# Electronic Supplementary Material (ESI) for Analytical Methods # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full ? _journal_coden_cambridge ? _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Debasis Das' _publ_contact_author_email dasdebasis2001@yahoo.com loop_ _publ_author_name D.Das S.Das A.Sahana A.Banerjee S.Lohar S.Guha J.Sanmartin data_be47jea1n _database_code_depnum_ccdc_archive 'CCDC 855224' #TrackingRef '- NATA CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N S' _chemical_formula_weight 237.31 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1, z+1/2' 'x+1/2, -y+1, z+1/2' _cell_length_a 10.7541(18) _cell_length_b 20.966(4) _cell_length_c 10.5543(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2379.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9146 _exptl_absorpt_correction_T_max 0.9830 _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 ? _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 2392 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2392 _reflns_number_gt 2227 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^ > 2\s(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^)+(0.0388P)^2^+0.8275P] 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(7) _refine_ls_number_reflns 2392 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.014 _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 C1 C 0.95964(16) 0.83014(8) 0.97874(16) 0.0180(4) Uani 1 1 d . . . C2 C 0.98177(18) 0.77330(9) 0.91739(18) 0.0218(4) Uani 1 1 d . . . H2 H 1.0545 0.7495 0.9369 0.026 Uiso 1 1 calc R . . C3 C 0.89801(19) 0.75016(9) 0.8264(2) 0.0262(4) Uani 1 1 d . . . H3 H 0.9156 0.7113 0.7836 0.031 Uiso 1 1 calc R . . C4 C 0.79145(17) 0.78282(9) 0.79855(19) 0.0238(4) Uani 1 1 d . . . H4 H 0.7368 0.7671 0.7351 0.029 Uiso 1 1 calc R . . C5 C 0.76176(17) 0.83995(9) 0.86359(18) 0.0197(4) Uani 1 1 d . . . C6 C 0.65008(17) 0.87346(9) 0.84037(18) 0.0220(4) Uani 1 1 d . . . H6 H 0.5940 0.8582 0.7778 0.026 Uiso 1 1 calc R . . C7 C 0.62168(18) 0.92727(8) 0.90644(19) 0.0232(4) Uani 1 1 d . . . H7 H 0.5457 0.9489 0.8903 0.028 Uiso 1 1 calc R . . C8 C 0.70447(17) 0.95119(10) 0.99884(19) 0.0221(4) Uani 1 1 d . . . H8 H 0.6834 0.9885 1.0451 0.027 Uiso 1 1 calc R . . C9 C 0.81500(19) 0.92084(9) 1.0222(2) 0.0200(4) Uani 1 1 d . . . H9 H 0.8711 0.9380 1.0828 0.024 Uiso 1 1 calc R . . C10 C 0.84625(16) 0.86390(8) 0.95646(17) 0.0168(4) Uani 1 1 d . . . C11 C 1.16051(16) 0.85138(9) 1.04536(17) 0.0190(4) Uani 1 1 d . . . H11 H 1.1869 0.8280 0.9731 0.023 Uiso 1 1 calc R . . C12 C 1.25344(18) 0.87896(8) 1.12763(17) 0.0188(4) Uani 1 1 d . . . C13 C 1.38038(17) 0.87373(9) 1.11697(19) 0.0220(4) Uani 1 1 d . . . H13 H 1.4208 0.8488 1.0541 0.026 Uiso 1 1 calc R . . C14 C 1.44395(17) 0.90947(9) 1.20953(19) 0.0239(4) Uani 1 1 d . . . H14 H 1.5320 0.9110 1.2163 0.029 Uiso 1 1 calc R . . C15 C 1.36590(18) 0.94141(10) 1.28795(18) 0.0252(5) Uani 1 1 d . . . H15 H 1.3931 0.9680 1.3554 0.030 Uiso 1 1 calc R . . N1 N 1.04382(14) 0.85737(7) 1.06643(14) 0.0183(3) Uani 1 1 d . . . S1 S 1.21213(4) 0.92842(2) 1.25150(5) 0.02205(12) 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 C1 0.0169(9) 0.0214(9) 0.0158(9) 0.0008(7) 0.0013(7) -0.0030(7) C2 0.0195(9) 0.0205(9) 0.0254(10) -0.0021(8) 0.0015(8) 0.0006(7) C3 0.0265(10) 0.0238(10) 0.0282(11) -0.0081(8) 0.0035(8) -0.0025(8) C4 0.0224(10) 0.0268(10) 0.0222(10) -0.0037(8) -0.0016(8) -0.0065(8) C5 0.0194(9) 0.0223(9) 0.0174(9) 0.0017(7) 0.0022(7) -0.0052(7) C6 0.0209(9) 0.0244(10) 0.0207(10) 0.0038(7) -0.0037(7) -0.0064(8) C7 0.0191(10) 0.0226(10) 0.0279(11) 0.0060(8) -0.0015(8) 0.0004(7) C8 0.0237(10) 0.0190(9) 0.0236(10) -0.0020(8) 0.0000(8) 0.0017(8) C9 0.0211(10) 0.0216(10) 0.0173(9) -0.0001(7) -0.0002(8) -0.0031(8) C10 0.0179(9) 0.0184(9) 0.0141(9) 0.0013(7) 0.0021(7) -0.0035(7) C11 0.0202(9) 0.0207(9) 0.0161(9) 0.0007(7) 0.0003(8) 0.0001(7) C12 0.0208(8) 0.0190(9) 0.0166(9) 0.0032(7) -0.0001(7) 0.0010(7) C13 0.0211(9) 0.0226(9) 0.0224(10) 0.0019(7) -0.0009(8) -0.0005(7) C14 0.0160(9) 0.0294(10) 0.0262(10) 0.0046(8) -0.0018(8) 0.0008(8) C15 0.0238(10) 0.0300(10) 0.0219(11) 0.0037(8) -0.0041(8) -0.0096(8) N1 0.0201(8) 0.0186(7) 0.0163(8) 0.0023(6) -0.0017(6) -0.0004(6) S1 0.0202(2) 0.0269(2) 0.0191(2) -0.0016(2) 0.0017(2) -0.00265(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.377(3) . ? C1 N1 1.415(2) . ? C1 C10 1.429(2) . ? C2 C3 1.403(3) . ? C2 H2 0.9500 . ? C3 C4 1.367(3) . ? C3 H3 0.9500 . ? C4 C5 1.417(3) . ? C4 H4 0.9500 . ? C5 C6 1.413(3) . ? C5 C10 1.428(3) . ? C6 C7 1.361(3) . ? C6 H6 0.9500 . ? C7 C8 1.413(3) . ? C7 H7 0.9500 . ? C8 C9 1.371(3) . ? C8 H8 0.9500 . ? C9 C10 1.421(3) . ? C9 H9 0.9500 . ? C11 N1 1.281(2) . ? C11 C12 1.445(3) . ? C11 H11 0.9500 . ? C12 C13 1.374(3) . ? C12 S1 1.7268(19) . ? C13 C14 1.408(3) . ? C13 H13 0.9500 . ? C14 C15 1.356(3) . ? C14 H14 0.9500 . ? C15 S1 1.7194(19) . ? C15 H15 0.9500 . ? 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 C2 C1 N1 123.11(16) . . ? C2 C1 C10 119.91(16) . . ? N1 C1 C10 116.98(15) . . ? C1 C2 C3 120.67(17) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.81(17) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.54(18) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 121.86(17) . . ? C6 C5 C10 119.02(16) . . ? C4 C5 C10 119.11(17) . . ? C7 C6 C5 120.94(18) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.43(18) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.41(18) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.47(19) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 118.70(16) . . ? C9 C10 C1 122.50(17) . . ? C5 C10 C1 118.80(16) . . ? N1 C11 C12 122.30(17) . . ? N1 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C13 C12 C11 127.31(17) . . ? C13 C12 S1 111.43(14) . . ? C11 C12 S1 121.16(14) . . ? C12 C13 C14 112.53(18) . . ? C12 C13 H13 123.7 . . ? C14 C13 H13 123.7 . . ? C15 C14 C13 112.69(17) . . ? C15 C14 H14 123.7 . . ? C13 C14 H14 123.7 . . ? C14 C15 S1 112.38(15) . . ? C14 C15 H15 123.8 . . ? S1 C15 H15 123.8 . . ? C11 N1 C1 118.28(15) . . ? C15 S1 C12 90.98(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 N1 C1 C2 C3 -176.66(17) . . . . ? C10 C1 C2 C3 4.4(3) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C2 C3 C4 C5 -1.7(3) . . . . ? C3 C4 C5 C6 -177.54(19) . . . . ? C3 C4 C5 C10 1.6(3) . . . . ? C4 C5 C6 C7 178.12(18) . . . . ? C10 C5 C6 C7 -1.0(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C10 -1.8(3) . . . . ? C8 C9 C10 C5 1.5(3) . . . . ? C8 C9 C10 C1 -179.21(17) . . . . ? C6 C5 C10 C9 -0.1(3) . . . . ? C4 C5 C10 C9 -179.29(16) . . . . ? C6 C5 C10 C1 -179.42(16) . . . . ? C4 C5 C10 C1 1.4(3) . . . . ? C2 C1 C10 C9 176.34(17) . . . . ? N1 C1 C10 C9 -2.7(2) . . . . ? C2 C1 C10 C5 -4.4(3) . . . . ? N1 C1 C10 C5 176.61(15) . . . . ? N1 C11 C12 C13 177.49(18) . . . . ? N1 C11 C12 S1 -6.4(3) . . . . ? C11 C12 C13 C14 176.79(17) . . . . ? S1 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C13 C14 C15 S1 0.3(2) . . . . ? C12 C11 N1 C1 178.34(15) . . . . ? C2 C1 N1 C11 36.3(2) . . . . ? C10 C1 N1 C11 -144.76(17) . . . . ? C14 C15 S1 C12 -0.10(15) . . . . ? C13 C12 S1 C15 -0.14(14) . . . . ? C11 C12 S1 C15 -176.84(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.177 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.040