# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Prof Jay Kochi' _publ_contact_author_address ; University of Houston 4800 Calhoun Houston Tx 77204 UNITED STATES OF AMERICA ; _publ_contact_author_email JKOCHI@UH.EDU _publ_section_title ; Structural Effects of Carbon-Monoxide Coordination to Carbon Centers. p and s Bindings in Aliphatic Acyl versus Aromatic Aroyl Cations ; loop_ _publ_author_name 'Jay Kochi' 'Milya G. Davlieva' 'Sergey V. Lindeman' data_mil-bsx _database_code_depnum_ccdc_archive 'CCDC 239194' _audit_creation_method SHELXL _chemical_name_systematic ; 4'-Methoxyphenyloxocarbonium hexafluoroantimonate ; _chemical_name_common "4'-Methoxyphenyloxocarbonium hexafluoroantimonate" _chemical_formula_moiety 'C8 H7 O2, F6 Sb' _chemical_formula_structural '(C8 H7 O2)^+^, (F6 Sb)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C8 H7 F6 O2 Sb' _chemical_formula_weight 370.89 _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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.0609(15) _cell_length_b 10.4108(8) _cell_length_c 28.690(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.537(2) _cell_angle_gamma 90.00 _cell_volume 5691.2(7) _cell_formula_units_Z 20 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6165 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.164 _exptl_crystal_density_method none _exptl_crystal_F_000 3520 _exptl_absorpt_coefficient_mu 2.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.548 _exptl_absorpt_correction_T_max 0.819 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31114 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 32.00 _reflns_number_total 9116 _reflns_number_gt 7508 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+69.1965P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9116 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1626 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.06783(2) 0.58231(4) 0.391401(15) 0.04751(12) Uani 1 1 d . . . F1 F -0.0268(2) 0.6060(5) 0.4033(2) 0.0772(14) Uani 1 1 d . A . F2 F 0.1630(2) 0.5628(6) 0.3804(2) 0.0855(16) Uani 1 1 d . A . F3 F 0.0920(4) 0.7254(7) 0.4286(3) 0.094(3) Uani 0.841(10) 1 d P A 1 F4 F 0.0730(3) 0.4827(7) 0.4461(3) 0.092(2) Uani 0.841(10) 1 d P A 1 F5 F 0.0464(4) 0.4385(10) 0.3586(4) 0.134(4) Uani 0.841(10) 1 d P A 1 F6 F 0.0595(4) 0.6907(12) 0.3415(3) 0.132(5) Uani 0.841(10) 1 d P A 1 F3A F 0.096(3) 0.603(5) 0.4444(17) 0.112(15) Uiso 0.159(10) 1 d P A 2 F4A F 0.075(2) 0.420(4) 0.3964(16) 0.102(14) Uiso 0.159(10) 1 d P A 2 F5A F 0.0480(14) 0.571(3) 0.3237(9) 0.055(7) Uiso 0.159(10) 1 d P A 2 F6A F 0.080(2) 0.761(4) 0.3770(14) 0.082(11) Uiso 0.159(10) 1 d P A 2 Sb2 Sb 0.19999(3) 0.50929(4) 0.204640(15) 0.05189(13) Uani 1 1 d . . . F7 F 0.1914(4) 0.4474(6) 0.26499(17) 0.0980(19) Uani 1 1 d . B . F8 F 0.2093(2) 0.5734(4) 0.14376(14) 0.0605(10) Uani 1 1 d . B . F9 F 0.2780(5) 0.6016(9) 0.2237(3) 0.127(4) Uani 0.898(8) 1 d P B 1 F10 F 0.2539(4) 0.3678(6) 0.1883(2) 0.091(2) Uani 0.898(8) 1 d P B 1 F11 F 0.1198(3) 0.4214(6) 0.1847(2) 0.0819(18) Uani 0.898(8) 1 d P B 1 F12 F 0.1445(5) 0.6513(6) 0.2171(2) 0.106(3) Uani 0.898(8) 1 d P B 1 F9A F 0.302(3) 0.497(5) 0.1992(19) 0.077(14) Uiso 0.102(8) 1 d P B 2 F10A F 0.180(2) 0.346(4) 0.1822(15) 0.063(12) Uiso 0.102(8) 1 d P B 2 F11A F 0.109(2) 0.540(4) 0.2108(15) 0.062(12) Uiso 0.102(8) 1 d P B 2 F12A F 0.213(3) 0.674(5) 0.2263(16) 0.066(12) Uiso 0.102(8) 1 d P B 2 Sb3 Sb 0.2500 0.2500 0.5000 0.03917(13) Uani 1 2 d S . . F13 F 0.2367(4) 0.3678(8) 0.4520(3) 0.117(2) Uani 1 1 d . . . F14 F 0.3313(3) 0.2026(8) 0.4711(2) 0.104(2) Uani 1 1 d . . . F15 F 0.1974(5) 0.1303(9) 0.4666(3) 0.142(3) Uani 1 1 d . . . O1 O 0.8090(3) 0.7020(5) 0.6520(2) 0.0607(12) Uani 1 1 d . . . O2 O 0.5136(4) 0.3859(7) 0.6342(3) 0.0834(19) Uani 1 1 d . . . C1 C 0.6952(3) 0.5828(6) 0.6474(2) 0.0445(12) Uani 1 1 d . . . C2 C 0.6920(4) 0.4513(6) 0.6621(2) 0.0518(15) Uani 1 1 d . . . H2 H 0.7318 0.4079 0.6751 0.062 Uiso 1 1 calc R . . C3 C 0.6281(4) 0.3917(6) 0.6564(2) 0.0585(18) Uani 1 1 d . . . H3 H 0.6235 0.3045 0.6655 0.070 Uiso 1 1 calc R . . C4 C 0.5706(4) 0.4552(7) 0.6379(2) 0.0552(17) Uani 1 1 d . . . C5 C 0.5753(4) 0.5842(6) 0.6245(2) 0.0499(14) Uani 1 1 d . . . H5 H 0.5350 0.6272 0.6120 0.060 Uiso 1 1 calc R . . C6 C 0.6370(4) 0.6480(6) 0.6291(2) 0.0475(13) Uani 1 1 d . . . H6 H 0.6404 0.7356 0.6202 0.057 Uiso 1 1 calc R . . C7 C 0.7589(4) 0.6457(6) 0.6504(2) 0.0494(14) Uani 1 1 d . . . C8 C 0.4556(6) 0.4398(9) 0.6186(4) 0.083(3) Uani 1 1 d . . . H81 H 0.4175 0.3767 0.6185 0.125 Uiso 1 1 calc R . . H82 H 0.4622 0.4710 0.5868 0.125 Uiso 1 1 calc R . . H83 H 0.4438 0.5121 0.6388 0.125 Uiso 1 1 calc R . . O1A O 0.1803(4) 0.9305(7) 0.4038(3) 0.0860(19) Uani 1 1 d . . . O2A O 0.4602(3) 0.6355(6) 0.4856(2) 0.0652(13) Uani 1 1 d . . . C1A C 0.2894(4) 0.8219(7) 0.4341(2) 0.0535(15) Uani 1 1 d . . . C2A C 0.2846(4) 0.6934(7) 0.4484(2) 0.0532(16) Uani 1 1 d . . . H2A H 0.2413 0.6485 0.4458 0.064 Uiso 1 1 calc R . . C3A C 0.3430(4) 0.6345(7) 0.4659(2) 0.0550(16) Uani 1 1 d . . . H3A H 0.3410 0.5477 0.4759 0.066 Uiso 1 1 calc R . . C4A C 0.4063(4) 0.7028(7) 0.4690(2) 0.0526(16) Uani 1 1 d . . . C5A C 0.4107(4) 0.8322(7) 0.4550(2) 0.0586(18) Uani 1 1 d . . . H5A H 0.4539 0.8773 0.4579 0.070 Uiso 1 1 calc R . . C6A C 0.3526(4) 0.8915(7) 0.4375(3) 0.0595(18) Uani 1 1 d . . . H6A H 0.3544 0.9785 0.4276 0.071 Uiso 1 1 calc R . . C7A C 0.2300(5) 0.8820(9) 0.4172(3) 0.067(2) Uani 1 1 d . . . C8A C 0.5272(4) 0.6985(10) 0.4934(3) 0.072(2) Uani 1 1 d . . . H81A H 0.5605 0.6380 0.5079 0.108 Uiso 1 1 calc R . . H82A H 0.5213 0.7726 0.5140 0.108 Uiso 1 1 calc R . . H83A H 0.5452 0.7276 0.4635 0.108 Uiso 1 1 calc R . . O1B O 0.5196(7) 0.0655(12) 0.2552(5) 0.080(4) Uiso 0.50 1 d P . 1 O2B O 0.4687(9) 0.689(2) 0.2509(8) 0.122(6) Uiso 0.50 1 d P . 1 C1B C 0.5000 0.3010(8) 0.2500 0.0441(17) Uiso 1 2 d S . 1 C2B C 0.4349(9) 0.3482(19) 0.2359(6) 0.056(4) Uiso 0.50 1 d P . 1 H2B H 0.3977 0.2920 0.2269 0.067 Uiso 0.50 1 d PR . 1 C3B C 0.4269(10) 0.4835(17) 0.2354(6) 0.060(4) Uiso 0.50 1 d P . 1 H3B H 0.3834 0.5211 0.2258 0.072 Uiso 0.50 1 d PR . 1 C4B C 0.4820(8) 0.5593(15) 0.2489(6) 0.059(4) Uiso 0.50 1 d P . 1 C5B C 0.5469(8) 0.5161(13) 0.2594(4) 0.042(2) Uiso 0.50 1 d P . 1 H5B H 0.5838 0.5751 0.2661 0.050 Uiso 0.50 1 d PR . 1 C6B C 0.5598(7) 0.3851(14) 0.2604(5) 0.038(3) Uiso 0.50 1 d P . 1 H6B H 0.6056 0.3530 0.2671 0.045 Uiso 0.50 1 d PR . 1 C7B C 0.5135(7) 0.1729(12) 0.2516(7) 0.054(3) Uiso 0.50 1 d P . 1 C8B C 0.5233(15) 0.778(3) 0.2696(10) 0.113(8) Uiso 0.50 1 d P . 1 H81B H 0.5255 0.8539 0.2496 0.169 Uiso 0.50 1 d PR . 1 H82B H 0.5690 0.7344 0.2703 0.169 Uiso 0.50 1 d PR . 1 H83B H 0.5116 0.8038 0.3013 0.169 Uiso 0.50 1 d PR . 1 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 0.0394(2) 0.0523(2) 0.0507(2) 0.00197(17) -0.00189(16) 0.00283(16) F1 0.047(2) 0.074(3) 0.112(4) 0.005(3) 0.010(2) 0.005(2) F2 0.040(2) 0.106(4) 0.111(4) -0.018(3) 0.005(2) 0.007(2) F3 0.092(5) 0.081(4) 0.112(6) -0.025(4) 0.025(4) -0.038(4) F4 0.075(4) 0.106(5) 0.095(5) 0.055(4) -0.002(3) -0.012(4) F5 0.068(4) 0.154(8) 0.177(10) -0.109(8) -0.013(5) 0.001(5) F6 0.093(5) 0.214(12) 0.089(6) 0.087(7) 0.001(4) 0.014(6) Sb2 0.0712(3) 0.0426(2) 0.0418(2) 0.00190(16) -0.00055(19) 0.00523(19) F7 0.156(6) 0.092(4) 0.047(2) 0.020(3) 0.003(3) -0.007(4) F8 0.079(3) 0.058(2) 0.0445(19) 0.0047(17) 0.0055(18) 0.017(2) F9 0.146(7) 0.145(7) 0.086(5) 0.024(5) -0.041(5) -0.082(6) F10 0.100(5) 0.079(4) 0.096(4) 0.025(3) 0.023(3) 0.049(4) F11 0.073(4) 0.087(4) 0.085(4) 0.008(3) -0.007(3) -0.006(3) F12 0.173(8) 0.068(4) 0.078(4) -0.003(3) 0.038(4) 0.048(4) Sb3 0.0383(3) 0.0407(3) 0.0387(2) 0.00534(19) 0.00539(19) -0.0112(2) F13 0.106(5) 0.130(6) 0.115(5) 0.065(5) 0.015(4) 0.011(4) F14 0.057(3) 0.162(6) 0.093(4) -0.013(4) 0.026(3) 0.012(3) F15 0.138(6) 0.161(7) 0.128(6) -0.058(6) 0.023(5) -0.078(6) O1 0.051(3) 0.055(3) 0.076(3) 0.004(2) 0.009(2) -0.001(2) O2 0.078(4) 0.076(4) 0.098(5) -0.017(3) 0.030(4) -0.026(3) C1 0.055(3) 0.042(3) 0.037(3) -0.002(2) 0.011(2) -0.002(3) C2 0.067(4) 0.047(3) 0.043(3) 0.003(2) 0.018(3) -0.002(3) C3 0.083(5) 0.039(3) 0.054(4) 0.005(3) 0.025(4) -0.002(3) C4 0.062(4) 0.050(3) 0.055(4) -0.011(3) 0.030(3) -0.018(3) C5 0.052(3) 0.047(3) 0.052(3) -0.005(3) 0.008(3) 0.000(3) C6 0.054(3) 0.039(3) 0.050(3) 0.000(2) 0.008(3) -0.005(2) C7 0.053(4) 0.047(3) 0.048(3) 0.002(3) 0.004(3) 0.007(3) C8 0.082(6) 0.066(5) 0.102(7) -0.011(5) 0.026(5) 0.007(5) O1A 0.079(4) 0.081(4) 0.099(5) 0.016(4) 0.011(4) -0.013(4) O2A 0.055(3) 0.069(3) 0.072(3) -0.004(3) 0.007(2) -0.009(3) C1A 0.059(4) 0.060(4) 0.042(3) -0.006(3) 0.009(3) -0.015(3) C2A 0.055(4) 0.057(4) 0.049(3) -0.008(3) 0.011(3) -0.021(3) C3A 0.058(4) 0.049(3) 0.058(4) -0.003(3) 0.012(3) -0.021(3) C4A 0.054(4) 0.059(4) 0.046(3) -0.012(3) 0.014(3) -0.023(3) C5A 0.063(4) 0.062(4) 0.050(3) -0.006(3) 0.008(3) -0.031(4) C6A 0.070(5) 0.053(4) 0.056(4) 0.000(3) 0.006(3) -0.021(3) C7A 0.073(5) 0.067(5) 0.061(4) 0.004(4) 0.012(4) -0.023(4) C8A 0.049(4) 0.096(6) 0.073(5) -0.009(5) 0.005(3) -0.018(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 F3A 1.62(5) . ? Sb1 F4A 1.70(4) . ? Sb1 F5 1.809(7) . ? Sb1 F6 1.825(7) . ? Sb1 F2 1.861(4) . ? Sb1 F1 1.862(4) . ? Sb1 F4 1.881(6) . ? Sb1 F3 1.882(6) . ? Sb1 F6A 1.92(4) . ? Sb1 F5A 1.97(3) . ? Sb2 F11A 1.79(4) . ? Sb2 F9 1.841(7) . ? Sb2 F12A 1.84(5) . ? Sb2 F10A 1.85(4) . ? Sb2 F12 1.858(6) . ? Sb2 F11 1.859(6) . ? Sb2 F7 1.859(5) . ? Sb2 F10 1.863(5) . ? Sb2 F8 1.883(4) . ? Sb2 F9A 1.96(5) . ? Sb3 F14 1.845(5) 7_556 ? Sb3 F14 1.845(5) . ? Sb3 F15 1.850(7) . ? Sb3 F15 1.850(7) 7_556 ? Sb3 F13 1.855(6) 7_556 ? Sb3 F13 1.855(6) . ? O1 C7 1.119(8) . ? O2 C4 1.305(9) . ? O2 C8 1.308(12) . ? C1 C7 1.380(9) . ? C1 C6 1.391(9) . ? C1 C2 1.435(9) . ? C2 C3 1.372(11) . ? C2 H2 0.9500 . ? C3 C4 1.374(11) . ? C3 H3 0.9500 . ? C4 C5 1.401(10) . ? C5 C6 1.354(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? O1A C7A 1.131(11) . ? O2A C4A 1.321(10) . ? O2A C8A 1.448(9) . ? C1A C7A 1.371(13) . ? C1A C2A 1.403(10) . ? C1A C6A 1.406(10) . ? C2A C3A 1.355(11) . ? C2A H2A 0.9500 . ? C3A C4A 1.402(9) . ? C3A H3A 0.9500 . ? C4A C5A 1.408(10) . ? C5A C6A 1.353(12) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C8A H81A 0.9800 . ? C8A H82A 0.9800 . ? C8A H83A 0.9800 . ? O1B C7B 1.129(16) . ? O2B C4B 1.37(2) . ? O2B C8B 1.48(3) . ? C1B C7B 1.358(15) . ? C1B C6B 1.462(14) . ? C1B C2B 1.385(18) . ? C2B C3B 1.42(2) . ? C2B H2B 0.9500 . ? C3B C4B 1.36(2) . ? C3B H3B 0.9503 . ? C4B C5B 1.34(2) . ? C5B C6B 1.39(2) . ? C5B H5B 0.9500 . ? C6B H6B 0.9499 . ? C8B H81B 0.9799 . ? C8B H82B 0.9800 . ? C8B H83B 0.9801 . ? 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 F3A Sb1 F4A 92(2) . . ? F3A Sb1 F5 131.7(19) . . ? F4A Sb1 F5 40.3(16) . . ? F3A Sb1 F6 132.5(19) . . ? F4A Sb1 F6 133.3(16) . . ? F5 Sb1 F6 95.2(6) . . ? F3A Sb1 F2 82.5(17) . . ? F4A Sb1 F2 80.5(15) . . ? F5 Sb1 F2 91.7(3) . . ? F6 Sb1 F2 90.0(3) . . ? F3A Sb1 F1 96.5(17) . . ? F4A Sb1 F1 100.8(15) . . ? F5 Sb1 F1 89.9(3) . . ? F6 Sb1 F1 89.9(3) . . ? F2 Sb1 F1 178.4(3) . . ? F3A Sb1 F4 43.9(18) . . ? F4A Sb1 F4 51.6(16) . . ? F5 Sb1 F4 89.1(5) . . ? F6 Sb1 F4 174.8(5) . . ? F2 Sb1 F4 93.0(3) . . ? F1 Sb1 F4 87.1(3) . . ? F3A Sb1 F3 44.8(18) . . ? F4A Sb1 F3 136.2(17) . . ? F5 Sb1 F3 176.5(5) . . ? F6 Sb1 F3 88.2(5) . . ? F2 Sb1 F3 87.6(3) . . ? F1 Sb1 F3 90.8(3) . . ? F4 Sb1 F3 87.6(4) . . ? F3A Sb1 F6A 92(2) . . ? F4A Sb1 F6A 166.2(18) . . ? F5 Sb1 F6A 135.8(13) . . ? F6 Sb1 F6A 40.7(12) . . ? F2 Sb1 F6A 86.8(11) . . ? F1 Sb1 F6A 92.1(11) . . ? F4 Sb1 F6A 135.1(12) . . ? F3 Sb1 F6A 47.6(12) . . ? F3A Sb1 F5A 170(2) . . ? F4A Sb1 F5A 92.1(18) . . ? F5 Sb1 F5A 53.4(9) . . ? F6 Sb1 F5A 41.8(8) . . ? F2 Sb1 F5A 89.3(8) . . ? F1 Sb1 F5A 91.6(8) . . ? F4 Sb1 F5A 142.5(9) . . ? F3 Sb1 F5A 130.0(9) . . ? F6A Sb1 F5A 82.4(15) . . ? F11A Sb2 F9 131.2(15) . . ? F11A Sb2 F12A 85(2) . . ? F9 Sb2 F12A 46.9(16) . . ? F11A Sb2 F10A 91(2) . . ? F9 Sb2 F10A 137.5(15) . . ? F12A Sb2 F10A 176(2) . . ? F11A Sb2 F12 43.5(15) . . ? F9 Sb2 F12 89.3(5) . . ? F12A Sb2 F12 42.4(16) . . ? F10A Sb2 F12 133.2(15) . . ? F11A Sb2 F11 47.4(15) . . ? F9 Sb2 F11 178.0(4) . . ? F12A Sb2 F11 131.4(17) . . ? F10A Sb2 F11 44.2(14) . . ? F12 Sb2 F11 89.0(4) . . ? F11A Sb2 F7 82.0(14) . . ? F9 Sb2 F7 89.7(3) . . ? F12A Sb2 F7 91.4(15) . . ? F10A Sb2 F7 89.1(14) . . ? F12 Sb2 F7 91.9(3) . . ? F11 Sb2 F7 91.3(3) . . ? F11A Sb2 F10 135.6(15) . . ? F9 Sb2 F10 92.3(4) . . ? F12A Sb2 F10 139.1(17) . . ? F10A Sb2 F10 45.3(14) . . ? F12 Sb2 F10 176.5(3) . . ? F11 Sb2 F10 89.3(3) . . ? F7 Sb2 F10 91.3(3) . . ? F11A Sb2 F8 98.2(14) . . ? F9 Sb2 F8 89.7(3) . . ? F12A Sb2 F8 88.1(15) . . ? F10A Sb2 F8 91.5(14) . . ? F12 Sb2 F8 87.9(2) . . ? F11 Sb2 F8 89.2(2) . . ? F7 Sb2 F8 179.4(3) . . ? F10 Sb2 F8 88.9(2) . . ? F11A Sb2 F9A 173(2) . . ? F9 Sb2 F9A 42.6(16) . . ? F12A Sb2 F9A 88(2) . . ? F10A Sb2 F9A 96(2) . . ? F12 Sb2 F9A 129.8(17) . . ? F11 Sb2 F9A 138.8(17) . . ? F7 Sb2 F9A 99.4(16) . . ? F10 Sb2 F9A 51.0(16) . . ? F8 Sb2 F9A 80.3(16) . . ? F14 Sb3 F14 180.0(3) 7_556 . ? F14 Sb3 F15 87.9(4) 7_556 . ? F14 Sb3 F15 92.1(4) . . ? F14 Sb3 F15 92.1(4) 7_556 7_556 ? F14 Sb3 F15 87.9(4) . 7_556 ? F15 Sb3 F15 180.0(4) . 7_556 ? F14 Sb3 F13 86.8(3) 7_556 7_556 ? F14 Sb3 F13 93.2(3) . 7_556 ? F15 Sb3 F13 90.1(4) . 7_556 ? F15 Sb3 F13 89.9(4) 7_556 7_556 ? F14 Sb3 F13 93.2(3) 7_556 . ? F14 Sb3 F13 86.8(3) . . ? F15 Sb3 F13 89.9(4) . . ? F15 Sb3 F13 90.1(4) 7_556 . ? F13 Sb3 F13 180.0(3) 7_556 . ? C4 O2 C8 118.9(8) . . ? C7 C1 C6 118.9(6) . . ? C7 C1 C2 118.6(6) . . ? C6 C1 C2 122.5(6) . . ? C3 C2 C1 116.1(7) . . ? C3 C2 H2 121.9 . . ? C1 C2 H2 121.9 . . ? C2 C3 C4 121.7(6) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? O2 C4 C3 114.8(7) . . ? O2 C4 C5 124.6(8) . . ? C3 C4 C5 120.7(7) . . ? C6 C5 C4 120.4(7) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 118.7(6) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? O1 C7 C1 176.6(7) . . ? O2 C8 H81 109.5 . . ? O2 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? O2 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? C4A O2A C8A 119.3(7) . . ? C7A C1A C2A 118.6(7) . . ? C7A C1A C6A 119.1(7) . . ? C2A C1A C6A 122.3(7) . . ? C3A C2A C1A 118.7(6) . . ? C3A C2A H2A 120.7 . . ? C1A C2A H2A 120.7 . . ? C2A C3A C4A 119.5(7) . . ? C2A C3A H3A 120.3 . . ? C4A C3A H3A 120.3 . . ? O2A C4A C3A 114.4(7) . . ? O2A C4A C5A 124.0(6) . . ? C3A C4A C5A 121.6(8) . . ? C6A C5A C4A 119.3(6) . . ? C6A C5A H5A 120.4 . . ? C4A C5A H5A 120.4 . . ? C5A C6A C1A 118.7(7) . . ? C5A C6A H6A 120.6 . . ? C1A C6A H6A 120.6 . . ? O1A C7A C1A 178.7(9) . . ? O2A C8A H81A 109.5 . . ? O2A C8A H82A 109.5 . . ? H81A C8A H82A 109.5 . . ? O2A C8A H83A 109.5 . . ? H81A C8A H83A 109.5 . . ? H82A C8A H83A 109.5 . . ? C4B O2B C8B 120.0(18) . . ? C7B C1B C6B 115.8(9) . . ? C7B C1B C2B 121.7(11) . . ? C6B C1B C2B 122.3(13) . . ? C3B C2B C1B 116.8(16) . . ? C3B C2B H2B 122.1 . . ? C1B C2B H2B 121.1 . . ? C4B C3B C2B 119.5(17) . . ? C4B C3B H3B 120.3 . . ? C2B C3B H3B 120.3 . . ? C5B C4B C3B 124.6(14) . . ? C5B C4B O2B 119.3(15) . . ? C3B C4B O2B 116.0(15) . . ? C4B C5B C6B 119.8(14) . . ? C4B C5B H5B 120.1 . . ? C6B C5B H5B 120.1 . . ? C5B C6B C1B 116.6(12) . . ? C5B C6B H6B 120.9 . . ? C1B C6B H6B 122.5 . . ? O1B C7B C1B 174.0(18) . . ? O2B C8B H81B 109.5 . . ? O2B C8B H82B 109.5 . . ? H81B C8B H82B 109.5 . . ? O2B C8B H83B 109.5 . . ? H81B C8B H83B 109.5 . . ? H82B C8B H83B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.762 _refine_diff_density_min -2.133 _refine_diff_density_rms 0.156 data_milzsx _database_code_depnum_ccdc_archive 'CCDC 239195' _audit_creation_method SHELXL _chemical_name_systematic ; 4'-Fluorophenyloxocarbonium hexafluoroantimonate ; _chemical_name_common "4'-Fluorophenyloxocarbonium hexafluoroantimonate" _chemical_formula_moiety 'C7 H4 F O, F6 Sb' _chemical_formula_structural '(C7 H4 F O)^+^, (F6 Sb)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C7 H4 F7 O Sb' _chemical_formula_weight 358.85 _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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.5856(15) _cell_length_b 12.3958(15) _cell_length_c 13.0791(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.252(2) _cell_angle_gamma 90.00 _cell_volume 2038.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3906 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.338 _exptl_crystal_density_method none _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 2.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.757 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22251 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 31.84 _reflns_number_total 6591 _reflns_number_gt 4157 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections except for 28 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+1.0892P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6566 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.27393(2) -0.00575(2) 0.019693(19) 0.02744(8) Uani 1 1 d . . . F11 F 0.1510(3) 0.0714(3) -0.0116(3) 0.0838(12) Uani 1 1 d . . . F12 F 0.3550(3) 0.0975(3) -0.0457(3) 0.0703(10) Uani 1 1 d . . . F13 F 0.2571(3) -0.0808(3) -0.1032(2) 0.0755(11) Uani 1 1 d . . . F14 F 0.3955(3) -0.0849(3) 0.0515(3) 0.0771(11) Uani 1 1 d . . . F15 F 0.1924(3) -0.1081(2) 0.0852(2) 0.0583(8) Uani 1 1 d . . . F16 F 0.2949(3) 0.0705(3) 0.1400(2) 0.0804(12) Uani 1 1 d . . . Sb2 Sb 0.23194(2) 0.49406(2) 0.03897(2) 0.03037(8) Uani 1 1 d . . . F21 F 0.2398(3) 0.3458(2) 0.0226(3) 0.0823(12) Uani 1 1 d . . . F22 F 0.3018(3) 0.4761(3) 0.1662(2) 0.0677(10) Uani 1 1 d . . . F23 F 0.3629(3) 0.5120(3) -0.0174(3) 0.0822(12) Uani 1 1 d . . . F24 F 0.1023(3) 0.4811(3) 0.1021(4) 0.0970(15) Uani 1 1 d . . . F25 F 0.1636(4) 0.5099(3) -0.0882(3) 0.0787(12) Uani 1 1 d . . . F26 F 0.2237(3) 0.6422(2) 0.0593(3) 0.0699(10) Uani 1 1 d . . . O1 O 0.0389(3) 0.4867(2) 0.7213(2) 0.0409(7) Uani 1 1 d . . . F1 F 0.0089(3) 1.00444(19) 0.8011(3) 0.0598(9) Uani 1 1 d . . . C1 C 0.0270(3) 0.6861(3) 0.7513(3) 0.0254(8) Uani 1 1 d . . . C2 C 0.0231(3) 0.7556(3) 0.6668(3) 0.0328(9) Uani 1 1 d . . . H2 H 0.0251 0.7282 0.5990 0.026(11) Uiso 1 1 calc R . . C3 C 0.0164(4) 0.8642(3) 0.6846(4) 0.0380(10) Uani 1 1 d . . . H3 H 0.0127 0.9143 0.6296 0.035(12) Uiso 1 1 calc R . . C4 C 0.0152(3) 0.8991(3) 0.7852(4) 0.0365(10) Uani 1 1 d . . . C5 C 0.0193(3) 0.8319(4) 0.8678(3) 0.0372(10) Uani 1 1 d . . . H5 H 0.0174 0.8601 0.9352 0.059(15) Uiso 1 1 calc R . . C6 C 0.0264(3) 0.7228(3) 0.8516(3) 0.0320(9) Uani 1 1 d . . . H6 H 0.0309 0.6737 0.9074 0.030(11) Uiso 1 1 calc R . . C7 C 0.0341(3) 0.5753(3) 0.7338(3) 0.0308(9) Uani 1 1 d . . . O2 O 0.2212(3) 0.2549(3) 0.2486(3) 0.0487(9) Uani 1 1 d . . . F2 F 0.7366(2) 0.2759(3) 0.2325(3) 0.0742(11) Uani 1 1 d . . . C11 C 0.4195(3) 0.2573(3) 0.2439(3) 0.0254(8) Uani 1 1 d . . . C12 C 0.4803(3) 0.2479(3) 0.3346(3) 0.0313(9) Uani 1 1 d . . . H12 H 0.4474 0.2378 0.3980 0.025(11) Uiso 1 1 calc R . . C13 C 0.5887(4) 0.2534(3) 0.3303(4) 0.0399(11) Uani 1 1 d . . . H13 H 0.6330 0.2472 0.3906 0.039(13) Uiso 1 1 calc R . . C14 C 0.6316(3) 0.2682(4) 0.2362(4) 0.0423(12) Uani 1 1 d . . . C15 C 0.5724(4) 0.2749(4) 0.1453(4) 0.0413(11) Uani 1 1 d . . . H15 H 0.6061 0.2830 0.0820 0.052(15) Uiso 1 1 calc R . . C16 C 0.4650(3) 0.2698(3) 0.1486(3) 0.0339(9) Uani 1 1 d . . . H16 H 0.4216 0.2746 0.0877 0.036(12) Uiso 1 1 calc R . . C17 C 0.3095(4) 0.2553(3) 0.2473(3) 0.0329(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.02709(14) 0.02539(14) 0.02986(13) 0.00301(11) 0.00115(10) -0.00146(11) F11 0.053(2) 0.089(3) 0.110(3) 0.041(2) 0.011(2) 0.0366(19) F12 0.076(2) 0.055(2) 0.082(2) 0.0137(17) 0.0369(19) -0.0211(17) F13 0.077(2) 0.099(3) 0.0513(19) -0.0343(18) 0.0071(17) -0.017(2) F14 0.0455(19) 0.074(2) 0.110(3) 0.010(2) -0.0186(19) 0.0182(17) F15 0.068(2) 0.0470(17) 0.0608(18) 0.0158(14) 0.0104(16) -0.0190(15) F16 0.110(3) 0.076(2) 0.0566(19) -0.0339(17) 0.020(2) -0.040(2) Sb2 0.03001(15) 0.02583(15) 0.03505(14) 0.00128(11) -0.00154(11) 0.00240(11) F21 0.121(3) 0.0299(16) 0.092(3) -0.0092(16) -0.049(2) 0.0078(17) F22 0.082(3) 0.078(2) 0.0413(16) 0.0023(15) -0.0158(17) 0.0071(19) F23 0.055(2) 0.113(3) 0.080(2) 0.000(2) 0.0293(19) 0.006(2) F24 0.046(2) 0.121(4) 0.126(4) 0.026(3) 0.030(2) -0.014(2) F25 0.105(3) 0.070(2) 0.0571(19) -0.0019(16) -0.044(2) 0.0170(19) F26 0.095(3) 0.0342(16) 0.081(2) -0.0130(15) 0.007(2) 0.0101(17) O1 0.055(2) 0.0259(16) 0.0418(17) -0.0037(12) 0.0010(15) 0.0019(14) F1 0.076(2) 0.0248(14) 0.078(2) -0.0114(13) -0.0101(19) 0.0038(13) C1 0.0192(18) 0.0227(18) 0.034(2) -0.0020(15) -0.0005(15) -0.0014(15) C2 0.032(2) 0.033(2) 0.034(2) 0.0022(17) 0.0021(18) 0.0035(18) C3 0.037(3) 0.031(2) 0.046(3) 0.0107(19) 0.002(2) 0.0048(19) C4 0.030(2) 0.022(2) 0.058(3) -0.0059(18) -0.005(2) 0.0012(16) C5 0.036(3) 0.038(2) 0.037(2) -0.0110(19) -0.0092(19) 0.0043(19) C6 0.031(2) 0.032(2) 0.032(2) 0.0030(17) 0.0005(18) -0.0012(17) C7 0.032(2) 0.031(2) 0.029(2) 0.0008(16) -0.0027(17) 0.0011(17) O2 0.0272(17) 0.059(2) 0.060(2) -0.0041(17) 0.0017(16) -0.0004(17) F2 0.0201(15) 0.081(2) 0.122(3) -0.027(2) 0.0033(17) -0.0050(15) C11 0.022(2) 0.0243(19) 0.029(2) -0.0028(14) -0.0002(15) 0.0014(15) C12 0.038(2) 0.024(2) 0.032(2) -0.0053(15) -0.0020(18) 0.0064(17) C13 0.040(3) 0.030(2) 0.048(3) -0.0078(19) -0.020(2) 0.007(2) C14 0.019(2) 0.031(2) 0.076(4) -0.012(2) 0.004(2) -0.0040(18) C15 0.036(3) 0.038(2) 0.051(3) 0.000(2) 0.016(2) -0.003(2) C16 0.033(2) 0.039(2) 0.029(2) 0.0027(17) -0.0026(18) 0.0052(19) C17 0.037(3) 0.028(2) 0.033(2) -0.0024(15) -0.0012(18) 0.0018(19) _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 F16 1.845(3) . ? Sb1 F11 1.851(3) . ? Sb1 F14 1.851(3) . ? Sb1 F13 1.862(3) . ? Sb1 F15 1.862(3) . ? Sb1 F12 1.866(3) . ? Sb2 F23 1.845(4) . ? Sb2 F25 1.852(3) . ? Sb2 F21 1.854(3) . ? Sb2 F26 1.859(3) . ? Sb2 F24 1.864(4) . ? Sb2 F22 1.865(3) . ? O1 C7 1.113(5) . ? F1 C4 1.325(5) . ? C1 C6 1.389(6) . ? C1 C7 1.396(5) . ? C1 C2 1.401(6) . ? C2 C3 1.370(6) . ? C2 H2 0.9500 . ? C3 C4 1.386(6) . ? C3 H3 0.9500 . ? C4 C5 1.363(6) . ? C5 C6 1.373(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O2 C17 1.112(6) . ? F2 C14 1.328(5) . ? C11 C17 1.387(6) . ? C11 C12 1.391(5) . ? C11 C16 1.401(6) . ? C12 C13 1.369(6) . ? C12 H12 0.9500 . ? C13 C14 1.376(7) . ? C13 H13 0.9500 . ? C14 C15 1.380(7) . ? C15 C16 1.356(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 F16 Sb1 F11 90.78(19) . . ? F16 Sb1 F14 89.49(18) . . ? F11 Sb1 F14 179.04(17) . . ? F16 Sb1 F13 178.05(16) . . ? F11 Sb1 F13 90.10(18) . . ? F14 Sb1 F13 89.66(17) . . ? F16 Sb1 F15 91.13(14) . . ? F11 Sb1 F15 89.04(15) . . ? F14 Sb1 F15 90.04(15) . . ? F13 Sb1 F15 90.63(15) . . ? F16 Sb1 F12 88.67(15) . . ? F11 Sb1 F12 90.67(16) . . ? F14 Sb1 F12 90.25(16) . . ? F13 Sb1 F12 89.58(16) . . ? F15 Sb1 F12 179.64(15) . . ? F23 Sb2 F25 91.09(19) . . ? F23 Sb2 F21 91.22(18) . . ? F25 Sb2 F21 91.52(14) . . ? F23 Sb2 F26 89.61(16) . . ? F25 Sb2 F26 89.82(14) . . ? F21 Sb2 F26 178.41(17) . . ? F23 Sb2 F24 176.69(19) . . ? F25 Sb2 F24 91.3(2) . . ? F21 Sb2 F24 91.00(19) . . ? F26 Sb2 F24 88.12(17) . . ? F23 Sb2 F22 88.49(17) . . ? F25 Sb2 F22 179.07(16) . . ? F21 Sb2 F22 87.65(14) . . ? F26 Sb2 F22 91.01(15) . . ? F24 Sb2 F22 89.14(18) . . ? C6 C1 C7 118.6(4) . . ? C6 C1 C2 122.9(4) . . ? C7 C1 C2 118.4(4) . . ? C3 C2 C1 118.1(4) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 118.1(4) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? F1 C4 C5 118.6(4) . . ? F1 C4 C3 117.3(4) . . ? C5 C4 C3 124.1(4) . . ? C4 C5 C6 118.7(4) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 118.1(4) . . ? C5 C6 H6 120.9 . . ? C1 C6 H6 120.9 . . ? O1 C7 C1 178.9(5) . . ? C17 C11 C12 119.2(4) . . ? C17 C11 C16 118.3(4) . . ? C12 C11 C16 122.5(4) . . ? C13 C12 C11 118.5(4) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 118.0(4) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? F2 C14 C13 117.9(5) . . ? F2 C14 C15 117.9(5) . . ? C13 C14 C15 124.2(4) . . ? C16 C15 C14 118.3(4) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C15 C16 C11 118.5(4) . . ? C15 C16 H16 120.8 . . ? C11 C16 H16 120.8 . . ? O2 C17 C11 178.8(5) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.822 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.144 data_mil-fsx _database_code_depnum_ccdc_archive 'CCDC 239196' _audit_creation_method SHELXL _chemical_name_systematic ; Pentamethylphenyloxocarbonium hexafluoroantimonate, dichloromethane monosolvate ; _chemical_name_common ;Pentamethylphenyloxocarbonium hexafluoroantimonate, dichloromethane monosolvate ; _chemical_formula_moiety 'C12 H15 O, F6 Sb, C H2 Cl2' _chemical_formula_structural ; (C12 H15 O)^+^, (F6 Sb)^-^, (C H2 Cl2) ; _chemical_formula_analytical ? _chemical_formula_sum 'C13 H17 Cl2 F6 O Sb' _chemical_formula_weight 495.92 _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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6218(6) _cell_length_b 12.7753(9) _cell_length_c 18.2425(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.6410(10) _cell_angle_gamma 90.00 _cell_volume 1776.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6015 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method none _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.909 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.465 _exptl_absorpt_correction_T_max 0.826 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19127 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 31.79 _reflns_number_total 5693 _reflns_number_gt 5180 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections except for 18 with very negative F^2^ or flagged by us for potential systematic errors. Hydrogens of the solvent molecule were refined using riding approximation with Uiso = 1.2Uiso/eq of an adjacent carbon ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+1.2749P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5675 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.152695(16) 0.842080(10) 0.325228(7) 0.02401(5) Uani 1 1 d . . . F1 F -0.00323(17) 0.90004(12) 0.25625(8) 0.0406(3) Uani 1 1 d . . . F2 F -0.00980(18) 0.86740(13) 0.39928(8) 0.0381(3) Uani 1 1 d . . . F3 F 0.31017(19) 0.78192(14) 0.39255(9) 0.0474(4) Uani 1 1 d . . . F4 F 0.31111(18) 0.81564(12) 0.24957(8) 0.0379(3) Uani 1 1 d . . . F5 F 0.0453(2) 0.71129(11) 0.31005(9) 0.0444(3) Uani 1 1 d . . . F6 F 0.2521(2) 0.97375(12) 0.34039(9) 0.0456(4) Uani 1 1 d . . . O1 O 0.6570(2) 0.81196(16) 0.31444(9) 0.0370(4) Uani 1 1 d . . . C1 C 0.6882(2) 0.69939(16) 0.42620(11) 0.0239(3) Uani 1 1 d . . . C2 C 0.7140(2) 0.59128(16) 0.41337(12) 0.0275(4) Uani 1 1 d . . . C3 C 0.7375(2) 0.52852(16) 0.47500(13) 0.0305(4) Uani 1 1 d . . . C4 C 0.7345(2) 0.57425(17) 0.54569(12) 0.0296(4) Uani 1 1 d . . . C5 C 0.7082(2) 0.68266(17) 0.55621(11) 0.0267(4) Uani 1 1 d . . . C6 C 0.6833(2) 0.74780(15) 0.49588(11) 0.0239(3) Uani 1 1 d . . . C7 C 0.6695(2) 0.76309(17) 0.36470(11) 0.0273(4) Uani 1 1 d . . . C8 C 0.7159(3) 0.5493(2) 0.33618(14) 0.0402(5) Uani 1 1 d . . . H8A H 0.8362 0.5305 0.3231 0.060 Uiso 1 1 calc R . . H8B H 0.6717 0.6029 0.3023 0.060 Uiso 1 1 calc R . . H8C H 0.6409 0.4871 0.3330 0.060 Uiso 1 1 calc R . . C9 C 0.7692(3) 0.41268(19) 0.46619(19) 0.0463(6) Uani 1 1 d . . . H9A H 0.6675 0.3738 0.4842 0.069 Uiso 1 1 calc R . . H9B H 0.8739 0.3924 0.4944 0.069 Uiso 1 1 calc R . . H9C H 0.7867 0.3965 0.4143 0.069 Uiso 1 1 calc R . . C10 C 0.7587(3) 0.5044(2) 0.61147(16) 0.0460(6) Uani 1 1 d . . . H10A H 0.7265 0.5427 0.6559 0.069 Uiso 1 1 calc R . . H10B H 0.8817 0.4825 0.6152 0.069 Uiso 1 1 calc R . . H10C H 0.6837 0.4425 0.6062 0.069 Uiso 1 1 calc R . . C11 C 0.7068(3) 0.7293(2) 0.63247(12) 0.0397(5) Uani 1 1 d . . . H11A H 0.7136 0.8058 0.6291 0.060 Uiso 1 1 calc R . . H11B H 0.8078 0.7030 0.6606 0.060 Uiso 1 1 calc R . . H11C H 0.5981 0.7094 0.6571 0.060 Uiso 1 1 calc R . . C12 C 0.6504(3) 0.86369(17) 0.50196(12) 0.0315(4) Uani 1 1 d . . . H12A H 0.5403 0.8757 0.5279 0.047 Uiso 1 1 calc R . . H12B H 0.6421 0.8942 0.4528 0.047 Uiso 1 1 calc R . . H12C H 0.7474 0.8966 0.5291 0.047 Uiso 1 1 calc R . . Cl1 Cl 0.36540(8) 0.93671(5) 0.67716(4) 0.04403(14) Uani 1 1 d . . . Cl2 Cl 0.13442(11) 0.86498(6) 0.55869(4) 0.05003(16) Uani 1 1 d . . . C1S C 0.1601(3) 0.8815(2) 0.65347(14) 0.0402(5) Uani 1 1 d . . . H21A H 0.1484 0.8127 0.6779 0.048 Uiso 1 1 calc R . . H21B H 0.0655 0.9275 0.6716 0.048 Uiso 1 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 0.02283(7) 0.02723(7) 0.02198(7) 0.00158(4) -0.00010(4) -0.00196(4) F1 0.0312(6) 0.0552(9) 0.0353(7) 0.0135(7) -0.0063(5) -0.0008(6) F2 0.0328(6) 0.0528(8) 0.0288(7) -0.0053(6) 0.0065(5) -0.0017(6) F3 0.0350(7) 0.0675(10) 0.0394(8) 0.0182(7) -0.0040(6) 0.0078(7) F4 0.0348(7) 0.0460(7) 0.0332(7) -0.0020(6) 0.0099(5) -0.0001(6) F5 0.0513(8) 0.0317(7) 0.0503(9) -0.0037(6) 0.0092(7) -0.0135(6) F6 0.0473(8) 0.0389(8) 0.0504(9) -0.0087(7) 0.0010(7) -0.0160(6) O1 0.0342(8) 0.0503(10) 0.0266(8) 0.0074(7) -0.0005(6) -0.0008(7) C1 0.0213(7) 0.0277(9) 0.0228(8) 0.0005(7) 0.0009(6) -0.0004(6) C2 0.0199(7) 0.0294(9) 0.0333(10) -0.0064(8) 0.0012(7) -0.0019(7) C3 0.0210(8) 0.0251(9) 0.0454(12) 0.0016(8) 0.0001(8) -0.0002(7) C4 0.0200(8) 0.0336(10) 0.0352(11) 0.0106(8) -0.0031(7) -0.0030(7) C5 0.0219(8) 0.0353(10) 0.0229(9) 0.0030(8) 0.0002(7) -0.0003(7) C6 0.0201(7) 0.0285(9) 0.0230(8) 0.0000(7) 0.0010(6) 0.0001(6) C7 0.0231(8) 0.0342(10) 0.0248(9) -0.0028(8) 0.0014(7) 0.0004(7) C8 0.0378(11) 0.0416(13) 0.0412(13) -0.0162(10) 0.0014(9) -0.0014(9) C9 0.0367(12) 0.0268(10) 0.075(2) 0.0022(11) 0.0041(12) 0.0015(9) C10 0.0418(12) 0.0464(14) 0.0495(15) 0.0229(12) -0.0109(11) -0.0065(10) C11 0.0452(12) 0.0521(14) 0.0219(10) 0.0022(9) -0.0002(9) 0.0024(11) C12 0.0383(11) 0.0288(9) 0.0274(10) -0.0023(8) 0.0037(8) 0.0026(8) Cl1 0.0437(3) 0.0434(3) 0.0449(3) -0.0037(2) -0.0050(2) 0.0010(2) Cl2 0.0614(4) 0.0535(4) 0.0351(3) -0.0050(3) -0.0009(3) -0.0089(3) C1S 0.0372(11) 0.0516(14) 0.0318(11) 0.0035(10) 0.0031(9) 0.0024(10) _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 F6 1.8644(14) . ? Sb1 F2 1.8711(14) . ? Sb1 F3 1.8726(14) . ? Sb1 F1 1.8737(13) . ? Sb1 F4 1.8746(13) . ? Sb1 F5 1.8796(14) . ? O1 C7 1.112(3) . ? C1 C7 1.392(3) . ? C1 C6 1.414(3) . ? C1 C2 1.415(3) . ? C2 C3 1.391(3) . ? C2 C8 1.507(3) . ? C3 C4 1.416(3) . ? C3 C9 1.508(3) . ? C4 C5 1.413(3) . ? C4 C10 1.505(3) . ? C5 C6 1.391(3) . ? C5 C11 1.514(3) . ? C6 C12 1.506(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? Cl1 C1S 1.766(3) . ? Cl2 C1S 1.751(3) . ? C1S H21A 0.9900 . ? C1S H21B 0.9900 . ? 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 F6 Sb1 F2 90.47(7) . . ? F6 Sb1 F3 90.95(8) . . ? F2 Sb1 F3 91.26(7) . . ? F6 Sb1 F1 89.82(7) . . ? F2 Sb1 F1 89.80(6) . . ? F3 Sb1 F1 178.68(7) . . ? F6 Sb1 F4 90.44(7) . . ? F2 Sb1 F4 178.63(6) . . ? F3 Sb1 F4 89.74(7) . . ? F1 Sb1 F4 89.18(7) . . ? F6 Sb1 F5 178.18(7) . . ? F2 Sb1 F5 88.25(7) . . ? F3 Sb1 F5 90.37(8) . . ? F1 Sb1 F5 88.89(7) . . ? F4 Sb1 F5 90.82(7) . . ? C7 C1 C6 117.72(18) . . ? C7 C1 C2 116.77(18) . . ? C6 C1 C2 125.49(18) . . ? C3 C2 C1 116.48(19) . . ? C3 C2 C8 123.2(2) . . ? C1 C2 C8 120.3(2) . . ? C2 C3 C4 119.67(19) . . ? C2 C3 C9 119.9(2) . . ? C4 C3 C9 120.4(2) . . ? C5 C4 C3 122.14(19) . . ? C5 C4 C10 119.3(2) . . ? C3 C4 C10 118.6(2) . . ? C6 C5 C4 119.81(19) . . ? C6 C5 C11 119.3(2) . . ? C4 C5 C11 120.89(19) . . ? C5 C6 C1 116.40(18) . . ? C5 C6 C12 123.45(19) . . ? C1 C6 C12 120.14(18) . . ? O1 C7 C1 178.1(2) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Cl2 C1S Cl1 112.26(14) . . ? Cl2 C1S H21A 109.2 . . ? Cl1 C1S H21A 109.2 . . ? Cl2 C1S H21B 109.2 . . ? Cl1 C1S H21B 109.2 . . ? H21A C1S H21B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.430 _refine_diff_density_min -0.529 _refine_diff_density_rms 0.101 data_milrsx _database_code_depnum_ccdc_archive 'CCDC 239197' _audit_creation_method SHELXL _chemical_name_systematic ; 2',4',6'-Trimethylphenyloxocarbonium hexachloroantimonate ; _chemical_name_common "2',4',6'-Trimethylphenyloxocarbonium hexachloroantimonate" _chemical_formula_moiety 'C10 H11 O, Cl6 Sb' _chemical_formula_structural '(C10 H11 O)^+^, (Cl6 Sb)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C10 H11 Cl6 O Sb' _chemical_formula_weight 481.64 _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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2849(5) _cell_length_b 25.0381(12) _cell_length_c 14.9209(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.6650(10) _cell_angle_gamma 90.00 _cell_volume 3355.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8148 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.907 _exptl_crystal_density_method none _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 2.585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.633 _exptl_absorpt_correction_T_max 0.834 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 36634 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 31.86 _reflns_number_total 10746 _reflns_number_gt 9254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections except for 7 with very negative F^2^ or flagged by us for potential systematic errors. One disordered Me-group was refined in the framework of the riding/rotating model. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+2.2044P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10739 _refine_ls_number_parameters 350 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.009116(13) 0.122223(5) 0.777176(9) 0.02462(4) Uani 1 1 d . . . Cl1 Cl -0.18979(6) 0.06258(2) 0.77016(5) 0.04367(13) Uani 1 1 d . . . Cl2 Cl -0.10248(7) 0.15186(3) 0.62481(4) 0.04864(15) Uani 1 1 d . . . Cl3 Cl 0.20905(6) 0.18195(3) 0.78317(5) 0.05114(16) Uani 1 1 d . . . Cl4 Cl 0.12297(7) 0.09408(3) 0.92956(4) 0.04900(15) Uani 1 1 d . . . Cl5 Cl 0.13611(8) 0.05436(3) 0.71833(5) 0.05281(16) Uani 1 1 d . . . Cl6 Cl -0.11909(8) 0.18973(2) 0.83616(5) 0.04991(15) Uani 1 1 d . . . Sb2 Sb 0.502225(13) 0.131827(5) 0.275771(9) 0.02390(4) Uani 1 1 d . . . Cl7 Cl 0.70153(6) 0.07562(2) 0.26269(4) 0.03841(12) Uani 1 1 d . . . Cl8 Cl 0.61084(6) 0.14187(2) 0.43592(4) 0.03702(11) Uani 1 1 d . . . Cl9 Cl 0.36943(6) 0.05602(2) 0.30439(4) 0.04036(12) Uani 1 1 d . . . Cl10 Cl 0.63814(7) 0.20747(2) 0.24656(4) 0.04319(13) Uani 1 1 d . . . Cl11 Cl 0.39313(7) 0.12375(3) 0.11582(4) 0.04392(13) Uani 1 1 d . . . Cl12 Cl 0.30484(7) 0.18825(3) 0.28988(5) 0.05101(16) Uani 1 1 d . . . O1 O 0.2377(3) 0.25450(11) 0.5555(2) 0.1079(11) Uani 1 1 d . . . C1 C 0.2460(2) 0.15631(10) 0.53091(16) 0.0369(5) Uani 1 1 d . . . C2 C 0.1256(2) 0.13420(10) 0.46295(16) 0.0359(5) Uani 1 1 d . . . C3 C 0.1287(3) 0.08007(10) 0.45158(17) 0.0419(5) Uani 1 1 d . . . H3 H 0.0505 0.0633 0.4069 0.052(8) Uiso 1 1 calc R . . C4 C 0.2448(3) 0.04869(11) 0.5043(2) 0.0472(6) Uani 1 1 d . . . C5 C 0.3612(3) 0.07255(12) 0.56938(18) 0.0488(6) Uani 1 1 d . . . H5 H 0.4396 0.0507 0.6038 0.060(9) Uiso 1 1 calc R . . C6 C 0.3666(3) 0.12612(12) 0.58545(17) 0.0434(6) Uani 1 1 d . . . C7 C 0.0043(3) 0.16885(12) 0.4071(2) 0.0492(6) Uani 1 1 d . . . H7A H -0.0499 0.1856 0.4481 0.099(13) Uiso 1 1 calc R . . H7B H -0.0645 0.1470 0.3608 0.110(15) Uiso 1 1 calc R . . H7C H 0.0479 0.1966 0.3757 0.114(16) Uiso 1 1 calc R . . C8 C 0.2420(5) -0.01034(13) 0.4896(3) 0.0759(11) Uani 1 1 d . . . H8A H 0.1391 -0.0221 0.4643 0.114 Uiso 0.50 1 calc PR . . H8B H 0.2837 -0.0283 0.5488 0.114 Uiso 0.50 1 calc PR . . H8C H 0.3015 -0.0193 0.4460 0.114 Uiso 0.50 1 calc PR . . H8D H 0.3438 -0.0244 0.5085 0.114 Uiso 0.50 1 calc PR . . H8E H 0.1992 -0.0182 0.4239 0.114 Uiso 0.50 1 calc PR . . H8F H 0.1814 -0.0272 0.5267 0.114 Uiso 0.50 1 calc PR . . C9 C 0.4907(3) 0.15343(17) 0.6550(2) 0.0653(9) Uani 1 1 d . . . H9A H 0.5424 0.1274 0.7010 0.15(2) Uiso 1 1 calc R . . H9B H 0.4494 0.1819 0.6861 0.16(2) Uiso 1 1 calc R . . H9C H 0.5612 0.1688 0.6231 0.117(16) Uiso 1 1 calc R . . C10 C 0.2434(3) 0.21029(13) 0.5455(2) 0.0595(7) Uani 1 1 d . . . O2 O 0.9597(3) 0.20939(10) 0.15519(19) 0.0802(8) Uani 1 1 d . . . C11 C 0.7967(2) 0.14159(9) 0.05500(16) 0.0338(4) Uani 1 1 d . . . C12 C 0.6647(2) 0.15962(9) -0.00777(16) 0.0351(4) Uani 1 1 d . . . C13 C 0.5784(2) 0.12106(9) -0.06121(16) 0.0362(5) Uani 1 1 d . . . H13 H 0.4882 0.1312 -0.1040 0.049(8) Uiso 1 1 calc R . . C14 C 0.6197(2) 0.06726(10) -0.05428(17) 0.0374(5) Uani 1 1 d . . . C15 C 0.7514(3) 0.05157(9) 0.00871(19) 0.0394(5) Uani 1 1 d . . . H15 H 0.7779 0.0148 0.0126 0.053(8) Uiso 1 1 calc R . . C16 C 0.8437(2) 0.08724(9) 0.06507(16) 0.0341(4) Uani 1 1 d . . . C17 C 0.6224(3) 0.21745(10) -0.0147(2) 0.0530(7) Uani 1 1 d . . . H17A H 0.6918 0.2374 -0.0418 0.122(17) Uiso 1 1 calc R . . H17B H 0.6267 0.2314 0.0473 0.127(17) Uiso 1 1 calc R . . H17C H 0.5210 0.2214 -0.0541 0.107(14) Uiso 1 1 calc R . . C18 C 0.5217(3) 0.02705(13) -0.1147(2) 0.0571(7) Uani 1 1 d . . . H18A H 0.5275 0.0317 -0.1789 0.115(16) Uiso 1 1 calc R . . H18B H 0.4186 0.0321 -0.1112 0.093(13) Uiso 1 1 calc R . . H18C H 0.5548 -0.0090 -0.0937 0.105(15) Uiso 1 1 calc R . . C19 C 0.9851(3) 0.07114(12) 0.1337(2) 0.0505(7) Uani 1 1 d . . . H19A H 1.0675 0.0931 0.1245 0.123(16) Uiso 1 1 calc R . . H19B H 1.0059 0.0334 0.1246 0.105(14) Uiso 1 1 calc R . . H19C H 0.9741 0.0764 0.1967 0.104(14) Uiso 1 1 calc R . . C20 C 0.8859(3) 0.17899(11) 0.1106(2) 0.0494(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.02322(6) 0.02441(6) 0.02564(7) 0.00223(4) 0.00510(4) 0.00038(4) Cl1 0.0386(3) 0.0409(3) 0.0531(4) -0.0002(2) 0.0145(2) -0.0139(2) Cl2 0.0455(3) 0.0653(4) 0.0305(3) 0.0151(3) 0.0010(2) -0.0008(3) Cl3 0.0340(3) 0.0476(3) 0.0679(4) 0.0092(3) 0.0057(3) -0.0146(2) Cl4 0.0550(3) 0.0534(4) 0.0311(3) 0.0102(2) -0.0030(2) 0.0052(3) Cl5 0.0554(4) 0.0487(4) 0.0625(4) -0.0064(3) 0.0303(3) 0.0139(3) Cl6 0.0565(3) 0.0358(3) 0.0621(4) -0.0057(3) 0.0238(3) 0.0125(3) Sb2 0.02385(6) 0.02249(6) 0.02440(7) -0.00047(4) 0.00432(4) -0.00075(4) Cl7 0.0327(2) 0.0391(3) 0.0445(3) -0.0059(2) 0.0118(2) 0.0074(2) Cl8 0.0467(3) 0.0363(3) 0.0250(2) -0.00439(19) 0.0034(2) -0.0026(2) Cl9 0.0441(3) 0.0351(3) 0.0449(3) -0.0021(2) 0.0167(2) -0.0147(2) Cl10 0.0506(3) 0.0322(3) 0.0456(3) 0.0050(2) 0.0099(2) -0.0145(2) Cl11 0.0464(3) 0.0527(4) 0.0264(3) 0.0009(2) -0.0022(2) -0.0060(2) Cl12 0.0416(3) 0.0473(3) 0.0645(4) -0.0011(3) 0.0140(3) 0.0193(3) O1 0.117(2) 0.0483(15) 0.143(3) -0.0262(17) 0.004(2) -0.0111(15) C1 0.0299(10) 0.0423(12) 0.0396(13) -0.0022(9) 0.0111(9) -0.0015(8) C2 0.0309(10) 0.0456(13) 0.0326(11) 0.0028(9) 0.0105(8) -0.0004(9) C3 0.0486(13) 0.0459(13) 0.0325(12) -0.0004(10) 0.0127(10) -0.0071(10) C4 0.0706(17) 0.0398(13) 0.0399(13) 0.0070(10) 0.0299(12) 0.0071(12) C5 0.0476(13) 0.0645(18) 0.0380(14) 0.0142(12) 0.0175(11) 0.0190(12) C6 0.0304(10) 0.0690(18) 0.0331(12) 0.0043(11) 0.0119(9) 0.0048(10) C7 0.0340(11) 0.0617(17) 0.0487(15) 0.0095(13) 0.0047(10) 0.0052(11) C8 0.127(3) 0.0420(17) 0.068(2) 0.0091(15) 0.041(2) 0.0099(18) C9 0.0309(12) 0.111(3) 0.0489(17) -0.0064(18) 0.0012(11) -0.0024(15) C10 0.0503(15) 0.0553(18) 0.068(2) -0.0083(15) 0.0054(14) -0.0071(13) O2 0.0629(13) 0.0598(14) 0.102(2) -0.0173(13) -0.0093(13) -0.0140(11) C11 0.0351(10) 0.0311(10) 0.0356(11) 0.0044(8) 0.0097(8) -0.0019(8) C12 0.0407(11) 0.0315(11) 0.0352(11) 0.0065(8) 0.0133(9) 0.0059(8) C13 0.0327(10) 0.0445(13) 0.0315(11) 0.0025(9) 0.0081(8) 0.0044(9) C14 0.0373(11) 0.0413(12) 0.0372(12) -0.0069(9) 0.0164(9) -0.0059(9) C15 0.0435(12) 0.0311(11) 0.0487(14) 0.0046(10) 0.0213(10) 0.0050(9) C16 0.0326(10) 0.0382(11) 0.0340(11) 0.0086(9) 0.0130(8) 0.0044(8) C17 0.0694(18) 0.0342(13) 0.0541(17) 0.0096(11) 0.0129(14) 0.0153(12) C18 0.0565(16) 0.0560(18) 0.0602(19) -0.0197(14) 0.0174(14) -0.0147(13) C19 0.0375(12) 0.0626(18) 0.0504(16) 0.0170(13) 0.0093(11) 0.0139(11) C20 0.0454(13) 0.0426(14) 0.0557(17) 0.0031(12) 0.0049(12) -0.0018(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 Sb1 Cl1 2.3567(5) . ? Sb1 Cl4 2.3594(6) . ? Sb1 Cl5 2.3607(6) . ? Sb1 Cl6 2.3620(6) . ? Sb1 Cl2 2.3664(6) . ? Sb1 Cl3 2.3678(6) . ? Sb2 Cl11 2.3535(6) . ? Sb2 Cl8 2.3601(5) . ? Sb2 Cl9 2.3605(5) . ? Sb2 Cl12 2.3652(6) . ? Sb2 Cl7 2.3719(5) . ? Sb2 Cl10 2.3767(5) . ? O1 C10 1.120(4) . ? C1 C10 1.370(4) . ? C1 C2 1.418(3) . ? C1 C6 1.423(3) . ? C2 C3 1.367(3) . ? C2 C7 1.497(3) . ? C3 C4 1.403(4) . ? C3 H3 0.9500 . ? C4 C5 1.392(4) . ? C4 C8 1.493(4) . ? C5 C6 1.361(4) . ? C5 H5 0.9500 . ? C6 C9 1.506(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8 H8D 0.9800 . ? C8 H8E 0.9800 . ? C8 H8F 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O2 C20 1.123(3) . ? C11 C20 1.380(3) . ? C11 C12 1.415(3) . ? C11 C16 1.425(3) . ? C12 C13 1.374(3) . ? C12 C17 1.497(3) . ? C13 C14 1.397(3) . ? C13 H13 0.9500 . ? C14 C15 1.397(3) . ? C14 C18 1.497(3) . ? C15 C16 1.369(3) . ? C15 H15 0.9500 . ? C16 C19 1.501(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 Sb1 Cl4 90.49(2) . . ? Cl1 Sb1 Cl5 89.25(2) . . ? Cl4 Sb1 Cl5 89.96(3) . . ? Cl1 Sb1 Cl6 90.39(2) . . ? Cl4 Sb1 Cl6 89.98(3) . . ? Cl5 Sb1 Cl6 179.64(3) . . ? Cl1 Sb1 Cl2 90.48(2) . . ? Cl4 Sb1 Cl2 178.97(3) . . ? Cl5 Sb1 Cl2 90.39(3) . . ? Cl6 Sb1 Cl2 89.67(3) . . ? Cl1 Sb1 Cl3 179.60(3) . . ? Cl4 Sb1 Cl3 89.80(2) . . ? Cl5 Sb1 Cl3 90.46(3) . . ? Cl6 Sb1 Cl3 89.89(3) . . ? Cl2 Sb1 Cl3 89.24(2) . . ? Cl11 Sb2 Cl8 178.81(2) . . ? Cl11 Sb2 Cl9 90.22(2) . . ? Cl8 Sb2 Cl9 90.65(2) . . ? Cl11 Sb2 Cl12 89.85(2) . . ? Cl8 Sb2 Cl12 89.33(2) . . ? Cl9 Sb2 Cl12 90.70(2) . . ? Cl11 Sb2 Cl7 90.57(2) . . ? Cl8 Sb2 Cl7 90.24(2) . . ? Cl9 Sb2 Cl7 89.54(2) . . ? Cl12 Sb2 Cl7 179.52(2) . . ? Cl11 Sb2 Cl10 89.70(2) . . ? Cl8 Sb2 Cl10 89.44(2) . . ? Cl9 Sb2 Cl10 179.31(2) . . ? Cl12 Sb2 Cl10 89.98(2) . . ? Cl7 Sb2 Cl10 89.78(2) . . ? C10 C1 C2 117.1(2) . . ? C10 C1 C6 118.4(2) . . ? C2 C1 C6 124.4(2) . . ? C3 C2 C1 116.0(2) . . ? C3 C2 C7 122.8(2) . . ? C1 C2 C7 121.2(2) . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 C8 120.6(3) . . ? C3 C4 C8 119.3(3) . . ? C6 C5 C4 122.2(2) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 115.7(2) . . ? C5 C6 C9 123.8(3) . . ? C1 C6 C9 120.4(3) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C8 H8D 109.5 . . ? H8A C8 H8D 141.1 . . ? H8B C8 H8D 56.3 . . ? H8C C8 H8D 56.3 . . ? C4 C8 H8E 109.5 . . ? H8A C8 H8E 56.3 . . ? H8B C8 H8E 141.1 . . ? H8C C8 H8E 56.3 . . ? H8D C8 H8E 109.5 . . ? C4 C8 H8F 109.5 . . ? H8A C8 H8F 56.3 . . ? H8B C8 H8F 56.3 . . ? H8C C8 H8F 141.1 . . ? H8D C8 H8F 109.5 . . ? H8E C8 H8F 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 C1 178.1(4) . . ? C20 C11 C12 118.0(2) . . ? C20 C11 C16 117.6(2) . . ? C12 C11 C16 124.4(2) . . ? C13 C12 C11 116.1(2) . . ? C13 C12 C17 122.4(2) . . ? C11 C12 C17 121.5(2) . . ? C12 C13 C14 121.7(2) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 C18 120.8(2) . . ? C13 C14 C18 119.3(2) . . ? C16 C15 C14 122.3(2) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C11 115.5(2) . . ? C15 C16 C19 123.2(2) . . ? C11 C16 C19 121.3(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 C11 179.2(4) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.780 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.092 data_milqsx _database_code_depnum_ccdc_archive 'CCDC 239198' _audit_creation_method SHELXL _chemical_name_systematic ; 4'-Methylphenyloxocarbonium hexachloroantimonate ; _chemical_name_common "4'-Methylphenyloxocarbonium hexachloroantimonate" _chemical_formula_moiety 'C8 H7 O, Cl6 Sb' _chemical_formula_structural '(C8 H7 O)^+^, (Cl6 Sb)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C8 H7 Cl6 O Sb' _chemical_formula_weight 453.59 _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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7482(7) _cell_length_b 10.2038(6) _cell_length_c 12.4473(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.4280(10) _cell_angle_gamma 90.00 _cell_volume 1489.47(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5031 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.023 _exptl_crystal_density_method none _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 2.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.529 _exptl_absorpt_correction_T_max 0.748 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15992 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 31.81 _reflns_number_total 4714 _reflns_number_gt 4366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections except for 18 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.4449P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4697 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0202 _refine_ls_wR_factor_ref 0.0508 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.756112(7) 0.016571(9) 0.160872(7) 0.02026(4) Uani 1 1 d . . . Cl1 Cl 0.93424(3) 0.12861(4) 0.16989(3) 0.02958(8) Uani 1 1 d . . . Cl2 Cl 0.58033(3) -0.09365(5) 0.15574(4) 0.03782(10) Uani 1 1 d . . . Cl3 Cl 0.70252(3) 0.13657(4) 0.31326(3) 0.03011(8) Uani 1 1 d . . . Cl4 Cl 0.83916(4) -0.14898(4) 0.27484(3) 0.03209(8) Uani 1 1 d . . . Cl5 Cl 0.81360(3) -0.10263(4) 0.01001(3) 0.02909(8) Uani 1 1 d . . . Cl6 Cl 0.67921(4) 0.18198(4) 0.04575(3) 0.03748(9) Uani 1 1 d . . . O1 O 0.92439(10) 0.33663(13) 0.38727(9) 0.0336(3) Uani 1 1 d . . . C1 C 0.80868(13) 0.45496(17) 0.24193(13) 0.0279(3) Uani 1 1 d . . . C2 C 0.85748(15) 0.48050(17) 0.14373(14) 0.0308(3) Uani 1 1 d . . . H2 H 0.9344 0.4578 0.1332 0.041(6) Uiso 1 1 calc R . . C3 C 0.79033(15) 0.53947(18) 0.06322(14) 0.0308(3) Uani 1 1 d . . . H3 H 0.8217 0.5580 -0.0037 0.040(6) Uiso 1 1 calc R . . C4 C 0.67653(13) 0.57271(15) 0.07810(12) 0.0263(3) Uani 1 1 d . . . C5 C 0.63118(13) 0.54779(18) 0.17732(14) 0.0295(3) Uani 1 1 d . . . H5 H 0.5546 0.5719 0.1879 0.046(6) Uiso 1 1 calc R . . C6 C 0.69546(15) 0.48879(17) 0.26027(14) 0.0302(3) Uani 1 1 d . . . H6 H 0.6642 0.4716 0.3275 0.036(6) Uiso 1 1 calc R . . C7 C 0.87316(13) 0.39009(17) 0.32284(13) 0.0287(3) Uani 1 1 d . . . C8 C 0.60444(14) 0.63267(17) -0.01203(13) 0.0313(3) Uani 1 1 d . . . H8A H 0.5292 0.6540 0.0131 0.063(8) Uiso 1 1 calc R . . H8B H 0.5959 0.5704 -0.0719 0.059(7) Uiso 1 1 calc R . . H8C H 0.6410 0.7128 -0.0363 0.094(11) Uiso 1 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 0.01935(5) 0.02208(6) 0.01929(5) -0.00087(3) 0.00063(3) 0.00023(3) Cl1 0.02284(15) 0.02967(18) 0.03632(19) -0.00322(14) 0.00257(14) -0.00431(13) Cl2 0.02362(17) 0.0396(2) 0.0508(2) -0.01529(18) 0.00737(16) -0.00815(15) Cl3 0.03572(19) 0.02802(18) 0.02747(17) -0.00668(13) 0.00927(14) -0.00321(14) Cl4 0.0387(2) 0.02918(18) 0.02825(18) 0.00617(14) 0.00108(15) 0.00590(15) Cl5 0.03253(18) 0.03155(19) 0.02359(16) -0.00565(13) 0.00491(13) 0.00013(14) Cl6 0.0418(2) 0.0365(2) 0.0332(2) 0.00680(16) -0.00527(16) 0.01175(17) O1 0.0319(6) 0.0390(7) 0.0294(6) 0.0024(5) -0.0032(5) 0.0001(5) C1 0.0269(7) 0.0301(7) 0.0263(7) -0.0003(6) -0.0022(6) -0.0028(6) C2 0.0257(7) 0.0384(9) 0.0283(8) -0.0001(6) 0.0011(6) 0.0017(6) C3 0.0319(8) 0.0363(9) 0.0243(7) 0.0005(6) 0.0027(6) 0.0002(6) C4 0.0288(7) 0.0225(7) 0.0270(7) -0.0039(5) -0.0032(5) -0.0022(5) C5 0.0228(7) 0.0341(8) 0.0314(8) -0.0019(6) -0.0002(6) -0.0003(6) C6 0.0272(7) 0.0389(9) 0.0246(7) 0.0007(6) 0.0018(6) -0.0050(6) C7 0.0270(7) 0.0309(8) 0.0283(7) -0.0023(6) 0.0017(6) -0.0042(6) C8 0.0342(8) 0.0295(8) 0.0292(8) -0.0016(6) -0.0072(6) 0.0012(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 Cl2 2.3490(4) . ? Sb1 Cl6 2.3587(4) . ? Sb1 Cl5 2.3692(4) . ? Sb1 Cl3 2.3742(4) . ? Sb1 Cl4 2.3775(4) . ? Sb1 Cl1 2.3813(4) . ? O1 C7 1.116(2) . ? C1 C7 1.391(2) . ? C1 C2 1.405(2) . ? C1 C6 1.406(2) . ? C2 C3 1.376(2) . ? C2 H2 0.9500 . ? C3 C4 1.402(2) . ? C3 H3 0.9500 . ? C4 C5 1.397(2) . ? C4 C8 1.496(2) . ? C5 C6 1.380(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 Cl6 91.253(18) . . ? Cl2 Sb1 Cl5 91.400(15) . . ? Cl6 Sb1 Cl5 90.165(16) . . ? Cl2 Sb1 Cl3 89.656(15) . . ? Cl6 Sb1 Cl3 90.348(16) . . ? Cl5 Sb1 Cl3 178.816(13) . . ? Cl2 Sb1 Cl4 90.274(17) . . ? Cl6 Sb1 Cl4 178.258(15) . . ? Cl5 Sb1 Cl4 88.961(15) . . ? Cl3 Sb1 Cl4 90.498(15) . . ? Cl2 Sb1 Cl1 178.856(15) . . ? Cl6 Sb1 Cl1 89.353(16) . . ? Cl5 Sb1 Cl1 89.568(14) . . ? Cl3 Sb1 Cl1 89.370(14) . . ? Cl4 Sb1 Cl1 89.134(15) . . ? C7 C1 C2 119.03(15) . . ? C7 C1 C6 118.60(15) . . ? C2 C1 C6 122.33(15) . . ? C3 C2 C1 117.95(16) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 121.26(16) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.32(14) . . ? C5 C4 C8 120.58(14) . . ? C3 C4 C8 120.10(15) . . ? C6 C5 C4 121.33(15) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 117.78(15) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? O1 C7 C1 179.15(19) . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.035 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.092 data_mil-psx _database_code_depnum_ccdc_archive 'CCDC 239199' _audit_creation_method SHELXL _chemical_name_systematic ; Ethyloxocarbonium tetrachlorogallate ; _chemical_name_common 'Ethyloxocarbonium tetrachlorogallate' _chemical_formula_moiety 'C3 H5 O, Cl4 Ga' _chemical_formula_structural '(C3 H5 O)^+^, (Cl4 Ga)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C3 H5 Cl4 Ga O' _chemical_formula_weight 268.59 _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' 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1459(12) _cell_length_b 9.487(2) _cell_length_c 13.931(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.909(4) _cell_angle_gamma 90.00 _cell_volume 935.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1184 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.907 _exptl_crystal_density_method none _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 4.012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.480 _exptl_absorpt_correction_T_max 0.852 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8621 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 31.93 _reflns_number_total 3008 _reflns_number_gt 1829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections except for 7 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3002 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.18793(5) 0.75142(4) 0.10310(3) 0.02729(12) Uani 1 1 d . . . Cl1 Cl -0.06767(14) 0.87669(10) 0.09663(7) 0.0407(2) Uani 1 1 d . . . Cl2 Cl 0.43233(14) 0.89042(11) 0.13012(8) 0.0444(3) Uani 1 1 d . . . Cl3 Cl 0.19598(15) 0.63360(10) -0.02844(7) 0.0422(2) Uani 1 1 d . . . Cl4 Cl 0.19347(15) 0.60899(11) 0.22611(7) 0.0435(3) Uani 1 1 d . . . O1 O 0.6860(5) 0.5855(3) 0.1851(2) 0.0522(8) Uani 1 1 d . . . C1 C 0.7346(6) 0.6482(4) 0.2503(3) 0.0379(9) Uani 1 1 d . . . C2 C 0.7944(6) 0.7319(4) 0.3338(3) 0.0390(9) Uani 1 1 d . . . H2A H 0.8575 0.8178 0.3137 0.048(12) Uiso 1 1 calc R . . H2B H 0.8883 0.6782 0.3783 0.064(15) Uiso 1 1 calc R . . C3 C 0.6325(6) 0.7750(4) 0.3877(3) 0.0403(10) Uani 1 1 d . . . H3A H 0.5378 0.8268 0.3437 0.076(17) Uiso 1 1 calc R . . H3B H 0.6808 0.8354 0.4426 0.052(12) Uiso 1 1 calc R . . H3C H 0.5746 0.6906 0.4115 0.046(12) Uiso 1 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 Ga1 0.0285(2) 0.0276(2) 0.0264(2) -0.00109(15) 0.00606(14) -0.00031(17) Cl1 0.0377(5) 0.0411(5) 0.0449(6) 0.0014(4) 0.0112(4) 0.0102(4) Cl2 0.0356(5) 0.0402(5) 0.0569(6) -0.0039(4) 0.0042(4) -0.0104(4) Cl3 0.0488(6) 0.0448(6) 0.0345(5) -0.0108(4) 0.0111(4) 0.0023(5) Cl4 0.0541(6) 0.0416(5) 0.0362(5) 0.0116(4) 0.0108(4) 0.0051(5) O1 0.060(2) 0.0490(18) 0.0508(18) -0.0171(14) 0.0187(15) -0.0100(16) C1 0.041(2) 0.035(2) 0.040(2) 0.0028(17) 0.0165(18) 0.0026(18) C2 0.037(2) 0.041(2) 0.039(2) -0.0103(17) 0.0039(17) -0.0005(18) C3 0.051(3) 0.039(2) 0.032(2) -0.0085(16) 0.0078(19) 0.0018(19) _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 Ga1 Cl3 2.1541(10) . ? Ga1 Cl1 2.1704(10) . ? Ga1 Cl4 2.1784(10) . ? Ga1 Cl2 2.1794(10) . ? O1 C1 1.102(5) . ? C1 C2 1.424(6) . ? C2 C3 1.519(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? 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 Ga1 Cl1 111.69(4) . . ? Cl3 Ga1 Cl4 110.34(5) . . ? Cl1 Ga1 Cl4 107.24(4) . . ? Cl3 Ga1 Cl2 110.26(5) . . ? Cl1 Ga1 Cl2 109.01(4) . . ? Cl4 Ga1 Cl2 108.18(4) . . ? O1 C1 C2 178.6(5) . . ? C1 C2 C3 113.0(4) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.236 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.135 data_vovmsx _database_code_depnum_ccdc_archive 'CCDC 239200' _audit_creation_method SHELXL _chemical_name_systematic ; Methyloxocarbonium hexafluoroantimonate ; _chemical_name_common 'Methyloxocarbonium hexafluoroantimonate' _chemical_formula_moiety 'F6 Sb, C2 H3 O' _chemical_formula_structural '(C2 H3 O)^+^, (F6 Sb)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C2 H3 F6 O Sb' _chemical_formula_weight 278.79 _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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.7299(7) _cell_length_b 7.7373(9) _cell_length_c 7.7479(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.187(2) _cell_angle_gamma 90.00 _cell_volume 338.08(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3008 _cell_measurement_theta_min 4 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.739 _exptl_crystal_density_method none _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 4.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.368 _exptl_absorpt_correction_T_max 0.661 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3629 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 31.79 _reflns_number_total 1150 _reflns_number_gt 1108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement on F^2^ for all reflections except for 8 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0842P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1142 _refine_ls_number_parameters 57 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0507 _refine_ls_wR_factor_gt 0.0502 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.40221(3) 0.2500 0.26728(2) 0.02147(7) Uani 1 2 d S . . F1 F 0.6168(3) 0.0801(3) 0.2293(3) 0.0634(7) Uani 1 1 d . . . F2 F 0.1842(4) 0.0816(2) 0.3071(3) 0.0534(5) Uani 1 1 d . . . F3 F 0.5242(5) 0.2500 0.5066(3) 0.0677(10) Uani 1 2 d S . . F4 F 0.2721(5) 0.2500 0.0305(3) 0.0669(9) Uani 1 2 d S . . O1 O -0.2364(5) 0.2500 0.8764(4) 0.0423(6) Uani 1 2 d S . . C1 C -0.1084(5) 0.2500 0.7846(4) 0.0289(6) Uani 1 2 d S . . C2 C 0.0579(5) 0.2500 0.6689(4) 0.0268(5) Uani 1 2 d S . . H21 H 0.1531 0.1514 0.6863 0.042(8) Uiso 1 1 d R . . H22 H -0.0170 0.2500 0.5583 0.063(16) Uiso 1 2 d SR . . 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 0.01984(10) 0.02077(10) 0.02273(11) 0.000 0.00084(6) 0.000 F1 0.0601(12) 0.0507(12) 0.0880(18) 0.0157(9) 0.0367(12) 0.0316(9) F2 0.0541(10) 0.0330(8) 0.0802(13) -0.0077(8) 0.0314(10) -0.0173(7) F3 0.0452(14) 0.127(3) 0.0262(11) 0.000 -0.0059(9) 0.000 F4 0.0533(15) 0.115(3) 0.0276(11) 0.000 -0.0054(10) 0.000 O1 0.0428(14) 0.0516(16) 0.0366(13) 0.000 0.0181(11) 0.000 C1 0.0301(14) 0.0278(15) 0.0290(14) 0.000 0.0056(11) 0.000 C2 0.0257(12) 0.0277(13) 0.0280(13) 0.000 0.0069(10) 0.000 _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 F4 1.854(3) . ? Sb1 F1 1.8589(19) 4_565 ? Sb1 F1 1.8589(18) . ? Sb1 F3 1.862(3) . ? Sb1 F2 1.8683(16) . ? Sb1 F2 1.8683(16) 4_565 ? O1 C1 1.108(4) . ? C1 C2 1.419(4) . ? C2 H21 0.9339 . ? C2 H22 0.8878 . ? 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 F4 Sb1 F1 90.28(10) . 4_565 ? F4 Sb1 F1 90.28(10) . . ? F1 Sb1 F1 90.04(16) 4_565 . ? F4 Sb1 F3 178.36(10) . . ? F1 Sb1 F3 90.88(9) 4_565 . ? F1 Sb1 F3 90.88(9) . . ? F4 Sb1 F2 89.99(10) . . ? F1 Sb1 F2 179.16(7) 4_565 . ? F1 Sb1 F2 90.75(12) . . ? F3 Sb1 F2 88.83(10) . . ? F4 Sb1 F2 89.99(10) . 4_565 ? F1 Sb1 F2 90.75(12) 4_565 4_565 ? F1 Sb1 F2 179.16(7) . 4_565 ? F3 Sb1 F2 88.83(10) . 4_565 ? F2 Sb1 F2 88.45(12) . 4_565 ? O1 C1 C2 179.2(3) . . ? C1 C2 H21 110.4 . . ? C1 C2 H22 110.2 . . ? H21 C2 H22 108.0 . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.015 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.107 data_milosx _database_code_depnum_ccdc_archive 'CCDC 249788' _audit_creation_method SHELXL _chemical_name_systematic ; Methyloxocarbonium hexachloroantimonate ; _chemical_name_common ? _chemical_formula_moiety 'C2 H3 O, Cl6 Sb' _chemical_formula_structural '(C2 H3 O)^+^, (Cl6 Sb)^-^' _chemical_formula_analytical ? _chemical_formula_sum 'C2 H3 Cl6 O Sb' _chemical_formula_weight 377.49 _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' 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 'I m m 2' _symmetry_space_group_name_Hall 'I 2 -2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, z' '-x, y, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.1080(7) _cell_length_b 9.0055(9) _cell_length_c 7.9518(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 509.00(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2525 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.463 _exptl_crystal_density_method none _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 4.222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.560 _exptl_absorpt_correction_T_max 0.713 _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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2638 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 31.33 _reflns_number_total 907 _reflns_number_gt 898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Regular (racemic) twin. Refinement on F^2^ for all reflections except for 5 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.2670P] 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 mixed _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 0.50(4) _refine_ls_number_reflns 902 _refine_ls_number_parameters 35 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0157 _refine_ls_R_factor_gt 0.0156 _refine_ls_wR_factor_ref 0.0402 _refine_ls_wR_factor_gt 0.0399 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.0000 0.0000 0.67871(12) 0.02094(4) Uani 1 4 d S . . Cl1 Cl 0.0000 0.0000 0.38004(14) 0.0370(4) Uani 1 4 d S . . Cl2 Cl 0.23738(5) 0.18472(4) 0.6768(3) 0.03385(8) Uani 1 1 d . . . Cl3 Cl 0.0000 0.0000 0.97443(12) 0.0391(5) Uani 1 4 d S . . O1 O 0.0000 0.5000 0.8415(10) 0.063(2) Uani 1 4 d S . . C1 C 0.0000 0.5000 0.674(4) 0.0600(16) Uani 1 4 d S . . C2 C 0.0000 0.5000 0.5214(7) 0.0277(12) Uani 1 4 d S . . H2A H 0.1298 0.4944 0.4804 0.042 Uiso 0.25 1 calc PR . . H2B H -0.0587 0.5915 0.4804 0.042 Uiso 0.25 1 calc PR . . H2C H -0.0711 0.4141 0.4804 0.042 Uiso 0.25 1 calc PR . . 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 0.02217(7) 0.01842(7) 0.02223(7) 0.000 0.000 0.000 Cl1 0.0437(8) 0.0431(9) 0.0243(7) 0.000 0.000 0.000 Cl2 0.02671(14) 0.02521(15) 0.04963(19) -0.0056(7) 0.0048(6) -0.00621(12) Cl3 0.0303(7) 0.0675(14) 0.0196(7) 0.000 0.000 0.000 O1 0.060(4) 0.066(5) 0.064(4) 0.000 0.000 0.000 C1 0.0260(13) 0.0241(14) 0.130(5) 0.000 0.000 0.000 C2 0.037(3) 0.024(2) 0.021(2) 0.000 0.000 0.000 _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 2.3515(17) . ? Sb1 Cl2 2.3695(4) 2 ? Sb1 Cl2 2.3695(4) . ? Sb1 Cl2 2.3695(4) 4 ? Sb1 Cl2 2.3695(4) 3 ? Sb1 Cl1 2.3749(18) . ? O1 C1 1.33(4) . ? C1 C2 1.22(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? 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 Cl2 90.36(4) . 2 ? Cl3 Sb1 Cl2 90.36(4) . . ? Cl2 Sb1 Cl2 179.28(9) 2 . ? Cl3 Sb1 Cl2 90.36(4) . 4 ? Cl2 Sb1 Cl2 89.186(19) 2 4 ? Cl2 Sb1 Cl2 90.810(19) . 4 ? Cl3 Sb1 Cl2 90.36(4) . 3 ? Cl2 Sb1 Cl2 90.810(19) 2 3 ? Cl2 Sb1 Cl2 89.186(19) . 3 ? Cl2 Sb1 Cl2 179.28(9) 4 3 ? Cl3 Sb1 Cl1 180.0 . . ? Cl2 Sb1 Cl1 89.64(4) 2 . ? Cl2 Sb1 Cl1 89.64(4) . . ? Cl2 Sb1 Cl1 89.64(4) 4 . ? Cl2 Sb1 Cl1 89.64(4) 3 . ? C2 C1 O1 180.000(4) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 31.33 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.353 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.104