# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Phil Andrews' _publ_contact_author_email PHIL.ANDREWS@SCI.MONASH.EDU.AU _publ_section_title ; Bismuth(III) 5-Sulfosalicylate Complexes: Structure, Solubility and Activity against Helicobacter pylori ; loop_ _publ_author_name 'Phil Andrews' 'Glen Deacon' 'Richard. L. Ferrero' 'Peter Junk' 'Abdulgader Karrar' 'Ish Kumar' ; J.G.MacLellan ; # Attachment '1a.CIF' data_jon44 _database_code_depnum_ccdc_archive 'CCDC 716563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 Bi O7 S' _chemical_formula_sum 'C13 H11 Bi O7 S' _chemical_formula_weight 520.26 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.4684(4) _cell_length_b 6.3564(3) _cell_length_c 23.0087(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.552(2) _cell_angle_gamma 90.00 _cell_volume 1517.75(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 11295 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 30.51 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 11.785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.207 _exptl_absorpt_correction_T_max 0.274 _exptl_absorpt_process_details SORTAV _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7824 _diffrn_reflns_av_R_equivalents 0.0910 _diffrn_reflns_av_sigmaI/netI 0.1064 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2896 _reflns_number_gt 2036 _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^)+(0.0728P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2896 _refine_ls_number_parameters 205 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.045 _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 0.11142(4) 0.73428(7) 0.34686(2) 0.01139(19) Uani 1 1 d . . . S1 S 0.0815(3) 0.8197(5) 0.68195(14) 0.0122(7) Uani 1 1 d . . . O1 O -0.0498(9) 0.8855(12) 0.6571(4) 0.013(2) Uani 1 1 d . . . O2 O 0.1674(9) 0.9998(13) 0.6921(4) 0.015(2) Uani 1 1 d . . . O3 O 0.0808(9) 0.6844(14) 0.7340(4) 0.017(2) Uani 1 1 d . . . O4 O 0.0928(9) 0.8181(14) 0.4484(4) 0.017(2) Uani 1 1 d U . . O5 O 0.1918(9) 0.5298(14) 0.4278(4) 0.016(2) Uani 1 1 d U . . O6 O 0.2906(11) 0.2847(15) 0.5102(5) 0.034(3) Uani 1 1 d U . . H1 H 0.2716 0.3336 0.4762 0.040 Uiso 1 1 calc R . . O7 O 0.2250(10) 0.4344(14) 0.3105(4) 0.017(2) Uani 1 1 d D . . C1 C 0.1386(12) 0.6583(19) 0.6276(5) 0.008(3) Uani 1 1 d U . . C2 C 0.1199(12) 0.715(2) 0.5707(6) 0.016(3) Uani 1 1 d . . . H2 H 0.0733 0.8403 0.5593 0.019 Uiso 1 1 calc R . . C3 C 0.1683(12) 0.5935(17) 0.5288(5) 0.007(3) Uani 1 1 d . . . C4 C 0.2424(14) 0.406(2) 0.5480(6) 0.021(3) Uani 1 1 d . . . C5 C 0.2608(14) 0.358(2) 0.6062(6) 0.020(3) Uani 1 1 d . . . H5 H 0.3111 0.2385 0.6192 0.024 Uiso 1 1 calc R . . C6 C 0.2077(13) 0.480(2) 0.6467(6) 0.017(3) Uani 1 1 d . . . H6 H 0.2186 0.4420 0.6870 0.020 Uiso 1 1 calc R . . C7 C 0.1485(14) 0.649(2) 0.4658(6) 0.017(3) Uani 1 1 d U . . C8 C 0.3039(13) 0.8922(19) 0.3519(6) 0.014(3) Uani 1 1 d . . . C9 C 0.3680(13) 0.890(2) 0.3040(6) 0.019(3) Uani 1 1 d . . . H9 H 0.3338 0.8122 0.2702 0.023 Uiso 1 1 calc R . . C10 C 0.4822(13) 0.998(2) 0.3040(7) 0.028(4) Uani 1 1 d . . . H10 H 0.5263 0.9956 0.2705 0.034 Uiso 1 1 calc R . . C11 C 0.5316(15) 1.111(2) 0.3531(8) 0.035(4) Uani 1 1 d . . . H11 H 0.6086 1.1897 0.3527 0.041 Uiso 1 1 calc R . . C12 C 0.4691(16) 1.110(2) 0.4036(8) 0.035(4) Uani 1 1 d . . . H12 H 0.5049 1.1822 0.4381 0.042 Uiso 1 1 calc R . . C13 C 0.3521(14) 1.000(2) 0.4015(6) 0.022(3) Uani 1 1 d . . . H13 H 0.3064 1.0004 0.4345 0.026 Uiso 1 1 calc R . . H7A H 0.190(13) 0.334(14) 0.326(6) 0.026 Uiso 1 1 d D . . H7B H 0.218(14) 0.41(2) 0.2744(14) 0.026 Uiso 1 1 d 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 0.0136(3) 0.0106(3) 0.0106(3) -0.0002(2) 0.00389(19) -0.0008(2) S1 0.0143(17) 0.0134(16) 0.0094(17) -0.0011(13) 0.0034(14) -0.0002(14) O1 0.022(6) 0.007(4) 0.011(5) 0.004(3) 0.003(4) -0.003(4) O2 0.024(6) 0.008(5) 0.014(5) -0.006(4) 0.007(4) -0.010(4) O3 0.020(5) 0.022(5) 0.010(5) 0.001(4) 0.004(4) 0.007(5) O4 0.022(5) 0.013(4) 0.018(5) 0.000(4) 0.006(4) 0.001(4) O5 0.020(5) 0.016(4) 0.013(5) -0.001(4) 0.007(4) 0.001(4) O6 0.039(4) 0.034(4) 0.029(4) -0.006(3) 0.008(4) 0.019(4) O7 0.028(6) 0.011(5) 0.012(5) 0.004(4) 0.007(5) -0.004(4) C1 0.005(4) 0.008(4) 0.011(5) -0.001(4) 0.002(4) 0.004(4) C2 0.011(6) 0.026(8) 0.012(7) -0.002(6) 0.006(5) -0.008(6) C3 0.006(6) 0.002(6) 0.015(7) 0.001(5) 0.002(5) 0.000(5) C4 0.029(9) 0.020(8) 0.016(8) 0.004(6) 0.013(7) 0.009(7) C5 0.025(9) 0.024(8) 0.012(8) 0.005(6) 0.004(7) 0.010(6) C6 0.021(8) 0.020(7) 0.011(8) 0.004(6) 0.009(6) 0.003(6) C7 0.019(6) 0.014(5) 0.021(6) -0.003(5) 0.007(5) -0.006(5) C8 0.018(8) 0.010(7) 0.013(8) 0.000(5) -0.006(6) -0.009(6) C9 0.014(8) 0.020(7) 0.022(9) 0.004(6) -0.001(6) -0.005(6) C10 0.012(8) 0.032(9) 0.042(11) 0.008(8) 0.007(7) 0.005(7) C11 0.009(8) 0.024(9) 0.073(14) 0.014(8) 0.015(9) 0.001(7) C12 0.028(10) 0.017(8) 0.058(13) -0.010(8) 0.002(9) -0.003(7) C13 0.017(8) 0.018(8) 0.030(10) 0.001(6) -0.003(7) -0.002(6) _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 C8 2.240(13) . ? Bi1 O5 2.336(9) . ? Bi1 O4 2.428(9) . ? Bi1 O7 2.452(9) . ? Bi1 O1 2.500(8) 3_576 ? Bi1 O3 2.625(9) 4_575 ? Bi1 C7 2.766(14) . ? S1 O2 1.455(9) . ? S1 O3 1.475(9) . ? S1 O1 1.478(10) . ? S1 C1 1.780(12) . ? O1 Bi1 2.500(8) 3_576 ? O3 Bi1 2.625(9) 4_576 ? O4 C7 1.264(16) . ? O5 C7 1.282(15) . ? O6 C4 1.313(15) . ? O6 H1 0.8400 . ? O7 H7A 0.84(11) . ? O7 H7B 0.84(4) . ? C1 C2 1.348(19) . ? C1 C6 1.385(18) . ? C2 C3 1.386(17) . ? C2 H2 0.9500 . ? C3 C4 1.456(17) . ? C3 C7 1.479(18) . ? C4 C5 1.363(18) . ? C5 C6 1.384(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.363(17) . ? C8 C13 1.370(18) . ? C9 C10 1.380(18) . ? C9 H9 0.9500 . ? C10 C11 1.38(2) . ? C10 H10 0.9500 . ? C11 C12 1.41(2) . ? C11 H11 0.9500 . ? C12 C13 1.41(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 C8 Bi1 O5 88.9(4) . . ? C8 Bi1 O4 92.2(4) . . ? O5 Bi1 O4 54.6(3) . . ? C8 Bi1 O7 83.8(4) . . ? O5 Bi1 O7 72.5(3) . . ? O4 Bi1 O7 127.1(3) . . ? C8 Bi1 O1 78.2(4) . 3_576 ? O5 Bi1 O1 129.1(3) . 3_576 ? O4 Bi1 O1 76.7(3) . 3_576 ? O7 Bi1 O1 150.9(3) . 3_576 ? C8 Bi1 O3 87.4(4) . 4_575 ? O5 Bi1 O3 152.0(3) . 4_575 ? O4 Bi1 O3 153.3(3) . 4_575 ? O7 Bi1 O3 79.4(3) . 4_575 ? O1 Bi1 O3 77.1(3) 3_576 4_575 ? C8 Bi1 C7 91.7(4) . . ? O5 Bi1 C7 27.5(3) . . ? O4 Bi1 C7 27.2(3) . . ? O7 Bi1 C7 100.0(4) . . ? O1 Bi1 C7 103.2(3) 3_576 . ? O3 Bi1 C7 178.9(3) 4_575 . ? O2 S1 O3 113.4(6) . . ? O2 S1 O1 111.3(5) . . ? O3 S1 O1 112.1(5) . . ? O2 S1 C1 108.0(5) . . ? O3 S1 C1 105.8(5) . . ? O1 S1 C1 105.8(6) . . ? S1 O1 Bi1 120.7(5) . 3_576 ? S1 O3 Bi1 132.5(5) . 4_576 ? C7 O4 Bi1 91.5(7) . . ? C7 O5 Bi1 95.3(9) . . ? C4 O6 H1 109.5 . . ? Bi1 O7 H7A 101(10) . . ? Bi1 O7 H7B 120(10) . . ? H7A O7 H7B 107(10) . . ? C2 C1 C6 122.1(12) . . ? C2 C1 S1 120.5(10) . . ? C6 C1 S1 117.4(10) . . ? C1 C2 C3 120.4(13) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 118.3(12) . . ? C2 C3 C7 122.2(12) . . ? C4 C3 C7 119.5(11) . . ? O6 C4 C5 120.0(13) . . ? O6 C4 C3 121.0(13) . . ? C5 C4 C3 118.9(12) . . ? C4 C5 C6 121.2(14) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 119.0(13) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O4 C7 O5 118.4(13) . . ? O4 C7 C3 120.8(11) . . ? O5 C7 C3 120.7(13) . . ? O4 C7 Bi1 61.3(7) . . ? O5 C7 Bi1 57.2(7) . . ? C3 C7 Bi1 177.6(9) . . ? C9 C8 C13 120.8(13) . . ? C9 C8 Bi1 119.3(10) . . ? C13 C8 Bi1 119.9(10) . . ? C8 C9 C10 120.9(14) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 119.4(14) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.6(14) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 118.1(15) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C8 C13 C12 120.2(14) . . ? C8 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7A O1 0.84(11) 2.10(12) 2.901(12) 160(15) 3_566 O7 H7B O2 0.84(4) 1.99(8) 2.744(13) 150(14) 4_575 O6 H1 O5 0.84 1.80 2.564(14) 149.8 . _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 3.278 _refine_diff_density_min -2.592 _refine_diff_density_rms 0.376 # Attachment '1b.CIF' data_j104abs _database_code_depnum_ccdc_archive 'CCDC 716564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 Bi O7 S' _chemical_formula_sum 'C15 H15 Bi O7 S' _chemical_formula_weight 548.31 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.8439(2) _cell_length_b 11.1140(4) _cell_length_c 19.2058(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.179(2) _cell_angle_gamma 90.00 _cell_volume 1674.30(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 20721 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 30.51 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 10.689 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1274 _exptl_absorpt_correction_T_max 0.2491 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14807 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3234 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0767P)^2^+4.3034P] 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 3234 _refine_ls_number_parameters 281 _refine_ls_number_restraints 106 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.028 _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 0.22261(5) 0.32518(3) 0.436605(16) 0.02779(16) Uani 1 1 d . . . S1 S 0.1968(3) -0.37031(18) 0.48535(10) 0.0195(4) Uani 1 1 d D . . O1 O 0.0332(12) -0.3100(9) 0.5037(7) 0.015(2) Uani 0.50 1 d PDU . 2 C1 C 0.3234(10) -0.2532(7) 0.4510(4) 0.0194(18) Uani 1 1 d . . . O2 O 0.3321(14) -0.4456(11) 0.5184(7) 0.018(3) Uani 0.50 1 d PDU . 1 C2 C 0.2712(10) -0.1335(7) 0.4562(4) 0.0171(17) Uani 1 1 d . . . H2 H 0.1660 -0.1136 0.4777 0.020 Uiso 1 1 calc R . . O3 O 0.1370(9) -0.4441(6) 0.4292(3) 0.0383(17) Uani 1 1 d . . . C3 C 0.3758(11) -0.0438(7) 0.4295(4) 0.0195(18) Uani 1 1 d . . . O4 O 0.1754(8) 0.1132(5) 0.4570(3) 0.0269(14) Uani 1 1 d . . . C4 C 0.5322(12) -0.0739(9) 0.3989(5) 0.031(2) Uani 1 1 d . . . O5 O 0.4168(8) 0.1650(5) 0.4073(3) 0.0278(15) Uani 1 1 d . . . C5 C 0.5791(13) -0.1934(9) 0.3929(6) 0.034(2) Uani 1 1 d . . . H5 H 0.6835 -0.2137 0.3709 0.041 Uiso 1 1 calc R . . O6 O 0.6405(9) 0.0095(6) 0.3731(4) 0.046(2) Uani 1 1 d . . . H6 H 0.5999 0.0785 0.3795 0.055 Uiso 1 1 calc R . . C6 C 0.4769(12) -0.2823(8) 0.4182(5) 0.027(2) Uani 1 1 d . . . H1 H 0.5100 -0.3641 0.4136 0.032 Uiso 1 1 calc R . . O7 O 0.4609(8) 0.4162(6) 0.3743(3) 0.0342(16) Uani 1 1 d . . . H7 H 0.5343 0.4430 0.4022 0.041 Uiso 1 1 calc R . . C7 C 0.3171(12) 0.0838(8) 0.4315(4) 0.025(2) Uani 1 1 d . . . C8 C 0.0983(11) 0.3037(7) 0.3343(4) 0.0246(17) Uani 1 1 d DU . . C9 C -0.0312(17) 0.2151(12) 0.3357(8) 0.020(3) Uani 0.50 1 d PDU . 1 H9 H -0.0534 0.1686 0.3762 0.024 Uiso 0.50 1 calc PR . 1 C10 C -0.123(2) 0.2002(13) 0.2752(7) 0.022(3) Uani 0.50 1 d PDU . 1 H10 H -0.2121 0.1422 0.2736 0.026 Uiso 0.50 1 calc PR . 1 C11 C -0.088(2) 0.2690(15) 0.2163(9) 0.023(3) Uani 0.50 1 d PDU . 1 H11 H -0.1522 0.2581 0.1748 0.028 Uiso 0.50 1 calc PR . 1 C12 C 0.043(2) 0.3537(17) 0.2187(10) 0.021(3) Uani 0.50 1 d PDU . 1 H12 H 0.0696 0.3984 0.1780 0.025 Uiso 0.50 1 calc PR . 1 C13 C 0.136(2) 0.3743(16) 0.2795(8) 0.021(3) Uani 0.50 1 d PDU . 1 H13 H 0.2211 0.4350 0.2822 0.025 Uiso 0.50 1 calc PR . 1 C14 C 0.5421(17) 0.3864(12) 0.3085(6) 0.056(3) Uani 1 1 d . . . H14A H 0.4564 0.3530 0.2758 0.067 Uiso 1 1 calc R . . H14B H 0.6311 0.3246 0.3162 0.067 Uiso 1 1 calc R . . C15 C 0.6204(16) 0.4964(11) 0.2779(6) 0.055(3) Uani 1 1 d . . . H15A H 0.5312 0.5559 0.2682 0.082 Uiso 1 1 calc R . . H15B H 0.6786 0.4754 0.2345 0.082 Uiso 1 1 calc R . . H15C H 0.7030 0.5303 0.3109 0.082 Uiso 1 1 calc R . . O1' O 0.0987(16) -0.3127(10) 0.5399(6) 0.024(3) Uani 0.50 1 d PDU . 1 O2' O 0.2675(17) -0.4310(12) 0.5454(5) 0.020(3) Uani 0.50 1 d PDU . 2 C9A C 0.0590(19) 0.1946(13) 0.3004(8) 0.029(3) Uani 0.50 1 d PDU . 2 H9A H 0.0718 0.1224 0.3263 0.035 Uiso 0.50 1 calc PR . 2 C10A C 0.003(2) 0.1848(14) 0.2316(8) 0.030(3) Uani 0.50 1 d PDU . 2 H10A H -0.0237 0.1084 0.2122 0.036 Uiso 0.50 1 calc PR . 2 C11A C -0.014(3) 0.2884(14) 0.1922(10) 0.029(3) Uani 0.50 1 d PDU . 2 H11A H -0.0520 0.2831 0.1453 0.034 Uiso 0.50 1 calc PR . 2 C12A C 0.023(3) 0.3992(18) 0.2207(10) 0.028(4) Uani 0.50 1 d PDU . 2 H12A H 0.0121 0.4706 0.1938 0.033 Uiso 0.50 1 calc PR . 2 C13A C 0.077(3) 0.4037(15) 0.2898(9) 0.027(4) Uani 0.50 1 d PDU . 2 H13A H 0.1013 0.4809 0.3087 0.033 Uiso 0.50 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0536(3) 0.0081(2) 0.0217(2) -0.00055(13) 0.00335(16) -0.00196(15) S1 0.0292(12) 0.0083(9) 0.0209(10) 0.0003(8) 0.0013(9) 0.0003(8) O1 0.016(6) 0.010(5) 0.020(6) 0.009(5) 0.004(5) -0.004(4) C1 0.022(4) 0.007(4) 0.030(5) -0.005(3) -0.006(4) -0.001(3) O2 0.023(8) 0.018(6) 0.013(7) 0.005(6) -0.002(5) -0.003(5) C2 0.017(4) 0.017(4) 0.018(4) -0.004(3) -0.002(3) -0.002(3) O3 0.056(4) 0.028(4) 0.032(4) 0.009(3) -0.014(3) -0.024(3) C3 0.028(5) 0.008(4) 0.023(4) -0.001(3) 0.002(4) -0.001(3) O4 0.042(4) 0.006(3) 0.032(3) 0.003(3) 0.005(3) 0.000(3) C4 0.035(5) 0.025(5) 0.034(5) -0.009(4) 0.010(4) -0.014(4) O5 0.037(4) 0.016(3) 0.030(3) 0.004(3) 0.000(3) -0.010(3) C5 0.029(5) 0.030(5) 0.044(6) -0.014(5) 0.013(5) -0.004(4) O6 0.048(4) 0.025(4) 0.065(5) -0.013(4) 0.026(4) -0.017(3) C6 0.030(5) 0.015(4) 0.034(5) -0.005(4) 0.003(4) -0.001(4) O7 0.046(4) 0.024(3) 0.032(4) 0.007(3) -0.018(3) -0.016(3) C7 0.043(6) 0.015(4) 0.017(4) 0.001(3) -0.005(4) -0.004(4) C8 0.027(4) 0.017(4) 0.029(4) -0.007(3) -0.001(3) -0.002(3) C9 0.026(6) 0.014(6) 0.020(6) -0.002(5) -0.003(5) -0.006(5) C10 0.023(6) 0.017(6) 0.025(6) -0.002(5) -0.003(6) -0.007(5) C11 0.026(7) 0.016(6) 0.028(7) -0.002(6) 0.004(6) -0.006(6) C12 0.028(7) 0.010(7) 0.023(7) -0.002(6) 0.005(6) -0.003(6) C13 0.025(7) 0.017(6) 0.021(6) -0.005(6) 0.015(6) -0.003(6) C14 0.076(9) 0.056(8) 0.036(6) -0.009(6) -0.005(6) -0.022(7) C15 0.055(8) 0.050(8) 0.060(8) 0.008(6) 0.014(6) 0.000(6) O1' 0.028(7) 0.018(5) 0.028(7) 0.000(6) 0.012(5) -0.002(5) O2' 0.031(8) 0.015(5) 0.016(7) 0.004(5) 0.003(5) -0.002(5) C9A 0.040(7) 0.011(6) 0.037(7) 0.002(6) -0.008(6) 0.002(6) C10A 0.044(7) 0.012(6) 0.035(7) -0.001(6) -0.011(6) 0.000(6) C11A 0.042(8) 0.016(7) 0.027(7) -0.002(6) -0.014(7) -0.002(6) C12A 0.041(8) 0.020(7) 0.023(7) -0.009(7) -0.008(6) -0.002(7) C13A 0.037(7) 0.018(7) 0.027(7) -0.012(6) -0.001(6) -0.004(6) _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 C8 2.204(9) . ? Bi1 O1 2.320(9) 3_556 ? Bi1 O5 2.411(6) . ? Bi1 O4 2.417(6) . ? Bi1 O7 2.441(6) . ? Bi1 O1' 2.566(12) 3_556 ? Bi1 O3 2.654(7) 1_565 ? Bi1 C7 2.785(9) . ? S1 O3 1.432(7) . ? S1 O2' 1.445(8) . ? S1 O1' 1.450(8) . ? S1 O1 1.491(8) . ? S1 O2 1.492(8) . ? S1 C1 1.766(9) . ? O1 Bi1 2.320(9) 3_556 ? C1 C2 1.396(11) . ? C1 C6 1.398(12) . ? C2 C3 1.390(11) . ? C2 H2 0.9500 . ? O3 Bi1 2.654(7) 1_545 ? C3 C4 1.402(12) . ? C3 C7 1.492(11) . ? O4 C7 1.259(12) . ? C4 O6 1.353(11) . ? C4 C5 1.382(13) . ? O5 C7 1.281(10) . ? C5 C6 1.363(13) . ? C5 H5 0.9500 . ? O6 H6 0.8400 . ? C6 H1 0.9500 . ? O7 C14 1.456(13) . ? O7 H7 0.8400 . ? C8 C13 1.346(15) . ? C8 C9A 1.410(14) . ? C8 C13A 1.411(15) . ? C8 C9 1.415(13) . ? C9 C10 1.376(15) . ? C9 H9 0.9500 . ? C10 C11 1.395(16) . ? C10 H10 0.9500 . ? C11 C12 1.394(17) . ? C11 H11 0.9500 . ? C12 C13 1.393(16) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.490(16) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O1' Bi1 2.566(12) 3_556 ? C9A C10A 1.396(16) . ? C9A H9A 0.9500 . ? C10A C11A 1.383(16) . ? C10A H10A 0.9500 . ? C11A C12A 1.378(16) . ? C11A H11A 0.9500 . ? C12A C13A 1.393(16) . ? C12A H12A 0.9500 . ? C13A H13A 0.9500 . ? 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 C8 Bi1 O1 93.0(4) . 3_556 ? C8 Bi1 O5 89.4(3) . . ? O1 Bi1 O5 127.6(3) 3_556 . ? C8 Bi1 O4 88.4(2) . . ? O1 Bi1 O4 73.5(3) 3_556 . ? O5 Bi1 O4 54.2(2) . . ? C8 Bi1 O7 86.8(3) . . ? O1 Bi1 O7 159.5(3) 3_556 . ? O5 Bi1 O7 72.9(2) . . ? O4 Bi1 O7 126.9(2) . . ? C8 Bi1 O1' 73.7(4) . 3_556 ? O1 Bi1 O1' 19.5(3) 3_556 3_556 ? O5 Bi1 O1' 128.5(3) . 3_556 ? O4 Bi1 O1' 76.6(3) . 3_556 ? O7 Bi1 O1' 149.6(3) . 3_556 ? C8 Bi1 O3 86.9(2) . 1_565 ? O1 Bi1 O3 83.0(3) 3_556 1_565 ? O5 Bi1 O3 149.4(2) . 1_565 ? O4 Bi1 O3 155.7(2) . 1_565 ? O7 Bi1 O3 76.6(2) . 1_565 ? O1' Bi1 O3 79.2(3) 3_556 1_565 ? C8 Bi1 C7 88.9(3) . . ? O1 Bi1 C7 100.3(3) 3_556 . ? O5 Bi1 C7 27.4(2) . . ? O4 Bi1 C7 26.8(2) . . ? O7 Bi1 C7 100.2(3) . . ? O1' Bi1 C7 102.5(3) 3_556 . ? O3 Bi1 C7 174.9(2) 1_565 . ? O3 S1 O2' 117.2(6) . . ? O3 S1 O1' 128.5(7) . . ? O2' S1 O1' 80.4(8) . . ? O3 S1 O1 98.9(6) . . ? O2' S1 O1 110.5(7) . . ? O1' S1 O1 34.1(6) . . ? O3 S1 O2 103.3(6) . . ? O2' S1 O2 29.3(5) . . ? O1' S1 O2 108.6(8) . . ? O1 S1 O2 139.8(7) . . ? O3 S1 C1 108.9(4) . . ? O2' S1 C1 115.3(6) . . ? O1' S1 C1 104.2(6) . . ? O1 S1 C1 104.0(5) . . ? O2 S1 C1 99.9(6) . . ? S1 O1 Bi1 146.1(6) . 3_556 ? C2 C1 C6 120.4(8) . . ? C2 C1 S1 120.7(6) . . ? C6 C1 S1 119.0(6) . . ? C3 C2 C1 118.9(7) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? S1 O3 Bi1 115.5(4) . 1_545 ? C2 C3 C4 120.1(8) . . ? C2 C3 C7 119.4(8) . . ? C4 C3 C7 120.5(8) . . ? C7 O4 Bi1 93.1(5) . . ? O6 C4 C5 117.4(8) . . ? O6 C4 C3 122.7(9) . . ? C5 C4 C3 119.9(8) . . ? C7 O5 Bi1 92.8(6) . . ? C6 C5 C4 120.6(9) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C4 O6 H6 109.5 . . ? C5 C6 C1 120.1(8) . . ? C5 C6 H1 119.9 . . ? C1 C6 H1 119.9 . . ? C14 O7 Bi1 132.0(6) . . ? C14 O7 H7 109.5 . . ? Bi1 O7 H7 111.0 . . ? O4 C7 O5 120.0(8) . . ? O4 C7 C3 121.9(8) . . ? O5 C7 C3 118.1(8) . . ? O4 C7 Bi1 60.1(4) . . ? O5 C7 Bi1 59.9(5) . . ? C3 C7 Bi1 177.4(6) . . ? C13 C8 C9A 100.9(11) . . ? C13 C8 C13A 25.0(9) . . ? C9A C8 C13A 111.9(12) . . ? C13 C8 C9 125.5(12) . . ? C9A C8 C9 41.8(8) . . ? C13A C8 C9 118.4(11) . . ? C13 C8 Bi1 122.4(9) . . ? C9A C8 Bi1 126.9(8) . . ? C13A C8 Bi1 120.4(9) . . ? C9 C8 Bi1 111.9(8) . . ? C10 C9 C8 116.2(13) . . ? C10 C9 H9 121.9 . . ? C8 C9 H9 121.9 . . ? C9 C10 C11 121.0(15) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 119.5(16) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 121.5(17) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C8 C13 C12 116.3(16) . . ? C8 C13 H13 121.8 . . ? C12 C13 H13 121.8 . . ? O7 C14 C15 109.7(10) . . ? O7 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? O7 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S1 O1' Bi1 128.8(8) . 3_556 ? C10A C9A C8 124.9(14) . . ? C10A C9A H9A 117.5 . . ? C8 C9A H9A 117.5 . . ? C11A C10A C9A 118.8(16) . . ? C11A C10A H10A 120.6 . . ? C9A C10A H10A 120.6 . . ? C12A C11A C10A 120.5(17) . . ? C12A C11A H11A 119.8 . . ? C10A C11A H11A 119.8 . . ? C11A C12A C13A 118.2(19) . . ? C11A C12A H12A 120.9 . . ? C13A C12A H12A 120.9 . . ? C12A C13A C8 125.7(16) . . ? C12A C13A H13A 117.2 . . ? C8 C13A H13A 117.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O5 0.84 1.81 2.550(10) 146.1 . O7 H7 O2 0.84 1.85 2.640(13) 156.6 3_656 O7 H7 O2' 0.84 1.85 2.632(13) 153.3 3_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 4.289 _refine_diff_density_min -2.363 _refine_diff_density_rms 0.239 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 716565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Bi O15 S2, H2 O' _chemical_formula_sum 'C14 H17 Bi O16 S2' _chemical_formula_weight 714.38 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5840(2) _cell_length_b 11.0003(3) _cell_length_c 12.3515(4) _cell_angle_alpha 82.173(2) _cell_angle_beta 86.677(2) _cell_angle_gamma 87.428(2) _cell_volume 1018.41(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 14568 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 30.18 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 8.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.295 _exptl_absorpt_correction_T_max 0.374 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _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 KAPPA 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 9836 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3579 _reflns_number_gt 3115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0365P)^2^+0.8437P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3579 _refine_ls_number_parameters 324 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _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 0.38841(3) 0.11340(2) 0.85440(2) 0.01812(9) Uani 1 1 d D . . S1 S 0.3248(2) -0.18046(13) 0.92515(14) 0.0194(4) Uani 1 1 d . . . O1 O 0.4746(6) -0.1161(4) 0.9621(4) 0.0199(10) Uani 1 1 d . . . C1 C 0.4182(8) -0.2879(5) 0.8427(6) 0.0191(14) Uani 1 1 d . . . S2 S 0.0551(2) 0.24617(15) 0.67224(14) 0.0230(4) Uani 1 1 d . . . O2 O 0.2270(6) -0.0896(4) 0.8520(4) 0.0232(11) Uani 1 1 d . . . C2 C 0.3920(8) -0.4120(5) 0.8723(5) 0.0182(14) Uani 1 1 d . . . H2 H 0.3284 -0.4400 0.9389 0.022 Uiso 1 1 calc R . . O3 O 0.2207(6) -0.2439(4) 1.0131(4) 0.0266(11) Uani 1 1 d . . . C3 C 0.4596(8) -0.4960(5) 0.8035(5) 0.0180(14) Uani 1 1 d . . . O4 O 0.3359(6) -0.6706(4) 0.9158(4) 0.0215(10) Uani 1 1 d . . . C4 C 0.5537(8) -0.4527(6) 0.7058(5) 0.0182(14) Uani 1 1 d . . . O5 O 0.4895(6) -0.7016(4) 0.7667(4) 0.0229(10) Uani 1 1 d . . . C5 C 0.5800(9) -0.3265(6) 0.6790(6) 0.0235(15) Uani 1 1 d . . . H5 H 0.6452 -0.2975 0.6133 0.028 Uiso 1 1 calc R . . O6 O 0.6235(6) -0.5260(4) 0.6356(4) 0.0264(11) Uani 1 1 d . . . H1 H 0.6023 -0.5993 0.6597 0.032 Uiso 1 1 calc R . . C6 C 0.5129(10) -0.2452(6) 0.7460(6) 0.0254(16) Uani 1 1 d . . . H6 H 0.5306 -0.1598 0.7269 0.030 Uiso 1 1 calc R . . O7 O 0.1188(6) 0.1844(4) 0.7774(4) 0.0214(10) Uani 1 1 d . . . C7 C 0.4251(9) -0.6285(6) 0.8324(6) 0.0204(15) Uani 1 1 d . . . O8 O 0.1620(7) 0.2133(4) 0.5788(4) 0.0326(12) Uani 1 1 d . . . C8 C 0.0734(9) 0.4052(6) 0.6740(6) 0.0249(16) Uani 1 1 d . . . O9 O -0.1315(6) 0.2248(4) 0.6674(4) 0.0300(12) Uani 1 1 d . . . C9 C -0.0057(9) 0.4575(6) 0.7581(6) 0.0236(16) Uani 1 1 d . . . H9 H -0.0633 0.4083 0.8178 0.028 Uiso 1 1 calc R . . O10 O -0.1608(7) 0.5725(4) 0.9244(4) 0.0323(12) Uani 1 1 d . . . H10 H -0.2053 0.6131 0.9727 0.039 Uiso 1 1 calc R . . C10 C -0.0016(9) 0.5868(6) 0.7560(5) 0.0230(15) Uani 1 1 d . . . O11 O -0.0937(7) 0.7591(4) 0.8412(4) 0.0298(12) Uani 1 1 d . . . C11 C 0.0870(9) 0.6562(6) 0.6677(5) 0.0216(15) Uani 1 1 d . . . O12 O 0.0984(7) 0.7782(4) 0.6579(4) 0.0306(12) Uani 1 1 d . . . H11 H 0.0250 0.8066 0.7024 0.037 Uiso 1 1 calc R . . C12 C 0.1706(10) 0.5992(6) 0.5836(6) 0.0255(16) Uani 1 1 d . . . H12 H 0.2330 0.6462 0.5245 0.031 Uiso 1 1 calc R . . O13 O 0.1423(7) 0.0875(5) 1.0083(5) 0.0344(13) Uani 1 1 d D . . C13 C 0.1616(9) 0.4730(6) 0.5870(6) 0.0217(15) Uani 1 1 d . . . H13 H 0.2163 0.4334 0.5294 0.026 Uiso 1 1 calc R . . H13A H 0.056(6) 0.120(6) 0.977(5) 0.026 Uiso 1 1 d D . . H13B H 0.135(10) 0.140(5) 1.049(5) 0.026 Uiso 1 1 d D . . O14 O 0.4277(8) 0.0720(5) 0.6708(4) 0.0360(13) Uani 1 1 d D . . C14 C -0.0891(9) 0.6468(6) 0.8444(6) 0.0273(17) Uani 1 1 d . . . H14A H 0.527(4) 0.071(8) 0.642(6) 0.033 Uiso 1 1 d D . . H14B H 0.366(8) 0.112(6) 0.626(3) 0.033 Uiso 1 1 d D . . O15 O 0.6950(7) 0.0635(5) 0.8157(5) 0.0414(14) Uani 1 1 d D . . H15A H 0.743(11) 0.100(8) 0.858(6) 0.050 Uiso 1 1 d D . . H15B H 0.753(10) 0.108(7) 0.770(5) 0.050 Uiso 1 1 d D . . O16 O 0.7122(11) 0.0632(9) 0.5368(7) 0.093(3) Uani 1 1 d D . . H16A H 0.789(11) 0.115(8) 0.528(10) 0.111 Uiso 1 1 d D . . H16B H 0.762(14) 0.000(6) 0.565(12) 0.111 Uiso 1 1 d 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 0.02152(14) 0.00510(12) 0.02866(15) -0.00321(9) -0.00704(10) -0.00041(8) S1 0.0211(9) 0.0072(7) 0.0317(9) -0.0048(7) -0.0104(7) -0.0025(6) O1 0.019(2) 0.013(2) 0.030(3) -0.0095(19) -0.015(2) -0.0008(18) C1 0.019(4) 0.007(3) 0.035(4) -0.008(3) -0.013(3) 0.000(2) S2 0.0300(10) 0.0135(8) 0.0264(9) 0.0006(7) -0.0124(8) -0.0075(7) O2 0.023(3) 0.010(2) 0.039(3) -0.006(2) -0.014(2) 0.0012(18) C2 0.021(3) 0.009(3) 0.026(4) 0.000(3) -0.014(3) 0.000(3) O3 0.034(3) 0.012(2) 0.036(3) -0.008(2) -0.006(2) -0.008(2) C3 0.018(3) 0.009(3) 0.028(4) -0.003(3) -0.015(3) 0.003(2) O4 0.027(3) 0.008(2) 0.030(3) -0.001(2) -0.012(2) -0.0017(19) C4 0.022(4) 0.012(3) 0.022(3) -0.004(3) -0.012(3) -0.001(3) O5 0.026(3) 0.008(2) 0.035(3) -0.004(2) -0.006(2) 0.0005(19) C5 0.027(4) 0.015(3) 0.029(4) -0.001(3) -0.012(3) -0.005(3) O6 0.040(3) 0.009(2) 0.031(3) -0.004(2) -0.002(2) -0.001(2) C6 0.038(4) 0.009(3) 0.031(4) -0.001(3) -0.015(3) -0.004(3) O7 0.028(3) 0.010(2) 0.026(2) 0.0019(19) -0.013(2) -0.0007(19) C7 0.020(4) 0.010(3) 0.032(4) -0.002(3) -0.012(3) 0.001(3) O8 0.054(4) 0.019(3) 0.025(3) -0.001(2) -0.009(2) -0.008(2) C8 0.019(4) 0.020(3) 0.037(4) -0.001(3) -0.014(3) -0.001(3) O9 0.033(3) 0.021(3) 0.038(3) 0.002(2) -0.019(2) -0.016(2) C9 0.030(4) 0.019(3) 0.024(4) 0.002(3) -0.017(3) -0.010(3) O10 0.048(3) 0.018(2) 0.032(3) -0.004(2) 0.002(3) -0.009(2) C10 0.026(4) 0.021(3) 0.025(4) -0.006(3) -0.016(3) -0.003(3) O11 0.039(3) 0.013(2) 0.040(3) -0.007(2) -0.010(2) -0.005(2) C11 0.024(4) 0.015(3) 0.026(4) 0.002(3) -0.011(3) -0.002(3) O12 0.037(3) 0.020(3) 0.035(3) -0.003(2) -0.001(2) -0.005(2) C12 0.034(4) 0.018(4) 0.024(4) 0.003(3) -0.007(3) -0.003(3) O13 0.020(3) 0.027(3) 0.060(4) -0.022(3) -0.004(3) 0.003(2) C13 0.024(4) 0.017(3) 0.027(4) -0.005(3) -0.012(3) -0.004(3) O14 0.053(4) 0.019(3) 0.037(3) -0.008(2) 0.004(3) -0.005(3) C14 0.028(4) 0.026(4) 0.030(4) -0.002(3) -0.017(3) -0.007(3) O15 0.027(3) 0.032(3) 0.058(4) 0.013(3) 0.006(3) 0.009(2) O16 0.086(6) 0.137(8) 0.067(6) -0.045(6) 0.018(5) -0.074(6) _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 O5 2.312(4) 1_565 ? Bi1 O7 2.362(4) . ? Bi1 O14 2.372(5) . ? Bi1 O15 2.401(5) . ? Bi1 O1 2.551(4) 2_657 ? Bi1 O13 2.582(6) . ? Bi1 O4 2.598(4) 1_565 ? Bi1 O2 2.599(4) . ? Bi1 O1 2.759(4) . ? Bi1 C7 2.840(6) 1_565 ? S1 O3 1.426(5) . ? S1 O2 1.459(5) . ? S1 O1 1.490(4) . ? S1 C1 1.762(6) . ? O1 Bi1 2.551(4) 2_657 ? C1 C2 1.384(8) . ? C1 C6 1.394(10) . ? S2 O8 1.449(5) . ? S2 O9 1.451(5) . ? S2 O7 1.478(4) . ? S2 C8 1.764(7) . ? C2 C3 1.399(9) . ? C2 H2 0.9500 . ? C3 C4 1.402(9) . ? C3 C7 1.484(9) . ? O4 C7 1.246(8) . ? O4 Bi1 2.598(4) 1_545 ? C4 O6 1.335(8) . ? C4 C5 1.403(9) . ? O5 C7 1.281(8) . ? O5 Bi1 2.312(4) 1_545 ? C5 C6 1.363(10) . ? C5 H5 0.9500 . ? O6 H1 0.8400 . ? C6 H6 0.9500 . ? C7 Bi1 2.840(6) 1_545 ? C8 C9 1.352(10) . ? C8 C13 1.379(10) . ? C9 C10 1.421(9) . ? C9 H9 0.9500 . ? O10 C14 1.303(9) . ? O10 H10 0.8400 . ? C10 C11 1.399(10) . ? C10 C14 1.463(10) . ? O11 C14 1.230(8) . ? C11 O12 1.337(8) . ? C11 C12 1.393(10) . ? O12 H11 0.8400 . ? C12 C13 1.388(9) . ? C12 H12 0.9500 . ? O13 H13A 0.82(5) . ? O13 H13B 0.81(6) . ? C13 H13 0.9500 . ? O14 H14A 0.81(4) . ? O14 H14B 0.82(5) . ? O15 H15A 0.81(9) . ? O15 H15B 0.82(10) . ? O16 H16A 0.83(9) . ? O16 H16B 0.82(10) . ? 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 Bi1 O7 83.69(15) 1_565 . ? O5 Bi1 O14 78.53(17) 1_565 . ? O7 Bi1 O14 76.41(18) . . ? O5 Bi1 O15 77.96(18) 1_565 . ? O7 Bi1 O15 145.05(19) . . ? O14 Bi1 O15 71.0(2) . . ? O5 Bi1 O1 98.22(15) 1_565 2_657 ? O7 Bi1 O1 135.72(15) . 2_657 ? O14 Bi1 O1 147.59(18) . 2_657 ? O15 Bi1 O1 76.80(19) . 2_657 ? O5 Bi1 O13 125.66(16) 1_565 . ? O7 Bi1 O13 72.21(17) . . ? O14 Bi1 O13 136.64(18) . . ? O15 Bi1 O13 142.11(19) . . ? O1 Bi1 O13 71.12(16) 2_657 . ? O5 Bi1 O4 52.34(15) 1_565 1_565 ? O7 Bi1 O4 76.61(14) . 1_565 ? O14 Bi1 O4 125.68(16) . 1_565 ? O15 Bi1 O4 112.97(18) . 1_565 ? O1 Bi1 O4 70.47(13) 2_657 1_565 ? O13 Bi1 O4 74.66(15) . 1_565 ? O5 Bi1 O2 150.74(15) 1_565 . ? O7 Bi1 O2 77.71(14) . . ? O14 Bi1 O2 75.29(17) . . ? O15 Bi1 O2 105.16(17) . . ? O1 Bi1 O2 110.88(14) 2_657 . ? O13 Bi1 O2 69.41(15) . . ? O4 Bi1 O2 140.69(15) 1_565 . ? O5 Bi1 O1 146.96(14) 1_565 . ? O7 Bi1 O1 128.38(13) . . ? O14 Bi1 O1 99.56(15) . . ? O15 Bi1 O1 70.46(16) . . ? O1 Bi1 O1 65.72(14) 2_657 . ? O13 Bi1 O1 78.22(15) . . ? O4 Bi1 O1 133.87(13) 1_565 . ? O2 Bi1 O1 52.32(12) . . ? O5 Bi1 C7 26.33(18) 1_565 1_565 ? O7 Bi1 C7 79.02(16) . 1_565 ? O14 Bi1 C7 102.52(19) . 1_565 ? O15 Bi1 C7 95.9(2) . 1_565 ? O1 Bi1 C7 83.78(16) 2_657 1_565 ? O13 Bi1 C7 100.06(19) . 1_565 ? O4 Bi1 C7 26.00(17) 1_565 1_565 ? O2 Bi1 C7 156.47(16) . 1_565 ? O1 Bi1 C7 148.48(15) . 1_565 ? O3 S1 O2 114.9(3) . . ? O3 S1 O1 113.4(3) . . ? O2 S1 O1 106.7(3) . . ? O3 S1 C1 108.7(3) . . ? O2 S1 C1 105.9(3) . . ? O1 S1 C1 106.7(3) . . ? S1 O1 Bi1 134.6(3) . 2_657 ? S1 O1 Bi1 96.5(2) . . ? Bi1 O1 Bi1 114.28(14) 2_657 . ? C2 C1 C6 121.0(6) . . ? C2 C1 S1 120.2(6) . . ? C6 C1 S1 118.8(5) . . ? O8 S2 O9 113.8(3) . . ? O8 S2 O7 112.6(3) . . ? O9 S2 O7 109.3(3) . . ? O8 S2 C8 107.5(3) . . ? O9 S2 C8 106.8(3) . . ? O7 S2 C8 106.5(3) . . ? S1 O2 Bi1 104.4(2) . . ? C1 C2 C3 119.6(6) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 119.2(6) . . ? C2 C3 C7 119.9(6) . . ? C4 C3 C7 120.9(6) . . ? C7 O4 Bi1 87.9(4) . 1_545 ? O6 C4 C3 123.4(6) . . ? O6 C4 C5 116.9(6) . . ? C3 C4 C5 119.7(6) . . ? C7 O5 Bi1 100.5(4) . 1_545 ? C6 C5 C4 120.8(7) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C4 O6 H1 109.5 . . ? C5 C6 C1 119.6(6) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? S2 O7 Bi1 138.9(3) . . ? O4 C7 O5 119.3(6) . . ? O4 C7 C3 123.2(6) . . ? O5 C7 C3 117.5(6) . . ? O4 C7 Bi1 66.1(3) . 1_545 ? O5 C7 Bi1 53.2(3) . 1_545 ? C3 C7 Bi1 170.7(5) . 1_545 ? C9 C8 C13 122.1(6) . . ? C9 C8 S2 119.0(5) . . ? C13 C8 S2 118.8(6) . . ? C8 C9 C10 119.2(6) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C14 O10 H10 109.5 . . ? C11 C10 C9 118.9(6) . . ? C11 C10 C14 120.4(6) . . ? C9 C10 C14 120.7(6) . . ? O12 C11 C12 115.9(6) . . ? O12 C11 C10 123.6(6) . . ? C12 C11 C10 120.4(6) . . ? C11 O12 H11 109.5 . . ? C13 C12 C11 119.2(7) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? Bi1 O13 H13A 102(5) . . ? Bi1 O13 H13B 116(5) . . ? H13A O13 H13B 90(7) . . ? C8 C13 C12 120.0(7) . . ? C8 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? Bi1 O14 H14A 119(6) . . ? Bi1 O14 H14B 117(3) . . ? H14A O14 H14B 106(8) . . ? O11 C14 O10 123.7(7) . . ? O11 C14 C10 121.4(7) . . ? O10 C14 C10 114.9(6) . . ? Bi1 O15 H15A 102(7) . . ? Bi1 O15 H15B 120(7) . . ? H15A O15 H15B 83(8) . . ? H16A O16 H16B 105(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O15 H15B O9 0.82(7) 1.89(7) 2.698(7) 174(9) 1_655 O13 H13B O11 0.82(5) 1.87(6) 2.676(7) 170(8) 2_567 O10 H10 O4 0.84 1.82 2.640(7) 166.4 2_557 O12 H11 O11 0.84 1.91 2.609(7) 140.1 . O14 H14B O8 0.82(5) 1.93(3) 2.696(8) 155(5) . O6 H1 O5 0.84 1.82 2.554(6) 145.7 . O14 H14A O16 0.81(4) 1.86(3) 2.649(10) 161(8) . O13 H13A O3 0.82(5) 2.46(4) 3.185(7) 148(7) 2_557 O15 H15A O3 0.81(9) 2.42(4) 3.199(8) 159(9) 2_657 O16 H16A O9 0.83(9) 2.35(11) 2.892(9) 124(11) 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.725 _refine_diff_density_min -1.320 _refine_diff_density_rms 0.157