# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 Cl4 N Sb' _chemical_formula_sum 'C19 H22 Cl4 N Sb' _chemical_formula_weight 527.93 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' Sb Sb -0.5866 1.5461 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4060(6) _cell_length_b 12.1400(6) _cell_length_c 16.5341(10) _cell_angle_alpha 90 _cell_angle_beta 94.589(5) _cell_angle_gamma 90 _cell_volume 2082.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16771 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 1.841 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.029 0 0 1 0.099 -1 0 0 0.128 1 0 0 0.092 0 1 0 0.015 0 -1 0 0.057 1 0 -1 0.039 0 1 -1 0.010 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.746 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16729 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4706 _reflns_number_gt 3694 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0015P)^2^+2.6028P] 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 4706 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0619 _refine_ls_wR_factor_gt 0.0546 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 Sb1 Sb 0.64248(2) 0.194796(18) 0.625922(13) 0.01756(6) Uani 1 1 d . . . Cl2 Cl 0.78050(8) 0.07207(7) 0.56120(5) 0.02625(18) Uani 1 1 d . . . Cl1 Cl 0.51118(7) 0.32169(7) 0.69458(5) 0.02723(19) Uani 1 1 d . . . Cl4 Cl 0.49680(9) 0.05059(8) 0.64298(6) 0.0354(2) Uani 1 1 d . . . Cl3 Cl 0.76444(8) 0.16217(7) 0.74770(5) 0.02771(19) Uani 1 1 d . . . C12 C 1.1407(3) 0.3400(3) 0.6307(2) 0.0245(7) Uani 1 1 d . . . H12 H 1.2117 0.3187 0.6037 0.029 Uiso 1 1 d R . . N1 N 0.7828(2) 0.3341(2) 0.60145(15) 0.0165(5) Uani 1 1 d . . . C13 C 1.0169(3) 0.3223(3) 0.5937(2) 0.0199(7) Uani 1 1 d . . . C8 C 0.9128(3) 0.3540(3) 0.63752(19) 0.0173(7) Uani 1 1 d . . . C14 C 0.8194(3) 0.4510(3) 0.75787(19) 0.0214(7) Uani 1 1 d . . . H14 H 0.7382 0.4251 0.7301 0.026 Uiso 1 1 d R . . C1 C 0.5605(3) 0.2588(3) 0.51403(19) 0.0206(7) Uani 1 1 d . . . C11 C 1.1601(3) 0.3875(3) 0.7059(2) 0.0271(8) Uani 1 1 d . . . H11 H 1.2435 0.3989 0.7289 0.033 Uiso 1 1 d R . . C15 C 0.8216(3) 0.5772(3) 0.7530(2) 0.0273(8) Uani 1 1 d . . . H15A H 0.9025 0.6041 0.7773 0.033 Uiso 1 1 d R . . H15B H 0.7525 0.6067 0.7815 0.033 Uiso 1 1 d R . . H15C H 0.8111 0.5995 0.6972 0.033 Uiso 1 1 d R . . C5 C 0.4118(3) 0.2726(3) 0.3978(2) 0.0351(9) Uani 1 1 d . . . H5 H 0.3410 0.2455 0.3659 0.042 Uiso 1 1 d R . . C6 C 0.4549(3) 0.2180(3) 0.4686(2) 0.0268(8) Uani 1 1 d . . . H6 H 0.4136 0.1548 0.4851 0.032 Uiso 1 1 d R . . C3 C 0.5789(3) 0.4078(3) 0.4197(2) 0.0277(8) Uani 1 1 d . . . H3 H 0.6198 0.4714 0.4038 0.033 Uiso 1 1 d R . . C2 C 0.6235(3) 0.3531(3) 0.48990(19) 0.0198(7) Uani 1 1 d . . . C4 C 0.4726(3) 0.3674(4) 0.3740(2) 0.0355(9) Uani 1 1 d . . . H4 H 0.4420 0.4039 0.3269 0.043 Uiso 1 1 d R . . C17 C 1.0031(3) 0.2701(3) 0.5096(2) 0.0216(7) Uani 1 1 d . . . H17 H 0.9126 0.2487 0.4983 0.026 Uiso 1 1 d R . . C7 C 0.7418(3) 0.3856(3) 0.53686(19) 0.0195(7) Uani 1 1 d . . . H7 H 0.7885 0.4453 0.5198 0.023 Uiso 1 1 d R . . C9 C 0.9299(3) 0.4040(3) 0.71366(19) 0.0190(7) Uani 1 1 d . . . C10 C 1.0556(3) 0.4193(3) 0.7472(2) 0.0243(7) Uani 1 1 d . . . H10 H 1.0697 0.4508 0.7984 0.029 Uiso 1 1 d R . . C18 C 1.0371(4) 0.3514(3) 0.4440(2) 0.0341(9) Uani 1 1 d . . . H18A H 0.9852 0.4163 0.4472 0.041 Uiso 1 1 d R . . H18B H 1.0206 0.3182 0.3915 0.041 Uiso 1 1 d R . . H18C H 1.1266 0.3709 0.4523 0.041 Uiso 1 1 d R . . C19 C 1.0852(3) 0.1665(3) 0.5055(2) 0.0319(9) Uani 1 1 d . . . H19A H 1.1743 0.1850 0.5180 0.038 Uiso 1 1 d R . . H19B H 1.0740 0.1356 0.4520 0.038 Uiso 1 1 d R . . H19C H 1.0591 0.1137 0.5442 0.038 Uiso 1 1 d R . . C16 C 0.8228(3) 0.4146(3) 0.8461(2) 0.0306(8) Uani 1 1 d . . . H16A H 0.8260 0.3357 0.8492 0.037 Uiso 1 1 d R . . H16B H 0.7466 0.4406 0.8692 0.037 Uiso 1 1 d R . . H16C H 0.8977 0.4450 0.8757 0.037 Uiso 1 1 d 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 Sb1 0.01660(10) 0.01708(10) 0.01952(11) 0.00058(9) 0.00475(7) -0.00045(10) Cl2 0.0303(4) 0.0210(4) 0.0287(5) -0.0006(4) 0.0106(3) 0.0047(4) Cl1 0.0219(4) 0.0298(5) 0.0312(5) -0.0041(4) 0.0098(3) 0.0039(4) Cl4 0.0349(5) 0.0282(5) 0.0450(6) -0.0015(4) 0.0148(4) -0.0137(4) Cl3 0.0341(4) 0.0269(5) 0.0219(4) 0.0056(3) 0.0009(3) 0.0027(4) C12 0.0175(15) 0.0212(16) 0.035(2) -0.0053(16) 0.0054(13) 0.0010(15) N1 0.0154(12) 0.0173(14) 0.0173(14) -0.0005(11) 0.0046(10) 0.0014(11) C13 0.0182(15) 0.0162(16) 0.0256(17) 0.0009(14) 0.0024(13) -0.0016(13) C8 0.0160(15) 0.0149(15) 0.0208(17) 0.0022(13) -0.0004(12) -0.0001(13) C14 0.0210(16) 0.0257(18) 0.0173(17) -0.0031(14) 0.0016(13) -0.0002(14) C1 0.0175(15) 0.0227(17) 0.0216(18) -0.0020(14) 0.0014(13) 0.0047(14) C11 0.0155(16) 0.0283(19) 0.037(2) -0.0032(16) -0.0030(14) -0.0028(15) C15 0.0245(17) 0.0293(19) 0.0284(19) 0.0010(16) 0.0043(14) 0.0062(16) C5 0.0229(17) 0.051(3) 0.031(2) -0.0085(18) -0.0063(15) 0.0005(18) C6 0.0203(16) 0.030(2) 0.030(2) -0.0034(15) 0.0027(14) -0.0019(15) C3 0.0285(18) 0.033(2) 0.0219(18) 0.0018(16) 0.0011(14) 0.0032(16) C2 0.0206(16) 0.0197(16) 0.0190(17) -0.0011(13) 0.0021(13) 0.0030(14) C4 0.0296(19) 0.050(3) 0.025(2) 0.0040(18) -0.0066(16) 0.0069(19) C17 0.0192(15) 0.0209(17) 0.0255(18) -0.0032(14) 0.0063(13) -0.0001(14) C7 0.0214(16) 0.0176(16) 0.0202(17) 0.0001(14) 0.0056(13) 0.0011(14) C9 0.0194(15) 0.0186(16) 0.0188(17) -0.0008(13) 0.0013(12) -0.0021(14) C10 0.0238(17) 0.0274(18) 0.0209(18) -0.0039(15) -0.0026(13) -0.0002(15) C18 0.043(2) 0.032(2) 0.029(2) -0.0023(16) 0.0147(17) -0.0067(18) C19 0.0261(18) 0.032(2) 0.039(2) -0.0148(17) 0.0078(15) 0.0039(16) C16 0.037(2) 0.030(2) 0.025(2) -0.0018(16) 0.0045(15) 0.0056(17) _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 Sb1 C1 2.121(3) . ? Sb1 N1 2.291(2) . ? Sb1 Cl3 2.3265(9) . ? Sb1 Cl4 2.3475(9) . ? Sb1 Cl2 2.3819(8) . ? Sb1 Cl1 2.4035(8) . ? C12 C11 1.370(5) . ? C12 C13 1.398(4) . ? C12 H12 0.9300 . ? N1 C7 1.281(4) . ? N1 C8 1.454(4) . ? C13 C8 1.404(4) . ? C13 C17 1.524(4) . ? C8 C9 1.396(4) . ? C14 C16 1.522(5) . ? C14 C9 1.522(4) . ? C14 C15 1.534(5) . ? C14 H14 0.9800 . ? C1 C6 1.374(5) . ? C1 C2 1.394(5) . ? C11 C10 1.384(5) . ? C11 H11 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9599 . ? C5 C4 1.385(6) . ? C5 C6 1.388(5) . ? C5 H5 0.9299 . ? C6 H6 0.9301 . ? C3 C4 1.379(5) . ? C3 C2 1.384(5) . ? C3 H3 0.9301 . ? C2 C7 1.456(4) . ? C4 H4 0.9300 . ? C17 C19 1.526(5) . ? C17 C18 1.529(5) . ? C17 H17 0.9800 . ? C7 H7 0.9299 . ? C9 C10 1.392(4) . ? C10 H10 0.9300 . ? C18 H18A 0.9601 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9601 . ? C19 H19B 0.9600 . ? C19 H19C 0.9601 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 Sb1 N1 78.08(11) . . ? C1 Sb1 Cl3 166.03(9) . . ? N1 Sb1 Cl3 88.12(7) . . ? C1 Sb1 Cl4 99.17(9) . . ? N1 Sb1 Cl4 176.74(7) . . ? Cl3 Sb1 Cl4 94.70(3) . . ? C1 Sb1 Cl2 92.98(9) . . ? N1 Sb1 Cl2 88.07(6) . . ? Cl3 Sb1 Cl2 88.60(3) . . ? Cl4 Sb1 Cl2 90.34(3) . . ? C1 Sb1 Cl1 88.46(9) . . ? N1 Sb1 Cl1 90.29(6) . . ? Cl3 Sb1 Cl1 89.52(3) . . ? Cl4 Sb1 Cl1 91.39(3) . . ? Cl2 Sb1 Cl1 177.55(3) . . ? C11 C12 C13 121.6(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C7 N1 C8 119.9(3) . . ? C7 N1 Sb1 109.4(2) . . ? C8 N1 Sb1 129.47(19) . . ? C12 C13 C8 117.1(3) . . ? C12 C13 C17 118.6(3) . . ? C8 C13 C17 124.3(3) . . ? C9 C8 C13 122.4(3) . . ? C9 C8 N1 119.3(3) . . ? C13 C8 N1 118.3(3) . . ? C16 C14 C9 113.0(3) . . ? C16 C14 C15 109.9(3) . . ? C9 C14 C15 109.5(3) . . ? C16 C14 H14 108.0 . . ? C9 C14 H14 108.1 . . ? C15 C14 H14 108.2 . . ? C6 C1 C2 120.9(3) . . ? C6 C1 Sb1 126.4(3) . . ? C2 C1 Sb1 112.6(2) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 120.0 . . ? C14 C15 H15A 109.6 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.4 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.7(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 121.0 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.3 . . ? C3 C2 C1 120.0(3) . . ? C3 C2 C7 122.0(3) . . ? C1 C2 C7 117.8(3) . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 120.0 . . ? C13 C17 C19 111.8(3) . . ? C13 C17 C18 111.6(3) . . ? C19 C17 C18 109.7(3) . . ? C13 C17 H17 107.7 . . ? C19 C17 H17 107.8 . . ? C18 C17 H17 108.0 . . ? N1 C7 C2 121.6(3) . . ? N1 C7 H7 119.1 . . ? C2 C7 H7 119.3 . . ? C10 C9 C8 117.7(3) . . ? C10 C9 C14 118.7(3) . . ? C8 C9 C14 123.3(3) . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C17 C18 H18A 109.1 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.6 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.4 . . ? C17 C19 H19B 109.6 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.4 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 C16 H16A 109.8 . . ? C14 C16 H16B 109.3 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.4 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.483 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.119 _database_code_depnum_ccdc_archive 'CCDC 943195' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H32 N Sb' _chemical_formula_sum 'C31 H32 N Sb' _chemical_formula_weight 540.33 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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9640(9) _cell_length_b 11.2940(5) _cell_length_c 16.7969(12) _cell_angle_alpha 90 _cell_angle_beta 111.179(5) _cell_angle_gamma 90 _cell_volume 2647.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 20009 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.060 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.204 0 -1 0 0.212 0 0 1 0.114 0 0 -1 0.038 1 0 0 0.166 -1 0 0 0.033 1 0 -1 0.128 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19973 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.40 _reflns_number_total 6519 _reflns_number_gt 5230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+3.6548P] 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 6519 _refine_ls_number_parameters 317 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0570 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.210 _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 Sb1 Sb 0.270513(12) 0.059763(15) 0.823949(11) 0.02399(6) Uani 1 1 d . . . C16 C 0.1764(2) 0.3915(3) 1.0535(2) 0.0476(9) Uani 1 1 d . . . H16A H 0.1708 0.4407 1.0053 0.057 Uiso 1 1 d R . . H16B H 0.2407 0.3959 1.0944 0.057 Uiso 1 1 d R . . H16C H 0.1324 0.4183 1.0793 0.057 Uiso 1 1 d R . . N1 N 0.12941(16) 0.0843(2) 0.89824(14) 0.0265(5) Uani 1 1 d . . . C8 C 0.05084(18) 0.1630(2) 0.88557(17) 0.0265(5) Uani 1 1 d . . . C26 C 0.40223(19) 0.0159(2) 0.80354(17) 0.0267(5) Uani 1 1 d . . . C7 C 0.13085(19) -0.0153(3) 0.93331(17) 0.0292(6) Uani 1 1 d . . . H7 H 0.0800 -0.0357 0.9501 0.035 Uiso 1 1 d R . . C9 C 0.06075(19) 0.2526(3) 0.94611(17) 0.0283(6) Uani 1 1 d . B . C20 C 0.33461(18) 0.1957(2) 0.91594(17) 0.0255(5) Uani 1 1 d . . . C2 C 0.20944(19) -0.0999(2) 0.94765(17) 0.0276(6) Uani 1 1 d . . . C21 C 0.3789(2) 0.1751(3) 1.00278(18) 0.0319(6) Uani 1 1 d . . . H21 H 0.3839 0.0982 1.0237 0.038 Uiso 1 1 d R . . C4 C 0.2856(2) -0.2804(3) 1.0160(2) 0.0387(7) Uani 1 1 d . . . H4 H 0.2870 -0.3459 1.0500 0.046 Uiso 1 1 d R . . C31 C 0.4871(2) 0.0769(3) 0.84134(19) 0.0340(6) Uani 1 1 d . . . H31 H 0.4907 0.1350 0.8816 0.041 Uiso 1 1 d R . . C6 C 0.3528(2) -0.1677(2) 0.93043(18) 0.0298(6) Uani 1 1 d . . . H6 H 0.4001 -0.1592 0.9070 0.036 Uiso 1 1 d R . . C27 C 0.4000(2) -0.0712(3) 0.74386(18) 0.0361(7) Uani 1 1 d . . . H27 H 0.3436 -0.1132 0.7170 0.043 Uiso 1 1 d R . . C1 C 0.28029(19) -0.0836(2) 0.91199(16) 0.0254(5) Uani 1 1 d . . . C17 C -0.0369(2) 0.0627(3) 0.74244(18) 0.0402(7) Uani 1 1 d DU . . H17 H 0.0128 0.0026 0.7671 0.048 Uiso 1 1 calc R A 1 C14 C 0.1531(2) 0.2641(3) 1.02310(18) 0.0373(7) Uani 1 1 d . . . H14 H 0.2051 0.2355 1.0055 0.045 Uiso 1 1 d R . . C12 C -0.1043(2) 0.2352(3) 0.7999(2) 0.0406(7) Uani 1 1 d . . . H12 H -0.1591 0.2314 0.7509 0.049 Uiso 1 1 d R B . C3 C 0.2122(2) -0.1982(3) 0.99875(19) 0.0358(7) Uani 1 1 d . . . H3 H 0.1644 -0.2089 1.0213 0.043 Uiso 1 1 d R . . C25 C 0.3297(2) 0.3111(3) 0.8867(2) 0.0375(7) Uani 1 1 d . . . H25 H 0.3003 0.3266 0.8287 0.045 Uiso 1 1 d R . . C10 C -0.0155(2) 0.3299(3) 0.93198(19) 0.0346(6) Uani 1 1 d . . . H10 H -0.0118 0.3883 0.9720 0.042 Uiso 1 1 d R B . C30 C 0.5670(2) 0.0531(3) 0.8208(2) 0.0413(7) Uani 1 1 d . . . H30 H 0.6231 0.0960 0.8467 0.050 Uiso 1 1 d R . . C5 C 0.3560(2) -0.2645(3) 0.98249(19) 0.0354(7) Uani 1 1 d . . . H5 H 0.4061 -0.3186 0.9950 0.043 Uiso 1 1 d R . . C28 C 0.4795(2) -0.0964(3) 0.7238(2) 0.0437(8) Uani 1 1 d . . . H28 H 0.4763 -0.1556 0.6844 0.052 Uiso 1 1 d R . . C11 C -0.0977(2) 0.3211(3) 0.8592(2) 0.0394(7) Uani 1 1 d . B . H11 H -0.1481 0.3737 0.8507 0.047 Uiso 1 1 d R . . C29 C 0.5634(2) -0.0335(3) 0.7618(2) 0.0433(8) Uani 1 1 d . . . H29 H 0.6169 -0.0501 0.7481 0.052 Uiso 1 1 d R . . C13 C -0.0308(2) 0.1536(3) 0.81095(18) 0.0334(6) Uani 1 1 d . B . C23 C 0.4104(2) 0.3825(3) 1.0285(2) 0.0451(8) Uani 1 1 d . . . H23 H 0.4356 0.4448 1.0662 0.054 Uiso 1 1 d R . . C22 C 0.4161(2) 0.2682(3) 1.0589(2) 0.0393(7) Uani 1 1 d . . . H22 H 0.4449 0.2538 1.1171 0.047 Uiso 1 1 d R . . C15 C 0.1518(3) 0.1853(4) 1.0966(2) 0.0565(10) Uani 1 1 d . . . H15A H 0.0961 0.2034 1.1098 0.068 Uiso 1 1 d R . . H15B H 0.2084 0.1993 1.1460 0.068 Uiso 1 1 d R . . H15C H 0.1499 0.1038 1.0799 0.068 Uiso 1 1 d R . . C18 C -0.1384(6) -0.0008(8) 0.7097(5) 0.063(3) Uani 0.648(15) 1 d PD B 1 H18A H -0.1487 -0.0387 0.7568 0.094 Uiso 0.648(15) 1 calc PR B 1 H18B H -0.1402 -0.0590 0.6675 0.094 Uiso 0.648(15) 1 calc PR B 1 H18C H -0.1877 0.0570 0.6849 0.094 Uiso 0.648(15) 1 calc PR B 1 C24 C 0.3676(3) 0.4041(3) 0.9425(2) 0.0485(9) Uani 1 1 d . . . H24 H 0.3645 0.4811 0.9221 0.058 Uiso 1 1 d R . . C19 C -0.0198(6) 0.1191(6) 0.6717(5) 0.0451(17) Uani 0.648(15) 1 d PD B 1 H19A H -0.0234 0.0610 0.6289 0.068 Uiso 0.648(15) 1 calc PR B 1 H19B H 0.0427 0.1547 0.6918 0.068 Uiso 0.648(15) 1 calc PR B 1 H19C H -0.0674 0.1791 0.6475 0.068 Uiso 0.648(15) 1 calc PR B 1 C18A C -0.0823(12) -0.0452(10) 0.7481(9) 0.054(4) Uani 0.352(15) 1 d PD B 2 H18D H -0.0823 -0.0970 0.7028 0.081 Uiso 0.352(15) 1 calc PR B 2 H18E H -0.1472 -0.0298 0.7432 0.081 Uiso 0.352(15) 1 calc PR B 2 H18F H -0.0484 -0.0820 0.8021 0.081 Uiso 0.352(15) 1 calc PR B 2 C19A C -0.0728(13) 0.1176(11) 0.6501(7) 0.048(3) Uani 0.352(15) 1 d PD B 2 H19D H -0.0377 0.1888 0.6504 0.072 Uiso 0.352(15) 1 calc PR B 2 H19E H -0.1399 0.1357 0.6326 0.072 Uiso 0.352(15) 1 calc PR B 2 H19F H -0.0628 0.0618 0.6110 0.072 Uiso 0.352(15) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.02446(9) 0.02291(9) 0.02170(9) 0.00133(7) 0.00485(6) 0.00040(7) C16 0.0356(17) 0.058(2) 0.0413(18) -0.0200(16) 0.0037(14) 0.0005(16) N1 0.0260(11) 0.0277(12) 0.0243(11) 0.0000(9) 0.0073(9) -0.0007(9) C8 0.0242(13) 0.0280(14) 0.0279(13) 0.0037(11) 0.0100(11) 0.0007(11) C26 0.0300(14) 0.0261(13) 0.0240(13) 0.0025(11) 0.0097(11) 0.0024(11) C7 0.0252(13) 0.0329(15) 0.0284(14) 0.0020(11) 0.0084(11) -0.0019(11) C9 0.0245(13) 0.0358(15) 0.0244(13) 0.0043(11) 0.0087(11) 0.0019(11) C20 0.0245(13) 0.0233(13) 0.0305(14) -0.0022(11) 0.0122(11) -0.0003(10) C2 0.0271(13) 0.0230(13) 0.0282(13) 0.0014(11) 0.0045(11) -0.0031(11) C21 0.0294(14) 0.0327(15) 0.0309(14) 0.0026(12) 0.0077(11) 0.0037(12) C4 0.0435(17) 0.0254(14) 0.0388(17) 0.0106(12) 0.0048(14) -0.0037(13) C31 0.0334(15) 0.0349(16) 0.0343(15) -0.0074(12) 0.0131(12) -0.0016(12) C6 0.0309(14) 0.0246(13) 0.0316(14) -0.0015(11) 0.0085(12) -0.0006(11) C27 0.0376(16) 0.0374(17) 0.0305(14) -0.0073(13) 0.0091(12) -0.0021(13) C1 0.0253(13) 0.0216(13) 0.0247(13) -0.0017(10) 0.0035(10) -0.0048(10) C17 0.0420(17) 0.0366(16) 0.0280(14) 0.0002(13) -0.0043(12) 0.0044(14) C14 0.0326(15) 0.0477(18) 0.0283(14) -0.0072(13) 0.0069(12) 0.0078(14) C12 0.0300(15) 0.0433(18) 0.0390(17) 0.0045(14) 0.0012(13) 0.0033(13) C3 0.0351(15) 0.0324(16) 0.0373(16) 0.0080(13) 0.0100(13) -0.0060(13) C25 0.0510(19) 0.0281(15) 0.0352(16) 0.0008(12) 0.0176(14) -0.0012(13) C10 0.0296(14) 0.0389(17) 0.0377(16) 0.0023(13) 0.0149(12) 0.0051(13) C30 0.0314(15) 0.0467(19) 0.0463(18) -0.0052(15) 0.0147(14) -0.0014(14) C5 0.0341(16) 0.0244(14) 0.0399(16) 0.0001(12) 0.0038(13) 0.0018(12) C28 0.053(2) 0.0457(19) 0.0352(17) -0.0089(14) 0.0188(15) 0.0080(16) C11 0.0285(15) 0.0405(17) 0.0472(18) 0.0099(15) 0.0114(13) 0.0101(13) C29 0.0388(17) 0.056(2) 0.0398(17) 0.0014(15) 0.0203(14) 0.0114(15) C13 0.0301(14) 0.0345(16) 0.0297(14) 0.0044(12) 0.0038(12) -0.0001(12) C23 0.0377(17) 0.0368(18) 0.061(2) -0.0216(16) 0.0182(16) -0.0059(14) C22 0.0313(15) 0.0504(19) 0.0318(15) -0.0138(14) 0.0061(13) -0.0022(14) C15 0.070(3) 0.059(2) 0.0316(17) 0.0026(16) 0.0070(17) 0.017(2) C18 0.070(5) 0.075(5) 0.044(4) -0.013(4) 0.021(4) -0.041(4) C24 0.067(2) 0.0236(15) 0.056(2) -0.0057(15) 0.0233(19) -0.0040(15) C19 0.044(4) 0.054(4) 0.044(4) -0.001(3) 0.024(3) -0.003(3) C18A 0.075(10) 0.039(6) 0.044(7) -0.015(5) 0.016(7) -0.019(6) C19A 0.059(9) 0.051(6) 0.034(6) 0.004(5) 0.018(6) 0.003(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 Sb1 C20 2.143(3) . ? Sb1 C1 2.162(3) . ? Sb1 C26 2.176(3) . ? C16 C14 1.524(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9601 . ? C16 H16C 0.9600 . ? N1 C7 1.266(4) . ? N1 C8 1.427(3) . ? C8 C13 1.403(4) . ? C8 C9 1.404(4) . ? C26 C31 1.382(4) . ? C26 C27 1.396(4) . ? C7 C2 1.466(4) . ? C7 H7 0.9301 . ? C9 C10 1.387(4) . ? C9 C14 1.519(4) . ? C20 C21 1.387(4) . ? C20 C25 1.385(4) . ? C2 C3 1.395(4) . ? C2 C1 1.405(4) . ? C21 C22 1.388(4) . ? C21 H21 0.9300 . ? C4 C5 1.375(4) . ? C4 C3 1.385(4) . ? C4 H4 0.9300 . ? C31 C30 1.384(4) . ? C31 H31 0.9300 . ? C6 C1 1.390(4) . ? C6 C5 1.390(4) . ? C6 H6 0.9299 . ? C27 C28 1.379(4) . ? C27 H27 0.9301 . ? C17 C18A 1.415(9) . ? C17 C19 1.451(6) . ? C17 C13 1.520(4) . ? C17 C19A 1.574(10) . ? C17 C18 1.587(7) . ? C17 H17 0.9800 . ? C14 C15 1.527(5) . ? C14 H14 0.9800 . ? C12 C11 1.368(5) . ? C12 C13 1.395(4) . ? C12 H12 0.9301 . ? C3 H3 0.9301 . ? C25 C24 1.384(4) . ? C25 H25 0.9299 . ? C10 C11 1.389(4) . ? C10 H10 0.9299 . ? C30 C29 1.380(5) . ? C30 H30 0.9299 . ? C5 H5 0.9300 . ? C28 C29 1.381(5) . ? C28 H28 0.9300 . ? C11 H11 0.9300 . ? C29 H29 0.9300 . ? C23 C24 1.375(5) . ? C23 C22 1.378(5) . ? C23 H23 0.9300 . ? C22 H22 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9599 . ? C15 H15C 0.9601 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C24 H24 0.9301 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18A H18D 0.9600 . ? C18A H18E 0.9600 . ? C18A H18F 0.9600 . ? C19A H19D 0.9600 . ? C19A H19E 0.9600 . ? C19A H19F 0.9600 . ? 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 C20 Sb1 C1 98.12(10) . . ? C20 Sb1 C26 94.70(10) . . ? C1 Sb1 C26 95.50(10) . . ? C14 C16 H16A 108.9 . . ? C14 C16 H16B 109.7 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.7 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 N1 C8 119.8(2) . . ? C13 C8 C9 122.1(3) . . ? C13 C8 N1 119.4(2) . . ? C9 C8 N1 118.4(2) . . ? C31 C26 C27 117.5(3) . . ? C31 C26 Sb1 123.3(2) . . ? C27 C26 Sb1 119.0(2) . . ? N1 C7 C2 122.2(3) . . ? N1 C7 H7 118.9 . . ? C2 C7 H7 118.9 . . ? C10 C9 C8 117.7(3) . . ? C10 C9 C14 122.1(3) . . ? C8 C9 C14 120.3(2) . . ? C21 C20 C25 118.3(3) . . ? C21 C20 Sb1 123.9(2) . . ? C25 C20 Sb1 117.8(2) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 C7 117.6(3) . . ? C1 C2 C7 121.9(2) . . ? C20 C21 C22 120.6(3) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.6 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.2 . . ? C26 C31 C30 121.5(3) . . ? C26 C31 H31 119.2 . . ? C30 C31 H31 119.3 . . ? C1 C6 C5 121.6(3) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C28 C27 C26 121.4(3) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.3 . . ? C6 C1 C2 117.6(2) . . ? C6 C1 Sb1 121.2(2) . . ? C2 C1 Sb1 120.95(19) . . ? C18A C17 C19 131.6(6) . . ? C18A C17 C13 115.5(5) . . ? C19 C17 C13 110.1(4) . . ? C18A C17 C19A 113.8(6) . . ? C19 C17 C19A 28.1(5) . . ? C13 C17 C19A 112.7(5) . . ? C18A C17 C18 38.0(6) . . ? C19 C17 C18 110.1(4) . . ? C13 C17 C18 110.8(4) . . ? C19A C17 C18 83.9(6) . . ? C18A C17 H17 71.7 . . ? C19 C17 H17 108.6 . . ? C13 C17 H17 108.6 . . ? C19A C17 H17 128.7 . . ? C18 C17 H17 108.6 . . ? C9 C14 C16 113.2(3) . . ? C9 C14 C15 111.4(3) . . ? C16 C14 C15 110.3(3) . . ? C9 C14 H14 107.0 . . ? C16 C14 H14 107.5 . . ? C15 C14 H14 107.1 . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.2 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.8 . . ? C24 C25 C20 121.2(3) . . ? C24 C25 H25 119.3 . . ? C20 C25 H25 119.5 . . ? C9 C10 C11 121.2(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.3 . . ? C29 C30 C31 120.2(3) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 119.9 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 120.0 . . ? C27 C28 C29 120.1(3) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 120.2 . . ? C12 C11 C10 119.9(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.1 . . ? C30 C29 C28 119.4(3) . . ? C30 C29 H29 120.5 . . ? C28 C29 H29 120.2 . . ? C12 C13 C8 117.3(3) . . ? C12 C13 C17 121.1(3) . . ? C8 C13 C17 121.5(3) . . ? C24 C23 C22 119.9(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.0 . . ? C23 C22 C21 120.2(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 120.0 . . ? C14 C15 H15A 109.2 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.4 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C23 C24 C25 119.9(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 120.4 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C18A H18D 109.5 . . ? C17 C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17 C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? C17 C19A H19D 109.5 . . ? C17 C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C17 C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.113 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 943196' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H32 Cl2 N Sb' _chemical_formula_sum 'C31 H32 Cl2 N Sb' _chemical_formula_weight 611.23 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.70201(10) _cell_length_b 20.1570(5) _cell_length_c 12.8980(9) _cell_angle_alpha 90 _cell_angle_beta 94.132(4) _cell_angle_gamma 90 _cell_volume 2775.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 20177 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 1.207 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.110 0 0 1 0.161 1 0 0 0.188 -1 0 0 0.084 0 1 0 0.033 0 -1 0 0.092 1 0 1 0.193 1 0 -1 0.157 -1 0 1 0.120 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.731 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20167 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10603 _reflns_number_gt 10071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+3.0967P] 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 0.398(14) _refine_ls_number_reflns 10603 _refine_ls_number_parameters 632 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0550 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 Sb1 Sb 0.33939(2) 0.228741(11) 0.966673(17) 0.01882(5) Uani 1 1 d . . . Sb2 Sb 0.18440(2) 0.509023(11) 0.482960(17) 0.02023(6) Uani 1 1 d . . . Cl3 Cl 0.29150(9) 0.40346(5) 0.53194(7) 0.0266(2) Uani 1 1 d . . . Cl2 Cl 0.23592(8) 0.33604(4) 0.91957(7) 0.02313(19) Uani 1 1 d . . . Cl1 Cl 0.46523(10) 0.13563(5) 1.03394(8) 0.0317(2) Uani 1 1 d . . . Cl4 Cl 0.06548(11) 0.60415(5) 0.41462(8) 0.0353(2) Uani 1 1 d . . . N2 N -0.0002(3) 0.43663(16) 0.3979(2) 0.0177(7) Uani 1 1 d . . . N1 N 0.5306(3) 0.30104(16) 1.0430(2) 0.0196(6) Uani 1 1 d . . . C108 C -0.1219(3) 0.41752(19) 0.4277(3) 0.0204(7) Uani 1 1 d . . . C20 C 0.4333(3) 0.2289(2) 0.8264(3) 0.0236(7) Uani 1 1 d . . . C26 C 0.1743(3) 0.17172(19) 0.9263(3) 0.0220(8) Uani 1 1 d . . . C21 C 0.3634(4) 0.2459(2) 0.7360(3) 0.0292(10) Uani 1 1 d . . . H21 H 0.2825 0.2623 0.7386 0.035 Uiso 1 1 d R . . C118 C -0.0252(5) 0.3355(3) 0.6802(3) 0.0432(12) Uani 1 1 d . . . 118A H -0.0586 0.3761 0.7057 0.052 Uiso 1 1 d R . . 118B H 0.0565 0.3278 0.7138 0.052 Uiso 1 1 d R . . 118C H -0.0797 0.2994 0.6949 0.052 Uiso 1 1 d R . . C3 C 0.3699(4) 0.3105(2) 1.2813(3) 0.0226(8) Uani 1 1 d . . . H3 H 0.4247 0.3385 1.3195 0.027 Uiso 1 1 d R . . C113 C -0.1321(3) 0.3720(2) 0.5088(3) 0.0220(8) Uani 1 1 d . . . C107 C 0.0305(3) 0.42123(18) 0.3077(3) 0.0207(8) Uani 1 1 d . . . H107 H -0.0219 0.3936 0.2665 0.025 Uiso 1 1 d R . . C104 C 0.2758(3) 0.4590(2) 0.1243(3) 0.0254(8) Uani 1 1 d . . . H104 H 0.2943 0.4486 0.0569 0.031 Uiso 1 1 d R . . C101 C 0.2250(3) 0.48744(18) 0.3274(3) 0.0202(7) Uani 1 1 d . . . C109 C -0.2287(3) 0.4464(2) 0.3748(3) 0.0227(8) Uani 1 1 d . . . C1 C 0.3092(3) 0.25355(19) 1.1225(3) 0.0199(7) Uani 1 1 d . . . C4 C 0.2659(4) 0.2862(2) 1.3259(3) 0.0251(8) Uani 1 1 d . . . H4 H 0.2512 0.2972 1.3940 0.030 Uiso 1 1 d R . . C27 C 0.1653(4) 0.1059(2) 0.9546(3) 0.0290(9) Uani 1 1 d . . . H27 H 0.2314 0.0852 0.9926 0.035 Uiso 1 1 d R . . C7 C 0.5073(3) 0.31645(19) 1.1351(3) 0.0195(8) Uani 1 1 d . . . H7 H 0.5640 0.3427 1.1747 0.023 Uiso 1 1 d R . . C10 C 0.7787(4) 0.3807(2) 0.8999(3) 0.0296(9) Uani 1 1 d . . . H10 H 0.7867 0.4117 0.8474 0.035 Uiso 1 1 d R . . C28 C 0.0568(4) 0.0700(2) 0.9260(3) 0.0359(10) Uani 1 1 d . . . H28 H 0.0509 0.0256 0.9448 0.043 Uiso 1 1 d R . . C105 C 0.3517(3) 0.5023(2) 0.1835(3) 0.0252(8) Uani 1 1 d . . . H105 H 0.4195 0.5221 0.1545 0.030 Uiso 1 1 d R . . C115 C -0.2865(4) 0.5627(2) 0.3192(4) 0.0391(11) Uani 1 1 d . . . 115A H -0.3750 0.5560 0.3224 0.047 Uiso 1 1 d R . . 115B H -0.2723 0.5959 0.2680 0.047 Uiso 1 1 d R . . 115C H -0.2508 0.5770 0.3859 0.047 Uiso 1 1 d R . . C17 C 0.7553(3) 0.2359(2) 1.1445(3) 0.0294(9) Uani 1 1 d . . . H17 H 0.6673 0.2266 1.1552 0.035 Uiso 1 1 d R . . C15 C 0.5240(4) 0.4633(2) 0.9198(4) 0.0417(11) Uani 1 1 d . . . H15A H 0.5151 0.4595 0.9931 0.050 Uiso 1 1 d R . . H15B H 0.4495 0.4825 0.8865 0.050 Uiso 1 1 d R . . H15C H 0.5947 0.4910 0.9083 0.050 Uiso 1 1 d R . . C103 C 0.1730(4) 0.43111(19) 0.1648(3) 0.0225(8) Uani 1 1 d . . . H103 H 0.1213 0.4027 0.1243 0.027 Uiso 1 1 d R . . C13 C 0.7594(3) 0.2883(2) 1.0600(3) 0.0241(8) Uani 1 1 d . . . C6 C 0.2034(3) 0.2290(3) 1.1660(3) 0.0264(7) Uani 1 1 d . . . H6 H 0.1468 0.2020 1.1276 0.032 Uiso 1 1 d R . . C2 C 0.3934(3) 0.29408(19) 1.1798(3) 0.0194(7) Uani 1 1 d . . . C25 C 0.5549(4) 0.2054(2) 0.8234(4) 0.0287(10) Uani 1 1 d . . . H25 H 0.6010 0.1936 0.8845 0.034 Uiso 1 1 d R . . C5 C 0.1829(4) 0.2450(2) 1.2685(3) 0.0265(9) Uani 1 1 d . . . H5 H 0.1134 0.2282 1.2990 0.032 Uiso 1 1 d R . . C106 C 0.3268(3) 0.5159(2) 0.2858(3) 0.0238(8) Uani 1 1 d . . . H106 H 0.3790 0.5443 0.3257 0.029 Uiso 1 1 d R . . C14 C 0.5453(3) 0.3950(2) 0.8749(3) 0.0228(8) Uani 1 1 d . . . H14 H 0.4730 0.3674 0.8890 0.027 Uiso 1 1 d R . . C111 C -0.3567(4) 0.3800(2) 0.4835(3) 0.0325(10) Uani 1 1 d . . . H111 H -0.4359 0.3672 0.5012 0.039 Uiso 1 1 d R . . C31 C 0.0724(4) 0.2017(2) 0.8731(4) 0.0374(10) Uani 1 1 d . . . H31 H 0.0750 0.2466 0.8573 0.045 Uiso 1 1 d R . . C123 C -0.0329(4) 0.5189(3) 0.8021(3) 0.0446(12) Uani 1 1 d . . . H123 H -0.0714 0.5230 0.8642 0.054 Uiso 1 1 d R . . C9 C 0.6606(3) 0.36324(19) 0.9285(3) 0.0229(8) Uani 1 1 d . . . C110 C -0.3449(4) 0.4256(2) 0.4057(3) 0.0295(9) Uani 1 1 d . . . H110 H -0.4169 0.4430 0.3713 0.035 Uiso 1 1 d R . . C30 C -0.0354(4) 0.1644(3) 0.8452(4) 0.0483(13) Uani 1 1 d . . . H30 H -0.1015 0.1838 0.8053 0.058 Uiso 1 1 d R . . C12 C 0.8750(4) 0.3069(2) 1.0266(3) 0.0338(10) Uani 1 1 d . . . H12 H 0.9472 0.2875 1.0576 0.041 Uiso 1 1 d R . . C122 C -0.0969(5) 0.5361(3) 0.7100(4) 0.0447(14) Uani 1 1 d . . . H122 H -0.1782 0.5524 0.7098 0.054 Uiso 1 1 d R . . C112 C -0.2502(4) 0.3538(2) 0.5356(3) 0.0286(9) Uani 1 1 d . . . H112 H -0.2577 0.3233 0.5889 0.034 Uiso 1 1 d R . . C117 C -0.0159(4) 0.3412(2) 0.5627(3) 0.0251(8) Uani 1 1 d . . . H117 H 0.0550 0.3704 0.5512 0.030 Uiso 1 1 d R . . C114 C -0.2247(4) 0.4978(2) 0.2893(3) 0.0271(9) Uani 1 1 d . . . H114 H -0.1365 0.5068 0.2790 0.033 Uiso 1 1 d R . . C22 C 0.4162(4) 0.2385(2) 0.6410(3) 0.0362(10) Uani 1 1 d . . . H22 H 0.3695 0.2489 0.5795 0.043 Uiso 1 1 d R . . C11 C 0.8853(4) 0.3534(2) 0.9494(3) 0.0333(10) Uani 1 1 d . . . H11 H 0.9640 0.3658 0.9301 0.040 Uiso 1 1 d R . . C102 C 0.1455(3) 0.44574(19) 0.2664(3) 0.0196(8) Uani 1 1 d . . . C8 C 0.6522(3) 0.31816(19) 1.0095(3) 0.0219(8) Uani 1 1 d . . . C116 C -0.2861(4) 0.4708(2) 0.1874(3) 0.0360(10) Uani 1 1 d . . . 116A H -0.2422 0.4320 0.1670 0.043 Uiso 1 1 d R . . 116B H -0.2830 0.5041 0.1345 0.043 Uiso 1 1 d R . . 116C H -0.3718 0.4597 0.1966 0.043 Uiso 1 1 d R . . C126 C 0.3416(4) 0.5659(2) 0.5426(3) 0.0265(9) Uani 1 1 d . . . C18 C 0.8160(4) 0.2633(2) 1.2474(3) 0.0405(11) Uani 1 1 d . . . H18A H 0.9004 0.2762 1.2367 0.049 Uiso 1 1 d R . . H18B H 0.8167 0.2297 1.3002 0.049 Uiso 1 1 d R . . H18C H 0.7699 0.3012 1.2689 0.049 Uiso 1 1 d R . . C124 C 0.0867(5) 0.4954(3) 0.8032(3) 0.0409(12) Uani 1 1 d . . . H124 H 0.1295 0.4835 0.8658 0.049 Uiso 1 1 d R . . C29 C -0.0417(4) 0.0995(2) 0.8724(4) 0.0384(10) Uani 1 1 d . . . H29 H -0.1143 0.0754 0.8548 0.046 Uiso 1 1 d R . . C24 C 0.6065(4) 0.1986(2) 0.7273(4) 0.0376(11) Uani 1 1 d . . . H24 H 0.6886 0.1841 0.7242 0.045 Uiso 1 1 d R . . C23 C 0.5361(4) 0.2150(2) 0.6376(3) 0.0394(12) Uani 1 1 d . . . H23 H 0.5699 0.2099 0.5737 0.047 Uiso 1 1 d R . . C125 C 0.1449(4) 0.4889(2) 0.7102(3) 0.0304(9) Uani 1 1 d . . . H125 H 0.2260 0.4722 0.7108 0.037 Uiso 1 1 d R . . C120 C 0.0818(3) 0.5072(2) 0.6173(3) 0.0244(7) Uani 1 1 d . . . C121 C -0.0397(4) 0.5299(2) 0.6165(3) 0.0339(11) Uani 1 1 d . . . H121 H -0.0831 0.5412 0.5539 0.041 Uiso 1 1 d R . . C131 C 0.4624(4) 0.5404(2) 0.5441(4) 0.0423(11) Uani 1 1 d . . . H131 H 0.4759 0.4993 0.5139 0.051 Uiso 1 1 d R . . C119 C 0.0107(5) 0.2745(2) 0.5144(4) 0.0425(11) Uani 1 1 d . . . 119A H -0.0580 0.2449 0.5233 0.051 Uiso 1 1 d R . . 119B H 0.0862 0.2560 0.5473 0.051 Uiso 1 1 d R . . 119C H 0.0205 0.2805 0.4416 0.051 Uiso 1 1 d R . . C19 C 0.8166(5) 0.1713(2) 1.1142(4) 0.0465(13) Uani 1 1 d . . . H19A H 0.7769 0.1552 1.0500 0.056 Uiso 1 1 d R . . H19B H 0.8084 0.1389 1.1678 0.056 Uiso 1 1 d R . . H19C H 0.9038 0.1792 1.1059 0.056 Uiso 1 1 d R . . C127 C 0.3222(4) 0.6262(2) 0.5879(4) 0.0387(11) Uani 1 1 d . . . H127 H 0.2417 0.6436 0.5869 0.046 Uiso 1 1 d R . . C16 C 0.5507(4) 0.3990(3) 0.7578(3) 0.0378(11) Uani 1 1 d . . . H16A H 0.6127 0.4311 0.7416 0.045 Uiso 1 1 d R . . H16B H 0.4704 0.4122 0.7264 0.045 Uiso 1 1 d R . . H16C H 0.5727 0.3564 0.7314 0.045 Uiso 1 1 d R . . C128 C 0.4228(5) 0.6614(3) 0.6350(4) 0.0518(14) Uani 1 1 d . . . H128 H 0.4092 0.7024 0.6653 0.062 Uiso 1 1 d R . . C129 C 0.5411(5) 0.6354(3) 0.6367(4) 0.0537(14) Uani 1 1 d . . . H129 H 0.6081 0.6583 0.6697 0.064 Uiso 1 1 d R . . C130 C 0.5613(5) 0.5755(3) 0.5898(4) 0.0518(14) Uani 1 1 d . . . H130 H 0.6423 0.5590 0.5880 0.062 Uiso 1 1 d 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 Sb1 0.01858(11) 0.01879(11) 0.01885(11) -0.00111(10) -0.00026(8) 0.00050(11) Sb2 0.02131(12) 0.02109(12) 0.01816(11) -0.00248(10) 0.00057(8) -0.00017(10) Cl3 0.0241(5) 0.0267(5) 0.0281(5) -0.0012(4) -0.0048(4) 0.0039(4) Cl2 0.0201(4) 0.0214(4) 0.0274(5) -0.0008(4) -0.0017(3) 0.0026(4) Cl1 0.0334(5) 0.0240(5) 0.0373(6) 0.0061(4) -0.0016(4) 0.0068(4) Cl4 0.0469(6) 0.0269(5) 0.0322(5) 0.0022(4) 0.0032(5) 0.0121(5) N2 0.0176(15) 0.0151(15) 0.0201(16) 0.0019(12) -0.0004(12) 0.0005(13) N1 0.0193(15) 0.0209(16) 0.0180(15) 0.0025(12) -0.0026(12) 0.0012(13) C108 0.0208(18) 0.0221(18) 0.0184(17) 0.0000(14) 0.0018(14) -0.0020(15) C20 0.0252(17) 0.0195(16) 0.0259(17) -0.0025(19) 0.0006(13) -0.0020(19) C26 0.0252(19) 0.0231(19) 0.0177(17) -0.0058(14) 0.0005(14) -0.0072(16) C21 0.032(2) 0.034(3) 0.022(2) 0.0028(16) 0.0021(16) 0.0032(18) C118 0.037(3) 0.064(3) 0.028(2) 0.015(2) -0.0021(19) 0.005(2) C3 0.024(2) 0.023(2) 0.0204(19) -0.0019(15) -0.0015(15) 0.0007(16) C113 0.0179(17) 0.027(2) 0.0208(18) 0.0002(15) 0.0001(13) -0.0025(15) C107 0.0216(18) 0.0180(18) 0.0213(18) 0.0015(14) -0.0056(14) 0.0013(15) C104 0.0257(19) 0.032(2) 0.0195(18) -0.0007(16) 0.0061(14) 0.0052(17) C101 0.0194(17) 0.0188(18) 0.0219(18) -0.0026(14) -0.0026(14) 0.0037(14) C109 0.0206(18) 0.0244(19) 0.0229(18) 0.0026(15) 0.0010(14) -0.0019(15) C1 0.0183(17) 0.0254(19) 0.0158(17) 0.0026(14) -0.0005(13) 0.0021(15) C4 0.031(2) 0.027(2) 0.0166(17) -0.0027(15) 0.0016(14) 0.0052(17) C27 0.033(2) 0.028(2) 0.026(2) 0.0000(16) 0.0017(16) -0.0040(18) C7 0.0183(18) 0.0171(18) 0.0222(19) 0.0010(15) -0.0041(14) -0.0044(15) C10 0.0236(19) 0.035(2) 0.031(2) 0.0051(17) 0.0069(15) -0.0020(18) C28 0.048(3) 0.029(2) 0.031(2) -0.0035(18) 0.0029(19) -0.013(2) C105 0.0161(16) 0.032(2) 0.0281(18) 0.0031(18) 0.0062(13) 0.0023(17) C115 0.036(2) 0.037(3) 0.043(3) 0.005(2) 0.001(2) 0.002(2) C17 0.0216(17) 0.030(2) 0.036(2) 0.0042(19) -0.0047(15) -0.0002(18) C15 0.035(2) 0.041(3) 0.049(3) -0.009(2) -0.004(2) 0.009(2) C103 0.0246(19) 0.023(2) 0.0196(18) -0.0016(15) -0.0004(14) 0.0031(15) C13 0.0174(17) 0.0240(19) 0.030(2) 0.0019(16) -0.0028(14) -0.0008(15) C6 0.0185(16) 0.0307(19) 0.0295(19) -0.001(2) -0.0012(13) -0.001(2) C2 0.0185(17) 0.0201(18) 0.0191(17) -0.0015(14) -0.0023(13) 0.0020(15) C25 0.023(2) 0.029(2) 0.034(2) -0.0033(18) 0.0019(17) 0.0007(18) C5 0.0228(19) 0.033(3) 0.0244(19) 0.0008(16) 0.0042(15) 0.0000(17) C106 0.0188(17) 0.029(2) 0.0234(17) -0.0017(18) -0.0005(13) -0.0015(18) C14 0.0186(18) 0.025(2) 0.0241(19) 0.0029(15) -0.0019(14) -0.0019(16) C111 0.0156(18) 0.045(3) 0.037(2) 0.005(2) 0.0030(16) -0.0084(18) C31 0.031(2) 0.033(2) 0.047(3) 0.0023(19) -0.0112(19) -0.0067(18) C123 0.049(3) 0.055(3) 0.032(2) -0.012(2) 0.0174(19) -0.009(3) C9 0.0231(18) 0.0220(19) 0.0233(18) -0.0013(15) 0.0007(14) -0.0004(15) C110 0.0196(18) 0.033(2) 0.035(2) 0.0017(18) -0.0029(16) 0.0036(17) C30 0.034(3) 0.042(3) 0.065(3) -0.001(2) -0.022(2) -0.012(2) C12 0.0193(19) 0.038(2) 0.043(2) 0.0012(19) -0.0001(17) 0.0055(18) C122 0.031(2) 0.068(4) 0.037(3) -0.010(2) 0.014(2) 0.005(2) C112 0.028(2) 0.032(2) 0.026(2) 0.0045(16) 0.0026(15) -0.0033(17) C117 0.0218(19) 0.029(2) 0.0248(19) 0.0057(16) 0.0003(15) -0.0012(16) C114 0.0232(18) 0.030(2) 0.0274(19) 0.0082(16) -0.0023(14) -0.0021(17) C22 0.041(2) 0.045(3) 0.0227(19) 0.0006(19) 0.0016(16) 0.002(2) C11 0.022(2) 0.042(3) 0.036(2) 0.0066(19) 0.0072(16) -0.0005(19) C102 0.0167(18) 0.0201(19) 0.0224(18) 0.0026(15) 0.0038(14) 0.0046(15) C8 0.0153(17) 0.0254(19) 0.0244(19) -0.0051(15) -0.0026(14) -0.0026(16) C116 0.033(2) 0.040(3) 0.033(2) 0.0106(19) -0.0070(18) -0.007(2) C126 0.028(2) 0.030(2) 0.0208(19) -0.0059(16) -0.0006(15) -0.0100(17) C18 0.036(2) 0.046(3) 0.037(2) 0.017(2) -0.0139(19) -0.008(2) C124 0.052(3) 0.047(3) 0.023(2) -0.001(2) 0.0014(19) -0.003(2) C29 0.035(2) 0.040(3) 0.040(3) -0.008(2) 0.0003(19) -0.017(2) C24 0.029(2) 0.041(3) 0.044(3) -0.009(2) 0.0116(19) 0.000(2) C23 0.045(2) 0.046(3) 0.029(2) -0.0047(19) 0.0113(18) -0.006(2) C125 0.031(2) 0.034(2) 0.026(2) -0.0010(16) 0.0009(16) 0.0003(18) C120 0.0280(18) 0.0260(19) 0.0187(16) -0.0076(19) -0.0021(13) -0.002(2) C121 0.028(2) 0.047(3) 0.027(2) -0.0058(19) 0.0025(17) 0.003(2) C131 0.035(2) 0.037(3) 0.055(3) -0.008(2) -0.004(2) -0.008(2) C119 0.039(2) 0.037(3) 0.051(3) 0.001(2) -0.001(2) 0.009(2) C19 0.040(3) 0.029(2) 0.070(4) 0.013(2) 0.000(2) 0.007(2) C127 0.036(2) 0.042(3) 0.039(3) -0.014(2) 0.0105(19) -0.011(2) C16 0.042(3) 0.045(3) 0.025(2) 0.0055(19) -0.0026(18) -0.004(2) C128 0.062(3) 0.053(3) 0.042(3) -0.024(2) 0.014(2) -0.023(3) C129 0.048(3) 0.062(3) 0.050(3) -0.010(3) -0.009(2) -0.027(3) C130 0.034(3) 0.065(4) 0.055(3) -0.006(3) -0.009(2) -0.012(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 Sb1 C1 2.118(4) . ? Sb1 C20 2.132(3) . ? Sb1 C26 2.140(4) . ? Sb1 Cl1 2.4332(10) . ? Sb1 Cl2 2.4852(9) . ? Sb2 C120 2.118(4) . ? Sb2 C101 2.128(4) . ? Sb2 C126 2.132(4) . ? Sb2 Cl4 2.4314(10) . ? Sb2 Cl3 2.4771(9) . ? N2 C107 1.269(5) . ? N2 C108 1.437(5) . ? N1 C7 1.270(5) . ? N1 C8 1.443(5) . ? C108 C113 1.402(5) . ? C108 C109 1.413(5) . ? C20 C21 1.382(5) . ? C20 C25 1.387(5) . ? C26 C27 1.381(6) . ? C26 C31 1.385(5) . ? C21 C22 1.394(5) . ? C21 H21 0.9300 . ? C118 C117 1.531(6) . ? C118 118A 0.9600 . ? C118 118B 0.9600 . ? C118 118C 0.9599 . ? C3 C4 1.379(6) . ? C3 C2 1.391(5) . ? C3 H3 0.9300 . ? C113 C112 1.383(5) . ? C113 C117 1.514(5) . ? C107 C102 1.462(5) . ? C107 H107 0.9300 . ? C104 C103 1.371(5) . ? C104 C105 1.384(6) . ? C104 H104 0.9301 . ? C101 C106 1.374(5) . ? C101 C102 1.398(5) . ? C109 C110 1.397(5) . ? C109 C114 1.516(5) . ? C1 C2 1.390(5) . ? C1 C6 1.390(5) . ? C4 C5 1.390(6) . ? C4 H4 0.9300 . ? C27 C28 1.395(6) . ? C27 H27 0.9300 . ? C7 C2 1.456(5) . ? C7 H7 0.9299 . ? C10 C11 1.380(6) . ? C10 C9 1.387(5) . ? C10 H10 0.9299 . ? C28 C29 1.357(6) . ? C28 H28 0.9300 . ? C105 C106 1.392(5) . ? C105 H105 0.9300 . ? C115 C114 1.528(6) . ? C115 115A 0.9601 . ? C115 115B 0.9600 . ? C115 115C 0.9600 . ? C17 C13 1.520(6) . ? C17 C19 1.523(6) . ? C17 C18 1.537(6) . ? C17 H17 0.9800 . ? C15 C14 1.517(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9598 . ? C15 H15C 0.9600 . ? C103 C102 1.395(5) . ? C103 H103 0.9299 . ? C13 C12 1.390(6) . ? C13 C8 1.413(5) . ? C6 C5 1.393(5) . ? C6 H6 0.9300 . ? C25 C24 1.400(6) . ? C25 H25 0.9300 . ? C5 H5 0.9299 . ? C106 H106 0.9300 . ? C14 C9 1.512(5) . ? C14 C16 1.518(5) . ? C14 H14 0.9799 . ? C111 C110 1.374(6) . ? C111 C112 1.385(6) . ? C111 H111 0.9300 . ? C31 C30 1.401(6) . ? C31 H31 0.9301 . ? C123 C124 1.365(7) . ? C123 C122 1.372(7) . ? C123 H123 0.9300 . ? C9 C8 1.392(5) . ? C110 H110 0.9300 . ? C30 C29 1.357(7) . ? C30 H30 0.9301 . ? C12 C11 1.378(6) . ? C12 H12 0.9299 . ? C122 C121 1.396(6) . ? C122 H122 0.9300 . ? C112 H112 0.9300 . ? C117 C119 1.517(6) . ? C117 H117 0.9801 . ? C114 C116 1.526(6) . ? C114 H114 0.9800 . ? C22 C23 1.371(6) . ? C22 H22 0.9301 . ? C11 H11 0.9299 . ? C116 116A 0.9600 . ? C116 116B 0.9601 . ? C116 116C 0.9601 . ? C126 C127 1.373(6) . ? C126 C131 1.390(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C124 C125 1.396(5) . ? C124 H124 0.9300 . ? C29 H29 0.9300 . ? C24 C23 1.374(7) . ? C24 H24 0.9301 . ? C23 H23 0.9301 . ? C125 C120 1.383(5) . ? C125 H125 0.9300 . ? C120 C121 1.378(6) . ? C121 H121 0.9300 . ? C131 C130 1.371(6) . ? C131 H131 0.9299 . ? C119 119A 0.9599 . ? C119 119B 0.9599 . ? C119 119C 0.9600 . ? C19 H19A 0.9599 . ? C19 H19B 0.9600 . ? C19 H19C 0.9601 . ? C127 C128 1.391(6) . ? C127 H127 0.9301 . ? C16 H16A 0.9599 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C128 C129 1.369(8) . ? C128 H128 0.9299 . ? C129 C130 1.374(8) . ? C129 H129 0.9299 . ? C130 H130 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Sb1 C20 156.68(15) . . ? C1 Sb1 C26 100.25(14) . . ? C20 Sb1 C26 103.03(14) . . ? C1 Sb1 Cl1 87.84(10) . . ? C20 Sb1 Cl1 91.18(12) . . ? C26 Sb1 Cl1 95.65(11) . . ? C1 Sb1 Cl2 86.02(10) . . ? C20 Sb1 Cl2 91.18(13) . . ? C26 Sb1 Cl2 93.58(11) . . ? Cl1 Sb1 Cl2 169.70(3) . . ? C120 Sb2 C101 157.11(14) . . ? C120 Sb2 C126 98.96(15) . . ? C101 Sb2 C126 103.91(15) . . ? C120 Sb2 Cl4 91.22(13) . . ? C101 Sb2 Cl4 87.51(10) . . ? C126 Sb2 Cl4 94.93(12) . . ? C120 Sb2 Cl3 91.97(13) . . ? C101 Sb2 Cl3 86.71(10) . . ? C126 Sb2 Cl3 91.77(12) . . ? Cl4 Sb2 Cl3 172.04(4) . . ? C107 N2 C108 118.6(3) . . ? C7 N1 C8 117.7(3) . . ? C113 C108 C109 121.7(3) . . ? C113 C108 N2 119.8(3) . . ? C109 C108 N2 118.5(3) . . ? C21 C20 C25 120.8(4) . . ? C21 C20 Sb1 117.1(3) . . ? C25 C20 Sb1 121.6(3) . . ? C27 C26 C31 118.8(4) . . ? C27 C26 Sb1 121.6(3) . . ? C31 C26 Sb1 119.6(3) . . ? C20 C21 C22 119.1(4) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.4 . . ? C117 C118 118A 109.1 . . ? C117 C118 118B 109.7 . . ? 118A C118 118B 109.5 . . ? C117 C118 118C 109.6 . . ? 118A C118 118C 109.5 . . ? 118B C118 118C 109.5 . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.6 . . ? C112 C113 C108 118.8(3) . . ? C112 C113 C117 120.8(3) . . ? C108 C113 C117 120.3(3) . . ? N2 C107 C102 122.1(3) . . ? N2 C107 H107 119.0 . . ? C102 C107 H107 118.9 . . ? C103 C104 C105 120.3(3) . . ? C103 C104 H104 119.6 . . ? C105 C104 H104 120.1 . . ? C106 C101 C102 119.9(3) . . ? C106 C101 Sb2 120.3(3) . . ? C102 C101 Sb2 119.8(3) . . ? C110 C109 C108 116.4(3) . . ? C110 C109 C114 119.0(3) . . ? C108 C109 C114 124.6(3) . . ? C2 C1 C6 120.7(3) . . ? C2 C1 Sb1 120.4(3) . . ? C6 C1 Sb1 118.9(3) . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.1 . . ? C26 C27 C28 120.1(4) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 119.6 . . ? N1 C7 C2 121.4(3) . . ? N1 C7 H7 119.2 . . ? C2 C7 H7 119.4 . . ? C11 C10 C9 120.9(4) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.8 . . ? C29 C28 C27 120.6(4) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 120.0 . . ? C104 C105 C106 120.1(4) . . ? C104 C105 H105 119.6 . . ? C106 C105 H105 120.3 . . ? C114 C115 115A 109.7 . . ? C114 C115 115B 109.3 . . ? 115A C115 115B 109.5 . . ? C114 C115 115C 109.3 . . ? 115A C115 115C 109.5 . . ? 115B C115 115C 109.5 . . ? C13 C17 C19 111.9(4) . . ? C13 C17 C18 109.8(4) . . ? C19 C17 C18 111.5(4) . . ? C13 C17 H17 108.2 . . ? C19 C17 H17 108.0 . . ? C18 C17 H17 107.4 . . ? C14 C15 H15A 109.4 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.1 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C104 C103 C102 120.0(4) . . ? C104 C103 H103 120.0 . . ? C102 C103 H103 120.0 . . ? C12 C13 C8 116.9(4) . . ? C12 C13 C17 118.8(3) . . ? C8 C13 C17 124.2(3) . . ? C1 C6 C5 119.3(4) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.0 . . ? C1 C2 C3 119.1(4) . . ? C1 C2 C7 120.0(3) . . ? C3 C2 C7 120.8(3) . . ? C20 C25 C24 119.3(4) . . ? C20 C25 H25 120.3 . . ? C24 C25 H25 120.4 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 120.2 . . ? C101 C106 C105 120.0(4) . . ? C101 C106 H106 120.1 . . ? C105 C106 H106 119.9 . . ? C9 C14 C15 110.4(3) . . ? C9 C14 C16 113.0(3) . . ? C15 C14 C16 110.4(4) . . ? C9 C14 H14 107.8 . . ? C15 C14 H14 107.5 . . ? C16 C14 H14 107.6 . . ? C110 C111 C112 119.6(4) . . ? C110 C111 H111 119.9 . . ? C112 C111 H111 120.5 . . ? C26 C31 C30 119.9(4) . . ? C26 C31 H31 119.9 . . ? C30 C31 H31 120.2 . . ? C124 C123 C122 120.4(4) . . ? C124 C123 H123 119.7 . . ? C122 C123 H123 119.9 . . ? C10 C9 C8 118.3(3) . . ? C10 C9 C14 120.0(3) . . ? C8 C9 C14 121.6(3) . . ? C111 C110 C109 122.7(4) . . ? C111 C110 H110 118.9 . . ? C109 C110 H110 118.4 . . ? C29 C30 C31 120.4(4) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C11 C12 C13 121.8(4) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.0 . . ? C123 C122 C121 120.2(4) . . ? C123 C122 H122 120.0 . . ? C121 C122 H122 119.8 . . ? C113 C112 C111 120.8(4) . . ? C113 C112 H112 119.3 . . ? C111 C112 H112 119.9 . . ? C113 C117 C119 110.3(3) . . ? C113 C117 C118 112.0(3) . . ? C119 C117 C118 111.6(4) . . ? C113 C117 H117 107.7 . . ? C119 C117 H117 107.5 . . ? C118 C117 H117 107.5 . . ? C109 C114 C116 110.5(3) . . ? C109 C114 C115 111.5(3) . . ? C116 C114 C115 110.8(3) . . ? C109 C114 H114 107.7 . . ? C116 C114 H114 108.0 . . ? C115 C114 H114 108.3 . . ? C23 C22 C21 120.2(4) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.9 . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 120.2 . . ? C103 C102 C101 119.6(3) . . ? C103 C102 C107 120.8(3) . . ? C101 C102 C107 119.5(3) . . ? C9 C8 C13 122.0(3) . . ? C9 C8 N1 119.3(3) . . ? C13 C8 N1 118.7(3) . . ? C114 C116 116A 109.8 . . ? C114 C116 116B 109.2 . . ? 116A C116 116B 109.5 . . ? C114 C116 116C 109.4 . . ? 116A C116 116C 109.5 . . ? 116B C116 116C 109.5 . . ? C127 C126 C131 119.4(4) . . ? C127 C126 Sb2 119.4(3) . . ? C131 C126 Sb2 121.0(3) . . ? C17 C18 H18A 108.5 . . ? C17 C18 H18B 110.0 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.9 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C123 C124 C125 120.0(4) . . ? C123 C124 H124 120.1 . . ? C125 C124 H124 119.9 . . ? C28 C29 C30 120.2(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 119.8 . . ? C23 C24 C25 119.6(4) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C22 C23 C24 121.0(4) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.6 . . ? C120 C125 C124 119.9(4) . . ? C120 C125 H125 120.1 . . ? C124 C125 H125 120.0 . . ? C121 C120 C125 119.8(4) . . ? C121 C120 Sb2 122.2(3) . . ? C125 C120 Sb2 117.7(3) . . ? C120 C121 C122 119.6(4) . . ? C120 C121 H121 120.0 . . ? C122 C121 H121 120.4 . . ? C130 C131 C126 120.2(5) . . ? C130 C131 H131 120.1 . . ? C126 C131 H131 119.7 . . ? C117 C119 119A 109.5 . . ? C117 C119 119B 109.8 . . ? 119A C119 119B 109.5 . . ? C117 C119 119C 109.1 . . ? 119A C119 119C 109.5 . . ? 119B C119 119C 109.5 . . ? C17 C19 H19A 109.9 . . ? C17 C19 H19B 109.4 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.1 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C126 C127 C128 120.2(5) . . ? C126 C127 H127 119.8 . . ? C128 C127 H127 120.1 . . ? C14 C16 H16A 109.2 . . ? C14 C16 H16B 109.8 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.4 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C129 C128 C127 119.8(5) . . ? C129 C128 H128 120.4 . . ? C127 C128 H128 119.8 . . ? C128 C129 C130 120.3(5) . . ? C128 C129 H129 120.0 . . ? C130 C129 H129 119.7 . . ? C131 C130 C129 120.1(5) . . ? C131 C130 H130 119.7 . . ? C129 C130 H130 120.1 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.640 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 943197' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 Bi Cl N' _chemical_formula_sum 'C25 H27 Bi Cl N' _chemical_formula_weight 585.91 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' 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.2480(9) _cell_length_b 14.0750(14) _cell_length_c 14.5001(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2295.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16114 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 7.807 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.027 0 0 -1 0.092 1 0 0 0.114 -1 0 0 0.153 0 1 0 0.043 0 -1 0 0.074 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.345 _exptl_absorpt_correction_T_max 0.452 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16079 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5196 _reflns_number_gt 4321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0168P)^2^+16.3751P] 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 -0.027(12) _refine_ls_number_reflns 5196 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _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 0.52938(3) 0.49718(3) -0.033056(19) 0.02582(9) Uani 1 1 d . . . Cl1 Cl 0.5416(2) 0.64453(15) -0.14370(15) 0.0291(5) Uani 1 1 d . . . C15 C 0.6821(14) 0.1554(11) -0.0008(10) 0.079(5) Uani 1 1 d . . . H15A H 0.7248 0.1728 0.0540 0.095 Uiso 1 1 d R . . H15B H 0.7355 0.1549 -0.0524 0.095 Uiso 1 1 d R . . H15C H 0.6482 0.0933 0.0070 0.095 Uiso 1 1 d R . . C13 C 0.4126(9) 0.3023(7) 0.1970(6) 0.0268(19) Uani 1 1 d . . . C3 C 0.8272(7) 0.5108(9) 0.1697(6) 0.032(2) Uani 1 1 d . . . H3 H 0.8504 0.4718 0.2182 0.039 Uiso 1 1 d R . . C2 C 0.7281(7) 0.4860(7) 0.1185(6) 0.025(2) Uani 1 1 d . . . C12 C 0.3395(9) 0.2228(7) 0.2097(6) 0.030(2) Uani 1 1 d . . . H12 H 0.2871 0.2212 0.2593 0.036 Uiso 1 1 d R . . C7 C 0.6551(8) 0.4020(6) 0.1439(7) 0.0264(19) Uani 1 1 d . . . H7 H 0.6788 0.3635 0.1927 0.032 Uiso 1 1 d R . . N1 N 0.5615(6) 0.3824(5) 0.1004(5) 0.0228(16) Uani 1 1 d . . . C6 C 0.7610(8) 0.6199(7) 0.0220(7) 0.032(2) Uani 1 1 d . . . H6 H 0.7398 0.6574 -0.0282 0.038 Uiso 1 1 d R . . C1 C 0.6945(8) 0.5403(6) 0.0431(6) 0.0260(18) Uani 1 1 d . . . C21 C 0.2927(9) 0.5952(7) 0.0346(7) 0.035(2) Uani 1 1 d . . . H21 H 0.2673 0.5756 -0.0234 0.042 Uiso 1 1 d R . . C20 C 0.4074(8) 0.5754(6) 0.0618(6) 0.0255(19) Uani 1 1 d . . . C8 C 0.4895(8) 0.3007(6) 0.1202(6) 0.027(2) Uani 1 1 d . . . C9 C 0.4952(8) 0.2244(6) 0.0593(6) 0.029(2) Uani 1 1 d . . . C10 C 0.4204(9) 0.1470(7) 0.0757(7) 0.032(2) Uani 1 1 d . . . H10 H 0.4202 0.0958 0.0352 0.039 Uiso 1 1 d R . . C14 C 0.5827(9) 0.2228(6) -0.0202(6) 0.030(2) Uani 1 1 d . . . H14 H 0.6189 0.2860 -0.0244 0.036 Uiso 1 1 d R . . C18 C 0.4574(11) 0.3589(8) 0.3580(7) 0.045(3) Uani 1 1 d . . . H18A H 0.4137 0.3064 0.3834 0.054 Uiso 1 1 d R . . H18B H 0.4518 0.4124 0.3989 0.054 Uiso 1 1 d R . . H18C H 0.5393 0.3412 0.3509 0.054 Uiso 1 1 d R . . C5 C 0.8592(10) 0.6435(8) 0.0748(8) 0.040(3) Uani 1 1 d . . . H5 H 0.9034 0.6975 0.0608 0.048 Uiso 1 1 d R . . C11 C 0.3451(10) 0.1468(7) 0.1503(7) 0.036(2) Uani 1 1 d . . . H11 H 0.2970 0.0941 0.1606 0.043 Uiso 1 1 d R . . C17 C 0.4052(9) 0.3847(7) 0.2632(6) 0.031(2) Uani 1 1 d . . . H17 H 0.4541 0.4361 0.2379 0.037 Uiso 1 1 d R . . C4 C 0.8921(9) 0.5887(8) 0.1489(8) 0.039(2) Uani 1 1 d . . . H4 H 0.9573 0.6049 0.1851 0.047 Uiso 1 1 d R . . C25 C 0.4447(8) 0.6044(6) 0.1496(7) 0.031(2) Uani 1 1 d . . . H25 H 0.5225 0.5945 0.1690 0.037 Uiso 1 1 d R . . C19 C 0.2792(10) 0.4211(8) 0.2734(7) 0.042(3) Uani 1 1 d . . . H19A H 0.2475 0.4347 0.2134 0.051 Uiso 1 1 d R . . H19B H 0.2800 0.4782 0.3096 0.051 Uiso 1 1 d R . . H19C H 0.2306 0.3742 0.3032 0.051 Uiso 1 1 d R . . C16 C 0.5233(14) 0.2027(11) -0.1120(7) 0.069(4) Uani 1 1 d . . . H16A H 0.4894 0.1402 -0.1102 0.082 Uiso 1 1 d R . . H16B H 0.5807 0.2062 -0.1609 0.082 Uiso 1 1 d R . . H16C H 0.4616 0.2486 -0.1226 0.082 Uiso 1 1 d R . . C22 C 0.2150(9) 0.6408(8) 0.0911(7) 0.039(2) Uani 1 1 d . . . H22 H 0.1392 0.6559 0.0700 0.047 Uiso 1 1 d R . . C24 C 0.3617(9) 0.6499(8) 0.2078(8) 0.036(2) Uani 1 1 d . . . H24 H 0.3846 0.6679 0.2669 0.043 Uiso 1 1 d R . . C23 C 0.2489(9) 0.6672(7) 0.1791(7) 0.035(2) Uani 1 1 d . . . H23 H 0.1944 0.6960 0.2184 0.042 Uiso 1 1 d 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 0.02822(14) 0.02554(13) 0.02368(13) -0.0003(2) -0.00087(13) -0.0015(2) Cl1 0.0345(12) 0.0251(10) 0.0276(10) 0.0067(8) 0.0006(9) 0.0013(9) C15 0.078(11) 0.081(10) 0.079(10) 0.036(8) 0.051(8) 0.036(9) C13 0.025(5) 0.031(5) 0.024(5) 0.004(4) 0.003(4) -0.002(4) C3 0.028(4) 0.031(6) 0.038(5) -0.002(5) 0.003(3) 0.004(5) C2 0.018(4) 0.024(6) 0.032(4) 0.000(4) 0.005(3) -0.001(4) C12 0.031(5) 0.034(5) 0.026(5) 0.008(4) 0.006(4) -0.003(4) C7 0.028(5) 0.020(4) 0.031(5) -0.001(4) 0.002(4) 0.004(4) N1 0.029(4) 0.019(3) 0.021(3) 0.003(3) 0.003(3) -0.001(3) C6 0.021(4) 0.034(5) 0.040(6) -0.003(4) 0.004(4) -0.003(4) C1 0.026(4) 0.024(4) 0.028(5) -0.004(4) 0.006(4) -0.002(3) C21 0.039(5) 0.040(5) 0.027(5) 0.004(5) -0.004(5) 0.004(4) C20 0.027(5) 0.020(4) 0.029(5) -0.001(3) 0.004(4) -0.004(4) C8 0.036(5) 0.022(4) 0.024(4) 0.004(3) 0.001(4) -0.006(4) C9 0.039(6) 0.025(4) 0.022(4) 0.000(3) -0.003(3) -0.003(4) C10 0.040(6) 0.026(5) 0.032(5) -0.001(4) -0.002(4) -0.007(4) C14 0.036(5) 0.027(4) 0.028(5) -0.004(4) 0.006(4) -0.001(4) C18 0.054(7) 0.051(6) 0.029(5) -0.013(5) 0.000(5) 0.008(6) C5 0.036(6) 0.035(6) 0.049(6) -0.005(5) 0.009(5) -0.008(5) C11 0.042(6) 0.030(5) 0.035(5) 0.009(4) -0.004(5) -0.013(5) C17 0.029(5) 0.036(5) 0.028(5) 0.000(4) 0.009(4) -0.001(4) C4 0.027(5) 0.045(6) 0.046(6) -0.010(5) -0.002(5) 0.002(5) C25 0.026(5) 0.030(5) 0.036(5) -0.005(4) -0.004(4) 0.002(4) C19 0.045(7) 0.041(6) 0.041(6) 0.000(5) 0.005(5) 0.003(5) C16 0.082(10) 0.101(11) 0.023(5) -0.012(6) 0.008(6) -0.029(9) C22 0.021(5) 0.054(7) 0.041(6) 0.013(5) 0.000(4) 0.003(5) C24 0.029(5) 0.038(6) 0.042(6) -0.009(5) -0.003(5) 0.004(4) C23 0.034(6) 0.031(5) 0.039(6) 0.003(4) 0.008(4) 0.008(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 C20 2.233(9) . ? Bi1 C1 2.244(9) . ? Bi1 N1 2.547(7) . ? Bi1 Cl1 2.626(2) . ? C15 C14 1.492(16) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9599 . ? C13 C12 1.400(13) . ? C13 C8 1.411(13) . ? C13 C17 1.508(13) . ? C3 C4 1.351(15) . ? C3 C2 1.384(12) . ? C3 H3 0.9300 . ? C2 C1 1.386(13) . ? C2 C7 1.486(13) . ? C12 C11 1.374(14) . ? C12 H12 0.9301 . ? C7 N1 1.258(11) . ? C7 H7 0.9301 . ? N1 C8 1.435(10) . ? C6 C1 1.382(12) . ? C6 C5 1.383(14) . ? C6 H6 0.9301 . ? C21 C22 1.360(15) . ? C21 C20 1.377(13) . ? C21 H21 0.9301 . ? C20 C25 1.401(13) . ? C8 C9 1.393(12) . ? C9 C10 1.397(13) . ? C9 C14 1.516(13) . ? C10 C11 1.374(14) . ? C10 H10 0.9299 . ? C14 C16 1.515(15) . ? C14 H14 0.9801 . ? C18 C17 1.538(14) . ? C18 H18A 0.9601 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C5 C4 1.374(16) . ? C5 H5 0.9301 . ? C11 H11 0.9300 . ? C17 C19 1.514(14) . ? C17 H17 0.9800 . ? C4 H4 0.9300 . ? C25 C24 1.411(13) . ? C25 H25 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9599 . ? C16 H16C 0.9600 . ? C22 C23 1.383(15) . ? C22 H22 0.9299 . ? C24 C23 1.357(14) . ? C24 H24 0.9300 . ? C23 H23 0.9301 . ? 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 C20 Bi1 C1 94.2(3) . . ? C20 Bi1 N1 86.1(3) . . ? C1 Bi1 N1 71.4(3) . . ? C20 Bi1 Cl1 91.1(2) . . ? C1 Bi1 Cl1 92.5(2) . . ? N1 Bi1 Cl1 163.33(17) . . ? C14 C15 H15A 111.7 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 107.7 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C13 C8 116.9(9) . . ? C12 C13 C17 119.9(8) . . ? C8 C13 C17 123.2(8) . . ? C4 C3 C2 121.3(10) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 118.9 . . ? C3 C2 C1 120.2(9) . . ? C3 C2 C7 120.8(9) . . ? C1 C2 C7 118.9(8) . . ? C11 C12 C13 120.8(9) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.5 . . ? N1 C7 C2 120.8(8) . . ? N1 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C7 N1 C8 123.2(8) . . ? C7 N1 Bi1 111.1(6) . . ? C8 N1 Bi1 125.4(5) . . ? C1 C6 C5 120.3(10) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 120.1 . . ? C6 C1 C2 118.3(9) . . ? C6 C1 Bi1 124.0(7) . . ? C2 C1 Bi1 117.7(6) . . ? C22 C21 C20 121.7(10) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.1 . . ? C21 C20 C25 118.8(9) . . ? C21 C20 Bi1 119.9(7) . . ? C25 C20 Bi1 121.3(7) . . ? C9 C8 C13 122.8(8) . . ? C9 C8 N1 117.7(8) . . ? C13 C8 N1 119.5(8) . . ? C8 C9 C10 117.7(8) . . ? C8 C9 C14 121.6(8) . . ? C10 C9 C14 120.6(8) . . ? C11 C10 C9 120.5(9) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.8 . . ? C15 C14 C16 112.2(11) . . ? C15 C14 C9 110.6(8) . . ? C16 C14 C9 112.6(9) . . ? C15 C14 H14 106.2 . . ? C16 C14 H14 107.4 . . ? C9 C14 H14 107.6 . . ? C17 C18 H18A 109.1 . . ? C17 C18 H18B 110.0 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.3 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C5 C6 120.9(10) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 120.2 . . ? C10 C11 C12 121.3(9) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.6 . . ? C13 C17 C19 112.0(9) . . ? C13 C17 C18 111.5(8) . . ? C19 C17 C18 110.5(8) . . ? C13 C17 H17 107.4 . . ? C19 C17 H17 108.1 . . ? C18 C17 H17 107.1 . . ? C3 C4 C5 119.0(10) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 121.2 . . ? C20 C25 C24 118.5(9) . . ? C20 C25 H25 120.8 . . ? C24 C25 H25 120.6 . . ? C17 C19 H19A 109.1 . . ? C17 C19 H19B 109.2 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 110.1 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 C16 H16A 108.8 . . ? C14 C16 H16B 110.0 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C21 C22 C23 120.4(10) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.7 . . ? C23 C24 C25 121.1(10) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.4 . . ? C24 C23 C22 119.5(10) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.1 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.087 _refine_diff_density_min -1.536 _refine_diff_density_rms 0.175 _database_code_depnum_ccdc_archive 'CCDC 943198' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H32 Bi Cl2 N, 2(C H2 Cl2)' _chemical_formula_sum 'C33 H36 Bi Cl6 N' _chemical_formula_weight 868.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 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 9.3232(9) _cell_length_b 12.4339(12) _cell_length_c 15.6550(8) _cell_angle_alpha 79.541(4) _cell_angle_beta 74.971(6) _cell_angle_gamma 82.898(7) _cell_volume 1718.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 33131 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 5.622 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.062 -1 0 0 0.088 1 0 0 0.103 0 -1 0 0.066 0 1 0 0.089 0 -1 -1 0.153 0 0 -1 0.264 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.243 _exptl_absorpt_correction_T_max 0.480 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33049 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7843 _reflns_number_gt 7197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0418P)^2^+8.0906P] 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 7843 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.866347(18) -0.090152(13) 0.260279(11) 0.01650(6) Uani 1 1 d . . . Cl2 Cl 0.67215(15) -0.11237(11) 0.41651(8) 0.0272(3) Uani 1 1 d . . . Cl1 Cl 1.07591(14) -0.05921(10) 0.11797(8) 0.0246(2) Uani 1 1 d . . . Cl3 Cl 0.3093(3) 0.4948(2) 0.47683(18) 0.0832(8) Uani 1 1 d . . . Cl4 Cl 0.0910(3) 0.3988(3) 0.41451(18) 0.0876(9) Uani 1 1 d . . . N1 N 0.9033(5) 0.1320(3) 0.2505(3) 0.0193(8) Uani 1 1 d . . . C22 C 0.4340(6) -0.0184(5) 0.1879(4) 0.0353(13) Uani 1 1 d . . . H22 H 0.3381 -0.0399 0.2131 0.042 Uiso 1 1 d R . . C31 C 0.7571(7) -0.3256(5) 0.2912(4) 0.0341(13) Uani 1 1 d . . . H31 H 0.6678 -0.2904 0.3189 0.041 Uiso 1 1 d R . . C1 C 1.0219(6) -0.0675(4) 0.3387(3) 0.0228(7) Uani 1 1 d . . . C7 C 0.9878(6) 0.1357(4) 0.3013(3) 0.0214(10) Uani 1 1 d . . . H7 H 1.0110 0.2032 0.3094 0.026 Uiso 1 1 d R . . C3 C 1.1474(6) 0.0418(5) 0.4025(4) 0.0261(11) Uani 1 1 d . . . H3 H 1.1645 0.1103 0.4120 0.031 Uiso 1 1 d R . . C6 C 1.0890(6) -0.1624(4) 0.3779(4) 0.0264(11) Uani 1 1 d . . . H6 H 1.0681 -0.2308 0.3703 0.032 Uiso 1 1 d R . . C9 C 0.7028(6) 0.2678(4) 0.2257(3) 0.0220(10) Uani 1 1 d . . . C32 C 0.1851(10) 0.3916(7) 0.4992(6) 0.062(2) Uani 1 1 d . . . H32A H 0.2405 0.3204 0.5055 0.074 Uiso 1 1 d R . . H32B H 0.1126 0.3977 0.5554 0.074 Uiso 1 1 d R . . C20 C 0.6861(6) -0.0198(4) 0.1936(3) 0.0200(9) Uani 1 1 d . . . C8 C 0.8513(6) 0.2284(4) 0.1990(3) 0.0205(10) Uani 1 1 d . . . C13 C 0.9464(6) 0.2759(4) 0.1190(3) 0.0227(10) Uani 1 1 d . . . C26 C 0.8835(6) -0.2688(4) 0.2561(3) 0.0209(10) Uani 1 1 d . . . C15 C 0.6249(7) 0.2727(5) 0.3909(4) 0.0354(13) Uani 1 1 d . . . H15A H 0.7280 0.2667 0.3921 0.043 Uiso 1 1 d R . . H15B H 0.5679 0.2371 0.4469 0.043 Uiso 1 1 d R . . H15C H 0.5895 0.3487 0.3817 0.043 Uiso 1 1 d R . . C12 C 0.8866(7) 0.3638(4) 0.0675(4) 0.0301(12) Uani 1 1 d . . . H12 H 0.9481 0.3971 0.0151 0.036 Uiso 1 1 d R . . C21 C 0.5438(6) -0.0521(5) 0.2343(4) 0.0282(11) Uani 1 1 d . . . H21 H 0.5232 -0.0952 0.2905 0.034 Uiso 1 1 d R . . C2 C 1.0497(5) 0.0343(4) 0.3477(3) 0.0186(9) Uani 1 1 d . . . C23 C 0.4649(7) 0.0458(5) 0.1053(4) 0.0355(13) Uani 1 1 d . . . H23 H 0.3902 0.0671 0.0748 0.043 Uiso 1 1 d R . . C28 C 1.0220(8) -0.4314(5) 0.2088(5) 0.0407(15) Uani 1 1 d . . . H28 H 1.1112 -0.4672 0.1816 0.049 Uiso 1 1 d R . . C11 C 0.7397(7) 0.4045(5) 0.0922(4) 0.0339(13) Uani 1 1 d . . . H11 H 0.7026 0.4634 0.0561 0.041 Uiso 1 1 d R . . C24 C 0.6071(7) 0.0790(5) 0.0675(4) 0.0332(13) Uani 1 1 d . . . H24 H 0.6268 0.1246 0.0125 0.040 Uiso 1 1 d R . . C14 C 0.6074(6) 0.2178(4) 0.3149(4) 0.0246(10) Uani 1 1 d . . . H14 H 0.6445 0.1406 0.3264 0.030 Uiso 1 1 d R . . C5 C 1.1884(7) -0.1537(5) 0.4290(4) 0.0304(12) Uani 1 1 d . . . H5 H 1.2363 -0.2169 0.4542 0.036 Uiso 1 1 d R . . C18 C 1.2104(7) 0.3110(5) 0.1093(4) 0.0350(13) Uani 1 1 d . . . H18A H 1.3127 0.2838 0.0905 0.042 Uiso 1 1 d R . . H18B H 1.1857 0.3130 0.1725 0.042 Uiso 1 1 d R . . H18C H 1.1956 0.3836 0.0777 0.042 Uiso 1 1 d R . . C17 C 1.1113(6) 0.2351(4) 0.0893(4) 0.0256(11) Uani 1 1 d . . . H17 H 1.1260 0.1623 0.1237 0.031 Uiso 1 1 d R . . C30 C 0.7658(8) -0.4365(5) 0.2841(5) 0.0406(15) Uani 1 1 d . . . H30 H 0.6821 -0.4758 0.3078 0.049 Uiso 1 1 d R . . C25 C 0.7214(6) 0.0452(4) 0.1109(4) 0.0253(11) Uani 1 1 d . . . H25 H 0.8180 0.0652 0.0852 0.030 Uiso 1 1 d R . . C29 C 0.8973(8) -0.4886(5) 0.2428(5) 0.0373(14) Uani 1 1 d . . . H29 H 0.9021 -0.5623 0.2374 0.045 Uiso 1 1 d R . . C16 C 0.4431(7) 0.2211(6) 0.3161(5) 0.0401(14) Uani 1 1 d . . . H16A H 0.3964 0.2936 0.3215 0.048 Uiso 1 1 d R . . H16B H 0.3949 0.1700 0.3658 0.048 Uiso 1 1 d R . . H16C H 0.4348 0.2011 0.2612 0.048 Uiso 1 1 d R . . Cl6 Cl 0.4223(2) 0.63591(18) 0.07601(13) 0.0579(5) Uani 1 1 d . . . Cl5 Cl 0.3852(2) 0.6326(3) 0.26603(14) 0.0751(7) Uani 1 1 d . . . C10 C 0.6487(6) 0.3563(4) 0.1716(4) 0.0288(11) Uani 1 1 d . . . H10 H 0.5497 0.3834 0.1885 0.035 Uiso 1 1 d R . . C4 C 1.2161(6) -0.0523(4) 0.4416(3) 0.0228(7) Uani 1 1 d . . . H4 H 1.2811 -0.0467 0.4764 0.027 Uiso 1 1 d R . . C19 C 1.1547(7) 0.2238(5) -0.0107(4) 0.0344(13) Uani 1 1 d . . . H19A H 1.1723 0.2945 -0.0464 0.041 Uiso 1 1 d R . . H19B H 1.0748 0.1944 -0.0250 0.041 Uiso 1 1 d R . . H19C H 1.2434 0.1753 -0.0230 0.041 Uiso 1 1 d R . . C27 C 1.0158(7) -0.3211(4) 0.2137(4) 0.0319(12) Uani 1 1 d . . . H27 H 1.1003 -0.2827 0.1895 0.038 Uiso 1 1 d R . . C33 C 0.4850(13) 0.6803(10) 0.1577(6) 0.083(3) Uani 1 1 d . . . H33A H 0.4817 0.7598 0.1478 0.100 Uiso 1 1 d R . . H33B H 0.5882 0.6520 0.1519 0.100 Uiso 1 1 d 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 0.01691(10) 0.01530(9) 0.01734(9) -0.00124(6) -0.00364(7) -0.00454(6) Cl2 0.0272(6) 0.0331(6) 0.0184(5) -0.0030(5) 0.0013(5) -0.0074(5) Cl1 0.0227(6) 0.0272(6) 0.0211(5) -0.0038(5) 0.0020(5) -0.0073(5) Cl3 0.0851(17) 0.0780(16) 0.0678(14) 0.0027(12) 0.0089(13) -0.0156(13) Cl4 0.0837(17) 0.111(2) 0.0691(15) -0.0328(14) -0.0319(13) 0.0435(16) N1 0.021(2) 0.0151(18) 0.0209(19) -0.0025(15) -0.0024(16) -0.0048(15) C22 0.019(3) 0.050(4) 0.038(3) -0.011(3) -0.007(2) 0.000(2) C31 0.032(3) 0.024(3) 0.048(4) -0.007(2) -0.008(3) -0.008(2) C1 0.0198(16) 0.0353(19) 0.0184(16) -0.0069(14) -0.0092(13) -0.0083(14) C7 0.023(2) 0.021(2) 0.020(2) -0.0049(19) -0.0008(19) -0.0069(18) C3 0.026(3) 0.034(3) 0.024(2) -0.006(2) -0.011(2) -0.010(2) C6 0.033(3) 0.021(2) 0.026(3) 0.000(2) -0.009(2) -0.003(2) C9 0.023(2) 0.018(2) 0.026(2) -0.0021(19) -0.005(2) -0.0074(18) C32 0.068(5) 0.054(5) 0.053(5) 0.006(4) -0.015(4) 0.012(4) C20 0.023(2) 0.018(2) 0.022(2) -0.0074(18) -0.0078(19) -0.0025(18) C8 0.023(2) 0.016(2) 0.022(2) -0.0012(18) -0.0038(19) -0.0043(18) C13 0.028(3) 0.016(2) 0.023(2) -0.0030(19) -0.001(2) -0.0062(19) C26 0.023(2) 0.018(2) 0.023(2) -0.0034(19) -0.008(2) 0.0003(18) C15 0.036(3) 0.041(3) 0.026(3) 0.003(2) -0.002(2) -0.013(3) C12 0.036(3) 0.024(3) 0.025(3) 0.003(2) -0.001(2) -0.005(2) C21 0.023(3) 0.035(3) 0.025(3) -0.001(2) -0.006(2) -0.003(2) C2 0.017(2) 0.024(2) 0.015(2) -0.0029(18) -0.0024(18) -0.0088(18) C23 0.030(3) 0.046(3) 0.037(3) -0.018(3) -0.018(3) 0.010(3) C28 0.045(4) 0.028(3) 0.047(4) -0.011(3) -0.008(3) 0.006(3) C11 0.037(3) 0.029(3) 0.033(3) 0.003(2) -0.011(3) 0.001(2) C24 0.040(3) 0.033(3) 0.026(3) -0.004(2) -0.014(2) 0.007(2) C14 0.021(2) 0.021(2) 0.029(3) -0.003(2) 0.000(2) -0.0063(19) C5 0.033(3) 0.029(3) 0.032(3) -0.005(2) -0.016(2) 0.003(2) C18 0.029(3) 0.031(3) 0.041(3) -0.004(3) -0.002(3) -0.008(2) C17 0.027(3) 0.019(2) 0.026(3) 0.000(2) 0.001(2) -0.006(2) C30 0.043(4) 0.026(3) 0.057(4) -0.011(3) -0.013(3) -0.014(3) C25 0.026(3) 0.024(2) 0.023(2) -0.004(2) -0.003(2) 0.001(2) C29 0.052(4) 0.018(2) 0.048(4) -0.010(2) -0.020(3) -0.001(2) C16 0.026(3) 0.051(4) 0.041(3) -0.007(3) 0.000(3) -0.013(3) Cl6 0.0540(11) 0.0697(12) 0.0463(10) -0.0067(9) -0.0081(9) -0.0028(9) Cl5 0.0440(11) 0.130(2) 0.0439(10) -0.0037(12) -0.0036(9) -0.0087(12) C10 0.026(3) 0.024(2) 0.036(3) -0.006(2) -0.007(2) 0.001(2) C4 0.0198(16) 0.0353(19) 0.0184(16) -0.0069(14) -0.0092(13) -0.0083(14) C19 0.035(3) 0.035(3) 0.029(3) -0.006(2) 0.001(2) -0.007(2) C27 0.033(3) 0.022(3) 0.040(3) -0.003(2) -0.008(3) -0.003(2) C33 0.108(8) 0.105(8) 0.040(4) 0.005(5) -0.008(5) -0.064(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 C1 2.200(5) . ? Bi1 C20 2.212(5) . ? Bi1 C26 2.218(5) . ? Bi1 Cl1 2.5585(12) . ? Bi1 Cl2 2.6302(12) . ? Bi1 N1 2.798(4) . ? Cl3 C32 1.762(10) . ? Cl4 C32 1.754(9) . ? N1 C7 1.265(7) . ? N1 C8 1.425(6) . ? C22 C23 1.371(9) . ? C22 C21 1.386(8) . ? C22 H22 0.9300 . ? C31 C26 1.385(8) . ? C31 C30 1.394(8) . ? C31 H31 0.9300 . ? C1 C2 1.361(7) . ? C1 C6 1.383(7) . ? C7 C2 1.469(7) . ? C7 H7 0.9300 . ? C3 C4 1.384(8) . ? C3 C2 1.424(7) . ? C3 H3 0.9301 . ? C6 C5 1.397(8) . ? C6 H6 0.9300 . ? C9 C10 1.389(7) . ? C9 C8 1.392(7) . ? C9 C14 1.519(7) . ? C32 H32A 0.9699 . ? C32 H32B 0.9700 . ? C20 C25 1.380(7) . ? C20 C21 1.388(7) . ? C8 C13 1.410(7) . ? C13 C12 1.385(7) . ? C13 C17 1.536(7) . ? C26 C27 1.385(8) . ? C15 C14 1.528(8) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C12 C11 1.381(8) . ? C12 H12 0.9300 . ? C21 H21 0.9300 . ? C23 C24 1.385(9) . ? C23 H23 0.9299 . ? C28 C29 1.374(10) . ? C28 C27 1.381(8) . ? C28 H28 0.9300 . ? C11 C10 1.390(8) . ? C11 H11 0.9300 . ? C24 C25 1.391(8) . ? C24 H24 0.9300 . ? C14 C16 1.522(8) . ? C14 H14 0.9799 . ? C5 C4 1.375(8) . ? C5 H5 0.9300 . ? C18 C17 1.522(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9601 . ? C18 H18C 0.9600 . ? C17 C19 1.540(8) . ? C17 H17 0.9800 . ? C30 C29 1.374(9) . ? C30 H30 0.9300 . ? C25 H25 0.9301 . ? C29 H29 0.9299 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9601 . ? Cl6 C33 1.733(10) . ? Cl5 C33 1.746(9) . ? C10 H10 0.9300 . ? C4 H4 0.9300 . ? C19 H19A 0.9601 . ? C19 H19B 0.9601 . ? C19 H19C 0.9600 . ? C27 H27 0.9300 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? 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 C20 148.73(19) . . ? C1 Bi1 C26 105.93(19) . . ? C20 Bi1 C26 104.98(18) . . ? C1 Bi1 Cl1 88.99(13) . . ? C20 Bi1 Cl1 94.80(13) . . ? C26 Bi1 Cl1 91.58(13) . . ? C1 Bi1 Cl2 84.11(13) . . ? C20 Bi1 Cl2 90.26(13) . . ? C26 Bi1 Cl2 91.92(13) . . ? Cl1 Bi1 Cl2 172.90(4) . . ? C1 Bi1 N1 68.48(17) . . ? C20 Bi1 N1 81.77(15) . . ? C26 Bi1 N1 169.02(16) . . ? Cl1 Bi1 N1 79.09(9) . . ? Cl2 Bi1 N1 96.76(9) . . ? C7 N1 C8 121.9(4) . . ? C7 N1 Bi1 106.2(3) . . ? C8 N1 Bi1 131.9(3) . . ? C23 C22 C21 120.9(6) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.4 . . ? C26 C31 C30 118.9(6) . . ? C26 C31 H31 120.6 . . ? C30 C31 H31 120.5 . . ? C2 C1 C6 122.4(5) . . ? C2 C1 Bi1 121.5(4) . . ? C6 C1 Bi1 116.0(4) . . ? N1 C7 C2 120.6(4) . . ? N1 C7 H7 119.9 . . ? C2 C7 H7 119.5 . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 119.8 . . ? C1 C6 C5 118.9(5) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.6 . . ? C10 C9 C8 118.5(5) . . ? C10 C9 C14 121.8(5) . . ? C8 C9 C14 119.6(4) . . ? Cl4 C32 Cl3 112.8(5) . . ? Cl4 C32 H32A 108.8 . . ? Cl3 C32 H32A 109.0 . . ? Cl4 C32 H32B 109.1 . . ? Cl3 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C25 C20 C21 123.1(5) . . ? C25 C20 Bi1 119.2(4) . . ? C21 C20 Bi1 117.4(4) . . ? C9 C8 C13 121.6(5) . . ? C9 C8 N1 118.4(4) . . ? C13 C8 N1 119.8(4) . . ? C12 C13 C8 117.5(5) . . ? C12 C13 C17 120.1(5) . . ? C8 C13 C17 122.4(4) . . ? C27 C26 C31 120.5(5) . . ? C27 C26 Bi1 120.5(4) . . ? C31 C26 Bi1 118.9(4) . . ? C14 C15 H15A 109.6 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C12 C13 122.1(5) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 118.7 . . ? C22 C21 C20 117.6(5) . . ? C22 C21 H21 121.3 . . ? C20 C21 H21 121.1 . . ? C1 C2 C3 118.1(5) . . ? C1 C2 C7 123.0(4) . . ? C3 C2 C7 118.9(4) . . ? C22 C23 C24 120.1(5) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 120.1 . . ? C29 C28 C27 120.7(6) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.7 . . ? C12 C11 C10 119.2(5) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.7 . . ? C23 C24 C25 120.9(5) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.3 . . ? C9 C14 C16 113.6(5) . . ? C9 C14 C15 110.9(4) . . ? C16 C14 C15 109.8(5) . . ? C9 C14 H14 107.1 . . ? C16 C14 H14 107.8 . . ? C15 C14 H14 107.3 . . ? C4 C5 C6 120.3(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 119.7 . . ? C17 C18 H18A 109.2 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.8 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C18 C17 C13 110.6(4) . . ? C18 C17 C19 110.9(5) . . ? C13 C17 C19 111.1(5) . . ? C18 C17 H17 108.1 . . ? C13 C17 H17 107.9 . . ? C19 C17 H17 108.0 . . ? C29 C30 C31 120.6(6) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.9 . . ? C20 C25 C24 117.3(5) . . ? C20 C25 H25 121.1 . . ? C24 C25 H25 121.6 . . ? C30 C29 C28 119.8(5) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 119.9 . . ? C14 C16 H16A 110.1 . . ? C14 C16 H16B 109.4 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 108.9 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C10 C11 121.1(5) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.4 . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 119.6 . . ? C17 C19 H19A 109.7 . . ? C17 C19 H19B 109.1 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.6 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C28 C27 C26 119.4(6) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.5 . . ? Cl6 C33 Cl5 112.8(5) . . ? Cl6 C33 H33A 110.1 . . ? Cl5 C33 H33A 110.3 . . ? Cl6 C33 H33B 107.6 . . ? Cl5 C33 H33B 108.1 . . ? H33A C33 H33B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.516 _refine_diff_density_min -3.508 _refine_diff_density_rms 0.178 _database_code_depnum_ccdc_archive 'CCDC 943199' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H32 Bi N' _chemical_formula_sum 'C31 H32 Bi N' _chemical_formula_weight 627.56 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9641(12) _cell_length_b 11.3640(5) _cell_length_c 16.8440(7) _cell_angle_alpha 90 _cell_angle_beta 111.475(5) _cell_angle_gamma 90 _cell_volume 2665.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 19396 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 6.632 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 1 0.093 0 1 0 0.095 0 0 -1 0.097 0 0 1 0.051 -1 1 0 0.061 1 0 0 0.071 -1 0 0 0.094 1 -1 -1 0.055 1 1 -1 0.094 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.334 _exptl_absorpt_correction_T_max 0.507 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19322 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6037 _reflns_number_gt 4611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0254P)^2^+13.3446P] 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 6037 _refine_ls_number_parameters 317 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_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_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 0.732996(16) -0.06434(2) 0.681814(14) 0.02745(8) Uani 1 1 d . B . C20 C 0.5942(5) -0.0160(6) 0.6998(4) 0.0313(14) Uani 1 1 d . . . N1 N 0.8748(4) -0.0846(5) 0.6035(3) 0.0283(11) Uani 1 1 d . B . C15 C 0.8238(5) -0.3899(8) 0.4494(6) 0.051(2) Uani 1 1 d . B . H15A H 0.8615 -0.4156 0.4172 0.061 Uiso 1 1 d R . . H15B H 0.7569 -0.3951 0.4146 0.061 Uiso 1 1 d R . . H15C H 0.8372 -0.4391 0.4988 0.061 Uiso 1 1 d R . . C17 C 1.0433(5) -0.0643(7) 0.7577(5) 0.0461(18) Uani 1 1 d D . . H17 H 0.9949 -0.0034 0.7320 0.055 Uiso 1 1 calc R A 1 C2 C 0.7934(5) 0.0980(6) 0.5528(4) 0.0313(14) Uani 1 1 d . B . C26 C 0.6623(4) -0.1989(6) 0.5826(4) 0.0306(14) Uani 1 1 d . . . C31 C 0.6203(4) -0.1754(7) 0.4958(4) 0.0343(15) Uani 1 1 d . . . H31 H 0.6180 -0.0984 0.4765 0.041 Uiso 1 1 d R . . C9 C 0.9425(4) -0.2518(6) 0.5546(4) 0.0297(14) Uani 1 1 d . B . C8 C 0.9532(4) -0.1630(6) 0.6148(4) 0.0298(14) Uani 1 1 d . . . C7 C 0.8714(4) 0.0133(6) 0.5666(4) 0.0311(14) Uani 1 1 d . . . H7 H 0.9207 0.0325 0.5478 0.037 Uiso 1 1 d R B . C5 C 0.6459(5) 0.2625(6) 0.5182(5) 0.0398(17) Uani 1 1 d . . . H5 H 0.5956 0.3159 0.5055 0.048 Uiso 1 1 d R . . C1 C 0.7230(4) 0.0842(5) 0.5895(4) 0.0296(14) Uani 1 1 d . . . C11 C 1.1012(5) -0.3205(7) 0.6403(5) 0.0414(17) Uani 1 1 d . B . H11 H 1.1518 -0.3725 0.6483 0.050 Uiso 1 1 d R . . C10 C 1.0181(5) -0.3294(7) 0.5687(5) 0.0394(16) Uani 1 1 d . . . H10 H 1.0132 -0.3887 0.5292 0.047 Uiso 1 1 d R B . C4 C 0.7163(5) 0.2774(6) 0.4840(5) 0.0426(18) Uani 1 1 d . B . H4 H 0.7147 0.3420 0.4496 0.051 Uiso 1 1 d R . . C6 C 0.6509(5) 0.1677(6) 0.5716(5) 0.0351(15) Uani 1 1 d . B . H6 H 0.6044 0.1600 0.5959 0.042 Uiso 1 1 d R . . C30 C 0.5823(5) -0.2649(8) 0.4379(5) 0.049(2) Uani 1 1 d . . . H30 H 0.5544 -0.2480 0.3800 0.059 Uiso 1 1 d R . . C27 C 0.6642(5) -0.3148(6) 0.6086(5) 0.0406(16) Uani 1 1 d . . . H27 H 0.6918 -0.3332 0.6663 0.049 Uiso 1 1 d R . . C14 C 0.8493(5) -0.2635(7) 0.4780(5) 0.0386(16) Uani 1 1 d . . . H14 H 0.7980 -0.2334 0.4955 0.046 Uiso 1 1 d R B . C13 C 1.0363(5) -0.1535(6) 0.6891(4) 0.0354(15) Uani 1 1 d . B . C3 C 0.7896(5) 0.1950(6) 0.5019(5) 0.0391(16) Uani 1 1 d . . . H3 H 0.8371 0.2050 0.4791 0.047 Uiso 1 1 d R B . C29 C 0.5858(6) -0.3802(8) 0.4663(6) 0.053(2) Uani 1 1 d . . . H29 H 0.5598 -0.4407 0.4275 0.063 Uiso 1 1 d R . . C16 C 0.8502(6) -0.1870(8) 0.4042(5) 0.056(2) Uani 1 1 d . B . H16A H 0.8623 -0.1068 0.4229 0.067 Uiso 1 1 d R . . H16B H 0.7892 -0.1922 0.3581 0.067 Uiso 1 1 d R . . H16C H 0.8998 -0.2138 0.3853 0.067 Uiso 1 1 d R . . C25 C 0.5096(5) -0.0769(6) 0.6607(5) 0.0373(16) Uani 1 1 d . . . H25 H 0.5071 -0.1347 0.6209 0.045 Uiso 1 1 d R . . C12 C 1.1089(5) -0.2351(7) 0.7001(5) 0.0442(18) Uani 1 1 d . . . H12 H 1.1639 -0.2326 0.7492 0.053 Uiso 1 1 d R B . C28 C 0.6257(7) -0.4043(7) 0.5510(7) 0.058(2) Uani 1 1 d . . . H28 H 0.6282 -0.4816 0.5699 0.069 Uiso 1 1 d R . . C21 C 0.5942(5) 0.0712(7) 0.7579(5) 0.0398(16) Uani 1 1 d . . . H21 H 0.6501 0.1139 0.7851 0.048 Uiso 1 1 d R . . C24 C 0.4281(5) -0.0536(7) 0.6796(5) 0.0435(18) Uani 1 1 d . . . H24 H 0.3722 -0.0966 0.6532 0.052 Uiso 1 1 d R . . C22 C 0.5135(6) 0.0952(7) 0.7762(5) 0.0469(19) Uani 1 1 d . . . H22 H 0.5155 0.1542 0.8151 0.056 Uiso 1 1 d R . . C23 C 0.4309(6) 0.0333(7) 0.7377(5) 0.0465(19) Uani 1 1 d . . . H23 H 0.3769 0.0497 0.7507 0.056 Uiso 1 1 d R . . C18 C 1.0220(15) -0.1169(18) 0.8258(15) 0.050(5) Uani 0.64(4) 1 d P B 1 H18A H 1.0261 -0.0583 0.8681 0.074 Uiso 0.64(4) 1 calc PR B 1 H18B H 1.0673 -0.1786 0.8511 0.074 Uiso 0.64(4) 1 calc PR B 1 H18C H 0.9582 -0.1490 0.8039 0.074 Uiso 0.64(4) 1 calc PR B 1 C19 C 1.1469(15) -0.002(2) 0.7910(12) 0.059(6) Uani 0.64(4) 1 d P B 1 H19A H 1.1582 0.0331 0.7436 0.089 Uiso 0.64(4) 1 calc PR B 1 H19B H 1.1957 -0.0592 0.8176 0.089 Uiso 0.64(4) 1 calc PR B 1 H19C H 1.1486 0.0583 0.8316 0.089 Uiso 0.64(4) 1 calc PR B 1 C19A C 1.092(5) 0.046(3) 0.757(3) 0.084(16) Uani 0.36(4) 1 d PD B 2 H19D H 1.0907 0.0954 0.8029 0.126 Uiso 0.36(4) 1 calc PR B 2 H19E H 1.0603 0.0860 0.7036 0.126 Uiso 0.36(4) 1 calc PR B 2 H19F H 1.1576 0.0310 0.7637 0.126 Uiso 0.36(4) 1 calc PR B 2 C18A C 1.072(4) -0.118(3) 0.8476(15) 0.061(11) Uani 0.36(4) 1 d PD B 2 H18D H 1.0388 -0.1912 0.8442 0.092 Uiso 0.36(4) 1 calc PR B 2 H18E H 1.0549 -0.0645 0.8839 0.092 Uiso 0.36(4) 1 calc PR B 2 H18F H 1.1400 -0.1314 0.8706 0.092 Uiso 0.36(4) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02888(13) 0.02832(13) 0.02121(12) 0.00174(11) 0.00451(8) 0.00088(11) C20 0.035(3) 0.036(3) 0.023(3) -0.001(3) 0.011(3) 0.005(3) N1 0.027(3) 0.032(3) 0.023(3) 0.002(2) 0.005(2) 0.001(2) C15 0.038(4) 0.064(5) 0.046(5) -0.020(4) 0.011(4) 0.008(4) C17 0.047(4) 0.046(4) 0.028(4) 0.001(4) -0.006(3) 0.004(4) C2 0.033(3) 0.027(3) 0.028(3) -0.003(3) 0.005(3) -0.005(3) C26 0.032(3) 0.025(3) 0.040(4) 0.003(3) 0.020(3) 0.003(3) C31 0.030(3) 0.039(4) 0.026(3) -0.003(3) 0.002(3) -0.002(3) C9 0.028(3) 0.038(4) 0.022(3) 0.002(3) 0.008(3) 0.004(3) C8 0.025(3) 0.036(4) 0.026(3) 0.006(3) 0.007(2) 0.003(3) C7 0.027(3) 0.037(4) 0.026(3) 0.003(3) 0.005(3) -0.004(3) C5 0.040(4) 0.022(3) 0.047(4) -0.001(3) 0.004(3) 0.005(3) C1 0.030(3) 0.026(3) 0.028(3) -0.005(3) 0.005(3) -0.004(3) C11 0.031(3) 0.046(4) 0.046(4) 0.011(4) 0.012(3) 0.008(3) C10 0.035(4) 0.048(4) 0.037(4) 0.002(4) 0.016(3) 0.004(3) C4 0.051(4) 0.026(3) 0.039(4) 0.014(3) 0.004(3) -0.003(3) C6 0.031(3) 0.032(4) 0.038(4) -0.007(3) 0.007(3) -0.007(3) C30 0.032(4) 0.069(6) 0.043(5) -0.011(4) 0.009(3) 0.000(4) C27 0.045(4) 0.028(3) 0.050(4) -0.001(4) 0.019(3) -0.004(3) C14 0.031(3) 0.051(4) 0.030(4) -0.008(3) 0.006(3) 0.007(3) C13 0.031(3) 0.039(4) 0.028(3) 0.003(3) 0.001(3) -0.001(3) C3 0.041(4) 0.037(4) 0.037(4) 0.003(3) 0.010(3) -0.009(3) C29 0.049(5) 0.044(5) 0.062(6) -0.025(4) 0.016(4) -0.007(4) C16 0.067(5) 0.060(5) 0.028(4) -0.001(4) 0.003(4) 0.017(5) C25 0.037(3) 0.041(4) 0.034(4) -0.004(3) 0.013(3) 0.004(3) C12 0.032(4) 0.052(5) 0.040(4) 0.010(4) 0.003(3) 0.000(3) C28 0.071(6) 0.025(4) 0.076(7) -0.004(4) 0.026(5) -0.002(4) C21 0.048(4) 0.043(4) 0.029(3) -0.006(3) 0.014(3) -0.004(4) C24 0.036(4) 0.051(5) 0.043(4) -0.003(4) 0.014(3) 0.002(3) C22 0.061(5) 0.044(4) 0.037(4) -0.011(4) 0.018(4) 0.009(4) C23 0.044(4) 0.057(5) 0.042(4) 0.001(4) 0.021(4) 0.015(4) C18 0.041(9) 0.066(10) 0.045(10) -0.001(8) 0.019(8) 0.001(9) C19 0.070(11) 0.058(12) 0.041(9) -0.012(8) 0.009(8) -0.039(9) C19A 0.14(4) 0.052(19) 0.09(3) 0.001(19) 0.07(3) -0.01(2) C18A 0.09(3) 0.073(19) 0.022(13) 0.009(13) 0.016(16) 0.01(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 C26 2.226(7) . ? Bi1 C1 2.263(7) . ? Bi1 C20 2.274(6) . ? C20 C25 1.380(10) . ? C20 C21 1.393(9) . ? N1 C7 1.267(8) . ? N1 C8 1.430(8) . ? C15 C14 1.518(11) . ? C15 H15A 0.9600 . ? C15 H15B 0.9599 . ? C15 H15C 0.9600 . ? C17 C18 1.43(2) . ? C17 C19A 1.458(17) . ? C17 C13 1.511(10) . ? C17 C18A 1.540(16) . ? C17 C19 1.608(16) . ? C17 H17 0.9800 . ? C2 C3 1.386(10) . ? C2 C1 1.411(9) . ? C2 C7 1.464(9) . ? C26 C27 1.385(9) . ? C26 C31 1.389(9) . ? C31 C30 1.379(11) . ? C31 H31 0.9300 . ? C9 C10 1.385(9) . ? C9 C8 1.398(9) . ? C9 C14 1.520(9) . ? C8 C13 1.408(9) . ? C7 H7 0.9300 . ? C5 C4 1.384(11) . ? C5 C6 1.388(10) . ? C5 H5 0.9300 . ? C1 C6 1.386(9) . ? C11 C12 1.372(11) . ? C11 C10 1.383(10) . ? C11 H11 0.9299 . ? C10 H10 0.9299 . ? C4 C3 1.389(10) . ? C4 H4 0.9301 . ? C6 H6 0.9300 . ? C30 C29 1.389(12) . ? C30 H30 0.9301 . ? C27 C28 1.378(12) . ? C27 H27 0.9299 . ? C14 C16 1.520(11) . ? C14 H14 0.9802 . ? C13 C12 1.389(10) . ? C3 H3 0.9300 . ? C29 C28 1.356(13) . ? C29 H29 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9601 . ? C16 H16C 0.9601 . ? C25 C24 1.393(9) . ? C25 H25 0.9301 . ? C12 H12 0.9300 . ? C28 H28 0.9300 . ? C21 C22 1.378(10) . ? C21 H21 0.9300 . ? C24 C23 1.380(11) . ? C24 H24 0.9300 . ? C22 C23 1.363(12) . ? C22 H22 0.9298 . ? C23 H23 0.9301 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C19A H19D 0.9600 . ? C19A H19E 0.9600 . ? C19A H19F 0.9600 . ? C18A H18D 0.9600 . ? C18A H18E 0.9600 . ? C18A H18F 0.9600 . ? 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 C26 Bi1 C1 95.9(2) . . ? C26 Bi1 C20 93.4(2) . . ? C1 Bi1 C20 94.5(2) . . ? C25 C20 C21 117.1(6) . . ? C25 C20 Bi1 122.6(5) . . ? C21 C20 Bi1 120.0(5) . . ? C7 N1 C8 119.7(5) . . ? C14 C15 H15A 109.6 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.1 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C17 C19A 128.9(17) . . ? C18 C17 C13 111.1(10) . . ? C19A C17 C13 117.8(14) . . ? C18 C17 C18A 27.0(16) . . ? C19A C17 C18A 113.0(15) . . ? C13 C17 C18A 113.8(14) . . ? C18 C17 C19 112.0(10) . . ? C19A C17 C19 37(2) . . ? C13 C17 C19 110.6(9) . . ? C18A C17 C19 86.9(19) . . ? C18 C17 H17 107.7 . . ? C19A C17 H17 71.2 . . ? C13 C17 H17 107.7 . . ? C18A C17 H17 127.4 . . ? C19 C17 H17 107.6 . . ? C3 C2 C1 119.5(6) . . ? C3 C2 C7 118.0(6) . . ? C1 C2 C7 122.5(6) . . ? C27 C26 C31 117.7(7) . . ? C27 C26 Bi1 117.8(5) . . ? C31 C26 Bi1 124.5(5) . . ? C30 C31 C26 120.9(7) . . ? C30 C31 H31 119.6 . . ? C26 C31 H31 119.6 . . ? C10 C9 C8 117.8(6) . . ? C10 C9 C14 121.8(6) . . ? C8 C9 C14 120.4(6) . . ? C9 C8 C13 122.0(6) . . ? C9 C8 N1 118.8(6) . . ? C13 C8 N1 119.0(6) . . ? N1 C7 C2 122.7(6) . . ? N1 C7 H7 118.7 . . ? C2 C7 H7 118.6 . . ? C4 C5 C6 119.8(6) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.1 . . ? C6 C1 C2 118.4(6) . . ? C6 C1 Bi1 120.7(5) . . ? C2 C1 Bi1 120.8(5) . . ? C12 C11 C10 120.0(7) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 120.2 . . ? C11 C10 C9 121.3(7) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.6 . . ? C5 C4 C3 119.2(6) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.4 . . ? C5 C6 C1 121.6(7) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.3 . . ? C31 C30 C29 119.9(8) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.1 . . ? C28 C27 C26 121.6(8) . . ? C28 C27 H27 118.8 . . ? C26 C27 H27 119.6 . . ? C16 C14 C9 111.4(6) . . ? C16 C14 C15 111.0(7) . . ? C9 C14 C15 113.4(6) . . ? C16 C14 H14 106.8 . . ? C9 C14 H14 106.8 . . ? C15 C14 H14 107.0 . . ? C12 C13 C8 117.4(7) . . ? C12 C13 C17 121.0(6) . . ? C8 C13 C17 121.5(6) . . ? C2 C3 C4 121.4(7) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C28 C29 C30 120.0(8) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 120.1 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.7 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.2 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C20 C25 C24 121.5(7) . . ? C20 C25 H25 119.1 . . ? C24 C25 H25 119.4 . . ? C11 C12 C13 121.5(7) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.5 . . ? C29 C28 C27 120.0(8) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 120.1 . . ? C22 C21 C20 121.5(7) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.1 . . ? C23 C24 C25 119.8(7) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.0 . . ? C23 C22 C21 120.6(7) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 119.5(7) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.4 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C19A H19D 109.5 . . ? C17 C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C17 C19A H19F 109.4 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C17 C18A H18D 109.4 . . ? C17 C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17 C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.653 _refine_diff_density_min -2.394 _refine_diff_density_rms 0.170 _database_code_depnum_ccdc_archive 'CCDC 943200' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 Cl N Sb' _chemical_formula_sum 'C25 H27 Cl N Sb' _chemical_formula_weight 498.68 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.2619(7) _cell_length_b 13.9830(8) _cell_length_c 14.3511(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2259.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 21059 _cell_measurement_theta_min 1 _cell_measurement_theta_max 30.5 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 1.349 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 1 0.136 0 1 -1 0.094 -1 0 0 0.066 1 1 1 0.115 1 -1 -1 0.060 0 -1 -1 0.093 0 1 1 0.167 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.726 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21034 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.50 _reflns_number_total 6823 _reflns_number_gt 5959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0096P)^2^+1.8583P] 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 -0.026(18) _refine_ls_number_reflns 6823 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0585 _refine_ls_wR_factor_gt 0.0518 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 1.034062(13) 0.999865(15) 0.973484(9) 0.01759(4) Uani 1 1 d . . . Cl1 Cl 1.04403(7) 0.85716(5) 0.86708(4) 0.02618(13) Uani 1 1 d . . . N1 N 1.05831(19) 1.11204(15) 1.10165(14) 0.0178(4) Uani 1 1 d . . . C2 C 1.2276(2) 1.0143(2) 1.12166(17) 0.0205(6) Uani 1 1 d . . . C9 C 0.9888(2) 1.27002(18) 1.05705(17) 0.0211(5) Uani 1 1 d . . . C7 C 1.1543(2) 1.09705(18) 1.14610(18) 0.0203(5) Uani 1 1 d . . . H7 H 1.1778 1.1381 1.1936 0.024 Uiso 1 1 d R . . C14 C 1.0768(3) 1.27306(18) 0.97658(19) 0.0250(6) Uani 1 1 d . . . H14 H 1.1183 1.2115 0.9749 0.030 Uiso 1 1 d R . . C20 C 0.9142(2) 0.92492(18) 1.06384(16) 0.0181(5) Uani 1 1 d . . . C21 C 0.9482(3) 0.89213(19) 1.15183(19) 0.0249(6) Uani 1 1 d . . . H21 H 1.0254 0.9017 1.1727 0.030 Uiso 1 1 d R . . C12 C 0.8343(3) 1.2727(2) 1.20904(19) 0.0253(6) Uani 1 1 d . . . H12 H 0.7834 1.2748 1.2600 0.030 Uiso 1 1 d R . . C22 C 0.8671(3) 0.8455(2) 1.2086(2) 0.0291(7) Uani 1 1 d . . . H22 H 0.8901 0.8242 1.2672 0.035 Uiso 1 1 d R . . C25 C 0.7985(3) 0.9098(2) 1.0348(2) 0.0255(6) Uani 1 1 d . . . H25 H 0.7743 0.9326 0.9770 0.031 Uiso 1 1 d R . . C5 C 1.3625(3) 0.8567(2) 1.0753(2) 0.0301(6) Uani 1 1 d . . . H5 H 1.4076 0.8032 1.0599 0.036 Uiso 1 1 d R . . C1 C 1.1934(2) 0.95789(19) 1.04539(17) 0.0196(5) Uani 1 1 d . . . C10 C 0.9131(3) 1.3474(2) 1.07264(19) 0.0266(6) Uani 1 1 d . . . H10 H 0.9148 1.3994 1.0322 0.032 Uiso 1 1 d R . . C6 C 1.2628(2) 0.87902(19) 1.0229(2) 0.0252(5) Uani 1 1 d . . . H6 H 1.2420 0.8408 0.9724 0.030 Uiso 1 1 d R . . C17 C 0.9000(3) 1.1096(2) 1.26482(18) 0.0256(6) Uani 1 1 d . . . H17 H 0.9486 1.0574 1.2399 0.031 Uiso 1 1 d R . . C18 C 0.7732(3) 1.0724(2) 1.2748(2) 0.0335(7) Uani 1 1 d . . . H18A H 0.7415 1.0578 1.2143 0.040 Uiso 1 1 d R . . H18B H 0.7728 1.0158 1.3126 0.040 Uiso 1 1 d R . . H18C H 0.7253 1.1207 1.3038 0.040 Uiso 1 1 d R . . C23 C 0.7515(3) 0.8303(2) 1.1783(2) 0.0279(6) Uani 1 1 d . . . H23 H 0.6972 0.7992 1.2166 0.033 Uiso 1 1 d R . . C24 C 0.7182(3) 0.8616(2) 1.0912(2) 0.0291(6) Uani 1 1 d . . . H24 H 0.6415 0.8502 1.0700 0.035 Uiso 1 1 d R . . C11 C 0.8367(3) 1.3485(2) 1.1477(2) 0.0278(6) Uani 1 1 d . . . H11 H 0.7862 1.4003 1.1568 0.033 Uiso 1 1 d R . . C13 C 0.9063(3) 1.1928(2) 1.19646(18) 0.0217(5) Uani 1 1 d . . . C8 C 0.9838(2) 1.19344(17) 1.11998(17) 0.0178(5) Uani 1 1 d . . . C3 C 1.3289(2) 0.9933(3) 1.17343(17) 0.0255(5) Uani 1 1 d . . . H3 H 1.3510 1.0319 1.2232 0.031 Uiso 1 1 d R . . C19 C 0.9509(3) 1.1374(2) 1.3601(2) 0.0377(7) Uani 1 1 d . . . H19A H 0.9078 1.1913 1.3841 0.045 Uiso 1 1 d R . . H19B H 0.9436 1.0846 1.4025 0.045 Uiso 1 1 d R . . H19C H 1.0331 1.1541 1.3533 0.045 Uiso 1 1 d R . . C4 C 1.3961(3) 0.9137(2) 1.1505(2) 0.0301(6) Uani 1 1 d . . . H4 H 1.4635 0.8985 1.1848 0.036 Uiso 1 1 d R . . C15 C 1.0163(4) 1.2866(3) 0.8831(2) 0.0511(11) Uani 1 1 d . . . H15A H 0.9770 1.3475 0.8822 0.061 Uiso 1 1 d R . . H15B H 1.0746 1.2844 0.8344 0.061 Uiso 1 1 d R . . H15C H 0.9590 1.2367 0.8736 0.061 Uiso 1 1 d R . . C16 C 1.1707(4) 1.3497(3) 0.9942(3) 0.0553(11) Uani 1 1 d . . . H16A H 1.2100 1.3381 1.0524 0.066 Uiso 1 1 d R . . H16B H 1.2279 1.3491 0.9446 0.066 Uiso 1 1 d R . . H16C H 1.1322 1.4110 0.9962 0.066 Uiso 1 1 d 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 Sb1 0.01882(7) 0.01792(6) 0.01605(6) 0.00098(9) -0.00052(6) 0.00062(11) Cl1 0.0312(3) 0.0245(3) 0.0227(3) -0.0058(2) 0.0011(3) -0.0013(3) N1 0.0186(11) 0.0178(9) 0.0170(9) -0.0011(7) 0.0035(8) 0.0012(8) C2 0.0155(10) 0.0239(17) 0.0221(10) 0.0020(10) 0.0022(9) -0.0029(11) C9 0.0241(14) 0.0203(12) 0.0188(11) -0.0009(9) -0.0004(10) 0.0014(10) C7 0.0222(13) 0.0220(12) 0.0168(11) -0.0014(9) 0.0014(10) -0.0013(10) C14 0.0338(15) 0.0203(12) 0.0209(11) 0.0024(10) 0.0071(12) 0.0031(11) C20 0.0181(12) 0.0199(11) 0.0161(10) 0.0001(9) -0.0003(9) 0.0016(10) C21 0.0220(15) 0.0261(13) 0.0265(12) 0.0059(10) -0.0042(12) -0.0008(11) C12 0.0213(14) 0.0342(16) 0.0204(12) -0.0071(11) 0.0038(11) 0.0037(12) C22 0.0329(17) 0.0284(16) 0.0260(14) 0.0101(12) 0.0022(13) -0.0005(13) C25 0.0207(13) 0.0343(15) 0.0214(12) -0.0016(11) -0.0022(12) 0.0013(11) C5 0.0227(14) 0.0294(15) 0.0382(16) 0.0027(13) 0.0061(13) 0.0068(12) C1 0.0157(12) 0.0208(12) 0.0222(12) 0.0008(9) 0.0023(10) -0.0014(10) C10 0.0311(15) 0.0236(13) 0.0250(13) 0.0013(11) -0.0028(12) 0.0061(12) C6 0.0204(13) 0.0247(13) 0.0304(13) 0.0003(12) 0.0053(13) 0.0003(10) C17 0.0274(15) 0.0281(14) 0.0212(12) 0.0014(10) 0.0055(12) 0.0025(12) C18 0.0361(18) 0.0372(17) 0.0271(14) 0.0016(13) 0.0051(14) -0.0061(15) C23 0.0269(15) 0.0260(14) 0.0308(15) -0.0007(12) 0.0050(13) -0.0027(12) C24 0.0199(14) 0.0364(16) 0.0308(14) -0.0052(13) 0.0001(12) -0.0044(12) C11 0.0269(15) 0.0274(14) 0.0290(14) -0.0081(11) -0.0037(12) 0.0095(12) C13 0.0238(14) 0.0242(13) 0.0171(11) -0.0025(10) -0.0014(11) -0.0001(12) C8 0.0186(13) 0.0178(11) 0.0171(10) -0.0022(9) -0.0015(10) 0.0009(9) C3 0.0188(11) 0.0327(14) 0.0250(11) 0.0038(15) -0.0009(9) -0.0044(16) C19 0.0395(19) 0.0477(18) 0.0259(13) 0.0085(13) -0.0048(14) -0.0098(16) C4 0.0164(13) 0.0396(16) 0.0342(15) 0.0090(13) 0.0000(12) 0.0046(12) C15 0.052(2) 0.080(3) 0.0221(14) 0.0095(16) 0.0033(16) 0.024(2) C16 0.056(2) 0.055(2) 0.055(2) -0.0206(19) 0.031(2) -0.027(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 Sb1 C20 2.145(3) . ? Sb1 C1 2.152(3) . ? Sb1 N1 2.433(2) . ? Sb1 Cl1 2.5151(7) . ? N1 C7 1.273(3) . ? N1 C8 1.438(3) . ? C2 C3 1.393(4) . ? C2 C1 1.403(4) . ? C2 C7 1.463(4) . ? C9 C10 1.396(4) . ? C9 C8 1.402(3) . ? C9 C14 1.522(4) . ? C7 H7 0.9300 . ? C14 C15 1.516(4) . ? C14 C16 1.527(5) . ? C14 H14 0.9800 . ? C20 C25 1.384(4) . ? C20 C21 1.397(3) . ? C21 C22 1.386(4) . ? C21 H21 0.9299 . ? C12 C11 1.378(4) . ? C12 C13 1.392(4) . ? C12 H12 0.9299 . ? C22 C23 1.388(4) . ? C22 H22 0.9299 . ? C25 C24 1.388(4) . ? C25 H25 0.9300 . ? C5 C6 1.387(4) . ? C5 C4 1.393(4) . ? C5 H5 0.9300 . ? C1 C6 1.390(4) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C6 H6 0.9300 . ? C17 C13 1.523(4) . ? C17 C18 1.527(4) . ? C17 C19 1.533(4) . ? C17 H17 0.9800 . ? C18 H18A 0.9599 . ? C18 H18B 0.9600 . ? C18 H18C 0.9599 . ? C23 C24 1.377(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C11 H11 0.9300 . ? C13 C8 1.403(4) . ? C3 C4 1.386(5) . ? C3 H3 0.9300 . ? C19 H19A 0.9599 . ? C19 H19B 0.9601 . ? C19 H19C 0.9600 . ? C4 H4 0.9301 . ? C15 H15A 0.9599 . ? C15 H15B 0.9599 . ? C15 H15C 0.9600 . ? C16 H16A 0.9599 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C20 Sb1 C1 95.84(10) . . ? C20 Sb1 N1 85.91(8) . . ? C1 Sb1 N1 73.72(9) . . ? C20 Sb1 Cl1 90.43(7) . . ? C1 Sb1 Cl1 92.15(7) . . ? N1 Sb1 Cl1 164.92(5) . . ? C7 N1 C8 122.3(2) . . ? C7 N1 Sb1 111.60(17) . . ? C8 N1 Sb1 125.66(16) . . ? C3 C2 C1 121.5(3) . . ? C3 C2 C7 120.1(3) . . ? C1 C2 C7 118.5(2) . . ? C10 C9 C8 117.7(2) . . ? C10 C9 C14 119.8(2) . . ? C8 C9 C14 122.4(2) . . ? N1 C7 C2 119.3(2) . . ? N1 C7 H7 120.5 . . ? C2 C7 H7 120.2 . . ? C15 C14 C9 112.4(3) . . ? C15 C14 C16 111.7(3) . . ? C9 C14 C16 110.2(2) . . ? C15 C14 H14 107.6 . . ? C9 C14 H14 107.7 . . ? C16 C14 H14 106.9 . . ? C25 C20 C21 118.7(3) . . ? C25 C20 Sb1 119.01(19) . . ? C21 C20 Sb1 122.3(2) . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 120.0 . . ? C11 C12 C13 121.5(3) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.2 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.7 . . ? C20 C25 C24 120.8(3) . . ? C20 C25 H25 119.5 . . ? C24 C25 H25 119.7 . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.7 . . ? C6 C1 C2 118.2(3) . . ? C6 C1 Sb1 125.0(2) . . ? C2 C1 Sb1 116.71(19) . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.6 . . ? C5 C6 C1 120.5(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.6 . . ? C13 C17 C18 111.3(3) . . ? C13 C17 C19 111.3(2) . . ? C18 C17 C19 110.6(2) . . ? C13 C17 H17 107.9 . . ? C18 C17 H17 107.6 . . ? C19 C17 H17 107.8 . . ? C17 C18 H18A 109.6 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.0 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C23 C22 119.4(3) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 120.4(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C12 C13 C8 117.3(3) . . ? C12 C13 C17 120.2(3) . . ? C8 C13 C17 122.5(2) . . ? C9 C8 C13 122.3(2) . . ? C9 C8 N1 117.6(2) . . ? C13 C8 N1 120.1(2) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.5 . . ? C17 C19 H19A 109.3 . . ? C17 C19 H19B 109.8 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.4 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.1 . . ? C14 C15 H15A 109.3 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.7 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 110.2 . . ? C14 C16 H16B 109.6 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 108.6 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.502 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 943201'