#------------------------------------------------------------------------------ #$Date: 2011-01-02 20:00:31 +0000 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206936.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_2206936 loop_ _publ_author_name 'Xu, Liang-Zhong' 'Yu, Guan-Ping' 'Yin, Shu-Mei' 'Zhou, Kai' 'Yang, Shuang-Hua' _publ_section_title ; 2-{5-[(1H-1,2,4-Triazol-1-yl)methyl]-1,3,4-oxadiazol-2-ylthio}-1-(2,4-dichlorophenyl)ethanone ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3375 _journal_page_last o3376 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H9 Cl2 N5 O2 S' _chemical_formula_moiety 'C13 H9 Cl2 N5 O2 S' _chemical_formula_sum 'C13 H9 Cl2 N5 O2 S' _chemical_formula_weight 370.21 _chemical_name_systematic ; 2-(5-((1H-1,2,4-triazol-1-yl)methyl)-1,3,4-oxadiazol-2-ylthio)-1 -(2,4-dichlorophenyl)ethanone ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.217(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3130(13) _cell_length_b 25.231(4) _cell_length_c 8.4269(15) _cell_measurement_reflns_used 2652 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 25.62 _cell_measurement_theta_min 2.57 _cell_volume 1542.5(5) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8564 _diffrn_reflns_theta_full 26.40 _diffrn_reflns_theta_max 26.40 _diffrn_reflns_theta_min 1.61 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.572 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.458 _refine_diff_density_min -0.350 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 3149 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0399 _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^)+(0.0334P)^2^+0.9960P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.0968 _reflns_number_gt 2155 _reflns_number_total 3149 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6581.cif _[local]_cod_cif_authors_sg_H-M P21/c _[local]_cod_cif_authors_sg_Hall '-P 2yb c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 ; _cod_database_code 2206936 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 0.49983(10) 0.31043(3) 0.47413(9) 0.0475(2) Uani d . 1 S Cl1 0.20912(12) 0.46420(3) 0.64374(8) 0.0635(3) Uani d . 1 Cl Cl2 0.26195(13) 0.51360(4) 1.25679(10) 0.0725(3) Uani d . 1 Cl O1 0.8175(2) 0.26011(6) 0.5168(2) 0.0389(4) Uani d . 1 O O2 0.4529(3) 0.30945(7) 0.8152(2) 0.0594(6) Uani d . 1 O N1 0.8287(3) 0.33526(8) 0.6529(3) 0.0418(5) Uani d . 1 N N2 1.0024(3) 0.30981(8) 0.6816(2) 0.0413(5) Uani d . 1 N N3 1.0583(3) 0.17445(8) 0.6414(2) 0.0348(5) Uani d . 1 N N4 1.0617(3) 0.16429(9) 0.7998(3) 0.0489(6) Uani d . 1 N N5 0.9179(3) 0.09881(9) 0.6516(3) 0.0522(6) Uani d . 1 N C1 0.4360(4) 0.36590(10) 0.5891(3) 0.0396(6) Uani d . 1 C H1A 0.5251 0.3941 0.5830 0.048 Uiso calc R 1 H H1B 0.3170 0.3790 0.5411 0.048 Uiso calc R 1 H C2 0.4249(3) 0.35352(10) 0.7635(3) 0.0389(6) Uani d . 1 C C3 0.3839(3) 0.39733(10) 0.8748(3) 0.0364(6) Uani d . 1 C C4 0.2895(3) 0.44484(10) 0.8380(3) 0.0390(6) Uani d . 1 C C5 0.2521(4) 0.48029(10) 0.9551(3) 0.0437(6) Uani d . 1 C H5 0.1862 0.5112 0.9279 0.052 Uiso calc R 1 H C6 0.3135(4) 0.46912(11) 1.1113(3) 0.0458(7) Uani d . 1 C C7 0.4119(4) 0.42401(12) 1.1544(3) 0.0514(7) Uani d . 1 C H7 0.4563 0.4176 1.2610 0.062 Uiso calc R 1 H C8 0.4439(4) 0.38849(11) 1.0372(3) 0.0458(7) Uani d . 1 C H8 0.5077 0.3574 1.0669 0.055 Uiso calc R 1 H C9 0.7275(3) 0.30448(9) 0.5574(3) 0.0361(6) Uani d . 1 C C10 0.9885(3) 0.26711(10) 0.6000(3) 0.0348(6) Uani d . 1 C C11 1.1267(3) 0.22441(10) 0.5879(3) 0.0406(6) Uani d . 1 C H11A 1.1514 0.2211 0.4779 0.049 Uiso calc R 1 H H11B 1.2413 0.2335 0.6532 0.049 Uiso calc R 1 H C12 0.9718(4) 0.13549(10) 0.5575(3) 0.0444(6) Uani d . 1 C H12 0.9519 0.1343 0.4463 0.053 Uiso calc R 1 H C13 0.9758(4) 0.11856(12) 0.7975(3) 0.0514(7) Uani d . 1 C H13 0.9561 0.1009 0.8909 0.062 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 0.0437(4) 0.0417(4) 0.0543(4) 0.0074(3) -0.0050(3) -0.0131(3) Cl1 0.0918(6) 0.0580(5) 0.0394(4) 0.0347(4) 0.0034(4) 0.0054(3) Cl2 0.0855(6) 0.0830(6) 0.0536(5) -0.0218(5) 0.0263(4) -0.0234(4) O1 0.0383(10) 0.0324(9) 0.0449(10) 0.0029(7) 0.0009(8) -0.0085(8) O2 0.0743(14) 0.0371(11) 0.0694(14) 0.0104(10) 0.0188(11) 0.0157(10) N1 0.0425(13) 0.0385(12) 0.0437(13) 0.0021(10) 0.0032(10) -0.0089(10) N2 0.0390(12) 0.0422(13) 0.0420(12) -0.0014(10) 0.0025(10) -0.0083(10) N3 0.0355(11) 0.0347(11) 0.0342(11) 0.0045(9) 0.0042(9) -0.0017(9) N4 0.0623(16) 0.0490(14) 0.0350(12) 0.0005(12) 0.0040(11) 0.0008(11) N5 0.0537(15) 0.0434(13) 0.0576(15) -0.0030(11) -0.0006(12) 0.0032(12) C1 0.0385(14) 0.0354(14) 0.0439(15) 0.0066(11) 0.0011(12) -0.0018(11) C2 0.0298(13) 0.0358(14) 0.0511(16) -0.0002(11) 0.0055(11) 0.0061(12) C3 0.0312(13) 0.0394(14) 0.0390(14) -0.0035(11) 0.0069(11) 0.0087(11) C4 0.0410(15) 0.0396(14) 0.0367(14) 0.0010(11) 0.0068(11) 0.0070(11) C5 0.0469(16) 0.0418(15) 0.0443(16) -0.0006(12) 0.0135(13) 0.0014(12) C6 0.0464(16) 0.0537(17) 0.0394(15) -0.0170(13) 0.0143(13) -0.0052(13) C7 0.0515(17) 0.066(2) 0.0353(15) -0.0150(15) 0.0007(13) 0.0082(14) C8 0.0401(15) 0.0496(16) 0.0470(16) -0.0032(12) 0.0021(12) 0.0160(13) C9 0.0420(14) 0.0323(13) 0.0346(13) 0.0028(11) 0.0073(11) -0.0011(11) C10 0.0350(14) 0.0357(14) 0.0340(13) -0.0001(10) 0.0050(11) 0.0008(11) C11 0.0370(14) 0.0421(15) 0.0432(14) 0.0009(11) 0.0074(12) 0.0001(12) C12 0.0490(16) 0.0421(15) 0.0401(15) 0.0006(12) -0.0023(12) -0.0044(13) C13 0.0559(18) 0.0528(18) 0.0464(17) 0.0054(14) 0.0098(14) 0.0092(14) 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' Cl Cl 0.1484 0.1585 '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 C1 98.68(12) yes C9 O1 C10 101.82(18) yes C9 N1 N2 105.47(19) ? C10 N2 N1 106.4(2) ? C12 N3 N4 109.5(2) ? C12 N3 C11 129.8(2) ? N4 N3 C11 120.4(2) ? C13 N4 N3 101.7(2) ? C12 N5 C13 102.0(2) ? C2 C1 S1 114.31(17) ? C2 C1 H1A 108.7 ? S1 C1 H1A 108.7 ? C2 C1 H1B 108.7 ? S1 C1 H1B 108.7 ? H1A C1 H1B 107.6 ? O2 C2 C3 119.5(2) ? O2 C2 C1 121.0(2) ? C3 C2 C1 119.5(2) ? C4 C3 C8 116.0(2) ? C4 C3 C2 128.5(2) ? C8 C3 C2 115.4(2) ? C5 C4 C3 122.1(2) ? C5 C4 Cl1 114.6(2) ? C3 C4 Cl1 123.3(2) ? C6 C5 C4 118.9(3) ? C6 C5 H5 120.5 ? C4 C5 H5 120.5 ? C5 C6 C7 121.7(3) ? C5 C6 Cl2 118.2(2) ? C7 C6 Cl2 120.1(2) ? C6 C7 C8 118.8(3) ? C6 C7 H7 120.6 ? C8 C7 H7 120.6 ? C7 C8 C3 122.5(3) ? C7 C8 H8 118.8 ? C3 C8 H8 118.8 ? N1 C9 O1 113.3(2) ? N1 C9 S1 130.63(19) ? O1 C9 S1 116.08(17) ? N2 C10 O1 113.1(2) ? N2 C10 C11 129.7(2) ? O1 C10 C11 117.2(2) ? N3 C11 C10 110.1(2) ? N3 C11 H11A 109.6 ? C10 C11 H11A 109.6 ? N3 C11 H11B 109.6 ? C10 C11 H11B 109.6 ? H11A C11 H11B 108.1 ? N5 C12 N3 111.2(2) ? N5 C12 H12 124.4 ? N3 C12 H12 124.4 ? N4 C13 N5 115.7(2) ? N4 C13 H13 122.1 ? N5 C13 H13 122.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C9 1.730(3) yes S1 C1 1.797(2) yes Cl1 C4 1.738(2) ? Cl2 C6 1.738(3) ? O1 C9 1.364(3) yes O1 C10 1.366(3) yes O2 C2 1.202(3) ? N1 C9 1.284(3) yes N1 N2 1.417(3) yes N2 C10 1.275(3) yes N3 C12 1.324(3) ? N3 N4 1.357(3) ? N3 C11 1.449(3) ? N4 C13 1.313(4) ? N5 C12 1.311(3) ? N5 C13 1.345(4) ? C1 C2 1.515(4) ? C1 H1A 0.9700 ? C1 H1B 0.9700 ? C2 C3 1.504(3) ? C3 C4 1.399(3) ? C3 C8 1.401(3) ? C4 C5 1.385(3) ? C5 C6 1.365(4) ? C5 H5 0.9300 ? C6 C7 1.371(4) ? C7 C8 1.375(4) ? C7 H7 0.9300 ? C8 H8 0.9300 ? C10 C11 1.489(3) ? C11 H11A 0.9700 ? C11 H11B 0.9700 ? C12 H12 0.9300 ? C13 H13 0.9300 ? 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 C5 H5 N5 2_656 0.93 2.41 3.319(4) 167.2 C1 H1B Cl1 . 0.97 2.48 3.051(2) 117.2 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 C9 N1 N2 C10 0.7(3) C12 N3 N4 C13 0.5(3) C11 N3 N4 C13 174.8(2) C9 S1 C1 C2 -70.0(2) S1 C1 C2 O2 -1.8(3) S1 C1 C2 C3 176.37(18) O2 C2 C3 C4 -156.2(3) C1 C2 C3 C4 25.6(4) O2 C2 C3 C8 21.7(3) C1 C2 C3 C8 -156.5(2) C8 C3 C4 C5 -2.0(4) C2 C3 C4 C5 176.0(2) C8 C3 C4 Cl1 178.23(19) C2 C3 C4 Cl1 -3.8(4) C3 C4 C5 C6 1.7(4) Cl1 C4 C5 C6 -178.5(2) C4 C5 C6 C7 0.5(4) C4 C5 C6 Cl2 -179.00(19) C5 C6 C7 C8 -2.1(4) Cl2 C6 C7 C8 177.3(2) C6 C7 C8 C3 1.8(4) C4 C3 C8 C7 0.2(4) C2 C3 C8 C7 -178.0(2) N2 N1 C9 O1 -0.5(3) N2 N1 C9 S1 179.50(19) C10 O1 C9 N1 0.2(3) C10 O1 C9 S1 -179.86(16) C1 S1 C9 N1 -10.0(3) C1 S1 C9 O1 170.03(18) N1 N2 C10 O1 -0.6(3) N1 N2 C10 C11 -178.3(2) C9 O1 C10 N2 0.3(3) C9 O1 C10 C11 178.3(2) C12 N3 C11 C10 95.6(3) N4 N3 C11 C10 -77.4(3) N2 C10 C11 N3 119.4(3) O1 C10 C11 N3 -58.2(3) C13 N5 C12 N3 0.7(3) N4 N3 C12 N5 -0.8(3) C11 N3 C12 N5 -174.4(2) N3 N4 C13 N5 -0.1(3) C12 N5 C13 N4 -0.4(3)