# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2010 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ren-Gen Xiong' _publ_contact_author_email XIONGRG@SEU.EDU.CN _publ_section_title ; The First homochiral compound with temperature-independence of piezoelectric properties ; loop_ _publ_author_name 'Ren-Gen Xiong.' 'Hong-Lin Cai.' 'Li-Zhuang Chen.' 'Tong Zhang.' # Attachment 'Compound-1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 750368' #TrackingRef 'Compound-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 Cl6 N2 O4' _chemical_formula_weight 426.92 _chemical_absolute_configuration SYN loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 6.337(4) _cell_length_b 19.790(5) _cell_length_c 6.947(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.21(3) _cell_angle_gamma 90.00 _cell_volume 867.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8845 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8749 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3933 _reflns_number_gt 2709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0536P)^2^+0.1423P] 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 -0.03(10) _refine_ls_number_reflns 3933 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.48148(18) 0.67437(8) 0.25321(18) 0.0523(4) Uani 1 1 d . . . Cl2 Cl 0.8500(3) 0.64205(9) 0.0619(2) 0.0761(6) Uani 1 1 d . . . Cl5 Cl 0.6401(3) 0.99711(9) 0.3815(3) 0.0847(6) Uani 1 1 d . . . Cl4 Cl 1.0125(2) 0.96113(9) 0.2061(3) 0.0775(6) Uani 1 1 d . . . Cl3 Cl 0.8256(3) 0.60174(9) 0.4576(3) 0.0825(6) Uani 1 1 d . . . O1 O 1.0493(5) 0.7439(2) 0.3215(5) 0.0456(9) Uani 1 1 d . . . Cl6 Cl 0.6596(4) 1.01614(10) -0.0279(3) 0.1028(7) Uani 1 1 d . . . O3 O 0.4570(5) 0.8815(2) 0.1689(5) 0.0539(11) Uani 1 1 d . . . N2 N 0.1359(6) 0.8444(2) 0.8958(6) 0.0434(11) Uani 1 1 d . . . H2D H 0.2437 0.8569 0.9817 0.052 Uiso 1 1 calc R . . H2C H 0.0139 0.8541 0.9466 0.052 Uiso 1 1 calc R . . C9 C 0.6364(7) 0.8918(3) 0.1157(7) 0.0388(11) Uani 1 1 d . . . C3 C 0.1475(8) 0.7704(3) 0.8615(7) 0.0411(12) Uani 1 1 d . . . H3B H 0.0267 0.7564 0.7749 0.049 Uiso 1 1 calc R . . H3A H 0.1414 0.7466 0.9830 0.049 Uiso 1 1 calc R . . O2 O 0.7676(5) 0.7663(2) 0.4807(5) 0.0539(11) Uani 1 1 d . . . N1 N 0.3605(6) 0.7917(2) 0.5897(5) 0.0383(10) Uani 1 1 d . . . H1D H 0.4825 0.7822 0.5385 0.046 Uiso 1 1 calc R . . H1C H 0.2529 0.7789 0.5040 0.046 Uiso 1 1 calc R . . O4 O 0.7412(5) 0.8560(2) 0.0146(5) 0.0520(10) Uani 1 1 d . . . C1 C 0.3473(8) 0.8655(3) 0.6209(7) 0.0427(13) Uani 1 1 d . . . H1B H 0.3480 0.8887 0.4980 0.051 Uiso 1 1 calc R . . H1A H 0.4700 0.8804 0.7037 0.051 Uiso 1 1 calc R . . C7 C 0.8699(7) 0.7334(3) 0.3700(7) 0.0392(12) Uani 1 1 d . . . C8 C 0.7350(8) 0.9632(3) 0.1704(8) 0.0479(13) Uani 1 1 d . . . C4 C 0.3512(7) 0.7516(3) 0.7738(6) 0.0379(11) Uani 1 1 d . . . H4 H 0.4730 0.7634 0.8647 0.045 Uiso 1 1 calc R . . C6 C 0.7620(7) 0.6664(2) 0.2852(7) 0.0416(12) Uani 1 1 d . . . C2 C 0.1469(8) 0.8833(3) 0.7136(8) 0.0527(14) Uani 1 1 d . . . H2B H 0.1455 0.9314 0.7415 0.063 Uiso 1 1 calc R . . H2A H 0.0240 0.8731 0.6248 0.063 Uiso 1 1 calc R . . C5 C 0.3564(8) 0.6771(3) 0.7312(8) 0.0587(14) Uani 1 1 d . . . H5C H 0.3439 0.6521 0.8481 0.088 Uiso 1 1 calc R . . H5B H 0.4879 0.6659 0.6803 0.088 Uiso 1 1 calc R . . H5A H 0.2406 0.6657 0.6380 0.088 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 Cl1 0.0321(7) 0.0750(10) 0.0489(7) -0.0142(7) -0.0007(5) -0.0061(7) Cl2 0.0634(10) 0.0864(12) 0.0839(12) -0.0430(10) 0.0369(8) -0.0235(9) Cl5 0.0944(14) 0.0741(11) 0.0930(13) -0.0430(10) 0.0488(10) -0.0271(10) Cl4 0.0453(9) 0.0874(13) 0.1005(14) -0.0389(10) 0.0102(8) -0.0186(9) Cl3 0.0671(10) 0.0652(10) 0.1129(15) 0.0314(10) -0.0046(10) 0.0016(8) O1 0.0263(19) 0.066(3) 0.0447(19) -0.0099(18) 0.0052(14) -0.0109(18) Cl6 0.145(2) 0.0663(12) 0.0934(15) 0.0296(10) -0.0063(13) 0.0058(12) O3 0.030(2) 0.079(3) 0.054(2) -0.017(2) 0.0101(16) -0.0105(19) N2 0.031(2) 0.062(3) 0.038(2) -0.010(2) 0.0075(17) -0.004(2) C9 0.032(3) 0.044(3) 0.039(3) 0.001(2) -0.001(2) 0.000(2) C3 0.042(3) 0.050(3) 0.032(3) 0.001(2) 0.0058(19) -0.006(2) O2 0.032(2) 0.074(3) 0.056(2) -0.025(2) 0.0037(17) -0.0037(19) N1 0.031(2) 0.050(3) 0.035(2) -0.0055(18) 0.0078(16) -0.0012(19) O4 0.038(2) 0.056(2) 0.064(2) -0.026(2) 0.0160(17) -0.0045(18) C1 0.041(3) 0.047(3) 0.041(3) 0.001(2) 0.009(2) -0.007(3) C7 0.028(3) 0.051(3) 0.037(3) -0.003(2) -0.0029(19) 0.003(2) C8 0.050(3) 0.044(3) 0.051(3) 0.000(2) 0.014(2) -0.001(3) C4 0.032(3) 0.053(3) 0.029(2) 0.000(2) 0.0007(17) 0.000(2) C6 0.035(3) 0.041(3) 0.050(3) -0.004(2) 0.009(2) -0.001(2) C2 0.055(4) 0.055(3) 0.049(3) -0.007(3) 0.010(2) 0.002(3) C5 0.074(4) 0.052(3) 0.050(3) -0.005(3) 0.003(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.778(5) . ? Cl2 C6 1.762(5) . ? Cl5 C8 1.767(5) . ? Cl4 C8 1.754(6) . ? Cl3 C6 1.774(5) . ? O1 C7 1.233(5) . ? Cl6 C8 1.761(6) . ? O3 C9 1.244(6) . ? N2 C3 1.487(7) . ? N2 C2 1.489(7) . ? N2 H2D 0.9000 . ? N2 H2C 0.9000 . ? C9 O4 1.233(6) . ? C9 C8 1.577(8) . ? C3 C4 1.522(7) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? O2 C7 1.236(6) . ? N1 C1 1.479(7) . ? N1 C4 1.511(6) . ? N1 H1D 0.9000 . ? N1 H1C 0.9000 . ? C1 C2 1.518(7) . ? C1 H1B 0.9700 . ? C1 H1A 0.9700 . ? C7 C6 1.580(7) . ? C4 C5 1.505(8) . ? C4 H4 0.9800 . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C5 H5C 0.9600 . ? C5 H5B 0.9600 . ? C5 H5A 0.9600 . ? 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 C3 N2 C2 111.5(4) . . ? C3 N2 H2D 109.3 . . ? C2 N2 H2D 109.3 . . ? C3 N2 H2C 109.3 . . ? C2 N2 H2C 109.3 . . ? H2D N2 H2C 108.0 . . ? O4 C9 O3 128.9(5) . . ? O4 C9 C8 115.5(4) . . ? O3 C9 C8 115.4(5) . . ? N2 C3 C4 111.1(4) . . ? N2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? N2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? H3B C3 H3A 108.0 . . ? C1 N1 C4 112.8(4) . . ? C1 N1 H1D 109.0 . . ? C4 N1 H1D 109.0 . . ? C1 N1 H1C 109.0 . . ? C4 N1 H1C 109.0 . . ? H1D N1 H1C 107.8 . . ? N1 C1 C2 110.6(4) . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? H1B C1 H1A 108.1 . . ? O1 C7 O2 129.0(5) . . ? O1 C7 C6 114.8(4) . . ? O2 C7 C6 116.2(4) . . ? C9 C8 Cl4 112.5(4) . . ? C9 C8 Cl6 105.7(4) . . ? Cl4 C8 Cl6 108.8(3) . . ? C9 C8 Cl5 112.5(3) . . ? Cl4 C8 Cl5 107.7(3) . . ? Cl6 C8 Cl5 109.6(3) . . ? C5 C4 N1 110.2(4) . . ? C5 C4 C3 110.6(4) . . ? N1 C4 C3 108.1(4) . . ? C5 C4 H4 109.3 . . ? N1 C4 H4 109.3 . . ? C3 C4 H4 109.3 . . ? C7 C6 Cl2 113.4(3) . . ? C7 C6 Cl3 106.8(3) . . ? Cl2 C6 Cl3 109.0(3) . . ? C7 C6 Cl1 111.5(3) . . ? Cl2 C6 Cl1 107.9(3) . . ? Cl3 C6 Cl1 108.1(3) . . ? N2 C2 C1 110.2(4) . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? H2B C2 H2A 108.1 . . ? C4 C5 H5C 109.5 . . ? C4 C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? C4 C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.332 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.064 # Attachment 'Compound-2.cif' data_zh _database_code_depnum_ccdc_archive 'CCDC 750369' #TrackingRef 'Compound-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H54 Bi Cl7 N4 O5' _chemical_formula_weight 1128.00 _chemical_absolute_configuration SYN loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.2119(18) _cell_length_b 11.087(2) _cell_length_c 11.866(2) _cell_angle_alpha 85.70(3) _cell_angle_beta 76.62(3) _cell_angle_gamma 72.83(3) _cell_volume 1126.4(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 4.375 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8873 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 ? _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 11777 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0882 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9737 _reflns_number_gt 9708 _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 -0.0011(15) _refine_ls_number_reflns 9737 _refine_ls_number_parameters 514 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _refine_ls_shift/su_max 0.003 _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 Bi1 Bi 0.0590 0.4073 0.4219 0.02921(5) Uani 1 1 d . . . C1 C 0.6508(8) 1.1675(6) 0.5596(6) 0.0521(16) Uani 1 1 d . . . H1A H 0.6294 1.2319 0.6122 0.063 Uiso 1 1 calc R . . C2 C 0.6001(7) 1.0633(6) 0.5917(5) 0.0425(14) Uani 1 1 d . . . H2A H 0.5412 1.0590 0.6662 0.051 Uiso 1 1 calc R . . C3 C 0.6331(6) 0.9654(5) 0.5180(5) 0.0333(12) Uani 1 1 d . . . C4 C 0.7260(6) 0.9712(5) 0.4052(5) 0.0314(12) Uani 1 1 d . . . C5 C 0.7731(8) 1.0811(7) 0.3729(6) 0.0394(15) Uani 1 1 d . . . C6 C 0.8622(8) 1.0975(7) 0.2591(6) 0.0485(16) Uani 1 1 d . . . H6A H 0.8921 1.1709 0.2400 0.058 Uiso 1 1 calc R . . C7 C 0.9018(9) 1.0052(7) 0.1806(7) 0.0484(19) Uani 1 1 d . . . H7A H 0.9594 1.0152 0.1069 0.058 Uiso 1 1 calc R . . C8 C 0.8565(7) 0.8922(6) 0.2090(5) 0.0450(14) Uani 1 1 d . . . C9 C 0.7743(7) 0.8729(6) 0.3217(6) 0.0403(14) Uani 1 1 d . . . H9A H 0.7517 0.7967 0.3414 0.048 Uiso 1 1 calc R . . C10 C 0.8310(9) 0.7063(6) 0.1367(6) 0.0579(19) Uani 1 1 d . . . H10A H 0.8692 0.6556 0.0681 0.087 Uiso 1 1 calc R . . H10B H 0.7196 0.7377 0.1507 0.087 Uiso 1 1 calc R . . H10C H 0.8604 0.6558 0.2016 0.087 Uiso 1 1 calc R . . C11 C 0.5622(7) 0.8544(6) 0.5592(5) 0.0406(13) Uani 1 1 d . . . H11A H 0.6453 0.7747 0.5554 0.049 Uiso 1 1 calc R . . C12 C 0.4514(7) 0.8484(5) 0.4813(5) 0.0319(12) Uani 1 1 d . . . H12A H 0.5158 0.8251 0.4037 0.038 Uiso 1 1 calc R . . C13 C 0.3227(8) 0.9682(5) 0.4680(6) 0.0402(15) Uani 1 1 d . . . H13A H 0.3606 1.0177 0.4031 0.048 Uiso 1 1 calc R . . H13B H 0.2926 1.0188 0.5375 0.048 Uiso 1 1 calc R . . C14 C 0.1820(7) 0.9341(6) 0.4477(6) 0.0485(15) Uani 1 1 d . . . H14A H 0.1110 1.0079 0.4188 0.058 Uiso 1 1 calc R . . C15 C 0.0992(7) 0.8895(6) 0.5643(6) 0.0520(16) Uani 1 1 d . . . H15A H 0.0504 0.9601 0.6169 0.062 Uiso 1 1 calc R . . H15B H 0.0190 0.8544 0.5525 0.062 Uiso 1 1 calc R . . C16 C 0.2211(9) 0.7884(7) 0.6158(7) 0.052(2) Uani 1 1 d . . . H16A H 0.2435 0.8234 0.6802 0.062 Uiso 1 1 calc R . . H16B H 0.1810 0.7176 0.6446 0.062 Uiso 1 1 calc R . . C17 C 0.3275(8) 0.7056(6) 0.4195(6) 0.0463(17) Uani 1 1 d . . . H17A H 0.2663 0.6466 0.4431 0.056 Uiso 1 1 calc R . . H17B H 0.4214 0.6636 0.3643 0.056 Uiso 1 1 calc R . . C18 C 0.2326(8) 0.8226(5) 0.3614(5) 0.0448(15) Uani 1 1 d . . . H18A H 0.1377 0.8047 0.3530 0.054 Uiso 1 1 calc R . . C19 C 0.3153(12) 0.8522(8) 0.2434(6) 0.083(3) Uani 1 1 d D . . H19A H 0.3483 0.9242 0.2401 0.099 Uiso 1 1 calc R . . C20 C 0.3479(11) 0.7984(8) 0.1492(7) 0.086(3) Uani 1 1 d D . . H20A H 0.3194 0.7255 0.1443 0.103 Uiso 1 1 calc R . . H20B H 0.4010 0.8309 0.0833 0.103 Uiso 1 1 calc R . . C21 C 0.5344(7) 0.4045(7) 1.1813(5) 0.0519(17) Uani 1 1 d . . . H21A H 0.4865 0.4547 1.2465 0.062 Uiso 1 1 calc R . . C22 C 0.6295(6) 0.4484(6) 1.0895(5) 0.0402(13) Uani 1 1 d . . . H22A H 0.6443 0.5272 1.0936 0.048 Uiso 1 1 calc R . . C23 C 0.7023(6) 0.3755(5) 0.9921(5) 0.0326(11) Uani 1 1 d . . . C24 C 0.6779(6) 0.2545(5) 0.9885(4) 0.0298(11) Uani 1 1 d . . . C25 C 0.5803(6) 0.2149(5) 1.0861(5) 0.0351(12) Uani 1 1 d . . . C26 C 0.5556(7) 0.0970(6) 1.0906(6) 0.0459(15) Uani 1 1 d . . . H26A H 0.4894 0.0734 1.1545 0.055 Uiso 1 1 calc R . . C27 C 0.6295(7) 0.0157(6) 1.0003(6) 0.0453(15) Uani 1 1 d . . . H27A H 0.6175 -0.0651 1.0056 0.054 Uiso 1 1 calc R . . C28 C 0.7232(7) 0.0509(6) 0.8994(5) 0.0392(13) Uani 1 1 d . . . C29 C 0.7460(6) 0.1710(5) 0.8957(5) 0.0329(12) Uani 1 1 d . . . H29A H 0.8078 0.1957 0.8298 0.040 Uiso 1 1 calc R . . C30 C 0.7957(9) -0.1500(6) 0.8144(6) 0.061(2) Uani 1 1 d . . . H30A H 0.8511 -0.1905 0.7419 0.091 Uiso 1 1 calc R . . H30B H 0.6903 -0.1546 0.8309 0.091 Uiso 1 1 calc R . . H30C H 0.8457 -0.1919 0.8751 0.091 Uiso 1 1 calc R . . C31 C 0.8119(6) 0.4237(4) 0.8933(4) 0.0271(10) Uani 1 1 d . . . H31A H 0.7875 0.4121 0.8195 0.032 Uiso 1 1 calc R . . C32 C 0.9796(6) 0.3463(5) 0.8925(4) 0.0335(12) Uani 1 1 d . . . H32A H 0.9856 0.2578 0.8829 0.040 Uiso 1 1 calc R . . C33 C 1.0363(7) 0.3530(6) 1.0044(5) 0.0370(13) Uani 1 1 d . . . H33A H 0.9869 0.4354 1.0397 0.044 Uiso 1 1 calc R . . H33B H 1.0105 0.2895 1.0597 0.044 Uiso 1 1 calc R . . C34 C 1.2146(8) 0.3291(6) 0.9692(5) 0.0466(15) Uani 1 1 d . . . H34A H 1.2591 0.3092 1.0381 0.056 Uiso 1 1 calc R . . C35 C 1.2445(9) 0.4510(7) 0.9122(7) 0.065(2) Uani 1 1 d . . . H35A H 1.2146 0.5162 0.9701 0.078 Uiso 1 1 calc R . . H35B H 1.3545 0.4360 0.8776 0.078 Uiso 1 1 calc R . . C36 C 1.1491(9) 0.4939(7) 0.8189(7) 0.059(2) Uani 1 1 d . . . H36A H 1.2118 0.5205 0.7496 0.070 Uiso 1 1 calc R . . H36B H 1.0586 0.5644 0.8466 0.070 Uiso 1 1 calc R . . C37 C 1.2373(7) 0.2658(8) 0.7677(5) 0.062(2) Uani 1 1 d . . . H37A H 1.3213 0.2873 0.7121 0.075 Uiso 1 1 calc R . . H37B H 1.2115 0.1990 0.7353 0.075 Uiso 1 1 calc R . . C38 C 1.2892(7) 0.2202(7) 0.8820(5) 0.0524(17) Uani 1 1 d . . . H38A H 1.4024 0.2047 0.8668 0.063 Uiso 1 1 calc R . . C39 C 1.2534(8) 0.0991(7) 0.9316(7) 0.0622(19) Uani 1 1 d D . . H39A H 1.2704 0.0784 1.0058 0.075 Uiso 1 1 calc R . . C40 C 1.2032(11) 0.0204(8) 0.8878(9) 0.102(3) Uani 1 1 d D . . H40A H 1.1833 0.0343 0.8139 0.122 Uiso 1 1 calc R . . H40B H 1.1870 -0.0503 0.9302 0.122 Uiso 1 1 calc R . . Cl1 Cl -0.0507(3) 0.5935(2) 0.5821(2) 0.0590(7) Uani 1 1 d . . . Cl2 Cl -0.0400(3) 0.2549(2) 0.60789(19) 0.0455(5) Uani 1 1 d . . . Cl3 Cl 0.3399(3) 0.3480(2) 0.46556(19) 0.0541(6) Uani 1 1 d . . . Cl4 Cl 0.1461(3) 0.5564(2) 0.2571(2) 0.0507(6) Uani 1 1 d . . . Cl5 Cl 0.1797(3) 0.2135(2) 0.26993(19) 0.0424(5) Uani 1 1 d . . . Cl6 Cl -0.2342(3) 0.4501(2) 0.3623(2) 0.0528(6) Uani 1 1 d . . . Cl7 Cl 0.4867(2) 0.66662(17) 0.84590(16) 0.0579(4) Uani 1 1 d . . . N1 N 0.7317(6) 1.1754(5) 0.4515(6) 0.0496(14) Uani 1 1 d . . . H1B H 0.7587 1.2431 0.4306 0.060 Uiso 1 1 calc R . . N2 N 0.3697(6) 0.7436(5) 0.5224(4) 0.0385(12) Uani 1 1 d . . . H2 H 0.4378 0.6786 0.5502 0.046 Uiso 1 1 d R . . N3 N 0.5105(6) 0.2951(5) 1.1786(4) 0.0429(12) Uani 1 1 d . . . H3A H 0.4490 0.2720 1.2366 0.051 Uiso 1 1 calc R . . N4 N 1.0972(6) 0.3797(5) 0.7915(4) 0.0437(12) Uani 1 1 d . . . H4 H 1.0503 0.4294 0.7250 0.052 Uiso 1 1 d R . . O1 O 0.8959(5) 0.8092(4) 0.1215(4) 0.0562(12) Uani 1 1 d . . . O2 O 0.4805(5) 0.8807(4) 0.6745(3) 0.0548(12) Uani 1 1 d . . . H2B H 0.4419 0.8237 0.7001 0.082 Uiso 1 1 calc R . . O3 O 0.7954(6) -0.0238(4) 0.8078(4) 0.0526(12) Uani 1 1 d . . . O4 O 0.7977(5) 0.5528(4) 0.9056(4) 0.0435(10) Uani 1 1 d . . . H4A H 0.7081 0.5950 0.9055 0.065 Uiso 1 1 calc R . . O1W O 0.5387(7) 0.5243(5) 0.6183(5) 0.0764(16) Uani 1 1 d . . . H1WB H 0.6205 0.4895 0.5684 0.115 Uiso 1 1 d R . . H1WC H 0.5640 0.5434 0.6776 0.115 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02768(8) 0.03380(8) 0.02798(8) 0.00065(6) -0.00505(6) -0.01262(6) C1 0.044(4) 0.053(4) 0.060(4) -0.011(3) -0.010(3) -0.015(3) C2 0.045(3) 0.046(3) 0.040(3) -0.005(3) -0.012(3) -0.016(3) C3 0.033(3) 0.037(3) 0.039(3) 0.004(2) -0.016(2) -0.019(2) C4 0.032(3) 0.032(3) 0.043(3) 0.003(2) -0.014(2) -0.025(2) C5 0.032(3) 0.051(4) 0.043(4) 0.005(3) -0.016(3) -0.020(3) C6 0.041(4) 0.051(4) 0.056(4) 0.011(3) -0.008(3) -0.021(3) C7 0.040(4) 0.060(4) 0.049(5) 0.003(4) -0.002(3) -0.028(3) C8 0.034(3) 0.058(4) 0.041(3) -0.004(3) -0.009(3) -0.010(3) C9 0.027(3) 0.046(4) 0.048(4) 0.004(3) -0.009(3) -0.011(3) C10 0.076(5) 0.043(4) 0.065(5) -0.010(3) -0.031(4) -0.019(4) C11 0.043(3) 0.046(3) 0.034(3) 0.005(3) -0.009(3) -0.015(3) C12 0.042(3) 0.030(3) 0.035(3) 0.000(2) -0.008(3) -0.029(3) C13 0.051(4) 0.029(3) 0.052(4) 0.012(3) -0.022(3) -0.021(3) C14 0.040(3) 0.048(3) 0.060(4) 0.015(3) -0.017(3) -0.016(3) C15 0.045(4) 0.057(4) 0.058(4) -0.008(3) -0.006(3) -0.024(3) C16 0.056(5) 0.048(4) 0.045(5) 0.018(4) 0.000(4) -0.021(4) C17 0.055(4) 0.040(4) 0.060(5) -0.003(3) -0.018(4) -0.032(3) C18 0.066(4) 0.041(3) 0.051(4) 0.008(3) -0.026(3) -0.041(3) C19 0.142(8) 0.105(7) 0.047(4) 0.017(4) -0.028(5) -0.102(7) C20 0.110(8) 0.076(6) 0.074(6) -0.009(5) 0.020(5) -0.058(6) C21 0.038(3) 0.070(5) 0.037(3) -0.012(3) 0.004(3) -0.005(3) C22 0.035(3) 0.047(3) 0.040(3) -0.009(3) -0.002(3) -0.015(3) C23 0.027(3) 0.037(3) 0.034(3) 0.001(2) -0.007(2) -0.010(2) C24 0.026(3) 0.034(3) 0.030(3) 0.004(2) -0.004(2) -0.012(2) C25 0.025(3) 0.039(3) 0.038(3) 0.010(3) -0.002(2) -0.010(2) C26 0.032(3) 0.047(3) 0.053(4) 0.008(3) 0.000(3) -0.011(3) C27 0.036(3) 0.041(3) 0.062(4) 0.007(3) -0.006(3) -0.019(3) C28 0.037(3) 0.040(3) 0.044(3) -0.004(3) -0.009(3) -0.014(3) C29 0.036(3) 0.030(3) 0.033(3) 0.011(2) -0.001(2) -0.018(2) C30 0.092(6) 0.040(3) 0.066(5) -0.006(3) -0.022(4) -0.040(4) C31 0.033(3) 0.022(2) 0.032(3) 0.000(2) -0.009(2) -0.015(2) C32 0.028(3) 0.043(3) 0.029(3) 0.003(2) -0.003(2) -0.012(2) C33 0.045(4) 0.043(3) 0.031(3) 0.009(3) -0.015(3) -0.021(3) C34 0.046(4) 0.066(4) 0.034(3) 0.016(3) -0.021(3) -0.020(3) C35 0.062(5) 0.066(5) 0.090(6) 0.015(4) -0.036(5) -0.043(4) C36 0.066(5) 0.051(4) 0.076(5) 0.032(4) -0.029(4) -0.040(4) C37 0.029(3) 0.112(6) 0.035(3) -0.009(4) 0.003(3) -0.010(4) C38 0.030(3) 0.073(5) 0.043(4) 0.004(3) -0.006(3) -0.001(3) C39 0.042(4) 0.060(4) 0.077(5) 0.001(4) -0.017(4) 0.000(3) C40 0.099(8) 0.077(6) 0.099(8) -0.029(6) 0.012(6) -0.001(6) Cl1 0.0681(17) 0.0496(13) 0.0566(15) -0.0233(11) -0.0024(13) -0.0161(12) Cl2 0.0584(12) 0.0530(12) 0.0335(9) 0.0065(8) -0.0070(8) -0.0328(10) Cl3 0.0384(10) 0.0860(16) 0.0444(10) 0.0180(10) -0.0182(8) -0.0250(10) Cl4 0.0547(13) 0.0539(12) 0.0518(12) 0.0205(10) -0.0184(10) -0.0282(10) Cl5 0.0500(13) 0.0375(10) 0.0373(11) -0.0046(8) 0.0000(9) -0.0153(9) Cl6 0.0491(11) 0.0559(11) 0.0658(14) 0.0136(10) -0.0274(10) -0.0259(9) Cl7 0.0577(10) 0.0563(10) 0.0580(10) 0.0166(8) -0.0153(8) -0.0158(8) N1 0.045(3) 0.037(3) 0.071(4) 0.001(3) -0.015(3) -0.017(3) N2 0.045(3) 0.028(2) 0.039(3) 0.015(2) -0.007(2) -0.010(2) N3 0.035(3) 0.052(3) 0.038(3) -0.003(2) 0.009(2) -0.018(2) N4 0.036(3) 0.066(3) 0.031(3) 0.013(2) -0.011(2) -0.019(3) O1 0.058(3) 0.060(3) 0.043(3) -0.006(2) -0.001(2) -0.011(2) O2 0.070(3) 0.067(3) 0.035(2) 0.010(2) -0.009(2) -0.035(3) O3 0.078(3) 0.037(2) 0.042(2) -0.0105(19) 0.001(2) -0.025(2) O4 0.046(3) 0.031(2) 0.053(3) 0.0034(19) -0.006(2) -0.015(2) O1W 0.081(4) 0.060(3) 0.082(4) -0.008(3) -0.025(3) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 Cl4 2.602(2) . ? Bi1 Cl3 2.638(2) . ? Bi1 Cl5 2.711(2) . ? Bi1 Cl1 2.714(3) . ? Bi1 Cl2 2.824(2) . ? Bi1 Cl6 2.845(2) . ? C1 N1 1.337(9) . ? C1 C2 1.368(8) . ? C1 H1A 0.9300 . ? C2 C3 1.364(8) . ? C2 H2A 0.9300 . ? C3 C4 1.419(8) . ? C3 C11 1.554(7) . ? C4 C5 1.410(8) . ? C4 C9 1.428(9) . ? C5 N1 1.362(9) . ? C5 C6 1.438(10) . ? C6 C7 1.347(10) . ? C6 H6A 0.9300 . ? C7 C8 1.426(9) . ? C7 H7A 0.9300 . ? C8 O1 1.353(8) . ? C8 C9 1.411(8) . ? C9 H9A 0.9300 . ? C10 O1 1.419(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 O2 1.407(7) . ? C11 C12 1.545(8) . ? C11 H11A 0.9800 . ? C12 C13 1.523(8) . ? C12 N2 1.554(7) . ? C12 H12A 0.9800 . ? C13 C14 1.526(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.540(9) . ? C14 C18 1.557(9) . ? C14 H14A 0.9800 . ? C15 C16 1.538(10) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N2 1.525(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.488(8) . ? C17 C18 1.548(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.494(9) . ? C18 H18A 0.9800 . ? C19 C20 1.239(9) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C20 H20B 0.9300 . ? C21 N3 1.300(8) . ? C21 C22 1.386(8) . ? C21 H21A 0.9300 . ? C22 C23 1.378(8) . ? C22 H22A 0.9300 . ? C23 C24 1.429(7) . ? C23 C31 1.536(7) . ? C24 C29 1.398(8) . ? C24 C25 1.420(7) . ? C25 N3 1.375(8) . ? C25 C26 1.387(8) . ? C26 C27 1.367(9) . ? C26 H26A 0.9300 . ? C27 C28 1.407(8) . ? C27 H27A 0.9300 . ? C28 O3 1.336(7) . ? C28 C29 1.404(7) . ? C29 H29A 0.9300 . ? C30 O3 1.396(6) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 O4 1.414(6) . ? C31 C32 1.528(7) . ? C31 H31A 0.9800 . ? C32 N4 1.523(7) . ? C32 C33 1.548(8) . ? C32 H32A 0.9800 . ? C33 C34 1.544(8) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.535(9) . ? C34 C38 1.540(10) . ? C34 H34A 0.9800 . ? C35 C36 1.533(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 N4 1.558(8) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 N4 1.504(8) . ? C37 C38 1.542(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.520(10) . ? C38 H38A 0.9800 . ? C39 C40 1.289(10) . ? C39 H39A 0.9300 . ? C40 H40A 0.9300 . ? C40 H40B 0.9300 . ? N1 H1B 0.8600 . ? N2 H2 0.9027 . ? N3 H3A 0.8600 . ? N4 H4 1.0316 . ? O2 H2B 0.8200 . ? O4 H4A 0.8200 . ? O1W H1WB 0.8499 . ? O1W H1WC 0.8500 . ? 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 Cl4 Bi1 Cl3 88.59(8) . . ? Cl4 Bi1 Cl5 88.74(8) . . ? Cl3 Bi1 Cl5 85.51(8) . . ? Cl4 Bi1 Cl1 93.06(9) . . ? Cl3 Bi1 Cl1 91.69(9) . . ? Cl5 Bi1 Cl1 176.63(10) . . ? Cl4 Bi1 Cl2 177.38(10) . . ? Cl3 Bi1 Cl2 91.40(8) . . ? Cl5 Bi1 Cl2 93.87(7) . . ? Cl1 Bi1 Cl2 84.32(8) . . ? Cl4 Bi1 Cl6 92.09(8) . . ? Cl3 Bi1 Cl6 174.58(9) . . ? Cl5 Bi1 Cl6 89.13(8) . . ? Cl1 Bi1 Cl6 93.64(9) . . ? Cl2 Bi1 Cl6 88.17(7) . . ? N1 C1 C2 119.0(6) . . ? N1 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? C3 C2 C1 122.1(6) . . ? C3 C2 H2A 118.9 . . ? C1 C2 H2A 118.9 . . ? C2 C3 C4 118.7(5) . . ? C2 C3 C11 118.6(5) . . ? C4 C3 C11 122.7(5) . . ? C5 C4 C3 118.2(6) . . ? C5 C4 C9 117.6(6) . . ? C3 C4 C9 124.2(5) . . ? N1 C5 C4 119.0(6) . . ? N1 C5 C6 118.9(6) . . ? C4 C5 C6 122.1(7) . . ? C7 C6 C5 119.1(7) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C6 C7 C8 120.9(7) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? O1 C8 C9 123.9(6) . . ? O1 C8 C7 115.6(6) . . ? C9 C8 C7 120.5(6) . . ? C8 C9 C4 119.6(6) . . ? C8 C9 H9A 120.2 . . ? C4 C9 H9A 120.2 . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 C12 111.0(5) . . ? O2 C11 C3 106.3(5) . . ? C12 C11 C3 109.2(4) . . ? O2 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? C3 C11 H11A 110.1 . . ? C13 C12 C11 117.6(5) . . ? C13 C12 N2 106.2(4) . . ? C11 C12 N2 111.6(4) . . ? C13 C12 H12A 107.0 . . ? C11 C12 H12A 107.0 . . ? N2 C12 H12A 107.0 . . ? C12 C13 C14 109.8(5) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C15 107.7(5) . . ? C13 C14 C18 111.3(5) . . ? C15 C14 C18 107.2(5) . . ? C13 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? C18 C14 H14A 110.2 . . ? C16 C15 C14 108.4(5) . . ? C16 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? C16 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? N2 C16 C15 109.2(5) . . ? N2 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N2 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? N2 C17 C18 110.5(5) . . ? N2 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? N2 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C19 C18 C17 114.0(7) . . ? C19 C18 C14 113.4(5) . . ? C17 C18 C14 107.2(5) . . ? C19 C18 H18A 107.3 . . ? C17 C18 H18A 107.3 . . ? C14 C18 H18A 107.3 . . ? C20 C19 C18 131.9(7) . . ? C20 C19 H19A 114.1 . . ? C18 C19 H19A 114.1 . . ? C19 C20 H20A 120.0 . . ? C19 C20 H20B 120.0 . . ? H20A C20 H20B 120.0 . . ? N3 C21 C22 121.7(6) . . ? N3 C21 H21A 119.1 . . ? C22 C21 H21A 119.1 . . ? C23 C22 C21 120.2(6) . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C22 C23 C24 118.6(5) . . ? C22 C23 C31 119.3(5) . . ? C24 C23 C31 122.0(5) . . ? C29 C24 C25 117.5(5) . . ? C29 C24 C23 124.3(5) . . ? C25 C24 C23 118.2(5) . . ? N3 C25 C26 119.5(5) . . ? N3 C25 C24 119.0(5) . . ? C26 C25 C24 121.5(6) . . ? C27 C26 C25 119.4(6) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C26 C27 C28 121.8(6) . . ? C26 C27 H27A 119.1 . . ? C28 C27 H27A 119.1 . . ? O3 C28 C29 117.6(5) . . ? O3 C28 C27 124.3(5) . . ? C29 C28 C27 118.1(5) . . ? C24 C29 C28 121.6(5) . . ? C24 C29 H29A 119.2 . . ? C28 C29 H29A 119.2 . . ? O3 C30 H30A 109.5 . . ? O3 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O3 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O4 C31 C32 109.0(4) . . ? O4 C31 C23 112.1(4) . . ? C32 C31 C23 108.7(4) . . ? O4 C31 H31A 109.0 . . ? C32 C31 H31A 109.0 . . ? C23 C31 H31A 109.0 . . ? N4 C32 C31 113.0(4) . . ? N4 C32 C33 107.3(4) . . ? C31 C32 C33 115.6(5) . . ? N4 C32 H32A 106.9 . . ? C31 C32 H32A 106.9 . . ? C33 C32 H32A 106.9 . . ? C34 C33 C32 107.2(5) . . ? C34 C33 H33A 110.3 . . ? C32 C33 H33A 110.3 . . ? C34 C33 H33B 110.3 . . ? C32 C33 H33B 110.3 . . ? H33A C33 H33B 108.5 . . ? C35 C34 C38 109.4(6) . . ? C35 C34 C33 107.1(6) . . ? C38 C34 C33 110.7(5) . . ? C35 C34 H34A 109.9 . . ? C38 C34 H34A 109.9 . . ? C33 C34 H34A 109.9 . . ? C36 C35 C34 109.1(5) . . ? C36 C35 H35A 109.9 . . ? C34 C35 H35A 109.9 . . ? C36 C35 H35B 109.9 . . ? C34 C35 H35B 109.9 . . ? H35A C35 H35B 108.3 . . ? C35 C36 N4 107.6(5) . . ? C35 C36 H36A 110.2 . . ? N4 C36 H36A 110.2 . . ? C35 C36 H36B 110.2 . . ? N4 C36 H36B 110.2 . . ? H36A C36 H36B 108.5 . . ? N4 C37 C38 109.1(5) . . ? N4 C37 H37A 109.9 . . ? C38 C37 H37A 109.9 . . ? N4 C37 H37B 109.9 . . ? C38 C37 H37B 109.9 . . ? H37A C37 H37B 108.3 . . ? C39 C38 C34 111.4(5) . . ? C39 C38 C37 114.7(7) . . ? C34 C38 C37 107.6(5) . . ? C39 C38 H38A 107.6 . . ? C34 C38 H38A 107.6 . . ? C37 C38 H38A 107.6 . . ? C40 C39 C38 130.7(9) . . ? C40 C39 H39A 114.6 . . ? C38 C39 H39A 114.6 . . ? C39 C40 H40A 120.0 . . ? C39 C40 H40B 120.0 . . ? H40A C40 H40B 120.0 . . ? C1 N1 C5 122.9(6) . . ? C1 N1 H1B 118.6 . . ? C5 N1 H1B 118.6 . . ? C17 N2 C16 108.3(6) . . ? C17 N2 C12 106.9(4) . . ? C16 N2 C12 113.0(5) . . ? C17 N2 H2 111.4 . . ? C16 N2 H2 109.5 . . ? C12 N2 H2 107.8 . . ? C21 N3 C25 122.3(5) . . ? C21 N3 H3A 118.9 . . ? C25 N3 H3A 118.9 . . ? C37 N4 C32 107.3(5) . . ? C37 N4 C36 109.0(5) . . ? C32 N4 C36 112.2(5) . . ? C37 N4 H4 121.2 . . ? C32 N4 H4 114.9 . . ? C36 N4 H4 91.1 . . ? C8 O1 C10 118.7(5) . . ? C11 O2 H2B 109.5 . . ? C28 O3 C30 119.6(5) . . ? C31 O4 H4A 109.5 . . ? H1WB O1W H1WC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.075 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.095