#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204973.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_2204973 loop_ _publ_author_name 'Yang, Zhi-Ping' 'Zhong, Ping' 'Hu, Mao-Lin' 'Li, Shu-Yan' 'Tang, Ri-Yuan' _publ_section_title 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(dimethylsulfonyl)amino]-1H-pyrazole-3-carbonitrile _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o116 _journal_page_last o117 _journal_paper_doi 10.1107/S1600536804032428 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H9 Cl2 F3 N4 O4 S2' _chemical_formula_moiety 'C13 H9 Cl2 F3 N4 O4 S2' _chemical_formula_sum 'C13 H9 Cl2 F3 N4 O4 S2' _chemical_formula_weight 477.26 _chemical_melting_point .505E-305 _chemical_name_systematic ; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(dimethylsulfonyl)amino]- 1H-pyrazole-3-carbonitrile ; _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 _cell_angle_alpha 75.198(2) _cell_angle_beta 87.9180(10) _cell_angle_gamma 65.3950(10) _cell_formula_units_Z 2 _cell_length_a 8.4681(7) _cell_length_b 8.9652(8) _cell_length_c 14.3497(12) _cell_measurement_reflns_used 2990 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.20 _cell_measurement_theta_min 2.58 _cell_volume 954.57(14) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXTL (Bruker, 2002)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Bruker APEX area-detector diffractometer' _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 0.0116 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5126 _diffrn_reflns_theta_full 25.25 _diffrn_reflns_theta_max 25.25 _diffrn_reflns_theta_min 1.47 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_T_max 0.8663 _exptl_absorpt_correction_T_min 0.7864 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _refine_diff_density_max 1.003 _refine_diff_density_min -0.569 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 3400 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0490 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+0.9462P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1314 _refine_ls_wR_factor_ref 0.1355 _reflns_number_gt 3039 _reflns_number_total 3400 _reflns_threshold_expression I>2\s(I) _cod_data_source_file su6147.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: '_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 2204973 _cod_database_fobs_code 2204973 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 Cl1 0.63806(13) -0.07675(11) 0.35855(7) 0.0637(3) Uani d . 1 Cl Cl2 0.54128(11) 0.57366(11) 0.20484(6) 0.0566(3) Uani d . 1 Cl S1 0.09064(9) 0.62016(9) 0.11416(5) 0.0406(2) Uani d . 1 S S2 0.11411(9) 0.32356(10) 0.26949(6) 0.0457(2) Uani d . 1 S F1 0.9338(4) 0.1418(7) 0.5862(3) 0.183(2) Uani d . 1 F F2 0.6873(5) 0.2252(5) 0.63245(19) 0.1220(12) Uani d . 1 F F3 0.7714(6) 0.4027(5) 0.5639(2) 0.1389(15) Uani d . 1 F O1 0.1988(3) 0.6478(3) 0.04046(16) 0.0518(6) Uani d . 1 O O2 -0.0700(3) 0.6183(3) 0.09034(18) 0.0588(6) Uani d . 1 O O3 0.2501(3) 0.1886(4) 0.33577(18) 0.0686(8) Uani d . 1 O O4 -0.0190(3) 0.4541(3) 0.30256(18) 0.0595(6) Uani d . 1 O N1 0.5313(3) 0.2477(3) 0.20099(16) 0.0372(5) Uani d . 1 N N2 0.6538(3) 0.1553(3) 0.15152(18) 0.0416(6) Uani d . 1 N N3 0.7268(4) 0.0237(4) -0.0576(2) 0.0630(8) Uani d . 1 N C1 0.7825(5) 0.2554(6) 0.5602(3) 0.0696(11) Uani d . 1 C C2 0.7101(4) 0.2577(5) 0.4660(2) 0.0500(8) Uani d . 1 C C3 0.7006(4) 0.1116(5) 0.4575(2) 0.0514(8) Uani d . 1 C H3 0.7345 0.0161 0.5100 0.062 Uiso calc R 1 H C4 0.6403(4) 0.1090(4) 0.3704(2) 0.0441(7) Uani d . 1 C C5 0.5851(3) 0.2531(4) 0.2927(2) 0.0380(6) Uani d . 1 C C6 0.5963(4) 0.3982(4) 0.3027(2) 0.0405(7) Uani d . 1 C C7 0.6592(4) 0.4017(4) 0.3894(2) 0.0484(8) Uani d . 1 C H7 0.6671 0.4990 0.3959 0.058 Uiso calc R 1 H C8 0.3681(3) 0.3180(3) 0.15375(19) 0.0344(6) Uani d . 1 C C9 0.3875(4) 0.2699(4) 0.0699(2) 0.0383(6) Uani d . 1 C H9 0.3014 0.2971 0.0221 0.046 Uiso calc R 1 H C10 0.5663(4) 0.1705(4) 0.0719(2) 0.0391(6) Uani d . 1 C C11 0.6577(4) 0.0882(4) 0.0002(2) 0.0453(7) Uani d . 1 C N4 0.2174(3) 0.4232(3) 0.19054(16) 0.0373(5) Uani d . 1 N C12 0.0549(5) 0.7585(4) 0.1880(3) 0.0560(9) Uani d . 1 C H12A 0.1647 0.7495 0.2104 0.084 Uiso calc R 1 H H12B -0.0054 0.7284 0.2424 0.084 Uiso calc R 1 H H12C -0.0142 0.8733 0.1514 0.084 Uiso calc R 1 H C13 0.0234(5) 0.2389(5) 0.2005(3) 0.0588(9) Uani d . 1 C H13A -0.0312 0.1750 0.2419 0.088 Uiso calc R 1 H H13B 0.1136 0.1655 0.1695 0.088 Uiso calc R 1 H H13C -0.0619 0.3298 0.1524 0.088 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 Cl1 0.0647(6) 0.0521(5) 0.0668(6) -0.0237(4) -0.0099(4) -0.0025(4) Cl2 0.0582(5) 0.0567(5) 0.0492(5) -0.0271(4) -0.0058(4) 0.0017(4) S1 0.0372(4) 0.0401(4) 0.0386(4) -0.0120(3) -0.0080(3) -0.0067(3) S2 0.0344(4) 0.0562(5) 0.0407(4) -0.0190(3) 0.0043(3) -0.0037(3) F1 0.0699(18) 0.276(5) 0.141(3) 0.038(2) -0.061(2) -0.137(3) F2 0.136(3) 0.190(4) 0.0505(15) -0.071(3) 0.0097(16) -0.0472(19) F3 0.213(4) 0.146(3) 0.085(2) -0.100(3) -0.050(2) -0.025(2) O1 0.0631(14) 0.0452(12) 0.0417(12) -0.0213(11) 0.0024(10) -0.0051(10) O2 0.0427(12) 0.0582(14) 0.0659(15) -0.0158(11) -0.0236(11) -0.0058(12) O3 0.0512(14) 0.0780(18) 0.0530(15) -0.0258(13) -0.0037(11) 0.0205(13) O4 0.0479(13) 0.0796(17) 0.0571(14) -0.0296(12) 0.0197(11) -0.0255(13) N1 0.0283(11) 0.0477(14) 0.0309(12) -0.0127(10) -0.0017(9) -0.0079(10) N2 0.0311(12) 0.0489(14) 0.0390(13) -0.0114(10) 0.0022(10) -0.0113(11) N3 0.076(2) 0.0578(18) 0.067(2) -0.0322(16) 0.0259(17) -0.0320(16) C1 0.060(2) 0.092(3) 0.050(2) -0.016(2) -0.0089(18) -0.031(2) C2 0.0343(15) 0.073(2) 0.0337(16) -0.0139(15) -0.0021(12) -0.0143(15) C3 0.0421(16) 0.062(2) 0.0346(16) -0.0131(15) -0.0048(13) -0.0022(14) C4 0.0329(14) 0.0510(18) 0.0415(16) -0.0144(13) -0.0028(12) -0.0054(13) C5 0.0257(13) 0.0516(17) 0.0310(14) -0.0126(12) -0.0009(11) -0.0073(12) C6 0.0289(13) 0.0499(17) 0.0354(15) -0.0126(12) -0.0002(11) -0.0060(13) C7 0.0346(15) 0.062(2) 0.0489(18) -0.0169(14) 0.0033(13) -0.0222(16) C8 0.0275(12) 0.0388(14) 0.0336(14) -0.0143(11) -0.0029(10) -0.0031(11) C9 0.0364(14) 0.0431(15) 0.0354(14) -0.0173(12) -0.0049(11) -0.0085(12) C10 0.0403(15) 0.0394(15) 0.0385(15) -0.0180(12) 0.0027(12) -0.0095(12) C11 0.0487(17) 0.0420(16) 0.0469(18) -0.0206(14) 0.0048(14) -0.0121(14) N4 0.0287(11) 0.0442(13) 0.0332(12) -0.0125(10) -0.0001(9) -0.0053(10) C12 0.0542(19) 0.0520(19) 0.063(2) -0.0172(16) 0.0026(16) -0.0256(17) C13 0.0502(19) 0.059(2) 0.074(2) -0.0299(17) 0.0099(17) -0.0180(18) 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 '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 O1 S1 O2 120.15(15) no O1 S1 N4 105.04(12) yes O2 S1 N4 107.25(13) no O1 S1 C12 110.46(16) yes O2 S1 C12 109.47(17) no N4 S1 C12 102.93(15) yes O4 S2 O3 120.18(17) no O4 S2 N4 105.36(14) no O3 S2 N4 104.65(13) no O4 S2 C13 110.50(16) no O3 S2 C13 109.46(19) no N4 S2 C13 105.46(15) no N2 N1 C8 111.8(2) yes N2 N1 C5 117.6(2) yes C8 N1 C5 130.5(2) yes C10 N2 N1 104.2(2) yes F1 C1 F3 111.1(4) yes F1 C1 F2 104.9(4) no F3 C1 F2 100.6(4) no F1 C1 C2 113.8(3) yes F3 C1 C2 113.6(4) no F2 C1 C2 111.6(4) no C3 C2 C7 121.5(3) no C3 C2 C1 118.3(3) yes C7 C2 C1 120.1(4) no C4 C3 C2 119.2(3) yes C4 C3 H3 120.4 no C2 C3 H3 120.4 no C3 C4 C5 120.4(3) no C3 C4 Cl1 119.0(3) no C5 C4 Cl1 120.6(2) no C6 C5 C4 119.5(3) no C6 C5 N1 120.0(3) no C4 C5 N1 120.3(3) no C7 C6 C5 120.7(3) no C7 C6 Cl2 119.2(3) no C5 C6 Cl2 120.0(2) no C2 C7 C6 118.6(3) no C2 C7 H7 120.7 no C6 C7 H7 120.7 no C9 C8 N1 106.9(2) yes C9 C8 N4 130.4(2) yes N1 C8 N4 122.7(2) yes C8 C9 C10 104.3(2) yes C8 C9 H9 127.8 no C10 C9 H9 127.8 no N2 C10 C9 112.7(3) yes N2 C10 C11 119.8(3) yes C9 C10 C11 127.5(3) yes N3 C11 C10 178.6(4) yes C8 N4 S2 116.78(19) yes C8 N4 S1 116.76(18) no S2 N4 S1 117.75(13) yes S1 C12 H12A 109.5 no S1 C12 H12B 109.5 no H12A C12 H12B 109.5 no S1 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no S2 C13 H13A 109.5 no S2 C13 H13B 109.5 no H13A C13 H13B 109.5 no S2 C13 H13C 109.5 no H13A C13 H13C 109.5 no H13B C13 H13C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C4 1.724(3) yes Cl2 C6 1.723(3) no S1 O1 1.415(2) no S1 O2 1.422(2) no S1 N4 1.729(2) yes S1 C12 1.757(3) yes S2 O4 1.418(2) no S2 O3 1.423(2) no S2 N4 1.705(2) yes S2 C13 1.752(4) yes F1 C1 1.254(5) yes F2 C1 1.333(5) no F3 C1 1.299(6) no N1 N2 1.341(3) yes N1 C8 1.375(3) yes N1 C5 1.427(3) yes N2 C10 1.330(4) yes N3 C11 1.136(4) yes C1 C2 1.496(5) yes C2 C3 1.381(5) no C2 C7 1.381(5) no C3 C4 1.377(4) no C3 H3 0.9300 no C4 C5 1.389(4) no C5 C6 1.386(4) no C6 C7 1.384(4) no C7 H7 0.9300 no C8 C9 1.360(4) yes C8 N4 1.414(4) yes C9 C10 1.398(4) yes C9 H9 0.9300 no C10 C11 1.435(4) yes C12 H12A 0.9600 no C12 H12B 0.9600 no C12 H12C 0.9600 no C13 H13A 0.9600 no C13 H13B 0.9600 no C13 H13C 0.9600 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130043 2 PubChem 46193431