# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Vishnu Ji Ram' _publ_contact_author_address ;Department of Chemistry University of Lucknow Lucknow 226007 India ; _publ_contact_author_email vjram@yahoo.com loop_ _publ_author_name _publ_author_address H.Maurya ;Department of Chemistry University of Lucknow Lucknow 226007 India ; V.Tandon ;Department of Chemistry University of Lucknow Lucknow 226007 India ; 'Brijesh Kumar' ;Division of SAIF, Central Drug Research Institute, Lucknow-226001, India ; 'Abhinav Kumar' ;Department of Chemistry University of Lucknow Lucknow 226007 India ; V.Huch ;Institute of Inorganic Chemistry, University of Saarland, Saarbrucken, Germany ; V.Ram '' # Attachment '- 5. sh2992 9d.cif' data_sh2992 _database_code_depnum_ccdc_archive 'CCDC 831577' #TrackingRef '- 5. sh2992 9d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 N O S2' _chemical_formula_weight 373.47 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8038(4) _cell_length_b 16.2989(5) _cell_length_c 19.3777(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.682(2) _cell_angle_gamma 90.00 _cell_volume 3589.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 132(2) _cell_measurement_reflns_used 9897 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 33.24 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.16 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7178 _exptl_absorpt_correction_T_max 0.9394 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 132(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 48753 _diffrn_reflns_av_R_equivalents 0.1175 _diffrn_reflns_av_sigmaI/netI 0.1259 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 33.33 _reflns_number_total 13628 _reflns_number_gt 8352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0700P)^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 13628 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1403 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.2007 _refine_ls_wR_factor_gt 0.1800 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 S1 S 0.09971(6) 0.77189(4) 0.27510(3) 0.02067(14) Uani 1 1 d . . . S2 S 0.65447(6) 0.97312(4) 0.47060(4) 0.02811(17) Uani 1 1 d . . . O1 O 0.29436(14) 0.82616(9) 0.48518(9) 0.0152(3) Uani 1 1 d . . . N1 N 0.3034(2) 0.76594(17) 0.64987(14) 0.0411(7) Uani 1 1 d . . . C1 C 0.4132(2) 0.83425(13) 0.51327(13) 0.0147(4) Uani 1 1 d . . . C2 C 0.4809(2) 0.86260(13) 0.46619(13) 0.0147(4) Uani 1 1 d . . . C3 C 0.6114(2) 0.87312(15) 0.49511(15) 0.0216(5) Uani 1 1 d . . . H3A H 0.6527 0.8299 0.4754 0.026 Uiso 1 1 calc R . . H3B H 0.6339 0.8676 0.5480 0.026 Uiso 1 1 calc R . . C4 C 0.5970(2) 0.96177(14) 0.37762(17) 0.0239(6) Uani 1 1 d . . . C5 C 0.6511(3) 1.00175(16) 0.3307(2) 0.0359(8) Uani 1 1 d . . . H5 H 0.7139 1.0390 0.3492 0.043 Uiso 1 1 calc R . . C6 C 0.6138(3) 0.98722(17) 0.2579(2) 0.0388(9) Uani 1 1 d . . . H6 H 0.6490 1.0160 0.2264 0.047 Uiso 1 1 calc R . . C7 C 0.5252(3) 0.93091(17) 0.23044(18) 0.0353(8) Uani 1 1 d . . . H7 H 0.5037 0.9180 0.1808 0.042 Uiso 1 1 calc R . . C8 C 0.4678(2) 0.89330(15) 0.27588(15) 0.0243(6) Uani 1 1 d . . . H8 H 0.4070 0.8548 0.2568 0.029 Uiso 1 1 calc R . . C9 C 0.4979(2) 0.91113(13) 0.34914(14) 0.0191(5) Uani 1 1 d . . . C10 C 0.4270(2) 0.88162(12) 0.39673(13) 0.0143(4) Uani 1 1 d . . . C11 C 0.2990(2) 0.88004(13) 0.37146(13) 0.0136(4) Uani 1 1 d . . . C12 C 0.2274(2) 0.91874(14) 0.30282(13) 0.0184(5) Uani 1 1 d . . . H12A H 0.2802 0.9542 0.2839 0.022 Uiso 1 1 calc R . . H12B H 0.1676 0.9547 0.3144 0.022 Uiso 1 1 calc R . . C13 C 0.1646(2) 0.86017(15) 0.24332(14) 0.0211(5) Uani 1 1 d . . . H13A H 0.2216 0.8407 0.2177 0.025 Uiso 1 1 calc R . . H13B H 0.1019 0.8906 0.2085 0.025 Uiso 1 1 calc R . . C14 C 0.0380(2) 0.81840(14) 0.33954(14) 0.0181(5) Uani 1 1 d . . . C15 C -0.0841(2) 0.81598(15) 0.32825(15) 0.0223(5) Uani 1 1 d . . . H15 H -0.1327 0.7932 0.2853 0.027 Uiso 1 1 calc R . . C16 C -0.1342(2) 0.84720(16) 0.38038(16) 0.0262(6) Uani 1 1 d . . . H16 H -0.2172 0.8456 0.3728 0.031 Uiso 1 1 calc R . . C17 C -0.0640(2) 0.88029(16) 0.44266(16) 0.0265(6) Uani 1 1 d . . . H17 H -0.0990 0.9026 0.4773 0.032 Uiso 1 1 calc R . . C18 C 0.0586(2) 0.88148(15) 0.45552(15) 0.0222(5) Uani 1 1 d . . . H18 H 0.1066 0.9032 0.4992 0.027 Uiso 1 1 calc R . . C19 C 0.1100(2) 0.85048(13) 0.40374(13) 0.0148(4) Uani 1 1 d . . . C20 C 0.2390(2) 0.85295(13) 0.41750(12) 0.0139(4) Uani 1 1 d . . . C21 C 0.4541(2) 0.81222(15) 0.58341(14) 0.0212(5) Uani 1 1 d . . . H21 H 0.5360 0.8143 0.6068 0.025 Uiso 1 1 calc R . . S3 S 0.39715(5) 0.20763(3) 0.21958(3) 0.01766(13) Uani 1 1 d . . . S4 S -0.16264(6) 0.05781(4) -0.01775(4) 0.02514(16) Uani 1 1 d . . . O2 O 0.20814(15) 0.20422(10) 0.00268(9) 0.0181(3) Uani 1 1 d . . . N2 N 0.1967(4) 0.3091(3) -0.14838(18) 0.1042(19) Uani 1 1 d . . . C22 C 0.3723(2) 0.78606(16) 0.62112(14) 0.0268(6) Uani 1 1 d . . . C23 C 0.0888(2) 0.20470(14) -0.02590(13) 0.0183(5) Uani 1 1 d . . . C24 C 0.0172(2) 0.16478(13) 0.01381(13) 0.0161(5) Uani 1 1 d . . . C25 C -0.1141(2) 0.16320(15) -0.01594(14) 0.0202(5) Uani 1 1 d . . . H25A H -0.1365 0.1864 -0.0650 0.024 Uiso 1 1 calc R . . H25B H -0.1515 0.1966 0.0145 0.024 Uiso 1 1 calc R . . C26 C -0.1083(2) 0.04180(14) 0.07478(16) 0.0217(5) Uani 1 1 d . . . C27 C -0.1686(3) -0.01198(16) 0.1094(2) 0.0350(8) Uani 1 1 d . . . H27 H -0.2325 -0.0436 0.0819 0.042 Uiso 1 1 calc R . . C28 C -0.1350(3) -0.01891(18) 0.1831(2) 0.0398(9) Uani 1 1 d . . . H28 H -0.1736 -0.0572 0.2060 0.048 Uiso 1 1 calc R . . C29 C -0.0449(3) 0.02984(18) 0.22402(18) 0.0334(7) Uani 1 1 d . . . H29 H -0.0271 0.0290 0.2748 0.040 Uiso 1 1 calc R . . C30 C 0.0189(2) 0.07986(15) 0.19002(15) 0.0224(5) Uani 1 1 d . . . H30 H 0.0817 0.1120 0.2181 0.027 Uiso 1 1 calc R . . C31 C -0.0079(2) 0.08359(13) 0.11511(14) 0.0167(5) Uani 1 1 d . . . C32 C 0.0688(2) 0.12716(13) 0.07768(13) 0.0141(4) Uani 1 1 d . . . C33 C 0.1966(2) 0.12278(13) 0.10347(12) 0.0132(4) Uani 1 1 d . . . C34 C 0.2643(2) 0.06880(13) 0.16388(13) 0.0156(4) Uani 1 1 d . . . H34A H 0.3237 0.0378 0.1468 0.019 Uiso 1 1 calc R . . H34B H 0.2090 0.0283 0.1747 0.019 Uiso 1 1 calc R . . C35 C 0.3274(2) 0.11221(14) 0.23364(13) 0.0182(5) Uani 1 1 d . . . H35A H 0.3880 0.0750 0.2627 0.022 Uiso 1 1 calc R . . H35B H 0.2698 0.1237 0.2612 0.022 Uiso 1 1 calc R . . C36 C 0.4602(2) 0.17852(13) 0.14975(13) 0.0162(4) Uani 1 1 d . . . C37 C 0.5829(2) 0.17732(14) 0.16330(14) 0.0191(5) Uani 1 1 d . . . H37 H 0.6310 0.1888 0.2101 0.023 Uiso 1 1 calc R . . C38 C 0.6345(2) 0.15942(15) 0.10848(16) 0.0236(6) Uani 1 1 d . . . H38 H 0.7178 0.1577 0.1181 0.028 Uiso 1 1 calc R . . C39 C 0.5647(2) 0.14413(15) 0.04013(15) 0.0233(5) Uani 1 1 d . . . H39 H 0.6002 0.1319 0.0028 0.028 Uiso 1 1 calc R . . C40 C 0.4424(2) 0.14651(14) 0.02556(15) 0.0214(5) Uani 1 1 d . . . H40 H 0.3951 0.1371 -0.0219 0.026 Uiso 1 1 calc R . . C41 C 0.3893(2) 0.16268(13) 0.08030(13) 0.0157(4) Uani 1 1 d . . . C42 C 0.2597(2) 0.16206(13) 0.06463(12) 0.0148(4) Uani 1 1 d . . . C43 C 0.0499(3) 0.24448(18) -0.08936(15) 0.0306(6) Uani 1 1 d . . . H43 H -0.0322 0.2481 -0.1117 0.037 Uiso 1 1 calc R . . C44 C 0.1301(3) 0.2804(3) -0.12239(17) 0.0552(11) 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 0.0225(3) 0.0203(3) 0.0175(3) -0.0022(2) 0.0025(2) -0.0017(2) S2 0.0168(3) 0.0200(3) 0.0500(5) -0.0094(3) 0.0131(3) -0.0052(2) O1 0.0133(8) 0.0182(7) 0.0134(8) 0.0030(6) 0.0025(6) -0.0016(6) N1 0.0421(17) 0.0588(17) 0.0179(12) 0.0055(12) 0.0004(12) -0.0257(13) C1 0.0116(11) 0.0143(10) 0.0168(11) -0.0005(8) 0.0016(9) -0.0001(8) C2 0.0115(11) 0.0137(10) 0.0190(12) -0.0003(8) 0.0041(9) 0.0003(8) C3 0.0127(11) 0.0226(11) 0.0287(14) -0.0023(10) 0.0045(10) -0.0019(9) C4 0.0191(13) 0.0130(10) 0.0448(17) 0.0035(10) 0.0175(12) 0.0040(9) C5 0.0240(15) 0.0198(12) 0.073(2) 0.0124(13) 0.0295(16) 0.0062(11) C6 0.0378(18) 0.0319(15) 0.061(2) 0.0260(15) 0.0385(18) 0.0159(13) C7 0.0402(18) 0.0362(15) 0.0407(18) 0.0190(13) 0.0300(16) 0.0214(13) C8 0.0264(14) 0.0218(12) 0.0308(15) 0.0089(10) 0.0181(12) 0.0119(10) C9 0.0196(12) 0.0133(10) 0.0296(14) 0.0055(9) 0.0155(11) 0.0057(9) C10 0.0147(11) 0.0101(9) 0.0205(12) 0.0005(8) 0.0088(9) 0.0013(8) C11 0.0147(11) 0.0119(9) 0.0149(11) 0.0001(8) 0.0051(9) -0.0012(8) C12 0.0196(12) 0.0194(11) 0.0175(12) 0.0061(9) 0.0073(10) 0.0030(9) C13 0.0233(13) 0.0255(12) 0.0152(12) 0.0037(9) 0.0064(10) 0.0021(10) C14 0.0166(12) 0.0172(10) 0.0214(12) 0.0059(9) 0.0067(10) 0.0021(9) C15 0.0160(12) 0.0213(11) 0.0269(14) 0.0069(10) 0.0012(10) -0.0008(9) C16 0.0161(13) 0.0259(13) 0.0382(17) 0.0097(11) 0.0101(12) 0.0031(10) C17 0.0196(13) 0.0290(13) 0.0360(16) 0.0038(11) 0.0164(12) 0.0043(11) C18 0.0197(13) 0.0254(12) 0.0237(13) 0.0018(10) 0.0096(11) 0.0003(10) C19 0.0137(11) 0.0140(10) 0.0176(11) 0.0036(8) 0.0057(9) 0.0014(8) C20 0.0152(11) 0.0130(9) 0.0139(11) 0.0006(8) 0.0046(9) -0.0005(8) C21 0.0175(12) 0.0257(12) 0.0172(12) 0.0022(9) -0.0004(10) -0.0047(10) S3 0.0167(3) 0.0181(3) 0.0171(3) -0.0033(2) 0.0029(2) -0.0031(2) S4 0.0145(3) 0.0250(3) 0.0340(4) -0.0127(3) 0.0030(3) -0.0032(2) O2 0.0146(8) 0.0259(8) 0.0123(8) 0.0038(6) 0.0009(7) -0.0059(7) N2 0.074(3) 0.195(5) 0.0291(19) 0.039(2) -0.0111(18) -0.085(3) C22 0.0283(15) 0.0313(14) 0.0144(12) 0.0048(10) -0.0052(11) -0.0103(11) C23 0.0161(12) 0.0228(11) 0.0138(11) -0.0015(9) 0.0004(9) -0.0044(9) C24 0.0156(11) 0.0169(10) 0.0156(11) -0.0034(8) 0.0038(9) -0.0002(8) C25 0.0152(12) 0.0232(12) 0.0206(13) -0.0008(9) 0.0020(10) 0.0014(9) C26 0.0129(12) 0.0154(10) 0.0392(16) -0.0020(10) 0.0111(11) 0.0010(9) C27 0.0167(14) 0.0218(13) 0.072(2) 0.0082(13) 0.0217(15) -0.0014(10) C28 0.0279(17) 0.0335(15) 0.068(3) 0.0237(15) 0.0304(17) 0.0054(13) C29 0.0278(16) 0.0407(16) 0.0403(18) 0.0226(14) 0.0242(14) 0.0172(13) C30 0.0194(13) 0.0267(12) 0.0238(13) 0.0072(10) 0.0107(11) 0.0077(10) C31 0.0139(11) 0.0130(10) 0.0252(13) -0.0001(9) 0.0088(10) 0.0018(8) C32 0.0132(11) 0.0126(9) 0.0164(11) -0.0024(8) 0.0041(9) -0.0007(8) C33 0.0125(10) 0.0133(9) 0.0138(11) -0.0022(8) 0.0037(9) -0.0025(8) C34 0.0139(11) 0.0157(10) 0.0177(11) 0.0018(8) 0.0050(9) -0.0018(8) C35 0.0179(12) 0.0221(11) 0.0150(11) 0.0009(9) 0.0052(10) -0.0035(9) C36 0.0154(11) 0.0139(10) 0.0193(12) 0.0014(8) 0.0046(9) -0.0013(8) C37 0.0142(11) 0.0171(11) 0.0245(13) 0.0006(9) 0.0028(10) -0.0024(9) C38 0.0160(12) 0.0198(11) 0.0369(16) 0.0025(10) 0.0106(12) 0.0002(9) C39 0.0215(13) 0.0232(12) 0.0299(15) -0.0013(10) 0.0148(12) -0.0031(10) C40 0.0197(13) 0.0245(12) 0.0211(13) -0.0033(10) 0.0076(10) -0.0067(10) C41 0.0134(11) 0.0152(10) 0.0187(12) 0.0014(8) 0.0046(9) -0.0035(8) C42 0.0143(11) 0.0174(10) 0.0117(11) -0.0011(8) 0.0018(9) -0.0027(8) C43 0.0264(15) 0.0445(16) 0.0163(13) 0.0083(12) -0.0019(11) -0.0099(12) C44 0.044(2) 0.091(3) 0.0193(16) 0.0226(17) -0.0110(14) -0.034(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C14 1.777(2) . ? S1 C13 1.814(2) . ? S2 C4 1.755(3) . ? S2 C3 1.809(2) . ? O1 C1 1.367(3) . ? O1 C20 1.369(3) . ? N1 C22 1.151(3) . ? C1 C21 1.362(3) . ? C1 C2 1.442(3) . ? C2 C10 1.360(3) . ? C2 C3 1.500(3) . ? C4 C5 1.405(4) . ? C4 C9 1.417(4) . ? C5 C6 1.380(5) . ? C6 C7 1.385(5) . ? C7 C8 1.390(3) . ? C8 C9 1.398(4) . ? C9 C10 1.483(3) . ? C10 C11 1.457(3) . ? C11 C20 1.354(3) . ? C11 C12 1.508(3) . ? C12 C13 1.526(4) . ? C14 C15 1.398(3) . ? C14 C19 1.404(4) . ? C15 C16 1.398(4) . ? C16 C17 1.376(4) . ? C17 C18 1.400(4) . ? C18 C19 1.400(3) . ? C19 C20 1.475(3) . ? C21 C22 1.425(3) . ? S3 C36 1.776(2) . ? S3 C35 1.814(2) . ? S4 C26 1.753(3) . ? S4 C25 1.808(2) . ? O2 C23 1.367(3) . ? O2 C42 1.374(3) . ? N2 C44 1.143(4) . ? C23 C43 1.356(4) . ? C23 C24 1.443(3) . ? C24 C32 1.368(3) . ? C24 C25 1.500(3) . ? C26 C31 1.406(4) . ? C26 C27 1.407(3) . ? C27 C28 1.380(5) . ? C28 C29 1.391(5) . ? C29 C30 1.391(3) . ? C30 C31 1.401(4) . ? C31 C32 1.485(3) . ? C32 C33 1.458(3) . ? C33 C42 1.354(3) . ? C33 C34 1.509(3) . ? C34 C35 1.529(3) . ? C36 C37 1.400(3) . ? C36 C41 1.403(4) . ? C37 C38 1.391(3) . ? C38 C39 1.380(4) . ? C39 C40 1.395(4) . ? C40 C41 1.395(3) . ? C41 C42 1.478(3) . ? C43 C44 1.405(4) . ? 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 C14 S1 C13 101.03(11) . . ? C4 S2 C3 96.69(12) . . ? C1 O1 C20 121.55(17) . . ? C21 C1 O1 114.9(2) . . ? C21 C1 C2 127.4(2) . . ? O1 C1 C2 117.6(2) . . ? C10 C2 C1 120.5(2) . . ? C10 C2 C3 120.2(2) . . ? C1 C2 C3 119.3(2) . . ? C2 C3 S2 109.77(17) . . ? C5 C4 C9 119.4(3) . . ? C5 C4 S2 119.9(2) . . ? C9 C4 S2 120.71(19) . . ? C6 C5 C4 120.4(3) . . ? C5 C6 C7 120.4(2) . . ? C6 C7 C8 119.7(3) . . ? C7 C8 C9 121.2(3) . . ? C8 C9 C4 118.2(2) . . ? C8 C9 C10 122.2(2) . . ? C4 C9 C10 119.5(2) . . ? C2 C10 C11 119.61(19) . . ? C2 C10 C9 119.8(2) . . ? C11 C10 C9 120.3(2) . . ? C20 C11 C10 117.6(2) . . ? C20 C11 C12 116.7(2) . . ? C10 C11 C12 124.90(19) . . ? C11 C12 C13 116.54(19) . . ? C12 C13 S1 113.78(16) . . ? C15 C14 C19 120.0(2) . . ? C15 C14 S1 118.6(2) . . ? C19 C14 S1 121.09(18) . . ? C14 C15 C16 119.8(3) . . ? C17 C16 C15 120.2(2) . . ? C16 C17 C18 120.7(2) . . ? C19 C18 C17 119.6(3) . . ? C18 C19 C14 119.6(2) . . ? C18 C19 C20 119.2(2) . . ? C14 C19 C20 121.3(2) . . ? C11 C20 O1 122.4(2) . . ? C11 C20 C19 126.1(2) . . ? O1 C20 C19 111.50(18) . . ? C1 C21 C22 118.9(2) . . ? C36 S3 C35 100.73(10) . . ? C26 S4 C25 95.46(12) . . ? C23 O2 C42 121.40(17) . . ? N1 C22 C21 177.9(3) . . ? C43 C23 O2 115.4(2) . . ? C43 C23 C24 126.6(2) . . ? O2 C23 C24 118.0(2) . . ? C32 C24 C23 120.2(2) . . ? C32 C24 C25 120.0(2) . . ? C23 C24 C25 119.7(2) . . ? C24 C25 S4 108.24(16) . . ? C31 C26 C27 119.7(3) . . ? C31 C26 S4 121.11(18) . . ? C27 C26 S4 119.2(2) . . ? C28 C27 C26 120.2(3) . . ? C27 C28 C29 120.3(2) . . ? C30 C29 C28 119.5(3) . . ? C29 C30 C31 121.1(3) . . ? C30 C31 C26 118.4(2) . . ? C30 C31 C32 122.0(2) . . ? C26 C31 C32 119.6(2) . . ? C24 C32 C33 119.89(19) . . ? C24 C32 C31 118.4(2) . . ? C33 C32 C31 121.4(2) . . ? C42 C33 C32 117.4(2) . . ? C42 C33 C34 116.8(2) . . ? C32 C33 C34 125.22(18) . . ? C33 C34 C35 116.44(19) . . ? C34 C35 S3 113.33(16) . . ? C37 C36 C41 119.7(2) . . ? C37 C36 S3 119.08(19) . . ? C41 C36 S3 121.04(18) . . ? C38 C37 C36 120.3(2) . . ? C39 C38 C37 120.0(2) . . ? C38 C39 C40 120.4(2) . . ? C39 C40 C41 120.3(3) . . ? C40 C41 C36 119.3(2) . . ? C40 C41 C42 119.7(2) . . ? C36 C41 C42 121.0(2) . . ? C33 C42 O2 122.8(2) . . ? C33 C42 C41 125.7(2) . . ? O2 C42 C41 111.43(18) . . ? C23 C43 C44 120.5(3) . . ? N2 C44 C43 178.9(4) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 33.33 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.759 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.128 data_sh2996 _database_code_depnum_ccdc_archive 'CCDC 831578' #TrackingRef '- 3. sh2996 4f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 Cl N2 O2 S' _chemical_formula_weight 344.80 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' S S 0.1246 0.1234 '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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.7105(6) _cell_length_b 8.3893(6) _cell_length_c 41.097(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3003.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 132(2) _cell_measurement_reflns_used 9226 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 30.73 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.93 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7051 _exptl_absorpt_correction_T_max 0.9501 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 132(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 54973 _diffrn_reflns_av_R_equivalents 0.1281 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -58 _diffrn_reflns_limit_l_max 60 _diffrn_reflns_theta_min 0.99 _diffrn_reflns_theta_max 31.28 _reflns_number_total 9542 _reflns_number_gt 7801 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0792P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(6) _refine_ls_number_reflns 9542 _refine_ls_number_parameters 415 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1430 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.05096(8) 0.92301(8) 0.486035(18) 0.01897(14) Uani 1 1 d . . . Cl1 Cl -0.24084(9) 0.38312(11) 0.57144(2) 0.03200(19) Uani 1 1 d . . . O1 O 0.0980(2) 0.4041(2) 0.46867(5) 0.0166(4) Uani 1 1 d . . . O2 O 0.1903(3) 0.1919(2) 0.44391(6) 0.0243(5) Uani 1 1 d . . . N1 N 0.4767(3) 0.2814(3) 0.39107(7) 0.0258(6) Uani 1 1 d . . . N2 N 0.3472(2) 0.7117(3) 0.41076(6) 0.0143(4) Uani 1 1 d . . . C1 C -0.0320(3) 0.7677(3) 0.50828(7) 0.0175(5) Uani 1 1 d . . . C2 C -0.1448(3) 0.8049(4) 0.53149(8) 0.0229(6) Uani 1 1 d . . . H2 H -0.1766 0.9125 0.5340 0.028 Uiso 1 1 calc R . . C3 C -0.2108(4) 0.6876(4) 0.55081(8) 0.0237(6) Uani 1 1 d . . . H3 H -0.2863 0.7138 0.5666 0.028 Uiso 1 1 calc R . . C4 C -0.1632(3) 0.5299(4) 0.54635(8) 0.0211(6) Uani 1 1 d . . . C5 C -0.0566(3) 0.4883(4) 0.52311(8) 0.0185(6) Uani 1 1 d . . . H5 H -0.0279 0.3799 0.5203 0.022 Uiso 1 1 calc R . . C6 C 0.0094(3) 0.6073(3) 0.50350(7) 0.0149(5) Uani 1 1 d . . . C7 C 0.1113(3) 0.5616(3) 0.47664(7) 0.0155(5) Uani 1 1 d . . . C8 C 0.1990(3) 0.3355(3) 0.44678(7) 0.0155(5) Uani 1 1 d . . . C9 C 0.2954(3) 0.4408(3) 0.42851(7) 0.0141(5) Uani 1 1 d . . . C10 C 0.2864(3) 0.6097(3) 0.43196(7) 0.0127(5) Uani 1 1 d . . . C11 C 0.2034(3) 0.6654(3) 0.46078(7) 0.0142(5) Uani 1 1 d . . . C12 C 0.2303(3) 0.8229(3) 0.47741(7) 0.0160(5) Uani 1 1 d . . . H12A H 0.2944 0.8915 0.4633 0.019 Uiso 1 1 calc R . . H12B H 0.2867 0.8050 0.4980 0.019 Uiso 1 1 calc R . . C13 C 0.3042(3) 0.8844(3) 0.40811(7) 0.0167(5) Uani 1 1 d . . . H13A H 0.3731 0.9521 0.4214 0.020 Uiso 1 1 calc R . . H13B H 0.1967 0.9025 0.4150 0.020 Uiso 1 1 calc R . . C14 C 0.3251(3) 0.9174(3) 0.37173(7) 0.0184(5) Uani 1 1 d . . . H14A H 0.2336 0.8837 0.3592 0.022 Uiso 1 1 calc R . . H14B H 0.3446 1.0319 0.3676 0.022 Uiso 1 1 calc R . . C15 C 0.4638(3) 0.8173(3) 0.36308(8) 0.0204(6) Uani 1 1 d . . . H15A H 0.5598 0.8669 0.3710 0.024 Uiso 1 1 calc R . . H15B H 0.4714 0.8006 0.3393 0.024 Uiso 1 1 calc R . . C16 C 0.4303(3) 0.6614(3) 0.38083(7) 0.0182(5) Uani 1 1 d . . . H16A H 0.3657 0.5904 0.3673 0.022 Uiso 1 1 calc R . . H16B H 0.5267 0.6052 0.3864 0.022 Uiso 1 1 calc R . . C17 C 0.3952(3) 0.3565(3) 0.40692(7) 0.0179(5) Uani 1 1 d . . . S3 S 0.21921(8) 0.57816(8) 0.190953(17) 0.01814(14) Uani 1 1 d . . . Cl2 Cl 0.50695(9) 1.12004(11) 0.10549(2) 0.03196(19) Uani 1 1 d . . . O3 O 0.1710(2) 1.0954(2) 0.20820(5) 0.0178(4) Uani 1 1 d . . . O4 O 0.0780(3) 1.3087(2) 0.23314(6) 0.0243(5) Uani 1 1 d . . . N3 N -0.2076(3) 1.2185(3) 0.28607(7) 0.0240(5) Uani 1 1 d . . . N4 N -0.0781(3) 0.7883(3) 0.26636(6) 0.0148(4) Uani 1 1 d . . . C18 C 0.3012(3) 0.7338(3) 0.16819(7) 0.0177(5) Uani 1 1 d . . . C19 C 0.4129(3) 0.6973(4) 0.14515(8) 0.0222(6) Uani 1 1 d . . . H19 H 0.4450 0.5899 0.1424 0.027 Uiso 1 1 calc R . . C20 C 0.4774(3) 0.8153(4) 0.12627(7) 0.0237(6) Uani 1 1 d . . . H20 H 0.5544 0.7895 0.1108 0.028 Uiso 1 1 calc R . . C21 C 0.4294(3) 0.9718(4) 0.13002(8) 0.0216(6) Uani 1 1 d . . . C22 C 0.3237(3) 1.0130(3) 0.15380(8) 0.0184(6) Uani 1 1 d . . . H22 H 0.2957 1.1215 0.1568 0.022 Uiso 1 1 calc R . . C23 C 0.2583(3) 0.8948(3) 0.17347(7) 0.0164(5) Uani 1 1 d . . . C24 C 0.1573(3) 0.9380(3) 0.20035(7) 0.0147(5) Uani 1 1 d . . . C25 C 0.0701(3) 1.1654(3) 0.23018(8) 0.0172(5) Uani 1 1 d . . . C26 C -0.0271(3) 1.0597(3) 0.24864(7) 0.0153(5) Uani 1 1 d . . . C27 C -0.0168(3) 0.8911(3) 0.24542(8) 0.0139(5) Uani 1 1 d . . . C28 C 0.0653(3) 0.8362(3) 0.21658(7) 0.0141(5) Uani 1 1 d . . . C29 C 0.0401(3) 0.6773(3) 0.19950(8) 0.0170(5) Uani 1 1 d . . . H29A H -0.0158 0.6956 0.1789 0.020 Uiso 1 1 calc R . . H29B H -0.0242 0.6079 0.2134 0.020 Uiso 1 1 calc R . . C30 C -0.1623(3) 0.8385(3) 0.29596(7) 0.0178(5) Uani 1 1 d . . . H30A H -0.2588 0.8940 0.2902 0.021 Uiso 1 1 calc R . . H30B H -0.0986 0.9101 0.3095 0.021 Uiso 1 1 calc R . . C31 C -0.1953(4) 0.6832(3) 0.31361(7) 0.0203(6) Uani 1 1 d . . . H31A H -0.2910 0.6332 0.3055 0.024 Uiso 1 1 calc R . . H31B H -0.2037 0.7001 0.3374 0.024 Uiso 1 1 calc R . . C32 C -0.0549(4) 0.5821(3) 0.30518(8) 0.0208(6) Uani 1 1 d . . . H32A H 0.0365 0.6161 0.3177 0.025 Uiso 1 1 calc R . . H32B H -0.0742 0.4674 0.3092 0.025 Uiso 1 1 calc R . . C33 C -0.0365(3) 0.6168(3) 0.26920(7) 0.0177(5) Uani 1 1 d . . . H33A H 0.0706 0.5982 0.2621 0.021 Uiso 1 1 calc R . . H33B H -0.1062 0.5495 0.2560 0.021 Uiso 1 1 calc R . . C34 C -0.1266(3) 1.1433(3) 0.27008(7) 0.0170(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 0.0217(3) 0.0155(3) 0.0197(4) -0.0005(3) 0.0030(3) 0.0024(2) Cl1 0.0244(4) 0.0445(4) 0.0271(4) 0.0192(3) 0.0045(3) -0.0004(3) O1 0.0200(10) 0.0116(9) 0.0181(11) 0.0001(7) 0.0047(8) -0.0019(7) O2 0.0299(11) 0.0119(9) 0.0311(13) 0.0012(8) 0.0045(9) -0.0017(7) N1 0.0306(14) 0.0197(12) 0.0273(15) -0.0052(10) -0.0001(11) 0.0067(10) N2 0.0163(10) 0.0123(10) 0.0143(11) -0.0025(8) 0.0020(8) -0.0009(8) C1 0.0181(12) 0.0202(12) 0.0143(13) 0.0007(10) -0.0008(10) 0.0002(9) C2 0.0224(14) 0.0261(14) 0.0203(15) -0.0033(11) 0.0013(11) 0.0029(11) C3 0.0196(13) 0.0365(16) 0.0151(14) -0.0008(12) 0.0046(11) 0.0027(12) C4 0.0164(13) 0.0320(14) 0.0150(16) 0.0080(13) -0.0037(10) -0.0030(11) C5 0.0142(11) 0.0236(14) 0.0176(18) 0.0053(11) -0.0026(10) -0.0026(10) C6 0.0136(12) 0.0168(12) 0.0143(13) 0.0012(10) -0.0003(10) 0.0001(9) C7 0.0177(13) 0.0124(12) 0.0164(14) -0.0006(10) -0.0022(10) -0.0005(9) C8 0.0166(12) 0.0176(12) 0.0124(14) -0.0021(10) -0.0010(10) 0.0018(9) C9 0.0147(11) 0.0138(13) 0.0139(13) -0.0026(10) -0.0017(10) 0.0013(8) C10 0.0146(12) 0.0130(11) 0.0104(13) -0.0009(9) -0.0019(9) -0.0015(8) C11 0.0149(12) 0.0146(11) 0.0131(14) -0.0028(10) -0.0024(9) 0.0006(8) C12 0.0191(12) 0.0146(11) 0.0142(14) -0.0002(10) 0.0007(9) -0.0018(9) C13 0.0212(13) 0.0084(10) 0.0204(14) 0.0001(9) 0.0018(11) -0.0020(9) C14 0.0263(14) 0.0166(11) 0.0124(13) 0.0025(10) 0.0047(10) -0.0003(10) C15 0.0232(13) 0.0185(12) 0.0194(14) 0.0002(11) 0.0028(11) -0.0021(10) C16 0.0205(13) 0.0174(12) 0.0165(14) -0.0028(11) 0.0049(10) 0.0046(10) C17 0.0190(12) 0.0132(11) 0.0217(15) -0.0030(10) -0.0022(11) 0.0002(9) S3 0.0199(3) 0.0154(3) 0.0191(4) -0.0001(3) 0.0026(3) 0.0013(2) Cl2 0.0244(3) 0.0457(4) 0.0257(4) 0.0176(3) 0.0006(3) -0.0061(3) O3 0.0197(10) 0.0140(9) 0.0195(12) -0.0003(8) -0.0002(8) -0.0017(7) O4 0.0306(11) 0.0144(9) 0.0280(13) -0.0003(8) 0.0025(9) -0.0012(8) N3 0.0260(13) 0.0207(12) 0.0252(15) -0.0033(10) 0.0000(11) 0.0026(9) N4 0.0159(10) 0.0149(10) 0.0136(11) 0.0008(8) 0.0020(8) 0.0011(8) C18 0.0183(12) 0.0192(12) 0.0158(14) -0.0002(10) -0.0007(10) -0.0015(9) C19 0.0238(13) 0.0270(15) 0.0159(14) -0.0030(11) 0.0002(11) 0.0027(11) C20 0.0210(13) 0.0352(15) 0.0148(15) 0.0005(12) 0.0013(11) -0.0024(11) C21 0.0162(12) 0.0336(15) 0.0150(16) 0.0040(13) 0.0000(11) -0.0063(11) C22 0.0175(12) 0.0199(14) 0.0178(18) 0.0033(10) -0.0028(11) -0.0039(10) C23 0.0144(12) 0.0201(12) 0.0148(14) 0.0009(10) -0.0015(10) -0.0019(9) C24 0.0136(12) 0.0151(12) 0.0153(14) 0.0015(10) -0.0020(10) -0.0008(8) C25 0.0166(12) 0.0168(12) 0.0182(15) -0.0001(11) -0.0021(10) 0.0009(9) C26 0.0158(12) 0.0140(13) 0.0161(14) -0.0003(10) -0.0036(10) 0.0020(9) C27 0.0117(11) 0.0143(11) 0.0157(14) 0.0004(10) -0.0018(10) 0.0007(9) C28 0.0167(12) 0.0122(11) 0.0134(14) 0.0017(10) 0.0016(10) -0.0007(9) C29 0.0171(12) 0.0151(12) 0.0189(14) -0.0045(10) 0.0022(10) -0.0014(9) C30 0.0174(13) 0.0183(12) 0.0177(14) -0.0017(11) 0.0018(10) 0.0020(9) C31 0.0243(14) 0.0209(12) 0.0158(14) 0.0012(10) 0.0068(11) -0.0022(10) C32 0.0252(14) 0.0164(11) 0.0209(15) 0.0028(11) -0.0004(11) -0.0012(10) C33 0.0216(13) 0.0128(11) 0.0187(14) -0.0013(9) 0.0037(11) 0.0005(9) C34 0.0217(13) 0.0133(12) 0.0161(14) 0.0008(10) -0.0060(11) 0.0017(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 C1 1.749(3) . ? S1 C12 1.809(3) . ? Cl1 C4 1.743(3) . ? O1 C7 1.366(3) . ? O1 C8 1.383(3) . ? O2 C8 1.213(3) . ? N1 C17 1.151(4) . ? N2 C10 1.331(4) . ? N2 C16 1.488(4) . ? N2 C13 1.500(3) . ? C1 C2 1.405(4) . ? C1 C6 1.406(4) . ? C2 C3 1.389(5) . ? C3 C4 1.399(5) . ? C4 C5 1.377(5) . ? C5 C6 1.406(4) . ? C6 C7 1.467(4) . ? C7 C11 1.352(4) . ? C8 C9 1.431(4) . ? C9 C10 1.427(3) . ? C9 C17 1.429(4) . ? C10 C11 1.464(4) . ? C11 C12 1.506(4) . ? C13 C14 1.531(4) . ? C14 C15 1.514(4) . ? C15 C16 1.526(4) . ? S3 C18 1.758(3) . ? S3 C29 1.803(3) . ? Cl2 C21 1.738(3) . ? O3 C24 1.365(3) . ? O3 C25 1.390(4) . ? O4 C25 1.210(3) . ? N3 C34 1.152(4) . ? N4 C27 1.330(4) . ? N4 C30 1.481(4) . ? N4 C33 1.489(3) . ? C18 C19 1.392(4) . ? C18 C23 1.417(4) . ? C19 C20 1.377(4) . ? C20 C21 1.387(5) . ? C21 C22 1.386(5) . ? C22 C23 1.401(4) . ? C23 C24 1.458(4) . ? C24 C28 1.348(4) . ? C25 C26 1.442(4) . ? C26 C34 1.421(4) . ? C26 C27 1.424(3) . ? C27 C28 1.459(4) . ? C28 C29 1.522(4) . ? C30 C31 1.519(4) . ? C31 C32 1.528(4) . ? C32 C33 1.516(4) . ? 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 C1 S1 C12 96.51(13) . . ? C7 O1 C8 120.3(2) . . ? C10 N2 C16 123.5(2) . . ? C10 N2 C13 124.7(2) . . ? C16 N2 C13 109.6(2) . . ? C2 C1 C6 119.2(3) . . ? C2 C1 S1 118.6(2) . . ? C6 C1 S1 122.2(2) . . ? C3 C2 C1 121.3(3) . . ? C2 C3 C4 118.2(3) . . ? C5 C4 C3 122.1(3) . . ? C5 C4 Cl1 119.5(3) . . ? C3 C4 Cl1 118.4(2) . . ? C4 C5 C6 119.6(3) . . ? C5 C6 C1 119.6(3) . . ? C5 C6 C7 119.5(2) . . ? C1 C6 C7 120.7(2) . . ? C11 C7 O1 123.9(2) . . ? C11 C7 C6 123.6(2) . . ? O1 C7 C6 112.5(2) . . ? O2 C8 O1 115.9(3) . . ? O2 C8 C9 126.7(3) . . ? O1 C8 C9 117.2(2) . . ? C10 C9 C17 125.9(3) . . ? C10 C9 C8 121.9(2) . . ? C17 C9 C8 112.2(2) . . ? N2 C10 C9 123.5(3) . . ? N2 C10 C11 121.4(2) . . ? C9 C10 C11 115.1(2) . . ? C7 C11 C10 118.5(2) . . ? C7 C11 C12 116.0(2) . . ? C10 C11 C12 124.8(2) . . ? C11 C12 S1 111.24(18) . . ? N2 C13 C14 102.5(2) . . ? C15 C14 C13 102.9(2) . . ? C14 C15 C16 102.2(2) . . ? N2 C16 C15 104.2(2) . . ? N1 C17 C9 175.6(3) . . ? C18 S3 C29 96.46(13) . . ? C24 O3 C25 120.5(2) . . ? C27 N4 C30 123.1(2) . . ? C27 N4 C33 125.4(2) . . ? C30 N4 C33 109.3(2) . . ? C19 C18 C23 119.9(3) . . ? C19 C18 S3 118.8(2) . . ? C23 C18 S3 121.2(2) . . ? C20 C19 C18 120.7(3) . . ? C19 C20 C21 119.7(3) . . ? C22 C21 C20 121.0(3) . . ? C22 C21 Cl2 119.2(3) . . ? C20 C21 Cl2 119.7(2) . . ? C21 C22 C23 120.0(3) . . ? C22 C23 C18 118.6(3) . . ? C22 C23 C24 120.4(3) . . ? C18 C23 C24 120.8(2) . . ? C28 C24 O3 123.2(3) . . ? C28 C24 C23 125.2(3) . . ? O3 C24 C23 111.5(2) . . ? O4 C25 O3 116.7(3) . . ? O4 C25 C26 126.2(3) . . ? O3 C25 C26 117.0(2) . . ? C34 C26 C27 125.9(3) . . ? C34 C26 C25 112.4(2) . . ? C27 C26 C25 121.7(3) . . ? N4 C27 C26 124.0(3) . . ? N4 C27 C28 121.2(2) . . ? C26 C27 C28 114.8(2) . . ? C24 C28 C27 119.6(2) . . ? C24 C28 C29 114.4(3) . . ? C27 C28 C29 125.5(2) . . ? C28 C29 S3 111.64(19) . . ? N4 C30 C31 104.0(2) . . ? C30 C31 C32 102.5(2) . . ? C33 C32 C31 101.5(2) . . ? N4 C33 C32 103.7(2) . . ? N3 C34 C26 175.8(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 31.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.425 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.083 # Attachment '- 4. sh3000 9c.cif' data_sh3000 _database_code_depnum_ccdc_archive 'CCDC 831579' #TrackingRef '- 4. sh3000 9c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 N O2 S' _chemical_formula_weight 371.44 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.723(2) _cell_length_b 9.374(4) _cell_length_c 24.947(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.26(3) _cell_angle_gamma 90.00 _cell_volume 1798.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8655 _exptl_absorpt_correction_T_max 0.9652 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21353 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 28.12 _reflns_number_total 4276 _reflns_number_gt 3335 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0666P)^2^+0.1091P] 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 4276 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 S1 S 0.37349(5) 0.83858(4) 0.191899(15) 0.04462(13) Uani 1 1 d . . . O1 O 0.31909(13) 0.59459(9) 0.01064(4) 0.0331(2) Uani 1 1 d . . . O2 O 0.19868(15) 0.15145(9) 0.04762(4) 0.0410(2) Uani 1 1 d . . . N1 N 0.2999(2) 0.82281(15) -0.09573(5) 0.0490(3) Uani 1 1 d . . . C1 C 0.40741(16) 0.57332(12) 0.11950(5) 0.0284(2) Uani 1 1 d . . . C2 C 0.47954(16) 0.56030(14) 0.17706(5) 0.0321(3) Uani 1 1 d . . . C3 C 0.57214(19) 0.43902(15) 0.19612(6) 0.0374(3) Uani 1 1 d . . . C4 C 0.6373(2) 0.42726(18) 0.25007(6) 0.0463(4) Uani 1 1 d . . . C5 C 0.6138(2) 0.53700(19) 0.28600(6) 0.0511(4) Uani 1 1 d . . . C6 C 0.5301(2) 0.66020(18) 0.26801(6) 0.0465(4) Uani 1 1 d . . . C7 C 0.46484(19) 0.67416(15) 0.21387(5) 0.0369(3) Uani 1 1 d . . . C8 C 0.4621(2) 0.83779(14) 0.12659(6) 0.0413(3) Uani 1 1 d . . . C9 C 0.40693(17) 0.70490(13) 0.09544(5) 0.0312(3) Uani 1 1 d . . . C10 C 0.36193(16) 0.71620(12) 0.03830(5) 0.0289(3) Uani 1 1 d . . . C11 C 0.28631(15) 0.46601(11) 0.03533(5) 0.0274(2) Uani 1 1 d . . . C12 C 0.20323(16) 0.37003(12) -0.00712(5) 0.0281(2) Uani 1 1 d . . . C13 C 0.15967(17) 0.42753(13) -0.05936(5) 0.0314(3) Uani 1 1 d . . . C14 C 0.08510(17) 0.34783(14) -0.10256(5) 0.0331(3) Uani 1 1 d . . . C15 C 0.05334(18) 0.20364(15) -0.09382(6) 0.0375(3) Uani 1 1 d . . . C16 C 0.09341(19) 0.14331(14) -0.04365(6) 0.0377(3) Uani 1 1 d . . . C17 C 0.16626(17) 0.22436(13) -0.00024(5) 0.0323(3) Uani 1 1 d . . . C18 C 0.1479(2) 0.22412(14) 0.09496(6) 0.0384(3) Uani 1 1 d . . . C19 C 0.29291(19) 0.31560(13) 0.12029(5) 0.0336(3) Uani 1 1 d . . . C20 C 0.33185(16) 0.44959(12) 0.08925(5) 0.0275(2) Uani 1 1 d . . . C21 C 0.36691(18) 0.83612(13) 0.00732(6) 0.0348(3) Uani 1 1 d . . . C22 C 0.32958(18) 0.82884(13) -0.04953(6) 0.0361(3) Uani 1 1 d . . . C23 C 0.0402(2) 0.41493(18) -0.15721(6) 0.0418(3) Uani 1 1 d . . . H1 H 0.595(2) 0.3655(18) 0.1706(7) 0.039(4) Uiso 1 1 d . . . H2 H 0.702(2) 0.339(2) 0.2600(7) 0.051(5) Uiso 1 1 d . . . H3 H 0.661(2) 0.5318(19) 0.3236(7) 0.050(5) Uiso 1 1 d . . . H4 H 0.523(3) 0.734(2) 0.2923(8) 0.059(5) Uiso 1 1 d . . . H5 H 0.425(3) 0.924(2) 0.1073(8) 0.056(5) Uiso 1 1 d . . . H6 H 0.592(3) 0.8451(19) 0.1318(7) 0.049(5) Uiso 1 1 d . . . H7 H 0.391(2) 0.925(2) 0.0224(7) 0.051(5) Uiso 1 1 d . . . H8 H 0.185(2) 0.5298(19) -0.0647(6) 0.040(4) Uiso 1 1 d . . . H9 H 0.009(2) 0.144(2) -0.1233(7) 0.048(5) Uiso 1 1 d . . . H10 H 0.071(2) 0.044(2) -0.0357(7) 0.048(5) Uiso 1 1 d . . . H11 H 0.039(2) 0.2815(19) 0.0851(7) 0.047(5) Uiso 1 1 d . . . H12 H 0.121(2) 0.1451(17) 0.1199(6) 0.036(4) Uiso 1 1 d . . . H13 H 0.258(2) 0.3443(19) 0.1575(8) 0.052(5) Uiso 1 1 d . . . H14 H 0.393(2) 0.2517(19) 0.1260(7) 0.042(4) Uiso 1 1 d . . . H15 H -0.077(3) 0.392(3) -0.1703(10) 0.086(7) Uiso 1 1 d . . . H16 H 0.057(3) 0.521(3) -0.1562(9) 0.080(7) Uiso 1 1 d . . . H17 H 0.118(3) 0.379(3) -0.1831(9) 0.071(6) 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 0.0528(2) 0.03574(19) 0.0447(2) -0.01431(14) 0.00136(16) 0.00089(15) O1 0.0456(5) 0.0210(4) 0.0320(4) -0.0013(3) -0.0010(4) -0.0063(3) O2 0.0604(7) 0.0221(4) 0.0398(5) -0.0014(4) 0.0011(5) -0.0018(4) N1 0.0568(8) 0.0485(7) 0.0414(7) 0.0068(5) 0.0023(6) 0.0063(6) C1 0.0266(6) 0.0267(5) 0.0317(6) -0.0036(4) 0.0024(4) -0.0016(4) C2 0.0299(6) 0.0336(6) 0.0325(6) -0.0020(5) 0.0010(5) -0.0045(5) C3 0.0366(7) 0.0389(7) 0.0360(7) 0.0008(5) 0.0005(5) -0.0020(5) C4 0.0466(9) 0.0512(8) 0.0396(8) 0.0079(6) -0.0047(6) -0.0026(7) C5 0.0608(10) 0.0607(10) 0.0307(7) 0.0034(7) -0.0025(6) -0.0141(8) C6 0.0592(10) 0.0492(8) 0.0315(7) -0.0083(6) 0.0053(6) -0.0130(7) C7 0.0371(7) 0.0398(7) 0.0339(6) -0.0071(5) 0.0039(5) -0.0084(5) C8 0.0542(9) 0.0274(6) 0.0411(7) -0.0076(5) -0.0025(6) -0.0097(6) C9 0.0316(6) 0.0254(5) 0.0361(6) -0.0050(5) 0.0009(5) -0.0037(5) C10 0.0274(6) 0.0225(5) 0.0365(6) -0.0036(4) 0.0021(5) -0.0029(4) C11 0.0275(6) 0.0194(5) 0.0354(6) -0.0016(4) 0.0029(5) -0.0017(4) C12 0.0274(6) 0.0225(5) 0.0344(6) -0.0050(4) 0.0026(5) -0.0002(4) C13 0.0314(6) 0.0267(6) 0.0359(6) -0.0036(5) 0.0015(5) -0.0001(5) C14 0.0291(6) 0.0343(6) 0.0356(6) -0.0066(5) 0.0017(5) 0.0002(5) C15 0.0374(7) 0.0348(7) 0.0402(7) -0.0124(5) 0.0022(5) -0.0047(5) C16 0.0419(8) 0.0253(6) 0.0459(8) -0.0093(5) 0.0041(6) -0.0055(5) C17 0.0345(6) 0.0253(6) 0.0370(6) -0.0043(5) 0.0024(5) -0.0010(5) C18 0.0452(8) 0.0301(6) 0.0407(7) -0.0007(5) 0.0077(6) -0.0095(6) C19 0.0386(7) 0.0261(6) 0.0362(7) 0.0006(5) 0.0035(5) -0.0030(5) C20 0.0264(6) 0.0226(5) 0.0338(6) -0.0035(4) 0.0036(4) -0.0008(4) C21 0.0397(7) 0.0241(6) 0.0406(7) -0.0007(5) 0.0027(5) -0.0052(5) C22 0.0384(7) 0.0255(6) 0.0444(8) 0.0048(5) 0.0040(6) -0.0003(5) C23 0.0430(8) 0.0460(8) 0.0356(7) -0.0023(6) -0.0011(6) -0.0045(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 S1 C7 1.7615(16) . ? S1 C8 1.8242(17) . ? O1 C10 1.3577(14) . ? O1 C11 1.3873(14) . ? O2 C17 1.3786(16) . ? O2 C18 1.4482(18) . ? N1 C22 1.1558(19) . ? C1 C9 1.3715(17) . ? C1 C20 1.4745(16) . ? C1 C2 1.4968(18) . ? C2 C3 1.4027(19) . ? C2 C7 1.4194(18) . ? C3 C4 1.397(2) . ? C4 C5 1.387(2) . ? C5 C6 1.378(3) . ? C6 C7 1.404(2) . ? C8 C9 1.5089(17) . ? C9 C10 1.4399(18) . ? C10 C21 1.3667(18) . ? C11 C20 1.3676(18) . ? C11 C12 1.4893(16) . ? C12 C17 1.4087(17) . ? C12 C13 1.4218(18) . ? C13 C14 1.3920(17) . ? C14 C15 1.394(2) . ? C14 C23 1.512(2) . ? C15 C16 1.382(2) . ? C16 C17 1.3982(18) . ? C18 C19 1.5028(19) . ? C19 C20 1.5200(17) . ? C21 C22 1.423(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 C7 S1 C8 95.85(7) . . ? C10 O1 C11 123.35(10) . . ? C17 O2 C18 115.58(10) . . ? C9 C1 C20 119.89(11) . . ? C9 C1 C2 118.62(11) . . ? C20 C1 C2 121.45(11) . . ? C3 C2 C7 117.30(12) . . ? C3 C2 C1 121.64(12) . . ? C7 C2 C1 120.97(12) . . ? C4 C3 C2 121.19(14) . . ? C5 C4 C3 120.45(15) . . ? C6 C5 C4 119.76(14) . . ? C5 C6 C7 120.51(14) . . ? C6 C7 C2 120.63(14) . . ? C6 C7 S1 118.63(11) . . ? C2 C7 S1 120.67(11) . . ? C9 C8 S1 110.60(10) . . ? C1 C9 C10 119.35(11) . . ? C1 C9 C8 121.85(12) . . ? C10 C9 C8 118.70(11) . . ? O1 C10 C21 114.92(11) . . ? O1 C10 C9 117.82(10) . . ? C21 C10 C9 127.13(11) . . ? C20 C11 O1 119.57(10) . . ? C20 C11 C12 133.36(11) . . ? O1 C11 C12 107.07(10) . . ? C17 C12 C13 116.46(11) . . ? C17 C12 C11 125.30(11) . . ? C13 C12 C11 118.23(11) . . ? C14 C13 C12 123.54(12) . . ? C13 C14 C15 117.73(12) . . ? C13 C14 C23 121.27(12) . . ? C15 C14 C23 121.00(12) . . ? C16 C15 C14 120.68(12) . . ? C15 C16 C17 121.31(13) . . ? O2 C17 C16 115.44(11) . . ? O2 C17 C12 124.29(11) . . ? C16 C17 C12 120.26(12) . . ? O2 C18 C19 111.37(12) . . ? C18 C19 C20 115.59(11) . . ? C11 C20 C1 117.96(11) . . ? C11 C20 C19 123.30(10) . . ? C1 C20 C19 118.48(11) . . ? C10 C21 C22 120.71(12) . . ? N1 C22 C21 179.73(17) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.235 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.044