####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_asr1r _audit_block_doi 10.5517/ccndh6q _database_code_depnum_ccdc_archive 'CCDC 607823' loop_ _citation_id _citation_doi _citation_year 1 10.1016/j.tet.2006.12.075 2007 _audit_update_record ; 2006-05-17 deposited with the CCDC. 2021-05-11 downloaded from the CCDC. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N S3' _chemical_formula_sum 'C11 H9 N S3' _chemical_formula_weight 251.37 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.4197(7) _cell_length_b 7.2797(4) _cell_length_c 11.8980(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.161(2) _cell_angle_gamma 90.00 _cell_volume 1104.43(10) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9805 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 32.66 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 21868 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0074 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2532 _reflns_number_gt 2403 _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^)+(0.0227P)^2^+1.2500P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2532 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.001 _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 0.60033(3) 0.61360(6) 0.85829(4) 0.02107(11) Uani 1 1 d . . . S2 S 0.43105(3) 0.61888(6) 0.87410(3) 0.01751(11) Uani 1 1 d . . . S3 S 0.25684(3) 0.62476(6) 0.87478(3) 0.01838(11) Uani 1 1 d . . . N1 N 0.45104(11) 0.6226(2) 0.65228(12) 0.0191(3) Uani 1 1 d . . . C1 C 0.55284(12) 0.6172(2) 0.70800(14) 0.0166(3) Uani 1 1 d . . . C2 C 0.38506(12) 0.6262(2) 0.71853(13) 0.0141(3) Uani 1 1 d . . . C3 C 0.27614(12) 0.6360(2) 0.66100(13) 0.0166(3) Uani 1 1 d . . . H3A H 0.2508 0.6415 0.5771 0.020 Uiso 1 1 calc R . . C4 C 0.20543(12) 0.6378(2) 0.72436(13) 0.0135(3) Uani 1 1 d . . . C11 C 0.62817(13) 0.6137(3) 0.63704(16) 0.0234(4) Uani 1 1 d . . . H11A H 0.5890 0.5982 0.5530 0.035 Uiso 1 1 calc R . . H11B H 0.6772 0.5111 0.6635 0.035 Uiso 1 1 calc R . . H11C H 0.6673 0.7295 0.6484 0.035 Uiso 1 1 calc R . . C41 C 0.09030(12) 0.6519(2) 0.66768(13) 0.0140(3) Uani 1 1 d . . . C42 C 0.04910(12) 0.7383(2) 0.55749(14) 0.0172(3) Uani 1 1 d . . . H42A H 0.0951 0.7876 0.5186 0.021 Uiso 1 1 calc R . . C43 C -0.05931(12) 0.7520(2) 0.50479(14) 0.0199(3) Uani 1 1 d . . . H43A H -0.0867 0.8112 0.4303 0.024 Uiso 1 1 calc R . . C44 C -0.12759(12) 0.6794(2) 0.56072(14) 0.0187(3) Uani 1 1 d . . . H44A H -0.2013 0.6895 0.5247 0.022 Uiso 1 1 calc R . . C45 C -0.08737(12) 0.5920(2) 0.66962(15) 0.0186(3) Uani 1 1 d . . . H45A H -0.1337 0.5409 0.7075 0.022 Uiso 1 1 calc R . . C46 C 0.02083(12) 0.5791(2) 0.72334(14) 0.0161(3) Uani 1 1 d . . . H46A H 0.0477 0.5206 0.7981 0.019 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 0.01220(18) 0.0309(2) 0.0188(2) 0.00074(16) 0.00299(14) 0.00148(16) S2 0.01380(19) 0.0253(2) 0.01269(18) 0.00104(14) 0.00303(14) 0.00160(15) S3 0.01338(18) 0.0300(2) 0.01217(18) 0.00149(15) 0.00458(14) 0.00186(15) N1 0.0137(6) 0.0281(7) 0.0170(6) 0.0015(6) 0.0068(5) 0.0015(5) C1 0.0148(7) 0.0158(7) 0.0196(7) 0.0021(6) 0.0062(6) -0.0001(6) C2 0.0146(7) 0.0151(7) 0.0128(7) 0.0006(5) 0.0045(5) -0.0005(5) C3 0.0135(7) 0.0238(8) 0.0121(7) -0.0005(6) 0.0035(5) 0.0002(6) C4 0.0130(7) 0.0137(7) 0.0135(7) 0.0010(5) 0.0036(5) 0.0004(5) C11 0.0151(7) 0.0325(9) 0.0251(8) 0.0040(7) 0.0101(6) 0.0025(7) C41 0.0120(7) 0.0151(7) 0.0145(7) -0.0020(6) 0.0037(5) 0.0007(5) C42 0.0151(7) 0.0216(8) 0.0161(7) 0.0011(6) 0.0066(6) 0.0000(6) C43 0.0174(7) 0.0257(8) 0.0152(7) 0.0016(6) 0.0032(6) 0.0033(6) C44 0.0126(7) 0.0229(8) 0.0195(7) -0.0034(6) 0.0032(6) 0.0018(6) C45 0.0135(7) 0.0222(8) 0.0218(8) -0.0017(6) 0.0081(6) -0.0025(6) C46 0.0143(7) 0.0177(7) 0.0164(7) 0.0014(6) 0.0052(6) 0.0000(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 C1 1.7012(17) . ? S1 S2 2.3374(5) . ? S2 C2 1.7600(15) . ? S2 S3 2.3408(5) . ? S3 C4 1.7083(15) . ? N1 C1 1.320(2) . ? N1 C2 1.357(2) . ? C1 C11 1.506(2) . ? C2 C3 1.409(2) . ? C3 C4 1.384(2) . ? C3 H3A 0.9500 . ? C4 C41 1.484(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C41 C42 1.403(2) . ? C41 C46 1.405(2) . ? C42 C43 1.397(2) . ? C42 H42A 0.9500 . ? C43 C44 1.393(2) . ? C43 H43A 0.9500 . ? C44 C45 1.393(2) . ? C44 H44A 0.9500 . ? C45 C46 1.395(2) . ? C45 H45A 0.9500 . ? C46 H46A 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 S2 91.68(6) . . ? C2 S2 S1 86.96(5) . . ? C2 S2 S3 88.84(5) . . ? S1 S2 S3 175.80(2) . . ? C4 S3 S2 94.31(5) . . ? C1 N1 C2 117.99(14) . . ? N1 C1 C11 119.30(15) . . ? N1 C1 S1 121.22(12) . . ? C11 C1 S1 119.48(12) . . ? N1 C2 C3 118.98(14) . . ? N1 C2 S2 122.14(12) . . ? C3 C2 S2 118.88(11) . . ? C4 C3 C2 121.29(14) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C41 123.13(14) . . ? C3 C4 S3 116.66(11) . . ? C41 C4 S3 120.21(11) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C42 C41 C46 118.92(14) . . ? C42 C41 C4 120.45(14) . . ? C46 C41 C4 120.63(14) . . ? C43 C42 C41 120.23(14) . . ? C43 C42 H42A 119.9 . . ? C41 C42 H42A 119.9 . . ? C44 C43 C42 120.43(15) . . ? C44 C43 H43A 119.8 . . ? C42 C43 H43A 119.8 . . ? C45 C44 C43 119.72(14) . . ? C45 C44 H44A 120.1 . . ? C43 C44 H44A 120.1 . . ? C44 C45 C46 120.21(15) . . ? C44 C45 H45A 119.9 . . ? C46 C45 H45A 119.9 . . ? C45 C46 C41 120.49(15) . . ? C45 C46 H46A 119.8 . . ? C41 C46 H46A 119.8 . . ? 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 C1 S1 S2 C2 -0.89(7) . . . . ? C1 S1 S2 S3 -0.6(4) . . . . ? C2 S2 S3 C4 -1.39(7) . . . . ? S1 S2 S3 C4 -1.7(4) . . . . ? C2 N1 C1 C11 -179.80(15) . . . . ? C2 N1 C1 S1 0.3(2) . . . . ? S2 S1 C1 N1 0.51(14) . . . . ? S2 S1 C1 C11 -179.36(13) . . . . ? C1 N1 C2 C3 178.67(15) . . . . ? C1 N1 C2 S2 -1.4(2) . . . . ? S1 S2 C2 N1 1.36(13) . . . . ? S3 S2 C2 N1 -178.61(13) . . . . ? S1 S2 C2 C3 -178.69(13) . . . . ? S3 S2 C2 C3 1.33(13) . . . . ? N1 C2 C3 C4 179.20(15) . . . . ? S2 C2 C3 C4 -0.7(2) . . . . ? C2 C3 C4 C41 178.67(14) . . . . ? C2 C3 C4 S3 -0.8(2) . . . . ? S2 S3 C4 C3 1.38(13) . . . . ? S2 S3 C4 C41 -178.07(12) . . . . ? C3 C4 C41 C42 -26.8(2) . . . . ? S3 C4 C41 C42 152.66(13) . . . . ? C3 C4 C41 C46 153.23(16) . . . . ? S3 C4 C41 C46 -27.4(2) . . . . ? C46 C41 C42 C43 0.3(2) . . . . ? C4 C41 C42 C43 -179.69(15) . . . . ? C41 C42 C43 C44 -0.3(3) . . . . ? C42 C43 C44 C45 -0.3(3) . . . . ? C43 C44 C45 C46 0.8(2) . . . . ? C44 C45 C46 C41 -0.8(2) . . . . ? C42 C41 C46 C45 0.2(2) . . . . ? C4 C41 C46 C45 -179.76(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.342 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.054