# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Andrew Boa' 'Stephen J. Archibald' 'Nela Pesa' _publ_contact_author_name 'Dr Andrew Boa' _publ_contact_author_address ; Department of Chemistry University of Hull Cottingham Road Hull HU6 7RX UNITED KINGDOM ; _publ_contact_author_email A.N.BOA@HULL.AC.UK _publ_section_title ; On the sulfimidation of benzo (b) thiophene ; data_anb10101 _database_code_CSD 209586 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H27 Cl2 N3 O6 S4' _chemical_formula_weight 712.68 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' S S 0.1246 0.1234 '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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5409(10) _cell_length_b 13.9647(9) _cell_length_c 23.344(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.450(8) _cell_angle_gamma 90.00 _cell_volume 3090.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.529 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_type 'Stoe IPDSII image plate' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16166 _diffrn_reflns_av_R_equivalents 0.0852 _diffrn_reflns_av_sigmaI/netI 0.2169 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8100 _reflns_number_gt 3099 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _computing_publication_material 'SHELXL 97 (Sheldrick, 1997)' _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^)+(0.0125P)^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 8100 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1216 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0558 _refine_ls_goodness_of_fit_ref 0.607 _refine_ls_restrained_S_all 0.607 _refine_ls_shift/su_max 0.011 _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 C1 C 0.1134(3) 0.66654(18) 0.06484(12) 0.0245(6) Uani 1 1 d . . . C2 C 0.0267(3) 0.68658(17) 0.01391(12) 0.0238(6) Uani 1 1 d . . . C3 C -0.0743(3) 0.76823(19) 0.01211(11) 0.0289(7) Uani 1 1 d . . . C4 C -0.1464(3) 0.77802(18) 0.06872(10) 0.0218(6) Uani 1 1 d . . . H4 H -0.2108 0.8329 0.0646 0.026 Uiso 1 1 calc R . . C5 C 0.2133(3) 0.59345(19) 0.06807(13) 0.0319(7) Uani 1 1 d . . . H5 H 0.2702 0.5815 0.1023 0.038 Uiso 1 1 calc R . . C6 C 0.2264(3) 0.5390(2) 0.01950(14) 0.0351(8) Uani 1 1 d . . . H6 H 0.2942 0.4910 0.0207 0.042 Uiso 1 1 calc R . . C7 C 0.1393(3) 0.5556(2) -0.03072(14) 0.0369(8) Uani 1 1 d . . . H7 H 0.1469 0.5172 -0.0628 0.044 Uiso 1 1 calc R . . C8 C 0.0406(3) 0.62843(19) -0.03401(12) 0.0316(7) Uani 1 1 d . . . H8 H -0.0169 0.6389 -0.0683 0.038 Uiso 1 1 calc R . . C9 C -0.0505(3) 0.88237(18) 0.22322(12) 0.0277(7) Uani 1 1 d . . . C10 C 0.0722(3) 0.87115(19) 0.26101(13) 0.0322(7) Uani 1 1 d . . . H10 H 0.1604 0.8720 0.2476 0.039 Uiso 1 1 calc R . . C11 C 0.0596(3) 0.85871(19) 0.31908(12) 0.0319(7) Uani 1 1 d . . . H11 H 0.1409 0.8509 0.3446 0.038 Uiso 1 1 calc R . . C12 C -0.0697(3) 0.85748(19) 0.34028(13) 0.0309(7) Uani 1 1 d . . . C13 C -0.1894(3) 0.8706(2) 0.30107(14) 0.0379(8) Uani 1 1 d . . . H13 H -0.2776 0.8709 0.3144 0.045 Uiso 1 1 calc R . . C14 C -0.1807(3) 0.88314(19) 0.24284(13) 0.0353(8) Uani 1 1 d . . . H14 H -0.2619 0.8920 0.2174 0.042 Uiso 1 1 calc R . . C15 C -0.0796(4) 0.8461(2) 0.40382(13) 0.0442(9) Uani 1 1 d . . . H15A H -0.1769 0.8473 0.4108 0.066 Uiso 1 1 calc R . . H15B H -0.0300 0.8976 0.4245 0.066 Uiso 1 1 calc R . . H15C H -0.0382 0.7861 0.4168 0.066 Uiso 1 1 calc R . . C16 C 0.0178(3) 0.58585(18) 0.26361(11) 0.0261(7) Uani 1 1 d . . . C17 C 0.1182(4) 0.55770(19) 0.30794(13) 0.0377(8) Uani 1 1 d . . . H17 H 0.2079 0.5393 0.3003 0.045 Uiso 1 1 calc R . . C18 C 0.0823(4) 0.5574(2) 0.36393(14) 0.0486(10) Uani 1 1 d . . . H18 H 0.1488 0.5375 0.3938 0.058 Uiso 1 1 calc R . . C19 C -0.0477(4) 0.5856(2) 0.37641(13) 0.0461(9) Uani 1 1 d . . . C20 C -0.1461(4) 0.6164(2) 0.33159(13) 0.0415(8) Uani 1 1 d . . . H20 H -0.2346 0.6369 0.3395 0.050 Uiso 1 1 calc R . . C21 C -0.1129(3) 0.61662(19) 0.27489(12) 0.0333(7) Uani 1 1 d . . . H21 H -0.1787 0.6374 0.2451 0.040 Uiso 1 1 calc R . . C22 C -0.0867(5) 0.5801(3) 0.43740(14) 0.0728(14) Uani 1 1 d . . . H22A H -0.1812 0.6033 0.4382 0.109 Uiso 1 1 calc R . . H22B H -0.0227 0.6188 0.4623 0.109 Uiso 1 1 calc R . . H22C H -0.0810 0.5149 0.4504 0.109 Uiso 1 1 calc R . . C23 C -0.4482(3) 0.70739(18) 0.14349(11) 0.0212(6) Uani 1 1 d . . . C24 C -0.4461(3) 0.6285(2) 0.18009(13) 0.0316(7) Uani 1 1 d . . . H24 H -0.4163 0.5690 0.1682 0.038 Uiso 1 1 calc R . . C25 C -0.4886(3) 0.6395(2) 0.23390(13) 0.0326(7) Uani 1 1 d . . . H25 H -0.4878 0.5866 0.2581 0.039 Uiso 1 1 calc R . . C26 C -0.5329(3) 0.72762(19) 0.25339(11) 0.0264(7) Uani 1 1 d . . . C27 C -0.5344(3) 0.80473(19) 0.21576(12) 0.0279(7) Uani 1 1 d . . . H27 H -0.5636 0.8643 0.2277 0.033 Uiso 1 1 calc R . . C28 C -0.4939(3) 0.79551(18) 0.16112(11) 0.0256(6) Uani 1 1 d . . . H28 H -0.4972 0.8479 0.1364 0.031 Uiso 1 1 calc R . . C29 C -0.5802(3) 0.7369(2) 0.31249(13) 0.0414(8) Uani 1 1 d . . . H29A H -0.5702 0.6763 0.3319 0.062 Uiso 1 1 calc R . . H29B H -0.6772 0.7565 0.3090 0.062 Uiso 1 1 calc R . . H29C H -0.5232 0.7839 0.3342 0.062 Uiso 1 1 calc R . . S1 S 0.12498(7) 0.74047(5) 0.12813(3) 0.02531(16) Uani 1 1 d . . . S2 S -0.03634(9) 0.90570(5) 0.15004(3) 0.03208(19) Uani 1 1 d . . . S3 S 0.05591(8) 0.57603(5) 0.19196(3) 0.02666(17) Uani 1 1 d . . . S4 S -0.39916(8) 0.69257(5) 0.07338(3) 0.02742(17) Uani 1 1 d . . . O1 O 0.0981(2) 0.94746(13) 0.14588(9) 0.0427(6) Uani 1 1 d . . . O2 O -0.1623(3) 0.95147(13) 0.12500(9) 0.0444(6) Uani 1 1 d . . . O3 O 0.1499(2) 0.49645(12) 0.18883(9) 0.0397(5) Uani 1 1 d . . . O4 O -0.0763(2) 0.57220(12) 0.15492(8) 0.0289(5) Uani 1 1 d . . . O5 O -0.4391(2) 0.59761(14) 0.05502(8) 0.0396(6) Uani 1 1 d . . . O6 O -0.4485(2) 0.77385(14) 0.04009(8) 0.0390(5) Uani 1 1 d . . . N1 N -0.0384(2) 0.79630(14) 0.11743(9) 0.0237(5) Uani 1 1 d . . . N2 N 0.1422(2) 0.67518(14) 0.18337(10) 0.0257(6) Uani 1 1 d . . . N3 N -0.2270(2) 0.69373(16) 0.07681(9) 0.0247(5) Uani 1 1 d . . . H3 H -0.181(3) 0.6466(17) 0.0956(12) 0.030 Uiso 1 1 d . . . Cl1 Cl 0.01990(10) 0.87741(5) 0.00242(4) 0.0446(2) Uani 1 1 d . . . Cl2 Cl -0.21051(8) 0.75997(6) -0.04630(3) 0.0432(2) 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 0.0191(15) 0.0247(15) 0.0305(16) -0.0062(12) 0.0065(12) -0.0048(12) C2 0.0234(15) 0.0220(14) 0.0280(15) 0.0010(12) 0.0119(12) -0.0041(12) C3 0.0304(17) 0.0336(16) 0.0224(13) 0.0054(12) 0.0014(12) -0.0006(13) C4 0.0225(14) 0.0230(14) 0.0194(12) 0.0000(11) 0.0003(11) 0.0029(12) C5 0.0249(17) 0.0340(16) 0.0374(17) -0.0026(14) 0.0059(14) -0.0015(14) C6 0.0270(18) 0.0332(17) 0.047(2) -0.0066(14) 0.0143(16) -0.0001(14) C7 0.040(2) 0.0322(17) 0.0425(19) -0.0104(14) 0.0212(16) -0.0081(15) C8 0.0342(18) 0.0358(17) 0.0262(16) -0.0016(13) 0.0095(14) -0.0095(15) C9 0.0288(17) 0.0211(14) 0.0328(16) -0.0073(12) 0.0023(13) -0.0028(12) C10 0.0267(17) 0.0333(16) 0.0367(18) -0.0089(13) 0.0040(14) 0.0011(13) C11 0.0231(17) 0.0364(17) 0.0350(17) -0.0086(13) -0.0020(14) 0.0051(13) C12 0.0298(18) 0.0296(17) 0.0333(17) -0.0077(13) 0.0040(14) 0.0034(13) C13 0.0267(18) 0.0439(19) 0.045(2) -0.0040(15) 0.0115(15) -0.0030(15) C14 0.0271(18) 0.0323(17) 0.0438(19) -0.0086(14) -0.0078(15) -0.0002(13) C15 0.046(2) 0.051(2) 0.0378(19) -0.0078(16) 0.0125(17) 0.0086(17) C16 0.0322(17) 0.0207(14) 0.0242(14) 0.0023(12) -0.0024(13) -0.0027(13) C17 0.045(2) 0.0271(16) 0.0376(19) -0.0027(13) -0.0101(16) 0.0003(14) C18 0.076(3) 0.0298(18) 0.0343(19) 0.0016(14) -0.0192(19) -0.0173(18) C19 0.076(3) 0.0336(18) 0.0286(17) -0.0042(14) 0.0049(18) -0.0266(19) C20 0.048(2) 0.0393(19) 0.0383(19) -0.0050(15) 0.0102(17) -0.0143(16) C21 0.0391(19) 0.0320(17) 0.0276(16) -0.0003(13) -0.0009(14) -0.0033(15) C22 0.109(4) 0.075(3) 0.034(2) -0.0091(19) 0.009(2) -0.047(3) C23 0.0160(13) 0.0262(15) 0.0212(13) -0.0026(11) 0.0001(11) 0.0016(12) C24 0.0323(18) 0.0254(15) 0.0383(18) -0.0014(13) 0.0089(15) 0.0066(13) C25 0.0360(18) 0.0260(16) 0.0369(18) 0.0060(13) 0.0089(15) 0.0062(14) C26 0.0209(15) 0.0289(16) 0.0293(15) -0.0020(13) 0.0022(12) -0.0024(12) C27 0.0234(16) 0.0251(15) 0.0361(17) -0.0077(13) 0.0071(13) 0.0006(12) C28 0.0275(16) 0.0205(14) 0.0288(15) 0.0050(12) 0.0033(13) -0.0031(12) C29 0.042(2) 0.0474(19) 0.0377(18) -0.0031(15) 0.0151(15) 0.0060(16) S1 0.0221(3) 0.0242(4) 0.0287(4) -0.0024(3) -0.0011(3) -0.0018(3) S2 0.0436(5) 0.0195(4) 0.0313(4) -0.0051(3) -0.0042(4) 0.0011(4) S3 0.0285(4) 0.0210(4) 0.0290(4) 0.0005(3) -0.0031(3) 0.0019(3) S4 0.0190(4) 0.0400(4) 0.0226(3) -0.0054(3) -0.0006(3) 0.0000(3) O1 0.0586(16) 0.0301(11) 0.0392(13) -0.0065(9) 0.0045(11) -0.0223(11) O2 0.0617(16) 0.0264(11) 0.0410(13) -0.0093(10) -0.0121(12) 0.0158(11) O3 0.0434(14) 0.0238(10) 0.0524(14) 0.0023(10) 0.0067(11) 0.0139(10) O4 0.0326(12) 0.0271(10) 0.0248(10) -0.0005(8) -0.0069(9) -0.0056(9) O5 0.0280(12) 0.0498(13) 0.0413(13) -0.0225(11) 0.0055(10) -0.0063(10) O6 0.0321(12) 0.0577(14) 0.0265(10) 0.0061(10) 0.0008(9) 0.0159(11) N1 0.0241(13) 0.0189(11) 0.0266(12) -0.0064(9) -0.0040(10) 0.0041(10) N2 0.0260(13) 0.0191(11) 0.0302(13) 0.0001(10) -0.0042(11) -0.0016(10) N3 0.0181(12) 0.0296(13) 0.0261(12) 0.0020(11) 0.0010(10) 0.0022(11) Cl1 0.0550(6) 0.0297(4) 0.0519(5) 0.0115(4) 0.0186(4) -0.0038(4) Cl2 0.0377(5) 0.0708(6) 0.0201(3) -0.0006(4) -0.0017(3) 0.0082(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 C1 C5 1.393(4) . ? C1 C2 1.398(4) . ? C1 S1 1.795(3) . ? C2 C8 1.401(4) . ? C2 C3 1.490(4) . ? C3 C4 1.563(4) . ? C3 Cl2 1.778(3) . ? C3 Cl1 1.797(3) . ? C4 N3 1.430(3) . ? C4 N1 1.469(3) . ? C5 C6 1.382(4) . ? C6 C7 1.378(4) . ? C7 C8 1.382(4) . ? C9 C14 1.372(4) . ? C9 C10 1.393(4) . ? C9 S2 1.759(3) . ? C10 C11 1.385(4) . ? C11 C12 1.380(4) . ? C12 C13 1.393(4) . ? C12 C15 1.505(4) . ? C13 C14 1.382(4) . ? C16 C21 1.372(4) . ? C16 C17 1.385(4) . ? C16 S3 1.757(3) . ? C17 C18 1.388(5) . ? C18 C19 1.364(5) . ? C19 C20 1.393(4) . ? C19 C22 1.514(5) . ? C20 C21 1.395(4) . ? C23 C28 1.383(3) . ? C23 C24 1.393(4) . ? C23 S4 1.764(3) . ? C24 C25 1.371(4) . ? C25 C26 1.394(4) . ? C26 C27 1.389(4) . ? C26 C29 1.505(4) . ? C27 C28 1.380(4) . ? S1 N2 1.573(2) . ? S1 N1 1.735(2) . ? S2 O1 1.422(2) . ? S2 O2 1.427(2) . ? S2 N1 1.706(2) . ? S3 O3 1.4349(19) . ? S3 O4 1.4481(19) . ? S3 N2 1.634(2) . ? S4 O6 1.4256(19) . ? S4 O5 1.4320(19) . ? S4 N3 1.636(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 C5 C1 C2 121.9(3) . . ? C5 C1 S1 113.5(2) . . ? C2 C1 S1 124.1(2) . . ? C1 C2 C8 117.6(3) . . ? C1 C2 C3 119.7(2) . . ? C8 C2 C3 122.7(2) . . ? C2 C3 C4 112.8(2) . . ? C2 C3 Cl2 112.72(19) . . ? C4 C3 Cl2 107.50(19) . . ? C2 C3 Cl1 108.8(2) . . ? C4 C3 Cl1 107.83(18) . . ? Cl2 C3 Cl1 106.93(14) . . ? N3 C4 N1 112.4(2) . . ? N3 C4 C3 109.5(2) . . ? N1 C4 C3 109.4(2) . . ? C6 C5 C1 118.9(3) . . ? C7 C6 C5 120.3(3) . . ? C6 C7 C8 120.8(3) . . ? C7 C8 C2 120.5(3) . . ? C14 C9 C10 121.2(3) . . ? C14 C9 S2 119.6(2) . . ? C10 C9 S2 119.0(3) . . ? C11 C10 C9 118.3(3) . . ? C12 C11 C10 122.2(3) . . ? C11 C12 C13 117.6(3) . . ? C11 C12 C15 120.8(3) . . ? C13 C12 C15 121.6(3) . . ? C14 C13 C12 121.8(3) . . ? C9 C14 C13 119.0(3) . . ? C21 C16 C17 120.8(3) . . ? C21 C16 S3 119.8(2) . . ? C17 C16 S3 119.3(3) . . ? C16 C17 C18 118.8(3) . . ? C19 C18 C17 121.8(3) . . ? C18 C19 C20 118.8(3) . . ? C18 C19 C22 120.8(3) . . ? C20 C19 C22 120.4(4) . . ? C19 C20 C21 120.5(3) . . ? C16 C21 C20 119.3(3) . . ? C28 C23 C24 120.3(3) . . ? C28 C23 S4 120.4(2) . . ? C24 C23 S4 119.3(2) . . ? C25 C24 C23 119.2(3) . . ? C24 C25 C26 122.0(3) . . ? C27 C26 C25 117.4(3) . . ? C27 C26 C29 122.0(3) . . ? C25 C26 C29 120.6(3) . . ? C28 C27 C26 121.9(3) . . ? C27 C28 C23 119.2(2) . . ? N2 S1 N1 112.80(12) . . ? N2 S1 C1 109.42(11) . . ? N1 S1 C1 99.71(11) . . ? O1 S2 O2 120.85(13) . . ? O1 S2 N1 107.57(13) . . ? O2 S2 N1 104.58(11) . . ? O1 S2 C9 108.08(13) . . ? O2 S2 C9 109.13(15) . . ? N1 S2 C9 105.62(12) . . ? O3 S3 O4 116.65(12) . . ? O3 S3 N2 108.89(13) . . ? O4 S3 N2 112.02(11) . . ? O3 S3 C16 107.84(13) . . ? O4 S3 C16 108.16(14) . . ? N2 S3 C16 102.21(12) . . ? O6 S4 O5 120.90(12) . . ? O6 S4 N3 106.69(12) . . ? O5 S4 N3 104.83(12) . . ? O6 S4 C23 107.85(13) . . ? O5 S4 C23 107.27(13) . . ? N3 S4 C23 108.86(12) . . ? C4 N1 S2 118.20(17) . . ? C4 N1 S1 125.05(18) . . ? S2 N1 S1 111.92(11) . . ? S1 N2 S3 125.74(13) . . ? C4 N3 S4 123.59(18) . . ? 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 C5 C1 C2 C8 1.8(4) . . . . ? S1 C1 C2 C8 172.9(2) . . . . ? C5 C1 C2 C3 -177.4(3) . . . . ? S1 C1 C2 C3 -6.4(4) . . . . ? C1 C2 C3 C4 -39.4(3) . . . . ? C8 C2 C3 C4 141.5(3) . . . . ? C1 C2 C3 Cl2 -161.3(2) . . . . ? C8 C2 C3 Cl2 19.5(3) . . . . ? C1 C2 C3 Cl1 80.2(3) . . . . ? C8 C2 C3 Cl1 -98.9(3) . . . . ? C2 C3 C4 N3 -62.0(3) . . . . ? Cl2 C3 C4 N3 62.9(2) . . . . ? Cl1 C3 C4 N3 177.86(16) . . . . ? C2 C3 C4 N1 61.6(3) . . . . ? Cl2 C3 C4 N1 -173.47(17) . . . . ? Cl1 C3 C4 N1 -58.5(2) . . . . ? C2 C1 C5 C6 -0.3(4) . . . . ? S1 C1 C5 C6 -172.2(2) . . . . ? C1 C5 C6 C7 -1.6(4) . . . . ? C5 C6 C7 C8 2.0(5) . . . . ? C6 C7 C8 C2 -0.4(5) . . . . ? C1 C2 C8 C7 -1.4(4) . . . . ? C3 C2 C8 C7 177.8(3) . . . . ? C14 C9 C10 C11 1.3(4) . . . . ? S2 C9 C10 C11 176.1(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C10 C11 C12 C15 -178.6(3) . . . . ? C11 C12 C13 C14 0.8(4) . . . . ? C15 C12 C13 C14 178.6(3) . . . . ? C10 C9 C14 C13 -1.3(4) . . . . ? S2 C9 C14 C13 -176.0(2) . . . . ? C12 C13 C14 C9 0.2(4) . . . . ? C21 C16 C17 C18 2.6(4) . . . . ? S3 C16 C17 C18 -174.1(2) . . . . ? C16 C17 C18 C19 -1.1(5) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? C17 C18 C19 C22 177.1(3) . . . . ? C18 C19 C20 C21 1.2(5) . . . . ? C22 C19 C20 C21 -176.6(3) . . . . ? C17 C16 C21 C20 -2.1(4) . . . . ? S3 C16 C21 C20 174.6(2) . . . . ? C19 C20 C21 C16 0.2(4) . . . . ? C28 C23 C24 C25 -0.6(4) . . . . ? S4 C23 C24 C25 -177.9(2) . . . . ? C23 C24 C25 C26 -0.5(5) . . . . ? C24 C25 C26 C27 0.8(4) . . . . ? C24 C25 C26 C29 179.4(3) . . . . ? C25 C26 C27 C28 -0.1(4) . . . . ? C29 C26 C27 C28 -178.6(3) . . . . ? C26 C27 C28 C23 -1.0(4) . . . . ? C24 C23 C28 C27 1.3(4) . . . . ? S4 C23 C28 C27 178.7(2) . . . . ? C5 C1 S1 N2 -45.2(3) . . . . ? C2 C1 S1 N2 143.0(2) . . . . ? C5 C1 S1 N1 -163.7(2) . . . . ? C2 C1 S1 N1 24.5(3) . . . . ? C14 C9 S2 O1 151.1(2) . . . . ? C10 C9 S2 O1 -23.7(3) . . . . ? C14 C9 S2 O2 18.0(3) . . . . ? C10 C9 S2 O2 -156.9(2) . . . . ? C14 C9 S2 N1 -94.0(2) . . . . ? C10 C9 S2 N1 91.2(2) . . . . ? C21 C16 S3 O3 -146.2(2) . . . . ? C17 C16 S3 O3 30.5(3) . . . . ? C21 C16 S3 O4 -19.3(3) . . . . ? C17 C16 S3 O4 157.5(2) . . . . ? C21 C16 S3 N2 99.1(2) . . . . ? C17 C16 S3 N2 -84.2(2) . . . . ? C28 C23 S4 O6 -14.0(2) . . . . ? C24 C23 S4 O6 163.4(2) . . . . ? C28 C23 S4 O5 -145.7(2) . . . . ? C24 C23 S4 O5 31.7(2) . . . . ? C28 C23 S4 N3 101.4(2) . . . . ? C24 C23 S4 N3 -81.3(2) . . . . ? N3 C4 N1 S2 -125.9(2) . . . . ? C3 C4 N1 S2 112.2(2) . . . . ? N3 C4 N1 S1 80.8(3) . . . . ? C3 C4 N1 S1 -41.1(3) . . . . ? O1 S2 N1 C4 -121.2(2) . . . . ? O2 S2 N1 C4 8.4(3) . . . . ? C9 S2 N1 C4 123.5(2) . . . . ? O1 S2 N1 S1 35.42(17) . . . . ? O2 S2 N1 S1 165.07(15) . . . . ? C9 S2 N1 S1 -79.83(16) . . . . ? N2 S1 N1 C4 -114.3(2) . . . . ? C1 S1 N1 C4 1.6(2) . . . . ? N2 S1 N1 S2 90.92(15) . . . . ? C1 S1 N1 S2 -153.12(14) . . . . ? N1 S1 N2 S3 67.7(2) . . . . ? C1 S1 N2 S3 -42.4(2) . . . . ? O3 S3 N2 S1 107.13(19) . . . . ? O4 S3 N2 S1 -23.4(2) . . . . ? C16 S3 N2 S1 -138.96(18) . . . . ? N1 C4 N3 S4 125.1(2) . . . . ? C3 C4 N3 S4 -113.1(2) . . . . ? O6 S4 N3 C4 22.5(2) . . . . ? O5 S4 N3 C4 151.9(2) . . . . ? C23 S4 N3 C4 -93.6(2) . . . . ? _diffrn_reflns_theta_full 30.00 _refine_diff_density_max 0.288 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.055