# Copyright The Royal Society of Chemistry, 1998 # CCDC Number: 186/1192 data_1 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Data were truncated at 24.7\%. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _audit_creation_method SHELXL _chemical_name_systematic ; Tetrachloro bis-2,6-dimethylphenoxy bis tetrahydrofuran dibismuthate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[Bi2 Cl4 (thf)2 (O -2,6-Me2 C6 H3)2]' _chemical_formula_analytical ? _chemical_formula_sum 'C12 H17 Bi Cl2 O2' _chemical_formula_weight 473.14 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 '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 14.266(3) _cell_length_b 14.629(3) _cell_length_c 14.468(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.90(3) _cell_angle_gamma 90.00 _cell_volume 2974.4(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 142 _cell_measurement_theta_min 14.450 _cell_measurement_theta_max 22.333 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.113 _exptl_crystal_density_method ? _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 12.203 _exptl_absorpt_correction_type 'Sadabs' _exptl_absorpt_correction_T_min 0.582097 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 9327 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3396 _reflns_number_observed 2357 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0279P)^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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00015(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3396 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_obs 0.0395 _refine_ls_wR_factor_all 0.0745 _refine_ls_wR_factor_obs 0.0652 _refine_ls_goodness_of_fit_all 0.960 _refine_ls_goodness_of_fit_obs 1.019 _refine_ls_restrained_S_all 0.960 _refine_ls_restrained_S_obs 1.019 _refine_ls_shift/esd_max -0.005 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.45761(2) 0.59781(2) 0.87065(2) 0.02191(11) Uani 1 d . . Cl1 Cl 0.4411(2) 0.76475(15) 0.8767(2) 0.0407(6) Uani 1 d . . Cl2 Cl 0.56367(14) 0.6044(2) 1.03448(13) 0.0352(5) Uani 1 d . . O1 O 0.5843(3) 0.6029(4) 0.8017(3) 0.0247(11) Uani 1 d . . C1 C 0.6781(5) 0.5846(6) 0.8432(5) 0.025(2) Uani 1 d . . C2 C 0.7087(6) 0.4947(6) 0.8475(6) 0.032(2) Uani 1 d . . C3 C 0.8046(7) 0.4774(7) 0.8804(6) 0.043(3) Uani 1 d . . H3A H 0.8275(7) 0.4163(7) 0.8819(6) 0.051 Uiso 1 calc R . C4 C 0.8665(7) 0.5470(10) 0.9106(7) 0.057(3) Uani 1 d . . H4A H 0.9315(7) 0.5342(10) 0.9345(7) 0.069 Uiso 1 calc R . C5 C 0.8337(7) 0.6362(9) 0.9059(6) 0.050(3) Uani 1 d . . H5A H 0.8775(7) 0.6839(9) 0.9265(6) 0.060 Uiso 1 calc R . C6 C 0.7387(6) 0.6589(6) 0.8719(5) 0.032(2) Uani 1 d . . C7 C 0.6408(7) 0.4172(5) 0.8144(6) 0.043(2) Uani 1 d . . H7A H 0.6751(7) 0.3589(5) 0.8228(6) 0.064 Uiso 1 calc R . H7B H 0.6142(7) 0.4257(5) 0.7478(6) 0.064 Uiso 1 calc R . H7C H 0.5891(7) 0.4167(5) 0.8511(6) 0.064 Uiso 1 calc R . C8 C 0.7028(6) 0.7556(6) 0.8692(6) 0.038(2) Uani 1 d . . H8A H 0.6347(6) 0.7566(6) 0.8430(6) 0.058 Uiso 1 calc R . H8B H 0.7374(6) 0.7927(6) 0.8298(6) 0.058 Uiso 1 calc R . H8C H 0.7129(6) 0.7807(6) 0.9329(6) 0.058 Uiso 1 calc R . O2 O 0.2758(4) 0.5962(5) 0.8878(4) 0.048(2) Uani 1 d . . C9 C 0.2267(6) 0.5104(7) 0.8791(6) 0.039(2) Uani 1 d . . H9A H 0.2356(6) 0.4780(7) 0.9401(6) 0.047 Uiso 1 calc R . H9B H 0.2502(6) 0.4709(7) 0.8324(6) 0.047 Uiso 1 calc R . C10 C 0.1209(7) 0.5346(8) 0.8464(7) 0.056(3) Uani 1 d . . H10A H 0.1027(7) 0.5274(8) 0.7776(7) 0.067 Uiso 1 calc R . H10B H 0.0793(7) 0.4956(8) 0.8779(7) 0.067 Uiso 1 calc R . C11 C 0.1148(8) 0.6306(10) 0.8739(8) 0.078(4) Uani 1 d . . H11A H 0.0665(8) 0.6633(10) 0.8284(8) 0.093 Uiso 1 calc R . H11B H 0.0966(8) 0.6349(10) 0.9368(8) 0.093 Uiso 1 calc R . C12 C 0.2086(8) 0.6705(8) 0.8753(9) 0.068(4) Uani 1 d . . H12A H 0.2110(8) 0.7027(8) 0.8156(9) 0.082 Uiso 1 calc R . H12B H 0.2235(8) 0.7148(8) 0.9274(9) 0.082 Uiso 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 0.01892(15) 0.0287(2) 0.01782(14) 0.0018(2) 0.00241(9) 0.0009(2) Cl1 0.0423(15) 0.0353(12) 0.0434(13) -0.0055(11) 0.0046(11) 0.0096(10) Cl2 0.0347(11) 0.0453(13) 0.0223(9) 0.0012(10) -0.0042(8) -0.0099(11) O1 0.016(2) 0.034(3) 0.022(2) -0.001(3) 0.001(2) -0.002(3) C1 0.017(4) 0.039(5) 0.017(4) 0.003(4) 0.001(3) 0.005(4) C2 0.030(5) 0.040(6) 0.026(5) 0.003(4) 0.008(4) 0.012(4) C3 0.041(6) 0.063(7) 0.028(5) 0.015(5) 0.019(4) 0.024(5) C4 0.018(5) 0.124(11) 0.032(5) 0.012(6) 0.010(4) 0.010(6) C5 0.024(5) 0.100(9) 0.024(5) -0.002(5) 0.001(4) -0.010(6) C6 0.021(4) 0.057(6) 0.018(4) -0.007(4) 0.004(3) -0.003(4) C7 0.070(7) 0.024(5) 0.037(5) 0.003(4) 0.017(5) 0.007(5) C8 0.041(6) 0.042(6) 0.031(5) -0.006(4) 0.003(4) -0.020(5) O2 0.030(3) 0.048(4) 0.067(4) 0.012(4) 0.011(3) 0.000(4) C9 0.031(5) 0.062(7) 0.030(5) -0.001(5) 0.018(4) -0.001(5) C10 0.027(6) 0.091(9) 0.050(6) 0.011(6) 0.007(5) -0.007(6) C11 0.041(7) 0.132(12) 0.058(8) -0.004(8) 0.001(6) 0.019(8) C12 0.052(8) 0.068(8) 0.090(9) 0.011(7) 0.024(7) 0.030(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 O1 2.211(5) . ? Bi1 Cl1 2.456(2) . ? Bi1 O1 2.463(5) 2_656 ? Bi1 Cl2 2.585(2) . ? Bi1 O2 2.648(6) . ? Bi1 Cl2 3.297(2) 5_667 ? O1 C1 1.396(8) . ? O1 Bi1 2.463(5) 2_656 ? C1 C2 1.383(11) . ? C1 C6 1.406(11) . ? C2 C3 1.393(12) . ? C2 C7 1.515(12) . ? C3 C4 1.370(14) . ? C4 C5 1.383(15) . ? C5 C6 1.400(12) . ? C6 C8 1.503(12) . ? O2 C9 1.433(10) . ? O2 C12 1.439(11) . ? C9 C10 1.543(12) . ? C10 C11 1.47(2) . ? C11 C12 1.457(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Bi1 Cl1 94.18(15) . . ? O1 Bi1 O1 67.5(2) . 2_656 ? Cl1 Bi1 O1 89.86(14) . 2_656 ? O1 Bi1 Cl2 91.00(13) . . ? Cl1 Bi1 Cl2 88.55(7) . . ? O1 Bi1 Cl2 158.26(12) 2_656 . ? O1 Bi1 O2 158.9(2) . . ? Cl1 Bi1 O2 84.5(2) . . ? O1 Bi1 O2 91.4(2) 2_656 . ? Cl2 Bi1 O2 110.03(15) . . ? O1 Bi1 Cl2 111.06(14) . 5_667 ? Cl1 Bi1 Cl2 149.43(7) . 5_667 ? O1 Bi1 Cl2 115.15(13) 2_656 5_667 ? Cl2 Bi1 Cl2 74.53(7) . 5_667 ? O2 Bi1 Cl2 77.95(15) . 5_667 ? C1 O1 Bi1 126.7(4) . . ? C1 O1 Bi1 118.5(4) . 2_656 ? Bi1 O1 Bi1 112.4(2) . 2_656 ? C2 C1 O1 118.3(7) . . ? C2 C1 C6 123.3(7) . . ? O1 C1 C6 118.2(7) . . ? C1 C2 C3 118.1(9) . . ? C1 C2 C7 121.2(7) . . ? C3 C2 C7 120.6(8) . . ? C4 C3 C2 121.0(9) . . ? C3 C4 C5 119.4(9) . . ? C4 C5 C6 122.7(9) . . ? C5 C6 C1 115.4(9) . . ? C5 C6 C8 122.5(9) . . ? C1 C6 C8 122.1(7) . . ? C9 O2 C12 110.2(7) . . ? C9 O2 Bi1 118.1(5) . . ? C12 O2 Bi1 128.5(6) . . ? O2 C9 C10 105.2(8) . . ? C11 C10 C9 103.8(9) . . ? C12 C11 C10 106.8(10) . . ? O2 C12 C11 106.9(10) . . ? _refine_diff_density_max 1.455 _refine_diff_density_min -1.560 _refine_diff_density_rms 0.209 #=END data_2 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _audit_creation_method SHELXL _chemical_name_systematic ; Tetrachloro bis-2,4,6-trimethylphenoxy bis tetrahydrofuran dibismuthate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[Bi2 Cl4 (thf)2 (O -2,4,6-Me3 C6 H2)2]' _chemical_formula_analytical ? _chemical_formula_sum 'C13 H19 Bi Cl2 O2' _chemical_formula_weight 487.16 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 '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 15.769(3) _cell_length_b 13.743(3) _cell_length_c 14.405(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.58(3) _cell_angle_gamma 90.00 _cell_volume 3107.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 235 _cell_measurement_theta_min 14.450 _cell_measurement_theta_max 22.550 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.083 _exptl_crystal_density_method ? _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 11.685 _exptl_absorpt_correction_type 'Sadabs' _exptl_absorpt_correction_T_min 0.293096 _exptl_absorpt_correction_T_max 0.491504 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 9560 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3549 _reflns_number_observed 2874 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0201P)^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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00018(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3549 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_obs 0.0241 _refine_ls_wR_factor_all 0.0496 _refine_ls_wR_factor_obs 0.0466 _refine_ls_goodness_of_fit_all 1.035 _refine_ls_goodness_of_fit_obs 1.086 _refine_ls_restrained_S_all 1.035 _refine_ls_restrained_S_obs 1.086 _refine_ls_shift/esd_max -0.008 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.039840(9) 0.605366(13) 0.125886(10) 0.02268(6) Uani 1 d . . Cl1 Cl 0.05564(7) 0.78319(9) 0.12736(8) 0.0369(3) Uani 1 d . . Cl2 Cl -0.05004(7) 0.61559(10) -0.03244(8) 0.0369(3) Uani 1 d . . O1 O -0.0741(2) 0.6075(2) 0.2012(2) 0.0240(6) Uani 1 d . . O2 O 0.2002(2) 0.6155(3) 0.0796(3) 0.0496(10) Uani 1 d . . C1 C -0.1595(2) 0.5948(3) 0.1711(3) 0.0222(9) Uani 1 d . . C2 C -0.1940(3) 0.5019(4) 0.1783(3) 0.0276(10) Uani 1 d . . C3 C -0.2824(3) 0.4916(4) 0.1589(3) 0.0355(12) Uani 1 d . . H3A H -0.3072(3) 0.4291(4) 0.1644(3) 0.043 Uiso 1 calc R . C4 C -0.3351(3) 0.5697(4) 0.1319(3) 0.0374(13) Uani 1 d . . C5 C -0.2977(3) 0.6589(4) 0.1211(3) 0.0332(12) Uani 1 d . . H5A H -0.3328(3) 0.7120(4) 0.0994(3) 0.040 Uiso 1 calc R . C6 C -0.2100(3) 0.6750(4) 0.1407(3) 0.0280(10) Uani 1 d . . C7 C -0.1728(3) 0.7738(4) 0.1302(3) 0.0349(12) Uani 1 d . . H7A H -0.1110(3) 0.7713(4) 0.1468(3) 0.052 Uiso 1 calc R . H7B H -0.1984(3) 0.8196(4) 0.1716(3) 0.052 Uiso 1 calc R . H7C H -0.1844(3) 0.7955(4) 0.0654(3) 0.052 Uiso 1 calc R . C8 C -0.4313(3) 0.5571(5) 0.1151(4) 0.052(2) Uani 1 d . . H8A H -0.4462(3) 0.4891(5) 0.1261(4) 0.077 Uiso 1 calc R . H8B H -0.4506(3) 0.5749(5) 0.0506(4) 0.077 Uiso 1 calc R . H8C H -0.4592(3) 0.5992(5) 0.1579(4) 0.077 Uiso 1 calc R . C9 C -0.1392(3) 0.4153(3) 0.2047(3) 0.0374(12) Uani 1 d . . H9A H -0.1751(3) 0.3571(3) 0.2061(3) 0.056 Uiso 1 calc R . H9B H -0.1088(3) 0.4257(3) 0.2665(3) 0.056 Uiso 1 calc R . H9C H -0.0980(3) 0.4063(3) 0.1588(3) 0.056 Uiso 1 calc R . C10 C 0.2442(3) 0.5237(5) 0.0814(4) 0.0471(15) Uani 1 d . . H10A H 0.2319(3) 0.4897(5) 0.0210(4) 0.057 Uiso 1 calc R . H10B H 0.2254(3) 0.4817(5) 0.1314(4) 0.057 Uiso 1 calc R . C11 C 0.3388(3) 0.5446(6) 0.0995(5) 0.076(2) Uani 1 d . . H11A H 0.3625(3) 0.5153(6) 0.1592(5) 0.091 Uiso 1 calc R . H11B H 0.3699(3) 0.5182(6) 0.0486(5) 0.091 Uiso 1 calc R . C12 C 0.3454(3) 0.6505(5) 0.1031(5) 0.068(2) Uani 1 d . . H12A H 0.3652(3) 0.6758(5) 0.0446(5) 0.082 Uiso 1 calc R . H12B H 0.3866(3) 0.6708(5) 0.1559(5) 0.082 Uiso 1 calc R . C13 C 0.2583(3) 0.6892(5) 0.1158(4) 0.0443(14) Uani 1 d . . H13A H 0.2522(3) 0.7011(5) 0.1826(4) 0.053 Uiso 1 calc R . H13B H 0.2477(3) 0.7509(5) 0.0810(4) 0.053 Uiso 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 0.01516(8) 0.02976(10) 0.02294(9) -0.00513(9) 0.00102(5) 0.00034(8) Cl1 0.0343(6) 0.0344(7) 0.0423(7) 0.0010(6) 0.0057(5) -0.0103(5) Cl2 0.0368(6) 0.0413(8) 0.0303(6) -0.0059(6) -0.0090(5) 0.0088(6) O1 0.0150(13) 0.033(2) 0.0246(14) 0.0021(15) 0.0032(10) 0.0011(14) O2 0.019(2) 0.061(3) 0.069(2) -0.019(2) 0.003(2) 0.002(2) C1 0.017(2) 0.031(3) 0.019(2) 0.001(2) 0.0004(15) -0.001(2) C2 0.025(2) 0.037(3) 0.020(2) 0.001(2) -0.004(2) -0.002(2) C3 0.023(2) 0.045(3) 0.037(3) 0.001(2) 0.001(2) -0.011(2) C4 0.020(2) 0.064(4) 0.027(2) -0.001(2) -0.001(2) -0.002(2) C5 0.024(2) 0.052(4) 0.023(2) 0.000(2) -0.003(2) 0.016(2) C6 0.022(2) 0.041(3) 0.020(2) 0.002(2) -0.001(2) 0.004(2) C7 0.034(3) 0.033(3) 0.038(3) 0.007(2) 0.000(2) 0.010(2) C8 0.019(2) 0.081(5) 0.053(3) -0.004(3) -0.002(2) 0.003(3) C9 0.031(3) 0.033(3) 0.046(3) 0.001(2) -0.007(2) -0.006(2) C10 0.028(3) 0.062(4) 0.051(3) -0.019(3) 0.003(2) 0.008(3) C11 0.027(3) 0.097(6) 0.101(5) -0.056(5) -0.001(3) 0.003(3) C12 0.029(3) 0.082(5) 0.095(5) 0.037(4) 0.012(3) 0.001(3) C13 0.027(2) 0.064(4) 0.043(3) 0.002(3) 0.007(2) -0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O1 2.187(3) . ? Bi1 Cl1 2.4563(13) . ? Bi1 O1 2.497(3) 2 ? Bi1 Cl2 2.5695(13) . ? Bi1 O2 2.680(3) . ? Bi1 Cl2 3.3317(14) 5_565 ? O1 C1 1.386(4) . ? O1 Bi1 2.497(3) 2 ? O2 C13 1.429(6) . ? O2 C10 1.439(6) . ? C1 C2 1.396(6) . ? C1 C6 1.404(6) . ? C2 C3 1.402(6) . ? C2 C9 1.497(6) . ? C3 C4 1.390(7) . ? C4 C5 1.375(7) . ? C4 C8 1.524(6) . ? C5 C6 1.402(6) . ? C6 C7 1.494(7) . ? C10 C11 1.516(7) . ? C11 C12 1.460(9) . ? C12 C13 1.501(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Bi1 Cl1 93.99(9) . . ? O1 Bi1 O1 67.25(11) . 2 ? Cl1 Bi1 O1 88.14(8) . 2 ? O1 Bi1 Cl2 91.77(8) . . ? Cl1 Bi1 Cl2 90.00(4) . . ? O1 Bi1 Cl2 158.73(7) 2 . ? O1 Bi1 O2 164.30(11) . . ? Cl1 Bi1 O2 81.55(9) . . ? O1 Bi1 O2 97.45(10) 2 . ? Cl2 Bi1 O2 103.22(9) . . ? O1 Bi1 Cl2 106.69(8) . 5_565 ? Cl1 Bi1 Cl2 154.34(4) . 5_565 ? O1 Bi1 Cl2 113.56(7) 2 5_565 ? Cl2 Bi1 Cl2 74.65(4) . 5_565 ? O2 Bi1 Cl2 82.14(9) . 5_565 ? C1 O1 Bi1 131.6(2) . . ? C1 O1 Bi1 114.8(2) . 2 ? Bi1 O1 Bi1 112.73(11) . 2 ? C13 O2 C10 108.9(4) . . ? C13 O2 Bi1 122.2(3) . . ? C10 O2 Bi1 114.5(3) . . ? O1 C1 C2 117.8(4) . . ? O1 C1 C6 120.2(4) . . ? C2 C1 C6 121.9(4) . . ? C1 C2 C3 117.7(4) . . ? C1 C2 C9 121.8(4) . . ? C3 C2 C9 120.5(4) . . ? C4 C3 C2 122.2(5) . . ? C5 C4 C3 118.0(4) . . ? C5 C4 C8 121.0(5) . . ? C3 C4 C8 121.0(5) . . ? C4 C5 C6 122.9(5) . . ? C5 C6 C1 117.2(5) . . ? C5 C6 C7 120.8(4) . . ? C1 C6 C7 121.9(4) . . ? O2 C10 C11 107.6(5) . . ? C12 C11 C10 105.1(5) . . ? C11 C12 C13 107.1(5) . . ? O2 C13 C12 105.5(5) . . ? _refine_diff_density_max 1.370 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.127 #=END data_3 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full hemisphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _audit_creation_method SHELXL _chemical_name_systematic ; Bis tetramethyl ammonium hexa-2,6-dimethylphenoxy dichloro dibismuthate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[N Me4]2 [Bi2 (O-2,6-Me2 C6 H3)6 Cl2]' _chemical_formula_analytical ? _chemical_formula_sum 'C28 H39 Bi Cl N O3' _chemical_formula_weight 682.03 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(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 12.418(3) _cell_length_b 13.841(3) _cell_length_c 16.892(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.77(3) _cell_angle_gamma 90.00 _cell_volume 2902.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 399 _cell_measurement_theta_min 14.536 _cell_measurement_theta_max 22.550 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method ? _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 6.194 _exptl_absorpt_correction_type 'Sadabs' _exptl_absorpt_correction_T_min 0.216696 _exptl_absorpt_correction_T_max 0.403385 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 17745 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6572 _reflns_number_observed 4980 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0297P)^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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00018(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6572 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_obs 0.0282 _refine_ls_wR_factor_all 0.0598 _refine_ls_wR_factor_obs 0.0558 _refine_ls_goodness_of_fit_all 0.895 _refine_ls_goodness_of_fit_obs 0.967 _refine_ls_restrained_S_all 0.895 _refine_ls_restrained_S_obs 0.967 _refine_ls_shift/esd_max 0.089 _refine_ls_shift/esd_mean 0.004 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.350976(11) 0.085841(10) -0.001815(8) 0.03081(6) Uani 1 d . . Cl1 Cl 0.48874(8) -0.02514(8) 0.11562(6) 0.0432(2) Uani 1 d . . O1 O 0.2921(2) 0.1973(2) -0.08088(15) 0.0404(7) Uani 1 d . . O2 O 0.2346(2) 0.1327(2) 0.08175(14) 0.0365(6) Uani 1 d . . O3 O 0.2391(2) -0.0187(2) -0.0438(2) 0.0362(6) Uani 1 d . . C1 C 0.2578(3) 0.2863(3) -0.0596(2) 0.0324(9) Uani 1 d . . C2 C 0.3310(3) 0.3593(3) -0.0379(2) 0.0378(9) Uani 1 d . . C3 C 0.2927(4) 0.4498(3) -0.0221(2) 0.0463(11) Uani 1 d . . H3A H 0.3424(4) 0.4997(3) -0.0081(2) 0.056 Uiso 1 calc R . C4 C 0.1844(4) 0.4707(3) -0.0260(3) 0.0525(12) Uani 1 d . . H4A H 0.1595(4) 0.5339(3) -0.0144(3) 0.063 Uiso 1 calc R . C5 C 0.1125(4) 0.3987(3) -0.0468(3) 0.0494(11) Uani 1 d . . H5A H 0.0377(4) 0.4130(3) -0.0496(3) 0.059 Uiso 1 calc R . C6 C 0.1468(3) 0.3057(3) -0.0640(2) 0.0371(9) Uani 1 d . . C7 C 0.4512(3) 0.3373(4) -0.0326(3) 0.0624(14) Uani 1 d . . H7A H 0.4631(3) 0.2693(4) -0.0459(3) 0.094 Uiso 1 calc R . H7B H 0.4789(3) 0.3500(4) 0.0213(3) 0.094 Uiso 1 calc R . H7C H 0.4889(3) 0.3785(4) -0.0700(3) 0.094 Uiso 1 calc R . C8 C 0.0701(3) 0.2275(3) -0.0873(3) 0.0529(12) Uani 1 d . . H8A H 0.1101(3) 0.1678(3) -0.0968(3) 0.079 Uiso 1 calc R . H8B H 0.0300(3) 0.2462(3) -0.1358(3) 0.079 Uiso 1 calc R . H8C H 0.0196(3) 0.2170(3) -0.0447(3) 0.079 Uiso 1 calc R . C9 C 0.2290(3) 0.1024(3) 0.1572(2) 0.0394(10) Uani 1 d . . C10 C 0.2998(4) 0.1407(4) 0.2155(3) 0.0587(14) Uani 1 d . . C11 C 0.2846(7) 0.1136(6) 0.2937(4) 0.110(3) Uani 1 d . . H11A H 0.3312(7) 0.1386(6) 0.3344(4) 0.131 Uiso 1 calc R . C12 C 0.2040(9) 0.0516(8) 0.3129(5) 0.140(5) Uani 1 d . . H12A H 0.1945(9) 0.0348(8) 0.3667(5) 0.168 Uiso 1 calc R . C13 C 0.1370(7) 0.0138(5) 0.2557(5) 0.106(3) Uani 1 d . . H13A H 0.0825(7) -0.0303(5) 0.2705(5) 0.127 Uiso 1 calc R . C14 C 0.1461(4) 0.0380(3) 0.1758(3) 0.064(2) Uani 1 d . . C15 C 0.3870(4) 0.2079(4) 0.1938(4) 0.099(2) Uani 1 d . . H15A H 0.4279(4) 0.2275(4) 0.2416(4) 0.148 Uiso 1 calc R . H15B H 0.3555(4) 0.2652(4) 0.1680(4) 0.148 Uiso 1 calc R . H15C H 0.4351(4) 0.1755(4) 0.1573(4) 0.148 Uiso 1 calc R . C16 C 0.0713(5) -0.0001(4) 0.1123(4) 0.103(3) Uani 1 d . . H16A H 0.0919(5) 0.0256(4) 0.0609(4) 0.154 Uiso 1 calc R . H16B H -0.0026(5) 0.0198(4) 0.1230(4) 0.154 Uiso 1 calc R . H16C H 0.0754(5) -0.0708(4) 0.1114(4) 0.154 Uiso 1 calc R . C17 C 0.2644(3) -0.0973(3) -0.0885(2) 0.0325(9) Uani 1 d . . C18 C 0.2863(3) -0.1851(3) -0.0515(3) 0.0463(11) Uani 1 d . . C19 C 0.3122(3) -0.2647(3) -0.1012(4) 0.0618(15) Uani 1 d . . H19A H 0.3286(3) -0.3256(3) -0.0778(4) 0.074 Uiso 1 calc R . C20 C 0.3139(4) -0.2552(4) -0.1811(4) 0.068(2) Uani 1 d . . H20A H 0.3333(4) -0.3087(4) -0.2128(4) 0.082 Uiso 1 calc R . C21 C 0.2879(4) -0.1697(4) -0.2160(3) 0.0595(14) Uani 1 d . . H21A H 0.2883(4) -0.1648(4) -0.2721(3) 0.071 Uiso 1 calc R . C22 C 0.2609(3) -0.0891(3) -0.1719(2) 0.0391(9) Uani 1 d . . C23 C 0.2797(4) -0.1961(3) 0.0362(3) 0.0637(14) Uani 1 d . . H23A H 0.2975(4) -0.2627(3) 0.0512(3) 0.096 Uiso 1 calc R . H23B H 0.2064(4) -0.1809(3) 0.0523(3) 0.096 Uiso 1 calc R . H23C H 0.3308(4) -0.1517(3) 0.0626(3) 0.096 Uiso 1 calc R . C24 C 0.2279(4) 0.0042(3) -0.2099(2) 0.0528(12) Uani 1 d . . H24A H 0.2122(4) 0.0517(3) -0.1688(2) 0.079 Uiso 1 calc R . H24B H 0.1634(4) -0.0061(3) -0.2438(2) 0.079 Uiso 1 calc R . H24C H 0.2866(4) 0.0282(3) -0.2421(2) 0.079 Uiso 1 calc R . C25 C 0.0045(4) -0.2609(4) -0.2620(3) 0.0669(14) Uani 1 d . . H25A H -0.0428(4) -0.2042(4) -0.2648(3) 0.100 Uiso 1 calc R . H25B H -0.0078(4) -0.3007(4) -0.3093(3) 0.100 Uiso 1 calc R . H25C H 0.0798(4) -0.2397(4) -0.2590(3) 0.100 Uiso 1 calc R . C26 C -0.1329(4) -0.3521(4) -0.1958(4) 0.077(2) Uani 1 d . . H26A H -0.1813(4) -0.2962(4) -0.1989(4) 0.116 Uiso 1 calc R . H26B H -0.1484(4) -0.3903(4) -0.1486(4) 0.116 Uiso 1 calc R . H26C H -0.1437(4) -0.3922(4) -0.2432(4) 0.116 Uiso 1 calc R . C27 C -0.0015(4) -0.2581(4) -0.1185(3) 0.0606(13) Uani 1 d . . H27A H -0.0485(4) -0.2013(4) -0.1215(3) 0.091 Uiso 1 calc R . H27B H 0.0739(4) -0.2372(4) -0.1149(3) 0.091 Uiso 1 calc R . H27C H -0.0181(4) -0.2962(4) -0.0715(3) 0.091 Uiso 1 calc R . C28 C 0.0514(4) -0.4036(3) -0.1862(3) 0.0618(14) Uani 1 d . . H28A H 0.0350(4) -0.4415(3) -0.1390(3) 0.093 Uiso 1 calc R . H28B H 0.1269(4) -0.3827(3) -0.1828(3) 0.093 Uiso 1 calc R . H28C H 0.0395(4) -0.4434(3) -0.2336(3) 0.093 Uiso 1 calc R . N1 N -0.0193(3) -0.3181(2) -0.1907(2) 0.0417(8) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02721(8) 0.03222(8) 0.03307(9) 0.00122(7) 0.00192(5) 0.00324(7) Cl1 0.0417(6) 0.0499(6) 0.0380(6) 0.0058(5) 0.0029(5) 0.0061(5) O1 0.055(2) 0.0311(15) 0.0349(15) 0.0030(12) 0.0020(14) 0.0053(13) O2 0.037(2) 0.040(2) 0.0325(15) -0.0025(12) 0.0017(12) 0.0004(13) O3 0.0348(15) 0.0330(15) 0.041(2) -0.0030(12) 0.0099(13) -0.0012(12) C1 0.040(2) 0.029(2) 0.028(2) 0.002(2) -0.003(2) 0.002(2) C2 0.035(2) 0.039(2) 0.039(2) 0.002(2) -0.005(2) 0.000(2) C3 0.057(3) 0.033(2) 0.048(3) -0.001(2) -0.011(2) -0.009(2) C4 0.067(3) 0.028(2) 0.062(3) 0.001(2) -0.009(3) 0.009(2) C5 0.039(2) 0.052(3) 0.057(3) 0.004(2) -0.006(2) 0.012(2) C6 0.041(2) 0.036(2) 0.034(2) 0.005(2) -0.011(2) -0.001(2) C7 0.037(3) 0.059(3) 0.091(4) -0.007(3) -0.004(3) -0.006(2) C8 0.042(3) 0.054(3) 0.062(3) 0.006(2) -0.012(2) -0.010(2) C9 0.041(2) 0.038(2) 0.040(2) -0.009(2) 0.006(2) 0.011(2) C10 0.056(3) 0.072(3) 0.047(3) -0.024(2) -0.011(2) 0.035(3) C11 0.130(7) 0.152(7) 0.045(4) -0.024(4) -0.018(4) 0.104(6) C12 0.194(12) 0.163(9) 0.065(5) 0.060(6) 0.063(6) 0.140(9) C13 0.126(7) 0.075(5) 0.122(6) 0.047(5) 0.090(6) 0.054(4) C14 0.075(4) 0.038(3) 0.083(4) 0.000(3) 0.051(3) 0.007(3) C15 0.047(3) 0.106(5) 0.142(6) -0.083(4) -0.031(4) 0.013(3) C16 0.072(4) 0.066(4) 0.174(7) -0.053(4) 0.065(5) -0.042(3) C17 0.024(2) 0.028(2) 0.046(2) -0.003(2) 0.005(2) -0.004(2) C18 0.031(2) 0.037(2) 0.070(3) 0.003(2) -0.012(2) -0.005(2) C19 0.032(2) 0.029(2) 0.124(5) 0.000(3) -0.014(3) -0.006(2) C20 0.050(3) 0.056(3) 0.099(4) -0.039(3) 0.000(3) -0.005(3) C21 0.039(3) 0.081(4) 0.059(3) -0.030(3) 0.008(2) -0.015(3) C22 0.028(2) 0.048(2) 0.042(2) -0.012(2) 0.005(2) -0.007(2) C23 0.054(3) 0.055(3) 0.081(4) 0.029(3) -0.013(3) -0.013(2) C24 0.053(3) 0.069(3) 0.036(2) 0.011(2) 0.002(2) -0.008(2) C25 0.090(4) 0.051(3) 0.059(3) 0.003(3) -0.002(3) -0.011(3) C26 0.037(3) 0.060(3) 0.135(5) -0.017(3) -0.001(3) -0.006(3) C27 0.057(3) 0.066(3) 0.059(3) -0.021(3) 0.000(3) 0.011(3) C28 0.067(3) 0.059(3) 0.058(3) -0.010(2) -0.014(3) 0.026(3) N1 0.035(2) 0.040(2) 0.050(2) -0.006(2) -0.004(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O3 2.113(3) . ? Bi1 O2 2.152(3) . ? Bi1 O1 2.154(3) . ? Bi1 Cl1 2.9326(13) 3_655 ? Bi1 Cl1 3.0020(12) . ? Cl1 Bi1 2.9325(13) 3_655 ? O1 C1 1.356(4) . ? O2 C9 1.345(5) . ? O3 C17 1.366(4) . ? C1 C2 1.400(5) . ? C1 C6 1.405(5) . ? C2 C3 1.369(6) . ? C2 C7 1.524(5) . ? C3 C4 1.376(6) . ? C4 C5 1.376(6) . ? C5 C6 1.389(5) . ? C6 C8 1.487(5) . ? C9 C14 1.404(6) . ? C9 C10 1.405(6) . ? C10 C11 1.391(8) . ? C10 C15 1.482(8) . ? C11 C12 1.365(12) . ? C12 C13 1.360(12) . ? C13 C14 1.399(8) . ? C14 C16 1.493(8) . ? C17 C18 1.389(5) . ? C17 C22 1.414(6) . ? C18 C19 1.427(6) . ? C18 C23 1.494(6) . ? C19 C20 1.358(7) . ? C20 C21 1.356(7) . ? C21 C22 1.388(6) . ? C22 C24 1.493(6) . ? C25 N1 1.479(5) . ? C26 N1 1.486(5) . ? C27 N1 1.486(5) . ? C28 N1 1.475(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Bi1 O2 88.79(10) . . ? O3 Bi1 O1 94.30(11) . . ? O2 Bi1 O1 88.21(10) . . ? O3 Bi1 Cl1 92.07(7) . 3_655 ? O2 Bi1 Cl1 179.04(7) . 3_655 ? O1 Bi1 Cl1 91.31(7) . 3_655 ? O3 Bi1 Cl1 103.13(8) . . ? O2 Bi1 Cl1 95.83(7) . . ? O1 Bi1 Cl1 162.17(8) . . ? Cl1 Bi1 Cl1 84.38(3) 3_655 . ? Bi1 Cl1 Bi1 95.62(3) 3_655 . ? C1 O1 Bi1 126.1(2) . . ? C9 O2 Bi1 125.6(2) . . ? C17 O3 Bi1 124.8(2) . . ? O1 C1 C2 121.2(4) . . ? O1 C1 C6 118.4(3) . . ? C2 C1 C6 120.3(3) . . ? C3 C2 C1 119.0(4) . . ? C3 C2 C7 121.1(4) . . ? C1 C2 C7 119.9(4) . . ? C2 C3 C4 121.8(4) . . ? C5 C4 C3 119.1(4) . . ? C4 C5 C6 121.6(4) . . ? C5 C6 C1 118.2(4) . . ? C5 C6 C8 122.2(4) . . ? C1 C6 C8 119.7(4) . . ? O2 C9 C14 118.0(4) . . ? O2 C9 C10 119.8(4) . . ? C14 C9 C10 122.0(5) . . ? C9 C10 C11 117.7(6) . . ? C9 C10 C15 120.6(5) . . ? C11 C10 C15 121.7(6) . . ? C10 C11 C12 121.1(8) . . ? C13 C12 C11 120.7(7) . . ? C12 C13 C14 121.8(8) . . ? C13 C14 C9 116.8(6) . . ? C13 C14 C16 122.8(6) . . ? C9 C14 C16 120.5(5) . . ? O3 C17 C18 119.6(4) . . ? O3 C17 C22 119.0(3) . . ? C18 C17 C22 121.2(4) . . ? C17 C18 C19 117.1(4) . . ? C17 C18 C23 121.2(4) . . ? C19 C18 C23 121.7(4) . . ? C20 C19 C18 121.4(5) . . ? C19 C20 C21 120.4(5) . . ? C20 C21 C22 121.8(5) . . ? C21 C22 C17 118.0(4) . . ? C21 C22 C24 122.1(4) . . ? C17 C22 C24 119.9(4) . . ? C28 N1 C25 109.8(4) . . ? C28 N1 C27 109.4(3) . . ? C25 N1 C27 109.9(4) . . ? C28 N1 C26 108.2(4) . . ? C25 N1 C26 109.6(4) . . ? C27 N1 C26 110.0(4) . . ? _refine_diff_density_max 1.250 _refine_diff_density_min -0.839 _refine_diff_density_rms 0.096 #=END data_5 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _audit_creation_method SHELXL _chemical_name_systematic ; Bis tetraphenylphosphonium Tribromo Bis trimethylphenoxy bismuthate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[P Ph4]2 [Bi Br3 (O -2,4,6-Me3 C6 H2)2]' _chemical_formula_analytical ? _chemical_formula_sum 'C66 H62 Bi Br3 O2 P2' _chemical_formula_weight 1397.81 _chemical_melting_point ? _chemical_compound_source ? 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5964(5) _cell_length_b 13.1136(6) _cell_length_c 38.747(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.7700(10) _cell_angle_gamma 90.00 _cell_volume 5862.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 267 _cell_measurement_theta_min 14.450 _cell_measurement_theta_max 22.550 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method ? _exptl_crystal_F_000 2768 _exptl_absorpt_coefficient_mu 5.150 _exptl_absorpt_correction_type 'Sadabs' _exptl_absorpt_correction_T_min 0.445101 _exptl_absorpt_correction_T_max 0.491535 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 36656 _diffrn_reflns_av_R_equivalents 0.1043 _diffrn_reflns_av_sigmaI/netI 0.1449 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 13388 _reflns_number_observed 7431 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+39.5212P] 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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00084(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 13385 _refine_ls_number_parameters 668 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1477 _refine_ls_R_factor_obs 0.0659 _refine_ls_wR_factor_all 0.1716 _refine_ls_wR_factor_obs 0.1326 _refine_ls_goodness_of_fit_all 1.009 _refine_ls_goodness_of_fit_obs 1.063 _refine_ls_restrained_S_all 1.010 _refine_ls_restrained_S_obs 1.063 _refine_ls_shift/esd_max 0.004 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi1 Bi 0.35938(3) -0.85301(3) 0.880238(10) 0.02521(13) Uani 1 d . . Br1 Br 0.35463(11) -0.73529(10) 0.94104(3) 0.0438(3) Uani 1 d . . Br2 Br 0.33821(13) -0.97599(12) 0.82107(4) 0.0632(4) Uani 1 d . . Br3 Br 0.59655(10) -0.75429(9) 0.86890(3) 0.0410(3) Uani 1 d . . O1 O 0.2534(6) -0.9685(5) 0.9031(2) 0.035(2) Uani 1 d . . O2 O 0.2142(6) -0.7667(6) 0.8595(2) 0.033(2) Uani 1 d . . P1 P 0.0743(2) -0.3952(2) 0.93851(7) 0.0219(6) Uani 1 d . . P2 P -0.3882(2) -0.3207(2) 0.81873(7) 0.0255(6) Uani 1 d . . C1 C 0.2591(9) -1.0016(7) 0.9364(3) 0.027(2) Uani 1 d . . C2 C 0.3631(9) -1.0348(7) 0.9541(3) 0.029(2) Uani 1 d . . C3 C 0.3617(8) -1.0707(8) 0.9879(3) 0.030(3) Uani 1 d . . H3A H 0.4326(8) -1.0920(8) 1.0002(3) 0.036 Uiso 1 calc R . C4 C 0.2608(9) -1.0765(7) 1.0043(2) 0.025(2) Uani 1 d . . C5 C 0.1592(9) -1.0478(7) 0.9853(3) 0.026(2) Uani 1 d . . H5A H 0.0887(9) -1.0545(7) 0.9957(3) 0.032 Uiso 1 calc R . C6 C 0.1548(9) -1.0099(8) 0.9522(3) 0.031(3) Uani 1 d . . C7 C 0.4746(9) -1.0344(9) 0.9366(3) 0.038(3) Uani 1 d . . H7A H 0.5382(9) -1.0601(9) 0.9529(3) 0.057 Uiso 1 calc R . H7B H 0.4920(9) -0.9647(9) 0.9297(3) 0.057 Uiso 1 calc R . H7C H 0.4655(9) -1.0783(9) 0.9161(3) 0.057 Uiso 1 calc R . C8 C 0.2598(10) -1.1152(9) 1.0410(3) 0.039(3) Uani 1 d . . H8A H 0.3390(10) -1.1321(9) 1.0506(3) 0.058 Uiso 1 calc R . H8B H 0.2112(10) -1.1764(9) 1.0410(3) 0.058 Uiso 1 calc R . H8C H 0.2285(10) -1.0623(9) 1.0554(3) 0.058 Uiso 1 calc R . C9 C 0.0424(9) -0.9798(8) 0.9315(3) 0.034(3) Uani 1 d . . H9A H 0.0586(9) -0.9548(8) 0.9087(3) 0.050 Uiso 1 calc R . H9B H 0.0048(9) -0.9258(8) 0.9438(3) 0.050 Uiso 1 calc R . H9C H -0.0089(9) -1.0392(8) 0.9287(3) 0.050 Uiso 1 calc R . C10 C 0.1714(8) -0.7580(8) 0.8259(3) 0.027(2) Uani 1 d . . C11 C 0.0808(9) -0.8194(9) 0.8123(3) 0.034(3) Uani 1 d . . C12 C 0.0334(11) -0.8036(11) 0.7780(3) 0.051(3) Uani 1 d . . H12A H -0.0293(11) -0.8453(11) 0.7688(3) 0.061 Uiso 1 calc R . C13 C 0.0744(10) -0.7300(12) 0.7572(3) 0.053(4) Uani 1 d . . C14 C 0.1665(10) -0.6724(10) 0.7705(3) 0.046(3) Uani 1 d . . H14A H 0.1979(10) -0.6236(10) 0.7560(3) 0.055 Uiso 1 calc R . C15 C 0.2164(10) -0.6825(9) 0.8047(3) 0.041(3) Uani 1 d . . C16 C 0.0345(11) -0.9016(10) 0.8353(4) 0.060(4) Uani 1 d . . H16A H -0.0290(11) -0.9384(10) 0.8221(4) 0.089 Uiso 1 calc R . H16B H 0.0060(11) -0.8696(10) 0.8557(4) 0.089 Uiso 1 calc R . H16C H 0.0970(11) -0.9495(10) 0.8428(4) 0.089 Uiso 1 calc R . C17 C 0.0169(13) -0.7155(16) 0.7208(3) 0.099(7) Uani 1 d . . H17A H -0.0471(13) -0.7640(16) 0.7164(3) 0.148 Uiso 1 calc R . H17B H 0.0737(13) -0.7271(16) 0.7041(3) 0.148 Uiso 1 calc R . H17C H -0.0131(13) -0.6457(16) 0.7182(3) 0.148 Uiso 1 calc R . C18 C 0.3127(10) -0.6182(9) 0.8192(4) 0.060(4) Uani 1 d . . H18A H 0.3345(10) -0.6375(9) 0.8435(4) 0.090 Uiso 1 calc R . H18B H 0.2886(10) -0.5465(9) 0.8182(4) 0.090 Uiso 1 calc R . H18C H 0.3792(10) -0.6275(9) 0.8058(4) 0.090 Uiso 1 calc R . C21 C 0.1212(8) -0.3387(7) 0.9001(2) 0.024(2) Uani 1 d . . C22 C 0.1455(9) -0.2349(8) 0.8995(3) 0.031(2) Uani 1 d . . H22A H 0.1313(9) -0.1942(8) 0.9189(3) 0.037 Uiso 1 calc R . C23 C 0.1896(9) -0.1892(9) 0.8716(3) 0.036(3) Uani 1 d . . H23A H 0.2078(9) -0.1186(9) 0.8720(3) 0.043 Uiso 1 calc R . C24 C 0.2068(10) -0.2480(9) 0.8430(3) 0.038(3) Uani 1 d . . H24A H 0.2387(10) -0.2183(9) 0.8237(3) 0.045 Uiso 1 calc R . C25 C 0.1774(10) -0.3502(9) 0.8425(3) 0.039(3) Uani 1 d . . H25A H 0.1861(10) -0.3896(9) 0.8223(3) 0.047 Uiso 1 calc R . C26 C 0.1360(9) -0.3957(8) 0.8705(3) 0.029(2) Uani 1 d . . H26A H 0.1173(9) -0.4662(8) 0.8698(3) 0.035 Uiso 1 calc R . C31 C 0.0075(8) -0.5154(7) 0.9278(2) 0.020(2) Uani 1 d . . C32 C 0.0713(9) -0.5953(8) 0.9164(3) 0.027(2) Uani 1 d . . H32A H 0.1526(9) -0.5879(8) 0.9158(3) 0.032 Uiso 1 calc R . C33 C 0.0176(9) -0.6866(8) 0.9059(2) 0.026(2) Uani 1 d . . H33A H 0.0618(9) -0.7413(8) 0.8980(2) 0.031 Uiso 1 calc R . C34 C -0.1013(9) -0.6973(8) 0.9071(3) 0.031(3) Uani 1 d . . H34A H -0.1385(9) -0.7593(8) 0.8999(3) 0.037 Uiso 1 calc R . C35 C -0.1662(9) -0.6175(8) 0.9189(3) 0.032(3) Uani 1 d . . H35A H -0.2475(9) -0.6249(8) 0.9195(3) 0.039 Uiso 1 calc R . C36 C -0.1123(8) -0.5277(8) 0.9299(2) 0.025(2) Uani 1 d . . H36A H -0.1560(8) -0.4742(8) 0.9388(2) 0.030 Uiso 1 calc R . C41 C -0.0280(8) -0.3105(7) 0.9556(3) 0.024(2) Uani 1 d . . C42 C -0.1125(9) -0.2657(8) 0.9323(3) 0.031(2) Uani 1 d . . H42A H -0.1110(9) -0.2750(8) 0.9081(3) 0.037 Uiso 1 calc R . C43 C -0.1994(10) -0.2069(8) 0.9450(3) 0.039(3) Uani 1 d . . H43A H -0.2579(10) -0.1767(8) 0.9293(3) 0.047 Uiso 1 calc R . C44 C -0.2002(10) -0.1927(9) 0.9805(3) 0.039(3) Uani 1 d . . H44A H -0.2605(10) -0.1543(9) 0.9891(3) 0.047 Uiso 1 calc R . C45 C -0.1130(9) -0.2344(8) 1.0033(3) 0.034(3) Uani 1 d . . H45A H -0.1118(9) -0.2225(8) 1.0276(3) 0.041 Uiso 1 calc R . C46 C -0.0274(8) -0.2938(7) 0.9906(3) 0.023(2) Uani 1 d . . H46A H 0.0320(8) -0.3231(7) 1.0062(3) 0.028 Uiso 1 calc R . C51 C 0.1975(8) -0.4111(7) 0.9701(2) 0.024(2) Uani 1 d . . C52 C 0.2684(9) -0.3271(7) 0.9796(3) 0.026(2) Uani 1 d . . H52A H 0.2506(9) -0.2622(7) 0.9696(3) 0.031 Uiso 1 calc R . C53 C 0.3625(9) -0.3380(8) 1.0032(3) 0.031(2) Uani 1 d . . H53A H 0.4088(9) -0.2804(8) 1.0101(3) 0.037 Uiso 1 calc R . C54 C 0.3910(9) -0.4325(8) 1.0172(3) 0.031(2) Uani 1 d . . H54A H 0.4581(9) -0.4397(8) 1.0332(3) 0.038 Uiso 1 calc R . C55 C 0.3233(8) -0.5162(8) 1.0082(2) 0.028(2) Uani 1 d . . H55A H 0.3436(8) -0.5808(8) 1.0181(2) 0.033 Uiso 1 calc R . C56 C 0.2256(8) -0.5067(8) 0.9847(3) 0.028(2) Uani 1 d . . H56A H 0.1782(8) -0.5644(8) 0.9786(3) 0.034 Uiso 1 calc R . C61 C -0.3240(9) -0.1988(8) 0.8284(3) 0.030(2) Uani 1 d . . C62 C -0.3935(10) -0.1107(8) 0.8261(3) 0.041(3) Uani 1 d . . H62A H -0.4719(10) -0.1146(8) 0.8164(3) 0.049 Uiso 1 calc R . C63 C -0.3479(12) -0.0196(9) 0.8378(4) 0.054(4) Uani 1 d . . H63A H -0.3946(12) 0.0400(9) 0.8353(4) 0.064 Uiso 1 calc R . C64 C -0.2365(12) -0.0121(10) 0.8532(4) 0.055(4) Uani 1 d . . H64A H -0.2074(12) 0.0513(10) 0.8622(4) 0.066 Uiso 1 calc R . C65 C -0.1665(10) -0.0987(9) 0.8556(3) 0.045(3) Uani 1 d . . H65A H -0.0886(10) -0.0938(9) 0.8657(3) 0.054 Uiso 1 calc R . C66 C -0.2085(9) -0.1901(9) 0.8435(3) 0.035(3) Uani 1 d . . H66A H -0.1598(9) -0.2485(9) 0.8453(3) 0.042 Uiso 1 calc R . C71 C -0.4965(9) -0.3079(9) 0.7825(3) 0.031(3) Uani 1 d . . C72 C -0.4763(10) -0.2481(10) 0.7542(3) 0.050(3) Uani 1 d . . H72A H -0.4069(10) -0.2096(10) 0.7542(3) 0.060 Uiso 1 calc R . C73 C -0.5586(12) -0.2456(12) 0.7261(3) 0.064(4) Uani 1 d . . H73A H -0.5430(12) -0.2089(12) 0.7060(3) 0.077 Uiso 1 calc R . C74 C -0.6620(11) -0.2945(12) 0.7265(4) 0.060(4) Uani 1 d . . H74A H -0.7205(11) -0.2866(12) 0.7077(4) 0.072 Uiso 1 calc R . C75 C -0.6809(12) -0.3549(12) 0.7539(4) 0.065(4) Uani 1 d . . H75A H -0.7503(12) -0.3937(12) 0.7533(4) 0.078 Uiso 1 calc R . C76 C -0.6001(9) -0.3601(9) 0.7824(3) 0.038(3) Uani 1 d . . H76A H -0.6156(9) -0.3994(9) 0.8020(3) 0.046 Uiso 1 calc R . C81 C -0.2810(9) -0.4114(8) 0.8090(3) 0.029(2) Uani 1 d . . C82 C -0.2102(10) -0.4591(9) 0.8357(3) 0.039(3) Uani 1 d . . H82A H -0.2205(10) -0.4442(9) 0.8592(3) 0.046 Uiso 1 calc R . C83 C -0.1256(10) -0.5277(9) 0.8283(3) 0.043(3) Uani 1 d . . H83A H -0.0787(10) -0.5605(9) 0.8465(3) 0.052 Uiso 1 calc R . C84 C -0.1101(11) -0.5476(9) 0.7950(3) 0.047(3) Uani 1 d . . H84A H -0.0507(11) -0.5935(9) 0.7899(3) 0.057 Uiso 1 calc R . C85 C -0.1790(11) -0.5024(10) 0.7680(3) 0.050(3) Uani 1 d . . H85A H -0.1683(11) -0.5195(10) 0.7447(3) 0.060 Uiso 1 calc R . C86 C -0.2625(10) -0.4331(9) 0.7747(3) 0.038(3) Uani 1 d . . H86A H -0.3075(10) -0.4001(9) 0.7561(3) 0.046 Uiso 1 calc R . C91 C -0.4537(8) -0.3640(8) 0.8563(2) 0.026(2) Uani 1 d . . C92 C -0.4665(9) -0.4674(8) 0.8628(3) 0.029(2) Uani 1 d . . H92A H -0.4382(9) -0.5164(8) 0.8477(3) 0.035 Uiso 1 calc R . C93 C -0.5200(9) -0.4989(9) 0.8911(3) 0.035(3) Uani 1 d . . H93A H -0.5293(9) -0.5696(9) 0.8954(3) 0.042 Uiso 1 calc R . C94 C -0.5607(8) -0.4268(9) 0.9135(3) 0.032(3) Uani 1 d . . H94A H -0.5972(8) -0.4484(9) 0.9332(3) 0.039 Uiso 1 calc R . C95 C -0.5481(10) -0.3258(9) 0.9072(3) 0.039(3) Uani 1 d . . H95A H -0.5770(10) -0.2769(9) 0.9222(3) 0.047 Uiso 1 calc R . C96 C -0.4935(9) -0.2934(9) 0.8790(3) 0.034(3) Uani 1 d . . H96A H -0.4833(9) -0.2226(9) 0.8751(3) 0.040 Uiso 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 0.0254(2) 0.0272(2) 0.0235(2) -0.0006(2) 0.00506(13) -0.0059(2) Br1 0.0455(7) 0.0477(8) 0.0386(7) -0.0071(6) 0.0066(5) -0.0057(6) Br2 0.0664(10) 0.0680(10) 0.0557(9) -0.0080(8) 0.0078(7) 0.0035(8) Br3 0.0338(6) 0.0418(7) 0.0476(7) -0.0037(6) 0.0045(5) -0.0066(5) O1 0.042(5) 0.036(4) 0.027(4) 0.004(3) 0.005(3) -0.021(4) O2 0.030(4) 0.049(5) 0.019(4) -0.003(3) 0.002(3) 0.005(3) P1 0.0229(14) 0.0207(13) 0.0221(14) -0.0010(11) 0.0024(11) -0.0016(11) P2 0.0271(14) 0.0258(14) 0.0245(14) 0.0019(11) 0.0066(11) -0.0018(11) C1 0.039(6) 0.020(5) 0.023(5) -0.004(4) -0.001(5) -0.014(5) C2 0.046(7) 0.018(5) 0.022(5) 0.005(4) 0.005(5) -0.015(5) C3 0.015(5) 0.024(6) 0.051(7) -0.007(5) 0.000(5) -0.008(4) C4 0.045(7) 0.009(5) 0.019(5) -0.006(4) -0.002(5) -0.003(4) C5 0.033(6) 0.017(5) 0.031(6) -0.005(5) 0.014(5) -0.010(4) C6 0.032(6) 0.025(6) 0.036(6) -0.007(5) 0.002(5) -0.008(5) C7 0.036(7) 0.042(7) 0.037(7) 0.001(6) 0.012(5) -0.012(5) C8 0.043(7) 0.038(7) 0.037(7) 0.012(5) 0.013(5) -0.005(5) C9 0.034(6) 0.030(6) 0.035(6) 0.000(5) -0.005(5) -0.001(5) C10 0.022(5) 0.033(6) 0.027(6) -0.002(5) 0.007(4) 0.004(5) C11 0.022(6) 0.043(7) 0.038(7) -0.006(5) 0.008(5) 0.001(5) C12 0.044(8) 0.069(9) 0.041(8) -0.023(7) 0.005(6) 0.000(7) C13 0.030(7) 0.099(12) 0.030(7) 0.000(7) -0.003(5) 0.026(7) C14 0.031(7) 0.063(9) 0.047(8) 0.014(7) 0.020(6) 0.016(6) C15 0.031(6) 0.049(8) 0.045(7) -0.008(6) 0.005(5) -0.003(5) C16 0.042(8) 0.056(9) 0.081(11) 0.003(8) 0.006(7) -0.016(7) C17 0.061(10) 0.198(21) 0.035(8) 0.001(11) -0.010(7) 0.048(12) C18 0.034(7) 0.040(8) 0.104(12) 0.011(8) -0.004(7) -0.010(6) C21 0.023(5) 0.026(6) 0.023(5) 0.002(4) -0.005(4) 0.001(4) C22 0.035(6) 0.021(6) 0.037(6) 0.000(5) 0.006(5) -0.006(5) C23 0.039(7) 0.033(6) 0.034(6) 0.003(5) -0.001(5) -0.009(5) C24 0.042(7) 0.048(8) 0.023(6) 0.008(6) 0.006(5) -0.003(6) C25 0.055(7) 0.032(6) 0.030(6) 0.008(6) 0.006(5) -0.006(6) C26 0.040(7) 0.020(5) 0.027(6) -0.003(5) 0.000(5) -0.005(5) C31 0.018(5) 0.018(5) 0.024(5) -0.002(4) 0.001(4) -0.001(4) C32 0.026(6) 0.028(6) 0.027(6) 0.001(5) 0.003(4) 0.001(5) C33 0.032(6) 0.020(5) 0.026(6) -0.001(4) 0.008(5) 0.004(4) C34 0.045(7) 0.019(5) 0.029(6) 0.001(5) 0.002(5) -0.009(5) C35 0.025(6) 0.037(7) 0.037(6) -0.006(5) 0.009(5) -0.004(5) C36 0.030(6) 0.029(6) 0.017(5) -0.001(4) 0.003(4) 0.003(5) C41 0.025(5) 0.019(5) 0.028(6) 0.004(4) 0.011(4) 0.000(4) C42 0.040(7) 0.025(6) 0.027(6) 0.003(5) 0.000(5) 0.010(5) C43 0.032(7) 0.031(7) 0.053(8) -0.002(6) -0.004(6) 0.006(5) C44 0.038(7) 0.028(6) 0.053(8) -0.004(6) 0.014(6) -0.003(5) C45 0.036(6) 0.028(6) 0.040(7) 0.003(5) 0.011(5) -0.005(5) C46 0.021(5) 0.017(5) 0.031(6) 0.001(4) 0.003(4) -0.001(4) C51 0.018(5) 0.026(6) 0.026(5) -0.006(5) 0.002(4) 0.005(4) C52 0.034(6) 0.017(5) 0.027(6) 0.003(4) 0.003(4) 0.006(4) C53 0.028(6) 0.027(6) 0.036(6) -0.005(5) -0.003(5) -0.002(5) C54 0.025(6) 0.035(6) 0.035(6) -0.004(5) 0.005(5) 0.006(5) C55 0.027(6) 0.036(6) 0.019(5) 0.012(5) 0.001(4) 0.008(5) C56 0.019(5) 0.030(6) 0.035(6) 0.000(5) 0.007(4) 0.002(4) C61 0.037(6) 0.028(6) 0.028(6) 0.002(5) 0.017(5) -0.003(5) C62 0.039(7) 0.021(6) 0.064(9) 0.001(6) 0.017(6) -0.009(5) C63 0.054(9) 0.021(6) 0.091(11) -0.001(7) 0.034(8) 0.003(6) C64 0.059(9) 0.038(8) 0.072(10) -0.008(7) 0.018(8) -0.014(7) C65 0.038(7) 0.042(7) 0.056(8) -0.007(7) 0.007(6) -0.023(6) C66 0.021(6) 0.042(7) 0.042(7) -0.003(6) 0.004(5) -0.002(5) C71 0.027(6) 0.038(6) 0.030(6) 0.001(5) 0.005(5) 0.007(5) C72 0.039(7) 0.069(10) 0.040(7) 0.017(7) -0.005(6) -0.011(7) C73 0.055(9) 0.099(12) 0.037(8) 0.030(8) -0.001(6) 0.009(8) C74 0.032(7) 0.096(12) 0.049(9) 0.012(8) -0.009(6) -0.001(7) C75 0.052(9) 0.083(11) 0.055(9) 0.018(9) -0.015(7) -0.029(8) C76 0.043(7) 0.041(7) 0.029(6) 0.005(6) -0.001(5) -0.017(6) C81 0.029(6) 0.027(6) 0.032(6) 0.001(5) 0.009(5) -0.003(5) C82 0.047(7) 0.041(7) 0.027(6) -0.003(5) -0.001(5) 0.006(6) C83 0.032(7) 0.041(7) 0.057(8) 0.011(6) 0.013(6) 0.009(6) C84 0.051(8) 0.036(7) 0.057(9) -0.012(7) 0.020(7) 0.011(6) C85 0.059(9) 0.046(8) 0.049(8) -0.006(7) 0.024(7) 0.010(7) C86 0.056(8) 0.042(7) 0.018(6) 0.003(5) 0.012(5) 0.005(6) C91 0.028(5) 0.034(6) 0.016(5) -0.003(5) 0.000(4) -0.005(5) C92 0.038(6) 0.022(6) 0.027(6) -0.008(5) 0.005(5) -0.006(5) C93 0.035(6) 0.032(6) 0.037(7) 0.006(5) 0.007(5) -0.006(5) C94 0.022(6) 0.045(7) 0.032(6) 0.006(5) 0.010(5) -0.002(5) C95 0.045(7) 0.034(7) 0.042(7) -0.005(5) 0.018(6) 0.007(5) C96 0.043(7) 0.030(6) 0.030(6) -0.002(5) 0.014(5) -0.003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O2 2.119(7) . ? Bi1 O1 2.193(7) . ? Bi1 Br2 2.793(2) . ? Bi1 Br1 2.8218(13) . ? Bi1 Br3 3.1107(12) . ? O1 C1 1.357(12) . ? O2 C10 1.353(11) . ? P1 C31 1.786(9) . ? P1 C21 1.794(10) . ? P1 C51 1.797(10) . ? P1 C41 1.800(10) . ? P2 C81 1.788(11) . ? P2 C61 1.787(11) . ? P2 C71 1.795(11) . ? P2 C91 1.802(10) . ? C1 C2 1.394(14) . ? C1 C6 1.414(14) . ? C2 C3 1.395(14) . ? C2 C7 1.518(14) . ? C3 C4 1.388(14) . ? C4 C5 1.377(14) . ? C4 C8 1.513(14) . ? C5 C6 1.371(14) . ? C6 C9 1.513(14) . ? C10 C11 1.385(14) . ? C10 C15 1.42(2) . ? C11 C12 1.40(2) . ? C11 C16 1.53(2) . ? C12 C13 1.37(2) . ? C13 C14 1.37(2) . ? C13 C17 1.51(2) . ? C14 C15 1.40(2) . ? C15 C18 1.47(2) . ? C21 C22 1.391(13) . ? C21 C26 1.395(14) . ? C22 C23 1.380(14) . ? C23 C24 1.381(15) . ? C24 C25 1.38(2) . ? C25 C26 1.368(14) . ? C31 C32 1.381(13) . ? C31 C36 1.409(13) . ? C32 C33 1.392(14) . ? C33 C34 1.392(14) . ? C34 C35 1.392(14) . ? C35 C36 1.380(14) . ? C41 C46 1.371(13) . ? C41 C42 1.393(13) . ? C42 C43 1.396(15) . ? C43 C44 1.39(2) . ? C44 C45 1.388(15) . ? C45 C46 1.392(14) . ? C51 C52 1.402(13) . ? C51 C56 1.402(14) . ? C52 C53 1.359(13) . ? C53 C54 1.378(14) . ? C54 C55 1.373(14) . ? C55 C56 1.386(13) . ? C61 C62 1.406(15) . ? C61 C66 1.412(14) . ? C62 C63 1.37(2) . ? C63 C64 1.37(2) . ? C64 C65 1.39(2) . ? C65 C66 1.36(2) . ? C71 C76 1.383(15) . ? C71 C72 1.39(2) . ? C72 C73 1.37(2) . ? C73 C74 1.36(2) . ? C74 C75 1.36(2) . ? C75 C76 1.38(2) . ? C81 C86 1.398(14) . ? C81 C82 1.403(14) . ? C82 C83 1.382(15) . ? C83 C84 1.35(2) . ? C84 C85 1.38(2) . ? C85 C86 1.37(2) . ? C91 C92 1.389(14) . ? C91 C96 1.387(14) . ? C92 C93 1.376(14) . ? C93 C94 1.398(15) . ? C94 C95 1.36(2) . ? C95 C96 1.384(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Bi1 O1 93.8(3) . . ? O2 Bi1 Br2 89.8(2) . . ? O1 Bi1 Br2 85.8(2) . . ? O2 Bi1 Br1 86.7(2) . . ? O1 Bi1 Br1 88.9(2) . . ? Br2 Bi1 Br1 173.48(4) . . ? O2 Bi1 Br3 113.8(2) . . ? O1 Bi1 Br3 152.1(2) . . ? Br2 Bi1 Br3 97.49(4) . . ? Br1 Bi1 Br3 88.97(4) . . ? C1 O1 Bi1 129.0(6) . . ? C10 O2 Bi1 127.7(6) . . ? C31 P1 C21 109.4(5) . . ? C31 P1 C51 110.6(4) . . ? C21 P1 C51 109.0(5) . . ? C31 P1 C41 110.1(4) . . ? C21 P1 C41 108.4(5) . . ? C51 P1 C41 109.2(5) . . ? C81 P2 C61 110.8(5) . . ? C81 P2 C71 110.1(5) . . ? C61 P2 C71 108.9(5) . . ? C81 P2 C91 108.6(5) . . ? C61 P2 C91 108.3(5) . . ? C71 P2 C91 110.1(5) . . ? O1 C1 C2 121.5(9) . . ? O1 C1 C6 118.4(9) . . ? C2 C1 C6 119.9(10) . . ? C1 C2 C3 118.4(10) . . ? C1 C2 C7 121.0(9) . . ? C3 C2 C7 120.6(10) . . ? C4 C3 C2 122.5(10) . . ? C5 C4 C3 117.1(9) . . ? C5 C4 C8 120.4(10) . . ? C3 C4 C8 122.4(10) . . ? C6 C5 C4 123.2(10) . . ? C5 C6 C1 118.7(10) . . ? C5 C6 C9 122.7(10) . . ? C1 C6 C9 118.6(10) . . ? O2 C10 C11 120.4(10) . . ? O2 C10 C15 119.8(9) . . ? C11 C10 C15 119.7(10) . . ? C10 C11 C12 118.9(11) . . ? C10 C11 C16 119.1(10) . . ? C12 C11 C16 122.0(11) . . ? C13 C12 C11 122.3(12) . . ? C14 C13 C12 118.1(11) . . ? C14 C13 C17 122.5(15) . . ? C12 C13 C17 119.4(14) . . ? C13 C14 C15 122.7(12) . . ? C14 C15 C10 118.3(11) . . ? C14 C15 C18 122.5(12) . . ? C10 C15 C18 119.2(11) . . ? C22 C21 C26 117.9(10) . . ? C22 C21 P1 119.8(8) . . ? C26 C21 P1 122.2(8) . . ? C23 C22 C21 122.0(10) . . ? C22 C23 C24 118.8(11) . . ? C23 C24 C25 119.8(10) . . ? C26 C25 C24 121.1(11) . . ? C25 C26 C21 120.1(10) . . ? C32 C31 C36 119.7(9) . . ? C32 C31 P1 120.6(7) . . ? C36 C31 P1 119.7(7) . . ? C31 C32 C33 120.5(9) . . ? C32 C33 C34 119.5(9) . . ? C35 C34 C33 120.4(10) . . ? C36 C35 C34 120.0(10) . . ? C35 C36 C31 119.9(9) . . ? C46 C41 C42 120.4(9) . . ? C46 C41 P1 121.6(8) . . ? C42 C41 P1 117.9(8) . . ? C41 C42 C43 119.4(10) . . ? C44 C43 C42 119.9(11) . . ? C45 C44 C43 120.2(11) . . ? C44 C45 C46 119.6(11) . . ? C41 C46 C45 120.5(10) . . ? C52 C51 C56 119.3(9) . . ? C52 C51 P1 119.6(7) . . ? C56 C51 P1 121.1(8) . . ? C53 C52 C51 120.3(9) . . ? C52 C53 C54 120.2(10) . . ? C55 C54 C53 120.8(10) . . ? C54 C55 C56 120.2(10) . . ? C55 C56 C51 119.2(10) . . ? C62 C61 C66 118.3(10) . . ? C62 C61 P2 119.8(8) . . ? C66 C61 P2 121.1(8) . . ? C63 C62 C61 119.8(11) . . ? C62 C63 C64 121.6(12) . . ? C63 C64 C65 119.2(12) . . ? C66 C65 C64 120.7(11) . . ? C65 C66 C61 120.4(11) . . ? C76 C71 C72 119.6(10) . . ? C76 C71 P2 119.7(8) . . ? C72 C71 P2 120.7(9) . . ? C73 C72 C71 118.7(12) . . ? C74 C73 C72 121.6(12) . . ? C75 C74 C73 119.6(12) . . ? C74 C75 C76 120.3(12) . . ? C75 C76 C71 119.9(11) . . ? C86 C81 C82 118.5(10) . . ? C86 C81 P2 120.9(8) . . ? C82 C81 P2 120.6(8) . . ? C83 C82 C81 120.8(11) . . ? C84 C83 C82 119.4(11) . . ? C83 C84 C85 121.3(11) . . ? C86 C85 C84 120.4(11) . . ? C85 C86 C81 119.6(11) . . ? C92 C91 C96 119.2(9) . . ? C92 C91 P2 121.1(8) . . ? C96 C91 P2 119.7(8) . . ? C93 C92 C91 120.2(10) . . ? C92 C93 C94 119.9(10) . . ? C95 C94 C93 119.9(10) . . ? C94 C95 C96 120.6(10) . . ? C95 C96 C91 120.2(10) . . ? _refine_diff_density_max 1.169 _refine_diff_density_min -2.228 _refine_diff_density_rms 0.195 _publ_section_references ; Siemens (1995a). SHELXTL. Version 5.03 Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1995b). SMART and SAINT Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (1996). SADABS. University of G\"ottingen, Germany. ;