#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206972.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_2206972 loop_ _publ_author_name 'Zhong, Ping' 'Zhang, Xiao-Hong' 'Xiao, Hong-Ping' 'Hu, Mao-Lin' _publ_section_title 5-(2,4-Dichlorobenzamido)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile _journal_coeditor_code HG6237 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3110 _journal_page_last o3111 _journal_paper_doi 10.1107/S1600536805027054 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H7 Cl4 F3 N4 O' _chemical_formula_moiety 'C18 H7 Cl4 F3 N4 O' _chemical_formula_sum 'C18 H7 Cl4 F3 N4 O' _chemical_formula_weight 494.08 _chemical_melting_point 505 _chemical_name_systematic ; 5-(2,4-Dichlorobenzamido)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]- 1H-pyrazole-3-carbonitrile ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 99.31(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.7760(11) _cell_length_b 16.4530(16) _cell_length_c 16.6220(16) _cell_measurement_reflns_used 1812 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.26 _cell_measurement_theta_min 2.83 _cell_volume 2098.6(5) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \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 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10608 _diffrn_reflns_theta_full 25.20 _diffrn_reflns_theta_max 25.20 _diffrn_reflns_theta_min 1.75 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.608 _exptl_absorpt_correction_T_max 0.9037 _exptl_absorpt_correction_T_min 0.8154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.17 _refine_diff_density_max 1.019 _refine_diff_density_min -0.689 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 3779 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0925 _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^)+(0.1073P)^2^+5.2953P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2336 _refine_ls_wR_factor_ref 0.2440 _reflns_number_gt 3196 _reflns_number_total 3779 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hg6237.cif _cod_data_source_block I _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 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2206972 _cod_database_fobs_code 2206972 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 Cl1 0.85543(18) 0.91195(11) 0.22140(10) 0.0767(5) Uani d . 1 Cl Cl2 0.3192(2) 0.72751(11) 0.27660(11) 0.0820(5) Uani d . 1 Cl Cl3 0.9410(4) 0.73550(16) 0.05278(14) 0.1392(12) Uani d . 1 Cl Cl4 0.7241(3) 0.49917(13) -0.15813(9) 0.0939(7) Uani d . 1 Cl O1 0.9513(6) 0.5777(3) 0.2392(2) 0.0816(14) Uani d . 1 O F1 0.0914(11) 0.9348(5) 0.0479(6) 0.237(5) Uani d . 1 F F2 0.1704(16) 1.0236(5) 0.1032(6) 0.261(6) Uani d . 1 F F3 0.2869(10) 0.9906(9) 0.0181(6) 0.335(9) Uani d . 1 F N1 0.6910(5) 0.7792(2) 0.3001(2) 0.0449(9) Uani d . 1 N N2 0.7298(6) 0.8052(3) 0.3781(2) 0.0504(10) Uani d . 1 N N3 0.9928(7) 0.7688(3) 0.5611(3) 0.0726(15) Uani d . 1 N N4 0.7663(6) 0.6815(3) 0.2071(2) 0.0544(11) Uani d . 1 N H4 0.6938 0.7041 0.1691 0.065 Uiso calc R 1 H C1 0.2354(10) 0.9653(5) 0.0729(5) 0.085(2) Uani d . 1 C C2 0.3539(7) 0.9168(3) 0.1324(3) 0.0535(13) Uani d . 1 C C3 0.2871(6) 0.8542(3) 0.1729(3) 0.0527(13) Uani d . 1 C H3 0.1683 0.8429 0.1631 0.063 Uiso calc R 1 H C4 0.3983(6) 0.8088(3) 0.2280(3) 0.0469(11) Uani d . 1 C C5 0.5741(6) 0.8257(3) 0.2430(2) 0.0393(10) Uani d . 1 C C6 0.6372(6) 0.8890(3) 0.2017(3) 0.0454(11) Uani d . 1 C C7 0.5268(7) 0.9348(3) 0.1460(3) 0.0516(12) Uani d . 1 C H7 0.5700 0.9772 0.1182 0.062 Uiso calc R 1 H C8 0.8497(6) 0.7522(3) 0.4112(3) 0.0454(11) Uani d . 1 C C9 0.8913(7) 0.6949(3) 0.3565(3) 0.0517(12) Uani d . 1 C H9 0.9725 0.6531 0.3661 0.062 Uiso calc R 1 H C10 0.7853(6) 0.7139(3) 0.2845(3) 0.0436(11) Uani d . 1 C C11 0.9263(7) 0.7620(3) 0.4954(3) 0.0549(13) Uani d . 1 C C12 0.8574(7) 0.6152(3) 0.1881(3) 0.0531(12) Uani d . 1 C C13 0.8246(7) 0.5903(3) 0.1004(3) 0.0507(12) Uani d . 1 C C14 0.8574(8) 0.6381(4) 0.0366(3) 0.0651(15) Uani d . 1 C C15 0.8280(9) 0.6100(4) -0.0433(3) 0.0728(17) Uani d . 1 C H15 0.8531 0.6426 -0.0856 0.087 Uiso calc R 1 H C16 0.7623(7) 0.5346(4) -0.0585(3) 0.0573(14) Uani d . 1 C C17 0.7324(10) 0.4848(4) 0.0033(4) 0.0770(18) Uani d . 1 C H17 0.6906 0.4323 -0.0076 0.092 Uiso calc R 1 H C18 0.7651(10) 0.5136(3) 0.0823(3) 0.0734(18) Uani d . 1 C H18 0.7458 0.4794 0.1245 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 0.0423(7) 0.1033(13) 0.0825(11) -0.0104(7) 0.0046(7) 0.0070(9) Cl2 0.0810(11) 0.0840(11) 0.0812(11) -0.0192(8) 0.0142(8) 0.0197(9) Cl3 0.215(3) 0.1225(18) 0.0915(15) -0.102(2) 0.0596(17) -0.0308(13) Cl4 0.1062(14) 0.1224(16) 0.0481(9) 0.0302(11) -0.0022(8) -0.0317(9) O1 0.110(3) 0.086(3) 0.044(2) 0.052(3) -0.003(2) 0.001(2) F1 0.172(6) 0.208(8) 0.267(10) -0.032(6) -0.153(7) 0.126(7) F2 0.332(12) 0.166(7) 0.226(9) 0.162(8) -0.128(9) -0.013(7) F3 0.158(6) 0.65(2) 0.216(8) 0.207(10) 0.090(6) 0.340(13) N1 0.050(2) 0.054(2) 0.0269(18) 0.0114(18) -0.0046(16) -0.0026(16) N2 0.062(3) 0.061(3) 0.0250(18) 0.007(2) -0.0003(17) -0.0046(17) N3 0.092(4) 0.086(4) 0.031(2) -0.014(3) -0.016(2) 0.011(2) N4 0.066(3) 0.061(3) 0.032(2) 0.023(2) -0.0080(18) -0.0019(18) C1 0.082(5) 0.091(5) 0.069(4) 0.032(4) -0.024(4) 0.020(4) C2 0.057(3) 0.060(3) 0.040(3) 0.014(2) -0.003(2) 0.000(2) C3 0.036(2) 0.074(3) 0.045(3) 0.005(2) -0.004(2) -0.004(2) C4 0.051(3) 0.051(3) 0.038(2) 0.002(2) 0.005(2) -0.003(2) C5 0.043(2) 0.047(2) 0.026(2) 0.008(2) -0.0006(17) -0.0060(18) C6 0.040(2) 0.056(3) 0.039(2) 0.002(2) 0.0005(19) -0.003(2) C7 0.058(3) 0.057(3) 0.039(3) 0.004(2) 0.005(2) 0.007(2) C8 0.054(3) 0.051(3) 0.027(2) 0.000(2) -0.0066(19) 0.0018(19) C9 0.057(3) 0.053(3) 0.040(3) 0.013(2) -0.008(2) 0.003(2) C10 0.051(3) 0.048(3) 0.030(2) 0.006(2) -0.0007(19) -0.0022(19) C11 0.070(3) 0.054(3) 0.037(3) -0.007(3) -0.002(2) 0.004(2) C12 0.061(3) 0.058(3) 0.039(3) 0.015(3) 0.002(2) -0.003(2) C13 0.054(3) 0.055(3) 0.042(3) 0.015(2) 0.006(2) -0.003(2) C14 0.072(4) 0.073(4) 0.052(3) -0.016(3) 0.018(3) -0.008(3) C15 0.085(4) 0.091(5) 0.046(3) -0.011(4) 0.022(3) -0.002(3) C16 0.054(3) 0.074(4) 0.042(3) 0.019(3) 0.003(2) -0.016(3) C17 0.115(5) 0.055(3) 0.059(4) 0.008(3) 0.008(3) -0.013(3) C18 0.124(6) 0.050(3) 0.046(3) 0.011(3) 0.013(3) 0.002(2) 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' 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 C10 N1 N2 113.1(4) yes C10 N1 C5 127.4(4) yes N2 N1 C5 119.2(4) yes C8 N2 N1 102.9(4) yes C12 N4 C10 122.9(4) ? C12 N4 H4 118.5 ? C10 N4 H4 118.5 ? F3 C1 F2 105.4(11) yes F3 C1 F1 107.4(9) ? F2 C1 F1 92.5(9) ? F3 C1 C2 118.4(7) ? F2 C1 C2 113.7(7) ? F1 C1 C2 116.1(7) ? C7 C2 C3 121.6(5) yes C7 C2 C1 119.2(6) yes C3 C2 C1 119.2(6) ? C4 C3 C2 119.1(5) ? C4 C3 H3 120.5 ? C2 C3 H3 120.5 ? C3 C4 C5 120.7(5) yes C3 C4 Cl2 120.0(4) ? C5 C4 Cl2 119.3(4) ? C4 C5 C6 118.9(4) ? C4 C5 N1 121.3(4) ? C6 C5 N1 119.7(4) yes C7 C6 C5 120.9(4) ? C7 C6 Cl1 119.7(4) ? C5 C6 Cl1 119.4(3) ? C2 C7 C6 118.9(5) yes C2 C7 H7 120.5 ? C6 C7 H7 120.5 ? N2 C8 C9 113.4(4) yes N2 C8 C11 118.8(4) ? C9 C8 C11 127.8(5) ? C10 C9 C8 104.2(4) yes C10 C9 H9 127.9 ? C8 C9 H9 127.9 ? N1 C10 C9 106.4(4) ? N1 C10 N4 120.5(4) yes C9 C10 N4 133.1(4) yes N3 C11 C8 177.3(7) ? O1 C12 N4 121.8(5) yes O1 C12 C13 122.6(5) ? N4 C12 C13 115.5(4) yes C18 C13 C14 117.3(5) yes C18 C13 C12 117.8(5) ? C14 C13 C12 124.8(5) ? C13 C14 C15 121.5(6) ? C13 C14 Cl3 121.4(4) ? C15 C14 Cl3 117.1(5) yes C16 C15 C14 119.0(6) ? C16 C15 H15 120.5 ? C14 C15 H15 120.5 ? C15 C16 C17 121.1(5) ? C15 C16 Cl4 119.3(5) ? C17 C16 Cl4 119.6(5) ? C16 C17 C18 118.9(6) yes C16 C17 H17 120.6 ? C18 C17 H17 120.6 ? C13 C18 C17 122.2(6) yes C13 C18 H18 118.9 ? C17 C18 H18 118.9 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C6 1.718(5) ? Cl2 C4 1.726(5) ? Cl3 C14 1.733(6) ? Cl4 C16 1.735(5) ? O1 C12 1.197(6) yes F1 C1 1.235(10) yes F2 C1 1.230(11) ? F3 C1 1.132(9) ? N1 C10 1.349(6) yes N1 N2 1.352(5) yes N1 C5 1.425(5) yes N2 C8 1.330(6) yes N3 C11 1.135(6) ? N4 C12 1.366(6) yes N4 C10 1.377(6) yes N4 H4 0.8600 ? C1 C2 1.473(7) yes C2 C7 1.359(7) ? C2 C3 1.377(8) ? C3 C4 1.375(7) ? C3 H3 0.9300 ? C4 C5 1.378(7) ? C5 C6 1.381(7) yes C6 C7 1.380(7) ? C7 H7 0.9300 ? C8 C9 1.385(7) yes C8 C11 1.439(6) ? C9 C10 1.375(6) ? C9 H9 0.9300 ? C12 C13 1.496(7) ? C13 C18 1.361(8) yes C13 C14 1.377(8) yes C14 C15 1.390(8) ? C15 C16 1.350(9) ? C15 H15 0.9300 ? C16 C17 1.363(9) ? C17 C18 1.380(8) ? C17 H17 0.9300 ? C18 H18 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 N4 H4 N3 4_575 0.86 2.23 3.068(6) 166 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 C10 N1 N2 C8 -1.4(5) yes C5 N1 N2 C8 -175.3(4) yes F3 C1 C2 C7 32.5(15) ? F2 C1 C2 C7 -92.0(11) ? F1 C1 C2 C7 162.4(9) yes F3 C1 C2 C3 -147.4(12) ? F2 C1 C2 C3 88.2(11) ? F1 C1 C2 C3 -17.4(12) ? C7 C2 C3 C4 -0.3(8) yes C1 C2 C3 C4 179.6(6) ? C2 C3 C4 C5 0.4(7) ? C2 C3 C4 Cl2 -177.5(4) ? C3 C4 C5 C6 -0.2(7) ? Cl2 C4 C5 C6 177.7(3) ? C3 C4 C5 N1 179.9(4) yes Cl2 C4 C5 N1 -2.2(6) ? C10 N1 C5 C4 93.6(6) ? N2 N1 C5 C4 -93.5(5) yes C10 N1 C5 C6 -86.3(6) yes N2 N1 C5 C6 86.6(5) yes C4 C5 C6 C7 -0.1(7) ? N1 C5 C6 C7 179.8(4) yes C4 C5 C6 Cl1 178.7(4) ? N1 C5 C6 Cl1 -1.4(6) ? C3 C2 C7 C6 0.0(8) yes C1 C2 C7 C6 -179.8(5) ? C5 C6 C7 C2 0.2(7) ? Cl1 C6 C7 C2 -178.6(4) ? N1 N2 C8 C9 1.6(6) ? N1 N2 C8 C11 178.5(4) ? N2 C8 C9 C10 -1.2(6) ? C11 C8 C9 C10 -177.8(5) ? N2 N1 C10 C9 0.7(6) ? C5 N1 C10 C9 174.0(5) ? N2 N1 C10 N4 -177.7(4) yes C5 N1 C10 N4 -4.4(8) ? C8 C9 C10 N1 0.3(6) ? C8 C9 C10 N4 178.4(5) ? C12 N4 C10 N1 -179.5(5) yes C12 N4 C10 C9 2.6(9) ? N2 C8 C11 N3 -143(12) ? C9 C8 C11 N3 33(13) ? C10 N4 C12 O1 5.1(9) ? C10 N4 C12 C13 -177.9(5) ? O1 C12 C13 C18 55.2(8) ? N4 C12 C13 C18 -121.8(6) ? O1 C12 C13 C14 -121.8(7) ? N4 C12 C13 C14 61.2(7) yes C18 C13 C14 C15 1.2(9) ? C12 C13 C14 C15 178.2(6) ? C18 C13 C14 Cl3 -177.6(5) ? C12 C13 C14 Cl3 -0.6(8) ? C13 C14 C15 C16 1.4(10) ? Cl3 C14 C15 C16 -179.7(5) yes C14 C15 C16 C17 -3.0(10) ? C14 C15 C16 Cl4 179.7(5) ? C15 C16 C17 C18 2.0(10) ? Cl4 C16 C17 C18 179.3(5) ? C14 C13 C18 C17 -2.2(10) ? C12 C13 C18 C17 -179.5(6) ? C16 C17 C18 C13 0.7(11) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21128793 2 PubChem 139068439