# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jack Passmore' _publ_contact_author_email PASSMORE@UNB.CA _publ_section_title ; The preparation of the MF6- (M = As, Sb) salts of 1,4-benzoquinodal bridged bis-1,3,2-dithiazolylium utilizing the cycloaddition and oxidative dehydrogenation chemistry of SNSMF6 and observation of a hybrid semiquinoidal-thiazyl radical cation by EPR ; loop_ _publ_author_name 'Jack Passmore' 'Andreas Decken' 'Aaron Mailman' # Attachment 'CCDC_732425.cif' data_jp080360 _database_code_depnum_ccdc_archive 'CCDC 732425' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; Hydrogen atoms were included in calculated positions and refined using a riding model. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 N2 O2 S4, C2 H3 N, 2 (As F6)' _chemical_formula_sum 'C8 H3 As2 F12 N3 O2 S4' _chemical_formula_weight 679.21 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.0499 2.0058 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc ' _symmetry_int_tables_number 15 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 18.343(4) _cell_length_b 8.0690(13) _cell_length_c 15.085(3) _cell_angle_alpha 90.00 _cell_angle_beta 120.246(4) _cell_angle_gamma 90.00 _cell_volume 1928.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 4113 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 28.23 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 4.024 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.170403 _exptl_absorpt_correction_T_max 0.298778 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6425 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2155 _reflns_number_gt 1996 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0268P)^2^+1.3198P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2155 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0517 _refine_ls_wR_factor_gt 0.0506 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 S1 S 0.18824(3) 0.89370(6) 1.12557(3) 0.02731(11) Uani 1 1 d . . . S2 S 0.12852(3) 0.95612(6) 0.92324(3) 0.02815(11) Uani 1 1 d . . . N1 N 0.20650(11) 0.90588(19) 1.03269(13) 0.0297(4) Uani 1 1 d . . . C1 C -0.03284(11) 1.0406(2) 0.88897(13) 0.0227(3) Uani 1 1 d . . . C2 C 0.05466(11) 0.9800(2) 0.95885(13) 0.0224(3) Uani 1 1 d . . . C3 C 0.08504(11) 0.9483(2) 1.06081(13) 0.0223(3) Uani 1 1 d . . . O1 O -0.05928(9) 1.08218(16) 0.80142(10) 0.0310(3) Uani 1 1 d . . . As1 As 0.147072(11) 0.42071(2) 0.078461(13) 0.02364(7) Uani 1 1 d . . . F1 F 0.11284(9) 0.57860(15) -0.01035(9) 0.0426(3) Uani 1 1 d . . . F2 F 0.18155(10) 0.26206(16) 0.16766(10) 0.0580(4) Uani 1 1 d . . . F3 F 0.12248(9) 0.53706(17) 0.15502(10) 0.0454(3) Uani 1 1 d . . . F4 F 0.24735(7) 0.50685(17) 0.14102(10) 0.0415(3) Uani 1 1 d . . . F5 F 0.17321(9) 0.30438(18) 0.00307(11) 0.0556(4) Uani 1 1 d . . . F6 F 0.04820(7) 0.33072(15) 0.01686(10) 0.0421(3) Uani 1 1 d . . . C4 C 1.0000 0.6122(4) 0.7500 0.0377(7) Uani 1 2 d S . . C5 C 1.0000 0.4327(4) 0.7500 0.0460(8) Uani 1 2 d S . . H5A H 0.9930 0.3922 0.8065 0.069 Uiso 0.50 1 calc PR . . H5B H 1.0536 0.3922 0.7589 0.069 Uiso 0.50 1 calc PR . . H5C H 0.9534 0.3922 0.6846 0.069 Uiso 0.50 1 calc PR . . N2 N 1.0000 0.7526(4) 0.7500 0.0538(8) Uani 1 2 d S . . 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 S1 0.0228(2) 0.0302(2) 0.0263(2) -0.00105(17) 0.01045(18) 0.00290(19) S2 0.0263(2) 0.0343(2) 0.0295(2) -0.00046(18) 0.0183(2) 0.0009(2) N1 0.0254(8) 0.0304(8) 0.0362(8) -0.0034(6) 0.0178(7) 0.0005(7) C1 0.0238(9) 0.0218(8) 0.0235(8) -0.0039(7) 0.0126(7) -0.0027(7) C2 0.0237(9) 0.0209(8) 0.0258(8) -0.0034(7) 0.0148(7) -0.0026(7) C3 0.0227(8) 0.0197(8) 0.0239(8) -0.0020(6) 0.0113(7) -0.0008(7) O1 0.0333(7) 0.0377(8) 0.0235(6) 0.0031(5) 0.0154(6) 0.0036(6) As1 0.01998(11) 0.02090(11) 0.02724(11) -0.00415(6) 0.00982(8) -0.00125(7) F1 0.0490(8) 0.0349(7) 0.0354(6) 0.0022(5) 0.0149(6) -0.0041(6) F2 0.0602(9) 0.0331(7) 0.0460(7) 0.0080(6) 0.0010(7) -0.0067(7) F3 0.0525(8) 0.0471(7) 0.0527(8) -0.0169(6) 0.0385(7) -0.0124(7) F4 0.0247(6) 0.0436(7) 0.0504(7) -0.0103(6) 0.0145(5) -0.0067(6) F5 0.0510(8) 0.0541(8) 0.0695(9) -0.0286(7) 0.0362(7) -0.0002(7) F6 0.0266(6) 0.0333(6) 0.0558(7) -0.0078(6) 0.0128(6) -0.0067(5) C4 0.0488(19) 0.0343(16) 0.0269(13) 0.000 0.0167(13) 0.000 C5 0.071(2) 0.0305(15) 0.0452(18) 0.000 0.0355(18) 0.000 N2 0.068(2) 0.0340(15) 0.0400(14) 0.000 0.0130(14) 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 S1 N1 1.5993(17) . ? S1 C3 1.6939(19) . ? S2 N1 1.5991(18) . ? S2 C2 1.7013(17) . ? C1 O1 1.203(2) . ? C1 C2 1.491(2) . ? C1 C3 1.493(2) 5_577 ? C2 C3 1.371(2) . ? C3 C1 1.493(2) 5_577 ? As1 F3 1.7156(12) . ? As1 F5 1.7187(12) . ? As1 F1 1.7218(12) . ? As1 F6 1.7269(12) . ? As1 F2 1.7298(13) . ? As1 F4 1.7344(12) . ? C4 N2 1.133(4) . ? C4 C5 1.448(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 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 N1 S1 C3 98.35(9) . . ? N1 S2 C2 98.24(9) . . ? S2 N1 S1 116.55(10) . . ? O1 C1 C2 124.25(16) . . ? O1 C1 C3 122.25(17) . 5_577 ? C2 C1 C3 113.46(14) . 5_577 ? C3 C2 C1 122.63(15) . . ? C3 C2 S2 113.25(14) . . ? C1 C2 S2 123.99(13) . . ? C2 C3 C1 123.78(16) . 5_577 ? C2 C3 S1 113.60(13) . . ? C1 C3 S1 122.61(13) 5_577 . ? F3 As1 F5 179.18(7) . . ? F3 As1 F1 90.14(7) . . ? F5 As1 F1 90.18(7) . . ? F3 As1 F6 91.80(6) . . ? F5 As1 F6 88.95(7) . . ? F1 As1 F6 91.14(6) . . ? F3 As1 F2 89.91(8) . . ? F5 As1 F2 89.77(8) . . ? F1 As1 F2 179.94(8) . . ? F6 As1 F2 88.89(6) . . ? F3 As1 F4 88.90(6) . . ? F5 As1 F4 90.34(7) . . ? F1 As1 F4 89.89(6) . . ? F6 As1 F4 178.76(6) . . ? F2 As1 F4 90.08(7) . . ? N2 C4 C5 180.000(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.499 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.070 # Attachment 'CCDC_732426.cif' data_jp040304 _database_code_depnum_ccdc_archive 'CCDC 732426' _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2004). SADABS 2004. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C6 H4 N O2 S2, C6 H4 O2, F6 Sb' _chemical_formula_sum 'C12 H8 F6 N O4 S2 Sb' _chemical_melting_point ? _exptl_crystal_description Irregular _exptl_crystal_colour Black _diffrn_ambient_temperature 173(1) _chemical_formula_weight 530.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 9.0959(5) _cell_length_b 12.9028(7) _cell_length_c 14.3415(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.500(1) _cell_angle_gamma 90.00 _cell_volume 1680.02(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 6373 _cell_measurement_theta_min 2.582 _cell_measurement_theta_max 25.627 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.973 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5058 _exptl_absorpt_correction_T_max 0.8271 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8267 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2856 _reflns_number_gt 2672 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+0.9181P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2856 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0539 _refine_ls_wR_factor_gt 0.0531 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.02599(7) 0.60533(5) 0.84936(5) 0.03351(16) Uani 1 1 d . . . N N 1.0844(2) 0.66854(17) 0.76306(15) 0.0348(5) Uani 1 1 d . . . S2 S 1.05456(8) 0.79026(5) 0.76268(4) 0.03221(15) Uani 1 1 d . . . C3 C 0.9502(3) 0.70503(18) 0.90826(17) 0.0265(5) Uani 1 1 d . . . C4 C 0.9657(3) 0.80032(19) 0.86343(16) 0.0248(5) Uani 1 1 d . . . C5 C 0.9124(3) 0.89224(18) 0.90153(17) 0.0273(5) Uani 1 1 d . . . C6 C 0.8423(3) 0.8831(2) 0.98323(18) 0.0303(5) Uani 1 1 d . . . C7 C 0.8257(3) 0.7880(2) 1.02745(19) 0.0311(6) Uani 1 1 d . . . C8 C 0.8781(3) 0.6978(2) 0.99179(18) 0.0298(5) Uani 1 1 d . . . O1 O 0.8671(2) 0.60183(15) 1.02825(17) 0.0417(5) Uani 1 1 d . . . O2 O 0.9364(2) 0.97991(15) 0.85306(14) 0.0374(5) Uani 1 1 d . . . C11 C 0.3790(3) 0.44004(19) 0.79331(17) 0.0303(5) Uani 1 1 d . . . C12 C 0.4580(3) 0.4189(2) 0.70893(19) 0.0384(6) Uani 1 1 d . . . C13 C 0.5731(3) 0.4745(2) 0.68862(19) 0.0390(6) Uani 1 1 d . . . C14 C 0.6295(3) 0.5589(2) 0.74994(18) 0.0355(6) Uani 1 1 d . . . C15 C 0.5530(3) 0.5776(2) 0.83546(19) 0.0369(6) Uani 1 1 d . . . C16 C 0.4370(3) 0.5222(2) 0.85601(18) 0.0328(6) Uani 1 1 d . . . O3 O 0.2678(2) 0.39176(15) 0.80959(13) 0.0405(4) Uani 1 1 d . . . O4 O 0.7370(2) 0.60955(18) 0.73140(14) 0.0516(5) Uani 1 1 d . . . Sb Sb 0.353861(17) 0.768436(12) 0.048686(11) 0.02525(8) Uani 1 1 d . . . F1 F 0.2228(2) 0.66146(16) 0.07372(14) 0.0600(5) Uani 1 1 d . . . F2 F 0.4814(2) 0.87594(13) 0.02249(12) 0.0517(4) Uani 1 1 d . . . F3 F 0.30307(19) 0.75499(13) -0.07907(11) 0.0412(4) Uani 1 1 d . . . F4 F 0.1996(2) 0.86496(14) 0.05556(12) 0.0551(5) Uani 1 1 d . . . F5 F 0.4018(2) 0.78365(14) 0.17593(11) 0.0514(5) Uani 1 1 d . . . F6 F 0.50627(18) 0.67310(13) 0.03806(11) 0.0449(4) Uani 1 1 d . . . H1 H 0.831(3) 0.603(2) 1.065(2) 0.024(9) Uiso 1 1 d . . . H2 H 0.905(4) 1.024(3) 0.875(2) 0.053(11) Uiso 1 1 d . . . H6 H 0.810(3) 0.939(2) 1.0101(18) 0.028(7) Uiso 1 1 d . . . H7 H 0.779(3) 0.782(2) 1.080(2) 0.029(7) Uiso 1 1 d . . . H12 H 0.426(3) 0.372(3) 0.674(2) 0.046(9) Uiso 1 1 d . . . H13 H 0.621(3) 0.465(2) 0.6341(19) 0.040(8) Uiso 1 1 d . . . H15 H 0.586(3) 0.630(2) 0.873(2) 0.045(8) Uiso 1 1 d . . . H16 H 0.390(3) 0.531(2) 0.9074(19) 0.031(7) Uiso 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 S1 0.0340(3) 0.0252(3) 0.0418(4) -0.0044(3) 0.0066(3) 0.0039(3) N 0.0347(12) 0.0351(12) 0.0351(12) -0.0095(10) 0.0065(9) 0.0010(10) S2 0.0382(4) 0.0330(3) 0.0263(3) -0.0022(3) 0.0085(3) 0.0027(3) C3 0.0215(12) 0.0248(12) 0.0329(13) -0.0040(10) -0.0002(10) 0.0020(10) C4 0.0225(12) 0.0294(12) 0.0228(12) -0.0004(10) 0.0028(9) 0.0027(10) C5 0.0278(13) 0.0257(12) 0.0282(13) -0.0014(10) 0.0003(10) 0.0016(10) C6 0.0293(13) 0.0290(13) 0.0331(14) -0.0063(11) 0.0051(11) 0.0034(11) C7 0.0261(13) 0.0415(15) 0.0265(13) 0.0000(11) 0.0076(11) -0.0003(11) C8 0.0230(12) 0.0317(13) 0.0347(14) 0.0040(11) 0.0032(10) -0.0014(10) O1 0.0454(12) 0.0338(11) 0.0478(13) 0.0107(10) 0.0194(11) -0.0004(9) O2 0.0528(12) 0.0227(9) 0.0379(11) -0.0001(8) 0.0128(9) 0.0026(9) C11 0.0313(13) 0.0307(13) 0.0287(13) 0.0075(10) 0.0000(10) 0.0031(11) C12 0.0458(17) 0.0393(15) 0.0301(14) -0.0066(12) 0.0019(12) -0.0014(13) C13 0.0391(16) 0.0491(16) 0.0295(14) -0.0028(12) 0.0086(12) 0.0023(13) C14 0.0309(14) 0.0413(15) 0.0344(14) 0.0081(12) 0.0013(11) 0.0003(12) C15 0.0423(16) 0.0357(15) 0.0325(14) -0.0021(12) 0.0022(12) -0.0046(12) C16 0.0385(15) 0.0345(14) 0.0261(13) 0.0004(11) 0.0080(11) 0.0025(11) O3 0.0381(11) 0.0444(11) 0.0386(11) 0.0085(9) -0.0009(8) -0.0116(9) O4 0.0401(11) 0.0713(15) 0.0436(12) 0.0090(10) 0.0046(9) -0.0160(11) Sb 0.02661(11) 0.02486(12) 0.02432(11) -0.00047(6) 0.00178(7) 0.00289(6) F1 0.0457(11) 0.0675(13) 0.0669(12) 0.0163(10) 0.0049(9) -0.0194(9) F2 0.0583(11) 0.0403(9) 0.0558(11) 0.0070(8) -0.0018(8) -0.0174(8) F3 0.0436(10) 0.0530(9) 0.0262(8) -0.0043(7) -0.0047(7) 0.0074(7) F4 0.0524(11) 0.0577(11) 0.0549(11) -0.0119(9) 0.0014(8) 0.0310(9) F5 0.0597(12) 0.0700(12) 0.0238(8) -0.0041(8) -0.0019(8) 0.0062(9) F6 0.0430(9) 0.0447(9) 0.0465(9) -0.0033(8) -0.0019(7) 0.0196(8) _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 S1 N 1.600(2) . ? S1 C3 1.707(2) . ? N S2 1.594(2) . ? S2 C4 1.703(2) . ? C3 C4 1.399(4) . ? C3 C8 1.403(3) . ? C4 C5 1.404(3) . ? C5 O2 1.352(3) . ? C5 C6 1.373(3) . ? C6 C7 1.394(4) . ? C6 H6 0.87(3) . ? C7 C8 1.368(4) . ? C7 H7 0.88(3) . ? C8 O1 1.351(3) . ? O1 H1 0.64(3) . ? O2 H2 0.72(3) . ? C11 O3 1.222(3) . ? C11 C16 1.467(4) . ? C11 C12 1.470(4) . ? C12 C13 1.317(4) . ? C12 H12 0.83(3) . ? C13 C14 1.471(4) . ? C13 H13 0.93(3) . ? C14 O4 1.219(3) . ? C14 C15 1.467(4) . ? C15 C16 1.323(4) . ? C15 H15 0.90(3) . ? C16 H16 0.88(3) . ? Sb F5 1.8606(16) . ? Sb F2 1.8612(16) . ? Sb F6 1.8665(15) . ? Sb F3 1.8700(15) . ? Sb F1 1.8729(17) . ? Sb F4 1.8830(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N S1 C3 99.32(12) . . ? S2 N S1 116.14(13) . . ? N S2 C4 99.31(12) . . ? C4 C3 C8 121.1(2) . . ? C4 C3 S1 112.31(19) . . ? C8 C3 S1 126.6(2) . . ? C3 C4 C5 121.1(2) . . ? C3 C4 S2 112.93(18) . . ? C5 C4 S2 125.98(19) . . ? O2 C5 C6 127.5(2) . . ? O2 C5 C4 115.8(2) . . ? C6 C5 C4 116.7(2) . . ? C5 C6 C7 122.2(2) . . ? C5 C6 H6 119.5(17) . . ? C7 C6 H6 118.3(17) . . ? C8 C7 C6 121.9(2) . . ? C8 C7 H7 116.2(17) . . ? C6 C7 H7 121.9(17) . . ? O1 C8 C7 126.8(2) . . ? O1 C8 C3 116.2(2) . . ? C7 C8 C3 117.0(2) . . ? C8 O1 H1 111(3) . . ? C5 O2 H2 111(3) . . ? O3 C11 C16 121.4(2) . . ? O3 C11 C12 121.0(2) . . ? C16 C11 C12 117.6(2) . . ? C13 C12 C11 121.1(3) . . ? C13 C12 H12 121(2) . . ? C11 C12 H12 118(2) . . ? C12 C13 C14 121.6(3) . . ? C12 C13 H13 122.3(18) . . ? C14 C13 H13 116.1(18) . . ? O4 C14 C15 121.4(3) . . ? O4 C14 C13 121.4(3) . . ? C15 C14 C13 117.1(2) . . ? C16 C15 C14 121.5(3) . . ? C16 C15 H15 120.7(19) . . ? C14 C15 H15 117.7(19) . . ? C15 C16 C11 121.1(2) . . ? C15 C16 H16 123.6(18) . . ? C11 C16 H16 115.3(18) . . ? F5 Sb F2 90.44(8) . . ? F5 Sb F6 91.08(8) . . ? F2 Sb F6 89.97(8) . . ? F5 Sb F3 178.96(7) . . ? F2 Sb F3 89.49(8) . . ? F6 Sb F3 89.95(7) . . ? F5 Sb F1 90.20(8) . . ? F2 Sb F1 178.95(8) . . ? F6 Sb F1 90.84(9) . . ? F3 Sb F1 89.85(8) . . ? F5 Sb F4 90.55(8) . . ? F2 Sb F4 89.61(9) . . ? F6 Sb F4 178.32(7) . . ? F3 Sb F4 88.42(7) . . ? F1 Sb F4 89.56(9) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.702 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.093 # Attachment 'CCDC_732427.cif' data_jp071099 _database_code_depnum_ccdc_archive 'CCDC 732427' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 F12 N2 O2 S4 Sb2' _chemical_formula_weight 731.82 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' O O 0.0106 0.0060 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7574(12) _cell_length_b 7.6967(14) _cell_length_c 17.669(3) _cell_angle_alpha 87.882(2) _cell_angle_beta 88.198(2) _cell_angle_gamma 70.539(2) _cell_volume 865.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 5370 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 28.39 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.733 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.249193 _exptl_absorpt_correction_T_max 0.685305 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997b)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6005 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3757 _reflns_number_gt 3649 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+1.5170P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3757 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _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 S1 S 1.05305(14) 0.67725(12) 0.15085(5) 0.02273(18) Uani 1 1 d . . . S2 S 0.73274(13) 0.53646(12) 0.14921(4) 0.02015(17) Uani 1 1 d . . . S3 S 0.70051(13) 0.01613(12) 0.36711(4) 0.01907(16) Uani 1 1 d . . . S4 S 0.98800(13) 0.19039(12) 0.34054(4) 0.02028(16) Uani 1 1 d . . . C1 C 1.0308(5) 0.5865(4) 0.06650(17) 0.0184(6) Uani 1 1 d . . . C2 C 0.8704(5) 0.5145(4) 0.06602(17) 0.0183(6) Uani 1 1 d . . . C3 C 0.8261(5) 0.4189(5) -0.00032(18) 0.0209(6) Uani 1 1 d . . . C4 C 0.8557(5) 0.0058(4) 0.44209(17) 0.0167(6) Uani 1 1 d . . . C5 C 1.0008(5) 0.0929(4) 0.42889(17) 0.0161(6) Uani 1 1 d . . . C6 C 1.1615(5) 0.0948(4) 0.48522(17) 0.0163(6) Uani 1 1 d . . . N1 N 0.8631(5) 0.6361(4) 0.19541(16) 0.0220(6) Uani 1 1 d . . . N2 N 0.7990(5) 0.1328(4) 0.30946(15) 0.0213(6) Uani 1 1 d . . . O1 O 0.6886(5) 0.3523(5) 0.00066(16) 0.0395(7) Uani 1 1 d . . . O2 O 1.2934(4) 0.1652(3) 0.47263(13) 0.0224(5) Uani 1 1 d . . . Sb1 Sb 0.39138(3) 0.10196(3) 0.141753(11) 0.01865(7) Uani 1 1 d . . . Sb2 Sb 0.34487(3) 0.58995(3) 0.367135(11) 0.01697(7) Uani 1 1 d . . . F1 F 0.4330(4) 0.3270(3) 0.15716(13) 0.0342(5) Uani 1 1 d . . . F2 F 0.3471(4) -0.1206(3) 0.12492(14) 0.0361(5) Uani 1 1 d . . . F3 F 0.1110(3) 0.2058(3) 0.17675(12) 0.0321(5) Uani 1 1 d . . . F4 F 0.4689(4) 0.0208(3) 0.24099(12) 0.0325(5) Uani 1 1 d . . . F5 F 0.6699(4) -0.0006(3) 0.10842(14) 0.0386(5) Uani 1 1 d . . . F6 F 0.2986(4) 0.1899(3) 0.04407(11) 0.0342(5) Uani 1 1 d . . . F7 F 0.4052(4) 0.7885(3) 0.40793(13) 0.0301(5) Uani 1 1 d . . . F8 F 0.2741(4) 0.3986(3) 0.32521(13) 0.0333(5) Uani 1 1 d . . . F9 F 0.1389(3) 0.6157(3) 0.44338(12) 0.0313(5) Uani 1 1 d . . . F10 F 0.5510(3) 0.4181(3) 0.42462(12) 0.0294(5) Uani 1 1 d . . . F11 F 0.5459(4) 0.5731(3) 0.29016(13) 0.0348(5) Uani 1 1 d . . . F12 F 0.1410(4) 0.7619(3) 0.30662(12) 0.0307(5) 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 S1 0.0231(4) 0.0301(4) 0.0173(4) -0.0068(3) 0.0033(3) -0.0118(3) S2 0.0196(4) 0.0247(4) 0.0164(4) -0.0024(3) 0.0048(3) -0.0079(3) S3 0.0182(4) 0.0255(4) 0.0152(3) 0.0010(3) -0.0027(3) -0.0094(3) S4 0.0221(4) 0.0254(4) 0.0155(3) 0.0037(3) -0.0019(3) -0.0111(3) C1 0.0166(14) 0.0205(15) 0.0158(14) -0.0021(11) 0.0019(12) -0.0029(12) C2 0.0200(15) 0.0185(15) 0.0146(14) -0.0014(11) 0.0041(12) -0.0044(12) C3 0.0196(15) 0.0251(16) 0.0183(15) -0.0022(12) 0.0028(12) -0.0078(13) C4 0.0146(14) 0.0180(14) 0.0162(14) -0.0013(11) -0.0002(11) -0.0036(12) C5 0.0166(14) 0.0163(14) 0.0136(13) -0.0001(11) 0.0008(11) -0.0032(12) C6 0.0153(14) 0.0162(14) 0.0150(14) -0.0030(11) 0.0021(11) -0.0022(12) N1 0.0202(14) 0.0259(15) 0.0198(13) -0.0057(11) 0.0028(11) -0.0072(12) N2 0.0216(14) 0.0272(15) 0.0152(12) 0.0023(10) -0.0022(10) -0.0087(12) O1 0.0449(17) 0.0601(19) 0.0297(14) -0.0144(13) 0.0138(13) -0.0389(16) O2 0.0218(12) 0.0272(12) 0.0218(11) 0.0006(9) 0.0012(9) -0.0134(10) Sb1 0.02089(13) 0.01720(12) 0.01665(12) 0.00023(8) -0.00269(8) -0.00461(9) Sb2 0.01856(12) 0.01695(12) 0.01536(11) -0.00344(8) 0.00256(8) -0.00580(9) F1 0.0443(14) 0.0257(11) 0.0372(12) -0.0009(9) -0.0006(10) -0.0177(10) F2 0.0478(15) 0.0266(11) 0.0380(13) -0.0032(9) -0.0085(11) -0.0171(11) F3 0.0212(10) 0.0385(12) 0.0291(11) 0.0030(9) 0.0037(9) -0.0005(9) F4 0.0407(13) 0.0369(12) 0.0207(10) 0.0058(9) -0.0121(9) -0.0135(10) F5 0.0255(12) 0.0393(13) 0.0424(13) 0.0024(10) 0.0070(10) -0.0005(10) F6 0.0421(13) 0.0356(12) 0.0159(9) 0.0036(8) -0.0059(9) -0.0013(10) F7 0.0335(12) 0.0237(10) 0.0347(12) -0.0085(9) -0.0039(10) -0.0103(9) F8 0.0426(13) 0.0288(11) 0.0353(12) -0.0090(9) -0.0021(10) -0.0198(10) F9 0.0277(11) 0.0362(12) 0.0263(11) -0.0016(9) 0.0117(9) -0.0066(9) F10 0.0279(11) 0.0267(11) 0.0271(11) -0.0011(8) -0.0047(9) 0.0002(9) F11 0.0375(13) 0.0389(13) 0.0287(11) -0.0053(9) 0.0176(10) -0.0151(11) F12 0.0331(12) 0.0298(11) 0.0248(10) 0.0003(8) -0.0067(9) -0.0043(9) _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 S1 N1 1.599(3) . ? S1 C1 1.701(3) . ? S2 N1 1.604(3) . ? S2 C2 1.698(3) . ? S3 N2 1.604(3) . ? S3 C4 1.699(3) . ? S4 N2 1.603(3) . ? S4 C5 1.699(3) . ? C1 C2 1.372(5) . ? C1 C3 1.486(4) 2_765 ? C2 C3 1.496(4) . ? C3 O1 1.201(4) . ? C3 C1 1.486(4) 2_765 ? C4 C5 1.370(4) . ? C4 C6 1.497(4) 2_756 ? C5 C6 1.500(4) . ? C6 O2 1.199(4) . ? C6 C4 1.497(4) 2_756 ? Sb1 F5 1.867(2) . ? Sb1 F4 1.870(2) . ? Sb1 F2 1.870(2) . ? Sb1 F1 1.875(2) . ? Sb1 F6 1.879(2) . ? Sb1 F3 1.888(2) . ? Sb2 F10 1.866(2) . ? Sb2 F11 1.869(2) . ? Sb2 F9 1.873(2) . ? Sb2 F8 1.875(2) . ? Sb2 F7 1.880(2) . ? Sb2 F12 1.888(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C1 98.27(15) . . ? N1 S2 C2 98.14(16) . . ? N2 S3 C4 98.14(15) . . ? N2 S4 C5 98.51(15) . . ? C2 C1 C3 123.1(3) . 2_765 ? C2 C1 S1 113.3(2) . . ? C3 C1 S1 123.5(2) 2_765 . ? C1 C2 C3 123.3(3) . . ? C1 C2 S2 113.6(2) . . ? C3 C2 S2 123.0(2) . . ? O1 C3 C1 123.8(3) . 2_765 ? O1 C3 C2 122.7(3) . . ? C1 C3 C2 113.5(3) 2_765 . ? C5 C4 C6 123.5(3) . 2_756 ? C5 C4 S3 113.8(2) . . ? C6 C4 S3 122.6(2) 2_756 . ? C4 C5 C6 123.6(3) . . ? C4 C5 S4 113.2(2) . . ? C6 C5 S4 123.2(2) . . ? O2 C6 C4 123.5(3) . 2_756 ? O2 C6 C5 123.6(3) . . ? C4 C6 C5 112.9(3) 2_756 . ? S1 N1 S2 116.65(17) . . ? S4 N2 S3 116.33(17) . . ? F5 Sb1 F4 90.43(11) . . ? F5 Sb1 F2 89.95(12) . . ? F4 Sb1 F2 89.51(10) . . ? F5 Sb1 F1 90.35(11) . . ? F4 Sb1 F1 91.43(10) . . ? F2 Sb1 F1 179.01(10) . . ? F5 Sb1 F6 92.68(11) . . ? F4 Sb1 F6 176.88(11) . . ? F2 Sb1 F6 90.72(10) . . ? F1 Sb1 F6 88.33(10) . . ? F5 Sb1 F3 179.24(10) . . ? F4 Sb1 F3 88.87(10) . . ? F2 Sb1 F3 90.34(11) . . ? F1 Sb1 F3 89.38(11) . . ? F6 Sb1 F3 88.01(10) . . ? F10 Sb2 F11 88.87(11) . . ? F10 Sb2 F9 92.80(10) . . ? F11 Sb2 F9 177.98(10) . . ? F10 Sb2 F8 90.15(10) . . ? F11 Sb2 F8 90.49(10) . . ? F9 Sb2 F8 90.65(10) . . ? F10 Sb2 F7 92.05(10) . . ? F11 Sb2 F7 90.29(10) . . ? F9 Sb2 F7 88.50(10) . . ? F8 Sb2 F7 177.67(10) . . ? F10 Sb2 F12 178.45(9) . . ? F11 Sb2 F12 89.65(11) . . ? F9 Sb2 F12 88.69(10) . . ? F8 Sb2 F12 89.41(10) . . ? F7 Sb2 F12 88.40(10) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.096 _refine_diff_density_min -1.073 _refine_diff_density_rms 0.134