data_anass3m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_contact_author ; Madeleine Helliwell ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS ADDRESS ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; The structure was solved by the direct methods. All non-H atoms were refined anisotropically. H atoms bonded to C were included in calculated positions; those bonded to N were found by difference Fourier methods and refined isotropically. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison, Wisconsin, USA. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori and R. Spagna SIR2004: an improved tool for crystal structure determination and refinement J. Appl. Cryst. (2005). 38, 381-388 Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G, M. (2005). CELL_NOW. University of G\"ottingen, Germany. Sheldrick, G, M. (2007). TWINABS. University of G\"ottingen, Germany. Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 N S2' _chemical_formula_sum 'C16 H13 N S2' _chemical_formula_weight 283.39 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5616(17) _cell_length_b 9.1731(16) _cell_length_c 15.889(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.058(3) _cell_angle_gamma 90.00 _cell_volume 1392.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 915 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.36 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.366 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 '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 10816 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 26.44 _reflns_number_total 2859 _reflns_number_gt 2616 _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^)+(0.0441P)^2^+0.3687P] 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 2859 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.69515(4) 0.68521(4) 1.14748(2) 0.01774(11) Uani 1 1 d . . . S2 S 0.96911(4) 0.55263(4) 1.12932(2) 0.01869(11) Uani 1 1 d . . . N1 N 0.78932(12) 0.59997(13) 1.00010(7) 0.0160(3) Uani 1 1 d . . . H1N H 0.853(2) 0.5610(18) 0.9693(11) 0.024(5) Uiso 1 1 d . . . C1 C 0.81952(14) 0.61174(15) 1.08305(9) 0.0159(3) Uani 1 1 d . . . C2 C 0.59810(14) 0.80371(15) 1.07228(9) 0.0176(3) Uani 1 1 d . . . H2 H 0.5070 0.8288 1.0976 0.021 Uiso 1 1 calc R . . C3 C 0.56599(15) 0.71901(16) 0.99371(9) 0.0173(3) Uani 1 1 d . . . H3 H 0.4757 0.7286 0.9673 0.021 Uiso 1 1 calc R . . C4 C 0.65844(14) 0.63022(15) 0.95882(9) 0.0162(3) Uani 1 1 d . . . C5 C 0.67803(14) 0.94509(15) 1.06082(9) 0.0167(3) Uani 1 1 d . . . C6 C 0.74668(16) 0.97603(16) 0.98698(9) 0.0213(3) Uani 1 1 d . . . H6 H 0.7398 0.9100 0.9410 0.026 Uiso 1 1 calc R . . C7 C 0.82495(17) 1.10251(17) 0.98021(10) 0.0244(3) Uani 1 1 d . . . H7 H 0.8723 1.1220 0.9299 0.029 Uiso 1 1 calc R . . C8 C 0.83443(15) 1.20059(16) 1.04652(9) 0.0209(3) Uani 1 1 d . . . H8 H 0.8886 1.2869 1.0419 0.025 Uiso 1 1 calc R . . C9 C 0.76444(16) 1.17206(16) 1.11971(9) 0.0206(3) Uani 1 1 d . . . H9 H 0.7693 1.2398 1.1650 0.025 Uiso 1 1 calc R . . C10 C 0.68749(15) 1.04519(16) 1.12699(9) 0.0192(3) Uani 1 1 d . . . H10 H 0.6406 1.0260 1.1775 0.023 Uiso 1 1 calc R . . C11 C 0.63404(14) 0.55695(15) 0.87658(9) 0.0166(3) Uani 1 1 d . . . C12 C 0.55876(15) 0.62852(16) 0.81139(9) 0.0192(3) Uani 1 1 d . . . H12 H 0.5263 0.7252 0.8196 0.023 Uiso 1 1 calc R . . C13 C 0.53136(15) 0.55930(17) 0.73513(9) 0.0227(3) Uani 1 1 d . . . H13 H 0.4784 0.6077 0.6918 0.027 Uiso 1 1 calc R . . C14 C 0.58121(15) 0.41925(18) 0.72184(9) 0.0230(3) Uani 1 1 d . . . H14 H 0.5628 0.3722 0.6693 0.028 Uiso 1 1 calc R . . C15 C 0.65784(15) 0.34805(17) 0.78524(9) 0.0210(3) Uani 1 1 d . . . H15 H 0.6933 0.2529 0.7759 0.025 Uiso 1 1 calc R . . C16 C 0.68264(14) 0.41601(16) 0.86235(9) 0.0177(3) Uani 1 1 d . . . H16 H 0.7333 0.3659 0.9060 0.021 Uiso 1 1 calc R . . 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 0.0178(2) 0.0194(2) 0.01627(19) 0.00174(13) 0.00341(14) 0.00180(13) S2 0.01534(19) 0.0232(2) 0.01726(19) -0.00267(14) -0.00263(14) 0.00208(13) N1 0.0116(6) 0.0197(6) 0.0165(6) -0.0024(5) 0.0007(5) 0.0003(5) C1 0.0145(7) 0.0137(7) 0.0194(7) 0.0001(5) 0.0016(5) -0.0029(5) C2 0.0133(7) 0.0193(7) 0.0202(7) 0.0021(6) 0.0024(6) 0.0032(5) C3 0.0131(7) 0.0187(7) 0.0201(7) 0.0020(6) -0.0006(5) -0.0010(5) C4 0.0137(7) 0.0163(7) 0.0185(7) 0.0034(5) -0.0015(5) -0.0029(5) C5 0.0134(7) 0.0178(7) 0.0189(7) 0.0017(5) -0.0006(5) 0.0036(5) C6 0.0263(8) 0.0185(7) 0.0194(7) -0.0026(6) 0.0045(6) -0.0002(6) C7 0.0285(9) 0.0221(8) 0.0230(8) 0.0022(6) 0.0071(6) -0.0002(6) C8 0.0190(7) 0.0177(7) 0.0258(8) 0.0023(6) -0.0038(6) -0.0007(6) C9 0.0223(8) 0.0202(7) 0.0188(7) -0.0019(6) -0.0061(6) 0.0037(6) C10 0.0187(7) 0.0229(8) 0.0158(7) 0.0015(6) 0.0002(6) 0.0049(6) C11 0.0114(7) 0.0211(7) 0.0174(7) 0.0016(6) 0.0009(5) -0.0040(5) C12 0.0144(7) 0.0222(8) 0.0211(7) 0.0046(6) 0.0015(6) -0.0015(6) C13 0.0155(7) 0.0354(9) 0.0172(7) 0.0071(6) -0.0005(6) -0.0020(6) C14 0.0160(7) 0.0367(9) 0.0164(7) -0.0043(6) 0.0018(6) -0.0056(6) C15 0.0141(7) 0.0253(8) 0.0237(8) -0.0045(6) 0.0032(6) -0.0029(6) C16 0.0130(7) 0.0209(7) 0.0190(7) 0.0001(6) -0.0003(5) -0.0016(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 1.7332(14) . ? S1 C2 1.8414(14) . ? S2 C1 1.6748(14) . ? N1 C1 1.3434(18) . ? N1 C4 1.4193(18) . ? N1 H1N 0.875(19) . ? C2 C3 1.493(2) . ? C2 C5 1.520(2) . ? C2 H2 1.0000 . ? C3 C4 1.337(2) . ? C3 H3 0.9500 . ? C4 C11 1.480(2) . ? C5 C6 1.394(2) . ? C5 C10 1.396(2) . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 C8 1.386(2) . ? C7 H7 0.9500 . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.384(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.395(2) . ? C11 C12 1.403(2) . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.389(2) . ? C13 H13 0.9500 . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 H16 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 C1 S1 C2 100.76(7) . . ? C1 N1 C4 126.34(12) . . ? C1 N1 H1N 116.9(12) . . ? C4 N1 H1N 116.4(12) . . ? N1 C1 S2 123.69(11) . . ? N1 C1 S1 118.87(11) . . ? S2 C1 S1 117.38(8) . . ? C3 C2 C5 115.68(12) . . ? C3 C2 S1 108.61(10) . . ? C5 C2 S1 109.73(9) . . ? C3 C2 H2 107.5 . . ? C5 C2 H2 107.5 . . ? S1 C2 H2 107.5 . . ? C4 C3 C2 123.00(13) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C3 C4 N1 120.84(13) . . ? C3 C4 C11 123.85(13) . . ? N1 C4 C11 115.31(12) . . ? C6 C5 C10 118.69(14) . . ? C6 C5 C2 121.91(13) . . ? C10 C5 C2 119.36(13) . . ? C7 C6 C5 120.48(14) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.32(14) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.63(14) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 120.17(14) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 120.69(14) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C16 C11 C12 118.63(13) . . ? C16 C11 C4 121.39(13) . . ? C12 C11 C4 119.97(13) . . ? C13 C12 C11 120.49(14) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.13(14) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.01(14) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.91(15) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 120.80(14) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? 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 C4 N1 C1 S2 171.26(11) . . . . ? C4 N1 C1 S1 -6.0(2) . . . . ? C2 S1 C1 N1 -27.24(12) . . . . ? C2 S1 C1 S2 155.32(8) . . . . ? C1 S1 C2 C3 47.34(11) . . . . ? C1 S1 C2 C5 -79.99(10) . . . . ? C5 C2 C3 C4 81.74(17) . . . . ? S1 C2 C3 C4 -42.12(17) . . . . ? C2 C3 C4 N1 6.6(2) . . . . ? C2 C3 C4 C11 -173.55(13) . . . . ? C1 N1 C4 C3 22.8(2) . . . . ? C1 N1 C4 C11 -157.05(13) . . . . ? C3 C2 C5 C6 -15.31(19) . . . . ? S1 C2 C5 C6 107.96(14) . . . . ? C3 C2 C5 C10 166.94(13) . . . . ? S1 C2 C5 C10 -69.79(15) . . . . ? C10 C5 C6 C7 1.2(2) . . . . ? C2 C5 C6 C7 -176.53(14) . . . . ? C5 C6 C7 C8 -0.8(2) . . . . ? C6 C7 C8 C9 -0.4(2) . . . . ? C7 C8 C9 C10 1.1(2) . . . . ? C8 C9 C10 C5 -0.6(2) . . . . ? C6 C5 C10 C9 -0.5(2) . . . . ? C2 C5 C10 C9 177.29(13) . . . . ? C3 C4 C11 C16 -143.61(15) . . . . ? N1 C4 C11 C16 36.24(18) . . . . ? C3 C4 C11 C12 35.4(2) . . . . ? N1 C4 C11 C12 -144.76(13) . . . . ? C16 C11 C12 C13 1.1(2) . . . . ? C4 C11 C12 C13 -177.89(13) . . . . ? C11 C12 C13 C14 -1.5(2) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C13 C14 C15 C16 1.0(2) . . . . ? C14 C15 C16 C11 -1.4(2) . . . . ? C12 C11 C16 C15 0.3(2) . . . . ? C4 C11 C16 C15 179.35(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N S2 0.875(19) 2.571(19) 3.4444(13) 176.4(15) 3_767 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.353 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.052