# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_platon _database_code_depnum_ccdc_archive 'CCDC 876574' #TrackingRef 'platon.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N O2 S' _chemical_formula_weight 257.31 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' 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 10.5093(14) _cell_length_b 13.6166(17) _cell_length_c 9.1287(12) _cell_angle_alpha 90.00 _cell_angle_beta 114.028(6) _cell_angle_gamma 90.00 _cell_volume 1193.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5668 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 29.94 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15718 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 29.94 _reflns_number_total 3382 _reflns_number_gt 3340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0345P)^2^+0.2869P] 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 0.0049(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3109 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _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 0.19664(4) 0.03386(3) 0.35189(5) 0.04736(14) Uani 1 1 d . . . O2 O -0.13855(12) 0.40800(8) -0.11190(15) 0.0584(3) Uani 1 1 d . . . O1 O 0.33087(13) 0.09770(8) 0.03293(14) 0.0571(3) Uani 1 1 d . . . N1 N 0.21164(13) 0.09647(9) 0.19618(15) 0.0449(3) Uani 1 1 d . . . C12 C -0.08157(18) 0.23443(12) -0.1067(2) 0.0560(5) Uani 1 1 d . . . H12 H -0.1557 0.2228 -0.2047 0.067 Uiso 1 1 calc R . . C13 C 0.00702(19) 0.15904(12) -0.0258(2) 0.0572(5) Uani 1 1 d . . . H13 H -0.0076 0.0964 -0.0703 0.069 Uiso 1 1 calc R . . C8 C 0.11635(16) 0.17518(10) 0.11919(18) 0.0418(4) Uani 1 1 d . . . C9 C 0.13568(16) 0.26729(11) 0.1882(2) 0.0480(4) Uani 1 1 d . . . H9 H 0.2073 0.2781 0.2885 0.058 Uiso 1 1 calc R . . C10 C 0.04853(17) 0.34302(11) 0.1079(2) 0.0515(4) Uani 1 1 d . . . H10 H 0.0621 0.4052 0.1538 0.062 Uiso 1 1 calc R . . C11 C -0.05900(15) 0.32728(11) -0.04043(19) 0.0436(4) Uani 1 1 d . . . C14 C -0.2300(2) 0.40059(15) -0.2778(2) 0.0714(6) Uani 1 1 d . . . H14A H -0.3037 0.3553 -0.2904 0.107 Uiso 1 1 calc R . . H14B H -0.1788 0.3776 -0.3374 0.107 Uiso 1 1 calc R . . H14C H -0.2689 0.4640 -0.3172 0.107 Uiso 1 1 calc R . . C6 C 0.37376(15) -0.02615(10) 0.23797(18) 0.0406(3) Uani 1 1 d . . . C5 C 0.47487(17) -0.08520(12) 0.2197(2) 0.0502(4) Uani 1 1 d . . . H5 H 0.5071 -0.0712 0.1411 0.060 Uiso 1 1 calc R . . C4 C 0.52605(18) -0.16450(13) 0.3202(2) 0.0562(4) Uani 1 1 d . . . H4 H 0.5927 -0.2049 0.3086 0.067 Uiso 1 1 calc R . . C3 C 0.47895(18) -0.18465(12) 0.4388(2) 0.0556(4) Uani 1 1 d . . . H3 H 0.5156 -0.2382 0.5063 0.067 Uiso 1 1 calc R . . C2 C 0.37931(17) -0.12741(12) 0.45913(19) 0.0506(4) Uani 1 1 d . . . H2 H 0.3488 -0.1413 0.5392 0.061 Uiso 1 1 calc R . . C1 C 0.32556(15) -0.04778(11) 0.35566(18) 0.0419(4) Uani 1 1 d . . . C7 C 0.30786(16) 0.06074(11) 0.14214(19) 0.0430(4) 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 S1 0.0515(3) 0.0497(2) 0.0446(2) 0.00021(18) 0.02335(19) 0.00277(17) O2 0.0584(7) 0.0460(6) 0.0640(8) 0.0062(6) 0.0178(6) 0.0095(5) O1 0.0702(8) 0.0536(7) 0.0589(8) 0.0100(6) 0.0380(7) 0.0061(6) N1 0.0522(8) 0.0418(7) 0.0446(7) 0.0034(6) 0.0236(6) 0.0060(6) C12 0.0585(10) 0.0496(9) 0.0453(9) -0.0071(8) 0.0062(8) 0.0013(8) C13 0.0674(11) 0.0388(8) 0.0527(10) -0.0106(7) 0.0116(9) 0.0014(8) C8 0.0451(8) 0.0389(8) 0.0431(9) -0.0017(6) 0.0198(7) 0.0016(6) C9 0.0433(8) 0.0489(9) 0.0472(9) -0.0113(7) 0.0139(7) -0.0010(7) C10 0.0521(9) 0.0398(8) 0.0591(11) -0.0120(7) 0.0191(8) 0.0003(7) C11 0.0444(8) 0.0400(8) 0.0496(9) 0.0027(7) 0.0223(7) 0.0015(6) C14 0.0745(13) 0.0723(12) 0.0609(12) 0.0174(10) 0.0211(10) 0.0159(10) C6 0.0407(8) 0.0386(8) 0.0399(8) -0.0041(6) 0.0138(7) -0.0032(6) C5 0.0505(10) 0.0514(9) 0.0509(10) -0.0019(8) 0.0230(8) 0.0017(7) C4 0.0498(10) 0.0524(10) 0.0633(11) -0.0005(8) 0.0197(9) 0.0103(8) C3 0.0529(10) 0.0491(9) 0.0535(10) 0.0070(8) 0.0100(8) 0.0047(8) C2 0.0528(10) 0.0539(10) 0.0434(9) 0.0048(7) 0.0179(8) -0.0016(8) C1 0.0417(8) 0.0408(8) 0.0390(8) -0.0052(6) 0.0121(7) -0.0043(6) C7 0.0460(9) 0.0401(8) 0.0431(9) -0.0037(7) 0.0183(7) -0.0021(6) _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 N1 1.7189(13) . ? S1 C1 1.7420(16) . ? O2 C11 1.3742(18) . ? O2 C14 1.429(2) . ? O1 C7 1.2255(18) . ? N1 C7 1.382(2) . ? N1 C8 1.4395(19) . ? C12 C11 1.380(2) . ? C12 C13 1.381(2) . ? C12 H12 0.9300 . ? C13 C8 1.372(2) . ? C13 H13 0.9300 . ? C8 C9 1.381(2) . ? C9 C10 1.376(2) . ? C9 H9 0.9300 . ? C10 C11 1.382(2) . ? C10 H10 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C6 C1 1.393(2) . ? C6 C5 1.395(2) . ? C6 C7 1.467(2) . ? C5 C4 1.376(2) . ? C5 H5 0.9300 . ? C4 C3 1.389(3) . ? C4 H4 0.9300 . ? C3 C2 1.377(2) . ? C3 H3 0.9300 . ? C2 C1 1.397(2) . ? C2 H2 0.9300 . ? 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 S1 C1 90.02(7) . . ? C11 O2 C14 117.59(13) . . ? C7 N1 C8 123.55(13) . . ? C7 N1 S1 116.59(10) . . ? C8 N1 S1 119.55(10) . . ? C11 C12 C13 119.27(15) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C8 C13 C12 120.95(14) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C8 C9 119.70(14) . . ? C13 C8 N1 119.65(13) . . ? C9 C8 N1 120.64(14) . . ? C10 C9 C8 119.70(15) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.47(14) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 O2 124.20(14) . . ? C12 C11 C10 119.84(14) . . ? O2 C11 C10 115.96(13) . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 C6 C5 120.26(14) . . ? C1 C6 C7 113.50(14) . . ? C5 C6 C7 126.24(15) . . ? C4 C5 C6 118.84(16) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C4 C3 120.52(16) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C2 C3 C4 121.66(16) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C2 C1 117.94(16) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C6 C1 C2 120.76(15) . . ? C6 C1 S1 111.96(11) . . ? C2 C1 S1 127.28(13) . . ? O1 C7 N1 124.16(14) . . ? O1 C7 C6 127.93(15) . . ? N1 C7 C6 107.91(14) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 29.94 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.204 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.037