#------------------------------------------------------------------------------ #$Date: 2017-03-21 19:55:39 +0200 (Tue, 21 Mar 2017) $ #$Revision: 194389 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/81/2218189.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_2218189 loop_ _publ_author_name 'Zareef, Muhammad' 'Arfan, Muhammad' 'Iqbal, Rashid' 'Parvez, Masood' _publ_section_title ; 4-Ethyl-3-(3-pyridyl)-1H-1,2,4-triazole-5(4H)-thione 0.095-hydrate ; _journal_coeditor_code LH2615 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o945 _journal_paper_doi 10.1107/S1600536808011744 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C9 H10 N4 S, 0.095H2 O' _chemical_formula_moiety 'C9 H10 N4 S, 0.095(H2 O)' _chemical_formula_sum 'C9 H10.19 N4 O0.095 S' _chemical_formula_weight 207.96 _chemical_melting_point_gt 440 _chemical_melting_point_lt 441 _chemical_name_systematic ; 4-Ethyl-3-(3-pyridyl)-1H-1,2,4-triazole-5(4H)-thione 0.095-hydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.25(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.076(5) _cell_length_b 8.877(5) _cell_length_c 16.216(8) _cell_measurement_reflns_used 3392 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.4 _cell_measurement_theta_min 3.6 _cell_volume 2023.0(17) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f' _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 0.030 _diffrn_reflns_av_sigmaI/netI 0.054 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3392 _diffrn_reflns_theta_full 27.4 _diffrn_reflns_theta_max 27.4 _diffrn_reflns_theta_min 3.6 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.24 _refine_diff_density_min -0.25 _refine_ls_extinction_coef 0.0038(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 2297 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.075 _refine_ls_R_factor_gt 0.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+1.636P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.091 _refine_ls_wR_factor_ref 0.107 _reflns_number_gt 1616 _reflns_number_total 2297 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh2615.cif _cod_data_source_block I _cod_depositor_comments ; Marking attached hydrogen atoms. Antanas Vaitkus, 2017-03-21 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_enum 1527 2010-12-29 10:47:43Z saulius 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_sg_symbol_H-M 'C 2/c' _cod_database_code 2218189 _cod_database_fobs_code 2218189 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_type_symbol _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_attached_hydrogens S S1 -0.12974(4) 0.05644(7) -0.11164(3) 0.0415(2) Uani d . 1 0 O O1 0.0000 -0.0319(16) -0.2500 0.070(4) Uani d SP 0.19 2 N N1 -0.07296(10) 0.26787(18) 0.09536(9) 0.0256(4) Uani d . 1 0 N N2 -0.13013(11) 0.19176(19) 0.03795(10) 0.0276(4) Uani d . 1 0 H H2 -0.1854(16) 0.158(3) 0.0530(12) 0.033 Uiso d . 1 0 N N3 0.00251(10) 0.22103(18) -0.01818(9) 0.0228(4) Uani d . 1 0 N N4 0.21945(11) 0.53359(19) 0.10227(10) 0.0290(4) Uani d . 1 0 C C1 0.00713(12) 0.2838(2) 0.05951(10) 0.0217(4) Uani d . 1 0 C C2 -0.08639(13) 0.1576(2) -0.03071(12) 0.0267(4) Uani d . 1 0 C C3 0.14695(12) 0.4604(2) 0.06268(11) 0.0246(4) Uani d . 1 0 H H3 0.1343 0.4794 0.0055 0.029 Uiso calc R 1 0 C C4 0.08963(12) 0.3582(2) 0.10142(11) 0.0220(4) Uani d . 1 0 C C5 0.10899(13) 0.3310(2) 0.18541(11) 0.0263(4) Uani d . 1 0 H H5 0.0714 0.2616 0.2140 0.032 Uiso calc R 1 0 C C6 0.18343(14) 0.4061(2) 0.22654(12) 0.0313(5) Uani d . 1 0 H H6 0.1977 0.3897 0.2838 0.038 Uiso calc R 1 0 C C7 0.23642(13) 0.5050(2) 0.18282(12) 0.0313(5) Uani d . 1 0 H H7 0.2878 0.5559 0.2113 0.038 Uiso calc R 1 0 C C8 0.07912(14) 0.1998(2) -0.07478(12) 0.0300(5) Uani d . 1 0 H H8A 0.0756 0.0962 -0.0973 0.036 Uiso calc R 1 0 H H8B 0.1412 0.2110 -0.0436 0.036 Uiso calc R 1 0 C C9 0.07367(17) 0.3113(3) -0.14570(13) 0.0406(6) Uani d . 1 0 H H9A 0.1216 0.2857 -0.1849 0.049 Uiso calc R 1 0 H H9B 0.0856 0.4132 -0.1243 0.049 Uiso calc R 1 0 H H9C 0.0102 0.3072 -0.1738 0.049 Uiso calc R 1 0 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 0.0476(4) 0.0346(4) 0.0398(3) -0.0034(3) -0.0202(3) -0.0060(2) O1 0.107(12) 0.043(9) 0.063(9) 0.000 0.034(9) 0.000 N1 0.0194(8) 0.0271(10) 0.0300(8) -0.0060(7) -0.0022(6) 0.0005(7) N2 0.0201(8) 0.0283(10) 0.0339(9) -0.0080(7) -0.0032(7) 0.0017(7) N3 0.0228(8) 0.0221(9) 0.0232(8) -0.0008(7) -0.0026(6) 0.0016(6) N4 0.0220(8) 0.0282(10) 0.0367(9) -0.0042(7) 0.0002(7) 0.0000(7) C1 0.0209(9) 0.0215(10) 0.0225(9) -0.0007(8) -0.0008(7) 0.0031(7) C2 0.0256(10) 0.0221(11) 0.0315(10) -0.0015(8) -0.0076(8) 0.0044(8) C3 0.0199(9) 0.0269(11) 0.0267(9) -0.0012(8) -0.0001(7) 0.0024(8) C4 0.0180(9) 0.0212(10) 0.0267(9) -0.0001(7) 0.0005(7) -0.0007(8) C5 0.0234(10) 0.0288(11) 0.0268(9) -0.0024(8) 0.0027(7) -0.0005(8) C6 0.0298(10) 0.0399(13) 0.0237(9) -0.0020(9) -0.0034(8) -0.0027(9) C7 0.0226(10) 0.0333(12) 0.0373(11) -0.0047(9) -0.0052(8) -0.0081(9) C8 0.0316(10) 0.0289(12) 0.0299(10) 0.0029(9) 0.0044(8) -0.0006(9) C9 0.0540(14) 0.0397(14) 0.0289(11) 0.0010(11) 0.0096(10) 0.0024(10) 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' O O 0.0106 0.0060 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C2 S1 O1 . . 120.21(15) S1 O1 S1 . 2_554 150.4(5) S1 O1 N1 . 5 77.57(10) S1 O1 N1 2_554 5 122.08(18) C1 N1 N2 . . 103.82(16) C2 N2 N1 . . 113.35(16) C2 N2 H2 . . 127.4(14) N1 N2 H2 . . 118.2(14) C1 N3 C2 . . 107.22(15) C1 N3 C8 . . 128.79(15) C2 N3 C8 . . 123.33(16) C7 N4 C3 . . 117.62(17) N1 C1 N3 . . 111.53(16) N1 C1 C4 . . 121.52(16) N3 C1 C4 . . 126.94(16) N2 C2 N3 . . 104.00(16) N2 C2 S1 . . 127.52(15) N3 C2 S1 . . 128.46(16) N4 C3 C4 . . 123.08(17) N4 C3 H3 . . 118.5 C4 C3 H3 . . 118.5 C3 C4 C5 . . 117.95(16) C3 C4 C1 . . 123.31(16) C5 C4 C1 . . 118.66(16) C6 C5 C4 . . 119.26(18) C6 C5 H5 . . 120.4 C4 C5 H5 . . 120.4 C7 C6 C5 . . 118.57(18) C7 C6 H6 . . 120.7 C5 C6 H6 . . 120.7 N4 C7 C6 . . 123.51(17) N4 C7 H7 . . 118.2 C6 C7 H7 . . 118.2 N3 C8 C9 . . 112.54(17) N3 C8 H8A . . 109.1 C9 C8 H8A . . 109.1 N3 C8 H8B . . 109.1 C9 C8 H8B . . 109.1 H8A C8 H8B . . 107.8 C8 C9 H9A . . 109.5 C8 C9 H9B . . 109.5 H9A C9 H9B . . 109.5 C8 C9 H9C . . 109.5 H9A C9 H9C . . 109.5 H9B C9 H9C . . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance S1 C2 . 1.676(2) S1 O1 . 3.074(4) O1 S1 2_554 3.074(4) O1 N1 5 3.382(9) N1 C1 . 1.305(2) N1 N2 . 1.373(2) N2 C2 . 1.337(3) N2 H2 . 0.88(2) N3 C1 . 1.376(2) N3 C2 . 1.377(2) N3 C8 . 1.467(2) N4 C7 . 1.339(3) N4 C3 . 1.342(2) C1 C4 . 1.469(2) C3 C4 . 1.388(3) C3 H3 . 0.9500 C4 C5 . 1.395(3) C5 C6 . 1.381(3) C5 H5 . 0.9500 C6 C7 . 1.375(3) C6 H6 . 0.9500 C7 H7 . 0.9500 C8 C9 . 1.516(3) C8 H8A . 0.9900 C8 H8B . 0.9900 C9 H9A . 0.9800 C9 H9B . 0.9800 C9 H9C . 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H2 N4 3_445 0.88(2) 1.94(2) 2.792(3) 162(2) 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_site_symmetry_4 _geom_torsion C2 S1 O1 S1 2_554 -60.83(15) C2 S1 O1 N1 5 74.7(3) C1 N1 N2 C2 . 1.6(2) N2 N1 C1 N3 . 0.1(2) N2 N1 C1 C4 . -178.76(16) C2 N3 C1 N1 . -1.8(2) C8 N3 C1 N1 . -172.57(17) C2 N3 C1 C4 . 177.06(18) C8 N3 C1 C4 . 6.3(3) N1 N2 C2 N3 . -2.7(2) N1 N2 C2 S1 . 175.75(14) C1 N3 C2 N2 . 2.6(2) C8 N3 C2 N2 . 174.01(16) C1 N3 C2 S1 . -175.82(15) C8 N3 C2 S1 . -4.4(3) O1 S1 C2 N2 . -172.6(3) O1 S1 C2 N3 . 5.5(3) C7 N4 C3 C4 . 0.2(3) N4 C3 C4 C5 . -0.1(3) N4 C3 C4 C1 . 176.65(18) N1 C1 C4 C3 . -137.4(2) N3 C1 C4 C3 . 43.9(3) N1 C1 C4 C5 . 39.3(3) N3 C1 C4 C5 . -139.4(2) C3 C4 C5 C6 . 0.2(3) C1 C4 C5 C6 . -176.73(18) C4 C5 C6 C7 . -0.3(3) C3 N4 C7 C6 . -0.4(3) C5 C6 C7 N4 . 0.4(3) C1 N3 C8 C9 . -105.1(2) C2 N3 C8 C9 . 85.4(2)