data_global _name_of_contact_person 'Cara L. Nygren' _e-mail_of_contact_person 'chem9995@buffalo.edu' _authors'_names ; Cara L. Nygren Philip Coppens ; _authors'_address ; Department of Chemistry State University of New York at Buffalo Buffalo, NY 14260-3000, USA ; _crystallization_solvent 'benzene' _journal_name 'private communication' data_MRMV _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N O2 S' _chemical_formula_sum 'C13 H17 N O2 S' _chemical_formula_weight 251.34 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.3043(4) _cell_length_b 10.2934(3) _cell_length_c 10.2398(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.0530(10) _cell_angle_gamma 90.00 _cell_volume 1191.30(6) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 6287 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.23 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details '(SADABS v2.10; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 13984 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2947 _reflns_number_gt 2507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2 (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.6766P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2947 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.19139(11) 0.80446(13) 0.91747(13) 0.0146(3) Uani 1 1 d . . . H1 H 0.1971 0.7587 0.8316 0.018 Uiso 1 1 calc R . . C2 C 0.08355(12) 0.75755(14) 0.98875(13) 0.0170(3) Uani 1 1 d . . . H2A H 0.0830 0.7950 1.0778 0.020 Uiso 1 1 calc R . . H2B H 0.0857 0.6617 0.9967 0.020 Uiso 1 1 calc R . . C3 C -0.02754(12) 0.79878(13) 0.91359(12) 0.0150(3) Uani 1 1 d . . . C4 C -0.13279(12) 0.73192(14) 0.93560(13) 0.0181(3) Uani 1 1 d . . . H4 H -0.1334 0.6642 0.9986 0.022 Uiso 1 1 calc R . . C5 C -0.23641(13) 0.76213(15) 0.86757(14) 0.0212(3) Uani 1 1 d . . . H5 H -0.3074 0.7161 0.8844 0.025 Uiso 1 1 calc R . . C6 C -0.23537(13) 0.86048(15) 0.77439(14) 0.0219(3) Uani 1 1 d . . . H6 H -0.3052 0.8805 0.7253 0.026 Uiso 1 1 calc R . . C7 C -0.13190(13) 0.92917(14) 0.75354(13) 0.0197(3) Uani 1 1 d . . . H7 H -0.1323 0.9976 0.6913 0.024 Uiso 1 1 calc R . . C8 C -0.02685(12) 0.90013(13) 0.82189(12) 0.0158(3) Uani 1 1 d . . . C9 C 0.08442(12) 0.97746(14) 0.79389(13) 0.0175(3) Uani 1 1 d . . . H9A H 0.1132 0.9541 0.7062 0.021 Uiso 1 1 calc R . . H9B H 0.0654 1.0713 0.7935 0.021 Uiso 1 1 calc R . . C10 C 0.18119(12) 0.95102(13) 0.89527(13) 0.0172(3) Uani 1 1 d . . . H10 H 0.1577 0.9923 0.9793 0.021 Uiso 1 1 calc R . . C11 C 0.30764(12) 0.99108(14) 0.86736(14) 0.0194(3) Uani 1 1 d . . . H11A H 0.3191 1.0857 0.8798 0.023 Uiso 1 1 calc R . . H11B H 0.3299 0.9672 0.7774 0.023 Uiso 1 1 calc R . . C12 C 0.37815(12) 0.91328(14) 0.96856(14) 0.0195(3) Uani 1 1 d . . . H12A H 0.4571 0.8904 0.9353 0.023 Uiso 1 1 calc R . . H12B H 0.3885 0.9634 1.0505 0.023 Uiso 1 1 calc R . . C13 C 0.42845(12) 0.63400(14) 0.82799(13) 0.0190(3) Uani 1 1 d . . . H13A H 0.4748 0.5537 0.8239 0.028 Uiso 1 1 calc R . . H13B H 0.4786 0.7079 0.8050 0.028 Uiso 1 1 calc R . . H13C H 0.3613 0.6287 0.7663 0.028 Uiso 1 1 calc R . . N1 N 0.30587(10) 0.79344(11) 0.99100(11) 0.0157(2) Uani 1 1 d . . . O1 O 0.47649(9) 0.66694(10) 1.07493(10) 0.0204(2) Uani 1 1 d . . . O2 O 0.29001(9) 0.55521(9) 1.01148(9) 0.0177(2) Uani 1 1 d . . . S1 S 0.37560(3) 0.65515(3) 0.98805(3) 0.01430(10) 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 0.0138(6) 0.0145(6) 0.0154(6) 0.0006(5) -0.0005(5) 0.0012(5) C2 0.0153(6) 0.0187(7) 0.0170(6) 0.0037(5) 0.0008(5) 0.0011(5) C3 0.0156(6) 0.0165(6) 0.0129(6) -0.0019(5) 0.0007(5) 0.0029(5) C4 0.0193(7) 0.0170(6) 0.0181(6) -0.0011(5) 0.0025(5) 0.0003(5) C5 0.0167(7) 0.0236(7) 0.0234(7) -0.0054(6) 0.0003(5) -0.0008(6) C6 0.0183(7) 0.0267(8) 0.0205(6) -0.0044(6) -0.0045(5) 0.0057(6) C7 0.0237(7) 0.0205(7) 0.0148(6) -0.0003(5) -0.0012(5) 0.0055(6) C8 0.0182(6) 0.0161(6) 0.0130(6) -0.0020(5) 0.0014(5) 0.0015(5) C9 0.0206(7) 0.0165(6) 0.0154(6) 0.0033(5) 0.0012(5) 0.0009(5) C10 0.0204(7) 0.0147(6) 0.0165(6) 0.0004(5) 0.0020(5) -0.0001(5) C11 0.0221(7) 0.0162(7) 0.0198(6) 0.0004(5) 0.0004(5) -0.0028(6) C12 0.0175(7) 0.0155(7) 0.0253(7) 0.0000(5) -0.0001(5) -0.0043(5) C13 0.0187(7) 0.0227(7) 0.0156(6) 0.0004(5) 0.0033(5) 0.0028(5) N1 0.0131(5) 0.0137(5) 0.0203(6) -0.0001(4) -0.0014(4) -0.0008(4) O1 0.0177(5) 0.0234(5) 0.0199(5) -0.0009(4) -0.0046(4) 0.0026(4) O2 0.0190(5) 0.0145(5) 0.0196(5) 0.0022(4) 0.0011(4) -0.0006(4) S1 0.01408(17) 0.01524(17) 0.01355(15) 0.00046(11) -0.00034(11) 0.00109(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4895(16) . ? C1 C2 1.5115(18) . ? C1 C10 1.5296(19) . ? C1 H1 1.0000 . ? C2 C3 1.5211(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.3963(19) . ? C3 C8 1.4037(19) . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 C6 1.391(2) . ? C5 H5 0.9500 . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 C8 1.3996(18) . ? C7 H7 0.9500 . ? C8 C9 1.5203(19) . ? C9 C10 1.5188(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5199(19) . ? C10 H10 1.0000 . ? C11 C12 1.523(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N1 1.4997(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 S1 1.7682(13) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 S1 1.6277(12) . ? O1 S1 1.4386(10) . ? O2 S1 1.4354(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 115.63(11) . . ? N1 C1 C10 102.27(10) . . ? C2 C1 C10 109.12(11) . . ? N1 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? C10 C1 H1 109.8 . . ? C1 C2 C3 109.40(11) . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C8 119.31(12) . . ? C4 C3 C2 118.61(12) . . ? C8 C3 C2 122.08(12) . . ? C5 C4 C3 121.51(13) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 119.33(14) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 119.63(13) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 121.63(13) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 118.57(13) . . ? C7 C8 C9 119.42(12) . . ? C3 C8 C9 122.01(12) . . ? C10 C9 C8 111.43(11) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 119.40(11) . . ? C9 C10 C1 109.25(11) . . ? C11 C10 C1 103.12(11) . . ? C9 C10 H10 108.2 . . ? C11 C10 H10 108.2 . . ? C1 C10 H10 108.2 . . ? C10 C11 C12 102.22(11) . . ? C10 C11 H11A 111.3 . . ? C12 C11 H11A 111.3 . . ? C10 C11 H11B 111.3 . . ? C12 C11 H11B 111.3 . . ? H11A C11 H11B 109.2 . . ? N1 C12 C11 104.88(11) . . ? N1 C12 H12A 110.8 . . ? C11 C12 H12A 110.8 . . ? N1 C12 H12B 110.8 . . ? C11 C12 H12B 110.8 . . ? H12A C12 H12B 108.8 . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 N1 C12 109.31(10) . . ? C1 N1 S1 118.28(9) . . ? C12 N1 S1 116.81(9) . . ? O2 S1 O1 119.09(6) . . ? O2 S1 N1 107.19(6) . . ? O1 S1 N1 107.06(6) . . ? O2 S1 C13 107.88(6) . . ? O1 S1 C13 107.82(7) . . ? N1 S1 C13 107.27(6) . . ? 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 N1 C1 C2 C3 169.01(11) . . . . ? C10 C1 C2 C3 54.43(14) . . . . ? C1 C2 C3 C4 159.08(12) . . . . ? C1 C2 C3 C8 -19.93(17) . . . . ? C8 C3 C4 C5 0.9(2) . . . . ? C2 C3 C4 C5 -178.11(12) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C7 -1.8(2) . . . . ? C5 C6 C7 C8 1.6(2) . . . . ? C6 C7 C8 C3 0.0(2) . . . . ? C6 C7 C8 C9 179.22(13) . . . . ? C4 C3 C8 C7 -1.18(19) . . . . ? C2 C3 C8 C7 177.82(12) . . . . ? C4 C3 C8 C9 179.57(12) . . . . ? C2 C3 C8 C9 -1.4(2) . . . . ? C7 C8 C9 C10 168.47(12) . . . . ? C3 C8 C9 C10 -12.28(18) . . . . ? C8 C9 C10 C11 164.75(12) . . . . ? C8 C9 C10 C1 46.54(15) . . . . ? N1 C1 C10 C9 166.55(10) . . . . ? C2 C1 C10 C9 -70.49(14) . . . . ? N1 C1 C10 C11 38.58(12) . . . . ? C2 C1 C10 C11 161.53(11) . . . . ? C9 C10 C11 C12 -163.56(12) . . . . ? C1 C10 C11 C12 -42.24(13) . . . . ? C10 C11 C12 N1 29.35(13) . . . . ? C2 C1 N1 C12 -138.81(12) . . . . ? C10 C1 N1 C12 -20.37(13) . . . . ? C2 C1 N1 S1 84.20(13) . . . . ? C10 C1 N1 S1 -157.36(9) . . . . ? C11 C12 N1 C1 -5.54(14) . . . . ? C11 C12 N1 S1 132.15(10) . . . . ? C1 N1 S1 O2 -46.14(11) . . . . ? C12 N1 S1 O2 -179.98(9) . . . . ? C1 N1 S1 O1 -174.99(9) . . . . ? C12 N1 S1 O1 51.17(11) . . . . ? C1 N1 S1 C13 69.50(11) . . . . ? C12 N1 S1 C13 -64.34(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.466 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.052