# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Silvestru, Cristian' _publ_contact_author_email cristi@chem.ubbcluj.ro _publ_section_title ; Organobismuth compounds with the pincer ligand 2,6-(Me2NCH2)2C6H3: Monoorganobismuth(III) carbonate, sulfate, nitrate, and a diorganobismuthenium(III) salt ; loop_ _publ_author_name C.Silvestru H.Breunig M.Nema A.Soran R.Varga # Attachment '- Compound 4 - CCDC 773764.cif' data_433r _database_code_depnum_ccdc_archive 'CCDC 773764' #TrackingRef '- Compound 4 - CCDC 773764.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H19 Bi N4 O6, O ' _chemical_formula_sum 'C12 H19 Bi N4 O7' _chemical_formula_weight 540.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.218(6) _cell_length_b 9.495(7) _cell_length_c 10.582(7) _cell_angle_alpha 80.515(12) _cell_angle_beta 72.286(11) _cell_angle_gamma 89.410(11) _cell_volume 869.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2954 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 23.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.064 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 10.181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2129 _exptl_absorpt_correction_T_max 0.2353 _exptl_absorpt_process_details 'Bruker , 2000.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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_% ? _diffrn_reflns_number 6166 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0898 _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 2.05 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3019 _reflns_number_gt 2676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0173P)^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 SHELXL _refine_ls_extinction_coef 0.0028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3019 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.72644(4) 0.69605(3) 0.81513(3) 0.02986(16) Uani 1 1 d . . . C1 C 0.7369(10) 0.9305(9) 0.7481(9) 0.030(2) Uani 1 1 d . . . C2 C 0.7873(10) 1.0167(9) 0.8210(9) 0.034(2) Uani 1 1 d . . . C3 C 0.7955(11) 1.1656(9) 0.7765(12) 0.048(3) Uani 1 1 d . . . H3 H 0.8298 1.2268 0.8226 0.058 Uiso 1 1 calc R . . C4 C 0.7525(11) 1.2210(10) 0.6640(11) 0.049(3) Uani 1 1 d . . . H4 H 0.7577 1.3194 0.6358 0.059 Uiso 1 1 calc R . . C5 C 0.7028(10) 1.1340(10) 0.5943(10) 0.042(2) Uani 1 1 d . . . H5 H 0.6758 1.1724 0.5183 0.051 Uiso 1 1 calc R . . C6 C 0.6930(9) 0.9856(9) 0.6382(9) 0.031(2) Uani 1 1 d . . . C7 C 0.8457(11) 0.9498(10) 0.9345(9) 0.041(2) Uani 1 1 d . . . H7A H 0.9541 0.9362 0.8995 0.050 Uiso 1 1 calc R . . H7B H 0.8306 1.0134 0.9999 0.050 Uiso 1 1 calc R . . C8 C 0.6149(11) 0.8313(10) 1.0950(10) 0.043(2) Uani 1 1 d . . . H8A H 0.6272 0.8837 1.1616 0.065 Uiso 1 1 calc R . . H8B H 0.5658 0.7398 1.1384 0.065 Uiso 1 1 calc R . . H8C H 0.5536 0.8837 1.0461 0.065 Uiso 1 1 calc R . . C9 C 0.8583(12) 0.7230(11) 1.0766(11) 0.051(3) Uani 1 1 d . . . H9A H 0.9549 0.7059 1.0151 0.076 Uiso 1 1 calc R . . H9B H 0.8047 0.6334 1.1201 0.076 Uiso 1 1 calc R . . H9C H 0.8745 0.7733 1.1431 0.076 Uiso 1 1 calc R . . C10 C 0.6306(11) 0.8839(9) 0.5684(10) 0.038(2) Uani 1 1 d . . . H10A H 0.5215 0.8689 0.6105 0.046 Uiso 1 1 calc R . . H10B H 0.6488 0.9259 0.4747 0.046 Uiso 1 1 calc R . . C11 C 0.6125(13) 0.6364(11) 0.5459(12) 0.058(3) Uani 1 1 d . . . H11A H 0.5953 0.6701 0.4612 0.087 Uiso 1 1 calc R . . H11B H 0.5164 0.6187 0.6156 0.087 Uiso 1 1 calc R . . H11C H 0.6665 0.5495 0.5410 0.087 Uiso 1 1 calc R . . C12 C 0.8580(12) 0.7634(11) 0.4788(10) 0.052(3) Uani 1 1 d . . . H12A H 0.8506 0.7941 0.3900 0.079 Uiso 1 1 calc R . . H12B H 0.9069 0.6737 0.4822 0.079 Uiso 1 1 calc R . . H12C H 0.9168 0.8335 0.5003 0.079 Uiso 1 1 calc R . . N1 N 0.7661(8) 0.8111(7) 1.0008(7) 0.0325(17) Uani 1 1 d . . . N2 N 0.7042(8) 0.7462(7) 0.5768(7) 0.0342(18) Uani 1 1 d . . . N3 N 0.3733(10) 0.6180(10) 0.9169(9) 0.048(2) Uani 1 1 d . . . N4 N 1.0608(11) 0.6074(9) 0.6996(8) 0.045(2) Uani 1 1 d . . . O1 O 0.4531(7) 0.7379(7) 0.8787(7) 0.0500(19) Uani 1 1 d . . . O2 O 0.4356(9) 0.5105(8) 0.8877(9) 0.066(2) Uani 1 1 d . . . O3 O 0.2402(9) 0.6174(9) 0.9771(9) 0.071(2) Uani 1 1 d . . . O4 O 0.9999(7) 0.7239(7) 0.7374(7) 0.0479(18) Uani 1 1 d . . . O5 O 0.9790(10) 0.5126(8) 0.6920(9) 0.081(3) Uani 1 1 d . . . O6 O 1.2001(9) 0.6008(8) 0.6751(9) 0.071(2) Uani 1 1 d . . . O7 O 0.2393(10) 0.9138(9) 0.7582(9) 0.085(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0282(2) 0.0315(2) 0.0344(2) -0.00715(14) -0.01556(17) 0.00531(13) C1 0.027(5) 0.037(5) 0.031(5) -0.011(4) -0.012(4) 0.002(4) C2 0.025(5) 0.041(5) 0.035(6) -0.008(4) -0.005(4) 0.004(4) C3 0.034(6) 0.034(5) 0.077(8) -0.020(5) -0.012(6) -0.005(4) C4 0.043(6) 0.039(5) 0.061(8) -0.006(5) -0.010(6) 0.008(5) C5 0.031(6) 0.042(5) 0.050(7) 0.003(5) -0.012(5) 0.001(4) C6 0.019(5) 0.034(5) 0.038(6) -0.010(4) -0.004(4) 0.002(4) C7 0.037(6) 0.059(6) 0.037(6) -0.020(5) -0.017(5) -0.002(5) C8 0.040(6) 0.046(6) 0.038(6) -0.015(5) 0.000(5) 0.004(4) C9 0.054(7) 0.058(6) 0.053(7) -0.007(5) -0.038(6) 0.009(5) C10 0.038(6) 0.043(5) 0.041(6) -0.003(4) -0.025(5) 0.008(4) C11 0.063(8) 0.058(7) 0.073(8) -0.031(6) -0.040(7) 0.009(5) C12 0.061(8) 0.062(7) 0.041(7) -0.017(5) -0.022(6) 0.015(5) N1 0.032(4) 0.047(4) 0.024(4) -0.010(3) -0.014(4) 0.003(3) N2 0.032(4) 0.043(4) 0.037(5) -0.016(3) -0.020(4) 0.011(3) N3 0.040(6) 0.067(6) 0.043(6) -0.008(5) -0.023(5) 0.006(5) N4 0.050(6) 0.046(5) 0.033(5) -0.007(4) -0.004(5) 0.022(4) O1 0.037(4) 0.037(4) 0.074(5) -0.008(3) -0.015(4) 0.002(3) O2 0.067(5) 0.041(4) 0.097(7) -0.015(4) -0.033(5) 0.001(4) O3 0.036(5) 0.092(6) 0.079(6) -0.016(5) -0.008(5) 0.000(4) O4 0.034(4) 0.045(4) 0.068(5) -0.020(3) -0.016(4) 0.010(3) O5 0.075(6) 0.057(5) 0.110(8) -0.048(5) -0.008(6) 0.005(4) O6 0.044(5) 0.083(6) 0.079(6) -0.013(5) -0.008(5) 0.031(4) O7 0.092(7) 0.081(6) 0.088(7) -0.025(5) -0.034(6) 0.016(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 C1 2.216(8) . ? Bi1 O4 2.404(7) . ? Bi1 O1 2.448(7) . ? Bi1 N1 2.518(7) . ? Bi1 N2 2.558(7) . ? C1 C6 1.369(12) . ? C1 C2 1.383(11) . ? C2 C3 1.410(12) . ? C2 C7 1.507(12) . ? C3 C4 1.388(14) . ? C3 H3 0.9300 . ? C4 C5 1.361(13) . ? C4 H4 0.9300 . ? C5 C6 1.404(12) . ? C5 H5 0.9300 . ? C6 C10 1.521(12) . ? C7 N1 1.472(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.478(11) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.497(11) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N2 1.469(11) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.486(11) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.472(12) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N3 O3 1.197(10) . ? N3 O2 1.205(10) . ? N3 O1 1.298(10) . ? N4 O5 1.209(10) . ? N4 O6 1.233(10) . ? N4 O4 1.302(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 O4 83.8(3) . . ? C1 Bi1 O1 80.8(3) . . ? O4 Bi1 O1 164.5(2) . . ? C1 Bi1 N1 72.7(3) . . ? O4 Bi1 N1 80.7(2) . . ? O1 Bi1 N1 93.5(2) . . ? C1 Bi1 N2 71.4(3) . . ? O4 Bi1 N2 93.4(2) . . ? O1 Bi1 N2 82.9(2) . . ? N1 Bi1 N2 144.0(2) . . ? C6 C1 C2 122.2(8) . . ? C6 C1 Bi1 119.8(6) . . ? C2 C1 Bi1 118.1(6) . . ? C1 C2 C3 117.6(9) . . ? C1 C2 C7 119.7(8) . . ? C3 C2 C7 122.3(8) . . ? C4 C3 C2 120.0(9) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 121.2(9) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.3(10) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.6(8) . . ? C1 C6 C10 118.9(7) . . ? C5 C6 C10 121.5(8) . . ? N1 C7 C2 111.0(7) . . ? N1 C7 H7A 109.4 . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C2 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C6 110.6(7) . . ? N2 C10 H10A 109.5 . . ? C6 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 N1 C8 110.8(7) . . ? C7 N1 C9 110.4(7) . . ? C8 N1 C9 109.2(7) . . ? C7 N1 Bi1 105.7(5) . . ? C8 N1 Bi1 108.2(5) . . ? C9 N1 Bi1 112.6(5) . . ? C10 N2 C12 108.6(7) . . ? C10 N2 C11 109.5(7) . . ? C12 N2 C11 110.1(7) . . ? C10 N2 Bi1 104.7(5) . . ? C12 N2 Bi1 109.2(5) . . ? C11 N2 Bi1 114.5(6) . . ? O3 N3 O2 121.9(10) . . ? O3 N3 O1 119.6(9) . . ? O2 N3 O1 118.4(9) . . ? O5 N4 O6 124.0(9) . . ? O5 N4 O4 118.9(9) . . ? O6 N4 O4 117.0(9) . . ? N3 O1 Bi1 111.0(6) . . ? N4 O4 Bi1 110.8(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Bi1 C1 C6 110.7(7) . . . . ? O1 Bi1 C1 C6 -70.6(7) . . . . ? N1 Bi1 C1 C6 -167.2(8) . . . . ? N2 Bi1 C1 C6 15.0(6) . . . . ? O4 Bi1 C1 C2 -69.9(7) . . . . ? O1 Bi1 C1 C2 108.9(7) . . . . ? N1 Bi1 C1 C2 12.3(6) . . . . ? N2 Bi1 C1 C2 -165.5(7) . . . . ? C6 C1 C2 C3 -1.4(13) . . . . ? Bi1 C1 C2 C3 179.2(6) . . . . ? C6 C1 C2 C7 -175.3(8) . . . . ? Bi1 C1 C2 C7 5.3(11) . . . . ? C1 C2 C3 C4 0.6(14) . . . . ? C7 C2 C3 C4 174.3(9) . . . . ? C2 C3 C4 C5 -0.4(15) . . . . ? C3 C4 C5 C6 0.9(15) . . . . ? C2 C1 C6 C5 1.9(13) . . . . ? Bi1 C1 C6 C5 -178.6(6) . . . . ? C2 C1 C6 C10 -176.6(8) . . . . ? Bi1 C1 C6 C10 2.8(11) . . . . ? C4 C5 C6 C1 -1.7(13) . . . . ? C4 C5 C6 C10 176.8(9) . . . . ? C1 C2 C7 N1 -32.1(12) . . . . ? C3 C2 C7 N1 154.3(8) . . . . ? C1 C6 C10 N2 -32.7(11) . . . . ? C5 C6 C10 N2 148.8(8) . . . . ? C2 C7 N1 C8 -79.3(9) . . . . ? C2 C7 N1 C9 159.7(8) . . . . ? C2 C7 N1 Bi1 37.7(8) . . . . ? C1 Bi1 N1 C7 -27.2(6) . . . . ? O4 Bi1 N1 C7 59.1(6) . . . . ? O1 Bi1 N1 C7 -106.4(6) . . . . ? N2 Bi1 N1 C7 -23.7(8) . . . . ? C1 Bi1 N1 C8 91.4(6) . . . . ? O4 Bi1 N1 C8 177.8(6) . . . . ? O1 Bi1 N1 C8 12.2(5) . . . . ? N2 Bi1 N1 C8 94.9(6) . . . . ? C1 Bi1 N1 C9 -147.8(7) . . . . ? O4 Bi1 N1 C9 -61.4(6) . . . . ? O1 Bi1 N1 C9 133.0(6) . . . . ? N2 Bi1 N1 C9 -144.3(6) . . . . ? C6 C10 N2 C12 -76.5(9) . . . . ? C6 C10 N2 C11 163.3(8) . . . . ? C6 C10 N2 Bi1 40.0(8) . . . . ? C1 Bi1 N2 C10 -29.8(5) . . . . ? O4 Bi1 N2 C10 -112.1(5) . . . . ? O1 Bi1 N2 C10 52.8(5) . . . . ? N1 Bi1 N2 C10 -33.3(7) . . . . ? C1 Bi1 N2 C12 86.3(6) . . . . ? O4 Bi1 N2 C12 4.0(6) . . . . ? O1 Bi1 N2 C12 168.9(6) . . . . ? N1 Bi1 N2 C12 82.8(6) . . . . ? C1 Bi1 N2 C11 -149.8(7) . . . . ? O4 Bi1 N2 C11 127.9(6) . . . . ? O1 Bi1 N2 C11 -67.2(6) . . . . ? N1 Bi1 N2 C11 -153.3(6) . . . . ? O3 N3 O1 Bi1 164.6(8) . . . . ? O2 N3 O1 Bi1 -17.0(10) . . . . ? C1 Bi1 O1 N3 171.8(6) . . . . ? O4 Bi1 O1 N3 176.4(7) . . . . ? N1 Bi1 O1 N3 -116.3(6) . . . . ? N2 Bi1 O1 N3 99.6(6) . . . . ? O5 N4 O4 Bi1 8.9(11) . . . . ? O6 N4 O4 Bi1 -170.3(7) . . . . ? C1 Bi1 O4 N4 -152.2(6) . . . . ? O1 Bi1 O4 N4 -156.8(8) . . . . ? N1 Bi1 O4 N4 134.3(6) . . . . ? N2 Bi1 O4 N4 -81.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.975 _refine_diff_density_min -1.681 _refine_diff_density_rms 0.195 # Attachment '- Compound 3 - CCDC 773765.cif' data_51alb _database_code_depnum_ccdc_archive 'CCDC 773765' #TrackingRef '- Compound 3 - CCDC 773765.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H19 Bi N2 O4 S' _chemical_formula_sum 'C12 H19 Bi N2 O4 S' _chemical_formula_weight 496.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'Pc ' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 9.0893(18) _cell_length_b 8.5626(17) _cell_length_c 11.564(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.525(3) _cell_angle_gamma 90.00 _cell_volume 837.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3838 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 25.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.969 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 10.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.053 _exptl_absorpt_correction_T_max 0.123 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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_% ? _diffrn_reflns_number 7704 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2932 _reflns_number_gt 2858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0421P)^2^+2.7879P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.016(16) _refine_ls_number_reflns 2932 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 -0.00300(4) 0.90605(4) 0.74980(4) 0.02904(15) Uani 1 1 d . . . C1 C 0.1756(15) 0.7359(14) 0.7472(12) 0.032(3) Uani 1 1 d . . . C2 C 0.3327(16) 0.7656(18) 0.8247(15) 0.045(4) Uani 1 1 d . . . C3 C 0.445(2) 0.658(2) 0.8138(19) 0.060(5) Uani 1 1 d . . . H3 H 0.5504 0.6693 0.8646 0.072 Uiso 1 1 calc R . . C4 C 0.404(2) 0.541(2) 0.733(2) 0.074(6) Uani 1 1 d . . . H4 H 0.4816 0.4740 0.7289 0.089 Uiso 1 1 calc R . . C5 C 0.242(2) 0.515(2) 0.6528(19) 0.061(5) Uani 1 1 d . . . H5 H 0.2146 0.4338 0.5951 0.073 Uiso 1 1 calc R . . C6 C 0.1315(19) 0.6146(14) 0.6655(15) 0.036(3) Uani 1 1 d . . . C7 C 0.3698(18) 0.8946(17) 0.9095(16) 0.048(4) Uani 1 1 d . . . H7A H 0.4796 0.9241 0.9302 0.058 Uiso 1 1 calc R . . H7B H 0.3561 0.8636 0.9855 0.058 Uiso 1 1 calc R . . C8 C 0.323(2) 1.136(3) 0.7699(17) 0.071(6) Uani 1 1 d . . . H8A H 0.2432 1.2127 0.7294 0.106 Uiso 1 1 calc R . . H8B H 0.3418 1.0727 0.7084 0.106 Uiso 1 1 calc R . . H8C H 0.4188 1.1880 0.8196 0.106 Uiso 1 1 calc R . . C9 C 0.260(2) 1.147(2) 0.9482(16) 0.056(4) Uani 1 1 d . . . H9A H 0.2215 1.0974 1.0059 0.084 Uiso 1 1 calc R . . H9B H 0.1908 1.2318 0.9077 0.084 Uiso 1 1 calc R . . H9C H 0.3644 1.1875 0.9921 0.084 Uiso 1 1 calc R . . C10 C -0.043(2) 0.6093(17) 0.5811(16) 0.046(4) Uani 1 1 d . . . H10A H -0.0595 0.6738 0.5084 0.055 Uiso 1 1 calc R . . H10B H -0.0719 0.5030 0.5534 0.055 Uiso 1 1 calc R . . C11 C -0.155(2) 0.555(2) 0.7399(19) 0.057(4) Uani 1 1 d . . . H11A H -0.1904 0.6087 0.7975 0.085 Uiso 1 1 calc R . . H11B H -0.0527 0.5095 0.7839 0.085 Uiso 1 1 calc R . . H11C H -0.2285 0.4740 0.6991 0.085 Uiso 1 1 calc R . . C12 C -0.300(2) 0.706(3) 0.561(2) 0.078(6) Uani 1 1 d . . . H12A H -0.2923 0.7860 0.5054 0.118 Uiso 1 1 calc R . . H12B H -0.3625 0.7428 0.6065 0.118 Uiso 1 1 calc R . . H12C H -0.3491 0.6150 0.5138 0.118 Uiso 1 1 calc R . . N1 N 0.2654(15) 1.0323(16) 0.8537(11) 0.044(3) Uani 1 1 d . . . N2 N -0.1425(14) 0.6656(15) 0.6471(11) 0.042(3) Uani 1 1 d . . . O1 O -0.0243(13) 0.9651(12) 0.5479(9) 0.044(2) Uani 1 1 d . . . O2 O 0.0236(12) 1.1873(11) 0.4473(9) 0.040(2) Uani 1 1 d . . . O3 O -0.1166(17) 1.2133(14) 0.5897(11) 0.063(3) Uani 1 1 d . . . O4 O -0.2385(16) 1.0924(14) 0.3872(12) 0.061(3) Uani 1 1 d . . . S1 S -0.0932(5) 1.1177(4) 0.4940(3) 0.0373(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 Bi1 0.0323(2) 0.0277(2) 0.0269(2) -0.0052(3) 0.01062(15) -0.0019(4) C1 0.033(7) 0.030(7) 0.036(7) 0.011(6) 0.016(5) 0.010(5) C2 0.032(7) 0.046(9) 0.057(9) 0.013(7) 0.016(7) 0.003(6) C3 0.043(9) 0.050(10) 0.084(13) 0.012(10) 0.020(9) 0.010(8) C4 0.055(12) 0.059(11) 0.133(19) 0.013(13) 0.063(13) 0.016(10) C5 0.068(12) 0.042(9) 0.097(14) -0.002(9) 0.059(11) 0.008(8) C6 0.052(9) 0.016(6) 0.046(9) 0.007(6) 0.023(7) 0.004(6) C7 0.027(7) 0.060(10) 0.047(9) -0.002(7) 0.001(7) -0.007(6) C8 0.043(9) 0.137(17) 0.051(10) 0.043(11) 0.038(8) 0.020(10) C9 0.073(12) 0.040(8) 0.058(10) -0.017(8) 0.028(9) -0.024(9) C10 0.065(11) 0.034(8) 0.040(9) -0.013(6) 0.019(8) -0.013(7) C11 0.067(12) 0.042(8) 0.073(12) -0.012(9) 0.038(10) -0.004(8) C12 0.038(9) 0.101(16) 0.076(13) -0.020(12) -0.003(9) -0.010(10) N1 0.044(7) 0.047(7) 0.037(7) -0.011(6) 0.011(5) -0.016(6) N2 0.038(7) 0.043(7) 0.044(7) -0.003(6) 0.012(5) -0.013(6) O1 0.059(6) 0.036(5) 0.043(6) 0.017(5) 0.025(5) 0.015(5) O2 0.056(6) 0.033(5) 0.035(5) 0.000(4) 0.024(5) -0.010(4) O3 0.097(10) 0.045(6) 0.058(7) -0.009(5) 0.041(7) 0.007(6) O4 0.048(7) 0.086(10) 0.047(7) 0.004(5) 0.015(6) 0.007(5) S1 0.051(2) 0.0303(17) 0.0352(19) 0.0022(14) 0.0209(16) 0.0079(15) _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 C1 2.189(12) . ? Bi1 O1 2.327(9) . ? Bi1 O2 2.347(9) 2_575 ? Bi1 N2 2.481(12) . ? Bi1 N1 2.532(12) . ? C1 C6 1.361(19) . ? C1 C2 1.40(2) . ? C2 C3 1.41(2) . ? C2 C7 1.43(2) . ? C3 C4 1.32(3) . ? C3 H3 0.9300 . ? C4 C5 1.44(3) . ? C4 H4 0.9300 . ? C5 C6 1.37(2) . ? C5 H5 0.9300 . ? C6 C10 1.53(3) . ? C7 N1 1.50(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.54(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.49(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N2 1.46(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.47(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.45(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O1 S1 1.484(10) . ? O2 S1 1.481(10) . ? O2 Bi1 2.347(9) 2_574 ? O3 S1 1.453(11) . ? O4 S1 1.455(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 C1 Bi1 O1 85.4(4) . . ? C1 Bi1 O2 88.6(4) . 2_575 ? O1 Bi1 O2 172.5(3) . 2_575 ? C1 Bi1 N2 72.1(5) . . ? O1 Bi1 N2 82.0(4) . . ? O2 Bi1 N2 92.0(4) 2_575 . ? C1 Bi1 N1 72.6(5) . . ? O1 Bi1 N1 95.4(4) . . ? O2 Bi1 N1 86.9(4) 2_575 . ? N2 Bi1 N1 144.7(4) . . ? C6 C1 C2 123.6(13) . . ? C6 C1 Bi1 119.1(10) . . ? C2 C1 Bi1 117.1(10) . . ? C1 C2 C3 114.9(15) . . ? C1 C2 C7 120.4(13) . . ? C3 C2 C7 124.6(15) . . ? C4 C3 C2 122.0(17) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 122.2(16) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C6 C5 C4 116.5(17) . . ? C6 C5 H5 121.7 . . ? C4 C5 H5 121.7 . . ? C1 C6 C5 120.7(16) . . ? C1 C6 C10 116.0(13) . . ? C5 C6 C10 122.9(15) . . ? C2 C7 N1 111.0(13) . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7A 109.4 . . ? C2 C7 H7B 109.4 . . ? N1 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C6 110.7(13) . . ? N2 C10 H10A 109.5 . . ? C6 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 N1 C7 113.0(13) . . ? C9 N1 C8 100.9(14) . . ? C7 N1 C8 114.6(13) . . ? C9 N1 Bi1 110.3(10) . . ? C7 N1 Bi1 102.4(8) . . ? C8 N1 Bi1 115.9(10) . . ? C12 N2 C10 111.3(14) . . ? C12 N2 C11 109.6(15) . . ? C10 N2 C11 113.3(13) . . ? C12 N2 Bi1 109.5(11) . . ? C10 N2 Bi1 102.5(8) . . ? C11 N2 Bi1 110.4(10) . . ? S1 O1 Bi1 118.7(6) . . ? S1 O2 Bi1 112.7(5) . 2_574 ? O3 S1 O4 112.9(8) . . ? O3 S1 O2 112.0(7) . . ? O4 S1 O2 107.4(7) . . ? O3 S1 O1 109.5(7) . . ? O4 S1 O1 109.7(7) . . ? O2 S1 O1 105.0(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Bi1 C1 C6 -63.7(11) . . . . ? O2 Bi1 C1 C6 111.9(11) 2_575 . . . ? N2 Bi1 C1 C6 19.3(10) . . . . ? N1 Bi1 C1 C6 -160.8(11) . . . . ? O1 Bi1 C1 C2 111.8(10) . . . . ? O2 Bi1 C1 C2 -72.6(10) 2_575 . . . ? N2 Bi1 C1 C2 -165.2(11) . . . . ? N1 Bi1 C1 C2 14.7(10) . . . . ? C6 C1 C2 C3 -1(2) . . . . ? Bi1 C1 C2 C3 -176.1(11) . . . . ? C6 C1 C2 C7 -179.2(14) . . . . ? Bi1 C1 C2 C7 5.5(18) . . . . ? C1 C2 C3 C4 2(3) . . . . ? C7 C2 C3 C4 -179.7(19) . . . . ? C2 C3 C4 C5 -1(3) . . . . ? C3 C4 C5 C6 -2(3) . . . . ? C2 C1 C6 C5 -1(2) . . . . ? Bi1 C1 C6 C5 173.7(12) . . . . ? C2 C1 C6 C10 -174.9(14) . . . . ? Bi1 C1 C6 C10 0.3(18) . . . . ? C4 C5 C6 C1 3(2) . . . . ? C4 C5 C6 C10 175.6(16) . . . . ? C1 C2 C7 N1 -36(2) . . . . ? C3 C2 C7 N1 145.4(16) . . . . ? C1 C6 C10 N2 -35.3(18) . . . . ? C5 C6 C10 N2 151.4(15) . . . . ? C2 C7 N1 C9 160.8(14) . . . . ? C2 C7 N1 C8 -84.2(17) . . . . ? C2 C7 N1 Bi1 42.2(14) . . . . ? C1 Bi1 N1 C9 -150.6(12) . . . . ? O1 Bi1 N1 C9 125.9(11) . . . . ? O2 Bi1 N1 C9 -61.2(11) 2_575 . . . ? N2 Bi1 N1 C9 -150.3(10) . . . . ? C1 Bi1 N1 C7 -30.1(9) . . . . ? O1 Bi1 N1 C7 -113.5(9) . . . . ? O2 Bi1 N1 C7 59.4(9) 2_575 . . . ? N2 Bi1 N1 C7 -29.8(13) . . . . ? C1 Bi1 N1 C8 95.5(12) . . . . ? O1 Bi1 N1 C8 12.1(12) . . . . ? O2 Bi1 N1 C8 -175.0(12) 2_575 . . . ? N2 Bi1 N1 C8 95.8(13) . . . . ? C6 C10 N2 C12 162.8(14) . . . . ? C6 C10 N2 C11 -73.1(16) . . . . ? C6 C10 N2 Bi1 45.9(12) . . . . ? C1 Bi1 N2 C12 -152.9(13) . . . . ? O1 Bi1 N2 C12 -65.2(12) . . . . ? O2 Bi1 N2 C12 119.2(12) 2_575 . . . ? N1 Bi1 N2 C12 -153.2(12) . . . . ? C1 Bi1 N2 C10 -34.7(9) . . . . ? O1 Bi1 N2 C10 53.0(9) . . . . ? O2 Bi1 N2 C10 -122.5(9) 2_575 . . . ? N1 Bi1 N2 C10 -35.0(13) . . . . ? C1 Bi1 N2 C11 86.3(11) . . . . ? O1 Bi1 N2 C11 174.0(11) . . . . ? O2 Bi1 N2 C11 -1.6(10) 2_575 . . . ? N1 Bi1 N2 C11 86.0(12) . . . . ? C1 Bi1 O1 S1 -159.6(8) . . . . ? N2 Bi1 O1 S1 127.9(7) . . . . ? N1 Bi1 O1 S1 -87.6(7) . . . . ? Bi1 O2 S1 O3 -158.6(7) 2_574 . . . ? Bi1 O2 S1 O4 -34.1(8) 2_574 . . . ? Bi1 O2 S1 O1 82.7(6) 2_574 . . . ? Bi1 O1 S1 O3 7.6(10) . . . . ? Bi1 O1 S1 O4 -116.8(8) . . . . ? Bi1 O1 S1 O2 128.0(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.963 _refine_diff_density_min -1.824 _refine_diff_density_rms 0.210 # Attachment '- Compound 2 - CCDC 773767.cif' data_nm3 _database_code_depnum_ccdc_archive 'CCDC 773767' #TrackingRef '- Compound 2 - CCDC 773767.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H38 Bi2 N4 O6, C H2 Cl2' _chemical_formula_sum 'C27 H40 Bi2 Cl2 N4 O6' _chemical_formula_weight 1005.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 '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 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8147(16) _cell_length_b 17.108(4) _cell_length_c 21.837(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.410(18) _cell_angle_gamma 90.00 _cell_volume 3228.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 68 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 14.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1912 _exptl_absorpt_coefficient_mu 11.098 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.048 _exptl_absorpt_correction_T_max 0.112 _exptl_absorpt_process_details 'N. Walker and D. Stuart, Acta Crystallogr.Sect A 1983, 39, 158-166.' _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_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 13630 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.0960 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5677 _reflns_number_gt 4212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0589P)^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 5677 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.39955(4) 0.16786(2) 0.15968(2) 0.02167(13) Uani 1 1 d . . . Bi2 Bi 0.26557(4) -0.06386(2) 0.31359(2) 0.02455(14) Uani 1 1 d . . . C1 C 0.3846(12) 0.0610(7) 0.0994(6) 0.029(3) Uani 1 1 d . . . C2 C 0.2595(12) 0.0522(7) 0.0488(6) 0.029(3) Uani 1 1 d . . . C3 C 0.2590(14) -0.0123(7) 0.0113(6) 0.040(3) Uani 1 1 d . . . H3 H 0.1793 -0.0184 -0.0247 0.048 Uiso 1 1 calc R . . C4 C 0.3754(15) -0.0693(7) 0.0257(7) 0.037(3) Uani 1 1 d . . . H4 H 0.3744 -0.1138 -0.0005 0.044 Uiso 1 1 calc R . . C5 C 0.4905(13) -0.0604(7) 0.0776(6) 0.032(3) Uani 1 1 d . . . H5 H 0.5680 -0.0995 0.0874 0.039 Uiso 1 1 calc R . . C6 C 0.4962(12) 0.0052(6) 0.1166(6) 0.025(3) Uani 1 1 d . . . C10 C 0.6113(12) 0.0126(6) 0.1751(6) 0.032(3) Uani 1 1 d . . . H10A H 0.7049 -0.0175 0.1712 0.038 Uiso 1 1 calc R . . H10B H 0.5685 -0.0107 0.2096 0.038 Uiso 1 1 calc R . . C12 C 0.7168(13) 0.1008(8) 0.2589(7) 0.044(4) Uani 1 1 d . . . H12A H 0.7988 0.0620 0.2716 0.067 Uiso 1 1 calc R . . H12B H 0.6331 0.0915 0.2816 0.067 Uiso 1 1 calc R . . H12C H 0.7590 0.1534 0.2684 0.067 Uiso 1 1 calc R . . C11 C 0.7709(12) 0.1191(7) 0.1567(7) 0.034(3) Uani 1 1 d . . . H11A H 0.8690 0.0925 0.1729 0.051 Uiso 1 1 calc R . . H11B H 0.7856 0.1758 0.1613 0.051 Uiso 1 1 calc R . . H11C H 0.7363 0.1062 0.1124 0.051 Uiso 1 1 calc R . . C7 C 0.1269(13) 0.1113(7) 0.0394(6) 0.032(3) Uani 1 1 d . . . H7A H 0.0729 0.1102 -0.0048 0.038 Uiso 1 1 calc R . . H7B H 0.0517 0.0956 0.0653 0.038 Uiso 1 1 calc R . . C9 C 0.0529(13) 0.2379(8) 0.0671(7) 0.041(3) Uani 1 1 d . . . H9A H -0.0277 0.2394 0.0291 0.061 Uiso 1 1 calc R . . H9B H 0.0888 0.2911 0.0784 0.061 Uiso 1 1 calc R . . H9C H 0.0106 0.2149 0.1012 0.061 Uiso 1 1 calc R . . C8 C 0.2430(14) 0.2248(7) 0.0041(6) 0.037(3) Uani 1 1 d . . . H8A H 0.1580 0.2371 -0.0308 0.055 Uiso 1 1 calc R . . H8B H 0.3124 0.1867 -0.0096 0.055 Uiso 1 1 calc R . . H8C H 0.3007 0.2726 0.0181 0.055 Uiso 1 1 calc R . . C25 C 0.2156(11) 0.0848(6) 0.2258(5) 0.016(2) Uani 1 1 d . . . C13 C 0.0248(10) -0.0997(6) 0.3177(5) 0.018(2) Uani 1 1 d . . . C18 C -0.0407(14) -0.0665(7) 0.3637(6) 0.031(3) Uani 1 1 d . . . C17 C -0.1990(13) -0.0776(7) 0.3611(7) 0.036(3) Uani 1 1 d . . . H17 H -0.2494 -0.0539 0.3909 0.043 Uiso 1 1 calc R . . C16 C -0.2822(12) -0.1250(8) 0.3129(7) 0.037(3) Uani 1 1 d . . . H16 H -0.3891 -0.1341 0.3114 0.045 Uiso 1 1 calc R . . C15 C -0.2158(13) -0.1571(7) 0.2697(7) 0.040(4) Uani 1 1 d . . . H15 H -0.2758 -0.1878 0.2376 0.048 Uiso 1 1 calc R . . C14 C -0.0556(11) -0.1461(6) 0.2711(6) 0.027(3) Uani 1 1 d . . . C19 C 0.0278(15) -0.1844(7) 0.2256(7) 0.040(3) Uani 1 1 d . . . H19A H 0.0823 -0.2315 0.2451 0.048 Uiso 1 1 calc R . . H19B H -0.0485 -0.2014 0.1884 0.048 Uiso 1 1 calc R . . C20 C 0.2535(17) -0.1755(9) 0.1782(8) 0.054(4) Uani 1 1 d . . . H20A H 0.1977 -0.2100 0.1456 0.081 Uiso 1 1 calc R . . H20B H 0.3182 -0.2069 0.2108 0.081 Uiso 1 1 calc R . . H20C H 0.3192 -0.1397 0.1599 0.081 Uiso 1 1 calc R . . C21 C 0.0600(16) -0.0771(8) 0.1576(6) 0.041(3) Uani 1 1 d . . . H21A H 0.1313 -0.0366 0.1487 0.062 Uiso 1 1 calc R . . H21B H -0.0260 -0.0526 0.1728 0.062 Uiso 1 1 calc R . . H21C H 0.0196 -0.1065 0.1194 0.062 Uiso 1 1 calc R . . C22 C 0.0589(14) -0.0264(8) 0.4188(7) 0.042(3) Uani 1 1 d . . . H22A H -0.0066 0.0083 0.4390 0.051 Uiso 1 1 calc R . . H22B H 0.1055 -0.0662 0.4498 0.051 Uiso 1 1 calc R . . C24 C 0.3160(16) 0.0306(8) 0.4533(7) 0.048(4) Uani 1 1 d . . . H24A H 0.4040 0.0537 0.4386 0.073 Uiso 1 1 calc R . . H24B H 0.3458 -0.0204 0.4723 0.073 Uiso 1 1 calc R . . H24C H 0.2848 0.0653 0.4844 0.073 Uiso 1 1 calc R . . C23 C 0.1241(15) 0.0979(7) 0.3785(7) 0.044(4) Uani 1 1 d . . . H23A H 0.1085 0.1289 0.4145 0.066 Uiso 1 1 calc R . . H23B H 0.0252 0.0920 0.3492 0.066 Uiso 1 1 calc R . . H23C H 0.1982 0.1246 0.3577 0.066 Uiso 1 1 calc R . . C26 C 0.3860(12) -0.2000(7) 0.3805(7) 0.033(3) Uani 1 1 d . . . C27 C 0.6250(15) 0.2091(9) 0.4499(8) 0.051(4) Uani 1 1 d . . . H27A H 0.5866 0.1907 0.4871 0.061 Uiso 1 1 calc R . . H27B H 0.6802 0.2591 0.4610 0.061 Uiso 1 1 calc R . . Cl1 Cl 0.7549(5) 0.1400(3) 0.4305(2) 0.0664(12) Uani 1 1 d . . . Cl2 Cl 0.4682(4) 0.2251(2) 0.3889(2) 0.0550(10) Uani 1 1 d . . . N2 N 0.6559(10) 0.0940(6) 0.1911(5) 0.031(2) Uani 1 1 d . . . N1 N 0.1796(9) 0.1916(5) 0.0561(5) 0.028(2) Uani 1 1 d . . . N3 N 0.1426(11) -0.1305(6) 0.2054(5) 0.033(2) Uani 1 1 d . . . N4 N 0.1844(11) 0.0206(5) 0.3997(5) 0.030(2) Uani 1 1 d . . . O6 O 0.5456(8) 0.2414(4) 0.0896(4) 0.0286(19) Uani 1 1 d . . . O2 O 0.1541(8) 0.1303(5) 0.1825(4) 0.033(2) Uani 1 1 d . . . O1 O 0.3638(8) 0.0789(5) 0.2412(4) 0.031(2) Uani 1 1 d . . . O3 O 0.1310(8) 0.0429(5) 0.2541(4) 0.031(2) Uani 1 1 d . . . O4 O 0.3467(8) -0.1997(5) 0.3211(4) 0.0282(19) Uani 1 1 d . . . O5 O 0.3554(9) -0.1366(5) 0.4103(4) 0.0317(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02248(19) 0.0208(2) 0.0215(3) -0.00001(19) 0.00391(17) -0.00134(16) Bi2 0.02101(19) 0.0248(2) 0.0285(3) 0.0052(2) 0.00656(18) 0.00178(16) C1 0.026(5) 0.032(6) 0.029(8) -0.009(6) 0.006(5) -0.002(5) C2 0.031(5) 0.035(7) 0.023(7) -0.003(6) 0.007(5) -0.013(5) C3 0.046(7) 0.041(7) 0.029(8) -0.009(6) -0.002(6) -0.031(6) C4 0.059(7) 0.023(6) 0.028(8) 0.002(6) 0.008(7) -0.005(6) C5 0.036(6) 0.030(6) 0.036(9) -0.005(6) 0.021(6) -0.002(5) C6 0.027(5) 0.025(5) 0.023(7) -0.009(5) 0.008(5) -0.010(5) C10 0.029(5) 0.027(6) 0.040(9) 0.011(6) 0.009(6) 0.000(5) C12 0.034(6) 0.044(7) 0.052(11) 0.011(7) 0.001(6) -0.003(6) C11 0.024(5) 0.036(7) 0.043(9) 0.004(6) 0.008(5) 0.006(5) C7 0.037(6) 0.041(7) 0.014(7) 0.001(6) -0.003(5) -0.013(6) C9 0.037(6) 0.047(8) 0.035(9) 0.018(7) -0.003(6) 0.007(6) C8 0.043(6) 0.039(7) 0.027(8) 0.007(6) 0.005(6) -0.005(6) C25 0.022(5) 0.023(5) 0.003(6) 0.005(5) 0.004(4) 0.002(4) C13 0.018(4) 0.027(5) 0.009(6) 0.012(5) 0.002(4) 0.004(4) C18 0.042(6) 0.032(6) 0.020(7) 0.010(6) 0.010(6) 0.003(6) C17 0.032(6) 0.037(7) 0.044(9) 0.016(7) 0.019(6) 0.013(6) C16 0.025(5) 0.048(8) 0.044(9) 0.014(7) 0.022(6) 0.005(6) C15 0.033(6) 0.036(7) 0.042(10) 0.008(7) -0.014(6) -0.006(6) C14 0.020(5) 0.021(5) 0.041(9) 0.009(6) 0.006(5) -0.004(4) C19 0.050(7) 0.023(6) 0.043(10) -0.005(6) -0.001(7) 0.001(6) C20 0.069(9) 0.054(9) 0.046(11) 0.000(8) 0.029(8) 0.020(8) C21 0.063(8) 0.040(7) 0.022(8) -0.005(6) 0.010(7) 0.004(7) C22 0.052(7) 0.032(7) 0.047(10) -0.009(7) 0.017(7) -0.006(6) C24 0.065(8) 0.041(7) 0.029(9) -0.005(7) -0.015(7) -0.004(7) C23 0.047(7) 0.021(6) 0.059(11) -0.002(7) 0.000(7) 0.006(6) C26 0.024(5) 0.029(6) 0.050(10) -0.015(7) 0.017(6) -0.005(5) C27 0.050(7) 0.052(8) 0.053(11) -0.010(8) 0.017(8) -0.002(7) Cl1 0.083(3) 0.070(3) 0.049(3) 0.006(2) 0.019(2) 0.033(2) Cl2 0.0435(16) 0.058(2) 0.062(3) 0.008(2) 0.0076(18) -0.0025(17) N2 0.025(4) 0.026(5) 0.042(8) 0.000(5) 0.007(5) 0.001(4) N1 0.022(4) 0.021(5) 0.039(7) -0.004(5) -0.001(4) -0.001(4) N3 0.038(5) 0.029(5) 0.035(7) 0.007(5) 0.011(5) 0.011(5) N4 0.040(5) 0.025(5) 0.022(6) -0.009(5) -0.003(5) 0.007(4) O6 0.030(4) 0.033(4) 0.021(5) -0.013(4) 0.000(3) -0.010(4) O2 0.021(3) 0.036(5) 0.044(6) 0.010(4) 0.012(4) 0.001(3) O1 0.027(4) 0.036(4) 0.030(6) 0.010(4) 0.006(4) 0.000(4) O3 0.027(4) 0.038(4) 0.030(6) 0.011(4) 0.008(4) 0.010(4) O4 0.029(4) 0.036(4) 0.017(5) 0.008(4) -0.001(4) 0.002(4) O5 0.047(4) 0.037(4) 0.011(5) 0.005(4) 0.006(4) 0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.242(11) . ? Bi1 O2 2.402(7) . ? Bi1 O1 2.411(8) . ? Bi1 O6 2.522(8) . ? Bi1 N2 2.561(9) . ? Bi1 N1 2.703(10) . ? Bi1 C25 2.768(10) . ? Bi2 C13 2.228(9) . ? Bi2 O3 2.412(7) . ? Bi2 O4 2.428(8) . ? Bi2 O5 2.444(8) . ? Bi2 N4 2.583(10) . ? Bi2 N3 2.653(11) . ? Bi2 C26 2.841(14) . ? C1 C6 1.369(15) . ? C1 C2 1.406(16) . ? C2 C3 1.374(17) . ? C2 C7 1.528(16) . ? C3 C4 1.405(17) . ? C3 H3 0.9500 . ? C4 C5 1.373(18) . ? C4 H4 0.9500 . ? C5 C6 1.403(16) . ? C5 H5 0.9500 . ? C6 C10 1.470(16) . ? C10 N2 1.471(15) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C12 N2 1.477(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C11 N2 1.442(14) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C7 N1 1.473(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 N1 1.428(14) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C8 N1 1.475(16) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C25 O2 1.262(13) . ? C25 O3 1.278(12) . ? C25 O1 1.287(12) . ? C13 C14 1.373(16) . ? C13 C18 1.375(16) . ? C18 C17 1.399(16) . ? C18 C22 1.507(18) . ? C17 C16 1.413(19) . ? C17 H17 0.9500 . ? C16 C15 1.323(19) . ? C16 H16 0.9500 . ? C15 C14 1.419(15) . ? C15 H15 0.9500 . ? C14 C19 1.499(18) . ? C19 N3 1.498(16) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N3 1.460(16) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N3 1.467(16) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N4 1.493(15) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C24 N4 1.485(15) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C23 N4 1.467(15) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C26 O4 1.275(16) . ? C26 O6 1.280(15) 2_645 ? C26 O5 1.320(14) . ? C27 Cl2 1.742(15) . ? C27 Cl1 1.755(14) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? O6 C26 1.280(15) 2_655 ? 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 Bi1 O2 87.3(3) . . ? C1 Bi1 O1 85.3(4) . . ? O2 Bi1 O1 54.8(3) . . ? C1 Bi1 O6 91.7(3) . . ? O2 Bi1 O6 148.0(3) . . ? O1 Bi1 O6 157.0(2) . . ? C1 Bi1 N2 72.6(4) . . ? O2 Bi1 N2 126.6(3) . . ? O1 Bi1 N2 74.2(3) . . ? O6 Bi1 N2 83.1(3) . . ? C1 Bi1 N1 71.5(4) . . ? O2 Bi1 N1 71.8(3) . . ? O1 Bi1 N1 122.4(3) . . ? O6 Bi1 N1 77.6(3) . . ? N2 Bi1 N1 138.3(3) . . ? C1 Bi1 C25 85.1(4) . . ? O2 Bi1 C25 27.1(3) . . ? O1 Bi1 C25 27.7(3) . . ? O6 Bi1 C25 174.1(3) . . ? N2 Bi1 C25 100.6(3) . . ? N1 Bi1 C25 96.7(3) . . ? C13 Bi2 O3 81.9(3) . . ? C13 Bi2 O4 90.2(3) . . ? O3 Bi2 O4 150.2(3) . . ? C13 Bi2 O5 88.5(3) . . ? O3 Bi2 O5 153.0(3) . . ? O4 Bi2 O5 54.1(3) . . ? C13 Bi2 N4 73.8(4) . . ? O3 Bi2 N4 77.9(3) . . ? O4 Bi2 N4 127.4(3) . . ? O5 Bi2 N4 75.2(3) . . ? C13 Bi2 N3 72.1(4) . . ? O3 Bi2 N3 77.0(3) . . ? O4 Bi2 N3 73.2(3) . . ? O5 Bi2 N3 123.8(3) . . ? N4 Bi2 N3 140.0(3) . . ? C13 Bi2 C26 90.9(3) . . ? O3 Bi2 C26 172.5(3) . . ? O4 Bi2 C26 26.6(3) . . ? O5 Bi2 C26 27.7(3) . . ? N4 Bi2 C26 102.3(3) . . ? N3 Bi2 C26 98.7(3) . . ? C6 C1 C2 123.4(11) . . ? C6 C1 Bi1 116.9(8) . . ? C2 C1 Bi1 119.6(8) . . ? C3 C2 C1 117.7(11) . . ? C3 C2 C7 122.6(11) . . ? C1 C2 C7 119.6(10) . . ? C2 C3 C4 120.5(12) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.7(12) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.5(11) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 116.9(11) . . ? C1 C6 C10 120.9(10) . . ? C5 C6 C10 122.1(11) . . ? C6 C10 N2 113.1(9) . . ? C6 C10 H10A 108.9 . . ? N2 C10 H10A 108.9 . . ? C6 C10 H10B 108.9 . . ? N2 C10 H10B 108.9 . . ? H10A C10 H10B 107.8 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C7 C2 112.9(9) . . ? N1 C7 H7A 109.0 . . ? C2 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C25 O3 120.3(9) . . ? O2 C25 O1 120.5(9) . . ? O3 C25 O1 119.2(9) . . ? O2 C25 Bi1 60.1(5) . . ? O3 C25 Bi1 176.5(8) . . ? O1 C25 Bi1 60.5(5) . . ? C14 C13 C18 123.4(10) . . ? C14 C13 Bi2 119.0(8) . . ? C18 C13 Bi2 117.2(8) . . ? C13 C18 C17 118.2(12) . . ? C13 C18 C22 120.6(11) . . ? C17 C18 C22 120.9(12) . . ? C18 C17 C16 118.4(12) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C15 C16 C17 122.1(11) . . ? C15 C16 H16 119.0 . . ? C17 C16 H16 119.0 . . ? C16 C15 C14 120.6(13) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C13 C14 C15 117.2(12) . . ? C13 C14 C19 119.7(9) . . ? C15 C14 C19 123.0(12) . . ? N3 C19 C14 112.0(9) . . ? N3 C19 H19A 109.2 . . ? C14 C19 H19A 109.2 . . ? N3 C19 H19B 109.2 . . ? C14 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N4 C22 C18 111.6(11) . . ? N4 C22 H22A 109.3 . . ? C18 C22 H22A 109.3 . . ? N4 C22 H22B 109.3 . . ? C18 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? N4 C24 H24A 109.5 . . ? N4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N4 C23 H23A 109.5 . . ? N4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O4 C26 O6 121.8(11) . 2_645 ? O4 C26 O5 117.3(12) . . ? O6 C26 O5 120.9(13) 2_645 . ? O4 C26 Bi2 58.4(6) . . ? O6 C26 Bi2 174.0(7) 2_645 . ? O5 C26 Bi2 59.2(6) . . ? Cl2 C27 Cl1 112.2(9) . . ? Cl2 C27 H27A 109.2 . . ? Cl1 C27 H27A 109.2 . . ? Cl2 C27 H27B 109.2 . . ? Cl1 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C11 N2 C10 110.0(10) . . ? C11 N2 C12 110.2(9) . . ? C10 N2 C12 109.8(10) . . ? C11 N2 Bi1 112.8(7) . . ? C10 N2 Bi1 102.9(6) . . ? C12 N2 Bi1 110.9(7) . . ? C9 N1 C7 109.9(9) . . ? C9 N1 C8 110.1(9) . . ? C7 N1 C8 108.5(10) . . ? C9 N1 Bi1 113.5(8) . . ? C7 N1 Bi1 101.8(7) . . ? C8 N1 Bi1 112.6(6) . . ? C20 N3 C21 108.4(11) . . ? C20 N3 C19 109.9(10) . . ? C21 N3 C19 108.8(10) . . ? C20 N3 Bi2 113.6(8) . . ? C21 N3 Bi2 115.1(7) . . ? C19 N3 Bi2 100.6(8) . . ? C23 N4 C24 108.8(10) . . ? C23 N4 C22 109.4(9) . . ? C24 N4 C22 110.4(11) . . ? C23 N4 Bi2 114.2(9) . . ? C24 N4 Bi2 110.7(8) . . ? C22 N4 Bi2 103.3(7) . . ? C26 O6 Bi1 109.1(8) 2_655 . ? C25 O2 Bi1 92.8(5) . . ? C25 O1 Bi1 91.8(6) . . ? C25 O3 Bi2 114.4(6) . . ? C26 O4 Bi2 95.1(7) . . ? C26 O5 Bi2 93.1(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Bi1 C1 C6 -117.1(9) . . . . ? O1 Bi1 C1 C6 -62.3(9) . . . . ? O6 Bi1 C1 C6 94.9(9) . . . . ? N2 Bi1 C1 C6 12.7(8) . . . . ? N1 Bi1 C1 C6 171.2(10) . . . . ? C25 Bi1 C1 C6 -90.1(9) . . . . ? O2 Bi1 C1 C2 59.5(9) . . . . ? O1 Bi1 C1 C2 114.4(9) . . . . ? O6 Bi1 C1 C2 -88.5(9) . . . . ? N2 Bi1 C1 C2 -170.7(10) . . . . ? N1 Bi1 C1 C2 -12.1(9) . . . . ? C25 Bi1 C1 C2 86.6(9) . . . . ? C6 C1 C2 C3 -6.7(18) . . . . ? Bi1 C1 C2 C3 176.8(9) . . . . ? C6 C1 C2 C7 170.1(11) . . . . ? Bi1 C1 C2 C7 -6.3(15) . . . . ? C1 C2 C3 C4 3.6(18) . . . . ? C7 C2 C3 C4 -173.2(11) . . . . ? C2 C3 C4 C5 0.0(19) . . . . ? C3 C4 C5 C6 -0.9(18) . . . . ? C2 C1 C6 C5 5.8(17) . . . . ? Bi1 C1 C6 C5 -177.6(8) . . . . ? C2 C1 C6 C10 -171.1(11) . . . . ? Bi1 C1 C6 C10 5.4(14) . . . . ? C4 C5 C6 C1 -1.9(17) . . . . ? C4 C5 C6 C10 175.0(11) . . . . ? C1 C6 C10 N2 -34.1(15) . . . . ? C5 C6 C10 N2 149.1(10) . . . . ? C3 C2 C7 N1 -147.0(12) . . . . ? C1 C2 C7 N1 36.3(16) . . . . ? C1 Bi1 C25 O2 -93.6(7) . . . . ? O1 Bi1 C25 O2 177.3(11) . . . . ? N2 Bi1 C25 O2 -164.9(7) . . . . ? N1 Bi1 C25 O2 -22.9(7) . . . . ? C1 Bi1 C25 O1 89.1(7) . . . . ? O2 Bi1 C25 O1 -177.3(11) . . . . ? N2 Bi1 C25 O1 17.8(7) . . . . ? N1 Bi1 C25 O1 159.7(7) . . . . ? O3 Bi2 C13 C14 88.7(8) . . . . ? O4 Bi2 C13 C14 -62.5(8) . . . . ? O5 Bi2 C13 C14 -116.6(8) . . . . ? N4 Bi2 C13 C14 168.4(9) . . . . ? N3 Bi2 C13 C14 9.8(8) . . . . ? C26 Bi2 C13 C14 -89.0(9) . . . . ? O3 Bi2 C13 C18 -84.3(8) . . . . ? O4 Bi2 C13 C18 124.5(8) . . . . ? O5 Bi2 C13 C18 70.4(8) . . . . ? N4 Bi2 C13 C18 -4.6(8) . . . . ? N3 Bi2 C13 C18 -163.2(9) . . . . ? C26 Bi2 C13 C18 98.0(9) . . . . ? C14 C13 C18 C17 -3.2(18) . . . . ? Bi2 C13 C18 C17 169.5(9) . . . . ? C14 C13 C18 C22 170.7(11) . . . . ? Bi2 C13 C18 C22 -16.6(14) . . . . ? C13 C18 C17 C16 2.7(18) . . . . ? C22 C18 C17 C16 -171.2(11) . . . . ? C18 C17 C16 C15 -2(2) . . . . ? C17 C16 C15 C14 1(2) . . . . ? C18 C13 C14 C15 2.6(17) . . . . ? Bi2 C13 C14 C15 -170.0(9) . . . . ? C18 C13 C14 C19 -175.7(11) . . . . ? Bi2 C13 C14 C19 11.8(14) . . . . ? C16 C15 C14 C13 -1.5(19) . . . . ? C16 C15 C14 C19 176.6(12) . . . . ? C13 C14 C19 N3 -41.5(16) . . . . ? C15 C14 C19 N3 140.4(12) . . . . ? C13 C18 C22 N4 40.2(15) . . . . ? C17 C18 C22 N4 -146.0(11) . . . . ? C13 Bi2 C26 O4 88.7(6) . . . . ? O5 Bi2 C26 O4 173.7(10) . . . . ? N4 Bi2 C26 O4 162.3(6) . . . . ? N3 Bi2 C26 O4 16.6(6) . . . . ? C13 Bi2 C26 O5 -85.0(6) . . . . ? O4 Bi2 C26 O5 -173.7(10) . . . . ? N4 Bi2 C26 O5 -11.3(6) . . . . ? N3 Bi2 C26 O5 -157.0(6) . . . . ? C6 C10 N2 C11 -81.6(11) . . . . ? C6 C10 N2 C12 156.9(10) . . . . ? C6 C10 N2 Bi1 38.8(11) . . . . ? C1 Bi1 N2 C11 91.2(9) . . . . ? O2 Bi1 N2 C11 164.1(7) . . . . ? O1 Bi1 N2 C11 -178.8(9) . . . . ? O6 Bi1 N2 C11 -2.7(8) . . . . ? N1 Bi1 N2 C11 59.8(9) . . . . ? C25 Bi1 N2 C11 172.7(8) . . . . ? C1 Bi1 N2 C10 -27.2(8) . . . . ? O2 Bi1 N2 C10 45.7(9) . . . . ? O1 Bi1 N2 C10 62.7(7) . . . . ? O6 Bi1 N2 C10 -121.2(8) . . . . ? N1 Bi1 N2 C10 -58.7(9) . . . . ? C25 Bi1 N2 C10 54.2(8) . . . . ? C1 Bi1 N2 C12 -144.6(8) . . . . ? O2 Bi1 N2 C12 -71.7(8) . . . . ? O1 Bi1 N2 C12 -54.7(7) . . . . ? O6 Bi1 N2 C12 121.4(8) . . . . ? N1 Bi1 N2 C12 -176.1(7) . . . . ? C25 Bi1 N2 C12 -63.2(8) . . . . ? C2 C7 N1 C9 -160.2(11) . . . . ? C2 C7 N1 C8 79.3(12) . . . . ? C2 C7 N1 Bi1 -39.7(11) . . . . ? C1 Bi1 N1 C9 145.9(8) . . . . ? O2 Bi1 N1 C9 52.6(7) . . . . ? O1 Bi1 N1 C9 74.4(8) . . . . ? O6 Bi1 N1 C9 -118.0(8) . . . . ? N2 Bi1 N1 C9 177.6(7) . . . . ? C25 Bi1 N1 C9 63.4(8) . . . . ? C1 Bi1 N1 C7 27.9(7) . . . . ? O2 Bi1 N1 C7 -65.4(7) . . . . ? O1 Bi1 N1 C7 -43.6(8) . . . . ? O6 Bi1 N1 C7 124.0(7) . . . . ? N2 Bi1 N1 C7 59.6(8) . . . . ? C25 Bi1 N1 C7 -54.6(7) . . . . ? C1 Bi1 N1 C8 -88.1(8) . . . . ? O2 Bi1 N1 C8 178.6(8) . . . . ? O1 Bi1 N1 C8 -159.7(7) . . . . ? O6 Bi1 N1 C8 7.9(7) . . . . ? N2 Bi1 N1 C8 -56.4(9) . . . . ? C25 Bi1 N1 C8 -170.7(7) . . . . ? C14 C19 N3 C20 161.9(11) . . . . ? C14 C19 N3 C21 -79.5(13) . . . . ? C14 C19 N3 Bi2 41.8(11) . . . . ? C13 Bi2 N3 C20 -145.0(9) . . . . ? O3 Bi2 N3 C20 129.5(9) . . . . ? O4 Bi2 N3 C20 -49.2(9) . . . . ? O5 Bi2 N3 C20 -69.4(9) . . . . ? N4 Bi2 N3 C20 -178.0(8) . . . . ? C26 Bi2 N3 C20 -56.8(9) . . . . ? C13 Bi2 N3 C21 89.1(8) . . . . ? O3 Bi2 N3 C21 3.6(8) . . . . ? O4 Bi2 N3 C21 -175.0(9) . . . . ? O5 Bi2 N3 C21 164.7(8) . . . . ? N4 Bi2 N3 C21 56.2(10) . . . . ? C26 Bi2 N3 C21 177.3(8) . . . . ? C13 Bi2 N3 C19 -27.6(6) . . . . ? O3 Bi2 N3 C19 -113.2(6) . . . . ? O4 Bi2 N3 C19 68.2(6) . . . . ? O5 Bi2 N3 C19 47.9(7) . . . . ? N4 Bi2 N3 C19 -60.6(8) . . . . ? C26 Bi2 N3 C19 60.5(6) . . . . ? C18 C22 N4 C23 84.7(13) . . . . ? C18 C22 N4 C24 -155.6(11) . . . . ? C18 C22 N4 Bi2 -37.3(11) . . . . ? C13 Bi2 N4 C23 -95.7(8) . . . . ? O3 Bi2 N4 C23 -10.7(7) . . . . ? O4 Bi2 N4 C23 -173.2(7) . . . . ? O5 Bi2 N4 C23 171.6(8) . . . . ? N3 Bi2 N4 C23 -63.0(9) . . . . ? C26 Bi2 N4 C23 177.0(8) . . . . ? C13 Bi2 N4 C24 141.2(9) . . . . ? O3 Bi2 N4 C24 -133.9(8) . . . . ? O4 Bi2 N4 C24 63.7(9) . . . . ? O5 Bi2 N4 C24 48.4(8) . . . . ? N3 Bi2 N4 C24 173.8(7) . . . . ? C26 Bi2 N4 C24 53.8(9) . . . . ? C13 Bi2 N4 C22 23.0(7) . . . . ? O3 Bi2 N4 C22 108.0(7) . . . . ? O4 Bi2 N4 C22 -54.5(8) . . . . ? O5 Bi2 N4 C22 -69.8(7) . . . . ? N3 Bi2 N4 C22 55.7(9) . . . . ? C26 Bi2 N4 C22 -64.3(7) . . . . ? C1 Bi1 O6 C26 -161.5(7) . . . 2_655 ? O2 Bi1 O6 C26 110.9(8) . . . 2_655 ? O1 Bi1 O6 C26 -79.8(10) . . . 2_655 ? N2 Bi1 O6 C26 -89.3(7) . . . 2_655 ? N1 Bi1 O6 C26 127.9(7) . . . 2_655 ? O3 C25 O2 Bi1 -175.9(9) . . . . ? O1 C25 O2 Bi1 2.7(11) . . . . ? C1 Bi1 O2 C25 84.6(7) . . . . ? O1 Bi1 O2 C25 -1.5(6) . . . . ? O6 Bi1 O2 C25 173.4(6) . . . . ? N2 Bi1 O2 C25 18.6(8) . . . . ? N1 Bi1 O2 C25 156.0(7) . . . . ? O2 C25 O1 Bi1 -2.7(11) . . . . ? O3 C25 O1 Bi1 176.0(9) . . . . ? C1 Bi1 O1 C25 -88.5(7) . . . . ? O2 Bi1 O1 C25 1.5(6) . . . . ? O6 Bi1 O1 C25 -171.6(6) . . . . ? N2 Bi1 O1 C25 -161.8(7) . . . . ? N1 Bi1 O1 C25 -24.0(8) . . . . ? O2 C25 O3 Bi2 163.7(8) . . . . ? O1 C25 O3 Bi2 -14.9(13) . . . . ? C13 Bi2 O3 C25 -168.5(8) . . . . ? O4 Bi2 O3 C25 -92.4(9) . . . . ? O5 Bi2 O3 C25 121.3(8) . . . . ? N4 Bi2 O3 C25 116.5(8) . . . . ? N3 Bi2 O3 C25 -95.0(8) . . . . ? O6 C26 O4 Bi2 -173.0(9) 2_645 . . . ? O5 C26 O4 Bi2 6.1(10) . . . . ? C13 Bi2 O4 C26 -91.6(6) . . . . ? O3 Bi2 O4 C26 -165.5(6) . . . . ? O5 Bi2 O4 C26 -3.6(6) . . . . ? N4 Bi2 O4 C26 -21.9(7) . . . . ? N3 Bi2 O4 C26 -162.8(6) . . . . ? O4 C26 O5 Bi2 -6.1(10) . . . . ? O6 C26 O5 Bi2 173.1(9) 2_645 . . . ? C13 Bi2 O5 C26 94.9(6) . . . . ? O3 Bi2 O5 C26 163.6(6) . . . . ? O4 Bi2 O5 C26 3.5(5) . . . . ? N4 Bi2 O5 C26 168.5(6) . . . . ? N3 Bi2 O5 C26 27.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.698 _refine_diff_density_min -2.005 _refine_diff_density_rms 0.250