#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200383.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_2200383 loop_ _publ_author_name 'Wei-Qiang Chen' 'Miao Du' 'Lin-Hong Weng' 'Gui-Yu Jin' _publ_section_title ; Ethyl 1-phenyl-3-sulfanyl-5-(4H-1,2,4-triazol-4-yl)pyrazole-4-carboxylate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o619 _journal_page_last o621 _journal_paper_doi 10.1107/S1600536801010091 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C15 H15 N5 O2 S' _chemical_formula_moiety 'C15 H15 N5 O2 S' _chemical_formula_sum 'C15 H15 N5 O2 S' _chemical_formula_weight 329.38 _chemical_name_systematic ; Ethyl 1-phenyl-3-sulfanyl-5-(4H-1,2,4-triazol-4-yl)pyrazole-4-carboxylate ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.669(5) _cell_length_b 17.063(9) _cell_length_c 17.875(10) _cell_measurement_reflns_used 11458 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.02 _cell_measurement_theta_min 2.28 _cell_volume 2949(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'XP (Bruker, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_measured_fraction_theta_full 1.0 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0581 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11622 _diffrn_reflns_theta_full 22.48 _diffrn_reflns_theta_max 25.02 _diffrn_standards_decay_% none _diffrn_standards_interval_count none _diffrn_standards_number none _exptl_absorpt_coefficient_mu .238 _exptl_absorpt_correction_T_max .9652 _exptl_absorpt_correction_T_min .9429 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 1376 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .194 _refine_diff_density_min -.265 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 208 _refine_ls_number_reflns 2614 _refine_ls_R_factor_all .0611 _refine_ls_R_factor_gt .0380 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.8570P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1106 _reflns_number_gt 1880 _reflns_number_total 2614 _reflns_threshold_expression I>2.0\s(I) _cod_data_source_file bt6051.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 2200383 _cod_database_fobs_code 2200383 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 .12479(6) .04165(4) .03864(4) .0566(2) Uani d . 1 . . S N1 .41216(17) .13451(10) .14576(10) .0386(4) Uani d . 1 . . N N2 .28698(17) .13683(10) .11354(10) .0426(5) Uani d . 1 . . N N3 .59841(17) .04882(10) .16515(10) .0381(4) Uani d . 1 . . N N4 .8160(2) .03795(17) .17932(14) .0791(8) Uani d . 1 . . N N5 .7537(2) .00862(14) .24043(13) .0625(6) Uani d . 1 . . N O1 .31105(18) -.09285(10) .03928(10) .0606(5) Uani d . 1 . . O O2 .51746(16) -.08857(8) .08832(9) .0487(4) Uani d . 1 . . O C1 .4708(2) .06543(12) .13590(12) .0360(5) Uani d . 1 . . C C2 .3840(2) .02021(12) .09644(12) .0369(5) Uani d . 1 . . C C3 .2703(2) .06771(13) .08458(12) .0409(5) Uani d . 1 . . C C4 .0301(3) .12862(14) .04463(15) .0585(7) Uani d . 1 . . C H4A -.0574 .1219 .0201 .088 Uiso calc R 1 . . H H4B .0806 .1701 .0208 .088 Uiso calc R 1 . . H H4C .0152 .1416 .0963 .088 Uiso calc R 1 . . H C5 .3982(2) -.05895(13) .07177(13) .0414(5) Uani d . 1 . . C C6 .7211(2) .06113(19) .13576(15) .0663(8) Uani d . 1 . . C H6A .7362 .0838 .0892 .080 Uiso calc R 1 . . H C7 .6251(3) .01562(15) .23047(14) .0543(7) Uani d . 1 . . C H7A .5581 -.0004 .2645 .065 Uiso calc R 1 . . H C8 .4651(2) .20372(12) .17602(12) .0398(5) Uani d . 1 . . C C9 .5439(3) .20235(14) .23805(14) .0507(6) Uani d . 1 . . C H9A .5613 .1554 .2627 .061 Uiso calc R 1 . . H C10 .5974(3) .27019(16) .26387(16) .0598(7) Uani d . 1 . . C H10A .6543 .2697 .3058 .072 Uiso calc R 1 . . H C11 .5694(3) .33810(16) .22973(16) .0628(7) Uani d . 1 . . C H11A .6069 .3845 .2480 .075 Uiso calc R 1 . . H C12 .4876(3) .33943(15) .16946(16) .0608(7) Uani d . 1 . . C H12A .4663 .3870 .1467 .073 Uiso calc R 1 . . H C13 .4356(3) .27205(13) .14139(13) .0487(6) Uani d . 1 . . C H13A .3803 .2727 .0988 .058 Uiso calc R 1 . . H C14 .5418(3) -.16603(14) .06275(15) .0561(7) Uani d . 1 . . C H14A .5442 -.1673 .0085 .067 Uiso calc R 1 . . H H14B .4690 -.2008 .0799 .067 Uiso calc R 1 . . H C15 .6737(3) -.19033(17) .0930(2) .0817(10) Uani d . 1 . . C H15A .6942 -.2426 .0765 .123 Uiso calc R 1 . . H H15B .6697 -.1893 .1467 .123 Uiso calc R 1 . . H H15C .7447 -.1553 .0760 .123 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 .0413(4) .0503(4) .0784(5) -.0009(3) -.0199(3) -.0123(3) N1 .0341(9) .0391(10) .0425(10) -.0030(8) -.0056(8) -.0051(8) N2 .0346(10) .0423(11) .0510(11) -.0020(8) -.0079(8) -.0050(9) N3 .0337(9) .0409(10) .0398(10) .0010(8) -.0051(8) -.0032(8) N4 .0418(12) .129(2) .0668(17) .0135(14) -.0089(12) -.0151(16) N5 .0587(14) .0658(14) .0630(15) .0174(11) -.0181(12) -.0096(11) O1 .0560(10) .0487(10) .0773(13) -.0024(9) -.0223(9) -.0157(9) O2 .0458(9) .0399(9) .0604(11) .0040(7) -.0072(8) -.0107(7) C1 .0337(11) .0378(12) .0364(12) -.0004(9) -.0006(9) .0014(9) C2 .0364(11) .0366(12) .0376(12) -.0036(9) -.0030(9) -.0022(9) C3 .0365(12) .0429(13) .0433(13) -.0036(10) -.0018(10) -.0013(10) C4 .0458(14) .0557(16) .0741(18) .0058(12) -.0112(13) -.0058(13) C5 .0428(13) .0412(13) .0404(13) -.0031(10) -.0030(10) -.0010(10) C6 .0383(14) .111(2) .0492(16) .0013(14) .0022(12) .0009(15) C7 .0552(16) .0526(15) .0552(16) .0034(12) -.0125(12) .0065(11) C8 .0361(11) .0382(12) .0451(13) -.0063(9) .0016(10) -.0080(10) C9 .0543(15) .0458(14) .0520(15) .0009(11) -.0092(12) -.0079(11) C10 .0533(15) .0613(18) .0646(17) -.0025(12) -.0104(13) -.0235(14) C11 .0620(17) .0509(16) .076(2) -.0144(13) .0046(15) -.0197(14) C12 .0778(18) .0406(14) .0640(17) -.0066(13) .0076(15) -.0033(12) C13 .0552(14) .0407(14) .0500(14) -.0035(11) -.0006(12) -.0015(11) C14 .0633(16) .0407(14) .0644(17) .0067(12) .0007(13) -.0092(11) C15 .0634(18) .0635(18) .118(3) .0164(15) -.0017(18) -.0011(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .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 C3 S1 C4 100.55(12) yes C1 N1 N2 110.90(16) yes C1 N1 C8 130.53(18) yes N2 N1 C8 118.17(17) yes C3 N2 N1 104.87(17) yes C6 N3 C7 104.2(2) yes C6 N3 C1 128.8(2) yes C7 N3 C1 127.0(2) yes C6 N4 N5 106.9(2) yes C7 N5 N4 107.0(2) yes C5 O2 C14 116.01(18) yes N1 C1 C2 108.39(18) no N1 C1 N3 121.39(18) no C2 C1 N3 130.2(2) no C1 C2 C3 103.95(19) no C1 C2 C5 130.3(2) no C3 C2 C5 125.69(19) no N2 C3 C2 111.88(19) no N2 C3 S1 122.47(17) no C2 C3 S1 125.65(17) no S1 C4 H4A 109.5 no S1 C4 H4B 109.5 no H4A C4 H4B 109.5 no S1 C4 H4C 109.5 no H4A C4 H4C 109.5 no H4B C4 H4C 109.5 no O1 C5 O2 124.0(2) no O1 C5 C2 123.4(2) no O2 C5 C2 112.60(19) no N4 C6 N3 111.0(3) no N4 C6 H6A 124.5 no N3 C6 H6A 124.5 no N5 C7 N3 111.0(2) no N5 C7 H7A 124.5 no N3 C7 H7A 124.5 no C9 C8 C13 120.8(2) no C9 C8 N1 120.8(2) no C13 C8 N1 118.4(2) no C8 C9 C10 118.9(2) no C8 C9 H9A 120.5 no C10 C9 H9A 120.5 no C11 C10 C9 120.6(3) no C11 C10 H10A 119.7 no C9 C10 H10A 119.7 no C12 C11 C10 120.2(2) no C12 C11 H11A 119.9 no C10 C11 H11A 119.9 no C11 C12 C13 120.3(3) no C11 C12 H12A 119.8 no C13 C12 H12A 119.8 no C8 C13 C12 119.1(2) no C8 C13 H13A 120.5 no C12 C13 H13A 120.5 no O2 C14 C15 107.0(2) no O2 C14 H14A 110.3 no C15 C14 H14A 110.3 no O2 C14 H14B 110.3 no C15 C14 H14B 110.3 no H14A C14 H14B 108.6 no C14 C15 H15A 109.5 no C14 C15 H15B 109.5 no H15A C15 H15B 109.5 no C14 C15 H15C 109.5 no H15A C15 H15C 109.5 no H15B C15 H15C 109.5 no 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 C3 . 1.689(2) yes S1 C4 . 1.747(3) yes N1 C1 . 1.320(3) yes N1 N2 . 1.341(2) yes N1 C8 . 1.396(3) yes N2 C3 . 1.298(3) yes N3 C6 . 1.314(3) yes N3 C7 . 1.323(3) yes N3 C1 . 1.370(3) yes N4 C6 . 1.266(3) yes N4 N5 . 1.344(3) yes N5 C7 . 1.261(3) yes O1 C5 . 1.175(3) yes O2 C5 . 1.294(3) yes O2 C14 . 1.418(3) yes C1 C2 . 1.340(3) no C2 C3 . 1.383(3) no C2 C5 . 1.427(3) no C4 H4A . .9600 no C4 H4B . .9600 no C4 H4C . .9600 no C6 H6A . .9300 no C7 H7A . .9300 no C8 C9 . 1.346(3) no C8 C13 . 1.350(3) no C9 C10 . 1.349(3) no C9 H9A . .9300 no C10 C11 . 1.337(4) no C10 H10A . .9300 no C11 C12 . 1.337(4) no C11 H11A . .9300 no C12 C13 . 1.351(3) no C12 H12A . .9300 no C13 H13A . .9300 no C14 C15 . 1.446(4) no C14 H14A . .9700 no C14 H14B . .9700 no C15 H15A . .9600 no C15 H15B . .9600 no C15 H15C . .9600 no 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 _geom_hbond_publ_flag C6 H6A O1 5_655 .930 2.346 3.190(4) 150.8 yes C11 H11A N5 8_765 .930 2.514 3.381(3) 155.2 yes