# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/461 data_st-587 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H11 N O S' _chemical_formula_weight 265.32 _chemical_melting_point ? _chemical_compound_source ? 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.131(1) _cell_length_b 12.598(2) _cell_length_c 13.699(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1230.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 228(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description plates _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method ? _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type n/a _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 228(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 ? _diffrn_measurement_method ? _diffrn_standards_number 3 _diffrn_standards_interval_count 147 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.50 _diffrn_reflns_number 903 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 22.00 _reflns_number_total 903 _reflns_number_observed 787 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 40 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.2499P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(13) _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 -0.06(19) _refine_ls_number_reflns 863 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_obs 0.0322 _refine_ls_wR_factor_all 0.0897 _refine_ls_wR_factor_obs 0.0769 _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.048 _refine_ls_restrained_S_all 1.123 _refine_ls_restrained_S_obs 1.048 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.2822(5) 0.6864(3) 0.5416(3) 0.0491(11) Uani 1 d . . H1A H -0.1878(5) 0.7089(3) 0.5084(3) 0.059 Uiso 1 calc R . H1B H -0.3693(5) 0.7297(3) 0.5587(3) 0.059 Uiso 1 calc R . O2 O -0.6053(4) 0.7055(2) 0.6327(2) 0.0468(9) Uani 1 d . . S1 S 0.0447(2) 0.54364(9) 0.47035(9) 0.0433(4) Uani 1 d . . C2 C -0.2935(6) 0.5821(3) 0.5671(3) 0.0310(11) Uani 1 d . . C3 C -0.5984(6) 0.6087(3) 0.6538(3) 0.0340(12) Uani 1 d . . C4 C -0.9030(6) 0.6288(4) 0.7395(3) 0.0444(13) Uani 1 d . . H4 H -0.9022(6) 0.6998(4) 0.7209(3) 0.053 Uiso 1 calc R . C5 C -1.0511(9) 0.5908(4) 0.7934(4) 0.0507(13) Uani 1 d . . H5 H -1.1507(9) 0.6349(4) 0.8100(4) 0.061 Uiso 1 calc R . C6 C -1.0491(8) 0.4853(4) 0.8228(3) 0.0542(15) Uani 1 d . . H6 H -1.1478(8) 0.4586(4) 0.8598(3) 0.065 Uiso 1 calc R . C7 C -0.9023(7) 0.4200(4) 0.7976(3) 0.0461(13) Uani 1 d . . H7 H -0.9011(7) 0.3499(4) 0.8188(3) 0.055 Uiso 1 calc R . C8 C -0.5992(6) 0.3846(3) 0.7101(3) 0.0398(12) Uani 1 d . . H8A H -0.5442(6) 0.3545(3) 0.7686(3) 0.048 Uiso 1 calc R . H8B H -0.6540(6) 0.3265(3) 0.6734(3) 0.048 Uiso 1 calc R . C9 C -0.3019(6) 0.3654(3) 0.6209(3) 0.0357(11) Uani 1 d . . H9 H -0.3044(6) 0.2942(3) 0.6387(3) 0.043 Uiso 1 calc R . C10 C 0.0069(6) 0.3505(4) 0.5260(3) 0.0454(12) Uani 1 d . . H10 H 0.0301(6) 0.2785(4) 0.5353(3) 0.054 Uiso 1 calc R . C11 C 0.1212(7) 0.4146(4) 0.4746(4) 0.0488(12) Uani 1 d . . H11 H 0.2306(7) 0.3913(4) 0.4445(4) 0.059 Uiso 1 calc R . C12 C -0.1525(6) 0.5118(3) 0.5395(3) 0.0313(10) Uani 1 d . . C13 C -0.1534(6) 0.4038(3) 0.5648(3) 0.0322(11) Uani 1 d . . C14 C -0.4448(6) 0.4316(3) 0.6501(3) 0.0306(10) Uani 1 d . . C15 C -0.4446(6) 0.5415(3) 0.6239(3) 0.0302(9) Uani 1 d . . C16 C -0.7546(6) 0.5641(3) 0.7119(3) 0.0325(11) Uani 1 d . . C17 C -0.7548(5) 0.4583(4) 0.7404(3) 0.0352(11) Uani 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 N1 0.049(2) 0.031(2) 0.067(3) 0.013(2) 0.018(2) 0.001(2) O2 0.051(2) 0.033(2) 0.057(2) 0.0088(15) 0.001(2) 0.005(2) S1 0.0420(6) 0.0457(7) 0.0423(6) 0.0025(6) 0.0091(7) -0.0029(6) C2 0.034(3) 0.028(2) 0.032(2) 0.004(2) -0.006(2) -0.002(2) C3 0.039(3) 0.030(3) 0.033(3) 0.004(2) -0.009(2) -0.004(2) C4 0.038(3) 0.056(3) 0.039(3) -0.004(2) -0.009(3) 0.005(3) C5 0.038(3) 0.071(4) 0.043(3) -0.009(3) 0.000(3) 0.004(3) C6 0.036(3) 0.089(4) 0.038(3) -0.008(3) 0.013(3) -0.016(3) C7 0.046(3) 0.054(3) 0.038(3) 0.001(2) -0.001(3) -0.010(3) C8 0.045(3) 0.035(2) 0.039(3) 0.003(2) 0.000(2) -0.007(2) C9 0.049(3) 0.024(2) 0.035(2) 0.003(2) -0.001(2) 0.000(2) C10 0.053(3) 0.038(2) 0.045(3) -0.001(2) 0.003(3) 0.011(2) C11 0.044(3) 0.054(3) 0.048(3) -0.006(3) 0.014(3) 0.012(2) C12 0.035(2) 0.034(2) 0.025(2) -0.001(2) -0.004(2) -0.002(2) C13 0.036(3) 0.031(3) 0.030(2) -0.006(2) -0.001(2) -0.003(2) C14 0.030(2) 0.031(2) 0.031(2) -0.001(2) -0.004(2) -0.004(2) C15 0.033(2) 0.028(2) 0.029(2) -0.001(2) -0.005(2) -0.003(2) C16 0.033(3) 0.035(3) 0.030(2) -0.005(2) -0.001(2) 0.000(2) C17 0.031(2) 0.045(3) 0.029(2) -0.003(2) -0.005(2) -0.006(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 N1 C2 1.362(5) . ? O2 C3 1.254(5) . ? S1 C11 1.716(5) . ? S1 C12 1.742(4) . ? C2 C12 1.392(6) . ? C2 C15 1.424(6) . ? C3 C15 1.444(6) . ? C3 C16 1.481(6) . ? C4 C5 1.375(6) . ? C4 C16 1.387(6) . ? C5 C6 1.388(7) . ? C6 C7 1.375(7) . ? C7 C17 1.397(6) . ? C8 C14 1.496(6) . ? C8 C17 1.506(6) . ? C9 C14 1.376(6) . ? C9 C13 1.395(6) . ? C10 C11 1.346(6) . ? C10 C13 1.429(6) . ? C12 C13 1.404(5) . ? C14 C15 1.431(6) . ? C16 C17 1.389(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 C11 S1 C12 91.2(2) . . ? N1 C2 C12 120.0(4) . . ? N1 C2 C15 122.1(4) . . ? C12 C2 C15 117.9(3) . . ? O2 C3 C15 122.3(4) . . ? O2 C3 C16 117.6(4) . . ? C15 C3 C16 120.1(4) . . ? C5 C4 C16 121.8(5) . . ? C4 C5 C6 118.7(6) . . ? C7 C6 C5 120.5(5) . . ? C6 C7 C17 120.5(5) . . ? C14 C8 C17 116.7(4) . . ? C14 C9 C13 120.8(4) . . ? C11 C10 C13 113.4(4) . . ? C10 C11 S1 113.2(3) . . ? C2 C12 C13 123.1(4) . . ? C2 C12 S1 125.8(3) . . ? C13 C12 S1 111.1(3) . . ? C9 C13 C12 118.4(4) . . ? C9 C13 C10 130.5(4) . . ? C12 C13 C10 111.1(4) . . ? C9 C14 C15 120.8(4) . . ? C9 C14 C8 117.7(4) . . ? C15 C14 C8 121.5(4) . . ? C2 C15 C14 119.0(4) . . ? C2 C15 C3 121.3(3) . . ? C14 C15 C3 119.7(4) . . ? C4 C16 C17 119.1(4) . . ? C4 C16 C3 119.8(4) . . ? C17 C16 C3 121.1(4) . . ? C16 C17 C7 119.3(4) . . ? C16 C17 C8 120.9(4) . . ? C7 C17 C8 119.8(4) . . ? _refine_diff_density_max 0.145 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.035