# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 loop_ _publ_author_name 'S.V.Rosokha' 'S.V.Lindeman' 'J.K.Kochi' _publ_contact_author_name 'Prof J Kochi' _publ_contact_author_address ; Department of Chemistry University of Houston Houston Texas 77204-5641 UNITED STATES OF AMERICA ; _publ_contact_author_email 'JKOCHI@MAIL.UH.EDU' _publ_requested_journal 'Perkin Transactions 2' _publ_section_title ; Novel bis-Arene (sandwich) complexes with NO+ acceptor. Isolation, X-ray crystallography and electronic structure. ; data_raj-csx _database_code_CSD 181218 _audit_creation_method SHELXL _chemical_name_systematic ; Toluene/nitrozonium hexachloroantimonate molecular complex 2:1 ; _chemical_name_common ? _chemical_formula_moiety ; 2(C7 H8), (N O)^+^, (Cl6 Sb)^-^ ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H16 Cl6 N O Sb' _chemical_formula_weight 548.73 _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' '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' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 11.215(2) _cell_length_b 15.911(3) _cell_length_c 11.501(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2052.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4242 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 36.3 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method none _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 2.127 _exptl_absorpt_correction_type 'Empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.803 _exptl_absorpt_correction_T_max 0.928 _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 131 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 25541 _diffrn_reflns_av_R_equivalents 0.1157 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 36.31 _reflns_number_total 4945 _reflns_number_observed 2234 _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 16 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^)+(0.0268P)^2^+4.1054P] 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=1.2Uiso/eq of an adjacent carbon atom (1.5Uiso/eq for Me-hydrogens) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4929 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1657 _refine_ls_R_factor_obs 0.0610 _refine_ls_wR_factor_all 0.1186 _refine_ls_wR_factor_obs 0.0828 _refine_ls_goodness_of_fit_all 1.093 _refine_ls_goodness_of_fit_obs 1.168 _refine_ls_restrained_S_all 1.112 _refine_ls_restrained_S_obs 1.168 _refine_ls_shift/esd_max 0.069 _refine_ls_shift/esd_mean 0.002 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 0.93345(3) 0.7500 -0.49925(5) 0.01539(8) Uani 1 d S . Cl1 Cl 0.93420(12) 0.60172(6) -0.4975(2) 0.0407(3) Uani 1 d . . Cl2 Cl 1.0861(2) 0.7500 -0.6401(2) 0.0350(5) Uani 1 d S . Cl3 Cl 1.0781(2) 0.7500 -0.34819(15) 0.0283(4) Uani 1 d S . Cl4 Cl 0.7809(2) 0.7500 -0.3564(2) 0.0287(5) Uani 1 d S . Cl5 Cl 0.7845(2) 0.7500 -0.6449(2) 0.0335(5) Uani 1 d S . N1 N 0.9696(8) 0.7500 -0.1119(6) 0.021(2) Uiso 0.77(2) d SP 1 O1 O 0.8686(7) 0.7500 -0.1137(7) 0.017(2) Uiso 0.77(2) d SP 1 O1A O 0.9008(26) 0.7500 -0.1233(23) 0.020(7) Uiso 0.23(2) d SP 2 N1A N 0.8238(27) 0.7500 -0.0574(26) 0.031(8) Uiso 0.23(2) d SP 2 C1 C 0.8528(5) 0.5635(3) -0.1087(4) 0.0243(9) Uani 1 d . . C2 C 0.8002(4) 0.5913(3) -0.0048(6) 0.0317(9) Uani 1 d . . H2A H 0.7165(4) 0.5861(3) 0.0054(6) 0.038 Uiso 1 calc R . C3 C 0.8688(6) 0.6261(3) 0.0829(4) 0.0351(13) Uani 1 d . . H3A H 0.8321(6) 0.6440(3) 0.1531(4) 0.042 Uiso 1 calc R . C4 C 0.9895(5) 0.6351(3) 0.0690(5) 0.0348(13) Uani 1 d . . H4A H 1.0367(5) 0.6586(3) 0.1294(5) 0.042 Uiso 1 calc R . C5 C 1.0417(5) 0.6096(3) -0.0338(5) 0.0359(14) Uani 1 d . . H5A H 1.1249(5) 0.6173(3) -0.0451(5) 0.043 Uiso 1 calc R . C6 C 0.9737(5) 0.5729(3) -0.1207(5) 0.0305(11) Uani 1 d . . H6A H 1.0116(5) 0.5538(3) -0.1897(5) 0.037 Uiso 1 calc R . C7 C 0.7784(6) 0.5238(4) -0.2022(5) 0.054(2) Uani 1 d . . H7D H 0.8302(7) 0.5045(26) -0.2654(19) 0.081 Uiso 1 calc R . H7A H 0.7216(28) 0.5652(10) -0.2325(28) 0.081 Uiso 1 calc R . H7B H 0.7347(33) 0.4758(18) -0.1699(11) 0.081 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 Sb1 0.01092(12) 0.0223(2) 0.01297(13) 0.000 0.0002(3) 0.000 Cl1 0.0398(6) 0.0234(5) 0.0588(7) -0.0043(9) -0.0042(11) -0.0014(5) Cl2 0.0187(10) 0.0654(14) 0.0210(9) 0.000 0.0075(8) 0.000 Cl3 0.0138(9) 0.0524(12) 0.0189(8) 0.000 -0.0039(8) 0.000 Cl4 0.0162(10) 0.0531(13) 0.0169(10) 0.000 0.0012(8) 0.000 Cl5 0.0197(11) 0.0620(15) 0.0189(10) 0.000 -0.0064(8) 0.000 C1 0.031(2) 0.016(2) 0.026(2) 0.007(2) -0.005(2) -0.001(2) C2 0.024(2) 0.031(2) 0.041(2) 0.014(3) 0.006(3) 0.001(2) C3 0.055(4) 0.027(3) 0.023(2) 0.007(2) 0.006(2) 0.012(2) C4 0.048(4) 0.022(2) 0.035(3) 0.001(2) -0.017(3) -0.001(2) C5 0.021(2) 0.027(2) 0.059(4) 0.017(2) -0.009(2) -0.004(2) C6 0.036(3) 0.023(2) 0.032(3) 0.004(2) 0.012(2) 0.006(2) C7 0.081(5) 0.033(3) 0.048(3) 0.007(3) -0.029(4) -0.023(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 Sb1 Cl2 2.357(2) . ? Sb1 Cl1 2.3594(11) . ? Sb1 Cl1 2.3595(11) 7_575 ? Sb1 Cl5 2.366(2) . ? Sb1 Cl4 2.373(2) . ? Sb1 Cl3 2.377(2) . ? N1 O1 1.133(11) . ? O1A N1A 1.15(4) . ? C1 C6 1.372(7) . ? C1 C2 1.404(7) . ? C1 C7 1.500(7) . ? C2 C3 1.385(8) . ? C3 C4 1.370(8) . ? C4 C5 1.380(7) . ? C5 C6 1.386(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 Sb1 Cl1 90.19(4) . . ? Cl2 Sb1 Cl1 90.19(4) . 7_575 ? Cl1 Sb1 Cl1 178.92(10) . 7_575 ? Cl2 Sb1 Cl5 91.51(8) . . ? Cl1 Sb1 Cl5 90.50(4) . . ? Cl1 Sb1 Cl5 90.50(4) 7_575 . ? Cl2 Sb1 Cl4 179.57(8) . . ? Cl1 Sb1 Cl4 89.80(4) . . ? Cl1 Sb1 Cl4 89.80(4) 7_575 . ? Cl5 Sb1 Cl4 88.92(5) . . ? Cl2 Sb1 Cl3 90.37(6) . . ? Cl1 Sb1 Cl3 89.50(4) . . ? Cl1 Sb1 Cl3 89.50(4) 7_575 . ? Cl5 Sb1 Cl3 178.12(8) . . ? Cl4 Sb1 Cl3 89.20(7) . . ? C6 C1 C2 117.8(5) . . ? C6 C1 C7 121.6(5) . . ? C2 C1 C7 120.6(5) . . ? C3 C2 C1 120.8(5) . . ? C4 C3 C2 120.3(5) . . ? C3 C4 C5 119.3(5) . . ? C4 C5 C6 120.5(5) . . ? C1 C6 C5 121.2(5) . . ? _refine_diff_density_max 0.798 _refine_diff_density_min -1.263 _refine_diff_density_rms 0.170 data_ros-lsx _database_code_CSD 187240 _audit_creation_method SHELXL _chemical_name_systematic ; o-Xylene/Nitrosonium hexachloroantimonate molecular complex 2:1 ; _chemical_name_common ? _chemical_formula_moiety '2(C8 H10), (N O)^+^, (Cl6 Sb)^-^' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H20 Cl6 N O Sb' _chemical_formula_weight 576.78 _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' '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' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.666(2) _cell_length_b 16.482(3) _cell_length_c 23.254(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.369(4) _cell_angle_gamma 90.00 _cell_volume 4469.9(14) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7308 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description 'prism' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method none _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 1.957 _exptl_absorpt_correction_type 'semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.667 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens/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 47115 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4802 _reflns_number_observed 4519 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker AXS, 1997-01)' _computing_cell_refinement 'SAINT V6.28a (Bruker AXS, 1997-01)' _computing_data_reduction 'SAINT & SADABS V2.03 (Sheldrick, 2001)' _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 54 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^)+(0.1471P)^2^+86.8004P] 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 = 1.2Uiso/eq of an adjacent atom (1.5Uiso/eq for Me-groups) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4748 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_obs 0.0930 _refine_ls_wR_factor_all 0.2540 _refine_ls_wR_factor_obs 0.2419 _refine_ls_goodness_of_fit_all 1.070 _refine_ls_goodness_of_fit_obs 1.091 _refine_ls_restrained_S_all 1.122 _refine_ls_restrained_S_obs 1.091 _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 Sb1 Sb 0.54007(7) 0.19790(5) 0.24587(4) 0.0223(4) Uani 1 d . . Cl1 Cl 0.6814(3) 0.1993(3) 0.3210(2) 0.0414(10) Uani 1 d . . Cl2 Cl 0.6846(3) 0.1760(2) 0.1779(2) 0.0349(9) Uani 1 d . . Cl3 Cl 0.3964(3) 0.1945(2) 0.1730(2) 0.0393(10) Uani 1 d . . Cl4 Cl 0.3961(3) 0.2224(2) 0.3143(2) 0.0372(9) Uani 1 d . . Cl5 Cl 0.5633(3) 0.3397(2) 0.2337(2) 0.0466(11) Uani 1 d . . Cl6 Cl 0.5205(3) 0.0566(2) 0.2569(2) 0.0384(9) Uani 1 d . . Sb2 Sb -0.04436(7) 0.74831(5) 0.00138(4) 0.0207(4) Uani 1 d . . Cl7 Cl -0.1933(3) 0.7585(3) -0.0693(2) 0.0461(11) Uani 1 d . . Cl8 Cl 0.0942(3) 0.7661(2) -0.07000(15) 0.0312(8) Uani 1 d . . Cl9 Cl -0.1828(3) 0.7292(3) 0.0735(2) 0.0408(10) Uani 1 d . . Cl10 Cl 0.1019(3) 0.7388(2) 0.07347(14) 0.0306(8) Uani 1 d . . Cl11 Cl -0.0509(4) 0.8898(2) 0.0156(2) 0.0475(10) Uani 1 d . . Cl12 Cl -0.0360(3) 0.6070(2) -0.0136(2) 0.0411(10) Uani 1 d . . C1 C 0.1233(12) 0.3951(8) 0.2833(6) 0.030(3) Uani 1 d . . C2 C 0.0201(13) 0.3733(9) 0.3131(7) 0.036(4) Uani 1 d . . H2A H 0.0131(13) 0.3844(9) 0.3530(7) 0.044 Uiso 1 calc R . C3 C -0.0670(13) 0.3363(10) 0.2827(9) 0.049(5) Uani 1 d . . H3A H -0.1340(13) 0.3202(10) 0.3021(9) 0.059 Uiso 1 calc R . C4 C -0.0598(12) 0.3220(8) 0.2245(6) 0.029(3) Uani 1 d . . H4A H -0.1229(12) 0.3007(8) 0.2028(6) 0.034 Uiso 1 calc R . C5 C 0.0406(14) 0.3395(9) 0.1994(7) 0.041(4) Uani 1 d . . H5A H 0.0492(14) 0.3243(9) 0.1604(7) 0.049 Uiso 1 calc R . C6 C 0.1329(12) 0.3788(9) 0.2274(7) 0.036(4) Uani 1 d . . C7 C 0.2178(14) 0.4384(9) 0.3191(8) 0.046(4) Uani 1 d . . H7A H 0.2866(35) 0.4044(32) 0.3209(42) 0.069 Uiso 1 calc R . H7B H 0.1907(39) 0.4479(62) 0.3581(16) 0.069 Uiso 1 calc R . H7C H 0.2360(71) 0.4904(33) 0.3011(28) 0.069 Uiso 1 calc R . C8 C 0.2380(13) 0.3999(10) 0.1965(7) 0.044(4) Uani 1 d . . H8A H 0.3028(23) 0.3689(51) 0.2126(32) 0.067 Uiso 1 calc R . H8B H 0.2534(54) 0.4581(16) 0.2008(40) 0.067 Uiso 1 calc R . H8C H 0.2275(37) 0.3868(62) 0.1556(11) 0.067 Uiso 1 calc R . C11 C 0.0211(11) 0.0572(9) 0.2974(6) 0.028(3) Uani 1 d . . C12 C -0.0471(12) 0.0932(9) 0.2545(7) 0.032(3) Uani 1 d . . H12A H -0.1236(12) 0.1086(9) 0.2625(7) 0.038 Uiso 1 calc R . C13 C -0.0045(14) 0.1066(8) 0.2011(7) 0.038(4) Uani 1 d . . H13A H -0.0528(14) 0.1286(8) 0.1715(7) 0.046 Uiso 1 calc R . C14 C 0.1064(14) 0.0885(9) 0.1899(7) 0.042(4) Uani 1 d . . H14A H 0.1372(14) 0.1002(9) 0.1534(7) 0.051 Uiso 1 calc R . C15 C 0.1741(13) 0.0526(10) 0.2329(8) 0.047(4) Uani 1 d . . H15A H 0.2504(13) 0.0376(10) 0.2243(8) 0.056 Uiso 1 calc R . C16 C 0.1360(11) 0.0381(7) 0.2862(6) 0.022(3) Uani 1 d . . C17 C -0.0275(16) 0.0465(11) 0.3575(7) 0.052(4) Uani 1 d . . H17A H 0.0205(59) 0.0760(58) 0.3857(10) 0.078 Uiso 1 calc R . H17B H -0.0284(92) -0.0113(12) 0.3675(21) 0.078 Uiso 1 calc R . H17C H -0.1059(40) 0.0680(64) 0.3580(15) 0.078 Uiso 1 calc R . C18 C 0.2127(13) -0.0028(10) 0.3312(7) 0.045(4) Uani 1 d . . H18A H 0.2849(40) -0.0189(60) 0.3138(13) 0.067 Uiso 1 calc R . H18B H 0.1740(42) -0.0510(39) 0.3460(35) 0.067 Uiso 1 calc R . H18C H 0.2286(77) 0.0351(25) 0.3629(23) 0.067 Uiso 1 calc R . C21 C 0.3724(12) 0.9298(8) 0.0572(6) 0.032(3) Uani 1 d . . C22 C 0.4655(17) 0.9013(10) 0.0904(8) 0.055(5) Uani 1 d . . H22A H 0.4655(17) 0.9059(10) 0.1312(8) 0.066 Uiso 1 calc R . C23 C 0.5599(14) 0.8654(9) 0.0628(7) 0.043(4) Uani 1 d . . H23A H 0.6238(14) 0.8447(9) 0.0842(7) 0.052 Uiso 1 calc R . C24 C 0.5555(14) 0.8616(11) 0.0045(9) 0.050(5) Uani 1 d . . H24A H 0.6179(14) 0.8381(11) -0.0150(9) 0.059 Uiso 1 calc R . C25 C 0.4657(13) 0.8902(8) -0.0263(6) 0.030(3) Uani 1 d . . H25A H 0.4666(13) 0.8863(8) -0.0671(6) 0.036 Uiso 1 calc R . C26 C 0.3737(14) 0.9245(9) -0.0014(7) 0.042(4) Uani 1 d . . C27 C 0.2741(16) 0.9705(11) 0.0905(10) 0.068(6) Uani 1 d . . H27A H 0.2850(70) 0.9601(73) 0.1318(12) 0.102 Uiso 1 calc R . H27B H 0.2004(19) 0.9479(64) 0.0772(46) 0.102 Uiso 1 calc R . H27C H 0.2749(78) 1.0291(17) 0.0835(49) 0.102 Uiso 1 calc R . C28 C 0.2720(15) 0.9573(11) -0.0351(9) 0.058(5) Uani 1 d . . H28A H 0.2755(61) 0.9389(65) -0.0751(16) 0.087 Uiso 1 calc R . H28B H 0.2733(62) 1.0167(11) -0.0340(47) 0.087 Uiso 1 calc R . H28C H 0.2011(15) 0.9375(65) -0.0182(35) 0.087 Uiso 1 calc R . C31 C 0.4746(12) 0.5959(8) 0.0278(5) 0.026(3) Uani 1 d . . C32 C 0.5350(12) 0.6418(8) -0.0113(7) 0.032(3) Uani 1 d . . H32A H 0.6144(12) 0.6522(8) -0.0052(7) 0.038 Uiso 1 calc R . C33 C 0.4777(17) 0.6721(10) -0.0593(9) 0.057(5) Uani 1 d . . H33A H 0.5172(17) 0.7052(10) -0.0857(9) 0.068 Uiso 1 calc R . C34 C 0.3604(16) 0.6538(11) -0.0692(9) 0.057(5) Uani 1 d . . H34A H 0.3200(16) 0.6736(11) -0.1023(9) 0.068 Uiso 1 calc R . C35 C 0.3072(13) 0.6068(10) -0.0295(7) 0.039(4) Uani 1 d . . H35A H 0.2289(13) 0.5934(10) -0.0367(7) 0.046 Uiso 1 calc R . C36 C 0.3575(12) 0.5778(8) 0.0193(6) 0.028(3) Uani 1 d . . C37 C 0.5386(17) 0.5631(11) 0.0819(7) 0.057(5) Uani 1 d . . H37A H 0.6214(17) 0.5648(72) 0.0759(22) 0.085 Uiso 1 calc R . H37B H 0.5149(82) 0.5070(28) 0.0889(32) 0.085 Uiso 1 calc R . H37C H 0.5199(87) 0.5967(47) 0.1152(13) 0.085 Uiso 1 calc R . C38 C 0.2944(13) 0.5276(8) 0.0615(7) 0.038(4) Uani 1 d . . H38A H 0.2231(44) 0.5075(50) 0.0435(15) 0.057 Uiso 1 calc R . H38B H 0.2764(77) 0.5608(19) 0.0951(20) 0.057 Uiso 1 calc R . H38C H 0.3421(36) 0.4815(35) 0.0737(34) 0.057 Uiso 1 calc R . O1 O 0.0974(15) 0.2163(8) 0.2963(7) 0.066(4) Uani 1 d . . N1 N 0.1541(12) 0.2207(9) 0.2636(13) 0.080(8) Uani 1 d . . O2 O 0.3988(15) 0.7469(7) 0.0526(6) 0.063(4) Uani 1 d . . N2 N 0.3369(12) 0.7625(9) 0.0246(9) 0.046(4) 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 Sb1 0.0215(6) 0.0201(6) 0.0251(6) 0.0025(4) -0.0012(4) 0.0011(3) Cl1 0.022(2) 0.063(3) 0.039(2) 0.000(2) -0.006(2) 0.000(2) Cl2 0.027(2) 0.047(2) 0.031(2) -0.003(2) 0.0052(14) 0.001(2) Cl3 0.026(2) 0.055(2) 0.037(2) 0.012(2) -0.009(2) -0.003(2) Cl4 0.023(2) 0.044(2) 0.044(2) 0.003(2) 0.009(2) 0.005(2) Cl5 0.047(2) 0.023(2) 0.070(3) 0.015(2) 0.010(2) -0.005(2) Cl6 0.043(2) 0.028(2) 0.045(2) 0.003(2) 0.002(2) 0.001(2) Sb2 0.0217(6) 0.0232(6) 0.0170(5) 0.0005(3) -0.0024(4) 0.0022(4) Cl7 0.030(2) 0.079(3) 0.028(2) 0.001(2) -0.006(2) 0.010(2) Cl8 0.023(2) 0.043(2) 0.027(2) 0.006(2) 0.0043(14) 0.0011(15) Cl9 0.031(2) 0.066(3) 0.026(2) 0.001(2) 0.0030(15) 0.002(2) Cl10 0.029(2) 0.041(2) 0.021(2) -0.0022(15) -0.0043(14) 0.0023(15) Cl11 0.070(3) 0.020(2) 0.052(2) -0.006(2) 0.000(2) 0.013(2) Cl12 0.061(3) 0.030(2) 0.032(2) -0.007(2) 0.002(2) -0.015(2) C1 0.038(9) 0.019(7) 0.033(9) 0.001(6) -0.004(7) 0.000(6) C2 0.057(11) 0.023(8) 0.029(8) 0.012(6) 0.002(7) 0.007(7) C3 0.027(9) 0.042(10) 0.078(14) 0.015(9) -0.004(8) -0.010(7) C4 0.026(8) 0.031(8) 0.029(8) 0.009(6) -0.010(6) -0.005(6) C5 0.047(11) 0.025(8) 0.052(10) 0.000(7) 0.000(8) 0.001(7) C6 0.032(9) 0.025(8) 0.050(10) -0.004(7) 0.006(7) -0.013(6) C7 0.057(11) 0.012(7) 0.068(12) 0.006(7) -0.014(8) 0.006(7) C8 0.051(10) 0.032(9) 0.051(10) 0.001(8) 0.009(8) -0.004(7) C11 0.024(8) 0.031(8) 0.028(8) 0.006(6) -0.004(6) -0.013(6) C12 0.027(8) 0.019(8) 0.048(10) 0.002(7) -0.001(7) -0.004(6) C13 0.057(11) 0.017(7) 0.040(9) 0.017(7) -0.003(8) 0.001(7) C14 0.053(11) 0.027(8) 0.047(10) 0.012(7) 0.010(8) 0.003(7) C15 0.030(9) 0.039(10) 0.072(13) 0.001(9) 0.001(8) 0.004(7) C16 0.022(7) 0.012(6) 0.031(8) -0.005(6) -0.013(6) -0.007(5) C17 0.077(13) 0.038(10) 0.042(10) -0.007(8) -0.003(8) -0.003(8) C18 0.045(10) 0.036(9) 0.052(10) 0.016(8) -0.014(7) -0.002(7) C21 0.039(9) 0.014(7) 0.044(10) -0.003(6) 0.006(7) 0.008(6) C22 0.095(15) 0.033(9) 0.037(10) 0.001(8) 0.002(9) -0.014(9) C23 0.051(11) 0.029(8) 0.048(11) -0.006(8) -0.014(8) 0.012(7) C24 0.026(9) 0.048(11) 0.075(13) -0.015(10) 0.002(8) 0.005(8) C25 0.050(10) 0.011(7) 0.030(8) -0.005(6) 0.011(7) -0.008(6) C26 0.057(11) 0.018(7) 0.050(11) 0.011(7) 0.001(8) 0.003(7) C27 0.071(13) 0.039(11) 0.094(16) -0.029(11) 0.018(11) 0.007(9) C28 0.060(12) 0.033(9) 0.081(14) -0.008(9) -0.011(10) 0.007(8) C31 0.042(9) 0.023(7) 0.012(7) -0.009(6) 0.005(6) 0.016(6) C32 0.023(8) 0.022(8) 0.050(10) -0.002(7) -0.001(7) 0.008(6) C33 0.073(14) 0.026(9) 0.071(13) 0.013(9) 0.023(10) -0.004(8) C34 0.054(12) 0.043(10) 0.073(13) 0.012(10) -0.005(10) 0.015(9) C35 0.029(9) 0.041(9) 0.045(10) 0.001(8) 0.003(7) -0.003(7) C36 0.027(8) 0.026(7) 0.032(8) -0.005(6) 0.006(6) 0.005(6) C37 0.087(14) 0.048(11) 0.034(9) -0.009(8) -0.021(9) 0.015(9) C38 0.049(10) 0.016(7) 0.051(10) -0.009(7) 0.018(7) -0.007(6) O1 0.096(13) 0.025(7) 0.074(10) 0.006(7) -0.053(9) 0.000(8) N1 0.008(8) 0.021(8) 0.210(26) 0.028(12) 0.005(10) 0.004(6) O2 0.101(13) 0.027(7) 0.064(10) -0.018(6) 0.040(9) -0.011(7) N2 0.018(8) 0.032(8) 0.089(13) -0.004(8) 0.000(7) -0.007(6) _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 Cl3 2.355(4) . ? Sb1 Cl6 2.355(4) . ? Sb1 Cl2 2.366(3) . ? Sb1 Cl5 2.371(4) . ? Sb1 Cl1 2.373(4) . ? Sb1 Cl4 2.375(4) . ? Sb2 Cl12 2.357(4) . ? Sb2 Cl11 2.357(4) . ? Sb2 Cl8 2.362(3) . ? Sb2 Cl10 2.368(3) . ? Sb2 Cl7 2.369(4) . ? Sb2 Cl9 2.377(4) . ? C1 C6 1.34(2) . ? C1 C2 1.45(2) . ? C1 C7 1.54(2) . ? C2 C3 1.37(2) . ? C3 C4 1.38(2) . ? C4 C5 1.35(2) . ? C5 C6 1.40(2) . ? C6 C8 1.48(2) . ? C11 C12 1.39(2) . ? C11 C16 1.41(2) . ? C11 C17 1.53(2) . ? C12 C13 1.37(2) . ? C13 C14 1.36(2) . ? C14 C15 1.39(2) . ? C15 C16 1.35(2) . ? C16 C18 1.52(2) . ? C21 C26 1.37(2) . ? C21 C22 1.40(2) . ? C21 C27 1.55(2) . ? C22 C23 1.42(2) . ? C23 C24 1.36(2) . ? C24 C25 1.34(2) . ? C25 C26 1.36(2) . ? C26 C28 1.51(2) . ? C31 C32 1.39(2) . ? C31 C36 1.41(2) . ? C31 C37 1.55(2) . ? C32 C33 1.38(2) . ? C33 C34 1.42(3) . ? C34 C35 1.37(2) . ? C35 C36 1.35(2) . ? C36 C38 1.49(2) . ? O1 N1 1.02(2) . ? O2 N2 0.99(2) . ? 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 Cl3 Sb1 Cl6 89.16(14) . . ? Cl3 Sb1 Cl2 91.29(13) . . ? Cl6 Sb1 Cl2 89.71(14) . . ? Cl3 Sb1 Cl5 91.10(15) . . ? Cl6 Sb1 Cl5 178.82(14) . . ? Cl2 Sb1 Cl5 89.14(14) . . ? Cl3 Sb1 Cl1 178.41(13) . . ? Cl6 Sb1 Cl1 89.83(14) . . ? Cl2 Sb1 Cl1 89.94(13) . . ? Cl5 Sb1 Cl1 89.9(2) . . ? Cl3 Sb1 Cl4 89.04(14) . . ? Cl6 Sb1 Cl4 91.30(14) . . ? Cl2 Sb1 Cl4 178.94(14) . . ? Cl5 Sb1 Cl4 89.85(14) . . ? Cl1 Sb1 Cl4 89.75(13) . . ? Cl12 Sb2 Cl11 179.32(14) . . ? Cl12 Sb2 Cl8 89.29(13) . . ? Cl11 Sb2 Cl8 90.04(14) . . ? Cl12 Sb2 Cl10 90.44(13) . . ? Cl11 Sb2 Cl10 89.50(14) . . ? Cl8 Sb2 Cl10 90.70(12) . . ? Cl12 Sb2 Cl7 90.01(15) . . ? Cl11 Sb2 Cl7 90.1(2) . . ? Cl8 Sb2 Cl7 90.38(13) . . ? Cl10 Sb2 Cl7 178.84(13) . . ? Cl12 Sb2 Cl9 90.26(15) . . ? Cl11 Sb2 Cl9 90.4(2) . . ? Cl8 Sb2 Cl9 179.43(13) . . ? Cl10 Sb2 Cl9 88.96(12) . . ? Cl7 Sb2 Cl9 89.97(14) . . ? C6 C1 C2 120.4(13) . . ? C6 C1 C7 123.0(14) . . ? C2 C1 C7 116.6(13) . . ? C3 C2 C1 118.5(15) . . ? C2 C3 C4 121.5(15) . . ? C5 C4 C3 117.4(13) . . ? C4 C5 C6 124.3(16) . . ? C1 C6 C5 117.5(14) . . ? C1 C6 C8 121.1(14) . . ? C5 C6 C8 121.4(15) . . ? C12 C11 C16 119.5(13) . . ? C12 C11 C17 119.0(13) . . ? C16 C11 C17 121.3(12) . . ? C13 C12 C11 120.3(14) . . ? C14 C13 C12 120.5(14) . . ? C13 C14 C15 118.8(15) . . ? C16 C15 C14 122.8(15) . . ? C15 C16 C11 117.8(12) . . ? C15 C16 C18 120.8(13) . . ? C11 C16 C18 121.3(12) . . ? C26 C21 C22 120.2(14) . . ? C26 C21 C27 123.4(15) . . ? C22 C21 C27 116.4(15) . . ? C21 C22 C23 119.4(16) . . ? C24 C23 C22 117.4(15) . . ? C25 C24 C23 122.0(16) . . ? C24 C25 C26 122.3(16) . . ? C25 C26 C21 118.7(14) . . ? C25 C26 C28 123.3(16) . . ? C21 C26 C28 118.0(15) . . ? C32 C31 C36 122.0(12) . . ? C32 C31 C37 118.8(14) . . ? C36 C31 C37 119.2(13) . . ? C33 C32 C31 118.9(14) . . ? C32 C33 C34 120.2(16) . . ? C35 C34 C33 117.6(17) . . ? C36 C35 C34 125.0(15) . . ? C35 C36 C31 116.3(13) . . ? C35 C36 C38 122.4(13) . . ? C31 C36 C38 121.3(13) . . ? _refine_diff_density_max 3.941 _refine_diff_density_min -1.705 _refine_diff_density_rms 0.267 data_ros-csx _database_code_CSD 181220 _audit_creation_method SHELXL _chemical_name_systematic ; Mesitylene/nitrozonium hexachloroantimonate molecular complex 2:1 ; _chemical_name_common ? _chemical_formula_moiety ; 2(C9 H12), (N O)^+^, (Cl6 Sb)^-^ ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H24 Cl6 N O Sb' _chemical_formula_weight 604.83 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sb' 'Sb' -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M Cm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' _cell_length_a 12.502(3) _cell_length_b 10.516(2) _cell_length_c 9.852(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.46(5) _cell_angle_gamma 90.00 _cell_volume 1221.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3169 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 34.1 _exptl_crystal_description 'prism' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method none _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 1.795 _exptl_absorpt_correction_type 'Empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_T_max 1.000 _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 284 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.3 _diffrn_reflns_number 8122 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 35.68 _reflns_number_total 4169 _reflns_number_observed 3559 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V5.625 (Siemens, 1997-01)' _computing_cell_refinement 'SAINT V6.02 (Siemens, 1997-01)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 2001)' _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 3 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^)+(0.0349P)^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=1.2Uiso/eq of an adjacent carbon atom (1.5Uiso/eq for Me-hydrogens) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 4166 _refine_ls_number_parameters 179 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_obs 0.0310 _refine_ls_wR_factor_all 0.0658 _refine_ls_wR_factor_obs 0.0629 _refine_ls_goodness_of_fit_all 0.940 _refine_ls_goodness_of_fit_obs 0.980 _refine_ls_restrained_S_all 0.945 _refine_ls_restrained_S_obs 0.980 _refine_ls_shift/esd_max -0.047 _refine_ls_shift/esd_mean 0.006 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 -0.18907(4) -0.5000 -0.28179(6) 0.01923(6) Uani 1 d S . Cl1 Cl -0.05445(7) -0.34115(12) -0.27814(9) 0.0275(3) Uani 1 d . . Cl2 Cl -0.32428(8) -0.33919(12) -0.28669(11) 0.0315(3) Uani 1 d . . Cl3 Cl -0.2537(2) -0.5000 -0.5371(2) 0.0320(4) Uani 1 d S . Cl4 Cl -0.1293(2) -0.5000 -0.0278(2) 0.0310(4) Uani 1 d S . O1 O 0.4625(3) -0.5000 0.7549(4) 0.0345(7) Uani 1 d S . N1 N 0.4392(3) -0.5000 0.6381(4) 0.0240(7) Uani 1 d S . C1 C 0.2474(6) -0.5000 0.4657(8) 0.0256(13) Uani 1 d S . C2 C 0.2932(3) -0.6142(3) 0.4385(3) 0.0250(5) Uani 1 d . . H2 H 0.2514(30) -0.6973(34) 0.4519(37) 0.009(8) Uiso 1 d . . C3 C 0.3828(3) -0.6161(3) 0.3824(3) 0.0246(5) Uani 1 d . . C4 C 0.4257(3) -0.5000 0.3555(5) 0.0242(8) Uani 1 d S . H4 H 0.4822(41) -0.5000 0.3213(49) 0.019(11) Uiso 1 d S . C5 C 0.1503(5) -0.5000 0.5253(7) 0.0403(12) Uani 1 d S . H5A H 0.1436(34) -0.4156(17) 0.5638(61) 0.060 Uiso 0.50 calc PR -1 H5B H 0.1650(25) -0.5632(41) 0.6025(45) 0.060 Uiso 0.50 calc PR -1 H5C H 0.0796(10) -0.5212(58) 0.4484(16) 0.060 Uiso 0.50 calc PR -1 C6 C 0.4316(4) -0.7397(4) 0.3532(4) 0.0340(7) Uani 1 d . . H6A H 0.4959(50) -0.7154(62) 0.3933(59) 0.069(19) Uiso 1 d . . H6B H 0.3882(36) -0.7696(37) 0.2594(44) 0.034(10) Uiso 1 d . . H6C H 0.4117(52) -0.8007(58) 0.3970(60) 0.069(17) Uiso 1 d . . C11 C 0.3651(6) -0.5000 0.9875(7) 0.0234(12) Uani 1 d S . C12 C 0.4248(3) -0.6142(3) 1.0118(3) 0.0242(5) Uani 1 d . . H12 H 0.3694(59) -0.6772(69) 1.0014(68) 0.071(20) Uiso 1 d . . C13 C 0.5428(3) -0.6157(3) 1.0618(3) 0.0257(6) Uani 1 d . . C14 C 0.6007(4) -0.5000 1.0865(5) 0.0281(8) Uani 1 d S . H14 H 0.6813(48) -0.5000 1.1230(57) 0.029(13) Uiso 1 d S . C15 C 0.2364(4) -0.5000 0.9387(6) 0.0321(9) Uani 1 d S . H15A H 0.2079(4) -0.4157(15) 0.9013(55) 0.048 Uiso 0.50 calc PR -1 H15B H 0.2114(4) -0.5206(51) 1.0205(15) 0.048 Uiso 0.50 calc PR -1 H15C H 0.2067(4) -0.5637(36) 0.8628(42) 0.048 Uiso 0.50 calc PR -1 C16 C 0.6083(4) -0.7388(4) 1.0895(5) 0.0377(8) Uani 1 d . . H16A H 0.6567(74) -0.7189(79) 1.0457(93) 0.128(33) Uiso 1 d . . H16B H 0.5838(52) -0.7901(55) 1.1055(63) 0.060(19) Uiso 1 d . . H16C H 0.6554(42) -0.7447(42) 1.1826(53) 0.042(11) 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 0.01689(9) 0.01677(9) 0.02527(11) 0.000 0.00868(7) 0.000 Cl1 0.0235(6) 0.0266(6) 0.0336(7) 0.0022(6) 0.0109(6) -0.0074(6) Cl2 0.0240(7) 0.0214(6) 0.0509(8) 0.0004(7) 0.0150(6) 0.0041(6) Cl3 0.0311(10) 0.0342(10) 0.0265(9) 0.000 0.0040(7) 0.000 Cl4 0.0377(11) 0.0333(10) 0.0253(9) 0.000 0.0150(8) 0.000 O1 0.029(2) 0.051(2) 0.022(2) 0.000 0.0066(12) 0.000 N1 0.0184(15) 0.025(2) 0.031(2) 0.000 0.0104(13) 0.000 C1 0.025(3) 0.024(3) 0.028(3) 0.000 0.008(2) 0.000 C2 0.0274(14) 0.0226(13) 0.0251(14) 0.0013(11) 0.0089(11) 0.0011(11) C3 0.0303(14) 0.0244(14) 0.0186(12) 0.0020(11) 0.0073(11) 0.0047(11) C4 0.020(2) 0.028(2) 0.023(2) 0.000 0.0059(15) 0.000 C5 0.043(3) 0.026(2) 0.064(3) 0.000 0.034(3) 0.000 C6 0.040(2) 0.030(2) 0.035(2) 0.0038(14) 0.017(2) 0.010(2) C11 0.021(2) 0.026(3) 0.022(2) 0.000 0.007(2) 0.000 C12 0.0274(14) 0.0229(13) 0.0220(13) -0.0014(11) 0.0079(11) -0.0006(11) C13 0.0279(14) 0.0294(14) 0.0203(13) -0.0001(11) 0.0086(11) 0.0045(12) C14 0.025(2) 0.037(2) 0.022(2) 0.000 0.009(2) 0.000 C15 0.023(2) 0.028(2) 0.045(3) 0.000 0.011(2) 0.000 C16 0.035(2) 0.036(2) 0.040(2) 0.003(2) 0.009(2) 0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 Cl4 2.361(2) . ? Sb1 Cl1 2.3630(12) 2_545 ? Sb1 Cl1 2.3631(12) . ? Sb1 Cl3 2.372(2) . ? Sb1 Cl2 2.3801(12) 2_545 ? Sb1 Cl2 2.3801(12) . ? O1 N1 1.089(5) . ? C1 C2 1.395(4) 2_545 ? C1 C2 1.395(4) . ? C1 C5 1.514(8) . ? C2 C3 1.404(4) . ? C2 H2 1.05(4) . ? C3 C4 1.394(3) . ? C3 C6 1.504(4) . ? C4 C3 1.394(3) 2_545 ? C4 H4 0.88(5) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.81(6) . ? C6 H6B 0.96(4) . ? C6 H6C 0.86(6) . ? C11 C12 1.391(5) 2_545 ? C11 C12 1.391(5) . ? C11 C15 1.519(8) . ? C12 C13 1.391(4) . ? C12 H12 0.94(7) . ? C13 C14 1.395(4) . ? C13 C16 1.508(5) . ? C14 C13 1.395(4) 2_545 ? C14 H14 0.95(6) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 H16A 0.88(8) . ? C16 H16B 0.66(6) . ? C16 H16C 0.91(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 Cl4 Sb1 Cl1 90.65(5) . 2_545 ? Cl4 Sb1 Cl1 90.65(5) . . ? Cl1 Sb1 Cl1 89.97(6) 2_545 . ? Cl4 Sb1 Cl3 178.64(9) . . ? Cl1 Sb1 Cl3 90.31(5) 2_545 . ? Cl1 Sb1 Cl3 90.31(5) . . ? Cl4 Sb1 Cl2 89.63(6) . 2_545 ? Cl1 Sb1 Cl2 89.74(2) 2_545 2_545 ? Cl1 Sb1 Cl2 179.60(5) . 2_545 ? Cl3 Sb1 Cl2 89.41(6) . 2_545 ? Cl4 Sb1 Cl2 89.63(6) . . ? Cl1 Sb1 Cl2 179.60(6) 2_545 . ? Cl1 Sb1 Cl2 89.74(2) . . ? Cl3 Sb1 Cl2 89.41(6) . . ? Cl2 Sb1 Cl2 90.55(6) 2_545 . ? C2 C1 C2 118.9(5) 2_545 . ? C2 C1 C5 120.5(3) 2_545 . ? C2 C1 C5 120.5(3) . . ? C1 C2 C3 121.4(3) . . ? C1 C2 H2 116.1(18) . . ? C3 C2 H2 122.3(18) . . ? C4 C3 C2 118.1(3) . . ? C4 C3 C6 120.9(3) . . ? C2 C3 C6 121.0(3) . . ? C3 C4 C3 122.3(4) 2_545 . ? C3 C4 H4 118.9(2) 2_545 . ? C3 C4 H4 118.9(2) . . ? C1 C5 H5A 109.47(11) . . ? C1 C5 H5B 109.5(3) . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5(4) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 91.9(45) . . ? C3 C6 H6B 109.5(24) . . ? H6A C6 H6B 136.7(44) . . ? C3 C6 H6C 110.2(38) . . ? H6A C6 H6C 113.5(61) . . ? H6B C6 H6C 94.2(43) . . ? C12 C11 C12 119.3(6) 2_545 . ? C12 C11 C15 120.3(3) 2_545 . ? C12 C11 C15 120.3(3) . . ? C13 C12 C11 121.0(4) . . ? C13 C12 H12 133.4(43) . . ? C11 C12 H12 104.9(43) . . ? C12 C13 C14 118.7(3) . . ? C12 C13 C16 121.5(3) . . ? C14 C13 C16 119.9(3) . . ? C13 C14 C13 121.4(4) . 2_545 ? C13 C14 H14 119.3(2) . . ? C13 C14 H14 119.3(2) 2_545 . ? C11 C15 H15A 109.47(10) . . ? C11 C15 H15B 109.5(3) . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5(2) . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 97.3(53) . . ? C13 C16 H16B 118.3(52) . . ? H16A C16 H16B 139.4(67) . . ? C13 C16 H16C 111.7(28) . . ? H16A C16 H16C 101.0(61) . . ? H16B C16 H16C 84.3(53) . . ? _refine_diff_density_max 1.415 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.107