# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Haibo Mei' _publ_contact_author_email mhbchem@yahoo.cn loop_ _publ_author_name 'Haibo Mei' 'Yiwen Xiong' 'Jianlin Han' 'Yi Pan' data_xx _database_code_depnum_ccdc_archive 'CCDC 787957' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-2-methyl-N-((S)-1,1,1-trifluoro-4-oxo-4-phenylbutan-2-yl) propane-2-sulfinamide ; _chemical_name_common ; (S)-2-methyl-N-((S)-1,1,1-trifluoro-4-oxo-4-phenylbutan-2-yl) propane-2-sulfinamide ; _chemical_melting_point 146-148 _chemical_formula_moiety 'C14 H18 F3 N O2 S' _chemical_formula_sum 'C14 H18 F3 N O2 S' _chemical_formula_weight 321.35 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P212121 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9351(14) _cell_length_b 11.7459(15) _cell_length_c 24.978(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3208.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4337 _cell_measurement_theta_min 4.760 _cell_measurement_theta_max 45.929 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9371 _exptl_absorpt_correction_T_max 0.9501 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17456 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6290 _reflns_number_gt 4010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.001P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(5) _chemical_absolute_configuration unk _refine_ls_number_reflns 6290 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 C1 C 0.4375(2) 0.0450(2) 0.22532(9) 0.0646(7) Uani 1 1 d . . . C2 C 0.3776(3) 0.1351(2) 0.24914(11) 0.0906(9) Uani 1 1 d . . . H2 H 0.3971 0.2090 0.2389 0.109 Uiso 1 1 calc R . . C3 C 0.2896(3) 0.1179(4) 0.28776(13) 0.1109(11) Uani 1 1 d . . . H3 H 0.2493 0.1796 0.3030 0.133 Uiso 1 1 calc R . . C4 C 0.2623(3) 0.0104(4) 0.30332(12) 0.1112(11) Uani 1 1 d . . . H4 H 0.2031 -0.0014 0.3294 0.133 Uiso 1 1 calc R . . C5 C 0.3212(3) -0.0816(3) 0.28091(12) 0.0984(9) Uani 1 1 d . . . H5 H 0.3027 -0.1551 0.2921 0.118 Uiso 1 1 calc R . . C6 C 0.4079(2) -0.0637(2) 0.24166(10) 0.0752(7) Uani 1 1 d . . . H6 H 0.4469 -0.1257 0.2260 0.090 Uiso 1 1 calc R . . C7 C 0.5289(3) 0.0687(2) 0.18343(10) 0.0683(7) Uani 1 1 d . . . C8 C 0.6031(2) -0.02757(19) 0.16098(8) 0.0656(7) Uani 1 1 d . . . H8A H 0.5492 -0.0911 0.1535 0.079 Uiso 1 1 calc R . . H8B H 0.6615 -0.0523 0.1878 0.079 Uiso 1 1 calc R . . C9 C 0.6721(2) 0.0036(2) 0.10994(8) 0.0621(6) Uani 1 1 d . . . H9 H 0.7028 0.0815 0.1140 0.074 Uiso 1 1 calc R . . C10 C 0.7809(3) -0.0737(3) 0.10194(12) 0.0898(9) Uani 1 1 d . . . C11 C 0.4504(2) 0.1046(2) -0.00784(9) 0.0666(7) Uani 1 1 d . . . C12 C 0.4084(2) -0.0093(2) -0.02903(10) 0.0838(8) Uani 1 1 d . . . H12A H 0.4066 -0.0636 -0.0003 0.126 Uiso 1 1 calc R . . H12B H 0.4639 -0.0349 -0.0562 0.126 Uiso 1 1 calc R . . H12C H 0.3279 -0.0017 -0.0440 0.126 Uiso 1 1 calc R . . C13 C 0.3726(3) 0.1468(2) 0.03834(10) 0.1038(10) Uani 1 1 d . . . H13A H 0.2935 0.1685 0.0252 0.156 Uiso 1 1 calc R . . H13B H 0.4114 0.2113 0.0547 0.156 Uiso 1 1 calc R . . H13C H 0.3637 0.0872 0.0643 0.156 Uiso 1 1 calc R . . C14 C 0.4548(3) 0.1917(2) -0.05294(10) 0.1099(11) Uani 1 1 d . . . H14A H 0.4996 0.1609 -0.0826 0.165 Uiso 1 1 calc R . . H14B H 0.4944 0.2597 -0.0405 0.165 Uiso 1 1 calc R . . H14C H 0.3730 0.2096 -0.0642 0.165 Uiso 1 1 calc R . . C15 C 0.1792(2) 0.34940(19) 0.18694(8) 0.0525(6) Uani 1 1 d . . . C16 C 0.0896(3) 0.3811(2) 0.22328(10) 0.0758(8) Uani 1 1 d . . . H16 H 0.0960 0.4505 0.2410 0.091 Uiso 1 1 calc R . . C17 C -0.0076(3) 0.3121(3) 0.23342(12) 0.0952(10) Uani 1 1 d . . . H17 H -0.0673 0.3354 0.2576 0.114 Uiso 1 1 calc R . . C18 C -0.0185(3) 0.2093(3) 0.20863(12) 0.0942(9) Uani 1 1 d . . . H18 H -0.0849 0.1624 0.2159 0.113 Uiso 1 1 calc R . . C19 C 0.0694(3) 0.1756(2) 0.17278(12) 0.0886(9) Uani 1 1 d . . . H19 H 0.0627 0.1055 0.1557 0.106 Uiso 1 1 calc R . . C20 C 0.1674(2) 0.24549(19) 0.16213(9) 0.0683(7) Uani 1 1 d . . . H20 H 0.2266 0.2221 0.1378 0.082 Uiso 1 1 calc R . . C21 C 0.2837(2) 0.42748(19) 0.17781(9) 0.0524(6) Uani 1 1 d . . . C22 C 0.36487(19) 0.40710(17) 0.12979(8) 0.0530(5) Uani 1 1 d . . . H22A H 0.3150 0.3827 0.0998 0.064 Uiso 1 1 calc R . . H22B H 0.4223 0.3465 0.1379 0.064 Uiso 1 1 calc R . . C23 C 0.43525(18) 0.51380(17) 0.11422(8) 0.0502(5) Uani 1 1 d . . . H23 H 0.4722 0.5455 0.1467 0.060 Uiso 1 1 calc R . . C24 C 0.5356(2) 0.4875(2) 0.07553(11) 0.0669(7) Uani 1 1 d . . . C25 C 0.1960(2) 0.76597(18) 0.09976(9) 0.0630(6) Uani 1 1 d . . . C26 C 0.1172(2) 0.6891(2) 0.13428(10) 0.0821(8) Uani 1 1 d . . . H26A H 0.0347 0.7171 0.1345 0.123 Uiso 1 1 calc R . . H26B H 0.1486 0.6884 0.1702 0.123 Uiso 1 1 calc R . . H26C H 0.1185 0.6132 0.1200 0.123 Uiso 1 1 calc R . . C27 C 0.1861(3) 0.88976(19) 0.11837(11) 0.1061(10) Uani 1 1 d . . . H27A H 0.1036 0.9158 0.1137 0.159 Uiso 1 1 calc R . . H27B H 0.2403 0.9364 0.0975 0.159 Uiso 1 1 calc R . . H27C H 0.2082 0.8947 0.1555 0.159 Uiso 1 1 calc R . . C28 C 0.1657(2) 0.75623(19) 0.04061(9) 0.0785(8) Uani 1 1 d . . . H28A H 0.1658 0.6775 0.0303 0.118 Uiso 1 1 calc R . . H28B H 0.2258 0.7968 0.0201 0.118 Uiso 1 1 calc R . . H28C H 0.0863 0.7883 0.0341 0.118 Uiso 1 1 calc R . . F1 F 0.85771(15) -0.06701(17) 0.14399(6) 0.1373(7) Uani 1 1 d . . . F2 F 0.75070(17) -0.18204(17) 0.09754(7) 0.1152(6) Uani 1 1 d . . . F3 F 0.84571(15) -0.04745(17) 0.05933(6) 0.1300(7) Uani 1 1 d . . . F4 F 0.60962(13) 0.40459(12) 0.09200(5) 0.0864(4) Uani 1 1 d . . . F5 F 0.49430(14) 0.45545(13) 0.02782(6) 0.0970(5) Uani 1 1 d . . . F6 F 0.60708(14) 0.57840(13) 0.06697(6) 0.1009(5) Uani 1 1 d . . . N1 N 0.59146(16) 0.00174(15) 0.06450(7) 0.0589(5) Uani 1 1 d . . . H1 H 0.5336 -0.0477 0.0628 0.071 Uiso 1 1 calc R . . N2 N 0.35337(16) 0.59759(13) 0.09234(6) 0.0532(5) Uani 1 1 d . . . H2A H 0.3014 0.5776 0.0683 0.064 Uiso 1 1 calc R . . O1 O 0.5457(2) 0.16509(15) 0.16772(8) 0.1090(7) Uani 1 1 d . . . O2 O 0.67787(13) 0.04476(12) -0.03007(6) 0.0705(5) Uani 1 1 d . . . O3 O 0.30356(15) 0.50561(14) 0.20844(6) 0.0754(5) Uani 1 1 d . . . O4 O 0.42801(15) 0.80277(13) 0.07541(8) 0.0904(6) Uani 1 1 d . . . S1 S 0.60989(6) 0.09436(5) 0.01563(2) 0.05810(16) Uani 1 1 d . . . S2 S 0.35695(6) 0.72982(5) 0.11225(3) 0.06337(18) 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 C1 0.0691(18) 0.0735(18) 0.0512(15) -0.0007(15) -0.0135(14) 0.0115(15) C2 0.104(2) 0.098(2) 0.0703(18) -0.0099(17) -0.0125(19) 0.031(2) C3 0.098(3) 0.150(3) 0.085(2) -0.017(2) 0.000(2) 0.050(3) C4 0.077(2) 0.178(4) 0.079(2) 0.007(3) 0.0043(18) 0.014(3) C5 0.081(2) 0.125(3) 0.089(2) 0.009(2) 0.004(2) -0.011(2) C6 0.0657(19) 0.089(2) 0.0706(17) -0.0003(16) -0.0011(15) 0.0004(16) C7 0.085(2) 0.0659(17) 0.0535(16) 0.0024(15) -0.0093(15) -0.0024(16) C8 0.0733(17) 0.0712(16) 0.0524(14) 0.0045(13) -0.0021(14) -0.0039(15) C9 0.0615(16) 0.0721(15) 0.0526(14) 0.0042(13) -0.0067(14) -0.0147(14) C10 0.061(2) 0.132(3) 0.076(2) 0.018(2) -0.0040(18) -0.004(2) C11 0.0646(17) 0.0719(15) 0.0632(15) 0.0101(15) 0.0100(14) 0.0189(14) C12 0.0603(17) 0.106(2) 0.0848(18) -0.0054(18) -0.0175(15) 0.0022(17) C13 0.093(2) 0.118(2) 0.1006(19) -0.0019(18) 0.032(2) 0.0377(19) C14 0.118(3) 0.114(2) 0.098(2) 0.043(2) 0.0030(19) 0.036(2) C15 0.0574(16) 0.0534(14) 0.0466(14) 0.0109(12) 0.0014(12) 0.0075(13) C16 0.084(2) 0.0714(17) 0.0718(17) 0.0023(15) 0.0227(17) 0.0026(17) C17 0.091(2) 0.101(2) 0.094(2) 0.013(2) 0.0413(19) 0.002(2) C18 0.084(2) 0.088(2) 0.111(3) 0.029(2) 0.022(2) -0.0149(19) C19 0.090(2) 0.0630(16) 0.113(2) 0.0137(18) 0.016(2) -0.0094(18) C20 0.0704(18) 0.0605(16) 0.0739(16) 0.0085(15) 0.0159(14) 0.0008(14) C21 0.0538(15) 0.0551(15) 0.0482(14) 0.0076(12) -0.0041(12) 0.0061(13) C22 0.0510(13) 0.0524(12) 0.0554(13) 0.0057(12) 0.0016(12) 0.0044(12) C23 0.0420(13) 0.0545(13) 0.0541(13) 0.0052(12) -0.0038(12) -0.0009(11) C24 0.0516(16) 0.0755(18) 0.0736(19) 0.0169(17) 0.0039(15) 0.0014(16) C25 0.0571(16) 0.0507(14) 0.0812(17) -0.0062(13) -0.0040(14) 0.0005(12) C26 0.0646(17) 0.0865(17) 0.0952(18) -0.0022(16) 0.0149(17) 0.0060(16) C27 0.094(2) 0.0633(16) 0.161(3) -0.022(2) -0.010(2) 0.0100(16) C28 0.0696(18) 0.0760(17) 0.0900(19) 0.0153(15) -0.0174(16) 0.0014(14) F1 0.0743(11) 0.237(2) 0.1011(11) 0.0214(14) -0.0276(11) 0.0128(14) F2 0.1042(14) 0.1176(14) 0.1236(15) 0.0040(13) 0.0132(11) 0.0394(12) F3 0.0720(11) 0.222(2) 0.0964(11) 0.0421(13) 0.0225(10) 0.0159(12) F4 0.0609(9) 0.0960(9) 0.1023(10) 0.0161(9) 0.0117(8) 0.0261(9) F5 0.0898(11) 0.1384(13) 0.0627(9) -0.0023(10) 0.0120(9) 0.0175(10) F6 0.0699(10) 0.0985(11) 0.1344(12) 0.0282(10) 0.0333(10) -0.0073(10) N1 0.0569(12) 0.0635(11) 0.0565(11) 0.0068(10) -0.0037(10) -0.0180(10) N2 0.0529(11) 0.0465(10) 0.0601(10) 0.0012(9) -0.0146(9) -0.0040(10) O1 0.167(2) 0.0632(11) 0.0963(14) 0.0106(12) 0.0215(14) 0.0001(14) O2 0.0640(11) 0.0897(11) 0.0577(9) 0.0034(9) 0.0179(9) 0.0073(9) O3 0.0858(13) 0.0844(11) 0.0559(10) -0.0121(10) 0.0022(9) -0.0139(11) O4 0.0673(12) 0.0580(9) 0.1459(15) 0.0225(11) -0.0024(12) -0.0185(9) S1 0.0634(4) 0.0559(3) 0.0550(3) 0.0023(3) 0.0091(3) -0.0070(3) S2 0.0600(4) 0.0492(3) 0.0809(4) -0.0040(4) -0.0136(4) -0.0079(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.378(3) . ? C1 C2 1.380(3) . ? C1 C7 1.474(3) . ? C2 C3 1.377(4) . ? C2 H2 0.9300 . ? C3 C4 1.354(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(4) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.213(3) . ? C7 C8 1.500(3) . ? C8 C9 1.526(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.438(2) . ? C9 C10 1.510(4) . ? C9 H9 0.9800 . ? C10 F3 1.315(3) . ? C10 F2 1.319(3) . ? C10 F1 1.347(3) . ? C11 C12 1.510(3) . ? C11 C13 1.516(3) . ? C11 C14 1.523(3) . ? C11 S1 1.844(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.375(3) . ? C15 C16 1.387(3) . ? C15 C21 1.483(3) . ? C16 C17 1.360(3) . ? C16 H16 0.9300 . ? C17 C18 1.362(4) . ? C17 H17 0.9300 . ? C18 C19 1.372(4) . ? C18 H18 0.9300 . ? C19 C20 1.376(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 O3 1.214(2) . ? C21 C22 1.511(3) . ? C22 C23 1.521(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N2 1.438(2) . ? C23 C24 1.494(3) . ? C23 H23 0.9800 . ? C24 F5 1.329(3) . ? C24 F4 1.332(3) . ? C24 F6 1.341(3) . ? C25 C26 1.517(3) . ? C25 C28 1.519(3) . ? C25 C27 1.530(3) . ? C25 S2 1.837(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? N1 S1 1.6474(17) . ? N1 H1 0.8600 . ? N2 S2 1.6312(16) . ? N2 H2A 0.8600 . ? O2 S1 1.4816(15) . ? O4 S2 1.4780(17) . ? 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 C6 C1 C2 118.1(3) . . ? C6 C1 C7 123.0(3) . . ? C2 C1 C7 118.9(3) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 119.4(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 120.8(3) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? O1 C7 C1 120.6(2) . . ? O1 C7 C8 120.1(2) . . ? C1 C7 C8 119.3(2) . . ? C7 C8 C9 113.53(19) . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N1 C9 C10 111.7(2) . . ? N1 C9 C8 110.66(18) . . ? C10 C9 C8 110.9(2) . . ? N1 C9 H9 107.8 . . ? C10 C9 H9 107.8 . . ? C8 C9 H9 107.8 . . ? F3 C10 F2 107.1(3) . . ? F3 C10 F1 106.4(2) . . ? F2 C10 F1 106.1(3) . . ? F3 C10 C9 113.0(3) . . ? F2 C10 C9 113.2(2) . . ? F1 C10 C9 110.7(3) . . ? C12 C11 C13 112.7(2) . . ? C12 C11 C14 110.2(2) . . ? C13 C11 C14 111.1(2) . . ? C12 C11 S1 109.97(16) . . ? C13 C11 S1 108.05(18) . . ? C14 C11 S1 104.43(19) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 117.8(2) . . ? C20 C15 C21 123.5(2) . . ? C16 C15 C21 118.6(2) . . ? C17 C16 C15 121.0(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C19 119.5(3) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 121.0(2) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? O3 C21 C15 120.5(2) . . ? O3 C21 C22 121.0(2) . . ? C15 C21 C22 118.5(2) . . ? C21 C22 C23 111.68(18) . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? N2 C23 C24 110.66(18) . . ? N2 C23 C22 110.24(16) . . ? C24 C23 C22 111.50(18) . . ? N2 C23 H23 108.1 . . ? C24 C23 H23 108.1 . . ? C22 C23 H23 108.1 . . ? F5 C24 F4 106.0(2) . . ? F5 C24 F6 106.3(2) . . ? F4 C24 F6 106.1(2) . . ? F5 C24 C23 112.9(2) . . ? F4 C24 C23 113.4(2) . . ? F6 C24 C23 111.5(2) . . ? C26 C25 C28 112.59(19) . . ? C26 C25 C27 110.6(2) . . ? C28 C25 C27 110.6(2) . . ? C26 C25 S2 108.06(16) . . ? C28 C25 S2 110.92(17) . . ? C27 C25 S2 103.66(17) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C9 N1 S1 120.01(15) . . ? C9 N1 H1 120.0 . . ? S1 N1 H1 120.0 . . ? C23 N2 S2 121.39(14) . . ? C23 N2 H2A 119.3 . . ? S2 N2 H2A 119.3 . . ? O2 S1 N1 111.87(9) . . ? O2 S1 C11 104.79(10) . . ? N1 S1 C11 99.37(10) . . ? O4 S2 N2 112.02(10) . . ? O4 S2 C25 105.30(10) . . ? N2 S2 C25 98.36(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.7(4) . . . . ? C7 C1 C2 C3 178.7(2) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? C7 C1 C6 C5 -179.7(2) . . . . ? C4 C5 C6 C1 1.0(4) . . . . ? C6 C1 C7 O1 174.8(3) . . . . ? C2 C1 C7 O1 -4.7(4) . . . . ? C6 C1 C7 C8 -6.4(4) . . . . ? C2 C1 C7 C8 174.2(2) . . . . ? O1 C7 C8 C9 -14.3(3) . . . . ? C1 C7 C8 C9 166.9(2) . . . . ? C7 C8 C9 N1 -78.8(2) . . . . ? C7 C8 C9 C10 156.7(2) . . . . ? N1 C9 C10 F3 58.3(3) . . . . ? C8 C9 C10 F3 -177.8(2) . . . . ? N1 C9 C10 F2 -63.6(3) . . . . ? C8 C9 C10 F2 60.3(3) . . . . ? N1 C9 C10 F1 177.4(2) . . . . ? C8 C9 C10 F1 -58.6(3) . . . . ? C20 C15 C16 C17 -0.9(4) . . . . ? C21 C15 C16 C17 -179.5(2) . . . . ? C15 C16 C17 C18 0.9(4) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C21 C15 C20 C19 178.9(2) . . . . ? C18 C19 C20 C15 0.0(4) . . . . ? C20 C15 C21 O3 -164.2(2) . . . . ? C16 C15 C21 O3 14.3(3) . . . . ? C20 C15 C21 C22 15.5(3) . . . . ? C16 C15 C21 C22 -166.01(19) . . . . ? O3 C21 C22 C23 -21.3(3) . . . . ? C15 C21 C22 C23 158.99(18) . . . . ? C21 C22 C23 N2 -69.9(2) . . . . ? C21 C22 C23 C24 166.81(19) . . . . ? N2 C23 C24 F5 -54.9(3) . . . . ? C22 C23 C24 F5 68.2(3) . . . . ? N2 C23 C24 F4 -175.59(19) . . . . ? C22 C23 C24 F4 -52.5(3) . . . . ? N2 C23 C24 F6 64.7(3) . . . . ? C22 C23 C24 F6 -172.2(2) . . . . ? C10 C9 N1 S1 -91.2(2) . . . . ? C8 C9 N1 S1 144.70(16) . . . . ? C24 C23 N2 S2 -103.9(2) . . . . ? C22 C23 N2 S2 132.24(16) . . . . ? C9 N1 S1 O2 98.59(17) . . . . ? C9 N1 S1 C11 -151.23(18) . . . . ? C12 C11 S1 O2 52.53(18) . . . . ? C13 C11 S1 O2 175.88(16) . . . . ? C14 C11 S1 O2 -65.72(18) . . . . ? C12 C11 S1 N1 -63.20(18) . . . . ? C13 C11 S1 N1 60.15(19) . . . . ? C14 C11 S1 N1 178.55(16) . . . . ? C23 N2 S2 O4 98.04(16) . . . . ? C23 N2 S2 C25 -151.65(16) . . . . ? C26 C25 S2 O4 176.93(15) . . . . ? C28 C25 S2 O4 53.07(18) . . . . ? C27 C25 S2 O4 -65.63(19) . . . . ? C26 C25 S2 N2 61.27(16) . . . . ? C28 C25 S2 N2 -62.59(17) . . . . ? C27 C25 S2 N2 178.71(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.141 _refine_diff_density_min -0.115 _refine_diff_density_rms 0.025