# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- Zhang.CIF' #==================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; 'Zhang, Xian-Ming' School of Chemistry & Material Science Shanxi Normal University Linfen 041004 Shanxi Province P. R. China ; _publ_contact_author_phone 86-357-2051402 _publ_contact_author_fax 86-357-2051402 _publ_contact_author_email zhangxm@dns.sxnu.edu.cn _publ_requested_coeditor_name ? _publ_contact_letter ; Dear Sir or Madam: Please consider this CIF as a supplmentary data for a manuscript submitted to Dalton Trans. Xian-Ming Zhang ; #================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Three novel Bi(III) complexes with in situ generated ligands Unusual aerobic oxidation of cyclohexanedione to dihydroxy benzoquinone ; loop_ _publ_author_name _publ_author_address 'Hui Gao' ; School of Chemistry & Material Science Shanxi Normal University Linfen 041004 Shanxi Province P. R. China ; 'Xian-Ming Zhang' ; School of Chemistry & Material Science Shanxi Normal University Linfen 041004 Shanxi Province P. R. China ; _publ_contact_author_name 'Zhang, Xian-Ming' #====================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 805102' #TrackingRef '- Zhang.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H5 Bi O16' _chemical_formula_weight 662.18 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' O O 0.0106 0.0060 '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 tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 9.8323(3) _cell_length_b 9.8323(3) _cell_length_c 28.2700(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2732.98(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3441 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 26.7 _exptl_crystal_description octahedron _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 6.514 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.3283 _exptl_absorpt_correction_T_max 0.6959 _exptl_absorpt_process_details 'SADABS, Sheldrick 1997' _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_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time no _diffrn_standards_decay_% no _diffrn_reflns_number 6783 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.97 _reflns_number_total 1488 _reflns_number_gt 1253 _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. The hydrogen atoms of carboxylic groups are not included in the refinement. The DMF molecules filled in channels can not be found in Fourer map and thus are not included in the refinement. ; _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^)+(0.1210P)^2^+4.7698P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1488 _refine_ls_number_parameters 94 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1628 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.004 _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 0.5000 0.2500 -0.1250 0.0359(3) Uani 1 4 d S . . C1 C 0.5740(9) 0.4020(9) -0.0284(3) 0.0405(18) Uani 1 1 d . . . C2 C 0.4607(9) 0.4915(9) -0.0494(3) 0.0389(17) Uani 1 1 d . . . C3 C 0.3942(9) 0.5862(9) -0.0213(3) 0.0423(18) Uani 1 1 d . . . C4 C 0.2809(13) 0.6705(12) -0.0418(4) 0.069(3) Uani 1 1 d . . . O1 O 0.6330(6) 0.3215(7) -0.05575(19) 0.0472(15) Uani 1 1 d . . . O2 O 0.4362(8) 0.4726(7) -0.0917(2) 0.0597(18) Uani 1 1 d . . . O3 O 0.3057(16) 0.761(2) -0.0670(10) 0.121(13) Uani 0.63(3) 1 d PU A 1 O3' O 0.270(5) 0.670(5) -0.0855(11) 0.130(17) Uani 0.37(3) 1 d PU A 2 O4 O 0.1606(16) 0.646(2) -0.0305(10) 0.146(12) Uani 0.63(3) 1 d PU A 1 O4' O 0.249(4) 0.773(3) -0.0237(9) 0.108(17) Uani 0.37(3) 1 d PU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0434(3) 0.0434(3) 0.0211(4) 0.000 0.000 0.000 C1 0.045(4) 0.043(4) 0.033(4) -0.005(3) -0.005(3) 0.002(3) C2 0.045(4) 0.046(4) 0.026(4) -0.003(3) -0.006(3) 0.002(3) C3 0.044(4) 0.047(4) 0.036(4) -0.005(4) -0.010(3) 0.011(4) C4 0.083(8) 0.065(7) 0.059(6) -0.020(5) -0.035(6) 0.024(6) O1 0.043(3) 0.064(4) 0.035(3) -0.015(3) -0.006(2) 0.014(3) O2 0.085(5) 0.065(4) 0.029(3) -0.002(3) -0.007(3) 0.019(4) O3 0.073(10) 0.117(17) 0.17(3) 0.106(19) -0.046(12) -0.027(10) O3' 0.17(4) 0.14(3) 0.08(2) -0.03(2) -0.05(2) 0.00(3) O4 0.043(9) 0.146(19) 0.25(3) 0.009(17) -0.056(12) 0.005(9) O4' 0.15(3) 0.11(2) 0.059(15) -0.029(15) -0.035(17) 0.11(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 Bi1 O1 2.457(6) . ? Bi1 O1 2.457(6) 11_665 ? Bi1 O1 2.457(6) 16_655 ? Bi1 O1 2.457(6) 6_554 ? Bi1 O2 2.463(7) 16_655 ? Bi1 O2 2.463(7) . ? Bi1 O2 2.463(7) 6_554 ? Bi1 O2 2.463(7) 11_665 ? C1 O1 1.249(10) . ? C1 C3 1.445(11) 9_665 ? C1 C2 1.538(12) . ? C2 O2 1.234(10) . ? C2 C3 1.387(12) . ? C3 C1 1.445(11) 9_665 ? C3 C4 1.505(12) . ? C4 O3 1.163(18) . ? C4 O4' 1.17(2) . ? C4 O3' 1.24(3) . ? C4 O4 1.25(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 O1 Bi1 O1 129.41(19) . 11_665 ? O1 Bi1 O1 129.41(19) . 16_655 ? O1 Bi1 O1 74.4(3) 11_665 16_655 ? O1 Bi1 O1 74.4(3) . 6_554 ? O1 Bi1 O1 129.41(19) 11_665 6_554 ? O1 Bi1 O1 129.41(19) 16_655 6_554 ? O1 Bi1 O2 148.2(2) . 16_655 ? O1 Bi1 O2 79.3(2) 11_665 16_655 ? O1 Bi1 O2 65.0(2) 16_655 16_655 ? O1 Bi1 O2 76.05(19) 6_554 16_655 ? O1 Bi1 O2 65.0(2) . . ? O1 Bi1 O2 148.2(2) 11_665 . ? O1 Bi1 O2 76.05(19) 16_655 . ? O1 Bi1 O2 79.3(2) 6_554 . ? O2 Bi1 O2 98.40(10) 16_655 . ? O1 Bi1 O2 79.3(2) . 6_554 ? O1 Bi1 O2 76.05(19) 11_665 6_554 ? O1 Bi1 O2 148.2(2) 16_655 6_554 ? O1 Bi1 O2 65.0(2) 6_554 6_554 ? O2 Bi1 O2 98.40(10) 16_655 6_554 ? O2 Bi1 O2 135.1(3) . 6_554 ? O1 Bi1 O2 76.05(19) . 11_665 ? O1 Bi1 O2 65.0(2) 11_665 11_665 ? O1 Bi1 O2 79.3(2) 16_655 11_665 ? O1 Bi1 O2 148.2(2) 6_554 11_665 ? O2 Bi1 O2 135.1(3) 16_655 11_665 ? O2 Bi1 O2 98.40(10) . 11_665 ? O2 Bi1 O2 98.40(10) 6_554 11_665 ? O1 C1 C3 123.6(8) . 9_665 ? O1 C1 C2 117.4(7) . . ? C3 C1 C2 119.1(7) 9_665 . ? O2 C2 C3 124.3(8) . . ? O2 C2 C1 115.4(8) . . ? C3 C2 C1 120.3(7) . . ? C2 C3 C1 120.5(7) . 9_665 ? C2 C3 C4 120.0(8) . . ? C1 C3 C4 119.3(8) 9_665 . ? O3 C4 O4' 71(2) . . ? O3 C4 O3' 54(2) . . ? O4' C4 O3' 115(2) . . ? O3 C4 O4 120.1(16) . . ? O4' C4 O4 78(2) . . ? O3' C4 O4 100(2) . . ? O3 C4 C3 120.0(15) . . ? O4' C4 C3 120.1(14) . . ? O3' C4 C3 116(2) . . ? O4 C4 C3 119.9(14) . . ? C1 O1 Bi1 115.3(5) . . ? C2 O2 Bi1 117.0(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.407 _refine_diff_density_min -0.915 _refine_diff_density_rms 0.294 #====================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 805103' #TrackingRef '- Zhang.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34 Bi2 N4 O20' _chemical_formula_weight 1140.53 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' Bi Bi -4.1077 10.2566 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6935(6) _cell_length_b 10.0302(6) _cell_length_c 11.5844(7) _cell_angle_alpha 65.9780(10) _cell_angle_beta 66.7680(10) _cell_angle_gamma 63.3430(10) _cell_volume 887.93(9) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3035 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.6 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 9.984 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.2400 _exptl_absorpt_correction_T_max 0.5022 _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_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% no _diffrn_reflns_number 4771 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3748 _reflns_number_gt 3440 _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^)+(0.0349P)^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_number_reflns 3748 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0668 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Bi1 Bi 0.27473(2) 0.38890(2) 0.265975(18) 0.02360(7) Uani 1 1 d . . . O1 O 0.1148(5) 0.5874(4) 0.1238(4) 0.0374(9) Uani 1 1 d . . . O2 O -0.1160(4) 0.7010(4) -0.2071(4) 0.0324(8) Uani 1 1 d . . . O3 O 0.1486(6) 0.8328(6) -0.1375(6) 0.0653(15) Uani 1 1 d . . . O4 O -0.1157(6) 0.9282(5) -0.1044(6) 0.0566(13) Uani 1 1 d . . . O5 O -0.0709(5) 0.6800(5) 0.5286(4) 0.0432(10) Uani 1 1 d . . . O6 O 0.1236(5) 0.5940(4) 0.3661(4) 0.0336(9) Uani 1 1 d . . . O7 O 0.4289(5) 0.3477(5) 0.0501(4) 0.0402(10) Uani 1 1 d . . . O8 O 0.5816(5) 0.4381(5) -0.1418(4) 0.0368(9) Uani 1 1 d . . . O9 O 0.4494(6) 0.3385(6) 0.4004(5) 0.0575(13) Uani 1 1 d . . . O10 O 0.4301(5) 0.0968(5) 0.3091(5) 0.0479(11) Uani 1 1 d . . . N1 N 0.6927(6) 0.2352(7) 0.4370(6) 0.0521(14) Uani 1 1 d . . . N2 N 0.5634(6) -0.1020(6) 0.2175(6) 0.0468(13) Uani 1 1 d . . . C1 C 0.0638(6) 0.5521(6) 0.0597(5) 0.0269(11) Uani 1 1 d . . . C2 C 0.0073(6) 0.6575(6) -0.0508(5) 0.0280(11) Uani 1 1 d . . . C3 C -0.0609(6) 0.6133(6) -0.1095(5) 0.0253(10) Uani 1 1 d . . . C4 C 0.0243(7) 0.8133(6) -0.1025(6) 0.0335(12) Uani 1 1 d . . . C5 C -0.1163(11) 1.0894(9) -0.1547(10) 0.081(3) Uani 1 1 d . . . H5A H -0.2241 1.1604 -0.1509 0.121 Uiso 1 1 calc R . . H5B H -0.0529 1.1073 -0.2437 0.121 Uiso 1 1 calc R . . H5C H -0.0724 1.1052 -0.1021 0.121 Uiso 1 1 calc R . . C6 C 0.0148(6) 0.5798(6) 0.4697(5) 0.0265(11) Uani 1 1 d . . . C7 C 0.5042(6) 0.4369(6) -0.0259(5) 0.0281(11) Uani 1 1 d . . . C8 C 0.5728(8) 0.2271(9) 0.4199(7) 0.0528(17) Uani 1 1 d . . . H8A H 0.5798 0.1305 0.4225 0.063 Uiso 1 1 calc R . . C9 C 0.6960(11) 0.3861(14) 0.4215(14) 0.121(5) Uani 1 1 d . . . H9A H 0.5972 0.4658 0.4059 0.182 Uiso 1 1 calc R . . H9B H 0.7832 0.4071 0.3488 0.182 Uiso 1 1 calc R . . H9C H 0.7099 0.3843 0.4998 0.182 Uiso 1 1 calc R . . C10 C 0.8331(9) 0.1016(12) 0.4617(10) 0.096(3) Uani 1 1 d . . . H10A H 0.8177 0.0096 0.4702 0.144 Uiso 1 1 calc R . . H10B H 0.8507 0.0919 0.5412 0.144 Uiso 1 1 calc R . . H10C H 0.9243 0.1144 0.3902 0.144 Uiso 1 1 calc R . . C11 C 0.4421(8) 0.0185(8) 0.2428(6) 0.0443(15) Uani 1 1 d . . . H11A H 0.3567 0.0495 0.2089 0.053 Uiso 1 1 calc R . . C12 C 0.5655(10) -0.1892(10) 0.1417(10) 0.076(3) Uani 1 1 d . . . H12A H 0.4657 -0.1442 0.1189 0.114 Uiso 1 1 calc R . . H12B H 0.5807 -0.2954 0.1930 0.114 Uiso 1 1 calc R . . H12C H 0.6513 -0.1855 0.0634 0.114 Uiso 1 1 calc R . . C13 C 0.7056(9) -0.1535(10) 0.2620(9) 0.072(2) Uani 1 1 d . . . H13A H 0.6890 -0.0871 0.3104 0.107 Uiso 1 1 calc R . . H13B H 0.7961 -0.1487 0.1876 0.107 Uiso 1 1 calc R . . H13C H 0.7250 -0.2585 0.3171 0.107 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 Bi1 0.02573(11) 0.02634(11) 0.02032(11) -0.00790(8) -0.00428(7) -0.01050(8) O1 0.051(2) 0.028(2) 0.047(3) -0.0094(18) -0.030(2) -0.0114(17) O2 0.043(2) 0.030(2) 0.030(2) -0.0009(16) -0.0197(18) -0.0159(17) O3 0.055(3) 0.046(3) 0.100(4) -0.004(3) -0.027(3) -0.031(2) O4 0.058(3) 0.025(2) 0.090(4) -0.008(2) -0.030(3) -0.015(2) O5 0.050(2) 0.039(2) 0.036(2) -0.0184(19) 0.009(2) -0.021(2) O6 0.046(2) 0.026(2) 0.029(2) -0.0085(16) 0.0006(17) -0.0202(17) O7 0.055(2) 0.042(2) 0.030(2) -0.0181(19) 0.0079(19) -0.032(2) O8 0.048(2) 0.044(2) 0.028(2) -0.0201(18) 0.0085(18) -0.0306(19) O9 0.059(3) 0.063(3) 0.067(3) -0.024(3) -0.042(3) -0.008(2) O10 0.060(3) 0.037(2) 0.048(3) -0.016(2) -0.021(2) -0.008(2) N1 0.038(3) 0.072(4) 0.048(3) -0.018(3) -0.017(3) -0.015(3) N2 0.048(3) 0.043(3) 0.058(4) -0.026(3) -0.014(3) -0.013(2) C1 0.028(3) 0.025(3) 0.030(3) -0.008(2) -0.014(2) -0.004(2) C2 0.032(3) 0.025(3) 0.032(3) -0.009(2) -0.011(2) -0.010(2) C3 0.025(2) 0.026(3) 0.026(3) -0.007(2) -0.009(2) -0.007(2) C4 0.043(3) 0.028(3) 0.038(3) -0.003(2) -0.020(3) -0.016(2) C5 0.092(6) 0.038(4) 0.126(8) -0.016(5) -0.033(6) -0.036(4) C6 0.033(3) 0.025(3) 0.025(3) -0.005(2) -0.012(2) -0.011(2) C7 0.031(3) 0.031(3) 0.031(3) -0.016(2) -0.003(2) -0.015(2) C8 0.051(4) 0.054(4) 0.062(5) -0.015(4) -0.029(4) -0.014(3) C9 0.065(6) 0.131(10) 0.216(15) -0.096(10) -0.030(8) -0.037(6) C10 0.046(5) 0.129(9) 0.077(7) -0.010(6) -0.034(5) -0.002(5) C11 0.047(4) 0.047(4) 0.044(4) -0.014(3) -0.016(3) -0.016(3) C12 0.074(5) 0.074(6) 0.104(7) -0.061(5) -0.021(5) -0.015(4) C13 0.047(4) 0.079(6) 0.090(7) -0.045(5) -0.012(4) -0.008(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 Bi1 O8 2.361(4) 2_665 ? Bi1 O6 2.371(3) . ? Bi1 O1 2.378(4) . ? Bi1 O7 2.449(4) . ? Bi1 O9 2.493(4) . ? Bi1 O5 2.494(4) 2_566 ? Bi1 O2 2.494(4) 2_565 ? Bi1 O10 2.558(4) . ? O1 C1 1.258(6) . ? O2 C3 1.258(6) . ? O2 Bi1 2.494(4) 2_565 ? O3 C4 1.190(7) . ? O4 C4 1.330(7) . ? O4 C5 1.476(8) . ? O5 C6 1.236(6) . ? O5 Bi1 2.494(4) 2_566 ? O6 C6 1.252(6) . ? O7 C7 1.243(6) . ? O8 C7 1.251(6) . ? O8 Bi1 2.361(4) 2_665 ? O9 C8 1.240(8) . ? O10 C11 1.248(7) . ? N1 C8 1.295(8) . ? N1 C10 1.445(9) . ? N1 C9 1.463(11) . ? N2 C11 1.293(8) . ? N2 C12 1.460(8) . ? N2 C13 1.461(9) . ? C1 C2 1.410(7) . ? C1 C3 1.528(7) 2_565 ? C2 C3 1.400(7) . ? C2 C4 1.490(7) . ? C3 C1 1.528(7) 2_565 ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C6 1.574(10) 2_566 ? C7 C7 1.568(9) 2_665 ? C8 H8A 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 O8 Bi1 O6 78.79(12) 2_665 . ? O8 Bi1 O1 76.11(14) 2_665 . ? O6 Bi1 O1 74.35(13) . . ? O8 Bi1 O7 68.49(12) 2_665 . ? O6 Bi1 O7 140.03(13) . . ? O1 Bi1 O7 75.98(15) . . ? O8 Bi1 O9 74.90(16) 2_665 . ? O6 Bi1 O9 79.09(15) . . ? O1 Bi1 O9 143.77(15) . . ? O7 Bi1 O9 112.20(16) . . ? O8 Bi1 O5 145.08(12) 2_665 2_566 ? O6 Bi1 O5 67.61(12) . 2_566 ? O1 Bi1 O5 102.62(15) . 2_566 ? O7 Bi1 O5 145.95(13) . 2_566 ? O9 Bi1 O5 89.25(17) . 2_566 ? O8 Bi1 O2 132.05(13) 2_665 2_565 ? O6 Bi1 O2 115.28(13) . 2_565 ? O1 Bi1 O2 65.77(12) . 2_565 ? O7 Bi1 O2 74.74(13) . 2_565 ? O9 Bi1 O2 149.88(15) . 2_565 ? O5 Bi1 O2 73.93(13) 2_566 2_565 ? O8 Bi1 O10 118.42(15) 2_665 . ? O6 Bi1 O10 143.93(14) . . ? O1 Bi1 O10 138.03(13) . . ? O7 Bi1 O10 74.49(14) . . ? O9 Bi1 O10 76.01(15) . . ? O5 Bi1 O10 86.29(14) 2_566 . ? O2 Bi1 O10 78.08(13) 2_565 . ? C1 O1 Bi1 120.1(3) . . ? C3 O2 Bi1 116.7(3) . 2_565 ? C4 O4 C5 118.0(5) . . ? C6 O5 Bi1 117.2(3) . 2_566 ? C6 O6 Bi1 120.9(3) . . ? C7 O7 Bi1 117.1(3) . . ? C7 O8 Bi1 119.8(3) . 2_665 ? C8 O9 Bi1 129.2(4) . . ? C11 O10 Bi1 122.8(4) . . ? C8 N1 C10 123.0(7) . . ? C8 N1 C9 120.1(7) . . ? C10 N1 C9 116.7(7) . . ? C11 N2 C12 121.8(6) . . ? C11 N2 C13 120.6(6) . . ? C12 N2 C13 117.7(6) . . ? O1 C1 C2 123.3(5) . . ? O1 C1 C3 116.6(5) . 2_565 ? C2 C1 C3 120.1(4) . 2_565 ? C3 C2 C1 119.7(5) . . ? C3 C2 C4 121.9(5) . . ? C1 C2 C4 118.3(5) . . ? O2 C3 C2 123.7(5) . . ? O2 C3 C1 116.2(4) . 2_565 ? C2 C3 C1 120.0(4) . 2_565 ? O3 C4 O4 123.9(5) . . ? O3 C4 C2 123.9(5) . . ? O4 C4 C2 112.2(5) . . ? O4 C5 H5A 109.5 . . ? O4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O5 C6 O6 125.8(5) . . ? O5 C6 C6 117.1(6) . 2_566 ? O6 C6 C6 117.1(5) . 2_566 ? O7 C7 O8 125.6(4) . . ? O7 C7 C7 117.3(6) . 2_665 ? O8 C7 C7 117.1(6) . 2_665 ? O9 C8 N1 125.0(7) . . ? O9 C8 H8A 117.5 . . ? N1 C8 H8A 117.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O10 C11 N2 125.5(6) . . ? O10 C11 H11A 117.3 . . ? N2 C11 H11A 117.3 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 1.228 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.152 #====================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 805104' #TrackingRef '- Zhang.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H38 Bi2 N4 O24' _chemical_formula_weight 1304.64 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1663(5) _cell_length_b 20.7198(10) _cell_length_c 11.3749(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.5330(10) _cell_angle_gamma 90.00 _cell_volume 2213.13(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3349 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 28.0 _exptl_crystal_description 'dark red' _exptl_crystal_colour block _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.958 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 8.031 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.2120 _exptl_absorpt_correction_T_max 0.5659 _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_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% no _diffrn_reflns_number 8865 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4661 _reflns_number_gt 3588 _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^)+(0.0358P)^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_number_reflns 4661 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0796 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 Bi1 Bi 0.46139(2) 0.903052(9) 0.187655(18) 0.03548(8) Uani 1 1 d . . . O1 O 0.4605(4) 0.8046(2) 0.3155(4) 0.0529(11) Uani 1 1 d . . . O2 O 0.6990(4) 0.85735(18) 0.3133(4) 0.0494(10) Uani 1 1 d . . . O3 O 0.9632(4) 0.68728(19) 0.5609(4) 0.0477(10) Uani 1 1 d . . . O4 O 0.7283(4) 0.63464(18) 0.5632(4) 0.0479(10) Uani 1 1 d . . . O5 O 1.0397(8) 0.8463(4) 0.5206(8) 0.160(4) Uani 1 1 d . . . O6 O 1.0185(5) 0.7880(3) 0.3550(5) 0.0828(15) Uani 1 1 d . . . O7 O 0.3643(6) 0.6597(4) 0.3369(6) 0.128(3) Uani 1 1 d . . . O8 O 0.4324(5) 0.6850(3) 0.5340(5) 0.0881(18) Uani 1 1 d . . . O9 O 0.5918(6) 1.0044(3) 0.3020(6) 0.0929(18) Uani 1 1 d . . . O10 O 0.2992(5) 0.9534(2) 0.2900(4) 0.0606(12) Uani 1 1 d . . . O11 O 0.3960(4) 1.06569(18) -0.0776(4) 0.0474(10) Uani 1 1 d . . . O12 O 0.3502(4) 0.98793(19) 0.0359(4) 0.0481(10) Uani 1 1 d . . . C1 C 0.5821(5) 0.7148(3) 0.4340(5) 0.0408(13) Uani 1 1 d . . . C2 C 0.5748(6) 0.7745(3) 0.3719(5) 0.0386(13) Uani 1 1 d . . . C3 C 0.7129(6) 0.8058(3) 0.3737(5) 0.0394(13) Uani 1 1 d . . . C4 C 0.8443(5) 0.7767(3) 0.4407(5) 0.0414(13) Uani 1 1 d . . . C5 C 0.8502(5) 0.7177(3) 0.5028(5) 0.0372(12) Uani 1 1 d . . . C6 C 0.7130(6) 0.6866(3) 0.5020(5) 0.0388(13) Uani 1 1 d . . . C7 C 0.4482(7) 0.6831(3) 0.4281(7) 0.0511(16) Uani 1 1 d . . . C8 C 0.9754(6) 0.8084(3) 0.4441(7) 0.0512(16) Uani 1 1 d . . . C9 C 0.3084(8) 0.6534(5) 0.5421(8) 0.101(3) Uani 1 1 d . . . H9A H 0.3100 0.6582 0.6266 0.151 Uiso 1 1 calc R . . H9B H 0.3100 0.6083 0.5229 0.151 Uiso 1 1 calc R . . H9C H 0.2233 0.6727 0.4821 0.151 Uiso 1 1 calc R . . C10 C 1.1452(8) 0.8167(5) 0.3509(9) 0.109(3) Uani 1 1 d . . . H10A H 1.1654 0.7981 0.2823 0.164 Uiso 1 1 calc R . . H10B H 1.2237 0.8089 0.4299 0.164 Uiso 1 1 calc R . . H10C H 1.1314 0.8624 0.3376 0.164 Uiso 1 1 calc R . . C11 C 0.6309(13) 1.1313(6) 0.2534(10) 0.138(4) Uani 1 1 d . . . H11A H 0.6737 1.0956 0.2275 0.206 Uiso 1 1 calc R . . H11B H 0.7039 1.1602 0.3053 0.206 Uiso 1 1 calc R . . H11C H 0.5682 1.1539 0.1794 0.206 Uiso 1 1 calc R . . C12 C 0.4821(12) 1.1547(5) 0.3725(10) 0.148(5) Uani 1 1 d . . . H12A H 0.4342 1.1334 0.4197 0.222 Uiso 1 1 calc R . . H12B H 0.4139 1.1780 0.3027 0.222 Uiso 1 1 calc R . . H12C H 0.5513 1.1843 0.4272 0.222 Uiso 1 1 calc R . . C13 C 0.5390(9) 1.0473(4) 0.3436(9) 0.100(3) Uani 1 1 d . . . C14 C 0.1500(10) 1.0184(7) 0.4115(8) 0.158(6) Uani 1 1 d . . . H14A H 0.2465 1.0036 0.4517 0.238 Uiso 1 1 calc R . . H14B H 0.0926 0.9985 0.4515 0.238 Uiso 1 1 calc R . . H14C H 0.1473 1.0645 0.4200 0.238 Uiso 1 1 calc R . . C15 C -0.0501(8) 1.0209(6) 0.2049(9) 0.123(4) Uani 1 1 d . . . H15A H -0.0764 1.0071 0.1183 0.185 Uiso 1 1 calc R . . H15B H -0.0575 1.0670 0.2073 0.185 Uiso 1 1 calc R . . H15C H -0.1126 1.0015 0.2401 0.185 Uiso 1 1 calc R . . C16 C 0.1746(8) 0.9719(3) 0.2311(7) 0.0672(19) Uani 1 1 d . . . H16A H 0.1349 0.9634 0.1442 0.081 Uiso 1 1 calc R . . C17 C 0.4266(5) 1.0157(3) -0.0119(5) 0.0397(13) Uani 1 1 d . . . N1 N 0.5518(7) 1.1080(3) 0.3247(5) 0.077(2) Uani 1 1 d . . . N2 N 0.0956(6) 1.0015(3) 0.2788(6) 0.0727(18) 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 Bi1 0.03300(13) 0.02947(12) 0.04489(13) 0.00118(9) 0.01594(9) 0.00047(9) O1 0.037(2) 0.056(3) 0.069(3) 0.021(2) 0.024(2) 0.008(2) O2 0.040(2) 0.042(2) 0.066(3) 0.019(2) 0.020(2) -0.0006(18) O3 0.030(2) 0.051(2) 0.065(3) 0.018(2) 0.0214(19) 0.0073(18) O4 0.039(2) 0.034(2) 0.071(3) 0.012(2) 0.022(2) -0.0015(17) O5 0.119(6) 0.194(8) 0.206(8) -0.110(7) 0.105(6) -0.103(6) O6 0.057(3) 0.091(4) 0.109(4) -0.018(3) 0.042(3) -0.028(3) O7 0.079(4) 0.205(8) 0.099(5) -0.040(5) 0.036(4) -0.082(5) O8 0.071(4) 0.121(5) 0.092(4) -0.022(3) 0.054(3) -0.050(3) O9 0.070(3) 0.074(4) 0.121(5) -0.044(3) 0.022(3) -0.008(3) O10 0.049(3) 0.068(3) 0.065(3) -0.012(2) 0.023(2) 0.005(2) O11 0.040(2) 0.039(2) 0.072(3) 0.018(2) 0.031(2) 0.0120(18) O12 0.033(2) 0.052(2) 0.065(3) 0.021(2) 0.024(2) 0.0076(18) C1 0.032(3) 0.042(3) 0.052(3) 0.010(3) 0.020(3) 0.000(2) C2 0.032(3) 0.045(3) 0.045(3) 0.004(3) 0.022(3) 0.003(2) C3 0.033(3) 0.041(3) 0.049(3) 0.004(3) 0.021(3) -0.003(2) C4 0.032(3) 0.035(3) 0.059(3) 0.010(3) 0.019(3) 0.003(2) C5 0.033(3) 0.033(3) 0.049(3) -0.001(2) 0.020(3) -0.001(2) C6 0.037(3) 0.036(3) 0.047(3) -0.002(2) 0.020(3) 0.000(2) C7 0.036(4) 0.046(4) 0.070(4) 0.005(3) 0.020(3) -0.002(3) C8 0.035(4) 0.045(4) 0.076(5) 0.003(3) 0.025(3) -0.001(3) C9 0.064(5) 0.145(9) 0.109(7) 0.010(6) 0.050(5) -0.040(5) C10 0.071(6) 0.148(9) 0.125(7) 0.001(7) 0.056(5) -0.051(6) C11 0.181(12) 0.114(9) 0.123(9) -0.004(8) 0.064(9) -0.019(8) C12 0.148(10) 0.113(9) 0.148(10) -0.054(8) 0.020(9) 0.043(8) C13 0.109(8) 0.054(5) 0.114(7) -0.033(5) 0.016(6) -0.015(5) C14 0.109(8) 0.274(17) 0.082(6) -0.069(8) 0.026(6) 0.048(9) C15 0.060(6) 0.139(10) 0.146(9) -0.003(7) 0.010(6) 0.037(5) C16 0.067(5) 0.078(5) 0.058(4) -0.009(4) 0.026(4) 0.000(4) C17 0.036(3) 0.034(3) 0.047(3) -0.001(3) 0.014(3) -0.001(2) N1 0.083(5) 0.069(5) 0.065(4) -0.018(3) 0.014(4) -0.005(3) N2 0.050(4) 0.091(5) 0.077(4) -0.012(4) 0.025(3) 0.018(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 O11 2.341(4) 3_675 ? Bi1 O3 2.367(4) 4_575 ? Bi1 O4 2.379(4) 4_575 ? Bi1 O12 2.419(4) . ? Bi1 O2 2.476(4) . ? Bi1 O1 2.507(4) . ? Bi1 O9 2.557(5) . ? Bi1 O10 2.576(4) . ? O1 C2 1.256(6) . ? O2 C3 1.248(6) . ? O3 C5 1.253(6) . ? O3 Bi1 2.367(4) 4_676 ? O4 C6 1.259(6) . ? O4 Bi1 2.379(4) 4_676 ? O5 C8 1.169(8) . ? O6 C8 1.319(8) . ? O6 C10 1.436(8) . ? O7 C7 1.166(7) . ? O8 C7 1.276(8) . ? O8 C9 1.456(8) . ? O9 C13 1.224(10) . ? O10 C16 1.245(7) . ? O11 C17 1.244(6) . ? O11 Bi1 2.341(4) 3_675 ? O12 C17 1.247(6) . ? C1 C6 1.386(7) . ? C1 C2 1.413(7) . ? C1 C7 1.490(8) . ? C2 C3 1.540(7) . ? C3 C4 1.396(7) . ? C4 C5 1.403(7) . ? C4 C8 1.472(8) . ? C5 C6 1.533(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N1 1.428(11) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N1 1.424(11) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N1 1.291(11) . ? C14 N2 1.438(9) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N2 1.452(8) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N2 1.284(8) . ? C16 H16A 0.9300 . ? C17 C17 1.555(11) 3_675 ? 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 O11 Bi1 O3 75.04(14) 3_675 4_575 ? O11 Bi1 O4 116.91(14) 3_675 4_575 ? O3 Bi1 O4 67.45(12) 4_575 4_575 ? O11 Bi1 O12 68.49(12) 3_675 . ? O3 Bi1 O12 104.52(14) 4_575 . ? O4 Bi1 O12 74.19(13) 4_575 . ? O11 Bi1 O2 75.35(13) 3_675 . ? O3 Bi1 O2 79.37(13) 4_575 . ? O4 Bi1 O2 138.34(13) 4_575 . ? O12 Bi1 O2 140.86(12) . . ? O11 Bi1 O1 132.52(13) 3_675 . ? O3 Bi1 O1 73.29(15) 4_575 . ? O4 Bi1 O1 81.59(13) 4_575 . ? O12 Bi1 O1 154.23(13) . . ? O2 Bi1 O1 64.76(12) . . ? O11 Bi1 O9 74.83(18) 3_675 . ? O3 Bi1 O9 146.69(17) 4_575 . ? O4 Bi1 O9 140.94(15) 4_575 . ? O12 Bi1 O9 77.02(17) . . ? O2 Bi1 O9 79.60(15) . . ? O1 Bi1 O9 119.32(17) . . ? O11 Bi1 O10 139.86(15) 3_675 . ? O3 Bi1 O10 138.73(13) 4_575 . ? O4 Bi1 O10 74.80(13) 4_575 . ? O12 Bi1 O10 79.79(14) . . ? O2 Bi1 O10 123.10(13) . . ? O1 Bi1 O10 85.55(14) . . ? O9 Bi1 O10 74.58(17) . . ? C2 O1 Bi1 119.4(3) . . ? C3 O2 Bi1 121.7(3) . . ? C5 O3 Bi1 119.9(3) . 4_676 ? C6 O4 Bi1 119.6(3) . 4_676 ? C8 O6 C10 117.4(6) . . ? C7 O8 C9 118.1(6) . . ? C13 O9 Bi1 125.1(6) . . ? C16 O10 Bi1 125.2(4) . . ? C17 O11 Bi1 119.2(3) . 3_675 ? C17 O12 Bi1 116.6(3) . . ? C6 C1 C2 120.2(5) . . ? C6 C1 C7 120.3(5) . . ? C2 C1 C7 119.4(5) . . ? O1 C2 C1 123.4(5) . . ? O1 C2 C3 117.3(5) . . ? C1 C2 C3 119.3(5) . . ? O2 C3 C4 123.6(5) . . ? O2 C3 C2 116.3(5) . . ? C4 C3 C2 120.1(5) . . ? C3 C4 C5 120.0(5) . . ? C3 C4 C8 119.2(5) . . ? C5 C4 C8 120.8(5) . . ? O3 C5 C4 123.8(5) . . ? O3 C5 C6 116.2(5) . . ? C4 C5 C6 120.0(5) . . ? O4 C6 C1 123.9(5) . . ? O4 C6 C5 115.8(5) . . ? C1 C6 C5 120.2(5) . . ? O7 C7 O8 122.7(7) . . ? O7 C7 C1 124.6(7) . . ? O8 C7 C1 112.7(6) . . ? O5 C8 O6 122.1(7) . . ? O5 C8 C4 124.2(7) . . ? O6 C8 C4 113.6(6) . . ? O8 C9 H9A 109.5 . . ? O8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O6 C10 H10A 109.5 . . ? O6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O9 C13 N1 123.8(11) . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O10 C16 N2 126.2(7) . . ? O10 C16 H16A 116.9 . . ? N2 C16 H16A 116.9 . . ? O11 C17 O12 126.3(5) . . ? O11 C17 C17 117.1(6) . 3_675 ? O12 C17 C17 116.5(6) . 3_675 ? C13 N1 C12 120.1(10) . . ? C13 N1 C11 122.6(9) . . ? C12 N1 C11 117.2(9) . . ? C16 N2 C14 120.6(6) . . ? C16 N2 C15 123.5(7) . . ? C14 N2 C15 115.9(7) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 1.938 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.122 #======================================