#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202183.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202183 loop_ _publ_author_name 'Zhang, Yu-Xia' _publ_section_title ; 5-[(2-Hydroxyphenyl)methyleneamino]-1,3,4-thiadiazole-2(3H)-thione ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o581 _journal_page_last o582 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C9 H7 N3 O S2' _chemical_formula_moiety 'C9 H7 N3 O S2' _chemical_formula_sum 'C9 H7 N3 O S2' _chemical_formula_weight 237.30 _chemical_name_systematic ; 5-[(2-Hydroxyphenyl)methleneamino]-1,3,4-thiadiazole-2(3H)-thione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 99.183(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.587(3) _cell_length_b 13.723(5) _cell_length_c 11.758(5) _cell_measurement_reflns_used 662 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 3.1 _cell_volume 1049.2(8) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_av_sigmaI/netI 0.033 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2862 _diffrn_reflns_theta_full 25.1 _diffrn_reflns_theta_max 25.1 _diffrn_reflns_theta_min 2.3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.48 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Blessing, 1995; Sheldrick, 1996)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.22 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1822 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.06 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.034 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.2779P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.077 _refine_ls_wR_factor_ref 0.085 _reflns_number_gt 1440 _reflns_number_total 1822 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tk6096.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1049.2(7) _cod_database_code 2202183 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.02404(9) 0.41301(5) 0.69266(5) 0.0463(2) Uani d . 1 . . S S2 -0.37268(10) 0.52545(5) 0.68937(5) 0.0553(2) Uani d . 1 . . S N2 -0.1020(3) 0.36578(15) 0.48081(15) 0.0490(5) Uani d . 1 . . N N1 0.2126(3) 0.29468(14) 0.54584(15) 0.0451(5) Uani d . 1 . . N N3 -0.2447(3) 0.42387(14) 0.51818(15) 0.0467(5) Uani d . 1 . . N H3A -0.3548 0.4395 0.4721 0.056 Uiso calc R 1 . . H C6 0.5334(3) 0.21686(16) 0.61021(17) 0.0389(5) Uani d . 1 . . C C5 0.6984(4) 0.20360(16) 0.70044(19) 0.0445(6) Uani d . 1 . . C H5 0.6946 0.2334 0.7711 0.053 Uiso calc R 1 . . H C7 0.3638(3) 0.27793(16) 0.62733(18) 0.0413(5) Uani d . 1 . . C H7 0.3632 0.3061 0.6992 0.050 Uiso calc R 1 . . H C8 0.0505(4) 0.35235(16) 0.56372(17) 0.0418(6) Uani d . 1 . . C C9 -0.2142(3) 0.45686(16) 0.62677(18) 0.0422(5) Uani d . 1 . . C C1 0.5415(4) 0.16994(19) 0.50441(19) 0.0512(6) Uani d . 1 . . C C4 0.8644(4) 0.14782(18) 0.6865(2) 0.0528(6) Uani d . 1 . . C H4 0.9729 0.1402 0.7469 0.063 Uiso calc R 1 . . H O1 0.3886(3) 0.17983(17) 0.41334(14) 0.0781(6) Uani d . 1 . . O H1 0.2950 0.2121 0.4326 0.117 Uiso calc R 1 . . H C3 0.8696(5) 0.10311(19) 0.5824(2) 0.0627(8) Uani d . 1 . . C H3 0.9835 0.0658 0.5727 0.075 Uiso calc R 1 . . H C2 0.7088(5) 0.1126(2) 0.4918(2) 0.0665(8) Uani d . 1 . . C H2 0.7134 0.0804 0.4226 0.080 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0449(4) 0.0553(4) 0.0351(3) 0.0079(3) -0.0048(2) -0.0032(3) S2 0.0478(4) 0.0715(5) 0.0436(3) 0.0128(3) -0.0018(3) -0.0044(3) N2 0.0479(12) 0.0623(13) 0.0345(10) 0.0063(10) -0.0005(9) 0.0006(9) N1 0.0472(12) 0.0529(12) 0.0340(10) 0.0069(10) 0.0025(9) 0.0004(8) N3 0.0418(11) 0.0608(12) 0.0342(10) 0.0058(10) -0.0040(8) 0.0020(9) C6 0.0442(13) 0.0413(12) 0.0315(11) 0.0006(10) 0.0066(10) 0.0035(9) C5 0.0513(14) 0.0470(13) 0.0339(11) 0.0025(12) 0.0032(10) 0.0028(10) C7 0.0473(14) 0.0471(13) 0.0296(11) -0.0016(11) 0.0063(10) 0.0011(9) C8 0.0460(14) 0.0476(13) 0.0304(11) -0.0014(11) 0.0017(10) 0.0029(10) C9 0.0411(13) 0.0455(13) 0.0377(12) -0.0039(11) -0.0011(10) 0.0044(10) C1 0.0621(17) 0.0565(15) 0.0335(12) 0.0081(13) 0.0030(11) 0.0002(11) C4 0.0528(15) 0.0550(15) 0.0479(14) 0.0107(13) -0.0001(11) 0.0057(12) O1 0.0837(15) 0.1076(16) 0.0364(9) 0.0337(13) -0.0111(9) -0.0168(10) C3 0.0703(19) 0.0609(17) 0.0582(16) 0.0254(15) 0.0145(14) 0.0017(13) C2 0.086(2) 0.0679(18) 0.0450(14) 0.0236(16) 0.0093(14) -0.0100(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C9 . 1.743(2) yes S1 C8 . 1.762(2) yes S2 C9 . 1.662(3) yes N2 C8 . 1.296(3) yes N2 N3 . 1.358(3) yes N1 C7 . 1.288(3) yes N1 C8 . 1.372(3) yes N3 C9 . 1.339(3) yes N3 H3A . 0.8600 ? C6 C5 . 1.404(3) ? C6 C1 . 1.409(3) ? C6 C7 . 1.436(3) ? C5 C4 . 1.366(3) ? C5 H5 . 0.9300 ? C7 H7 . 0.9300 ? C1 O1 . 1.354(3) yes C1 C2 . 1.382(4) ? C4 C3 . 1.375(3) ? C4 H4 . 0.9300 ? O1 H1 . 0.8200 ? C3 C2 . 1.383(4) ? C3 H3 . 0.9300 ? C2 H2 . 0.9300 ? 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C9 S1 C8 89.22(11) ? C8 N2 N3 109.48(19) ? C7 N1 C8 121.16(19) yes C9 N3 N2 120.04(18) ? C9 N3 H3A 120.0 ? N2 N3 H3A 120.0 ? C5 C6 C1 118.3(2) ? C5 C6 C7 119.69(19) ? C1 C6 C7 122.0(2) ? C4 C5 C6 121.3(2) ? C4 C5 H5 119.3 ? C6 C5 H5 119.3 ? N1 C7 C6 121.8(2) yes N1 C7 H7 119.1 ? C6 C7 H7 119.1 ? N2 C8 N1 119.7(2) ? N2 C8 S1 114.12(18) ? N1 C8 S1 126.19(16) ? N3 C9 S2 127.19(17) ? N3 C9 S1 107.13(17) ? S2 C9 S1 125.68(13) ? O1 C1 C2 118.5(2) ? O1 C1 C6 121.6(2) ? C2 C1 C6 119.9(2) ? C5 C4 C3 119.4(2) ? C5 C4 H4 120.3 ? C3 C4 H4 120.3 ? C1 O1 H1 109.5 ? C4 C3 C2 121.3(3) ? C4 C3 H3 119.4 ? C2 C3 H3 119.4 ? C1 C2 C3 119.8(2) ? C1 C2 H2 120.1 ? C3 C2 H2 120.1 ? 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 C8 N2 N3 C9 -0.4(3) C1 C6 C5 C4 0.8(3) C7 C6 C5 C4 -178.5(2) C8 N1 C7 C6 179.3(2) C5 C6 C7 N1 177.7(2) C1 C6 C7 N1 -1.6(3) N3 N2 C8 N1 179.24(19) N3 N2 C8 S1 -0.6(3) C7 N1 C8 N2 -178.2(2) C7 N1 C8 S1 1.6(3) C9 S1 C8 N2 1.12(19) C9 S1 C8 N1 -178.8(2) N2 N3 C9 S2 -178.03(17) N2 N3 C9 S1 1.2(3) C8 S1 C9 N3 -1.20(17) C8 S1 C9 S2 178.05(17) C5 C6 C1 O1 -179.6(2) C7 C6 C1 O1 -0.3(4) C5 C6 C1 C2 0.1(4) C7 C6 C1 C2 179.4(2) C6 C5 C4 C3 -0.5(4) C5 C4 C3 C2 -0.8(4) O1 C1 C2 C3 178.4(3) C6 C1 C2 C3 -1.3(4) C4 C3 C2 C1 1.7(5) _cod_database_fobs_code 2202183 _journal_paper_doi 10.1107/S1600536803006627