data_cs427 _publ_requested_journal test _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N O3 S' _chemical_formula_sum 'C14 H18 N O3 S' _chemical_formula_weight 280.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 9.4064(8) _cell_length_b 11.4106(8) _cell_length_c 12.0893(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.524(7) _cell_angle_gamma 90.00 _cell_volume 1286.40(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5583 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 26.8 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Oxford Diffraction Sapphire2 CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 14377 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 30.07 _reflns_number_total 3769 _reflns_number_gt 3450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis (Oxford Diffraction)' _computing_cell_refinement 'Crysalis (Oxford Diffraction)' _computing_data_reduction 'Crysalis (Oxford Diffraction)' _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^)+(0.0563P)^2^+0.9902P] 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 3769 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.54983(3) 0.23237(3) 0.19061(2) 0.01160(9) Uani 1 1 d . . . O1 O 0.39770(10) 0.21543(9) 0.17781(8) 0.0170(2) Uani 1 1 d . . . O2 O 0.61957(11) 0.25312(9) 0.30307(8) 0.01671(19) Uani 1 1 d . . . O3 O 0.86444(10) 0.26830(8) -0.04361(8) 0.01453(19) Uani 1 1 d . . . H3A H 0.8009 0.2595 -0.0987 0.022 Uiso 1 1 calc R . . N1 N 0.58164(11) 0.34792(9) 0.11716(9) 0.0127(2) Uani 1 1 d . . . H1 H 0.5227 0.4079 0.1160 0.015 Uiso 1 1 calc R . . C1 C 0.63094(13) 0.11428(11) 0.13142(10) 0.0124(2) Uani 1 1 d . . . C2 C 0.74278(13) 0.13654(11) 0.06931(10) 0.0117(2) Uani 1 1 d . . . C3 C 0.80525(13) 0.04096(11) 0.02224(11) 0.0148(2) Uani 1 1 d . . . H3 H 0.8809 0.0535 -0.0213 0.018 Uiso 1 1 calc R . . C4 C 0.75799(14) -0.07248(11) 0.03837(11) 0.0173(2) Uani 1 1 d . . . H4 H 0.8026 -0.1367 0.0067 0.021 Uiso 1 1 calc R . . C5 C 0.64591(15) -0.09274(11) 0.10054(12) 0.0181(3) Uani 1 1 d . . . H5 H 0.6145 -0.1705 0.1115 0.022 Uiso 1 1 calc R . . C6 C 0.58029(14) 0.00101(11) 0.14644(11) 0.0159(2) Uani 1 1 d . . . H6 H 0.5021 -0.0116 0.1875 0.019 Uiso 1 1 calc R . . C7 C 0.80132(13) 0.25952(10) 0.05639(10) 0.0110(2) Uani 1 1 d . . . C8 C 0.68839(13) 0.35517(10) 0.06118(10) 0.0115(2) Uani 1 1 d . . . C9 C 0.70479(13) 0.46873(11) 0.00005(10) 0.0139(2) Uani 1 1 d . . . H9A H 0.6256 0.4754 -0.0622 0.017 Uiso 1 1 calc R . . H9B H 0.7960 0.4666 -0.0326 0.017 Uiso 1 1 calc R . . C10 C 0.70424(14) 0.57773(11) 0.07432(11) 0.0168(2) Uani 1 1 d . . . H10A H 0.6832 0.6471 0.0258 0.020 Uiso 1 1 calc R . . H10B H 0.6253 0.5699 0.1206 0.020 Uiso 1 1 calc R . . C11 C 0.84338(14) 0.60005(12) 0.15135(12) 0.0180(2) Uani 1 1 d . . . H11A H 0.8277 0.6660 0.2015 0.022 Uiso 1 1 calc R . . H11B H 0.9177 0.6248 0.1053 0.022 Uiso 1 1 calc R . . C12 C 0.90115(15) 0.49510(12) 0.22316(11) 0.0183(3) Uani 1 1 d . . . H12A H 0.8191 0.4545 0.2498 0.022 Uiso 1 1 calc R . . H12B H 0.9632 0.5251 0.2896 0.022 Uiso 1 1 calc R . . C13 C 0.98812(14) 0.40377(12) 0.16377(12) 0.0174(2) Uani 1 1 d . . . H13A H 0.9973 0.4332 0.0880 0.021 Uiso 1 1 calc R . . H13B H 1.0860 0.3989 0.2052 0.021 Uiso 1 1 calc R . . C14 C 0.92519(13) 0.27978(11) 0.15302(11) 0.0135(2) Uani 1 1 d . . . H14A H 0.8896 0.2596 0.2241 0.016 Uiso 1 1 calc R . . H14B H 1.0037 0.2245 0.1432 0.016 Uiso 1 1 calc R . . 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 0.01203(15) 0.01149(15) 0.01160(15) 0.00003(9) 0.00276(10) -0.00043(9) O1 0.0121(4) 0.0188(4) 0.0208(5) -0.0008(4) 0.0049(3) -0.0022(3) O2 0.0198(5) 0.0193(4) 0.0108(4) -0.0012(3) 0.0012(3) 0.0013(3) O3 0.0147(4) 0.0180(4) 0.0117(4) 0.0007(3) 0.0045(3) -0.0014(3) N1 0.0128(4) 0.0106(4) 0.0147(5) 0.0007(4) 0.0016(4) 0.0003(3) C1 0.0141(5) 0.0113(5) 0.0121(5) 0.0000(4) 0.0022(4) -0.0003(4) C2 0.0128(5) 0.0115(5) 0.0106(5) 0.0008(4) 0.0006(4) -0.0002(4) C3 0.0146(5) 0.0142(5) 0.0156(5) -0.0010(4) 0.0024(4) 0.0012(4) C4 0.0200(6) 0.0126(5) 0.0192(6) -0.0025(4) 0.0026(5) 0.0016(4) C5 0.0230(6) 0.0110(5) 0.0205(6) 0.0004(4) 0.0033(5) -0.0012(4) C6 0.0178(6) 0.0134(5) 0.0171(6) 0.0017(4) 0.0045(4) -0.0022(4) C7 0.0107(5) 0.0121(5) 0.0105(5) 0.0007(4) 0.0019(4) -0.0004(4) C8 0.0117(5) 0.0116(5) 0.0103(5) -0.0003(4) -0.0019(4) -0.0014(4) C9 0.0147(5) 0.0118(5) 0.0146(5) 0.0022(4) 0.0002(4) -0.0012(4) C10 0.0178(6) 0.0121(5) 0.0200(6) -0.0006(4) 0.0005(5) -0.0016(4) C11 0.0188(6) 0.0141(5) 0.0204(6) -0.0009(5) -0.0003(5) -0.0032(4) C12 0.0204(6) 0.0175(6) 0.0161(6) -0.0019(5) -0.0011(5) -0.0033(5) C13 0.0136(5) 0.0167(6) 0.0205(6) 0.0013(5) -0.0025(4) -0.0034(4) C14 0.0122(5) 0.0141(5) 0.0134(5) 0.0008(4) -0.0013(4) -0.0002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4322(10) . ? S1 O2 1.4495(10) . ? S1 N1 1.6389(11) . ? S1 C1 1.7473(13) . ? O3 C7 1.4185(15) . ? N1 C8 1.2850(16) . ? C1 C2 1.3935(16) . ? C1 C6 1.3976(17) . ? C2 C3 1.3950(17) . ? C2 C7 1.5229(17) . ? C3 C4 1.3906(18) . ? C4 C5 1.3918(19) . ? C5 C6 1.3867(18) . ? C7 C8 1.5294(17) . ? C7 C14 1.5554(17) . ? C8 C9 1.5096(16) . ? C9 C10 1.5343(18) . ? C10 C11 1.5251(18) . ? C11 C12 1.5360(19) . ? C12 C13 1.557(2) . ? C13 C14 1.5326(18) . ? 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 O1 S1 O2 116.52(6) . . ? O1 S1 N1 107.50(6) . . ? O2 S1 N1 106.53(6) . . ? O1 S1 C1 109.59(6) . . ? O2 S1 C1 109.99(6) . . ? N1 S1 C1 106.14(6) . . ? C8 N1 S1 123.22(9) . . ? C2 C1 C6 122.20(11) . . ? C2 C1 S1 118.75(9) . . ? C6 C1 S1 119.04(9) . . ? C1 C2 C3 117.73(11) . . ? C1 C2 C7 122.13(11) . . ? C3 C2 C7 120.08(11) . . ? C4 C3 C2 120.73(12) . . ? C3 C4 C5 120.59(12) . . ? C6 C5 C4 119.76(12) . . ? C5 C6 C1 118.96(12) . . ? O3 C7 C2 110.47(10) . . ? O3 C7 C8 110.62(10) . . ? C2 C7 C8 113.04(10) . . ? O3 C7 C14 105.88(10) . . ? C2 C7 C14 107.78(10) . . ? C8 C7 C14 108.74(10) . . ? N1 C8 C9 116.75(11) . . ? N1 C8 C7 124.65(11) . . ? C9 C8 C7 118.56(10) . . ? C8 C9 C10 113.64(10) . . ? C11 C10 C9 115.11(11) . . ? C10 C11 C12 115.26(11) . . ? C11 C12 C13 115.44(11) . . ? C14 C13 C12 115.88(11) . . ? C13 C14 C7 116.35(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C8 -141.65(10) . . . . ? O2 S1 N1 C8 92.77(11) . . . . ? C1 S1 N1 C8 -24.43(12) . . . . ? O1 S1 C1 C2 138.56(10) . . . . ? O2 S1 C1 C2 -92.11(11) . . . . ? N1 S1 C1 C2 22.76(11) . . . . ? O1 S1 C1 C6 -40.49(12) . . . . ? O2 S1 C1 C6 88.84(11) . . . . ? N1 S1 C1 C6 -156.30(10) . . . . ? C6 C1 C2 C3 -0.56(18) . . . . ? S1 C1 C2 C3 -179.58(9) . . . . ? C6 C1 C2 C7 -177.82(11) . . . . ? S1 C1 C2 C7 3.16(16) . . . . ? C1 C2 C3 C4 -0.78(18) . . . . ? C7 C2 C3 C4 176.53(12) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C1 -1.6(2) . . . . ? C2 C1 C6 C5 1.7(2) . . . . ? S1 C1 C6 C5 -179.23(10) . . . . ? C1 C2 C7 O3 -154.46(11) . . . . ? C3 C2 C7 O3 28.34(15) . . . . ? C1 C2 C7 C8 -29.90(16) . . . . ? C3 C2 C7 C8 152.91(11) . . . . ? C1 C2 C7 C14 90.30(13) . . . . ? C3 C2 C7 C14 -86.90(13) . . . . ? S1 N1 C8 C9 -178.58(8) . . . . ? S1 N1 C8 C7 -1.09(17) . . . . ? O3 C7 C8 N1 154.75(11) . . . . ? C2 C7 C8 N1 30.26(16) . . . . ? C14 C7 C8 N1 -89.38(14) . . . . ? O3 C7 C8 C9 -27.80(14) . . . . ? C2 C7 C8 C9 -152.28(10) . . . . ? C14 C7 C8 C9 88.07(12) . . . . ? N1 C8 C9 C10 52.39(14) . . . . ? C7 C8 C9 C10 -125.26(11) . . . . ? C8 C9 C10 C11 76.67(14) . . . . ? C9 C10 C11 C12 -51.45(16) . . . . ? C10 C11 C12 C13 81.83(15) . . . . ? C11 C12 C13 C14 -117.90(13) . . . . ? C12 C13 C14 C7 80.35(14) . . . . ? O3 C7 C14 C13 68.60(13) . . . . ? C2 C7 C14 C13 -173.17(11) . . . . ? C8 C7 C14 C13 -50.29(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.84 1.95 2.7718(14) 164.8 4_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.503 _refine_diff_density_min -0.991 _refine_diff_density_rms 0.069