# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email arijiit2007@gmail.com _publ_contact_author_name 'Arijit Mukherjee' loop_ _publ_author_name 'Pawel Grobelny' 'Arijit Mukherjee' 'Gautam R. Desiraju' data_form_I _database_code_depnum_ccdc_archive 'CCDC 855682' #TrackingRef 'web_deposit_cif_file_0_ArijitMukherjee_1334771861.form I.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl N2 O2 S' _chemical_formula_weight 358.83 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 'P c a 21' 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 29.950(12) _cell_length_b 4.995(2) _cell_length_c 22.828(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3415(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7169 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21934 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1064 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.57 _reflns_number_total 21934 _reflns_number_gt 16796 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0775P)^2^+0.6229P] 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 SHELXL _refine_ls_extinction_coef 0.0039(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.42(6) _refine_ls_number_reflns 21934 _refine_ls_number_parameters 439 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.2089 _refine_ls_wR_factor_gt 0.1599 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 0.29796(9) 0.7107(6) 0.21945(13) 0.0240(6) Uani 1 1 d . . . C2 C 0.32882(9) 0.7562(6) 0.17514(14) 0.0276(7) Uani 1 1 d . . . H2 H 0.3544 0.8557 0.1825 0.033 Uiso 1 1 calc R . . C3 C 0.32101(9) 0.6511(6) 0.11933(14) 0.0280(6) Uani 1 1 d . . . H3 H 0.3415 0.6812 0.0895 0.034 Uiso 1 1 calc R . . C4 C 0.28257(9) 0.5010(6) 0.10809(13) 0.0233(6) Uani 1 1 d . . . C5 C 0.25281(9) 0.4480(6) 0.15429(13) 0.0250(6) Uani 1 1 d . . . H5 H 0.2279 0.3411 0.1476 0.030 Uiso 1 1 calc R . . C6 C 0.26006(9) 0.5530(6) 0.20961(13) 0.0260(6) Uani 1 1 d . . . H6 H 0.2400 0.5192 0.2398 0.031 Uiso 1 1 calc R . . C7 C 0.27538(9) 0.3955(6) 0.04816(12) 0.0241(6) Uani 1 1 d . . . C8 C 0.30813(9) 0.2291(6) 0.02464(13) 0.0252(6) Uani 1 1 d . . . H8 H 0.3339 0.1920 0.0458 0.030 Uiso 1 1 calc R . . C9 C 0.30213(10) 0.1209(7) -0.02968(15) 0.0341(7) Uani 1 1 d . . . C10 C 0.26356(12) 0.1778(8) -0.06075(15) 0.0426(9) Uani 1 1 d . . . H10 H 0.2591 0.0979 -0.0971 0.051 Uiso 1 1 calc R . . C11 C 0.23756(9) 0.4520(7) 0.01315(13) 0.0282(6) Uani 1 1 d . . . C12 C 0.20093(9) 0.6287(7) 0.03185(14) 0.0300(7) Uani 1 1 d . . . C13 C 0.15720(10) 0.5776(7) 0.01283(16) 0.0383(8) Uani 1 1 d . . . H13 H 0.1513 0.4371 -0.0128 0.046 Uiso 1 1 calc R . . C14 C 0.12339(10) 0.7380(8) 0.03265(17) 0.0433(9) Uani 1 1 d . . . H14 H 0.0944 0.7090 0.0195 0.052 Uiso 1 1 calc R . . C15 C 0.13166(9) 0.9407(7) 0.07153(16) 0.0373(8) Uani 1 1 d . . . C16 C 0.20627(9) 0.8506(6) 0.06795(14) 0.0290(6) Uani 1 1 d . . . H16 H 0.2353 0.8951 0.0788 0.035 Uiso 1 1 calc R . . C17 C 0.09476(11) 1.1040(8) 0.09839(19) 0.0510(10) Uani 1 1 d . . . H17A H 0.0854 1.0224 0.1344 0.077 Uiso 1 1 calc R . . H17B H 0.0700 1.1119 0.0718 0.077 Uiso 1 1 calc R . . H17C H 0.1054 1.2820 0.1061 0.077 Uiso 1 1 calc R . . C18 C 0.31556(12) 0.6223(8) 0.34048(15) 0.0415(8) Uani 1 1 d . . . H18A H 0.3192 0.7030 0.3783 0.062 Uiso 1 1 calc R . . H18B H 0.3420 0.5240 0.3306 0.062 Uiso 1 1 calc R . . H18C H 0.2905 0.5027 0.3412 0.062 Uiso 1 1 calc R . . C19 C 0.45507(9) 0.3867(6) 0.13966(12) 0.0239(6) Uani 1 1 d . . . C20 C 0.49325(9) 0.5417(6) 0.14744(13) 0.0272(6) Uani 1 1 d . . . H20 H 0.5130 0.5686 0.1166 0.033 Uiso 1 1 calc R . . C21 C 0.50146(9) 0.6554(6) 0.20182(13) 0.0270(6) Uani 1 1 d . . . H21 H 0.5269 0.7591 0.2075 0.032 Uiso 1 1 calc R . . C22 C 0.47123(9) 0.6143(6) 0.24875(13) 0.0247(6) Uani 1 1 d . . . C23 C 0.43258(9) 0.4686(6) 0.23892(14) 0.0283(6) Uani 1 1 d . . . H23 H 0.4120 0.4478 0.2691 0.034 Uiso 1 1 calc R . . C24 C 0.42402(9) 0.3532(6) 0.18486(14) 0.0278(6) Uani 1 1 d . . . H24 H 0.3980 0.2551 0.1787 0.033 Uiso 1 1 calc R . . C25 C 0.48060(9) 0.7270(6) 0.30847(13) 0.0264(6) Uani 1 1 d . . . C26 C 0.44887(10) 0.8994(7) 0.33352(14) 0.0314(7) Uani 1 1 d . . . H26 H 0.4222 0.9347 0.3141 0.038 Uiso 1 1 calc R . . C27 C 0.45731(12) 1.0147(8) 0.38635(15) 0.0382(8) Uani 1 1 d . . . C28 C 0.49682(13) 0.9508(9) 0.41449(16) 0.0475(9) Uani 1 1 d . . . H28 H 0.5025 1.0289 0.4507 0.057 Uiso 1 1 calc R . . C29 C 0.52002(10) 0.6701(7) 0.34065(13) 0.0299(7) Uani 1 1 d . . . C30 C 0.55637(10) 0.4914(7) 0.31900(14) 0.0287(7) Uani 1 1 d . . . C31 C 0.60076(10) 0.5437(7) 0.33365(15) 0.0352(7) Uani 1 1 d . . . H31 H 0.6078 0.6858 0.3583 0.042 Uiso 1 1 calc R . . C32 C 0.63398(10) 0.3834(7) 0.31129(16) 0.0396(8) Uani 1 1 d . . . H32 H 0.6636 0.4145 0.3216 0.048 Uiso 1 1 calc R . . C33 C 0.62354(10) 0.1769(7) 0.27373(16) 0.0375(8) Uani 1 1 d . . . C34 C 0.54892(9) 0.2694(6) 0.28478(16) 0.0323(7) Uani 1 1 d . . . H34 H 0.5194 0.2245 0.2770 0.039 Uiso 1 1 calc R . . C35 C 0.65898(10) 0.0121(9) 0.24398(18) 0.0462(10) Uani 1 1 d . . . H35A H 0.6480 -0.1662 0.2377 0.069 Uiso 1 1 calc R . . H35B H 0.6851 0.0055 0.2683 0.069 Uiso 1 1 calc R . . H35C H 0.6664 0.0918 0.2070 0.069 Uiso 1 1 calc R . . C36 C 0.43559(11) 0.4709(7) 0.02037(14) 0.0328(7) Uani 1 1 d . . . H36A H 0.4602 0.5943 0.0193 0.049 Uiso 1 1 calc R . . H36B H 0.4088 0.5648 0.0309 0.049 Uiso 1 1 calc R . . H36C H 0.4319 0.3908 -0.0175 0.049 Uiso 1 1 calc R . . N1 N 0.17330(8) 1.0062(6) 0.08849(13) 0.0350(7) Uani 1 1 d . . . N2 N 0.23269(9) 0.3440(6) -0.03992(12) 0.0365(6) Uani 1 1 d . . . N3 N 0.52706(10) 0.7839(6) 0.39261(12) 0.0403(7) Uani 1 1 d . . . N4 N 0.58093(8) 0.1104(6) 0.26133(13) 0.0354(7) Uani 1 1 d . . . O1 O 0.34590(7) 1.0389(5) 0.28250(10) 0.0346(5) Uani 1 1 d . . . O2 O 0.26515(7) 1.0073(5) 0.30327(10) 0.0356(5) Uani 1 1 d . . . O3 O 0.48754(7) 0.0851(5) 0.05568(9) 0.0333(5) Uani 1 1 d . . . O4 O 0.40686(7) 0.0526(4) 0.07876(11) 0.0336(5) Uani 1 1 d . . . S1 S 0.30627(2) 0.87556(16) 0.28743(3) 0.02688(17) Uani 1 1 d . . . S2 S 0.44651(2) 0.21747(15) 0.07288(3) 0.02585(16) Uani 1 1 d . . . Cl1 Cl 0.34179(3) -0.0950(2) -0.05920(4) 0.0489(2) Uani 1 1 d . . . Cl2 Cl 0.42036(4) 1.2372(2) 0.41689(4) 0.0540(3) 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 0.0260(13) 0.0212(16) 0.0246(15) -0.0021(12) -0.0005(10) 0.0000(10) C2 0.0201(12) 0.0319(19) 0.0308(16) -0.0010(13) 0.0005(11) -0.0056(11) C3 0.0242(13) 0.0303(18) 0.0296(16) -0.0020(13) 0.0006(11) -0.0019(11) C4 0.0228(13) 0.0189(15) 0.0282(16) -0.0052(12) -0.0018(10) 0.0009(10) C5 0.0215(12) 0.0227(16) 0.0307(16) -0.0040(12) -0.0010(10) -0.0040(10) C6 0.0253(13) 0.0240(16) 0.0288(15) 0.0006(12) 0.0049(11) -0.0026(11) C7 0.0269(13) 0.0245(16) 0.0207(14) 0.0016(12) -0.0019(10) 0.0047(11) C8 0.0265(13) 0.0216(17) 0.0276(16) -0.0028(12) 0.0019(10) 0.0044(10) C9 0.0386(17) 0.032(2) 0.0316(17) -0.0022(14) 0.0014(12) 0.0060(13) C10 0.056(2) 0.044(2) 0.0277(18) -0.0145(16) -0.0074(14) 0.0105(16) C11 0.0243(13) 0.0292(18) 0.0311(17) 0.0033(13) -0.0059(11) -0.0007(11) C12 0.0274(14) 0.0291(18) 0.0335(17) 0.0054(13) -0.0065(11) 0.0007(12) C13 0.0316(16) 0.037(2) 0.046(2) -0.0029(17) -0.0116(13) 0.0002(13) C14 0.0274(16) 0.043(2) 0.060(2) 0.0056(18) -0.0111(14) 0.0033(13) C15 0.0208(13) 0.042(2) 0.049(2) 0.0105(17) 0.0015(13) 0.0020(12) C16 0.0219(12) 0.0251(17) 0.0401(18) 0.0005(14) 0.0012(11) -0.0021(10) C17 0.0293(17) 0.050(3) 0.074(3) 0.005(2) 0.0035(16) 0.0072(15) C18 0.054(2) 0.042(2) 0.0283(18) 0.0026(16) -0.0068(15) 0.0074(16) C19 0.0265(13) 0.0229(17) 0.0222(15) -0.0020(12) -0.0030(10) -0.0045(10) C20 0.0280(14) 0.0278(17) 0.0256(15) -0.0001(12) 0.0025(11) -0.0044(11) C21 0.0232(13) 0.0302(17) 0.0276(16) -0.0009(13) -0.0016(10) -0.0047(10) C22 0.0289(14) 0.0193(16) 0.0258(15) 0.0029(12) -0.0029(11) 0.0019(11) C23 0.0245(13) 0.0322(18) 0.0283(16) -0.0009(13) 0.0033(11) 0.0026(12) C24 0.0231(13) 0.0293(18) 0.0311(17) -0.0026(13) 0.0019(10) -0.0034(11) C25 0.0299(14) 0.0254(17) 0.0240(15) 0.0036(12) 0.0010(10) -0.0003(11) C26 0.0364(16) 0.0304(19) 0.0276(16) -0.0012(14) 0.0023(12) 0.0021(12) C27 0.056(2) 0.034(2) 0.0246(17) -0.0019(14) 0.0044(13) 0.0081(16) C28 0.064(2) 0.058(3) 0.0199(17) -0.0103(17) -0.0070(15) 0.0095(19) C29 0.0368(16) 0.0274(18) 0.0253(16) 0.0002(13) -0.0026(12) -0.0028(12) C30 0.0290(15) 0.0273(18) 0.0299(17) 0.0087(13) -0.0026(11) 0.0010(11) C31 0.0375(16) 0.037(2) 0.0308(17) 0.0082(15) -0.0113(13) -0.0033(13) C32 0.0249(15) 0.045(2) 0.049(2) 0.0087(17) -0.0112(13) -0.0055(13) C33 0.0222(14) 0.043(2) 0.047(2) 0.0145(17) 0.0014(12) 0.0035(12) C34 0.0260(14) 0.0253(17) 0.045(2) 0.0073(15) 0.0014(13) 0.0008(10) C35 0.0278(17) 0.056(3) 0.055(2) 0.004(2) 0.0037(14) 0.0058(15) C36 0.0428(17) 0.0276(19) 0.0279(17) -0.0003(14) -0.0019(13) 0.0043(13) N1 0.0245(13) 0.0301(16) 0.0503(18) 0.0035(13) 0.0014(11) 0.0014(10) N2 0.0394(14) 0.0389(18) 0.0312(15) -0.0034(13) -0.0084(11) 0.0072(12) N3 0.0550(17) 0.0403(19) 0.0255(15) -0.0023(13) -0.0114(12) 0.0030(13) N4 0.0274(13) 0.0333(17) 0.0454(18) -0.0008(13) -0.0004(11) 0.0025(11) O1 0.0347(11) 0.0338(13) 0.0352(13) -0.0094(11) -0.0020(9) -0.0104(9) O2 0.0313(11) 0.0408(14) 0.0348(13) -0.0104(10) 0.0014(9) 0.0078(9) O3 0.0291(11) 0.0348(14) 0.0359(13) -0.0086(10) -0.0010(8) 0.0058(8) O4 0.0311(11) 0.0277(12) 0.0421(14) -0.0050(11) -0.0041(9) -0.0071(8) S1 0.0281(3) 0.0285(4) 0.0240(4) -0.0063(3) -0.0011(3) 0.0010(3) S2 0.0259(3) 0.0232(4) 0.0285(4) -0.0033(3) -0.0019(3) 0.0006(2) Cl1 0.0545(5) 0.0524(6) 0.0396(5) -0.0169(4) 0.0074(4) 0.0130(4) Cl2 0.0703(6) 0.0524(6) 0.0393(5) -0.0109(5) 0.0113(4) 0.0167(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.389(4) . ? C1 C6 1.400(4) . ? C1 S1 1.774(3) . ? C2 C3 1.398(4) . ? C2 H2 0.9300 . ? C3 C4 1.398(4) . ? C3 H3 0.9300 . ? C4 C5 1.406(4) . ? C4 C7 1.482(4) . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.393(4) . ? C7 C11 1.415(4) . ? C8 C9 1.365(4) . ? C8 H8 0.9300 . ? C9 C10 1.385(4) . ? C9 Cl1 1.740(3) . ? C10 N2 1.330(4) . ? C10 H10 0.9300 . ? C11 N2 1.334(4) . ? C11 C12 1.471(4) . ? C12 C16 1.390(5) . ? C12 C13 1.403(4) . ? C13 C14 1.368(5) . ? C13 H13 0.9300 . ? C14 C15 1.369(5) . ? C14 H14 0.9300 . ? C15 N1 1.346(4) . ? C15 C17 1.504(4) . ? C16 N1 1.341(4) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 S1 1.773(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.392(4) . ? C19 C24 1.399(4) . ? C19 S2 1.762(3) . ? C20 C21 1.387(4) . ? C20 H20 0.9300 . ? C21 C22 1.418(4) . ? C21 H21 0.9300 . ? C22 C23 1.386(4) . ? C22 C25 1.501(4) . ? C23 C24 1.386(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.404(4) . ? C25 C29 1.419(4) . ? C26 C27 1.360(5) . ? C26 H26 0.9300 . ? C27 C28 1.384(5) . ? C27 Cl2 1.716(4) . ? C28 N3 1.328(5) . ? C28 H28 0.9300 . ? C29 N3 1.332(4) . ? C29 C30 1.492(4) . ? C30 C34 1.375(5) . ? C30 C31 1.396(4) . ? C31 C32 1.376(5) . ? C31 H31 0.9300 . ? C32 C33 1.377(5) . ? C32 H32 0.9300 . ? C33 N4 1.349(4) . ? C33 C35 1.505(5) . ? C34 N4 1.355(4) . ? C34 H34 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 S2 1.774(3) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? O1 S1 1.444(2) . ? O2 S1 1.442(2) . ? O3 S2 1.450(2) . ? O4 S2 1.451(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 C2 C1 C6 121.0(3) . . ? C2 C1 S1 117.9(2) . . ? C6 C1 S1 121.0(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 C7 118.7(3) . . ? C5 C4 C7 122.3(2) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 119.1(3) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C8 C7 C11 117.7(3) . . ? C8 C7 C4 117.7(2) . . ? C11 C7 C4 124.5(3) . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 119.6(3) . . ? C8 C9 Cl1 120.5(2) . . ? C10 C9 Cl1 119.9(3) . . ? N2 C10 C9 121.6(3) . . ? N2 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? N2 C11 C7 121.3(3) . . ? N2 C11 C12 115.1(3) . . ? C7 C11 C12 123.6(3) . . ? C16 C12 C13 115.8(3) . . ? C16 C12 C11 124.4(3) . . ? C13 C12 C11 119.8(3) . . ? C14 C13 C12 118.8(3) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 120.9(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? N1 C15 C14 122.3(3) . . ? N1 C15 C17 115.6(3) . . ? C14 C15 C17 122.2(3) . . ? N1 C16 C12 125.8(3) . . ? N1 C16 H16 117.1 . . ? C12 C16 H16 117.1 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 121.2(3) . . ? C20 C19 S2 119.8(2) . . ? C24 C19 S2 119.0(2) . . ? C21 C20 C19 119.2(3) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 120.2(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.2(3) . . ? C23 C22 C25 120.0(3) . . ? C21 C22 C25 120.8(3) . . ? C24 C23 C22 121.1(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C19 119.0(3) . . ? C23 C24 H24 120.5 . . ? C19 C24 H24 120.5 . . ? C26 C25 C29 118.4(3) . . ? C26 C25 C22 118.2(3) . . ? C29 C25 C22 123.4(3) . . ? C27 C26 C25 119.7(3) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 118.2(3) . . ? C26 C27 Cl2 121.0(3) . . ? C28 C27 Cl2 120.8(3) . . ? N3 C28 C27 123.6(3) . . ? N3 C28 H28 118.2 . . ? C27 C28 H28 118.2 . . ? N3 C29 C25 120.5(3) . . ? N3 C29 C30 115.8(3) . . ? C25 C29 C30 123.7(3) . . ? C34 C30 C31 116.2(3) . . ? C34 C30 C29 123.5(3) . . ? C31 C30 C29 120.2(3) . . ? C32 C31 C30 119.4(3) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C31 C32 C33 120.2(3) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? N4 C33 C32 122.0(3) . . ? N4 C33 C35 116.0(3) . . ? C32 C33 C35 122.0(3) . . ? N4 C34 C30 125.6(3) . . ? N4 C34 H34 117.2 . . ? C30 C34 H34 117.2 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? S2 C36 H36A 109.5 . . ? S2 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? S2 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C16 N1 C15 116.1(3) . . ? C10 N2 C11 120.0(3) . . ? C28 N3 C29 119.6(3) . . ? C33 N4 C34 116.2(3) . . ? O2 S1 O1 117.61(14) . . ? O2 S1 C18 106.74(16) . . ? O1 S1 C18 109.09(16) . . ? O2 S1 C1 108.13(13) . . ? O1 S1 C1 108.03(14) . . ? C18 S1 C1 106.75(17) . . ? O3 S2 O4 117.38(14) . . ? O3 S2 C19 109.27(13) . . ? O4 S2 C19 108.14(14) . . ? O3 S2 C36 107.38(15) . . ? O4 S2 C36 108.45(15) . . ? C19 S2 C36 105.61(16) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.679 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.091 # Attachment 'web_deposit_cif_file_1_ArijitMukherjee_1334771861.Form IV.cif' data_Form_IV _database_code_depnum_ccdc_archive 'CCDC 855683' #TrackingRef 'web_deposit_cif_file_1_ArijitMukherjee_1334771861.Form IV.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl N2 O2 S' _chemical_formula_weight 358.83 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0520(16) _cell_length_b 10.412(2) _cell_length_c 10.455(2) _cell_angle_alpha 85.62(3) _cell_angle_beta 83.17(3) _cell_angle_gamma 80.56(3) _cell_volume 857.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2083 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6781 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2939 _reflns_number_gt 2579 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.1314P)^2^+0.1572P] 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 2939 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _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 C1 C 1.2606(2) 0.67205(19) 1.23771(18) 0.0256(4) Uani 1 1 d . . . H1 H 1.3506 0.6456 1.2868 0.031 Uiso 1 1 calc R . . C2 C 1.1170(2) 0.75112(18) 1.29128(18) 0.0240(4) Uani 1 1 d . . . C3 C 0.9854(2) 0.79605(17) 1.21790(17) 0.0226(4) Uani 1 1 d . . . H3 H 0.8891 0.8492 1.2529 0.027 Uiso 1 1 calc R . . C4 C 0.9989(2) 0.76068(16) 1.09063(17) 0.0205(4) Uani 1 1 d . . . C5 C 1.1441(2) 0.67387(17) 1.04470(17) 0.0200(4) Uani 1 1 d . . . C6 C 0.8612(2) 0.81420(16) 1.00942(17) 0.0193(4) Uani 1 1 d . . . C7 C 0.8976(2) 0.88955(17) 0.89592(17) 0.0223(4) Uani 1 1 d . . . H7 H 1.0058 0.9105 0.8745 0.027 Uiso 1 1 calc R . . C8 C 0.7725(2) 0.93296(17) 0.81545(17) 0.0224(4) Uani 1 1 d . . . H8 H 0.7962 0.9828 0.7398 0.027 Uiso 1 1 calc R . . C9 C 0.6110(2) 0.90123(17) 0.84890(16) 0.0184(4) Uani 1 1 d . . . C10 C 0.5708(2) 0.83120(17) 0.96389(16) 0.0196(4) Uani 1 1 d . . . H10 H 0.4612 0.8137 0.9865 0.023 Uiso 1 1 calc R . . C11 C 0.6957(2) 0.78774(17) 1.04432(16) 0.0205(4) Uani 1 1 d . . . H11 H 0.6700 0.7410 1.1215 0.025 Uiso 1 1 calc R . . C12 C 0.5195(3) 0.8299(2) 0.62088(19) 0.0317(5) Uani 1 1 d . . . H12A H 0.5204 0.7436 0.6607 0.048 Uiso 1 1 calc R . . H12B H 0.6308 0.8386 0.5804 0.048 Uiso 1 1 calc R . . H12C H 0.4408 0.8446 0.5571 0.048 Uiso 1 1 calc R . . C13 C 1.1679(2) 0.61695(16) 0.91613(17) 0.0201(4) Uani 1 1 d . . . C14 C 1.3315(2) 0.57976(18) 0.85502(18) 0.0239(4) Uani 1 1 d . . . H14 H 1.4222 0.5948 0.8961 0.029 Uiso 1 1 calc R . . C15 C 1.2356(2) 0.50060(17) 0.68239(18) 0.0246(4) Uani 1 1 d . . . C16 C 1.0688(2) 0.53422(18) 0.73559(18) 0.0245(4) Uani 1 1 d . . . H16 H 0.9806 0.5185 0.6921 0.029 Uiso 1 1 calc R . . C17 C 1.0342(2) 0.59090(17) 0.85297(18) 0.0227(4) Uani 1 1 d . . . H17 H 0.9229 0.6116 0.8898 0.027 Uiso 1 1 calc R . . C18 C 1.2799(3) 0.4316(2) 0.5593(2) 0.0358(5) Uani 1 1 d . . . H18A H 1.3465 0.4814 0.4984 0.054 Uiso 1 1 calc R . . H18B H 1.1779 0.4222 0.5243 0.054 Uiso 1 1 calc R . . H18C H 1.3437 0.3469 0.5764 0.054 Uiso 1 1 calc R . . N1 N 1.36644(19) 0.52419(16) 0.74184(16) 0.0266(4) Uani 1 1 d . . . N2 N 1.27288(19) 0.63300(16) 1.11776(15) 0.0246(4) Uani 1 1 d . . . O1 O 0.29521(16) 0.92509(15) 0.80358(13) 0.0325(4) Uani 1 1 d . . . O2 O 0.47548(17) 1.07274(13) 0.67995(13) 0.0306(4) Uani 1 1 d . . . S1 S 0.45778(5) 0.94535(4) 0.73919(4) 0.0217(2) Uani 1 1 d . . . Cl1 Cl 1.10406(7) 0.79245(5) 1.45087(4) 0.0350(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 0.0244(9) 0.0276(10) 0.0252(9) 0.0025(8) -0.0078(8) -0.0033(8) C2 0.0295(10) 0.0217(9) 0.0221(9) -0.0002(7) -0.0055(8) -0.0062(8) C3 0.0239(9) 0.0192(9) 0.0245(9) -0.0023(7) -0.0030(7) -0.0020(7) C4 0.0217(9) 0.0176(9) 0.0226(9) 0.0004(7) -0.0036(7) -0.0044(7) C5 0.0194(9) 0.0185(8) 0.0226(9) 0.0021(7) -0.0038(7) -0.0049(7) C6 0.0189(8) 0.0159(8) 0.0224(8) -0.0036(6) -0.0023(7) 0.0002(6) C7 0.0185(9) 0.0209(9) 0.0269(9) 0.0034(7) -0.0018(7) -0.0046(7) C8 0.0234(9) 0.0206(9) 0.0218(9) 0.0041(7) -0.0006(7) -0.0034(7) C9 0.0174(8) 0.0183(8) 0.0193(8) -0.0032(7) -0.0036(7) 0.0000(7) C10 0.0159(8) 0.0218(9) 0.0207(8) -0.0038(7) 0.0014(7) -0.0035(7) C11 0.0234(9) 0.0192(8) 0.0182(8) 0.0003(6) -0.0006(7) -0.0033(7) C12 0.0369(11) 0.0355(11) 0.0235(10) -0.0096(8) -0.0052(8) -0.0033(9) C13 0.0227(9) 0.0157(8) 0.0218(9) 0.0024(7) -0.0040(7) -0.0031(7) C14 0.0222(9) 0.0233(9) 0.0260(9) -0.0014(7) -0.0050(7) -0.0008(7) C15 0.0307(10) 0.0188(9) 0.0234(9) 0.0008(7) -0.0025(8) -0.0024(7) C16 0.0275(9) 0.0211(9) 0.0268(9) -0.0009(7) -0.0070(8) -0.0067(7) C17 0.0226(9) 0.0191(9) 0.0261(9) -0.0004(7) -0.0029(7) -0.0027(7) C18 0.0395(12) 0.0400(12) 0.0283(10) -0.0105(9) -0.0023(9) -0.0043(10) N1 0.0255(9) 0.0266(8) 0.0259(8) -0.0031(6) -0.0008(7) 0.0006(7) N2 0.0216(8) 0.0268(8) 0.0244(8) 0.0004(6) -0.0048(6) -0.0005(6) O1 0.0177(7) 0.0432(9) 0.0353(8) -0.0033(6) -0.0035(6) -0.0005(6) O2 0.0368(8) 0.0257(7) 0.0280(7) 0.0033(6) -0.0094(6) 0.0013(6) S1 0.0192(3) 0.0241(3) 0.0208(3) -0.0024(2) -0.0045(2) 0.0014(2) Cl1 0.0411(4) 0.0419(4) 0.0224(3) -0.0067(2) -0.0090(2) -0.0013(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 1.335(2) . ? C1 C2 1.390(3) . ? C1 H1 0.9300 . ? C2 C3 1.381(3) . ? C2 Cl1 1.7418(19) . ? C3 C4 1.395(2) . ? C3 H3 0.9300 . ? C4 C5 1.415(3) . ? C4 C6 1.486(2) . ? C5 N2 1.354(2) . ? C5 C13 1.489(2) . ? C6 C7 1.400(2) . ? C6 C11 1.405(2) . ? C7 C8 1.386(3) . ? C7 H7 0.9300 . ? C8 C9 1.392(2) . ? C8 H8 0.9300 . ? C9 C10 1.390(2) . ? C9 S1 1.7663(18) . ? C10 C11 1.384(2) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 S1 1.763(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C17 1.401(3) . ? C13 C14 1.401(3) . ? C14 N1 1.336(2) . ? C14 H14 0.9300 . ? C15 N1 1.349(3) . ? C15 C16 1.391(3) . ? C15 C18 1.499(3) . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O1 S1 1.4389(15) . ? O2 S1 1.4417(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 N2 C1 C2 121.80(17) . . ? N2 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.85(17) . . ? C3 C2 Cl1 120.42(14) . . ? C1 C2 Cl1 119.73(15) . . ? C2 C3 C4 119.15(16) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 117.99(17) . . ? C3 C4 C6 119.26(15) . . ? C5 C4 C6 122.75(16) . . ? N2 C5 C4 121.64(16) . . ? N2 C5 C13 114.27(15) . . ? C4 C5 C13 124.07(16) . . ? C7 C6 C11 119.76(16) . . ? C7 C6 C4 119.66(15) . . ? C11 C6 C4 120.56(15) . . ? C8 C7 C6 120.04(17) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.36(16) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 121.33(16) . . ? C10 C9 S1 119.73(14) . . ? C8 C9 S1 118.89(13) . . ? C11 C10 C9 119.32(16) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C6 120.07(16) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? S1 C12 H12A 109.5 . . ? S1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C17 C13 C14 116.33(16) . . ? C17 C13 C5 123.54(16) . . ? C14 C13 C5 120.04(16) . . ? N1 C14 C13 124.64(17) . . ? N1 C14 H14 117.7 . . ? C13 C14 H14 117.7 . . ? N1 C15 C16 121.46(17) . . ? N1 C15 C18 116.54(17) . . ? C16 C15 C18 121.95(17) . . ? C17 C16 C15 120.04(17) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C13 119.49(17) . . ? C16 C17 H17 120.3 . . ? C13 C17 H17 120.3 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 N1 C15 118.02(16) . . ? C1 N2 C5 119.38(16) . . ? O1 S1 O2 118.41(9) . . ? O1 S1 C12 108.33(10) . . ? O2 S1 C12 108.43(10) . . ? O1 S1 C9 108.64(8) . . ? O2 S1 C9 108.78(9) . . ? C12 S1 C9 103.19(9) . . ? 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 N2 C1 C2 C3 -2.9(3) . . . . ? N2 C1 C2 Cl1 176.89(14) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? Cl1 C2 C3 C4 -179.59(13) . . . . ? C2 C3 C4 C5 3.4(3) . . . . ? C2 C3 C4 C6 -176.99(16) . . . . ? C3 C4 C5 N2 -4.7(3) . . . . ? C6 C4 C5 N2 175.68(16) . . . . ? C3 C4 C5 C13 173.55(16) . . . . ? C6 C4 C5 C13 -6.0(3) . . . . ? C3 C4 C6 C7 119.89(19) . . . . ? C5 C4 C6 C7 -60.5(2) . . . . ? C3 C4 C6 C11 -61.3(2) . . . . ? C5 C4 C6 C11 118.25(19) . . . . ? C11 C6 C7 C8 -2.9(3) . . . . ? C4 C6 C7 C8 175.94(16) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 2.6(3) . . . . ? C7 C8 C9 S1 -174.74(14) . . . . ? C8 C9 C10 C11 -2.6(3) . . . . ? S1 C9 C10 C11 174.70(12) . . . . ? C9 C10 C11 C6 -0.1(3) . . . . ? C7 C6 C11 C10 2.8(3) . . . . ? C4 C6 C11 C10 -175.96(15) . . . . ? N2 C5 C13 C17 147.81(17) . . . . ? C4 C5 C13 C17 -30.6(3) . . . . ? N2 C5 C13 C14 -28.6(2) . . . . ? C4 C5 C13 C14 152.95(18) . . . . ? C17 C13 C14 N1 1.1(3) . . . . ? C5 C13 C14 N1 177.81(16) . . . . ? N1 C15 C16 C17 -1.2(3) . . . . ? C18 C15 C16 C17 176.22(17) . . . . ? C15 C16 C17 C13 1.5(3) . . . . ? C14 C13 C17 C16 -1.4(3) . . . . ? C5 C13 C17 C16 -178.01(16) . . . . ? C13 C14 N1 C15 -0.8(3) . . . . ? C16 C15 N1 C14 0.8(3) . . . . ? C18 C15 N1 C14 -176.75(17) . . . . ? C2 C1 N2 C5 1.7(3) . . . . ? C4 C5 N2 C1 2.2(3) . . . . ? C13 C5 N2 C1 -176.25(16) . . . . ? C10 C9 S1 O1 13.34(17) . . . . ? C8 C9 S1 O1 -169.31(13) . . . . ? C10 C9 S1 O2 143.51(14) . . . . ? C8 C9 S1 O2 -39.15(16) . . . . ? C10 C9 S1 C12 -101.48(16) . . . . ? C8 C9 S1 C12 75.86(16) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.424 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.105 # Attachment 'web_deposit_cif_file_2_ArijitMukherjee_1334771861.hemihydrate I.cif' data_hemihydrate_I _database_code_depnum_ccdc_archive 'CCDC 855684' #TrackingRef 'web_deposit_cif_file_2_ArijitMukherjee_1334771861.hemihydrate I.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Cl N2 O2.50 S' _chemical_formula_weight 367.84 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 'P c c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 20.9182(15) _cell_length_b 12.4873(8) _cell_length_c 12.8222(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3349.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 29621 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.843 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32897 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3846 _reflns_number_gt 3410 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0369P)^2^+2.1178P] 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 3846 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 C1 C 0.37795(7) 0.58936(12) 0.45789(12) 0.0186(3) Uani 1 1 d . . . C2 C 0.33964(7) 0.65687(13) 0.39934(12) 0.0204(3) Uani 1 1 d . . . H2 H 0.3058 0.6930 0.4305 0.024 Uiso 1 1 calc R . . C3 C 0.35213(7) 0.67026(13) 0.29348(12) 0.0199(3) Uani 1 1 d . . . H3 H 0.3261 0.7145 0.2534 0.024 Uiso 1 1 calc R . . C4 C 0.40363(7) 0.61733(12) 0.24747(12) 0.0176(3) Uani 1 1 d . . . C5 C 0.44266(7) 0.55137(12) 0.30848(12) 0.0195(3) Uani 1 1 d . . . H5 H 0.4776 0.5173 0.2784 0.023 Uiso 1 1 calc R . . C6 C 0.42970(7) 0.53635(13) 0.41318(12) 0.0210(3) Uani 1 1 d . . . H6 H 0.4552 0.4914 0.4533 0.025 Uiso 1 1 calc R . . C7 C 0.41353(7) 0.62194(12) 0.13252(12) 0.0178(3) Uani 1 1 d . . . C8 C 0.36206(7) 0.59112(13) 0.07045(12) 0.0203(3) Uani 1 1 d . . . H8 H 0.3223 0.5783 0.1002 0.024 Uiso 1 1 calc R . . C9 C 0.37077(7) 0.57985(12) -0.03592(12) 0.0205(3) Uani 1 1 d . . . C10 C 0.43034(8) 0.59984(13) -0.07846(12) 0.0224(3) Uani 1 1 d . . . H10 H 0.4366 0.5880 -0.1493 0.027 Uiso 1 1 calc R . . C11 C 0.47153(7) 0.64829(12) 0.08241(12) 0.0184(3) Uani 1 1 d . . . C12 C 0.52776(7) 0.69650(12) 0.13565(12) 0.0182(3) Uani 1 1 d . . . C13 C 0.58760(7) 0.69295(13) 0.08810(13) 0.0224(3) Uani 1 1 d . . . H13 H 0.5916 0.6532 0.0271 0.027 Uiso 1 1 calc R . . C14 C 0.63514(7) 0.79895(12) 0.21332(13) 0.0202(3) Uani 1 1 d . . . C15 C 0.57796(8) 0.80295(12) 0.26843(12) 0.0208(3) Uani 1 1 d . . . H15 H 0.5760 0.8393 0.3316 0.025 Uiso 1 1 calc R . . C16 C 0.52425(7) 0.75310(12) 0.22958(12) 0.0203(3) Uani 1 1 d . . . H16 H 0.4858 0.7571 0.2657 0.024 Uiso 1 1 calc R . . C17 C 0.69314(8) 0.85900(15) 0.24928(16) 0.0277(4) Uani 1 1 d . . . C18 C 0.34308(12) 0.43416(16) 0.60415(17) 0.0376(5) Uani 1 1 d . . . N1 N 0.47891(6) 0.63543(11) -0.02145(10) 0.0221(3) Uani 1 1 d . . . N2 N 0.63986(6) 0.74283(12) 0.12413(11) 0.0236(3) Uani 1 1 d . . . O1 O 0.30547(6) 0.63232(11) 0.61783(9) 0.0329(3) Uani 1 1 d . . . O2 O 0.41921(6) 0.59072(11) 0.64963(10) 0.0331(3) Uani 1 1 d . . . O3 O 0.7500 0.7500 0.48911(15) 0.0346(8) Uani 0.995(10) 2 d SP . . S1 S 0.361349(19) 0.57084(3) 0.59226(3) 0.02068(11) Uani 1 1 d . . . Cl1 Cl 0.308190(19) 0.54048(4) -0.11517(3) 0.02997(12) Uani 1 1 d . . . H3O H 0.7198(14) 0.753(2) 0.529(2) 0.052(8) Uiso 1 1 d . . . H17A H 0.7291(11) 0.8460(18) 0.2056(18) 0.044(6) Uiso 1 1 d . . . H17B H 0.6844(11) 0.934(2) 0.2505(18) 0.051(7) Uiso 1 1 d . . . H17C H 0.7039(12) 0.838(2) 0.321(2) 0.065(8) Uiso 1 1 d . . . H18A H 0.3077(11) 0.4169(19) 0.565(2) 0.045(7) Uiso 1 1 d . . . H18B H 0.3815(12) 0.393(2) 0.5810(19) 0.051(7) Uiso 1 1 d . . . H18C H 0.3346(12) 0.425(2) 0.676(2) 0.056(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 C1 0.0192(7) 0.0211(7) 0.0156(7) 0.0002(6) -0.0005(6) -0.0052(6) C2 0.0179(7) 0.0220(8) 0.0212(8) -0.0009(6) 0.0030(6) -0.0008(6) C3 0.0186(7) 0.0206(7) 0.0205(7) 0.0033(6) 0.0008(6) 0.0013(6) C4 0.0156(7) 0.0189(7) 0.0184(7) 0.0010(6) 0.0015(6) -0.0043(6) C5 0.0159(7) 0.0214(8) 0.0212(8) -0.0011(6) 0.0015(6) 0.0000(6) C6 0.0193(7) 0.0235(8) 0.0203(8) 0.0020(6) -0.0030(6) -0.0001(6) C7 0.0180(7) 0.0179(7) 0.0174(7) 0.0003(6) 0.0018(6) 0.0012(6) C8 0.0184(7) 0.0220(8) 0.0206(7) 0.0029(6) 0.0017(6) -0.0013(6) C9 0.0206(8) 0.0209(8) 0.0200(7) -0.0001(6) -0.0040(6) -0.0001(6) C10 0.0250(8) 0.0259(8) 0.0164(7) -0.0015(6) 0.0020(6) -0.0016(6) C11 0.0184(7) 0.0177(7) 0.0190(7) 0.0005(6) 0.0012(6) 0.0003(6) C12 0.0176(7) 0.0179(7) 0.0193(7) 0.0016(6) -0.0001(6) -0.0006(6) C13 0.0205(8) 0.0261(8) 0.0205(8) -0.0047(6) 0.0027(6) -0.0013(6) C14 0.0197(7) 0.0174(7) 0.0236(8) 0.0013(6) -0.0022(6) 0.0010(6) C15 0.0247(8) 0.0192(7) 0.0185(7) -0.0011(6) 0.0007(6) -0.0003(6) C16 0.0199(7) 0.0196(7) 0.0214(7) 0.0005(6) 0.0047(6) -0.0007(6) C17 0.0214(8) 0.0269(9) 0.0349(10) -0.0049(7) -0.0019(7) -0.0024(7) C18 0.0569(14) 0.0271(9) 0.0289(10) 0.0003(8) 0.0117(9) -0.0142(9) N1 0.0214(7) 0.0264(7) 0.0185(6) -0.0006(5) 0.0032(5) -0.0022(5) N2 0.0171(6) 0.0273(7) 0.0264(7) -0.0030(6) 0.0015(5) -0.0006(5) O1 0.0352(7) 0.0432(8) 0.0202(6) -0.0018(5) 0.0055(5) 0.0074(6) O2 0.0328(7) 0.0448(8) 0.0216(6) 0.0008(5) -0.0078(5) -0.0095(6) O3 0.0226(12) 0.0593(14) 0.0219(11) 0.000 0.000 -0.0043(9) S1 0.0245(2) 0.0232(2) 0.01438(18) -0.00066(14) 0.00003(14) -0.00454(15) Cl1 0.0234(2) 0.0421(3) 0.0245(2) -0.00514(17) -0.00625(15) -0.00326(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.384(2) . ? C1 C6 1.392(2) . ? C1 S1 1.7727(15) . ? C2 C3 1.392(2) . ? C2 H2 0.9300 . ? C3 C4 1.395(2) . ? C3 H3 0.9300 . ? C4 C5 1.399(2) . ? C4 C7 1.489(2) . ? C5 C6 1.382(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.393(2) . ? C7 C11 1.412(2) . ? C8 C9 1.383(2) . ? C8 H8 0.9300 . ? C9 C10 1.383(2) . ? C9 Cl1 1.7286(16) . ? C10 N1 1.328(2) . ? C10 H10 0.9300 . ? C11 N1 1.350(2) . ? C11 C12 1.487(2) . ? C12 C13 1.393(2) . ? C12 C16 1.398(2) . ? C13 N2 1.340(2) . ? C13 H13 0.9300 . ? C14 N2 1.345(2) . ? C14 C15 1.390(2) . ? C14 C17 1.499(2) . ? C15 C16 1.378(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.95(2) . ? C17 H17B 0.96(3) . ? C17 H17C 0.99(3) . ? C18 S1 1.756(2) . ? C18 H18A 0.92(2) . ? C18 H18B 1.00(3) . ? C18 H18C 0.94(3) . ? O1 S1 1.4363(13) . ? O2 S1 1.4380(12) . ? O3 H3O 0.81(3) . ? 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 C2 C1 C6 121.08(14) . . ? C2 C1 S1 119.55(12) . . ? C6 C1 S1 119.37(12) . . ? C1 C2 C3 119.55(14) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 120.02(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.55(14) . . ? C3 C4 C7 120.51(14) . . ? C5 C4 C7 119.67(14) . . ? C6 C5 C4 120.57(14) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 119.19(15) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C8 C7 C11 117.94(14) . . ? C8 C7 C4 116.56(13) . . ? C11 C7 C4 125.37(14) . . ? C9 C8 C7 119.31(14) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C8 119.29(14) . . ? C10 C9 Cl1 120.13(12) . . ? C8 C9 Cl1 120.58(12) . . ? N1 C10 C9 122.18(14) . . ? N1 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? N1 C11 C7 121.30(14) . . ? N1 C11 C12 114.23(13) . . ? C7 C11 C12 124.41(14) . . ? C13 C12 C16 116.12(14) . . ? C13 C12 C11 119.80(14) . . ? C16 C12 C11 123.94(14) . . ? N2 C13 C12 124.56(15) . . ? N2 C13 H13 117.7 . . ? C12 C13 H13 117.7 . . ? N2 C14 C15 120.94(14) . . ? N2 C14 C17 117.58(14) . . ? C15 C14 C17 121.46(15) . . ? C16 C15 C14 120.11(14) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C12 119.79(14) . . ? C15 C16 H16 120.1 . . ? C12 C16 H16 120.1 . . ? C14 C17 H17A 111.9(14) . . ? C14 C17 H17B 110.0(14) . . ? H17A C17 H17B 109.2(19) . . ? C14 C17 H17C 109.9(16) . . ? H17A C17 H17C 109(2) . . ? H17B C17 H17C 107(2) . . ? S1 C18 H18A 110.8(15) . . ? S1 C18 H18B 107.2(14) . . ? H18A C18 H18B 111(2) . . ? S1 C18 H18C 104.0(15) . . ? H18A C18 H18C 111(2) . . ? H18B C18 H18C 112(2) . . ? C10 N1 C11 119.68(14) . . ? C13 N2 C14 118.39(14) . . ? O1 S1 O2 118.42(8) . . ? O1 S1 C18 108.82(10) . . ? O2 S1 C18 107.86(11) . . ? O1 S1 C1 108.15(8) . . ? O2 S1 C1 108.05(7) . . ? C18 S1 C1 104.70(9) . . ? 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 1.4(2) . . . . ? S1 C1 C2 C3 -179.11(12) . . . . ? C1 C2 C3 C4 -1.1(2) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C2 C3 C4 C7 173.66(14) . . . . ? C3 C4 C5 C6 1.5(2) . . . . ? C7 C4 C5 C6 -172.51(14) . . . . ? C4 C5 C6 C1 -1.2(2) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? S1 C1 C6 C5 -179.71(12) . . . . ? C3 C4 C7 C8 -54.2(2) . . . . ? C5 C4 C7 C8 119.83(16) . . . . ? C3 C4 C7 C11 130.03(17) . . . . ? C5 C4 C7 C11 -56.0(2) . . . . ? C11 C7 C8 C9 4.7(2) . . . . ? C4 C7 C8 C9 -171.42(14) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? C7 C8 C9 Cl1 179.37(12) . . . . ? C8 C9 C10 N1 -3.8(3) . . . . ? Cl1 C9 C10 N1 176.52(13) . . . . ? C8 C7 C11 N1 -5.6(2) . . . . ? C4 C7 C11 N1 170.19(15) . . . . ? C8 C7 C11 C12 171.32(14) . . . . ? C4 C7 C11 C12 -12.9(2) . . . . ? N1 C11 C12 C13 -20.3(2) . . . . ? C7 C11 C12 C13 162.60(15) . . . . ? N1 C11 C12 C16 155.14(15) . . . . ? C7 C11 C12 C16 -21.9(2) . . . . ? C16 C12 C13 N2 -2.7(2) . . . . ? C11 C12 C13 N2 173.09(15) . . . . ? N2 C14 C15 C16 -3.0(2) . . . . ? C17 C14 C15 C16 175.41(15) . . . . ? C14 C15 C16 C12 1.4(2) . . . . ? C13 C12 C16 C15 1.3(2) . . . . ? C11 C12 C16 C15 -174.31(14) . . . . ? C9 C10 N1 C11 3.1(2) . . . . ? C7 C11 N1 C10 1.7(2) . . . . ? C12 C11 N1 C10 -175.49(14) . . . . ? C12 C13 N2 C14 1.2(3) . . . . ? C15 C14 N2 C13 1.7(2) . . . . ? C17 C14 N2 C13 -176.77(15) . . . . ? C2 C1 S1 O1 1.53(15) . . . . ? C6 C1 S1 O1 -178.99(13) . . . . ? C2 C1 S1 O2 -127.78(13) . . . . ? C6 C1 S1 O2 51.69(15) . . . . ? C2 C1 S1 C18 117.45(15) . . . . ? C6 C1 S1 C18 -63.07(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.375 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.053 # Attachment 'web_deposit_cif_file_3_ArijitMukherjee_1334771861.hemihydrate II.cif' data_hemihydrate_II _database_code_depnum_ccdc_archive 'CCDC 855685' #TrackingRef 'web_deposit_cif_file_3_ArijitMukherjee_1334771861.hemihydrate II.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl N2 O2.69 S' _chemical_formula_weight 370.83 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.889(2) _cell_length_b 12.359(3) _cell_length_c 12.803(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.496(7) _cell_angle_gamma 90.00 _cell_volume 1719.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14184 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 766.4 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17788 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3938 _reflns_number_gt 3066 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0495P)^2^+1.0116P] 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 3938 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C1 C 0.7451(2) 0.42266(17) 0.09560(15) 0.0215(4) Uani 1 1 d . . . C2 C 0.8293(2) 0.36464(18) 0.15859(17) 0.0254(5) Uani 1 1 d . . . H2 H 0.8960 0.3312 0.1299 0.030 Uiso 1 1 calc R . . C3 C 0.8131(2) 0.35694(19) 0.26504(17) 0.0258(5) Uani 1 1 d . . . H3 H 0.8692 0.3179 0.3078 0.031 Uiso 1 1 calc R . . C4 C 0.71369(19) 0.40714(17) 0.30840(15) 0.0204(4) Uani 1 1 d . . . C5 C 0.63025(19) 0.46531(17) 0.24337(16) 0.0224(4) Uani 1 1 d . . . H5 H 0.5640 0.4996 0.2718 0.027 Uiso 1 1 calc R . . C6 C 0.6448(2) 0.47268(17) 0.13689(17) 0.0237(5) Uani 1 1 d . . . H6 H 0.5881 0.5106 0.0937 0.028 Uiso 1 1 calc R . . C7 C 0.70156(18) 0.40021(17) 0.42385(15) 0.0205(4) Uani 1 1 d . . . C8 C 0.8016(2) 0.43277(19) 0.48867(17) 0.0240(5) Uani 1 1 d . . . C9 C 0.79146(19) 0.43288(18) 0.59573(17) 0.0236(5) Uani 1 1 d . . . C10 C 0.6828(2) 0.40182(19) 0.63638(17) 0.0258(5) Uani 1 1 d . . . C11 C 0.59455(19) 0.36548(16) 0.47045(16) 0.0201(4) Uani 1 1 d . . . C12 C 0.48290(19) 0.32354(17) 0.41132(16) 0.0212(4) Uani 1 1 d . . . C13 C 0.3696(2) 0.33567(19) 0.45292(18) 0.0265(5) Uani 1 1 d . . . C14 C 0.2662(2) 0.24943(19) 0.3149(2) 0.0332(6) Uani 1 1 d . . . C15 C 0.3745(2) 0.23566(19) 0.2667(2) 0.0328(6) Uani 1 1 d . . . C16 C 0.4840(2) 0.27034(17) 0.31533(18) 0.0263(5) Uani 1 1 d . . . C17 C 0.1465(3) 0.2069(2) 0.2673(2) 0.0491(7) Uani 1 1 d . . . H17A H 0.0832 0.2601 0.2742 0.074 Uiso 1 1 calc R . . H17B H 0.1250 0.1417 0.3026 0.074 Uiso 1 1 calc R . . H17C H 0.1547 0.1917 0.1945 0.074 Uiso 1 1 calc R . . C18 C 0.8188(3) 0.5680(2) -0.0549(2) 0.0451(7) Uani 1 1 d . . . H18A H 0.7583 0.6177 -0.0319 0.068 Uiso 1 1 calc R . . H18B H 0.8321 0.5812 -0.1272 0.068 Uiso 1 1 calc R . . H18C H 0.8947 0.5779 -0.0137 0.068 Uiso 1 1 calc R . . N1 N 0.58691(17) 0.36806(15) 0.57556(14) 0.0248(4) Uani 1 1 d . . . N2 N 0.26334(17) 0.29920(17) 0.40827(17) 0.0327(5) Uani 1 1 d . . . O1 O 0.86381(18) 0.36318(15) -0.06488(13) 0.0429(5) Uani 1 1 d . . . O2 O 0.65034(18) 0.42398(18) -0.09630(13) 0.0494(5) Uani 1 1 d . . . O3 O 0.0443(2) 0.3011(2) 0.5110(2) 0.0468(11) Uani 0.694(7) 1 d P . . S1 S 0.76650(5) 0.43486(4) -0.03987(4) 0.02535(15) Uani 1 1 d . . . Cl1 Cl 0.91357(5) 0.47422(5) 0.67962(4) 0.03461(17) Uani 1 1 d . . . H8 H 0.878(2) 0.458(2) 0.458(2) 0.034(7) Uiso 1 1 d . . . H10 H 0.672(2) 0.401(2) 0.712(2) 0.033(7) Uiso 1 1 d . . . H13 H 0.365(2) 0.3715(19) 0.5165(19) 0.026(6) Uiso 1 1 d . . . H15 H 0.373(2) 0.199(2) 0.202(2) 0.039(7) Uiso 1 1 d . . . H16 H 0.559(2) 0.255(2) 0.285(2) 0.034(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 C1 0.0263(11) 0.0238(11) 0.0144(9) -0.0003(8) 0.0016(8) -0.0026(9) C2 0.0244(11) 0.0303(12) 0.0221(11) -0.0003(9) 0.0071(9) 0.0035(9) C3 0.0214(11) 0.0344(12) 0.0216(11) 0.0049(9) 0.0017(9) 0.0066(9) C4 0.0203(10) 0.0250(11) 0.0159(10) 0.0007(8) 0.0022(8) -0.0014(8) C5 0.0192(10) 0.0265(11) 0.0216(10) -0.0003(8) 0.0018(8) 0.0022(8) C6 0.0240(11) 0.0265(11) 0.0202(10) 0.0031(9) -0.0021(9) 0.0014(9) C7 0.0202(10) 0.0246(10) 0.0168(10) 0.0020(8) 0.0012(8) 0.0034(8) C8 0.0191(11) 0.0323(12) 0.0206(10) 0.0041(9) 0.0017(9) 0.0009(9) C9 0.0200(11) 0.0306(11) 0.0197(10) 0.0017(9) -0.0029(8) 0.0019(9) C10 0.0279(12) 0.0335(12) 0.0157(10) 0.0021(9) 0.0000(9) 0.0008(10) C11 0.0216(11) 0.0212(10) 0.0178(10) 0.0018(8) 0.0024(8) 0.0021(8) C12 0.0220(11) 0.0199(10) 0.0216(10) 0.0041(8) -0.0012(9) -0.0006(8) C13 0.0246(12) 0.0299(12) 0.0251(11) 0.0024(9) 0.0007(9) -0.0012(9) C14 0.0343(14) 0.0265(12) 0.0368(13) 0.0094(10) -0.0150(11) -0.0085(10) C15 0.0452(15) 0.0251(12) 0.0270(12) -0.0018(10) -0.0057(11) -0.0077(11) C16 0.0327(13) 0.0203(11) 0.0261(11) -0.0002(9) 0.0026(10) -0.0011(9) C17 0.0396(16) 0.0493(17) 0.0557(18) 0.0074(14) -0.0195(14) -0.0155(13) C18 0.081(2) 0.0278(13) 0.0287(13) 0.0011(10) 0.0163(14) -0.0080(14) N1 0.0235(10) 0.0316(10) 0.0195(9) 0.0019(7) 0.0028(7) -0.0027(8) N2 0.0218(10) 0.0345(11) 0.0412(12) 0.0101(9) -0.0030(9) -0.0038(8) O1 0.0638(13) 0.0418(11) 0.0249(9) 0.0019(8) 0.0173(9) 0.0152(9) O2 0.0445(11) 0.0822(15) 0.0208(9) -0.0018(9) -0.0043(8) -0.0114(10) O3 0.0392(17) 0.058(2) 0.0434(18) -0.0055(13) 0.0069(13) 0.0088(13) S1 0.0364(3) 0.0262(3) 0.0137(2) -0.0011(2) 0.0033(2) -0.0025(2) Cl1 0.0250(3) 0.0552(4) 0.0226(3) 0.0013(3) -0.0066(2) -0.0032(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.384(3) . ? C1 C6 1.388(3) . ? C1 S1 1.770(2) . ? C2 C3 1.388(3) . ? C2 H2 0.9300 . ? C3 C4 1.392(3) . ? C3 H3 0.9300 . ? C4 C5 1.394(3) . ? C4 C7 1.494(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.388(3) . ? C7 C11 1.408(3) . ? C8 C9 1.382(3) . ? C8 H8 0.98(3) . ? C9 C10 1.376(3) . ? C9 Cl1 1.735(2) . ? C10 N1 1.331(3) . ? C10 H10 0.99(2) . ? C11 N1 1.354(3) . ? C11 C12 1.486(3) . ? C12 C13 1.381(3) . ? C12 C16 1.395(3) . ? C13 N2 1.337(3) . ? C13 H13 0.93(2) . ? C14 N2 1.346(3) . ? C14 C15 1.375(4) . ? C14 C17 1.500(3) . ? C15 C16 1.380(3) . ? C15 H15 0.94(3) . ? C16 H16 0.95(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 S1 1.756(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O1 S1 1.4322(18) . ? O2 S1 1.4242(19) . ? 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 C2 C1 C6 121.19(19) . . ? C2 C1 S1 119.55(16) . . ? C6 C1 S1 119.26(16) . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.08(19) . . ? C3 C4 C7 119.11(19) . . ? C5 C4 C7 121.78(18) . . ? C6 C5 C4 120.82(19) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C8 C7 C11 118.32(18) . . ? C8 C7 C4 117.48(18) . . ? C11 C7 C4 124.18(19) . . ? C9 C8 C7 119.1(2) . . ? C9 C8 H8 120.8(15) . . ? C7 C8 H8 120.1(15) . . ? C10 C9 C8 119.8(2) . . ? C10 C9 Cl1 119.49(17) . . ? C8 C9 Cl1 120.68(17) . . ? N1 C10 C9 121.9(2) . . ? N1 C10 H10 115.8(15) . . ? C9 C10 H10 122.3(15) . . ? N1 C11 C7 121.10(19) . . ? N1 C11 C12 114.63(18) . . ? C7 C11 C12 124.27(18) . . ? C13 C12 C16 116.6(2) . . ? C13 C12 C11 119.21(19) . . ? C16 C12 C11 124.2(2) . . ? N2 C13 C12 124.6(2) . . ? N2 C13 H13 116.3(15) . . ? C12 C13 H13 119.1(15) . . ? N2 C14 C15 121.5(2) . . ? N2 C14 C17 117.0(2) . . ? C15 C14 C17 121.4(2) . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15 119.3(17) . . ? C16 C15 H15 120.6(17) . . ? C15 C16 C12 119.4(2) . . ? C15 C16 H16 119.8(16) . . ? C12 C16 H16 120.8(16) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 N1 C11 119.70(18) . . ? C13 N2 C14 117.8(2) . . ? O2 S1 O1 118.32(12) . . ? O2 S1 C18 108.49(14) . . ? O1 S1 C18 107.81(13) . . ? O2 S1 C1 108.86(11) . . ? O1 S1 C1 108.03(10) . . ? C18 S1 C1 104.46(11) . . ? 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 -0.3(3) . . . . ? S1 C1 C2 C3 178.92(17) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C2 C3 C4 C7 -178.0(2) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 178.5(2) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? S1 C1 C6 C5 -178.31(16) . . . . ? C3 C4 C7 C8 53.8(3) . . . . ? C5 C4 C7 C8 -124.2(2) . . . . ? C3 C4 C7 C11 -127.9(2) . . . . ? C5 C4 C7 C11 54.2(3) . . . . ? C11 C7 C8 C9 -1.8(3) . . . . ? C4 C7 C8 C9 176.6(2) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C7 C8 C9 Cl1 -179.35(17) . . . . ? C8 C9 C10 N1 2.1(4) . . . . ? Cl1 C9 C10 N1 -179.09(17) . . . . ? C8 C7 C11 N1 2.8(3) . . . . ? C4 C7 C11 N1 -175.5(2) . . . . ? C8 C7 C11 C12 -177.0(2) . . . . ? C4 C7 C11 C12 4.7(3) . . . . ? N1 C11 C12 C13 28.1(3) . . . . ? C7 C11 C12 C13 -152.0(2) . . . . ? N1 C11 C12 C16 -151.0(2) . . . . ? C7 C11 C12 C16 28.9(3) . . . . ? C16 C12 C13 N2 0.8(3) . . . . ? C11 C12 C13 N2 -178.4(2) . . . . ? N2 C14 C15 C16 1.9(4) . . . . ? C17 C14 C15 C16 -176.4(2) . . . . ? C14 C15 C16 C12 -2.8(3) . . . . ? C13 C12 C16 C15 1.5(3) . . . . ? C11 C12 C16 C15 -179.4(2) . . . . ? C9 C10 N1 C11 -1.1(3) . . . . ? C7 C11 N1 C10 -1.4(3) . . . . ? C12 C11 N1 C10 178.44(19) . . . . ? C12 C13 N2 C14 -1.7(3) . . . . ? C15 C14 N2 C13 0.3(3) . . . . ? C17 C14 N2 C13 178.7(2) . . . . ? C2 C1 S1 O2 139.24(19) . . . . ? C6 C1 S1 O2 -41.5(2) . . . . ? C2 C1 S1 O1 9.6(2) . . . . ? C6 C1 S1 O1 -171.19(18) . . . . ? C2 C1 S1 C18 -105.0(2) . . . . ? C6 C1 S1 C18 74.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.474 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.064