# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'K.C.Kumara Swamy' _publ_contact_author_email kckssc@uohyd.ernet.in loop_ _publ_author_name 'K. C. Kumara Swamy' 'O. Anjaneyulu' D.Maddileti data_compound5 _database_code_depnum_ccdc_archive 'CCDC 825245' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Bi N3 O9' _chemical_formula_weight 701.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6708(10) _cell_length_b 11.4133(12) _cell_length_c 11.5410(12) _cell_angle_alpha 77.802(2) _cell_angle_beta 78.026(3) _cell_angle_gamma 72.353(2) _cell_volume 1172.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 7.581 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3124 _exptl_absorpt_correction_T_max 0.5177 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12596 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.41 _reflns_number_total 4774 _reflns_number_gt 4366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^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 4774 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0500 _refine_ls_wR_factor_gt 0.0489 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi Bi 0.499710(12) 0.137094(11) 0.087302(10) 0.04319(5) Uani 1 1 d . . . O1 O 0.5142(3) 0.3085(2) -0.0599(2) 0.0532(6) Uani 1 1 d . . . O2 O 0.4504(3) 0.4304(3) -0.2278(2) 0.0728(8) Uani 1 1 d . . . O3 O 0.2394(4) 0.4180(3) -0.3160(3) 0.0843(9) Uani 1 1 d . . . H3O H 0.3105 0.4411 -0.3123 0.126 Uiso 1 1 calc R . . O4 O 0.5921(3) 0.0147(2) 0.2697(2) 0.0575(6) Uani 1 1 d . . . O5 O 0.7514(4) -0.0329(3) 0.3978(3) 0.0782(8) Uani 1 1 d . . . O6 O 0.9387(3) 0.0935(3) 0.3693(3) 0.0835(9) Uani 1 1 d . . . H6O H 0.9039 0.0343 0.3960 0.125 Uiso 1 1 calc R . . O7 O 0.3572(3) -0.0165(3) 0.1758(2) 0.0666(7) Uani 1 1 d . . . O8 O 0.1702(3) -0.0987(3) 0.2001(2) 0.0661(7) Uani 1 1 d . . . O9 O 0.1323(3) -0.2612(3) 0.3804(3) 0.0718(7) Uani 1 1 d . . . H9O H 0.1160 -0.2138 0.3176 0.108 Uiso 1 1 calc R . . N1 N 0.2948(3) 0.1991(3) -0.0423(2) 0.0446(6) Uani 1 1 d . . . N2 N 0.7018(3) 0.2012(3) 0.1417(3) 0.0496(7) Uani 1 1 d . . . N3 N 0.4458(3) -0.1577(3) 0.3806(2) 0.0481(6) Uani 1 1 d . . . H3N H 0.4889 -0.1029 0.3397 0.058 Uiso 1 1 calc R . . C1 C 0.3472(3) 0.2666(3) 0.2077(3) 0.0435(7) Uani 1 1 d . . . C2 C 0.3348(4) 0.3918(4) 0.1802(4) 0.0654(10) Uani 1 1 d . . . H2 H 0.3885 0.4226 0.1101 0.078 Uiso 1 1 calc R . . C3 C 0.2435(5) 0.4731(4) 0.2552(4) 0.0829(13) Uani 1 1 d . . . H3 H 0.2362 0.5578 0.2356 0.099 Uiso 1 1 calc R . . C4 C 0.1641(4) 0.4282(4) 0.3580(4) 0.0729(11) Uani 1 1 d . . . H4 H 0.1016 0.4830 0.4078 0.087 Uiso 1 1 calc R . . C5 C 0.1758(4) 0.3038(4) 0.3882(3) 0.0625(10) Uani 1 1 d . . . H5 H 0.1220 0.2737 0.4587 0.075 Uiso 1 1 calc R . . C6 C 0.2681(4) 0.2222(4) 0.3134(3) 0.0531(8) Uani 1 1 d . . . H6 H 0.2769 0.1373 0.3345 0.064 Uiso 1 1 calc R . . C7 C 0.1882(4) 0.1451(3) -0.0343(3) 0.0488(8) Uani 1 1 d . . . H7 H 0.1756 0.0831 0.0304 0.059 Uiso 1 1 calc R . . C8 C 0.0951(4) 0.1785(4) -0.1200(3) 0.0594(9) Uani 1 1 d . . . H8 H 0.0226 0.1385 -0.1135 0.071 Uiso 1 1 calc R . . C9 C 0.1119(4) 0.2711(4) -0.2135(4) 0.0645(10) Uani 1 1 d . . . H9 H 0.0497 0.2955 -0.2710 0.077 Uiso 1 1 calc R . . C10 C 0.2215(4) 0.3286(3) -0.2229(3) 0.0550(9) Uani 1 1 d . . . C11 C 0.3119(4) 0.2901(3) -0.1349(3) 0.0444(7) Uani 1 1 d . . . C12 C 0.4333(4) 0.3475(3) -0.1418(3) 0.0508(8) Uani 1 1 d . . . C13 C 0.7504(4) 0.2962(4) 0.0803(4) 0.0613(10) Uani 1 1 d . . . H13 H 0.7081 0.3426 0.0137 0.074 Uiso 1 1 calc R . . C14 C 0.8632(5) 0.3286(5) 0.1124(4) 0.0769(12) Uani 1 1 d . . . H14 H 0.8951 0.3964 0.0686 0.092 Uiso 1 1 calc R . . C15 C 0.9257(4) 0.2601(5) 0.2083(4) 0.0775(13) Uani 1 1 d . . . H15 H 1.0012 0.2809 0.2307 0.093 Uiso 1 1 calc R . . C16 C 0.8782(4) 0.1598(4) 0.2729(4) 0.0637(10) Uani 1 1 d . . . C17 C 0.7621(4) 0.1327(3) 0.2383(3) 0.0497(8) Uani 1 1 d . . . C18 C 0.6992(4) 0.0302(4) 0.3078(3) 0.0533(9) Uani 1 1 d . . . C19 C 0.5006(4) -0.2288(4) 0.4765(3) 0.0603(9) Uani 1 1 d . . . H19 H 0.5835 -0.2194 0.4984 0.072 Uiso 1 1 calc R . . C20 C 0.4324(5) -0.3163(4) 0.5426(4) 0.0698(11) Uani 1 1 d . . . H20 H 0.4698 -0.3673 0.6096 0.084 Uiso 1 1 calc R . . C21 C 0.3109(5) -0.3288(4) 0.5109(4) 0.0654(10) Uani 1 1 d . . . H21 H 0.2657 -0.3887 0.5558 0.078 Uiso 1 1 calc R . . C22 C 0.2539(4) -0.2523(3) 0.4115(3) 0.0528(8) Uani 1 1 d . . . C23 C 0.3267(4) -0.1669(3) 0.3443(3) 0.0438(7) Uani 1 1 d . . . C24 C 0.2800(4) -0.0860(3) 0.2312(3) 0.0477(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.04623(8) 0.04533(8) 0.04156(8) -0.00258(5) -0.01427(5) -0.01553(5) O1 0.0555(14) 0.0583(14) 0.0512(13) 0.0024(11) -0.0153(11) -0.0261(11) O2 0.0866(19) 0.0694(18) 0.0648(17) 0.0216(14) -0.0207(15) -0.0407(16) O3 0.101(2) 0.082(2) 0.0682(18) 0.0320(16) -0.0409(17) -0.0332(18) O4 0.0568(15) 0.0623(16) 0.0591(15) 0.0069(12) -0.0282(12) -0.0229(12) O5 0.084(2) 0.088(2) 0.0669(18) 0.0054(16) -0.0426(16) -0.0210(17) O6 0.0651(18) 0.114(3) 0.084(2) -0.0198(18) -0.0365(17) -0.0230(17) O7 0.0829(18) 0.0745(18) 0.0560(15) 0.0183(13) -0.0346(14) -0.0449(15) O8 0.0762(17) 0.0707(17) 0.0659(16) 0.0065(13) -0.0365(14) -0.0360(14) O9 0.0809(19) 0.074(2) 0.0723(19) 0.0079(14) -0.0227(15) -0.0437(16) N1 0.0467(15) 0.0483(16) 0.0398(14) -0.0002(12) -0.0126(12) -0.0152(12) N2 0.0436(15) 0.0563(18) 0.0526(16) -0.0095(14) -0.0112(13) -0.0157(13) N3 0.0543(16) 0.0490(16) 0.0430(15) -0.0016(12) -0.0156(13) -0.0155(13) C1 0.0382(16) 0.055(2) 0.0412(17) -0.0076(14) -0.0115(13) -0.0141(14) C2 0.071(3) 0.054(2) 0.062(2) -0.0049(18) 0.0050(19) -0.0162(19) C3 0.090(3) 0.064(3) 0.082(3) -0.015(2) 0.005(3) -0.012(2) C4 0.058(2) 0.082(3) 0.071(3) -0.027(2) 0.001(2) -0.005(2) C5 0.051(2) 0.088(3) 0.048(2) -0.007(2) -0.0069(16) -0.022(2) C6 0.052(2) 0.063(2) 0.0487(19) -0.0034(17) -0.0156(16) -0.0201(17) C7 0.0477(18) 0.0509(19) 0.0503(19) -0.0010(15) -0.0160(15) -0.0163(15) C8 0.052(2) 0.065(2) 0.067(2) -0.0049(19) -0.0268(18) -0.0166(18) C9 0.064(2) 0.067(2) 0.064(2) 0.0031(19) -0.036(2) -0.012(2) C10 0.064(2) 0.051(2) 0.0472(19) 0.0044(16) -0.0207(17) -0.0118(17) C11 0.0501(18) 0.0410(17) 0.0400(17) -0.0011(14) -0.0120(14) -0.0095(14) C12 0.054(2) 0.0448(19) 0.051(2) -0.0035(16) -0.0075(16) -0.0128(16) C13 0.046(2) 0.071(3) 0.073(3) -0.011(2) -0.0105(18) -0.0239(18) C14 0.066(3) 0.093(3) 0.087(3) -0.014(3) -0.014(2) -0.042(2) C15 0.055(2) 0.104(4) 0.090(3) -0.029(3) -0.015(2) -0.035(2) C16 0.049(2) 0.084(3) 0.068(2) -0.029(2) -0.0167(18) -0.014(2) C17 0.0404(17) 0.061(2) 0.0521(19) -0.0192(17) -0.0094(15) -0.0122(15) C18 0.0494(19) 0.059(2) 0.052(2) -0.0125(17) -0.0194(16) -0.0061(16) C19 0.068(2) 0.064(2) 0.050(2) 0.0001(18) -0.0266(18) -0.0148(19) C20 0.085(3) 0.063(3) 0.050(2) 0.0115(19) -0.022(2) -0.011(2) C21 0.078(3) 0.055(2) 0.057(2) 0.0131(18) -0.015(2) -0.022(2) C22 0.063(2) 0.046(2) 0.049(2) -0.0041(16) -0.0094(17) -0.0179(17) C23 0.0512(18) 0.0384(17) 0.0426(17) -0.0054(14) -0.0142(14) -0.0094(14) C24 0.059(2) 0.0437(18) 0.0436(18) -0.0025(14) -0.0136(15) -0.0177(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi C1 2.233(3) . ? Bi O1 2.323(2) . ? Bi O4 2.442(2) . ? Bi O7 2.478(2) . ? Bi N2 2.513(3) . ? Bi N1 2.568(3) . ? O1 C12 1.274(4) . ? O2 C12 1.239(4) . ? O3 C10 1.339(5) . ? O3 H3O 0.8200 . ? O4 C18 1.276(4) . ? O5 C18 1.238(4) . ? O6 C16 1.341(5) . ? O6 H6O 0.8200 . ? O7 C24 1.242(4) . ? O8 C24 1.245(4) . ? O9 C22 1.336(5) . ? O9 H9O 0.8200 . ? N1 C7 1.332(4) . ? N1 C11 1.346(4) . ? N2 C13 1.321(5) . ? N2 C17 1.349(4) . ? N3 C19 1.329(4) . ? N3 C23 1.344(4) . ? N3 H3N 0.8600 . ? C1 C2 1.370(5) . ? C1 C6 1.385(5) . ? C2 C3 1.384(6) . ? C2 H2 0.9300 . ? C3 C4 1.364(6) . ? C3 H3 0.9300 . ? C4 C5 1.365(6) . ? C4 H4 0.9300 . ? C5 C6 1.387(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.391(5) . ? C7 H7 0.9300 . ? C8 C9 1.363(5) . ? C8 H8 0.9300 . ? C9 C10 1.382(5) . ? C9 H9 0.9300 . ? C10 C11 1.391(5) . ? C11 C12 1.490(5) . ? C13 C14 1.391(5) . ? C13 H13 0.9300 . ? C14 C15 1.351(6) . ? C14 H14 0.9300 . ? C15 C16 1.376(6) . ? C15 H15 0.9300 . ? C16 C17 1.402(5) . ? C17 C18 1.489(5) . ? C19 C20 1.372(6) . ? C19 H19 0.9300 . ? C20 C21 1.356(6) . ? C20 H20 0.9300 . ? C21 C22 1.390(5) . ? C21 H21 0.9300 . ? C22 C23 1.385(5) . ? C23 C24 1.498(4) . ? 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 C1 Bi O1 88.72(10) . . ? C1 Bi O4 85.48(10) . . ? O1 Bi O4 144.10(8) . . ? C1 Bi O7 88.74(11) . . ? O1 Bi O7 144.45(8) . . ? O4 Bi O7 70.88(8) . . ? C1 Bi N2 85.89(10) . . ? O1 Bi N2 78.58(9) . . ? O4 Bi N2 65.69(9) . . ? O7 Bi N2 136.51(9) . . ? C1 Bi N1 86.88(10) . . ? O1 Bi N1 67.49(8) . . ? O4 Bi N1 147.06(9) . . ? O7 Bi N1 76.97(8) . . ? N2 Bi N1 145.42(9) . . ? C12 O1 Bi 123.2(2) . . ? C10 O3 H3O 109.5 . . ? C18 O4 Bi 123.0(2) . . ? C16 O6 H6O 109.5 . . ? C24 O7 Bi 172.7(3) . . ? C22 O9 H9O 109.5 . . ? C7 N1 C11 119.1(3) . . ? C7 N1 Bi 128.1(2) . . ? C11 N1 Bi 112.4(2) . . ? C13 N2 C17 119.8(3) . . ? C13 N2 Bi 123.3(2) . . ? C17 N2 Bi 116.9(2) . . ? C19 N3 C23 123.5(3) . . ? C19 N3 H3N 118.3 . . ? C23 N3 H3N 118.3 . . ? C2 C1 C6 118.6(3) . . ? C2 C1 Bi 120.2(2) . . ? C6 C1 Bi 121.1(3) . . ? C1 C2 C3 121.0(4) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.5(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.4(4) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1 C7 C8 122.0(3) . . ? N1 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C9 C8 C7 118.8(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? O3 C10 C9 119.8(3) . . ? O3 C10 C11 121.8(4) . . ? C9 C10 C11 118.4(3) . . ? N1 C11 C10 121.7(3) . . ? N1 C11 C12 117.7(3) . . ? C10 C11 C12 120.6(3) . . ? O2 C12 O1 123.6(3) . . ? O2 C12 C11 117.9(3) . . ? O1 C12 C11 118.5(3) . . ? N2 C13 C14 121.8(4) . . ? N2 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C15 C14 C13 119.1(4) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.3(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O6 C16 C15 120.1(4) . . ? O6 C16 C17 121.4(4) . . ? C15 C16 C17 118.4(4) . . ? N2 C17 C16 120.6(4) . . ? N2 C17 C18 117.9(3) . . ? C16 C17 C18 121.5(3) . . ? O5 C18 O4 124.5(4) . . ? O5 C18 C17 119.1(3) . . ? O4 C18 C17 116.4(3) . . ? N3 C19 C20 118.7(4) . . ? N3 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C21 C20 C19 120.4(4) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.1(4) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? O9 C22 C23 120.5(3) . . ? O9 C22 C21 121.0(3) . . ? C23 C22 C21 118.5(4) . . ? N3 C23 C22 118.8(3) . . ? N3 C23 C24 118.5(3) . . ? C22 C23 C24 122.6(3) . . ? O7 C24 O8 126.6(3) . . ? O7 C24 C23 116.9(3) . . ? O8 C24 C23 116.4(3) . . ? 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 O9 H9O O8 0.82 1.79 2.524(4) 147.8 . O6 H6O O5 0.82 1.85 2.571(5) 145.6 . O3 H3O O2 0.82 1.79 2.514(4) 146.9 . N3 H3N O4 0.86 1.86 2.717(4) 172.3 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.825 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.092 #===END data_compound7 _database_code_depnum_ccdc_archive 'CCDC 825246' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H27 Bi N6 O12' _chemical_formula_weight 920.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9818(12) _cell_length_b 13.8686(16) _cell_length_c 13.9078(16) _cell_angle_alpha 73.185(2) _cell_angle_beta 70.121(2) _cell_angle_gamma 70.084(2) _cell_volume 1669.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.832 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 5.358 _exptl_absorpt_correction_T_min 0.6164 _exptl_absorpt_correction_T_max 0.6164 _exptl_absorpt_process_details 'SADABS, Sheldrick (1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 16124 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.04 _reflns_number_total 5870 _reflns_number_gt 5420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0334P)^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 5870 _refine_ls_number_parameters 494 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0584 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Bi Bi 0.258101(14) 0.247700(9) 0.758427(9) 0.03783(6) Uani 1 1 d . . . O8 O 0.4497(3) 0.4902(2) 0.7713(3) 0.0717(9) Uani 1 1 d . . . O7 O 0.3574(3) 0.3540(2) 0.81536(19) 0.0509(7) Uani 1 1 d . . . O2 O -0.2067(3) 0.3484(2) 0.7448(2) 0.0542(7) Uani 1 1 d . . . O4 O 0.3308(3) 0.1971(2) 0.59460(19) 0.0506(6) Uani 1 1 d . . . O5 O 0.5033(3) 0.1231(2) 0.4660(2) 0.0649(8) Uani 1 1 d . . . O11 O 0.2857(4) -0.0001(2) 1.0616(2) 0.0692(9) Uani 1 1 d . . . O10 O 0.3124(3) 0.1347(2) 0.9319(2) 0.0538(7) Uani 1 1 d . . . O9 O 0.4173(5) 0.6282(3) 0.6076(4) 0.0978(14) Uani 1 1 d . . . O3 O -0.3592(3) 0.4359(2) 0.9028(2) 0.0585(8) Uani 1 1 d . . . O12 O 0.1776(4) -0.1371(2) 1.0521(2) 0.0708(9) Uani 1 1 d . . . O6 O 0.7723(4) 0.0540(3) 0.4690(3) 0.0709(9) Uani 1 1 d . . . O1 O 0.0368(3) 0.28375(19) 0.71449(19) 0.0480(6) Uani 1 1 d . . . N1 N 0.0303(3) 0.3342(2) 0.8902(2) 0.0414(7) Uani 1 1 d . . . N3 N 0.2576(4) 0.4189(2) 0.6432(2) 0.0488(8) Uani 1 1 d . . . N4 N 0.2117(4) 0.0612(2) 0.8159(2) 0.0461(8) Uani 1 1 d . . . N2 N 0.5410(3) 0.1825(2) 0.6844(2) 0.0424(7) Uani 1 1 d . . . C2 C -0.2311(4) 0.4099(3) 0.9267(3) 0.0445(9) Uani 1 1 d . . . C3 C -0.2294(5) 0.4348(3) 1.0159(3) 0.0517(10) Uani 1 1 d . . . H3 H -0.3165 0.4692 1.0585 0.062 Uiso 1 1 calc R . . C4 C -0.0990(5) 0.4085(3) 1.0402(3) 0.0556(11) Uani 1 1 d . . . H4 H -0.0963 0.4244 1.0999 0.067 Uiso 1 1 calc R . . C5 C 0.0288(5) 0.3584(3) 0.9760(3) 0.0511(10) Uani 1 1 d . . . H5 H 0.1173 0.3409 0.9935 0.061 Uiso 1 1 calc R . . C1 C -0.0978(4) 0.3583(3) 0.8651(3) 0.0388(8) Uani 1 1 d . . . C6 C -0.0893(4) 0.3275(3) 0.7680(3) 0.0414(9) Uani 1 1 d . . . C16 C 0.2193(7) 0.5436(4) 0.4916(4) 0.0827(16) Uani 1 1 d . . . H16 H 0.1809 0.5654 0.4342 0.099 Uiso 1 1 calc R . . C17 C 0.2030(6) 0.4506(4) 0.5609(3) 0.0669(13) Uani 1 1 d . . . H17 H 0.1538 0.4104 0.5497 0.080 Uiso 1 1 calc R . . C15 C 0.2899(6) 0.6017(4) 0.5072(4) 0.0787(16) Uani 1 1 d . . . H15 H 0.3002 0.6638 0.4606 0.094 Uiso 1 1 calc R . . C14 C 0.3479(5) 0.5702(3) 0.5924(4) 0.0658(13) Uani 1 1 d . . . C13 C 0.3289(4) 0.4773(3) 0.6600(3) 0.0468(9) Uani 1 1 d . . . C18 C 0.3830(4) 0.4375(3) 0.7558(3) 0.0477(9) Uani 1 1 d . . . C19 C 0.2172(4) 0.0078(3) 0.9133(3) 0.0408(8) Uani 1 1 d . . . C24 C 0.2762(4) 0.0503(3) 0.9732(3) 0.0470(10) Uani 1 1 d . . . C20 C 0.1736(5) -0.0841(3) 0.9556(3) 0.0495(10) Uani 1 1 d . . . C21 C 0.1215(5) -0.1199(4) 0.8944(4) 0.0624(12) Uani 1 1 d . . . H21 H 0.0890 -0.1801 0.9208 0.075 Uiso 1 1 calc R . . C22 C 0.1190(5) -0.0664(3) 0.7973(4) 0.0624(12) Uani 1 1 d . . . H22 H 0.0865 -0.0906 0.7557 0.075 Uiso 1 1 calc R . . C23 C 0.1647(5) 0.0246(3) 0.7586(3) 0.0548(11) Uani 1 1 d . . . H23 H 0.1622 0.0608 0.6912 0.066 Uiso 1 1 calc R . . C12 C 0.4632(5) 0.1547(3) 0.5496(3) 0.0474(10) Uani 1 1 d . . . C7 C 0.5827(4) 0.1421(3) 0.5982(3) 0.0409(9) Uani 1 1 d . . . C8 C 0.7303(5) 0.0939(3) 0.5557(3) 0.0504(10) Uani 1 1 d . . . C9 C 0.8351(5) 0.0869(3) 0.6045(3) 0.0554(11) Uani 1 1 d . . . H9 H 0.9340 0.0528 0.5791 0.066 Uiso 1 1 calc R . . C10 C 0.7911(4) 0.1305(3) 0.6893(3) 0.0537(11) Uani 1 1 d . . . H10 H 0.8604 0.1291 0.7209 0.064 Uiso 1 1 calc R . . C11 C 0.6433(4) 0.1770(3) 0.7289(3) 0.0509(10) Uani 1 1 d . . . H11 H 0.6140 0.2054 0.7881 0.061 Uiso 1 1 calc R . . C30 C 0.4906(5) 0.2282(4) 0.2137(4) 0.0642(13) Uani 1 1 d . . . H30 H 0.5197 0.2466 0.2612 0.077 Uiso 1 1 calc R . . C34 C 0.4847(6) 0.2916(4) 0.1201(4) 0.0660(13) Uani 1 1 d . . . H34 H 0.5088 0.3547 0.1030 0.079 Uiso 1 1 calc R . . C33 C 0.4436(5) 0.2633(4) 0.0509(4) 0.0673(13) Uani 1 1 d . . . H33 H 0.4400 0.3072 -0.0135 0.081 Uiso 1 1 calc R . . C32 C 0.4093(4) 0.1757(3) 0.0739(3) 0.0419(9) Uani 1 1 d . . . H32 H 0.3822 0.1579 0.0250 0.050 Uiso 1 1 calc R . . C31 C 0.4113(5) 0.1123(4) 0.1624(4) 0.0694(14) Uani 1 1 d . . . H31 H 0.3849 0.0505 0.1762 0.083 Uiso 1 1 calc R . . N6 N 0.4526(6) 0.1355(4) 0.2374(4) 0.0921(15) Uani 1 1 d . . . H6 H 0.4543 0.0936 0.2965 0.110 Uiso 1 1 calc R . . N5 N 0.0380(8) 0.2118(6) 0.3556(6) 0.134(2) Uani 1 1 d . . . C25 C 0.1170(7) 0.2190(5) 0.4165(4) 0.0938(19) Uani 1 1 d . . . H25 H 0.1334 0.1673 0.4743 0.113 Uiso 1 1 calc R . . C26 C 0.1704(7) 0.3049(5) 0.3889(5) 0.098(2) Uani 1 1 d . . . H26 H 0.2274 0.3128 0.4255 0.118 Uiso 1 1 calc R . . C27 C 0.1358(8) 0.3784(5) 0.3048(6) 0.109(2) Uani 1 1 d . . . H27 H 0.1686 0.4382 0.2857 0.131 Uiso 1 1 calc R . . C28 C 0.0607(7) 0.3695(5) 0.2512(4) 0.0833(17) Uani 1 1 d . . . H28 H 0.0395 0.4222 0.1951 0.100 Uiso 1 1 calc R . . C29 C 0.0173(8) 0.2924(6) 0.2734(5) 0.099(2) Uani 1 1 d . . . H29 H -0.0343 0.2876 0.2313 0.119 Uiso 1 1 calc R . . H3O H -0.336(5) 0.408(3) 0.843(4) 0.075(15) Uiso 1 1 d . . . H60 H 0.689(5) 0.068(4) 0.451(4) 0.081(17) Uiso 1 1 d . . . H9O H 0.435(5) 0.600(4) 0.668(4) 0.065(17) Uiso 1 1 d . . . H12O H 0.232(6) -0.106(4) 1.070(4) 0.12(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.04231(10) 0.03921(9) 0.03082(9) -0.00291(6) -0.01281(6) -0.00988(6) O8 0.072(2) 0.080(2) 0.084(2) -0.0283(18) -0.0253(18) -0.0318(18) O7 0.0570(17) 0.0580(17) 0.0406(15) -0.0066(13) -0.0192(13) -0.0156(14) O2 0.0507(17) 0.0705(19) 0.0458(16) -0.0130(14) -0.0222(14) -0.0113(14) O4 0.0480(16) 0.0641(17) 0.0412(15) -0.0114(13) -0.0170(13) -0.0111(14) O5 0.074(2) 0.078(2) 0.0501(17) -0.0289(16) -0.0210(16) -0.0116(17) O11 0.103(2) 0.067(2) 0.0444(17) 0.0084(14) -0.0371(17) -0.0289(18) O10 0.0729(19) 0.0507(17) 0.0469(16) 0.0021(13) -0.0306(14) -0.0229(15) O9 0.117(3) 0.068(3) 0.116(4) 0.000(2) -0.028(3) -0.052(2) O3 0.0421(16) 0.076(2) 0.0557(18) -0.0214(16) -0.0161(14) -0.0042(14) O12 0.100(3) 0.0574(19) 0.0534(19) 0.0095(15) -0.0232(19) -0.0338(19) O6 0.061(2) 0.088(2) 0.061(2) -0.0421(18) -0.0092(17) -0.0002(18) O1 0.0460(15) 0.0585(16) 0.0409(14) -0.0156(13) -0.0163(12) -0.0062(13) N1 0.0437(18) 0.0471(18) 0.0387(17) -0.0089(14) -0.0171(15) -0.0121(14) N3 0.065(2) 0.0444(19) 0.0375(17) 0.0008(14) -0.0215(16) -0.0152(16) N4 0.055(2) 0.0442(19) 0.0416(18) -0.0052(15) -0.0190(16) -0.0126(15) N2 0.0463(18) 0.0451(18) 0.0340(16) -0.0073(14) -0.0117(15) -0.0097(15) C2 0.044(2) 0.044(2) 0.044(2) -0.0034(17) -0.0123(18) -0.0143(18) C3 0.054(3) 0.055(3) 0.043(2) -0.0131(19) -0.008(2) -0.013(2) C4 0.070(3) 0.063(3) 0.043(2) -0.016(2) -0.017(2) -0.021(2) C5 0.052(3) 0.062(3) 0.049(2) -0.014(2) -0.021(2) -0.017(2) C1 0.049(2) 0.0348(19) 0.0342(19) -0.0008(15) -0.0143(17) -0.0154(17) C6 0.049(2) 0.038(2) 0.037(2) 0.0000(16) -0.0156(19) -0.0140(18) C16 0.117(5) 0.069(3) 0.046(3) 0.010(2) -0.034(3) -0.011(3) C17 0.096(4) 0.059(3) 0.048(3) 0.003(2) -0.038(3) -0.017(3) C15 0.100(4) 0.054(3) 0.059(3) 0.012(2) -0.016(3) -0.017(3) C14 0.068(3) 0.045(3) 0.072(3) -0.008(2) -0.004(3) -0.018(2) C13 0.048(2) 0.044(2) 0.044(2) -0.0105(18) -0.0068(19) -0.0100(18) C18 0.040(2) 0.055(3) 0.047(2) -0.019(2) -0.0077(18) -0.0081(19) C19 0.042(2) 0.038(2) 0.038(2) -0.0054(16) -0.0095(17) -0.0079(17) C24 0.050(2) 0.049(2) 0.041(2) -0.0048(18) -0.0155(19) -0.0104(19) C20 0.052(2) 0.042(2) 0.045(2) -0.0035(18) -0.0064(19) -0.0112(19) C21 0.074(3) 0.048(3) 0.070(3) -0.008(2) -0.017(3) -0.027(2) C22 0.071(3) 0.060(3) 0.072(3) -0.019(2) -0.027(3) -0.024(2) C23 0.066(3) 0.058(3) 0.050(2) -0.008(2) -0.026(2) -0.019(2) C12 0.060(3) 0.043(2) 0.039(2) -0.0028(18) -0.017(2) -0.015(2) C7 0.049(2) 0.037(2) 0.0342(19) -0.0039(16) -0.0110(17) -0.0109(17) C8 0.054(3) 0.045(2) 0.045(2) -0.0097(18) -0.009(2) -0.0062(19) C9 0.042(2) 0.060(3) 0.054(3) -0.012(2) -0.010(2) -0.004(2) C10 0.046(2) 0.066(3) 0.049(2) -0.009(2) -0.018(2) -0.011(2) C11 0.054(3) 0.061(3) 0.039(2) -0.0073(19) -0.0189(19) -0.012(2) C30 0.066(3) 0.076(3) 0.062(3) -0.027(3) -0.016(2) -0.023(3) C34 0.073(3) 0.064(3) 0.066(3) -0.012(2) -0.013(3) -0.030(3) C33 0.061(3) 0.087(4) 0.047(3) -0.010(2) -0.018(2) -0.011(3) C32 0.044(2) 0.050(2) 0.037(2) -0.0138(18) -0.0156(18) -0.0098(18) C31 0.065(3) 0.065(3) 0.088(4) -0.033(3) -0.017(3) -0.020(3) N6 0.090(3) 0.100(4) 0.071(3) -0.018(3) -0.018(3) -0.009(3) N5 0.134(6) 0.140(6) 0.143(6) -0.038(5) -0.036(5) -0.045(4) C25 0.102(5) 0.087(4) 0.065(4) 0.010(3) -0.028(3) -0.008(4) C26 0.091(4) 0.114(5) 0.103(5) -0.060(4) -0.035(4) -0.002(4) C27 0.113(5) 0.052(3) 0.127(6) -0.001(4) -0.012(5) -0.015(3) C28 0.101(5) 0.071(4) 0.071(4) 0.026(3) -0.043(3) -0.028(3) C29 0.119(5) 0.116(6) 0.079(4) 0.001(4) -0.061(4) -0.035(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi O1 2.343(2) . ? Bi O4 2.380(3) . ? Bi O7 2.447(3) . ? Bi N3 2.449(3) . ? Bi N1 2.559(3) . ? Bi N2 2.583(3) . ? Bi O10 2.587(2) . ? Bi N4 2.630(3) . ? O8 C18 1.242(5) . ? O7 C18 1.263(4) . ? O2 C6 1.238(4) . ? O4 C12 1.267(5) . ? O5 C12 1.250(5) . ? O11 C24 1.243(4) . ? O10 C24 1.260(5) . ? O9 C14 1.323(6) . ? O9 H9O 0.87(4) . ? O3 C2 1.335(5) . ? O3 H3O 0.94(4) . ? O12 C20 1.337(5) . ? O12 H12O 0.93(5) . ? O6 C8 1.348(5) . ? O6 H60 0.89(5) . ? O1 C6 1.269(4) . ? N1 C5 1.324(5) . ? N1 C1 1.347(5) . ? N3 C17 1.330(5) . ? N3 C13 1.354(5) . ? N4 C23 1.327(5) . ? N4 C19 1.353(5) . ? N2 C11 1.334(5) . ? N2 C7 1.346(4) . ? C2 C3 1.387(6) . ? C2 C1 1.396(5) . ? C3 C4 1.358(6) . ? C3 H3 0.9300 . ? C4 C5 1.374(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C1 C6 1.499(5) . ? C16 C15 1.336(7) . ? C16 C17 1.391(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C15 C14 1.387(7) . ? C15 H15 0.9300 . ? C14 C13 1.387(6) . ? C13 C18 1.494(5) . ? C19 C20 1.388(5) . ? C19 C24 1.499(5) . ? C20 C21 1.401(6) . ? C21 C22 1.344(6) . ? C21 H21 0.9300 . ? C22 C23 1.387(6) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C12 C7 1.500(5) . ? C7 C8 1.390(5) . ? C8 C9 1.393(6) . ? C9 C10 1.353(6) . ? C9 H9 0.9300 . ? C10 C11 1.379(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C30 C34 1.351(7) . ? C30 N6 1.381(7) . ? C30 H30 0.9300 . ? C34 C33 1.358(7) . ? C34 H34 0.9300 . ? C33 C32 1.296(6) . ? C33 H33 0.9300 . ? C32 C31 1.291(6) . ? C32 H32 0.9300 . ? C31 N6 1.393(7) . ? C31 H31 0.9300 . ? N6 H6 0.8600 . ? N5 C29 1.365(8) . ? N5 C25 1.380(8) . ? C25 C26 1.371(8) . ? C25 H25 0.9300 . ? C26 C27 1.368(8) . ? C26 H26 0.9300 . ? C27 C28 1.277(9) . ? C27 H27 0.9300 . ? C28 C29 1.208(8) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? 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 Bi O4 74.99(9) . . ? O1 Bi O7 131.82(8) . . ? O4 Bi O7 129.41(9) . . ? O1 Bi N3 80.54(10) . . ? O4 Bi N3 80.75(10) . . ? O7 Bi N3 66.98(9) . . ? O1 Bi N1 66.81(9) . . ? O4 Bi N1 141.67(9) . . ? O7 Bi N1 78.11(9) . . ? N3 Bi N1 89.82(10) . . ? O1 Bi N2 140.94(9) . . ? O4 Bi N2 66.04(9) . . ? O7 Bi N2 76.00(9) . . ? N3 Bi N2 90.46(10) . . ? N1 Bi N2 151.69(9) . . ? O1 Bi O10 125.05(9) . . ? O4 Bi O10 128.12(9) . . ? O7 Bi O10 76.21(8) . . ? N3 Bi O10 143.04(9) . . ? N1 Bi O10 79.34(9) . . ? N2 Bi O10 83.56(9) . . ? O1 Bi N4 78.98(9) . . ? O4 Bi N4 78.66(9) . . ? O7 Bi N4 138.97(9) . . ? N3 Bi N4 154.03(10) . . ? N1 Bi N4 96.58(10) . . ? N2 Bi N4 95.45(10) . . ? O10 Bi N4 62.89(8) . . ? C18 O7 Bi 119.6(2) . . ? C12 O4 Bi 123.7(2) . . ? C24 O10 Bi 122.1(2) . . ? C14 O9 H9O 106(3) . . ? C2 O3 H3O 105(3) . . ? C20 O12 H12O 103(3) . . ? C8 O6 H60 105(3) . . ? C6 O1 Bi 124.0(2) . . ? C5 N1 C1 119.2(3) . . ? C5 N1 Bi 126.6(3) . . ? C1 N1 Bi 114.3(2) . . ? C17 N3 C13 120.0(4) . . ? C17 N3 Bi 122.5(3) . . ? C13 N3 Bi 117.2(2) . . ? C23 N4 C19 119.4(3) . . ? C23 N4 Bi 122.2(3) . . ? C19 N4 Bi 117.8(2) . . ? C11 N2 C7 119.4(3) . . ? C11 N2 Bi 125.9(3) . . ? C7 N2 Bi 114.4(2) . . ? O3 C2 C3 119.2(4) . . ? O3 C2 C1 122.4(3) . . ? C3 C2 C1 118.4(4) . . ? C4 C3 C2 119.2(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.7(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 122.3(4) . . ? N1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? N1 C1 C2 121.2(3) . . ? N1 C1 C6 116.7(3) . . ? C2 C1 C6 122.1(3) . . ? O2 C6 O1 124.6(3) . . ? O2 C6 C1 117.2(3) . . ? O1 C6 C1 118.2(3) . . ? C15 C16 C17 120.2(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? N3 C17 C16 120.3(5) . . ? N3 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C16 C15 C14 120.5(5) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? O9 C14 C15 120.3(5) . . ? O9 C14 C13 122.2(5) . . ? C15 C14 C13 117.6(5) . . ? N3 C13 C14 121.4(4) . . ? N3 C13 C18 116.5(3) . . ? C14 C13 C18 122.1(4) . . ? O8 C18 O7 124.7(4) . . ? O8 C18 C13 116.9(4) . . ? O7 C18 C13 118.4(3) . . ? N4 C19 C20 121.7(4) . . ? N4 C19 C24 117.2(3) . . ? C20 C19 C24 121.1(3) . . ? O11 C24 O10 123.9(4) . . ? O11 C24 C19 117.5(4) . . ? O10 C24 C19 118.6(3) . . ? O12 C20 C19 122.2(4) . . ? O12 C20 C21 119.9(4) . . ? C19 C20 C21 117.8(4) . . ? C22 C21 C20 119.5(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? N4 C23 C22 121.3(4) . . ? N4 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? O5 C12 O4 124.9(4) . . ? O5 C12 C7 116.7(4) . . ? O4 C12 C7 118.4(3) . . ? N2 C7 C8 121.0(3) . . ? N2 C7 C12 116.7(3) . . ? C8 C7 C12 122.2(3) . . ? O6 C8 C7 121.1(4) . . ? O6 C8 C9 120.1(4) . . ? C7 C8 C9 118.8(4) . . ? C10 C9 C8 119.1(4) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N2 C11 C10 121.8(4) . . ? N2 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C34 C30 N6 118.7(5) . . ? C34 C30 H30 120.7 . . ? N6 C30 H30 120.7 . . ? C30 C34 C33 120.2(5) . . ? C30 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C32 C33 C34 120.5(4) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C31 C32 C33 122.3(4) . . ? C31 C32 H32 118.8 . . ? C33 C32 H32 118.8 . . ? C32 C31 N6 120.7(5) . . ? C32 C31 H31 119.7 . . ? N6 C31 H31 119.7 . . ? C30 N6 C31 117.7(5) . . ? C30 N6 H6 121.2 . . ? C31 N6 H6 121.2 . . ? C29 N5 C25 116.8(6) . . ? C26 C25 N5 117.9(6) . . ? C26 C25 H25 121.1 . . ? N5 C25 H25 121.1 . . ? C27 C26 C25 116.6(6) . . ? C27 C26 H26 121.7 . . ? C25 C26 H26 121.7 . . ? C28 C27 C26 123.6(6) . . ? C28 C27 H27 118.2 . . ? C26 C27 H27 118.2 . . ? C29 C28 C27 119.9(6) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 N5 125.2(6) . . ? C28 C29 H29 117.4 . . ? N5 C29 H29 117.4 . . ? 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 O3 H3O O8 0.94(4) 2.45(4) 2.854(4) 106(3) 1_455 O3 H3O O2 0.94(4) 1.72(5) 2.574(4) 150(4) . O6 H60 O5 0.89(5) 1.71(5) 2.536(4) 153(5) . O9 H9O O8 0.87(4) 1.77(4) 2.552(5) 149(5) . O12 H12O O11 0.93(5) 1.68(5) 2.536(4) 150(5) . N6 H6 O5 0.86 2.73 3.332(6) 128.6 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.752 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.080 #===END data_compound8 _database_code_depnum_ccdc_archive 'CCDC 825247' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Bi N6 O7' _chemical_formula_weight 674.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.571(2) _cell_length_b 10.2872(8) _cell_length_c 17.0803(13) _cell_angle_alpha 90.00 _cell_angle_beta 109.0150(10) _cell_angle_gamma 90.00 _cell_volume 4580.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.956 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 7.755 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2576 _exptl_absorpt_correction_T_max 0.3358 _exptl_absorpt_process_details 'SADABS, Sheldrick (1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'not applicable' _diffrn_standards_interval_count 'not applicable' _diffrn_standards_interval_time 'not applicable' _diffrn_standards_decay_% none _diffrn_reflns_number 21163 _diffrn_reflns_av_R_equivalents 0.2527 _diffrn_reflns_av_sigmaI/netI 0.1195 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4001 _reflns_number_gt 3538 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^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 4001 _refine_ls_number_parameters 325 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1314 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Bi Bi 0.095788(9) 0.07279(2) 0.704406(12) 0.03046(17) Uani 1 1 d . . . O5 O 0.13916(18) 0.2238(5) 0.8082(3) 0.0373(11) Uani 1 1 d . . . N3 N 0.1421(3) -0.0737(5) 0.8328(4) 0.0355(14) Uani 1 1 d . . . O1 O 0.0764(2) 0.2623(4) 0.6180(3) 0.0430(12) Uani 1 1 d . . . O3 O 0.0817(2) -0.1638(6) 0.6840(3) 0.0557(14) Uani 1 1 d . . . O6 O 0.06657(18) 0.3310(5) 0.7982(3) 0.0433(11) Uani 1 1 d . . . N1 N 0.0666(2) 0.0251(6) 0.5455(3) 0.0342(12) Uani 1 1 d . . . C12 C 0.1074(3) 0.4083(6) 0.9599(4) 0.0336(15) Uani 1 1 d . . . H12 H 0.0726 0.4220 0.9333 0.040 Uiso 1 1 calc R . . C16 C 0.1724(3) 0.0585(6) 0.6868(4) 0.0336(15) Uani 1 1 d . . . C17 C 0.1930(4) -0.0614(7) 0.6791(5) 0.047(2) Uani 1 1 d . . . H17 H 0.1737 -0.1362 0.6769 0.056 Uiso 1 1 calc R . . C6 C 0.1249(3) -0.1945(6) 0.8275(4) 0.0380(15) Uani 1 1 d . . . O2 O 0.0340(2) 0.3525(5) 0.4968(3) 0.0516(14) Uani 1 1 d . . . C11 C 0.1367(3) 0.3489(6) 0.9225(4) 0.0336(14) Uani 1 1 d . . . C15 C 0.1112(3) 0.2999(6) 0.8354(4) 0.0325(14) Uani 1 1 d . . . C21 C 0.2011(3) 0.1688(7) 0.6888(4) 0.0456(17) Uani 1 1 d . . . H21 H 0.1873 0.2505 0.6918 0.055 Uiso 1 1 calc R . . C14 C 0.2114(3) 0.3678(7) 1.0410(4) 0.0411(16) Uani 1 1 d . . . H14 H 0.2462 0.3548 1.0685 0.049 Uiso 1 1 calc R . . C4 C 0.0634(3) -0.0905(7) 0.5075(5) 0.0416(18) Uani 1 1 d . . . H4 H 0.0717 -0.1660 0.5389 0.050 Uiso 1 1 calc R . . C1 C 0.0536(2) 0.1283(7) 0.4972(3) 0.0334(14) Uani 1 1 d . . . N5 N 0.1886(3) 0.3271(8) 0.9631(4) 0.0631(19) Uani 1 1 d . . . N2 N 0.0351(3) 0.0054(7) 0.3740(4) 0.0506(16) Uani 1 1 d . . . C2 C 0.0373(3) 0.1212(8) 0.4119(4) 0.0428(16) Uani 1 1 d . . . H2 H 0.0279 0.1965 0.3805 0.051 Uiso 1 1 calc R . . C5 C 0.0547(3) 0.2609(6) 0.5393(4) 0.0356(15) Uani 1 1 d . . . C18 C 0.2424(4) -0.0711(8) 0.6744(6) 0.054(2) Uani 1 1 d . . . H18 H 0.2560 -0.1517 0.6680 0.065 Uiso 1 1 calc R . . C3 C 0.0478(3) -0.0980(8) 0.4226(5) 0.0462(18) Uani 1 1 d . . . H3 H 0.0460 -0.1794 0.3982 0.055 Uiso 1 1 calc R . . C19 C 0.2706(4) 0.0395(10) 0.6792(5) 0.060(2) Uani 1 1 d . . . H19 H 0.3040 0.0339 0.6777 0.072 Uiso 1 1 calc R . . C20 C 0.2506(3) 0.1569(9) 0.6862(5) 0.058(2) Uani 1 1 d . . . H20 H 0.2704 0.2311 0.6893 0.069 Uiso 1 1 calc R . . C13 C 0.1813(4) 0.4281(8) 1.0768(5) 0.061(3) Uani 1 1 d . . . H13 H 0.1955 0.4583 1.1308 0.074 Uiso 1 1 calc R . . C7 C 0.1398(4) -0.2764(8) 0.8932(5) 0.0530(19) Uani 1 1 d . . . H7 H 0.1258 -0.3595 0.8876 0.064 Uiso 1 1 calc R . . N4 N 0.1741(4) -0.2419(8) 0.9661(4) 0.074(2) Uani 1 1 d . . . O4 O 0.0652(4) -0.3381(7) 0.7449(4) 0.111(3) Uani 1 1 d . . . C10 C 0.0875(4) -0.2359(7) 0.7447(5) 0.0490(19) Uani 1 1 d . . . C9 C 0.1754(3) -0.0371(8) 0.9050(5) 0.053(2) Uani 1 1 d . . . H9 H 0.1880 0.0475 0.9116 0.064 Uiso 1 1 calc R . . N6 N 0.1303(4) 0.4468(8) 1.0369(5) 0.072(2) Uani 1 1 d D . . H6 H 0.108(3) 0.495(9) 1.053(6) 0.087 Uiso 1 1 d D . . C8 C 0.1914(4) -0.1235(9) 0.9700(5) 0.071(3) Uani 1 1 d . . . H8 H 0.2157 -0.0959 1.0190 0.085 Uiso 1 1 calc R . . O7 O 0.9929(2) 0.4735(6) 0.8574(3) 0.0573(14) Uani 1 1 d D . . H7A H 0.977(3) 0.523(7) 0.817(4) 0.069 Uiso 1 1 d D . . H7B H 0.978(4) 0.395(5) 0.845(5) 0.069 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 Bi 0.0300(2) 0.0351(2) 0.0217(2) -0.00198(7) 0.00214(14) 0.00027(8) O5 0.034(3) 0.046(3) 0.031(2) -0.009(2) 0.0088(19) 0.003(2) N3 0.033(4) 0.042(4) 0.025(3) -0.001(2) 0.001(3) -0.003(2) O1 0.060(3) 0.039(2) 0.026(2) -0.0061(18) 0.008(2) 0.004(2) O3 0.050(3) 0.078(4) 0.031(3) -0.014(3) 0.002(2) -0.022(3) O6 0.037(3) 0.063(3) 0.026(2) 0.001(2) 0.003(2) 0.008(2) N1 0.033(3) 0.044(3) 0.022(3) -0.006(2) 0.005(2) -0.003(3) C12 0.034(4) 0.047(4) 0.017(3) -0.003(2) 0.005(3) 0.015(3) C16 0.038(4) 0.038(4) 0.021(3) -0.001(2) 0.005(3) 0.003(3) C17 0.057(5) 0.055(5) 0.035(4) 0.006(3) 0.024(4) 0.003(4) C6 0.042(4) 0.041(4) 0.030(3) -0.001(3) 0.010(3) -0.008(3) O2 0.077(4) 0.035(3) 0.035(3) 0.009(2) 0.007(3) 0.007(3) C11 0.035(4) 0.035(3) 0.026(3) 0.004(2) 0.003(3) 0.000(3) C15 0.038(4) 0.036(3) 0.023(3) 0.004(2) 0.007(3) -0.004(3) C21 0.045(4) 0.048(4) 0.044(4) -0.014(3) 0.015(3) -0.004(4) C14 0.027(3) 0.057(4) 0.027(3) -0.017(3) -0.007(3) 0.005(3) C4 0.040(4) 0.054(4) 0.029(4) -0.009(3) 0.009(3) 0.004(3) C1 0.030(3) 0.048(4) 0.022(3) -0.006(3) 0.007(2) -0.004(3) N5 0.045(4) 0.089(5) 0.051(4) -0.007(4) 0.010(3) -0.002(4) N2 0.045(4) 0.077(5) 0.031(3) -0.015(3) 0.013(3) -0.003(4) C2 0.035(4) 0.066(5) 0.025(3) -0.001(3) 0.007(3) -0.006(4) C5 0.037(4) 0.039(4) 0.029(3) -0.002(3) 0.009(3) -0.006(3) C18 0.053(6) 0.065(6) 0.047(5) 0.010(3) 0.020(4) 0.022(4) C3 0.042(4) 0.058(4) 0.037(4) -0.016(3) 0.012(3) -0.002(4) C19 0.047(5) 0.094(6) 0.042(5) -0.003(4) 0.019(4) 0.005(5) C20 0.047(5) 0.079(6) 0.051(5) -0.023(4) 0.021(4) -0.022(5) C13 0.056(6) 0.082(7) 0.030(4) -0.016(3) -0.007(4) 0.011(4) C7 0.069(6) 0.046(4) 0.044(4) 0.003(3) 0.019(4) -0.001(4) N4 0.097(7) 0.073(5) 0.039(4) 0.012(3) 0.002(4) 0.012(5) O4 0.159(8) 0.062(4) 0.080(5) -0.004(4) -0.005(5) -0.066(5) C10 0.066(5) 0.036(4) 0.037(4) -0.007(3) 0.005(4) 0.003(4) C9 0.053(5) 0.049(4) 0.040(4) -0.002(3) -0.008(4) -0.009(4) N6 0.074(7) 0.086(6) 0.054(5) -0.012(4) 0.018(4) 0.017(4) C8 0.090(7) 0.060(5) 0.037(4) 0.008(4) -0.015(4) 0.005(6) O7 0.060(4) 0.064(3) 0.040(3) 0.003(3) 0.006(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 Bi C16 2.233(8) . ? Bi O5 2.368(5) . ? Bi O1 2.398(5) . ? Bi O3 2.472(6) . ? Bi N1 2.613(5) . ? Bi N3 2.624(6) . ? O5 C15 1.287(8) . ? N3 C6 1.323(8) . ? N3 C9 1.330(10) . ? O1 C5 1.280(8) . ? O3 C10 1.242(10) . ? O6 C15 1.229(8) . ? N1 C1 1.321(9) . ? N1 C4 1.344(9) . ? C12 N6 1.320(11) . ? C12 C11 1.330(9) . ? C12 H12 0.9300 . ? C16 C21 1.377(10) . ? C16 C17 1.382(10) . ? C17 C18 1.395(15) . ? C17 H17 0.9300 . ? C6 C7 1.355(10) . ? C6 C10 1.514(10) . ? O2 C5 1.213(8) . ? C11 N5 1.389(10) . ? C11 C15 1.510(9) . ? C21 C20 1.387(12) . ? C21 H21 0.9300 . ? C14 C13 1.334(12) . ? C14 N5 1.340(9) . ? C14 H14 0.9300 . ? C4 C3 1.373(11) . ? C4 H4 0.9300 . ? C1 C2 1.378(9) . ? C1 C5 1.537(9) . ? N2 C3 1.324(10) . ? N2 C2 1.347(10) . ? C2 H2 0.9300 . ? C18 C19 1.365(13) . ? C18 H18 0.9300 . ? C3 H3 0.9300 . ? C19 C20 1.348(13) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C13 N6 1.360(14) . ? C13 H13 0.9300 . ? C7 N4 1.342(12) . ? C7 H7 0.9300 . ? N4 C8 1.302(12) . ? O4 C10 1.219(10) . ? C9 C8 1.378(12) . ? C9 H9 0.9300 . ? N6 H6 0.903(10) . ? C8 H8 0.9300 . ? O7 H7A 0.85(4) . ? O7 H7B 0.90(4) . ? 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 C16 Bi O5 82.8(2) . . ? C16 Bi O1 90.1(2) . . ? O5 Bi O1 83.36(15) . . ? C16 Bi O3 91.6(2) . . ? O5 Bi O3 140.33(17) . . ? O1 Bi O3 136.08(16) . . ? C16 Bi N1 80.4(2) . . ? O5 Bi N1 144.12(17) . . ? O1 Bi N1 65.27(16) . . ? O3 Bi N1 71.80(18) . . ? C16 Bi N3 81.4(2) . . ? O5 Bi N3 76.21(18) . . ? O1 Bi N3 158.67(18) . . ? O3 Bi N3 64.13(17) . . ? N1 Bi N3 131.42(17) . . ? C15 O5 Bi 117.0(4) . . ? C6 N3 C9 117.0(6) . . ? C6 N3 Bi 114.6(4) . . ? C9 N3 Bi 127.8(5) . . ? C5 O1 Bi 124.8(4) . . ? C10 O3 Bi 119.9(4) . . ? C1 N1 C4 116.6(6) . . ? C1 N1 Bi 115.3(4) . . ? C4 N1 Bi 128.1(5) . . ? N6 C12 C11 116.6(7) . . ? N6 C12 H12 121.7 . . ? C11 C12 H12 121.7 . . ? C21 C16 C17 119.1(8) . . ? C21 C16 Bi 120.2(5) . . ? C17 C16 Bi 120.5(6) . . ? C16 C17 C18 120.7(8) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? N3 C6 C7 121.5(7) . . ? N3 C6 C10 116.6(6) . . ? C7 C6 C10 122.0(7) . . ? C12 C11 N5 121.4(6) . . ? C12 C11 C15 117.8(6) . . ? N5 C11 C15 120.8(6) . . ? O6 C15 O5 126.0(6) . . ? O6 C15 C11 119.3(6) . . ? O5 C15 C11 114.7(6) . . ? C16 C21 C20 119.4(7) . . ? C16 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C13 C14 N5 116.1(7) . . ? C13 C14 H14 122.0 . . ? N5 C14 H14 122.0 . . ? N1 C4 C3 120.6(7) . . ? N1 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C1 C2 123.1(7) . . ? N1 C1 C5 117.4(5) . . ? C2 C1 C5 119.5(6) . . ? C14 N5 C11 121.3(7) . . ? C3 N2 C2 116.6(7) . . ? N2 C2 C1 120.2(8) . . ? N2 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? O2 C5 O1 125.9(6) . . ? O2 C5 C1 118.4(6) . . ? O1 C5 C1 115.6(6) . . ? C19 C18 C17 118.9(7) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? N2 C3 C4 123.0(7) . . ? N2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? C20 C19 C18 120.7(9) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 121.1(8) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C14 C13 N6 122.1(7) . . ? C14 C13 H13 119.0 . . ? N6 C13 H13 119.0 . . ? N4 C7 C6 122.4(8) . . ? N4 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C8 N4 C7 115.4(7) . . ? O4 C10 O3 126.1(7) . . ? O4 C10 C6 115.5(7) . . ? O3 C10 C6 118.4(7) . . ? N3 C9 C8 120.5(8) . . ? N3 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C12 N6 C13 122.6(8) . . ? C12 N6 H6 108(7) . . ? C13 N6 H6 129(7) . . ? N4 C8 C9 123.2(8) . . ? N4 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? H7A O7 H7B 106(6) . . ? 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 N6 H6 O2 0.903(10) 2.50(7) 3.255(11) 142(9) 6_566 N6 H6 O1 0.903(10) 2.97(5) 3.799(10) 153(9) 6_566 O7 H7B O6 0.90(4) 2.44(8) 3.010(7) 122(6) 2_656 O7 H7B O1 0.90(4) 2.27(7) 3.011(8) 139(8) 2_656 O7 H7A O4 0.85(4) 1.93(5) 2.748(9) 161(9) 2_666 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 3.703 _refine_diff_density_min -2.755 _refine_diff_density_rms 0.254 #===END data_compound9 _database_code_depnum_ccdc_archive 'CCDC 825248' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H19 Bi N2 O5' _chemical_formula_weight 648.41 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.120(2) _cell_length_b 13.740(3) _cell_length_c 16.630(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.00(3) _cell_angle_gamma 90.00 _cell_volume 2269.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 7.809 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3042 _exptl_absorpt_correction_T_max 0.5090 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8805 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3986 _reflns_number_gt 3130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^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 3986 _refine_ls_number_parameters 313 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.987 _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 C15 C 0.7398(7) 0.6233(5) 1.2370(5) 0.053(2) Uani 1 1 d . . . H15 H 0.7974 0.6248 1.2877 0.063 Uiso 1 1 calc R . . Bi Bi 0.19031(2) 0.600347(17) 1.015227(14) 0.03469(10) Uani 1 1 d . . . O1 O 0.1056(4) 0.6094(3) 1.1282(3) 0.0438(12) Uani 1 1 d . . . N1 N 0.3762(5) 0.6173(4) 1.1468(3) 0.0328(12) Uani 1 1 d . . . C6 C 0.3140(7) 0.8063(5) 0.9824(4) 0.0463(18) Uani 1 1 d . . . H6 H 0.3744 0.7681 0.9606 0.056 Uiso 1 1 calc R . . O3 O -0.0331(4) 0.6122(3) 0.9738(3) 0.0469(12) Uani 1 1 d . . . C21 C 0.2011(9) 0.6251(4) 0.7982(4) 0.046(2) Uani 1 1 d . . . N2 N 0.1217(6) 0.6224(3) 0.8563(3) 0.0408(15) Uani 1 1 d . . . C8 C 0.4024(7) 0.6222(5) 1.2927(4) 0.0450(18) Uani 1 1 d . . . H8 H 0.3616 0.6237 1.3382 0.054 Uiso 1 1 calc R . . O4 O -0.2177(5) 0.6216(4) 0.8802(3) 0.0717(17) Uani 1 1 d . . . C11 C 0.5145(7) 0.6191(4) 1.1551(4) 0.0360(16) Uani 1 1 d . . . C12 C 0.5694(7) 0.6198(5) 1.0851(4) 0.0448(18) Uani 1 1 d . . . H12 H 0.5130 0.6187 1.0339 0.054 Uiso 1 1 calc R . . C7 C 0.3247(6) 0.6188(4) 1.2141(4) 0.0363(16) Uani 1 1 d . . . C9 C 0.5383(7) 0.6233(5) 1.3020(4) 0.0460(19) Uani 1 1 d . . . H9 H 0.5914 0.6254 1.3542 0.055 Uiso 1 1 calc R . . C10 C 0.5988(7) 0.6215(4) 1.2330(4) 0.0413(18) Uani 1 1 d . . . C17 C -0.0115(8) 0.6232(4) 0.8331(4) 0.0446(19) Uani 1 1 d . . . C13 C 0.7063(8) 0.6221(5) 1.0903(5) 0.054(2) Uani 1 1 d . . . H13 H 0.7428 0.6231 1.0431 0.065 Uiso 1 1 calc R . . C1 C 0.2092(7) 0.7625(5) 1.0142(4) 0.0378(16) Uani 1 1 d . . . C16 C 0.1721(7) 0.6176(5) 1.2017(4) 0.0373(16) Uani 1 1 d . . . C22 C 0.3428(9) 0.6231(5) 0.8228(5) 0.055(2) Uani 1 1 d . . . H22 H 0.3820 0.6195 0.8780 0.066 Uiso 1 1 calc R . . C5 C 0.3266(8) 0.9076(5) 0.9837(5) 0.058(2) Uani 1 1 d . . . H5 H 0.3945 0.9370 0.9618 0.069 Uiso 1 1 calc R . . C3 C 0.1399(12) 0.9204(6) 1.0471(6) 0.082(3) Uani 1 1 d . . . H3 H 0.0805 0.9591 1.0694 0.098 Uiso 1 1 calc R . . C20 C 0.1439(11) 0.6287(5) 0.7146(4) 0.057(2) Uani 1 1 d . . . C18 C -0.0741(10) 0.6269(5) 0.7499(5) 0.064(3) Uani 1 1 d . . . H18 H -0.1675 0.6276 0.7350 0.077 Uiso 1 1 calc R . . C14 C 0.7911(8) 0.6228(5) 1.1684(6) 0.058(2) Uani 1 1 d . . . H14 H 0.8839 0.6229 1.1722 0.070 Uiso 1 1 calc R . . C2 C 0.1231(9) 0.8202(6) 1.0461(5) 0.068(2) Uani 1 1 d . . . H2 H 0.0531 0.7925 1.0671 0.081 Uiso 1 1 calc R . . O2 O 0.1194(5) 0.6232(4) 1.2614(3) 0.0637(16) Uani 1 1 d . . . C26 C -0.0950(8) 0.6200(5) 0.8983(5) 0.048(2) Uani 1 1 d . . . O5 O 0.3702(9) 0.2019(6) 0.0768(5) 0.105(2) Uani 1 1 d D . . H5A H 0.390(10) 0.253(6) 0.103(7) 0.126 Uiso 1 1 d D . . H5B H 0.288(6) 0.191(8) 0.080(7) 0.126 Uiso 1 1 d D . . C4 C 0.2396(11) 0.9631(6) 1.0169(5) 0.068(3) Uani 1 1 d . . . H4 H 0.2490 1.0305 1.0188 0.081 Uiso 1 1 calc R . . C23 C 0.4202(11) 0.6267(5) 0.7656(6) 0.073(3) Uani 1 1 d . . . H23 H 0.5133 0.6272 0.7821 0.088 Uiso 1 1 calc R . . C25 C 0.2297(16) 0.6313(6) 0.6575(6) 0.083(3) Uani 1 1 d . . . H25 H 0.1931 0.6343 0.6018 0.099 Uiso 1 1 calc R . . C19 C 0.0023(13) 0.6293(5) 0.6922(5) 0.077(3) Uani 1 1 d . . . H19 H -0.0385 0.6315 0.6371 0.092 Uiso 1 1 calc R . . C24 C 0.3654(16) 0.6296(6) 0.6827(7) 0.091(4) Uani 1 1 d . . . H24 H 0.4215 0.6303 0.6444 0.109 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 C15 0.034(4) 0.049(5) 0.069(6) 0.004(4) -0.007(4) 0.001(3) Bi 0.03195(15) 0.04137(15) 0.02974(15) 0.00071(12) 0.00330(10) -0.00030(12) O1 0.025(2) 0.074(3) 0.031(2) 0.001(2) 0.003(2) -0.001(2) N1 0.026(3) 0.043(3) 0.029(3) 0.000(2) 0.007(2) 0.002(2) C6 0.048(4) 0.049(4) 0.039(4) -0.001(3) 0.000(3) 0.014(4) O3 0.031(3) 0.073(3) 0.035(3) -0.001(2) 0.003(2) 0.003(2) C21 0.083(6) 0.027(3) 0.030(4) 0.000(3) 0.017(4) -0.008(4) N2 0.056(4) 0.032(3) 0.029(3) 0.003(2) -0.007(3) -0.001(3) C8 0.046(4) 0.056(4) 0.031(4) 0.002(3) 0.002(3) 0.001(4) O4 0.038(3) 0.100(4) 0.068(4) 0.006(3) -0.012(3) 0.000(3) C11 0.035(4) 0.036(4) 0.035(4) 0.004(3) 0.002(3) 0.001(3) C12 0.041(4) 0.053(4) 0.042(4) 0.003(3) 0.012(3) 0.001(3) C7 0.032(4) 0.042(4) 0.033(4) -0.001(3) 0.000(3) -0.004(3) C9 0.049(5) 0.053(4) 0.029(4) 0.002(3) -0.010(3) -0.001(3) C10 0.040(4) 0.033(4) 0.046(4) 0.002(3) -0.006(4) 0.001(3) C17 0.054(5) 0.037(4) 0.035(4) 0.003(3) -0.009(4) -0.006(3) C13 0.045(5) 0.052(4) 0.073(6) 0.006(4) 0.031(4) 0.006(4) C1 0.033(4) 0.054(4) 0.027(3) -0.001(3) 0.005(3) 0.002(3) C16 0.030(4) 0.051(4) 0.033(4) -0.003(3) 0.011(3) -0.001(3) C22 0.072(6) 0.048(4) 0.051(5) -0.003(4) 0.029(5) -0.002(4) C5 0.063(5) 0.052(5) 0.049(5) 0.013(4) -0.011(4) -0.009(4) C3 0.110(8) 0.050(5) 0.099(7) -0.005(5) 0.053(7) 0.020(5) C20 0.104(8) 0.042(4) 0.027(4) -0.003(3) 0.017(5) -0.012(4) C18 0.080(6) 0.054(5) 0.044(5) 0.007(4) -0.025(5) -0.016(4) C14 0.029(4) 0.048(4) 0.095(7) 0.009(4) 0.005(5) 0.002(3) C2 0.075(6) 0.065(5) 0.074(6) -0.002(4) 0.041(5) 0.016(5) O2 0.040(3) 0.118(5) 0.036(3) -0.011(3) 0.014(2) -0.006(3) C26 0.041(4) 0.045(4) 0.049(5) 0.000(3) -0.014(4) -0.001(3) O5 0.122(6) 0.122(6) 0.081(5) 0.009(4) 0.047(5) 0.003(6) C4 0.096(7) 0.043(5) 0.058(5) 0.000(4) 0.000(5) 0.006(5) C23 0.096(7) 0.045(5) 0.094(8) 0.002(5) 0.056(6) -0.003(5) C25 0.167(12) 0.045(5) 0.046(5) 0.001(4) 0.045(7) 0.007(7) C19 0.150(11) 0.044(4) 0.026(4) -0.002(3) -0.011(6) -0.015(5) C24 0.165(12) 0.054(5) 0.080(8) 0.004(5) 0.089(9) 0.006(7) _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 C15 C14 1.340(12) . ? C15 C10 1.416(10) . ? C15 H15 0.9300 . ? Bi O1 2.213(5) . ? Bi C1 2.237(7) . ? Bi O3 2.241(4) . ? Bi N1 2.610(5) . ? Bi N2 2.619(5) . ? O1 C16 1.283(7) . ? N1 C7 1.321(8) . ? N1 C11 1.381(8) . ? C6 C5 1.397(10) . ? C6 C1 1.407(10) . ? C6 H6 0.9300 . ? O3 C26 1.295(8) . ? C21 N2 1.370(9) . ? C21 C20 1.401(10) . ? C21 C22 1.414(11) . ? N2 C17 1.330(9) . ? C8 C9 1.354(10) . ? C8 C7 1.391(9) . ? C8 H8 0.9300 . ? O4 C26 1.221(9) . ? C11 C12 1.382(10) . ? C11 C10 1.409(9) . ? C12 C13 1.371(10) . ? C12 H12 0.9300 . ? C7 C16 1.519(9) . ? C9 C10 1.400(10) . ? C9 H9 0.9300 . ? C17 C18 1.409(10) . ? C17 C26 1.497(11) . ? C13 C14 1.413(11) . ? C13 H13 0.9300 . ? C1 C2 1.358(10) . ? C16 O2 1.216(8) . ? C22 C23 1.344(12) . ? C22 H22 0.9300 . ? C5 C4 1.359(12) . ? C5 H5 0.9300 . ? C3 C4 1.345(13) . ? C3 C2 1.386(12) . ? C3 H3 0.9300 . ? C20 C25 1.404(13) . ? C20 C19 1.411(14) . ? C18 C19 1.342(13) . ? C18 H18 0.9300 . ? C14 H14 0.9300 . ? C2 H2 0.9300 . ? O5 H5A 0.83(5) . ? O5 H5B 0.85(5) . ? C4 H4 0.9300 . ? C23 C24 1.385(15) . ? C23 H23 0.9300 . ? C25 C24 1.358(15) . ? C25 H25 0.9300 . ? C19 H19 0.9300 . ? C24 H24 0.9300 . ? 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 C14 C15 C10 120.7(7) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O1 Bi C1 89.9(2) . . ? O1 Bi O3 74.04(16) . . ? C1 Bi O3 90.5(2) . . ? O1 Bi N1 67.48(16) . . ? C1 Bi N1 82.46(18) . . ? O3 Bi N1 140.81(17) . . ? O1 Bi N2 141.21(18) . . ? C1 Bi N2 83.32(18) . . ? O3 Bi N2 67.90(19) . . ? N1 Bi N2 147.76(19) . . ? C16 O1 Bi 126.6(4) . . ? C7 N1 C11 118.2(5) . . ? C7 N1 Bi 111.9(4) . . ? C11 N1 Bi 129.8(4) . . ? C5 C6 C1 119.6(7) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C26 O3 Bi 125.2(5) . . ? N2 C21 C20 121.0(8) . . ? N2 C21 C22 119.6(7) . . ? C20 C21 C22 119.5(8) . . ? C17 N2 C21 119.6(6) . . ? C17 N2 Bi 110.6(5) . . ? C21 N2 Bi 129.6(5) . . ? C9 C8 C7 119.2(7) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? N1 C11 C12 118.7(6) . . ? N1 C11 C10 121.1(6) . . ? C12 C11 C10 120.3(6) . . ? C13 C12 C11 120.7(7) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N1 C7 C8 123.5(6) . . ? N1 C7 C16 116.1(5) . . ? C8 C7 C16 120.4(6) . . ? C8 C9 C10 120.0(6) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 118.1(6) . . ? C9 C10 C15 123.7(7) . . ? C11 C10 C15 118.1(7) . . ? N2 C17 C18 121.7(8) . . ? N2 C17 C26 118.1(6) . . ? C18 C17 C26 120.2(7) . . ? C12 C13 C14 119.2(8) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C2 C1 C6 118.8(7) . . ? C2 C1 Bi 121.1(6) . . ? C6 C1 Bi 120.1(5) . . ? O2 C16 O1 123.4(6) . . ? O2 C16 C7 118.8(6) . . ? O1 C16 C7 117.7(6) . . ? C23 C22 C21 119.3(9) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C4 C5 C6 120.1(8) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C3 C2 121.8(9) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C21 C20 C25 118.7(10) . . ? C21 C20 C19 118.0(9) . . ? C25 C20 C19 123.3(9) . . ? C19 C18 C17 119.4(9) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C15 C14 C13 121.1(7) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C1 C2 C3 119.9(9) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? O4 C26 O3 121.4(8) . . ? O4 C26 C17 120.5(7) . . ? O3 C26 C17 118.0(6) . . ? H5A O5 H5B 105(7) . . ? C3 C4 C5 119.8(8) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C22 C23 C24 122.0(11) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C24 C25 C20 120.7(10) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C18 C19 C20 120.4(8) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C25 C24 C23 119.8(10) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? 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 O5 H5B O2 0.85(5) 2.79(13) 2.883(9) 88(9) 2_546 O5 H5A O4 0.83(5) 2.50(10) 3.032(10) 123(9) 3_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.489 _refine_diff_density_min -0.806 _refine_diff_density_rms 0.135 #===END data_compound10 _database_code_depnum_ccdc_archive 'CCDC 825249' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 Bi O3' _chemical_formula_weight 474.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.340(2) _cell_length_b 9.7251(19) _cell_length_c 15.679(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.02(3) _cell_angle_gamma 90.00 _cell_volume 1547.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 11.399 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1628 _exptl_absorpt_correction_T_max 0.3416 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 14384 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2726 _reflns_number_gt 2523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+1.0448P] 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 2726 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0191 _refine_ls_wR_factor_ref 0.0471 _refine_ls_wR_factor_gt 0.0465 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 Bi Bi 0.290643(12) 0.533586(13) 0.213906(8) 0.03269(7) Uani 1 1 d . . . O1 O 0.1612(2) 0.7464(2) 0.22107(17) 0.0371(6) Uani 1 1 d . . . O2 O 0.0319(2) 0.8788(2) 0.28373(16) 0.0372(6) Uani 1 1 d . . . C15 C -0.1855(4) 0.6798(5) 0.2244(3) 0.0493(10) Uani 1 1 d . . . H15 H -0.2262 0.7468 0.2525 0.059 Uiso 1 1 calc R . . C1 C 0.3984(3) 0.6659(4) 0.1341(2) 0.0336(8) Uani 1 1 d . . . C2 C 0.4580(4) 0.7886(4) 0.1645(3) 0.0468(10) Uani 1 1 d . . . H2 H 0.4535 0.8186 0.2202 0.056 Uiso 1 1 calc R . . C3 C 0.5241(5) 0.8671(5) 0.1130(3) 0.0622(13) Uani 1 1 d . . . H3 H 0.5648 0.9486 0.1345 0.075 Uiso 1 1 calc R . . C4 C 0.5297(5) 0.8247(6) 0.0303(4) 0.0696(15) Uani 1 1 d . . . H4 H 0.5751 0.8770 -0.0040 0.084 Uiso 1 1 calc R . . C5 C 0.4687(5) 0.7055(5) -0.0018(3) 0.0621(13) Uani 1 1 d . . . H5 H 0.4714 0.6777 -0.0582 0.075 Uiso 1 1 calc R . . C6 C 0.4029(4) 0.6264(5) 0.0496(3) 0.0484(10) Uani 1 1 d . . . H6 H 0.3612 0.5458 0.0273 0.058 Uiso 1 1 calc R . . C7 C 0.4037(4) 0.6095(4) 0.3417(2) 0.0391(8) Uani 1 1 d . . . C8 C 0.3395(5) 0.6702(5) 0.4005(3) 0.0605(12) Uani 1 1 d . . . H8 H 0.2485 0.6800 0.3870 0.073 Uiso 1 1 calc R . . C9 C 0.4080(7) 0.7172(7) 0.4798(3) 0.0849(18) Uani 1 1 d . . . H9 H 0.3628 0.7584 0.5189 0.102 Uiso 1 1 calc R . . C10 C 0.5410(7) 0.7034(6) 0.5004(3) 0.0770(16) Uani 1 1 d . . . H10 H 0.5872 0.7361 0.5533 0.092 Uiso 1 1 calc R . . C11 C 0.6060(5) 0.6416(5) 0.4435(3) 0.0659(14) Uani 1 1 d . . . H11 H 0.6969 0.6305 0.4581 0.079 Uiso 1 1 calc R . . C12 C 0.5386(4) 0.5946(5) 0.3637(3) 0.0516(10) Uani 1 1 d . . . H12 H 0.5844 0.5531 0.3250 0.062 Uiso 1 1 calc R . . C13 C 0.0527(3) 0.7714(3) 0.2424(2) 0.0292(7) Uani 1 1 d . . . C14 C -0.0587(3) 0.6770(4) 0.2170(2) 0.0324(8) Uani 1 1 d . . . C16 C -0.1521(4) 0.4944(4) 0.1520(3) 0.0523(12) Uani 1 1 d . . . H16 H -0.1645 0.4119 0.1216 0.063 Uiso 1 1 calc R . . O3 O -0.0350(3) 0.5621(3) 0.17218(19) 0.0448(7) Uani 1 1 d . . . C17 C -0.2459(4) 0.5616(5) 0.1814(3) 0.0556(12) Uani 1 1 d . . . H17 H -0.3339 0.5361 0.1751 0.067 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 Bi 0.02766(9) 0.03038(10) 0.04022(10) -0.00102(6) 0.00697(6) 0.00174(5) O1 0.0275(13) 0.0339(14) 0.0518(15) -0.0031(12) 0.0121(11) 0.0006(11) O2 0.0325(14) 0.0310(13) 0.0511(15) -0.0075(12) 0.0156(11) -0.0041(11) C15 0.039(2) 0.038(2) 0.073(3) -0.008(2) 0.016(2) 0.0001(18) C1 0.0330(19) 0.0351(19) 0.0331(19) 0.0020(15) 0.0074(15) 0.0076(15) C2 0.061(3) 0.035(2) 0.046(2) 0.0005(18) 0.016(2) -0.0002(19) C3 0.076(3) 0.042(3) 0.072(3) 0.010(2) 0.022(3) -0.004(2) C4 0.080(4) 0.065(3) 0.075(3) 0.031(3) 0.042(3) 0.016(3) C5 0.085(3) 0.066(3) 0.042(3) 0.011(2) 0.029(2) 0.024(3) C6 0.058(3) 0.048(3) 0.039(2) -0.0010(18) 0.0097(19) 0.013(2) C7 0.046(2) 0.036(2) 0.0344(19) 0.0065(17) 0.0078(16) 0.0013(18) C8 0.071(3) 0.075(3) 0.037(2) -0.001(2) 0.014(2) 0.014(3) C9 0.122(5) 0.097(5) 0.037(3) -0.010(3) 0.020(3) 0.014(4) C10 0.113(5) 0.072(3) 0.037(3) 0.004(2) -0.009(3) -0.019(3) C11 0.064(3) 0.066(3) 0.060(3) 0.011(2) -0.009(2) -0.020(3) C12 0.046(3) 0.056(3) 0.051(2) 0.002(2) 0.006(2) -0.006(2) C13 0.0284(18) 0.0268(17) 0.0318(18) 0.0031(14) 0.0045(14) 0.0021(14) C14 0.0293(18) 0.0300(18) 0.0383(19) -0.0001(15) 0.0072(15) -0.0006(15) C16 0.041(3) 0.039(2) 0.073(3) -0.016(2) 0.003(2) -0.0099(19) O3 0.0354(15) 0.0381(14) 0.0604(18) -0.0135(13) 0.0077(13) -0.0030(11) C17 0.030(2) 0.055(3) 0.080(3) -0.009(2) 0.006(2) -0.014(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 Bi C1 2.235(4) . ? Bi C7 2.243(4) . ? Bi O2 2.368(2) 2_545 ? Bi O1 2.479(2) . ? O1 C13 1.254(4) . ? O2 C13 1.269(4) . ? O2 Bi 2.368(2) 2 ? C15 C14 1.338(5) . ? C15 C17 1.417(6) . ? C15 H15 0.9300 . ? C1 C2 1.385(5) . ? C1 C6 1.390(5) . ? C2 C3 1.383(6) . ? C2 H2 0.9300 . ? C3 C4 1.373(7) . ? C3 H3 0.9300 . ? C4 C5 1.369(8) . ? C4 H4 0.9300 . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.368(6) . ? C7 C12 1.379(6) . ? C8 C9 1.385(7) . ? C8 H8 0.9300 . ? C9 C10 1.358(9) . ? C9 H9 0.9300 . ? C10 C11 1.357(8) . ? C10 H10 0.9300 . ? C11 C12 1.388(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.468(5) . ? C14 O3 1.367(4) . ? C16 C17 1.323(7) . ? C16 O3 1.360(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 C1 Bi C7 94.60(13) . . ? C1 Bi O2 84.68(11) . 2_545 ? C7 Bi O2 85.71(12) . 2_545 ? C1 Bi O1 82.86(10) . . ? C7 Bi O1 83.02(12) . . ? O2 Bi O1 162.45(8) 2_545 . ? C13 O1 Bi 133.8(2) . . ? C13 O2 Bi 109.0(2) . 2 ? C14 C15 C17 107.0(4) . . ? C14 C15 H15 126.5 . . ? C17 C15 H15 126.5 . . ? C2 C1 C6 118.2(4) . . ? C2 C1 Bi 122.7(3) . . ? C6 C1 Bi 119.1(3) . . ? C3 C2 C1 120.8(4) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.8(4) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 118.3(4) . . ? C8 C7 Bi 120.5(3) . . ? C12 C7 Bi 121.2(3) . . ? C7 C8 C9 121.1(5) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 120.1(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.8(5) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C7 C12 C11 120.0(5) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? O1 C13 O2 122.9(3) . . ? O1 C13 C14 120.2(3) . . ? O2 C13 C14 116.9(3) . . ? C15 C14 O3 109.7(3) . . ? C15 C14 C13 134.0(4) . . ? O3 C14 C13 116.2(3) . . ? C17 C16 O3 111.1(4) . . ? C17 C16 H16 124.5 . . ? O3 C16 H16 124.5 . . ? C16 O3 C14 106.0(3) . . ? C16 C17 C15 106.3(4) . . ? C16 C17 H17 126.9 . . ? C15 C17 H17 126.9 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.758 _refine_diff_density_min -0.705 _refine_diff_density_rms 0.090 #===END data_compound11 _database_code_depnum_ccdc_archive 'CCDC 825250' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H39 Bi3 O6 S3' _chemical_formula_weight 1470.94 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 orthorhombic _symmetry_space_group_name_H-M 'P21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.238(2) _cell_length_b 17.369(4) _cell_length_c 30.368(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4872.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2760 _exptl_absorpt_coefficient_mu 10.984 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2174 _exptl_absorpt_correction_T_max 0.4063 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 46869 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8553 _reflns_number_gt 7614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(8) _refine_ls_number_reflns 8553 _refine_ls_number_parameters 558 _refine_ls_number_restraints 62 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.056 _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 0.03558(3) 0.230368(19) 0.832696(10) 0.04281(10) Uani 1 1 d . . . Bi2 Bi 0.52612(3) 0.272620(19) 0.846307(11) 0.04542(10) Uani 1 1 d . . . Bi3 Bi 0.32500(3) 0.744996(18) 0.974060(11) 0.04398(10) Uani 1 1 d . . . O1 O -0.0999(6) 0.1560(4) 0.7846(2) 0.0502(16) Uani 1 1 d . . . O2 O 0.2308(7) 0.2941(3) 0.8803(2) 0.0493(15) Uani 1 1 d . . . O3 O 0.3984(6) 0.3819(3) 0.8672(2) 0.0470(15) Uani 1 1 d . . . O4 O 0.7289(6) 0.1728(4) 0.8338(2) 0.0485(16) Uani 1 1 d . . . O5 O 0.4629(7) 0.8371(4) 0.9401(2) 0.0548(16) Uani 1 1 d . . . O6 O 0.1016(6) 0.6704(3) 1.00074(19) 0.0470(15) Uani 1 1 d . . . C1 C 0.1401(8) 0.1203(4) 0.8548(3) 0.042(2) Uani 1 1 d D . . C2 C 0.1169(10) 0.0501(4) 0.8335(3) 0.060(3) Uani 1 1 d D . . H2 H 0.0580 0.0486 0.8086 0.072 Uiso 1 1 calc R . . C3 C 0.1798(11) -0.0172(5) 0.8486(3) 0.066(3) Uani 1 1 d D . . H3 H 0.1621 -0.0636 0.8343 0.079 Uiso 1 1 calc R . . C4 C 0.2685(13) -0.0150(6) 0.8850(3) 0.074(3) Uani 1 1 d D . . H4 H 0.3113 -0.0603 0.8948 0.089 Uiso 1 1 calc R . . C5 C 0.2955(13) 0.0520(5) 0.9070(4) 0.077(4) Uani 1 1 d D . . H5 H 0.3548 0.0527 0.9318 0.093 Uiso 1 1 calc R . . C6 C 0.2310(11) 0.1200(5) 0.8912(3) 0.063(3) Uani 1 1 d D . . H6 H 0.2499 0.1661 0.9056 0.076 Uiso 1 1 calc R . . C7 C 0.1864(8) 0.2470(4) 0.7759(2) 0.043(2) Uani 1 1 d D . . C8 C 0.2429(10) 0.1859(5) 0.7518(3) 0.063(3) Uani 1 1 d D . . H8 H 0.2179 0.1357 0.7591 0.076 Uiso 1 1 calc R . . C9 C 0.3373(12) 0.1998(6) 0.7166(3) 0.085(4) Uani 1 1 d D . . H9 H 0.3741 0.1590 0.7003 0.102 Uiso 1 1 calc R . . C10 C 0.3755(12) 0.2751(6) 0.7062(4) 0.080(3) Uani 1 1 d D . . H10 H 0.4419 0.2844 0.6838 0.096 Uiso 1 1 calc R . . C11 C 0.3161(12) 0.3358(6) 0.7288(3) 0.069(3) Uani 1 1 d D . . H11 H 0.3383 0.3861 0.7207 0.083 Uiso 1 1 calc R . . C12 C 0.2238(10) 0.3222(5) 0.7634(3) 0.055(3) Uani 1 1 d D . . H12 H 0.1852 0.3637 0.7789 0.066 Uiso 1 1 calc R . . S1 S 0.2157(4) 0.51745(18) 0.89420(13) 0.0842(10) Uani 1 1 d . . . C13 C 0.2742(9) 0.3614(5) 0.8808(3) 0.041(2) Uani 1 1 d . . . C14 C 0.1758(11) 0.4209(5) 0.9005(3) 0.051(2) Uani 1 1 d . . . C15 C 0.0488(10) 0.4084(5) 0.9241(3) 0.052(2) Uani 1 1 d . . . H15 H 0.0085 0.3606 0.9305 0.062 Uiso 1 1 calc R . . C16 C -0.0073(14) 0.4792(8) 0.9362(4) 0.095(4) Uani 1 1 d . . . H16 H -0.0911 0.4834 0.9530 0.114 Uiso 1 1 calc R . . C17 C 0.0675(14) 0.5426(9) 0.9221(5) 0.101(5) Uani 1 1 d . . . H17 H 0.0394 0.5932 0.9275 0.121 Uiso 1 1 calc R . . C18 C 0.6055(10) 0.2660(5) 0.9153(3) 0.052(2) Uani 1 1 d D . . C19 C 0.6036(15) 0.3248(6) 0.9443(3) 0.114(6) Uani 1 1 d D . . H19 H 0.5680 0.3722 0.9350 0.136 Uiso 1 1 calc R . . C20 C 0.652(2) 0.3181(8) 0.9870(4) 0.147(8) Uani 1 1 d D . . H20 H 0.6470 0.3603 1.0058 0.176 Uiso 1 1 calc R . . C21 C 0.706(2) 0.2499(8) 1.0020(5) 0.147(8) Uani 1 1 d D . . H21 H 0.7462 0.2454 1.0299 0.177 Uiso 1 1 calc R . . C22 C 0.698(3) 0.1883(9) 0.9737(4) 0.207(13) Uani 1 1 d D . . H22 H 0.7251 0.1398 0.9837 0.248 Uiso 1 1 calc R . . C23 C 0.652(2) 0.1965(7) 0.9308(4) 0.151(8) Uani 1 1 d D . . H23 H 0.6528 0.1540 0.9122 0.181 Uiso 1 1 calc R . . C24 C 0.6917(10) 0.3558(5) 0.8210(3) 0.044(2) Uani 1 1 d D . . C25 C 0.7454(10) 0.4181(5) 0.8439(3) 0.070(3) Uani 1 1 d D . . H25 H 0.7133 0.4267 0.8725 0.084 Uiso 1 1 calc R . . C26 C 0.8446(12) 0.4680(7) 0.8259(4) 0.093(4) Uani 1 1 d D . . H26 H 0.8783 0.5102 0.8418 0.112 Uiso 1 1 calc R . . C27 C 0.8938(14) 0.4535(8) 0.7829(4) 0.117(6) Uani 1 1 d D . . H27 H 0.9603 0.4868 0.7700 0.141 Uiso 1 1 calc R . . C28 C 0.8451(12) 0.3903(7) 0.7592(4) 0.081(4) Uani 1 1 d D . . H28 H 0.8783 0.3803 0.7308 0.098 Uiso 1 1 calc R . . C29 C 0.7464(11) 0.3437(6) 0.7792(3) 0.060(3) Uani 1 1 d D . . H29 H 0.7137 0.3009 0.7637 0.072 Uiso 1 1 calc R . . C30 C 0.7726(9) 0.1446(5) 0.7989(3) 0.039(2) Uani 1 1 d . . . S2 S 0.7228(4) 0.0588(2) 0.72526(12) 0.0982(11) Uani 1 1 d . . . C31 C 0.6722(8) 0.0921(4) 0.7751(3) 0.046(2) Uani 1 1 d D . . C32 C 0.5291(6) 0.0660(3) 0.79271(19) 0.0103(12) Uiso 1 1 d D . . H32 H 0.4841 0.0774 0.8193 0.012 Uiso 1 1 calc R . . C33 C 0.4810(11) 0.0186(6) 0.7571(3) 0.120(7) Uani 1 1 d D . . H33 H 0.3932 -0.0075 0.7588 0.144 Uiso 1 1 calc R . . C34 C 0.5704(11) 0.0119(6) 0.7188(4) 0.086(4) Uani 1 1 d D . . H34 H 0.5453 -0.0154 0.6935 0.103 Uiso 1 1 calc R . . C35 C 0.1942(8) 0.7574(4) 0.9124(2) 0.046(2) Uani 1 1 d D . . C36 C 0.0551(8) 0.7864(5) 0.9120(3) 0.060(3) Uani 1 1 d D . . H36 H 0.0139 0.8047 0.9379 0.072 Uiso 1 1 calc R . . C37 C -0.0237(11) 0.7886(6) 0.8732(3) 0.080(4) Uani 1 1 d D . . H37 H -0.1178 0.8076 0.8733 0.096 Uiso 1 1 calc R . . C38 C 0.0364(13) 0.7629(6) 0.8345(3) 0.088(4) Uani 1 1 d D . . H38 H -0.0157 0.7645 0.8083 0.106 Uiso 1 1 calc R . . C39 C 0.1750(15) 0.7348(7) 0.8354(3) 0.098(5) Uani 1 1 d D . . H39 H 0.2176 0.7185 0.8093 0.117 Uiso 1 1 calc R . . C40 C 0.2527(12) 0.7301(6) 0.8739(2) 0.072(3) Uani 1 1 d D . . H40 H 0.3448 0.7085 0.8738 0.087 Uiso 1 1 calc R . . C41 C 0.2233(9) 0.8372(5) 1.0150(3) 0.047(2) Uani 1 1 d D . . C42 C 0.2095(10) 0.8218(6) 1.0601(3) 0.068(3) Uani 1 1 d D . . H42 H 0.2445 0.7759 1.0717 0.081 Uiso 1 1 calc R . . C43 C 0.1434(12) 0.8754(7) 1.0872(3) 0.086(4) Uani 1 1 d D . . H43 H 0.1360 0.8654 1.1172 0.103 Uiso 1 1 calc R . . C44 C 0.0882(13) 0.9437(7) 1.0707(4) 0.091(5) Uani 1 1 d D . . H44 H 0.0374 0.9775 1.0887 0.109 Uiso 1 1 calc R . . C45 C 0.1107(13) 0.9604(6) 1.0265(4) 0.099(5) Uani 1 1 d D . . H45 H 0.0818 1.0079 1.0153 0.119 Uiso 1 1 calc R . . C46 C 0.1760(11) 0.9068(5) 0.9988(3) 0.065(3) Uani 1 1 d D . . H46 H 0.1878 0.9181 0.9691 0.078 Uiso 1 1 calc R . . C47 C 0.0746(9) 0.6430(5) 1.0381(3) 0.045(2) Uani 1 1 d . . . S3 S 0.1498(5) 0.5604(3) 1.11007(15) 0.1236(16) Uani 1 1 d . . . C49 C 0.2969(7) 0.5486(4) 1.0352(2) 0.0265(16) Uiso 1 1 d D . . H49 H 0.3270 0.5549 1.0062 0.032 Uiso 1 1 calc R . . C48 C 0.1739(9) 0.5866(5) 1.0577(3) 0.051(2) Uani 1 1 d D . . C50 C 0.3593(14) 0.4994(7) 1.0686(4) 0.110(5) Uani 1 1 d D . . H50 H 0.4377 0.4672 1.0633 0.132 Uiso 1 1 calc R . . C51 C 0.2899(13) 0.5049(8) 1.1101(5) 0.121(7) Uani 1 1 d D . . H51 H 0.3221 0.4790 1.1351 0.146 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 0.03484(16) 0.0479(2) 0.04569(19) -0.00691(16) -0.00063(14) 0.00016(16) Bi2 0.03887(17) 0.0498(2) 0.04764(19) -0.00943(16) -0.00198(15) 0.00440(16) Bi3 0.03770(15) 0.0517(2) 0.04257(18) 0.00873(16) -0.00075(14) 0.00051(15) O1 0.035(3) 0.067(4) 0.048(4) -0.013(3) -0.001(3) 0.000(3) O2 0.050(4) 0.045(4) 0.053(4) -0.007(3) -0.002(3) -0.006(3) O3 0.038(3) 0.048(4) 0.055(4) -0.005(3) 0.007(3) 0.002(3) O4 0.041(4) 0.058(4) 0.047(4) -0.012(3) 0.004(3) 0.005(3) O5 0.042(4) 0.069(4) 0.054(4) 0.013(3) -0.005(3) -0.003(3) O6 0.043(3) 0.050(3) 0.047(4) 0.007(3) 0.000(3) 0.002(3) C1 0.045(5) 0.036(5) 0.046(5) 0.010(4) 0.001(4) -0.008(4) C2 0.062(6) 0.057(6) 0.061(7) -0.005(5) -0.014(5) -0.014(5) C3 0.087(8) 0.054(6) 0.057(7) 0.001(5) -0.005(6) -0.003(6) C4 0.090(9) 0.055(7) 0.077(9) 0.021(6) 0.007(7) 0.003(6) C5 0.087(9) 0.076(8) 0.069(8) 0.019(7) -0.013(7) -0.004(7) C6 0.078(8) 0.055(6) 0.057(7) 0.001(5) -0.026(6) -0.007(5) C7 0.033(4) 0.059(6) 0.038(5) -0.005(4) -0.011(3) 0.002(4) C8 0.083(7) 0.040(6) 0.067(7) 0.001(5) 0.013(6) 0.015(5) C9 0.099(9) 0.095(9) 0.062(8) 0.005(7) 0.027(7) 0.044(8) C10 0.076(7) 0.098(9) 0.065(8) 0.016(8) 0.023(6) -0.009(7) C11 0.081(8) 0.075(7) 0.051(7) 0.010(6) 0.008(6) -0.031(7) C12 0.055(6) 0.055(6) 0.056(6) -0.007(5) -0.010(5) -0.012(5) S1 0.076(2) 0.0642(18) 0.112(3) -0.0256(18) -0.001(2) 0.0086(15) C13 0.039(5) 0.044(5) 0.040(5) -0.011(4) -0.008(4) 0.005(4) C14 0.045(5) 0.054(5) 0.053(6) -0.010(4) -0.014(5) 0.006(5) C15 0.042(5) 0.059(6) 0.054(6) -0.013(5) 0.013(5) 0.010(5) C16 0.072(9) 0.138(13) 0.077(9) -0.025(9) 0.013(7) 0.009(9) C17 0.066(8) 0.116(11) 0.120(12) -0.068(10) -0.026(8) 0.035(8) C18 0.076(6) 0.040(5) 0.042(5) 0.007(4) -0.002(4) 0.007(5) C19 0.207(18) 0.077(9) 0.057(8) -0.012(7) -0.034(10) 0.026(10) C20 0.27(2) 0.109(12) 0.064(9) -0.010(9) -0.032(13) 0.046(15) C21 0.26(2) 0.121(11) 0.057(8) -0.022(8) -0.055(11) 0.071(15) C22 0.39(4) 0.166(17) 0.060(10) 0.012(12) -0.024(17) 0.14(2) C23 0.28(2) 0.124(13) 0.051(8) -0.006(9) 0.004(12) 0.080(16) C24 0.045(5) 0.047(5) 0.040(5) -0.001(4) -0.006(4) 0.017(4) C25 0.063(6) 0.089(8) 0.058(7) -0.007(6) -0.004(6) -0.018(6) C26 0.085(10) 0.111(11) 0.084(10) 0.008(8) 0.001(8) -0.030(8) C27 0.053(8) 0.151(15) 0.148(16) 0.069(13) 0.016(10) 0.014(10) C28 0.073(9) 0.094(9) 0.077(9) 0.005(8) 0.027(7) 0.017(7) C29 0.067(7) 0.062(7) 0.052(6) 0.006(5) 0.003(6) 0.021(6) C30 0.037(5) 0.039(5) 0.040(5) 0.005(4) -0.004(4) 0.005(4) S2 0.096(3) 0.104(3) 0.095(3) -0.020(2) -0.004(2) -0.008(2) C31 0.049(5) 0.036(5) 0.053(6) -0.005(4) -0.012(5) 0.012(4) C33 0.038(7) 0.141(13) 0.182(16) 0.093(12) 0.064(9) 0.026(7) C34 0.076(8) 0.046(6) 0.134(12) -0.012(7) -0.056(8) -0.010(5) C35 0.047(5) 0.045(5) 0.046(5) 0.013(4) -0.003(4) -0.007(4) C36 0.050(6) 0.094(8) 0.037(5) 0.010(5) -0.004(4) 0.001(5) C37 0.058(6) 0.115(10) 0.067(8) 0.031(7) -0.022(6) -0.012(7) C38 0.127(11) 0.075(8) 0.062(7) 0.014(7) -0.040(8) -0.027(9) C39 0.179(14) 0.081(8) 0.033(6) -0.011(6) -0.008(7) 0.037(10) C40 0.096(7) 0.076(7) 0.044(6) -0.005(6) 0.005(6) 0.028(7) C41 0.040(5) 0.063(6) 0.039(5) -0.001(4) 0.010(4) -0.003(4) C42 0.059(7) 0.084(8) 0.059(7) -0.008(6) 0.006(6) -0.009(6) C43 0.094(10) 0.126(11) 0.039(6) -0.033(7) 0.015(6) -0.020(9) C44 0.066(8) 0.118(12) 0.088(10) -0.064(10) 0.003(8) -0.008(8) C45 0.077(8) 0.062(7) 0.158(15) -0.028(9) -0.037(10) 0.005(6) C46 0.075(7) 0.057(6) 0.062(7) -0.004(5) -0.002(6) -0.007(6) C47 0.034(5) 0.052(5) 0.047(6) 0.011(4) -0.006(4) -0.005(4) S3 0.089(3) 0.161(4) 0.121(3) 0.059(3) -0.012(3) 0.005(3) C48 0.041(5) 0.053(5) 0.059(6) 0.020(5) -0.004(5) -0.007(5) C50 0.063(9) 0.117(11) 0.151(15) 0.023(11) 0.012(9) 0.032(8) C51 0.063(9) 0.094(10) 0.207(19) 0.083(12) -0.020(10) 0.009(7) _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 C7 2.236(8) . ? Bi1 C1 2.244(8) . ? Bi1 O1 2.317(6) . ? Bi1 O2 2.564(6) . ? Bi2 C18 2.223(8) . ? Bi2 C24 2.239(9) . ? Bi2 O3 2.324(6) . ? Bi2 O4 2.580(6) . ? Bi3 C41 2.235(8) . ? Bi3 C35 2.238(8) . ? Bi3 O5 2.290(6) . ? Bi3 O6 2.568(6) . ? O1 C30 1.272(10) 1_455 ? O2 C13 1.235(10) . ? O3 C13 1.270(11) . ? O4 C30 1.236(10) . ? O5 C47 1.273(11) 4_567 ? O6 C47 1.257(10) . ? C1 C6 1.390(8) . ? C1 C2 1.397(8) . ? C2 C3 1.384(8) . ? C2 H2 0.9300 . ? C3 C4 1.376(8) . ? C3 H3 0.9300 . ? C4 C5 1.365(9) . ? C4 H4 0.9300 . ? C5 C6 1.407(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.390(8) . ? C7 C12 1.403(8) . ? C8 C9 1.400(8) . ? C8 H8 0.9300 . ? C9 C10 1.391(9) . ? C9 H9 0.9300 . ? C10 C11 1.372(8) . ? C10 H10 0.9300 . ? C11 C12 1.373(8) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? S1 C17 1.669(13) . ? S1 C14 1.727(10) . ? C13 C14 1.501(12) . ? C14 C15 1.391(13) . ? C15 C16 1.386(15) . ? C15 H15 0.9300 . ? C16 C17 1.369(19) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.350(8) . ? C18 C23 1.366(9) . ? C19 C20 1.376(9) . ? C19 H19 0.9300 . ? C20 C21 1.364(9) . ? C20 H20 0.9300 . ? C21 C22 1.375(9) . ? C21 H21 0.9300 . ? C22 C23 1.376(9) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.378(8) . ? C24 C29 1.384(8) . ? C25 C26 1.375(9) . ? C25 H25 0.9300 . ? C26 C27 1.407(9) . ? C26 H26 0.9300 . ? C27 C28 1.386(9) . ? C27 H27 0.9300 . ? C28 C29 1.363(9) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 O1 1.272(10) 1_655 ? C30 C31 1.488(12) . ? S2 C34 1.638(10) . ? S2 C31 1.686(9) . ? C31 C32 1.496(8) . ? C32 C33 1.429(9) . ? C32 H32 0.9300 . ? C33 C34 1.433(9) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C40 1.374(8) . ? C35 C36 1.381(8) . ? C36 C37 1.384(8) . ? C36 H36 0.9300 . ? C37 C38 1.374(9) . ? C37 H37 0.9300 . ? C38 C39 1.371(9) . ? C38 H38 0.9300 . ? C39 C40 1.373(9) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C46 1.375(8) . ? C41 C42 1.401(8) . ? C42 C43 1.386(8) . ? C42 H42 0.9300 . ? C43 C44 1.385(9) . ? C43 H43 0.9300 . ? C44 C45 1.389(9) . ? C44 H44 0.9300 . ? C45 C46 1.393(8) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? C47 O5 1.273(10) 4_467 ? C47 C48 1.467(12) . ? S3 C51 1.613(13) . ? S3 C48 1.669(9) . ? C49 C50 1.446(9) . ? C49 C48 1.481(8) . ? C49 H49 0.9300 . ? C50 C51 1.419(9) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? 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 C7 Bi1 C1 94.2(3) . . ? C7 Bi1 O1 85.5(2) . . ? C1 Bi1 O1 86.9(2) . . ? C7 Bi1 O2 86.6(2) . . ? C1 Bi1 O2 84.1(2) . . ? O1 Bi1 O2 167.6(2) . . ? C18 Bi2 C24 97.5(3) . . ? C18 Bi2 O3 87.3(3) . . ? C24 Bi2 O3 85.0(2) . . ? C18 Bi2 O4 82.2(3) . . ? C24 Bi2 O4 83.5(2) . . ? O3 Bi2 O4 163.3(2) . . ? C41 Bi3 C35 99.7(3) . . ? C41 Bi3 O5 89.0(3) . . ? C35 Bi3 O5 81.8(2) . . ? C41 Bi3 O6 81.3(2) . . ? C35 Bi3 O6 83.0(2) . . ? O5 Bi3 O6 160.3(2) . . ? C30 O1 Bi1 111.8(6) 1_455 . ? C13 O2 Bi1 130.1(6) . . ? C13 O3 Bi2 108.6(5) . . ? C30 O4 Bi2 129.0(5) . . ? C47 O5 Bi3 114.1(6) 4_567 . ? C47 O6 Bi3 129.5(5) . . ? C6 C1 C2 117.3(8) . . ? C6 C1 Bi1 120.1(6) . . ? C2 C1 Bi1 122.6(6) . . ? C3 C2 C1 121.3(8) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 C2 119.6(9) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.8(10) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 118.0(10) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 122.1(9) . . ? C1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C8 C7 C12 118.4(8) . . ? C8 C7 Bi1 122.8(6) . . ? C12 C7 Bi1 118.8(5) . . ? C7 C8 C9 120.2(9) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 119.6(9) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 120.5(9) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.9(9) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 121.3(9) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C17 S1 C14 91.3(7) . . ? O2 C13 O3 123.7(8) . . ? O2 C13 C14 117.4(8) . . ? O3 C13 C14 118.9(8) . . ? C15 C14 C13 127.4(9) . . ? C15 C14 S1 112.9(7) . . ? C13 C14 S1 119.7(7) . . ? C16 C15 C14 108.3(10) . . ? C16 C15 H15 125.9 . . ? C14 C15 H15 125.9 . . ? C17 C16 C15 116.2(12) . . ? C17 C16 H16 121.9 . . ? C15 C16 H16 121.9 . . ? C16 C17 S1 111.2(10) . . ? C16 C17 H17 124.4 . . ? S1 C17 H17 124.4 . . ? C19 C18 C23 116.6(9) . . ? C19 C18 Bi2 124.9(7) . . ? C23 C18 Bi2 118.4(7) . . ? C18 C19 C20 123.2(11) . . ? C18 C19 H19 118.4 . . ? C20 C19 H19 118.4 . . ? C21 C20 C19 120.4(13) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 116.7(12) . . ? C20 C21 H21 121.7 . . ? C22 C21 H21 121.7 . . ? C21 C22 C23 121.8(13) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C18 C23 C22 121.0(12) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C25 C24 C29 116.8(9) . . ? C25 C24 Bi2 125.4(6) . . ? C29 C24 Bi2 117.8(7) . . ? C26 C25 C24 122.4(10) . . ? C26 C25 H25 118.8 . . ? C24 C25 H25 118.8 . . ? C25 C26 C27 118.1(12) . . ? C25 C26 H26 121.0 . . ? C27 C26 H26 121.0 . . ? C28 C27 C26 121.3(13) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C29 C28 C27 117.1(11) . . ? C29 C28 H28 121.5 . . ? C27 C28 H28 121.5 . . ? C28 C29 C24 124.3(10) . . ? C28 C29 H29 117.8 . . ? C24 C29 H29 117.8 . . ? O4 C30 O1 122.3(8) . 1_655 ? O4 C30 C31 117.1(8) . . ? O1 C30 C31 120.5(8) 1_655 . ? C34 S2 C31 92.3(5) . . ? C30 C31 C32 124.2(7) . . ? C30 C31 S2 118.3(6) . . ? C32 C31 S2 117.5(6) . . ? C33 C32 C31 100.3(6) . . ? C33 C32 H32 129.9 . . ? C31 C32 H32 129.9 . . ? C32 C33 C34 118.8(8) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C33 C34 S2 110.9(8) . . ? C33 C34 H34 124.5 . . ? S2 C34 H34 124.5 . . ? C40 C35 C36 118.9(8) . . ? C40 C35 Bi3 117.8(6) . . ? C36 C35 Bi3 123.1(6) . . ? C35 C36 C37 120.5(9) . . ? C35 C36 H36 119.7 . . ? C37 C36 H36 119.7 . . ? C38 C37 C36 120.4(10) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C39 C38 C37 118.4(10) . . ? C39 C38 H38 120.8 . . ? C37 C38 H38 120.8 . . ? C38 C39 C40 121.8(10) . . ? C38 C39 H39 119.1 . . ? C40 C39 H39 119.1 . . ? C39 C40 C35 119.9(9) . . ? C39 C40 H40 120.1 . . ? C35 C40 H40 120.1 . . ? C46 C41 C42 119.3(9) . . ? C46 C41 Bi3 124.4(6) . . ? C42 C41 Bi3 116.4(6) . . ? C43 C42 C41 119.5(10) . . ? C43 C42 H42 120.2 . . ? C41 C42 H42 120.2 . . ? C44 C43 C42 121.5(10) . . ? C44 C43 H43 119.3 . . ? C42 C43 H43 119.3 . . ? C43 C44 C45 118.3(11) . . ? C43 C44 H44 120.8 . . ? C45 C44 H44 120.8 . . ? C44 C45 C46 120.5(11) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? C41 C46 C45 120.6(9) . . ? C41 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? O6 C47 O5 121.7(8) . 4_467 ? O6 C47 C48 119.7(8) . . ? O5 C47 C48 118.6(8) 4_467 . ? C51 S3 C48 93.3(6) . . ? C50 C49 C48 104.2(7) . . ? C50 C49 H49 127.9 . . ? C48 C49 H49 127.9 . . ? C47 C48 C49 126.1(8) . . ? C47 C48 S3 119.0(7) . . ? C49 C48 S3 114.9(6) . . ? C51 C50 C49 113.8(10) . . ? C51 C50 H50 123.1 . . ? C49 C50 H50 123.1 . . ? C50 C51 S3 113.7(10) . . ? C50 C51 H51 123.2 . . ? S3 C51 H51 123.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.453 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.133 #===END data_compound12 _database_code_depnum_ccdc_archive 'CCDC 825251' #TrackingRef '- kck-dal-11-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 Bi O4 S2' _chemical_formula_weight 540.35 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6447(8) _cell_length_b 9.6012(9) _cell_length_c 10.6965(10) _cell_angle_alpha 81.2790(10) _cell_angle_beta 71.4180(10) _cell_angle_gamma 71.4290(10) _cell_volume 796.46(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 11.346 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1133 _exptl_absorpt_correction_T_max 0.2100 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7655 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2802 _reflns_number_gt 2685 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.4709P] 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 2802 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0556 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Bi Bi 0.288248(18) 0.205805(15) 0.571752(15) 0.01562(8) Uani 1 1 d . . . C1 C 0.4402(5) 0.2223(4) 0.6989(4) 0.0151(9) Uani 1 1 d . . . C2 C 0.5636(5) 0.2954(5) 0.6462(5) 0.0194(10) Uani 1 1 d . . . H2 H 0.5791 0.3372 0.5605 0.023 Uiso 1 1 calc R . . C3 C 0.6642(6) 0.3065(5) 0.7204(5) 0.0241(10) Uani 1 1 d . . . H3 H 0.7470 0.3552 0.6838 0.029 Uiso 1 1 calc R . . C4 C 0.6429(7) 0.2464(5) 0.8470(5) 0.0288(11) Uani 1 1 d . . . H4 H 0.7111 0.2538 0.8961 0.035 Uiso 1 1 calc R . . C5 C 0.5183(7) 0.1742(5) 0.9015(5) 0.0305(12) Uani 1 1 d . . . H5 H 0.5031 0.1335 0.9876 0.037 Uiso 1 1 calc R . . C6 C 0.4171(6) 0.1625(5) 0.8290(5) 0.0225(10) Uani 1 1 d . . . H6 H 0.3335 0.1148 0.8665 0.027 Uiso 1 1 calc R . . C7 C 0.0979(6) 0.4929(5) 0.6256(4) 0.0169(9) Uani 1 1 d . . . C8 C -0.0231(6) 0.6391(5) 0.6573(5) 0.0215(10) Uani 1 1 d . . . C10 C -0.2700(7) 0.8296(7) 0.7476(5) 0.0426(16) Uani 1 1 d . . . H10 H -0.3795 0.8825 0.7929 0.051 Uiso 1 1 calc R . . C11 C -0.1555(10) 0.8959(6) 0.6686(6) 0.0479(19) Uani 1 1 d . . . H11 H -0.1780 0.9977 0.6597 0.057 Uiso 1 1 calc R . . C12 C 0.2656(6) -0.0650(5) 0.7083(5) 0.0191(10) Uani 1 1 d . . . C13 C 0.2297(6) -0.1882(5) 0.7975(5) 0.0181(9) Uani 1 1 d . . . C15 C 0.0995(7) -0.3390(6) 0.9676(5) 0.0274(11) Uani 1 1 d . . . H15 H 0.0257 -0.3747 1.0396 0.033 Uiso 1 1 calc R . . C16 C 0.2469(7) -0.4304(5) 0.8962(5) 0.0285(11) Uani 1 1 d . . . H16 H 0.2796 -0.5311 0.9169 0.034 Uiso 1 1 calc R . . O1 O 0.2388(4) 0.4819(4) 0.5385(3) 0.0218(7) Uani 1 1 d . . . O2 O 0.0567(4) 0.3788(3) 0.6864(3) 0.0191(7) Uani 1 1 d . . . O3 O 0.1596(4) 0.0643(3) 0.7349(3) 0.0212(7) Uani 1 1 d . . . O4 O 0.3950(4) -0.0822(4) 0.6106(3) 0.0236(7) Uani 1 1 d . . . S1 S -0.2088(3) 0.6620(2) 0.7583(2) 0.0409(5) Uani 0.72 1 d P . . S2 S 0.0153(2) 0.79223(19) 0.59376(19) 0.0306(4) Uani 0.72 1 d P . . S3 S 0.0588(3) -0.1713(2) 0.9238(2) 0.0369(4) Uani 0.72 1 d P . . S4 S 0.3605(3) -0.3542(2) 0.7744(2) 0.0368(5) Uani 0.72 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.01386(11) 0.01240(11) 0.01834(11) -0.00116(7) -0.00316(7) -0.00207(7) C1 0.015(2) 0.009(2) 0.016(2) -0.0026(17) -0.0024(18) 0.0023(16) C2 0.019(2) 0.018(2) 0.018(2) -0.0022(19) -0.0032(19) -0.0018(18) C3 0.024(2) 0.017(2) 0.032(3) -0.007(2) -0.008(2) -0.0029(19) C4 0.039(3) 0.019(2) 0.032(3) -0.006(2) -0.021(2) 0.000(2) C5 0.049(3) 0.025(3) 0.019(3) -0.003(2) -0.014(2) -0.007(2) C6 0.026(2) 0.012(2) 0.025(3) -0.0022(19) -0.001(2) -0.0062(18) C7 0.020(2) 0.014(2) 0.016(2) -0.0030(18) -0.0080(19) -0.0007(18) C8 0.026(3) 0.018(2) 0.021(2) -0.0023(19) -0.014(2) 0.0013(19) C10 0.034(3) 0.050(4) 0.019(3) -0.008(3) -0.008(2) 0.024(3) C11 0.107(6) 0.011(3) 0.033(3) -0.003(2) -0.042(4) -0.006(3) C12 0.020(2) 0.018(2) 0.024(3) 0.0016(19) -0.009(2) -0.0095(18) C13 0.021(2) 0.013(2) 0.023(2) 0.0000(18) -0.011(2) -0.0049(18) C15 0.035(3) 0.034(3) 0.020(3) 0.002(2) -0.008(2) -0.021(2) C16 0.043(3) 0.016(2) 0.033(3) 0.004(2) -0.022(3) -0.010(2) O1 0.0205(17) 0.0173(17) 0.0237(18) 0.0018(14) -0.0034(15) -0.0045(13) O2 0.0147(15) 0.0150(15) 0.0208(17) -0.0007(13) 0.0010(13) -0.0012(12) O3 0.0190(16) 0.0158(15) 0.0253(18) 0.0000(13) -0.0019(14) -0.0052(13) O4 0.0186(17) 0.0218(17) 0.0264(19) 0.0027(14) -0.0020(15) -0.0067(13) S1 0.0400(11) 0.0378(11) 0.0384(12) -0.0006(9) -0.0123(9) -0.0020(9) S2 0.0293(9) 0.0273(9) 0.0379(11) -0.0085(8) -0.0132(8) -0.0052(7) S3 0.0433(11) 0.0366(10) 0.0352(11) 0.0039(9) -0.0136(9) -0.0177(9) S4 0.0443(11) 0.0240(9) 0.0470(12) 0.0023(8) -0.0196(10) -0.0121(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi C1 2.222(4) . ? Bi O3 2.266(3) . ? Bi O2 2.282(3) . ? Bi O1 2.535(3) . ? Bi O4 2.635(3) . ? C1 C2 1.386(6) . ? C1 C6 1.400(6) . ? C2 C3 1.386(7) . ? C2 H2 0.9300 . ? C3 C4 1.368(7) . ? C3 H3 0.9300 . ? C4 C5 1.390(7) . ? C4 H4 0.9300 . ? C5 C6 1.378(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.259(6) . ? C7 O2 1.278(5) . ? C7 C8 1.471(6) . ? C8 S1 1.593(5) . ? C8 S2 1.612(5) . ? C10 C11 1.344(9) . ? C10 S1 1.524(6) . ? C10 H10 0.9300 . ? C11 S2 1.537(7) . ? C11 H11 0.9300 . ? C12 O4 1.249(6) . ? C12 O3 1.295(5) . ? C12 C13 1.452(6) . ? C13 S4 1.635(5) . ? C13 S3 1.636(5) . ? C15 C16 1.359(7) . ? C15 S3 1.566(5) . ? C15 H15 0.9300 . ? C16 S4 1.597(5) . ? C16 H16 0.9300 . ? 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 C1 Bi O3 89.04(13) . . ? C1 Bi O2 90.98(13) . . ? O3 Bi O2 78.55(10) . . ? C1 Bi O1 83.20(13) . . ? O3 Bi O1 131.91(11) . . ? O2 Bi O1 54.34(10) . . ? C1 Bi O4 87.62(12) . . ? O3 Bi O4 53.09(10) . . ? O2 Bi O4 131.64(10) . . ? O1 Bi O4 169.29(10) . . ? C2 C1 C6 118.7(4) . . ? C2 C1 Bi 118.1(3) . . ? C6 C1 Bi 123.1(3) . . ? C3 C2 C1 120.5(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.7(5) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.6(5) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.1(4) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 O2 121.2(4) . . ? O1 C7 C8 119.8(4) . . ? O2 C7 C8 119.0(4) . . ? C7 C8 S1 122.9(4) . . ? C7 C8 S2 124.4(4) . . ? S1 C8 S2 112.7(3) . . ? C11 C10 S1 115.7(5) . . ? C11 C10 H10 122.2 . . ? S1 C10 H10 122.2 . . ? C10 C11 S2 115.5(4) . . ? C10 C11 H11 122.2 . . ? S2 C11 H11 122.2 . . ? O4 C12 O3 121.1(4) . . ? O4 C12 C13 121.5(4) . . ? O3 C12 C13 117.5(4) . . ? C12 C13 S4 120.7(4) . . ? C12 C13 S3 123.0(3) . . ? S4 C13 S3 116.2(3) . . ? C16 C15 S3 117.4(4) . . ? C16 C15 H15 121.3 . . ? S3 C15 H15 121.3 . . ? C15 C16 S4 115.9(4) . . ? C15 C16 H16 122.1 . . ? S4 C16 H16 122.1 . . ? C7 O1 Bi 86.5(3) . . ? C7 O2 Bi 97.7(2) . . ? C12 O3 Bi 100.9(3) . . ? C12 O4 Bi 84.9(3) . . ? C10 S1 C8 98.4(3) . . ? C11 S2 C8 97.5(3) . . ? C15 S3 C13 95.4(3) . . ? C16 S4 C13 95.1(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.318 _refine_diff_density_min -1.158 _refine_diff_density_rms 0.149 #===END