data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Kochi, J.' 'Le Magueres, Pierre' 'Lindeman, Sergey V.' _publ_contact_author_name 'Dr J Kochi' _publ_contact_author_address ; Dr J Kochi Chemistry University of Houston Houston TX 77204-5641 USA ; _publ_contact_author_email 'JKOCHI@POP.UH.EDU' data_juer-fs _database_code_CSD 162663 _audit_creation_method SHELXL _chemical_name_systematic ; Hexamethylbenzene Chloranil Molecular Complex ; _chemical_name_common ? _chemical_formula_moiety '(C12 H18) (C6 O2 Cl4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H18 Cl4 O2' _chemical_formula_weight 408.12 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.0658(1) _cell_length_b 8.6430(1) _cell_length_c 14.8612(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.874(1) _cell_angle_gamma 90.00 _cell_volume 888.15(2) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6325 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 36.1 _exptl_crystal_description 'prism' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method none _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.674 _exptl_absorpt_correction_type 'empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.977 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number 360 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.00 _diffrn_reflns_number 10533 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 36.13 _reflns_number_total 3933 _reflns_number_observed 3116 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 12 with very negative F^2^ or flagged by us for potential systematic errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.2797P] 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 ; riding and rotating model with U~iso~=1.2U~eq/iso~ of an adjacent atom (1.5U~eq/iso~ for methyl hydrogens) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3921 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_obs 0.0368 _refine_ls_wR_factor_all 0.1039 _refine_ls_wR_factor_obs 0.0883 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.055 _refine_ls_restrained_S_all 1.105 _refine_ls_restrained_S_obs 1.055 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl4 Cl 0.94170(5) 0.33601(3) 0.07087(2) 0.03052(8) Uani 1 d . . Cl5 Cl 0.83464(5) 0.25922(4) -0.14376(2) 0.02901(8) Uani 1 d . . O6 O 0.91906(15) -0.06284(12) -0.18006(6) 0.0304(2) Uani 1 d . . C2 C 0.4353(2) 0.14562(12) -0.03693(7) 0.0194(2) Uani 1 d . . C5 C 0.9238(2) 0.12322(13) -0.06258(7) 0.0199(2) Uani 1 d . . C6 C 0.9545(2) -0.03441(13) -0.09811(7) 0.0209(2) Uani 1 d . . C4 C 0.9675(2) 0.15543(13) 0.02825(7) 0.0204(2) Uani 1 d . . C3 C 0.4889(2) 0.12588(12) 0.05904(7) 0.0196(2) Uani 1 d . . C1 C 0.4483(2) 0.02042(13) -0.09594(7) 0.0197(2) Uani 1 d . . C11 C 0.3981(2) 0.0424(2) -0.19946(8) 0.0332(3) Uani 1 d . . H11A H 0.4158(18) 0.1490(4) -0.21394(9) 0.050 Uiso 1 calc R . H11B H 0.2658(6) 0.0135(15) -0.22233(14) 0.050 Uiso 1 calc R . H11C H 0.4810(13) -0.0213(12) -0.22760(10) 0.050 Uiso 1 calc R . C21 C 0.3652(2) 0.3032(2) -0.07533(11) 0.0346(3) Uani 1 d . . H21A H 0.2772(15) 0.2902(2) -0.1333(5) 0.052 Uiso 1 calc R . H21B H 0.4737(3) 0.3642(6) -0.0838(9) 0.052 Uiso 1 calc R . H21C H 0.3003(17) 0.3548(7) -0.0331(4) 0.052 Uiso 1 calc R . C31 C 0.4858(2) 0.2604(2) 0.12447(10) 0.0333(3) Uani 1 d . . H31A H 0.5981(10) 0.2558(8) 0.1733(5) 0.050 Uiso 1 calc R . H31B H 0.3714(9) 0.2544(8) 0.1497(7) 0.050 Uiso 1 calc R . H31C H 0.4859(19) 0.3561(2) 0.0917(2) 0.050 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl4 0.0369(2) 0.02157(13) 0.0342(2) -0.00757(10) 0.00993(12) -0.00164(11) Cl5 0.03063(15) 0.02963(14) 0.02619(13) 0.01120(10) 0.00454(10) -0.00038(11) O6 0.0376(5) 0.0371(5) 0.0158(3) -0.0046(3) 0.0035(3) -0.0046(4) C2 0.0191(4) 0.0177(4) 0.0210(4) 0.0046(3) 0.0031(3) -0.0003(3) C5 0.0213(4) 0.0209(4) 0.0177(4) 0.0021(3) 0.0049(3) -0.0027(4) C6 0.0231(5) 0.0239(5) 0.0158(4) -0.0008(3) 0.0043(3) -0.0038(4) C4 0.0232(5) 0.0193(4) 0.0193(4) -0.0016(3) 0.0058(3) -0.0028(4) C3 0.0212(4) 0.0178(4) 0.0198(4) -0.0042(3) 0.0044(3) -0.0045(3) C1 0.0191(4) 0.0258(5) 0.0131(4) 0.0012(3) 0.0009(3) -0.0033(4) C11 0.0317(6) 0.0513(8) 0.0143(4) 0.0041(5) -0.0007(4) -0.0022(6) C21 0.0335(6) 0.0236(5) 0.0479(8) 0.0154(5) 0.0111(6) 0.0071(5) C31 0.0396(7) 0.0269(6) 0.0363(6) -0.0146(5) 0.0143(6) -0.0097(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl4 C4 1.7082(11) . ? Cl5 C5 1.7092(11) . ? O6 C6 1.2168(13) . ? C2 C1 1.408(2) . ? C2 C3 1.4087(15) . ? C2 C21 1.520(2) . ? C5 C4 1.3504(15) . ? C5 C6 1.493(2) . ? C6 C4 1.497(2) 3_755 ? C4 C6 1.497(2) 3_755 ? C3 C1 1.413(2) 3_655 ? C3 C31 1.519(2) . ? C1 C3 1.413(2) 3_655 ? C1 C11 1.5180(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 119.95(9) . . ? C1 C2 C21 120.86(11) . . ? C3 C2 C21 119.19(11) . . ? C4 C5 C6 121.45(10) . . ? C4 C5 Cl5 122.62(9) . . ? C6 C5 Cl5 115.92(8) . . ? O6 C6 C5 121.55(11) . . ? O6 C6 C4 121.58(11) . 3_755 ? C5 C6 C4 116.86(9) . 3_755 ? C5 C4 C6 121.68(10) . 3_755 ? C5 C4 Cl4 122.62(9) . . ? C6 C4 Cl4 115.68(8) 3_755 . ? C2 C3 C1 119.93(9) . 3_655 ? C2 C3 C31 121.27(11) . . ? C1 C3 C31 118.78(10) 3_655 . ? C2 C1 C3 120.10(9) . 3_655 ? C2 C1 C11 120.23(11) . . ? C3 C1 C11 119.66(11) 3_655 . ? _refine_diff_density_max 0.535 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.066 data_pier-xsx _database_code_CSD 138877 _audit_creation_method SHELXL _chemical_name_systematic ; Octamethylbiphenylene/Tetracyanoethylene molecular complex 1:1 ; _chemical_name_common ? _chemical_formula_moiety '(C20 H24), (C6 N4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H24 N4' _chemical_formula_weight 392.49 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.137(2) _cell_length_b 7.2320(10) _cell_length_c 17.680(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.526(3) _cell_angle_gamma 90.00 _cell_volume 2053.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4149 _cell_measurement_theta_min 2 _cell_measurement_theta_max 35 _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method none _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 0.966 _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number 214 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.9 _diffrn_reflns_number 23371 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 35.80 _reflns_number_total 8872 _reflns_number_observed 5608 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 40 with very negative F^2^ or flagged by us for potential systematic errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8832 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_obs 0.0426 _refine_ls_wR_factor_all 0.1234 _refine_ls_wR_factor_obs 0.1019 _refine_ls_goodness_of_fit_all 0.917 _refine_ls_goodness_of_fit_obs 1.070 _refine_ls_restrained_S_all 1.024 _refine_ls_restrained_S_obs 1.070 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.27890(4) 0.40471(10) 0.17326(4) 0.01191(13) Uani 1 d . . C2 C 0.32472(5) 0.32492(10) 0.23422(4) 0.01307(13) Uani 1 d . . C3 C 0.40178(5) 0.24348(10) 0.21737(4) 0.01376(13) Uani 1 d . . C4 C 0.42629(5) 0.24158(10) 0.14292(4) 0.01338(13) Uani 1 d . . C5 C 0.37666(5) 0.32440(10) 0.08033(4) 0.01289(13) Uani 1 d . . C6 C 0.30394(4) 0.40451(10) 0.09838(4) 0.01151(12) Uani 1 d . . C7 C 0.22584(4) 0.50939(10) 0.07052(4) 0.01192(13) Uani 1 d . . C8 C 0.17908(5) 0.58858(10) 0.00964(4) 0.01306(13) Uani 1 d . . C9 C 0.10166(5) 0.66696(10) 0.02714(4) 0.01356(13) Uani 1 d . . C10 C 0.07639(5) 0.66377(10) 0.10140(4) 0.01399(13) Uani 1 d . . C11 C 0.12780(5) 0.58736(10) 0.16418(4) 0.01358(13) Uani 1 d . . C12 C 0.20080(4) 0.50969(10) 0.14553(4) 0.01183(13) Uani 1 d . . C13 C 0.29614(6) 0.32150(12) 0.31257(4) 0.0187(2) Uani 1 d . . C14 C 0.45819(6) 0.16285(12) 0.28232(5) 0.0194(2) Uani 1 d . . C15 C 0.50801(5) 0.15593(13) 0.12667(5) 0.0191(2) Uani 1 d . . C16 C 0.40342(5) 0.32106(12) 0.00126(5) 0.01807(15) Uani 1 d . . C17 C 0.20640(5) 0.59386(12) -0.06918(5) 0.0188(2) Uani 1 d . . C18 C 0.04534(5) 0.74996(12) -0.03722(5) 0.0192(2) Uani 1 d . . C19 C -0.00841(5) 0.73595(12) 0.11555(5) 0.0191(2) Uani 1 d . . C20 C 0.10285(6) 0.59248(13) 0.24401(5) 0.0201(2) Uani 1 d . . H13A H 0.3038(8) 0.2027(20) 0.3373(7) 0.044(4) Uiso 1 d . . H13B H 0.2353(8) 0.3443(17) 0.3108(7) 0.036(3) Uiso 1 d . . H13C H 0.3239(8) 0.4082(19) 0.3449(7) 0.038(3) Uiso 1 d . . H14A H 0.4506(10) 0.2194(25) 0.3285(9) 0.072(5) Uiso 1 d . . H14B H 0.5148(10) 0.1882(23) 0.2767(8) 0.064(5) Uiso 1 d . . H14C H 0.4496(10) 0.0346(25) 0.2877(8) 0.069(5) Uiso 1 d . . H15A H 0.5023(7) 0.0741(17) 0.0807(7) 0.033(3) Uiso 1 d . . H15B H 0.5321(9) 0.0790(21) 0.1677(8) 0.054(4) Uiso 1 d . . H15C H 0.5473(9) 0.2490(21) 0.1166(7) 0.050(4) Uiso 1 d . . H16A H 0.4584(9) 0.3581(20) -0.0011(8) 0.051(4) Uiso 1 d . . H16B H 0.3689(8) 0.3968(21) -0.0330(7) 0.048(4) Uiso 1 d . . H16C H 0.3991(8) 0.1963(21) -0.0205(7) 0.049(4) Uiso 1 d . . H17A H 0.2106(8) 0.7199(19) -0.0871(7) 0.041(4) Uiso 1 d . . H17B H 0.1685(8) 0.5250(21) -0.1050(7) 0.049(4) Uiso 1 d . . H17C H 0.2608(8) 0.5431(20) -0.0678(7) 0.047(4) Uiso 1 d . . H18A H 0.0759(9) 0.8189(22) -0.0722(8) 0.057(4) Uiso 1 d . . H18B H 0.0114(10) 0.8505(22) -0.0186(8) 0.060(4) Uiso 1 d . . H18C H 0.0096(10) 0.6593(23) -0.0608(8) 0.066(5) Uiso 1 d . . H19A H -0.0290(7) 0.6845(17) 0.1613(7) 0.033(3) Uiso 1 d . . H19B H -0.0497(7) 0.6977(17) 0.0761(6) 0.028(3) Uiso 1 d . . H19C H -0.0067(8) 0.8732(21) 0.1212(7) 0.044(4) Uiso 1 d . . H20A H 0.0822(8) 0.7180(19) 0.2586(7) 0.042(4) Uiso 1 d . . H20B H 0.1509(8) 0.5617(18) 0.2827(7) 0.040(3) Uiso 1 d . . H20C H 0.0611(8) 0.5057(20) 0.2512(7) 0.043(4) Uiso 1 d . . N1 N 0.39214(5) 0.69602(11) 0.54627(5) 0.0241(2) Uani 1 d . . N2 N 0.30850(5) 0.68507(11) 0.77717(4) 0.0227(2) Uani 1 d . . N3 N 0.19172(5) 0.40089(11) 0.46754(4) 0.0227(2) Uani 1 d . . N4 N 0.10612(5) 0.39120(11) 0.69857(5) 0.0262(2) Uani 1 d . . C21 C 0.28335(5) 0.59310(11) 0.63569(4) 0.01492(14) Uani 1 d . . C22 C 0.21528(5) 0.49183(11) 0.60936(4) 0.01496(14) Uani 1 d . . C23 C 0.34350(5) 0.64938(11) 0.58580(4) 0.01652(15) Uani 1 d . . C24 C 0.29703(5) 0.64411(11) 0.71445(4) 0.01686(15) Uani 1 d . . C25 C 0.20208(5) 0.44083(11) 0.53054(5) 0.01712(15) Uani 1 d . . C26 C 0.15490(5) 0.43592(11) 0.65903(5) 0.01790(15) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0128(3) 0.0112(3) 0.0120(3) 0.0000(2) 0.0026(2) 0.0005(2) C2 0.0148(3) 0.0129(3) 0.0115(3) 0.0004(2) 0.0011(2) -0.0003(3) C3 0.0137(3) 0.0128(3) 0.0144(3) 0.0003(3) -0.0005(2) -0.0001(3) C4 0.0113(3) 0.0126(3) 0.0162(3) -0.0011(2) 0.0009(2) 0.0001(2) C5 0.0125(3) 0.0131(3) 0.0135(3) -0.0015(2) 0.0030(2) -0.0003(2) C6 0.0122(3) 0.0116(3) 0.0109(3) 0.0002(2) 0.0022(2) 0.0004(2) C7 0.0123(3) 0.0116(3) 0.0121(3) -0.0003(2) 0.0024(2) 0.0008(2) C8 0.0147(3) 0.0123(3) 0.0121(3) 0.0000(2) 0.0011(2) 0.0000(3) C9 0.0133(3) 0.0120(3) 0.0151(3) 0.0001(2) 0.0003(2) 0.0005(2) C10 0.0125(3) 0.0122(3) 0.0175(3) -0.0001(3) 0.0025(2) 0.0004(2) C11 0.0131(3) 0.0130(3) 0.0153(3) 0.0003(2) 0.0045(2) 0.0004(3) C12 0.0124(3) 0.0116(3) 0.0118(3) 0.0009(2) 0.0026(2) 0.0004(2) C13 0.0223(4) 0.0226(4) 0.0115(3) 0.0026(3) 0.0031(3) 0.0023(3) C14 0.0182(4) 0.0208(4) 0.0183(4) 0.0021(3) -0.0036(3) 0.0028(3) C15 0.0124(3) 0.0218(4) 0.0231(4) -0.0017(3) 0.0023(3) 0.0035(3) C16 0.0170(4) 0.0230(4) 0.0150(3) -0.0012(3) 0.0057(3) 0.0025(3) C17 0.0219(4) 0.0225(4) 0.0122(3) 0.0015(3) 0.0029(3) 0.0041(3) C18 0.0181(4) 0.0190(4) 0.0195(4) 0.0023(3) -0.0035(3) 0.0030(3) C19 0.0130(3) 0.0194(4) 0.0256(4) 0.0007(3) 0.0047(3) 0.0038(3) C20 0.0198(4) 0.0248(4) 0.0170(4) 0.0020(3) 0.0088(3) 0.0048(3) N1 0.0200(3) 0.0230(4) 0.0307(4) 0.0059(3) 0.0092(3) 0.0019(3) N2 0.0235(4) 0.0242(4) 0.0201(3) -0.0015(3) 0.0013(3) 0.0016(3) N3 0.0229(3) 0.0241(4) 0.0210(3) -0.0032(3) 0.0011(3) 0.0010(3) N4 0.0216(3) 0.0235(4) 0.0352(4) 0.0065(3) 0.0117(3) 0.0023(3) C21 0.0151(3) 0.0152(3) 0.0148(3) 0.0002(3) 0.0032(2) 0.0002(3) C22 0.0150(3) 0.0149(3) 0.0154(3) 0.0003(3) 0.0034(3) 0.0000(3) C23 0.0148(3) 0.0155(3) 0.0195(4) 0.0011(3) 0.0028(3) 0.0006(3) C24 0.0162(3) 0.0159(3) 0.0185(3) 0.0003(3) 0.0017(3) 0.0007(3) C25 0.0157(3) 0.0157(3) 0.0198(4) -0.0012(3) 0.0010(3) 0.0002(3) C26 0.0162(3) 0.0155(3) 0.0224(4) 0.0010(3) 0.0039(3) 0.0005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3739(10) . ? C1 C6 1.4209(10) . ? C1 C12 1.5120(10) . ? C2 C3 1.4329(11) . ? C2 C13 1.5019(11) . ? C3 C4 1.4105(11) . ? C3 C14 1.5119(11) . ? C4 C5 1.4333(10) . ? C4 C15 1.5093(11) . ? C5 C6 1.3735(10) . ? C5 C16 1.5025(11) . ? C6 C7 1.5121(10) . ? C7 C8 1.3782(10) . ? C7 C12 1.4233(10) . ? C8 C9 1.4327(10) . ? C8 C17 1.5019(11) . ? C9 C10 1.4120(11) . ? C9 C18 1.5106(11) . ? C10 C11 1.4311(11) . ? C10 C19 1.5079(11) . ? C11 C12 1.3736(10) . ? C11 C20 1.5050(11) . ? N1 C23 1.1506(11) . ? N2 C24 1.1455(11) . ? N3 C25 1.1472(11) . ? N4 C26 1.1485(11) . ? C21 C22 1.3642(11) . ? C21 C23 1.4320(11) . ? C21 C24 1.4370(11) . ? C22 C26 1.4314(11) . ? C22 C25 1.4374(11) . ? 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 C2 C1 C6 123.41(7) . . ? C2 C1 C12 146.52(7) . . ? C6 C1 C12 90.07(5) . . ? C1 C2 C3 114.95(7) . . ? C1 C2 C13 122.72(7) . . ? C3 C2 C13 122.33(7) . . ? C4 C3 C2 121.67(7) . . ? C4 C3 C14 120.17(7) . . ? C2 C3 C14 118.14(7) . . ? C3 C4 C5 122.03(7) . . ? C3 C4 C15 120.68(7) . . ? C5 C4 C15 117.26(7) . . ? C6 C5 C4 115.04(7) . . ? C6 C5 C16 123.47(7) . . ? C4 C5 C16 121.48(7) . . ? C5 C6 C1 122.87(7) . . ? C5 C6 C7 147.11(7) . . ? C1 C6 C7 90.02(6) . . ? C8 C7 C12 122.95(7) . . ? C8 C7 C6 147.07(7) . . ? C12 C7 C6 89.98(6) . . ? C7 C8 C9 114.77(7) . . ? C7 C8 C17 123.20(7) . . ? C9 C8 C17 122.02(7) . . ? C10 C9 C8 122.02(7) . . ? C10 C9 C18 120.02(7) . . ? C8 C9 C18 117.94(7) . . ? C9 C10 C11 121.99(7) . . ? C9 C10 C19 119.78(7) . . ? C11 C10 C19 118.20(7) . . ? C12 C11 C10 114.73(7) . . ? C12 C11 C20 123.24(7) . . ? C10 C11 C20 122.03(7) . . ? C11 C12 C7 123.45(7) . . ? C11 C12 C1 146.61(7) . . ? C7 C12 C1 89.93(6) . . ? C22 C21 C23 120.91(7) . . ? C22 C21 C24 120.80(7) . . ? C23 C21 C24 118.29(7) . . ? C21 C22 C26 121.03(7) . . ? C21 C22 C25 120.52(7) . . ? C26 C22 C25 118.44(7) . . ? N1 C23 C21 179.26(9) . . ? N2 C24 C21 179.52(8) . . ? N3 C25 C22 179.68(8) . . ? N4 C26 C22 179.62(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.35(11) . . . . ? C12 C1 C2 C3 -178.86(10) . . . . ? C6 C1 C2 C13 -178.15(7) . . . . ? C12 C1 C2 C13 1.6(2) . . . . ? C1 C2 C3 C4 -1.96(11) . . . . ? C13 C2 C3 C4 177.54(7) . . . . ? C1 C2 C3 C14 176.45(7) . . . . ? C13 C2 C3 C14 -4.05(11) . . . . ? C2 C3 C4 C5 1.45(11) . . . . ? C14 C3 C4 C5 -176.92(7) . . . . ? C2 C3 C4 C15 179.64(7) . . . . ? C14 C3 C4 C15 1.26(11) . . . . ? C3 C4 C5 C6 -0.18(11) . . . . ? C15 C4 C5 C6 -178.42(7) . . . . ? C3 C4 C5 C16 -179.88(7) . . . . ? C15 C4 C5 C16 1.88(11) . . . . ? C4 C5 C6 C1 -0.47(11) . . . . ? C16 C5 C6 C1 179.22(7) . . . . ? C4 C5 C6 C7 179.52(10) . . . . ? C16 C5 C6 C7 -0.8(2) . . . . ? C2 C1 C6 C5 -0.15(12) . . . . ? C12 C1 C6 C5 179.96(7) . . . . ? C2 C1 C6 C7 179.85(7) . . . . ? C12 C1 C6 C7 -0.04(6) . . . . ? C5 C6 C7 C8 0.6(2) . . . . ? C1 C6 C7 C8 -179.41(12) . . . . ? C5 C6 C7 C12 -179.95(11) . . . . ? C1 C6 C7 C12 0.04(6) . . . . ? C12 C7 C8 C9 -1.79(11) . . . . ? C6 C7 C8 C9 177.56(10) . . . . ? C12 C7 C8 C17 178.05(7) . . . . ? C6 C7 C8 C17 -2.6(2) . . . . ? C7 C8 C9 C10 0.54(11) . . . . ? C17 C8 C9 C10 -179.30(7) . . . . ? C7 C8 C9 C18 -177.72(7) . . . . ? C17 C8 C9 C18 2.44(11) . . . . ? C8 C9 C10 C11 2.06(11) . . . . ? C18 C9 C10 C11 -179.71(7) . . . . ? C8 C9 C10 C19 -175.61(7) . . . . ? C18 C9 C10 C19 2.62(11) . . . . ? C9 C10 C11 C12 -3.26(11) . . . . ? C19 C10 C11 C12 174.44(7) . . . . ? C9 C10 C11 C20 176.86(7) . . . . ? C19 C10 C11 C20 -5.44(11) . . . . ? C10 C11 C12 C7 2.06(11) . . . . ? C20 C11 C12 C7 -178.06(7) . . . . ? C10 C11 C12 C1 -176.38(10) . . . . ? C20 C11 C12 C1 3.5(2) . . . . ? C8 C7 C12 C11 0.47(12) . . . . ? C6 C7 C12 C11 -179.18(7) . . . . ? C8 C7 C12 C1 179.61(7) . . . . ? C6 C7 C12 C1 -0.04(6) . . . . ? C2 C1 C12 C11 -1.1(2) . . . . ? C6 C1 C12 C11 178.74(11) . . . . ? C2 C1 C12 C7 -179.79(11) . . . . ? C6 C1 C12 C7 0.04(6) . . . . ? C23 C21 C22 C26 -179.78(8) . . . . ? C24 C21 C22 C26 0.98(11) . . . . ? C23 C21 C22 C25 -0.59(11) . . . . ? C24 C21 C22 C25 -179.83(7) . . . . ? C22 C21 C23 N1 161.8(75) . . . . ? C24 C21 C23 N1 -19.0(76) . . . . ? C22 C21 C24 N2 163.8(671) . . . . ? C23 C21 C24 N2 -15.5(122) . . . . ? C21 C22 C25 N3 -32.1(174) . . . . ? C26 C22 C25 N3 147.2(173) . . . . ? C21 C22 C26 N4 143.9(138) . . . . ? C25 C22 C26 N4 -35.3(138) . . . . ? _refine_diff_density_max 0.462 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.056 data_pier-ssx _database_code_CSD 138876 _audit_creation_method SHELXL _chemical_name_systematic ; Octamethylbiphenylene/7,7,8,8-Tetracyanoquinodimethane molecular complex 1:1 ; _chemical_name_common ? _chemical_formula_moiety '(C20 H24), (C12 H4 N4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C32 H28 N4' _chemical_formula_weight 468.58 _chemical_melting_point ? _chemical_compound_source 'chemical synthesis' 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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1081(8) _cell_length_b 9.6152(6) _cell_length_c 17.0229(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.980(2) _cell_angle_gamma 90.00 _cell_volume 2459.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4723 _cell_measurement_theta_min 2 _cell_measurement_theta_max 35 _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method none _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.977 _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number 144 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 30631 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 35.82 _reflns_number_total 10776 _reflns_number_observed 6765 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 34 with very negative F^2^ or flagged by us for potential systematic errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10742 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_obs 0.0455 _refine_ls_wR_factor_all 0.1329 _refine_ls_wR_factor_obs 0.1109 _refine_ls_goodness_of_fit_all 0.932 _refine_ls_goodness_of_fit_obs 1.053 _refine_ls_restrained_S_all 0.993 _refine_ls_restrained_S_obs 1.053 _refine_ls_shift/esd_max -0.011 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.32193(6) 0.51091(9) 0.48053(5) 0.01361(15) Uani 1 d . . C2 C 0.35294(6) 0.59556(9) 0.54289(5) 0.0156(2) Uani 1 d . . C3 C 0.42706(6) 0.68039(9) 0.52904(6) 0.0178(2) Uani 1 d . . C4 C 0.46269(6) 0.68196(9) 0.45554(6) 0.0180(2) Uani 1 d . . C5 C 0.42743(6) 0.59694(9) 0.39088(6) 0.0168(2) Uani 1 d . . C6 C 0.35870(6) 0.51080(9) 0.40701(5) 0.0141(2) Uani 1 d . . C7 C 0.29562(6) 0.39672(9) 0.37761(5) 0.01338(15) Uani 1 d . . C8 C 0.26933(6) 0.30408(9) 0.31811(5) 0.0145(2) Uani 1 d . . C9 C 0.20038(6) 0.21009(9) 0.33465(5) 0.0153(2) Uani 1 d . . C10 C 0.16346(6) 0.21115(9) 0.40747(5) 0.0154(2) Uani 1 d . . C11 C 0.19290(6) 0.30726(9) 0.46892(5) 0.0142(2) Uani 1 d . . C12 C 0.25846(6) 0.39761(9) 0.45125(5) 0.01327(15) Uani 1 d . . C13 C 0.31125(7) 0.60144(11) 0.61941(6) 0.0225(2) Uani 1 d . . C14 C 0.46926(8) 0.76817(12) 0.59608(7) 0.0271(2) Uani 1 d . . C15 C 0.54147(7) 0.77358(12) 0.44464(8) 0.0272(2) Uani 1 d . . C16 C 0.46271(8) 0.60335(12) 0.31180(7) 0.0258(2) Uani 1 d . . C17 C 0.31034(7) 0.29943(11) 0.24133(6) 0.0209(2) Uani 1 d . . C18 C 0.16804(7) 0.10638(11) 0.27160(6) 0.0210(2) Uani 1 d . . C19 C 0.09251(7) 0.10767(11) 0.42363(7) 0.0233(2) Uani 1 d . . C20 C 0.15462(7) 0.30623(11) 0.54663(6) 0.0204(2) Uani 1 d . . H13A H 0.2952(11) 0.6962(17) 0.6329(9) 0.045(4) Uiso 1 d . . H13B H 0.3502(11) 0.5631(17) 0.6631(10) 0.052(5) Uiso 1 d . . H13C H 0.2530(12) 0.5438(19) 0.6156(11) 0.063(5) Uiso 1 d . . H14A H 0.4477(20) 0.7457(30) 0.6437(18) 0.130(10) Uiso 1 d . . H14B H 0.4615(14) 0.8650(22) 0.5853(13) 0.078(6) Uiso 1 d . . H14C H 0.5317(14) 0.7633(20) 0.6033(11) 0.067(6) Uiso 1 d . . H15A H 0.5591(21) 0.7771(31) 0.3929(20) 0.136(11) Uiso 1 d . . H15B H 0.5937(14) 0.7540(22) 0.4780(12) 0.079(6) Uiso 1 d . . H15C H 0.5283(19) 0.8764(29) 0.4491(16) 0.122(10) Uiso 1 d . . H16A H 0.4638(10) 0.7002(16) 0.2944(9) 0.041(4) Uiso 1 d . . H16B H 0.4228(12) 0.5499(19) 0.2715(11) 0.056(5) Uiso 1 d . . H16C H 0.5215(13) 0.5668(19) 0.3106(11) 0.060(5) Uiso 1 d . . H17A H 0.3331(11) 0.2073(18) 0.2305(10) 0.048(5) Uiso 1 d . . H17B H 0.3593(12) 0.3685(17) 0.2428(10) 0.050(5) Uiso 1 d . . H17C H 0.2681(11) 0.3311(18) 0.1952(10) 0.051(5) Uiso 1 d . . H18A H 0.2192(14) 0.0556(20) 0.2554(11) 0.068(6) Uiso 1 d . . H18B H 0.1388(15) 0.1521(22) 0.2291(13) 0.078(6) Uiso 1 d . . H18C H 0.1373(13) 0.0327(20) 0.2914(12) 0.066(6) Uiso 1 d . . H19A H 0.0829(15) 0.1052(23) 0.4803(14) 0.092(7) Uiso 1 d . . H19B H 0.1035(11) 0.0143(18) 0.4088(10) 0.054(5) Uiso 1 d . . H19C H 0.0341(14) 0.1312(19) 0.3937(12) 0.072(6) Uiso 1 d . . H20A H 0.0904(11) 0.3153(16) 0.5415(9) 0.046(4) Uiso 1 d . . H20B H 0.1795(11) 0.3842(17) 0.5794(10) 0.046(4) Uiso 1 d . . H20C H 0.1680(10) 0.2230(17) 0.5747(9) 0.039(4) Uiso 1 d . . N1 N 0.28523(7) 0.98356(10) 0.56211(6) 0.0275(2) Uani 1 d . . N2 N 0.39627(6) 0.98280(9) 0.32877(5) 0.0242(2) Uani 1 d . . N3 N -0.06850(6) 0.36274(10) 0.39531(5) 0.0247(2) Uani 1 d . . N4 N 0.04110(6) 0.35988(10) 0.17078(5) 0.0250(2) Uani 1 d . . C21 C 0.22917(6) 0.77807(9) 0.39467(5) 0.0151(2) Uani 1 d . . C22 C 0.22841(6) 0.72458(9) 0.31554(5) 0.0165(2) Uani 1 d . . C23 C 0.17102(6) 0.62277(9) 0.28861(5) 0.0163(2) Uani 1 d . . C24 C 0.10894(6) 0.56548(9) 0.33857(5) 0.0146(2) Uani 1 d . . C25 C 0.10919(6) 0.61996(9) 0.41731(5) 0.0155(2) Uani 1 d . . C26 C 0.16654(6) 0.72164(9) 0.44422(5) 0.0156(2) Uani 1 d . . C27 C 0.28794(6) 0.88306(9) 0.42202(5) 0.0173(2) Uani 1 d . . C28 C 0.28732(6) 0.93965(10) 0.49962(6) 0.0198(2) Uani 1 d . . C29 C 0.34889(6) 0.94029(9) 0.37200(6) 0.0190(2) Uani 1 d . . C30 C 0.04962(6) 0.46148(9) 0.31152(5) 0.0157(2) Uani 1 d . . C31 C -0.01518(6) 0.40750(10) 0.35870(5) 0.0179(2) Uani 1 d . . C32 C 0.04626(6) 0.40601(10) 0.23350(6) 0.0176(2) Uani 1 d . . H22A H 0.2714(9) 0.7614(13) 0.2825(8) 0.025(3) Uiso 1 d . . H23A H 0.1701(9) 0.5856(14) 0.2351(8) 0.025(3) Uiso 1 d . . H25A H 0.0649(8) 0.5809(12) 0.4510(7) 0.017(3) Uiso 1 d . . H26A H 0.1631(9) 0.7534(13) 0.4969(8) 0.023(3) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0140(4) 0.0145(3) 0.0119(3) 0.0007(3) -0.0003(3) -0.0004(3) C2 0.0164(4) 0.0162(4) 0.0134(4) -0.0003(3) -0.0019(3) 0.0006(3) C3 0.0165(4) 0.0160(4) 0.0196(4) -0.0009(3) -0.0042(3) -0.0002(3) C4 0.0138(4) 0.0159(4) 0.0237(4) 0.0022(3) -0.0012(3) -0.0008(3) C5 0.0144(4) 0.0166(4) 0.0197(4) 0.0021(3) 0.0029(3) 0.0002(3) C6 0.0142(4) 0.0152(4) 0.0128(3) 0.0002(3) 0.0013(3) 0.0001(3) C7 0.0135(3) 0.0148(3) 0.0117(3) 0.0007(3) 0.0008(3) 0.0004(3) C8 0.0158(4) 0.0159(4) 0.0116(3) -0.0004(3) 0.0001(3) 0.0022(3) C9 0.0160(4) 0.0150(4) 0.0143(4) -0.0012(3) -0.0020(3) 0.0011(3) C10 0.0143(4) 0.0151(4) 0.0162(4) 0.0004(3) -0.0006(3) -0.0002(3) C11 0.0144(4) 0.0150(4) 0.0130(3) 0.0013(3) 0.0012(3) 0.0004(3) C12 0.0136(3) 0.0148(3) 0.0112(3) -0.0006(3) 0.0003(3) 0.0002(3) C13 0.0270(5) 0.0273(5) 0.0127(4) -0.0033(4) -0.0003(3) -0.0031(4) C14 0.0251(5) 0.0257(5) 0.0285(5) -0.0083(4) -0.0059(4) -0.0052(4) C15 0.0179(4) 0.0256(5) 0.0372(6) 0.0059(4) -0.0018(4) -0.0076(4) C16 0.0255(5) 0.0272(5) 0.0267(5) -0.0006(4) 0.0127(4) -0.0046(4) C17 0.0268(5) 0.0231(4) 0.0133(4) -0.0032(3) 0.0042(3) -0.0007(4) C18 0.0244(5) 0.0195(4) 0.0178(4) -0.0048(3) -0.0033(3) -0.0016(4) C19 0.0200(4) 0.0206(4) 0.0296(5) -0.0018(4) 0.0035(4) -0.0064(4) C20 0.0243(5) 0.0222(4) 0.0156(4) 0.0005(3) 0.0067(3) -0.0038(4) N1 0.0307(5) 0.0260(4) 0.0249(4) -0.0060(3) -0.0014(4) 0.0014(4) N2 0.0243(4) 0.0236(4) 0.0242(4) 0.0021(3) -0.0006(3) -0.0040(3) N3 0.0216(4) 0.0288(4) 0.0240(4) -0.0011(3) 0.0037(3) -0.0017(3) N4 0.0231(4) 0.0299(4) 0.0213(4) -0.0057(3) -0.0015(3) 0.0051(3) C21 0.0159(4) 0.0148(4) 0.0142(4) 0.0010(3) 0.0000(3) 0.0014(3) C22 0.0176(4) 0.0178(4) 0.0141(4) 0.0014(3) 0.0015(3) -0.0003(3) C23 0.0171(4) 0.0189(4) 0.0130(4) 0.0006(3) 0.0015(3) 0.0008(3) C24 0.0138(4) 0.0163(4) 0.0132(4) 0.0003(3) -0.0004(3) 0.0017(3) C25 0.0154(4) 0.0176(4) 0.0135(4) 0.0004(3) 0.0011(3) 0.0014(3) C26 0.0162(4) 0.0173(4) 0.0131(4) -0.0007(3) 0.0006(3) 0.0016(3) C27 0.0178(4) 0.0163(4) 0.0173(4) 0.0003(3) 0.0000(3) 0.0003(3) C28 0.0190(4) 0.0173(4) 0.0221(4) -0.0005(3) -0.0020(3) 0.0006(3) C29 0.0192(4) 0.0166(4) 0.0201(4) 0.0001(3) -0.0031(3) -0.0009(3) C30 0.0142(4) 0.0184(4) 0.0142(4) -0.0008(3) 0.0003(3) 0.0010(3) C31 0.0167(4) 0.0189(4) 0.0174(4) -0.0023(3) -0.0015(3) 0.0011(3) C32 0.0144(4) 0.0192(4) 0.0185(4) -0.0010(3) -0.0007(3) 0.0017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3802(12) . ? C1 C6 1.4213(12) . ? C1 C12 1.5017(12) . ? C2 C3 1.4247(13) . ? C2 C13 1.5060(14) . ? C3 C4 1.4128(14) . ? C3 C14 1.5066(14) . ? C4 C5 1.4287(13) . ? C4 C15 1.5076(14) . ? C5 C6 1.3780(12) . ? C5 C16 1.5000(14) . ? C6 C7 1.5041(12) . ? C7 C8 1.3760(12) . ? C7 C12 1.4261(12) . ? C8 C9 1.4291(13) . ? C8 C17 1.5042(13) . ? C9 C10 1.4113(13) . ? C9 C18 1.5085(13) . ? C10 C11 1.4314(12) . ? C10 C19 1.5087(14) . ? C11 C12 1.3741(12) . ? C11 C20 1.4980(13) . ? C13 H13A 0.98(2) . ? C13 H13B 0.97(2) . ? C13 H13C 1.04(2) . ? C14 H14A 0.93(3) . ? C14 H14B 0.95(2) . ? C14 H14C 0.94(2) . ? C15 H15A 0.95(3) . ? C15 H15B 0.94(2) . ? C15 H15C 1.01(3) . ? C16 H16A 0.98(2) . ? C16 H16B 1.01(2) . ? C16 H16C 0.96(2) . ? C17 H17A 0.97(2) . ? C17 H17B 0.99(2) . ? C17 H17C 1.01(2) . ? C18 H18A 0.98(2) . ? C18 H18B 0.92(2) . ? C18 H18C 0.93(2) . ? C19 H19A 0.99(2) . ? C19 H19B 0.95(2) . ? C19 H19C 1.00(2) . ? C20 H20A 0.97(2) . ? C20 H20B 0.99(2) . ? C20 H20C 0.94(2) . ? N1 C28 1.1480(13) . ? N2 C29 1.1536(13) . ? N3 C31 1.1520(13) . ? N4 C32 1.1512(12) . ? C21 C27 1.3920(13) . ? C21 C26 1.4380(13) . ? C21 C22 1.4407(13) . ? C22 C23 1.3556(13) . ? C22 H22A 0.969(13) . ? C23 C24 1.4397(13) . ? C23 H23A 0.978(13) . ? C24 C30 1.3889(12) . ? C24 C25 1.4389(12) . ? C25 C26 1.3541(13) . ? C25 H25A 0.999(12) . ? C26 H26A 0.953(13) . ? C27 C29 1.4280(14) . ? C27 C28 1.4296(13) . ? C30 C31 1.4272(13) . ? C30 C32 1.4272(13) . ? 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 C2 C1 C6 123.03(8) . . ? C2 C1 C12 146.82(8) . . ? C6 C1 C12 90.10(7) . . ? C1 C2 C3 114.84(8) . . ? C1 C2 C13 123.25(8) . . ? C3 C2 C13 121.90(8) . . ? C4 C3 C2 122.09(8) . . ? C4 C3 C14 119.65(9) . . ? C2 C3 C14 118.25(9) . . ? C3 C4 C5 122.02(8) . . ? C3 C4 C15 119.59(9) . . ? C5 C4 C15 118.38(9) . . ? C6 C5 C4 114.76(8) . . ? C6 C5 C16 123.30(9) . . ? C4 C5 C16 121.94(9) . . ? C5 C6 C1 123.14(8) . . ? C5 C6 C7 146.77(8) . . ? C1 C6 C7 90.07(7) . . ? C8 C7 C12 122.75(8) . . ? C8 C7 C6 147.28(8) . . ? C12 C7 C6 89.83(7) . . ? C7 C8 C9 115.14(8) . . ? C7 C8 C17 123.05(8) . . ? C9 C8 C17 121.81(8) . . ? C10 C9 C8 122.09(8) . . ? C10 C9 C18 120.09(8) . . ? C8 C9 C18 117.81(8) . . ? C9 C10 C11 121.70(8) . . ? C9 C10 C19 120.58(8) . . ? C11 C10 C19 117.71(8) . . ? C12 C11 C10 115.11(8) . . ? C12 C11 C20 123.43(8) . . ? C10 C11 C20 121.46(8) . . ? C11 C12 C7 123.19(8) . . ? C11 C12 C1 146.71(8) . . ? C7 C12 C1 89.99(7) . . ? C2 C13 H13A 112.0(9) . . ? C2 C13 H13B 111.9(10) . . ? H13A C13 H13B 108.6(13) . . ? C2 C13 H13C 110.7(10) . . ? H13A C13 H13C 106.5(14) . . ? H13B C13 H13C 106.7(14) . . ? C3 C14 H14A 111.8(18) . . ? C3 C14 H14B 111.5(13) . . ? H14A C14 H14B 110.3(22) . . ? C3 C14 H14C 114.3(12) . . ? H14A C14 H14C 108.2(21) . . ? H14B C14 H14C 100.1(17) . . ? C4 C15 H15A 115.9(19) . . ? C4 C15 H15B 115.6(13) . . ? H15A C15 H15B 105.7(21) . . ? C4 C15 H15C 113.4(16) . . ? H15A C15 H15C 96.4(22) . . ? H15B C15 H15C 108.0(20) . . ? C5 C16 H16A 109.2(9) . . ? C5 C16 H16B 110.3(10) . . ? H16A C16 H16B 108.0(14) . . ? C5 C16 H16C 114.9(11) . . ? H16A C16 H16C 107.4(14) . . ? H16B C16 H16C 106.9(15) . . ? C8 C17 H17A 112.1(10) . . ? C8 C17 H17B 109.4(9) . . ? H17A C17 H17B 109.6(14) . . ? C8 C17 H17C 112.6(10) . . ? H17A C17 H17C 109.6(14) . . ? H17B C17 H17C 103.2(13) . . ? C9 C18 H18A 108.9(11) . . ? C9 C18 H18B 109.7(13) . . ? H18A C18 H18B 110.2(17) . . ? C9 C18 H18C 112.5(12) . . ? H18A C18 H18C 99.3(16) . . ? H18B C18 H18C 115.6(17) . . ? C10 C19 H19A 111.9(13) . . ? C10 C19 H19B 115.3(11) . . ? H19A C19 H19B 106.4(16) . . ? C10 C19 H19C 111.4(11) . . ? H19A C19 H19C 106.9(17) . . ? H19B C19 H19C 104.3(15) . . ? C11 C20 H20A 113.3(10) . . ? C11 C20 H20B 109.6(10) . . ? H20A C20 H20B 107.6(13) . . ? C11 C20 H20C 111.8(9) . . ? H20A C20 H20C 106.4(13) . . ? H20B C20 H20C 108.1(13) . . ? C27 C21 C26 120.88(8) . . ? C27 C21 C22 120.95(8) . . ? C26 C21 C22 118.17(8) . . ? C23 C22 C21 121.10(9) . . ? C23 C22 H22A 120.8(8) . . ? C21 C22 H22A 118.1(8) . . ? C22 C23 C24 120.64(8) . . ? C22 C23 H23A 121.8(8) . . ? C24 C23 H23A 117.6(8) . . ? C30 C24 C25 120.66(8) . . ? C30 C24 C23 121.15(8) . . ? C25 C24 C23 118.19(8) . . ? C26 C25 C24 121.17(8) . . ? C26 C25 H25A 121.4(7) . . ? C24 C25 H25A 117.5(7) . . ? C25 C26 C21 120.73(8) . . ? C25 C26 H26A 117.0(8) . . ? C21 C26 H26A 122.3(8) . . ? C21 C27 C29 120.56(8) . . ? C21 C27 C28 121.31(9) . . ? C29 C27 C28 118.10(8) . . ? N1 C28 C27 178.57(11) . . ? N2 C29 C27 176.81(10) . . ? C24 C30 C31 122.14(8) . . ? C24 C30 C32 122.46(8) . . ? C31 C30 C32 115.33(8) . . ? N3 C31 C30 178.49(10) . . ? N4 C32 C30 178.02(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.97(12) . . . . ? C12 C1 C2 C3 174.66(12) . . . . ? C6 C1 C2 C13 176.76(9) . . . . ? C12 C1 C2 C13 -6.6(2) . . . . ? C1 C2 C3 C4 3.00(13) . . . . ? C13 C2 C3 C4 -175.74(9) . . . . ? C1 C2 C3 C14 -175.62(8) . . . . ? C13 C2 C3 C14 5.63(14) . . . . ? C2 C3 C4 C5 -0.97(14) . . . . ? C14 C3 C4 C5 177.63(9) . . . . ? C2 C3 C4 C15 -179.75(9) . . . . ? C14 C3 C4 C15 -1.15(14) . . . . ? C3 C4 C5 C6 -2.19(13) . . . . ? C15 C4 C5 C6 176.61(8) . . . . ? C3 C4 C5 C16 177.25(9) . . . . ? C15 C4 C5 C16 -3.95(14) . . . . ? C4 C5 C6 C1 3.28(13) . . . . ? C16 C5 C6 C1 -176.15(9) . . . . ? C4 C5 C6 C7 -175.07(12) . . . . ? C16 C5 C6 C7 5.5(2) . . . . ? C2 C1 C6 C5 -1.26(13) . . . . ? C12 C1 C6 C5 -179.41(8) . . . . ? C2 C1 C6 C7 177.84(8) . . . . ? C12 C1 C6 C7 -0.32(6) . . . . ? C5 C6 C7 C8 3.9(2) . . . . ? C1 C6 C7 C8 -174.73(14) . . . . ? C5 C6 C7 C12 178.95(14) . . . . ? C1 C6 C7 C12 0.33(7) . . . . ? C12 C7 C8 C9 1.30(12) . . . . ? C6 C7 C8 C9 175.42(12) . . . . ? C12 C7 C8 C17 -177.92(8) . . . . ? C6 C7 C8 C17 -3.8(2) . . . . ? C7 C8 C9 C10 -1.15(12) . . . . ? C17 C8 C9 C10 178.08(9) . . . . ? C7 C8 C9 C18 179.60(8) . . . . ? C17 C8 C9 C18 -1.18(13) . . . . ? C8 C9 C10 C11 0.28(13) . . . . ? C18 C9 C10 C11 179.52(8) . . . . ? C8 C9 C10 C19 -178.30(8) . . . . ? C18 C9 C10 C19 0.94(13) . . . . ? C9 C10 C11 C12 0.49(12) . . . . ? C19 C10 C11 C12 179.10(8) . . . . ? C9 C10 C11 C20 -178.89(9) . . . . ? C19 C10 C11 C20 -0.27(13) . . . . ? C10 C11 C12 C7 -0.35(12) . . . . ? C20 C11 C12 C7 179.01(9) . . . . ? C10 C11 C12 C1 -175.06(12) . . . . ? C20 C11 C12 C1 4.3(2) . . . . ? C8 C7 C12 C11 -0.59(13) . . . . ? C6 C7 C12 C11 -177.41(8) . . . . ? C8 C7 C12 C1 176.51(8) . . . . ? C6 C7 C12 C1 -0.31(6) . . . . ? C2 C1 C12 C11 -1.3(2) . . . . ? C6 C1 C12 C11 175.91(13) . . . . ? C2 C1 C12 C7 -176.84(13) . . . . ? C6 C1 C12 C7 0.33(7) . . . . ? C27 C21 C22 C23 -179.72(8) . . . . ? C26 C21 C22 C23 -0.73(13) . . . . ? C21 C22 C23 C24 0.15(13) . . . . ? C22 C23 C24 C30 179.77(8) . . . . ? C22 C23 C24 C25 0.45(13) . . . . ? C30 C24 C25 C26 -179.79(8) . . . . ? C23 C24 C25 C26 -0.46(13) . . . . ? C24 C25 C26 C21 -0.12(13) . . . . ? C27 C21 C26 C25 179.70(8) . . . . ? C22 C21 C26 C25 0.71(13) . . . . ? C26 C21 C27 C29 -178.89(8) . . . . ? C22 C21 C27 C29 0.07(13) . . . . ? C26 C21 C27 C28 -0.87(13) . . . . ? C22 C21 C27 C28 178.09(8) . . . . ? C21 C27 C28 N1 -8.2(40) . . . . ? C29 C27 C28 N1 169.9(39) . . . . ? C21 C27 C29 N2 5.2(18) . . . . ? C28 C27 C29 N2 -172.9(18) . . . . ? C25 C24 C30 C31 2.18(13) . . . . ? C23 C24 C30 C31 -177.13(8) . . . . ? C25 C24 C30 C32 179.05(8) . . . . ? C23 C24 C30 C32 -0.26(13) . . . . ? C24 C30 C31 N3 162.1(37) . . . . ? C32 C30 C31 N3 -15.0(38) . . . . ? C24 C30 C32 N4 -159.9(28) . . . . ? C31 C30 C32 N4 17.2(29) . . . . ? _refine_diff_density_max 0.499 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.056 data_pier-isx _database_code_CSD 162664 _audit_creation_method SHELXL _chemical_name_systematic ; Octamethylbiphenylene(0)/Octamethylbiphenylene(+1) hexachloroantimonate molecular complex, toluene monosolvate ; _chemical_name_common ? _chemical_formula_moiety ; (C20 H24), (C20 H24)+, (Cl6 Sb)-, (C7 H8) ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C47 H56 Cl6 Sb' _chemical_formula_weight 955.37 _chemical_melting_point ? _chemical_compound_source 'chemical synthesis' 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' '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 'triclinic' _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4774(1) _cell_length_b 12.6630(1) _cell_length_c 14.3832(2) _cell_angle_alpha 74.421(1) _cell_angle_beta 77.326(1) _cell_angle_gamma 86.717(1) _cell_volume 2135.73(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2 _cell_measurement_theta_max 36 _exptl_crystal_description 'prism' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method none _exptl_crystal_F_000 982 _exptl_absorpt_coefficient_mu 1.055 _exptl_absorpt_correction_type 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.650 _exptl_absorpt_correction_T_max 0.860 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30219 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.1447 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 36.09 _reflns_number_total 18187 _reflns_number_observed 9462 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 34 with very negative F^2^ or flagged by us for potential systematic errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0851P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ; riding and rotating model with Uiso=1.5Uiso/eq of an adjacent carbon atom ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 18153 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1540 _refine_ls_R_factor_obs 0.0724 _refine_ls_wR_factor_all 0.1970 _refine_ls_wR_factor_obs 0.1561 _refine_ls_goodness_of_fit_all 0.971 _refine_ls_goodness_of_fit_obs 1.103 _refine_ls_restrained_S_all 1.003 _refine_ls_restrained_S_obs 1.103 _refine_ls_shift/esd_max 0.035 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sb Sb 0.69450(2) 0.52120(2) 0.25370(2) 0.01426(7) Uani 1 d . . Cl1 Cl 0.62909(9) 0.41699(10) 0.16323(8) 0.0250(2) Uani 1 d . . Cl2 Cl 0.53630(8) 0.47813(10) 0.38053(8) 0.0234(2) Uani 1 d . . Cl3 Cl 0.60582(9) 0.67865(9) 0.17150(8) 0.0228(2) Uani 1 d . . Cl4 Cl 0.78321(9) 0.36402(10) 0.33536(9) 0.0247(2) Uani 1 d . . Cl5 Cl 0.85460(8) 0.56443(10) 0.12749(8) 0.0242(2) Uani 1 d . . Cl6 Cl 0.76056(9) 0.62744(10) 0.34262(8) 0.0258(2) Uani 1 d . . C1 C 0.7011(3) -0.0531(3) 0.6382(3) 0.0134(7) Uani 1 d . . C2 C 0.6180(3) -0.1232(3) 0.6427(3) 0.0147(7) Uani 1 d . . C3 C 0.5147(3) -0.0706(4) 0.6345(3) 0.0170(8) Uani 1 d . . C4 C 0.5009(3) 0.0430(4) 0.6224(3) 0.0178(8) Uani 1 d . . C5 C 0.5884(3) 0.1154(3) 0.6142(3) 0.0144(7) Uani 1 d . . C6 C 0.6868(3) 0.0627(3) 0.6228(3) 0.0129(7) Uani 1 d . . C7 C 0.8054(3) 0.0743(3) 0.6215(3) 0.0140(7) Uani 1 d . . C8 C 0.8910(3) 0.1457(3) 0.6081(3) 0.0150(7) Uani 1 d . . C9 C 0.9948(3) 0.0941(4) 0.6128(3) 0.0156(8) Uani 1 d . . C10 C 1.0086(3) -0.0207(3) 0.6302(3) 0.0138(7) Uani 1 d . . C11 C 0.9197(3) -0.0936(3) 0.6434(3) 0.0134(7) Uani 1 d . . C12 C 0.8201(3) -0.0411(3) 0.6381(3) 0.0129(7) Uani 1 d . . C13 C 0.6349(3) -0.2445(4) 0.6536(3) 0.0197(8) Uani 1 d . . H13A H 0.7082(10) -0.2652(6) 0.6665(22) 0.030 Uiso 1 calc R . H13B H 0.6284(24) -0.2616(5) 0.5926(8) 0.030 Uiso 1 calc R . H13C H 0.5792(15) -0.2855(4) 0.7088(14) 0.030 Uiso 1 calc R . C14 C 0.4184(3) -0.1410(4) 0.6396(3) 0.0235(10) Uani 1 d . . H14A H 0.3766(15) -0.1028(12) 0.5901(16) 0.035 Uiso 1 calc R . H14B H 0.3707(14) -0.1551(22) 0.7056(8) 0.035 Uiso 1 calc R . H14C H 0.4456(4) -0.2108(11) 0.6263(23) 0.035 Uiso 1 calc R . C15 C 0.3874(3) 0.0922(4) 0.6169(3) 0.0231(9) Uani 1 d . . H15A H 0.3319(4) 0.0461(15) 0.6686(16) 0.035 Uiso 1 calc R . H15B H 0.3722(12) 0.0962(25) 0.5521(10) 0.035 Uiso 1 calc R . H15C H 0.3851(9) 0.1661(11) 0.6266(24) 0.035 Uiso 1 calc R . C16 C 0.5729(4) 0.2366(4) 0.5953(3) 0.0211(9) Uani 1 d . . H16A H 0.6441(5) 0.2720(4) 0.5842(22) 0.032 Uiso 1 calc R . H16B H 0.5233(19) 0.2532(4) 0.6526(9) 0.032 Uiso 1 calc R . H16C H 0.5411(23) 0.2642(5) 0.5368(13) 0.032 Uiso 1 calc R . C17 C 0.8758(4) 0.2674(4) 0.5892(3) 0.0216(9) Uani 1 d . . H17A H 0.7976(4) 0.2850(4) 0.5940(22) 0.032 Uiso 1 calc R . H17B H 0.9169(20) 0.3036(4) 0.5230(9) 0.032 Uiso 1 calc R . H17C H 0.9028(22) 0.2930(5) 0.6384(14) 0.032 Uiso 1 calc R . C18 C 1.0947(3) 0.1634(4) 0.5974(3) 0.0216(9) Uani 1 d . . H18A H 1.1507(10) 0.1499(19) 0.5424(15) 0.032 Uiso 1 calc R . H18B H 1.1241(16) 0.1442(18) 0.6577(9) 0.032 Uiso 1 calc R . H18C H 1.0742(6) 0.2410(4) 0.5823(23) 0.032 Uiso 1 calc R . C19 C 1.1223(3) -0.0680(4) 0.6337(3) 0.0193(8) Uani 1 d . . H19A H 1.1469(11) -0.0531(22) 0.6892(14) 0.029 Uiso 1 calc R . H19B H 1.1734(6) -0.0341(18) 0.5719(10) 0.029 Uiso 1 calc R . H19C H 1.1202(6) -0.1473(5) 0.6425(22) 0.029 Uiso 1 calc R . C20 C 0.9363(3) -0.2145(3) 0.6611(3) 0.0170(8) Uani 1 d . . H20A H 0.8648(3) -0.2510(4) 0.6778(20) 0.025 Uiso 1 calc R . H20B H 0.9743(20) -0.2413(5) 0.7157(14) 0.025 Uiso 1 calc R . H20C H 0.9806(19) -0.2305(4) 0.6012(7) 0.025 Uiso 1 calc R . C21 C 1.0827(3) 0.9898(3) 0.1395(3) 0.0123(7) Uani 1 d . . C22 C 1.0022(3) 0.9177(3) 0.1419(3) 0.0143(7) Uani 1 d . . C23 C 0.9007(3) 0.9696(3) 0.1262(3) 0.0142(7) Uani 1 d . . C24 C 0.8839(3) 1.0841(4) 0.1119(3) 0.0148(7) Uani 1 d . . C25 C 0.9691(3) 1.1570(3) 0.1095(3) 0.0139(7) Uani 1 d . . C26 C 1.0668(3) 1.1053(3) 0.1228(3) 0.0130(7) Uani 1 d . . C27 C 1.1856(3) 1.1192(3) 0.1242(3) 0.0137(7) Uani 1 d . . C28 C 1.2696(3) 1.1911(3) 0.1107(3) 0.0136(7) Uani 1 d . . C29 C 1.3743(3) 1.1401(4) 0.1136(3) 0.0145(7) Uani 1 d . . C30 C 1.3898(3) 1.0264(4) 0.1303(3) 0.0152(8) Uani 1 d . . C31 C 1.3012(3) 0.9523(4) 0.1453(3) 0.0141(7) Uani 1 d . . C32 C 1.2011(3) 1.0030(3) 0.1404(3) 0.0124(7) Uani 1 d . . C33 C 1.0187(3) 0.7967(3) 0.1587(3) 0.0175(8) Uani 1 d . . H33A H 1.0905(10) 0.7769(5) 0.1755(21) 0.026 Uiso 1 calc R . H33B H 1.0157(24) 0.7757(5) 0.0986(8) 0.026 Uiso 1 calc R . H33C H 0.9607(14) 0.7582(3) 0.2132(14) 0.026 Uiso 1 calc R . C34 C 0.8081(3) 0.8981(4) 0.1248(3) 0.0185(8) Uani 1 d . . H34A H 0.7644(15) 0.9395(8) 0.0782(16) 0.028 Uiso 1 calc R . H34B H 0.7612(14) 0.8755(20) 0.1910(6) 0.028 Uiso 1 calc R . H34C H 0.8388(3) 0.8329(12) 0.1041(21) 0.028 Uiso 1 calc R . C35 C 0.7735(3) 1.1318(4) 0.0977(3) 0.0224(9) Uani 1 d . . H35A H 0.7156(3) 1.0885(16) 0.1490(15) 0.034 Uiso 1 calc R . H35B H 0.7631(12) 1.1301(25) 0.0326(10) 0.034 Uiso 1 calc R . H35C H 0.7699(10) 1.2077(9) 0.1025(24) 0.034 Uiso 1 calc R . C36 C 0.9498(3) 1.2779(4) 0.0947(3) 0.0190(8) Uani 1 d . . H36A H 1.0178(7) 1.3137(5) 0.0937(21) 0.029 Uiso 1 calc R . H36B H 0.8920(17) 1.2905(4) 0.1490(12) 0.029 Uiso 1 calc R . H36C H 0.9269(23) 1.3085(6) 0.0319(11) 0.029 Uiso 1 calc R . C37 C 1.2552(4) 1.3124(4) 0.0951(3) 0.0207(9) Uani 1 d . . H37A H 1.1771(4) 1.3307(5) 0.1005(21) 0.031 Uiso 1 calc R . H37B H 1.2964(19) 1.3502(4) 0.0293(9) 0.031 Uiso 1 calc R . H37C H 1.2827(22) 1.3356(5) 0.1454(13) 0.031 Uiso 1 calc R . C38 C 1.4728(3) 1.2127(4) 0.0955(3) 0.0233(9) Uani 1 d . . H38A H 1.5227(13) 1.2095(20) 0.0334(12) 0.035 Uiso 1 calc R . H38B H 1.5113(15) 1.1873(16) 0.1500(12) 0.035 Uiso 1 calc R . H38C H 1.4484(4) 1.2885(6) 0.0915(23) 0.035 Uiso 1 calc R . C39 C 1.5035(3) 0.9809(4) 0.1302(3) 0.0222(9) Uani 1 d . . H39A H 1.5303(11) 0.9960(23) 0.1845(15) 0.033 Uiso 1 calc R . H39B H 1.5525(6) 1.0154(19) 0.0672(10) 0.033 Uiso 1 calc R . H39C H 1.5018(5) 0.9015(6) 0.1388(23) 0.033 Uiso 1 calc R . C40 C 1.3179(3) 0.8310(4) 0.1650(3) 0.0193(8) Uani 1 d . . H40A H 1.2477(6) 0.7951(4) 0.1730(21) 0.029 Uiso 1 calc R . H40B H 1.3461(23) 0.8039(5) 0.2256(12) 0.029 Uiso 1 calc R . H40C H 1.3708(18) 0.8145(4) 0.1095(10) 0.029 Uiso 1 calc R . C1S C 1.2254(5) 0.5428(4) 0.2070(4) 0.0315(11) Uani 1 d . . C2S C 1.1117(5) 0.5204(4) 0.2411(4) 0.0356(13) Uani 1 d . . H2SA H 1.0657(5) 0.5300(4) 0.1949(4) 0.043 Uiso 1 calc R . C3S C 1.0672(4) 0.4850(4) 0.3406(4) 0.0357(12) Uani 1 d . . H3SA H 0.9905(4) 0.4712(4) 0.3626(4) 0.043 Uiso 1 calc R . C4S C 1.1330(4) 0.4692(4) 0.4086(4) 0.0292(10) Uani 1 d . . H4SA H 1.1021(4) 0.4434(4) 0.4772(4) 0.035 Uiso 1 calc R . C5S C 1.2439(4) 0.4909(4) 0.3765(4) 0.0280(10) Uani 1 d . . H5SA H 1.2896(4) 0.4813(4) 0.4230(4) 0.034 Uiso 1 calc R . C6S C 1.2882(4) 0.5267(4) 0.2769(4) 0.0258(10) Uani 1 d . . H6SA H 1.3649(4) 0.5407(4) 0.2559(4) 0.031 Uiso 1 calc R . C7S C 1.2728(6) 0.5819(5) 0.0996(4) 0.049(2) Uani 1 d . . H7SD H 1.3522(8) 0.5687(34) 0.0874(6) 0.074 Uiso 1 calc R . H7SA H 1.2588(33) 0.6606(9) 0.0768(8) 0.074 Uiso 1 calc R . H7SB H 1.2387(27) 0.5422(26) 0.0637(5) 0.074 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb 0.01556(12) 0.00800(12) 0.02042(14) -0.00555(10) -0.00414(9) 0.00020(8) Cl1 0.0319(6) 0.0200(6) 0.0281(6) -0.0119(5) -0.0087(4) -0.0052(4) Cl2 0.0210(5) 0.0208(6) 0.0250(5) -0.0045(5) 0.0003(4) -0.0005(4) Cl3 0.0248(5) 0.0151(5) 0.0272(5) -0.0031(4) -0.0075(4) 0.0050(4) Cl4 0.0252(5) 0.0155(5) 0.0330(6) -0.0042(5) -0.0095(4) 0.0058(4) Cl5 0.0177(5) 0.0251(6) 0.0271(5) -0.0051(5) -0.0006(4) -0.0019(4) Cl6 0.0339(6) 0.0191(6) 0.0306(6) -0.0116(5) -0.0120(5) -0.0048(4) C1 0.014(2) 0.009(2) 0.018(2) -0.005(2) -0.0034(14) -0.0013(14) C2 0.016(2) 0.012(2) 0.018(2) -0.007(2) -0.0034(14) 0.0016(14) C3 0.017(2) 0.017(2) 0.019(2) -0.006(2) -0.0046(14) -0.002(2) C4 0.015(2) 0.021(2) 0.019(2) -0.007(2) -0.0061(15) 0.004(2) C5 0.017(2) 0.011(2) 0.015(2) -0.003(2) -0.0028(14) -0.0008(14) C6 0.013(2) 0.009(2) 0.017(2) -0.0053(15) -0.0037(13) -0.0009(13) C7 0.017(2) 0.011(2) 0.016(2) -0.006(2) -0.0044(14) 0.0032(14) C8 0.019(2) 0.007(2) 0.019(2) -0.005(2) -0.0019(14) -0.0024(14) C9 0.016(2) 0.014(2) 0.017(2) -0.006(2) -0.0017(14) -0.0017(15) C10 0.014(2) 0.013(2) 0.015(2) -0.005(2) -0.0021(13) 0.0018(14) C11 0.016(2) 0.008(2) 0.019(2) -0.007(2) -0.0032(14) 0.0013(14) C12 0.015(2) 0.009(2) 0.016(2) -0.0036(15) -0.0040(13) -0.0009(14) C13 0.020(2) 0.010(2) 0.032(2) -0.008(2) -0.005(2) -0.0030(15) C14 0.016(2) 0.028(3) 0.029(2) -0.010(2) -0.006(2) -0.003(2) C15 0.016(2) 0.024(2) 0.032(2) -0.013(2) -0.005(2) 0.008(2) C16 0.023(2) 0.011(2) 0.029(2) -0.005(2) -0.006(2) 0.003(2) C17 0.022(2) 0.013(2) 0.031(2) -0.008(2) -0.005(2) 0.000(2) C18 0.020(2) 0.014(2) 0.031(2) -0.008(2) -0.004(2) -0.004(2) C19 0.013(2) 0.019(2) 0.029(2) -0.011(2) -0.004(2) 0.002(2) C20 0.019(2) 0.009(2) 0.024(2) -0.007(2) -0.005(2) 0.0041(15) C21 0.012(2) 0.010(2) 0.015(2) -0.0039(15) -0.0024(13) 0.0001(13) C22 0.016(2) 0.012(2) 0.016(2) -0.005(2) -0.0025(14) -0.0014(14) C23 0.011(2) 0.013(2) 0.019(2) -0.007(2) -0.0018(13) 0.0003(14) C24 0.013(2) 0.014(2) 0.017(2) -0.006(2) -0.0018(14) 0.0023(14) C25 0.014(2) 0.012(2) 0.017(2) -0.007(2) -0.0028(14) 0.0038(14) C26 0.013(2) 0.009(2) 0.018(2) -0.0061(15) -0.0023(13) 0.0009(13) C27 0.014(2) 0.011(2) 0.018(2) -0.008(2) -0.0045(14) -0.0013(14) C28 0.015(2) 0.011(2) 0.016(2) -0.0057(15) -0.0026(13) -0.0013(14) C29 0.014(2) 0.015(2) 0.016(2) -0.007(2) -0.0013(13) -0.0038(14) C30 0.011(2) 0.019(2) 0.017(2) -0.006(2) -0.0035(14) 0.0008(15) C31 0.013(2) 0.014(2) 0.017(2) -0.006(2) -0.0038(13) 0.0010(14) C32 0.011(2) 0.010(2) 0.017(2) -0.0060(15) -0.0018(13) -0.0014(13) C33 0.022(2) 0.009(2) 0.023(2) -0.006(2) -0.007(2) 0.001(2) C34 0.016(2) 0.017(2) 0.025(2) -0.008(2) -0.005(2) -0.005(2) C35 0.013(2) 0.021(2) 0.033(2) -0.007(2) -0.005(2) 0.001(2) C36 0.018(2) 0.014(2) 0.026(2) -0.008(2) -0.006(2) 0.003(2) C37 0.023(2) 0.012(2) 0.029(2) -0.007(2) -0.006(2) -0.003(2) C38 0.018(2) 0.023(3) 0.030(2) -0.009(2) -0.005(2) -0.006(2) C39 0.012(2) 0.029(3) 0.029(2) -0.012(2) -0.007(2) 0.002(2) C40 0.016(2) 0.014(2) 0.030(2) -0.009(2) -0.007(2) 0.0010(15) C1S 0.054(3) 0.008(2) 0.038(3) -0.011(2) -0.016(2) 0.006(2) C2S 0.046(3) 0.012(2) 0.062(4) -0.018(2) -0.030(3) 0.006(2) C3S 0.029(2) 0.013(2) 0.065(4) -0.013(3) -0.007(2) -0.001(2) C4S 0.033(2) 0.013(2) 0.042(3) -0.012(2) -0.002(2) 0.003(2) C5S 0.033(2) 0.017(2) 0.040(3) -0.012(2) -0.014(2) 0.006(2) C6S 0.027(2) 0.014(2) 0.038(3) -0.010(2) -0.007(2) 0.004(2) C7S 0.094(5) 0.015(3) 0.038(3) -0.009(2) -0.009(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb Cl2 2.3517(11) . ? Sb Cl5 2.3634(11) . ? Sb Cl1 2.3691(11) . ? Sb Cl4 2.3725(11) . ? Sb Cl6 2.3747(11) . ? Sb Cl3 2.3775(11) . ? C1 C2 1.382(5) . ? C1 C6 1.430(6) . ? C1 C12 1.501(5) . ? C2 C3 1.430(5) . ? C2 C13 1.509(6) . ? C3 C4 1.406(6) . ? C3 C14 1.515(6) . ? C4 C5 1.431(6) . ? C4 C15 1.524(5) . ? C5 C6 1.377(5) . ? C5 C16 1.494(6) . ? C6 C7 1.491(5) . ? C7 C8 1.386(5) . ? C7 C12 1.424(6) . ? C8 C9 1.424(5) . ? C8 C17 1.500(6) . ? C9 C10 1.414(6) . ? C9 C18 1.507(6) . ? C10 C11 1.431(5) . ? C10 C19 1.514(5) . ? C11 C12 1.382(5) . ? C11 C20 1.493(6) . ? C21 C22 1.385(5) . ? C21 C26 1.426(6) . ? C21 C32 1.499(5) . ? C22 C23 1.427(5) . ? C22 C33 1.496(6) . ? C23 C24 1.419(6) . ? C23 C34 1.516(5) . ? C24 C25 1.435(5) . ? C24 C35 1.505(5) . ? C25 C26 1.377(5) . ? C25 C36 1.501(6) . ? C26 C27 1.509(5) . ? C27 C28 1.375(5) . ? C27 C32 1.435(6) . ? C28 C29 1.428(5) . ? C28 C37 1.497(6) . ? C29 C30 1.404(6) . ? C29 C38 1.512(6) . ? C30 C31 1.433(6) . ? C30 C39 1.500(5) . ? C31 C32 1.378(5) . ? C31 C40 1.497(6) . ? C1S C6S 1.373(6) . ? C1S C2S 1.414(8) . ? C1S C7S 1.485(8) . ? C2S C3S 1.376(8) . ? C3S C4S 1.378(7) . ? C4S C5S 1.378(7) . ? C5S C6S 1.377(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Sb Cl5 179.40(4) . . ? Cl2 Sb Cl1 90.90(4) . . ? Cl5 Sb Cl1 89.60(4) . . ? Cl2 Sb Cl4 89.78(4) . . ? Cl5 Sb Cl4 89.86(4) . . ? Cl1 Sb Cl4 90.44(4) . . ? Cl2 Sb Cl6 89.56(4) . . ? Cl5 Sb Cl6 89.94(4) . . ? Cl1 Sb Cl6 179.31(5) . . ? Cl4 Sb Cl6 90.08(4) . . ? Cl2 Sb Cl3 90.33(4) . . ? Cl5 Sb Cl3 90.03(4) . . ? Cl1 Sb Cl3 89.49(4) . . ? Cl4 Sb Cl3 179.87(4) . . ? Cl6 Sb Cl3 89.99(4) . . ? C2 C1 C6 123.2(4) . . ? C2 C1 C12 146.7(4) . . ? C6 C1 C12 90.0(3) . . ? C1 C2 C3 114.2(4) . . ? C1 C2 C13 123.1(4) . . ? C3 C2 C13 122.7(4) . . ? C4 C3 C2 121.9(4) . . ? C4 C3 C14 120.0(4) . . ? C2 C3 C14 118.1(4) . . ? C3 C4 C5 123.4(4) . . ? C3 C4 C15 118.7(4) . . ? C5 C4 C15 117.9(4) . . ? C6 C5 C4 113.5(4) . . ? C6 C5 C16 124.3(4) . . ? C4 C5 C16 122.2(4) . . ? C5 C6 C1 123.6(4) . . ? C5 C6 C7 146.6(4) . . ? C1 C6 C7 89.7(3) . . ? C8 C7 C12 122.8(4) . . ? C8 C7 C6 146.5(4) . . ? C12 C7 C6 90.7(3) . . ? C7 C8 C9 114.5(4) . . ? C7 C8 C17 122.8(4) . . ? C9 C8 C17 122.7(4) . . ? C10 C9 C8 122.4(4) . . ? C10 C9 C18 118.2(4) . . ? C8 C9 C18 119.4(4) . . ? C9 C10 C11 122.7(3) . . ? C9 C10 C19 118.5(4) . . ? C11 C10 C19 118.8(4) . . ? C12 C11 C10 113.6(4) . . ? C12 C11 C20 124.6(3) . . ? C10 C11 C20 121.7(3) . . ? C11 C12 C7 124.0(3) . . ? C11 C12 C1 146.3(4) . . ? C7 C12 C1 89.6(3) . . ? C22 C21 C26 123.6(3) . . ? C22 C21 C32 145.8(4) . . ? C26 C21 C32 90.4(3) . . ? C21 C22 C23 113.7(4) . . ? C21 C22 C33 123.8(4) . . ? C23 C22 C33 122.4(3) . . ? C24 C23 C22 122.7(3) . . ? C24 C23 C34 119.4(3) . . ? C22 C23 C34 117.9(4) . . ? C23 C24 C25 122.3(3) . . ? C23 C24 C35 119.2(4) . . ? C25 C24 C35 118.4(4) . . ? C26 C25 C24 113.8(4) . . ? C26 C25 C36 124.5(4) . . ? C24 C25 C36 121.7(3) . . ? C25 C26 C21 123.8(4) . . ? C25 C26 C27 146.2(4) . . ? C21 C26 C27 89.9(3) . . ? C28 C27 C32 123.3(4) . . ? C28 C27 C26 146.8(4) . . ? C32 C27 C26 89.7(3) . . ? C27 C28 C29 114.0(4) . . ? C27 C28 C37 124.3(4) . . ? C29 C28 C37 121.7(4) . . ? C30 C29 C28 123.0(4) . . ? C30 C29 C38 118.9(4) . . ? C28 C29 C38 118.1(4) . . ? C29 C30 C31 122.3(4) . . ? C29 C30 C39 118.9(4) . . ? C31 C30 C39 118.7(4) . . ? C32 C31 C30 114.0(4) . . ? C32 C31 C40 124.0(4) . . ? C30 C31 C40 122.1(3) . . ? C31 C32 C27 123.4(3) . . ? C31 C32 C21 146.5(4) . . ? C27 C32 C21 90.0(3) . . ? C6S C1S C2S 117.3(5) . . ? C6S C1S C7S 122.4(5) . . ? C2S C1S C7S 120.3(5) . . ? C3S C2S C1S 120.5(5) . . ? C2S C3S C4S 120.5(5) . . ? C3S C4S C5S 119.6(5) . . ? C6S C5S C4S 119.8(5) . . ? C1S C6S C5S 122.2(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.4(6) . . . . ? C12 C1 C2 C3 -177.6(5) . . . . ? C6 C1 C2 C13 176.6(4) . . . . ? C12 C1 C2 C13 1.4(9) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C13 C2 C3 C4 -178.7(4) . . . . ? C1 C2 C3 C14 -179.5(4) . . . . ? C13 C2 C3 C14 1.6(6) . . . . ? C2 C3 C4 C5 2.1(6) . . . . ? C14 C3 C4 C5 -178.2(4) . . . . ? C2 C3 C4 C15 -178.4(4) . . . . ? C14 C3 C4 C15 1.3(6) . . . . ? C3 C4 C5 C6 -2.2(6) . . . . ? C15 C4 C5 C6 178.3(4) . . . . ? C3 C4 C5 C16 176.3(4) . . . . ? C15 C4 C5 C16 -3.2(6) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C16 C5 C6 C1 -178.3(4) . . . . ? C4 C5 C6 C7 178.4(5) . . . . ? C16 C5 C6 C7 0.0(9) . . . . ? C2 C1 C6 C5 2.3(6) . . . . ? C12 C1 C6 C5 179.7(4) . . . . ? C2 C1 C6 C7 -176.8(4) . . . . ? C12 C1 C6 C7 0.6(3) . . . . ? C5 C6 C7 C8 -2.9(11) . . . . ? C1 C6 C7 C8 175.7(6) . . . . ? C5 C6 C7 C12 -179.2(6) . . . . ? C1 C6 C7 C12 -0.6(3) . . . . ? C12 C7 C8 C9 -0.3(6) . . . . ? C6 C7 C8 C9 -176.0(5) . . . . ? C12 C7 C8 C17 179.1(4) . . . . ? C6 C7 C8 C17 3.4(9) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C17 C8 C9 C10 -179.7(4) . . . . ? C7 C8 C9 C18 178.9(4) . . . . ? C17 C8 C9 C18 -0.5(6) . . . . ? C8 C9 C10 C11 0.6(6) . . . . ? C18 C9 C10 C11 -178.5(4) . . . . ? C8 C9 C10 C19 179.9(4) . . . . ? C18 C9 C10 C19 0.7(6) . . . . ? C9 C10 C11 C12 -0.3(6) . . . . ? C19 C10 C11 C12 -179.6(3) . . . . ? C9 C10 C11 C20 179.6(4) . . . . ? C19 C10 C11 C20 0.3(6) . . . . ? C10 C11 C12 C7 -0.3(6) . . . . ? C20 C11 C12 C7 179.8(4) . . . . ? C10 C11 C12 C1 175.5(5) . . . . ? C20 C11 C12 C1 -4.4(9) . . . . ? C8 C7 C12 C11 0.7(6) . . . . ? C6 C7 C12 C11 178.3(4) . . . . ? C8 C7 C12 C1 -177.0(4) . . . . ? C6 C7 C12 C1 0.6(3) . . . . ? C2 C1 C12 C11 -1.1(11) . . . . ? C6 C1 C12 C11 -177.2(6) . . . . ? C2 C1 C12 C7 175.4(6) . . . . ? C6 C1 C12 C7 -0.6(3) . . . . ? C26 C21 C22 C23 -0.2(6) . . . . ? C32 C21 C22 C23 -172.8(5) . . . . ? C26 C21 C22 C33 179.6(4) . . . . ? C32 C21 C22 C33 6.9(8) . . . . ? C21 C22 C23 C24 -1.3(6) . . . . ? C33 C22 C23 C24 178.9(4) . . . . ? C21 C22 C23 C34 178.4(3) . . . . ? C33 C22 C23 C34 -1.3(6) . . . . ? C22 C23 C24 C25 1.6(6) . . . . ? C34 C23 C24 C25 -178.1(4) . . . . ? C22 C23 C24 C35 -178.9(4) . . . . ? C34 C23 C24 C35 1.4(6) . . . . ? C23 C24 C25 C26 -0.3(6) . . . . ? C35 C24 C25 C26 -179.8(4) . . . . ? C23 C24 C25 C36 -179.7(4) . . . . ? C35 C24 C25 C36 0.8(6) . . . . ? C24 C25 C26 C21 -1.2(6) . . . . ? C36 C25 C26 C21 178.2(4) . . . . ? C24 C25 C26 C27 174.6(5) . . . . ? C36 C25 C26 C27 -6.0(9) . . . . ? C22 C21 C26 C25 1.5(6) . . . . ? C32 C21 C26 C25 177.4(4) . . . . ? C22 C21 C26 C27 -176.2(4) . . . . ? C32 C21 C26 C27 -0.3(3) . . . . ? C25 C26 C27 C28 -2.5(11) . . . . ? C21 C26 C27 C28 174.0(6) . . . . ? C25 C26 C27 C32 -176.2(6) . . . . ? C21 C26 C27 C32 0.3(3) . . . . ? C32 C27 C28 C29 0.5(6) . . . . ? C26 C27 C28 C29 -172.0(5) . . . . ? C32 C27 C28 C37 -179.1(4) . . . . ? C26 C27 C28 C37 8.4(9) . . . . ? C27 C28 C29 C30 -1.1(6) . . . . ? C37 C28 C29 C30 178.5(4) . . . . ? C27 C28 C29 C38 177.6(4) . . . . ? C37 C28 C29 C38 -2.8(6) . . . . ? C28 C29 C30 C31 0.5(6) . . . . ? C38 C29 C30 C31 -178.2(4) . . . . ? C28 C29 C30 C39 178.9(4) . . . . ? C38 C29 C30 C39 0.3(6) . . . . ? C29 C30 C31 C32 0.8(6) . . . . ? C39 C30 C31 C32 -177.7(4) . . . . ? C29 C30 C31 C40 -178.8(4) . . . . ? C39 C30 C31 C40 2.7(6) . . . . ? C30 C31 C32 C27 -1.4(6) . . . . ? C40 C31 C32 C27 178.2(4) . . . . ? C30 C31 C32 C21 173.2(5) . . . . ? C40 C31 C32 C21 -7.2(9) . . . . ? C28 C27 C32 C31 0.8(6) . . . . ? C26 C27 C32 C31 176.7(4) . . . . ? C28 C27 C32 C21 -176.2(4) . . . . ? C26 C27 C32 C21 -0.3(3) . . . . ? C22 C21 C32 C31 -1.3(11) . . . . ? C26 C21 C32 C31 -175.2(6) . . . . ? C22 C21 C32 C27 174.2(6) . . . . ? C26 C21 C32 C27 0.3(3) . . . . ? C6S C1S C2S C3S 0.6(7) . . . . ? C7S C1S C2S C3S -179.5(5) . . . . ? C1S C2S C3S C4S -1.0(7) . . . . ? C2S C3S C4S C5S 1.1(7) . . . . ? C3S C4S C5S C6S -0.9(7) . . . . ? C2S C1S C6S C5S -0.4(7) . . . . ? C7S C1S C6S C5S 179.7(5) . . . . ? C4S C5S C6S C1S 0.6(7) . . . . ? _refine_diff_density_max 4.201 _refine_diff_density_min -4.415 _refine_diff_density_rms 0.210 data_pier-jsx _database_code_CSD 162665 _audit_creation_method SHELXL _chemical_name_systematic ; Octamethylbiphenylene hexachloroantimonate ; _chemical_name_common ? _chemical_formula_moiety '(C20 H24)^+^, (Cl6 Sb)^-^' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H24 Cl6 Sb' _chemical_formula_weight 598.84 _chemical_melting_point ? _chemical_compound_source 'chemical synthesis' 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' '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 'triclinic' _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6059(1) _cell_length_b 11.7390(2) _cell_length_c 13.2313(1) _cell_angle_alpha 115.116(1) _cell_angle_beta 100.611(1) _cell_angle_gamma 95.783(1) _cell_volume 1165.32(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7277 _cell_measurement_theta_min 2 _cell_measurement_theta_max 35 _exptl_crystal_description 'prism' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method none _exptl_crystal_F_000 594 _exptl_absorpt_coefficient_mu 1.876 _exptl_absorpt_correction_type 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.621 _exptl_absorpt_correction_T_max 0.724 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens/Bruker SMART 1K CCD' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15888 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 35.72 _reflns_number_total 9719 _reflns_number_observed 6977 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 2 with very negative F^2^ or flagged by us for potential systematic errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+1.8291P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9717 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_obs 0.0506 _refine_ls_wR_factor_all 0.0894 _refine_ls_wR_factor_obs 0.0753 _refine_ls_goodness_of_fit_all 1.125 _refine_ls_goodness_of_fit_obs 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_restrained_S_obs 1.128 _refine_ls_shift/esd_max 0.248 _refine_ls_shift/esd_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sb1 Sb 0.02286(3) 0.67449(2) 0.29286(2) 0.01599(5) Uani 1 d . . Cl1 Cl 0.28612(10) 0.62820(8) 0.30791(8) 0.0275(2) Uani 1 d . . Cl2 Cl -0.02761(10) 0.57514(7) 0.41030(7) 0.0223(2) Uani 1 d . . Cl3 Cl 0.12271(10) 0.87384(7) 0.46119(7) 0.0249(2) Uani 1 d . . Cl4 Cl -0.23840(10) 0.72326(8) 0.28187(7) 0.0259(2) Uani 1 d . . Cl5 Cl -0.08048(11) 0.47625(8) 0.12648(7) 0.0268(2) Uani 1 d . . Cl6 Cl 0.07361(11) 0.77330(8) 0.17615(7) 0.0270(2) Uani 1 d . . C1 C 0.3617(4) 0.9845(3) 0.1455(2) 0.0169(5) Uani 1 d . . C2 C 0.3767(4) 1.0218(3) 0.2615(3) 0.0200(6) Uani 1 d . . C3 C 0.3048(4) 1.1284(3) 0.3167(3) 0.0199(6) Uani 1 d . . C4 C 0.2233(4) 1.1902(3) 0.2559(3) 0.0209(6) Uani 1 d . . C5 C 0.2124(4) 1.1523(3) 0.1377(3) 0.0199(6) Uani 1 d . . C6 C 0.2842(4) 1.0494(3) 0.0853(2) 0.0168(5) Uani 1 d . . C7 C 0.3123(3) 0.9567(3) -0.0239(2) 0.0156(5) Uani 1 d . . C8 C 0.2821(4) 0.9136(3) -0.1415(3) 0.0170(5) Uani 1 d . . C9 C 0.3374(4) 0.7996(3) -0.2001(2) 0.0170(5) Uani 1 d . . C10 C 0.4122(4) 0.7323(3) -0.1409(3) 0.0181(5) Uani 1 d . . C11 C 0.4325(4) 0.7738(3) -0.0213(3) 0.0183(5) Uani 1 d . . C12 C 0.3869(3) 0.8894(3) 0.0355(3) 0.0165(5) Uani 1 d . . C13 C 0.4616(4) 0.9581(4) 0.3264(3) 0.0248(7) Uani 1 d . . C14 C 0.3110(5) 1.1757(4) 0.4428(3) 0.0292(7) Uani 1 d . . C15 C 0.1470(5) 1.3003(4) 0.3203(4) 0.0306(8) Uani 1 d . . C16 C 0.1280(5) 1.2176(4) 0.0742(3) 0.0285(7) Uani 1 d . . C17 C 0.1950(5) 0.9823(4) -0.2013(3) 0.0240(7) Uani 1 d . . C18 C 0.3122(5) 0.7399(3) -0.3288(3) 0.0236(6) Uani 1 d . . C19 C 0.4592(5) 0.6093(3) -0.2114(3) 0.0252(7) Uani 1 d . . C20 C 0.4908(5) 0.6949(4) 0.0372(3) 0.0274(7) Uani 1 d . . H13A H 0.3929(49) 0.9246(37) 0.3555(34) 0.029(10) Uiso 1 d . . H13B H 0.5530(56) 1.0218(45) 0.3830(40) 0.043(12) Uiso 1 d . . H13C H 0.4962(49) 0.8884(40) 0.2784(35) 0.033(11) Uiso 1 d . . H14A H 0.3246(59) 1.2693(50) 0.4863(42) 0.055(14) Uiso 1 d . . H14B H 0.4012(71) 1.1673(55) 0.4800(49) 0.076(18) Uiso 1 d . . H14C H 0.2151(67) 1.1538(51) 0.4523(44) 0.064(16) Uiso 1 d . . H15A H 0.0935(55) 1.2844(43) 0.3751(39) 0.048(13) Uiso 1 d . . H15B H 0.0804(59) 1.3215(46) 0.2735(42) 0.053(14) Uiso 1 d . . H15C H 0.2309(70) 1.3768(56) 0.3759(49) 0.074(18) Uiso 1 d . . H16A H 0.1643(53) 1.3095(45) 0.1159(38) 0.043(12) Uiso 1 d . . H16B H 0.0144(55) 1.1996(40) 0.0620(36) 0.037(12) Uiso 1 d . . H16C H 0.1497(59) 1.1897(47) -0.0006(43) 0.056(14) Uiso 1 d . . H17A H 0.1173(78) 0.9325(62) -0.2541(56) 0.088(21) Uiso 1 d . . H17B H 0.2596(69) 1.0202(54) -0.2265(48) 0.071(17) Uiso 1 d . . H17C H 0.1762(67) 1.0533(57) -0.1549(49) 0.072(18) Uiso 1 d . . H18A H 0.4027(50) 0.7207(37) -0.3558(34) 0.031(11) Uiso 1 d . . H18B H 0.2650(48) 0.7939(39) -0.3593(34) 0.031(10) Uiso 1 d . . H18C H 0.2416(54) 0.6677(44) -0.3622(37) 0.040(12) Uiso 1 d . . H19A H 0.5157(51) 0.6161(39) -0.2571(36) 0.033(11) Uiso 1 d . . H19B H 0.3711(52) 0.5434(41) -0.2532(36) 0.033(11) Uiso 1 d . . H19C H 0.5332(51) 0.5841(39) -0.1619(36) 0.036(11) Uiso 1 d . . H20A H 0.4371(48) 0.6069(40) -0.0067(34) 0.028(10) Uiso 1 d . . H20B H 0.4645(54) 0.7211(42) 0.1061(40) 0.042(12) Uiso 1 d . . H20C H 0.5932(60) 0.6954(44) 0.0413(39) 0.048(14) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.01730(9) 0.01778(9) 0.01445(9) 0.00885(7) 0.00260(7) 0.00549(7) Cl1 0.0203(4) 0.0315(4) 0.0362(5) 0.0188(4) 0.0081(3) 0.0106(3) Cl2 0.0265(4) 0.0249(4) 0.0205(4) 0.0146(3) 0.0056(3) 0.0061(3) Cl3 0.0313(4) 0.0201(3) 0.0184(4) 0.0063(3) 0.0017(3) 0.0040(3) Cl4 0.0220(4) 0.0344(4) 0.0254(4) 0.0164(3) 0.0046(3) 0.0132(3) Cl5 0.0307(4) 0.0219(4) 0.0202(4) 0.0041(3) 0.0034(3) 0.0038(3) Cl6 0.0312(4) 0.0318(4) 0.0239(4) 0.0194(3) 0.0045(3) 0.0043(3) C1 0.0164(13) 0.0201(13) 0.0159(13) 0.0093(11) 0.0053(11) 0.0033(11) C2 0.0168(14) 0.0246(15) 0.0197(14) 0.0113(12) 0.0053(11) 0.0013(11) C3 0.0175(14) 0.0247(15) 0.0169(14) 0.0092(12) 0.0059(11) -0.0003(11) C4 0.0199(15) 0.0225(14) 0.0206(15) 0.0084(12) 0.0092(12) 0.0039(12) C5 0.0194(15) 0.0212(14) 0.0210(15) 0.0112(12) 0.0051(12) 0.0047(11) C6 0.0163(13) 0.0199(13) 0.0167(13) 0.0104(11) 0.0047(11) 0.0043(11) C7 0.0130(13) 0.0169(13) 0.0169(13) 0.0089(11) 0.0015(10) 0.0016(10) C8 0.0149(13) 0.0177(13) 0.0178(13) 0.0086(11) 0.0020(11) 0.0016(10) C9 0.0152(13) 0.0177(13) 0.0159(13) 0.0072(11) 0.0022(10) -0.0011(10) C10 0.0154(13) 0.0163(13) 0.0200(14) 0.0069(11) 0.0025(11) 0.0019(11) C11 0.0151(13) 0.0187(13) 0.0215(14) 0.0113(12) 0.0010(11) 0.0021(11) C12 0.0121(13) 0.0186(13) 0.0196(13) 0.0102(11) 0.0025(10) 0.0015(10) C13 0.024(2) 0.033(2) 0.023(2) 0.0185(15) 0.0034(13) 0.0052(14) C14 0.037(2) 0.035(2) 0.017(2) 0.0120(15) 0.0108(15) 0.006(2) C15 0.037(2) 0.030(2) 0.030(2) 0.013(2) 0.018(2) 0.016(2) C16 0.033(2) 0.030(2) 0.030(2) 0.017(2) 0.011(2) 0.019(2) C17 0.031(2) 0.026(2) 0.0175(15) 0.0127(14) 0.0022(14) 0.0079(14) C18 0.028(2) 0.020(2) 0.0175(15) 0.0056(12) 0.0033(13) 0.0003(13) C19 0.026(2) 0.020(2) 0.025(2) 0.0067(13) 0.0050(14) 0.0082(14) C20 0.032(2) 0.025(2) 0.028(2) 0.0150(15) 0.0019(15) 0.0114(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 Cl5 2.3592(9) . ? Sb1 Cl6 2.3638(8) . ? Sb1 Cl4 2.3694(8) . ? Sb1 Cl3 2.3750(9) . ? Sb1 Cl1 2.3752(8) . ? Sb1 Cl2 2.3766(7) . ? C1 C2 1.381(4) . ? C1 C6 1.443(4) . ? C1 C12 1.483(4) . ? C2 C3 1.425(4) . ? C2 C13 1.503(4) . ? C3 C4 1.434(4) . ? C3 C14 1.506(4) . ? C4 C5 1.414(4) . ? C4 C15 1.506(4) . ? C5 C6 1.385(4) . ? C5 C16 1.501(4) . ? C6 C7 1.476(4) . ? C7 C8 1.379(4) . ? C7 C12 1.448(4) . ? C8 C9 1.416(4) . ? C8 C17 1.510(4) . ? C9 C10 1.448(4) . ? C9 C18 1.503(4) . ? C10 C11 1.413(4) . ? C10 C19 1.494(4) . ? C11 C12 1.383(4) . ? C11 C20 1.506(4) . ? C13 H13A 0.90(4) . ? C13 H13B 0.96(5) . ? C13 H13C 0.92(4) . ? C14 H14A 0.98(5) . ? C14 H14B 0.88(6) . ? C14 H14C 0.89(6) . ? C15 H15A 1.00(5) . ? C15 H15B 0.90(5) . ? C15 H15C 0.99(6) . ? C16 H16A 0.96(5) . ? C16 H16B 0.95(4) . ? C16 H16C 0.96(5) . ? C17 H17A 0.82(7) . ? C17 H17B 0.87(6) . ? C17 H17C 0.85(6) . ? C18 H18A 0.92(4) . ? C18 H18B 0.97(4) . ? C18 H18C 0.87(5) . ? C19 H19A 0.87(4) . ? C19 H19B 0.92(4) . ? C19 H19C 0.99(4) . ? C20 H20A 0.96(4) . ? C20 H20B 0.91(4) . ? C20 H20C 0.87(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl5 Sb1 Cl6 89.99(3) . . ? Cl5 Sb1 Cl4 90.33(3) . . ? Cl6 Sb1 Cl4 90.37(3) . . ? Cl5 Sb1 Cl3 179.04(3) . . ? Cl6 Sb1 Cl3 90.51(3) . . ? Cl4 Sb1 Cl3 88.85(3) . . ? Cl5 Sb1 Cl1 90.68(3) . . ? Cl6 Sb1 Cl1 90.15(3) . . ? Cl4 Sb1 Cl1 178.86(4) . . ? Cl3 Sb1 Cl1 90.14(3) . . ? Cl5 Sb1 Cl2 90.04(3) . . ? Cl6 Sb1 Cl2 179.89(3) . . ? Cl4 Sb1 Cl2 89.74(3) . . ? Cl3 Sb1 Cl2 89.46(3) . . ? Cl1 Sb1 Cl2 89.73(3) . . ? C2 C1 C6 123.3(3) . . ? C2 C1 C12 147.1(3) . . ? C6 C1 C12 89.5(2) . . ? C1 C2 C3 114.2(3) . . ? C1 C2 C13 124.1(3) . . ? C3 C2 C13 121.7(3) . . ? C2 C3 C4 122.3(3) . . ? C2 C3 C14 118.8(3) . . ? C4 C3 C14 118.9(3) . . ? C5 C4 C3 122.6(3) . . ? C5 C4 C15 118.6(3) . . ? C3 C4 C15 118.9(3) . . ? C6 C5 C4 114.5(3) . . ? C6 C5 C16 122.9(3) . . ? C4 C5 C16 122.5(3) . . ? C5 C6 C1 123.0(3) . . ? C5 C6 C7 146.1(3) . . ? C1 C6 C7 90.7(2) . . ? C8 C7 C12 123.8(3) . . ? C8 C7 C6 146.2(3) . . ? C12 C7 C6 89.6(2) . . ? C7 C8 C9 114.1(2) . . ? C7 C8 C17 122.3(3) . . ? C9 C8 C17 123.6(3) . . ? C8 C9 C10 122.1(3) . . ? C8 C9 C18 120.5(3) . . ? C10 C9 C18 117.3(3) . . ? C11 C10 C9 122.7(3) . . ? C11 C10 C19 119.1(3) . . ? C9 C10 C19 118.0(3) . . ? C12 C11 C10 114.2(2) . . ? C12 C11 C20 123.2(3) . . ? C10 C11 C20 122.5(3) . . ? C11 C12 C7 122.8(3) . . ? C11 C12 C1 146.5(3) . . ? C7 C12 C1 90.2(2) . . ? C2 C13 H13A 110.9(24) . . ? C2 C13 H13B 106.1(26) . . ? H13A C13 H13B 114.9(36) . . ? C2 C13 H13C 111.4(25) . . ? H13A C13 H13C 103.8(34) . . ? H13B C13 H13C 109.8(36) . . ? C3 C14 H14A 114.3(27) . . ? C3 C14 H14B 111.1(36) . . ? H14A C14 H14B 97.8(46) . . ? C3 C14 H14C 110.9(35) . . ? H14A C14 H14C 98.1(40) . . ? H14B C14 H14C 123.1(48) . . ? C4 C15 H15A 111.8(25) . . ? C4 C15 H15B 113.0(30) . . ? H15A C15 H15B 111.8(39) . . ? C4 C15 H15C 110.7(30) . . ? H15A C15 H15C 99.5(39) . . ? H15B C15 H15C 109.3(42) . . ? C5 C16 H16A 111.0(26) . . ? C5 C16 H16B 112.7(25) . . ? H16A C16 H16B 107.7(34) . . ? C5 C16 H16C 110.6(27) . . ? H16A C16 H16C 107.7(38) . . ? H16B C16 H16C 106.9(38) . . ? C8 C17 H17A 110.8(42) . . ? C8 C17 H17B 111.9(35) . . ? H17A C17 H17B 110.9(51) . . ? C8 C17 H17C 113.5(36) . . ? H17A C17 H17C 115.9(53) . . ? H17B C17 H17C 92.7(46) . . ? C9 C18 H18A 115.9(25) . . ? C9 C18 H18B 110.5(23) . . ? H18A C18 H18B 108.6(31) . . ? C9 C18 H18C 110.8(28) . . ? H18A C18 H18C 105.8(35) . . ? H18B C18 H18C 104.6(36) . . ? C10 C19 H19A 112.8(26) . . ? C10 C19 H19B 111.9(24) . . ? H19A C19 H19B 109.6(38) . . ? C10 C19 H19C 110.9(24) . . ? H19A C19 H19C 102.6(34) . . ? H19B C19 H19C 108.5(33) . . ? C11 C20 H20A 111.0(23) . . ? C11 C20 H20B 110.3(26) . . ? H20A C20 H20B 104.8(35) . . ? C11 C20 H20C 110.1(30) . . ? H20A C20 H20C 105.9(36) . . ? H20B C20 H20C 114.5(41) . . ? _refine_diff_density_max 0.741 _refine_diff_density_min -0.902 _refine_diff_density_rms 0.155 data_pier-gsx _database_code_CSD 158741 _audit_creation_method SHELXL _chemical_name_systematic ; Octamethylbiphenylene hexachloroantimonate, dichloromethane monosolvate ; _chemical_name_common ? _chemical_formula_moiety '(C20 H24)^+^, (Cl6 Sb)^-^, (C H2 Cl2)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H26 Cl8 Sb' _chemical_formula_weight 683.77 _chemical_melting_point ? _chemical_compound_source 'chemical synthesis' 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' '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 'triclinic' _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6343(2) _cell_length_b 10.6007(2) _cell_length_c 13.8761(2) _cell_angle_alpha 81.964(1) _cell_angle_beta 70.035(1) _cell_angle_gamma 80.276(1) _cell_volume 1307.70(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2 _cell_measurement_theta_max 36 _exptl_crystal_description 'prism' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method ? _exptl_crystal_F_000 678 _exptl_absorpt_coefficient_mu 1.881 _exptl_absorpt_correction_type 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.598 _exptl_absorpt_correction_T_max 0.726 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16484 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 36.21 _reflns_number_total 11276 _reflns_number_observed 8130 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 17 with very negative F^2^ or flagged by us for potential systematic errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0173P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11259 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_obs 0.0369 _refine_ls_wR_factor_all 0.0792 _refine_ls_wR_factor_obs 0.0671 _refine_ls_goodness_of_fit_all 0.987 _refine_ls_goodness_of_fit_obs 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_restrained_S_obs 1.028 _refine_ls_shift/esd_max 0.014 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sb Sb -0.16610(2) 0.942814(13) 0.238060(10) 0.01298(4) Uani 1 d . . Cl1 Cl 0.04315(7) 0.86857(6) 0.10233(4) 0.02742(13) Uani 1 d . . Cl2 Cl -0.22228(7) 0.72894(5) 0.29244(4) 0.02203(11) Uani 1 d . . Cl3 Cl -0.11422(7) 1.15854(5) 0.18896(5) 0.02646(12) Uani 1 d . . Cl4 Cl -0.37311(7) 1.01617(5) 0.37772(4) 0.02396(12) Uani 1 d . . Cl5 Cl -0.31652(7) 0.96929(6) 0.13124(4) 0.02502(12) Uani 1 d . . Cl6 Cl -0.01570(7) 0.91594(6) 0.34731(5) 0.02727(13) Uani 1 d . . C1 C 0.5114(2) 1.6945(2) -0.1120(2) 0.0139(4) Uani 1 d . . C2 C 0.6082(2) 1.7815(2) -0.1678(2) 0.0158(4) Uani 1 d . . C3 C 0.6486(2) 1.7805(2) -0.2757(2) 0.0178(4) Uani 1 d . . C4 C 0.5938(3) 1.6970(2) -0.3233(2) 0.0178(4) Uani 1 d . . C5 C 0.4870(2) 1.6146(2) -0.2652(2) 0.0161(4) Uani 1 d . . C6 C 0.4528(2) 1.6129(2) -0.1598(2) 0.0140(4) Uani 1 d . . C7 C 0.3610(2) 1.5623(2) -0.05732(15) 0.0134(4) Uani 1 d . . C8 C 0.2532(2) 1.4841(2) -0.0025(2) 0.0146(4) Uani 1 d . . C9 C 0.2005(2) 1.4946(2) 0.1058(2) 0.0139(4) Uani 1 d . . C10 C 0.2571(2) 1.5776(2) 0.1527(2) 0.0144(4) Uani 1 d . . C11 C 0.3654(2) 1.6582(2) 0.09560(15) 0.0138(4) Uani 1 d . . C12 C 0.4174(2) 1.6462(2) -0.00928(15) 0.0129(3) Uani 1 d . . C13 C 0.6656(3) 1.8719(2) -0.1204(2) 0.0221(5) Uani 1 d . . C14 C 0.7512(4) 1.8743(3) -0.3436(2) 0.0295(6) Uani 1 d . . C15 C 0.6491(3) 1.6989(3) -0.4390(2) 0.0234(5) Uani 1 d . . C16 C 0.4152(3) 1.5390(3) -0.3146(2) 0.0259(5) Uani 1 d . . C17 C 0.1955(3) 1.3958(2) -0.0518(2) 0.0201(4) Uani 1 d . . C18 C 0.0763(3) 1.4229(2) 0.1735(2) 0.0186(4) Uani 1 d . . C19 C 0.1899(3) 1.5831(2) 0.2677(2) 0.0191(4) Uani 1 d . . C20 C 0.4151(3) 1.7512(2) 0.1457(2) 0.0220(5) Uani 1 d . . H13A H 0.7789(38) 1.8592(29) -0.1428(22) 0.044(9) Uiso 1 d . . H13B H 0.6300(34) 1.8584(28) -0.0517(23) 0.037(8) Uiso 1 d . . H13C H 0.6326(34) 1.9598(30) -0.1374(21) 0.037(8) Uiso 1 d . . H14A H 0.7656(43) 1.8778(36) -0.4103(30) 0.069(12) Uiso 1 d . . H14B H 0.8359(56) 1.8624(44) -0.3322(33) 0.094(16) Uiso 1 d . . H14C H 0.7144(49) 1.9530(42) -0.3248(30) 0.077(13) Uiso 1 d . . H15A H 0.7488(32) 1.6978(24) -0.4648(18) 0.018(7) Uiso 1 d . . H15B H 0.6153(34) 1.7762(30) -0.4669(22) 0.037(8) Uiso 1 d . . H15C H 0.6300(38) 1.6283(32) -0.4643(24) 0.050(10) Uiso 1 d . . H16A H 0.3773(37) 1.5886(31) -0.3691(24) 0.046(9) Uiso 1 d . . H16B H 0.3215(38) 1.5113(32) -0.2703(24) 0.048(9) Uiso 1 d . . H16C H 0.4831(35) 1.4642(29) -0.3431(21) 0.036(8) Uiso 1 d . . H17A H 0.1999(30) 1.3075(26) -0.0234(19) 0.024(7) Uiso 1 d . . H17B H 0.2507(37) 1.3909(30) -0.1199(24) 0.047(9) Uiso 1 d . . H17C H 0.0886(34) 1.4242(27) -0.0428(20) 0.031(8) Uiso 1 d . . H18A H 0.1009(34) 1.3670(29) 0.2315(22) 0.039(8) Uiso 1 d . . H18B H 0.0372(32) 1.3703(26) 0.1410(20) 0.029(7) Uiso 1 d . . H18C H -0.0023(33) 1.4786(27) 0.2088(20) 0.026(7) Uiso 1 d . . H19A H 0.1907(36) 1.4922(31) 0.3005(22) 0.045(9) Uiso 1 d . . H19B H 0.0958(32) 1.6287(26) 0.2857(19) 0.024(7) Uiso 1 d . . H19C H 0.2388(29) 1.6240(24) 0.2954(18) 0.016(6) Uiso 1 d . . H20A H 0.3300(32) 1.8082(26) 0.1844(19) 0.023(7) Uiso 1 d . . H20B H 0.4847(33) 1.8088(27) 0.0988(20) 0.030(8) Uiso 1 d . . H20C H 0.4680(37) 1.7078(31) 0.1901(23) 0.045(9) Uiso 1 d . . Cl7 Cl -0.10732(9) 1.37553(7) 0.45662(5) 0.0377(2) Uani 1 d . . Cl8 Cl -0.35225(8) 1.22631(6) 0.56781(5) 0.03023(13) Uani 1 d . . C21 C -0.1758(3) 1.2263(3) 0.4726(2) 0.0280(5) Uani 1 d . . H21A H -0.1847(34) 1.2156(28) 0.4161(23) 0.035(8) Uiso 1 d . . H21B H -0.1044(39) 1.1641(33) 0.4931(25) 0.053(10) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb 0.01212(6) 0.01388(6) 0.01353(6) -0.00300(4) -0.00351(5) -0.00322(4) Cl1 0.0203(3) 0.0323(3) 0.0202(3) -0.0022(2) 0.0017(2) 0.0048(2) Cl2 0.0300(3) 0.0160(2) 0.0207(2) -0.0024(2) -0.0062(2) -0.0083(2) Cl3 0.0295(3) 0.0180(2) 0.0319(3) 0.0015(2) -0.0079(3) -0.0104(2) Cl4 0.0222(3) 0.0239(3) 0.0201(2) -0.0070(2) 0.0014(2) -0.0009(2) Cl5 0.0247(3) 0.0290(3) 0.0274(3) -0.0057(2) -0.0162(2) -0.0012(2) Cl6 0.0299(3) 0.0302(3) 0.0306(3) -0.0043(2) -0.0203(3) -0.0048(2) C1 0.0135(10) 0.0133(8) 0.0150(9) -0.0014(7) -0.0059(7) 0.0001(7) C2 0.0134(10) 0.0136(9) 0.0206(10) 0.0015(7) -0.0064(8) -0.0028(7) C3 0.0157(10) 0.0169(9) 0.0188(10) 0.0034(7) -0.0050(8) -0.0022(8) C4 0.0166(11) 0.0187(10) 0.0136(9) 0.0012(7) -0.0016(8) 0.0003(8) C5 0.0173(10) 0.0158(9) 0.0147(9) -0.0028(7) -0.0048(8) -0.0006(7) C6 0.0137(10) 0.0124(8) 0.0155(9) -0.0011(7) -0.0046(7) -0.0007(7) C7 0.0146(10) 0.0118(8) 0.0138(8) -0.0013(7) -0.0048(7) -0.0010(7) C8 0.0136(10) 0.0127(8) 0.0173(9) -0.0029(7) -0.0051(8) 0.0001(7) C9 0.0105(9) 0.0124(8) 0.0163(9) -0.0003(7) -0.0018(7) -0.0009(7) C10 0.0131(10) 0.0149(9) 0.0153(9) -0.0025(7) -0.0054(8) 0.0009(7) C11 0.0134(10) 0.0137(8) 0.0151(9) -0.0029(7) -0.0055(7) -0.0008(7) C12 0.0114(9) 0.0126(8) 0.0147(8) -0.0012(7) -0.0043(7) -0.0020(7) C13 0.0219(12) 0.0211(11) 0.0249(12) 0.0003(9) -0.0076(10) -0.0090(9) C14 0.0278(15) 0.0320(14) 0.0255(13) 0.0096(11) -0.0053(11) -0.0124(11) C15 0.0255(13) 0.0261(12) 0.0140(10) 0.0020(8) -0.0018(9) -0.0041(10) C16 0.037(2) 0.0270(12) 0.0177(10) -0.0032(9) -0.0102(11) -0.0100(11) C17 0.0214(12) 0.0202(10) 0.0202(10) -0.0055(8) -0.0055(9) -0.0067(9) C18 0.0148(10) 0.0200(10) 0.0185(10) -0.0009(8) -0.0011(8) -0.0060(8) C19 0.0180(11) 0.0242(11) 0.0135(9) -0.0041(8) -0.0026(8) -0.0014(9) C20 0.0229(12) 0.0252(11) 0.0195(10) -0.0091(9) -0.0041(9) -0.0079(9) Cl7 0.0428(4) 0.0406(4) 0.0268(3) -0.0041(3) -0.0020(3) -0.0162(3) Cl8 0.0302(3) 0.0330(3) 0.0282(3) -0.0084(2) -0.0067(3) -0.0073(3) C21 0.0326(15) 0.0284(13) 0.0234(12) -0.0086(10) -0.0096(11) 0.0014(11) _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 Sb Cl1 2.3487(6) . ? Sb Cl5 2.3642(6) . ? Sb Cl4 2.3655(6) . ? Sb Cl2 2.3791(5) . ? Sb Cl3 2.3794(5) . ? Sb Cl6 2.3913(6) . ? C1 C2 1.384(3) . ? C1 C6 1.445(3) . ? C1 C12 1.478(3) . ? C2 C3 1.413(3) . ? C2 C13 1.504(3) . ? C3 C4 1.435(3) . ? C3 C14 1.513(3) . ? C4 C5 1.418(3) . ? C4 C15 1.507(3) . ? C5 C6 1.383(3) . ? C5 C16 1.502(3) . ? C6 C7 1.476(3) . ? C7 C8 1.386(3) . ? C7 C12 1.451(3) . ? C8 C9 1.425(3) . ? C8 C17 1.506(3) . ? C9 C10 1.436(3) . ? C9 C18 1.494(3) . ? C10 C11 1.413(3) . ? C10 C19 1.508(3) . ? C11 C12 1.385(3) . ? C11 C20 1.504(3) . ? C13 H13A 1.02(3) . ? C13 H13B 0.90(3) . ? C13 H13C 0.96(3) . ? C14 H14A 0.88(4) . ? C14 H14B 0.87(5) . ? C14 H14C 0.89(4) . ? C15 H15A 0.90(3) . ? C15 H15B 0.91(3) . ? C15 H15C 0.94(3) . ? C16 H16A 1.00(3) . ? C16 H16B 0.97(3) . ? C16 H16C 0.97(3) . ? C17 H17A 0.96(3) . ? C17 H17B 0.92(3) . ? C17 H17C 0.99(3) . ? C18 H18A 1.00(3) . ? C18 H18B 0.96(3) . ? C18 H18C 0.92(3) . ? C19 H19A 1.01(3) . ? C19 H19B 0.92(3) . ? C19 H19C 0.89(3) . ? C20 H20A 0.97(3) . ? C20 H20B 0.99(3) . ? C20 H20C 0.95(3) . ? Cl7 C21 1.772(3) . ? Cl8 C21 1.761(3) . ? C21 H21A 0.84(3) . ? C21 H21B 0.96(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Sb Cl5 90.63(2) . . ? Cl1 Sb Cl4 178.50(2) . . ? Cl5 Sb Cl4 90.86(2) . . ? Cl1 Sb Cl2 90.48(2) . . ? Cl5 Sb Cl2 90.42(2) . . ? Cl4 Sb Cl2 89.32(2) . . ? Cl1 Sb Cl3 91.17(2) . . ? Cl5 Sb Cl3 90.26(2) . . ? Cl4 Sb Cl3 89.02(2) . . ? Cl2 Sb Cl3 178.21(2) . . ? Cl1 Sb Cl6 89.79(2) . . ? Cl5 Sb Cl6 179.54(2) . . ? Cl4 Sb Cl6 88.72(2) . . ? Cl2 Sb Cl6 89.40(2) . . ? Cl3 Sb Cl6 89.91(2) . . ? C2 C1 C6 122.9(2) . . ? C2 C1 C12 146.7(2) . . ? C6 C1 C12 90.1(2) . . ? C1 C2 C3 114.2(2) . . ? C1 C2 C13 124.2(2) . . ? C3 C2 C13 121.6(2) . . ? C2 C3 C4 123.0(2) . . ? C2 C3 C14 118.2(2) . . ? C4 C3 C14 118.8(2) . . ? C5 C4 C3 122.1(2) . . ? C5 C4 C15 118.9(2) . . ? C3 C4 C15 118.9(2) . . ? C6 C5 C4 114.1(2) . . ? C6 C5 C16 123.4(2) . . ? C4 C5 C16 122.5(2) . . ? C5 C6 C1 123.4(2) . . ? C5 C6 C7 146.3(2) . . ? C1 C6 C7 90.1(2) . . ? C8 C7 C12 123.3(2) . . ? C8 C7 C6 146.6(2) . . ? C12 C7 C6 89.94(15) . . ? C7 C8 C9 114.0(2) . . ? C7 C8 C17 123.5(2) . . ? C9 C8 C17 122.5(2) . . ? C8 C9 C10 122.4(2) . . ? C8 C9 C18 119.7(2) . . ? C10 C9 C18 117.8(2) . . ? C11 C10 C9 123.0(2) . . ? C11 C10 C19 119.4(2) . . ? C9 C10 C19 117.6(2) . . ? C12 C11 C10 114.2(2) . . ? C12 C11 C20 123.8(2) . . ? C10 C11 C20 122.0(2) . . ? C11 C12 C7 123.1(2) . . ? C11 C12 C1 146.8(2) . . ? C7 C12 C1 89.8(2) . . ? C2 C13 H13A 111.7(17) . . ? C2 C13 H13B 109.5(18) . . ? H13A C13 H13B 108.5(26) . . ? C2 C13 H13C 111.9(18) . . ? H13A C13 H13C 108.6(23) . . ? H13B C13 H13C 106.5(26) . . ? C3 C14 H14A 116.0(24) . . ? C3 C14 H14B 111.3(28) . . ? H14A C14 H14B 110.5(37) . . ? C3 C14 H14C 109.3(26) . . ? H14A C14 H14C 106.6(33) . . ? H14B C14 H14C 102.3(37) . . ? C4 C15 H15A 111.5(16) . . ? C4 C15 H15B 109.5(18) . . ? H15A C15 H15B 102.5(23) . . ? C4 C15 H15C 114.5(18) . . ? H15A C15 H15C 104.9(26) . . ? H15B C15 H15C 113.2(27) . . ? C5 C16 H16A 115.1(18) . . ? C5 C16 H16B 115.3(18) . . ? H16A C16 H16B 97.0(26) . . ? C5 C16 H16C 110.8(18) . . ? H16A C16 H16C 108.8(24) . . ? H16B C16 H16C 108.9(25) . . ? C8 C17 H17A 115.2(16) . . ? C8 C17 H17B 111.4(19) . . ? H17A C17 H17B 103.5(24) . . ? C8 C17 H17C 110.1(16) . . ? H17A C17 H17C 105.0(22) . . ? H17B C17 H17C 111.4(26) . . ? C9 C18 H18A 113.5(17) . . ? C9 C18 H18B 117.0(16) . . ? H18A C18 H18B 106.5(22) . . ? C9 C18 H18C 110.5(16) . . ? H18A C18 H18C 101.2(23) . . ? H18B C18 H18C 106.7(24) . . ? C10 C19 H19A 107.7(17) . . ? C10 C19 H19B 111.7(16) . . ? H19A C19 H19B 112.5(24) . . ? C10 C19 H19C 114.7(15) . . ? H19A C19 H19C 107.2(23) . . ? H19B C19 H19C 103.1(22) . . ? C11 C20 H20A 110.6(16) . . ? C11 C20 H20B 116.1(16) . . ? H20A C20 H20B 105.1(22) . . ? C11 C20 H20C 111.7(19) . . ? H20A C20 H20C 109.6(24) . . ? H20B C20 H20C 103.4(24) . . ? Cl8 C21 Cl7 111.63(14) . . ? Cl8 C21 H21A 108.1(21) . . ? Cl7 C21 H21A 107.0(19) . . ? Cl8 C21 H21B 110.1(19) . . ? Cl7 C21 H21B 105.2(19) . . ? H21A C21 H21B 114.6(29) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.0(3) . . . . ? C12 C1 C2 C3 -173.7(3) . . . . ? C6 C1 C2 C13 177.1(2) . . . . ? C12 C1 C2 C13 5.3(5) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C13 C2 C3 C4 -178.9(2) . . . . ? C1 C2 C3 C14 178.5(2) . . . . ? C13 C2 C3 C14 -0.5(3) . . . . ? C2 C3 C4 C5 4.1(3) . . . . ? C14 C3 C4 C5 -174.2(2) . . . . ? C2 C3 C4 C15 -177.2(2) . . . . ? C14 C3 C4 C15 4.5(3) . . . . ? C3 C4 C5 C6 -6.1(3) . . . . ? C15 C4 C5 C6 175.2(2) . . . . ? C3 C4 C5 C16 172.4(2) . . . . ? C15 C4 C5 C16 -6.3(3) . . . . ? C4 C5 C6 C1 4.4(3) . . . . ? C16 C5 C6 C1 -174.1(2) . . . . ? C4 C5 C6 C7 177.5(3) . . . . ? C16 C5 C6 C7 -1.0(5) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? C12 C1 C6 C5 175.0(2) . . . . ? C2 C1 C6 C7 -176.6(2) . . . . ? C12 C1 C6 C7 -1.1(2) . . . . ? C5 C6 C7 C8 1.1(6) . . . . ? C1 C6 C7 C8 175.3(3) . . . . ? C5 C6 C7 C12 -173.1(3) . . . . ? C1 C6 C7 C12 1.1(2) . . . . ? C12 C7 C8 C9 0.8(3) . . . . ? C6 C7 C8 C9 -172.2(3) . . . . ? C12 C7 C8 C17 -179.3(2) . . . . ? C6 C7 C8 C17 7.7(5) . . . . ? C7 C8 C9 C10 -1.0(3) . . . . ? C17 C8 C9 C10 179.2(2) . . . . ? C7 C8 C9 C18 175.6(2) . . . . ? C17 C8 C9 C18 -4.3(3) . . . . ? C8 C9 C10 C11 2.1(3) . . . . ? C18 C9 C10 C11 -174.5(2) . . . . ? C8 C9 C10 C19 178.4(2) . . . . ? C18 C9 C10 C19 1.8(3) . . . . ? C9 C10 C11 C12 -2.7(3) . . . . ? C19 C10 C11 C12 -179.0(2) . . . . ? C9 C10 C11 C20 175.6(2) . . . . ? C19 C10 C11 C20 -0.7(3) . . . . ? C10 C11 C12 C7 2.6(3) . . . . ? C20 C11 C12 C7 -175.7(2) . . . . ? C10 C11 C12 C1 174.3(3) . . . . ? C20 C11 C12 C1 -4.0(5) . . . . ? C8 C7 C12 C11 -1.8(3) . . . . ? C6 C7 C12 C11 174.4(2) . . . . ? C8 C7 C12 C1 -177.3(2) . . . . ? C6 C7 C12 C1 -1.1(2) . . . . ? C2 C1 C12 C11 1.1(6) . . . . ? C6 C1 C12 C11 -171.9(3) . . . . ? C2 C1 C12 C7 174.2(3) . . . . ? C6 C1 C12 C7 1.1(2) . . . . ? _refine_diff_density_max 0.899 _refine_diff_density_min -1.135 _refine_diff_density_rms 0.129