#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202183.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_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_ _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_bond_atom_site_label_1 _geom_bond_atom_site_label_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_ _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)