.026(2) 0.0336(13) -0.0007(10) 0.0036(11) -0.0026(12) _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 O1 C21 1.368(2) . ? O1 C24 1.426(3) . ? N1 C9 1.331(2) . ? N1 C1 1.351(2) . ? N2 C17 1.345(2) . ? N2 C13 1.348(2) . ? C1 C2 1.389(3) . ? C1 C13 1.493(2) . ? C2 C3 1.384(3) . ? C2 H2 1.01(2) . ? C3 C4 1.385(3) . ? C3 H3 0.94(2) . ? C4 C9 1.402(3) . ? C4 C5 1.503(3) . ? C5 C10 1.552(3) . ? C5 C6 1.569(3) . ? C5 H5 0.97(2) . ? C6 C11 1.508(4) . ? C6 C12 1.528(3) . ? C6 C7 1.555(3) . ? C7 C8 1.532(3) . ? C7 C10 1.534(4) . ? C7 H7 0.93(2) . ? C8 C9 1.517(3) . ? C8 H8A 1.01(2) . ? C8 H8B 0.96(3) . ? C10 H10A 1.00(3) . ? C10 H10B 0.91(3) . ? C11 H11A 1.02(4) . ? C11 H11B 0.93(4) . ? C11 H11C 0.96(3) . ? C12 H12A 0.95(3) . ? C12 H12B 0.94(3) . ? C12 H12C 0.90(3) . ? C13 C14 1.387(3) . ? C14 C15 1.373(3) . ? C14 H14 0.89(2) . ? C15 C16 1.373(3) . ? C15 H15 0.99(2) . ? C16 C17 1.402(3) . ? C16 H16 0.91(2) . ? C17 C18 1.487(3) . ? C18 C23 1.389(3) . ? C18 C19 1.400(3) . ? C19 C20 1.381(3) . ? C19 H19 0.96(3) . ? C20 C21 1.389(3) . ? C20 H20 0.93(2) . ? C21 C22 1.390(3) . ? C22 C23 1.392(3) . ? C22 H22 0.93(2) . ? C23 H23 0.94(2) . ? C24 H24A 0.93(2) . ? C24 H24B 0.94(2) . ? C24 H24C 1.04(3) . ? Cl1 C25 1.750(3) . ? Cl2 C25 1.754(3) . ? Cl3 C25 1.768(2) . ? C25 H25 0.93(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 C21 O1 C24 117.85(17) . . ? C9 N1 C1 118.35(15) . . ? C17 N2 C13 118.26(15) . . ? N1 C1 C2 121.89(16) . . ? N1 C1 C13 115.75(15) . . ? C2 C1 C13 122.32(15) . . ? C3 C2 C1 119.13(18) . . ? C3 C2 H2 122.1(13) . . ? C1 C2 H2 118.7(13) . . ? C2 C3 C4 119.66(19) . . ? C2 C3 H3 121.1(12) . . ? C4 C3 H3 119.3(12) . . ? C3 C4 C9 117.48(18) . . ? C3 C4 C5 125.93(18) . . ? C9 C4 C5 116.59(17) . . ? C4 C5 C10 107.00(17) . . ? C4 C5 C6 109.96(18) . . ? C10 C5 C6 87.20(17) . . ? C4 C5 H5 111.3(12) . . ? C10 C5 H5 121.3(14) . . ? C6 C5 H5 117.6(13) . . ? C11 C6 C12 108.8(2) . . ? C11 C6 C7 119.6(2) . . ? C12 C6 C7 111.88(18) . . ? C11 C6 C5 118.29(18) . . ? C12 C6 C5 112.0(2) . . ? C7 C6 C5 84.61(17) . . ? C8 C7 C10 109.4(2) . . ? C8 C7 C6 111.56(18) . . ? C10 C7 C6 88.36(17) . . ? C8 C7 H7 112.0(14) . . ? C10 C7 H7 119.0(17) . . ? C6 C7 H7 114.5(15) . . ? C9 C8 C7 110.15(17) . . ? C9 C8 H8A 110.4(12) . . ? C7 C8 H8A 111.0(13) . . ? C9 C8 H8B 108.1(15) . . ? C7 C8 H8B 111.1(15) . . ? H8A C8 H8B 106(2) . . ? N1 C9 C4 123.49(16) . . ? N1 C9 C8 118.41(17) . . ? C4 C9 C8 118.08(17) . . ? C7 C10 C5 85.89(18) . . ? C7 C10 H10A 114.4(15) . . ? C5 C10 H10A 112.7(14) . . ? C7 C10 H10B 118.2(17) . . ? C5 C10 H10B 118.1(16) . . ? H10A C10 H10B 107(2) . . ? C6 C11 H11A 115(2) . . ? C6 C11 H11B 108(2) . . ? H11A C11 H11B 99(3) . . ? C6 C11 H11C 114.9(18) . . ? H11A C11 H11C 106(3) . . ? H11B C11 H11C 113(3) . . ? C6 C12 H12A 110.5(16) . . ? C6 C12 H12B 111.1(15) . . ? H12A C12 H12B 111(2) . . ? C6 C12 H12C 112.5(17) . . ? H12A C12 H12C 100(3) . . ? H12B C12 H12C 112(3) . . ? N2 C13 C14 122.50(17) . . ? N2 C13 C1 116.72(15) . . ? C14 C13 C1 120.75(16) . . ? C15 C14 C13 118.96(18) . . ? C15 C14 H14 122.6(13) . . ? C13 C14 H14 118.4(13) . . ? C14 C15 C16 119.40(19) . . ? C14 C15 H15 120.7(12) . . ? C16 C15 H15 119.9(12) . . ? C15 C16 C17 119.2(2) . . ? C15 C16 H16 123.6(13) . . ? C17 C16 H16 117.2(13) . . ? N2 C17 C16 121.62(17) . . ? N2 C17 C18 116.54(16) . . ? C16 C17 C18 121.84(17) . . ? C23 C18 C19 117.50(17) . . ? C23 C18 C17 121.11(18) . . ? C19 C18 C17 121.37(18) . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H19 117.1(13) . . ? C18 C19 H19 121.6(12) . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20 120.2(14) . . ? C21 C20 H20 119.5(14) . . ? O1 C21 C20 115.25(18) . . ? O1 C21 C22 125.10(19) . . ? C20 C21 C22 119.64(18) . . ? C21 C22 C23 119.36(19) . . ? C21 C22 H22 118.7(12) . . ? C23 C22 H22 121.9(13) . . ? C18 C23 C22 121.94(19) . . ? C18 C23 H23 119.5(11) . . ? C22 C23 H23 118.6(12) . . ? O1 C24 H24A 108.4(13) . . ? O1 C24 H24B 102.2(14) . . ? H24A C24 H24B 114.2(19) . . ? O1 C24 H24C 111.5(15) . . ? H24A C24 H24C 111(2) . . ? H24B C24 H24C 109(2) . . ? Cl1 C25 Cl2 111.21(15) . . ? Cl1 C25 Cl3 111.00(16) . . ? Cl2 C25 Cl3 109.68(14) . . ? Cl1 C25 H25 110.5(13) . . ? Cl2 C25 H25 106.9(13) . . ? Cl3 C25 H25 107.4(13) . . ? 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 N1 C1 C2 -0.5(3) . . . . ? C9 N1 C1 C13 -178.2(2) . . . . ? N1 C1 C2 C3 0.0(3) . . . . ? C13 C1 C2 C3 177.5(2) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C9 -0.5(3) . . . . ? C2 C3 C4 C5 179.0(2) . . . . ? C3 C4 C5 C10 -133.6(2) . . . . ? C9 C4 C5 C10 45.9(3) . . . . ? C3 C4 C5 C6 133.1(2) . . . . ? C9 C4 C5 C6 -47.4(3) . . . . ? C4 C5 C6 C11 -41.1(3) . . . . ? C10 C5 C6 C11 -148.2(2) . . . . ? C4 C5 C6 C12 -168.85(19) . . . . ? C10 C5 C6 C12 84.1(2) . . . . ? C4 C5 C6 C7 79.71(18) . . . . ? C10 C5 C6 C7 -27.37(15) . . . . ? C11 C6 C7 C8 37.1(3) . . . . ? C12 C6 C7 C8 165.9(2) . . . . ? C5 C6 C7 C8 -82.5(2) . . . . ? C11 C6 C7 C10 147.3(2) . . . . ? C12 C6 C7 C10 -83.8(2) . . . . ? C5 C6 C7 C10 27.71(15) . . . . ? C10 C7 C8 C9 -46.5(3) . . . . ? C6 C7 C8 C9 49.6(3) . . . . ? C1 N1 C9 C4 0.6(3) . . . . ? C1 N1 C9 C8 179.2(2) . . . . ? C3 C4 C9 N1 -0.1(3) . . . . ? C5 C4 C9 N1 -179.6(2) . . . . ? C3 C4 C9 C8 -178.7(2) . . . . ? C5 C4 C9 C8 1.8(3) . . . . ? C7 C8 C9 N1 179.2(2) . . . . ? C7 C8 C9 C4 -2.1(3) . . . . ? C8 C7 C10 C5 84.33(19) . . . . ? C6 C7 C10 C5 -27.98(15) . . . . ? C4 C5 C10 C7 -82.30(19) . . . . ? C6 C5 C10 C7 27.73(15) . . . . ? C17 N2 C13 C14 1.6(3) . . . . ? C17 N2 C13 C1 -176.72(19) . . . . ? N1 C1 C13 N2 168.76(19) . . . . ? C2 C1 C13 N2 -8.9(3) . . . . ? N1 C1 C13 C14 -9.6(3) . . . . ? C2 C1 C13 C14 172.7(2) . . . . ? N2 C13 C14 C15 -2.8(3) . . . . ? C1 C13 C14 C15 175.5(2) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? C14 C15 C16 C17 1.7(3) . . . . ? C13 N2 C17 C16 1.3(3) . . . . ? C13 N2 C17 C18 -177.68(19) . . . . ? C15 C16 C17 N2 -2.9(3) . . . . ? C15 C16 C17 C18 175.9(2) . . . . ? N2 C17 C18 C23 14.9(3) . . . . ? C16 C17 C18 C23 -164.1(2) . . . . ? N2 C17 C18 C19 -166.7(2) . . . . ? C16 C17 C18 C19 14.3(3) . . . . ? C23 C18 C19 C20 -0.3(3) . . . . ? C17 C18 C19 C20 -178.8(2) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C24 O1 C21 C20 177.5(2) . . . . ? C24 O1 C21 C22 -0.8(3) . . . . ? C19 C20 C21 O1 -177.9(2) . . . . ? C19 C20 C21 C22 0.6(4) . . . . ? O1 C21 C22 C23 177.7(2) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? C19 C18 C23 C22 0.4(3) . . . . ? C17 C18 C23 C22 178.8(2) . . . . ? C21 C22 C23 C18 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.92 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.262 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.037 #=========================================================================== #================================================== data_cpd7 _database_code_CSD 179705 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 N4' _chemical_formula_weight 754.98 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 11.4989(5) _cell_length_b 14.7712(8) _cell_length_c 25.1410(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4270.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.95 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.068 _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 153(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 'STOE Image Plate Diffraction System' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31668 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0967 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.95 _reflns_number_total 8128 _reflns_number_gt 4620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe & Cie GmbH, Darmstadt, 1997)' _computing_cell_refinement 'CELL (Stoe & Cie GmbH, Darmstadt, 1997)' _computing_data_reduction 'INTEGRATE (Stoe & Cie GmbH, Darmstadt, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0173P)^2^] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00485(16) _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 2(2) _refine_ls_number_reflns 8128 _refine_ls_number_parameters 724 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0558 _refine_ls_wR_factor_gt 0.0487 _refine_ls_goodness_of_fit_ref 0.730 _refine_ls_restrained_S_all 0.730 _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 -0.68988(16) -0.49045(11) 0.19149(6) 0.0326(4) Uani 1 1 d . . . N2 N -0.48161(17) -0.48226(11) 0.29722(6) 0.0367(5) Uani 1 1 d . . . C1 C -0.6437(2) -0.45980(13) 0.23737(7) 0.0338(5) Uani 1 1 d . . . C2 C -0.6747(2) -0.37687(14) 0.25925(8) 0.0388(6) Uani 1 1 d . . . H2 H -0.633(2) -0.3573(13) 0.2911(8) 0.049(6) Uiso 1 1 d . . . C3 C -0.7564(2) -0.32438(14) 0.23322(8) 0.0383(6) Uani 1 1 d . . . H3 H -0.788(2) -0.2616(14) 0.2490(8) 0.057(7) Uiso 1 1 d . . . C4 C -0.8044(2) -0.35428(13) 0.18591(7) 0.0333(5) Uani 1 1 d . . . C5 C -0.7672(2) -0.43804(13) 0.16659(8) 0.0319(5) Uani 1 1 d . . . C6 C -0.8125(2) -0.47054(13) 0.11263(8) 0.0328(5) Uani 1 1 d . . . H6 H -0.7458(18) -0.4716(12) 0.0877(7) 0.036(6) Uiso 1 1 d . . . C7 C -0.9073(2) -0.40584(14) 0.09297(8) 0.0364(6) Uani 1 1 d . . . H7 H -0.944(2) -0.4332(14) 0.0571(9) 0.053(7) Uiso 1 1 d . . . C8 C -0.8647(2) -0.30521(14) 0.09373(8) 0.0409(6) Uani 1 1 d . . . C9 C -0.8967(2) -0.30666(14) 0.15450(8) 0.0366(6) Uani 1 1 d . . . H9 H -0.926(2) -0.2454(14) 0.1748(8) 0.050(6) Uiso 1 1 d . . . C10 C -0.9886(2) -0.38056(17) 0.14027(10) 0.0429(6) Uani 1 1 d . . . H10A H -1.063(2) -0.3567(16) 0.1289(9) 0.063(8) Uiso 1 1 d . . . H10B H -0.998(2) -0.4332(16) 0.1670(10) 0.066(8) Uiso 1 1 d . . . C11 C -0.9473(4) -0.24346(19) 0.06277(10) 0.0584(9) Uani 1 1 d . . . H11A H -0.919(2) -0.1701(19) 0.0673(9) 0.080(8) Uiso 1 1 d . . . H11B H -0.929(2) -0.2509(17) 0.0231(10) 0.079(8) Uiso 1 1 d . . . H11C H -1.032(3) -0.253(2) 0.0676(11) 0.096(13) Uiso 1 1 d . . . C12 C -0.7403(3) -0.28496(16) 0.07755(10) 0.0468(7) Uani 1 1 d . . . H12A H -0.7294(18) -0.2999(12) 0.0417(8) 0.037(6) Uiso 1 1 d . . . H12B H -0.724(2) -0.2148(16) 0.0813(8) 0.065(7) Uiso 1 1 d . . . H12C H -0.676(2) -0.3223(14) 0.1024(8) 0.059(7) Uiso 1 1 d . . . C13 C -0.5590(2) -0.52099(14) 0.26358(7) 0.0340(5) Uani 1 1 d . . . C14 C -0.5602(2) -0.61371(14) 0.25323(8) 0.0374(6) Uani 1 1 d . . . H14 H -0.6247(18) -0.6405(12) 0.2286(7) 0.032(5) Uiso 1 1 d . . . C15 C -0.4808(2) -0.66783(16) 0.27917(9) 0.0450(7) Uani 1 1 d . . . H15 H -0.4784(19) -0.7393(14) 0.2692(8) 0.050(6) Uiso 1 1 d . . . C16 C -0.4010(2) -0.62879(15) 0.31351(9) 0.0439(6) Uani 1 1 d . . . H16 H -0.340(2) -0.6681(14) 0.3332(8) 0.048(6) Uiso 1 1 d . . . C17 C -0.4029(2) -0.53592(15) 0.32159(8) 0.0390(6) Uani 1 1 d . . . C18 C -0.3170(2) -0.48898(15) 0.35645(8) 0.0414(6) Uani 1 1 d . . . C19 C -0.3447(3) -0.40643(18) 0.37939(10) 0.0578(8) Uani 1 1 d . . . H19 H -0.423(2) -0.3769(17) 0.3712(10) 0.079(9) Uiso 1 1 d . . . C20 C -0.2615(3) -0.3608(2) 0.41015(10) 0.0661(8) Uani 1 1 d . . . H20 H -0.283(2) -0.2935(18) 0.4228(10) 0.086(9) Uiso 1 1 d . . . C21 C -0.1532(3) -0.3966(2) 0.41797(9) 0.0606(8) Uani 1 1 d . . . H21 H -0.083(3) -0.3561(19) 0.4428(11) 0.105(10) Uiso 1 1 d . . . C22 C -0.1256(3) -0.47895(19) 0.39614(9) 0.0564(8) Uani 1 1 d . . . H22 H -0.045(3) -0.5083(18) 0.4042(10) 0.083(9) Uiso 1 1 d . . . C23 C -0.2063(2) -0.52556(17) 0.36553(9) 0.0456(6) Uani 1 1 d . . . H23 H -0.184(2) -0.5910(17) 0.3481(9) 0.083(8) Uiso 1 1 d . . . C24 C -0.8527(3) -0.56944(13) 0.11418(8) 0.0341(6) Uani 1 1 d . . . H24A H -0.7946(18) -0.6059(12) 0.1385(7) 0.033(5) Uiso 1 1 d . . . H24B H -0.932(2) -0.5700(13) 0.1254(8) 0.043(7) Uiso 1 1 d . . . C25 C -0.8494(2) -0.61446(13) 0.06011(7) 0.0303(5) Uani 1 1 d . . . C26 C -0.7438(2) -0.62980(13) 0.03492(8) 0.0344(6) Uani 1 1 d . . . H26 H -0.675(2) -0.6113(13) 0.0515(8) 0.043(6) Uiso 1 1 d . . . C27 C -0.7381(2) -0.67227(13) -0.01417(8) 0.0323(5) Uani 1 1 d . . . H27 H -0.658(2) -0.6852(14) -0.0305(8) 0.057(7) Uiso 1 1 d . . . C28 C -0.8383(2) -0.70034(12) -0.04015(7) 0.0312(5) Uani 1 1 d . . . C29 C -0.9444(2) -0.68491(14) -0.01562(8) 0.0372(6) Uani 1 1 d . . . H29 H -1.023(2) -0.7029(13) -0.0355(8) 0.051(7) Uiso 1 1 d . . . C30 C -0.9495(2) -0.64300(15) 0.03415(8) 0.0372(6) Uani 1 1 d . . . H30 H -1.030(2) -0.6345(13) 0.0523(8) 0.047(6) Uiso 1 1 d . . . C31 C -0.8284(3) -0.74765(14) -0.09356(8) 0.0353(6) Uani 1 1 d . . . H31A H -0.757(2) -0.7164(13) -0.1129(8) 0.044(6) Uiso 1 1 d . . . H31B H -0.906(2) -0.7463(14) -0.1116(8) 0.042(6) Uiso 1 1 d . . . N11 N -0.65000(17) -0.84068(10) -0.15857(6) 0.0307(4) Uani 1 1 d . . . N12 N -0.44586(16) -0.85853(11) -0.26737(6) 0.0343(5) Uani 1 1 d . . . C41 C -0.60037(19) -0.87394(13) -0.20346(7) 0.0306(5) Uani 1 1 d . . . C42 C -0.6423(2) -0.95018(13) -0.22890(8) 0.0332(5) Uani 1 1 d . . . H42 H -0.5968(18) -0.9730(12) -0.2613(7) 0.032(5) Uiso 1 1 d . . . C43 C -0.7378(2) -0.99442(14) -0.20810(7) 0.0336(5) Uani 1 1 d . . . H43 H -0.7690(18) -1.0513(12) -0.2255(7) 0.035(5) Uiso 1 1 d . . . C44 C -0.7891(2) -0.96241(13) -0.16204(7) 0.0312(5) Uani 1 1 d . . . C45 C -0.7415(2) -0.88421(12) -0.13898(7) 0.0287(5) Uani 1 1 d . . . C46 C -0.7960(2) -0.84824(13) -0.08783(7) 0.0293(5) Uani 1 1 d . . . H46 H -0.7322(18) -0.8507(12) -0.0583(7) 0.038(5) Uiso 1 1 d . . . C47 C -0.8993(2) -0.90723(14) -0.07184(8) 0.0335(5) Uani 1 1 d . . . H47 H -0.9404(18) -0.8841(13) -0.0378(8) 0.043(6) Uiso 1 1 d . . . C48 C -0.8687(2) -1.01055(14) -0.07322(7) 0.0374(6) Uani 1 1 d . . . C49 C -0.8924(2) -1.00306(15) -0.13476(8) 0.0352(5) Uani 1 1 d . . . H49 H -0.9238(19) -1.0569(13) -0.1529(8) 0.045(6) Uiso 1 1 d . . . C50 C -0.9764(2) -0.92362(17) -0.12158(9) 0.0376(6) Uani 1 1 d . . . H50A H -0.9757(19) -0.8731(14) -0.1481(8) 0.050(7) Uiso 1 1 d . . . H50B H -1.057(2) -0.9465(14) -0.1152(8) 0.058(8) Uiso 1 1 d . . . C51 C -0.9629(3) -1.06644(18) -0.04521(11) 0.0503(7) Uani 1 1 d . . . H51A H -0.948(2) -1.1337(17) -0.0554(9) 0.067(8) Uiso 1 1 d . . . H51B H -1.048(3) -1.0452(17) -0.0608(10) 0.081(10) Uiso 1 1 d . . . H51C H -0.958(3) -1.0615(17) -0.0021(11) 0.092(9) Uiso 1 1 d . . . C52 C -0.7500(2) -1.04061(16) -0.05399(10) 0.0430(6) Uani 1 1 d . . . H52A H -0.7446(19) -1.0319(12) -0.0136(8) 0.043(6) Uiso 1 1 d . . . H52B H -0.741(2) -1.1101(16) -0.0598(8) 0.062(7) Uiso 1 1 d . . . H52C H -0.685(2) -1.0076(14) -0.0728(8) 0.050(7) Uiso 1 1 d . . . C53 C -0.4972(2) -0.82351(13) -0.22375(8) 0.0326(5) Uani 1 1 d . . . C54 C -0.4571(2) -0.74535(14) -0.19885(9) 0.0385(6) Uani 1 1 d . . . H54 H -0.497(2) -0.7235(14) -0.1648(9) 0.056(7) Uiso 1 1 d . . . C55 C -0.3604(2) -0.70296(15) -0.21980(9) 0.0440(6) Uani 1 1 d . . . H55 H -0.323(2) -0.6479(14) -0.2028(8) 0.057(7) Uiso 1 1 d . . . C56 C -0.3068(2) -0.73831(14) -0.26459(9) 0.0405(6) Uani 1 1 d . . . H56 H -0.228(2) -0.7110(13) -0.2777(8) 0.048(7) Uiso 1 1 d . . . C57 C -0.3519(2) -0.81600(13) -0.28757(8) 0.0354(5) Uani 1 1 d . . . C58 C -0.2998(2) -0.85786(15) -0.33577(8) 0.0396(6) Uani 1 1 d . . . C59 C -0.2298(3) -0.80955(19) -0.37027(9) 0.0566(8) Uani 1 1 d . . . H59 H -0.2137(19) -0.7443(14) -0.3632(8) 0.049(7) Uiso 1 1 d . . . C60 C -0.1803(3) -0.8516(2) -0.41448(10) 0.0722(9) Uani 1 1 d . . . H60 H -0.128(3) -0.8140(18) -0.4362(10) 0.084(9) Uiso 1 1 d . . . C61 C -0.1998(3) -0.9413(2) -0.42423(11) 0.0708(9) Uani 1 1 d . . . H61 H -0.154(3) -0.9684(16) -0.4508(11) 0.083(9) Uiso 1 1 d . . . C62 C -0.2689(3) -0.9891(2) -0.39016(10) 0.0670(9) Uani 1 1 d . . . H62 H -0.291(2) -1.0511(17) -0.3998(10) 0.076(9) Uiso 1 1 d . . . C63 C -0.3192(2) -0.94864(16) -0.34621(9) 0.0489(7) Uani 1 1 d . . . H63 H -0.378(2) -0.9810(15) -0.3202(9) 0.068(8) 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 N1 0.0357(13) 0.0339(9) 0.0283(9) -0.0032(7) 0.0031(8) -0.0002(9) N2 0.0379(14) 0.0408(10) 0.0313(10) -0.0060(8) 0.0025(9) 0.0004(9) C1 0.0375(16) 0.0363(11) 0.0276(11) -0.0034(9) 0.0033(10) -0.0013(11) C2 0.0458(18) 0.0387(13) 0.0318(12) -0.0096(10) -0.0005(11) 0.0043(12) C3 0.0451(18) 0.0349(12) 0.0349(12) -0.0090(10) 0.0030(11) 0.0042(12) C4 0.0370(16) 0.0314(11) 0.0316(11) -0.0044(9) 0.0056(10) -0.0012(10) C5 0.0352(16) 0.0305(11) 0.0298(11) -0.0063(9) 0.0054(10) -0.0029(10) C6 0.0389(17) 0.0312(11) 0.0283(11) -0.0047(9) 0.0040(10) 0.0001(11) C7 0.0403(17) 0.0350(12) 0.0337(12) -0.0057(10) 0.0012(11) 0.0035(11) C8 0.0528(19) 0.0346(12) 0.0352(11) -0.0024(10) -0.0018(12) 0.0037(12) C9 0.0427(17) 0.0337(12) 0.0333(12) -0.0069(10) 0.0003(10) 0.0081(11) C10 0.0344(18) 0.0520(16) 0.0423(14) -0.0079(12) 0.0005(12) 0.0044(13) C11 0.085(3) 0.0500(17) 0.0400(17) -0.0012(12) -0.0102(16) 0.0184(17) C12 0.066(2) 0.0359(14) 0.0381(14) -0.0044(11) 0.0107(14) -0.0041(13) C13 0.0357(16) 0.0393(12) 0.0270(11) -0.0019(10) 0.0054(10) 0.0010(11) C14 0.0425(18) 0.0334(12) 0.0365(13) 0.0004(10) 0.0049(11) -0.0007(11) C15 0.055(2) 0.0328(13) 0.0469(14) 0.0009(11) -0.0014(13) 0.0035(12) C16 0.0477(19) 0.0430(14) 0.0410(14) 0.0045(11) -0.0030(12) 0.0040(13) C17 0.0428(17) 0.0433(13) 0.0307(11) 0.0008(10) 0.0037(11) 0.0006(12) C18 0.0481(19) 0.0470(13) 0.0290(11) -0.0014(10) 0.0008(11) -0.0027(12) C19 0.052(2) 0.0637(17) 0.0574(16) -0.0246(14) -0.0011(15) 0.0013(16) C20 0.068(3) 0.071(2) 0.0589(17) -0.0280(15) 0.0032(16) -0.0102(18) C21 0.059(2) 0.083(2) 0.0391(14) -0.0047(14) -0.0057(15) -0.0168(19) C22 0.057(2) 0.0700(19) 0.0424(15) 0.0136(14) -0.0103(13) -0.0070(17) C23 0.053(2) 0.0503(15) 0.0337(12) 0.0077(11) -0.0058(12) -0.0007(13) C24 0.0418(18) 0.0298(12) 0.0309(12) -0.0056(9) 0.0072(12) -0.0044(11) C25 0.0358(15) 0.0255(11) 0.0294(11) -0.0021(8) 0.0022(11) -0.0029(10) C26 0.0332(17) 0.0336(12) 0.0364(12) -0.0057(9) -0.0037(12) -0.0037(11) C27 0.0315(17) 0.0314(11) 0.0341(11) -0.0030(9) 0.0030(11) -0.0005(11) C28 0.0363(17) 0.0262(10) 0.0310(10) -0.0026(9) -0.0004(11) 0.0034(10) C29 0.0344(17) 0.0389(13) 0.0383(13) -0.0080(10) -0.0042(12) -0.0002(11) C30 0.0332(17) 0.0417(13) 0.0368(12) -0.0058(10) 0.0067(11) -0.0010(12) C31 0.0433(19) 0.0350(12) 0.0277(12) -0.0046(9) -0.0031(12) 0.0023(12) N11 0.0324(12) 0.0321(9) 0.0277(9) 0.0005(7) -0.0003(9) 0.0034(9) N12 0.0369(14) 0.0365(10) 0.0293(9) 0.0045(8) 0.0022(9) 0.0065(9) C41 0.0337(15) 0.0337(12) 0.0244(10) 0.0019(9) -0.0005(9) 0.0044(11) C42 0.0392(16) 0.0334(11) 0.0271(11) -0.0035(9) 0.0026(11) 0.0037(11) C43 0.0412(17) 0.0298(11) 0.0298(11) -0.0053(9) -0.0031(10) 0.0037(11) C44 0.0314(15) 0.0328(11) 0.0293(11) -0.0034(9) -0.0040(10) 0.0037(10) C45 0.0310(15) 0.0285(11) 0.0265(10) -0.0037(9) -0.0044(10) 0.0068(10) C46 0.0332(15) 0.0298(11) 0.0249(10) -0.0035(9) -0.0011(10) 0.0023(10) C47 0.0317(16) 0.0367(12) 0.0320(12) -0.0054(10) -0.0009(10) -0.0030(10) C48 0.0418(18) 0.0381(12) 0.0323(11) -0.0023(9) 0.0035(10) -0.0010(11) C49 0.0347(16) 0.0383(12) 0.0327(12) -0.0104(10) 0.0011(10) -0.0042(11) C50 0.0320(18) 0.0454(15) 0.0352(13) -0.0104(11) -0.0011(11) -0.0007(12) C51 0.060(2) 0.0423(15) 0.0482(16) -0.0004(12) 0.0096(14) -0.0138(14) C52 0.0479(19) 0.0403(14) 0.0409(14) -0.0001(11) -0.0008(13) 0.0058(13) C53 0.0353(16) 0.0323(12) 0.0302(11) 0.0044(9) 0.0015(10) 0.0058(11) C54 0.0461(18) 0.0328(12) 0.0366(13) 0.0022(10) 0.0041(12) -0.0013(12) C55 0.054(2) 0.0334(13) 0.0450(13) -0.0013(11) 0.0061(13) -0.0063(12) C56 0.0408(18) 0.0372(13) 0.0435(13) 0.0021(11) 0.0068(12) 0.0011(12) C57 0.0403(17) 0.0354(12) 0.0303(11) 0.0044(10) 0.0005(11) 0.0093(12) C58 0.0373(17) 0.0462(14) 0.0352(12) 0.0052(10) 0.0016(10) 0.0092(12) C59 0.065(2) 0.0585(17) 0.0461(15) 0.0043(13) 0.0151(14) -0.0082(15) C60 0.079(3) 0.088(2) 0.0499(16) -0.0007(16) 0.0298(16) -0.0100(19) C61 0.080(3) 0.079(2) 0.0527(18) -0.0113(16) 0.0251(17) 0.0052(18) C62 0.084(3) 0.0589(18) 0.0577(17) -0.0123(14) 0.0213(16) 0.0055(17) C63 0.058(2) 0.0460(15) 0.0430(14) -0.0060(11) 0.0108(13) 0.0079(13) _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 C5 1.335(3) . ? N1 C1 1.348(2) . ? N2 C17 1.350(3) . ? N2 C13 1.354(3) . ? C1 C2 1.389(3) . ? C1 C13 1.483(3) . ? C2 C3 1.383(3) . ? C3 C4 1.384(3) . ? C4 C5 1.396(3) . ? C4 C9 1.498(3) . ? C5 C6 1.531(3) . ? C6 C7 1.531(3) . ? C6 C24 1.533(3) . ? C7 C10 1.558(3) . ? C7 C8 1.565(3) . ? C8 C12 1.517(3) . ? C8 C11 1.529(3) . ? C8 C9 1.571(3) . ? C9 C10 1.561(3) . ? C13 C14 1.394(3) . ? C14 C15 1.377(3) . ? C15 C16 1.386(3) . ? C16 C17 1.387(3) . ? C17 C18 1.492(3) . ? C18 C19 1.386(3) . ? C18 C23 1.402(3) . ? C19 C20 1.403(4) . ? C20 C21 1.367(4) . ? C21 C22 1.372(4) . ? C22 C23 1.388(3) . ? C24 C25 1.514(3) . ? C25 C26 1.388(3) . ? C25 C30 1.389(3) . ? C26 C27 1.386(3) . ? C27 C28 1.388(3) . ? C28 C29 1.385(3) . ? C28 C31 1.518(3) . ? C29 C30 1.397(3) . ? C31 C46 1.539(3) . ? N11 C45 1.328(3) . ? N11 C41 1.357(2) . ? N12 C53 1.349(2) . ? N12 C57 1.349(3) . ? C41 C42 1.382(3) . ? C41 C53 1.491(3) . ? C42 C43 1.380(3) . ? C43 C44 1.383(3) . ? C44 C45 1.403(3) . ? C44 C49 1.497(3) . ? C45 C46 1.526(3) . ? C46 C47 1.528(3) . ? C47 C50 1.552(3) . ? C47 C48 1.567(3) . ? C48 C52 1.514(3) . ? C48 C51 1.533(3) . ? C48 C49 1.575(3) . ? C49 C50 1.556(3) . ? C53 C54 1.392(3) . ? C54 C55 1.380(3) . ? C55 C56 1.386(3) . ? C56 C57 1.386(3) . ? C57 C58 1.487(3) . ? C58 C59 1.382(3) . ? C58 C63 1.384(3) . ? C59 C60 1.395(3) . ? C60 C61 1.365(4) . ? C61 C62 1.366(4) . ? C62 C63 1.384(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 C5 N1 C1 117.96(16) . . ? C17 N2 C13 118.40(18) . . ? N1 C1 C2 122.2(2) . . ? N1 C1 C13 115.74(17) . . ? C2 C1 C13 122.01(19) . . ? C3 C2 C1 118.8(2) . . ? C2 C3 C4 119.9(2) . . ? C3 C4 C5 117.4(2) . . ? C3 C4 C9 125.87(18) . . ? C5 C4 C9 116.72(19) . . ? N1 C5 C4 123.71(18) . . ? N1 C5 C6 117.42(17) . . ? C4 C5 C6 118.81(19) . . ? C5 C6 C7 109.42(17) . . ? C5 C6 C24 112.26(16) . . ? C7 C6 C24 112.9(2) . . ? C6 C7 C10 109.28(18) . . ? C6 C7 C8 111.49(19) . . ? C10 C7 C8 87.17(17) . . ? C12 C8 C11 109.3(2) . . ? C12 C8 C7 118.60(19) . . ? C11 C8 C7 111.5(2) . . ? C12 C8 C9 118.94(19) . . ? C11 C8 C9 111.0(2) . . ? C7 C8 C9 85.75(16) . . ? C4 C9 C10 105.78(18) . . ? C4 C9 C8 110.68(18) . . ? C10 C9 C8 86.85(16) . . ? C7 C10 C9 86.35(18) . . ? N2 C13 C14 122.6(2) . . ? N2 C13 C1 116.83(18) . . ? C14 C13 C1 120.6(2) . . ? C15 C14 C13 118.4(2) . . ? C14 C15 C16 119.5(2) . . ? C15 C16 C17 119.5(2) . . ? N2 C17 C16 121.7(2) . . ? N2 C17 C18 115.96(19) . . ? C16 C17 C18 122.3(2) . . ? C19 C18 C23 118.7(2) . . ? C19 C18 C17 120.1(2) . . ? C23 C18 C17 121.2(2) . . ? C18 C19 C20 119.7(3) . . ? C21 C20 C19 121.0(3) . . ? C20 C21 C22 119.7(3) . . ? C21 C22 C23 120.5(3) . . ? C22 C23 C18 120.4(3) . . ? C25 C24 C6 112.84(17) . . ? C26 C25 C30 117.45(18) . . ? C26 C25 C24 120.2(2) . . ? C30 C25 C24 122.3(2) . . ? C27 C26 C25 121.5(2) . . ? C26 C27 C28 121.0(2) . . ? C29 C28 C27 118.19(18) . . ? C29 C28 C31 122.4(2) . . ? C27 C28 C31 119.4(2) . . ? C28 C29 C30 120.6(2) . . ? C25 C30 C29 121.3(2) . . ? C28 C31 C46 112.33(16) . . ? C45 N11 C41 117.81(17) . . ? C53 N12 C57 118.56(18) . . ? N11 C41 C42 122.2(2) . . ? N11 C41 C53 116.00(17) . . ? C42 C41 C53 121.79(18) . . ? C43 C42 C41 119.2(2) . . ? C42 C43 C44 119.6(2) . . ? C43 C44 C45 117.5(2) . . ? C43 C44 C49 125.79(19) . . ? C45 C44 C49 116.75(18) . . ? N11 C45 C44 123.65(18) . . ? N11 C45 C46 117.98(17) . . ? C44 C45 C46 118.35(19) . . ? C45 C46 C47 110.02(16) . . ? C45 C46 C31 110.89(16) . . ? C47 C46 C31 112.77(19) . . ? C46 C47 C50 108.73(18) . . ? C46 C47 C48 112.00(18) . . ? C50 C47 C48 87.64(16) . . ? C52 C48 C51 109.4(2) . . ? C52 C48 C47 118.78(19) . . ? C51 C48 C47 110.8(2) . . ? C52 C48 C49 119.35(18) . . ? C51 C48 C49 111.5(2) . . ? C47 C48 C49 85.09(15) . . ? C44 C49 C50 106.71(18) . . ? C44 C49 C48 109.94(18) . . ? C50 C49 C48 87.21(16) . . ? C47 C50 C49 86.25(17) . . ? N12 C53 C54 122.6(2) . . ? N12 C53 C41 115.78(18) . . ? C54 C53 C41 121.63(19) . . ? C55 C54 C53 118.1(2) . . ? C54 C55 C56 119.8(2) . . ? C57 C56 C55 119.0(2) . . ? N12 C57 C56 121.9(2) . . ? N12 C57 C58 115.85(19) . . ? C56 C57 C58 122.2(2) . . ? C59 C58 C63 118.4(2) . . ? C59 C58 C57 122.1(2) . . ? C63 C58 C57 119.5(2) . . ? C58 C59 C60 120.5(3) . . ? C61 C60 C59 120.5(3) . . ? C60 C61 C62 119.0(3) . . ? C61 C62 C63 121.4(3) . . ? C62 C63 C58 120.2(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 C5 N1 C1 C2 0.6(3) . . . . ? C5 N1 C1 C13 179.55(18) . . . . ? N1 C1 C2 C3 0.5(3) . . . . ? C13 C1 C2 C3 -178.5(2) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C2 C3 C4 C9 177.5(2) . . . . ? C1 N1 C5 C4 -1.3(3) . . . . ? C1 N1 C5 C6 175.79(18) . . . . ? C3 C4 C5 N1 0.9(3) . . . . ? C9 C4 C5 N1 -176.6(2) . . . . ? C3 C4 C5 C6 -176.1(2) . . . . ? C9 C4 C5 C6 6.4(3) . . . . ? N1 C5 C6 C7 175.17(18) . . . . ? C4 C5 C6 C7 -7.6(3) . . . . ? N1 C5 C6 C24 49.0(3) . . . . ? C4 C5 C6 C24 -133.8(2) . . . . ? C5 C6 C7 C10 -42.4(2) . . . . ? C24 C6 C7 C10 83.4(2) . . . . ? C5 C6 C7 C8 52.3(2) . . . . ? C24 C6 C7 C8 178.05(17) . . . . ? C6 C7 C8 C12 38.8(3) . . . . ? C10 C7 C8 C12 148.4(2) . . . . ? C6 C7 C8 C11 167.1(2) . . . . ? C10 C7 C8 C11 -83.3(2) . . . . ? C6 C7 C8 C9 -82.03(19) . . . . ? C10 C7 C8 C9 27.59(17) . . . . ? C3 C4 C9 C10 -132.9(2) . . . . ? C5 C4 C9 C10 44.4(3) . . . . ? C3 C4 C9 C8 134.5(2) . . . . ? C5 C4 C9 C8 -48.3(3) . . . . ? C12 C8 C9 C4 -42.4(2) . . . . ? C11 C8 C9 C4 -170.5(2) . . . . ? C7 C8 C9 C4 78.1(2) . . . . ? C12 C8 C9 C10 -148.0(2) . . . . ? C11 C8 C9 C10 83.8(2) . . . . ? C7 C8 C9 C10 -27.55(17) . . . . ? C6 C7 C10 C9 84.0(2) . . . . ? C8 C7 C10 C9 -27.78(17) . . . . ? C4 C9 C10 C7 -82.95(19) . . . . ? C8 C9 C10 C7 27.66(17) . . . . ? C17 N2 C13 C14 -0.1(3) . . . . ? C17 N2 C13 C1 -179.73(19) . . . . ? N1 C1 C13 N2 156.84(19) . . . . ? C2 C1 C13 N2 -24.2(3) . . . . ? N1 C1 C13 C14 -22.8(3) . . . . ? C2 C1 C13 C14 156.2(2) . . . . ? N2 C13 C14 C15 1.3(3) . . . . ? C1 C13 C14 C15 -179.0(2) . . . . ? C13 C14 C15 C16 -1.5(4) . . . . ? C14 C15 C16 C17 0.6(4) . . . . ? C13 N2 C17 C16 -0.9(3) . . . . ? C13 N2 C17 C18 177.61(19) . . . . ? C15 C16 C17 N2 0.7(3) . . . . ? C15 C16 C17 C18 -177.8(2) . . . . ? N2 C17 C18 C19 25.7(3) . . . . ? C16 C17 C18 C19 -155.8(2) . . . . ? N2 C17 C18 C23 -152.5(2) . . . . ? C16 C17 C18 C23 26.0(3) . . . . ? C23 C18 C19 C20 1.1(4) . . . . ? C17 C18 C19 C20 -177.1(2) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C19 C20 C21 C22 -1.0(4) . . . . ? C20 C21 C22 C23 1.0(4) . . . . ? C21 C22 C23 C18 0.1(4) . . . . ? C19 C18 C23 C22 -1.1(3) . . . . ? C17 C18 C23 C22 177.1(2) . . . . ? C5 C6 C24 C25 -155.9(2) . . . . ? C7 C6 C24 C25 79.9(3) . . . . ? C6 C24 C25 C26 66.7(3) . . . . ? C6 C24 C25 C30 -114.2(2) . . . . ? C30 C25 C26 C27 -0.2(3) . . . . ? C24 C25 C26 C27 178.88(19) . . . . ? C25 C26 C27 C28 0.6(3) . . . . ? C26 C27 C28 C29 -0.1(3) . . . . ? C26 C27 C28 C31 -179.26(18) . . . . ? C27 C28 C29 C30 -0.6(3) . . . . ? C31 C28 C29 C30 178.49(19) . . . . ? C26 C25 C30 C29 -0.5(3) . . . . ? C24 C25 C30 C29 -179.6(2) . . . . ? C28 C29 C30 C25 0.9(3) . . . . ? C29 C28 C31 C46 -99.3(3) . . . . ? C27 C28 C31 C46 79.7(3) . . . . ? C45 N11 C41 C42 0.3(3) . . . . ? C45 N11 C41 C53 -179.43(18) . . . . ? N11 C41 C42 C43 -0.1(3) . . . . ? C53 C41 C42 C43 179.6(2) . . . . ? C41 C42 C43 C44 -0.6(3) . . . . ? C42 C43 C44 C45 1.1(3) . . . . ? C42 C43 C44 C49 -179.8(2) . . . . ? C41 N11 C45 C44 0.2(3) . . . . ? C41 N11 C45 C46 178.68(17) . . . . ? C43 C44 C45 N11 -0.9(3) . . . . ? C49 C44 C45 N11 179.92(19) . . . . ? C43 C44 C45 C46 -179.38(19) . . . . ? C49 C44 C45 C46 1.4(3) . . . . ? N11 C45 C46 C47 -179.91(18) . . . . ? C44 C45 C46 C47 -1.3(2) . . . . ? N11 C45 C46 C31 54.6(3) . . . . ? C44 C45 C46 C31 -126.8(2) . . . . ? C28 C31 C46 C45 -158.0(2) . . . . ? C28 C31 C46 C47 78.1(3) . . . . ? C45 C46 C47 C50 -46.8(2) . . . . ? C31 C46 C47 C50 77.6(2) . . . . ? C45 C46 C47 C48 48.4(2) . . . . ? C31 C46 C47 C48 172.77(16) . . . . ? C46 C47 C48 C52 39.1(3) . . . . ? C50 C47 C48 C52 148.4(2) . . . . ? C46 C47 C48 C51 167.0(2) . . . . ? C50 C47 C48 C51 -83.7(2) . . . . ? C46 C47 C48 C49 -81.79(19) . . . . ? C50 C47 C48 C49 27.48(17) . . . . ? C43 C44 C49 C50 -133.3(2) . . . . ? C45 C44 C49 C50 45.8(2) . . . . ? C43 C44 C49 C48 133.5(2) . . . . ? C45 C44 C49 C48 -47.3(2) . . . . ? C52 C48 C49 C44 -41.0(3) . . . . ? C51 C48 C49 C44 -170.2(2) . . . . ? C47 C48 C49 C44 79.36(19) . . . . ? C52 C48 C49 C50 -147.8(2) . . . . ? C51 C48 C49 C50 83.0(2) . . . . ? C47 C48 C49 C50 -27.41(17) . . . . ? C46 C47 C50 C49 84.66(19) . . . . ? C48 C47 C50 C49 -27.80(16) . . . . ? C44 C49 C50 C47 -82.34(19) . . . . ? C48 C49 C50 C47 27.65(16) . . . . ? C57 N12 C53 C54 0.0(3) . . . . ? C57 N12 C53 C41 -179.88(19) . . . . ? N11 C41 C53 N12 177.89(18) . . . . ? C42 C41 C53 N12 -1.9(3) . . . . ? N11 C41 C53 C54 -2.0(3) . . . . ? C42 C41 C53 C54 178.2(2) . . . . ? N12 C53 C54 C55 -0.4(3) . . . . ? C41 C53 C54 C55 179.5(2) . . . . ? C53 C54 C55 C56 0.3(3) . . . . ? C54 C55 C56 C57 0.1(3) . . . . ? C53 N12 C57 C56 0.5(3) . . . . ? C53 N12 C57 C58 -179.75(18) . . . . ? C55 C56 C57 N12 -0.5(3) . . . . ? C55 C56 C57 C58 179.7(2) . . . . ? N12 C57 C58 C59 159.0(2) . . . . ? C56 C57 C58 C59 -21.3(4) . . . . ? N12 C57 C58 C63 -22.5(3) . . . . ? C56 C57 C58 C63 157.3(2) . . . . ? C63 C58 C59 C60 0.0(4) . . . . ? C57 C58 C59 C60 178.6(3) . . . . ? C58 C59 C60 C61 -0.3(5) . . . . ? C59 C60 C61 C62 0.2(5) . . . . ? C60 C61 C62 C63 0.0(5) . . . . ? C61 C62 C63 C58 -0.3(5) . . . . ? C59 C58 C63 C62 0.3(4) . . . . ? C57 C58 C63 C62 -178.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.95 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.142 _refine_diff_density_min -0.121 _refine_diff_density_rms 0.029 #=========================================================================== #======================= data_cpd8 _database_code_CSD 179706 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H46 N4 O2' _chemical_formula_weight 710.89 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 20.7692(18) _cell_length_b 6.0863(4) _cell_length_c 14.9639(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.673(10) _cell_angle_gamma 90.00 _cell_volume 1864.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6865 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 25.89 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.078 _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 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7379 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.89 _reflns_number_total 3471 _reflns_number_gt 2907 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0500P)^2^] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0184(16) _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 -1.4(15) _refine_ls_number_reflns 3471 _refine_ls_number_parameters 337 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.39923(6) -0.0476(2) -0.89411(9) 0.0213(3) Uani 1 1 d . . . N2 N -0.27798(6) -0.2703(3) -0.71555(9) 0.0252(3) Uani 1 1 d . . . O1 O -0.02963(6) -0.4265(3) -0.41285(8) 0.0397(4) Uani 1 1 d . . . C1 C -0.34088(7) -0.0686(3) -0.83884(11) 0.0230(4) Uani 1 1 d . . . C2 C -0.28862(7) 0.0698(3) -0.84541(11) 0.0282(4) Uani 1 1 d . . . H2 H -0.2476(8) 0.058(3) -0.8037(11) 0.024(4) Uiso 1 1 d . . . C3 C -0.29549(8) 0.2298(3) -0.91218(11) 0.0276(4) Uani 1 1 d . . . H3 H -0.2587(9) 0.336(4) -0.9198(12) 0.032(5) Uiso 1 1 d . . . C4 C -0.35416(7) 0.2499(3) -0.97073(11) 0.0227(4) Uani 1 1 d . . . C5 C -0.36751(8) 0.4122(3) -1.04713(11) 0.0247(4) Uani 1 1 d . . . H5 H -0.3286(9) 0.511(3) -1.0501(13) 0.033(5) Uiso 1 1 d . . . C6 C -0.40179(8) 0.2914(3) -1.13491(11) 0.0248(4) Uani 1 1 d . . . C7 C -0.46554(8) 0.3093(3) -1.09072(11) 0.0216(4) Uani 1 1 d . . . H7 H -0.5077(8) 0.329(3) -1.1348(11) 0.017(4) Uiso 1 1 d . . . C8 C -0.46962(7) 0.1211(3) -1.02435(11) 0.0201(4) Uani 1 1 d . . . H8 H -0.4737(8) -0.020(3) -1.0581(11) 0.018(4) Uiso 1 1 d . . . C9 C -0.40543(7) 0.1068(3) -0.95817(10) 0.0208(4) Uani 1 1 d . . . C10 C -0.43458(8) 0.5173(3) -1.04138(12) 0.0251(4) Uani 1 1 d . . . H10A H -0.4442(9) 0.650(4) -1.0817(13) 0.032(5) Uiso 1 1 d . . . H10B H -0.4428(8) 0.547(3) -0.9789(11) 0.021(4) Uiso 1 1 d . . . C11 C -0.37523(9) 0.0669(4) -1.15582(13) 0.0320(4) Uani 1 1 d . . . H11A H -0.3686(10) -0.036(4) -1.1004(14) 0.039(6) Uiso 1 1 d . . . H11B H -0.3313(12) 0.089(5) -1.1789(15) 0.061(7) Uiso 1 1 d . . . H25 H -0.4067(12) -0.010(4) -1.2039(16) 0.054(7) Uiso 1 1 d . . . C12 C -0.40755(9) 0.4353(4) -1.21940(12) 0.0324(5) Uani 1 1 d . . . H12A H -0.4240(10) 0.591(4) -1.2113(14) 0.045(6) Uiso 1 1 d . . . H12B H -0.3634(11) 0.454(4) -1.2369(14) 0.045(6) Uiso 1 1 d . . . H12C H -0.4374(10) 0.366(4) -1.2725(15) 0.044(6) Uiso 1 1 d . . . C13 C -0.33486(8) -0.2531(3) -0.77264(10) 0.0225(4) Uani 1 1 d . . . C14 C -0.38581(8) -0.4028(3) -0.77268(11) 0.0264(4) Uani 1 1 d . . . H14 H -0.4265(9) -0.378(3) -0.8154(12) 0.027(5) Uiso 1 1 d . . . C15 C -0.37634(9) -0.5775(4) -0.71349(12) 0.0304(4) Uani 1 1 d . . . H15 H -0.4108(10) -0.685(4) -0.7130(13) 0.038(6) Uiso 1 1 d . . . C16 C -0.31762(8) -0.5984(4) -0.65572(12) 0.0282(4) Uani 1 1 d . . . H16 H -0.3083(9) -0.723(4) -0.6137(13) 0.037(5) Uiso 1 1 d . . . C17 C -0.26926(8) -0.4393(3) -0.65691(10) 0.0247(4) Uani 1 1 d . . . C18 C -0.20624(8) -0.4445(3) -0.59273(11) 0.0258(4) Uani 1 1 d . . . C19 C -0.16451(8) -0.2635(4) -0.58464(12) 0.0291(4) Uani 1 1 d . . . H19 H -0.1775(9) -0.147(4) -0.6204(13) 0.032(5) Uiso 1 1 d . . . C20 C -0.10630(8) -0.2618(4) -0.52482(12) 0.0309(4) Uani 1 1 d . . . H20 H -0.0783(10) -0.131(4) -0.5208(13) 0.040(5) Uiso 1 1 d . . . C21 C -0.08806(8) -0.4436(4) -0.47061(11) 0.0303(4) Uani 1 1 d . . . C22 C -0.12858(9) -0.6241(4) -0.47632(13) 0.0374(5) Uani 1 1 d . . . H22 H -0.1169(10) -0.750(4) -0.4375(15) 0.045(6) Uiso 1 1 d . . . C23 C -0.18699(9) -0.6237(4) -0.53739(13) 0.0345(5) Uani 1 1 d . . . H12 H -0.2151(10) -0.754(4) -0.5430(14) 0.044(6) Uiso 1 1 d . . . C24 C -0.00348(11) -0.6230(5) -0.36845(17) 0.0539(7) Uani 1 1 d . . . H24A H 0.0420(12) -0.588(4) -0.3412(15) 0.053(6) Uiso 1 1 d . . . H24B H -0.0055(16) -0.769(7) -0.418(2) 0.113(12) Uiso 1 1 d . . . H24C H -0.0272(12) -0.665(5) -0.3209(17) 0.061(8) 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 N1 0.0167(6) 0.0230(9) 0.0234(7) -0.0008(6) 0.0009(5) 0.0017(6) N2 0.0208(7) 0.0299(9) 0.0243(7) 0.0009(7) 0.0017(5) 0.0016(7) O1 0.0267(6) 0.0577(10) 0.0314(6) 0.0094(7) -0.0051(5) -0.0020(7) C1 0.0190(8) 0.0261(11) 0.0235(8) -0.0030(8) 0.0027(6) 0.0021(7) C2 0.0165(8) 0.0378(13) 0.0282(8) 0.0028(9) -0.0022(7) 0.0000(8) C3 0.0184(8) 0.0323(12) 0.0319(9) 0.0007(9) 0.0034(7) -0.0049(8) C4 0.0200(8) 0.0234(11) 0.0250(8) -0.0034(8) 0.0048(6) -0.0005(8) C5 0.0203(8) 0.0248(11) 0.0290(9) -0.0006(8) 0.0040(7) -0.0039(7) C6 0.0231(8) 0.0262(11) 0.0254(8) -0.0003(7) 0.0048(7) 0.0009(7) C7 0.0178(8) 0.0221(10) 0.0242(8) -0.0001(7) 0.0016(6) 0.0022(6) C8 0.0165(8) 0.0189(10) 0.0242(8) -0.0026(7) 0.0011(6) 0.0014(7) C9 0.0180(8) 0.0221(10) 0.0215(7) -0.0033(7) 0.0013(6) 0.0019(7) C10 0.0255(8) 0.0210(11) 0.0289(9) 0.0004(8) 0.0049(7) 0.0003(7) C11 0.0301(9) 0.0336(12) 0.0331(9) -0.0042(10) 0.0081(8) 0.0040(9) C12 0.0325(10) 0.0376(13) 0.0277(9) 0.0020(9) 0.0062(7) -0.0015(9) C13 0.0195(8) 0.0275(11) 0.0204(8) -0.0017(7) 0.0027(6) 0.0033(7) C14 0.0206(8) 0.0339(12) 0.0230(8) -0.0007(8) -0.0015(6) -0.0016(8) C15 0.0288(9) 0.0337(12) 0.0280(9) -0.0004(8) 0.0022(7) -0.0084(9) C16 0.0282(9) 0.0297(12) 0.0257(9) 0.0047(8) 0.0017(7) 0.0003(8) C17 0.0235(8) 0.0293(11) 0.0210(8) 0.0009(8) 0.0030(6) 0.0038(8) C18 0.0208(8) 0.0335(11) 0.0232(8) 0.0020(8) 0.0042(6) 0.0007(8) C19 0.0261(9) 0.0366(12) 0.0246(8) 0.0070(9) 0.0045(7) 0.0034(9) C20 0.0254(9) 0.0379(13) 0.0289(9) 0.0025(8) 0.0032(7) -0.0041(9) C21 0.0217(8) 0.0464(13) 0.0225(8) 0.0027(9) 0.0029(6) 0.0038(9) C22 0.0306(10) 0.0438(15) 0.0357(10) 0.0146(10) -0.0005(8) 0.0030(10) C23 0.0278(9) 0.0353(13) 0.0377(10) 0.0076(9) -0.0021(8) -0.0030(9) C24 0.0325(11) 0.077(2) 0.0461(13) 0.0273(14) -0.0111(10) 0.0024(12) _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 C9 1.333(2) . ? N1 C1 1.354(2) . ? N2 C13 1.341(2) . ? N2 C17 1.344(2) . ? O1 C21 1.371(2) . ? O1 C24 1.430(3) . ? C1 C2 1.390(2) . ? C1 C13 1.489(2) . ? C2 C3 1.385(3) . ? C2 H2 0.969(17) . ? C3 C4 1.381(2) . ? C3 H3 1.02(2) . ? C4 C9 1.412(2) . ? C4 C5 1.501(2) . ? C5 C10 1.548(2) . ? C5 C6 1.568(2) . ? C5 H5 1.02(2) . ? C6 C11 1.526(3) . ? C6 C12 1.526(2) . ? C6 C7 1.580(2) . ? C7 C8 1.528(2) . ? C7 C10 1.550(2) . ? C7 H7 1.011(17) . ? C8 C9 1.524(2) . ? C8 C8 1.560(3) 2_453 ? C8 H8 0.990(19) . ? C10 H10A 1.01(2) . ? C10 H10B 0.994(17) . ? C11 H11A 1.03(2) . ? C11 H11B 1.04(2) . ? C11 H25 1.00(3) . ? C12 H12A 1.02(3) . ? C12 H12B 1.00(2) . ? C12 H12C 1.01(2) . ? C13 C14 1.396(2) . ? C14 C15 1.377(3) . ? C14 H14 0.982(18) . ? C15 C16 1.377(2) . ? C15 H15 0.97(2) . ? C16 C17 1.397(3) . ? C16 H16 0.98(2) . ? C17 C18 1.488(2) . ? C18 C23 1.387(3) . ? C18 C19 1.394(3) . ? C19 C20 1.378(3) . ? C19 H19 0.90(2) . ? C20 C21 1.387(3) . ? C20 H20 0.98(2) . ? C21 C22 1.378(3) . ? C22 C23 1.391(3) . ? C22 H22 0.97(3) . ? C23 H12 0.98(2) . ? C24 H24A 0.99(2) . ? C24 H24B 1.16(4) . ? C24 H24C 0.97(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 C9 N1 C1 118.31(14) . . ? C13 N2 C17 118.89(15) . . ? C21 O1 C24 117.14(18) . . ? N1 C1 C2 121.96(16) . . ? N1 C1 C13 116.36(14) . . ? C2 C1 C13 121.65(14) . . ? C3 C2 C1 119.32(14) . . ? C3 C2 H2 119.1(11) . . ? C1 C2 H2 121.5(11) . . ? C4 C3 C2 119.53(16) . . ? C4 C3 H3 118.0(11) . . ? C2 C3 H3 122.5(11) . . ? C3 C4 C9 117.73(16) . . ? C3 C4 C5 124.87(16) . . ? C9 C4 C5 117.39(14) . . ? C4 C5 C10 106.40(13) . . ? C4 C5 C6 109.21(15) . . ? C10 C5 C6 87.38(12) . . ? C4 C5 H5 112.1(11) . . ? C10 C5 H5 119.2(11) . . ? C6 C5 H5 119.6(11) . . ? C11 C6 C12 108.96(15) . . ? C11 C6 C5 117.59(15) . . ? C12 C6 C5 112.71(15) . . ? C11 C6 C7 120.33(15) . . ? C12 C6 C7 110.63(14) . . ? C5 C6 C7 84.92(12) . . ? C8 C7 C10 111.51(13) . . ? C8 C7 C6 111.23(13) . . ? C10 C7 C6 86.91(12) . . ? C8 C7 H7 112.2(10) . . ? C10 C7 H7 117.2(10) . . ? C6 C7 H7 115.4(9) . . ? C9 C8 C7 109.10(13) . . ? C9 C8 C8 112.61(16) . 2_453 ? C7 C8 C8 116.19(11) . 2_453 ? C9 C8 H8 105.9(10) . . ? C7 C8 H8 109.0(10) . . ? C8 C8 H8 103.4(10) 2_453 . ? N1 C9 C4 123.11(13) . . ? N1 C9 C8 118.41(14) . . ? C4 C9 C8 118.38(14) . . ? C5 C10 C7 86.63(13) . . ? C5 C10 H10A 112.8(11) . . ? C7 C10 H10A 110.1(11) . . ? C5 C10 H10B 115.1(10) . . ? C7 C10 H10B 118.2(10) . . ? H10A C10 H10B 111.8(15) . . ? C6 C11 H11A 112.5(12) . . ? C6 C11 H11B 108.6(16) . . ? H11A C11 H11B 110.0(18) . . ? C6 C11 H25 110.6(14) . . ? H11A C11 H25 106.0(18) . . ? H11B C11 H25 109.1(18) . . ? C6 C12 H12A 114.6(12) . . ? C6 C12 H12B 109.5(13) . . ? H12A C12 H12B 105.3(19) . . ? C6 C12 H12C 111.3(13) . . ? H12A C12 H12C 107.8(17) . . ? H12B C12 H12C 108.0(17) . . ? N2 C13 C14 122.41(16) . . ? N2 C13 C1 116.70(14) . . ? C14 C13 C1 120.86(14) . . ? C15 C14 C13 118.50(15) . . ? C15 C14 H14 123.4(12) . . ? C13 C14 H14 118.1(11) . . ? C14 C15 C16 119.41(18) . . ? C14 C15 H15 119.9(13) . . ? C16 C15 H15 120.7(13) . . ? C15 C16 C17 119.37(18) . . ? C15 C16 H16 122.0(12) . . ? C17 C16 H16 118.6(12) . . ? N2 C17 C16 121.36(15) . . ? N2 C17 C18 116.41(16) . . ? C16 C17 C18 122.23(15) . . ? C23 C18 C19 117.18(16) . . ? C23 C18 C17 122.41(17) . . ? C19 C18 C17 120.39(16) . . ? C20 C19 C18 121.80(19) . . ? C20 C19 H19 121.5(13) . . ? C18 C19 H19 116.7(13) . . ? C19 C20 C21 119.85(19) . . ? C19 C20 H20 119.5(12) . . ? C21 C20 H20 120.6(12) . . ? O1 C21 C22 124.53(18) . . ? O1 C21 C20 115.72(18) . . ? C22 C21 C20 119.74(16) . . ? C21 C22 C23 119.70(19) . . ? C21 C22 H22 120.4(13) . . ? C23 C22 H22 119.9(13) . . ? C18 C23 C22 121.7(2) . . ? C18 C23 H12 118.6(13) . . ? C22 C23 H12 119.6(13) . . ? O1 C24 H24A 106.0(15) . . ? O1 C24 H24B 111.8(18) . . ? H24A C24 H24B 111(2) . . ? O1 C24 H24C 111.1(16) . . ? H24A C24 H24C 108.9(19) . . ? H24B C24 H24C 108(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 N1 C1 C2 2.0(2) . . . . ? C9 N1 C1 C13 -175.88(14) . . . . ? N1 C1 C2 C3 -2.0(3) . . . . ? C13 C1 C2 C3 175.74(16) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C9 1.3(3) . . . . ? C2 C3 C4 C5 -178.49(16) . . . . ? C3 C4 C5 C10 -133.90(17) . . . . ? C9 C4 C5 C10 46.32(19) . . . . ? C3 C4 C5 C6 133.11(17) . . . . ? C9 C4 C5 C6 -46.66(19) . . . . ? C4 C5 C6 C11 -42.96(19) . . . . ? C10 C5 C6 C11 -149.42(16) . . . . ? C4 C5 C6 C12 -170.99(14) . . . . ? C10 C5 C6 C12 82.55(16) . . . . ? C4 C5 C6 C7 78.75(14) . . . . ? C10 C5 C6 C7 -27.71(12) . . . . ? C11 C6 C7 C8 34.9(2) . . . . ? C12 C6 C7 C8 163.42(14) . . . . ? C5 C6 C7 C8 -84.20(15) . . . . ? C11 C6 C7 C10 146.82(16) . . . . ? C12 C6 C7 C10 -84.68(16) . . . . ? C5 C6 C7 C10 27.70(13) . . . . ? C10 C7 C8 C9 -44.15(17) . . . . ? C6 C7 C8 C9 51.06(17) . . . . ? C10 C7 C8 C8 84.44(18) . . . 2_453 ? C6 C7 C8 C8 179.65(14) . . . 2_453 ? C1 N1 C9 C4 -0.3(2) . . . . ? C1 N1 C9 C8 176.10(14) . . . . ? C3 C4 C9 N1 -1.3(2) . . . . ? C5 C4 C9 N1 178.45(15) . . . . ? C3 C4 C9 C8 -177.74(16) . . . . ? C5 C4 C9 C8 2.1(2) . . . . ? C7 C8 C9 N1 179.73(14) . . . . ? C8 C8 C9 N1 49.18(16) 2_453 . . . ? C7 C8 C9 C4 -3.7(2) . . . . ? C8 C8 C9 C4 -134.26(12) 2_453 . . . ? C4 C5 C10 C7 -81.02(15) . . . . ? C6 C5 C10 C7 28.23(12) . . . . ? C8 C7 C10 C5 83.61(14) . . . . ? C6 C7 C10 C5 -28.01(12) . . . . ? C17 N2 C13 C14 0.9(2) . . . . ? C17 N2 C13 C1 -177.41(14) . . . . ? N1 C1 C13 N2 -177.75(15) . . . . ? C2 C1 C13 N2 4.4(2) . . . . ? N1 C1 C13 C14 4.0(2) . . . . ? C2 C1 C13 C14 -173.94(18) . . . . ? N2 C13 C14 C15 -1.8(3) . . . . ? C1 C13 C14 C15 176.37(16) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 1.4(3) . . . . ? C13 N2 C17 C16 1.3(2) . . . . ? C13 N2 C17 C18 -177.56(15) . . . . ? C15 C16 C17 N2 -2.4(3) . . . . ? C15 C16 C17 C18 176.36(17) . . . . ? N2 C17 C18 C23 -170.90(17) . . . . ? C16 C17 C18 C23 10.3(3) . . . . ? N2 C17 C18 C19 10.7(2) . . . . ? C16 C17 C18 C19 -168.17(17) . . . . ? C23 C18 C19 C20 0.4(3) . . . . ? C17 C18 C19 C20 178.96(16) . . . . ? C18 C19 C20 C21 -0.1(3) . . . . ? C24 O1 C21 C22 12.3(3) . . . . ? C24 O1 C21 C20 -168.71(18) . . . . ? C19 C20 C21 O1 -179.59(16) . . . . ? C19 C20 C21 C22 -0.6(3) . . . . ? O1 C21 C22 C23 179.86(17) . . . . ? C20 C21 C22 C23 1.0(3) . . . . ? C19 C18 C23 C22 -0.1(3) . . . . ? C17 C18 C23 C22 -178.56(17) . . . . ? C21 C22 C23 C18 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.89 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.344 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.111 #=========================================================================== #==================== data_cpd20 _database_code_CSD 179707 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Br N2' _chemical_formula_weight 329.24 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' 'Br' 'Br' -0.2901 2.4595 '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 'P 21 21 21' 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' _cell_length_a 6.1546(5) _cell_length_b 13.5496(13) _cell_length_c 17.5877(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1466.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4752 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.96 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 2.794 _exptl_absorpt_correction_type empirical_DIFABS _exptl_absorpt_correction_T_min 0.355 _exptl_absorpt_correction_T_max 0.772 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10465 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0937 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.96 _reflns_number_total 2871 _reflns_number_gt 1760 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0179P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(13) _refine_ls_number_reflns 2871 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0510 _refine_ls_goodness_of_fit_ref 0.783 _refine_ls_restrained_S_all 0.783 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.08345(7) -0.54840(3) -0.25131(4) 0.04187(12) Uani 1 1 d . . . N1 N -0.3094(6) -0.1334(2) -0.10252(19) 0.0266(8) Uani 1 1 d . . . N2 N -0.1633(6) -0.3645(2) -0.19033(19) 0.0302(9) Uani 1 1 d . . . C1 C -0.1853(8) -0.2114(3) -0.1220(2) 0.0249(10) Uani 1 1 d . . . C2 C 0.0209(8) -0.2264(3) -0.0924(2) 0.0268(12) Uani 1 1 d . . . H2 H 0.103(8) -0.285(3) -0.104(2) 0.027(10) Uiso 1 1 d . . . C3 C 0.0971(9) -0.1615(3) -0.0377(3) 0.0299(10) Uani 1 1 d . . . H3 H 0.230(7) -0.168(2) -0.024(2) 0.006(10) Uiso 1 1 d . . . C4 C -0.0276(7) -0.0827(3) -0.0150(2) 0.0243(10) Uani 1 1 d . . . C5 C 0.0305(8) -0.0089(3) 0.0449(3) 0.0247(11) Uani 1 1 d . . . H5 H 0.166(6) -0.027(2) 0.064(2) 0.015(10) Uiso 1 1 d . . . C6 C -0.0135(7) 0.0986(3) 0.0150(2) 0.0274(11) Uani 1 1 d . . . C7 C -0.2562(9) 0.0779(4) 0.0348(3) 0.0315(15) Uani 1 1 d . . . H7 H -0.339(7) 0.136(3) 0.050(2) 0.032(12) Uiso 1 1 d . . . C8 C -0.3667(8) 0.0180(3) -0.0282(3) 0.0315(12) Uani 1 1 d . . . H8A H -0.384(8) 0.064(3) -0.076(2) 0.036(11) Uiso 1 1 d . . . H8B H -0.505(8) -0.007(3) -0.012(2) 0.037(15) Uiso 1 1 d . . . C9 C -0.2328(8) -0.0707(4) -0.0496(3) 0.0237(12) Uani 1 1 d . . . C10 C -0.1735(8) 0.0053(3) 0.0965(3) 0.0338(12) Uani 1 1 d . . . H10A H -0.147(6) 0.044(3) 0.141(2) 0.037(11) Uiso 1 1 d . . . H10B H -0.287(6) -0.055(3) 0.1047(18) 0.018(9) Uiso 1 1 d . . . C11 C 0.0453(9) 0.1231(3) -0.0675(3) 0.0321(12) Uani 1 1 d . . . H11A H 0.007(7) 0.191(3) -0.0776(19) 0.022(10) Uiso 1 1 d . . . H11B H 0.003(7) 0.078(3) -0.098(2) 0.043(15) Uiso 1 1 d . . . H11C H 0.212(9) 0.126(3) -0.074(3) 0.064(17) Uiso 1 1 d . . . C12 C 0.0847(11) 0.1771(3) 0.0670(3) 0.0365(10) Uani 1 1 d . . . H12A H 0.267(11) 0.174(4) 0.059(3) 0.08(2) Uiso 1 1 d . . . H12B H 0.032(6) 0.251(2) 0.0493(19) 0.022(9) Uiso 1 1 d . . . H12C H 0.059(10) 0.161(3) 0.112(2) 0.049(15) Uiso 1 1 d . . . C13 C -0.2811(8) -0.2825(3) -0.1763(2) 0.0258(10) Uani 1 1 d . . . C14 C -0.4869(8) -0.2684(3) -0.2080(2) 0.0325(12) Uani 1 1 d . . . H14 H -0.550(6) -0.210(2) -0.1999(16) 0.009(9) Uiso 1 1 d . . . C15 C -0.5731(8) -0.3404(3) -0.2552(4) 0.0364(9) Uani 1 1 d . . . H15 H -0.718(8) -0.329(3) -0.268(3) 0.059(16) Uiso 1 1 d . . . C16 C -0.4577(8) -0.4263(3) -0.2679(2) 0.0350(12) Uani 1 1 d . . . H16 H -0.528(7) -0.479(3) -0.297(2) 0.035(12) Uiso 1 1 d . . . C17 C -0.2507(7) -0.4320(3) -0.2349(2) 0.0308(12) 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 Br1 0.0473(2) 0.03586(17) 0.0425(2) -0.0114(3) -0.0004(5) 0.0012(3) N1 0.021(2) 0.0287(18) 0.030(2) 0.0005(16) 0.0009(17) 0.0001(16) N2 0.032(3) 0.0340(19) 0.0246(19) 0.0000(16) 0.0000(16) -0.0063(16) C1 0.029(3) 0.021(2) 0.025(2) 0.0038(17) 0.003(2) 0.0008(18) C2 0.027(3) 0.020(2) 0.033(2) 0.0007(17) 0.007(2) 0.001(2) C3 0.022(3) 0.031(2) 0.037(2) 0.0093(18) -0.005(3) -0.001(2) C4 0.024(3) 0.0229(19) 0.026(2) 0.0055(16) 0.0009(19) -0.0006(17) C5 0.016(3) 0.030(2) 0.029(3) 0.0003(19) 0.001(2) 0.0056(18) C6 0.025(3) 0.030(2) 0.027(2) -0.0023(17) -0.0025(19) -0.0012(18) C7 0.032(4) 0.032(3) 0.031(3) -0.002(2) 0.001(3) 0.004(2) C8 0.019(3) 0.030(2) 0.045(3) -0.005(2) 0.001(2) 0.0025(19) C9 0.015(3) 0.027(3) 0.029(3) 0.001(2) 0.002(2) -0.001(2) C10 0.038(3) 0.032(2) 0.031(3) 0.000(2) 0.008(2) -0.004(2) C11 0.033(4) 0.026(2) 0.037(3) 0.001(2) 0.007(2) -0.004(2) C12 0.035(3) 0.034(2) 0.040(3) -0.003(2) 0.001(3) -0.003(3) C13 0.023(3) 0.031(2) 0.023(2) 0.0033(18) 0.004(2) -0.004(2) C14 0.031(3) 0.034(2) 0.033(2) 0.000(2) 0.002(2) 0.000(2) C15 0.029(3) 0.047(2) 0.033(2) -0.002(3) -0.003(4) -0.001(2) C16 0.045(3) 0.038(2) 0.022(3) 0.0003(15) 0.000(2) -0.013(2) C17 0.037(3) 0.035(2) 0.020(3) 0.0002(18) 0.005(2) -0.0068(18) _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 Br1 C17 1.905(4) . ? N1 C1 1.349(5) . ? N1 C9 1.346(6) . ? N2 C17 1.320(5) . ? N2 C13 1.349(5) . ? C1 C2 1.387(6) . ? C1 C13 1.478(6) . ? C2 C3 1.385(6) . ? C2 H2 0.96(4) . ? C3 C4 1.374(6) . ? C3 H3 0.86(4) . ? C4 C9 1.411(6) . ? C4 C5 1.495(6) . ? C5 C10 1.561(6) . ? C5 C6 1.573(6) . ? C5 H5 0.93(4) . ? C6 C12 1.527(6) . ? C6 C11 1.532(6) . ? C6 C7 1.559(7) . ? C7 C8 1.533(7) . ? C7 C10 1.550(7) . ? C7 H7 0.97(4) . ? C8 C9 1.505(6) . ? C8 H8A 1.06(4) . ? C8 H8B 0.96(5) . ? C10 H10A 0.95(4) . ? C10 H10B 1.09(4) . ? C11 H11A 0.97(4) . ? C11 H11B 0.85(4) . ? C11 H11C 1.03(6) . ? C12 H12A 1.13(6) . ? C12 H12B 1.09(3) . ? C12 H12C 0.83(4) . ? C13 C14 1.398(6) . ? C14 C15 1.386(6) . ? C14 H14 0.89(3) . ? C15 C16 1.381(5) . ? C15 H15 0.93(5) . ? C16 C17 1.402(6) . ? C16 H16 0.98(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 C1 N1 C9 118.2(4) . . ? C17 N2 C13 117.5(4) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 C13 116.7(4) . . ? C2 C1 C13 120.8(4) . . ? C3 C2 C1 118.6(4) . . ? C3 C2 H2 119(3) . . ? C1 C2 H2 122(3) . . ? C4 C3 C2 120.4(5) . . ? C4 C3 H3 122(2) . . ? C2 C3 H3 117(2) . . ? C3 C4 C9 117.7(4) . . ? C3 C4 C5 126.2(4) . . ? C9 C4 C5 116.1(4) . . ? C4 C5 C10 107.4(4) . . ? C4 C5 C6 110.0(3) . . ? C10 C5 C6 86.7(3) . . ? C4 C5 H5 107(2) . . ? C10 C5 H5 123(2) . . ? C6 C5 H5 121(2) . . ? C12 C6 C11 108.8(4) . . ? C12 C6 C7 111.7(4) . . ? C11 C6 C7 118.5(4) . . ? C12 C6 C5 112.1(3) . . ? C11 C6 C5 118.5(3) . . ? C7 C6 C5 85.6(3) . . ? C8 C7 C10 108.4(4) . . ? C8 C7 C6 111.0(4) . . ? C10 C7 C6 87.5(4) . . ? C8 C7 H7 113(3) . . ? C10 C7 H7 120(2) . . ? C6 C7 H7 115(2) . . ? C9 C8 C7 111.1(4) . . ? C9 C8 H8A 109(2) . . ? C7 C8 H8A 108(2) . . ? C9 C8 H8B 106(3) . . ? C7 C8 H8B 112(3) . . ? H8A C8 H8B 111(4) . . ? N1 C9 C4 122.6(4) . . ? N1 C9 C8 119.0(4) . . ? C4 C9 C8 118.3(4) . . ? C7 C10 C5 86.3(4) . . ? C7 C10 H10A 106(2) . . ? C5 C10 H10A 114(2) . . ? C7 C10 H10B 111.2(18) . . ? C5 C10 H10B 120.0(19) . . ? H10A C10 H10B 115(3) . . ? C6 C11 H11A 109(2) . . ? C6 C11 H11B 112(3) . . ? H11A C11 H11B 120(4) . . ? C6 C11 H11C 110(3) . . ? H11A C11 H11C 101(4) . . ? H11B C11 H11C 105(4) . . ? C6 C12 H12A 107(3) . . ? C6 C12 H12B 110.4(19) . . ? H12A C12 H12B 107(3) . . ? C6 C12 H12C 108(3) . . ? H12A C12 H12C 108(5) . . ? H12B C12 H12C 117(4) . . ? N2 C13 C14 121.7(4) . . ? N2 C13 C1 116.1(4) . . ? C14 C13 C1 122.0(4) . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14 124(2) . . ? C13 C14 H14 117(2) . . ? C16 C15 C14 119.6(5) . . ? C16 C15 H15 126(3) . . ? C14 C15 H15 113(3) . . ? C15 C16 C17 116.5(4) . . ? C15 C16 H16 118(2) . . ? C17 C16 H16 125(2) . . ? N2 C17 C16 125.3(4) . . ? N2 C17 Br1 116.4(3) . . ? C16 C17 Br1 118.3(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 C9 N1 C1 C2 -3.2(6) . . . . ? C9 N1 C1 C13 175.8(4) . . . . ? N1 C1 C2 C3 3.5(6) . . . . ? C13 C1 C2 C3 -175.5(4) . . . . ? C1 C2 C3 C4 -1.6(6) . . . . ? C2 C3 C4 C9 -0.3(6) . . . . ? C2 C3 C4 C5 177.9(4) . . . . ? C3 C4 C5 C10 -134.2(4) . . . . ? C9 C4 C5 C10 44.1(5) . . . . ? C3 C4 C5 C6 133.0(4) . . . . ? C9 C4 C5 C6 -48.8(5) . . . . ? C4 C5 C6 C12 -168.4(4) . . . . ? C10 C5 C6 C12 84.2(4) . . . . ? C4 C5 C6 C11 -40.4(5) . . . . ? C10 C5 C6 C11 -147.7(4) . . . . ? C4 C5 C6 C7 79.8(4) . . . . ? C10 C5 C6 C7 -27.5(3) . . . . ? C12 C6 C7 C8 166.9(4) . . . . ? C11 C6 C7 C8 39.1(6) . . . . ? C5 C6 C7 C8 -81.0(4) . . . . ? C12 C6 C7 C10 -84.4(4) . . . . ? C11 C6 C7 C10 147.9(4) . . . . ? C5 C6 C7 C10 27.7(3) . . . . ? C10 C7 C8 C9 -45.0(6) . . . . ? C6 C7 C8 C9 49.4(6) . . . . ? C1 N1 C9 C4 1.1(7) . . . . ? C1 N1 C9 C8 178.7(4) . . . . ? C3 C4 C9 N1 0.6(7) . . . . ? C5 C4 C9 N1 -177.8(4) . . . . ? C3 C4 C9 C8 -177.0(4) . . . . ? C5 C4 C9 C8 4.5(6) . . . . ? C7 C8 C9 N1 177.9(4) . . . . ? C7 C8 C9 C4 -4.3(7) . . . . ? C8 C7 C10 C5 83.4(4) . . . . ? C6 C7 C10 C5 -27.9(3) . . . . ? C4 C5 C10 C7 -82.3(4) . . . . ? C6 C5 C10 C7 27.7(3) . . . . ? C17 N2 C13 C14 -0.7(6) . . . . ? C17 N2 C13 C1 175.9(3) . . . . ? N1 C1 C13 N2 -174.5(4) . . . . ? C2 C1 C13 N2 4.5(5) . . . . ? N1 C1 C13 C14 2.1(6) . . . . ? C2 C1 C13 C14 -178.9(4) . . . . ? N2 C13 C14 C15 0.1(7) . . . . ? C1 C13 C14 C15 -176.3(4) . . . . ? C13 C14 C15 C16 2.2(8) . . . . ? C14 C15 C16 C17 -3.6(7) . . . . ? C13 N2 C17 C16 -1.1(6) . . . . ? C13 N2 C17 Br1 -178.4(3) . . . . ? C15 C16 C17 N2 3.2(6) . . . . ? C15 C16 C17 Br1 -179.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.384 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.064 #=========================================================================== #===============END data_cpd3 _database_code_CSD 196850 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H50 N4' _chemical_formula_sum 'C34 H50 N4' _chemical_formula_weight 514.78 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 11.4893(8) _cell_length_b 20.8542(16) _cell_length_c 6.4198(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1538.19(19) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5776 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 25.93 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.065 _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 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12014 _diffrn_reflns_av_R_equivalents 0.0715 _diffrn_reflns_av_sigmaI/netI 0.0853 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.93 _reflns_number_total 2938 _reflns_number_gt 1789 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0454P)^2^] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 2938 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.834 _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 N1 N 0.13020(14) 0.41124(8) 0.2106(3) 0.0266(4) Uani 1 1 d . . . N2 N 0.35112(15) 0.30393(10) 0.4161(4) 0.0411(5) Uani 1 1 d . . . C1 C 0.19659(18) 0.35825(10) 0.2257(4) 0.0279(5) Uani 1 1 d . . . C2 C 0.16894(18) 0.30235(11) 0.1240(4) 0.0324(6) Uani 1 1 d . . . H2 H 0.2156 0.2651 0.1420 0.039 Uiso 1 1 calc R . . C3 C 0.07138(19) 0.30078(11) -0.0063(4) 0.0326(6) Uani 1 1 d . . . H3 H 0.0505 0.2624 -0.0767 0.039 Uiso 1 1 calc R . . C4 C 0.00577(19) 0.35568(10) -0.0315(4) 0.0287(6) Uani 1 1 d . . . C5 C 0.03685(16) 0.40935(10) 0.0836(4) 0.0241(5) Uani 1 1 d . . . C6 C -0.03672(16) 0.46930(9) 0.0677(4) 0.0240(5) Uani 1 1 d . . . H6 H -0.0844 0.4708 0.1979 0.029 Uiso 1 1 calc R . . C7 C -0.12401(17) 0.46154(10) -0.1128(4) 0.0273(5) Uani 1 1 d . . . H7A H -0.1700 0.5008 -0.1477 0.033 Uiso 1 1 calc R . . C8 C -0.19770(18) 0.39891(10) -0.0805(4) 0.0303(6) Uani 1 1 d . . . C9 C -0.09290(18) 0.36357(10) -0.1854(4) 0.0319(6) Uani 1 1 d . . . H9A H -0.1120 0.3255 -0.2739 0.038 Uiso 1 1 calc R . . C10 C -0.06709(19) 0.42724(10) -0.3013(4) 0.0326(6) Uani 1 1 d . . . H10B H -0.1101 0.4324 -0.4339 0.039 Uiso 1 1 calc R . . H10A H 0.0168 0.4366 -0.3191 0.039 Uiso 1 1 calc R . . C11 C -0.23412(19) 0.37984(11) 0.1376(4) 0.0383(7) Uani 1 1 d . . . H11C H -0.2779 0.3395 0.1321 0.057 Uiso 1 1 calc R . . H11B H -0.2833 0.4135 0.1974 0.057 Uiso 1 1 calc R . . H11A H -0.1648 0.3741 0.2245 0.057 Uiso 1 1 calc R . . C12 C -0.3064(2) 0.39866(12) -0.2207(4) 0.0431(7) Uani 1 1 d . . . H12C H -0.3395 0.3554 -0.2250 0.065 Uiso 1 1 calc R . . H12B H -0.2848 0.4120 -0.3619 0.065 Uiso 1 1 calc R . . H12A H -0.3643 0.4285 -0.1645 0.065 Uiso 1 1 calc R . . C13 C 0.3109(2) 0.36660(11) 0.3500(4) 0.0355(6) Uani 1 1 d . . . C14 C 0.4001(2) 0.39367(15) 0.1869(6) 0.0673(10) Uani 1 1 d . . . H14C H 0.3654 0.4303 0.1141 0.101 Uiso 1 1 calc R . . H14B H 0.4195 0.3601 0.0859 0.101 Uiso 1 1 calc R . . H14A H 0.4709 0.4075 0.2591 0.101 Uiso 1 1 calc R . . C15 C 0.2960(2) 0.41529(14) 0.5242(5) 0.0611(10) Uani 1 1 d . . . H15C H 0.2731 0.4567 0.4650 0.092 Uiso 1 1 calc R . . H15B H 0.3697 0.4201 0.5994 0.092 Uiso 1 1 calc R . . H15A H 0.2356 0.4005 0.6206 0.092 Uiso 1 1 calc R . . C16 C 0.2755(2) 0.27632(16) 0.5745(5) 0.0642(9) Uani 1 1 d . . . H16C H 0.2923 0.2305 0.5887 0.096 Uiso 1 1 calc R . . H16B H 0.1940 0.2821 0.5334 0.096 Uiso 1 1 calc R . . H16A H 0.2892 0.2978 0.7080 0.096 Uiso 1 1 calc R . . C17 C 0.4711(2) 0.30241(15) 0.4939(5) 0.0556(8) Uani 1 1 d . . . H17C H 0.4935 0.2580 0.5236 0.083 Uiso 1 1 calc R . . H17B H 0.4765 0.3279 0.6217 0.083 Uiso 1 1 calc R . . H17A H 0.5235 0.3203 0.3883 0.083 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 N1 0.0219(9) 0.0311(10) 0.0270(12) -0.0024(9) -0.0027(8) 0.0030(8) N2 0.0274(10) 0.0471(12) 0.0489(15) 0.0012(11) -0.0098(10) 0.0057(9) C1 0.0261(11) 0.0282(12) 0.0295(15) -0.0011(10) -0.0020(10) 0.0024(10) C2 0.0313(12) 0.0283(12) 0.0375(17) -0.0017(11) -0.0042(11) 0.0047(10) C3 0.0317(12) 0.0270(12) 0.0389(17) -0.0082(11) -0.0050(11) -0.0013(11) C4 0.0247(11) 0.0313(12) 0.0301(16) -0.0042(10) -0.0032(10) -0.0018(10) C5 0.0225(11) 0.0275(12) 0.0225(14) -0.0011(10) 0.0016(10) 0.0000(9) C6 0.0204(10) 0.0281(11) 0.0234(14) 0.0018(11) -0.0012(10) -0.0011(9) C7 0.0209(11) 0.0316(11) 0.0293(15) 0.0035(11) -0.0048(10) -0.0013(9) C8 0.0229(10) 0.0369(13) 0.0312(16) 0.0007(11) -0.0087(11) -0.0037(10) C9 0.0284(11) 0.0337(12) 0.0337(16) -0.0065(12) -0.0092(11) -0.0030(10) C10 0.0302(12) 0.0457(14) 0.0221(15) -0.0012(11) -0.0041(11) -0.0016(10) C11 0.0276(12) 0.0414(14) 0.046(2) 0.0048(13) -0.0025(11) -0.0076(10) C12 0.0291(12) 0.0500(16) 0.0501(19) 0.0054(13) -0.0156(12) -0.0064(12) C13 0.0291(11) 0.0351(13) 0.0423(18) -0.0036(11) -0.0103(11) 0.0054(10) C14 0.0325(14) 0.089(2) 0.081(3) 0.035(2) -0.0103(16) -0.0199(14) C15 0.0453(16) 0.0627(18) 0.075(3) -0.0371(17) -0.0341(16) 0.0196(14) C16 0.0479(16) 0.096(2) 0.049(2) 0.0266(18) -0.0066(15) -0.0194(16) C17 0.0376(14) 0.0674(18) 0.062(2) -0.0128(16) -0.0219(14) 0.0162(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 N1 C1 1.346(3) . ? N1 C5 1.348(3) . ? N2 C13 1.450(3) . ? N2 C16 1.456(3) . ? N2 C17 1.466(3) . ? C1 C2 1.373(3) . ? C1 C13 1.546(3) . ? C2 C3 1.399(3) . ? C3 C4 1.380(3) . ? C4 C5 1.388(3) . ? C4 C9 1.513(3) . ? C5 C6 1.513(3) . ? C6 C6 1.534(4) 2_565 ? C6 C7 1.541(3) . ? C7 C10 1.550(3) . ? C7 C8 1.570(3) . ? C8 C11 1.515(3) . ? C8 C12 1.540(3) . ? C8 C9 1.564(3) . ? C9 C10 1.551(3) . ? C13 C15 1.520(3) . ? C13 C14 1.570(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 C1 N1 C5 118.07(18) . . ? C13 N2 C16 111.7(2) . . ? C13 N2 C17 114.8(2) . . ? C16 N2 C17 108.3(2) . . ? N1 C1 C2 122.10(19) . . ? N1 C1 C13 115.20(18) . . ? C2 C1 C13 122.51(19) . . ? C1 C2 C3 119.3(2) . . ? C4 C3 C2 119.2(2) . . ? C3 C4 C5 117.78(19) . . ? C3 C4 C9 125.16(19) . . ? C5 C4 C9 116.93(19) . . ? N1 C5 C4 123.39(18) . . ? N1 C5 C6 117.47(19) . . ? C4 C5 C6 119.13(18) . . ? C5 C6 C6 112.5(2) . 2_565 ? C5 C6 C7 109.12(18) . . ? C6 C6 C7 116.47(14) 2_565 . ? C6 C7 C10 111.15(17) . . ? C6 C7 C8 109.81(18) . . ? C10 C7 C8 86.95(16) . . ? C11 C8 C12 108.38(19) . . ? C11 C8 C9 119.15(19) . . ? C12 C8 C9 111.8(2) . . ? C11 C8 C7 119.30(19) . . ? C12 C8 C7 111.29(18) . . ? C9 C8 C7 85.41(16) . . ? C4 C9 C10 105.25(17) . . ? C4 C9 C8 110.29(19) . . ? C10 C9 C8 87.15(16) . . ? C9 C10 C7 86.57(18) . . ? N2 C13 C15 115.0(2) . . ? N2 C13 C1 108.68(18) . . ? C15 C13 C1 111.07(19) . . ? N2 C13 C14 108.1(2) . . ? C15 C13 C14 108.9(2) . . ? C1 C13 C14 104.5(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 C5 N1 C1 C2 -3.0(3) . . . . ? C5 N1 C1 C13 172.1(2) . . . . ? N1 C1 C2 C3 2.6(4) . . . . ? C13 C1 C2 C3 -172.1(2) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 -3.3(3) . . . . ? C2 C3 C4 C9 172.4(2) . . . . ? C1 N1 C5 C4 0.1(3) . . . . ? C1 N1 C5 C6 -179.82(19) . . . . ? C3 C4 C5 N1 3.0(3) . . . . ? C9 C4 C5 N1 -173.1(2) . . . . ? C3 C4 C5 C6 -177.0(2) . . . . ? C9 C4 C5 C6 6.9(3) . . . . ? N1 C5 C6 C6 38.8(2) . . . 2_565 ? C4 C5 C6 C6 -141.17(16) . . . 2_565 ? N1 C5 C6 C7 169.67(19) . . . . ? C4 C5 C6 C7 -10.3(3) . . . . ? C5 C6 C7 C10 -39.2(2) . . . . ? C6 C6 C7 C10 89.5(2) 2_565 . . . ? C5 C6 C7 C8 55.3(2) . . . . ? C6 C6 C7 C8 -176.01(18) 2_565 . . . ? C6 C7 C8 C11 37.2(3) . . . . ? C10 C7 C8 C11 148.57(19) . . . . ? C6 C7 C8 C12 164.53(19) . . . . ? C10 C7 C8 C12 -84.1(2) . . . . ? C6 C7 C8 C9 -83.84(19) . . . . ? C10 C7 C8 C9 27.56(16) . . . . ? C3 C4 C9 C10 -130.3(2) . . . . ? C5 C4 C9 C10 45.4(3) . . . . ? C3 C4 C9 C8 137.0(2) . . . . ? C5 C4 C9 C8 -47.2(3) . . . . ? C11 C8 C9 C4 -43.5(2) . . . . ? C12 C8 C9 C4 -171.22(18) . . . . ? C7 C8 C9 C4 77.67(19) . . . . ? C11 C8 C9 C10 -148.70(19) . . . . ? C12 C8 C9 C10 83.6(2) . . . . ? C7 C8 C9 C10 -27.54(16) . . . . ? C4 C9 C10 C7 -82.37(19) . . . . ? C8 C9 C10 C7 27.89(15) . . . . ? C6 C7 C10 C9 82.30(18) . . . . ? C8 C7 C10 C9 -27.78(15) . . . . ? C16 N2 C13 C15 55.8(3) . . . . ? C17 N2 C13 C15 -68.1(3) . . . . ? C16 N2 C13 C1 -69.4(3) . . . . ? C17 N2 C13 C1 166.8(2) . . . . ? C16 N2 C13 C14 177.7(2) . . . . ? C17 N2 C13 C14 53.8(3) . . . . ? N1 C1 C13 N2 160.0(2) . . . . ? C2 C1 C13 N2 -24.9(3) . . . . ? N1 C1 C13 C15 32.5(3) . . . . ? C2 C1 C13 C15 -152.4(2) . . . . ? N1 C1 C13 C14 -84.8(3) . . . . ? C2 C1 C13 C14 90.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.93 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.307 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.037 #================================================= data_cpd6d _database_code_CSD 196851 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Br N2' _chemical_formula_weight 329.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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' _cell_length_a 6.5403(8) _cell_length_b 11.3397(10) _cell_length_c 20.395(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1512.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 12.85 _cell_measurement_theta_max 25.55 _exptl_crystal_description bloc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 3.619 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_correction_T_min 0.140 _exptl_absorpt_correction_T_max 0.283 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE AED2 4-circle diffractometer' _diffrn_measurement_method 2\q/\w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1.5 _diffrn_reflns_number 6472 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 59.60 _reflns_number_total 2219 _reflns_number_gt 2163 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'STADI4 (Stoe STADI4 Software, 1997)' _computing_cell_refinement 'STADI4 (Stoe STADI4 Software 1997)' _computing_data_reduction 'X-RED (Stoe STADI4 Software, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.0247P)^2^+0.4004P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00282(18) _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(3) _refine_ls_number_reflns 2219 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 C1 C -0.1058(4) -0.2020(2) -0.33808(12) 0.0541(6) Uani 1 1 d . . . C2 C 0.0561(4) -0.1976(3) -0.38184(13) 0.0578(6) Uani 1 1 d . . . H2A H 0.0895 -0.1273 -0.4027 0.069 Uiso 1 1 calc R . . C3 C 0.1671(4) -0.2986(2) -0.39408(12) 0.0558(6) Uani 1 1 d . . . C4 C 0.3380(5) -0.3065(3) -0.44373(16) 0.0713(8) Uani 1 1 d . . . H4B H 0.4440 -0.2500 -0.4327 0.086 Uiso 1 1 calc R . . H4A H 0.2858 -0.2869 -0.4869 0.086 Uiso 1 1 calc R . . C5 C 0.4289(5) -0.4312(3) -0.44482(16) 0.0739(8) Uani 1 1 d . . . H5A H 0.5445 -0.4422 -0.4747 0.089 Uiso 1 1 calc R . . C6 C 0.2602(6) -0.5280(3) -0.44863(15) 0.0690(8) Uani 1 1 d . . . C7 C 0.2433(5) -0.5088(3) -0.37219(14) 0.0622(7) Uani 1 1 d . . . H7A H 0.2112 -0.5786 -0.3458 0.075 Uiso 1 1 calc R . . C8 C 0.1174(4) -0.4013(2) -0.35949(12) 0.0546(6) Uani 1 1 d . . . C9 C -0.0448(5) -0.3954(3) -0.31647(13) 0.0642(7) Uani 1 1 d . . . H9A H -0.0780 -0.4635 -0.2934 0.077 Uiso 1 1 calc R . . C10 C 0.4676(5) -0.4699(3) -0.37324(16) 0.0739(8) Uani 1 1 d . . . H10B H 0.5648 -0.5340 -0.3687 0.089 Uiso 1 1 calc R . . H10A H 0.4990 -0.4056 -0.3436 0.089 Uiso 1 1 calc R . . C11 C 0.0707(7) -0.5078(4) -0.49026(15) 0.0888(11) Uani 1 1 d . . . H11C H -0.0256 -0.5702 -0.4826 0.133 Uiso 1 1 calc R . . H11B H 0.1083 -0.5067 -0.5358 0.133 Uiso 1 1 calc R . . H11A H 0.0097 -0.4337 -0.4787 0.133 Uiso 1 1 calc R . . C12 C 0.3529(7) -0.6500(3) -0.46477(19) 0.0941(11) Uani 1 1 d . . . H12A H 0.3830 -0.6542 -0.5108 0.141 Uiso 1 1 calc R . . H12B H 0.2568 -0.7106 -0.4535 0.141 Uiso 1 1 calc R . . H12C H 0.4765 -0.6608 -0.4401 0.141 Uiso 1 1 calc R . . C13 C -0.2378(5) -0.0959(3) -0.32691(12) 0.0607(7) Uani 1 1 d . . . C14 C -0.4417(5) -0.1081(3) -0.30940(15) 0.0746(8) Uani 1 1 d . . . H14A H -0.4974 -0.1822 -0.3013 0.090 Uiso 1 1 calc R . . C15 C -0.5599(6) -0.0077(4) -0.30422(18) 0.0912(11) Uani 1 1 d . . . H15A H -0.6983 -0.0138 -0.2944 0.109 Uiso 1 1 calc R . . C16 C -0.4735(6) 0.1005(4) -0.31350(16) 0.0848(10) Uani 1 1 d . . . H16A H -0.5492 0.1695 -0.3092 0.102 Uiso 1 1 calc R . . C17 C -0.2690(6) 0.1029(3) -0.32946(14) 0.0706(8) Uani 1 1 d . . . Br1 Br -0.13826(7) 0.25114(3) -0.34164(2) 0.1002(2) Uani 1 1 d . . . N1 N -0.1576(4) -0.2998(2) -0.30544(11) 0.0632(6) Uani 1 1 d . . . N2 N -0.1504(4) 0.0100(2) -0.33707(12) 0.0621(6) 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 C1 0.0513(15) 0.0622(14) 0.0488(12) -0.0048(12) -0.0014(12) -0.0050(13) C2 0.0554(15) 0.0578(14) 0.0601(14) 0.0032(12) 0.0019(14) -0.0030(14) C3 0.0509(15) 0.0628(15) 0.0535(13) 0.0035(12) 0.0013(12) -0.0021(15) C4 0.0666(18) 0.0701(17) 0.0773(17) 0.0080(15) 0.0201(17) 0.0076(17) C5 0.0651(19) 0.0767(19) 0.0798(18) 0.0011(15) 0.0118(18) 0.0126(17) C6 0.0718(19) 0.0691(18) 0.0662(16) -0.0084(14) -0.0053(16) 0.0122(17) C7 0.0662(17) 0.0580(15) 0.0626(15) 0.0011(13) -0.0070(14) 0.0026(15) C8 0.0531(15) 0.0594(14) 0.0512(12) 0.0003(11) -0.0071(12) -0.0108(13) C9 0.0663(17) 0.0653(16) 0.0609(14) 0.0064(14) 0.0018(15) -0.0083(16) C10 0.0625(18) 0.0711(19) 0.0881(19) 0.0014(16) -0.0110(18) 0.0046(16) C11 0.097(3) 0.100(3) 0.0695(18) -0.0169(17) -0.019(2) 0.011(2) C12 0.103(3) 0.081(2) 0.098(2) -0.0263(19) -0.005(3) 0.023(2) C13 0.0569(15) 0.0770(19) 0.0482(13) -0.0126(13) 0.0002(12) -0.0006(15) C14 0.0644(18) 0.091(2) 0.0689(17) -0.0181(17) 0.0138(16) -0.0050(19) C15 0.067(2) 0.118(3) 0.089(2) -0.030(2) 0.0179(19) 0.014(2) C16 0.080(2) 0.097(2) 0.078(2) -0.0331(19) -0.0011(19) 0.024(2) C17 0.078(2) 0.0728(18) 0.0613(16) -0.0142(15) -0.0112(16) 0.0113(17) Br1 0.1143(4) 0.0658(2) 0.1206(3) -0.0060(2) -0.0249(3) 0.0097(3) N1 0.0586(14) 0.0739(14) 0.0572(12) -0.0028(11) 0.0086(12) -0.0082(13) N2 0.0618(14) 0.0610(13) 0.0637(12) -0.0088(11) -0.0062(13) 0.0013(12) _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 C1 N1 1.337(4) . ? C1 C2 1.386(4) . ? C1 C13 1.498(4) . ? C2 C3 1.378(4) . ? C2 H2A 0.9300 . ? C3 C8 1.400(4) . ? C3 C4 1.511(4) . ? C4 C5 1.534(4) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C10 1.545(4) . ? C5 C6 1.558(5) . ? C5 H5A 0.9800 . ? C6 C11 1.520(5) . ? C6 C12 1.546(4) . ? C6 C7 1.578(4) . ? C7 C8 1.494(4) . ? C7 C10 1.532(5) . ? C7 H7A 0.9800 . ? C8 C9 1.379(4) . ? C9 N1 1.331(4) . ? C9 H9A 0.9300 . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? C11 H11C 0.9600 . ? C11 H11B 0.9600 . ? C11 H11A 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.346(4) . ? C13 C14 1.388(5) . ? C14 C15 1.381(5) . ? C14 H14A 0.9300 . ? C15 C16 1.364(5) . ? C15 H15A 0.9300 . ? C16 C17 1.377(5) . ? C16 H16A 0.9300 . ? C17 N2 1.317(4) . ? C17 Br1 1.903(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 N1 C1 C2 123.0(3) . . ? N1 C1 C13 116.4(2) . . ? C2 C1 C13 120.6(2) . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C8 118.5(2) . . ? C2 C3 C4 124.1(3) . . ? C8 C3 C4 117.4(3) . . ? C3 C4 C5 110.5(2) . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? H4B C4 H4A 108.1 . . ? C4 C5 C10 108.2(3) . . ? C4 C5 C6 112.1(3) . . ? C10 C5 C6 87.9(2) . . ? C4 C5 H5A 115.2 . . ? C10 C5 H5A 115.2 . . ? C6 C5 H5A 115.2 . . ? C11 C6 C12 109.6(3) . . ? C11 C6 C5 119.9(3) . . ? C12 C6 C5 111.3(3) . . ? C11 C6 C7 118.3(3) . . ? C12 C6 C7 111.2(3) . . ? C5 C6 C7 84.4(2) . . ? C8 C7 C10 107.2(2) . . ? C8 C7 C6 108.8(2) . . ? C10 C7 C6 87.6(3) . . ? C8 C7 H7A 116.5 . . ? C10 C7 H7A 116.5 . . ? C6 C7 H7A 116.5 . . ? C9 C8 C3 117.3(3) . . ? C9 C8 C7 125.0(3) . . ? C3 C8 C7 117.6(3) . . ? N1 C9 C8 125.0(3) . . ? N1 C9 H9A 117.5 . . ? C8 C9 H9A 117.5 . . ? C7 C10 C5 86.5(2) . . ? C7 C10 H10B 114.2 . . ? C5 C10 H10B 114.2 . . ? C7 C10 H10A 114.2 . . ? C5 C10 H10A 114.2 . . ? H10B C10 H10A 111.4 . . ? C6 C11 H11C 109.5 . . ? C6 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C6 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 122.5(3) . . ? N2 C13 C1 116.6(3) . . ? C14 C13 C1 120.9(3) . . ? C15 C14 C13 118.4(4) . . ? C15 C14 H14A 120.8 . . ? C13 C14 H14A 120.8 . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C15 C16 C17 116.9(4) . . ? C15 C16 H16A 121.5 . . ? C17 C16 H16A 121.5 . . ? N2 C17 C16 125.8(4) . . ? N2 C17 Br1 115.2(3) . . ? C16 C17 Br1 119.0(3) . . ? C9 N1 C1 116.8(2) . . ? C17 N2 C13 116.4(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 N1 C1 C2 C3 1.7(4) . . . . ? C13 C1 C2 C3 -176.1(2) . . . . ? C1 C2 C3 C8 -2.7(4) . . . . ? C1 C2 C3 C4 176.1(3) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? C8 C3 C4 C5 -1.3(4) . . . . ? C3 C4 C5 C10 -47.2(4) . . . . ? C3 C4 C5 C6 48.0(4) . . . . ? C4 C5 C6 C11 37.8(4) . . . . ? C10 C5 C6 C11 146.6(3) . . . . ? C4 C5 C6 C12 167.6(3) . . . . ? C10 C5 C6 C12 -83.6(3) . . . . ? C4 C5 C6 C7 -81.8(3) . . . . ? C10 C5 C6 C7 27.0(2) . . . . ? C11 C6 C7 C8 -41.1(4) . . . . ? C12 C6 C7 C8 -169.2(3) . . . . ? C5 C6 C7 C8 80.1(3) . . . . ? C11 C6 C7 C10 -148.4(3) . . . . ? C12 C6 C7 C10 83.5(3) . . . . ? C5 C6 C7 C10 -27.3(2) . . . . ? C2 C3 C8 C9 1.9(4) . . . . ? C4 C3 C8 C9 -177.0(3) . . . . ? C2 C3 C8 C7 -178.4(2) . . . . ? C4 C3 C8 C7 2.7(4) . . . . ? C10 C7 C8 C9 -136.0(3) . . . . ? C6 C7 C8 C9 130.6(3) . . . . ? C10 C7 C8 C3 44.3(3) . . . . ? C6 C7 C8 C3 -49.1(4) . . . . ? C3 C8 C9 N1 0.1(4) . . . . ? C7 C8 C9 N1 -179.6(3) . . . . ? C8 C7 C10 C5 -81.5(3) . . . . ? C6 C7 C10 C5 27.4(2) . . . . ? C4 C5 C10 C7 84.8(3) . . . . ? C6 C5 C10 C7 -27.8(2) . . . . ? N1 C1 C13 N2 154.9(2) . . . . ? C2 C1 C13 N2 -27.2(4) . . . . ? N1 C1 C13 C14 -27.5(4) . . . . ? C2 C1 C13 C14 150.4(3) . . . . ? N2 C13 C14 C15 2.0(4) . . . . ? C1 C13 C14 C15 -175.5(3) . . . . ? C13 C14 C15 C16 -2.8(5) . . . . ? C14 C15 C16 C17 1.6(5) . . . . ? C15 C16 C17 N2 0.6(5) . . . . ? C15 C16 C17 Br1 -179.0(3) . . . . ? C8 C9 N1 C1 -1.2(4) . . . . ? C2 C1 N1 C9 0.3(4) . . . . ? C13 C1 N1 C9 178.1(2) . . . . ? C16 C17 N2 C13 -1.4(4) . . . . ? Br1 C17 N2 C13 178.18(19) . . . . ? C14 C13 N2 C17 0.1(4) . . . . ? C1 C13 N2 C17 177.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 59.60 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.037 #==============================================END