#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/37/2203734.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_2203734 loop_ _publ_author_name 'Li-Rong Wen' 'Gui-Long Zhao' 'Ming Li' 'Xue-Mei Li' 'Shu-Sheng Zhang' 'Ping-Kai Ouyang' _publ_section_title ;Ethyl 3-methyl-1-(3-methylbenzoyl)-5-(methylsulfanyl)-1H-pyrazole-4-carboxylate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1026 _journal_page_last o1028 _journal_paper_doi 10.1107/S1600536804011596 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C16 H18 N2 O3 S' _chemical_formula_moiety 'C16 H18 N2 O3 S' _chemical_formula_sum 'C16 H18 N2 O3 S' _chemical_formula_weight 318.38 _chemical_melting_point 388.5(5) _chemical_name_systematic ;Ethyl 3-methyl-1-(3-methylbenzoyl)-5-(methylsulfanyl)-1H-pyrazole-4-carboxylate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 81.745(5) _cell_angle_beta 73.352(5) _cell_angle_gamma 73.583(5) _cell_formula_units_Z 2 _cell_length_a 7.677(3) _cell_length_b 9.228(3) _cell_length_c 12.271(4) _cell_measurement_reflns_used 4133 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.00 _cell_measurement_theta_min 2.79 _cell_volume 797.1(5) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type ; Simens SMART 1000 CCD area-detector ; _diffrn_measurement_method \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 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4133 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.79 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_T_max 0.9661 _exptl_absorpt_correction_T_min 0.9378 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.213 _refine_diff_density_min -0.316 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2789 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0428 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.049P)^2^+0.2362P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.1089 _reflns_number_gt 2224 _reflns_number_total 2789 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6384.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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: '_chemical_melting_point' value '388--389 K' was changed to '388.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '388--389 K' was changed to '388.5(5)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_database_code 2203734 _cod_database_fobs_code 2203734 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_type_symbol S1 0.22441(9) 0.21759(6) 0.42329(5) 0.04722(19) Uani d . 1 S O1 0.2516(2) 0.51069(16) 0.31410(12) 0.0531(4) Uani d . 1 O O2 0.2780(3) 0.70988(17) 0.38665(14) 0.0631(5) Uani d . 1 O O3 0.2104(3) 0.48758(19) 0.84848(14) 0.0754(6) Uani d . 1 O N1 0.2424(2) 0.39648(18) 0.68027(14) 0.0391(4) Uani d . 1 N N2 0.2274(2) 0.27860(18) 0.62814(14) 0.0404(4) Uani d . 1 N C1 0.2393(3) 0.3771(3) 0.79767(18) 0.0482(5) Uani d . 1 C C2 0.2685(3) 0.2214(2) 0.85222(17) 0.0439(5) Uani d . 1 C C3 0.3944(3) 0.0966(3) 0.79842(19) 0.0542(6) Uani d . 1 C H3 0.4612 0.1068 0.7227 0.065 Uiso calc R 1 H C4 0.4199(4) -0.0427(3) 0.8580(2) 0.0663(7) Uani d . 1 C H4 0.5053 -0.1266 0.8226 0.080 Uiso calc R 1 H C5 0.3193(4) -0.0584(3) 0.9701(2) 0.0678(7) Uani d . 1 C H5 0.3364 -0.1536 1.0088 0.081 Uiso calc R 1 H C6 0.1939(4) 0.0643(3) 1.02589(19) 0.0550(6) Uani d . 1 C C7 0.1713(3) 0.2034(3) 0.96572(18) 0.0488(5) Uani d . 1 C H7 0.0886 0.2877 1.0021 0.059 Uiso calc R 1 H C8 0.0860(5) 0.0472(3) 1.1494(2) 0.0801(9) Uani d . 1 C H8A -0.0056 -0.0079 1.1550 0.120 Uiso calc R 1 H H8B 0.0237 0.1455 1.1775 0.120 Uiso calc R 1 H H8C 0.1717 -0.0070 1.1938 0.120 Uiso calc R 1 H C9 0.2558(3) 0.5219(2) 0.60699(17) 0.0373(5) Uani d . 1 C C10 0.2497(3) 0.4844(2) 0.50384(16) 0.0361(4) Uani d . 1 C C11 0.2330(3) 0.3318(2) 0.52228(16) 0.0354(4) Uani d . 1 C C12 0.2142(4) 0.0463(2) 0.5116(2) 0.0622(7) Uani d . 1 C H12A 0.3217 0.0137 0.5425 0.093 Uiso calc R 1 H H12B 0.2137 -0.0309 0.4669 0.093 Uiso calc R 1 H H12C 0.1015 0.0642 0.5728 0.093 Uiso calc R 1 H C13 0.2759(3) 0.6652(2) 0.6379(2) 0.0509(6) Uani d . 1 C H13A 0.3299 0.7202 0.5701 0.076 Uiso calc R 1 H H13B 0.3562 0.6424 0.6886 0.076 Uiso calc R 1 H H13C 0.1544 0.7255 0.6748 0.076 Uiso calc R 1 H C14 0.2616(3) 0.5824(2) 0.39850(17) 0.0411(5) Uani d . 1 C C15 0.2594(4) 0.5934(3) 0.20422(19) 0.0570(6) Uani d . 1 C H15A 0.3661 0.6376 0.1816 0.068 Uiso calc R 1 H H15B 0.1456 0.6741 0.2073 0.068 Uiso calc R 1 H C16 0.2784(5) 0.4832(3) 0.1217(2) 0.0840(9) Uani d . 1 C H16A 0.3988 0.4114 0.1122 0.126 Uiso calc R 1 H H16B 0.2679 0.5361 0.0497 0.126 Uiso calc R 1 H H16C 0.1808 0.4310 0.1501 0.126 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 0.0667(4) 0.0381(3) 0.0425(3) -0.0158(3) -0.0183(3) -0.0071(2) O1 0.0863(12) 0.0412(8) 0.0373(8) -0.0221(8) -0.0231(8) 0.0067(6) O2 0.1004(14) 0.0413(9) 0.0545(10) -0.0309(9) -0.0234(9) 0.0082(7) O3 0.1353(18) 0.0554(10) 0.0468(10) -0.0331(11) -0.0300(11) -0.0078(8) N1 0.0525(11) 0.0340(9) 0.0348(9) -0.0134(8) -0.0152(8) -0.0025(7) N2 0.0535(11) 0.0332(9) 0.0383(9) -0.0139(8) -0.0148(8) -0.0027(7) C1 0.0620(15) 0.0486(13) 0.0383(12) -0.0163(11) -0.0164(10) -0.0051(10) C2 0.0490(13) 0.0494(12) 0.0354(11) -0.0123(10) -0.0153(10) -0.0016(9) C3 0.0530(15) 0.0642(15) 0.0364(12) -0.0061(11) -0.0089(11) 0.0019(11) C4 0.0735(18) 0.0572(15) 0.0470(14) 0.0088(13) -0.0091(13) -0.0014(11) C5 0.088(2) 0.0542(15) 0.0472(14) -0.0054(13) -0.0143(14) 0.0070(12) C6 0.0659(16) 0.0590(15) 0.0369(12) -0.0148(12) -0.0119(11) 0.0014(11) C7 0.0551(14) 0.0533(13) 0.0383(11) -0.0109(11) -0.0135(10) -0.0071(10) C8 0.104(2) 0.0789(19) 0.0437(15) -0.0228(17) -0.0033(15) 0.0051(13) C9 0.0402(12) 0.0307(10) 0.0402(11) -0.0066(8) -0.0106(9) -0.0037(8) C10 0.0394(11) 0.0309(10) 0.0367(11) -0.0070(8) -0.0095(9) -0.0026(8) C11 0.0402(11) 0.0314(10) 0.0353(11) -0.0088(8) -0.0106(9) -0.0033(8) C12 0.0902(19) 0.0386(12) 0.0683(16) -0.0254(12) -0.0282(14) -0.0030(11) C13 0.0666(16) 0.0361(11) 0.0538(14) -0.0132(10) -0.0187(12) -0.0088(10) C14 0.0466(12) 0.0346(11) 0.0411(11) -0.0108(9) -0.0109(10) 0.0007(9) C15 0.0742(17) 0.0584(14) 0.0403(13) -0.0210(12) -0.0220(12) 0.0138(11) C16 0.125(3) 0.082(2) 0.0448(15) -0.0200(18) -0.0290(16) -0.0018(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' 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 C11 S1 C12 99.70(10) C14 O1 C15 117.30(16) C9 N1 N2 112.32(15) C9 N1 C1 128.35(16) N2 N1 C1 119.33(16) C11 N2 N1 104.49(15) O3 C1 N1 118.8(2) O3 C1 C2 123.2(2) N1 C1 C2 118.01(18) C3 C2 C7 119.2(2) C3 C2 C1 123.5(2) C7 C2 C1 117.1(2) C4 C3 C2 119.5(2) C4 C3 H3 120.3 C2 C3 H3 120.3 C3 C4 C5 120.3(2) C3 C4 H4 119.8 C5 C4 H4 119.8 C4 C5 C6 121.3(2) C4 C5 H5 119.3 C6 C5 H5 119.3 C7 C6 C5 117.8(2) C7 C6 C8 121.0(2) C5 C6 C8 121.2(2) C6 C7 C2 121.9(2) C6 C7 H7 119.1 C2 C7 H7 119.1 C6 C8 H8A 109.5 C6 C8 H8B 109.5 H8A C8 H8B 109.5 C6 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 N1 C9 C10 105.91(16) N1 C9 C13 124.71(18) C10 C9 C13 129.37(19) C9 C10 C11 105.51(17) C9 C10 C14 125.97(17) C11 C10 C14 128.51(17) N2 C11 C10 111.77(17) N2 C11 S1 120.27(14) C10 C11 S1 127.95(15) S1 C12 H12A 109.5 S1 C12 H12B 109.5 H12A C12 H12B 109.5 S1 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C9 C13 H13A 109.5 C9 C13 H13B 109.5 H13A C13 H13B 109.5 C9 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 O2 C14 O1 123.26(19) O2 C14 C10 126.17(19) O1 C14 C10 110.56(16) O1 C15 C16 106.90(19) O1 C15 H15A 110.3 C16 C15 H15A 110.3 O1 C15 H15B 110.3 C16 C15 H15B 110.3 H15A C15 H15B 108.6 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C11 1.7448(19) yes S1 C12 1.792(2) yes O1 C14 1.337(2) ? O1 C15 1.445(3) ? O2 C14 1.202(2) y O3 C1 1.205(3) y N1 C9 1.369(2) yes N1 N2 1.385(2) yes N1 C1 1.420(3) yes N2 C11 1.314(3) yes C1 C2 1.481(3) ? C2 C3 1.386(3) ? C2 C7 1.390(3) ? C3 C4 1.376(3) ? C3 H3 0.93 ? C4 C5 1.381(3) ? C4 H4 0.93 ? C5 C6 1.381(4) ? C5 H5 0.93 ? C6 C7 1.378(3) ? C6 C8 1.514(3) ? C7 H7 0.93 ? C8 H8A 0.96 ? C8 H8B 0.96 ? C8 H8C 0.96 ? C9 C10 1.376(3) y C9 C13 1.486(3) ? C10 C11 1.429(3) yes C10 C14 1.463(3) ? C12 H12A 0.96 ? C12 H12B 0.96 ? C12 H12C 0.96 ? C13 H13A 0.96 ? C13 H13B 0.96 ? C13 H13C 0.96 ? C15 C16 1.485(3) ? C15 H15A 0.97 ? C15 H15B 0.97 ? C16 H16A 0.96 ? C16 H16B 0.96 ? C16 H16C 0.96 ? 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 C3 H3 N2 1_555 0.93 2.48 2.853(3) 104 yes C12 H12B O2 1_545 0.96 2.58 3.508(3) 162 yes C13 H13A O2 1_555 0.96 2.42 3.047(3) 123 yes C13 H13B O3 1_555 0.96 2.45 2.850(3) 105 yes C8 H8A CgP 2_557 0.96 2.84 3.735(4) 155 yes 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 _geom_torsion_publ_flag C9 N1 N2 C11 0.4(2) ? C1 N1 N2 C11 179.46(18) ? C9 N1 C1 O3 15.2(4) ? N2 N1 C1 O3 -163.7(2) ? C9 N1 C1 C2 -165.9(2) ? N2 N1 C1 C2 15.2(3) ? O3 C1 C2 C3 -142.9(3) ? N1 C1 C2 C3 38.2(3) ? O3 C1 C2 C7 33.1(3) ? N1 C1 C2 C7 -145.7(2) ? C7 C2 C3 C4 0.4(4) ? C1 C2 C3 C4 176.4(2) ? C2 C3 C4 C5 0.7(4) ? C3 C4 C5 C6 -1.2(5) ? C4 C5 C6 C7 0.4(4) ? C4 C5 C6 C8 -179.0(3) ? C5 C6 C7 C2 0.8(4) ? C8 C6 C7 C2 -179.8(2) ? C3 C2 C7 C6 -1.2(3) ? C1 C2 C7 C6 -177.4(2) ? N2 N1 C9 C10 -0.1(2) ? C1 N1 C9 C10 -179.0(2) ? N2 N1 C9 C13 -179.20(19) ? C1 N1 C9 C13 1.9(3) ? N1 C9 C10 C11 -0.3(2) ? C13 C9 C10 C11 178.8(2) ? N1 C9 C10 C14 -179.29(19) ? C13 C9 C10 C14 -0.2(4) ? N1 N2 C11 C10 -0.6(2) ? N1 N2 C11 S1 178.35(13) ? C9 C10 C11 N2 0.5(2) ? C14 C10 C11 N2 179.54(19) ? C9 C10 C11 S1 -178.28(15) ? C14 C10 C11 S1 0.7(3) ? C12 S1 C11 N2 -1.2(2) yes C12 S1 C11 C10 177.55(19) yes C15 O1 C14 O2 -0.6(3) yes C15 O1 C14 C10 179.36(19) yes C9 C10 C14 O2 -0.2(4) ? C11 C10 C14 O2 -179.0(2) ? C9 C10 C14 O1 179.84(19) ? C11 C10 C14 O1 1.0(3) ? C14 O1 C15 C16 170.6(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130804 2 PubChem 139066720