# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jian-Wen Cheng ' _publ_contact_author_email jwcheng@zjnu.cn _publ_author_name 'Jian-Wen Cheng' #===end data_2 _database_code_depnum_ccdc_archive 'CCDC 857787' #TrackingRef '- supporting information 2-R1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Bi4 N4 O24' _chemical_formula_weight 1636.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6283(2) _cell_length_b 13.6543(3) _cell_length_c 14.4484(5) _cell_angle_alpha 112.633(2) _cell_angle_beta 101.662(2) _cell_angle_gamma 105.5220(10) _cell_volume 1751.53(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7074 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 27.53 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.103 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 20.142 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0856 _exptl_absorpt_correction_T_max 0.4325 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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-II area-detector diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 26923 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7914 _reflns_number_gt 5896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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 maximum peaks is 4.18 (0.91 from Bi3). ; _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^)+(0.0322P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7914 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.20426(3) -0.25187(2) -0.35431(2) 0.01917(8) Uani 1 1 d . . . Bi2 Bi 0.34284(3) 0.12042(2) -0.24174(2) 0.01864(8) Uani 1 1 d . . . Bi3 Bi 0.50317(3) 0.16401(2) 0.03035(2) 0.01829(8) Uani 1 1 d . . . Bi4 Bi 0.62816(3) 0.52851(2) 0.13168(2) 0.01846(7) Uani 1 1 d . . . C1 C -0.1024(7) -0.4172(6) -0.3888(6) 0.0236(17) Uani 1 1 d . . . C2 C -0.2412(8) -0.4559(7) -0.3991(7) 0.033(2) Uani 1 1 d . . . H2A H -0.2852 -0.5265 -0.4024 0.039 Uiso 1 1 calc R . . C3 C -0.3121(8) -0.3856(7) -0.4044(7) 0.035(2) Uani 1 1 d . . . H3A H -0.4049 -0.4083 -0.4094 0.042 Uiso 1 1 calc R . . C4 C -0.2472(8) -0.2821(6) -0.4025(6) 0.0289(18) Uani 1 1 d . . . H4A H -0.2951 -0.2354 -0.4073 0.035 Uiso 1 1 calc R . . C5 C -0.1086(7) -0.2506(6) -0.3929(6) 0.0236(16) Uani 1 1 d . . . C6 C -0.0143(8) -0.4856(6) -0.3867(6) 0.0256(17) Uani 1 1 d . . . C7 C -0.0239(8) -0.1381(6) -0.3882(6) 0.0230(16) Uani 1 1 d . . . C8 C 0.5728(7) 0.0348(6) -0.3530(6) 0.0214(16) Uani 1 1 d . . . C9 C 0.6815(7) 0.0367(6) -0.3914(6) 0.0276(18) Uani 1 1 d . . . H9A H 0.7175 -0.0202 -0.4024 0.033 Uiso 1 1 calc R . . C10 C 0.7358(8) 0.1274(6) -0.4134(7) 0.033(2) Uani 1 1 d . . . H10A H 0.8109 0.1331 -0.4375 0.039 Uiso 1 1 calc R . . C11 C 0.6773(8) 0.2077(6) -0.3990(6) 0.0266(18) Uani 1 1 d . . . H11A H 0.7080 0.2651 -0.4182 0.032 Uiso 1 1 calc R . . C12 C 0.5722(7) 0.2030(6) -0.3558(6) 0.0245(17) Uani 1 1 d . . . C13 C 0.5038(7) -0.0607(6) -0.3287(6) 0.0242(17) Uani 1 1 d . . . C14 C 0.5095(8) 0.2907(6) -0.3306(6) 0.0277(18) Uani 1 1 d . . . C15 C 0.2423(7) 0.0580(6) 0.1037(6) 0.0187(15) Uani 1 1 d . . . C16 C 0.1188(7) 0.0397(6) 0.1260(6) 0.0224(17) Uani 1 1 d . . . H16A H 0.0783 -0.0245 0.1341 0.027 Uiso 1 1 calc R . . C17 C 0.0585(7) 0.1187(6) 0.1358(6) 0.0248(17) Uani 1 1 d . . . H17A H -0.0241 0.1081 0.1503 0.030 Uiso 1 1 calc R . . C18 C 0.1200(7) 0.2140(6) 0.1240(6) 0.0227(17) Uani 1 1 d . . . H18A H 0.0793 0.2674 0.1292 0.027 Uiso 1 1 calc R . . C19 C 0.2444(7) 0.2277(6) 0.1042(6) 0.0178(15) Uani 1 1 d . . . C20 C 0.3086(7) -0.0280(6) 0.0836(6) 0.0214(16) Uani 1 1 d . . . C21 C 0.3220(7) 0.3298(6) 0.0924(6) 0.0204(16) Uani 1 1 d . . . C22 C 0.9288(7) 0.5076(6) 0.1326(5) 0.0182(15) Uani 1 1 d . . . C23 C 1.0645(7) 0.5337(6) 0.1341(6) 0.0237(17) Uani 1 1 d . . . H23A H 1.1096 0.4844 0.1360 0.028 Uiso 1 1 calc R . . C24 C 1.1316(7) 0.6348(6) 0.1326(6) 0.0251(17) Uani 1 1 d . . . H24A H 1.2216 0.6525 0.1307 0.030 Uiso 1 1 calc R . . C25 C 1.0654(7) 0.7093(6) 0.1338(6) 0.0252(17) Uani 1 1 d . . . H25A H 1.1098 0.7777 0.1334 0.030 Uiso 1 1 calc R . . C26 C 0.9305(7) 0.6791(6) 0.1357(6) 0.0214(16) Uani 1 1 d . . . C27 C 0.8465(7) 0.4007(6) 0.1339(6) 0.0194(15) Uani 1 1 d . . . C28 C 0.8543(7) 0.7588(6) 0.1499(6) 0.0197(15) Uani 1 1 d . . . N1 N -0.0389(6) -0.3162(5) -0.3847(5) 0.0211(13) Uani 1 1 d . . . N2 N 0.5201(6) 0.1164(5) -0.3332(5) 0.0187(13) Uani 1 1 d . . . N3 N 0.3026(5) 0.1512(4) 0.0935(5) 0.0171(13) Uani 1 1 d . . . N4 N 0.8647(6) 0.5791(5) 0.1324(5) 0.0182(13) Uani 1 1 d . . . O1 O -0.0698(5) -0.5868(4) -0.4049(5) 0.0343(14) Uani 1 1 d . . . OW1 O 0.4193(5) -0.2798(4) -0.2728(5) 0.0325(13) Uani 1 1 d . . . O2 O 0.1151(5) -0.4370(4) -0.3712(4) 0.0266(12) Uani 1 1 d . . . OW2 O 0.4025(6) -0.4955(5) -0.3283(5) 0.0441(16) Uani 1 1 d . . . O3 O 0.1061(5) -0.1170(4) -0.3700(4) 0.0305(13) Uani 1 1 d . . . OW3 O 0.1001(7) 0.1213(5) -0.3872(5) 0.0567(18) Uani 1 1 d . . . O4 O -0.0839(5) -0.0780(4) -0.4044(5) 0.0337(14) Uani 1 1 d . . . OW4 O 0.8454(6) 0.6509(5) 0.3495(5) 0.0420(15) Uani 1 1 d . . . O5 O 0.5465(6) -0.1402(5) -0.3458(5) 0.0394(15) Uani 1 1 d . . . O6 O 0.4008(5) -0.0555(4) -0.2976(4) 0.0223(11) Uani 1 1 d . . . O7 O 0.4230(5) 0.2833(4) -0.2809(4) 0.0272(13) Uani 1 1 d . . . O8 O 0.5422(7) 0.3651(5) -0.3605(5) 0.0492(18) Uani 1 1 d . . . O9 O 0.2634(6) -0.1134(5) 0.0936(6) 0.057(2) Uani 1 1 d . . . O10 O 0.4181(5) -0.0048(4) 0.0555(4) 0.0216(11) Uani 1 1 d . . . O11 O 0.4358(5) 0.3317(4) 0.0736(4) 0.0221(11) Uani 1 1 d . . . O12 O 0.2763(6) 0.4057(4) 0.1042(5) 0.0380(15) Uani 1 1 d . . . O13 O 0.9025(5) 0.3347(4) 0.1425(4) 0.0303(13) Uani 1 1 d . . . O14 O 0.7170(5) 0.3838(4) 0.1236(4) 0.0253(12) Uani 1 1 d . . . O15 O 0.7263(5) 0.7158(4) 0.1453(4) 0.0210(11) Uani 1 1 d . . . O16 O 0.9112(6) 0.8570(4) 0.1676(5) 0.0393(15) Uani 1 1 d . . . O17 O 0.2268(5) -0.1753(4) -0.1956(4) 0.0271(12) Uani 1 1 d . . . O18 O 0.3259(5) 0.0592(4) -0.1143(4) 0.0185(11) Uani 1 1 d . . . O19 O 0.5253(5) 0.2226(4) -0.1062(4) 0.0196(11) Uani 1 1 d . . . O20 O 0.5869(5) 0.4518(4) -0.0375(4) 0.0189(11) 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 0.01855(15) 0.01442(14) 0.02295(17) 0.00827(12) 0.00730(13) 0.00452(11) Bi2 0.01929(15) 0.01572(14) 0.02249(16) 0.00948(12) 0.00865(12) 0.00700(11) Bi3 0.01576(14) 0.01510(14) 0.02630(17) 0.01082(12) 0.00891(12) 0.00616(11) Bi4 0.01860(15) 0.01505(14) 0.02478(17) 0.01073(12) 0.00993(13) 0.00675(11) C1 0.021(4) 0.016(4) 0.023(4) 0.006(3) 0.006(3) -0.001(3) C2 0.022(4) 0.031(5) 0.046(6) 0.020(4) 0.016(4) 0.006(4) C3 0.022(4) 0.040(5) 0.045(6) 0.021(4) 0.019(4) 0.008(4) C4 0.023(4) 0.032(4) 0.038(5) 0.018(4) 0.014(4) 0.014(4) C5 0.022(4) 0.028(4) 0.020(4) 0.011(3) 0.006(3) 0.009(3) C6 0.028(4) 0.022(4) 0.026(5) 0.013(3) 0.009(4) 0.004(3) C7 0.023(4) 0.024(4) 0.022(4) 0.010(3) 0.008(3) 0.010(3) C8 0.018(4) 0.026(4) 0.026(4) 0.015(3) 0.010(3) 0.009(3) C9 0.023(4) 0.031(4) 0.037(5) 0.019(4) 0.015(4) 0.013(3) C10 0.029(4) 0.035(5) 0.053(6) 0.029(4) 0.030(4) 0.017(4) C11 0.030(4) 0.021(4) 0.025(5) 0.011(3) 0.012(4) 0.003(3) C12 0.022(4) 0.028(4) 0.029(5) 0.016(4) 0.014(4) 0.009(3) C13 0.019(4) 0.019(4) 0.031(5) 0.012(3) 0.005(4) 0.004(3) C14 0.030(4) 0.020(4) 0.036(5) 0.014(4) 0.018(4) 0.008(3) C15 0.017(4) 0.017(4) 0.023(4) 0.010(3) 0.011(3) 0.005(3) C16 0.019(4) 0.016(4) 0.034(5) 0.015(3) 0.013(4) 0.004(3) C17 0.020(4) 0.023(4) 0.034(5) 0.011(4) 0.019(4) 0.007(3) C18 0.021(4) 0.022(4) 0.027(5) 0.010(3) 0.012(4) 0.010(3) C19 0.022(4) 0.018(4) 0.019(4) 0.010(3) 0.011(3) 0.012(3) C20 0.017(4) 0.024(4) 0.031(5) 0.017(3) 0.013(3) 0.009(3) C21 0.019(4) 0.016(4) 0.021(4) 0.005(3) 0.005(3) 0.005(3) C22 0.021(4) 0.020(4) 0.015(4) 0.007(3) 0.011(3) 0.007(3) C23 0.021(4) 0.023(4) 0.032(5) 0.013(4) 0.011(4) 0.014(3) C24 0.017(4) 0.029(4) 0.021(4) 0.006(3) 0.007(3) 0.004(3) C25 0.023(4) 0.020(4) 0.030(5) 0.011(3) 0.013(4) 0.003(3) C26 0.023(4) 0.018(4) 0.020(4) 0.010(3) 0.004(3) 0.004(3) C27 0.016(4) 0.022(4) 0.019(4) 0.008(3) 0.006(3) 0.008(3) C28 0.018(4) 0.019(4) 0.021(4) 0.011(3) 0.006(3) 0.005(3) N1 0.013(3) 0.022(3) 0.021(4) 0.009(3) 0.003(3) 0.001(3) N2 0.018(3) 0.018(3) 0.018(3) 0.008(3) 0.004(3) 0.006(3) N3 0.010(3) 0.015(3) 0.021(3) 0.006(3) 0.007(3) 0.001(2) N4 0.015(3) 0.015(3) 0.024(4) 0.010(3) 0.007(3) 0.004(2) O1 0.034(3) 0.018(3) 0.052(4) 0.019(3) 0.017(3) 0.005(2) OW1 0.025(3) 0.029(3) 0.051(4) 0.024(3) 0.012(3) 0.013(2) O2 0.022(3) 0.021(3) 0.031(3) 0.010(2) 0.005(2) 0.005(2) OW2 0.048(4) 0.028(3) 0.053(4) 0.015(3) 0.017(3) 0.016(3) O3 0.021(3) 0.025(3) 0.051(4) 0.025(3) 0.013(3) 0.006(2) OW3 0.063(5) 0.040(4) 0.055(5) 0.023(3) 0.005(4) 0.012(3) O4 0.026(3) 0.032(3) 0.063(4) 0.032(3) 0.021(3) 0.019(3) OW4 0.047(4) 0.039(4) 0.039(4) 0.016(3) 0.016(3) 0.017(3) O5 0.045(4) 0.033(3) 0.064(4) 0.030(3) 0.036(3) 0.027(3) O6 0.019(3) 0.022(3) 0.030(3) 0.012(2) 0.015(2) 0.009(2) O7 0.036(3) 0.021(3) 0.040(3) 0.021(3) 0.025(3) 0.014(2) O8 0.071(4) 0.042(4) 0.082(5) 0.048(4) 0.061(4) 0.035(3) O9 0.050(4) 0.049(4) 0.133(7) 0.069(4) 0.070(5) 0.036(3) O10 0.026(3) 0.021(3) 0.032(3) 0.020(2) 0.020(3) 0.013(2) O11 0.015(3) 0.021(3) 0.039(3) 0.017(2) 0.016(2) 0.009(2) O12 0.041(3) 0.033(3) 0.078(5) 0.041(3) 0.046(4) 0.029(3) O13 0.034(3) 0.034(3) 0.046(4) 0.029(3) 0.024(3) 0.025(3) O14 0.016(3) 0.017(3) 0.040(3) 0.013(2) 0.008(2) 0.004(2) O15 0.015(3) 0.019(3) 0.028(3) 0.011(2) 0.007(2) 0.006(2) O16 0.035(3) 0.026(3) 0.077(5) 0.035(3) 0.031(3) 0.016(3) O17 0.038(3) 0.018(3) 0.025(3) 0.008(2) 0.015(3) 0.008(2) O18 0.019(3) 0.013(2) 0.022(3) 0.008(2) 0.007(2) 0.004(2) O19 0.015(2) 0.016(2) 0.027(3) 0.010(2) 0.007(2) 0.004(2) O20 0.016(2) 0.015(2) 0.024(3) 0.007(2) 0.006(2) 0.007(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 O17 2.051(5) . ? Bi1 O2 2.345(5) . ? Bi1 N1 2.382(5) . ? Bi1 O3 2.405(5) . ? Bi1 OW1 2.545(5) . ? Bi1 O6 2.616(4) . ? Bi2 O19 2.111(5) . ? Bi2 O18 2.315(4) . ? Bi2 O7 2.478(4) . ? Bi2 O6 2.511(5) . ? Bi2 N2 2.511(5) . ? Bi2 O15 2.526(5) 2_665 ? Bi2 Bi3 3.6961(4) . ? Bi3 O18 2.151(5) . ? Bi3 O19 2.427(4) . ? Bi3 O10 2.435(4) . ? Bi3 O11 2.470(4) . ? Bi3 N3 2.473(5) . ? Bi3 O10 2.506(5) 2_655 ? Bi4 O20 2.148(5) . ? Bi4 O14 2.382(5) . ? Bi4 O15 2.401(4) . ? Bi4 N4 2.419(5) . ? Bi4 O20 2.550(5) 2_665 ? Bi4 O11 2.596(4) . ? C1 N1 1.335(8) . ? C1 C2 1.382(10) . ? C1 C6 1.493(10) . ? C2 C3 1.385(10) . ? C3 C4 1.383(9) . ? C4 C5 1.381(10) . ? C5 N1 1.329(9) . ? C5 C7 1.526(9) . ? C6 O1 1.244(8) . ? C6 O2 1.286(8) . ? C7 O4 1.227(8) . ? C7 O3 1.282(8) . ? C8 N2 1.339(8) . ? C8 C9 1.377(9) . ? C8 C13 1.518(9) . ? C9 C10 1.401(9) . ? C10 C11 1.368(10) . ? C11 C12 1.384(9) . ? C12 N2 1.354(8) . ? C12 C14 1.483(10) . ? C13 O5 1.244(8) . ? C13 O6 1.274(8) . ? C14 O8 1.245(8) . ? C14 O7 1.282(8) . ? C15 N3 1.342(8) . ? C15 C16 1.395(9) . ? C15 C20 1.491(9) . ? C16 C17 1.373(9) . ? C17 C18 1.381(9) . ? C18 C19 1.388(9) . ? C19 N3 1.325(8) . ? C19 C21 1.509(8) . ? C20 O9 1.212(7) . ? C20 O10 1.308(7) . ? C21 O12 1.228(8) . ? C21 O11 1.288(8) . ? C22 N4 1.333(8) . ? C22 C23 1.383(9) . ? C22 C27 1.497(9) . ? C23 C24 1.385(9) . ? C24 C25 1.380(10) . ? C25 C26 1.391(9) . ? C26 N4 1.335(8) . ? C26 C28 1.499(9) . ? C27 O13 1.235(8) . ? C27 O14 1.300(8) . ? C28 O16 1.212(7) . ? C28 O15 1.306(8) . ? O10 Bi3 2.506(5) 2_655 ? O15 Bi2 2.526(5) 2_665 ? O20 Bi4 2.550(5) 2_665 ? 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 O17 Bi1 O2 92.63(18) . . ? O17 Bi1 N1 85.2(2) . . ? O2 Bi1 N1 68.07(18) . . ? O17 Bi1 O3 86.66(19) . . ? O2 Bi1 O3 135.08(16) . . ? N1 Bi1 O3 67.11(17) . . ? O17 Bi1 OW1 79.2(2) . . ? O2 Bi1 OW1 76.35(16) . . ? N1 Bi1 OW1 140.27(17) . . ? O3 Bi1 OW1 146.43(16) . . ? O17 Bi1 O6 82.28(16) . . ? O2 Bi1 O6 154.91(17) . . ? N1 Bi1 O6 135.27(17) . . ? O3 Bi1 O6 69.41(15) . . ? OW1 Bi1 O6 78.56(15) . . ? O19 Bi2 O18 71.11(16) . . ? O19 Bi2 O7 82.43(17) . . ? O18 Bi2 O7 147.75(16) . . ? O19 Bi2 O6 94.38(16) . . ? O18 Bi2 O6 73.83(15) . . ? O7 Bi2 O6 127.67(15) . . ? O19 Bi2 N2 80.91(17) . . ? O18 Bi2 N2 126.30(17) . . ? O7 Bi2 N2 64.45(16) . . ? O6 Bi2 N2 63.49(15) . . ? O19 Bi2 O15 80.82(16) . 2_665 ? O18 Bi2 O15 90.41(15) . 2_665 ? O7 Bi2 O15 66.89(15) . 2_665 ? O6 Bi2 O15 164.22(15) . 2_665 ? N2 Bi2 O15 129.66(15) . 2_665 ? O19 Bi2 Bi3 38.42(11) . . ? O18 Bi2 Bi3 32.76(11) . . ? O7 Bi2 Bi3 118.10(13) . . ? O6 Bi2 Bi3 83.49(11) . . ? N2 Bi2 Bi3 108.52(13) . . ? O15 Bi2 Bi3 83.50(11) 2_665 . ? O18 Bi3 O19 68.26(15) . . ? O18 Bi3 O10 80.80(16) . . ? O19 Bi3 O10 142.33(16) . . ? O18 Bi3 O11 92.52(16) . . ? O19 Bi3 O11 73.82(15) . . ? O10 Bi3 O11 130.30(14) . . ? O18 Bi3 N3 76.28(17) . . ? O19 Bi3 N3 123.15(17) . . ? O10 Bi3 N3 65.85(16) . . ? O11 Bi3 N3 64.73(15) . . ? O18 Bi3 O10 81.44(17) . 2_655 ? O19 Bi3 O10 90.11(14) . 2_655 ? O10 Bi3 O10 63.67(17) . 2_655 ? O11 Bi3 O10 163.92(15) . 2_655 ? N3 Bi3 O10 127.19(15) . 2_655 ? O18 Bi3 Bi2 35.61(11) . . ? O19 Bi3 Bi2 32.71(11) . . ? O10 Bi3 Bi2 114.35(12) . . ? O11 Bi3 Bi2 80.01(12) . . ? N3 Bi3 Bi2 100.76(14) . . ? O10 Bi3 Bi2 86.58(11) 2_655 . ? O20 Bi4 O14 84.11(17) . . ? O20 Bi4 O15 90.09(16) . . ? O14 Bi4 O15 133.44(15) . . ? O20 Bi4 N4 80.82(18) . . ? O14 Bi4 N4 66.92(16) . . ? O15 Bi4 N4 66.55(16) . . ? O20 Bi4 O20 69.78(18) . 2_665 ? O14 Bi4 O20 139.59(16) . 2_665 ? O15 Bi4 O20 78.47(15) . 2_665 ? N4 Bi4 O20 133.87(16) . 2_665 ? O20 Bi4 O11 80.44(16) . . ? O14 Bi4 O11 66.87(15) . . ? O15 Bi4 O11 156.89(16) . . ? N4 Bi4 O11 131.42(16) . . ? O20 Bi4 O11 78.47(14) 2_665 . ? N1 C1 C2 121.5(7) . . ? N1 C1 C6 114.9(6) . . ? C2 C1 C6 123.5(6) . . ? C1 C2 C3 117.5(7) . . ? C4 C3 C2 121.1(7) . . ? C5 C4 C3 117.5(7) . . ? N1 C5 C4 121.6(6) . . ? N1 C5 C7 115.4(6) . . ? C4 C5 C7 123.0(7) . . ? O1 C6 O2 123.7(7) . . ? O1 C6 C1 119.1(6) . . ? O2 C6 C1 117.1(6) . . ? O4 C7 O3 125.8(7) . . ? O4 C7 C5 118.9(7) . . ? O3 C7 C5 115.3(6) . . ? N2 C8 C9 123.2(6) . . ? N2 C8 C13 114.5(6) . . ? C9 C8 C13 122.2(7) . . ? C8 C9 C10 117.7(7) . . ? C11 C10 C9 119.4(7) . . ? C10 C11 C12 119.7(6) . . ? N2 C12 C11 121.2(7) . . ? N2 C12 C14 115.4(6) . . ? C11 C12 C14 123.4(6) . . ? O5 C13 O6 125.2(6) . . ? O5 C13 C8 118.3(6) . . ? O6 C13 C8 116.4(6) . . ? O8 C14 O7 124.4(7) . . ? O8 C14 C12 118.1(6) . . ? O7 C14 C12 117.5(6) . . ? N3 C15 C16 121.2(6) . . ? N3 C15 C20 116.9(6) . . ? C16 C15 C20 121.8(6) . . ? C17 C16 C15 118.5(6) . . ? C16 C17 C18 120.2(6) . . ? C17 C18 C19 118.1(7) . . ? N3 C19 C18 122.1(6) . . ? N3 C19 C21 115.4(6) . . ? C18 C19 C21 122.4(6) . . ? O9 C20 O10 122.7(7) . . ? O9 C20 C15 121.5(6) . . ? O10 C20 C15 115.9(5) . . ? O12 C21 O11 124.8(6) . . ? O12 C21 C19 119.1(6) . . ? O11 C21 C19 116.1(6) . . ? N4 C22 C23 121.1(6) . . ? N4 C22 C27 115.9(6) . . ? C23 C22 C27 123.0(6) . . ? C22 C23 C24 118.5(7) . . ? C25 C24 C23 120.2(7) . . ? C24 C25 C26 118.1(6) . . ? N4 C26 C25 121.1(7) . . ? N4 C26 C28 115.8(6) . . ? C25 C26 C28 122.9(6) . . ? O13 C27 O14 124.7(6) . . ? O13 C27 C22 119.7(6) . . ? O14 C27 C22 115.7(6) . . ? O16 C28 O15 123.5(7) . . ? O16 C28 C26 121.1(6) . . ? O15 C28 C26 115.4(6) . . ? C5 N1 C1 120.8(6) . . ? C5 N1 Bi1 120.5(4) . . ? C1 N1 Bi1 118.7(5) . . ? C8 N2 C12 118.6(6) . . ? C8 N2 Bi2 121.4(4) . . ? C12 N2 Bi2 119.8(4) . . ? C19 N3 C15 119.9(5) . . ? C19 N3 Bi3 120.6(4) . . ? C15 N3 Bi3 119.0(4) . . ? C22 N4 C26 120.9(6) . . ? C22 N4 Bi4 119.2(4) . . ? C26 N4 Bi4 119.9(5) . . ? C6 O2 Bi1 120.8(4) . . ? C7 O3 Bi1 121.6(4) . . ? C13 O6 Bi2 122.6(4) . . ? C13 O6 Bi1 116.3(4) . . ? Bi2 O6 Bi1 118.01(17) . . ? C14 O7 Bi2 122.6(4) . . ? C20 O10 Bi3 122.2(4) . . ? C20 O10 Bi3 118.6(4) . 2_655 ? Bi3 O10 Bi3 116.33(17) . 2_655 ? C21 O11 Bi3 121.7(4) . . ? C21 O11 Bi4 118.8(4) . . ? Bi3 O11 Bi4 117.44(17) . . ? C27 O14 Bi4 121.6(4) . . ? C28 O15 Bi4 121.9(4) . . ? C28 O15 Bi2 108.3(4) . 2_665 ? Bi4 O15 Bi2 122.96(18) . 2_665 ? Bi3 O18 Bi2 111.63(17) . . ? Bi2 O19 Bi3 108.87(17) . . ? Bi4 O20 Bi4 110.22(18) . 2_665 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 4.178 _refine_diff_density_min -2.042 _refine_diff_density_rms 0.235 #===end data_3 _database_code_depnum_ccdc_archive 'CCDC 857788' #TrackingRef '- supporting information 2-R1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H30 Bi5 N5 O30 S0' _chemical_formula_weight 2045.54 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' S S 0.1246 0.1234 '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' '-x, -y, -z' _cell_length_a 10.6201(3) _cell_length_b 13.5967(3) _cell_length_c 16.3708(4) _cell_angle_alpha 81.091(2) _cell_angle_beta 72.977(2) _cell_angle_gamma 74.7310(10) _cell_volume 2172.79(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6678 _cell_measurement_theta_min 1.31 _cell_measurement_theta_max 27.61 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1860 _exptl_absorpt_coefficient_mu 20.296 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1002 _exptl_absorpt_correction_T_max 0.2361 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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-II area-detector diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 34690 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 27.61 _reflns_number_total 9994 _reflns_number_gt 7055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0547P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9994 _refine_ls_number_parameters 694 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.17125(3) -0.24543(2) 0.30550(2) 0.01872(9) Uani 1 1 d . . . Bi2 Bi 0.05932(5) 0.05631(4) 0.38934(3) 0.01694(12) Uani 0.85 1 d P . . Bi2' Bi 0.0690(3) 0.0673(2) 0.34772(19) 0.0172(6) Uani 0.15 1 d P . . Bi3 Bi 0.31051(3) 0.16087(2) 0.12042(2) 0.02228(10) Uani 1 1 d . . . Bi4 Bi 0.04642(11) 0.34370(8) 0.48114(7) 0.0172(2) Uani 0.40 1 d P . . Bi4' Bi 0.07026(7) 0.34727(5) 0.43917(5) 0.01822(17) Uani 0.60 1 d P . . Bi5 Bi 0.17545(4) 0.47144(2) 0.21167(2) 0.02343(10) Uani 1 1 d . . . C1 C 0.4764(8) -0.3942(6) 0.2926(5) 0.0210(19) Uani 1 1 d . . . C2 C 0.6086(9) -0.4267(6) 0.2923(6) 0.026(2) Uani 1 1 d . . . H2A H 0.6511 -0.4959 0.2930 0.032 Uiso 1 1 calc R . . C3 C 0.6789(9) -0.3526(7) 0.2910(6) 0.029(2) Uani 1 1 d . . . H3A H 0.7694 -0.3717 0.2917 0.035 Uiso 1 1 calc R . . C4 C 0.6125(9) -0.2504(7) 0.2884(5) 0.025(2) Uani 1 1 d . . . H4A H 0.6591 -0.1998 0.2841 0.030 Uiso 1 1 calc R . . C5 C 0.4773(9) -0.2244(6) 0.2925(5) 0.0184(18) Uani 1 1 d . . . C6 C 0.3923(9) -0.4671(7) 0.2866(6) 0.026(2) Uani 1 1 d . . . C7 C 0.3937(9) -0.1154(6) 0.2948(5) 0.0197(18) Uani 1 1 d . . . C8 C -0.2035(8) 0.0380(6) 0.3223(5) 0.0207(19) Uani 1 1 d . . . C9 C -0.3255(8) 0.0645(6) 0.3009(5) 0.0213(19) Uani 1 1 d . . . H9A H -0.3665 0.0142 0.2952 0.026 Uiso 1 1 calc R . . C10 C -0.3851(8) 0.1663(6) 0.2882(5) 0.0231(19) Uani 1 1 d . . . H10A H -0.4687 0.1857 0.2758 0.028 Uiso 1 1 calc R . . C11 C -0.3195(9) 0.2406(6) 0.2942(5) 0.023(2) Uani 1 1 d . . . H11A H -0.3558 0.3097 0.2825 0.028 Uiso 1 1 calc R . . C12 C -0.2014(8) 0.2093(6) 0.3174(5) 0.0173(18) Uani 1 1 d . . . C13 C -0.1267(9) -0.0702(6) 0.3337(5) 0.0218(19) Uani 1 1 d . . . C14 C -0.1284(8) 0.2837(6) 0.3333(5) 0.0181(18) Uani 1 1 d . . . C15 C 0.6172(9) 0.0187(6) 0.0861(5) 0.023(2) Uani 1 1 d . . . C16 C 0.7531(9) -0.0112(7) 0.0787(6) 0.032(2) Uani 1 1 d . . . H16A H 0.7975 -0.0800 0.0781 0.039 Uiso 1 1 calc R . . C17 C 0.8228(10) 0.0637(7) 0.0723(6) 0.034(2) Uani 1 1 d . . . H17A H 0.9156 0.0453 0.0663 0.041 Uiso 1 1 calc R . . C18 C 0.7562(9) 0.1643(7) 0.0746(6) 0.029(2) Uani 1 1 d . . . H18A H 0.8030 0.2149 0.0697 0.035 Uiso 1 1 calc R . . C19 C 0.6190(9) 0.1894(6) 0.0844(5) 0.023(2) Uani 1 1 d . . . C20 C 0.5276(9) -0.0523(6) 0.0896(5) 0.0224(19) Uani 1 1 d . . . C21 C 0.5339(10) 0.2987(7) 0.0912(5) 0.026(2) Uani 1 1 d . . . C22 C 0.3449(8) 0.1995(6) 0.4849(5) 0.0187(18) Uani 1 1 d . . . C23 C 0.4721(9) 0.1682(6) 0.4984(5) 0.023(2) Uani 1 1 d . . . H23A H 0.5130 0.0990 0.5046 0.027 Uiso 1 1 calc R . . C24 C 0.5373(9) 0.2417(6) 0.5025(5) 0.0228(19) Uani 1 1 d . . . H24A H 0.6243 0.2223 0.5098 0.027 Uiso 1 1 calc R . . C25 C 0.4740(8) 0.3443(6) 0.4958(5) 0.0190(18) Uani 1 1 d . . . H25A H 0.5170 0.3947 0.4983 0.023 Uiso 1 1 calc R . . C26 C 0.3434(8) 0.3694(6) 0.4851(5) 0.0171(18) Uani 1 1 d . . . C27 C 0.2698(9) 0.1263(6) 0.4728(6) 0.023(2) Uani 1 1 d . . . C28 C 0.2599(9) 0.4782(6) 0.4811(6) 0.0219(19) Uani 1 1 d . . . C29 C -0.0567(9) 0.4465(6) 0.1185(6) 0.024(2) Uani 1 1 d . . . C30 C -0.1668(10) 0.4710(6) 0.0831(6) 0.030(2) Uani 1 1 d . . . H30A H -0.2014 0.4201 0.0715 0.036 Uiso 1 1 calc R . . C31 C -0.2235(10) 0.5742(7) 0.0656(7) 0.037(2) Uani 1 1 d . . . H31A H -0.2994 0.5934 0.0443 0.044 Uiso 1 1 calc R . . C32 C -0.1658(10) 0.6481(7) 0.0801(6) 0.031(2) Uani 1 1 d . . . H32A H -0.1992 0.7170 0.0658 0.037 Uiso 1 1 calc R . . C33 C -0.0580(9) 0.6174(6) 0.1163(6) 0.025(2) Uani 1 1 d . . . C34 C 0.0172(9) 0.3376(6) 0.1367(6) 0.023(2) Uani 1 1 d . . . C35 C 0.0053(9) 0.6931(6) 0.1394(6) 0.027(2) Uani 1 1 d . . . N1 N 0.4105(7) -0.2966(5) 0.2951(4) 0.0155(14) Uani 1 1 d . . . N2 N -0.1449(7) 0.1104(5) 0.3319(4) 0.0196(16) Uani 1 1 d . . . N3 N 0.5520(7) 0.1174(5) 0.0919(4) 0.0196(16) Uani 1 1 d . . . N4 N 0.2816(7) 0.2974(5) 0.4806(4) 0.0156(15) Uani 1 1 d . . . N5 N -0.0039(7) 0.5183(5) 0.1347(4) 0.0185(15) Uani 1 1 d . . . OW1 O 0.3122(7) 0.1468(4) 0.2480(4) 0.0291(15) Uani 1 1 d . . . O1 O 0.4453(7) -0.5554(4) 0.2753(5) 0.044(2) Uani 1 1 d . . . O2 O 0.2651(6) -0.4266(4) 0.2918(4) 0.0211(13) Uani 1 1 d . . . OW2 O 0.1105(7) 0.0858(5) 0.1882(4) 0.0385(18) Uani 1 1 d . . . OW3 O 0.3597(8) -0.2375(5) 0.1219(5) 0.047(2) Uani 1 1 d . . . O3 O 0.2647(6) -0.1049(4) 0.3049(4) 0.0238(14) Uani 1 1 d . . . OW4 O 0.1151(8) -0.0968(5) 0.1447(5) 0.049(2) Uani 1 1 d . . . O4 O 0.4510(6) -0.0461(4) 0.2849(4) 0.0317(16) Uani 1 1 d . . . OW5 O 0.4045(8) 0.5545(5) 0.0925(5) 0.051(2) Uani 1 1 d . . . O5 O -0.1735(7) -0.1397(4) 0.3230(5) 0.0384(18) Uani 1 1 d . . . O6 O -0.0141(6) -0.0831(4) 0.3535(4) 0.0246(14) Uani 1 1 d . . . O7 O -0.0268(6) 0.2436(4) 0.3643(4) 0.0227(14) Uani 1 1 d . . . O8 O -0.1695(6) 0.3758(4) 0.3152(4) 0.0329(16) Uani 1 1 d . . . O9 O 0.5814(6) -0.1418(4) 0.0736(4) 0.0336(16) Uani 1 1 d . . . O10 O 0.4001(6) -0.0131(4) 0.1060(4) 0.0268(15) Uani 1 1 d . . . O11 O 0.4059(7) 0.3078(4) 0.1065(4) 0.0363(17) Uani 1 1 d . . . O12 O 0.5904(6) 0.3702(5) 0.0771(4) 0.0352(17) Uani 1 1 d . . . O13 O 0.3207(7) 0.0360(5) 0.4715(5) 0.048(2) Uani 1 1 d . . . O14 O 0.1511(6) 0.1669(4) 0.4603(4) 0.0272(15) Uani 1 1 d . . . O15 O 0.1390(6) 0.4889(4) 0.4748(4) 0.0290(15) Uani 1 1 d . . . O16 O 0.3120(6) 0.5488(4) 0.4841(4) 0.0298(15) Uani 1 1 d . . . O17 O -0.0235(7) 0.2672(5) 0.1204(5) 0.0412(18) Uani 1 1 d . . . O18 O 0.1175(6) 0.3259(4) 0.1674(4) 0.0203(13) Uani 1 1 d . . . O19 O 0.0944(7) 0.6552(4) 0.1810(4) 0.0285(15) Uani 1 1 d . . . O20 O -0.0334(8) 0.7844(4) 0.1168(5) 0.047(2) Uani 1 1 d . . . O21 O -0.0307(6) -0.3241(4) 0.3807(4) 0.0222(13) Uani 1 1 d . . . O22 O 0.1606(6) -0.2655(4) 0.4381(3) 0.0201(13) Uani 1 1 d . . . O23 O -0.1028(6) 0.0783(4) 0.5036(4) 0.0218(13) Uani 1 1 d . . . O24 O 0.2296(7) 0.3331(4) 0.3149(4) 0.0267(15) Uani 1 1 d . . . O25 O 0.0062(6) 0.4930(4) 0.3200(4) 0.0265(15) 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 0.02260(19) 0.01208(15) 0.02275(18) -0.00330(12) -0.00703(13) -0.00393(13) Bi2 0.0167(2) 0.0121(2) 0.0244(3) -0.0044(2) -0.0062(2) -0.00487(15) Bi2' 0.0193(13) 0.0108(11) 0.0255(16) -0.0025(13) -0.0101(14) -0.0051(9) Bi3 0.0278(2) 0.01522(16) 0.02566(19) -0.00592(13) -0.01003(15) -0.00246(13) Bi4 0.0165(5) 0.0106(4) 0.0271(6) -0.0039(5) -0.0076(5) -0.0040(3) Bi4' 0.0139(3) 0.0116(3) 0.0287(4) -0.0062(3) -0.0011(3) -0.0046(2) Bi5 0.0277(2) 0.01858(16) 0.0259(2) -0.00805(14) -0.00115(14) -0.01177(14) C1 0.017(5) 0.022(4) 0.022(5) -0.005(4) -0.001(4) -0.003(3) C2 0.021(5) 0.020(4) 0.033(5) -0.007(4) -0.012(4) 0.011(4) C3 0.019(5) 0.041(6) 0.030(5) -0.008(4) -0.006(4) -0.010(4) C4 0.021(5) 0.031(5) 0.028(5) 0.002(4) -0.015(4) -0.008(4) C5 0.025(5) 0.016(4) 0.017(4) -0.004(3) -0.007(4) -0.007(3) C6 0.025(5) 0.029(5) 0.026(5) -0.004(4) -0.010(4) -0.006(4) C7 0.023(5) 0.018(4) 0.024(5) -0.004(3) -0.011(4) -0.007(4) C8 0.019(5) 0.019(4) 0.024(5) -0.006(4) -0.002(4) -0.008(4) C9 0.020(5) 0.025(4) 0.024(5) -0.006(4) -0.008(4) -0.009(4) C10 0.012(4) 0.029(5) 0.028(5) 0.000(4) -0.007(4) -0.004(4) C11 0.029(5) 0.019(4) 0.019(5) 0.001(3) -0.006(4) -0.003(4) C12 0.019(4) 0.018(4) 0.018(4) 0.002(3) -0.005(3) -0.012(3) C13 0.020(5) 0.025(5) 0.025(5) -0.003(4) -0.009(4) -0.010(4) C14 0.016(4) 0.015(4) 0.026(5) -0.008(3) -0.005(4) -0.006(3) C15 0.027(5) 0.027(5) 0.016(4) -0.004(4) -0.007(4) -0.003(4) C16 0.027(6) 0.028(5) 0.040(6) -0.008(4) -0.016(5) 0.007(4) C17 0.021(5) 0.038(6) 0.043(6) -0.010(5) -0.008(4) -0.001(4) C18 0.024(5) 0.033(5) 0.032(5) -0.005(4) -0.008(4) -0.007(4) C19 0.025(5) 0.020(4) 0.023(5) -0.002(4) -0.007(4) -0.004(4) C20 0.027(5) 0.018(4) 0.025(5) -0.003(4) -0.013(4) -0.003(4) C21 0.029(5) 0.035(5) 0.018(5) -0.009(4) -0.009(4) -0.008(4) C22 0.018(4) 0.019(4) 0.020(4) -0.007(3) 0.000(3) -0.007(3) C23 0.023(5) 0.022(4) 0.025(5) -0.007(4) -0.011(4) 0.001(4) C24 0.016(4) 0.027(5) 0.029(5) -0.005(4) -0.008(4) -0.006(4) C25 0.018(4) 0.022(4) 0.025(5) -0.005(4) -0.012(4) -0.010(4) C26 0.022(5) 0.012(4) 0.024(5) -0.001(3) -0.009(4) -0.010(3) C27 0.024(5) 0.015(4) 0.031(5) 0.001(4) -0.011(4) -0.006(4) C28 0.021(5) 0.018(4) 0.029(5) -0.005(4) -0.006(4) -0.007(4) C29 0.022(5) 0.024(5) 0.031(5) -0.003(4) -0.009(4) -0.012(4) C30 0.041(6) 0.022(5) 0.040(6) 0.001(4) -0.027(5) -0.013(4) C31 0.033(6) 0.032(5) 0.052(7) -0.004(5) -0.025(5) -0.002(4) C32 0.034(6) 0.026(5) 0.035(6) 0.001(4) -0.017(5) -0.005(4) C33 0.023(5) 0.022(4) 0.027(5) -0.002(4) 0.000(4) -0.006(4) C34 0.026(5) 0.022(4) 0.028(5) -0.010(4) -0.010(4) -0.009(4) C35 0.024(5) 0.019(4) 0.034(5) -0.006(4) -0.008(4) 0.002(4) N1 0.017(4) 0.016(3) 0.018(4) -0.004(3) -0.008(3) -0.005(3) N2 0.020(4) 0.015(3) 0.025(4) -0.006(3) 0.000(3) -0.011(3) N3 0.026(4) 0.015(3) 0.020(4) -0.005(3) -0.004(3) -0.008(3) N4 0.014(4) 0.012(3) 0.021(4) -0.003(3) -0.003(3) -0.004(3) N5 0.019(4) 0.016(3) 0.023(4) -0.004(3) -0.007(3) -0.005(3) OW1 0.036(4) 0.026(3) 0.029(4) -0.007(3) -0.018(3) -0.002(3) O1 0.036(4) 0.013(3) 0.092(6) -0.020(3) -0.033(4) 0.006(3) O2 0.021(3) 0.011(3) 0.033(4) -0.006(2) -0.006(3) -0.004(2) OW2 0.029(4) 0.025(3) 0.059(5) -0.009(3) 0.001(3) -0.012(3) OW3 0.070(6) 0.035(4) 0.049(5) -0.007(3) -0.027(4) -0.018(4) O3 0.022(3) 0.014(3) 0.036(4) -0.007(3) -0.005(3) -0.007(2) OW4 0.061(5) 0.035(4) 0.058(5) -0.012(4) -0.018(4) -0.017(4) O4 0.032(4) 0.014(3) 0.055(4) 0.005(3) -0.019(3) -0.011(3) OW5 0.058(5) 0.032(4) 0.052(5) -0.004(3) 0.003(4) -0.010(4) O5 0.039(4) 0.022(3) 0.071(5) -0.012(3) -0.026(4) -0.017(3) O6 0.019(3) 0.017(3) 0.038(4) -0.009(3) -0.004(3) -0.005(2) O7 0.022(3) 0.012(3) 0.040(4) -0.003(3) -0.018(3) -0.002(2) O8 0.030(4) 0.011(3) 0.064(5) -0.008(3) -0.025(3) 0.001(3) O9 0.031(4) 0.021(3) 0.051(4) -0.015(3) -0.013(3) 0.000(3) O10 0.029(4) 0.016(3) 0.036(4) -0.004(3) -0.010(3) -0.004(3) O11 0.027(4) 0.019(3) 0.061(5) -0.007(3) -0.006(3) -0.006(3) O12 0.026(4) 0.038(4) 0.050(4) 0.003(3) -0.011(3) -0.025(3) O13 0.036(4) 0.015(3) 0.106(7) -0.012(4) -0.041(4) 0.001(3) O14 0.028(4) 0.014(3) 0.049(4) -0.007(3) -0.021(3) -0.005(3) O15 0.020(3) 0.014(3) 0.058(5) -0.012(3) -0.013(3) -0.004(3) O16 0.032(4) 0.017(3) 0.052(4) -0.006(3) -0.021(3) -0.013(3) O17 0.054(5) 0.022(3) 0.065(5) -0.002(3) -0.039(4) -0.013(3) O18 0.018(3) 0.021(3) 0.030(3) -0.006(2) -0.015(3) -0.005(2) O19 0.038(4) 0.016(3) 0.043(4) -0.003(3) -0.028(3) -0.005(3) O20 0.066(5) 0.015(3) 0.075(6) -0.001(3) -0.048(5) -0.002(3) O21 0.023(3) 0.019(3) 0.026(3) 0.000(2) -0.007(3) -0.007(3) O22 0.021(3) 0.019(3) 0.020(3) -0.008(2) -0.007(2) 0.001(2) O23 0.020(3) 0.017(3) 0.026(3) -0.006(2) -0.008(3) 0.002(2) O24 0.046(4) 0.012(3) 0.024(3) -0.002(2) -0.012(3) -0.005(3) O25 0.028(4) 0.021(3) 0.030(4) -0.013(3) 0.000(3) -0.008(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 O22 2.119(5) . ? Bi1 O3 2.371(5) . ? Bi1 N1 2.413(7) . ? Bi1 O2 2.420(5) . ? Bi1 O21 2.552(6) . ? Bi1 O6 2.590(5) . ? Bi2 Bi2' 0.658(3) . ? Bi2 O23 2.138(6) . ? Bi2 O23 2.381(6) 2_556 ? Bi2 O6 2.436(6) . ? Bi2 O7 2.482(5) . ? Bi2 N2 2.503(7) . ? Bi2 O14 2.556(6) . ? Bi2 Bi2 3.6993(10) 2_556 ? Bi2' N2 2.273(8) . ? Bi2' O7 2.368(6) . ? Bi2' O6 2.411(6) . ? Bi2' OW2 2.501(8) . ? Bi2' O23 2.667(6) . ? Bi2' O3 2.718(6) . ? Bi3 OW1 2.073(6) . ? Bi3 O10 2.327(5) . ? Bi3 N3 2.394(7) . ? Bi3 O11 2.420(6) . ? Bi3 OW2 2.489(6) . ? Bi3 O18 2.649(5) . ? Bi4 Bi4' 0.6579(9) . ? Bi4 O21 2.198(6) 2_556 ? Bi4 O14 2.399(6) . ? Bi4 O15 2.403(6) . ? Bi4 N4 2.408(7) . ? Bi4 O22 2.609(6) 2_556 ? Bi4 O15 2.626(6) 2_566 ? Bi4' O24 2.230(6) . ? Bi4' O14 2.382(6) . ? Bi4' N4 2.431(7) . ? Bi4' O15 2.433(6) . ? Bi4' O7 2.567(6) . ? Bi4' O25 2.658(6) . ? Bi5 O25 2.117(6) . ? Bi5 O24 2.396(6) . ? Bi5 O19 2.443(5) . ? Bi5 N5 2.478(7) . ? Bi5 O18 2.483(5) . ? Bi5 O2 2.557(6) 1_565 ? C1 N1 1.328(10) . ? C1 C2 1.356(12) . ? C1 C6 1.529(12) . ? C2 C3 1.397(12) . ? C3 C4 1.383(12) . ? C4 C5 1.369(12) . ? C5 N1 1.342(10) . ? C5 C7 1.514(11) . ? C6 O1 1.202(10) . ? C6 O2 1.301(10) . ? C7 O4 1.217(9) . ? C7 O3 1.303(10) . ? C8 N2 1.345(10) . ? C8 C9 1.382(12) . ? C8 C13 1.496(11) . ? C9 C10 1.373(11) . ? C10 C11 1.399(11) . ? C11 C12 1.359(12) . ? C12 N2 1.336(10) . ? C12 C14 1.518(11) . ? C13 O5 1.233(9) . ? C13 O6 1.290(10) . ? C14 O8 1.233(9) . ? C14 O7 1.282(10) . ? C15 N3 1.342(10) . ? C15 C16 1.367(12) . ? C15 C20 1.508(12) . ? C16 C17 1.383(12) . ? C17 C18 1.366(12) . ? C18 C19 1.373(12) . ? C19 N3 1.326(10) . ? C19 C21 1.525(11) . ? C20 O9 1.232(9) . ? C20 O10 1.282(10) . ? C21 O12 1.231(10) . ? C21 O11 1.284(11) . ? C22 N4 1.325(9) . ? C22 C23 1.377(12) . ? C22 C27 1.497(11) . ? C23 C24 1.377(11) . ? C24 C25 1.382(11) . ? C25 C26 1.394(11) . ? C26 N4 1.335(9) . ? C26 C28 1.514(11) . ? C27 O13 1.205(9) . ? C27 O14 1.298(10) . ? C28 O16 1.241(10) . ? C28 O15 1.286(10) . ? C29 N5 1.339(10) . ? C29 C30 1.396(12) . ? C29 C34 1.512(12) . ? C30 C31 1.394(12) . ? C31 C32 1.387(13) . ? C32 C33 1.380(13) . ? C33 N5 1.342(10) . ? C33 C35 1.514(12) . ? C34 O17 1.241(9) . ? C34 O18 1.269(10) . ? C35 O20 1.235(10) . ? C35 O19 1.278(11) . ? O2 Bi5 2.557(6) 1_545 ? O15 Bi4 2.626(6) 2_566 ? O21 Bi4 2.198(6) 2_556 ? O22 Bi4 2.609(6) 2_556 ? O23 Bi2 2.381(6) 2_556 ? 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 O22 Bi1 O3 84.4(2) . . ? O22 Bi1 N1 81.4(2) . . ? O3 Bi1 N1 67.5(2) . . ? O22 Bi1 O2 91.1(2) . . ? O3 Bi1 O2 134.0(2) . . ? N1 Bi1 O2 66.5(2) . . ? O22 Bi1 O21 73.0(2) . . ? O3 Bi1 O21 142.68(18) . . ? N1 Bi1 O21 134.6(2) . . ? O2 Bi1 O21 76.91(18) . . ? O22 Bi1 O6 81.3(2) . . ? O3 Bi1 O6 67.95(19) . . ? N1 Bi1 O6 133.39(19) . . ? O2 Bi1 O6 156.22(18) . . ? O21 Bi1 O6 79.32(17) . . ? Bi2' Bi2 O23 138.7(3) . . ? Bi2' Bi2 O23 143.4(3) . 2_556 ? O23 Bi2 O23 70.2(2) . 2_556 ? Bi2' Bi2 O6 80.1(3) . . ? O23 Bi2 O6 92.5(2) . . ? O23 Bi2 O6 76.0(2) 2_556 . ? Bi2' Bi2 O7 72.5(3) . . ? O23 Bi2 O7 81.7(2) . . ? O23 Bi2 O7 143.79(19) 2_556 . ? O6 Bi2 O7 128.9(2) . . ? Bi2' Bi2 N2 62.3(3) . . ? O23 Bi2 N2 77.6(2) . . ? O23 Bi2 N2 127.5(2) 2_556 . ? O6 Bi2 N2 65.0(2) . . ? O7 Bi2 N2 64.22(19) . . ? Bi2' Bi2 O14 113.7(3) . . ? O23 Bi2 O14 81.8(2) . . ? O23 Bi2 O14 88.30(19) 2_556 . ? O6 Bi2 O14 164.3(2) . . ? O7 Bi2 O14 64.9(2) . . ? N2 Bi2 O14 127.12(19) . . ? Bi2' Bi2 Bi2 161.9(3) . 2_556 ? O23 Bi2 Bi2 37.27(15) . 2_556 ? O23 Bi2 Bi2 32.94(13) 2_556 2_556 ? O6 Bi2 Bi2 82.55(14) . 2_556 ? O7 Bi2 Bi2 115.83(14) . 2_556 ? N2 Bi2 Bi2 105.57(15) . 2_556 ? O14 Bi2 Bi2 84.18(14) . 2_556 ? Bi2 Bi2' N2 102.9(4) . . ? Bi2 Bi2' O7 92.2(3) . . ? N2 Bi2' O7 69.6(2) . . ? Bi2 Bi2' O6 84.3(3) . . ? N2 Bi2' O6 69.0(2) . . ? O7 Bi2' O6 136.4(2) . . ? Bi2 Bi2' OW2 172.8(4) . . ? N2 Bi2' OW2 77.9(2) . . ? O7 Bi2' OW2 94.8(2) . . ? O6 Bi2' OW2 89.3(2) . . ? Bi2 Bi2' O23 32.0(3) . . ? N2 Bi2' O23 72.1(2) . . ? O7 Bi2' O23 73.8(2) . . ? O6 Bi2' O23 81.2(2) . . ? OW2 Bi2' O23 149.9(2) . . ? Bi2 Bi2' O3 95.0(3) . . ? N2 Bi2' O3 128.5(2) . . ? O7 Bi2' O3 157.9(2) . . ? O6 Bi2' O3 65.3(2) . . ? OW2 Bi2' O3 79.3(2) . . ? O23 Bi2' O3 121.0(2) . . ? OW1 Bi3 O10 93.1(2) . . ? OW1 Bi3 N3 84.9(2) . . ? O10 Bi3 N3 68.0(2) . . ? OW1 Bi3 O11 85.6(2) . . ? O10 Bi3 O11 134.7(2) . . ? N3 Bi3 O11 66.8(2) . . ? OW1 Bi3 OW2 79.7(2) . . ? O10 Bi3 OW2 77.2(2) . . ? N3 Bi3 OW2 140.9(2) . . ? O11 Bi3 OW2 145.8(2) . . ? OW1 Bi3 O18 82.6(2) . . ? O10 Bi3 O18 155.51(19) . . ? N3 Bi3 O18 135.00(19) . . ? O11 Bi3 O18 69.22(19) . . ? OW2 Bi3 O18 78.35(18) . . ? Bi4' Bi4 O21 163.0(2) . 2_556 ? Bi4' Bi4 O14 80.6(2) . . ? O21 Bi4 O14 94.0(2) 2_556 . ? Bi4' Bi4 O15 84.8(2) . . ? O21 Bi4 O15 87.1(2) 2_556 . ? O14 Bi4 O15 132.0(2) . . ? Bi4' Bi4 N4 84.2(2) . . ? O21 Bi4 N4 78.9(2) 2_556 . ? O14 Bi4 N4 66.4(2) . . ? O15 Bi4 N4 66.8(2) . . ? Bi4' Bi4 O22 123.7(2) . 2_556 ? O21 Bi4 O22 70.7(2) 2_556 2_556 ? O14 Bi4 O22 81.23(19) . 2_556 ? O15 Bi4 O22 142.11(19) . 2_556 ? N4 Bi4 O22 133.5(2) . 2_556 ? Bi4' Bi4 O15 108.4(2) . 2_566 ? O21 Bi4 O15 81.8(2) 2_556 2_566 ? O14 Bi4 O15 160.8(2) . 2_566 ? O15 Bi4 O15 66.7(2) . 2_566 ? N4 Bi4 O15 130.1(2) . 2_566 ? O22 Bi4 O15 79.75(17) 2_556 2_566 ? Bi4 Bi4' O24 155.9(2) . . ? Bi4 Bi4' O14 83.6(2) . . ? O24 Bi4' O14 84.5(2) . . ? Bi4 Bi4' N4 80.2(2) . . ? O24 Bi4' N4 75.9(2) . . ? O14 Bi4' N4 66.3(2) . . ? Bi4 Bi4' O15 79.6(2) . . ? O24 Bi4' O15 92.9(2) . . ? O14 Bi4' O15 131.4(2) . . ? N4 Bi4' O15 66.0(2) . . ? Bi4 Bi4' O7 113.1(2) . . ? O24 Bi4' O7 80.6(2) . . ? O14 Bi4' O7 66.1(2) . . ? N4 Bi4' O7 128.33(19) . . ? O15 Bi4' O7 161.0(2) . . ? Bi4 Bi4' O25 131.30(19) . . ? O24 Bi4' O25 68.0(2) . . ? O14 Bi4' O25 141.33(19) . . ? N4 Bi4' O25 127.2(2) . . ? O15 Bi4' O25 78.6(2) . . ? O7 Bi4' O25 82.46(18) . . ? O25 Bi5 O24 75.0(2) . . ? O25 Bi5 O19 83.1(2) . . ? O24 Bi5 O19 147.76(19) . . ? O25 Bi5 N5 82.1(2) . . ? O24 Bi5 N5 132.4(2) . . ? O19 Bi5 N5 65.3(2) . . ? O25 Bi5 O18 94.2(2) . . ? O24 Bi5 O18 76.22(19) . . ? O19 Bi5 O18 129.50(19) . . ? N5 Bi5 O18 64.40(19) . . ? O25 Bi5 O2 82.7(2) . 1_565 ? O24 Bi5 O2 84.71(19) . 1_565 ? O19 Bi5 O2 69.12(19) . 1_565 ? N5 Bi5 O2 133.24(19) . 1_565 ? O18 Bi5 O2 160.81(18) . 1_565 ? N1 C1 C2 123.1(8) . . ? N1 C1 C6 114.5(8) . . ? C2 C1 C6 122.4(8) . . ? C1 C2 C3 117.7(8) . . ? C4 C3 C2 119.3(9) . . ? C5 C4 C3 119.2(8) . . ? N1 C5 C4 120.8(8) . . ? N1 C5 C7 115.8(7) . . ? C4 C5 C7 123.4(7) . . ? O1 C6 O2 123.9(8) . . ? O1 C6 C1 120.1(8) . . ? O2 C6 C1 116.0(7) . . ? O4 C7 O3 125.9(8) . . ? O4 C7 C5 118.7(8) . . ? O3 C7 C5 115.4(7) . . ? N2 C8 C9 120.8(8) . . ? N2 C8 C13 115.8(8) . . ? C9 C8 C13 123.4(7) . . ? C10 C9 C8 118.8(8) . . ? C9 C10 C11 119.7(8) . . ? C12 C11 C10 118.4(8) . . ? N2 C12 C11 122.0(7) . . ? N2 C12 C14 115.3(7) . . ? C11 C12 C14 122.7(7) . . ? O5 C13 O6 125.0(8) . . ? O5 C13 C8 118.7(8) . . ? O6 C13 C8 116.3(7) . . ? O8 C14 O7 125.6(8) . . ? O8 C14 C12 118.6(8) . . ? O7 C14 C12 115.8(7) . . ? N3 C15 C16 120.8(8) . . ? N3 C15 C20 114.3(8) . . ? C16 C15 C20 124.9(8) . . ? C15 C16 C17 118.1(8) . . ? C18 C17 C16 120.5(9) . . ? C17 C18 C19 118.7(9) . . ? N3 C19 C18 120.8(8) . . ? N3 C19 C21 116.1(8) . . ? C18 C19 C21 123.1(8) . . ? O9 C20 O10 124.8(8) . . ? O9 C20 C15 118.5(8) . . ? O10 C20 C15 116.7(7) . . ? O12 C21 O11 125.3(9) . . ? O12 C21 C19 119.5(8) . . ? O11 C21 C19 115.0(8) . . ? N4 C22 C23 121.8(7) . . ? N4 C22 C27 115.5(8) . . ? C23 C22 C27 122.7(8) . . ? C24 C23 C22 118.4(8) . . ? C23 C24 C25 120.3(8) . . ? C24 C25 C26 117.6(7) . . ? N4 C26 C25 121.5(7) . . ? N4 C26 C28 115.3(7) . . ? C25 C26 C28 123.2(7) . . ? O13 C27 O14 123.2(8) . . ? O13 C27 C22 120.9(8) . . ? O14 C27 C22 115.9(7) . . ? O16 C28 O15 125.5(8) . . ? O16 C28 C26 118.5(8) . . ? O15 C28 C26 116.0(7) . . ? N5 C29 C30 122.2(8) . . ? N5 C29 C34 114.8(8) . . ? C30 C29 C34 122.9(7) . . ? C31 C30 C29 117.9(8) . . ? C32 C31 C30 119.5(9) . . ? C33 C32 C31 118.8(9) . . ? N5 C33 C32 122.2(8) . . ? N5 C33 C35 115.5(8) . . ? C32 C33 C35 122.3(8) . . ? O17 C34 O18 125.2(8) . . ? O17 C34 C29 118.2(8) . . ? O18 C34 C29 116.6(7) . . ? O20 C35 O19 126.5(9) . . ? O20 C35 C33 117.6(9) . . ? O19 C35 C33 115.9(8) . . ? C1 N1 C5 119.8(7) . . ? C1 N1 Bi1 121.3(5) . . ? C5 N1 Bi1 118.9(5) . . ? C12 N2 C8 120.2(8) . . ? C12 N2 Bi2' 118.3(5) . . ? C8 N2 Bi2' 120.5(6) . . ? C12 N2 Bi2 121.0(5) . . ? C8 N2 Bi2 118.7(6) . . ? Bi2' N2 Bi2 14.84(9) . . ? C19 N3 C15 121.0(8) . . ? C19 N3 Bi3 120.3(5) . . ? C15 N3 Bi3 118.6(5) . . ? C22 N4 C26 120.2(7) . . ? C22 N4 Bi4 119.5(5) . . ? C26 N4 Bi4 119.9(5) . . ? C22 N4 Bi4' 119.5(5) . . ? C26 N4 Bi4' 119.4(5) . . ? Bi4 N4 Bi4' 15.62(5) . . ? C29 N5 C33 119.3(8) . . ? C29 N5 Bi5 120.7(6) . . ? C33 N5 Bi5 119.7(6) . . ? C6 O2 Bi1 121.4(5) . . ? C6 O2 Bi5 109.9(5) . 1_545 ? Bi1 O2 Bi5 121.6(2) . 1_545 ? Bi3 OW2 Bi2' 110.0(3) . . ? C7 O3 Bi1 122.1(5) . . ? C7 O3 Bi2' 125.7(5) . . ? Bi1 O3 Bi2' 111.7(2) . . ? C13 O6 Bi2' 117.3(5) . . ? C13 O6 Bi2 123.0(5) . . ? Bi2' O6 Bi2 15.59(7) . . ? C13 O6 Bi1 117.1(5) . . ? Bi2' O6 Bi1 114.9(2) . . ? Bi2 O6 Bi1 116.9(2) . . ? C14 O7 Bi2' 116.2(5) . . ? C14 O7 Bi2 123.5(5) . . ? Bi2' O7 Bi2 15.36(7) . . ? C14 O7 Bi4' 122.4(5) . . ? Bi2' O7 Bi4' 121.4(2) . . ? Bi2 O7 Bi4' 112.5(2) . . ? C20 O10 Bi3 122.1(5) . . ? C21 O11 Bi3 121.7(6) . . ? C27 O14 Bi4' 122.0(5) . . ? C27 O14 Bi4 120.7(5) . . ? Bi4' O14 Bi4 15.81(4) . . ? C27 O14 Bi2 115.5(5) . . ? Bi4' O14 Bi2 116.4(2) . . ? Bi4 O14 Bi2 123.0(3) . . ? C28 O15 Bi4 121.6(5) . . ? C28 O15 Bi4' 120.7(5) . . ? Bi4 O15 Bi4' 15.62(4) . . ? C28 O15 Bi4 120.4(5) . 2_566 ? Bi4 O15 Bi4 113.3(2) . 2_566 ? Bi4' O15 Bi4 118.4(2) . 2_566 ? C34 O18 Bi5 122.3(5) . . ? C34 O18 Bi3 113.6(5) . . ? Bi5 O18 Bi3 119.3(2) . . ? C35 O19 Bi5 123.2(5) . . ? Bi4 O21 Bi1 107.9(2) 2_556 . ? Bi1 O22 Bi4 108.4(2) . 2_556 ? Bi2 O23 Bi2 109.8(2) . 2_556 ? Bi2 O23 Bi2' 9.38(8) . . ? Bi2 O23 Bi2' 118.0(2) 2_556 . ? Bi4' O24 Bi5 111.2(2) . . ? Bi5 O25 Bi4' 105.6(2) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.307 _refine_diff_density_min -2.509 _refine_diff_density_rms 0.277 #===end data_1 _database_code_depnum_ccdc_archive 'CCDC 866521' #TrackingRef '- supporting information 2-R1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 Bi N O6' _chemical_formula_weight 409.11 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.344(2) _cell_length_b 9.1341(13) _cell_length_c 6.3124(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.830(9) _cell_angle_gamma 90.00 _cell_volume 868.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4576 _cell_measurement_theta_min 1.35 _cell_measurement_theta_max 25.00 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 20.300 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0481 _exptl_absorpt_correction_T_max 0.6869 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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-II area-detector diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 9273 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1526 _reflns_number_gt 1293 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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 maximum peaks is 4.89 (0.92 from Bi). ; _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^)+(0.1026P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0086(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1526 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Bi Bi 0.05852(3) -0.09943(4) 0.80123(7) 0.0221(3) Uani 1 1 d . . . OW O 0.4683(9) -0.1579(19) 1.511(3) 0.117(6) Uani 1 1 d . . . O1 O 0.1758(6) 0.1514(10) 0.3145(15) 0.035(2) Uani 1 1 d . . . O2 O 0.0826(5) 0.0277(9) 0.4758(13) 0.0306(19) Uani 1 1 d . . . O3 O 0.1498(5) -0.1737(9) 1.1230(12) 0.0281(18) Uani 1 1 d . . . O4 O 0.2836(6) -0.1682(9) 1.3330(14) 0.036(2) Uani 1 1 d . . . O5 O 0.0438(6) 0.1143(7) 0.9304(15) 0.027(2) Uani 1 1 d . . . N N 0.2062(6) -0.0150(9) 0.8223(14) 0.024(2) Uani 1 1 d . . . C1 C 0.1619(9) 0.0837(12) 0.466(2) 0.023(3) Uani 1 1 d . . . C2 C 0.2317(9) -0.1347(14) 1.165(2) 0.025(3) Uani 1 1 d . . . C3 C 0.2302(8) 0.0562(12) 0.6568(19) 0.026(3) Uani 1 1 d . . . C4 C 0.3168(10) 0.1057(12) 0.669(2) 0.032(3) Uani 1 1 d . . . H4A H 0.3328 0.1561 0.5537 0.038 Uiso 1 1 calc R . . C5 C 0.3776(10) 0.0792(14) 0.851(3) 0.040(4) Uani 1 1 d . . . H5A H 0.4358 0.1109 0.8605 0.047 Uiso 1 1 calc R . . C6 C 0.3530(8) 0.0049(13) 1.0227(19) 0.033(3) Uani 1 1 d . . . H6A H 0.3935 -0.0107 1.1501 0.039 Uiso 1 1 calc R . . C7 C 0.2657(9) -0.0455(13) 0.998(2) 0.029(3) 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 Bi 0.0301(4) 0.0176(4) 0.0195(4) 0.00123(14) 0.0066(3) 0.00084(14) OW 0.064(9) 0.097(11) 0.179(17) 0.059(13) -0.007(10) 0.011(8) O1 0.040(5) 0.029(5) 0.035(6) 0.001(4) 0.006(4) -0.004(4) O2 0.023(4) 0.044(5) 0.026(4) 0.010(4) 0.005(3) 0.003(4) O3 0.028(5) 0.028(5) 0.029(5) 0.005(4) 0.006(3) 0.002(3) O4 0.042(5) 0.033(5) 0.030(5) 0.005(4) -0.002(4) 0.000(4) O5 0.032(5) 0.017(4) 0.038(5) 0.000(3) 0.020(4) -0.004(3) N 0.031(5) 0.018(5) 0.022(5) 0.002(4) 0.004(4) 0.003(4) C1 0.026(7) 0.017(6) 0.024(7) 0.007(5) -0.001(5) 0.009(4) C2 0.033(7) 0.022(6) 0.024(7) 0.000(5) 0.011(6) 0.002(5) C3 0.042(7) 0.016(5) 0.024(7) 0.000(5) 0.016(5) 0.007(5) C4 0.048(9) 0.023(7) 0.027(8) 0.006(5) 0.015(7) -0.002(5) C5 0.022(7) 0.036(8) 0.057(11) 0.001(6) -0.001(7) -0.006(5) C6 0.036(7) 0.028(7) 0.034(7) 0.005(6) 0.003(6) -0.004(6) C7 0.043(8) 0.021(6) 0.026(7) 0.003(5) 0.014(6) 0.014(5) _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 Bi O5 2.144(7) . ? Bi O3 2.341(8) . ? Bi N 2.373(9) . ? Bi O2 2.448(8) . ? Bi O5 2.521(8) 3_557 ? Bi O2 2.599(8) 3_556 ? O1 C1 1.193(17) . ? O2 C1 1.332(15) . ? O2 Bi 2.599(8) 3_556 ? O3 C2 1.284(15) . ? O4 C2 1.238(15) . ? O5 Bi 2.521(8) 3_557 ? N C7 1.328(15) . ? N C3 1.340(14) . ? C1 C3 1.461(18) . ? C2 C7 1.502(18) . ? C3 C4 1.392(19) . ? C4 C5 1.36(2) . ? C5 C6 1.39(2) . ? C6 C7 1.398(17) . ? 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 O5 Bi O3 91.3(3) . . ? O5 Bi N 81.4(3) . . ? O3 Bi N 68.7(3) . . ? O5 Bi O2 86.0(3) . . ? O3 Bi O2 134.9(3) . . ? N Bi O2 66.4(3) . . ? O5 Bi O5 70.8(3) . 3_557 ? O3 Bi O5 75.4(3) . 3_557 ? N Bi O5 133.5(3) . 3_557 ? O2 Bi O5 143.2(3) . 3_557 ? O5 Bi O2 83.8(3) . 3_556 ? O3 Bi O2 160.8(2) . 3_556 ? N Bi O2 128.4(3) . 3_556 ? O2 Bi O2 63.5(3) . 3_556 ? O5 Bi O2 85.4(3) 3_557 3_556 ? C1 O2 Bi 120.2(7) . . ? C1 O2 Bi 121.7(7) . 3_556 ? Bi O2 Bi 116.5(3) . 3_556 ? C2 O3 Bi 120.2(8) . . ? Bi O5 Bi 109.2(3) . 3_557 ? C7 N C3 120.5(10) . . ? C7 N Bi 118.5(8) . . ? C3 N Bi 120.9(8) . . ? O1 C1 O2 122.5(12) . . ? O1 C1 C3 122.9(12) . . ? O2 C1 C3 114.6(11) . . ? O4 C2 O3 123.9(12) . . ? O4 C2 C7 118.8(12) . . ? O3 C2 C7 117.3(12) . . ? N C3 C4 121.0(11) . . ? N C3 C1 117.8(11) . . ? C4 C3 C1 121.2(11) . . ? C5 C4 C3 118.9(13) . . ? C4 C5 C6 120.2(13) . . ? C5 C6 C7 118.0(12) . . ? N C7 C6 121.2(11) . . ? N C7 C2 115.2(11) . . ? C6 C7 C2 123.6(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 4.891 _refine_diff_density_min -2.641 _refine_diff_density_rms 0.728