Supplementary Material (ESI) for Dalton Transactions This journal is (C) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;Fluorinated bismuth alkoxides: From monomers to polymers and oxo-clusters ; _publ_contact_author_name 'Phil Andrews' _publ_contact_author_email PHIL.ANDREWS@SCI.MONASH.EDU.AU loop_ _publ_author_name 'Phil Andrews' 'Peter Junk' 'Iryna Nuzhnaya' 'Leone Spiccia' # Attachment 'compound 5.cif' data_C:\compound5 _database_code_depnum_ccdc_archive 'CCDC 637419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common X-Seed _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H7 Bi F12 O2' _chemical_formula_weight 620.16 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' F F 0.0171 0.0103 '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 P21/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 12.8185(2) _cell_length_b 19.3178(3) _cell_length_c 13.3728(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.868(2) _cell_angle_gamma 90.00 _cell_volume 3214.91(10) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2288 _exptl_absorpt_coefficient_mu 11.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2867 _exptl_absorpt_correction_T_max 0.4031 _exptl_absorpt_process_details 'part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43063 _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 28.19 _reflns_number_total 7764 _reflns_number_gt 6446 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction Nonius _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0781P)^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 7764 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Bi1 Bi 0.08481(2) 0.221449(13) 0.312655(19) 0.01164(9) Uani 1 1 d . . . Bi2 Bi 0.32848(2) 0.234276(14) 0.572230(19) 0.01191(9) Uani 1 1 d . . . F6 F 0.2365(4) 0.2693(3) 0.1488(4) 0.0295(12) Uani 1 1 d . . . F4 F 0.2130(4) 0.2728(2) -0.0164(4) 0.0277(11) Uani 1 1 d . . . F5 F 0.1286(3) 0.3436(2) 0.0590(3) 0.0243(10) Uani 1 1 d . . . F20 F 0.5103(4) 0.1641(3) 0.3548(3) 0.0300(11) Uani 1 1 d . . . F2 F 0.0261(3) 0.1083(2) 0.0400(3) 0.0235(10) Uani 1 1 d . . . F1 F 0.1671(4) 0.1374(3) -0.0094(4) 0.0330(12) Uani 1 1 d . . . C1 C 0.0685(6) 0.2279(4) 0.0471(6) 0.0146(15) Uani 1 1 d . . . H1 H 0.0207 0.2347 -0.0232 0.018 Uiso 1 1 calc R . . F3 F 0.1683(4) 0.1383(3) 0.1517(4) 0.0303(11) Uani 1 1 d . . . O1 O 0.0090(4) 0.2422(3) 0.1195(3) 0.0137(10) Uani 1 1 d . . . F19 F 0.3818(4) 0.1026(3) 0.2637(3) 0.0330(12) Uani 1 1 d . . . O4 O 0.3454(4) 0.1775(3) 0.4424(4) 0.0173(11) Uani 1 1 d . . . C10 C 0.3920(6) 0.1117(4) 0.4443(5) 0.0168(15) Uani 1 1 d . . . H10 H 0.4457 0.1053 0.5116 0.020 Uiso 1 1 calc R . . C3 C 0.1634(6) 0.2780(4) 0.0598(6) 0.0188(16) Uani 1 1 d . . . F21 F 0.5164(4) 0.0529(3) 0.3684(4) 0.0325(12) Uani 1 1 d . . . C2 C 0.1077(6) 0.1520(4) 0.0561(6) 0.0182(16) Uani 1 1 d . . . C11 C 0.4503(6) 0.1073(4) 0.3558(6) 0.0225(17) Uani 1 1 d . . . F14 F 0.0848(4) 0.3968(3) 0.2454(3) 0.0274(11) Uani 1 1 d . . . F22 F 0.2708(4) 0.0515(3) 0.5189(4) 0.0328(12) Uani 1 1 d . . . F23 F 0.2199(4) 0.0695(3) 0.3568(4) 0.0302(11) Uani 1 1 d . . . O2 O 0.1269(4) 0.2155(3) 0.4888(4) 0.0141(10) Uani 1 1 d . . . F24 F 0.3420(4) -0.0063(3) 0.4153(4) 0.0388(13) Uani 1 1 d . . . O3 O -0.0339(4) 0.2956(3) 0.3182(4) 0.0161(10) Uani 1 1 d . . . C14 C -0.1471(6) 0.1626(4) 0.3143(5) 0.0169(15) Uani 1 1 d . . . H14 H -0.1588 0.2082 0.3359 0.020 Uiso 1 1 calc R . . C15 C -0.2267(6) 0.1124(4) 0.3055(6) 0.0211(17) Uani 1 1 d . . . H15 H -0.2928 0.1241 0.3215 0.025 Uiso 1 1 calc R . . C18 C -0.0336(6) 0.0784(4) 0.2587(5) 0.0181(16) Uani 1 1 d . . . H18 H 0.0324 0.0664 0.2429 0.022 Uiso 1 1 calc R . . C13 C -0.0492(5) 0.1450(4) 0.2911(5) 0.0155(15) Uani 1 1 d . . . C8 C 0.0015(6) 0.4150(4) 0.2838(6) 0.0198(16) Uani 1 1 d . . . C4 C 0.0492(6) 0.2026(4) 0.5451(5) 0.0160(15) Uani 1 1 d . . . H4 H -0.0234 0.2098 0.4980 0.019 Uiso 1 1 calc R . . C7 C -0.0130(6) 0.3610(4) 0.3627(6) 0.0187(15) Uani 1 1 d . . . H7 H 0.0543 0.3588 0.4189 0.022 Uiso 1 1 calc R . . C12 C 0.3056(7) 0.0553(4) 0.4328(6) 0.0223(17) Uani 1 1 d . . . F9 F 0.1546(4) 0.1130(3) 0.6407(3) 0.0288(11) Uani 1 1 d . . . F12 F 0.0768(4) 0.3176(3) 0.6060(4) 0.0309(11) Uani 1 1 d . . . F15 F -0.0840(4) 0.4178(3) 0.2036(3) 0.0279(11) Uani 1 1 d . . . F18 F -0.1225(4) 0.3282(3) 0.4735(4) 0.0312(12) Uani 1 1 d . . . F7 F 0.0382(4) 0.0836(3) 0.5044(4) 0.0307(11) Uani 1 1 d . . . F11 F 0.1456(4) 0.2386(3) 0.7126(4) 0.0315(12) Uani 1 1 d . . . F8 F -0.0144(4) 0.1149(3) 0.6385(4) 0.0394(13) Uani 1 1 d . . . F17 F -0.1980(4) 0.3881(3) 0.3416(4) 0.0381(13) Uani 1 1 d . . . F10 F -0.0255(4) 0.2531(3) 0.6720(4) 0.0361(12) Uani 1 1 d . . . F16 F -0.0893(5) 0.4365(3) 0.4662(5) 0.0531(16) Uani 1 1 d . . . C16 C -0.2110(6) 0.0459(4) 0.2738(6) 0.0246(18) Uani 1 1 d . . . H16 H -0.2658 0.0121 0.2688 0.030 Uiso 1 1 calc R . . C5 C 0.0563(6) 0.1275(4) 0.5818(6) 0.0226(17) Uani 1 1 d . . . C6 C 0.0612(6) 0.2531(5) 0.6350(6) 0.0209(16) Uani 1 1 d . . . C17 C -0.1153(6) 0.0289(4) 0.2494(6) 0.0211(16) Uani 1 1 d . . . H17 H -0.1048 -0.0165 0.2263 0.025 Uiso 1 1 calc R . . C9 C -0.1073(7) 0.3790(4) 0.4100(6) 0.0252(18) Uani 1 1 d . . . C19 C 0.3065(5) 0.3266(4) 0.4726(5) 0.0134(14) Uani 1 1 d . . . C24 C 0.2778(5) 0.3885(4) 0.5138(6) 0.0149(15) Uani 1 1 d . . . H24 H 0.2590 0.3879 0.5784 0.018 Uiso 1 1 calc R . . C20 C 0.3327(5) 0.3280(4) 0.3761(5) 0.0158(15) Uani 1 1 d . . . H20 H 0.3511 0.2865 0.3464 0.019 Uiso 1 1 calc R . . C23 C 0.2764(6) 0.4510(4) 0.4607(6) 0.0239(17) Uani 1 1 d . . . H23 H 0.2561 0.4927 0.4886 0.029 Uiso 1 1 calc R . . C22 C 0.3049(6) 0.4517(4) 0.3677(6) 0.0262(18) Uani 1 1 d . . . H22 H 0.3065 0.4943 0.3326 0.031 Uiso 1 1 calc R . . C21 C 0.3312(6) 0.3906(4) 0.3250(6) 0.0221(17) Uani 1 1 d . . . H21 H 0.3484 0.3917 0.2598 0.026 Uiso 1 1 calc R . . F13 F 0.0195(4) 0.4775(2) 0.3231(4) 0.0333(12) 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 0.00862(14) 0.01478(15) 0.01214(16) 0.00043(9) 0.00369(11) -0.00046(9) Bi2 0.00990(15) 0.01521(15) 0.01129(15) -0.00011(9) 0.00384(11) -0.00049(9) F6 0.015(2) 0.044(3) 0.025(3) 0.006(2) -0.003(2) -0.009(2) F4 0.030(3) 0.029(3) 0.034(3) -0.002(2) 0.026(2) -0.001(2) F5 0.022(2) 0.024(3) 0.030(3) -0.002(2) 0.012(2) -0.0029(19) F20 0.032(3) 0.036(3) 0.027(3) -0.003(2) 0.016(2) -0.005(2) F2 0.019(2) 0.020(2) 0.034(3) 0.0026(19) 0.012(2) -0.0004(18) F1 0.035(3) 0.026(3) 0.048(3) -0.005(2) 0.032(2) 0.003(2) C1 0.015(3) 0.015(4) 0.015(4) 0.002(3) 0.004(3) -0.001(3) F3 0.025(2) 0.028(3) 0.031(3) 0.003(2) -0.007(2) 0.006(2) O1 0.010(2) 0.023(3) 0.008(2) -0.005(2) 0.0031(19) 0.003(2) F19 0.030(3) 0.050(3) 0.018(3) -0.011(2) 0.003(2) 0.003(2) O4 0.022(3) 0.019(3) 0.012(2) -0.003(2) 0.006(2) 0.003(2) C10 0.018(4) 0.020(4) 0.012(4) -0.002(3) 0.001(3) 0.003(3) C3 0.010(3) 0.030(4) 0.019(4) 0.000(3) 0.006(3) -0.004(3) F21 0.031(3) 0.036(3) 0.032(3) -0.004(2) 0.011(2) 0.015(2) C2 0.010(3) 0.025(4) 0.021(4) -0.004(3) 0.006(3) 0.005(3) C11 0.022(4) 0.025(4) 0.021(4) -0.005(3) 0.006(3) 0.008(3) F14 0.025(2) 0.036(3) 0.025(2) 0.003(2) 0.014(2) -0.007(2) F22 0.030(3) 0.043(3) 0.025(3) 0.000(2) 0.007(2) -0.012(2) F23 0.020(2) 0.035(3) 0.029(3) -0.002(2) -0.007(2) -0.003(2) O2 0.011(2) 0.026(3) 0.006(2) 0.0020(19) 0.003(2) -0.002(2) F24 0.046(3) 0.020(3) 0.052(3) -0.005(2) 0.013(3) 0.001(2) O3 0.010(2) 0.015(3) 0.023(3) -0.003(2) 0.004(2) -0.001(2) C14 0.018(4) 0.018(4) 0.012(4) -0.003(3) 0.001(3) 0.000(3) C15 0.011(3) 0.030(4) 0.023(4) 0.002(3) 0.007(3) -0.003(3) C18 0.016(4) 0.025(4) 0.012(4) 0.008(3) 0.000(3) -0.002(3) C13 0.006(3) 0.024(4) 0.016(4) 0.000(3) 0.001(3) -0.001(3) C8 0.013(3) 0.023(4) 0.022(4) 0.000(3) 0.002(3) -0.004(3) C4 0.015(3) 0.024(4) 0.013(4) 0.001(3) 0.012(3) -0.004(3) C7 0.018(4) 0.017(4) 0.020(4) -0.001(3) 0.002(3) 0.001(3) C12 0.031(4) 0.012(4) 0.023(4) -0.003(3) 0.006(4) 0.001(3) F9 0.032(3) 0.028(3) 0.023(3) 0.008(2) 0.002(2) -0.001(2) F12 0.038(3) 0.025(3) 0.030(3) -0.005(2) 0.009(2) -0.003(2) F15 0.031(3) 0.032(3) 0.019(2) 0.009(2) 0.003(2) 0.002(2) F18 0.022(2) 0.044(3) 0.033(3) 0.014(2) 0.017(2) 0.005(2) F7 0.038(3) 0.026(3) 0.027(3) -0.001(2) 0.006(2) -0.009(2) F11 0.025(3) 0.041(3) 0.024(3) -0.006(2) -0.003(2) 0.001(2) F8 0.039(3) 0.046(3) 0.044(3) 0.017(3) 0.032(3) -0.003(2) F17 0.017(2) 0.060(4) 0.041(3) 0.014(3) 0.013(2) 0.014(2) F10 0.026(3) 0.057(3) 0.032(3) -0.019(3) 0.020(2) -0.009(3) F16 0.064(4) 0.045(4) 0.064(4) -0.029(3) 0.044(3) -0.009(3) C16 0.026(4) 0.027(5) 0.023(4) 0.006(3) 0.009(4) -0.008(3) C5 0.023(4) 0.031(5) 0.014(4) 0.002(3) 0.005(3) -0.004(3) C6 0.015(4) 0.034(5) 0.014(4) -0.002(3) 0.005(3) 0.000(3) C17 0.028(4) 0.015(4) 0.021(4) 0.004(3) 0.005(3) -0.001(3) C9 0.026(4) 0.023(4) 0.029(5) -0.005(3) 0.014(4) -0.002(3) C19 0.008(3) 0.015(3) 0.017(4) 0.000(3) 0.003(3) -0.002(3) C24 0.007(3) 0.023(4) 0.014(4) -0.001(3) 0.001(3) 0.002(3) C20 0.009(3) 0.021(4) 0.016(4) -0.001(3) 0.000(3) 0.002(3) C23 0.021(4) 0.014(4) 0.037(5) -0.004(3) 0.008(4) 0.002(3) C22 0.027(4) 0.017(4) 0.033(5) 0.010(3) 0.004(4) -0.002(3) C21 0.020(4) 0.029(5) 0.014(4) 0.008(3) -0.001(3) -0.002(3) F13 0.052(3) 0.017(2) 0.030(3) -0.001(2) 0.010(2) -0.009(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 O3 2.104(5) . ? Bi1 C13 2.231(7) . ? Bi1 O2 2.290(5) . ? Bi1 O1 2.563(5) . ? Bi2 O4 2.109(5) . ? Bi2 C19 2.204(7) . ? Bi2 O1 2.293(5) 4_666 ? Bi2 O2 2.583(5) . ? F6 C3 1.338(9) . ? F4 C3 1.328(9) . ? F5 C3 1.342(9) . ? F20 C11 1.343(9) . ? F2 C2 1.321(9) . ? F1 C2 1.323(8) . ? C1 O1 1.397(8) . ? C1 C3 1.531(10) . ? C1 C2 1.545(10) . ? F3 C2 1.353(9) . ? O1 Bi2 2.293(5) 4_565 ? F19 C11 1.333(9) . ? O4 C10 1.402(9) . ? C10 C12 1.535(11) . ? C10 C11 1.546(10) . ? F21 C11 1.335(9) . ? F14 C8 1.339(9) . ? F22 C12 1.332(9) . ? F23 C12 1.335(9) . ? O2 C4 1.407(8) . ? F24 C12 1.318(9) . ? O3 C7 1.395(9) . ? C14 C15 1.391(10) . ? C14 C13 1.405(10) . ? C15 C16 1.383(12) . ? C18 C13 1.387(11) . ? C18 C17 1.401(10) . ? C8 F13 1.315(9) . ? C8 F15 1.338(8) . ? C8 C7 1.525(11) . ? C4 C5 1.527(11) . ? C4 C6 1.527(11) . ? C7 C9 1.533(11) . ? F9 C5 1.346(9) . ? F12 C6 1.335(10) . ? F18 C9 1.342(9) . ? F7 C5 1.316(9) . ? F11 C6 1.337(9) . ? F8 C5 1.337(9) . ? F17 C9 1.307(9) . ? F10 C6 1.320(8) . ? F16 C9 1.329(9) . ? C16 C17 1.383(11) . ? C19 C24 1.402(10) . ? C19 C20 1.408(10) . ? C24 C23 1.400(11) . ? C20 C21 1.387(10) . ? C23 C22 1.377(11) . ? C22 C21 1.388(12) . ? 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 O3 Bi1 C13 85.1(2) . . ? O3 Bi1 O2 89.53(19) . . ? C13 Bi1 O2 94.8(2) . . ? O3 Bi1 O1 80.02(17) . . ? C13 Bi1 O1 83.0(2) . . ? O2 Bi1 O1 169.47(17) . . ? O4 Bi2 C19 87.0(2) . . ? O4 Bi2 O1 91.95(18) . 4_666 ? C19 Bi2 O1 88.9(2) . 4_666 ? O4 Bi2 O2 82.01(17) . . ? C19 Bi2 O2 83.3(2) . . ? O1 Bi2 O2 170.32(15) 4_666 . ? O1 C1 C3 110.5(6) . . ? O1 C1 C2 110.7(6) . . ? C3 C1 C2 110.9(6) . . ? C1 O1 Bi2 122.0(4) . 4_565 ? C1 O1 Bi1 122.0(4) . . ? Bi2 O1 Bi1 115.01(19) 4_565 . ? C10 O4 Bi2 125.7(4) . . ? O4 C10 C12 110.3(6) . . ? O4 C10 C11 108.5(6) . . ? C12 C10 C11 110.7(6) . . ? F4 C3 F6 108.1(6) . . ? F4 C3 F5 106.6(6) . . ? F6 C3 F5 106.6(6) . . ? F4 C3 C1 112.4(6) . . ? F6 C3 C1 112.8(6) . . ? F5 C3 C1 110.0(6) . . ? F2 C2 F1 108.3(6) . . ? F2 C2 F3 106.4(6) . . ? F1 C2 F3 107.0(6) . . ? F2 C2 C1 111.3(6) . . ? F1 C2 C1 112.3(6) . . ? F3 C2 C1 111.2(6) . . ? F19 C11 F21 108.7(6) . . ? F19 C11 F20 107.4(7) . . ? F21 C11 F20 107.2(6) . . ? F19 C11 C10 112.3(6) . . ? F21 C11 C10 110.8(6) . . ? F20 C11 C10 110.2(6) . . ? C4 O2 Bi1 122.4(4) . . ? C4 O2 Bi2 123.8(4) . . ? Bi1 O2 Bi2 113.71(19) . . ? C7 O3 Bi1 124.4(4) . . ? C15 C14 C13 119.2(7) . . ? C16 C15 C14 121.1(7) . . ? C13 C18 C17 120.1(7) . . ? C18 C13 C14 119.7(7) . . ? C18 C13 Bi1 119.4(5) . . ? C14 C13 Bi1 120.8(5) . . ? F13 C8 F15 108.4(6) . . ? F13 C8 F14 108.3(6) . . ? F15 C8 F14 106.2(6) . . ? F13 C8 C7 112.9(6) . . ? F15 C8 C7 111.8(6) . . ? F14 C8 C7 109.1(6) . . ? O2 C4 C5 110.2(6) . . ? O2 C4 C6 111.0(6) . . ? C5 C4 C6 111.5(6) . . ? O3 C7 C8 111.5(6) . . ? O3 C7 C9 107.0(6) . . ? C8 C7 C9 111.6(6) . . ? F24 C12 F22 108.1(7) . . ? F24 C12 F23 108.2(6) . . ? F22 C12 F23 106.5(6) . . ? F24 C12 C10 112.3(7) . . ? F22 C12 C10 109.6(6) . . ? F23 C12 C10 111.9(6) . . ? C15 C16 C17 119.7(7) . . ? F7 C5 F8 108.2(7) . . ? F7 C5 F9 106.8(7) . . ? F8 C5 F9 107.3(6) . . ? F7 C5 C4 112.0(6) . . ? F8 C5 C4 111.1(7) . . ? F9 C5 C4 111.3(6) . . ? F10 C6 F12 107.8(7) . . ? F10 C6 F11 107.8(6) . . ? F12 C6 F11 105.7(6) . . ? F10 C6 C4 111.1(6) . . ? F12 C6 C4 111.2(6) . . ? F11 C6 C4 112.8(7) . . ? C16 C17 C18 120.2(7) . . ? F17 C9 F16 106.8(7) . . ? F17 C9 F18 107.6(7) . . ? F16 C9 F18 106.5(7) . . ? F17 C9 C7 113.5(7) . . ? F16 C9 C7 112.0(7) . . ? F18 C9 C7 110.1(7) . . ? C24 C19 C20 119.2(7) . . ? C24 C19 Bi2 117.3(5) . . ? C20 C19 Bi2 123.0(5) . . ? C23 C24 C19 120.5(7) . . ? C21 C20 C19 119.3(7) . . ? C22 C23 C24 119.6(7) . . ? C23 C22 C21 120.4(7) . . ? C20 C21 C22 121.0(7) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 3.022 _refine_diff_density_min -4.847 _refine_diff_density_rms 0.377 # Attachment 'compound 7.cif' data_C:\compound2.CIF _database_code_depnum_ccdc_archive 'CCDC 637420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common X-Seed _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H13 Bi9 F78 O20' _chemical_formula_weight 4164.31 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' F F 0.0171 0.0103 '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 13.6373(3) _cell_length_b 14.1338(3) _cell_length_c 24.9763(6) _cell_angle_alpha 104.796(1) _cell_angle_beta 93.937(1) _cell_angle_gamma 113.026(1) _cell_volume 4206.08(16) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour transparent _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3712 _exptl_absorpt_coefficient_mu 18.988 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0922 _exptl_absorpt_correction_T_max 0.1629 _exptl_absorpt_process_details 'part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Nonius Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 75021 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 30.02 _reflns_number_total 24049 _reflns_number_gt 17639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction Nonius _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0112P)^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 24049 _refine_ls_number_parameters 1315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0533 _refine_ls_wR_factor_gt 0.0478 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi9 Bi 0.619142(15) 0.386267(16) 0.727879(8) 0.01008(4) Uani 1 1 d . . . Bi4 Bi 0.822079(15) 0.567093(16) 0.669230(8) 0.00955(4) Uani 1 1 d . . . Bi2 Bi 0.828963(15) 0.318078(16) 0.676365(8) 0.00978(4) Uani 1 1 d . . . Bi1 Bi 0.836043(15) 0.421479(16) 0.833252(8) 0.00950(4) Uani 1 1 d . . . Bi5 Bi 1.039278(15) 0.611601(16) 0.770621(8) 0.00969(4) Uani 1 1 d . . . Bi3 Bi 0.618384(15) 0.274347(16) 0.572039(8) 0.01123(5) Uani 1 1 d . . . Bi7 Bi 0.800782(15) 0.651437(16) 0.820873(8) 0.00981(4) Uani 1 1 d . . . Bi8 Bi 0.609015(16) 0.484529(17) 0.884600(8) 0.01133(5) Uani 1 1 d . . . Bi6 Bi 1.033276(16) 0.846326(16) 0.754037(9) 0.01206(5) Uani 1 1 d . . . O19 O 0.7235(3) 0.5498(3) 0.73212(14) 0.0096(8) Uani 1 1 d . . . O4 O 0.9138(3) 0.5742(3) 0.82260(14) 0.0095(8) Uani 1 1 d . . . O20 O 0.7476(3) 0.3424(3) 0.74907(14) 0.0116(8) Uani 1 1 d . . . O6 O 0.7110(3) 0.3793(3) 0.65247(14) 0.0101(8) Uani 1 1 d . . . O1 O 0.9641(3) 0.3986(3) 0.77975(14) 0.0120(8) Uani 1 1 d . . . O5 O 0.7035(3) 0.4809(3) 0.82109(14) 0.0108(8) Uani 1 1 d . . . O7 O 0.9180(3) 0.4938(3) 0.69577(14) 0.0107(8) Uani 1 1 d . . . O18 O 0.5016(3) 0.3425(3) 0.81210(15) 0.0140(8) Uani 1 1 d . . . O3 O 0.6868(3) 0.3807(3) 0.89975(16) 0.0152(9) Uani 1 1 d . . . O9 O 0.8076(3) 0.3093(3) 0.57937(14) 0.0122(8) Uani 1 1 d . . . O11 O 0.4948(3) 0.2947(3) 0.62063(15) 0.0149(9) Uani 1 1 d . . . O13 O 1.0941(3) 0.7108(3) 0.70467(15) 0.0146(8) Uani 1 1 d . . . O12 O 1.1051(3) 0.7940(3) 0.82849(15) 0.0137(8) Uani 1 1 d . . . O16 O 0.6120(3) 0.6073(3) 0.83116(15) 0.0162(9) Uani 1 1 d . . . O15 O 0.9051(3) 0.7869(3) 0.68018(15) 0.0177(9) Uani 1 1 d . . . O17 O 0.7868(3) 0.6241(3) 0.91338(14) 0.0149(8) Uani 1 1 d . . . O14 O 0.9227(3) 0.8799(3) 0.80646(16) 0.0195(9) Uani 1 1 d . . . F75 F 0.2362(2) 0.2151(3) 0.84155(13) 0.0220(8) Uani 1 1 d . . . O2 O 0.9334(3) 0.6874(3) 0.75176(14) 0.0085(8) Uani 1 1 d . . . F77 F 0.4209(3) 0.1187(3) 0.78939(15) 0.0303(9) Uani 1 1 d . . . F73 F 0.3636(3) 0.3737(3) 0.88345(14) 0.0256(8) Uani 1 1 d . . . O10 O 0.6548(3) 0.4350(3) 0.56355(15) 0.0148(8) Uani 1 1 d . . . F74 F 0.3848(2) 0.2322(3) 0.88609(13) 0.0240(8) Uani 1 1 d . . . F76 F 0.2677(3) 0.0967(3) 0.74706(15) 0.0345(10) Uani 1 1 d . . . O8 O 0.6479(3) 0.1804(3) 0.63718(15) 0.0154(9) Uani 1 1 d . . . F78 F 0.4139(3) 0.1728(3) 0.71722(13) 0.0274(9) Uani 1 1 d . . . F51 F 0.9308(3) 1.0505(3) 0.94107(14) 0.0384(10) Uani 1 1 d . . . F49 F 0.9437(3) 0.8991(3) 0.91833(16) 0.0401(10) Uani 1 1 d . . . F50 F 0.7966(3) 0.9061(3) 0.88852(15) 0.0400(10) Uani 1 1 d . . . F40 F 1.1838(4) 1.0017(3) 0.91468(19) 0.0588(13) Uani 1 1 d . . . C37 C 0.3905(4) 0.2762(4) 0.7999(2) 0.0114(11) Uani 1 1 d . . . H37 H 0.3535 0.3063 0.7775 0.014 Uiso 1 1 calc R . . C10 C 0.8576(4) 0.2671(4) 0.5392(2) 0.0150(12) Uani 1 1 d . . . H10 H 0.8328 0.2742 0.5024 0.018 Uiso 1 1 calc R . . F41 F 1.2456(3) 0.9967(3) 0.83825(18) 0.0683(15) Uani 1 1 d . . . C16 C 0.4061(4) 0.3057(5) 0.5970(2) 0.0192(13) Uani 1 1 d . . . H16 H 0.4323 0.3582 0.5752 0.023 Uiso 1 1 calc R . . F42 F 1.3454(3) 1.0143(3) 0.91357(18) 0.0536(13) Uani 1 1 d . . . C13 C 0.6577(4) 0.4677(4) 0.5160(2) 0.0150(12) Uani 1 1 d . . . H13 H 0.6555 0.5398 0.5270 0.018 Uiso 1 1 calc R . . C19 C 1.2013(4) 0.8436(5) 0.8673(2) 0.0187(13) Uani 1 1 d . . . H19 H 1.2560 0.8232 0.8488 0.022 Uiso 1 1 calc R . . C7 C 0.6160(4) 0.0713(4) 0.6293(2) 0.0180(13) Uani 1 1 d . . . H7 H 0.6618 0.0468 0.6047 0.022 Uiso 1 1 calc R . . C38 C 0.3438(4) 0.2731(5) 0.8530(2) 0.0149(12) Uani 1 1 d . . . C34 C 0.8495(4) 0.6912(4) 0.9656(2) 0.0146(12) Uani 1 1 d . . . H34 H 0.9097 0.7542 0.9597 0.018 Uiso 1 1 calc R . . C39 C 0.3727(4) 0.1641(5) 0.7631(3) 0.0205(14) Uani 1 1 d . . . C21 C 1.2446(5) 0.9646(5) 0.8845(3) 0.0357(18) Uani 1 1 d . . . C25 C 0.9490(4) 0.9786(4) 0.8463(2) 0.0189(13) Uani 1 1 d . . . H25 H 1.0299 1.0183 0.8570 0.023 Uiso 1 1 calc R . . C26 C 0.9030(5) 0.9599(5) 0.8994(3) 0.0235(14) Uani 1 1 d . . . C4 C 0.6343(4) 0.2874(5) 0.9138(2) 0.0165(13) Uani 1 1 d . . . H4 H 0.5629 0.2441 0.8874 0.020 Uiso 1 1 calc R . . C11 C 0.9803(5) 0.3350(5) 0.5566(3) 0.0200(13) Uani 1 1 d . . . F30 F 0.4683(2) 0.3836(3) 0.48827(14) 0.0246(8) Uani 1 1 d . . . F24 F 0.8514(3) 0.1311(3) 0.57981(15) 0.0300(9) Uani 1 1 d . . . F1 F 1.0574(3) 0.4592(3) 0.88887(13) 0.0270(9) Uani 1 1 d . . . F23 F 0.7172(3) 0.0949(3) 0.51619(14) 0.0315(9) Uani 1 1 d . . . F19 F 1.0167(2) 0.3419(3) 0.60907(14) 0.0304(9) Uani 1 1 d . . . F13 F 0.7441(3) 0.1047(3) 0.70756(16) 0.0372(10) Uani 1 1 d . . . F7 F 0.5691(3) 0.3826(3) 0.98170(14) 0.0296(9) Uani 1 1 d . . . F27 F 0.8481(3) 0.5480(3) 0.53562(14) 0.0308(9) Uani 1 1 d . . . F20 F 1.0045(3) 0.4360(3) 0.55608(16) 0.0333(9) Uani 1 1 d . . . F66 F 0.6700(3) 0.7563(3) 0.77639(14) 0.0249(8) Uani 1 1 d . . . F4 F 1.1351(3) 0.4119(3) 0.72853(15) 0.0365(10) Uani 1 1 d . . . F11 F 0.8035(3) 0.2788(3) 0.93200(16) 0.0416(11) Uani 1 1 d . . . F5 F 1.0162(3) 0.2483(3) 0.70361(14) 0.0352(10) Uani 1 1 d . . . F48 F 1.1691(3) 0.8728(3) 0.65819(15) 0.0357(10) Uani 1 1 d . . . F71 F 0.8345(3) 0.7920(3) 1.05445(14) 0.0343(10) Uani 1 1 d . . . F69 F 0.9749(3) 0.6989(3) 1.03929(14) 0.0331(9) Uani 1 1 d . . . F46 F 1.2499(3) 0.7976(3) 0.60388(14) 0.0320(9) Uani 1 1 d . . . F57 F 1.0307(3) 0.9923(3) 0.68135(15) 0.0337(9) Uani 1 1 d . . . F28 F 0.5579(3) 0.4259(3) 0.42429(14) 0.0319(9) Uani 1 1 d . . . F63 F 0.4545(3) 0.6048(3) 0.89719(16) 0.0351(10) Uani 1 1 d . . . F10 F 0.7068(3) 0.1929(3) 0.84935(15) 0.0344(9) Uani 1 1 d . . . F8 F 0.7006(3) 0.3516(3) 1.01311(14) 0.0335(9) Uani 1 1 d . . . F64 F 0.5023(3) 0.6507(3) 0.74202(16) 0.0437(11) Uani 1 1 d . . . F52 F 0.8000(3) 0.9951(3) 0.80033(16) 0.0390(10) Uani 1 1 d . . . F47 F 1.0770(3) 0.7219(3) 0.59437(15) 0.0382(10) Uani 1 1 d . . . F54 F 0.9564(3) 1.0677(3) 0.77925(15) 0.0402(10) Uani 1 1 d . . . F9 F 0.5415(3) 0.2221(3) 0.98254(15) 0.0355(10) Uani 1 1 d . . . F21 F 1.0350(3) 0.2952(3) 0.52289(14) 0.0314(9) Uani 1 1 d . . . F14 F 0.5886(3) 0.0935(3) 0.72424(15) 0.0320(9) Uani 1 1 d . . . F70 F 0.6903(3) 0.6548(3) 1.00464(15) 0.0390(10) Uani 1 1 d . . . F29 F 0.5531(3) 0.2923(3) 0.45129(15) 0.0350(10) Uani 1 1 d . . . F72 F 0.7525(3) 0.7975(3) 0.97953(16) 0.0399(10) Uani 1 1 d . . . F68 F 0.8258(3) 0.5542(3) 1.00858(15) 0.0366(10) Uani 1 1 d . . . F67 F 0.9481(3) 0.5856(3) 0.95755(14) 0.0341(10) Uani 1 1 d . . . F53 F 0.9244(3) 1.1407(3) 0.85873(15) 0.0378(10) Uani 1 1 d . . . F37 F 1.1558(3) 0.6944(3) 0.90079(16) 0.0430(11) Uani 1 1 d . . . F25 F 0.7724(3) 0.3889(3) 0.47705(15) 0.0377(10) Uani 1 1 d . . . F62 F 0.3902(3) 0.5371(3) 0.80878(16) 0.0373(10) Uani 1 1 d . . . F18 F 0.4830(3) 0.0369(3) 0.55426(16) 0.0436(11) Uani 1 1 d . . . F26 F 0.7720(3) 0.5219(3) 0.45152(15) 0.0411(11) Uani 1 1 d . . . F17 F 0.4708(3) -0.0978(3) 0.58116(18) 0.0475(12) Uani 1 1 d . . . F61 F 0.4019(3) 0.6940(3) 0.85304(17) 0.0400(11) Uani 1 1 d . . . F12 F 0.6601(3) 0.1329(3) 0.91875(17) 0.0431(11) Uani 1 1 d . . . F2 F 1.1824(3) 0.5196(3) 0.84275(15) 0.0356(10) Uani 1 1 d . . . F16 F 0.4292(3) 0.0217(3) 0.63092(15) 0.0383(10) Uani 1 1 d . . . F60 F 0.7038(3) 0.8309(3) 0.60595(16) 0.0450(11) Uani 1 1 d . . . F34 F 0.3731(3) 0.1662(3) 0.51571(15) 0.0451(11) Uani 1 1 d . . . F22 F 0.8678(3) 0.1032(3) 0.49253(16) 0.0398(11) Uani 1 1 d . . . F59 F 0.7723(3) 0.7197(3) 0.57630(16) 0.0431(11) Uani 1 1 d . . . F58 F 0.6866(3) 0.7063(3) 0.64358(17) 0.0482(12) Uani 1 1 d . . . F38 F 1.1089(3) 0.8178(4) 0.94254(16) 0.0499(12) Uani 1 1 d . . . F65 F 0.5475(3) 0.8091(3) 0.79872(18) 0.0460(11) Uani 1 1 d . . . F31 F 0.2821(3) 0.3788(4) 0.62636(16) 0.0513(13) Uani 1 1 d . . . F43 F 1.2826(3) 0.7104(4) 0.74735(17) 0.0537(13) Uani 1 1 d . . . F55 F 0.9646(3) 0.8934(4) 0.59545(16) 0.0555(13) Uani 1 1 d . . . C15 C 0.5593(5) 0.3916(5) 0.4690(2) 0.0181(13) Uani 1 1 d . . . F39 F 1.2759(3) 0.8462(3) 0.95647(16) 0.0484(12) Uani 1 1 d . . . F15 F 0.6063(3) -0.0501(3) 0.68158(17) 0.0475(11) Uani 1 1 d . . . F33 F 0.4328(4) 0.4401(4) 0.68115(19) 0.0812(19) Uani 1 1 d . . . F45 F 1.3630(3) 0.7626(4) 0.68250(18) 0.0695(16) Uani 1 1 d . . . F56 F 0.9005(3) 1.0047(3) 0.63473(19) 0.0576(13) Uani 1 1 d . . . F35 F 0.2406(3) 0.2096(4) 0.53194(18) 0.0617(14) Uani 1 1 d . . . F44 F 1.3127(3) 0.8674(4) 0.74194(18) 0.0649(14) Uani 1 1 d . . . C9 C 0.4978(5) 0.0069(5) 0.5996(3) 0.0267(15) Uani 1 1 d . . . F36 F 0.2852(3) 0.1231(4) 0.5805(2) 0.0639(14) Uani 1 1 d . . . C3 C 1.0876(5) 0.3278(6) 0.7471(3) 0.0260(16) Uani 1 1 d . . . C5 C 0.6120(5) 0.3091(5) 0.9737(3) 0.0243(14) Uani 1 1 d . . . C35 C 0.9003(5) 0.6325(5) 0.9936(2) 0.0203(13) Uani 1 1 d . . . C33 C 0.5704(4) 0.7246(5) 0.7890(3) 0.0234(14) Uani 1 1 d . . . C12 C 0.8260(5) 0.1488(5) 0.5316(3) 0.0217(14) Uani 1 1 d . . . C24 C 1.1693(5) 0.7781(5) 0.6324(3) 0.0237(14) Uani 1 1 d . . . C1 C 1.0309(4) 0.3535(5) 0.7956(2) 0.0159(13) Uani 1 1 d . . . H1 H 0.9847 0.2844 0.8025 0.019 Uiso 1 1 calc R . . C14 C 0.7627(5) 0.4825(5) 0.4943(3) 0.0237(14) Uani 1 1 d . . . C18 C 0.3243(5) 0.2000(6) 0.5572(3) 0.0330(17) Uani 1 1 d . . . C6 C 0.7017(5) 0.2214(5) 0.9041(3) 0.0257(15) Uani 1 1 d . . . C27 C 0.9048(5) 1.0458(5) 0.8219(3) 0.0266(15) Uani 1 1 d . . . C22 C 1.1759(4) 0.7163(5) 0.6728(2) 0.0215(14) Uani 1 1 d . . . H22 H 1.1610 0.6410 0.6501 0.026 Uiso 1 1 calc R . . C32 C 0.4525(5) 0.6288(5) 0.8490(3) 0.0240(15) Uani 1 1 d . . . C8 C 0.6363(5) 0.0544(5) 0.6857(3) 0.0274(16) Uani 1 1 d . . . C29 C 0.9387(6) 0.9342(5) 0.6425(3) 0.0338(17) Uani 1 1 d . . . C20 C 1.1862(5) 0.8013(5) 0.9174(3) 0.0278(16) Uani 1 1 d . . . C28 C 0.8593(5) 0.8505(5) 0.6652(2) 0.0228(14) Uani 1 1 d . . . H28 H 0.8409 0.8893 0.6996 0.027 Uiso 1 1 calc R . . C31 C 0.5674(4) 0.6813(4) 0.8383(2) 0.0163(13) Uani 1 1 d . . . H31 H 0.6116 0.7434 0.8727 0.020 Uiso 1 1 calc R . . C36 C 0.7817(5) 0.7342(5) 1.0018(3) 0.0266(15) Uani 1 1 d . . . C2 C 1.1107(5) 0.4286(5) 0.8494(3) 0.0234(15) Uani 1 1 d . . . C17 C 0.3571(6) 0.3518(7) 0.6441(3) 0.0373(19) Uani 1 1 d . . . C23 C 1.2860(6) 0.7657(7) 0.7106(3) 0.043(2) Uani 1 1 d . . . C30 C 0.7547(5) 0.7775(5) 0.6223(3) 0.0270(16) Uani 1 1 d . . . F6 F 1.1630(3) 0.2961(4) 0.76083(15) 0.0434(12) Uani 1 1 d . . . F3 F 1.1657(3) 0.3833(4) 0.87079(14) 0.0439(12) Uani 1 1 d . . . F32 F 0.3144(4) 0.2853(5) 0.67401(18) 0.0733(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 Bi9 0.00722(9) 0.00854(10) 0.01231(10) 0.00255(8) 0.00156(8) 0.00161(8) Bi4 0.01030(9) 0.00905(10) 0.00908(10) 0.00343(8) 0.00208(8) 0.00344(8) Bi2 0.01026(10) 0.00750(10) 0.01130(11) 0.00191(8) 0.00257(8) 0.00401(8) Bi1 0.00983(9) 0.00900(10) 0.01016(10) 0.00401(8) 0.00255(8) 0.00372(8) Bi5 0.00718(9) 0.00912(10) 0.01111(10) 0.00255(8) 0.00102(8) 0.00224(8) Bi3 0.01028(10) 0.00871(10) 0.01025(10) -0.00043(8) -0.00025(8) 0.00196(8) Bi7 0.01101(10) 0.00718(10) 0.01006(10) 0.00127(8) 0.00156(8) 0.00358(8) Bi8 0.01118(10) 0.01273(11) 0.01100(11) 0.00377(9) 0.00492(8) 0.00546(8) Bi6 0.01231(10) 0.00696(10) 0.01320(11) 0.00345(8) 0.00074(8) 0.00038(8) O19 0.0079(17) 0.0089(19) 0.0115(19) 0.0033(16) 0.0027(15) 0.0027(15) O4 0.0085(18) 0.0051(18) 0.014(2) 0.0007(16) 0.0008(15) 0.0036(15) O20 0.0107(18) 0.011(2) 0.0098(19) 0.0001(16) 0.0002(15) 0.0037(16) O6 0.0111(18) 0.0054(19) 0.012(2) 0.0004(15) 0.0017(15) 0.0026(15) O1 0.0133(19) 0.014(2) 0.013(2) 0.0045(17) 0.0036(16) 0.0090(16) O5 0.0135(19) 0.0076(19) 0.011(2) 0.0008(16) 0.0050(15) 0.0054(16) O7 0.0074(17) 0.0079(19) 0.014(2) 0.0009(16) 0.0039(15) 0.0023(15) O18 0.0090(18) 0.012(2) 0.015(2) 0.0014(17) 0.0057(16) 0.0004(16) O3 0.014(2) 0.017(2) 0.023(2) 0.0141(18) 0.0091(17) 0.0079(17) O9 0.0133(19) 0.018(2) 0.0054(19) 0.0047(16) 0.0042(15) 0.0062(17) O11 0.0114(19) 0.020(2) 0.015(2) 0.0060(17) 0.0007(16) 0.0076(17) O13 0.015(2) 0.014(2) 0.017(2) 0.0089(17) 0.0109(17) 0.0055(17) O12 0.0133(19) 0.011(2) 0.012(2) 0.0016(16) -0.0048(16) 0.0023(16) O16 0.015(2) 0.018(2) 0.021(2) 0.0107(18) 0.0051(17) 0.0097(17) O15 0.021(2) 0.012(2) 0.017(2) 0.0023(17) -0.0032(17) 0.0065(18) O17 0.016(2) 0.016(2) 0.0071(19) 0.0021(16) 0.0005(16) 0.0032(17) O14 0.021(2) 0.008(2) 0.023(2) -0.0020(18) 0.0027(18) 0.0045(17) F75 0.0132(17) 0.025(2) 0.029(2) 0.0139(17) 0.0099(15) 0.0055(15) O2 0.0087(17) 0.0046(18) 0.0102(19) 0.0015(15) 0.0012(14) 0.0014(14) F77 0.039(2) 0.018(2) 0.037(2) 0.0088(18) 0.0086(18) 0.0142(18) F73 0.0241(19) 0.022(2) 0.026(2) 0.0001(16) 0.0126(16) 0.0087(16) O10 0.020(2) 0.012(2) 0.013(2) 0.0033(17) 0.0027(16) 0.0081(17) F74 0.0236(19) 0.036(2) 0.022(2) 0.0175(17) 0.0080(15) 0.0167(17) F76 0.0192(19) 0.024(2) 0.038(2) -0.0025(18) 0.0061(17) -0.0068(16) O8 0.019(2) 0.006(2) 0.021(2) 0.0026(17) 0.0036(17) 0.0055(16) F78 0.028(2) 0.026(2) 0.019(2) 0.0007(16) 0.0098(16) 0.0060(17) F51 0.065(3) 0.022(2) 0.016(2) -0.0023(17) 0.0094(19) 0.010(2) F49 0.055(3) 0.039(3) 0.039(3) 0.022(2) 0.012(2) 0.025(2) F50 0.032(2) 0.042(3) 0.033(2) 0.012(2) 0.0137(18) 0.0014(19) F40 0.065(3) 0.025(3) 0.074(3) -0.009(2) -0.005(3) 0.024(2) C37 0.012(3) 0.011(3) 0.011(3) 0.003(2) 0.001(2) 0.006(2) C10 0.016(3) 0.019(3) 0.016(3) 0.009(3) 0.006(2) 0.011(2) F41 0.071(3) 0.034(3) 0.052(3) 0.032(2) -0.033(2) -0.030(2) C16 0.021(3) 0.025(4) 0.014(3) 0.005(3) 0.004(2) 0.012(3) F42 0.035(2) 0.028(2) 0.067(3) 0.016(2) -0.030(2) -0.0129(19) C13 0.017(3) 0.012(3) 0.016(3) 0.005(2) 0.002(2) 0.006(2) C19 0.021(3) 0.012(3) 0.020(3) 0.003(3) 0.003(3) 0.004(3) C7 0.020(3) 0.007(3) 0.024(3) 0.002(3) 0.006(3) 0.004(2) C38 0.016(3) 0.014(3) 0.020(3) 0.008(3) 0.007(2) 0.009(2) C34 0.012(3) 0.010(3) 0.017(3) 0.003(2) 0.001(2) 0.001(2) C39 0.014(3) 0.012(3) 0.028(4) 0.004(3) 0.004(3) -0.002(2) C21 0.035(4) 0.017(4) 0.034(4) 0.007(3) -0.016(3) -0.006(3) C25 0.015(3) 0.009(3) 0.030(4) 0.005(3) 0.011(3) 0.002(2) C26 0.024(3) 0.011(3) 0.030(4) 0.001(3) 0.001(3) 0.005(3) C4 0.014(3) 0.021(3) 0.020(3) 0.014(3) 0.007(2) 0.007(2) C11 0.018(3) 0.020(3) 0.023(3) 0.008(3) 0.009(3) 0.008(3) F30 0.0149(17) 0.026(2) 0.030(2) 0.0086(17) -0.0001(15) 0.0060(15) F24 0.043(2) 0.023(2) 0.034(2) 0.0129(18) 0.0080(18) 0.0206(18) F1 0.028(2) 0.047(3) 0.0150(19) 0.0064(17) 0.0054(15) 0.0269(19) F23 0.026(2) 0.021(2) 0.034(2) -0.0030(17) 0.0039(17) 0.0036(16) F19 0.0160(18) 0.042(2) 0.024(2) 0.0043(18) -0.0011(15) 0.0074(17) F13 0.025(2) 0.040(3) 0.056(3) 0.032(2) 0.0046(19) 0.0132(19) F7 0.039(2) 0.035(2) 0.026(2) 0.0160(18) 0.0183(17) 0.0221(19) F27 0.0190(19) 0.041(2) 0.030(2) 0.0129(19) 0.0035(16) 0.0095(18) F20 0.025(2) 0.024(2) 0.053(3) 0.018(2) 0.0184(18) 0.0067(17) F66 0.0242(19) 0.024(2) 0.035(2) 0.0176(17) 0.0117(16) 0.0122(16) F4 0.034(2) 0.054(3) 0.029(2) 0.020(2) 0.0174(18) 0.021(2) F11 0.026(2) 0.051(3) 0.054(3) 0.020(2) 0.0006(19) 0.022(2) F5 0.041(2) 0.047(3) 0.022(2) -0.0047(19) -0.0004(17) 0.034(2) F48 0.058(3) 0.024(2) 0.034(2) 0.0166(19) 0.028(2) 0.020(2) F71 0.036(2) 0.036(2) 0.019(2) -0.0051(18) 0.0031(17) 0.0132(19) F69 0.035(2) 0.025(2) 0.022(2) -0.0042(17) -0.0158(16) 0.0069(18) F46 0.028(2) 0.035(2) 0.028(2) 0.0114(18) 0.0173(17) 0.0051(18) F57 0.033(2) 0.019(2) 0.042(2) 0.0144(18) -0.0019(18) 0.0017(17) F28 0.032(2) 0.036(2) 0.021(2) 0.0139(18) -0.0037(16) 0.0066(18) F63 0.037(2) 0.041(3) 0.045(3) 0.023(2) 0.0286(19) 0.025(2) F10 0.050(2) 0.031(2) 0.037(2) 0.0162(19) 0.024(2) 0.025(2) F8 0.034(2) 0.039(2) 0.022(2) 0.0129(18) -0.0013(17) 0.0091(19) F64 0.034(2) 0.045(3) 0.039(3) 0.021(2) -0.0098(19) 0.001(2) F52 0.035(2) 0.034(2) 0.048(3) 0.010(2) -0.0040(19) 0.018(2) F47 0.031(2) 0.051(3) 0.025(2) 0.020(2) 0.0029(18) 0.005(2) F54 0.068(3) 0.025(2) 0.027(2) 0.0108(18) 0.016(2) 0.016(2) F9 0.034(2) 0.033(2) 0.037(2) 0.0214(19) 0.0156(18) 0.0021(18) F21 0.027(2) 0.040(2) 0.034(2) 0.0097(19) 0.0207(17) 0.0205(19) F14 0.039(2) 0.034(2) 0.030(2) 0.0157(19) 0.0159(18) 0.0168(19) F70 0.030(2) 0.042(3) 0.029(2) -0.0017(19) 0.0155(18) 0.0040(19) F29 0.042(2) 0.017(2) 0.036(2) -0.0041(18) -0.0089(18) 0.0133(18) F72 0.052(3) 0.042(3) 0.039(3) 0.011(2) 0.014(2) 0.034(2) F68 0.051(3) 0.021(2) 0.029(2) 0.0142(18) -0.0031(19) 0.0035(19) F67 0.042(2) 0.039(3) 0.026(2) 0.0019(19) 0.0012(18) 0.028(2) F53 0.071(3) 0.018(2) 0.025(2) 0.0012(17) 0.004(2) 0.024(2) F37 0.060(3) 0.017(2) 0.041(3) 0.0099(19) -0.021(2) 0.009(2) F25 0.039(2) 0.053(3) 0.035(2) 0.009(2) 0.0109(19) 0.036(2) F62 0.0196(19) 0.031(2) 0.053(3) 0.009(2) 0.0095(18) 0.0040(17) F18 0.037(2) 0.034(2) 0.030(2) 0.0044(19) -0.0062(18) -0.0098(19) F26 0.026(2) 0.071(3) 0.037(2) 0.040(2) 0.0123(18) 0.017(2) F17 0.041(2) 0.0079(19) 0.075(3) -0.006(2) 0.015(2) 0.0028(18) F61 0.035(2) 0.044(3) 0.071(3) 0.035(2) 0.029(2) 0.034(2) F12 0.055(3) 0.031(2) 0.065(3) 0.034(2) 0.028(2) 0.025(2) F2 0.0141(18) 0.041(3) 0.038(2) 0.001(2) 0.0001(16) 0.0053(18) F16 0.022(2) 0.037(2) 0.043(3) -0.005(2) 0.0128(18) 0.0087(18) F60 0.048(3) 0.035(3) 0.051(3) 0.001(2) -0.021(2) 0.029(2) F34 0.041(2) 0.049(3) 0.029(2) -0.014(2) -0.0111(19) 0.021(2) F22 0.041(2) 0.025(2) 0.048(3) -0.004(2) 0.023(2) 0.0161(19) F59 0.049(3) 0.032(2) 0.034(2) -0.009(2) -0.0188(19) 0.019(2) F58 0.027(2) 0.041(3) 0.061(3) 0.017(2) -0.012(2) 0.000(2) F38 0.060(3) 0.064(3) 0.035(3) 0.028(2) 0.022(2) 0.025(3) F65 0.050(3) 0.039(3) 0.082(3) 0.041(2) 0.031(2) 0.036(2) F31 0.059(3) 0.097(4) 0.037(3) 0.027(3) 0.016(2) 0.067(3) F43 0.033(2) 0.104(4) 0.053(3) 0.051(3) 0.020(2) 0.039(3) F55 0.071(3) 0.059(3) 0.024(2) 0.017(2) 0.012(2) 0.012(3) C15 0.020(3) 0.013(3) 0.025(3) 0.009(3) 0.007(3) 0.008(3) F39 0.046(3) 0.044(3) 0.034(2) 0.014(2) -0.0259(19) 0.001(2) F15 0.068(3) 0.026(2) 0.065(3) 0.031(2) 0.028(2) 0.024(2) F33 0.077(4) 0.099(5) 0.055(3) -0.038(3) -0.022(3) 0.069(4) F45 0.032(2) 0.140(5) 0.065(3) 0.062(3) 0.034(2) 0.042(3) F56 0.064(3) 0.027(2) 0.083(4) 0.031(2) -0.014(3) 0.017(2) F35 0.029(2) 0.084(4) 0.055(3) -0.004(3) -0.023(2) 0.027(2) F44 0.044(3) 0.057(3) 0.048(3) 0.004(3) -0.017(2) -0.014(2) C9 0.032(4) 0.004(3) 0.035(4) -0.001(3) 0.014(3) 0.002(3) F36 0.035(3) 0.040(3) 0.083(4) 0.019(3) -0.002(2) -0.016(2) C3 0.030(4) 0.041(4) 0.016(3) 0.004(3) -0.001(3) 0.028(3) C5 0.023(3) 0.020(4) 0.030(4) 0.011(3) 0.007(3) 0.007(3) C35 0.026(3) 0.018(3) 0.011(3) 0.002(3) -0.002(3) 0.006(3) C33 0.012(3) 0.023(4) 0.041(4) 0.012(3) 0.007(3) 0.011(3) C12 0.022(3) 0.022(4) 0.025(4) 0.006(3) 0.012(3) 0.012(3) C24 0.026(3) 0.017(3) 0.021(3) 0.006(3) 0.012(3) 0.000(3) C1 0.014(3) 0.024(3) 0.019(3) 0.013(3) 0.008(2) 0.013(3) C14 0.026(3) 0.026(4) 0.023(4) 0.011(3) 0.004(3) 0.012(3) C18 0.023(4) 0.034(4) 0.033(4) 0.004(3) -0.003(3) 0.008(3) C6 0.025(4) 0.026(4) 0.035(4) 0.019(3) 0.011(3) 0.014(3) C27 0.037(4) 0.015(3) 0.023(4) 0.003(3) 0.001(3) 0.009(3) C22 0.015(3) 0.021(3) 0.021(3) 0.003(3) 0.007(3) 0.002(3) C32 0.021(3) 0.022(4) 0.035(4) 0.009(3) 0.010(3) 0.015(3) C8 0.019(3) 0.018(3) 0.047(5) 0.015(3) 0.009(3) 0.007(3) C29 0.041(4) 0.017(4) 0.041(5) 0.016(3) -0.007(4) 0.007(3) C20 0.024(3) 0.026(4) 0.021(4) 0.001(3) -0.009(3) 0.004(3) C28 0.030(4) 0.014(3) 0.019(3) 0.000(3) -0.008(3) 0.009(3) C31 0.011(3) 0.014(3) 0.028(3) 0.005(3) 0.004(2) 0.010(2) C36 0.030(4) 0.023(4) 0.020(4) 0.002(3) 0.006(3) 0.008(3) C2 0.020(3) 0.036(4) 0.019(3) 0.006(3) -0.003(3) 0.020(3) C17 0.041(4) 0.066(6) 0.028(4) 0.016(4) 0.014(4) 0.044(4) C23 0.028(4) 0.071(6) 0.041(5) 0.027(5) 0.019(4) 0.023(4) C30 0.029(4) 0.016(3) 0.028(4) -0.002(3) -0.013(3) 0.010(3) F6 0.051(3) 0.082(3) 0.027(2) 0.015(2) 0.0098(19) 0.060(3) F3 0.054(3) 0.079(3) 0.021(2) 0.006(2) -0.0008(19) 0.058(3) F32 0.097(4) 0.148(5) 0.055(3) 0.073(4) 0.059(3) 0.099(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 Bi9 O20 2.150(3) . ? Bi9 O19 2.159(3) . ? Bi9 O5 2.318(3) . ? Bi9 O6 2.335(3) . ? Bi9 O11 2.759(3) . ? Bi9 Bi2 3.5779(3) . ? Bi9 Bi1 3.6103(3) . ? Bi9 Bi7 3.6164(3) . ? Bi9 Bi4 3.6431(3) . ? Bi4 O7 2.125(3) . ? Bi4 O19 2.136(3) . ? Bi4 O2 2.282(3) . ? Bi4 O6 2.391(3) . ? Bi4 Bi5 3.5044(3) . ? Bi4 Bi2 3.6061(3) . ? Bi2 O7 2.196(3) . ? Bi2 O20 2.214(3) . ? Bi2 O6 2.217(3) . ? Bi2 O9 2.385(3) . ? Bi2 O8 2.403(4) . ? Bi2 O1 2.750(3) . ? Bi2 Bi3 3.4899(3) . ? Bi1 O4 2.097(3) . ? Bi1 O20 2.127(3) . ? Bi1 O5 2.303(3) . ? Bi1 O1 2.341(3) . ? Bi1 O3 2.696(3) . ? Bi1 Bi7 3.5505(3) . ? Bi5 O2 2.197(3) . ? Bi5 O7 2.199(3) . ? Bi5 O4 2.200(3) . ? Bi5 O12 2.377(4) . ? Bi5 O13 2.402(4) . ? Bi5 Bi6 3.4777(3) . ? Bi3 O6 2.120(3) . ? Bi3 O10 2.196(4) . ? Bi3 O11 2.208(3) . ? Bi3 O9 2.414(3) . ? Bi3 O8 2.450(4) . ? Bi7 O4 2.214(3) . ? Bi7 O19 2.226(3) . ? Bi7 O5 2.253(4) . ? Bi7 O17 2.446(4) . ? Bi7 O16 2.450(3) . ? Bi7 O2 2.582(3) . ? Bi7 Bi8 3.5497(3) . ? Bi8 O5 2.115(3) . ? Bi8 O3 2.207(3) . ? Bi8 O18 2.221(4) . ? Bi8 O17 2.362(4) . ? Bi8 O16 2.435(4) . ? Bi6 O2 2.106(3) . ? Bi6 O14 2.174(4) . ? Bi6 O15 2.187(4) . ? Bi6 O12 2.446(3) . ? Bi6 O13 2.460(3) . ? O1 C1 1.388(6) . ? O18 C37 1.395(6) . ? O3 C4 1.381(6) . ? O9 C10 1.390(6) . ? O11 C16 1.390(6) . ? O13 C22 1.403(6) . ? O12 C19 1.383(6) . ? O16 C31 1.383(6) . ? O15 C28 1.384(6) . ? O17 C34 1.383(6) . ? O14 C25 1.384(6) . ? F75 C38 1.338(6) . ? F77 C39 1.327(7) . ? F73 C38 1.338(6) . ? O10 C13 1.378(6) . ? F74 C38 1.328(6) . ? F76 C39 1.333(6) . ? O8 C7 1.383(6) . ? F78 C39 1.323(6) . ? F51 C26 1.324(6) . ? F49 C26 1.348(7) . ? F50 C26 1.317(7) . ? F40 C21 1.325(8) . ? C37 C38 1.513(7) . ? C37 C39 1.530(7) . ? C10 C12 1.510(8) . ? C10 C11 1.531(7) . ? F41 C21 1.343(7) . ? C16 C18 1.499(8) . ? C16 C17 1.521(8) . ? F42 C21 1.326(7) . ? C13 C14 1.522(8) . ? C13 C15 1.532(7) . ? C19 C21 1.503(8) . ? C19 C20 1.511(8) . ? C7 C8 1.514(8) . ? C7 C9 1.524(8) . ? C34 C36 1.523(8) . ? C34 C35 1.528(8) . ? C25 C27 1.527(8) . ? C25 C26 1.545(8) . ? C4 C5 1.524(8) . ? C4 C6 1.536(8) . ? C11 F21 1.323(6) . ? C11 F19 1.335(6) . ? C11 F20 1.337(6) . ? F30 C15 1.337(6) . ? F24 C12 1.341(6) . ? F1 C2 1.348(6) . ? F23 C12 1.347(6) . ? F13 C8 1.356(7) . ? F7 C5 1.359(7) . ? F27 C14 1.335(7) . ? F66 C33 1.342(6) . ? F4 C3 1.330(7) . ? F11 C6 1.330(7) . ? F5 C3 1.329(7) . ? F48 C24 1.330(7) . ? F71 C36 1.332(7) . ? F69 C35 1.328(6) . ? F46 C24 1.328(6) . ? F57 C29 1.345(7) . ? F28 C15 1.327(6) . ? F63 C32 1.333(7) . ? F10 C6 1.337(7) . ? F8 C5 1.326(7) . ? F64 C33 1.341(7) . ? F52 C27 1.320(7) . ? F47 C24 1.337(7) . ? F54 C27 1.352(7) . ? F9 C5 1.316(7) . ? F14 C8 1.323(7) . ? F70 C36 1.332(7) . ? F29 C15 1.326(6) . ? F72 C36 1.331(7) . ? F68 C35 1.335(7) . ? F67 C35 1.338(6) . ? F53 C27 1.332(6) . ? F37 C20 1.338(7) . ? F25 C14 1.344(7) . ? F62 C32 1.329(7) . ? F18 C9 1.335(7) . ? F26 C14 1.317(6) . ? F17 C9 1.319(6) . ? F61 C32 1.341(6) . ? F12 C6 1.315(7) . ? F2 C2 1.336(7) . ? F16 C9 1.303(6) . ? F60 C30 1.322(6) . ? F34 C18 1.354(7) . ? F22 C12 1.317(6) . ? F59 C30 1.326(7) . ? F58 C30 1.330(7) . ? F38 C20 1.331(7) . ? F65 C33 1.319(6) . ? F31 C17 1.310(7) . ? F43 C23 1.341(8) . ? F55 C29 1.307(8) . ? F39 C20 1.328(6) . ? F15 C8 1.342(7) . ? F33 C17 1.324(8) . ? F45 C23 1.311(7) . ? F56 C29 1.338(7) . ? F35 C18 1.337(7) . ? F44 C23 1.337(9) . ? F36 C18 1.310(8) . ? C3 F6 1.329(6) . ? C3 C1 1.523(8) . ? C33 C31 1.504(8) . ? C24 C22 1.512(8) . ? C1 C2 1.512(8) . ? C22 C23 1.511(9) . ? C32 C31 1.524(8) . ? C29 C28 1.522(9) . ? C28 C30 1.524(8) . ? C2 F3 1.324(6) . ? C17 F32 1.331(8) . ? 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 O20 Bi9 O19 95.97(13) . . ? O20 Bi9 O5 70.68(12) . . ? O19 Bi9 O5 72.03(12) . . ? O20 Bi9 O6 72.30(12) . . ? O19 Bi9 O6 71.88(12) . . ? O5 Bi9 O6 124.12(12) . . ? O20 Bi9 O11 120.10(11) . . ? O19 Bi9 O11 105.02(12) . . ? O5 Bi9 O11 169.22(11) . . ? O6 Bi9 O11 62.87(11) . . ? O20 Bi9 Bi2 35.53(9) . . ? O19 Bi9 Bi2 85.93(8) . . ? O5 Bi9 Bi2 99.69(8) . . ? O6 Bi9 Bi2 37.02(8) . . ? O11 Bi9 Bi2 90.33(7) . . ? O20 Bi9 Bi1 32.21(9) . . ? O19 Bi9 Bi1 83.80(9) . . ? O5 Bi9 Bi1 38.47(8) . . ? O6 Bi9 Bi1 96.60(8) . . ? O11 Bi9 Bi1 152.31(7) . . ? Bi2 Bi9 Bi1 63.758(6) . . ? O20 Bi9 Bi7 84.32(9) . . ? O19 Bi9 Bi7 35.05(9) . . ? O5 Bi9 Bi7 37.09(9) . . ? O6 Bi9 Bi7 99.54(8) . . ? O11 Bi9 Bi7 138.51(8) . . ? Bi2 Bi9 Bi7 95.356(6) . . ? Bi1 Bi9 Bi7 58.852(6) . . ? O20 Bi9 Bi4 83.35(9) . . ? O19 Bi9 Bi4 31.79(9) . . ? O5 Bi9 Bi4 95.11(9) . . ? O6 Bi9 Bi4 40.12(8) . . ? O11 Bi9 Bi4 86.45(8) . . ? Bi2 Bi9 Bi4 59.912(6) . . ? Bi1 Bi9 Bi4 88.375(6) . . ? Bi7 Bi9 Bi4 61.966(6) . . ? O7 Bi4 O19 96.41(13) . . ? O7 Bi4 O2 73.96(12) . . ? O19 Bi4 O2 74.62(12) . . ? O7 Bi4 O6 70.68(12) . . ? O19 Bi4 O6 71.15(12) . . ? O2 Bi4 O6 126.63(12) . . ? O7 Bi4 Bi5 36.57(9) . . ? O19 Bi4 Bi5 87.89(9) . . ? O2 Bi4 Bi5 37.65(8) . . ? O6 Bi4 Bi5 101.26(8) . . ? O7 Bi4 Bi2 34.05(9) . . ? O19 Bi4 Bi2 85.53(9) . . ? O2 Bi4 Bi2 101.94(8) . . ? O6 Bi4 Bi2 36.80(8) . . ? Bi5 Bi4 Bi2 67.850(6) . . ? O7 Bi4 Bi9 82.58(9) . . ? O19 Bi4 Bi9 32.17(9) . . ? O2 Bi4 Bi9 98.45(8) . . ? O6 Bi4 Bi9 39.01(8) . . ? Bi5 Bi4 Bi9 93.831(7) . . ? Bi2 Bi4 Bi9 59.147(6) . . ? O7 Bi2 O20 90.09(12) . . ? O7 Bi2 O6 72.88(12) . . ? O20 Bi2 O6 73.45(12) . . ? O7 Bi2 O9 87.06(13) . . ? O20 Bi2 O9 139.40(12) . . ? O6 Bi2 O9 67.02(12) . . ? O7 Bi2 O8 138.57(12) . . ? O20 Bi2 O8 79.14(12) . . ? O6 Bi2 O8 65.69(12) . . ? O9 Bi2 O8 76.63(12) . . ? O7 Bi2 O1 71.37(12) . . ? O20 Bi2 O1 65.83(11) . . ? O6 Bi2 O1 124.63(11) . . ? O9 Bi2 O1 148.12(11) . . ? O8 Bi2 O1 134.83(12) . . ? O7 Bi2 Bi3 98.71(9) . . ? O20 Bi2 Bi3 97.16(9) . . ? O6 Bi2 Bi3 35.49(9) . . ? O9 Bi2 Bi3 43.67(8) . . ? O8 Bi2 Bi3 44.57(9) . . ? O1 Bi2 Bi3 159.60(7) . . ? O7 Bi2 Bi9 83.30(8) . . ? O20 Bi2 Bi9 34.34(9) . . ? O6 Bi2 Bi9 39.37(9) . . ? O9 Bi2 Bi9 105.25(8) . . ? O8 Bi2 Bi9 65.34(8) . . ? O1 Bi2 Bi9 95.48(7) . . ? Bi3 Bi2 Bi9 65.158(6) . . ? O7 Bi2 Bi4 32.82(9) . . ? O20 Bi2 Bi4 83.43(9) . . ? O6 Bi2 Bi4 40.24(9) . . ? O9 Bi2 Bi4 72.62(9) . . ? O8 Bi2 Bi4 105.81(8) . . ? O1 Bi2 Bi4 97.84(7) . . ? Bi3 Bi2 Bi4 67.820(6) . . ? Bi9 Bi2 Bi4 60.942(6) . . ? O4 Bi1 O20 95.61(13) . . ? O4 Bi1 O5 73.55(12) . . ? O20 Bi1 O5 71.36(12) . . ? O4 Bi1 O1 78.09(12) . . ? O20 Bi1 O1 75.32(12) . . ? O5 Bi1 O1 133.20(12) . . ? O4 Bi1 O3 122.06(12) . . ? O20 Bi1 O3 105.65(12) . . ? O5 Bi1 O3 64.10(11) . . ? O1 Bi1 O3 159.08(12) . . ? O4 Bi1 Bi7 35.63(9) . . ? O20 Bi1 Bi7 86.32(10) . . ? O5 Bi1 Bi7 38.31(9) . . ? O1 Bi1 Bi7 108.83(9) . . ? O3 Bi1 Bi7 92.05(8) . . ? O4 Bi1 Bi9 84.34(9) . . ? O20 Bi1 Bi9 32.60(9) . . ? O5 Bi1 Bi9 38.76(8) . . ? O1 Bi1 Bi9 102.74(8) . . ? O3 Bi1 Bi9 86.08(8) . . ? Bi7 Bi1 Bi9 60.660(6) . . ? O2 Bi5 O7 74.27(12) . . ? O2 Bi5 O4 73.60(12) . . ? O7 Bi5 O4 89.36(12) . . ? O2 Bi5 O12 68.05(12) . . ? O7 Bi5 O12 141.72(12) . . ? O4 Bi5 O12 86.50(12) . . ? O2 Bi5 O13 65.86(12) . . ? O7 Bi5 O13 81.51(12) . . ? O4 Bi5 O13 139.43(12) . . ? O12 Bi5 O13 77.31(12) . . ? O2 Bi5 Bi6 35.21(9) . . ? O7 Bi5 Bi6 98.82(9) . . ? O4 Bi5 Bi6 98.61(9) . . ? O12 Bi5 Bi6 44.65(8) . . ? O13 Bi5 Bi6 45.01(8) . . ? O2 Bi5 Bi4 39.38(9) . . ? O7 Bi5 Bi4 35.16(9) . . ? O4 Bi5 Bi4 83.20(9) . . ? O12 Bi5 Bi4 106.62(8) . . ? O13 Bi5 Bi4 66.76(8) . . ? Bi6 Bi5 Bi4 65.735(6) . . ? O6 Bi3 O10 77.29(13) . . ? O6 Bi3 O11 76.52(12) . . ? O10 Bi3 O11 87.08(13) . . ? O6 Bi3 O9 67.92(12) . . ? O10 Bi3 O9 90.80(12) . . ? O11 Bi3 O9 143.93(12) . . ? O6 Bi3 O8 66.18(12) . . ? O10 Bi3 O8 143.46(13) . . ? O11 Bi3 O8 85.34(12) . . ? O9 Bi3 O8 75.23(12) . . ? O6 Bi3 Bi2 37.37(9) . . ? O10 Bi3 Bi2 104.50(9) . . ? O11 Bi3 Bi2 103.02(9) . . ? O9 Bi3 Bi2 43.03(8) . . ? O8 Bi3 Bi2 43.49(8) . . ? O4 Bi7 O19 91.17(12) . . ? O4 Bi7 O5 72.42(12) . . ? O19 Bi7 O5 72.06(12) . . ? O4 Bi7 O17 81.70(12) . . ? O19 Bi7 O17 135.22(13) . . ? O5 Bi7 O17 63.61(12) . . ? O4 Bi7 O16 136.61(13) . . ? O19 Bi7 O16 82.58(12) . . ? O5 Bi7 O16 64.78(12) . . ? O17 Bi7 O16 73.55(12) . . ? O4 Bi7 O2 66.10(12) . . ? O19 Bi7 O2 67.27(11) . . ? O5 Bi7 O2 119.72(11) . . ? O17 Bi7 O2 142.32(11) . . ? O16 Bi7 O2 143.89(11) . . ? O4 Bi7 Bi8 95.64(9) . . ? O19 Bi7 Bi8 96.25(9) . . ? O5 Bi7 Bi8 34.36(8) . . ? O17 Bi7 Bi8 41.51(8) . . ? O16 Bi7 Bi8 43.22(9) . . ? O2 Bi7 Bi8 154.04(7) . . ? O4 Bi7 Bi1 33.49(9) . . ? O19 Bi7 Bi1 84.37(9) . . ? O5 Bi7 Bi1 39.31(8) . . ? O17 Bi7 Bi1 65.63(9) . . ? O16 Bi7 Bi1 103.15(9) . . ? O2 Bi7 Bi1 93.53(7) . . ? Bi8 Bi7 Bi1 63.968(6) . . ? O4 Bi7 Bi9 82.67(9) . . ? O19 Bi7 Bi9 33.84(9) . . ? O5 Bi7 Bi9 38.33(9) . . ? O17 Bi7 Bi9 101.45(9) . . ? O16 Bi7 Bi9 68.48(9) . . ? O2 Bi7 Bi9 93.60(7) . . ? Bi8 Bi7 Bi9 64.726(6) . . ? Bi1 Bi7 Bi9 60.488(6) . . ? O5 Bi8 O3 76.39(13) . . ? O5 Bi8 O18 74.76(13) . . ? O3 Bi8 O18 85.50(14) . . ? O5 Bi8 O17 67.07(13) . . ? O3 Bi8 O17 84.67(13) . . ? O18 Bi8 O17 141.82(12) . . ? O5 Bi8 O16 66.99(12) . . ? O3 Bi8 O16 142.76(12) . . ? O18 Bi8 O16 91.17(13) . . ? O17 Bi8 O16 75.30(12) . . ? O5 Bi8 Bi7 36.97(9) . . ? O3 Bi8 Bi7 101.37(9) . . ? O18 Bi8 Bi7 103.48(9) . . ? O17 Bi8 Bi7 43.33(8) . . ? O16 Bi8 Bi7 43.55(8) . . ? O2 Bi6 O14 81.01(13) . . ? O2 Bi6 O15 75.69(14) . . ? O14 Bi6 O15 88.52(14) . . ? O2 Bi6 O12 68.09(12) . . ? O14 Bi6 O12 88.75(13) . . ? O15 Bi6 O12 143.66(13) . . ? O2 Bi6 O13 66.04(12) . . ? O14 Bi6 O13 146.68(13) . . ? O15 Bi6 O13 88.03(13) . . ? O12 Bi6 O13 74.96(12) . . ? O2 Bi6 Bi5 36.97(9) . . ? O14 Bi6 Bi5 105.58(10) . . ? O15 Bi6 Bi5 103.52(10) . . ? O12 Bi6 Bi5 43.08(8) . . ? O13 Bi6 Bi5 43.67(8) . . ? Bi4 O19 Bi9 116.04(15) . . ? Bi4 O19 Bi7 117.87(14) . . ? Bi9 O19 Bi7 111.10(15) . . ? Bi1 O4 Bi5 123.04(15) . . ? Bi1 O4 Bi7 110.88(14) . . ? Bi5 O4 Bi7 116.60(15) . . ? Bi1 O20 Bi9 115.19(15) . . ? Bi1 O20 Bi2 121.97(15) . . ? Bi9 O20 Bi2 110.13(15) . . ? Bi3 O6 Bi2 107.14(14) . . ? Bi3 O6 Bi9 117.30(14) . . ? Bi2 O6 Bi9 103.61(14) . . ? Bi3 O6 Bi4 122.67(15) . . ? Bi2 O6 Bi4 102.96(13) . . ? Bi9 O6 Bi4 100.87(12) . . ? C1 O1 Bi1 120.9(3) . . ? C1 O1 Bi2 123.8(3) . . ? Bi1 O1 Bi2 96.10(11) . . ? Bi8 O5 Bi7 108.68(14) . . ? Bi8 O5 Bi1 116.66(15) . . ? Bi7 O5 Bi1 102.39(13) . . ? Bi8 O5 Bi9 119.82(15) . . ? Bi7 O5 Bi9 104.58(14) . . ? Bi1 O5 Bi9 102.78(12) . . ? Bi4 O7 Bi2 113.13(14) . . ? Bi4 O7 Bi5 108.26(15) . . ? Bi2 O7 Bi5 129.17(17) . . ? C37 O18 Bi8 133.1(3) . . ? C4 O3 Bi8 123.8(3) . . ? C4 O3 Bi1 128.8(3) . . ? Bi8 O3 Bi1 99.71(13) . . ? C10 O9 Bi2 126.3(3) . . ? C10 O9 Bi3 128.2(3) . . ? Bi2 O9 Bi3 93.30(11) . . ? C16 O11 Bi3 122.1(3) . . ? C16 O11 Bi9 131.5(3) . . ? Bi3 O11 Bi9 99.43(12) . . ? C22 O13 Bi5 128.6(3) . . ? C22 O13 Bi6 132.8(3) . . ? Bi5 O13 Bi6 91.32(11) . . ? C19 O12 Bi5 121.7(3) . . ? C19 O12 Bi6 132.8(3) . . ? Bi5 O12 Bi6 92.27(12) . . ? C31 O16 Bi8 130.1(3) . . ? C31 O16 Bi7 123.4(3) . . ? Bi8 O16 Bi7 93.22(12) . . ? C28 O15 Bi6 123.2(3) . . ? C34 O17 Bi8 133.1(3) . . ? C34 O17 Bi7 129.1(3) . . ? Bi8 O17 Bi7 95.15(12) . . ? C25 O14 Bi6 123.5(3) . . ? Bi6 O2 Bi5 107.83(13) . . ? Bi6 O2 Bi4 119.39(15) . . ? Bi5 O2 Bi4 102.96(13) . . ? Bi6 O2 Bi7 120.78(14) . . ? Bi5 O2 Bi7 103.29(13) . . ? Bi4 O2 Bi7 100.23(12) . . ? C13 O10 Bi3 130.1(3) . . ? C7 O8 Bi2 124.9(3) . . ? C7 O8 Bi3 130.4(3) . . ? Bi2 O8 Bi3 91.94(12) . . ? O18 C37 C38 111.7(4) . . ? O18 C37 C39 108.0(4) . . ? C38 C37 C39 112.5(5) . . ? O9 C10 C12 111.2(4) . . ? O9 C10 C11 108.5(5) . . ? C12 C10 C11 112.5(5) . . ? O11 C16 C18 111.2(5) . . ? O11 C16 C17 108.9(5) . . ? C18 C16 C17 111.7(5) . . ? O10 C13 C14 111.9(4) . . ? O10 C13 C15 112.5(5) . . ? C14 C13 C15 110.5(5) . . ? O12 C19 C21 111.7(5) . . ? O12 C19 C20 109.9(5) . . ? C21 C19 C20 112.2(5) . . ? O8 C7 C8 109.1(5) . . ? O8 C7 C9 110.6(5) . . ? C8 C7 C9 112.3(5) . . ? F74 C38 F75 106.7(4) . . ? F74 C38 F73 107.1(5) . . ? F75 C38 F73 107.3(4) . . ? F74 C38 C37 114.1(4) . . ? F75 C38 C37 112.0(4) . . ? F73 C38 C37 109.3(4) . . ? O17 C34 C36 109.8(4) . . ? O17 C34 C35 110.6(4) . . ? C36 C34 C35 112.5(5) . . ? F78 C39 F77 107.7(5) . . ? F78 C39 F76 108.1(5) . . ? F77 C39 F76 107.5(5) . . ? F78 C39 C37 109.1(5) . . ? F77 C39 C37 112.3(5) . . ? F76 C39 C37 112.0(5) . . ? F40 C21 F42 107.9(6) . . ? F40 C21 F41 106.3(6) . . ? F42 C21 F41 106.9(6) . . ? F40 C21 C19 112.8(6) . . ? F42 C21 C19 112.9(6) . . ? F41 C21 C19 109.6(5) . . ? O14 C25 C27 110.2(5) . . ? O14 C25 C26 109.4(5) . . ? C27 C25 C26 110.9(5) . . ? F50 C26 F51 108.9(5) . . ? F50 C26 F49 106.8(5) . . ? F51 C26 F49 107.2(5) . . ? F50 C26 C25 112.4(5) . . ? F51 C26 C25 113.2(5) . . ? F49 C26 C25 108.0(5) . . ? O3 C4 C5 113.1(5) . . ? O3 C4 C6 108.3(4) . . ? C5 C4 C6 112.0(5) . . ? F21 C11 F19 107.7(5) . . ? F21 C11 F20 108.6(5) . . ? F19 C11 F20 106.5(5) . . ? F21 C11 C10 112.5(5) . . ? F19 C11 C10 111.4(5) . . ? F20 C11 C10 109.8(5) . . ? F29 C15 F28 107.6(5) . . ? F29 C15 F30 106.8(5) . . ? F28 C15 F30 107.0(4) . . ? F29 C15 C13 112.6(5) . . ? F28 C15 C13 113.1(5) . . ? F30 C15 C13 109.5(5) . . ? F16 C9 F17 107.8(5) . . ? F16 C9 F18 107.5(5) . . ? F17 C9 F18 106.6(5) . . ? F16 C9 C7 113.6(5) . . ? F17 C9 C7 112.2(5) . . ? F18 C9 C7 108.8(5) . . ? F6 C3 F5 107.0(5) . . ? F6 C3 F4 107.4(5) . . ? F5 C3 F4 106.7(5) . . ? F6 C3 C1 112.9(5) . . ? F5 C3 C1 110.2(5) . . ? F4 C3 C1 112.2(5) . . ? F9 C5 F8 108.5(5) . . ? F9 C5 F7 107.4(5) . . ? F8 C5 F7 106.4(5) . . ? F9 C5 C4 112.6(5) . . ? F8 C5 C4 113.5(5) . . ? F7 C5 C4 108.1(5) . . ? F69 C35 F68 108.0(5) . . ? F69 C35 F67 107.7(5) . . ? F68 C35 F67 106.8(5) . . ? F69 C35 C34 112.3(5) . . ? F68 C35 C34 111.8(5) . . ? F67 C35 C34 110.0(5) . . ? F65 C33 F64 107.1(5) . . ? F65 C33 F66 106.6(5) . . ? F64 C33 F66 106.2(5) . . ? F65 C33 C31 113.4(5) . . ? F64 C33 C31 113.0(5) . . ? F66 C33 C31 110.1(4) . . ? F22 C12 F24 108.5(5) . . ? F22 C12 F23 107.1(5) . . ? F24 C12 F23 105.6(5) . . ? F22 C12 C10 114.1(5) . . ? F24 C12 C10 112.2(5) . . ? F23 C12 C10 108.8(5) . . ? F46 C24 F48 107.1(5) . . ? F46 C24 F47 106.9(5) . . ? F48 C24 F47 106.5(5) . . ? F46 C24 C22 113.4(5) . . ? F48 C24 C22 112.6(5) . . ? F47 C24 C22 110.1(5) . . ? O1 C1 C2 110.6(5) . . ? O1 C1 C3 108.6(4) . . ? C2 C1 C3 112.0(5) . . ? F26 C14 F27 108.5(5) . . ? F26 C14 F25 106.8(5) . . ? F27 C14 F25 105.7(5) . . ? F26 C14 C13 113.5(5) . . ? F27 C14 C13 110.2(5) . . ? F25 C14 C13 111.9(5) . . ? F36 C18 F35 107.8(6) . . ? F36 C18 F34 107.6(6) . . ? F35 C18 F34 106.5(6) . . ? F36 C18 C16 114.3(6) . . ? F35 C18 C16 112.2(6) . . ? F34 C18 C16 108.1(5) . . ? F12 C6 F11 108.3(5) . . ? F12 C6 F10 108.2(5) . . ? F11 C6 F10 106.5(5) . . ? F12 C6 C4 112.5(5) . . ? F11 C6 C4 111.8(5) . . ? F10 C6 C4 109.3(5) . . ? F52 C27 F53 108.6(5) . . ? F52 C27 F54 106.7(5) . . ? F53 C27 F54 106.4(5) . . ? F52 C27 C25 113.7(5) . . ? F53 C27 C25 113.4(5) . . ? F54 C27 C25 107.5(5) . . ? O13 C22 C23 111.0(5) . . ? O13 C22 C24 108.2(5) . . ? C23 C22 C24 112.8(5) . . ? F62 C32 F63 106.6(5) . . ? F62 C32 F61 107.2(5) . . ? F63 C32 F61 107.2(5) . . ? F62 C32 C31 113.0(5) . . ? F63 C32 C31 110.5(5) . . ? F61 C32 C31 112.1(5) . . ? F14 C8 F15 107.6(5) . . ? F14 C8 F13 106.2(5) . . ? F15 C8 F13 105.8(5) . . ? F14 C8 C7 114.4(5) . . ? F15 C8 C7 112.6(5) . . ? F13 C8 C7 109.7(5) . . ? F55 C29 F56 108.4(6) . . ? F55 C29 F57 107.7(6) . . ? F56 C29 F57 106.1(5) . . ? F55 C29 C28 114.3(6) . . ? F56 C29 C28 111.3(6) . . ? F57 C29 C28 108.6(5) . . ? F39 C20 F38 107.1(5) . . ? F39 C20 F37 107.7(5) . . ? F38 C20 F37 106.5(5) . . ? F39 C20 C19 112.9(5) . . ? F38 C20 C19 112.0(5) . . ? F37 C20 C19 110.3(5) . . ? O15 C28 C29 111.0(5) . . ? O15 C28 C30 108.8(5) . . ? C29 C28 C30 111.8(5) . . ? O16 C31 C33 111.8(4) . . ? O16 C31 C32 108.8(5) . . ? C33 C31 C32 112.2(5) . . ? F72 C36 F70 106.6(5) . . ? F72 C36 F71 107.5(5) . . ? F70 C36 F71 107.6(5) . . ? F72 C36 C34 110.0(5) . . ? F70 C36 C34 111.9(5) . . ? F71 C36 C34 112.9(5) . . ? F3 C2 F2 107.8(5) . . ? F3 C2 F1 107.1(5) . . ? F2 C2 F1 106.0(5) . . ? F3 C2 C1 113.0(5) . . ? F2 C2 C1 112.7(5) . . ? F1 C2 C1 109.8(4) . . ? F31 C17 F33 106.7(6) . . ? F31 C17 F32 107.6(6) . . ? F33 C17 F32 104.8(6) . . ? F31 C17 C16 113.5(6) . . ? F33 C17 C16 110.5(6) . . ? F32 C17 C16 113.2(6) . . ? F45 C23 F44 109.5(7) . . ? F45 C23 F43 107.8(6) . . ? F44 C23 F43 105.7(6) . . ? F45 C23 C22 112.6(6) . . ? F44 C23 C22 112.0(6) . . ? F43 C23 C22 108.9(6) . . ? F60 C30 F59 107.2(5) . . ? F60 C30 F58 107.9(5) . . ? F59 C30 F58 105.8(5) . . ? F60 C30 C28 113.4(5) . . ? F59 C30 C28 111.8(5) . . ? F58 C30 C28 110.4(5) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.633 _refine_diff_density_min -1.470 _refine_diff_density_rms 0.272 # Attachment 'compound 2.CIF' data_bif127 _database_code_depnum_ccdc_archive 'CCDC 663321' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 Bi F18 N2 O3' _chemical_formula_weight 868.29 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' F F 0.0171 0.0103 '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 trigonal _symmetry_space_group_name_H-M P3(2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 13.9674(3) _cell_length_b 13.9674(3) _cell_length_c 11.9283(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2015.30(8) _cell_formula_units_Z 3 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1230 _exptl_absorpt_coefficient_mu 6.712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6158 _exptl_absorpt_correction_T_max 0.6508 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50623 _diffrn_reflns_av_R_equivalents 0.0839 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 30.10 _reflns_number_total 7830 _reflns_number_gt 6865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_cell_refinement 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_data_reduction 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.014(4) _refine_ls_number_reflns 7830 _refine_ls_number_parameters 388 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0556 _refine_ls_wR_factor_gt 0.0522 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.002 _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 0.719750(14) 0.652822(14) 0.16514(2) 0.01595(4) Uani 1 1 d . . . O1 O 0.5783(3) 0.5143(3) 0.0836(3) 0.0183(7) Uani 1 1 d . . . O2 O 0.6603(3) 0.7559(3) 0.1096(3) 0.0203(8) Uani 1 1 d . . . N2 N 0.8866(3) 0.8422(3) 0.1897(3) 0.0215(9) Uani 1 1 d . . . O3 O 0.7938(3) 0.6696(3) 0.0043(3) 0.0243(8) Uani 1 1 d . . . C2 C 0.4869(4) 0.4237(4) 0.1278(4) 0.0176(10) Uani 1 1 d . . . H2 H 0.4495 0.4503 0.1806 0.021 Uiso 1 1 calc R . . C5 C 0.5830(4) 0.7239(4) 0.0252(4) 0.0201(11) Uani 1 1 d . . . H5 H 0.5710 0.6531 -0.0082 0.024 Uiso 1 1 calc R . . C8 C 0.7748(4) 0.5773(4) -0.0573(4) 0.0236(11) Uani 1 1 d . . . H8 H 0.7179 0.5093 -0.0179 0.028 Uiso 1 1 calc R . . F13 F 0.6366(3) 0.5843(3) -0.1637(3) 0.0446(9) Uani 1 1 d . . . F15 F 0.7076(3) 0.4924(3) -0.2333(3) 0.0478(10) Uani 1 1 d . . . F14 F 0.8008(3) 0.6708(3) -0.2321(3) 0.0491(10) Uani 1 1 d . . . C7 C 0.7315(5) 0.5825(5) -0.1723(5) 0.0341(14) Uani 1 1 d . . . F7 F 0.4446(2) 0.6327(3) 0.1586(3) 0.0361(8) Uani 1 1 d . . . F8 F 0.3922(3) 0.6647(3) 0.0001(3) 0.0476(10) Uani 1 1 d . . . F17 F 0.9650(3) 0.6641(3) -0.1094(3) 0.0537(11) Uani 1 1 d . . . F12 F 0.7155(3) 0.8215(3) -0.1139(3) 0.0385(9) Uani 1 1 d . . . F5 F 0.5754(4) 0.3175(4) 0.1308(4) 0.0702(14) Uani 1 1 d . . . F1 F 0.3819(3) 0.4291(3) -0.0216(3) 0.0604(12) Uani 1 1 d . . . F9 F 0.4820(3) 0.7976(3) 0.1173(3) 0.0490(10) Uani 1 1 d . . . F10 F 0.5520(3) 0.7900(3) -0.1468(3) 0.0497(10) Uani 1 1 d . . . F18 F 0.9148(3) 0.5675(3) 0.0401(3) 0.0499(10) Uani 1 1 d . . . F6 F 0.5839(3) 0.4077(3) 0.2777(3) 0.0572(12) Uani 1 1 d . . . F2 F 0.4507(3) 0.3240(3) -0.0419(3) 0.0566(11) Uani 1 1 d . . . F11 F 0.6539(3) 0.9124(3) -0.0251(3) 0.0516(10) Uani 1 1 d . . . F16 F 0.8705(3) 0.4871(3) -0.1200(3) 0.0545(11) Uani 1 1 d . . . F3 F 0.3129(3) 0.2760(3) 0.0687(3) 0.0691(14) Uani 1 1 d . . . F4 F 0.4321(3) 0.2610(3) 0.2337(3) 0.0692(14) Uani 1 1 d . . . C16 C 0.9681(5) 1.0325(5) 0.2429(5) 0.0347(14) Uani 1 1 d . . . H16 H 0.9594 1.0940 0.2612 0.042 Uiso 1 1 calc R . . C19 C 0.9852(5) 0.8524(5) 0.1909(5) 0.0305(13) Uani 1 1 d . . . H19 H 0.9915 0.7895 0.1726 0.037 Uiso 1 1 calc R . . C15 C 0.8779(4) 0.9316(4) 0.2146(5) 0.0278(12) Uani 1 1 d . . . H15 H 0.8068 0.9250 0.2128 0.033 Uiso 1 1 calc R . . C4 C 0.4741(4) 0.7057(5) 0.0750(5) 0.0297(13) Uani 1 1 d . . . C6 C 0.6258(5) 0.8124(5) -0.0647(5) 0.0311(13) Uani 1 1 d . . . C1 C 0.4080(5) 0.3616(5) 0.0337(5) 0.0354(15) Uani 1 1 d . . . C3 C 0.5181(5) 0.3501(5) 0.1920(5) 0.0374(15) Uani 1 1 d . . . C9 C 0.8815(5) 0.5747(5) -0.0630(5) 0.0333(14) Uani 1 1 d . . . C18 C 1.0806(5) 0.9499(5) 0.2174(6) 0.0454(17) Uani 1 1 d . . . H18 H 1.1505 0.9538 0.2174 0.054 Uiso 1 1 calc R . . C17 C 1.0716(5) 1.0414(5) 0.2438(6) 0.0439(17) Uani 1 1 d . . . H17 H 1.1355 1.1096 0.2624 0.053 Uiso 1 1 calc R . . N1 N 0.6342(4) 0.6890(4) 0.3560(4) 0.0259(10) Uani 1 1 d . . . C14 C 0.6282(5) 0.6304(5) 0.4464(4) 0.0295(13) Uani 1 1 d . . . H14 H 0.6512 0.5770 0.4406 0.035 Uiso 1 1 calc R . . C10 C 0.6000(5) 0.7620(5) 0.3648(4) 0.0275(13) Uani 1 1 d . . . H10 H 0.6030 0.8032 0.3003 0.033 Uiso 1 1 calc R . . C11 C 0.5604(5) 0.7805(5) 0.4637(5) 0.0337(14) Uani 1 1 d . . . H11 H 0.5368 0.8335 0.4676 0.040 Uiso 1 1 calc R . . C13 C 0.5900(5) 0.6442(5) 0.5479(5) 0.0332(14) Uani 1 1 d . . . H13 H 0.5874 0.6014 0.6110 0.040 Uiso 1 1 calc R . . C12 C 0.5563(5) 0.7196(5) 0.5569(5) 0.0342(14) Uani 1 1 d . . . H12 H 0.5300 0.7304 0.6265 0.041 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 0.01740(10) 0.01573(10) 0.01716(7) 0.00019(8) 0.00050(8) 0.01012(9) O1 0.0178(18) 0.0135(17) 0.0186(18) -0.0011(13) -0.0011(14) 0.0041(15) O2 0.0192(19) 0.0175(19) 0.029(2) 0.0009(15) -0.0041(15) 0.0126(16) N2 0.019(2) 0.022(2) 0.026(2) -0.0004(18) 0.0003(18) 0.012(2) O3 0.029(2) 0.020(2) 0.0217(19) 0.0005(15) 0.0100(15) 0.0100(17) C2 0.017(3) 0.012(2) 0.019(3) -0.0002(19) 0.0015(19) 0.004(2) C5 0.013(2) 0.022(3) 0.029(3) 0.000(2) -0.004(2) 0.012(2) C8 0.032(3) 0.020(3) 0.019(3) 0.001(2) 0.009(2) 0.013(2) F13 0.051(2) 0.065(3) 0.033(2) -0.0061(18) -0.0048(17) 0.040(2) F15 0.059(3) 0.053(2) 0.033(2) -0.0199(18) -0.0021(18) 0.029(2) F14 0.067(3) 0.048(2) 0.029(2) 0.0122(17) 0.0137(18) 0.027(2) C7 0.040(4) 0.039(4) 0.028(3) -0.001(3) 0.008(3) 0.023(3) F7 0.0235(18) 0.039(2) 0.042(2) 0.0090(16) 0.0127(15) 0.0121(16) F8 0.0213(19) 0.060(3) 0.060(3) 0.007(2) -0.0074(17) 0.0188(18) F17 0.032(2) 0.050(3) 0.073(3) 0.009(2) 0.024(2) 0.016(2) F12 0.0262(18) 0.047(2) 0.044(2) 0.0262(17) 0.0165(15) 0.0199(17) F5 0.093(4) 0.061(3) 0.089(4) -0.006(2) -0.018(3) 0.062(3) F1 0.052(3) 0.059(3) 0.070(3) 0.005(2) -0.032(2) 0.027(2) F9 0.037(2) 0.037(2) 0.082(3) 0.0014(19) 0.0201(19) 0.0256(18) F10 0.036(2) 0.082(3) 0.041(2) 0.021(2) -0.0046(17) 0.036(2) F18 0.052(2) 0.062(3) 0.050(2) -0.0056(19) -0.0103(19) 0.039(2) F6 0.064(3) 0.039(2) 0.043(2) 0.0108(18) -0.030(2) 0.006(2) F2 0.082(3) 0.046(2) 0.037(2) -0.0192(18) -0.012(2) 0.028(2) F11 0.071(3) 0.030(2) 0.061(3) 0.0179(18) 0.010(2) 0.031(2) F16 0.053(3) 0.053(3) 0.073(3) -0.027(2) -0.001(2) 0.038(2) F3 0.039(2) 0.053(3) 0.061(3) 0.007(2) -0.018(2) -0.018(2) F4 0.073(3) 0.032(2) 0.058(3) 0.0279(19) -0.015(2) -0.007(2) C16 0.030(3) 0.025(3) 0.046(4) -0.006(3) 0.002(3) 0.011(3) C19 0.027(3) 0.023(3) 0.045(4) -0.004(3) -0.002(3) 0.015(3) C15 0.023(3) 0.026(3) 0.036(3) -0.003(2) 0.003(2) 0.013(3) C4 0.019(3) 0.026(3) 0.043(4) 0.001(3) 0.003(2) 0.010(3) C6 0.032(3) 0.034(3) 0.036(3) 0.009(3) 0.003(3) 0.023(3) C1 0.036(4) 0.029(3) 0.032(3) -0.001(3) -0.012(3) 0.009(3) C3 0.043(4) 0.023(3) 0.036(4) 0.005(3) -0.012(3) 0.008(3) C9 0.033(3) 0.030(3) 0.038(4) -0.004(3) 0.010(3) 0.016(3) C18 0.021(3) 0.037(4) 0.079(5) -0.005(3) -0.004(3) 0.015(3) C17 0.024(3) 0.025(3) 0.073(5) -0.014(3) -0.005(3) 0.005(3) N1 0.033(3) 0.025(3) 0.025(2) 0.0027(19) 0.008(2) 0.018(2) C14 0.040(4) 0.031(3) 0.023(3) -0.002(2) 0.001(2) 0.022(3) C10 0.035(3) 0.026(3) 0.025(3) -0.002(2) 0.002(2) 0.018(3) C11 0.039(4) 0.038(4) 0.034(3) -0.012(3) -0.004(3) 0.026(3) C13 0.040(4) 0.026(3) 0.024(3) 0.004(2) 0.006(3) 0.009(3) C12 0.032(3) 0.032(3) 0.026(3) -0.009(3) 0.003(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 O2 2.097(3) . ? Bi1 O3 2.135(3) . ? Bi1 O1 2.184(3) . ? Bi1 N2 2.520(4) . ? Bi1 N1 2.734(4) . ? O1 C2 1.376(5) . ? O2 C5 1.377(6) . ? N2 C19 1.313(7) . ? N2 C15 1.346(6) . ? O3 C8 1.390(6) . ? C2 C1 1.507(7) . ? C2 C3 1.511(7) . ? C5 C6 1.515(7) . ? C5 C4 1.532(7) . ? C8 C9 1.510(8) . ? C8 C7 1.515(7) . ? F13 C7 1.343(7) . ? F15 C7 1.343(6) . ? F14 C7 1.332(7) . ? F7 C4 1.335(6) . ? F8 C4 1.334(6) . ? F17 C9 1.330(6) . ? F12 C6 1.330(6) . ? F5 C3 1.321(8) . ? F1 C1 1.343(7) . ? F9 C4 1.333(6) . ? F10 C6 1.341(6) . ? F18 C9 1.335(7) . ? F6 C3 1.340(6) . ? F2 C1 1.325(7) . ? F11 C6 1.333(7) . ? F16 C9 1.340(6) . ? F3 C1 1.334(7) . ? F4 C3 1.321(7) . ? C16 C15 1.383(8) . ? C16 C17 1.389(8) . ? C19 C18 1.384(8) . ? C18 C17 1.382(8) . ? N1 C10 1.329(6) . ? N1 C14 1.331(7) . ? C14 C13 1.374(7) . ? C10 C11 1.381(7) . ? C11 C12 1.384(8) . ? C13 C12 1.357(8) . ? 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 O2 Bi1 O3 88.69(14) . . ? O2 Bi1 O1 88.50(12) . . ? O3 Bi1 O1 82.60(12) . . ? O2 Bi1 N2 77.99(13) . . ? O3 Bi1 N2 81.15(13) . . ? O1 Bi1 N2 159.04(12) . . ? O2 Bi1 N1 77.08(13) . . ? O3 Bi1 N1 163.80(13) . . ? O1 Bi1 N1 104.42(13) . . ? N2 Bi1 N1 88.26(13) . . ? C2 O1 Bi1 131.0(3) . . ? C5 O2 Bi1 121.6(3) . . ? C19 N2 C15 118.3(5) . . ? C19 N2 Bi1 119.0(3) . . ? C15 N2 Bi1 122.3(3) . . ? C8 O3 Bi1 121.1(3) . . ? O1 C2 C1 108.6(4) . . ? O1 C2 C3 111.6(4) . . ? C1 C2 C3 111.2(4) . . ? O2 C5 C6 109.1(4) . . ? O2 C5 C4 108.8(4) . . ? C6 C5 C4 111.4(4) . . ? O3 C8 C9 108.3(4) . . ? O3 C8 C7 109.3(4) . . ? C9 C8 C7 112.5(4) . . ? F14 C7 F13 106.9(5) . . ? F14 C7 F15 107.7(5) . . ? F13 C7 F15 105.9(5) . . ? F14 C7 C8 114.0(5) . . ? F13 C7 C8 110.7(4) . . ? F15 C7 C8 111.3(5) . . ? C15 C16 C17 118.0(5) . . ? N2 C19 C18 123.4(5) . . ? N2 C15 C16 122.7(5) . . ? F9 C4 F8 107.9(5) . . ? F9 C4 F7 107.3(5) . . ? F8 C4 F7 107.6(4) . . ? F9 C4 C5 113.0(4) . . ? F8 C4 C5 112.3(5) . . ? F7 C4 C5 108.6(4) . . ? F12 C6 F11 106.6(5) . . ? F12 C6 F10 106.1(5) . . ? F11 C6 F10 107.0(5) . . ? F12 C6 C5 111.0(4) . . ? F11 C6 C5 113.2(5) . . ? F10 C6 C5 112.5(5) . . ? F2 C1 F3 107.5(5) . . ? F2 C1 F1 106.1(5) . . ? F3 C1 F1 106.5(5) . . ? F2 C1 C2 113.0(5) . . ? F3 C1 C2 113.4(5) . . ? F1 C1 C2 109.8(5) . . ? F5 C3 F4 107.8(5) . . ? F5 C3 F6 106.1(5) . . ? F4 C3 F6 107.8(5) . . ? F5 C3 C2 112.7(5) . . ? F4 C3 C2 113.3(5) . . ? F6 C3 C2 108.8(5) . . ? F17 C9 F18 106.2(5) . . ? F17 C9 F16 107.0(5) . . ? F18 C9 F16 106.5(5) . . ? F17 C9 C8 114.1(5) . . ? F18 C9 C8 110.2(4) . . ? F16 C9 C8 112.3(5) . . ? C17 C18 C19 118.3(6) . . ? C18 C17 C16 119.2(6) . . ? C10 N1 C14 118.2(5) . . ? C10 N1 Bi1 124.4(3) . . ? C14 N1 Bi1 117.4(3) . . ? N1 C14 C13 122.5(6) . . ? N1 C10 C11 122.8(5) . . ? C10 C11 C12 117.9(6) . . ? C12 C13 C14 119.2(6) . . ? C13 C12 C11 119.3(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.619 _refine_diff_density_min -1.206 _refine_diff_density_rms 0.143 # Attachment 'compound 3.CIF' data_bif78 _database_code_depnum_ccdc_archive 'CCDC 663322' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 Bi F18 O6' _chemical_formula_weight 926.41 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' F F 0.0171 0.0103 '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 P21/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 16.5066(4) _cell_length_b 9.5546(2) _cell_length_c 19.4747(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.201(1) _cell_angle_gamma 90.00 _cell_volume 3069.17(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 5.888 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6402 _exptl_absorpt_correction_T_max 0.7089 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 63395 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.60 _reflns_number_total 7071 _reflns_number_gt 5759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_cell_refinement 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_data_reduction 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _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^)+(0.0211P)^2^+8.9524P] 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 7071 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _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 0.247166(11) 0.012088(17) 0.381168(9) 0.01819(6) Uani 1 1 d . . . O1 O 0.2120(2) 0.1601(4) 0.45803(18) 0.0252(8) Uani 1 1 d . . . C2 C 0.2662(3) 0.2260(6) 0.5027(3) 0.0235(11) Uani 1 1 d . . . H2 H 0.3173 0.2444 0.4782 0.028 Uiso 1 1 calc R . . C1 C 0.2862(4) 0.1316(7) 0.5637(3) 0.0339(14) Uani 1 1 d . . . C3 C 0.2313(4) 0.3650(6) 0.5248(3) 0.0320(13) Uani 1 1 d . . . F4 F 0.1692(2) 0.3536(4) 0.56538(19) 0.0449(9) Uani 1 1 d . . . F5 F 0.2871(2) 0.4436(4) 0.5584(2) 0.0518(10) Uani 1 1 d . . . F3 F 0.3267(3) 0.0201(4) 0.54199(19) 0.0556(11) Uani 1 1 d . . . F2 F 0.2208(3) 0.0836(4) 0.59392(18) 0.0491(10) Uani 1 1 d . . . F6 F 0.2063(3) 0.4395(4) 0.4701(2) 0.0513(10) Uani 1 1 d . . . F1 F 0.3329(3) 0.1926(5) 0.61252(19) 0.0585(12) Uani 1 1 d . . . O2 O 0.3552(2) 0.1266(4) 0.36728(18) 0.0234(8) Uani 1 1 d . . . C5 C 0.3718(3) 0.2032(5) 0.3088(3) 0.0233(11) Uani 1 1 d . . . H5 H 0.3232 0.1991 0.2766 0.028 Uiso 1 1 calc R . . C4 C 0.3871(4) 0.3544(6) 0.3281(3) 0.0308(13) Uani 1 1 d . . . C6 C 0.4424(4) 0.1364(6) 0.2739(3) 0.0327(13) Uani 1 1 d . . . F12 F 0.4235(2) 0.0092(4) 0.2516(2) 0.0523(10) Uani 1 1 d . . . F9 F 0.3931(2) 0.4377(3) 0.27374(19) 0.0416(9) Uani 1 1 d . . . F8 F 0.3259(2) 0.4031(3) 0.36474(19) 0.0442(9) Uani 1 1 d . . . F7 F 0.4548(2) 0.3711(4) 0.3673(2) 0.0505(10) Uani 1 1 d . . . F11 F 0.4660(2) 0.2107(4) 0.21938(19) 0.0508(10) Uani 1 1 d . . . F10 F 0.5077(2) 0.1222(4) 0.31591(19) 0.0452(9) Uani 1 1 d . . . O3 O 0.1826(2) 0.1326(4) 0.30611(18) 0.0253(8) Uani 1 1 d . . . F17 F 0.0478(2) 0.1047(5) 0.3799(2) 0.0579(12) Uani 1 1 d . . . O4 O 0.2503(2) -0.1284(4) 0.2677(2) 0.0328(9) Uani 1 1 d . . . F18 F 0.0103(3) 0.1544(6) 0.2776(2) 0.0768(16) Uani 1 1 d . . . C8 C 0.1350(3) 0.2473(5) 0.3196(3) 0.0238(11) Uani 1 1 d . . . H8 H 0.1577 0.2946 0.3619 0.029 Uiso 1 1 calc R . . F16 F 0.0048(3) 0.3121(5) 0.3553(3) 0.0804(16) Uani 1 1 d . . . C9 C 0.0479(4) 0.2054(7) 0.3319(4) 0.0416(16) Uani 1 1 d . . . C13 C 0.2993(4) -0.2526(6) 0.2610(3) 0.0329(14) Uani 1 1 d . . . H13A H 0.2747 -0.3329 0.2846 0.040 Uiso 1 1 calc R . . H13B H 0.3547 -0.2372 0.2809 0.040 Uiso 1 1 calc R . . F15 F 0.1134(3) 0.2941(5) 0.20059(19) 0.0611(12) Uani 1 1 d . . . F14 F 0.2145(2) 0.3904(4) 0.2504(2) 0.0585(12) Uani 1 1 d . . . F13 F 0.0952(3) 0.4620(5) 0.2698(3) 0.0819(16) Uani 1 1 d . . . C7 C 0.1386(4) 0.3495(6) 0.2598(3) 0.0367(14) Uani 1 1 d . . . C12 C 0.3015(4) -0.2789(7) 0.1851(3) 0.0438(16) Uani 1 1 d . . . H12A H 0.3095 -0.3795 0.1751 0.053 Uiso 1 1 calc R . . H12B H 0.3449 -0.2239 0.1640 0.053 Uiso 1 1 calc R . . C10 C 0.2038(5) -0.1037(7) 0.2048(3) 0.0447(17) Uani 1 1 d . . . H10A H 0.2222 -0.0171 0.1822 0.054 Uiso 1 1 calc R . . H10B H 0.1455 -0.0946 0.2140 0.054 Uiso 1 1 calc R . . C11 C 0.2186(4) -0.2299(7) 0.1603(3) 0.0464(17) Uani 1 1 d . . . H11A H 0.2182 -0.2039 0.1111 0.056 Uiso 1 1 calc R . . H11B H 0.1772 -0.3031 0.1671 0.056 Uiso 1 1 calc R . . C15 C 0.0319(4) -0.3428(7) 0.4167(4) 0.0496(18) Uani 1 1 d . . . H15A H 0.0466 -0.4255 0.4451 0.060 Uiso 1 1 calc R . . H15B H -0.0102 -0.3694 0.3815 0.060 Uiso 1 1 calc R . . C16 C 0.0046(5) -0.2221(10) 0.4601(4) 0.072(3) Uani 1 1 d . . . H16A H -0.0285 -0.1551 0.4323 0.086 Uiso 1 1 calc R . . H16B H -0.0275 -0.2558 0.4987 0.086 Uiso 1 1 calc R . . C14 C 0.1043(5) -0.2803(8) 0.3850(4) 0.060(2) Uani 1 1 d . . . H14A H 0.1452 -0.3536 0.3770 0.072 Uiso 1 1 calc R . . H14B H 0.0885 -0.2369 0.3403 0.072 Uiso 1 1 calc R . . O5 O 0.1373(3) -0.1760(5) 0.4315(2) 0.0463(12) Uani 1 1 d . . . C17 C 0.0820(4) -0.1558(9) 0.4860(4) 0.0514(19) Uani 1 1 d . . . H17A H 0.0741 -0.0549 0.4952 0.062 Uiso 1 1 calc R . . H17B H 0.1025 -0.2017 0.5288 0.062 Uiso 1 1 calc R . . O6 O 0.3665(2) -0.1667(4) 0.4227(2) 0.0310(9) Uani 1 1 d . . . C20 C 0.4868(5) -0.2559(9) 0.4735(5) 0.072(3) Uani 1 1 d . . . H20A H 0.5145 -0.3270 0.4458 0.086 Uiso 1 1 calc R . . H20B H 0.5263 -0.2171 0.5080 0.086 Uiso 1 1 calc R . . C19 C 0.4180(4) -0.3171(10) 0.5068(5) 0.078(3) Uani 1 1 d . . . H19A H 0.4125 -0.2761 0.5531 0.094 Uiso 1 1 calc R . . H19B H 0.4252 -0.4195 0.5117 0.094 Uiso 1 1 calc R . . C21 C 0.4525(3) -0.1429(7) 0.4287(3) 0.0358(14) Uani 1 1 d . . . H21A H 0.4641 -0.0500 0.4494 0.043 Uiso 1 1 calc R . . H21B H 0.4764 -0.1463 0.3829 0.043 Uiso 1 1 calc R . . C18 C 0.3458(4) -0.2862(7) 0.4631(4) 0.0447(17) Uani 1 1 d . . . H18A H 0.3318 -0.3670 0.4331 0.054 Uiso 1 1 calc R . . H18B H 0.2989 -0.2650 0.4916 0.054 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 0.01828(9) 0.01764(9) 0.01878(9) 0.00169(8) 0.00221(6) -0.00059(8) O1 0.020(2) 0.035(2) 0.0208(19) -0.0055(16) 0.0050(15) 0.0007(16) C2 0.018(3) 0.035(3) 0.017(3) -0.002(2) 0.002(2) 0.000(2) C1 0.036(4) 0.045(4) 0.021(3) -0.001(3) 0.000(3) 0.002(3) C3 0.031(3) 0.032(3) 0.033(3) -0.002(2) 0.006(3) -0.003(2) F4 0.033(2) 0.052(2) 0.051(2) -0.0178(18) 0.0206(17) -0.0016(17) F5 0.045(2) 0.048(2) 0.062(3) -0.0224(19) 0.003(2) -0.0158(18) F3 0.071(3) 0.055(2) 0.042(2) 0.0050(19) 0.0066(19) 0.031(2) F2 0.061(3) 0.054(2) 0.033(2) 0.0117(17) 0.0169(19) -0.003(2) F6 0.070(3) 0.038(2) 0.046(2) 0.0033(17) 0.007(2) 0.0128(19) F1 0.058(3) 0.087(3) 0.029(2) -0.005(2) -0.0191(19) 0.003(2) O2 0.0164(19) 0.031(2) 0.023(2) 0.0060(15) 0.0025(15) -0.0028(15) C5 0.024(3) 0.028(3) 0.018(3) 0.006(2) 0.003(2) -0.003(2) C4 0.029(3) 0.029(3) 0.034(3) 0.004(2) 0.002(3) -0.002(2) C6 0.027(3) 0.039(3) 0.033(3) 0.002(3) 0.008(3) -0.001(3) F12 0.048(2) 0.043(2) 0.067(3) -0.019(2) 0.0217(19) -0.0012(18) F9 0.044(2) 0.0337(18) 0.048(2) 0.0212(16) 0.0036(17) -0.0049(16) F8 0.053(2) 0.0321(19) 0.048(2) -0.0061(16) 0.0190(19) 0.0010(17) F7 0.050(3) 0.040(2) 0.060(3) 0.0016(18) -0.023(2) -0.0152(18) F11 0.046(2) 0.068(3) 0.041(2) 0.0117(19) 0.0263(18) -0.002(2) F10 0.0185(19) 0.064(2) 0.053(2) 0.0046(19) 0.0062(17) 0.0078(17) O3 0.026(2) 0.0284(19) 0.022(2) -0.0037(15) -0.0014(16) 0.0076(16) F17 0.034(2) 0.083(3) 0.057(3) 0.031(2) 0.0109(19) -0.006(2) O4 0.037(2) 0.034(2) 0.027(2) -0.0065(17) -0.0069(18) 0.0154(18) F18 0.044(3) 0.113(4) 0.071(3) 0.022(3) -0.026(2) -0.039(3) C8 0.018(3) 0.029(3) 0.023(3) -0.001(2) -0.005(2) 0.008(2) F16 0.045(3) 0.090(4) 0.109(4) 0.010(3) 0.031(3) 0.032(3) C9 0.025(4) 0.053(4) 0.047(4) 0.010(3) -0.003(3) 0.003(3) C13 0.035(4) 0.029(3) 0.034(3) -0.008(2) -0.002(3) 0.010(2) F15 0.058(3) 0.094(3) 0.030(2) 0.016(2) -0.0109(19) -0.015(2) F14 0.044(3) 0.063(3) 0.068(3) 0.032(2) -0.007(2) -0.014(2) F13 0.113(4) 0.053(3) 0.081(3) 0.029(2) 0.018(3) 0.047(3) C7 0.028(3) 0.034(3) 0.048(4) 0.006(3) -0.002(3) 0.004(3) C12 0.043(4) 0.053(4) 0.035(4) -0.019(3) 0.000(3) 0.011(3) C10 0.061(5) 0.045(4) 0.027(3) -0.006(3) -0.012(3) 0.018(3) C11 0.051(5) 0.051(4) 0.036(4) -0.012(3) -0.006(3) 0.009(3) C15 0.034(4) 0.053(4) 0.063(5) 0.010(4) 0.009(3) -0.013(3) C16 0.044(5) 0.109(7) 0.063(6) -0.019(5) 0.013(4) -0.029(5) C14 0.058(5) 0.051(4) 0.073(6) -0.017(4) 0.024(4) -0.018(4) O5 0.033(3) 0.053(3) 0.054(3) 0.002(2) 0.015(2) -0.012(2) C17 0.037(4) 0.078(5) 0.039(4) 0.009(4) 0.006(3) -0.017(4) O6 0.025(2) 0.028(2) 0.040(2) 0.0059(17) -0.0050(18) 0.0015(16) C20 0.037(5) 0.078(6) 0.100(7) 0.055(5) -0.006(4) 0.001(4) C19 0.031(4) 0.101(7) 0.102(7) 0.069(6) -0.010(4) -0.009(4) C21 0.020(3) 0.048(4) 0.039(4) 0.003(3) 0.001(3) 0.004(3) C18 0.043(4) 0.029(3) 0.062(5) 0.013(3) -0.008(3) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O3 2.116(4) . ? Bi1 O2 2.118(3) . ? Bi1 O1 2.155(3) . ? Bi1 O4 2.588(4) . ? Bi1 O6 2.708(4) . ? Bi1 O5 2.760(4) . ? O1 C2 1.377(6) . ? C2 C3 1.516(8) . ? C2 C1 1.518(8) . ? C1 F2 1.330(7) . ? C1 F1 1.334(7) . ? C1 F3 1.335(7) . ? C3 F4 1.323(6) . ? C3 F6 1.333(7) . ? C3 F5 1.340(7) . ? O2 C5 1.390(6) . ? C5 C6 1.513(8) . ? C5 C4 1.512(7) . ? C4 F9 1.331(6) . ? C4 F7 1.338(7) . ? C4 F8 1.342(7) . ? C6 F12 1.324(7) . ? C6 F10 1.335(7) . ? C6 F11 1.347(7) . ? O3 C8 1.380(6) . ? F17 C9 1.342(7) . ? O4 C10 1.439(7) . ? O4 C13 1.445(6) . ? F18 C9 1.301(8) . ? C8 C9 1.519(8) . ? C8 C7 1.523(8) . ? F16 C9 1.334(8) . ? C13 C12 1.502(8) . ? F15 C7 1.321(7) . ? F14 C7 1.332(7) . ? F13 C7 1.311(7) . ? C12 C11 1.508(9) . ? C10 C11 1.510(8) . ? C15 C14 1.491(9) . ? C15 C16 1.509(11) . ? C16 C17 1.497(10) . ? C14 O5 1.439(8) . ? O5 C17 1.439(8) . ? O6 C18 1.435(7) . ? O6 C21 1.438(7) . ? C20 C19 1.453(10) . ? C20 C21 1.487(9) . ? C19 C18 1.467(9) . ? 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 O3 Bi1 O2 92.03(14) . . ? O3 Bi1 O1 88.91(14) . . ? O2 Bi1 O1 90.01(14) . . ? O3 Bi1 O4 73.64(12) . . ? O2 Bi1 O4 96.55(14) . . ? O1 Bi1 O4 161.51(13) . . ? O3 Bi1 O6 153.02(13) . . ? O2 Bi1 O6 75.97(13) . . ? O1 Bi1 O6 114.73(13) . . ? O4 Bi1 O6 83.68(12) . . ? O3 Bi1 O5 106.20(15) . . ? O2 Bi1 O5 161.72(14) . . ? O1 Bi1 O5 89.00(14) . . ? O4 Bi1 O5 90.05(14) . . ? O6 Bi1 O5 87.89(13) . . ? C2 O1 Bi1 123.6(3) . . ? O1 C2 C3 109.6(4) . . ? O1 C2 C1 109.9(5) . . ? C3 C2 C1 111.9(4) . . ? F2 C1 F1 107.0(5) . . ? F2 C1 F3 106.8(5) . . ? F1 C1 F3 107.0(5) . . ? F2 C1 C2 113.3(5) . . ? F1 C1 C2 113.6(5) . . ? F3 C1 C2 108.8(5) . . ? F4 C3 F6 107.3(5) . . ? F4 C3 F5 106.7(5) . . ? F6 C3 F5 106.1(5) . . ? F4 C3 C2 114.1(5) . . ? F6 C3 C2 110.6(5) . . ? F5 C3 C2 111.6(5) . . ? C5 O2 Bi1 124.7(3) . . ? O2 C5 C6 109.0(4) . . ? O2 C5 C4 109.6(4) . . ? C6 C5 C4 113.0(5) . . ? F9 C4 F7 107.2(5) . . ? F9 C4 F8 107.2(5) . . ? F7 C4 F8 106.6(5) . . ? F9 C4 C5 112.9(5) . . ? F7 C4 C5 112.6(5) . . ? F8 C4 C5 110.0(5) . . ? F12 C6 F10 106.5(5) . . ? F12 C6 F11 107.2(5) . . ? F10 C6 F11 106.6(5) . . ? F12 C6 C5 111.0(5) . . ? F10 C6 C5 112.7(5) . . ? F11 C6 C5 112.5(5) . . ? C8 O3 Bi1 125.1(3) . . ? C10 O4 C13 109.9(4) . . ? C10 O4 Bi1 127.9(3) . . ? C13 O4 Bi1 122.2(3) . . ? O3 C8 C9 111.7(5) . . ? O3 C8 C7 108.9(4) . . ? C9 C8 C7 110.7(5) . . ? F18 C9 F16 108.6(6) . . ? F18 C9 F17 106.5(6) . . ? F16 C9 F17 107.1(6) . . ? F18 C9 C8 113.3(6) . . ? F16 C9 C8 111.9(6) . . ? F17 C9 C8 109.0(5) . . ? O4 C13 C12 105.1(5) . . ? F13 C7 F15 107.7(5) . . ? F13 C7 F14 107.5(5) . . ? F15 C7 F14 105.4(5) . . ? F13 C7 C8 111.9(5) . . ? F15 C7 C8 113.0(5) . . ? F14 C7 C8 110.9(5) . . ? C13 C12 C11 101.9(5) . . ? O4 C10 C11 105.4(5) . . ? C10 C11 C12 103.2(5) . . ? C14 C15 C16 100.8(6) . . ? C17 C16 C15 104.1(7) . . ? O5 C14 C15 107.9(6) . . ? C14 O5 C17 108.8(5) . . ? C14 O5 Bi1 117.7(4) . . ? C17 O5 Bi1 128.2(4) . . ? O5 C17 C16 104.6(6) . . ? C18 O6 C21 109.7(4) . . ? C18 O6 Bi1 118.7(4) . . ? C21 O6 Bi1 128.9(3) . . ? C19 C20 C21 105.5(6) . . ? C20 C19 C18 106.9(6) . . ? O6 C21 C20 106.5(5) . . ? O6 C18 C19 105.8(5) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.107 _refine_diff_density_min -1.400 _refine_diff_density_rms 0.134 # Attachment 'compound 4.CIF' data_bida2 _database_code_depnum_ccdc_archive 'CCDC 663323' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 Bi2 F36 N6 O6' _chemical_formula_weight 1756.72 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' F F 0.0171 0.0103 '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 P21/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 17.123(3) _cell_length_b 17.976(4) _cell_length_c 19.379(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.56(3) _cell_angle_gamma 90.00 _cell_volume 5547.7(19) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.103 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3352 _exptl_absorpt_coefficient_mu 6.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6242 _exptl_absorpt_correction_T_max 0.6588 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54132 _diffrn_reflns_av_R_equivalents 0.1890 _diffrn_reflns_av_sigmaI/netI 0.1794 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 29.54 _reflns_number_total 15296 _reflns_number_gt 8134 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_cell_refinement 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_data_reduction 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _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^)+(0.0549P)^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 15296 _refine_ls_number_parameters 775 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1537 _refine_ls_R_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.1557 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi2 Bi 0.34668(2) 0.81038(2) 0.152315(18) 0.01588(10) Uani 1 1 d . . . Bi1 Bi 0.15760(2) 1.14839(2) -0.145055(18) 0.01621(10) Uani 1 1 d . . . O6 O 0.4183(4) 0.9043(4) 0.2090(3) 0.0260(16) Uani 1 1 d . . . O2 O 0.0629(3) 1.1218(4) -0.1054(3) 0.0212(15) Uani 1 1 d . . . N1 N 0.1916(5) 1.2619(4) -0.0575(4) 0.0194(18) Uani 1 1 d . . . O3 O 0.0801(4) 1.2344(4) -0.2111(3) 0.0268(17) Uani 1 1 d . . . O4 O 0.4286(4) 0.7532(4) 0.2525(3) 0.0230(16) Uani 1 1 d . . . O1 O 0.0904(4) 1.0843(4) -0.2460(3) 0.0251(16) Uani 1 1 d . . . C14 C 0.5226(5) 0.7861(6) 0.1494(6) 0.023(2) Uani 1 1 d . . . H14 H 0.5311 0.7976 0.2022 0.028 Uiso 1 1 calc R . . N6 N 0.2733(5) 0.6895(4) 0.0547(4) 0.024(2) Uani 1 1 d . . . N5 N 0.1988(6) 0.5759(5) -0.0220(5) 0.031(2) Uani 1 1 d . . . N2 N 0.2477(6) 1.3756(5) 0.0286(5) 0.035(2) Uani 1 1 d . . . F30 F 0.5536(3) 0.9105(3) 0.1349(3) 0.0344(15) Uani 1 1 d . . . F10 F -0.0558(4) 1.2393(4) -0.1389(4) 0.0436(18) Uani 1 1 d . . . F9 F 0.0019(3) 0.9871(3) -0.1667(3) 0.0378(16) Uani 1 1 d . . . F33 F 0.5898(4) 0.9114(4) 0.3000(4) 0.0492(19) Uani 1 1 d . . . F25 F 0.5036(4) 0.6570(3) 0.1619(4) 0.048(2) Uani 1 1 d . . . F29 F 0.5556(5) 0.8357(4) 0.0506(4) 0.066(2) Uani 1 1 d . . . F12 F -0.0635(4) 1.1618(4) -0.0574(4) 0.056(2) Uani 1 1 d . . . F36 F 0.3085(4) 0.9193(4) 0.2781(4) 0.058(2) Uani 1 1 d . . . F32 F 0.5281(4) 1.0159(3) 0.2706(4) 0.0455(18) Uani 1 1 d . . . F28 F 0.6548(4) 0.8327(4) 0.1575(4) 0.053(2) Uani 1 1 d . . . F7 F -0.0452(4) 1.0152(4) -0.0821(4) 0.0475(18) Uani 1 1 d . . . F6 F -0.0353(4) 0.9952(4) -0.3346(4) 0.052(2) Uani 1 1 d . . . F31 F 0.5590(4) 0.9733(4) 0.3816(4) 0.058(2) Uani 1 1 d . . . F4 F 0.0355(4) 1.0421(4) -0.3956(3) 0.0522(19) Uani 1 1 d . . . F8 F -0.1264(3) 1.0222(4) -0.1972(4) 0.050(2) Uani 1 1 d . . . F5 F 0.0493(4) 0.9271(4) -0.3645(3) 0.054(2) Uani 1 1 d . . . C13 C 0.5508(7) 0.7056(7) 0.1445(7) 0.037(3) Uani 1 1 d . . . N3 N 0.2990(5) 0.9200(4) 0.0562(4) 0.0203(18) Uani 1 1 d . . . C4 C -0.0482(6) 1.0356(6) -0.1512(6) 0.026(2) Uani 1 1 d . . . F3 F 0.2151(4) 0.9465(4) -0.2893(4) 0.0503(19) Uani 1 1 d . . . C2 C 0.1090(6) 1.0157(6) -0.2673(5) 0.023(2) Uani 1 1 d . . . H2 H 0.1086 0.9785 -0.2291 0.027 Uiso 1 1 calc R . . F27 F 0.5466(5) 0.6884(4) 0.0752(5) 0.066(2) Uani 1 1 d . . . F2 F 0.2023(4) 1.0611(4) -0.3215(4) 0.0471(18) Uani 1 1 d . . . F34 F 0.3679(4) 1.0246(4) 0.2770(5) 0.061(2) Uani 1 1 d . . . F26 F 0.6292(4) 0.6936(4) 0.1886(4) 0.060(2) Uani 1 1 d . . . C16 C 0.5301(7) 0.9538(7) 0.3071(6) 0.036(3) Uani 1 1 d . . . C27 C 0.3658(6) 0.9611(6) 0.0416(6) 0.034(3) Uani 1 1 d . . . H27A H 0.3954 0.9275 0.0188 0.040 Uiso 1 1 calc R . . H27B H 0.4072 0.9804 0.0887 0.040 Uiso 1 1 calc R . . F35 F 0.4019(5) 0.9630(5) 0.3782(4) 0.081(3) Uani 1 1 d . . . C15 C 0.5717(6) 0.8412(7) 0.1226(6) 0.032(3) Uani 1 1 d . . . C3 C 0.0387(7) 0.9955(6) -0.3406(5) 0.030(3) Uani 1 1 d . . . C17 C 0.4483(6) 0.9144(6) 0.2861(5) 0.028(3) Uani 1 1 d . . . H17 H 0.4579 0.8645 0.3106 0.034 Uiso 1 1 calc R . . C5 C -0.0210(6) 1.1149(6) -0.1521(5) 0.026(2) Uani 1 1 d . . . H5 H -0.0258 1.1276 -0.2038 0.031 Uiso 1 1 calc R . . C25 C 0.2393(7) 0.8911(6) -0.0150(5) 0.035(3) Uani 1 1 d . . . H25A H 0.1936 0.8640 -0.0062 0.042 Uiso 1 1 calc R . . H25B H 0.2687 0.8557 -0.0362 0.042 Uiso 1 1 calc R . . C29 C 0.2533(7) 0.9719(6) 0.0872(6) 0.035(3) Uani 1 1 d . . . H29A H 0.2930 0.9945 0.1334 0.042 Uiso 1 1 calc R . . H29B H 0.2101 0.9444 0.0995 0.042 Uiso 1 1 calc R . . C33 C 0.2562(8) 0.5546(7) 0.0507(6) 0.059(4) Uani 1 1 d . . . H33A H 0.2977 0.5189 0.0456 0.071 Uiso 1 1 calc R . . H33B H 0.2246 0.5293 0.0777 0.071 Uiso 1 1 calc R . . C6 C -0.0733(7) 1.1681(7) -0.1290(7) 0.037(3) Uani 1 1 d . . . C1 C 0.1939(7) 1.0135(6) -0.2737(6) 0.030(3) Uani 1 1 d . . . C34 C 0.3028(7) 0.6227(6) 0.0963(6) 0.043(3) Uani 1 1 d . . . H34A H 0.2931 0.6253 0.1435 0.051 Uiso 1 1 calc R . . H34B H 0.3639 0.6174 0.1082 0.051 Uiso 1 1 calc R . . C36 C 0.2864(8) 0.6878(7) -0.0147(7) 0.049(4) Uani 1 1 d . . . H36A H 0.3473 0.6886 -0.0052 0.059 Uiso 1 1 calc R . . H36B H 0.2605 0.7321 -0.0447 0.059 Uiso 1 1 calc R . . C32 C 0.1815(7) 0.6935(6) 0.0371(7) 0.038(3) Uani 1 1 d . . . H32A H 0.1591 0.7411 0.0118 0.046 Uiso 1 1 calc R . . H32B H 0.1698 0.6914 0.0835 0.046 Uiso 1 1 calc R . . C35 C 0.2458(8) 0.6150(7) -0.0586(7) 0.053(4) Uani 1 1 d . . . H35A H 0.2082 0.6283 -0.1095 0.064 Uiso 1 1 calc R . . H35B H 0.2906 0.5822 -0.0622 0.064 Uiso 1 1 calc R . . C31 C 0.1385(7) 0.6273(7) -0.0138(7) 0.047(3) Uani 1 1 d . . . H31A H 0.1018 0.6009 0.0074 0.057 Uiso 1 1 calc R . . H31B H 0.1028 0.6464 -0.0632 0.057 Uiso 1 1 calc R . . C18 C 0.3834(8) 0.9552(8) 0.3063(7) 0.047(3) Uani 1 1 d . . . F1 F 0.2526(3) 1.0323(3) -0.2059(3) 0.0361(15) Uani 1 1 d . . . F16 F -0.0267(4) 1.3448(3) -0.2739(4) 0.0437(17) Uani 1 1 d . . . F18 F -0.0906(4) 1.2404(4) -0.3036(4) 0.0517(19) Uani 1 1 d . . . F14 F 0.1916(4) 1.2429(4) -0.2807(4) 0.056(2) Uani 1 1 d . . . N4 N 0.2331(5) 1.0263(5) -0.0363(5) 0.026(2) Uani 1 1 d . . . F13 F 0.1307(5) 1.3488(4) -0.2887(5) 0.064(2) Uani 1 1 d . . . C11 C 0.4174(6) 0.6895(6) 0.2878(5) 0.024(2) Uani 1 1 d . . . H11 H 0.4046 0.6469 0.2522 0.029 Uiso 1 1 calc R . . F15 F 0.0993(5) 1.2775(5) -0.3845(4) 0.082(3) Uani 1 1 d . . . C8 C 0.0525(7) 1.2411(6) -0.2874(5) 0.030(3) Uani 1 1 d . . . H8 H 0.0416 1.1902 -0.3096 0.035 Uiso 1 1 calc R . . C28 C 0.3253(6) 1.0275(6) -0.0124(6) 0.030(3) Uani 1 1 d . . . H28A H 0.3470 1.0751 0.0130 0.036 Uiso 1 1 calc R . . H28B H 0.3414 1.0241 -0.0565 0.036 Uiso 1 1 calc R . . C30 C 0.2110(7) 1.0342(6) 0.0300(6) 0.043(3) Uani 1 1 d . . . H30A H 0.1493 1.0312 0.0154 0.052 Uiso 1 1 calc R . . H30B H 0.2296 1.0834 0.0529 0.052 Uiso 1 1 calc R . . C23 C 0.1229(6) 1.3059(6) -0.0509(6) 0.034(3) Uani 1 1 d . . . H23A H 0.0883 1.2739 -0.0318 0.041 Uiso 1 1 calc R . . H23B H 0.0867 1.3241 -0.1006 0.041 Uiso 1 1 calc R . . C10 C 0.3430(8) 0.7006(7) 0.3142(6) 0.042(3) Uani 1 1 d . . . C24 C 0.1561(7) 1.3731(7) 0.0018(7) 0.046(3) Uani 1 1 d . . . H24A H 0.1327 1.4198 -0.0249 0.056 Uiso 1 1 calc R . . H24B H 0.1377 1.3688 0.0445 0.056 Uiso 1 1 calc R . . C21 C 0.2429(8) 1.3108(6) -0.0846(7) 0.052(4) Uani 1 1 d . . . H21A H 0.2090 1.3281 -0.1353 0.062 Uiso 1 1 calc R . . H21B H 0.2915 1.2826 -0.0870 0.062 Uiso 1 1 calc R . . C26 C 0.2023(7) 0.9538(6) -0.0697(6) 0.042(3) Uani 1 1 d . . . H26A H 0.2174 0.9466 -0.1139 0.051 Uiso 1 1 calc R . . H26B H 0.1403 0.9526 -0.0861 0.051 Uiso 1 1 calc R . . C20 C 0.2797(8) 1.3065(6) 0.0688(7) 0.054(4) Uani 1 1 d . . . H20A H 0.2631 1.3034 0.1125 0.065 Uiso 1 1 calc R . . H20B H 0.3418 1.3062 0.0867 0.065 Uiso 1 1 calc R . . C9 C -0.0309(7) 1.2830(7) -0.3109(6) 0.041(3) Uani 1 1 d . . . C22 C 0.2738(9) 1.3774(7) -0.0335(8) 0.061(4) Uani 1 1 d . . . H22A H 0.3359 1.3789 -0.0152 0.073 Uiso 1 1 calc R . . H22B H 0.2524 1.4235 -0.0621 0.073 Uiso 1 1 calc R . . C12 C 0.5003(8) 0.6734(8) 0.3538(7) 0.051(4) Uani 1 1 d . . . C7 C 0.1173(8) 1.2781(7) -0.3108(6) 0.043(3) Uani 1 1 d . . . C19 C 0.2448(8) 1.2388(7) 0.0182(6) 0.052(4) Uani 1 1 d . . . H19A H 0.2921 1.2083 0.0161 0.062 Uiso 1 1 calc R . . H19B H 0.2115 1.2076 0.0393 0.062 Uiso 1 1 calc R . . F19 F 0.2740(4) 0.7136(4) 0.2558(4) 0.0464(18) Uani 1 1 d . . . F11 F -0.1563(4) 1.1598(4) -0.1672(4) 0.0472(19) Uani 1 1 d . . . F17 F -0.0575(5) 1.3002(4) -0.3845(4) 0.061(2) Uani 1 1 d . . . F22 F 0.5232(5) 0.7288(4) 0.4020(4) 0.069(2) Uani 1 1 d . . . F21 F 0.3300(5) 0.6415(4) 0.3485(4) 0.067(2) Uani 1 1 d . . . F24 F 0.5625(4) 0.6619(5) 0.3277(4) 0.068(2) Uani 1 1 d . . . F23 F 0.4940(5) 0.6130(4) 0.3895(4) 0.071(2) Uani 1 1 d . . . F20 F 0.3561(5) 0.7576(5) 0.3608(4) 0.071(3) Uani 1 1 d . . . O5 O 0.4361(4) 0.7921(4) 0.1054(3) 0.0220(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 Bi2 0.01230(17) 0.0192(2) 0.01654(17) 0.00215(15) 0.00581(13) -0.00085(16) Bi1 0.01310(17) 0.0188(2) 0.01764(17) -0.00098(15) 0.00672(13) 0.00076(16) O6 0.032(4) 0.029(4) 0.018(3) -0.002(3) 0.010(3) -0.002(3) O2 0.011(3) 0.035(4) 0.016(3) 0.006(3) 0.004(3) -0.003(3) N1 0.024(4) 0.015(4) 0.014(4) 0.008(3) 0.000(3) 0.011(4) O3 0.035(4) 0.027(4) 0.016(3) 0.006(3) 0.008(3) 0.012(3) O4 0.019(3) 0.028(4) 0.018(3) 0.006(3) 0.003(3) 0.001(3) O1 0.027(4) 0.024(4) 0.022(4) -0.003(3) 0.006(3) 0.003(3) C14 0.010(5) 0.030(6) 0.030(6) 0.003(5) 0.008(4) 0.005(4) N6 0.030(5) 0.017(5) 0.028(5) 0.000(4) 0.013(4) -0.011(4) N5 0.043(5) 0.019(5) 0.023(5) -0.004(4) 0.003(4) 0.002(4) N2 0.036(5) 0.028(6) 0.032(5) -0.006(4) 0.003(4) 0.000(5) F30 0.024(3) 0.032(4) 0.050(4) 0.004(3) 0.016(3) 0.000(3) F10 0.027(3) 0.026(4) 0.081(5) -0.009(4) 0.023(4) -0.001(3) F9 0.028(3) 0.034(4) 0.054(4) 0.002(3) 0.019(3) 0.005(3) F33 0.028(4) 0.067(5) 0.046(4) -0.006(4) 0.006(3) 0.010(4) F25 0.031(4) 0.024(4) 0.101(6) 0.011(4) 0.039(4) -0.001(3) F29 0.082(6) 0.084(6) 0.054(5) -0.010(4) 0.052(5) -0.034(5) F12 0.058(5) 0.063(5) 0.067(5) 0.000(4) 0.048(4) 0.017(4) F36 0.036(4) 0.094(6) 0.049(4) -0.029(4) 0.022(4) -0.026(4) F32 0.055(4) 0.021(4) 0.056(4) 0.004(3) 0.016(4) -0.018(3) F28 0.020(3) 0.032(4) 0.106(6) 0.005(4) 0.024(4) 0.001(3) F7 0.055(4) 0.048(5) 0.055(4) 0.010(4) 0.038(4) -0.002(4) F6 0.031(4) 0.069(6) 0.042(4) -0.016(4) -0.005(3) -0.002(4) F31 0.047(4) 0.075(6) 0.036(4) -0.018(4) -0.003(3) -0.018(4) F4 0.066(5) 0.056(5) 0.020(3) 0.001(3) -0.001(3) 0.002(4) F8 0.012(3) 0.040(4) 0.086(5) -0.017(4) 0.002(3) -0.008(3) F5 0.071(5) 0.045(5) 0.036(4) -0.028(3) 0.009(4) -0.002(4) C13 0.026(6) 0.036(8) 0.051(8) 0.012(6) 0.015(6) 0.010(6) N3 0.017(4) 0.024(5) 0.019(4) 0.003(4) 0.005(3) 0.006(4) C4 0.018(5) 0.020(6) 0.044(6) 0.006(5) 0.017(5) 0.000(5) F3 0.055(4) 0.041(5) 0.055(5) -0.016(4) 0.020(4) 0.020(4) C2 0.038(6) 0.022(6) 0.011(4) -0.004(4) 0.011(4) -0.005(5) F27 0.067(5) 0.059(6) 0.093(6) -0.016(5) 0.054(5) 0.006(4) F2 0.058(5) 0.055(5) 0.039(4) 0.012(4) 0.031(4) 0.008(4) F34 0.042(4) 0.050(5) 0.090(6) -0.025(5) 0.024(4) 0.006(4) F26 0.030(4) 0.046(5) 0.099(6) 0.026(4) 0.018(4) 0.001(4) C16 0.033(6) 0.045(8) 0.023(6) -0.015(5) 0.002(5) -0.011(6) C27 0.018(5) 0.037(7) 0.042(7) 0.014(5) 0.007(5) -0.009(5) F35 0.059(5) 0.152(9) 0.035(4) -0.044(5) 0.021(4) -0.028(5) C15 0.012(5) 0.044(8) 0.046(7) -0.003(6) 0.020(5) 0.001(5) C3 0.032(6) 0.033(7) 0.020(5) -0.014(5) 0.004(5) -0.003(5) C17 0.026(6) 0.037(7) 0.017(5) 0.000(5) 0.002(4) -0.009(5) C5 0.019(5) 0.035(7) 0.023(5) 0.002(5) 0.007(4) 0.010(5) C25 0.039(6) 0.036(7) 0.020(5) 0.009(5) 0.001(5) 0.007(6) C29 0.043(7) 0.036(7) 0.028(6) 0.010(5) 0.015(5) 0.015(6) C33 0.077(10) 0.039(8) 0.027(6) 0.000(6) -0.020(6) -0.010(7) C6 0.019(6) 0.046(8) 0.053(8) 0.004(6) 0.022(5) 0.005(6) C1 0.034(6) 0.021(6) 0.034(6) -0.004(5) 0.013(5) 0.007(5) C34 0.047(7) 0.025(7) 0.038(7) -0.012(5) -0.004(6) -0.013(6) C36 0.064(9) 0.046(9) 0.057(8) -0.010(7) 0.043(8) -0.015(7) C32 0.034(6) 0.031(7) 0.052(8) 0.003(6) 0.018(6) -0.005(6) C35 0.072(10) 0.050(9) 0.036(7) -0.014(6) 0.018(7) -0.001(8) C31 0.038(7) 0.038(8) 0.063(9) -0.019(7) 0.015(6) -0.024(6) C18 0.042(8) 0.066(11) 0.036(7) -0.010(7) 0.019(6) -0.018(7) F1 0.028(3) 0.042(4) 0.036(4) -0.007(3) 0.009(3) 0.005(3) F16 0.050(4) 0.027(4) 0.048(4) -0.002(3) 0.010(3) 0.013(3) F18 0.028(4) 0.052(5) 0.059(5) 0.000(4) -0.002(3) -0.004(4) F14 0.051(4) 0.070(6) 0.060(5) 0.023(4) 0.034(4) 0.024(4) N4 0.018(4) 0.032(6) 0.033(5) 0.013(4) 0.014(4) 0.006(4) F13 0.079(6) 0.038(5) 0.082(6) 0.019(4) 0.036(5) -0.005(4) C11 0.025(5) 0.027(6) 0.019(5) 0.003(4) 0.006(4) -0.009(5) F15 0.100(7) 0.127(8) 0.030(4) 0.028(5) 0.037(5) 0.037(6) C8 0.044(7) 0.027(6) 0.015(5) 0.002(4) 0.009(5) 0.017(5) C28 0.018(5) 0.032(7) 0.042(6) 0.018(5) 0.013(5) 0.003(5) C30 0.047(7) 0.041(8) 0.058(8) 0.038(6) 0.039(7) 0.030(6) C23 0.025(6) 0.041(8) 0.034(6) -0.023(5) 0.008(5) 0.002(5) C10 0.065(9) 0.036(8) 0.027(6) 0.009(6) 0.018(6) -0.013(7) C24 0.041(7) 0.034(8) 0.060(8) -0.028(6) 0.013(6) 0.006(6) C21 0.079(10) 0.035(8) 0.057(8) -0.032(7) 0.043(8) -0.035(7) C26 0.032(6) 0.045(8) 0.036(7) 0.022(6) -0.005(5) -0.010(6) C20 0.063(9) 0.028(8) 0.048(8) -0.004(6) -0.008(7) 0.008(7) C9 0.037(7) 0.040(8) 0.033(6) 0.001(6) -0.002(5) 0.001(6) C22 0.089(11) 0.035(8) 0.077(10) -0.037(7) 0.051(9) -0.049(8) C12 0.050(8) 0.050(9) 0.032(7) 0.016(6) -0.008(6) -0.008(7) C7 0.063(9) 0.039(8) 0.034(7) 0.016(6) 0.024(6) 0.015(7) C19 0.065(9) 0.039(8) 0.032(7) -0.008(6) -0.005(6) 0.004(7) F19 0.038(4) 0.054(5) 0.055(5) 0.017(4) 0.026(4) -0.003(3) F11 0.019(3) 0.030(4) 0.090(6) 0.001(4) 0.017(4) 0.007(3) F17 0.064(5) 0.060(5) 0.038(4) 0.010(4) -0.007(4) 0.014(4) F22 0.081(6) 0.064(6) 0.032(4) -0.004(4) -0.014(4) -0.032(5) F21 0.083(6) 0.078(6) 0.047(5) 0.028(4) 0.030(4) -0.017(5) F24 0.038(4) 0.090(7) 0.060(5) 0.024(5) -0.001(4) 0.011(4) F23 0.086(6) 0.055(5) 0.047(5) 0.026(4) -0.006(4) -0.010(5) F20 0.106(7) 0.081(6) 0.044(5) -0.018(4) 0.048(5) -0.016(5) O5 0.019(3) 0.025(4) 0.023(4) -0.002(3) 0.010(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi2 O5 2.074(6) . ? Bi2 O6 2.139(7) . ? Bi2 O4 2.189(6) . ? Bi2 N3 2.628(8) . ? Bi2 N6 2.851(8) . ? Bi1 O2 2.089(6) . ? Bi1 O3 2.131(6) . ? Bi1 O1 2.196(6) . ? Bi1 N1 2.580(8) . ? Bi1 N4 2.988(8) . ? O6 C17 1.400(11) . ? O2 C5 1.393(10) . ? N1 C23 1.461(12) . ? N1 C21 1.469(13) . ? N1 C19 1.473(13) . ? O3 C8 1.381(11) . ? O4 C11 1.383(11) . ? O1 C2 1.375(11) . ? C14 O5 1.416(10) . ? C14 C15 1.509(14) . ? C14 C13 1.540(15) . ? N6 C34 1.430(13) . ? N6 C36 1.444(13) . ? N6 C32 1.483(13) . ? N5 C35 1.436(14) . ? N5 C31 1.438(14) . ? N5 C33 1.442(13) . ? N2 C22 1.428(14) . ? N2 C24 1.461(13) . ? N2 C20 1.462(14) . ? F30 C15 1.325(12) . ? F10 C6 1.344(13) . ? F9 C4 1.332(11) . ? F33 C16 1.321(12) . ? F25 C13 1.315(12) . ? F29 C15 1.323(13) . ? F12 C6 1.340(13) . ? F36 C18 1.358(13) . ? F32 C16 1.315(13) . ? F28 C15 1.341(11) . ? F7 C4 1.369(11) . ? F6 C3 1.315(12) . ? F31 C16 1.388(11) . ? F4 C3 1.341(12) . ? F8 C4 1.329(11) . ? F5 C3 1.348(12) . ? C13 F26 1.318(12) . ? C13 F27 1.355(13) . ? N3 C27 1.474(12) . ? N3 C25 1.477(12) . ? N3 C29 1.479(12) . ? C4 C5 1.504(14) . ? F3 C1 1.325(11) . ? C2 C1 1.505(14) . ? C2 C3 1.531(13) . ? F2 C1 1.308(12) . ? F34 C18 1.357(15) . ? C16 C17 1.489(14) . ? C27 C28 1.570(13) . ? F35 C18 1.318(13) . ? C17 C18 1.498(16) . ? C5 C6 1.487(14) . ? C25 C26 1.517(13) . ? C29 C30 1.554(13) . ? C33 C34 1.549(14) . ? C6 F11 1.349(12) . ? C1 F1 1.370(11) . ? C36 C35 1.575(16) . ? C32 C31 1.549(15) . ? F16 C9 1.310(13) . ? F18 C9 1.325(13) . ? F14 C7 1.347(13) . ? N4 C26 1.464(13) . ? N4 C28 1.473(11) . ? N4 C30 1.474(13) . ? F13 C7 1.334(14) . ? C11 C10 1.549(15) . ? C11 C12 1.550(14) . ? F15 C7 1.346(13) . ? C8 C7 1.502(15) . ? C8 C9 1.528(15) . ? C23 C24 1.551(14) . ? C10 F21 1.314(12) . ? C10 F19 1.323(13) . ? C10 F20 1.329(13) . ? C21 C22 1.521(14) . ? C20 C19 1.540(15) . ? C9 F17 1.364(12) . ? C12 F23 1.313(14) . ? C12 F22 1.324(15) . ? C12 F24 1.351(15) . ? 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 Bi2 O6 88.5(2) . . ? O5 Bi2 O4 88.8(2) . . ? O6 Bi2 O4 81.7(2) . . ? O5 Bi2 N3 84.0(2) . . ? O6 Bi2 N3 75.1(2) . . ? O4 Bi2 N3 155.8(2) . . ? O5 Bi2 N6 78.8(2) . . ? O6 Bi2 N6 166.5(2) . . ? O4 Bi2 N6 102.3(2) . . ? N3 Bi2 N6 98.9(2) . . ? O2 Bi1 O3 89.5(2) . . ? O2 Bi1 O1 89.1(2) . . ? O3 Bi1 O1 80.7(2) . . ? O2 Bi1 N1 87.5(3) . . ? O3 Bi1 N1 76.2(2) . . ? O1 Bi1 N1 156.7(2) . . ? O2 Bi1 N4 76.5(2) . . ? O3 Bi1 N4 165.8(2) . . ? O1 Bi1 N4 101.1(2) . . ? N1 Bi1 N4 100.5(2) . . ? C17 O6 Bi2 124.5(6) . . ? C5 O2 Bi1 122.4(6) . . ? C23 N1 C21 108.3(9) . . ? C23 N1 C19 106.9(8) . . ? C21 N1 C19 107.0(9) . . ? C23 N1 Bi1 119.4(6) . . ? C21 N1 Bi1 104.9(6) . . ? C19 N1 Bi1 109.8(6) . . ? C8 O3 Bi1 126.8(6) . . ? C11 O4 Bi2 131.9(6) . . ? C2 O1 Bi1 129.4(6) . . ? O5 C14 C15 109.6(8) . . ? O5 C14 C13 108.5(8) . . ? C15 C14 C13 111.7(8) . . ? C34 N6 C36 111.3(9) . . ? C34 N6 C32 107.2(8) . . ? C36 N6 C32 107.5(9) . . ? C34 N6 Bi2 106.7(6) . . ? C36 N6 Bi2 117.0(6) . . ? C32 N6 Bi2 106.7(6) . . ? C35 N5 C31 107.2(9) . . ? C35 N5 C33 108.0(10) . . ? C31 N5 C33 108.7(10) . . ? C22 N2 C24 109.2(10) . . ? C22 N2 C20 107.3(10) . . ? C24 N2 C20 107.9(10) . . ? F25 C13 F26 107.5(9) . . ? F25 C13 F27 106.8(10) . . ? F26 C13 F27 106.0(9) . . ? F25 C13 C14 112.0(9) . . ? F26 C13 C14 112.5(10) . . ? F27 C13 C14 111.8(9) . . ? C27 N3 C25 108.4(8) . . ? C27 N3 C29 109.0(8) . . ? C25 N3 C29 108.3(8) . . ? C27 N3 Bi2 116.8(6) . . ? C25 N3 Bi2 109.0(6) . . ? C29 N3 Bi2 105.0(5) . . ? F8 C4 F9 107.7(9) . . ? F8 C4 F7 105.9(8) . . ? F9 C4 F7 104.5(8) . . ? F8 C4 C5 113.8(9) . . ? F9 C4 C5 112.9(8) . . ? F7 C4 C5 111.4(9) . . ? O1 C2 C1 112.6(8) . . ? O1 C2 C3 107.6(8) . . ? C1 C2 C3 111.8(8) . . ? F32 C16 F33 107.7(9) . . ? F32 C16 F31 106.0(9) . . ? F33 C16 F31 105.0(9) . . ? F32 C16 C17 114.9(9) . . ? F33 C16 C17 112.5(10) . . ? F31 C16 C17 110.1(9) . . ? N3 C27 C28 109.0(8) . . ? F29 C15 F30 106.8(10) . . ? F29 C15 F28 107.1(8) . . ? F30 C15 F28 107.0(9) . . ? F29 C15 C14 112.7(9) . . ? F30 C15 C14 111.0(8) . . ? F28 C15 C14 111.9(10) . . ? F6 C3 F4 108.3(9) . . ? F6 C3 F5 106.3(9) . . ? F4 C3 F5 105.6(8) . . ? F6 C3 C2 111.9(8) . . ? F4 C3 C2 112.2(9) . . ? F5 C3 C2 112.1(9) . . ? O6 C17 C16 107.0(8) . . ? O6 C17 C18 109.0(9) . . ? C16 C17 C18 114.1(10) . . ? O2 C5 C6 109.8(9) . . ? O2 C5 C4 109.1(8) . . ? C6 C5 C4 112.5(9) . . ? N3 C25 C26 111.1(9) . . ? N3 C29 C30 110.0(8) . . ? N5 C33 C34 111.7(10) . . ? F12 C6 F10 106.2(10) . . ? F12 C6 F11 105.4(8) . . ? F10 C6 F11 105.8(9) . . ? F12 C6 C5 113.4(10) . . ? F10 C6 C5 112.3(9) . . ? F11 C6 C5 113.2(10) . . ? F2 C1 F3 108.8(9) . . ? F2 C1 F1 106.6(9) . . ? F3 C1 F1 106.1(8) . . ? F2 C1 C2 113.7(9) . . ? F3 C1 C2 113.3(9) . . ? F1 C1 C2 107.8(8) . . ? N6 C34 C33 110.0(9) . . ? N6 C36 C35 109.4(9) . . ? N6 C32 C31 108.9(9) . . ? N5 C35 C36 110.9(9) . . ? N5 C31 C32 111.9(9) . . ? F35 C18 F34 106.1(11) . . ? F35 C18 F36 107.5(9) . . ? F34 C18 F36 104.9(11) . . ? F35 C18 C17 114.6(11) . . ? F34 C18 C17 113.0(10) . . ? F36 C18 C17 110.1(10) . . ? C26 N4 C28 108.9(8) . . ? C26 N4 C30 107.7(9) . . ? C28 N4 C30 108.3(8) . . ? C26 N4 Bi1 110.5(6) . . ? C28 N4 Bi1 110.3(5) . . ? C30 N4 Bi1 111.1(6) . . ? O4 C11 C10 109.7(9) . . ? O4 C11 C12 108.1(8) . . ? C10 C11 C12 111.5(9) . . ? O3 C8 C7 111.2(9) . . ? O3 C8 C9 106.1(8) . . ? C7 C8 C9 113.9(10) . . ? N4 C28 C27 111.0(8) . . ? N4 C30 C29 110.5(8) . . ? N1 C23 C24 111.5(8) . . ? F21 C10 F19 108.1(10) . . ? F21 C10 F20 107.3(9) . . ? F19 C10 F20 108.6(11) . . ? F21 C10 C11 112.1(10) . . ? F19 C10 C11 109.0(9) . . ? F20 C10 C11 111.7(10) . . ? N2 C24 C23 110.1(8) . . ? N1 C21 C22 110.4(9) . . ? N4 C26 C25 111.2(9) . . ? N2 C20 C19 110.5(10) . . ? F16 C9 F18 108.8(10) . . ? F16 C9 F17 108.1(10) . . ? F18 C9 F17 105.5(9) . . ? F16 C9 C8 113.4(9) . . ? F18 C9 C8 110.9(10) . . ? F17 C9 C8 109.9(10) . . ? N2 C22 C21 112.9(10) . . ? F23 C12 F22 108.1(10) . . ? F23 C12 F24 107.4(12) . . ? F22 C12 F24 108.1(11) . . ? F23 C12 C11 111.2(10) . . ? F22 C12 C11 112.7(11) . . ? F24 C12 C11 109.2(10) . . ? F13 C7 F15 107.2(10) . . ? F13 C7 F14 106.6(11) . . ? F15 C7 F14 105.6(10) . . ? F13 C7 C8 112.5(10) . . ? F15 C7 C8 114.2(11) . . ? F14 C7 C8 110.2(9) . . ? N1 C19 C20 111.4(10) . . ? C14 O5 Bi2 121.8(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.54 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 2.289 _refine_diff_density_min -3.771 _refine_diff_density_rms 0.277 # Attachment 'compound 6.CIF' data_mono1 _database_code_depnum_ccdc_archive 'CCDC 663324' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H8 Bi4 F48 O10, 2(C7 H8)' _chemical_formula_sum 'C38 H24 Bi4 F48 O10' _chemical_formula_weight 2388.49 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' F F 0.0171 0.0103 '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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.7084(12) _cell_length_b 12.0381(11) _cell_length_c 19.6916(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.155(2) _cell_angle_gamma 90.00 _cell_volume 3012.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 11.847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.110 _exptl_absorpt_correction_T_max 0.306 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19964 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.4706 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6513 _reflns_number_gt 2967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II v1.0 (Bruker ASX 2004)' _computing_cell_refinement 'Apex II v1.0 (Bruker ASX 2004)' _computing_data_reduction 'Apex II v1.0 (Bruker ASX 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour 1997)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6513 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0587 _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_restrained_S_all 0.866 _refine_ls_shift/su_max 0.002 _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 0.538881(19) 1.075361(15) 0.926855(10) 0.01255(7) Uani 1 1 d . . . Bi2 Bi 0.694680(19) 0.820779(16) 0.973465(10) 0.01347(7) Uani 1 1 d . . . O1 O 0.4424(4) 0.9737(4) 0.86823(19) 0.0171(9) Uani 1 1 d . . . C1 C 0.4379(7) 0.9339(6) 0.7490(3) 0.0313(18) Uani 1 1 d . . . O5 O 0.5773(4) 0.9385(3) 0.9933(2) 0.0162(9) Uani 1 1 d . . . O2 O 0.6917(4) 0.9567(4) 0.88841(19) 0.0177(9) Uani 1 1 d . . . O3 O 0.8144(4) 0.9133(4) 1.0158(2) 0.0183(9) Uani 1 1 d . . . O4 O 0.6201(4) 0.7875(3) 1.0757(2) 0.0188(9) Uani 1 1 d . . . F2 F 0.3340(5) 0.9385(5) 0.7464(3) 0.0607(18) Uani 1 1 d . . . F6 F 0.4826(4) 0.7580(4) 0.9013(2) 0.0402(12) Uani 1 1 d . . . C11 C 0.6265(6) 0.6876(5) 1.1118(3) 0.0208(14) Uani 1 1 d . . . H11 H 0.6992 0.6569 1.1070 0.025 Uiso 1 1 calc R . . C9 C 0.8848(5) 0.9071(6) 1.1268(3) 0.0205(13) Uani 1 1 d . . . C8 C 0.8099(6) 0.9658(5) 1.0787(3) 0.0185(13) Uani 1 1 d . . . H8 H 0.7367 0.9598 1.0969 0.022 Uiso 1 1 calc R . . F9 F 0.6817(4) 1.1322(4) 0.8008(2) 0.0351(10) Uani 1 1 d . . . F18 F 0.8631(4) 0.7995(3) 1.1292(2) 0.0325(10) Uani 1 1 d . . . F8 F 0.8504(4) 1.1434(4) 0.7906(2) 0.0424(12) Uani 1 1 d . . . F23 F 0.6772(4) 0.7810(5) 1.2109(2) 0.0405(12) Uani 1 1 d . . . F22 F 0.5112(4) 0.7596(4) 1.19570(19) 0.0325(10) Uani 1 1 d . . . F11 F 0.7214(5) 0.9271(4) 0.7433(2) 0.0450(14) Uani 1 1 d . . . F24 F 0.6071(4) 0.6189(4) 1.2236(2) 0.0466(13) Uani 1 1 d . . . F1 F 0.4735(5) 1.0344(4) 0.7343(2) 0.0447(13) Uani 1 1 d . . . F19 F 0.5719(5) 0.5897(4) 1.0154(3) 0.0442(13) Uani 1 1 d . . . F17 F 0.8786(5) 0.9462(4) 1.1905(2) 0.0412(13) Uani 1 1 d . . . F7 F 0.7764(5) 1.1740(3) 0.8874(3) 0.0407(12) Uani 1 1 d . . . F16 F 0.9853(4) 0.9157(4) 1.1064(3) 0.0437(13) Uani 1 1 d . . . F21 F 0.4495(4) 0.6431(4) 1.0833(3) 0.0441(12) Uani 1 1 d . . . F10 F 0.8891(5) 0.9290(5) 0.7598(3) 0.0597(17) Uani 1 1 d . . . F3 F 0.4735(6) 0.8657(5) 0.7013(2) 0.0610(18) Uani 1 1 d . . . F12 F 0.7909(5) 0.8079(4) 0.8086(3) 0.0486(14) Uani 1 1 d . . . F20 F 0.5476(5) 0.5074(4) 1.1114(3) 0.0592(16) Uani 1 1 d . . . C5 C 0.7808(5) 0.9879(5) 0.8531(3) 0.0208(13) Uani 1 1 d . . . H5 H 0.8432 0.9787 0.8836 0.025 Uiso 1 1 calc R . . C4 C 0.7741(6) 1.1083(6) 0.8315(4) 0.0269(14) Uani 1 1 d . . . C3 C 0.4453(6) 0.7814(6) 0.8388(3) 0.0269(15) Uani 1 1 d . . . F4 F 0.3442(4) 0.7652(4) 0.8392(2) 0.0403(11) Uani 1 1 d . . . F5 F 0.4876(5) 0.7070(4) 0.7962(3) 0.0533(15) Uani 1 1 d . . . C6 C 0.7967(6) 0.9147(6) 0.7897(3) 0.0268(15) Uani 1 1 d . . . C7 C 0.8362(8) 1.0879(5) 1.0675(4) 0.0314(18) Uani 1 1 d . . . C12 C 0.6060(6) 0.7119(6) 1.1868(4) 0.0282(16) Uani 1 1 d . . . C10 C 0.5480(7) 0.6046(6) 1.0811(4) 0.0334(18) Uani 1 1 d . . . C2 C 0.4788(5) 0.8987(5) 0.8190(3) 0.0194(13) Uani 1 1 d . . . H2 H 0.5575 0.9017 0.8184 0.023 Uiso 1 1 calc R . . F15 F 0.8478(4) 1.1431(4) 1.1260(2) 0.0383(11) Uani 1 1 d . . . F13 F 0.7584(5) 1.1367(4) 1.0332(2) 0.0455(14) Uani 1 1 d . . . F14 F 0.9227(5) 1.1013(4) 1.0318(3) 0.0529(15) Uani 1 1 d . . . C14 C 0.8219(7) 0.5056(7) 1.0004(5) 0.041(2) Uani 1 1 d . . . C19 C 0.8868(8) 0.5850(7) 1.0307(4) 0.038(2) Uani 1 1 d . . . H19 H 0.8997 0.5817 1.0781 0.046 Uiso 1 1 calc R . . C18 C 0.9323(7) 0.6680(7) 0.9928(4) 0.0321(17) Uani 1 1 d . . . H18 H 0.9749 0.7222 1.0146 0.038 Uiso 1 1 calc R . . C17 C 0.9163(7) 0.6736(6) 0.9219(4) 0.0349(18) Uani 1 1 d . . . H17 H 0.9487 0.7293 0.8949 0.042 Uiso 1 1 calc R . . C15 C 0.8062(9) 0.5122(7) 0.9300(5) 0.046(2) Uani 1 1 d . . . H15 H 0.7634 0.4585 0.9079 0.055 Uiso 1 1 calc R . . C16 C 0.8507(7) 0.5931(8) 0.8933(4) 0.039(2) Uani 1 1 d . . . H16 H 0.8370 0.5958 0.8459 0.047 Uiso 1 1 calc R . . C13 C 0.7775(11) 0.4122(9) 1.0422(7) 0.067(3) Uani 1 1 d . . . H13A H 0.7013 0.4080 1.0350 0.100 Uiso 1 1 calc R . . H13B H 0.7922 0.4259 1.0903 0.100 Uiso 1 1 calc R . . H13C H 0.8101 0.3420 1.0284 0.100 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 0.01351(12) 0.01565(11) 0.00850(10) 0.00250(6) 0.00270(9) -0.00192(8) Bi2 0.01358(12) 0.01440(11) 0.01245(11) -0.00178(6) 0.00195(9) 0.00104(8) O1 0.011(2) 0.029(2) 0.0107(17) -0.0049(15) 0.0059(17) 0.0014(18) C1 0.031(4) 0.050(4) 0.013(3) -0.008(3) 0.005(3) -0.017(3) O5 0.015(2) 0.0194(19) 0.0143(19) 0.0011(14) -0.0007(18) 0.0027(17) O2 0.016(2) 0.025(2) 0.0126(18) 0.0012(15) 0.0017(18) -0.0011(18) O3 0.012(2) 0.031(2) 0.0116(18) -0.0024(15) 0.0020(18) -0.0020(18) O4 0.022(2) 0.0138(18) 0.021(2) 0.0082(15) 0.0016(19) 0.0010(18) F2 0.038(3) 0.091(4) 0.052(3) 0.026(3) -0.024(3) -0.028(3) F6 0.053(3) 0.031(2) 0.037(2) 0.0019(17) -0.016(2) -0.003(2) C11 0.019(3) 0.018(3) 0.025(3) 0.007(2) -0.004(3) 0.003(3) C9 0.012(3) 0.032(3) 0.017(3) 0.002(2) 0.001(3) -0.002(3) C8 0.018(3) 0.018(3) 0.019(3) 0.000(2) -0.003(3) 0.000(2) F9 0.028(2) 0.037(2) 0.040(2) 0.0145(19) 0.008(2) 0.008(2) F18 0.045(3) 0.0221(18) 0.030(2) 0.0061(15) -0.006(2) 0.0077(19) F8 0.031(3) 0.054(3) 0.042(2) 0.023(2) 0.024(2) 0.001(2) F23 0.034(3) 0.066(3) 0.0217(19) 0.0041(19) -0.003(2) -0.007(3) F22 0.026(2) 0.050(3) 0.0215(18) 0.0147(17) 0.0110(18) 0.009(2) F11 0.053(4) 0.065(3) 0.017(2) -0.0071(18) -0.001(2) 0.002(3) F24 0.037(3) 0.056(3) 0.047(3) 0.042(2) 0.003(2) 0.004(3) F1 0.061(4) 0.054(3) 0.0193(19) 0.0071(18) 0.001(2) -0.018(3) F19 0.058(4) 0.030(2) 0.044(3) -0.0045(18) -0.006(3) -0.012(2) F17 0.063(4) 0.045(2) 0.0155(18) -0.0067(16) -0.013(2) 0.003(2) F7 0.051(3) 0.028(2) 0.043(3) -0.0019(17) 0.008(3) -0.015(2) F16 0.018(2) 0.065(3) 0.048(3) 0.006(2) -0.004(2) -0.002(2) F21 0.021(2) 0.046(3) 0.066(3) 0.004(2) 0.000(2) -0.015(2) F10 0.040(3) 0.090(5) 0.049(3) -0.016(3) 0.035(3) 0.006(3) F3 0.102(5) 0.066(4) 0.0147(19) -0.019(2) 0.006(3) -0.013(4) F12 0.069(4) 0.035(2) 0.042(3) -0.0111(19) 0.013(3) 0.020(2) F20 0.069(4) 0.025(2) 0.084(4) 0.018(2) 0.003(3) -0.013(3) C5 0.014(3) 0.025(3) 0.023(3) 0.004(2) 0.007(3) 0.000(3) C4 0.016(3) 0.029(3) 0.035(4) 0.014(3) 0.008(3) -0.006(3) C3 0.027(4) 0.027(3) 0.026(3) -0.012(3) 0.002(3) -0.001(3) F4 0.032(3) 0.039(2) 0.050(3) 0.000(2) 0.000(2) -0.016(2) F5 0.068(4) 0.034(2) 0.058(3) -0.023(2) 0.024(3) 0.002(3) C6 0.026(4) 0.042(4) 0.012(3) -0.001(2) 0.010(3) 0.002(3) C7 0.044(5) 0.020(3) 0.029(4) -0.002(2) 0.003(4) -0.005(3) C12 0.019(4) 0.037(4) 0.028(3) 0.023(3) 0.000(3) -0.002(3) C10 0.034(5) 0.019(3) 0.048(4) 0.003(3) -0.006(4) -0.005(3) C2 0.015(3) 0.030(3) 0.013(3) -0.012(2) 0.004(3) 0.000(3) F15 0.046(3) 0.025(2) 0.044(2) -0.0099(18) -0.003(2) -0.005(2) F13 0.072(4) 0.027(2) 0.037(2) 0.0084(18) -0.006(3) 0.013(2) F14 0.055(4) 0.038(2) 0.066(3) -0.001(2) 0.038(3) -0.020(3) C14 0.029(5) 0.029(4) 0.065(5) -0.003(4) 0.000(4) 0.009(3) C19 0.041(5) 0.043(4) 0.030(4) -0.005(3) 0.009(4) 0.018(4) C18 0.018(4) 0.048(4) 0.031(4) -0.010(3) 0.009(3) -0.005(3) C17 0.028(4) 0.041(4) 0.036(4) -0.001(3) 0.010(4) 0.003(3) C15 0.051(6) 0.032(4) 0.054(5) -0.012(4) -0.001(5) -0.006(4) C16 0.033(5) 0.050(5) 0.034(4) -0.015(3) -0.001(4) 0.011(4) C13 0.064(8) 0.045(5) 0.091(9) 0.014(5) 0.021(7) -0.004(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 Bi1 O1 2.080(4) . ? Bi1 O5 2.159(4) . ? Bi1 O5 2.166(5) 3_677 ? Bi1 O2 2.528(5) . ? Bi1 O4 2.610(5) 3_677 ? Bi1 Bi1 3.5472(5) 3_677 ? Bi2 O3 2.060(4) . ? Bi2 O5 2.095(4) . ? Bi2 O4 2.263(5) . ? Bi2 O2 2.342(4) . ? O1 C2 1.405(7) . ? C1 F2 1.322(11) . ? C1 F1 1.323(9) . ? C1 F3 1.329(9) . ? C1 C2 1.532(9) . ? O5 Bi1 2.166(5) 3_677 ? O2 C5 1.382(8) . ? O3 C8 1.393(7) . ? O4 C11 1.399(7) . ? O4 Bi1 2.610(5) 3_677 ? F6 C3 1.348(8) . ? C11 C12 1.530(10) . ? C11 C10 1.534(10) . ? C9 F18 1.326(8) . ? C9 F17 1.342(7) . ? C9 F16 1.345(9) . ? C9 C8 1.514(8) . ? C8 C7 1.524(9) . ? F9 C4 1.351(8) . ? F8 C4 1.331(9) . ? F23 C12 1.316(9) . ? F22 C12 1.347(9) . ? F11 C6 1.329(8) . ? F24 C12 1.334(7) . ? F19 C10 1.341(10) . ? F7 C4 1.354(9) . ? F21 C10 1.336(10) . ? F10 C6 1.327(10) . ? F12 C6 1.340(9) . ? F20 C10 1.314(9) . ? C5 C4 1.513(9) . ? C5 C6 1.542(9) . ? C3 F4 1.300(9) . ? C3 F5 1.340(8) . ? C3 C2 1.525(10) . ? C7 F14 1.316(11) . ? C7 F13 1.331(9) . ? C7 F15 1.338(8) . ? C14 C19 1.395(13) . ? C14 C15 1.404(13) . ? C14 C13 1.503(14) . ? C19 C18 1.375(13) . ? C18 C17 1.412(11) . ? C17 C16 1.396(12) . ? C15 C16 1.337(14) . ? 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 O5 91.14(16) . . ? O1 Bi1 O5 87.43(16) . 3_677 ? O5 Bi1 O5 69.8(2) . 3_677 ? O1 Bi1 O2 87.35(15) . . ? O5 Bi1 O2 65.03(16) . . ? O5 Bi1 O2 134.38(14) 3_677 . ? O1 Bi1 O4 84.60(15) . 3_677 ? O5 Bi1 O4 131.93(17) . 3_677 ? O5 Bi1 O4 62.18(14) 3_677 3_677 ? O2 Bi1 O4 161.24(13) . 3_677 ? O1 Bi1 Bi1 89.12(12) . 3_677 ? O5 Bi1 Bi1 34.97(13) . 3_677 ? O5 Bi1 Bi1 34.84(10) 3_677 3_677 ? O2 Bi1 Bi1 99.79(9) . 3_677 ? O4 Bi1 Bi1 97.00(10) 3_677 3_677 ? O3 Bi2 O5 94.83(17) . . ? O3 Bi2 O4 92.66(17) . . ? O5 Bi2 O4 69.74(16) . . ? O3 Bi2 O2 85.54(16) . . ? O5 Bi2 O2 69.54(16) . . ? O4 Bi2 O2 138.93(16) . . ? C2 O1 Bi1 124.5(4) . . ? F2 C1 F1 107.2(7) . . ? F2 C1 F3 109.9(6) . . ? F1 C1 F3 107.1(7) . . ? F2 C1 C2 112.5(7) . . ? F1 C1 C2 109.5(5) . . ? F3 C1 C2 110.4(7) . . ? Bi2 O5 Bi1 124.3(2) . . ? Bi2 O5 Bi1 124.78(19) . 3_677 ? Bi1 O5 Bi1 110.19(19) . 3_677 ? C5 O2 Bi2 122.5(4) . . ? C5 O2 Bi1 128.9(4) . . ? Bi2 O2 Bi1 101.06(17) . . ? C8 O3 Bi2 125.0(4) . . ? C11 O4 Bi2 125.5(4) . . ? C11 O4 Bi1 126.7(4) . 3_677 ? Bi2 O4 Bi1 101.35(14) . 3_677 ? O4 C11 C12 108.4(5) . . ? O4 C11 C10 108.9(5) . . ? C12 C11 C10 113.2(6) . . ? F18 C9 F17 107.3(5) . . ? F18 C9 F16 106.4(6) . . ? F17 C9 F16 108.1(6) . . ? F18 C9 C8 110.4(5) . . ? F17 C9 C8 112.4(6) . . ? F16 C9 C8 111.9(6) . . ? O3 C8 C9 108.5(5) . . ? O3 C8 C7 107.4(5) . . ? C9 C8 C7 113.8(6) . . ? O2 C5 C4 110.8(6) . . ? O2 C5 C6 111.2(6) . . ? C4 C5 C6 109.1(6) . . ? F8 C4 F9 107.2(5) . . ? F8 C4 F7 106.9(6) . . ? F9 C4 F7 104.9(6) . . ? F8 C4 C5 115.7(7) . . ? F9 C4 C5 112.2(6) . . ? F7 C4 C5 109.3(5) . . ? F4 C3 F5 107.6(6) . . ? F4 C3 F6 107.9(7) . . ? F5 C3 F6 106.9(6) . . ? F4 C3 C2 114.7(6) . . ? F5 C3 C2 110.2(6) . . ? F6 C3 C2 109.2(5) . . ? F10 C6 F11 108.5(6) . . ? F10 C6 F12 107.3(7) . . ? F11 C6 F12 105.0(6) . . ? F10 C6 C5 113.8(6) . . ? F11 C6 C5 113.4(6) . . ? F12 C6 C5 108.4(5) . . ? F14 C7 F13 107.2(6) . . ? F14 C7 F15 108.0(7) . . ? F13 C7 F15 107.3(6) . . ? F14 C7 C8 112.3(6) . . ? F13 C7 C8 109.7(6) . . ? F15 C7 C8 112.1(6) . . ? F23 C12 F24 109.2(5) . . ? F23 C12 F22 107.3(7) . . ? F24 C12 F22 107.2(6) . . ? F23 C12 C11 110.5(6) . . ? F24 C12 C11 111.3(7) . . ? F22 C12 C11 111.2(5) . . ? F20 C10 F21 106.8(7) . . ? F20 C10 F19 108.7(7) . . ? F21 C10 F19 107.0(6) . . ? F20 C10 C11 113.9(6) . . ? F21 C10 C11 111.7(6) . . ? F19 C10 C11 108.5(7) . . ? O1 C2 C3 109.0(6) . . ? O1 C2 C1 109.3(6) . . ? C3 C2 C1 113.0(5) . . ? C19 C14 C15 117.7(9) . . ? C19 C14 C13 120.1(9) . . ? C15 C14 C13 122.1(9) . . ? C18 C19 C14 121.0(8) . . ? C19 C18 C17 120.7(7) . . ? C16 C17 C18 116.7(8) . . ? C16 C15 C14 121.0(8) . . ? C15 C16 C17 122.7(8) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.989 _refine_diff_density_min -1.124 _refine_diff_density_rms 0.135 # Attachment 'compound 8.CIF' data_bitolet _database_code_depnum_ccdc_archive 'CCDC 663325' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 Bi4 F48 O12' _chemical_formula_weight 2352.46 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' F F 0.0171 0.0103 '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 10.1484(3) _cell_length_b 15.1108(5) _cell_length_c 19.1279(5) _cell_angle_alpha 94.013(2) _cell_angle_beta 91.126(2) _cell_angle_gamma 91.274(2) _cell_volume 2924.70(15) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 12.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3454 _exptl_absorpt_correction_T_max 0.3756 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 74379 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_sigmaI/netI 0.0913 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 30.14 _reflns_number_total 16986 _reflns_number_gt 12044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_cell_refinement 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_data_reduction 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _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^)+(0.0166P)^2^+7.3081P] 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 16986 _refine_ls_number_parameters 869 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.002 _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 0.10916(3) 0.796526(18) 0.015735(13) 0.01771(6) Uani 1 1 d . . . Bi2 Bi -0.02867(3) 0.973049(18) -0.090288(13) 0.01547(6) Uani 1 1 d . . . Bi3 Bi 0.39609(2) 0.304770(17) 0.428261(13) 0.01518(6) Uani 1 1 d . . . Bi4 Bi 0.46920(2) 0.466959(17) 0.585424(12) 0.01481(6) Uani 1 1 d . . . O12 O 0.5411(4) 0.5927(3) 0.6631(2) 0.0174(10) Uani 1 1 d . . . O2 O 0.0931(4) 0.8636(3) 0.1220(2) 0.0177(11) Uani 1 1 d . . . O10 O 0.4826(4) 0.4236(3) 0.4741(2) 0.0151(10) Uani 1 1 d . . . O9 O 0.3984(4) 0.2976(3) 0.5428(2) 0.0170(10) Uani 1 1 d . . . O4 O 0.0490(4) 0.8203(3) -0.1054(2) 0.0198(11) Uani 1 1 d . . . O6 O 0.1651(4) 1.0139(3) -0.1065(2) 0.0230(11) Uani 1 1 d . . . O11 O 0.6647(5) 0.4289(3) 0.5892(2) 0.0243(12) Uani 1 1 d . . . O3 O -0.0695(5) 0.7281(3) 0.0197(3) 0.0252(12) Uani 1 1 d . . . O7 O 0.3045(5) 0.1371(3) 0.4303(2) 0.0250(12) Uani 1 1 d . . . O8 O 0.5761(5) 0.2455(3) 0.4152(2) 0.0231(11) Uani 1 1 d . . . O1 O 0.1935(6) 0.6471(4) 0.0745(3) 0.0439(16) Uani 1 1 d . . . C31 C 0.4857(7) 0.6227(5) 0.7264(3) 0.0180(15) Uani 1 1 d . . . H31 H 0.4043 0.6557 0.7155 0.022 Uiso 1 1 calc R . . C6 C 0.1640(7) 0.8391(5) 0.1806(3) 0.0221(16) Uani 1 1 d . . . H6 H 0.1649 0.7729 0.1800 0.026 Uiso 1 1 calc R . . C15 C 0.2630(6) 0.9617(5) -0.1358(4) 0.0233(17) Uani 1 1 d . . . H15 H 0.2260 0.9008 -0.1486 0.028 Uiso 1 1 calc R . . C29 C 0.8747(8) 0.4981(6) 0.6099(4) 0.033(2) Uani 1 1 d . . . C25 C 0.3202(7) 0.2405(5) 0.5793(3) 0.0217(16) Uani 1 1 d . . . H25 H 0.3173 0.1808 0.5531 0.026 Uiso 1 1 calc R . . C9 C -0.1840(7) 0.7604(5) 0.0503(4) 0.0275(18) Uani 1 1 d . . . H9 H -0.1666 0.8213 0.0729 0.033 Uiso 1 1 calc R . . C22 C 0.6927(6) 0.2658(5) 0.4541(4) 0.0185(15) Uani 1 1 d . . . H22 H 0.6731 0.3079 0.4950 0.022 Uiso 1 1 calc R . . C28 C 0.7581(7) 0.4517(5) 0.6423(4) 0.0218(16) Uani 1 1 d . . . H28 H 0.7183 0.4933 0.6785 0.026 Uiso 1 1 calc R . . C27 C 0.7980(8) 0.3681(5) 0.6756(4) 0.0312(19) Uani 1 1 d . . . C8 C -0.2224(9) 0.6969(6) 0.1059(5) 0.041(2) Uani 1 1 d . . . C23 C 0.7904(7) 0.3095(5) 0.4078(4) 0.0268(18) Uani 1 1 d . . . C30 C 0.5827(8) 0.6871(5) 0.7667(4) 0.0278(18) Uani 1 1 d . . . C14 C 0.3738(8) 0.9563(6) -0.0826(4) 0.0293(19) Uani 1 1 d . . . C10 C -0.2866(8) 0.7636(6) -0.0071(5) 0.035(2) Uani 1 1 d . . . C24 C 0.3846(8) 0.2316(6) 0.6513(4) 0.032(2) Uani 1 1 d . . . C26 C 0.1819(8) 0.2733(6) 0.5848(4) 0.035(2) Uani 1 1 d . . . C7 C 0.0938(8) 0.8756(6) 0.2458(4) 0.032(2) Uani 1 1 d . . . C21 C 0.7441(8) 0.1800(6) 0.4806(5) 0.036(2) Uani 1 1 d . . . C16 C 0.3121(8) 1.0021(8) -0.2016(4) 0.045(3) Uani 1 1 d . . . F32 F 0.4054(5) 0.3100(3) 0.6866(2) 0.0393(12) Uani 1 1 d . . . F16 F -0.0712(4) 0.7280(3) -0.2717(2) 0.0312(11) Uani 1 1 d . . . F30 F 0.7470(4) 0.3887(3) 0.3910(2) 0.0374(12) Uani 1 1 d . . . F36 F 0.1354(4) 0.2859(3) 0.5198(2) 0.0362(12) Uani 1 1 d . . . F6 F 0.0746(4) 0.9639(3) 0.2450(2) 0.0353(11) Uani 1 1 d . . . F17 F -0.1491(4) 0.8361(3) -0.2068(2) 0.0338(11) Uani 1 1 d . . . F43 F 0.6180(4) 0.7513(3) 0.7260(2) 0.0345(11) Uani 1 1 d . . . F18 F 0.0465(4) 0.8463(3) -0.2460(2) 0.0332(11) Uani 1 1 d . . . F47 F 0.4042(5) 0.5692(3) 0.8315(2) 0.0394(12) Uani 1 1 d . . . F28 F 0.9077(4) 0.3255(4) 0.4380(3) 0.0464(14) Uani 1 1 d . . . F23 F 0.2121(5) 1.0035(4) -0.2484(2) 0.0552(16) Uani 1 1 d . . . F13 F 0.1624(5) 0.6587(3) -0.1063(2) 0.0438(13) Uani 1 1 d . . . F38 F 0.6978(5) 0.3372(3) 0.7100(3) 0.0522(15) Uani 1 1 d . . . F1 F 0.3578(4) 0.8459(3) 0.1171(2) 0.0378(12) Uani 1 1 d . . . F44 F 0.6927(4) 0.6472(3) 0.7858(2) 0.0420(13) Uani 1 1 d . . . F14 F 0.2292(4) 0.7319(3) -0.1918(2) 0.0428(13) Uani 1 1 d . . . F46 F 0.5437(5) 0.4879(3) 0.7753(2) 0.0459(14) Uani 1 1 d . . . F39 F 0.8359(5) 0.3058(3) 0.6301(3) 0.0481(14) Uani 1 1 d . . . F31 F 0.5007(5) 0.1938(3) 0.6433(2) 0.0453(13) Uani 1 1 d . . . F48 F 0.3477(5) 0.4987(3) 0.7342(2) 0.0422(13) Uani 1 1 d . . . F20 F 0.3275(4) 0.9202(4) -0.0252(2) 0.0480(15) Uani 1 1 d . . . F45 F 0.5316(5) 0.7255(3) 0.8246(2) 0.0406(12) Uani 1 1 d . . . F11 F -0.3021(5) 0.6876(4) -0.0459(2) 0.0455(13) Uani 1 1 d . . . F15 F 0.0963(5) 0.6215(3) -0.2109(2) 0.0485(14) Uani 1 1 d . . . F41 F 0.9347(5) 0.4485(4) 0.5625(2) 0.0478(14) Uani 1 1 d . . . F26 F 0.8617(5) 0.1899(3) 0.5115(3) 0.0432(13) Uani 1 1 d . . . F2 F 0.3116(5) 0.9632(3) 0.1812(3) 0.0439(13) Uani 1 1 d . . . F19 F 0.4269(4) 1.0335(3) -0.0604(2) 0.0438(13) Uani 1 1 d . . . F12 F -0.2527(4) 0.8259(4) -0.0507(3) 0.0516(15) Uani 1 1 d . . . F4 F 0.1616(5) 0.8638(3) 0.3049(2) 0.0464(14) Uani 1 1 d . . . F9 F -0.2458(5) 0.6145(3) 0.0798(3) 0.0520(14) Uani 1 1 d . . . F34 F 0.1757(5) 0.3519(4) 0.6207(3) 0.0534(15) Uani 1 1 d . . . F10 F -0.4055(4) 0.7851(4) 0.0167(3) 0.0516(14) Uani 1 1 d . . . F33 F 0.3121(5) 0.1804(4) 0.6901(2) 0.0547(15) Uani 1 1 d . . . F5 F -0.0231(5) 0.8368(3) 0.2502(2) 0.0462(14) Uani 1 1 d . . . F3 F 0.3817(5) 0.8487(4) 0.2294(2) 0.0530(15) Uani 1 1 d . . . F27 F 0.7536(5) 0.1166(3) 0.4286(3) 0.0567(15) Uani 1 1 d . . . F29 F 0.8091(5) 0.2633(4) 0.3476(2) 0.0544(15) Uani 1 1 d . . . F25 F 0.6616(5) 0.1510(3) 0.5272(3) 0.0538(15) Uani 1 1 d . . . F42 F 0.8316(4) 0.5692(3) 0.5778(3) 0.0550(16) Uani 1 1 d . . . F35 F 0.0995(5) 0.2183(4) 0.6120(3) 0.0611(18) Uani 1 1 d . . . F37 F 0.8971(5) 0.3837(4) 0.7223(3) 0.0615(17) Uani 1 1 d . . . C11 C 0.1242(9) 0.6902(5) -0.1668(4) 0.031(2) Uani 1 1 d . . . F7 F -0.1286(6) 0.6956(4) 0.1538(3) 0.0649(18) Uani 1 1 d . . . F21 F 0.4701(5) 0.9048(4) -0.1059(3) 0.0634(17) Uani 1 1 d . . . F40 F 0.9637(5) 0.5280(4) 0.6578(3) 0.0595(16) Uani 1 1 d . . . F8 F -0.3318(6) 0.7231(4) 0.1388(3) 0.0674(18) Uani 1 1 d . . . C13 C -0.0386(7) 0.7900(5) -0.2211(4) 0.0234(17) Uani 1 1 d . . . F22 F 0.3537(5) 1.0860(4) -0.1884(3) 0.071(2) Uani 1 1 d . . . C12 C 0.0097(7) 0.7525(5) -0.1544(4) 0.0224(17) Uani 1 1 d . . . H12 H -0.0648 0.7183 -0.1347 0.027 Uiso 1 1 calc R . . C18 C 0.3872(9) 0.0638(6) 0.4370(5) 0.046(2) Uani 1 1 d . . . H18A H 0.3352 0.0155 0.4565 0.055 Uiso 1 1 calc R . . H18B H 0.4591 0.0817 0.4711 0.055 Uiso 1 1 calc R . . C19 C 0.1844(8) 0.1174(6) 0.3913(4) 0.040(2) Uani 1 1 d . . . H19A H 0.2062 0.0910 0.3443 0.048 Uiso 1 1 calc R . . H19B H 0.1389 0.1736 0.3849 0.048 Uiso 1 1 calc R . . F24 F 0.4055(5) 0.9579(6) -0.2305(3) 0.094(3) Uani 1 1 d . . . C20 C 0.0906(8) 0.0545(6) 0.4255(5) 0.051(3) Uani 1 1 d . . . H20A H 0.1271 -0.0051 0.4232 0.076 Uiso 1 1 calc R . . H20B H 0.0050 0.0527 0.4007 0.076 Uiso 1 1 calc R . . H20C H 0.0792 0.0753 0.4746 0.076 Uiso 1 1 calc R . . C32 C 0.4466(8) 0.5455(5) 0.7683(4) 0.0278(19) Uani 1 1 d . . . C2 C 0.3301(9) 0.6299(7) 0.0816(6) 0.058(3) Uani 1 1 d . . . H2A H 0.3758 0.6863 0.0981 0.069 Uiso 1 1 calc R . . H2B H 0.3407 0.5885 0.1192 0.069 Uiso 1 1 calc R . . C17 C 0.4467(10) 0.0285(7) 0.3706(5) 0.065(3) Uani 1 1 d . . . H17A H 0.3767 0.0128 0.3356 0.098 Uiso 1 1 calc R . . H17B H 0.4970 -0.0243 0.3793 0.098 Uiso 1 1 calc R . . H17C H 0.5057 0.0739 0.3531 0.098 Uiso 1 1 calc R . . C3 C 0.1158(10) 0.5651(7) 0.0600(7) 0.077(4) Uani 1 1 d . . . H3A H 0.0235 0.5815 0.0505 0.093 Uiso 1 1 calc R . . H3B H 0.1486 0.5349 0.0164 0.093 Uiso 1 1 calc R . . C4 C 0.1143(16) 0.5046(8) 0.1108(7) 0.130(7) Uani 1 1 d . . . H4A H 0.0728 0.5308 0.1530 0.195 Uiso 1 1 calc R . . H4B H 0.2049 0.4888 0.1224 0.195 Uiso 1 1 calc R . . H4C H 0.0642 0.4512 0.0932 0.195 Uiso 1 1 calc R . . C5 C 0.3036(8) 0.8747(6) 0.1785(4) 0.0308(19) Uani 1 1 d . . . C1 C 0.3969(17) 0.5942(13) 0.0220(10) 0.192(10) Uani 1 1 d . . . H1A H 0.3820 0.5297 0.0170 0.288 Uiso 1 1 calc R . . H1B H 0.4916 0.6075 0.0279 0.288 Uiso 1 1 calc R . . H1C H 0.3633 0.6205 -0.0200 0.288 Uiso 1 1 calc R . . O5 O 0.0217(4) 0.9213(3) 0.0077(2) 0.0199(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 0.02205(15) 0.01304(14) 0.01826(14) 0.00335(10) -0.00271(10) 0.00093(11) Bi2 0.01892(14) 0.01475(14) 0.01278(13) 0.00256(10) -0.00254(10) -0.00098(11) Bi3 0.01804(14) 0.01072(13) 0.01668(13) 0.00139(10) -0.00218(10) -0.00115(10) Bi4 0.01941(14) 0.01211(13) 0.01317(13) 0.00344(10) 0.00019(10) -0.00133(11) O12 0.026(3) 0.013(3) 0.013(2) -0.0002(19) 0.0007(19) 0.001(2) O2 0.020(3) 0.019(3) 0.014(2) 0.004(2) -0.0040(19) 0.001(2) O10 0.026(3) 0.010(2) 0.009(2) 0.0008(18) -0.0025(18) -0.005(2) O9 0.020(3) 0.015(3) 0.016(2) 0.0056(19) 0.0017(19) -0.002(2) O4 0.026(3) 0.018(3) 0.016(2) 0.001(2) 0.000(2) 0.000(2) O6 0.019(3) 0.017(3) 0.034(3) 0.006(2) 0.002(2) -0.005(2) O11 0.027(3) 0.029(3) 0.016(3) 0.000(2) -0.008(2) 0.006(2) O3 0.023(3) 0.019(3) 0.032(3) 0.000(2) -0.005(2) -0.002(2) O7 0.032(3) 0.013(3) 0.030(3) 0.001(2) -0.005(2) -0.002(2) O8 0.025(3) 0.014(3) 0.029(3) -0.006(2) -0.004(2) 0.002(2) O1 0.041(4) 0.028(4) 0.064(4) 0.017(3) -0.016(3) -0.008(3) C31 0.020(4) 0.024(4) 0.009(3) -0.005(3) -0.009(3) 0.001(3) C6 0.023(4) 0.021(4) 0.021(4) 0.002(3) -0.009(3) -0.006(3) C15 0.014(4) 0.029(5) 0.027(4) 0.003(3) 0.000(3) -0.006(3) C29 0.027(5) 0.027(5) 0.047(5) 0.010(4) 0.000(4) 0.003(4) C25 0.027(4) 0.018(4) 0.020(4) 0.009(3) -0.005(3) -0.008(3) C9 0.024(4) 0.026(5) 0.032(4) 0.001(3) 0.003(3) -0.007(3) C22 0.016(4) 0.017(4) 0.023(4) 0.003(3) -0.002(3) 0.003(3) C28 0.017(4) 0.026(4) 0.023(4) 0.005(3) -0.001(3) 0.002(3) C27 0.039(5) 0.024(5) 0.031(5) 0.003(4) 0.000(4) 0.000(4) C8 0.046(6) 0.040(6) 0.037(5) 0.006(4) -0.004(4) -0.019(5) C23 0.025(4) 0.032(5) 0.024(4) 0.004(3) 0.001(3) 0.005(4) C30 0.032(5) 0.031(5) 0.019(4) -0.009(3) -0.005(3) 0.005(4) C14 0.026(4) 0.030(5) 0.033(5) 0.016(4) -0.008(3) -0.009(4) C10 0.023(5) 0.031(5) 0.051(6) 0.004(4) 0.002(4) 0.001(4) C24 0.035(5) 0.029(5) 0.034(5) 0.016(4) -0.001(4) 0.003(4) C26 0.025(5) 0.041(6) 0.041(5) 0.016(4) -0.004(4) -0.005(4) C7 0.044(5) 0.030(5) 0.024(4) 0.010(4) -0.004(4) -0.003(4) C21 0.030(5) 0.026(5) 0.052(6) 0.007(4) -0.001(4) 0.005(4) C16 0.024(5) 0.077(8) 0.034(5) 0.019(5) -0.004(4) -0.008(5) F32 0.065(3) 0.035(3) 0.017(2) -0.001(2) -0.009(2) -0.008(3) F16 0.044(3) 0.024(3) 0.024(2) -0.0053(19) -0.007(2) -0.003(2) F30 0.026(3) 0.038(3) 0.051(3) 0.023(2) 0.002(2) -0.005(2) F36 0.023(2) 0.058(4) 0.029(3) 0.018(2) -0.0040(19) 0.005(2) F6 0.050(3) 0.029(3) 0.027(3) 0.004(2) 0.000(2) 0.004(2) F17 0.029(3) 0.034(3) 0.037(3) -0.008(2) -0.006(2) 0.006(2) F43 0.047(3) 0.028(3) 0.027(3) -0.003(2) -0.011(2) -0.014(2) F18 0.037(3) 0.034(3) 0.028(2) 0.007(2) -0.007(2) -0.009(2) F47 0.060(3) 0.042(3) 0.018(2) 0.002(2) 0.016(2) 0.009(3) F28 0.018(3) 0.063(4) 0.060(3) 0.020(3) -0.010(2) -0.011(2) F23 0.040(3) 0.096(5) 0.031(3) 0.024(3) -0.005(2) -0.022(3) F13 0.063(3) 0.036(3) 0.034(3) 0.005(2) -0.008(2) 0.021(3) F38 0.053(3) 0.042(3) 0.067(4) 0.031(3) 0.016(3) 0.005(3) F1 0.022(2) 0.047(3) 0.045(3) 0.009(2) 0.002(2) -0.003(2) F44 0.033(3) 0.058(4) 0.035(3) 0.001(2) -0.017(2) 0.004(3) F14 0.034(3) 0.051(4) 0.044(3) 0.003(2) 0.007(2) 0.009(3) F46 0.062(3) 0.029(3) 0.051(3) 0.022(2) 0.015(3) 0.025(3) F39 0.060(4) 0.025(3) 0.060(3) 0.004(3) 0.001(3) 0.019(3) F31 0.050(3) 0.042(3) 0.046(3) 0.016(2) -0.015(2) 0.012(3) F48 0.056(3) 0.040(3) 0.029(3) 0.000(2) 0.012(2) -0.022(3) F20 0.034(3) 0.064(4) 0.049(3) 0.036(3) -0.014(2) -0.021(3) F45 0.050(3) 0.043(3) 0.026(3) -0.012(2) -0.001(2) -0.003(3) F11 0.043(3) 0.046(4) 0.046(3) -0.003(3) -0.023(2) -0.003(3) F15 0.076(4) 0.029(3) 0.038(3) -0.016(2) -0.012(3) 0.021(3) F41 0.039(3) 0.056(4) 0.050(3) 0.009(3) 0.021(2) 0.013(3) F26 0.037(3) 0.035(3) 0.058(3) 0.012(3) -0.011(2) 0.012(2) F2 0.042(3) 0.031(3) 0.059(3) 0.012(2) -0.006(2) -0.019(2) F19 0.037(3) 0.047(4) 0.048(3) 0.012(3) -0.014(2) -0.017(3) F12 0.037(3) 0.065(4) 0.057(3) 0.040(3) -0.008(2) -0.001(3) F4 0.078(4) 0.046(3) 0.016(2) 0.011(2) -0.012(2) 0.003(3) F9 0.074(4) 0.029(3) 0.053(3) 0.012(3) -0.006(3) -0.029(3) F34 0.050(3) 0.063(4) 0.047(3) -0.009(3) 0.005(2) 0.027(3) F10 0.028(3) 0.053(4) 0.075(4) 0.013(3) 0.006(3) -0.001(3) F33 0.072(4) 0.054(4) 0.041(3) 0.034(3) -0.004(3) -0.025(3) F5 0.045(3) 0.054(4) 0.039(3) 0.008(2) 0.013(2) -0.018(3) F3 0.040(3) 0.077(4) 0.045(3) 0.028(3) -0.023(2) -0.006(3) F27 0.061(4) 0.028(3) 0.078(4) -0.018(3) -0.014(3) 0.019(3) F29 0.051(3) 0.074(4) 0.037(3) -0.012(3) 0.025(2) -0.002(3) F25 0.050(3) 0.037(3) 0.079(4) 0.031(3) 0.008(3) 0.000(3) F42 0.033(3) 0.040(3) 0.099(4) 0.044(3) 0.020(3) 0.010(2) F35 0.031(3) 0.098(5) 0.060(4) 0.041(3) 0.012(2) -0.014(3) F37 0.064(4) 0.067(4) 0.054(4) 0.022(3) -0.039(3) 0.001(3) C11 0.049(6) 0.021(5) 0.023(4) -0.006(3) -0.011(4) 0.014(4) F7 0.087(4) 0.072(5) 0.036(3) 0.025(3) -0.022(3) -0.043(4) F21 0.040(3) 0.073(5) 0.077(4) 0.003(3) -0.010(3) 0.027(3) F40 0.033(3) 0.064(4) 0.080(4) 0.004(3) -0.018(3) -0.018(3) F8 0.076(4) 0.074(5) 0.052(4) 0.005(3) 0.031(3) -0.018(3) C13 0.029(4) 0.018(4) 0.023(4) -0.002(3) -0.005(3) 0.006(3) F22 0.065(4) 0.089(5) 0.063(4) 0.052(4) -0.021(3) -0.050(4) C12 0.026(4) 0.021(4) 0.021(4) 0.002(3) 0.001(3) 0.002(3) C18 0.048(6) 0.020(5) 0.072(7) 0.018(5) 0.007(5) 0.008(4) C19 0.045(6) 0.030(5) 0.042(5) -0.009(4) -0.012(4) -0.008(4) F24 0.041(4) 0.189(9) 0.054(4) 0.017(4) 0.030(3) 0.022(4) C20 0.035(5) 0.040(6) 0.076(7) -0.005(5) -0.004(5) -0.006(5) C32 0.037(5) 0.028(5) 0.019(4) 0.003(3) 0.005(3) 0.006(4) C2 0.045(7) 0.050(7) 0.080(8) 0.018(6) -0.015(6) 0.002(5) C17 0.073(8) 0.040(7) 0.080(8) -0.022(6) 0.029(6) -0.010(6) C3 0.052(7) 0.037(7) 0.148(12) 0.041(8) -0.010(7) 0.003(6) C4 0.238(19) 0.044(9) 0.105(12) 0.023(8) -0.070(12) -0.049(11) C5 0.029(5) 0.033(5) 0.032(5) 0.015(4) -0.010(4) -0.005(4) C1 0.116(15) 0.20(2) 0.24(2) -0.122(19) -0.019(15) 0.029(15) O5 0.028(3) 0.017(3) 0.016(2) 0.004(2) -0.004(2) 0.003(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 O3 2.072(5) . ? Bi1 O5 2.115(4) . ? Bi1 O2 2.218(4) . ? Bi1 O4 2.438(4) . ? Bi1 O1 2.738(5) . ? Bi2 O6 2.084(4) . ? Bi2 O5 2.138(4) . ? Bi2 O5 2.165(5) 2_575 ? Bi2 O4 2.456(5) . ? Bi2 O2 2.674(4) 2_575 ? Bi2 Bi2 3.5268(5) 2_575 ? Bi3 O8 2.064(5) . ? Bi3 O10 2.108(4) . ? Bi3 O9 2.201(4) . ? Bi3 O12 2.498(4) 2_666 ? Bi3 O7 2.683(5) . ? Bi4 O11 2.080(5) . ? Bi4 O10 2.125(4) 2_666 ? Bi4 O10 2.192(4) . ? Bi4 O12 2.419(5) . ? Bi4 O9 2.707(5) . ? Bi4 Bi4 3.5464(5) 2_666 ? O12 C31 1.395(7) . ? O12 Bi3 2.498(4) 2_666 ? O2 C6 1.396(8) . ? O2 Bi2 2.674(4) 2_575 ? O10 Bi4 2.125(4) 2_666 ? O9 C25 1.393(7) . ? O4 C12 1.385(8) . ? O6 C15 1.385(8) . ? O11 C28 1.395(8) . ? O3 C9 1.394(8) . ? O7 C18 1.415(9) . ? O7 C19 1.430(9) . ? O8 C22 1.403(8) . ? O1 C2 1.422(10) . ? O1 C3 1.460(12) . ? C31 C32 1.512(10) . ? C31 C30 1.528(10) . ? C6 C5 1.507(10) . ? C6 C7 1.524(10) . ? C15 C14 1.508(10) . ? C15 C16 1.524(10) . ? C29 F41 1.304(9) . ? C29 F40 1.323(9) . ? C29 F42 1.351(9) . ? C29 C28 1.527(10) . ? C25 C26 1.502(10) . ? C25 C24 1.529(10) . ? C9 C10 1.503(11) . ? C9 C8 1.531(11) . ? C22 C23 1.514(9) . ? C22 C21 1.523(10) . ? C28 C27 1.513(10) . ? C27 F39 1.307(9) . ? C27 F38 1.316(9) . ? C27 F37 1.338(9) . ? C8 F7 1.310(10) . ? C8 F9 1.324(10) . ? C8 F8 1.340(10) . ? C23 F29 1.323(8) . ? C23 F28 1.323(8) . ? C23 F30 1.341(8) . ? C30 F43 1.332(9) . ? C30 F45 1.334(8) . ? C30 F44 1.337(8) . ? C14 F19 1.314(9) . ? C14 F21 1.327(9) . ? C14 F20 1.347(8) . ? C10 F11 1.327(10) . ? C10 F10 1.337(8) . ? C10 F12 1.344(9) . ? C24 F31 1.328(9) . ? C24 F33 1.330(8) . ? C24 F32 1.332(9) . ? C26 F35 1.307(9) . ? C26 F34 1.333(10) . ? C26 F36 1.348(9) . ? C7 F5 1.318(9) . ? C7 F4 1.338(8) . ? C7 F6 1.354(9) . ? C21 F26 1.322(9) . ? C21 F25 1.324(9) . ? C21 F27 1.338(10) . ? C16 F24 1.284(10) . ? C16 F22 1.332(11) . ? C16 F23 1.343(9) . ? F16 C13 1.330(8) . ? F17 C13 1.356(8) . ? F18 C13 1.317(8) . ? F47 C32 1.320(8) . ? F13 C11 1.335(8) . ? F1 C5 1.355(9) . ? F14 C11 1.339(9) . ? F46 C32 1.340(8) . ? F48 C32 1.346(9) . ? F15 C11 1.313(9) . ? F2 C5 1.336(9) . ? F3 C5 1.330(8) . ? C11 C12 1.524(10) . ? C13 C12 1.510(9) . ? C18 C17 1.487(12) . ? C19 C20 1.520(11) . ? C2 C1 1.418(17) . ? C3 C4 1.380(14) . ? O5 Bi2 2.165(5) 2_575 ? 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 O3 Bi1 O5 94.20(18) . . ? O3 Bi1 O2 94.34(18) . . ? O5 Bi1 O2 70.73(16) . . ? O3 Bi1 O4 86.48(17) . . ? O5 Bi1 O4 68.69(16) . . ? O2 Bi1 O4 139.36(16) . . ? O3 Bi1 O1 80.57(18) . . ? O5 Bi1 O1 159.35(17) . . ? O2 Bi1 O1 89.64(17) . . ? O4 Bi1 O1 130.28(17) . . ? O6 Bi2 O5 92.55(18) . . ? O6 Bi2 O5 83.99(18) . 2_575 ? O5 Bi2 O5 69.9(2) . 2_575 ? O6 Bi2 O4 86.85(17) . . ? O5 Bi2 O4 68.00(16) . . ? O5 Bi2 O4 136.39(15) 2_575 . ? O6 Bi2 O2 85.61(16) . 2_575 ? O5 Bi2 O2 131.25(16) . 2_575 ? O5 Bi2 O2 61.41(14) 2_575 2_575 ? O4 Bi2 O2 159.60(13) . 2_575 ? O6 Bi2 Bi2 87.86(13) . 2_575 ? O5 Bi2 Bi2 35.22(13) . 2_575 ? O5 Bi2 Bi2 34.72(11) 2_575 2_575 ? O4 Bi2 Bi2 102.56(10) . 2_575 ? O2 Bi2 Bi2 96.08(9) 2_575 2_575 ? O8 Bi3 O10 92.91(18) . . ? O8 Bi3 O9 94.39(17) . . ? O10 Bi3 O9 71.89(16) . . ? O8 Bi3 O12 88.36(16) . 2_666 ? O10 Bi3 O12 68.87(15) . 2_666 ? O9 Bi3 O12 140.76(16) . 2_666 ? O8 Bi3 O7 83.79(17) . . ? O10 Bi3 O7 153.93(15) . . ? O9 Bi3 O7 82.55(16) . . ? O12 Bi3 O7 136.55(15) 2_666 . ? O11 Bi4 O10 91.82(18) . 2_666 ? O11 Bi4 O10 83.41(17) . . ? O10 Bi4 O10 69.54(19) 2_666 . ? O11 Bi4 O12 85.66(17) . . ? O10 Bi4 O12 70.23(15) 2_666 . ? O10 Bi4 O12 137.80(15) . . ? O11 Bi4 O9 88.95(17) . . ? O10 Bi4 O9 130.24(14) 2_666 . ? O10 Bi4 O9 61.14(14) . . ? O12 Bi4 O9 159.08(13) . . ? O11 Bi4 Bi4 87.03(12) . 2_666 ? O10 Bi4 Bi4 35.38(11) 2_666 2_666 ? O10 Bi4 Bi4 34.16(11) . 2_666 ? O12 Bi4 Bi4 104.78(10) . 2_666 ? O9 Bi4 Bi4 95.10(8) . 2_666 ? C31 O12 Bi4 127.6(4) . . ? C31 O12 Bi3 122.4(4) . 2_666 ? Bi4 O12 Bi3 97.95(15) . 2_666 ? C6 O2 Bi1 123.6(4) . . ? C6 O2 Bi2 128.0(4) . 2_575 ? Bi1 O2 Bi2 100.83(15) . 2_575 ? Bi3 O10 Bi4 122.42(19) . 2_666 ? Bi3 O10 Bi4 123.84(19) . . ? Bi4 O10 Bi4 110.47(19) 2_666 . ? C25 O9 Bi3 125.4(4) . . ? C25 O9 Bi4 126.2(4) . . ? Bi3 O9 Bi4 100.74(15) . . ? C12 O4 Bi1 123.5(4) . . ? C12 O4 Bi2 129.4(4) . . ? Bi1 O4 Bi2 99.71(17) . . ? C15 O6 Bi2 126.0(4) . . ? C28 O11 Bi4 127.1(4) . . ? C9 O3 Bi1 126.1(5) . . ? C18 O7 C19 114.9(6) . . ? C18 O7 Bi3 123.2(5) . . ? C19 O7 Bi3 115.2(4) . . ? C22 O8 Bi3 127.0(4) . . ? C2 O1 C3 111.5(7) . . ? C2 O1 Bi1 121.1(5) . . ? C3 O1 Bi1 117.9(5) . . ? O12 C31 C32 110.7(6) . . ? O12 C31 C30 109.2(6) . . ? C32 C31 C30 112.3(6) . . ? O2 C6 C5 109.6(5) . . ? O2 C6 C7 107.8(6) . . ? C5 C6 C7 111.8(7) . . ? O6 C15 C14 109.0(6) . . ? O6 C15 C16 109.3(6) . . ? C14 C15 C16 110.8(6) . . ? F41 C29 F40 107.8(7) . . ? F41 C29 F42 106.5(7) . . ? F40 C29 F42 106.9(7) . . ? F41 C29 C28 114.0(7) . . ? F40 C29 C28 112.0(7) . . ? F42 C29 C28 109.3(6) . . ? O9 C25 C26 110.8(6) . . ? O9 C25 C24 108.3(6) . . ? C26 C25 C24 112.1(6) . . ? O3 C9 C10 107.4(6) . . ? O3 C9 C8 106.9(6) . . ? C10 C9 C8 112.9(7) . . ? O8 C22 C23 108.8(6) . . ? O8 C22 C21 108.1(6) . . ? C23 C22 C21 112.2(6) . . ? O11 C28 C27 108.7(6) . . ? O11 C28 C29 108.1(6) . . ? C27 C28 C29 112.1(6) . . ? F39 C27 F38 108.6(7) . . ? F39 C27 F37 107.0(7) . . ? F38 C27 F37 106.7(7) . . ? F39 C27 C28 113.1(6) . . ? F38 C27 C28 109.3(6) . . ? F37 C27 C28 111.9(7) . . ? F7 C8 F9 108.2(8) . . ? F7 C8 F8 106.9(8) . . ? F9 C8 F8 106.7(7) . . ? F7 C8 C9 110.2(7) . . ? F9 C8 C9 113.3(7) . . ? F8 C8 C9 111.2(7) . . ? F29 C23 F28 107.2(6) . . ? F29 C23 F30 106.0(6) . . ? F28 C23 F30 105.7(7) . . ? F29 C23 C22 113.4(7) . . ? F28 C23 C22 113.6(6) . . ? F30 C23 C22 110.3(6) . . ? F43 C30 F45 107.7(6) . . ? F43 C30 F44 107.4(6) . . ? F45 C30 F44 107.4(6) . . ? F43 C30 C31 109.4(6) . . ? F45 C30 C31 112.7(6) . . ? F44 C30 C31 112.0(7) . . ? F19 C14 F21 107.7(6) . . ? F19 C14 F20 105.9(7) . . ? F21 C14 F20 106.4(6) . . ? F19 C14 C15 114.2(7) . . ? F21 C14 C15 112.8(7) . . ? F20 C14 C15 109.4(6) . . ? F11 C10 F10 106.9(7) . . ? F11 C10 F12 107.0(7) . . ? F10 C10 F12 106.2(6) . . ? F11 C10 C9 113.4(7) . . ? F10 C10 C9 113.0(7) . . ? F12 C10 C9 110.0(7) . . ? F31 C24 F33 107.3(6) . . ? F31 C24 F32 107.6(7) . . ? F33 C24 F32 108.7(7) . . ? F31 C24 C25 109.3(6) . . ? F33 C24 C25 111.5(7) . . ? F32 C24 C25 112.2(6) . . ? F35 C26 F34 108.3(7) . . ? F35 C26 F36 106.9(7) . . ? F34 C26 F36 105.8(7) . . ? F35 C26 C25 114.1(7) . . ? F34 C26 C25 112.7(7) . . ? F36 C26 C25 108.6(6) . . ? F5 C7 F4 107.8(6) . . ? F5 C7 F6 107.2(7) . . ? F4 C7 F6 106.3(7) . . ? F5 C7 C6 110.7(7) . . ? F4 C7 C6 112.6(7) . . ? F6 C7 C6 111.9(6) . . ? F26 C21 F25 107.5(7) . . ? F26 C21 F27 107.0(7) . . ? F25 C21 F27 108.2(7) . . ? F26 C21 C22 113.1(7) . . ? F25 C21 C22 109.1(6) . . ? F27 C21 C22 111.7(7) . . ? F24 C16 F22 108.6(8) . . ? F24 C16 F23 108.0(8) . . ? F22 C16 F23 106.5(8) . . ? F24 C16 C15 112.5(8) . . ? F22 C16 C15 111.8(8) . . ? F23 C16 C15 109.2(7) . . ? F15 C11 F13 107.2(7) . . ? F15 C11 F14 106.7(6) . . ? F13 C11 F14 106.9(7) . . ? F15 C11 C12 114.0(7) . . ? F13 C11 C12 109.8(6) . . ? F14 C11 C12 111.9(6) . . ? F18 C13 F16 108.6(6) . . ? F18 C13 F17 106.5(6) . . ? F16 C13 F17 106.8(6) . . ? F18 C13 C12 113.0(6) . . ? F16 C13 C12 113.3(6) . . ? F17 C13 C12 108.3(6) . . ? O4 C12 C13 110.4(6) . . ? O4 C12 C11 108.8(6) . . ? C13 C12 C11 112.3(6) . . ? O7 C18 C17 114.9(8) . . ? O7 C19 C20 114.1(7) . . ? F47 C32 F46 107.8(6) . . ? F47 C32 F48 106.8(6) . . ? F46 C32 F48 105.5(7) . . ? F47 C32 C31 113.9(7) . . ? F46 C32 C31 113.1(6) . . ? F48 C32 C31 109.0(6) . . ? C1 C2 O1 118.4(11) . . ? C4 C3 O1 117.8(11) . . ? F3 C5 F2 107.2(7) . . ? F3 C5 F1 106.8(7) . . ? F2 C5 F1 106.1(6) . . ? F3 C5 C6 113.9(6) . . ? F2 C5 C6 113.1(7) . . ? F1 C5 C6 109.3(7) . . ? Bi1 O5 Bi2 123.2(2) . . ? Bi1 O5 Bi2 124.1(2) . 2_575 ? Bi2 O5 Bi2 110.1(2) . 2_575 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.14 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.648 _refine_diff_density_min -1.800 _refine_diff_density_rms 0.259 # Attachment 'compound 9.CIF' data_bifl _database_code_depnum_ccdc_archive 'CCDC 663326' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Bi4 F48 O12' _chemical_formula_weight 2348.43 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 9.8435(3) _cell_length_b 14.5758(5) _cell_length_c 20.1015(7) _cell_angle_alpha 86.782(2) _cell_angle_beta 86.257(2) _cell_angle_gamma 87.184(2) _cell_volume 2870.42(17) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 12.433 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.358 _exptl_absorpt_correction_T_max 0.419 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 73105 _diffrn_reflns_av_R_equivalents 0.1266 _diffrn_reflns_av_sigmaI/netI 0.1231 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 30.14 _reflns_number_total 16905 _reflns_number_gt 11118 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_cell_refinement 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_data_reduction 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _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^)+(0.0411P)^2^+4.1153P] 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 16905 _refine_ls_number_parameters 865 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1155 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 -0.04033(4) 0.54367(2) 0.579421(18) 0.01778(9) Uani 1 1 d . . . Bi2 Bi 0.10652(4) 0.30309(3) 0.574881(19) 0.01891(9) Uani 1 1 d . . . Bi3 Bi 0.52309(4) 0.98183(2) 0.086476(18) 0.01835(9) Uani 1 1 d . . . Bi4 Bi 0.41599(4) 0.78324(3) -0.004083(19) 0.02084(9) Uani 1 1 d . . . O9 O 0.4661(6) 0.8202(4) 0.1077(3) 0.0204(15) Uani 1 1 d . . . O1 O 0.1596(7) 0.5839(5) 0.5796(3) 0.0248(16) Uani 1 1 d . . . O2 O 0.0199(7) 0.4229(4) 0.5277(3) 0.0220(15) Uani 1 1 d . . . O4 O 0.1011(6) 0.2824(4) 0.4666(3) 0.0216(15) Uani 1 1 d . . . O7 O 0.3159(6) 1.0162(5) 0.1045(3) 0.0237(16) Uani 1 1 d . . . O10 O 0.6067(7) 0.7182(5) -0.0107(4) 0.0253(16) Uani 1 1 d . . . O8 O 0.4855(7) 0.9166(4) -0.0032(3) 0.0219(15) Uani 1 1 d . . . O5 O -0.0797(6) 0.2451(5) 0.5988(3) 0.0230(16) Uani 1 1 d . . . O3 O 0.0259(7) 0.4167(4) 0.6566(3) 0.0218(15) Uani 1 1 d . . . O12 O 0.3450(10) 0.6302(7) -0.0602(6) 0.068(3) Uani 1 1 d . . . C2 C 0.2500(9) 0.5574(6) 0.6292(5) 0.0158(19) Uani 1 1 d . . . H2 H 0.2027 0.5166 0.6641 0.019 Uiso 1 1 calc R . . C22 C 0.4022(12) 0.6869(8) 0.1734(6) 0.034(3) Uani 1 1 d . . . C5 C -0.0394(10) 0.3905(7) 0.7174(5) 0.024(2) Uani 1 1 d . . . H5 H -0.1176 0.3521 0.7095 0.028 Uiso 1 1 calc R . . C21 C 0.5128(10) 0.7554(7) 0.1546(5) 0.026(2) Uani 1 1 d . . . H21 H 0.5942 0.7212 0.1342 0.031 Uiso 1 1 calc R . . C12 C -0.3045(10) 0.3079(8) 0.5881(6) 0.029(3) Uani 1 1 d . . . C11 C -0.1876(9) 0.2505(7) 0.5567(5) 0.023(2) Uani 1 1 d . . . H11 H -0.1567 0.2811 0.5129 0.027 Uiso 1 1 calc R . . C3 C 0.3727(11) 0.5050(8) 0.5984(6) 0.036(3) Uani 1 1 d . . . C20 C 0.5551(11) 0.8011(7) 0.2143(5) 0.027(2) Uani 1 1 d . . . C8 C 0.1710(10) 0.2130(7) 0.4336(5) 0.025(2) Uani 1 1 d . . . H8 H 0.1697 0.1555 0.4632 0.029 Uiso 1 1 calc R . . C6 C 0.0628(11) 0.3331(8) 0.7592(5) 0.029(3) Uani 1 1 d . . . C7 C 0.3174(11) 0.2369(8) 0.4170(6) 0.031(3) Uani 1 1 d . . . C4 C -0.0925(11) 0.4746(8) 0.7549(6) 0.031(3) Uani 1 1 d . . . C9 C 0.0993(12) 0.1968(8) 0.3712(6) 0.038(3) Uani 1 1 d . . . F6 F 0.3308(6) 0.4379(4) 0.5608(4) 0.0459(19) Uani 1 1 d . . . F24 F -0.2707(6) 0.3958(4) 0.5899(4) 0.0417(18) Uani 1 1 d . . . F22 F -0.4170(6) 0.3084(5) 0.5556(4) 0.053(2) Uani 1 1 d . . . O6 O 0.1982(8) 0.1273(5) 0.5796(4) 0.0316(18) Uani 1 1 d . . . F17 F 0.0879(7) 0.2719(5) 0.3310(3) 0.0444(18) Uani 1 1 d . . . F11 F 0.1698(7) 0.3777(5) 0.7731(4) 0.0471(19) Uani 1 1 d . . . F4 F 0.4524(7) 0.5559(5) 0.5578(4) 0.049(2) Uani 1 1 d . . . F10 F 0.1083(7) 0.2600(4) 0.7250(3) 0.0366(16) Uani 1 1 d . . . F13 F 0.3717(6) 0.2606(5) 0.4739(3) 0.0445(18) Uani 1 1 d . . . F7 F -0.1429(7) 0.4567(5) 0.8155(3) 0.0436(18) Uani 1 1 d . . . F2 F 0.3349(7) 0.7077(5) 0.6175(4) 0.0457(18) Uani 1 1 d . . . F19 F -0.1217(7) 0.1052(5) 0.5201(4) 0.0477(19) Uani 1 1 d . . . F18 F -0.0277(7) 0.1712(5) 0.3874(4) 0.051(2) Uani 1 1 d . . . F1 F 0.1842(7) 0.6795(5) 0.6969(4) 0.0473(19) Uani 1 1 d . . . F14 F 0.3322(7) 0.3082(5) 0.3736(4) 0.0489(19) Uani 1 1 d . . . F23 F -0.3351(7) 0.2788(5) 0.6507(3) 0.052(2) Uani 1 1 d . . . F12 F 0.0068(7) 0.3003(5) 0.8171(3) 0.053(2) Uani 1 1 d . . . F3 F 0.3883(7) 0.6231(5) 0.7041(4) 0.055(2) Uani 1 1 d . . . F9 F -0.1949(7) 0.5174(5) 0.7197(3) 0.0479(19) Uani 1 1 d . . . F20 F -0.3277(7) 0.1511(5) 0.5030(4) 0.062(2) Uani 1 1 d . . . F8 F -0.0003(7) 0.5387(5) 0.7566(4) 0.050(2) Uani 1 1 d . . . F21 F -0.2722(8) 0.1089(5) 0.6023(4) 0.056(2) Uani 1 1 d . . . F5 F 0.4475(7) 0.4636(6) 0.6444(4) 0.058(2) Uani 1 1 d . . . F15 F 0.3961(7) 0.1682(5) 0.3937(4) 0.061(2) Uani 1 1 d . . . F16 F 0.1611(9) 0.1311(6) 0.3358(4) 0.073(3) Uani 1 1 d . . . C13 C 0.3390(13) 0.1070(10) 0.5880(7) 0.054(4) Uani 1 1 d . . . H13A H 0.3777 0.1566 0.6115 0.064 Uiso 1 1 calc R . . H13B H 0.3892 0.1022 0.5439 0.064 Uiso 1 1 calc R . . C16 C 0.1177(12) 0.0555(8) 0.6162(6) 0.041(3) Uani 1 1 d . . . H16A H 0.0918 0.0091 0.5858 0.050 Uiso 1 1 calc R . . H16B H 0.0342 0.0827 0.6389 0.050 Uiso 1 1 calc R . . C32 C 0.2060(13) 0.5986(9) -0.0398(8) 0.057(4) Uani 1 1 d . . . H32A H 0.2051 0.5601 0.0024 0.068 Uiso 1 1 calc R . . H32B H 0.1388 0.6510 -0.0350 0.068 Uiso 1 1 calc R . . C14 C 0.3524(14) 0.0196(10) 0.6271(7) 0.057(4) Uani 1 1 d . . . H14A H 0.4270 0.0202 0.6578 0.068 Uiso 1 1 calc R . . H14B H 0.3699 -0.0325 0.5978 0.068 Uiso 1 1 calc R . . C29 C 0.4240(15) 0.5549(9) -0.0920(10) 0.086(6) Uani 1 1 d . . . H29A H 0.4781 0.5779 -0.1322 0.103 Uiso 1 1 calc R . . H29B H 0.4860 0.5226 -0.0607 0.103 Uiso 1 1 calc R . . C15 C 0.2131(15) 0.0135(10) 0.6661(8) 0.062(4) Uani 1 1 d . . . H15A H 0.1921 -0.0511 0.6788 0.074 Uiso 1 1 calc R . . H15B H 0.2093 0.0491 0.7068 0.074 Uiso 1 1 calc R . . C10 C -0.2266(12) 0.1522(8) 0.5451(6) 0.034(3) Uani 1 1 d . . . C31 C 0.1816(14) 0.5459(12) -0.0956(9) 0.078(6) Uani 1 1 d . . . H31A H 0.1562 0.5863 -0.1345 0.093 Uiso 1 1 calc R . . H31B H 0.1088 0.5023 -0.0840 0.093 Uiso 1 1 calc R . . C1 C 0.2914(11) 0.6432(8) 0.6611(6) 0.031(3) Uani 1 1 d . . . F32 F 0.5897(6) 0.7432(5) 0.2649(3) 0.0354(16) Uani 1 1 d . . . F31 F 0.4594(7) 0.8597(4) 0.2400(3) 0.0390(17) Uani 1 1 d . . . F33 F 0.6650(7) 0.8515(5) 0.1975(4) 0.0463(19) Uani 1 1 d . . . F35 F 0.3694(8) 0.6484(5) 0.1181(3) 0.051(2) Uani 1 1 d . . . F36 F 0.2885(6) 0.7276(5) 0.1994(4) 0.0471(19) Uani 1 1 d . . . F34 F 0.4401(8) 0.6193(5) 0.2156(3) 0.0482(19) Uani 1 1 d . . . C18 C 0.2209(10) 0.9601(7) 0.1377(5) 0.023(2) Uani 1 1 d . . . H18 H 0.2660 0.8992 0.1502 0.028 Uiso 1 1 calc R . . C17 C 0.1619(11) 1.0042(9) 0.2001(6) 0.033(3) Uani 1 1 d . . . C19 C 0.1102(11) 0.9466(8) 0.0887(6) 0.034(3) Uani 1 1 d . . . F27 F 0.2601(6) 1.0074(5) 0.2426(3) 0.0436(18) Uani 1 1 d . . . F39 F 0.9420(6) 0.7954(5) -0.0130(3) 0.0434(18) Uani 1 1 d . . . F28 F 0.1685(6) 0.9086(5) 0.0333(3) 0.0471(19) Uani 1 1 d . . . F29 F 0.0449(7) 1.0220(5) 0.0694(4) 0.0473(19) Uani 1 1 d . . . F40 F 0.8241(7) 0.6062(4) -0.0628(4) 0.0475(19) Uani 1 1 d . . . F42 F 0.6956(7) 0.6699(5) -0.1360(4) 0.051(2) Uani 1 1 d . . . F25 F 0.1141(7) 1.0900(5) 0.1887(4) 0.051(2) Uani 1 1 d . . . F38 F 0.8391(7) 0.7007(5) 0.0541(4) 0.0497(19) Uani 1 1 d . . . F41 F 0.8947(7) 0.7183(5) -0.1256(4) 0.054(2) Uani 1 1 d . . . F26 F 0.0641(7) 0.9580(6) 0.2314(4) 0.059(2) Uani 1 1 d . . . F30 F 0.0186(8) 0.8881(6) 0.1154(4) 0.063(2) Uani 1 1 d . . . C23 C 0.8216(11) 0.7712(7) 0.0117(6) 0.027(2) Uani 1 1 d . . . C24 C 0.7236(10) 0.7545(7) -0.0424(6) 0.027(2) Uani 1 1 d . . . H24 H 0.6995 0.8141 -0.0670 0.032 Uiso 1 1 calc R . . C25 C 0.7857(12) 0.6860(8) -0.0914(6) 0.036(3) Uani 1 1 d . . . F37 F 0.7688(6) 0.8411(5) 0.0475(4) 0.0470(19) Uani 1 1 d . . . C30 C 0.3194(15) 0.4950(12) -0.1097(11) 0.105(8) Uani 1 1 d . . . H30A H 0.3243 0.4362 -0.0826 0.125 Uiso 1 1 calc R . . H30B H 0.3322 0.4815 -0.1574 0.125 Uiso 1 1 calc R . . O11 O 0.4383(7) 0.8423(5) -0.1083(3) 0.0254(16) Uani 1 1 d . . . F45 F 0.4690(6) 0.9363(4) -0.2282(3) 0.0332(15) Uani 1 1 d . . . F43 F 0.5802(6) 0.8060(5) -0.2291(3) 0.0409(17) Uani 1 1 d . . . F47 F 0.2126(6) 0.9372(4) -0.1649(3) 0.0375(16) Uani 1 1 d . . . C28 C 0.2261(10) 0.8453(8) -0.1592(5) 0.026(2) Uani 1 1 d . . . C26 C 0.4545(10) 0.8451(7) -0.2252(5) 0.023(2) Uani 1 1 d . . . C27 C 0.3752(9) 0.8109(7) -0.1632(5) 0.021(2) Uani 1 1 d . . . H27 H 0.3798 0.7421 -0.1608 0.025 Uiso 1 1 calc R . . F44 F 0.3957(6) 0.8264(4) -0.2808(3) 0.0344(15) Uani 1 1 d . . . F48 F 0.1657(6) 0.8183(5) -0.1014(3) 0.0395(17) Uani 1 1 d . . . F46 F 0.1576(6) 0.8131(5) -0.2071(4) 0.048(2) 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 0.01975(18) 0.01693(19) 0.01699(19) -0.00530(14) 0.00137(14) -0.00263(14) Bi2 0.02005(18) 0.01631(19) 0.0206(2) -0.00256(14) -0.00067(14) -0.00183(14) Bi3 0.02260(19) 0.01653(19) 0.01603(19) -0.00393(14) 0.00228(14) -0.00298(14) Bi4 0.0265(2) 0.01468(19) 0.0215(2) -0.00480(15) 0.00469(15) -0.00573(15) O9 0.025(4) 0.018(4) 0.017(4) -0.003(3) 0.003(3) 0.003(3) O1 0.024(4) 0.030(4) 0.020(4) -0.003(3) 0.004(3) -0.012(3) O2 0.031(4) 0.014(4) 0.021(4) -0.009(3) -0.001(3) 0.002(3) O4 0.028(4) 0.012(3) 0.025(4) -0.005(3) 0.003(3) 0.001(3) O7 0.018(3) 0.024(4) 0.027(4) -0.001(3) 0.008(3) 0.000(3) O10 0.023(4) 0.020(4) 0.032(4) 0.000(3) 0.002(3) -0.002(3) O8 0.039(4) 0.014(3) 0.013(4) -0.004(3) 0.002(3) -0.007(3) O5 0.022(4) 0.027(4) 0.021(4) -0.002(3) -0.003(3) -0.010(3) O3 0.027(4) 0.020(4) 0.018(4) -0.002(3) 0.001(3) -0.001(3) O12 0.056(6) 0.057(7) 0.096(9) -0.043(6) 0.009(6) -0.014(5) C2 0.017(4) 0.017(5) 0.014(5) -0.003(4) -0.004(4) -0.004(4) C22 0.043(7) 0.030(7) 0.026(7) 0.005(5) 0.005(5) 0.003(5) C5 0.024(5) 0.026(6) 0.022(6) 0.002(4) -0.005(4) -0.006(4) C21 0.030(6) 0.022(6) 0.023(6) 0.002(4) 0.001(4) 0.003(4) C12 0.018(5) 0.038(7) 0.032(7) -0.009(5) -0.005(4) -0.003(5) C11 0.022(5) 0.027(6) 0.020(5) -0.002(4) -0.002(4) -0.004(4) C3 0.026(6) 0.033(7) 0.051(8) -0.017(6) -0.002(5) -0.007(5) C20 0.035(6) 0.024(6) 0.024(6) -0.006(5) -0.003(5) 0.003(5) C8 0.030(6) 0.018(5) 0.025(6) -0.005(4) 0.003(4) 0.003(4) C6 0.038(6) 0.038(7) 0.012(5) 0.004(5) -0.001(4) -0.001(5) C7 0.040(7) 0.023(6) 0.029(7) -0.002(5) 0.008(5) 0.009(5) C4 0.033(6) 0.032(7) 0.026(6) 0.002(5) 0.009(5) -0.006(5) C9 0.045(7) 0.019(6) 0.050(8) -0.024(6) 0.003(6) 0.011(5) F6 0.035(4) 0.029(4) 0.075(5) -0.030(4) 0.015(3) -0.008(3) F24 0.033(4) 0.030(4) 0.063(5) -0.014(3) 0.007(3) -0.001(3) F22 0.020(3) 0.069(5) 0.073(6) -0.024(4) -0.010(3) 0.004(3) O6 0.044(5) 0.020(4) 0.030(5) 0.005(3) 0.002(3) 0.000(3) F17 0.059(5) 0.045(5) 0.028(4) -0.001(3) -0.006(3) 0.008(4) F11 0.038(4) 0.060(5) 0.046(5) -0.011(4) -0.015(3) -0.012(4) F4 0.037(4) 0.056(5) 0.056(5) -0.020(4) 0.021(3) -0.023(3) F10 0.050(4) 0.027(4) 0.034(4) -0.001(3) -0.013(3) 0.003(3) F13 0.033(4) 0.068(5) 0.034(4) 0.002(4) -0.006(3) -0.007(3) F7 0.059(5) 0.043(4) 0.027(4) -0.007(3) 0.018(3) -0.006(3) F2 0.047(4) 0.036(4) 0.056(5) -0.011(4) -0.005(4) -0.017(3) F19 0.047(4) 0.036(4) 0.063(5) -0.023(4) -0.004(4) -0.008(3) F18 0.057(5) 0.050(5) 0.052(5) -0.012(4) -0.015(4) -0.024(4) F1 0.044(4) 0.047(5) 0.054(5) -0.031(4) 0.008(3) -0.007(3) F14 0.039(4) 0.063(5) 0.042(5) 0.015(4) 0.006(3) -0.013(4) F23 0.050(4) 0.069(5) 0.034(4) -0.003(4) 0.025(3) 0.000(4) F12 0.056(5) 0.071(6) 0.026(4) 0.018(4) 0.004(3) 0.008(4) F3 0.054(5) 0.053(5) 0.064(5) -0.013(4) -0.036(4) -0.004(4) F9 0.051(4) 0.049(5) 0.039(4) 0.001(4) 0.014(3) 0.023(4) F20 0.046(5) 0.061(5) 0.085(6) -0.029(5) -0.022(4) -0.015(4) F8 0.065(5) 0.040(4) 0.047(5) -0.026(4) 0.018(4) -0.014(4) F21 0.087(6) 0.037(4) 0.046(5) 0.001(4) 0.013(4) -0.036(4) F5 0.044(4) 0.071(6) 0.060(5) -0.008(4) -0.013(4) 0.027(4) F15 0.051(5) 0.067(6) 0.060(5) -0.012(4) 0.026(4) 0.026(4) F16 0.105(7) 0.058(6) 0.058(6) -0.041(5) -0.017(5) 0.028(5) C13 0.041(8) 0.066(10) 0.051(9) 0.022(8) -0.012(6) 0.013(7) C16 0.042(7) 0.036(7) 0.046(8) 0.014(6) -0.003(6) -0.009(6) C32 0.046(8) 0.042(9) 0.084(12) 0.001(8) -0.003(8) -0.019(7) C14 0.063(10) 0.048(9) 0.060(10) -0.003(8) -0.012(8) -0.002(7) C29 0.064(10) 0.020(8) 0.17(2) -0.036(10) 0.013(11) -0.013(7) C15 0.073(11) 0.044(9) 0.068(11) 0.015(8) -0.005(9) -0.018(8) C10 0.041(7) 0.033(7) 0.031(7) -0.004(5) -0.010(5) -0.010(5) C31 0.044(9) 0.101(14) 0.096(14) -0.060(11) -0.016(8) 0.001(9) C1 0.036(6) 0.032(7) 0.027(6) -0.018(5) -0.001(5) 0.000(5) F32 0.033(4) 0.046(4) 0.027(4) 0.004(3) -0.008(3) 0.001(3) F31 0.056(4) 0.026(4) 0.037(4) -0.014(3) -0.015(3) 0.009(3) F33 0.038(4) 0.055(5) 0.048(5) 0.006(4) -0.013(3) -0.021(3) F35 0.084(6) 0.041(4) 0.032(4) -0.002(3) 0.001(4) -0.037(4) F36 0.035(4) 0.060(5) 0.045(5) 0.003(4) 0.015(3) -0.017(3) F34 0.081(5) 0.025(4) 0.038(4) 0.010(3) 0.000(4) -0.011(4) C18 0.022(5) 0.025(6) 0.021(6) 0.001(4) 0.007(4) -0.006(4) C17 0.028(6) 0.048(8) 0.022(6) -0.006(5) 0.005(5) -0.005(5) C19 0.035(6) 0.042(7) 0.025(6) -0.014(5) 0.009(5) -0.006(6) F27 0.039(4) 0.064(5) 0.028(4) -0.019(4) -0.005(3) 0.012(3) F39 0.022(3) 0.057(5) 0.051(5) -0.011(4) 0.004(3) -0.001(3) F28 0.037(4) 0.063(5) 0.045(5) -0.033(4) -0.002(3) 0.002(3) F29 0.047(4) 0.051(5) 0.043(5) -0.006(4) -0.016(3) 0.022(4) F40 0.062(5) 0.023(4) 0.054(5) -0.001(3) 0.009(4) 0.017(3) F42 0.060(5) 0.056(5) 0.038(4) -0.018(4) -0.001(4) 0.001(4) F25 0.056(5) 0.052(5) 0.045(5) -0.022(4) -0.006(3) 0.025(4) F38 0.057(5) 0.049(5) 0.044(5) 0.010(4) -0.018(4) -0.007(4) F41 0.052(5) 0.053(5) 0.057(5) -0.020(4) 0.028(4) -0.008(4) F26 0.042(4) 0.088(6) 0.045(5) -0.004(4) 0.027(4) -0.017(4) F30 0.054(5) 0.075(6) 0.064(6) -0.001(5) -0.006(4) -0.039(4) C23 0.031(6) 0.013(5) 0.037(7) -0.006(5) 0.005(5) -0.002(4) C24 0.020(5) 0.015(5) 0.047(7) -0.006(5) 0.003(5) -0.007(4) C25 0.036(7) 0.034(7) 0.035(7) -0.007(6) 0.008(5) 0.009(5) F37 0.032(4) 0.057(5) 0.055(5) -0.032(4) -0.002(3) -0.003(3) C30 0.052(10) 0.076(13) 0.19(2) -0.087(14) -0.014(12) 0.008(9) O11 0.032(4) 0.026(4) 0.018(4) -0.006(3) 0.005(3) -0.007(3) F45 0.044(4) 0.033(4) 0.023(3) -0.004(3) 0.005(3) -0.015(3) F43 0.031(4) 0.049(4) 0.040(4) -0.003(3) 0.011(3) 0.003(3) F47 0.033(4) 0.037(4) 0.042(4) -0.008(3) 0.005(3) 0.002(3) C28 0.028(6) 0.029(6) 0.023(6) -0.014(5) -0.002(4) -0.004(5) C26 0.033(6) 0.016(5) 0.021(6) -0.008(4) 0.007(4) -0.005(4) C27 0.025(5) 0.018(5) 0.020(5) -0.010(4) -0.003(4) -0.002(4) F44 0.049(4) 0.036(4) 0.020(3) -0.007(3) -0.005(3) -0.003(3) F48 0.034(4) 0.048(4) 0.036(4) -0.005(3) 0.012(3) -0.009(3) F46 0.033(4) 0.065(5) 0.050(5) -0.033(4) -0.008(3) -0.005(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 O1 2.082(6) . ? Bi1 O2 2.133(6) . ? Bi1 O2 2.180(7) 2_566 ? Bi1 O3 2.439(7) . ? Bi1 O4 2.702(6) 2_566 ? Bi1 Bi1 3.5316(7) 2_566 ? Bi2 O5 2.073(6) . ? Bi2 O2 2.110(7) . ? Bi2 O4 2.219(7) . ? Bi2 O3 2.465(6) . ? Bi2 O6 2.672(7) . ? Bi3 O7 2.089(6) . ? Bi3 O8 2.146(6) . ? Bi3 O8 2.175(7) 2_675 ? Bi3 O9 2.457(7) . ? Bi3 O11 2.675(7) 2_675 ? Bi3 Bi3 3.5426(7) 2_675 ? Bi4 O10 2.061(7) . ? Bi4 O8 2.093(6) . ? Bi4 O11 2.221(7) . ? Bi4 O9 2.427(6) . ? Bi4 O12 2.697(9) . ? O9 C21 1.381(12) . ? O1 C2 1.405(11) . ? O2 Bi1 2.180(7) 2_566 ? O4 C8 1.372(11) . ? O4 Bi1 2.702(6) 2_566 ? O7 C18 1.385(11) . ? O10 C24 1.393(11) . ? O8 Bi3 2.175(7) 2_675 ? O5 C11 1.397(11) . ? O3 C5 1.385(11) . ? O12 C29 1.465(16) . ? O12 C32 1.490(15) . ? C2 C3 1.513(14) . ? C2 C1 1.521(13) . ? C22 F34 1.318(12) . ? C22 F36 1.330(12) . ? C22 F35 1.338(13) . ? C22 C21 1.529(15) . ? C5 C4 1.527(15) . ? C5 C6 1.539(14) . ? C21 C20 1.497(14) . ? C12 F22 1.322(11) . ? C12 F23 1.326(13) . ? C12 F24 1.341(12) . ? C12 C11 1.516(14) . ? C11 C10 1.535(14) . ? C3 F4 1.318(13) . ? C3 F5 1.320(14) . ? C3 F6 1.365(12) . ? C20 F32 1.335(12) . ? C20 F31 1.338(11) . ? C20 F33 1.352(12) . ? C8 C7 1.511(14) . ? C8 C9 1.515(16) . ? C6 F11 1.317(12) . ? C6 F12 1.329(12) . ? C6 F10 1.343(12) . ? C7 F15 1.324(12) . ? C7 F14 1.326(12) . ? C7 F13 1.361(13) . ? C4 F7 1.302(12) . ? C4 F8 1.338(12) . ? C4 F9 1.374(13) . ? C9 F16 1.325(11) . ? C9 F17 1.328(14) . ? C9 F18 1.337(13) . ? O6 C13 1.423(13) . ? O6 C16 1.478(13) . ? F2 C1 1.316(13) . ? F19 C10 1.299(13) . ? F1 C1 1.342(12) . ? F3 C1 1.339(13) . ? F20 C10 1.349(13) . ? F21 C10 1.341(13) . ? C13 C14 1.464(18) . ? C16 C15 1.502(18) . ? C32 C31 1.433(19) . ? C14 C15 1.538(19) . ? C29 C30 1.455(19) . ? C31 C30 1.531(19) . ? C18 C17 1.511(14) . ? C18 C19 1.543(15) . ? C17 F26 1.309(12) . ? C17 F25 1.326(14) . ? C17 F27 1.336(12) . ? C19 F29 1.299(13) . ? C19 F30 1.338(13) . ? C19 F28 1.352(11) . ? F39 C23 1.312(11) . ? F40 C25 1.318(13) . ? F42 C25 1.338(14) . ? F38 C23 1.308(12) . ? F41 C25 1.328(13) . ? C23 F37 1.344(11) . ? C23 C24 1.538(15) . ? C24 C25 1.521(14) . ? O11 C27 1.410(11) . ? O11 Bi3 2.675(7) 2_675 ? F45 C26 1.342(11) . ? F43 C26 1.336(11) . ? F47 C28 1.338(12) . ? C28 F48 1.319(12) . ? C28 F46 1.331(11) . ? C28 C27 1.527(13) . ? C26 F44 1.339(11) . ? C26 C27 1.500(13) . ? 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 O2 92.4(3) . . ? O1 Bi1 O2 85.2(3) . 2_566 ? O2 Bi1 O2 70.1(3) . 2_566 ? O1 Bi1 O3 86.7(2) . . ? O2 Bi1 O3 68.7(2) . . ? O2 Bi1 O3 137.5(2) 2_566 . ? O1 Bi1 O4 86.1(2) . 2_566 ? O2 Bi1 O4 131.0(2) . 2_566 ? O2 Bi1 O4 61.0(2) 2_566 2_566 ? O3 Bi1 O4 159.3(2) . 2_566 ? O1 Bi1 Bi1 88.51(18) . 2_566 ? O2 Bi1 Bi1 35.47(18) . 2_566 ? O2 Bi1 Bi1 34.60(16) 2_566 2_566 ? O3 Bi1 Bi1 103.62(15) . 2_566 ? O4 Bi1 Bi1 95.57(14) 2_566 2_566 ? O5 Bi2 O2 94.1(3) . . ? O5 Bi2 O4 93.9(2) . . ? O2 Bi2 O4 71.1(2) . . ? O5 Bi2 O3 84.7(2) . . ? O2 Bi2 O3 68.5(2) . . ? O4 Bi2 O3 139.3(2) . . ? O5 Bi2 O6 82.8(2) . . ? O2 Bi2 O6 154.0(2) . . ? O4 Bi2 O6 83.3(2) . . ? O3 Bi2 O6 136.3(2) . . ? O7 Bi3 O8 91.6(3) . . ? O7 Bi3 O8 85.4(3) . 2_675 ? O8 Bi3 O8 69.9(3) . 2_675 ? O7 Bi3 O9 87.4(2) . . ? O8 Bi3 O9 67.5(2) . . ? O8 Bi3 O9 136.4(2) 2_675 . ? O7 Bi3 O11 85.5(2) . 2_675 ? O8 Bi3 O11 131.1(2) . 2_675 ? O8 Bi3 O11 61.2(2) 2_675 2_675 ? O9 Bi3 O11 160.3(2) . 2_675 ? O7 Bi3 Bi3 88.20(19) . 2_675 ? O8 Bi3 Bi3 35.19(17) . 2_675 ? O8 Bi3 Bi3 34.67(16) 2_675 2_675 ? O9 Bi3 Bi3 102.28(15) . 2_675 ? O11 Bi3 Bi3 95.89(15) 2_675 2_675 ? O10 Bi4 O8 95.7(3) . . ? O10 Bi4 O11 92.6(3) . . ? O8 Bi4 O11 71.0(2) . . ? O10 Bi4 O9 86.6(2) . . ? O8 Bi4 O9 68.8(2) . . ? O11 Bi4 O9 139.5(2) . . ? O10 Bi4 O12 82.5(3) . . ? O8 Bi4 O12 155.8(3) . . ? O11 Bi4 O12 85.0(3) . . ? O9 Bi4 O12 134.7(3) . . ? C21 O9 Bi4 123.2(6) . . ? C21 O9 Bi3 129.9(6) . . ? Bi4 O9 Bi3 99.8(2) . . ? C2 O1 Bi1 125.0(6) . . ? Bi2 O2 Bi1 123.1(3) . . ? Bi2 O2 Bi1 124.2(3) . 2_566 ? Bi1 O2 Bi1 109.9(3) . 2_566 ? C8 O4 Bi2 124.9(6) . . ? C8 O4 Bi1 128.5(6) . 2_566 ? Bi2 O4 Bi1 100.3(2) . 2_566 ? C18 O7 Bi3 125.7(6) . . ? C24 O10 Bi4 125.9(6) . . ? Bi4 O8 Bi3 123.5(3) . . ? Bi4 O8 Bi3 124.5(3) . 2_675 ? Bi3 O8 Bi3 110.1(3) . 2_675 ? C11 O5 Bi2 124.1(6) . . ? C5 O3 Bi1 127.4(6) . . ? C5 O3 Bi2 121.7(6) . . ? Bi1 O3 Bi2 99.0(2) . . ? C29 O12 C32 108.5(10) . . ? C29 O12 Bi4 133.1(8) . . ? C32 O12 Bi4 115.8(7) . . ? O1 C2 C3 109.5(8) . . ? O1 C2 C1 108.7(8) . . ? C3 C2 C1 111.3(8) . . ? F34 C22 F36 108.1(9) . . ? F34 C22 F35 107.0(9) . . ? F36 C22 F35 106.8(10) . . ? F34 C22 C21 113.7(10) . . ? F36 C22 C21 112.1(9) . . ? F35 C22 C21 108.8(9) . . ? O3 C5 C4 111.0(8) . . ? O3 C5 C6 108.5(8) . . ? C4 C5 C6 109.7(9) . . ? O9 C21 C20 110.5(8) . . ? O9 C21 C22 109.3(9) . . ? C20 C21 C22 111.8(9) . . ? F22 C12 F23 107.7(9) . . ? F22 C12 F24 107.0(9) . . ? F23 C12 F24 106.6(9) . . ? F22 C12 C11 113.3(9) . . ? F23 C12 C11 111.5(9) . . ? F24 C12 C11 110.5(8) . . ? O5 C11 C12 109.0(8) . . ? O5 C11 C10 108.2(8) . . ? C12 C11 C10 112.8(9) . . ? F4 C3 F5 108.3(9) . . ? F4 C3 F6 105.8(10) . . ? F5 C3 F6 106.8(10) . . ? F4 C3 C2 114.0(10) . . ? F5 C3 C2 111.7(10) . . ? F6 C3 C2 109.7(8) . . ? F32 C20 F31 105.9(8) . . ? F32 C20 F33 106.3(8) . . ? F31 C20 F33 105.8(8) . . ? F32 C20 C21 114.5(9) . . ? F31 C20 C21 113.5(9) . . ? F33 C20 C21 110.1(9) . . ? O4 C8 C7 110.5(8) . . ? O4 C8 C9 108.7(8) . . ? C7 C8 C9 111.4(9) . . ? F11 C6 F12 106.7(9) . . ? F11 C6 F10 107.6(9) . . ? F12 C6 F10 106.7(9) . . ? F11 C6 C5 114.3(9) . . ? F12 C6 C5 112.8(9) . . ? F10 C6 C5 108.4(8) . . ? F15 C7 F14 107.0(9) . . ? F15 C7 F13 106.5(9) . . ? F14 C7 F13 106.2(9) . . ? F15 C7 C8 114.0(10) . . ? F14 C7 C8 114.0(9) . . ? F13 C7 C8 108.6(8) . . ? F7 C4 F8 108.5(9) . . ? F7 C4 F9 107.2(9) . . ? F8 C4 F9 104.3(9) . . ? F7 C4 C5 115.1(9) . . ? F8 C4 C5 113.4(8) . . ? F9 C4 C5 107.5(9) . . ? F16 C9 F17 107.5(10) . . ? F16 C9 F18 107.0(10) . . ? F17 C9 F18 106.2(10) . . ? F16 C9 C8 112.7(10) . . ? F17 C9 C8 112.8(9) . . ? F18 C9 C8 110.2(10) . . ? C13 O6 C16 109.1(9) . . ? C13 O6 Bi2 118.8(7) . . ? C16 O6 Bi2 120.7(6) . . ? O6 C13 C14 108.3(11) . . ? O6 C16 C15 103.6(10) . . ? C31 C32 O12 100.4(12) . . ? C13 C14 C15 103.1(11) . . ? C30 C29 O12 103.2(12) . . ? C16 C15 C14 102.1(12) . . ? F19 C10 F21 108.8(10) . . ? F19 C10 F20 108.4(9) . . ? F21 C10 F20 106.2(10) . . ? F19 C10 C11 110.2(9) . . ? F21 C10 C11 111.2(9) . . ? F20 C10 C11 112.0(10) . . ? C32 C31 C30 102.7(13) . . ? F2 C1 F3 108.4(9) . . ? F2 C1 F1 107.5(9) . . ? F3 C1 F1 106.1(9) . . ? F2 C1 C2 113.5(9) . . ? F3 C1 C2 111.4(9) . . ? F1 C1 C2 109.6(9) . . ? O7 C18 C17 109.9(8) . . ? O7 C18 C19 107.0(9) . . ? C17 C18 C19 111.6(8) . . ? F26 C17 F25 107.7(9) . . ? F26 C17 F27 106.7(10) . . ? F25 C17 F27 106.9(10) . . ? F26 C17 C18 113.2(10) . . ? F25 C17 C18 113.3(10) . . ? F27 C17 C18 108.8(9) . . ? F29 C19 F30 107.9(10) . . ? F29 C19 F28 107.3(10) . . ? F30 C19 F28 106.7(9) . . ? F29 C19 C18 114.4(10) . . ? F30 C19 C18 111.0(10) . . ? F28 C19 C18 109.3(9) . . ? F38 C23 F39 108.1(9) . . ? F38 C23 F37 106.6(9) . . ? F39 C23 F37 106.6(8) . . ? F38 C23 C24 113.8(9) . . ? F39 C23 C24 112.9(9) . . ? F37 C23 C24 108.3(8) . . ? O10 C24 C25 108.4(8) . . ? O10 C24 C23 107.6(9) . . ? C25 C24 C23 111.6(9) . . ? F40 C25 F41 106.8(9) . . ? F40 C25 F42 107.7(10) . . ? F41 C25 F42 106.9(10) . . ? F40 C25 C24 113.6(10) . . ? F41 C25 C24 111.4(10) . . ? F42 C25 C24 110.0(9) . . ? C29 C30 C31 107.0(13) . . ? C27 O11 Bi4 125.6(6) . . ? C27 O11 Bi3 125.6(6) . 2_675 ? Bi4 O11 Bi3 100.6(2) . 2_675 ? F48 C28 F46 107.6(9) . . ? F48 C28 F47 107.7(8) . . ? F46 C28 F47 107.2(9) . . ? F48 C28 C27 110.3(9) . . ? F46 C28 C27 111.7(8) . . ? F47 C28 C27 112.2(8) . . ? F43 C26 F44 107.0(8) . . ? F43 C26 F45 106.5(8) . . ? F44 C26 F45 106.4(8) . . ? F43 C26 C27 111.1(9) . . ? F44 C26 C27 112.2(8) . . ? F45 C26 C27 113.3(8) . . ? O11 C27 C26 107.2(8) . . ? O11 C27 C28 108.4(8) . . ? C26 C27 C28 113.8(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.14 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 3.259 _refine_diff_density_min -3.193 _refine_diff_density_rms 0.314 # Attachment 'compound 10.CIF' data_bit _database_code_depnum_ccdc_archive 'CCDC 663327' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 Bi2 F24 N4 O5' _chemical_formula_weight 1334.53 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' 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' F F 0.0171 0.0103 '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 P21/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 9.9443(3) _cell_length_b 33.6528(11) _cell_length_c 12.6212(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.258(2) _cell_angle_gamma 90.00 _cell_volume 3962.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2520 _exptl_absorpt_coefficient_mu 9.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4973 _exptl_absorpt_correction_T_max 0.6611 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 100981 _diffrn_reflns_av_R_equivalents 0.1512 _diffrn_reflns_av_sigmaI/netI 0.1026 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 30.18 _reflns_number_total 11692 _reflns_number_gt 8336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_cell_refinement 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_data_reduction 'Bruker APEX II v. 1.0 (Bruker AXS 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _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^)+(0.0477P)^2^+39.4897P] 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 11692 _refine_ls_number_parameters 540 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 0.21130(4) 0.145946(11) 0.01778(3) 0.01474(9) Uani 1 1 d . . . Bi2 Bi 0.45726(4) 0.105124(11) 0.25233(3) 0.01571(9) Uani 1 1 d . . . O2 O 0.4085(7) 0.11184(19) 0.0167(5) 0.0168(14) Uani 1 1 d . . . O3 O 0.3561(7) 0.15731(19) 0.1785(5) 0.0198(15) Uani 1 1 d . . . O1 O 0.2842(7) 0.19637(19) -0.0525(6) 0.0175(14) Uani 1 1 d . . . O4 O 0.2203(7) 0.0864(2) 0.1814(6) 0.0225(15) Uani 1 1 d . . . O5 O 0.4388(7) 0.1182(2) 0.4131(5) 0.0207(15) Uani 1 1 d . . . C1 C 0.3942(11) 0.1967(3) -0.1904(9) 0.026(2) Uani 1 1 d . . . C2 C 0.4171(10) 0.1969(3) -0.0648(8) 0.019(2) Uani 1 1 d . . . H2 H 0.4718 0.1726 -0.0289 0.023 Uiso 1 1 calc R . . F3 F 0.3285(7) 0.16328(19) -0.2358(5) 0.0320(15) Uani 1 1 d . . . F13 F -0.0452(7) 0.0775(2) 0.0158(6) 0.0370(17) Uani 1 1 d . . . F5 F 0.6364(7) 0.2324(2) -0.0060(6) 0.0384(17) Uani 1 1 d . . . F14 F -0.0479(7) 0.0751(2) 0.1847(6) 0.0385(17) Uani 1 1 d . . . F20 F 0.3855(8) 0.1773(2) 0.5481(5) 0.0386(17) Uani 1 1 d . . . F11 F 0.3825(7) 0.02835(19) 0.0184(6) 0.0396(17) Uani 1 1 d . . . F6 F 0.5082(7) 0.23575(19) 0.0996(5) 0.0359(16) Uani 1 1 d . . . F15 F -0.0773(7) 0.02156(19) 0.0843(6) 0.0373(17) Uani 1 1 d . . . F19 F 0.2530(8) 0.1825(2) 0.3748(5) 0.0379(17) Uani 1 1 d . . . F1 F 0.3169(7) 0.22670(19) -0.2473(5) 0.0331(15) Uani 1 1 d . . . F8 F 0.6467(7) 0.0643(2) 0.0631(6) 0.0413(17) Uani 1 1 d . . . F10 F 0.3561(9) 0.0256(2) -0.1581(7) 0.053(2) Uani 1 1 d . . . F4 F 0.4453(7) 0.26792(18) -0.0556(6) 0.0374(17) Uani 1 1 d . . . F24 F 0.4508(8) 0.1032(2) 0.6345(5) 0.0428(18) Uani 1 1 d . . . F7 F 0.6536(7) 0.1158(2) -0.0354(7) 0.0401(18) Uani 1 1 d . . . F9 F 0.6177(8) 0.0578(2) -0.1127(6) 0.0456(19) Uani 1 1 d . . . F22 F 0.3808(8) 0.05398(19) 0.5226(6) 0.0395(17) Uani 1 1 d . . . F12 F 0.2040(7) 0.0581(2) -0.1037(6) 0.0406(18) Uani 1 1 d . . . F17 F 0.1564(8) 0.0279(2) 0.3318(6) 0.0398(17) Uani 1 1 d . . . F2 F 0.5190(7) 0.1968(2) -0.2095(6) 0.0454(19) Uani 1 1 d . . . N4 N 0.6636(8) 0.1533(2) 0.3361(6) 0.0163(17) Uani 1 1 d . . . F18 F 0.3472(7) 0.0188(2) 0.2922(6) 0.0422(18) Uani 1 1 d . . . N2 N 0.0645(8) 0.2019(2) 0.0567(7) 0.0151(16) Uani 1 1 d . . . F16 F 0.1637(8) -0.01713(19) 0.2121(6) 0.0406(18) Uani 1 1 d . . . F21 F 0.1631(8) 0.1608(2) 0.4965(7) 0.050(2) Uani 1 1 d . . . F23 F 0.2292(9) 0.0872(3) 0.5756(7) 0.061(2) Uani 1 1 d . . . C22 C 0.7776(9) 0.1384(3) 0.4399(9) 0.020(2) Uani 1 1 d . . . H22A H 0.7391 0.1376 0.5025 0.024 Uiso 1 1 calc R . . H22B H 0.8590 0.1572 0.4613 0.024 Uiso 1 1 calc R . . N1 N -0.0540(10) 0.1643(3) -0.1783(7) 0.026(2) Uani 1 1 d . . . N3 N 0.7232(9) 0.0672(3) 0.4082(6) 0.0209(18) Uani 1 1 d . . . C23 C 0.6091(11) 0.1910(3) 0.3629(8) 0.020(2) Uani 1 1 d . . . H23A H 0.5715 0.1868 0.4243 0.030 Uiso 1 1 calc R . . H23B H 0.5323 0.2008 0.2960 0.030 Uiso 1 1 calc R . . H23C H 0.6870 0.2105 0.3865 0.030 Uiso 1 1 calc R . . C24 C 0.7217(11) 0.1599(3) 0.2445(8) 0.023(2) Uani 1 1 d . . . H24A H 0.6470 0.1713 0.1788 0.035 Uiso 1 1 calc R . . H24B H 0.7536 0.1345 0.2234 0.035 Uiso 1 1 calc R . . H24C H 0.8031 0.1783 0.2705 0.035 Uiso 1 1 calc R . . C7 C -0.0046(12) 0.0560(3) 0.1108(10) 0.027(2) Uani 1 1 d . . . C5 C 0.4272(12) 0.0877(3) -0.0673(8) 0.024(2) Uani 1 1 d . . . H5 H 0.3903 0.1021 -0.1412 0.029 Uiso 1 1 calc R . . C8 C 0.1568(11) 0.0497(3) 0.1510(9) 0.021(2) Uani 1 1 d . . . H8 H 0.1830 0.0392 0.0866 0.026 Uiso 1 1 calc R . . C15 C -0.1300(11) 0.1908(3) -0.1292(9) 0.024(2) Uani 1 1 d . . . H15A H -0.1829 0.1749 -0.0906 0.028 Uiso 1 1 calc R . . H15B H -0.2013 0.2060 -0.1904 0.028 Uiso 1 1 calc R . . C17 C 0.1613(11) 0.2331(3) 0.1255(9) 0.025(2) Uani 1 1 d . . . H17A H 0.2165 0.2448 0.0823 0.037 Uiso 1 1 calc R . . H17B H 0.2270 0.2213 0.1952 0.037 Uiso 1 1 calc R . . H17C H 0.1041 0.2539 0.1444 0.037 Uiso 1 1 calc R . . C11 C 0.3177(11) 0.1177(3) 0.4410(8) 0.023(2) Uani 1 1 d . . . H11 H 0.2368 0.1068 0.3759 0.028 Uiso 1 1 calc R . . C20 C 0.7058(11) 0.0563(3) 0.5149(9) 0.028(2) Uani 1 1 d . . . H20A H 0.7965 0.0459 0.5670 0.042 Uiso 1 1 calc R . . H20B H 0.6311 0.0360 0.5010 0.042 Uiso 1 1 calc R . . H20C H 0.6781 0.0799 0.5481 0.042 Uiso 1 1 calc R . . C21 C 0.8315(11) 0.0979(3) 0.4259(9) 0.026(2) Uani 1 1 d . . . H21A H 0.8652 0.0982 0.3608 0.031 Uiso 1 1 calc R . . H21B H 0.9145 0.0913 0.4942 0.031 Uiso 1 1 calc R . . C6 C 0.3464(12) 0.0492(3) -0.0772(9) 0.025(2) Uani 1 1 d . . . C10 C 0.2789(13) 0.1595(4) 0.4667(9) 0.032(3) Uani 1 1 d . . . C18 C -0.0137(12) 0.1837(3) 0.1254(9) 0.028(2) Uani 1 1 d . . . H18A H -0.0723 0.2040 0.1444 0.041 Uiso 1 1 calc R . . H18B H 0.0553 0.1728 0.1950 0.041 Uiso 1 1 calc R . . H18C H -0.0756 0.1623 0.0823 0.041 Uiso 1 1 calc R . . C4 C 0.5883(13) 0.0807(4) -0.0365(10) 0.031(3) Uani 1 1 d . . . C12 C 0.3439(13) 0.0901(4) 0.5443(9) 0.033(3) Uani 1 1 d . . . C16 C -0.0344(12) 0.2194(3) -0.0466(10) 0.029(3) Uani 1 1 d . . . H16A H 0.0222 0.2341 -0.0847 0.034 Uiso 1 1 calc R . . H16B H -0.0952 0.2390 -0.0256 0.034 Uiso 1 1 calc R . . C14 C -0.1400(13) 0.1291(4) -0.2277(10) 0.039(3) Uani 1 1 d . . . H14A H -0.2370 0.1374 -0.2742 0.059 Uiso 1 1 calc R . . H14B H -0.1448 0.1116 -0.1672 0.059 Uiso 1 1 calc R . . H14C H -0.0954 0.1149 -0.2748 0.059 Uiso 1 1 calc R . . C13 C -0.0142(13) 0.1843(4) -0.2673(9) 0.035(3) Uani 1 1 d . . . H13A H -0.1004 0.1950 -0.3248 0.053 Uiso 1 1 calc R . . H13B H 0.0318 0.1651 -0.3023 0.053 Uiso 1 1 calc R . . H13C H 0.0526 0.2060 -0.2339 0.053 Uiso 1 1 calc R . . C19 C 0.7597(16) 0.0315(4) 0.3577(11) 0.045(3) Uani 1 1 d . . . H19A H 0.7626 0.0379 0.2827 0.067 Uiso 1 1 calc R . . H19B H 0.6872 0.0109 0.3505 0.067 Uiso 1 1 calc R . . H19C H 0.8538 0.0216 0.4059 0.067 Uiso 1 1 calc R . . C3 C 0.5014(10) 0.2339(3) -0.0082(9) 0.021(2) Uani 1 1 d . . . C9 C 0.2025(11) 0.0195(3) 0.2469(10) 0.027(2) 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 0.01473(17) 0.01544(18) 0.01319(17) -0.00006(13) 0.00376(13) -0.00088(14) Bi2 0.01714(18) 0.01591(18) 0.01290(17) 0.00048(13) 0.00370(13) -0.00031(14) O2 0.016(3) 0.022(4) 0.014(3) -0.003(3) 0.006(3) 0.002(3) O3 0.026(4) 0.016(3) 0.015(3) 0.002(3) 0.004(3) -0.001(3) O1 0.017(3) 0.017(3) 0.021(4) 0.005(3) 0.009(3) 0.001(3) O4 0.019(4) 0.019(4) 0.029(4) 0.004(3) 0.007(3) -0.002(3) O5 0.018(4) 0.030(4) 0.014(3) 0.002(3) 0.006(3) -0.001(3) C1 0.021(5) 0.041(7) 0.021(6) 0.001(5) 0.014(4) 0.000(5) C2 0.017(5) 0.023(5) 0.017(5) 0.003(4) 0.008(4) 0.000(4) F3 0.045(4) 0.030(4) 0.020(3) -0.004(3) 0.011(3) -0.001(3) F13 0.021(3) 0.045(4) 0.034(4) 0.011(3) -0.005(3) -0.004(3) F5 0.019(3) 0.041(4) 0.053(5) -0.012(3) 0.009(3) -0.006(3) F14 0.033(4) 0.040(4) 0.049(4) -0.005(3) 0.023(3) -0.001(3) F20 0.059(5) 0.036(4) 0.018(3) -0.011(3) 0.010(3) -0.004(3) F11 0.039(4) 0.028(4) 0.057(5) 0.010(3) 0.024(4) 0.004(3) F6 0.041(4) 0.033(4) 0.030(4) -0.010(3) 0.008(3) -0.007(3) F15 0.026(4) 0.030(4) 0.049(4) -0.001(3) 0.004(3) -0.014(3) F19 0.051(4) 0.037(4) 0.025(4) 0.002(3) 0.012(3) 0.013(3) F1 0.037(4) 0.034(4) 0.026(3) 0.014(3) 0.008(3) 0.005(3) F8 0.032(4) 0.045(4) 0.044(4) 0.005(3) 0.009(3) 0.014(3) F10 0.066(5) 0.043(5) 0.059(5) -0.035(4) 0.034(4) -0.015(4) F4 0.033(4) 0.019(3) 0.049(4) 0.006(3) 0.000(3) 0.001(3) F24 0.060(5) 0.045(4) 0.018(3) 0.003(3) 0.007(3) 0.006(4) F7 0.032(4) 0.030(4) 0.067(5) -0.004(3) 0.029(4) -0.004(3) F9 0.047(5) 0.047(5) 0.053(5) -0.015(4) 0.031(4) 0.006(4) F22 0.057(5) 0.024(4) 0.040(4) 0.003(3) 0.019(4) -0.004(3) F12 0.024(4) 0.040(4) 0.054(5) -0.010(3) 0.009(3) -0.011(3) F17 0.054(5) 0.038(4) 0.029(4) 0.010(3) 0.017(3) -0.001(3) F2 0.028(4) 0.086(6) 0.030(4) 0.004(4) 0.019(3) -0.003(4) N4 0.018(4) 0.020(4) 0.014(4) -0.005(3) 0.010(3) -0.003(3) F18 0.024(4) 0.035(4) 0.057(5) 0.015(3) 0.001(3) 0.003(3) N2 0.014(4) 0.011(4) 0.023(4) -0.001(3) 0.010(3) -0.004(3) F16 0.047(4) 0.023(4) 0.048(4) 0.004(3) 0.011(4) -0.008(3) F21 0.042(5) 0.058(5) 0.060(5) -0.005(4) 0.032(4) 0.008(4) F23 0.061(5) 0.083(6) 0.064(6) 0.030(5) 0.052(5) 0.013(5) C22 0.003(4) 0.024(5) 0.030(6) 0.007(4) 0.002(4) -0.003(4) N1 0.030(5) 0.025(5) 0.017(4) 0.002(4) 0.002(4) -0.003(4) N3 0.030(5) 0.023(5) 0.006(4) 0.001(3) 0.002(3) 0.004(4) C23 0.022(5) 0.019(5) 0.019(5) -0.006(4) 0.008(4) -0.002(4) C24 0.025(5) 0.025(6) 0.018(5) 0.000(4) 0.006(4) -0.005(4) C7 0.028(6) 0.021(6) 0.033(6) -0.001(5) 0.013(5) -0.006(4) C5 0.032(6) 0.022(6) 0.013(5) 0.002(4) 0.002(4) 0.004(4) C8 0.026(6) 0.019(5) 0.023(5) -0.006(4) 0.013(4) -0.008(4) C15 0.016(5) 0.030(6) 0.020(5) 0.004(4) 0.001(4) -0.003(4) C17 0.023(5) 0.023(6) 0.026(6) -0.003(4) 0.006(4) 0.005(4) C11 0.024(5) 0.035(6) 0.013(5) -0.003(4) 0.009(4) -0.004(5) C20 0.021(5) 0.037(7) 0.024(6) -0.001(5) 0.005(5) 0.003(5) C21 0.024(6) 0.031(6) 0.015(5) 0.001(4) -0.002(4) -0.004(5) C6 0.031(6) 0.022(6) 0.027(6) -0.007(4) 0.014(5) -0.001(4) C10 0.035(7) 0.042(7) 0.017(6) 0.002(5) 0.006(5) 0.008(5) C18 0.027(6) 0.034(6) 0.030(6) -0.001(5) 0.020(5) 0.001(5) C4 0.034(7) 0.032(7) 0.038(7) -0.004(5) 0.026(6) 0.004(5) C12 0.040(7) 0.039(7) 0.018(6) 0.007(5) 0.009(5) -0.002(6) C16 0.036(7) 0.017(5) 0.036(7) 0.006(5) 0.016(5) 0.010(5) C14 0.038(7) 0.032(7) 0.028(7) 0.005(5) -0.013(5) -0.009(5) C13 0.034(7) 0.051(8) 0.015(6) 0.005(5) 0.001(5) -0.003(6) C19 0.075(10) 0.029(7) 0.040(8) 0.008(6) 0.033(7) 0.009(7) C3 0.014(5) 0.022(6) 0.022(5) 0.001(4) 0.001(4) 0.004(4) C9 0.021(6) 0.023(6) 0.032(6) 0.005(5) 0.004(5) -0.002(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 O3 2.076(6) . ? Bi1 O1 2.153(6) . ? Bi1 O2 2.276(6) . ? Bi1 N2 2.532(8) . ? Bi2 O3 2.077(6) . ? Bi2 O5 2.146(7) . ? Bi2 O4 2.300(7) . ? Bi2 N4 2.542(8) . ? O2 C5 1.399(12) . ? O1 C2 1.383(11) . ? O4 C8 1.379(11) . ? O5 C11 1.367(12) . ? C1 F1 1.321(12) . ? C1 F3 1.326(13) . ? C1 F2 1.344(11) . ? C1 C2 1.521(14) . ? C2 C3 1.533(14) . ? F13 C7 1.338(13) . ? F5 C3 1.335(11) . ? F14 C7 1.322(13) . ? F20 C10 1.337(13) . ? F11 C6 1.333(13) . ? F6 C3 1.339(12) . ? F15 C7 1.344(12) . ? F19 C10 1.342(13) . ? F8 C4 1.309(14) . ? F10 C6 1.323(12) . ? F4 C3 1.322(11) . ? F24 C12 1.335(13) . ? F7 C4 1.346(13) . ? F9 C4 1.341(12) . ? F22 C12 1.324(14) . ? F12 C6 1.371(12) . ? F17 C9 1.334(13) . ? N4 C23 1.462(12) . ? N4 C24 1.478(12) . ? N4 C22 1.492(12) . ? F18 C9 1.353(12) . ? N2 C16 1.459(13) . ? N2 C18 1.483(12) . ? N2 C17 1.485(12) . ? F16 C9 1.320(12) . ? F21 C10 1.330(13) . ? F23 C12 1.334(14) . ? C22 C21 1.496(14) . ? N1 C15 1.440(14) . ? N1 C14 1.468(14) . ? N1 C13 1.476(14) . ? N3 C21 1.453(13) . ? N3 C20 1.462(13) . ? N3 C19 1.464(14) . ? C7 C8 1.522(15) . ? C5 C6 1.507(15) . ? C5 C4 1.531(15) . ? C8 C9 1.525(15) . ? C15 C16 1.493(15) . ? C11 C10 1.521(16) . ? C11 C12 1.549(15) . ? 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 O3 Bi1 O1 92.2(3) . . ? O3 Bi1 O2 77.9(2) . . ? O1 Bi1 O2 88.9(2) . . ? O3 Bi1 N2 85.7(3) . . ? O1 Bi1 N2 78.0(2) . . ? O2 Bi1 N2 158.7(2) . . ? O3 Bi2 O5 93.7(3) . . ? O3 Bi2 O4 77.6(3) . . ? O5 Bi2 O4 90.7(3) . . ? O3 Bi2 N4 81.0(3) . . ? O5 Bi2 N4 78.2(2) . . ? O4 Bi2 N4 155.2(2) . . ? C5 O2 Bi1 129.6(6) . . ? Bi1 O3 Bi2 110.3(3) . . ? C2 O1 Bi1 121.8(6) . . ? C8 O4 Bi2 131.5(6) . . ? C11 O5 Bi2 127.7(6) . . ? F1 C1 F3 107.8(9) . . ? F1 C1 F2 107.4(9) . . ? F3 C1 F2 105.8(9) . . ? F1 C1 C2 114.3(9) . . ? F3 C1 C2 109.2(8) . . ? F2 C1 C2 111.9(9) . . ? O1 C2 C1 108.2(8) . . ? O1 C2 C3 110.3(8) . . ? C1 C2 C3 110.5(8) . . ? C23 N4 C24 109.2(8) . . ? C23 N4 C22 108.6(7) . . ? C24 N4 C22 110.7(8) . . ? C23 N4 Bi2 109.8(6) . . ? C24 N4 Bi2 104.4(6) . . ? C22 N4 Bi2 114.1(5) . . ? C16 N2 C18 111.2(8) . . ? C16 N2 C17 109.6(8) . . ? C18 N2 C17 108.3(8) . . ? C16 N2 Bi1 112.5(6) . . ? C18 N2 Bi1 105.1(6) . . ? C17 N2 Bi1 109.9(6) . . ? N4 C22 C21 113.5(8) . . ? C15 N1 C14 111.6(9) . . ? C15 N1 C13 111.4(9) . . ? C14 N1 C13 108.3(9) . . ? C21 N3 C20 110.7(8) . . ? C21 N3 C19 111.7(9) . . ? C20 N3 C19 108.8(8) . . ? F14 C7 F13 107.3(9) . . ? F14 C7 F15 108.5(9) . . ? F13 C7 F15 105.9(9) . . ? F14 C7 C8 113.3(9) . . ? F13 C7 C8 109.2(9) . . ? F15 C7 C8 112.2(9) . . ? O2 C5 C6 110.8(9) . . ? O2 C5 C4 107.4(8) . . ? C6 C5 C4 111.6(9) . . ? O4 C8 C7 107.3(8) . . ? O4 C8 C9 113.3(9) . . ? C7 C8 C9 110.3(8) . . ? N1 C15 C16 113.4(9) . . ? O5 C11 C10 110.8(9) . . ? O5 C11 C12 108.5(9) . . ? C10 C11 C12 110.9(9) . . ? N3 C21 C22 112.9(9) . . ? F10 C6 F11 108.3(9) . . ? F10 C6 F12 106.8(9) . . ? F11 C6 F12 105.5(9) . . ? F10 C6 C5 113.7(9) . . ? F11 C6 C5 114.1(9) . . ? F12 C6 C5 107.9(9) . . ? F21 C10 F20 107.5(9) . . ? F21 C10 F19 107.4(9) . . ? F20 C10 F19 105.6(10) . . ? F21 C10 C11 113.5(10) . . ? F20 C10 C11 112.8(9) . . ? F19 C10 C11 109.6(9) . . ? F8 C4 F9 108.2(9) . . ? F8 C4 F7 107.9(10) . . ? F9 C4 F7 106.7(9) . . ? F8 C4 C5 112.7(9) . . ? F9 C4 C5 112.0(10) . . ? F7 C4 C5 109.0(9) . . ? F22 C12 F23 108.8(10) . . ? F22 C12 F24 106.5(10) . . ? F23 C12 F24 106.3(10) . . ? F22 C12 C11 110.8(9) . . ? F23 C12 C11 112.4(10) . . ? F24 C12 C11 111.8(9) . . ? N2 C16 C15 115.6(8) . . ? F4 C3 F5 107.8(9) . . ? F4 C3 F6 106.6(8) . . ? F5 C3 F6 106.5(8) . . ? F4 C3 C2 114.6(8) . . ? F5 C3 C2 111.2(8) . . ? F6 C3 C2 109.8(8) . . ? F16 C9 F17 108.8(9) . . ? F16 C9 F18 105.6(9) . . ? F17 C9 F18 106.0(9) . . ? F16 C9 C8 112.7(9) . . ? F17 C9 C8 113.9(9) . . ? F18 C9 C8 109.2(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.18 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.478 _refine_diff_density_min -2.089 _refine_diff_density_rms 0.307