# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Juan Marco' _publ_contact_author_email ALBERTO.MARCO@UV.ES _publ_section_title ; Convergent, stereoselective syntheses of the glycosidase inhibitors broussonetines D and M ; _publ_author_name 'Juan Marco' # Attachment 'Comp9a.CIF' data_str928m _database_code_depnum_ccdc_archive 'CCDC 711360' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'C38 H45 N3 O11' _chemical_formula_sum 'C38 H45 N3 O11' _chemical_formula_weight 719.77 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_Int_Tables_number 4 _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3976(11) _cell_length_b 22.631(3) _cell_length_c 10.2340(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.952(4) _cell_angle_gamma 90.00 _cell_volume 1895.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 10933 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9771 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10933 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.2375 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6578 _reflns_number_gt 2514 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0091(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 1(2) _refine_ls_number_reflns 6578 _refine_ls_number_parameters 475 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2248 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.2022 _refine_ls_wR_factor_gt 0.1408 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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 O1 O 0.9184(8) 0.2824(2) 0.5504(6) 0.0654(18) Uani 1 1 d . . . N1 N 1.0957(7) 0.2251(2) 0.4747(6) 0.0359(15) Uani 1 1 d . . . C1 C 0.9293(11) 0.2294(4) 0.6239(9) 0.057(2) Uani 1 1 d . . . H1A H 0.8214 0.2159 0.6295 0.068 Uiso 1 1 calc R . . H1B H 0.9944 0.2351 0.7141 0.068 Uiso 1 1 calc R . . O2 O 1.1698(7) 0.1497(2) 0.3572(5) 0.0502(15) Uani 1 1 d . . . N2 N 1.3279(10) -0.1306(4) 0.4259(9) 0.060(2) Uani 1 1 d . . . C2 C 1.0092(9) 0.1852(3) 0.5498(8) 0.048(2) Uani 1 1 d . . . H2 H 0.9243 0.1637 0.4861 0.057 Uiso 1 1 calc R . . O3 O 1.2535(6) 0.2441(2) 0.3324(5) 0.0490(15) Uani 1 1 d . . . C3 C 1.1234(9) 0.1402(3) 0.6380(7) 0.037(2) Uani 1 1 d . . . H3 H 1.1801 0.1175 0.5807 0.045 Uiso 1 1 calc R . . N3 N 0.9242(12) -0.0960(5) 0.0101(9) 0.079(3) Uani 1 1 d . . . O4 O 1.1507(6) 0.0578(2) 0.7810(5) 0.0435(14) Uani 1 1 d . . . C4 C 1.0330(9) 0.0980(3) 0.7089(8) 0.042(2) Uani 1 1 d . . . H4 H 0.9864 0.1204 0.7734 0.050 Uiso 1 1 calc R . . O5 O 1.2417(6) 0.1706(2) 0.7359(5) 0.0430(14) Uani 1 1 d . . . C5 C 0.8980(9) 0.0624(3) 0.6208(7) 0.0395(19) Uani 1 1 d . . . H5 H 0.8160 0.0891 0.5685 0.047 Uiso 1 1 calc R . . O6 O 0.9764(6) 0.0292(2) 0.5317(5) 0.0471(15) Uani 1 1 d . . . C6 C 0.8178(11) 0.0205(4) 0.6992(9) 0.062(3) Uani 1 1 d . . . H6A H 0.7790 0.0428 0.7668 0.075 Uiso 1 1 calc R . . H6B H 0.8998 -0.0070 0.7457 0.075 Uiso 1 1 calc R . . O7 O 0.8075(7) 0.0589(3) 0.3419(6) 0.0657(18) Uani 1 1 d . . . C7 C 0.6742(11) -0.0152(4) 0.6174(9) 0.061(3) Uani 1 1 d . . . H7A H 0.7026 -0.0290 0.5359 0.073 Uiso 1 1 calc R . . H7B H 0.6566 -0.0497 0.6688 0.073 Uiso 1 1 calc R . . O8 O 1.3779(8) -0.1187(3) 0.5451(8) 0.081(2) Uani 1 1 d . . . C8 C 0.5230(15) 0.0182(4) 0.5821(13) 0.096(4) Uani 1 1 d . . . H8A H 0.4726 0.0244 0.6531 0.115 Uiso 1 1 calc R . . O9 O 1.3901(8) -0.1677(3) 0.3658(7) 0.088(2) Uani 1 1 d . . . C9 C 0.4508(16) 0.0397(4) 0.4770(13) 0.102(4) Uani 1 1 d . . . H9A H 0.4925 0.0357 0.4006 0.122 Uiso 1 1 calc R . . H9B H 0.3536 0.0601 0.4727 0.122 Uiso 1 1 calc R . . C10 C 1.0499(11) 0.2878(4) 0.4866(8) 0.048(2) Uani 1 1 d . . . O10 O 0.8205(11) -0.0652(3) -0.0553(7) 0.096(3) Uani 1 1 d . . . O11 O 0.9729(10) -0.1427(4) -0.0323(8) 0.123(3) Uani 1 1 d . . . C11 C 1.1863(11) 0.3212(4) 0.5735(10) 0.089(4) Uani 1 1 d . . . H11A H 1.1693 0.3628 0.5582 0.133 Uiso 1 1 calc R . . H11B H 1.2878 0.3098 0.5524 0.133 Uiso 1 1 calc R . . H11C H 1.1899 0.3125 0.6659 0.133 Uiso 1 1 calc R . . C12 C 0.9824(12) 0.3173(4) 0.3557(9) 0.080(3) Uani 1 1 d . . . H12A H 0.9108 0.2905 0.2977 0.120 Uiso 1 1 calc R . . H12B H 1.0705 0.3284 0.3150 0.120 Uiso 1 1 calc R . . H12C H 0.9226 0.3519 0.3702 0.120 Uiso 1 1 calc R . . C13 C 1.1710(11) 0.2026(4) 0.3847(8) 0.046(2) Uani 1 1 d . . . C14 C 1.3595(10) 0.2296(3) 0.2405(9) 0.051(2) Uani 1 1 d . . . C15 C 1.5015(13) 0.1897(6) 0.3132(12) 0.126(5) Uani 1 1 d . . . H15A H 1.5718 0.2118 0.3831 0.190 Uiso 1 1 calc R . . H15B H 1.5626 0.1762 0.2502 0.190 Uiso 1 1 calc R . . H15C H 1.4580 0.1563 0.3516 0.190 Uiso 1 1 calc R . . C16 C 1.2570(15) 0.2029(5) 0.1137(11) 0.116(5) Uani 1 1 d . . . H16A H 1.2258 0.1634 0.1318 0.174 Uiso 1 1 calc R . . H16B H 1.3193 0.2018 0.0457 0.174 Uiso 1 1 calc R . . H16C H 1.1608 0.2264 0.0831 0.174 Uiso 1 1 calc R . . C17 C 1.4171(13) 0.2898(4) 0.2058(10) 0.086(3) Uani 1 1 d . . . H17A H 1.3263 0.3166 0.1877 0.129 Uiso 1 1 calc R . . H17B H 1.4624 0.2866 0.1279 0.129 Uiso 1 1 calc R . . H17C H 1.4991 0.3043 0.2798 0.129 Uiso 1 1 calc R . . C18 C 1.1744(10) 0.0566(3) 0.9233(7) 0.051(2) Uani 1 1 d . . . H18A H 1.0701 0.0529 0.9484 0.061 Uiso 1 1 calc R . . H18B H 1.2264 0.0929 0.9616 0.061 Uiso 1 1 calc R . . C19 C 1.2814(10) 0.0043(3) 0.9742(8) 0.044(2) Uani 1 1 d . . . C20 C 1.3760(11) 0.0047(4) 1.1017(9) 0.064(3) Uani 1 1 d . . . H20 H 1.3763 0.0379 1.1556 0.077 Uiso 1 1 calc R . . C21 C 1.4737(11) -0.0448(5) 1.1529(11) 0.079(3) Uani 1 1 d . . . H21 H 1.5363 -0.0449 1.2402 0.094 Uiso 1 1 calc R . . C22 C 1.4737(14) -0.0926(6) 1.0711(14) 0.093(4) Uani 1 1 d . . . H22 H 1.5400 -0.1249 1.1018 0.112 Uiso 1 1 calc R . . C23 C 1.3789(16) -0.0932(5) 0.9470(12) 0.107(4) Uani 1 1 d . . . H23 H 1.3764 -0.1264 0.8931 0.128 Uiso 1 1 calc R . . C24 C 1.2857(13) -0.0449(4) 0.8992(10) 0.074(3) Uani 1 1 d . . . H24 H 1.2228 -0.0458 0.8120 0.089 Uiso 1 1 calc R . . C25 C 1.3994(10) 0.1780(4) 0.7030(8) 0.062(2) Uani 1 1 d . . . H25A H 1.4029 0.2157 0.6584 0.075 Uiso 1 1 calc R . . H25B H 1.4162 0.1469 0.6423 0.075 Uiso 1 1 calc R . . C26 C 1.5312(9) 0.1758(4) 0.8279(7) 0.043(2) Uani 1 1 d . . . C27 C 1.5643(12) 0.1238(4) 0.9028(9) 0.060(3) Uani 1 1 d . . . H27 H 1.5011 0.0904 0.8751 0.072 Uiso 1 1 calc R . . C28 C 1.6882(16) 0.1207(6) 1.0165(11) 0.088(4) Uani 1 1 d . . . H28 H 1.7066 0.0854 1.0641 0.106 Uiso 1 1 calc R . . C29 C 1.7816(13) 0.1671(9) 1.0594(12) 0.103(5) Uani 1 1 d . . . H29 H 1.8664 0.1642 1.1351 0.123 Uiso 1 1 calc R . . C30 C 1.7523(15) 0.2192(7) 0.9915(13) 0.111(5) Uani 1 1 d . . . H30 H 1.8166 0.2520 1.0226 0.133 Uiso 1 1 calc R . . C31 C 1.6275(12) 0.2244(4) 0.8760(9) 0.070(3) Uani 1 1 d . . . H31 H 1.6090 0.2604 0.8313 0.085 Uiso 1 1 calc R . . C32 C 0.9138(10) 0.0277(3) 0.4007(8) 0.043(2) Uani 1 1 d . . . C33 C 0.9942(9) -0.0196(3) 0.3380(7) 0.0367(19) Uani 1 1 d . . . C34 C 0.9310(10) -0.0345(3) 0.2028(8) 0.043(2) Uani 1 1 d . . . H34 H 0.8441 -0.0134 0.1514 0.052 Uiso 1 1 calc R . . C35 C 0.9984(12) -0.0801(4) 0.1486(8) 0.052(2) Uani 1 1 d . . . C36 C 1.1277(11) -0.1128(4) 0.2174(10) 0.058(3) Uani 1 1 d . . . H36 H 1.1714 -0.1439 0.1775 0.070 Uiso 1 1 calc R . . C37 C 1.1886(10) -0.0972(3) 0.3471(10) 0.048(2) Uani 1 1 d . . . C38 C 1.1242(9) -0.0511(3) 0.4095(8) 0.041(2) Uani 1 1 d . . . H38 H 1.1690 -0.0418 0.4987 0.050 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 O1 0.085(5) 0.044(4) 0.078(5) 0.016(3) 0.041(4) 0.025(3) N1 0.040(4) 0.031(4) 0.040(4) -0.002(3) 0.017(3) -0.002(3) C1 0.067(7) 0.044(5) 0.062(6) 0.012(5) 0.020(5) 0.007(5) O2 0.076(4) 0.035(3) 0.044(3) -0.003(3) 0.023(3) 0.005(3) N2 0.051(6) 0.056(6) 0.074(6) 0.000(5) 0.016(5) 0.008(4) C2 0.041(5) 0.048(5) 0.059(6) 0.010(5) 0.020(4) 0.012(4) O3 0.065(4) 0.038(3) 0.049(4) -0.005(3) 0.024(3) -0.006(3) C3 0.037(5) 0.039(5) 0.033(5) 0.000(4) 0.002(4) 0.009(4) N3 0.090(8) 0.096(8) 0.051(6) -0.025(6) 0.014(5) -0.031(6) O4 0.062(4) 0.039(3) 0.026(3) 0.000(2) 0.001(3) 0.019(3) C4 0.041(5) 0.041(5) 0.041(5) 0.007(4) 0.007(4) 0.003(4) O5 0.040(3) 0.043(3) 0.044(3) -0.009(3) 0.004(3) 0.001(3) C5 0.051(6) 0.030(4) 0.037(5) -0.003(4) 0.009(4) -0.006(4) O6 0.054(4) 0.040(3) 0.045(4) -0.001(3) 0.008(3) 0.005(3) C6 0.064(6) 0.053(6) 0.061(6) 0.008(5) -0.005(5) -0.016(5) O7 0.070(5) 0.062(4) 0.056(4) 0.016(3) -0.006(3) 0.025(4) C7 0.066(7) 0.044(5) 0.068(7) 0.008(5) 0.004(5) -0.007(5) O8 0.077(5) 0.049(4) 0.096(6) -0.005(4) -0.027(4) 0.011(3) C8 0.093(9) 0.067(8) 0.103(10) -0.003(7) -0.030(7) -0.011(7) O9 0.059(5) 0.097(6) 0.113(6) -0.004(5) 0.031(4) 0.020(4) C9 0.109(10) 0.069(8) 0.112(11) -0.010(7) -0.008(9) 0.006(7) C10 0.065(6) 0.036(5) 0.045(6) 0.002(4) 0.017(5) 0.001(5) O10 0.123(7) 0.111(7) 0.042(5) 0.000(4) -0.005(4) 0.002(5) O11 0.138(7) 0.135(7) 0.087(6) -0.071(6) 0.006(5) 0.006(6) C11 0.075(8) 0.057(6) 0.128(10) -0.041(7) 0.007(7) 0.003(6) C12 0.095(8) 0.073(7) 0.079(7) 0.030(6) 0.034(6) 0.033(6) C13 0.058(6) 0.042(6) 0.038(5) 0.003(5) 0.011(5) -0.010(5) C14 0.060(6) 0.035(5) 0.073(7) -0.011(5) 0.048(5) -0.004(4) C15 0.087(9) 0.148(11) 0.171(13) 0.070(10) 0.085(9) 0.048(8) C16 0.162(12) 0.116(9) 0.099(9) -0.063(7) 0.090(9) -0.073(9) C17 0.126(9) 0.058(6) 0.095(9) -0.001(6) 0.071(7) -0.036(6) C18 0.073(7) 0.046(5) 0.037(5) 0.008(4) 0.017(4) 0.017(5) C19 0.046(5) 0.041(5) 0.045(6) 0.001(4) 0.008(4) -0.002(4) C20 0.080(7) 0.050(6) 0.050(6) 0.006(5) -0.008(5) -0.015(5) C21 0.053(7) 0.083(8) 0.086(8) 0.030(7) -0.014(6) 0.015(6) C22 0.069(8) 0.084(9) 0.128(11) 0.041(8) 0.022(8) 0.025(7) C23 0.142(11) 0.066(8) 0.090(9) -0.010(7) -0.022(9) 0.037(8) C24 0.121(9) 0.046(6) 0.058(6) -0.001(5) 0.025(6) 0.024(6) C25 0.053(6) 0.083(6) 0.047(6) 0.015(5) 0.005(5) 0.012(5) C26 0.047(5) 0.045(5) 0.038(5) 0.006(4) 0.010(4) 0.005(5) C27 0.065(7) 0.050(6) 0.067(7) 0.000(5) 0.020(6) 0.011(5) C28 0.091(10) 0.106(10) 0.064(8) 0.021(7) 0.009(7) 0.035(8) C29 0.042(7) 0.193(16) 0.067(8) 0.006(11) -0.003(6) -0.003(10) C30 0.093(10) 0.155(14) 0.079(10) -0.007(9) 0.008(8) -0.063(9) C31 0.086(8) 0.064(6) 0.058(7) 0.013(5) 0.010(6) -0.028(6) C32 0.050(6) 0.038(5) 0.035(5) 0.005(4) -0.003(4) -0.005(5) C33 0.043(5) 0.034(4) 0.031(5) 0.010(4) 0.005(4) 0.000(4) C34 0.051(6) 0.044(5) 0.036(5) 0.000(4) 0.014(4) -0.013(4) C35 0.072(7) 0.054(6) 0.029(5) -0.001(5) 0.010(5) -0.022(5) C36 0.061(7) 0.040(5) 0.075(7) -0.022(5) 0.021(6) -0.004(5) C37 0.045(6) 0.028(5) 0.070(6) 0.001(5) 0.012(5) -0.003(4) C38 0.039(5) 0.051(5) 0.037(5) 0.001(4) 0.013(4) -0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.408(9) . ? O1 C1 1.409(9) . ? N1 C13 1.331(10) . ? N1 C2 1.478(9) . ? N1 C10 1.483(9) . ? C1 C2 1.500(10) . ? O2 C13 1.229(8) . ? N2 O9 1.224(9) . ? N2 O8 1.228(9) . ? N2 C37 1.472(10) . ? C2 C3 1.543(9) . ? O3 C13 1.348(9) . ? O3 C14 1.469(9) . ? C3 O5 1.420(8) . ? C3 C4 1.505(10) . ? N3 O10 1.196(10) . ? N3 O11 1.247(10) . ? N3 C35 1.459(11) . ? O4 C4 1.423(8) . ? O4 C18 1.425(8) . ? C4 C5 1.513(9) . ? O5 C25 1.447(9) . ? C5 O6 1.450(8) . ? C5 C6 1.497(10) . ? O6 C32 1.326(9) . ? C6 C7 1.534(11) . ? O7 C32 1.192(8) . ? C7 C8 1.452(14) . ? C8 C9 1.212(13) . ? C10 C11 1.489(10) . ? C10 C12 1.489(11) . ? C14 C16 1.513(12) . ? C14 C17 1.515(10) . ? C14 C15 1.547(12) . ? C18 C19 1.507(10) . ? C19 C24 1.358(10) . ? C19 C20 1.367(10) . ? C20 C21 1.419(12) . ? C21 C22 1.367(14) . ? C22 C23 1.339(14) . ? C23 C24 1.369(12) . ? C25 C26 1.493(10) . ? C26 C31 1.388(11) . ? C26 C27 1.398(11) . ? C27 C28 1.378(13) . ? C28 C29 1.326(15) . ? C29 C30 1.362(16) . ? C30 C31 1.398(14) . ? C32 C33 1.485(10) . ? C33 C38 1.370(9) . ? C33 C34 1.408(9) . ? C34 C35 1.355(11) . ? C35 C36 1.371(11) . ? C36 C37 1.357(11) . ? C37 C38 1.394(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O1 C1 111.0(6) . . ? C13 N1 C2 119.4(6) . . ? C13 N1 C10 126.6(6) . . ? C2 N1 C10 112.1(6) . . ? O1 C1 C2 106.3(7) . . ? O9 N2 O8 124.1(8) . . ? O9 N2 C37 116.9(9) . . ? O8 N2 C37 118.9(8) . . ? N1 C2 C1 100.5(6) . . ? N1 C2 C3 113.2(6) . . ? C1 C2 C3 115.7(7) . . ? C13 O3 C14 122.5(6) . . ? O5 C3 C4 108.4(6) . . ? O5 C3 C2 109.8(6) . . ? C4 C3 C2 112.7(6) . . ? O10 N3 O11 123.7(9) . . ? O10 N3 C35 119.9(10) . . ? O11 N3 C35 116.4(10) . . ? C4 O4 C18 117.6(5) . . ? O4 C4 C3 106.8(6) . . ? O4 C4 C5 108.0(6) . . ? C3 C4 C5 116.3(7) . . ? C3 O5 C25 115.1(6) . . ? O6 C5 C6 109.3(6) . . ? O6 C5 C4 105.4(6) . . ? C6 C5 C4 112.7(6) . . ? C32 O6 C5 121.1(6) . . ? C5 C6 C7 115.8(7) . . ? C8 C7 C6 113.4(8) . . ? C9 C8 C7 131.7(14) . . ? O1 C10 N1 101.5(6) . . ? O1 C10 C11 110.2(8) . . ? N1 C10 C11 110.8(7) . . ? O1 C10 C12 106.0(7) . . ? N1 C10 C12 114.1(7) . . ? C11 C10 C12 113.4(8) . . ? O2 C13 N1 123.5(8) . . ? O2 C13 O3 124.5(8) . . ? N1 C13 O3 111.9(7) . . ? O3 C14 C16 109.2(7) . . ? O3 C14 C17 102.7(6) . . ? C16 C14 C17 107.9(8) . . ? O3 C14 C15 109.5(7) . . ? C16 C14 C15 114.1(9) . . ? C17 C14 C15 112.7(8) . . ? O4 C18 C19 107.7(6) . . ? C24 C19 C20 117.5(8) . . ? C24 C19 C18 122.5(8) . . ? C20 C19 C18 119.9(8) . . ? C19 C20 C21 120.7(9) . . ? C22 C21 C20 118.6(10) . . ? C23 C22 C21 120.4(10) . . ? C22 C23 C24 120.1(10) . . ? C19 C24 C23 122.6(9) . . ? O5 C25 C26 109.8(7) . . ? C31 C26 C27 116.4(7) . . ? C31 C26 C25 122.6(8) . . ? C27 C26 C25 121.1(8) . . ? C28 C27 C26 121.7(9) . . ? C29 C28 C27 121.2(11) . . ? C28 C29 C30 119.4(10) . . ? C29 C30 C31 121.3(11) . . ? C26 C31 C30 120.0(9) . . ? O7 C32 O6 125.3(8) . . ? O7 C32 C33 124.8(8) . . ? O6 C32 C33 109.9(7) . . ? C38 C33 C34 118.7(7) . . ? C38 C33 C32 121.9(7) . . ? C34 C33 C32 119.4(7) . . ? C35 C34 C33 119.0(8) . . ? C34 C35 C36 123.8(8) . . ? C34 C35 N3 117.3(9) . . ? C36 C35 N3 118.9(9) . . ? C37 C36 C35 116.4(8) . . ? C36 C37 C38 122.8(8) . . ? C36 C37 N2 118.7(9) . . ? C38 C37 N2 118.4(8) . . ? C33 C38 C37 119.3(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 O1 C1 C2 -31.7(9) . . . . ? C13 N1 C2 C1 -173.5(7) . . . . ? C10 N1 C2 C1 -8.4(8) . . . . ? C13 N1 C2 C3 62.4(9) . . . . ? C10 N1 C2 C3 -132.4(7) . . . . ? O1 C1 C2 N1 22.9(8) . . . . ? O1 C1 C2 C3 145.2(7) . . . . ? N1 C2 C3 O5 61.7(8) . . . . ? C1 C2 C3 O5 -53.5(9) . . . . ? N1 C2 C3 C4 -177.3(6) . . . . ? C1 C2 C3 C4 67.4(9) . . . . ? C18 O4 C4 C3 118.2(7) . . . . ? C18 O4 C4 C5 -116.0(7) . . . . ? O5 C3 C4 O4 -60.8(7) . . . . ? C2 C3 C4 O4 177.5(6) . . . . ? O5 C3 C4 C5 178.6(6) . . . . ? C2 C3 C4 C5 56.8(9) . . . . ? C4 C3 O5 C25 138.0(6) . . . . ? C2 C3 O5 C25 -98.5(7) . . . . ? O4 C4 C5 O6 -60.7(7) . . . . ? C3 C4 C5 O6 59.3(8) . . . . ? O4 C4 C5 C6 58.4(9) . . . . ? C3 C4 C5 C6 178.5(7) . . . . ? C6 C5 O6 C32 106.6(7) . . . . ? C4 C5 O6 C32 -132.0(7) . . . . ? O6 C5 C6 C7 -65.9(9) . . . . ? C4 C5 C6 C7 177.3(7) . . . . ? C5 C6 C7 C8 -78.6(11) . . . . ? C6 C7 C8 C9 105.7(14) . . . . ? C1 O1 C10 N1 24.8(8) . . . . ? C1 O1 C10 C11 -92.6(8) . . . . ? C1 O1 C10 C12 144.3(7) . . . . ? C13 N1 C10 O1 154.9(7) . . . . ? C2 N1 C10 O1 -9.0(8) . . . . ? C13 N1 C10 C11 -88.1(10) . . . . ? C2 N1 C10 C11 108.1(8) . . . . ? C13 N1 C10 C12 41.3(11) . . . . ? C2 N1 C10 C12 -122.6(8) . . . . ? C2 N1 C13 O2 1.8(12) . . . . ? C10 N1 C13 O2 -161.0(7) . . . . ? C2 N1 C13 O3 -175.5(6) . . . . ? C10 N1 C13 O3 21.7(11) . . . . ? C14 O3 C13 O2 -3.3(12) . . . . ? C14 O3 C13 N1 174.0(7) . . . . ? C13 O3 C14 C16 63.2(10) . . . . ? C13 O3 C14 C17 177.6(7) . . . . ? C13 O3 C14 C15 -62.4(10) . . . . ? C4 O4 C18 C19 170.5(6) . . . . ? O4 C18 C19 C24 -27.8(11) . . . . ? O4 C18 C19 C20 153.9(7) . . . . ? C24 C19 C20 C21 -0.4(13) . . . . ? C18 C19 C20 C21 178.0(8) . . . . ? C19 C20 C21 C22 1.3(14) . . . . ? C20 C21 C22 C23 -2.3(17) . . . . ? C21 C22 C23 C24 2(2) . . . . ? C20 C19 C24 C23 0.5(15) . . . . ? C18 C19 C24 C23 -177.8(10) . . . . ? C22 C23 C24 C19 -1.6(19) . . . . ? C3 O5 C25 C26 -146.7(7) . . . . ? O5 C25 C26 C31 -113.6(9) . . . . ? O5 C25 C26 C27 66.7(10) . . . . ? C31 C26 C27 C28 -1.3(13) . . . . ? C25 C26 C27 C28 178.4(9) . . . . ? C26 C27 C28 C29 -0.2(17) . . . . ? C27 C28 C29 C30 1(2) . . . . ? C28 C29 C30 C31 -1(2) . . . . ? C27 C26 C31 C30 1.6(14) . . . . ? C25 C26 C31 C30 -178.2(10) . . . . ? C29 C30 C31 C26 -0.4(18) . . . . ? C5 O6 C32 O7 12.0(12) . . . . ? C5 O6 C32 C33 -167.1(6) . . . . ? O7 C32 C33 C38 175.0(8) . . . . ? O6 C32 C33 C38 -5.9(9) . . . . ? O7 C32 C33 C34 -8.0(11) . . . . ? O6 C32 C33 C34 171.1(6) . . . . ? C38 C33 C34 C35 1.2(10) . . . . ? C32 C33 C34 C35 -175.9(7) . . . . ? C33 C34 C35 C36 -0.8(12) . . . . ? C33 C34 C35 N3 177.1(7) . . . . ? O10 N3 C35 C34 8.3(13) . . . . ? O11 N3 C35 C34 -170.5(8) . . . . ? O10 N3 C35 C36 -173.7(9) . . . . ? O11 N3 C35 C36 7.5(12) . . . . ? C34 C35 C36 C37 -0.1(12) . . . . ? N3 C35 C36 C37 -178.0(8) . . . . ? C35 C36 C37 C38 0.7(12) . . . . ? C35 C36 C37 N2 -179.8(7) . . . . ? O9 N2 C37 C36 6.1(11) . . . . ? O8 N2 C37 C36 -176.2(8) . . . . ? O9 N2 C37 C38 -174.4(7) . . . . ? O8 N2 C37 C38 3.3(11) . . . . ? C34 C33 C38 C37 -0.7(10) . . . . ? C32 C33 C38 C37 176.3(7) . . . . ? C36 C37 C38 C33 -0.3(11) . . . . ? N2 C37 C38 C33 -179.8(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052