# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _audit_creation_method SHELXL-97 _audit_update_record ; ? Checkcif ; _journal_coden_Cambridge 177 _publ_contact_author_email pila@istm.cnr.it _publ_contact_author_name 'Dr. Tullio Pilati' _publ_contact_author_address ; C.N.R.-Istituto di Scienze e Tecnologie Molecolari Via C. Golgi, 19 20133 Milano Italy ; _publ_contact_author_fax ++39-02-50314300 _publ_contact_author_phone ++39-02-50314245 _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Polycyclic Compounds from Aminopolyols and alfa-Dicarbonyls: Structure and Application in the Synthesis of Exoditopic Ligand ; loop_ _publ_author_name 'G. Giovenzana' 'G. Palmisano' 'E. Del Grosso' 'L. Giovannelli' 'A. Penoni' 'T. Pilati' data_p55 _database_code_depnum_ccdc_archive 'CCDC 260606' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4aR*,4bR*,8aS*,8bS*)-[6a-(Hydroxymethyl)hexahydro-2H,6H-1,4,5,8-tetraoxa- 6b,8c-diazadicyclopent[cd,ij]-s-indacen-2(3H)-yl]methanol ; _chemical_name_common Glytham _chemical_formula_moiety 'C12 H18 N2 O6' _chemical_formula_sum 'C12 H18 N2 O6' _chemical_formula_weight 286.28 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2236(12) _cell_length_b 9.575(2) _cell_length_c 10.455(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.630(10) _cell_angle_gamma 90.00 _cell_volume 622.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4616 _cell_measurement_theta_min 2.886 _cell_measurement_theta_max 32.534 _exptl_crystal_description 'oblique prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _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 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 11124 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 32.82 _reflns_number_total 2200 _reflns_number_gt 1884 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _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 'w=1/[\s^2^(Fo^2^)+(0.0721P)^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 none _refine_ls_number_reflns 2200 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.58477(7) 0.60784(5) 0.58910(4) 0.02444(12) Uani 1 d . . . C2 C 0.69808(8) 0.57247(6) 0.47303(5) 0.02643(13) Uani 1 d . . . O3 O 0.66017(8) 0.68263(4) 0.38455(5) 0.03417(13) Uani 1 d . . . C4 C 0.68607(11) 0.80380(6) 0.46344(7) 0.03462(15) Uani 1 d . . . C5 C 0.57571(8) 0.76504(6) 0.58710(5) 0.02616(13) Uani 1 d . . . C6 C 0.33285(10) 0.79740(6) 0.57637(7) 0.03304(14) Uani 1 d . . . O7 O 0.23469(7) 0.67171(4) 0.52903(5) 0.03325(13) Uani 1 d . . . C8 C 0.35881(9) 0.56483(5) 0.58999(5) 0.02653(13) Uani 1 d . . . C9 C 0.68623(15) 0.82554(7) 0.70656(8) 0.0454(2) Uani 1 d . . . O10 O 0.67319(12) 0.97292(5) 0.69600(6) 0.0625(2) Uani 1 d . . . H2 H 0.8488(15) 0.5683(9) 0.4998(9) 0.040(2) Uiso 1 d . . . H4A H 0.832(2) 0.8270(10) 0.4822(12) 0.058(3) Uiso 1 d . . . H4B H 0.6126(15) 0.8824(10) 0.4131(9) 0.048(2) Uiso 1 d . . . H6A H 0.2833(17) 0.8219(9) 0.6627(11) 0.046(3) Uiso 1 d . . . H6B H 0.2905(15) 0.8721(11) 0.5141(10) 0.051(2) Uiso 1 d . . . H8 H 0.3190(13) 0.5618(8) 0.6777(8) 0.0316(19) Uiso 1 d . . . H9A H 0.8356(17) 0.7954(10) 0.7084(11) 0.046(2) Uiso 1 d . . . H9B H 0.6149(18) 0.7912(11) 0.7821(13) 0.063(3) Uiso 1 d . . . H10 H 0.751(2) 1.0123(16) 0.7577(15) 0.084(4) 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 0.0280(2) 0.0208(2) 0.0237(2) -0.00093(14) -0.00675(16) -0.00013(14) C2 0.0230(2) 0.0226(2) 0.0337(3) -0.00105(18) -0.00006(19) -0.00031(17) O3 0.0455(3) 0.0265(2) 0.0311(2) 0.00205(14) 0.00862(19) -0.00186(16) C4 0.0393(3) 0.0231(3) 0.0418(3) 0.0011(2) 0.0054(3) -0.0035(2) C5 0.0316(3) 0.0207(2) 0.0253(2) -0.00170(17) -0.00807(19) 0.00012(17) C6 0.0349(3) 0.0239(2) 0.0402(3) -0.0063(2) 0.0011(2) 0.0030(2) O7 0.0261(2) 0.0257(2) 0.0475(3) -0.00510(16) -0.00330(18) 0.00377(14) C8 0.0287(2) 0.0235(2) 0.0275(3) -0.00206(18) 0.00281(19) -0.00036(18) C9 0.0689(5) 0.0254(3) 0.0390(4) -0.0028(2) -0.0305(3) -0.0015(3) O10 0.1020(5) 0.0256(2) 0.0553(3) -0.0055(2) -0.0462(4) -0.0026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.4658(7) . NO N1 C2 1.4708(7) . NO N1 C5 1.5063(8) . NO C2 O3 1.4156(7) . NO C2 C8 1.5055(8) 3_666 NO C2 H2 0.967(9) . NO O3 C4 1.4284(8) . NO C4 C5 1.5370(9) . NO C4 H4A 0.948(13) . NO C4 H4B 1.015(10) . NO C5 C9 1.5132(8) . NO C5 C6 1.5419(9) . NO C6 O7 1.4278(7) . NO C6 H6A 0.995(11) . NO C6 H6B 0.995(10) . NO O7 C8 1.4160(7) . NO C8 C2 1.5055(8) 3_666 NO C8 H8 0.961(9) . NO C9 O10 1.4175(9) . NO C9 H9A 0.973(10) . NO C9 H9B 0.980(12) . NO O10 H10 0.873(15) . NO loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C2 115.91(4) . . NO C8 N1 C5 104.21(4) . . NO C2 N1 C5 103.75(4) . . NO O3 C2 N1 107.20(4) . . NO O3 C2 C8 109.63(5) . 3_666 NO N1 C2 C8 116.75(4) . 3_666 NO O3 C2 H2 110.5(5) . . NO N1 C2 H2 105.4(6) . . NO C8 C2 H2 107.2(5) 3_666 . NO C2 O3 C4 102.52(5) . . NO O3 C4 C5 104.28(5) . . NO O3 C4 H4A 113.0(7) . . NO C5 C4 H4A 110.2(7) . . NO O3 C4 H4B 105.4(5) . . NO C5 C4 H4B 114.0(5) . . NO H4A C4 H4B 109.8(8) . . NO N1 C5 C9 110.84(4) . . NO N1 C5 C4 103.60(4) . . NO C9 C5 C4 113.46(6) . . NO N1 C5 C6 103.75(4) . . NO C9 C5 C6 112.96(6) . . NO C4 C5 C6 111.39(5) . . NO O7 C6 C5 104.97(4) . . NO O7 C6 H6A 111.6(5) . . NO C5 C6 H6A 109.0(6) . . NO O7 C6 H6B 106.5(6) . . NO C5 C6 H6B 114.9(6) . . NO H6A C6 H6B 109.9(8) . . NO C8 O7 C6 103.72(5) . . NO O7 C8 N1 107.33(4) . . NO O7 C8 C2 108.76(5) . 3_666 NO N1 C8 C2 116.68(4) . 3_666 NO O7 C8 H8 107.0(5) . . NO N1 C8 H8 107.7(5) . . NO C2 C8 H8 109.0(5) 3_666 . NO O10 C9 C5 107.13(5) . . NO O10 C9 H9A 110.4(6) . . NO C5 C9 H9A 107.5(6) . . NO O10 C9 H9B 111.8(7) . . NO C5 C9 H9B 109.3(7) . . NO H9A C9 H9B 110.6(9) . . NO C9 O10 H10 110.2(10) . . NO 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 C8 N1 C2 O3 86.87(5) . . . . NO C5 N1 C2 O3 -26.71(5) . . . . NO C8 N1 C2 C8 -36.49(7) . . . 3_666 NO C5 N1 C2 C8 -150.06(4) . . . 3_666 NO N1 C2 O3 C4 43.00(6) . . . . NO C8 C2 O3 C4 170.64(4) 3_666 . . . NO C2 O3 C4 C5 -40.86(6) . . . . NO C8 N1 C5 C9 117.25(6) . . . . NO C2 N1 C5 C9 -121.00(6) . . . . NO C8 N1 C5 C4 -120.72(5) . . . . NO C2 N1 C5 C4 1.02(5) . . . . NO C8 N1 C5 C6 -4.27(5) . . . . NO C2 N1 C5 C6 117.47(5) . . . . NO O3 C4 C5 N1 24.31(6) . . . . NO O3 C4 C5 C9 144.57(5) . . . . NO O3 C4 C5 C6 -86.63(6) . . . . NO N1 C5 C6 O7 -19.67(6) . . . . NO C9 C5 C6 O7 -139.76(6) . . . . NO C4 C5 C6 O7 91.17(6) . . . . NO C5 C6 O7 C8 36.75(6) . . . . NO C6 O7 C8 N1 -40.93(6) . . . . NO C6 O7 C8 C2 -168.00(4) . . . 3_666 NO C2 N1 C8 O7 -85.81(5) . . . . NO C5 N1 C8 O7 27.50(5) . . . . NO C2 N1 C8 C2 36.46(7) . . . 3_666 NO C5 N1 C8 C2 149.77(5) . . . 3_666 NO N1 C5 C9 O10 179.14(6) . . . . NO C4 C5 C9 O10 63.07(8) . . . . NO C6 C5 C9 O10 -64.92(9) . . . . NO _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 32.82 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.267 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.050 #===END data_p59 _database_code_depnum_ccdc_archive 'CCDC 260607' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R*,2R*,5S*)-1-Hydroxymethyl-4,5-diphenyl-3,6-dioxa-8-azabicyclo[3.2.1]octan- 4-ol ; _chemical_formula_moiety 'C18 H19 N O4' _chemical_formula_sum 'C18 H19 N O4' _chemical_formula_weight 313.34 _chemical_absolute_configuration unk 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.6300(19) _cell_length_b 12.6665(15) _cell_length_c 7.9832(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.946(3) _cell_angle_gamma 90.00 _cell_volume 1576.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4617 _cell_measurement_theta_min 2.616 _cell_measurement_theta_max 26.493 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_special_details ; Most part of crystals are multiple twinned ; _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 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 27040 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1826 _reflns_number_gt 1702 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _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 'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.0978P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 1826 _refine_ls_number_parameters 284 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.121 _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 C1 C 0.03120(12) 0.70531(15) 0.1513(2) 0.0424(4) Uani 1 d . . . O2 O -0.04694(9) 0.75491(12) 0.18473(16) 0.0521(3) Uani 1 d . . . C3 C -0.09610(13) 0.69854(19) 0.2989(2) 0.0516(5) Uani 1 d . . . C4 C -0.04143(12) 0.66960(15) 0.4573(2) 0.0449(4) Uani 1 d . . . N5 N 0.02730(10) 0.60082(11) 0.40133(17) 0.0392(3) Uani 1 d . . . C6 C 0.08112(12) 0.67654(13) 0.3232(2) 0.0398(4) Uani 1 d . . . O7 O 0.08332(9) 0.76957(10) 0.42645(16) 0.0488(3) Uani 1 d . . . C8 C 0.00827(15) 0.76759(17) 0.5202(3) 0.0524(5) Uani 1 d . . . O9 O 0.01618(10) 0.60905(11) 0.06810(16) 0.0477(3) Uani 1 d . . . C10 C 0.07952(13) 0.78223(15) 0.0469(2) 0.0462(4) Uani 1 d . . . C11 C 0.0684(2) 0.88991(18) 0.0591(3) 0.0649(6) Uani 1 d . . . C12 C 0.1127(2) 0.9577(2) -0.0395(4) 0.0819(8) Uani 1 d . . . C13 C 0.1682(2) 0.9186(2) -0.1507(4) 0.0753(8) Uani 1 d . . . C14 C 0.17938(16) 0.8130(2) -0.1650(3) 0.0668(6) Uani 1 d . . . C15 C 0.13624(14) 0.74455(19) -0.0654(3) 0.0533(5) Uani 1 d . . . C16 C 0.17134(12) 0.63740(15) 0.3073(2) 0.0433(4) Uani 1 d . . . C17 C 0.18570(14) 0.53478(18) 0.2532(3) 0.0529(5) Uani 1 d . . . C18 C 0.26843(17) 0.4982(3) 0.2388(3) 0.0689(6) Uani 1 d . . . C19 C 0.33719(17) 0.5627(3) 0.2815(4) 0.0763(8) Uani 1 d . . . C20 C 0.32402(17) 0.6626(3) 0.3378(3) 0.0724(7) Uani 1 d . . . C21 C 0.24149(15) 0.7010(2) 0.3488(3) 0.0575(5) Uani 1 d . . . C22 C -0.09395(14) 0.61490(19) 0.5845(2) 0.0515(5) Uani 1 d . . . O23 O -0.04334(12) 0.58868(13) 0.73312(17) 0.0559(4) Uani 1 d . . . H21 H 0.2323(16) 0.771(2) 0.384(4) 0.057(7) Uiso 1 d . . . H31 H -0.1227(15) 0.630(2) 0.250(3) 0.045(6) Uiso 1 d . . . H32 H -0.1395(15) 0.7452(17) 0.328(3) 0.038(5) Uiso 1 d . . . H5 H 0.0563(15) 0.5691(18) 0.489(3) 0.044(5) Uiso 1 d . . . H81 H 0.0262(17) 0.767(2) 0.638(4) 0.056(7) Uiso 1 d . . . H82 H -0.0249(17) 0.830(2) 0.495(3) 0.054(6) Uiso 1 d . . . H9 H -0.006(2) 0.620(3) -0.036(5) 0.075(8) Uiso 1 d . . . H11 H 0.0280(19) 0.913(2) 0.130(4) 0.065(8) Uiso 1 d . . . H12 H 0.111(2) 1.033(3) -0.030(5) 0.097(11) Uiso 1 d . . . H13 H 0.199(2) 0.961(3) -0.212(5) 0.085(9) Uiso 1 d . . . H14 H 0.219(2) 0.783(3) -0.245(4) 0.083(9) Uiso 1 d . . . H15 H 0.1412(18) 0.677(3) -0.079(4) 0.064(7) Uiso 1 d . . . H17 H 0.1342(15) 0.486(2) 0.233(3) 0.051(6) Uiso 1 d . . . H18 H 0.278(2) 0.432(3) 0.203(5) 0.084(10) Uiso 1 d . . . H19 H 0.393(3) 0.542(3) 0.278(5) 0.101(11) Uiso 1 d . . . H20 H 0.370(3) 0.702(3) 0.355(5) 0.092(11) Uiso 1 d . . . H221 H -0.1412(16) 0.658(2) 0.617(3) 0.049(6) Uiso 1 d . . . H222 H -0.1181(15) 0.549(2) 0.541(3) 0.049(6) Uiso 1 d . . . H23 H -0.0288(17) 0.526(2) 0.731(4) 0.054(7) 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 C1 0.0528(10) 0.0419(9) 0.0309(8) 0.0013(6) -0.0082(6) 0.0049(7) O2 0.0548(7) 0.0604(8) 0.0402(7) 0.0105(6) -0.0029(6) 0.0134(6) C3 0.0479(10) 0.0650(13) 0.0411(9) 0.0050(8) -0.0036(8) 0.0117(9) C4 0.0495(9) 0.0509(10) 0.0338(8) 0.0005(7) -0.0013(7) 0.0074(8) N5 0.0458(7) 0.0415(7) 0.0294(6) 0.0018(5) -0.0046(5) 0.0033(6) C6 0.0514(9) 0.0372(8) 0.0296(7) -0.0015(6) -0.0065(6) 0.0009(7) O7 0.0630(8) 0.0439(7) 0.0386(6) -0.0081(5) -0.0022(6) -0.0016(6) C8 0.0672(12) 0.0485(10) 0.0410(10) -0.0051(8) -0.0005(8) 0.0088(9) O9 0.0637(8) 0.0475(7) 0.0296(6) 0.0002(5) -0.0117(5) -0.0039(6) C10 0.0576(10) 0.0455(9) 0.0340(8) 0.0048(7) -0.0079(7) 0.0028(8) C11 0.0946(18) 0.0450(11) 0.0554(13) 0.0053(10) 0.0078(12) 0.0078(11) C12 0.114(2) 0.0476(12) 0.0832(19) 0.0179(12) 0.0026(17) -0.0007(14) C13 0.0800(17) 0.0761(17) 0.0689(16) 0.0283(13) -0.0013(13) -0.0156(14) C14 0.0522(12) 0.0909(18) 0.0567(13) 0.0116(12) 0.0008(10) -0.0030(11) C15 0.0553(11) 0.0550(12) 0.0489(11) 0.0031(8) -0.0003(8) 0.0020(9) C16 0.0497(9) 0.0506(9) 0.0283(7) 0.0071(7) -0.0059(6) 0.0008(7) C17 0.0573(11) 0.0533(11) 0.0471(10) 0.0016(8) -0.0042(8) 0.0068(9) C18 0.0696(15) 0.0719(16) 0.0650(14) 0.0034(12) 0.0034(11) 0.0221(12) C19 0.0539(13) 0.106(2) 0.0692(15) 0.0147(15) 0.0061(11) 0.0166(14) C20 0.0496(11) 0.102(2) 0.0648(14) 0.0143(14) -0.0036(10) -0.0139(13) C21 0.0595(12) 0.0622(13) 0.0500(11) 0.0035(9) -0.0024(9) -0.0086(10) C22 0.0529(11) 0.0647(12) 0.0365(9) 0.0016(8) 0.0014(8) 0.0067(10) O23 0.0806(10) 0.0549(8) 0.0314(6) 0.0002(6) -0.0024(6) 0.0122(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O9 1.400(2) . NO C1 O2 1.415(2) . NO C1 C10 1.517(3) . NO C1 C6 1.574(2) . NO O2 C3 1.424(3) . NO C3 C4 1.521(2) . NO C3 H31 1.03(3) . NO C3 H32 0.94(2) . NO C4 N5 1.476(2) . NO C4 C22 1.517(3) . NO C4 C8 1.531(3) . NO N5 C6 1.445(2) . NO N5 H5 0.90(3) . NO C6 O7 1.437(2) . NO C6 C16 1.508(3) . NO O7 C8 1.435(3) . NO C8 H81 0.97(3) . NO C8 H82 0.96(3) . NO O9 H9 0.89(4) . NO C10 C11 1.379(3) . NO C10 C15 1.388(3) . NO C11 C12 1.383(4) . NO C11 H11 0.92(3) . NO C12 C13 1.375(5) . NO C12 H12 0.96(4) . NO C13 C14 1.355(4) . NO C13 H13 0.89(4) . NO C14 C15 1.383(3) . NO C14 H14 0.99(4) . NO C15 H15 0.87(3) . NO C16 C21 1.382(3) . NO C16 C17 1.393(3) . NO C17 C18 1.386(3) . NO C17 H17 1.02(2) . NO C18 C19 1.374(5) . NO C18 H18 0.90(4) . NO C19 C20 1.363(5) . NO C19 H19 0.92(4) . NO C20 C21 1.387(4) . NO C20 H20 0.88(4) . NO C21 H21 0.94(3) . NO C22 O23 1.419(2) . NO C22 H221 0.97(3) . NO C22 H222 0.97(3) . NO O23 H23 0.83(3) . NO 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 O9 C1 O2 110.93(16) . . NO O9 C1 C10 111.87(15) . . NO O2 C1 C10 106.70(15) . . NO O9 C1 C6 105.58(13) . . NO O2 C1 C6 108.69(14) . . NO C10 C1 C6 113.08(15) . . NO C1 O2 C3 114.14(14) . . NO O2 C3 C4 110.85(17) . . NO O2 C3 H31 113.7(13) . . NO C4 C3 H31 107.7(14) . . NO O2 C3 H32 105.8(13) . . NO C4 C3 H32 108.6(14) . . NO H31 C3 H32 110.1(19) . . NO N5 C4 C22 111.82(16) . . NO N5 C4 C3 105.64(15) . . NO C22 C4 C3 111.57(17) . . NO N5 C4 C8 102.39(16) . . NO C22 C4 C8 115.86(17) . . NO C3 C4 C8 108.72(17) . . NO C6 N5 C4 101.31(13) . . NO C6 N5 H5 110.8(15) . . NO C4 N5 H5 111.4(15) . . NO O7 C6 N5 106.76(14) . . NO O7 C6 C16 109.39(15) . . NO N5 C6 C16 113.16(14) . . NO O7 C6 C1 107.53(13) . . NO N5 C6 C1 105.17(13) . . NO C16 C6 C1 114.39(14) . . NO C8 O7 C6 107.26(15) . . NO O7 C8 C4 104.92(15) . . NO O7 C8 H81 108.5(16) . . NO C4 C8 H81 114.8(16) . . NO O7 C8 H82 109.0(15) . . NO C4 C8 H82 110.4(15) . . NO H81 C8 H82 109(2) . . NO C1 O9 H9 111(2) . . NO C11 C10 C15 118.3(2) . . NO C11 C10 C1 121.8(2) . . NO C15 C10 C1 119.88(18) . . NO C10 C11 C12 120.2(3) . . NO C10 C11 H11 117.2(19) . . NO C12 C11 H11 122.4(19) . . NO C13 C12 C11 120.4(3) . . NO C13 C12 H12 116(2) . . NO C11 C12 H12 124(2) . . NO C14 C13 C12 120.0(3) . . NO C14 C13 H13 118(2) . . NO C12 C13 H13 122(2) . . NO C13 C14 C15 120.0(3) . . NO C13 C14 H14 121.2(19) . . NO C15 C14 H14 118.8(19) . . NO C14 C15 C10 120.9(2) . . NO C14 C15 H15 119.6(19) . . NO C10 C15 H15 119.3(19) . . NO C21 C16 C17 118.4(2) . . NO C21 C16 C6 121.28(19) . . NO C17 C16 C6 120.29(17) . . NO C18 C17 C16 120.6(2) . . NO C18 C17 H17 121.2(13) . . NO C16 C17 H17 118.0(13) . . NO C19 C18 C17 119.9(3) . . NO C19 C18 H18 119(2) . . NO C17 C18 H18 121(2) . . NO C20 C19 C18 120.0(2) . . NO C20 C19 H19 116(3) . . NO C18 C19 H19 124(3) . . NO C19 C20 C21 120.6(3) . . NO C19 C20 H20 116(3) . . NO C21 C20 H20 123(3) . . NO C16 C21 C20 120.4(3) . . NO C16 C21 H21 118.9(16) . . NO C20 C21 H21 120.7(16) . . NO O23 C22 C4 111.74(17) . . NO O23 C22 H221 107.7(15) . . NO C4 C22 H221 112.1(15) . . NO O23 C22 H222 106.1(15) . . NO C4 C22 H222 111.7(15) . . NO H221 C22 H222 107(2) . . NO C22 O23 H23 110(2) . . NO 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 O9 C1 O2 C3 65.05(19) . . . . NO C10 C1 O2 C3 -172.86(15) . . . . NO C6 C1 O2 C3 -50.6(2) . . . . NO C1 O2 C3 C4 50.9(2) . . . . NO O2 C3 C4 N5 -61.5(2) . . . . NO O2 C3 C4 C22 176.79(17) . . . . NO O2 C3 C4 C8 47.8(2) . . . . NO C22 C4 N5 C6 -164.49(14) . . . . NO C3 C4 N5 C6 73.95(17) . . . . NO C8 C4 N5 C6 -39.80(17) . . . . NO C4 N5 C6 O7 39.46(16) . . . . NO C4 N5 C6 C16 159.86(13) . . . . NO C4 N5 C6 C1 -74.59(15) . . . . NO O9 C1 C6 O7 -168.97(15) . . . . NO O2 C1 C6 O7 -49.90(19) . . . . NO C10 C1 C6 O7 68.39(19) . . . . NO O9 C1 C6 N5 -55.46(17) . . . . NO O2 C1 C6 N5 63.62(17) . . . . NO C10 C1 C6 N5 -178.10(15) . . . . NO O9 C1 C6 C16 69.33(18) . . . . NO O2 C1 C6 C16 -171.60(15) . . . . NO C10 C1 C6 C16 -53.3(2) . . . . NO N5 C6 O7 C8 -22.71(18) . . . . NO C16 C6 O7 C8 -145.49(15) . . . . NO C1 C6 O7 C8 89.73(17) . . . . NO C6 O7 C8 C4 -3.21(19) . . . . NO N5 C4 C8 O7 26.97(19) . . . . NO C22 C4 C8 O7 148.94(16) . . . . NO C3 C4 C8 O7 -84.49(19) . . . . NO O9 C1 C10 C11 149.6(2) . . . . NO O2 C1 C10 C11 28.1(3) . . . . NO C6 C1 C10 C11 -91.3(2) . . . . NO O9 C1 C10 C15 -29.9(2) . . . . NO O2 C1 C10 C15 -151.41(18) . . . . NO C6 C1 C10 C15 89.1(2) . . . . NO C15 C10 C11 C12 0.4(4) . . . . NO C1 C10 C11 C12 -179.2(2) . . . . NO C10 C11 C12 C13 0.0(5) . . . . NO C11 C12 C13 C14 0.4(5) . . . . NO C12 C13 C14 C15 -1.2(4) . . . . NO C13 C14 C15 C10 1.6(3) . . . . NO C11 C10 C15 C14 -1.2(3) . . . . NO C1 C10 C15 C14 178.3(2) . . . . NO O7 C6 C16 C21 -16.0(2) . . . . NO N5 C6 C16 C21 -134.93(18) . . . . NO C1 C6 C16 C21 104.6(2) . . . . NO O7 C6 C16 C17 162.70(16) . . . . NO N5 C6 C16 C17 43.8(2) . . . . NO C1 C6 C16 C17 -76.6(2) . . . . NO C21 C16 C17 C18 -1.0(3) . . . . NO C6 C16 C17 C18 -179.83(19) . . . . NO C16 C17 C18 C19 1.4(4) . . . . NO C17 C18 C19 C20 -0.1(4) . . . . NO C18 C19 C20 C21 -1.6(4) . . . . NO C17 C16 C21 C20 -0.6(3) . . . . NO C6 C16 C21 C20 178.2(2) . . . . NO C19 C20 C21 C16 1.9(4) . . . . NO N5 C4 C22 O23 62.5(2) . . . . NO C3 C4 C22 O23 -179.44(17) . . . . NO C8 C4 C22 O23 -54.3(2) . . . . NO _diffrn_measured_fraction_theta_max 0.499 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.499 _refine_diff_density_max 0.206 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.038 #===END