data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O2 S ' _chemical_formula_sum 'C15 H12 N2 O2 S' _chemical_formula_weight 284.33 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' 'O' 'O' 0.0106 0.0060 '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' '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 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.9349(8) _cell_length_b 6.3377(5) _cell_length_c 10.5783(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.752(3) _cell_angle_gamma 90.00 _cell_volume 659.97(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 12459 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.0 _cell_measurement_temperature 180(1) _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_T_max 0.968 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12985 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3719 _reflns_number_gt 3655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-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^ > 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^)+(0.0498P)^2^+0.0632P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 3719 _refine_ls_number_parameters 185 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0704 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.38118(2) 0.19812(4) 0.07511(2) 0.02097(7) Uani 1 1 d . . . O1 O 0.72537(9) 0.64945(17) 0.32903(10) 0.0408(3) Uani 1 1 d . . . O2 O 0.16220(9) 0.75472(14) 0.47426(8) 0.02817(18) Uani 1 1 d . . . N1 N 0.64575(9) 0.15805(14) 0.09518(9) 0.02055(18) Uani 1 1 d . . . N2 N 0.57408(9) 0.41387(14) 0.22686(8) 0.01994(17) Uani 1 1 d . . . C1 C 0.54129(10) 0.25936(16) 0.13628(9) 0.01803(18) Uani 1 1 d . . . C2 C 0.70695(11) 0.49645(19) 0.26014(10) 0.0242(2) Uani 1 1 d . . . C3 C 0.81490(10) 0.38301(18) 0.20725(9) 0.02135(19) Uani 1 1 d . . . C4 C 0.95146(11) 0.4417(2) 0.23803(10) 0.0264(2) Uani 1 1 d . . . H4 H 0.9750 0.5592 0.2923 0.032 Uiso 1 1 calc R . . C5 C 1.05163(11) 0.3290(2) 0.18965(10) 0.0267(2) Uani 1 1 d . . . H5 H 1.1442 0.3683 0.2107 0.032 Uiso 1 1 calc R . . C6 C 1.01657(10) 0.1567(2) 0.10949(11) 0.0273(2) Uani 1 1 d . . . H6 H 1.0859 0.0797 0.0762 0.033 Uiso 1 1 calc R . . C7 C 0.88249(10) 0.0967(2) 0.07797(11) 0.0259(2) Uani 1 1 d . . . H7 H 0.8593 -0.0204 0.0233 0.031 Uiso 1 1 calc R . . C8 C 0.78169(9) 0.2111(2) 0.12783(9) 0.02009(17) Uani 1 1 d . . . C9 C 0.46691(10) 0.50768(17) 0.28857(9) 0.01977(18) Uani 1 1 d . . . C10 C 0.42443(11) 0.40430(17) 0.39236(10) 0.02182(19) Uani 1 1 d . . . H10 H 0.4647 0.2741 0.4214 0.026 Uiso 1 1 calc R . . C11 C 0.32281(11) 0.49303(18) 0.45289(10) 0.02226(19) Uani 1 1 d . . . H11 H 0.2932 0.4235 0.5238 0.027 Uiso 1 1 calc R . . C12 C 0.26387(10) 0.68431(19) 0.40993(9) 0.02035(17) Uani 1 1 d . . . C13 C 0.30852(12) 0.78939(17) 0.30769(10) 0.0229(2) Uani 1 1 d . . . H13 H 0.2694 0.9206 0.2792 0.028 Uiso 1 1 calc R . . C14 C 0.41157(10) 0.6997(2) 0.24747(9) 0.02290(18) Uani 1 1 d . . . H14 H 0.4435 0.7707 0.1783 0.027 Uiso 1 1 calc R . . C15 C 0.09041(14) 0.9396(2) 0.42638(13) 0.0327(2) Uani 1 1 d . . . H15A H 0.0117 0.9610 0.4717 0.049 Uiso 1 1 calc R . . H15B H 0.0595 0.9224 0.3350 0.049 Uiso 1 1 calc R . . H15C H 0.1507 1.0623 0.4396 0.049 Uiso 1 1 calc R . . H1 H 0.6297(15) 0.070(3) 0.0416(15) 0.024(4) 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 0.01602(10) 0.01977(11) 0.02682(11) 0.00081(10) 0.00175(7) -0.00038(9) O1 0.0303(4) 0.0397(6) 0.0518(6) -0.0285(5) 0.0041(4) -0.0031(4) O2 0.0291(4) 0.0280(4) 0.0305(4) 0.0034(3) 0.0152(3) 0.0062(3) N1 0.0161(3) 0.0204(5) 0.0249(4) -0.0074(3) 0.0017(3) -0.0003(3) N2 0.0185(4) 0.0199(4) 0.0218(4) -0.0038(3) 0.0040(3) 0.0015(3) C1 0.0176(4) 0.0173(4) 0.0194(4) 0.0007(3) 0.0032(3) 0.0003(3) C2 0.0214(5) 0.0247(5) 0.0264(5) -0.0081(4) 0.0029(4) -0.0010(4) C3 0.0187(4) 0.0239(5) 0.0212(4) -0.0038(4) 0.0020(3) -0.0011(4) C4 0.0214(5) 0.0311(6) 0.0262(5) -0.0057(4) 0.0018(4) -0.0055(4) C5 0.0185(4) 0.0364(6) 0.0250(5) 0.0004(4) 0.0022(4) -0.0041(4) C6 0.0183(4) 0.0346(7) 0.0300(5) -0.0027(4) 0.0068(4) 0.0010(4) C7 0.0198(5) 0.0286(6) 0.0299(5) -0.0092(4) 0.0055(4) -0.0003(4) C8 0.0167(4) 0.0225(4) 0.0213(4) -0.0026(4) 0.0030(3) 0.0004(4) C9 0.0201(4) 0.0191(4) 0.0208(4) -0.0013(3) 0.0054(3) 0.0026(4) C10 0.0238(4) 0.0184(4) 0.0233(4) 0.0033(3) 0.0035(4) 0.0023(4) C11 0.0244(5) 0.0216(4) 0.0216(4) 0.0037(4) 0.0061(4) -0.0001(4) C12 0.0211(4) 0.0196(4) 0.0212(4) -0.0010(4) 0.0059(3) -0.0004(4) C13 0.0281(5) 0.0180(4) 0.0237(4) 0.0038(4) 0.0075(4) 0.0041(4) C14 0.0275(4) 0.0205(4) 0.0222(4) 0.0042(4) 0.0088(3) 0.0042(5) C15 0.0313(5) 0.0304(6) 0.0381(6) 0.0011(5) 0.0115(5) 0.0109(5) _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 1.6799(10) . ? O1 C2 1.2119(14) . ? O2 C12 1.3667(12) . ? O2 C15 1.4287(15) . ? N1 C1 1.3417(12) . ? N1 C8 1.3893(12) . ? N1 H1 0.798(17) . ? N2 C1 1.3780(13) . ? N2 C2 1.4196(13) . ? N2 C9 1.4493(12) . ? C2 C3 1.4635(14) . ? C3 C8 1.3884(15) . ? C3 C4 1.4020(14) . ? C4 C5 1.3784(15) . ? C4 H4 0.9500 . ? C5 C6 1.3973(17) . ? C5 H5 0.9500 . ? C6 C7 1.3822(14) . ? C6 H6 0.9500 . ? C7 C8 1.3961(14) . ? C7 H7 0.9500 . ? C9 C14 1.3810(15) . ? C9 C10 1.3920(13) . ? C10 C11 1.3857(14) . ? C10 H10 0.9500 . ? C11 C12 1.3955(16) . ? C11 H11 0.9500 . ? C12 C13 1.3926(14) . ? C13 C14 1.3976(13) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C12 O2 C15 117.29(9) . . ? C1 N1 C8 124.90(9) . . ? C1 N1 H1 118.5(11) . . ? C8 N1 H1 116.2(11) . . ? C1 N2 C2 123.99(8) . . ? C1 N2 C9 119.05(8) . . ? C2 N2 C9 116.88(8) . . ? N1 C1 N2 116.41(9) . . ? N1 C1 S1 119.89(7) . . ? N2 C1 S1 123.69(7) . . ? O1 C2 N2 120.27(10) . . ? O1 C2 C3 124.33(10) . . ? N2 C2 C3 115.40(9) . . ? C8 C3 C4 119.48(9) . . ? C8 C3 C2 119.36(9) . . ? C4 C3 C2 121.13(9) . . ? C5 C4 C3 120.06(10) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.79(10) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.98(10) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 118.88(10) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C3 C8 N1 118.94(9) . . ? C3 C8 C7 120.81(9) . . ? N1 C8 C7 120.22(10) . . ? C14 C9 C10 120.85(9) . . ? C14 C9 N2 120.34(9) . . ? C10 C9 N2 118.78(9) . . ? C11 C10 C9 119.39(9) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.13(9) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? O2 C12 C13 124.39(10) . . ? O2 C12 C11 115.30(9) . . ? C13 C12 C11 120.31(9) . . ? C12 C13 C14 119.28(10) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C9 C14 C13 120.00(9) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 C8 N1 C1 N2 -6.47(15) . . . . ? C8 N1 C1 S1 172.35(8) . . . . ? C2 N2 C1 N1 12.14(15) . . . . ? C9 N2 C1 N1 -171.14(9) . . . . ? C2 N2 C1 S1 -166.63(8) . . . . ? C9 N2 C1 S1 10.10(13) . . . . ? C1 N2 C2 O1 170.97(12) . . . . ? C9 N2 C2 O1 -5.83(16) . . . . ? C1 N2 C2 C3 -9.77(15) . . . . ? C9 N2 C2 C3 173.44(9) . . . . ? O1 C2 C3 C8 -179.13(12) . . . . ? N2 C2 C3 C8 1.64(15) . . . . ? O1 C2 C3 C4 2.53(18) . . . . ? N2 C2 C3 C4 -176.70(10) . . . . ? C8 C3 C4 C5 -0.03(17) . . . . ? C2 C3 C4 C5 178.31(11) . . . . ? C3 C4 C5 C6 0.25(17) . . . . ? C4 C5 C6 C7 -0.18(18) . . . . ? C5 C6 C7 C8 -0.11(18) . . . . ? C4 C3 C8 N1 -178.24(10) . . . . ? C2 C3 C8 N1 3.39(15) . . . . ? C4 C3 C8 C7 -0.26(16) . . . . ? C2 C3 C8 C7 -178.63(10) . . . . ? C1 N1 C8 C3 -1.04(16) . . . . ? C1 N1 C8 C7 -179.03(10) . . . . ? C6 C7 C8 C3 0.33(18) . . . . ? C6 C7 C8 N1 178.28(10) . . . . ? C1 N2 C9 C14 -98.78(12) . . . . ? C2 N2 C9 C14 78.18(13) . . . . ? C1 N2 C9 C10 83.40(12) . . . . ? C2 N2 C9 C10 -99.64(12) . . . . ? C14 C9 C10 C11 1.68(16) . . . . ? N2 C9 C10 C11 179.49(10) . . . . ? C9 C10 C11 C12 -0.01(16) . . . . ? C15 O2 C12 C13 5.19(16) . . . . ? C15 O2 C12 C11 -174.39(10) . . . . ? C10 C11 C12 O2 178.31(10) . . . . ? C10 C11 C12 C13 -1.29(16) . . . . ? O2 C12 C13 C14 -178.63(10) . . . . ? C11 C12 C13 C14 0.93(16) . . . . ? C10 C9 C14 C13 -2.04(16) . . . . ? N2 C9 C14 C13 -179.82(10) . . . . ? C12 C13 C14 C9 0.72(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.347 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.049