data_cd22225 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 N O2 S3' _chemical_formula_weight 327.47 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7960(11) _cell_length_b 9.6353(12) _cell_length_c 9.7145(13) _cell_angle_alpha 101.895(2) _cell_angle_beta 93.023(2) _cell_angle_gamma 107.367(2) _cell_volume 763.14(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 882 _cell_measurement_theta_min 4.554 _cell_measurement_theta_max 41.686 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.485 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.52381 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _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_% ? _diffrn_reflns_number 4729 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.1066 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3415 _reflns_number_gt 1713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0421P)^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 3415 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 0.811 _refine_ls_restrained_S_all 0.811 _refine_ls_shift/su_max 0.073 _refine_ls_shift/su_mean 0.017 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 0.17851(12) 0.39397(9) 1.06904(9) 0.0642(3) Uani 1 1 d . . . S2 S 0.10643(12) 0.35590(10) 0.76545(10) 0.0697(3) Uani 1 1 d . . . S3 S 0.37213(10) 0.69572(10) 0.81846(9) 0.0488(3) Uani 1 1 d . . . O1 O 0.3882(3) 0.5918(3) 0.6986(2) 0.0640(7) Uani 1 1 d . . . O2 O 0.5074(2) 0.8205(2) 0.8839(2) 0.0615(6) Uani 1 1 d . . . N N 0.3185(3) 0.6017(3) 0.9469(2) 0.0425(6) Uani 1 1 d . . . C1 C 0.2058(4) 0.4587(3) 0.9158(3) 0.0461(8) Uani 1 1 d . . . C2 C 0.3421(4) 0.6747(3) 1.1009(3) 0.0478(8) Uani 1 1 d . . . C3 C 0.4844(5) 0.8118(4) 1.1655(4) 0.0627(11) Uani 1 1 d . . . C4 C 0.4834(7) 0.8544(5) 1.3238(4) 0.0726(13) Uani 1 1 d . . . C5 C 0.4692(6) 0.7286(5) 1.3974(4) 0.0780(13) Uani 1 1 d . . . C6 C 0.3294(5) 0.5919(5) 1.3301(4) 0.0631(11) Uani 1 1 d . . . C7 C 0.3357(5) 0.5518(4) 1.1738(4) 0.0567(9) Uani 1 1 d . . . C8 C 0.2140(3) 0.7607(3) 0.7791(3) 0.0404(7) Uani 1 1 d . . . C9 C 0.2015(4) 0.8889(3) 0.8672(3) 0.0457(8) Uani 1 1 d . . . C10 C 0.0819(4) 0.9438(4) 0.8303(4) 0.0524(9) Uani 1 1 d . . . C11 C -0.0263(4) 0.8762(4) 0.7108(4) 0.0530(9) Uani 1 1 d . . . C12 C -0.0126(4) 0.7474(4) 0.6247(4) 0.0590(10) Uani 1 1 d . . . C13 C 0.1078(4) 0.6900(4) 0.6585(3) 0.0538(9) Uani 1 1 d . . . C14 C -0.1575(6) 0.9380(7) 0.6738(8) 0.0902(16) Uani 1 1 d . . . H1 H 0.234(4) 0.693(3) 1.121(3) 0.073(11) Uiso 1 1 d . . . H2 H 0.471(4) 0.892(4) 1.122(3) 0.071(11) Uiso 1 1 d . . . H3 H 0.574(4) 0.779(4) 1.139(3) 0.070(12) Uiso 1 1 d . . . H4 H 0.420(6) 0.917(6) 1.343(5) 0.17(3) Uiso 1 1 d . . . H5 H 0.567(4) 0.926(4) 1.362(3) 0.053(10) Uiso 1 1 d . . . H6 H 0.454(4) 0.756(3) 1.492(3) 0.059(10) Uiso 1 1 d . . . H7 H 0.586(8) 0.722(7) 1.395(6) 0.21(3) Uiso 1 1 d . . . H8 H 0.241(4) 0.616(3) 1.351(3) 0.059(11) Uiso 1 1 d . . . H9 H 0.331(4) 0.517(4) 1.367(4) 0.084(14) Uiso 1 1 d . . . H10 H 0.436(4) 0.531(4) 1.159(4) 0.094(14) Uiso 1 1 d . . . H11 H 0.276(3) 0.940(3) 0.952(3) 0.047(8) Uiso 1 1 d . . . H12 H 0.079(3) 1.027(3) 0.890(3) 0.047(9) Uiso 1 1 d . . . H13 H -0.091(4) 0.691(3) 0.539(3) 0.057(9) Uiso 1 1 d . . . H14 H 0.107(4) 0.594(4) 0.595(4) 0.086(12) Uiso 1 1 d . . . H15 H -0.258(6) 0.886(5) 0.713(4) 0.114(17) Uiso 1 1 d . . . H16 H -0.127(6) 1.037(6) 0.696(5) 0.14(2) Uiso 1 1 d . . . H17 H -0.189(7) 0.907(6) 0.578(6) 0.16(3) 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 0.0818(7) 0.0478(5) 0.0526(6) 0.0187(4) 0.0075(5) 0.0006(5) S2 0.0862(8) 0.0585(6) 0.0525(6) 0.0032(5) -0.0049(5) 0.0145(5) S3 0.0507(5) 0.0586(6) 0.0471(5) 0.0253(4) 0.0147(4) 0.0217(4) O1 0.0846(18) 0.0772(16) 0.0520(14) 0.0254(13) 0.0299(13) 0.0470(14) O2 0.0403(13) 0.0708(16) 0.0747(17) 0.0405(13) 0.0065(12) 0.0037(12) N 0.0451(16) 0.0456(15) 0.0376(15) 0.0146(12) 0.0043(11) 0.0125(12) C1 0.048(2) 0.0434(19) 0.051(2) 0.0159(15) 0.0088(15) 0.0164(16) C2 0.051(2) 0.047(2) 0.043(2) 0.0133(15) 0.0049(16) 0.0111(17) C3 0.072(3) 0.052(2) 0.057(2) 0.0204(19) -0.002(2) 0.006(2) C4 0.094(3) 0.054(3) 0.052(3) -0.001(2) -0.011(2) 0.009(3) C5 0.094(4) 0.081(3) 0.040(2) 0.013(2) -0.004(2) 0.003(3) C6 0.076(3) 0.069(3) 0.046(2) 0.021(2) 0.015(2) 0.019(2) C7 0.067(3) 0.055(2) 0.046(2) 0.0193(17) 0.0035(18) 0.0101(19) C8 0.0448(19) 0.0434(18) 0.0348(17) 0.0160(14) 0.0075(14) 0.0116(14) C9 0.049(2) 0.0422(19) 0.0398(19) 0.0087(15) 0.0015(16) 0.0062(16) C10 0.055(2) 0.039(2) 0.063(2) 0.0093(18) 0.0095(19) 0.0145(17) C11 0.046(2) 0.049(2) 0.064(2) 0.0208(18) 0.0009(17) 0.0110(17) C12 0.065(2) 0.056(2) 0.046(2) 0.0094(18) -0.0121(19) 0.0095(19) C13 0.071(3) 0.050(2) 0.040(2) 0.0099(17) 0.0036(18) 0.0212(19) C14 0.060(3) 0.083(4) 0.135(5) 0.037(4) -0.010(3) 0.030(3) _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 1.730(3) . ? S1 C7 1.794(4) . ? S2 C1 1.622(3) . ? S3 O1 1.414(2) . ? S3 O2 1.420(2) . ? S3 N 1.695(2) . ? S3 C8 1.743(3) . ? N C1 1.397(4) . ? N C2 1.490(4) . ? C2 C7 1.489(4) . ? C2 C3 1.514(5) . ? C2 H1 1.04(3) . ? C3 C4 1.509(5) . ? C3 H2 0.98(3) . ? C3 H3 0.96(3) . ? C4 C5 1.508(6) . ? C4 H4 0.93(5) . ? C4 H5 0.84(3) . ? C5 C6 1.506(6) . ? C5 H6 0.93(3) . ? C5 H7 1.05(6) . ? C6 C7 1.496(5) . ? C6 H8 0.90(3) . ? C6 H9 0.88(4) . ? C7 H10 0.97(3) . ? C8 C13 1.372(4) . ? C8 C9 1.387(4) . ? C9 C10 1.374(4) . ? C9 H11 0.97(3) . ? C10 C11 1.371(4) . ? C10 H12 0.90(3) . ? C11 C12 1.388(4) . ? C11 C14 1.506(5) . ? C12 C13 1.387(5) . ? C12 H13 1.00(3) . ? C13 H14 0.99(3) . ? C14 H15 1.01(4) . ? C14 H16 0.88(5) . ? C14 H17 0.91(5) . ? 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 C7 93.12(15) . . ? O1 S3 O2 119.31(15) . . ? O1 S3 N 107.31(13) . . ? O2 S3 N 104.90(13) . . ? O1 S3 C8 109.72(14) . . ? O2 S3 C8 108.51(14) . . ? N S3 C8 106.26(13) . . ? C1 N C2 112.1(2) . . ? C1 N S3 121.3(2) . . ? C2 N S3 123.87(19) . . ? N C1 S2 129.9(2) . . ? N C1 S1 109.9(2) . . ? S2 C1 S1 120.25(18) . . ? C7 C2 N 104.6(3) . . ? C7 C2 C3 111.1(3) . . ? N C2 C3 121.5(3) . . ? C7 C2 H1 100.6(17) . . ? N C2 H1 105.0(18) . . ? C3 C2 H1 111.8(17) . . ? C4 C3 C2 109.8(3) . . ? C4 C3 H2 110.4(19) . . ? C2 C3 H2 105.9(19) . . ? C4 C3 H3 113(2) . . ? C2 C3 H3 103(2) . . ? H2 C3 H3 114(3) . . ? C5 C4 C3 114.7(4) . . ? C5 C4 H4 121(3) . . ? C3 C4 H4 109(3) . . ? C5 C4 H5 109(2) . . ? C3 C4 H5 110(2) . . ? H4 C4 H5 91(4) . . ? C6 C5 C4 112.3(4) . . ? C6 C5 H6 107(2) . . ? C4 C5 H6 111.3(19) . . ? C6 C5 H7 119(3) . . ? C4 C5 H7 100(3) . . ? H6 C5 H7 108(4) . . ? C7 C6 C5 109.5(3) . . ? C7 C6 H8 112(2) . . ? C5 C6 H8 106(2) . . ? C7 C6 H9 110(2) . . ? C5 C6 H9 110(2) . . ? H8 C6 H9 109(3) . . ? C2 C7 C6 114.7(3) . . ? C2 C7 S1 104.4(2) . . ? C6 C7 S1 117.9(3) . . ? C2 C7 H10 104(2) . . ? C6 C7 H10 108(2) . . ? S1 C7 H10 106(2) . . ? C13 C8 C9 120.5(3) . . ? C13 C8 S3 120.2(3) . . ? C9 C8 S3 119.2(2) . . ? C10 C9 C8 118.6(3) . . ? C10 C9 H11 120.1(16) . . ? C8 C9 H11 121.3(16) . . ? C11 C10 C9 122.6(3) . . ? C11 C10 H12 122.3(19) . . ? C9 C10 H12 115.2(19) . . ? C10 C11 C12 117.9(3) . . ? C10 C11 C14 121.4(4) . . ? C12 C11 C14 120.6(4) . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H13 117.8(16) . . ? C11 C12 H13 121.4(16) . . ? C8 C13 C12 119.6(3) . . ? C8 C13 H14 123(2) . . ? C12 C13 H14 117(2) . . ? C11 C14 H15 109(2) . . ? C11 C14 H16 113(3) . . ? H15 C14 H16 115(4) . . ? C11 C14 H17 109(4) . . ? H15 C14 H17 102(4) . . ? H16 C14 H17 108(5) . . ? 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 S3 N C1 -41.5(3) . . . . ? O2 S3 N C1 -169.3(2) . . . . ? C8 S3 N C1 75.8(2) . . . . ? O1 S3 N C2 158.6(2) . . . . ? O2 S3 N C2 30.8(3) . . . . ? C8 S3 N C2 -84.0(3) . . . . ? C2 N C1 S2 161.8(2) . . . . ? S3 N C1 S2 -0.2(4) . . . . ? C2 N C1 S1 -18.2(3) . . . . ? S3 N C1 S1 179.80(14) . . . . ? C7 S1 C1 N -5.8(2) . . . . ? C7 S1 C1 S2 174.2(2) . . . . ? C1 N C2 C7 38.5(3) . . . . ? S3 N C2 C7 -160.0(2) . . . . ? C1 N C2 C3 165.0(3) . . . . ? S3 N C2 C3 -33.5(4) . . . . ? C7 C2 C3 C4 -52.5(5) . . . . ? N C2 C3 C4 -176.0(3) . . . . ? C2 C3 C4 C5 51.7(6) . . . . ? C3 C4 C5 C6 -52.0(6) . . . . ? C4 C5 C6 C7 51.0(6) . . . . ? N C2 C7 C6 -170.3(3) . . . . ? C3 C2 C7 C6 56.9(5) . . . . ? N C2 C7 S1 -39.8(3) . . . . ? C3 C2 C7 S1 -172.5(3) . . . . ? C5 C6 C7 C2 -55.2(5) . . . . ? C5 C6 C7 S1 -178.8(3) . . . . ? C1 S1 C7 C2 27.3(3) . . . . ? C1 S1 C7 C6 155.9(3) . . . . ? O1 S3 C8 C13 12.7(3) . . . . ? O2 S3 C8 C13 144.6(3) . . . . ? N S3 C8 C13 -103.0(3) . . . . ? O1 S3 C8 C9 -164.1(2) . . . . ? O2 S3 C8 C9 -32.2(3) . . . . ? N S3 C8 C9 80.2(3) . . . . ? C13 C8 C9 C10 -0.6(5) . . . . ? S3 C8 C9 C10 176.2(2) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? C9 C10 C11 C14 179.3(4) . . . . ? C10 C11 C12 C13 -0.4(5) . . . . ? C14 C11 C12 C13 -179.9(4) . . . . ? C9 C8 C13 C12 0.1(5) . . . . ? S3 C8 C13 C12 -176.7(3) . . . . ? C11 C12 C13 C8 0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.244 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.054