#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214397.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_2214397 loop_ _publ_author_name 'Yu, Xiao-Chun' 'Li, Shu-Yan' 'Zhong, Ping' _publ_section_title 4-Bromo-5-[(4-chlorobenzylidene)amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile _journal_coeditor_code TK2157 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3098 _journal_page_last o3098 _journal_paper_doi 10.1107/S1600536807026256 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C18 H7 Br Cl3 F3 N4' _chemical_formula_moiety 'C18 H7 Br Cl3 F3 N4' _chemical_formula_sum 'C18 H7 Br Cl3 F3 N4' _chemical_formula_weight 522.54 _chemical_melting_point 488.5(5) _chemical_name_systematic ; 4-Bromo-5-[(4-chlorobenzylidene)amino]-1-[2,6-dichloro-4- (trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.0338(7) _cell_length_b 11.5819(8) _cell_length_c 34.499(3) _cell_measurement_reflns_used 4261 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.3 _cell_measurement_theta_min 2.4 _cell_volume 4009.1(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 0.949 _diffrn_measured_fraction_theta_max 0.949 _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 0.036 _diffrn_reflns_av_sigmaI/netI 0.042 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_number 23679 _diffrn_reflns_theta_full 28.3 _diffrn_reflns_theta_max 28.3 _diffrn_reflns_theta_min 1.2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.490 _exptl_absorpt_correction_T_max 0.691 _exptl_absorpt_correction_T_min 0.444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 2048 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _refine_diff_density_max 1.20 _refine_diff_density_min -0.84 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4736 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all 0.095 _refine_ls_R_factor_gt 0.058 _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^)+(0.0966P)^2^+3.5182P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.158 _refine_ls_wR_factor_ref 0.186 _reflns_number_gt 3014 _reflns_number_total 4736 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk2157.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: '_chemical_melting_point' value '488-489' was changed to '488.5(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 '488-489' was changed to '488.5(5)' - the average value was taken and precision was estimated. '_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 ; _cod_database_code 2214397 _cod_database_fobs_code 2214397 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_type_symbol _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 Br Br1 1.01932(6) 0.22489(5) 0.020072(16) 0.0781(2) Uani d . 1 Cl Cl1 0.50245(14) 0.43701(13) 0.08080(3) 0.0729(4) Uani d . 1 Cl Cl2 0.81344(15) 0.17122(15) 0.17059(4) 0.0894(5) Uani d . 1 Cl Cl3 1.32776(14) 0.77979(12) 0.17945(4) 0.0804(4) Uani d . 1 F F1 0.4269(6) 0.3602(5) 0.25418(13) 0.150(2) Uani d . 1 F F2 0.3552(4) 0.4993(4) 0.22440(9) 0.1293(18) Uani d . 1 F F3 0.5420(6) 0.5033(7) 0.25062(15) 0.200(4) Uani d . 1 N N1 0.7224(3) 0.2693(3) 0.09621(9) 0.0474(8) Uani d . 1 N N2 0.6684(3) 0.1819(3) 0.07601(10) 0.0530(8) Uani d . 1 N N3 0.7249(5) -0.0086(4) 0.00155(12) 0.0825(14) Uani d . 1 N N4 0.9101(3) 0.3884(3) 0.10357(9) 0.0471(8) Uani d . 1 C C1 0.4628(5) 0.4421(5) 0.23040(13) 0.0639(13) Uani d . 1 C C2 0.5282(4) 0.3954(4) 0.19469(12) 0.0484(9) Uani d . 1 C C3 0.4871(4) 0.4337(4) 0.15874(12) 0.0474(9) Uani d . 1 H H3 0.4178 0.4867 0.1564 0.057 Uiso calc R 1 C C4 0.5516(4) 0.3913(3) 0.12611(11) 0.0443(9) Uani d . 1 C C5 0.6547(4) 0.3127(3) 0.12953(11) 0.0438(9) Uani d . 1 C C6 0.6911(4) 0.2741(4) 0.16625(13) 0.0527(10) Uani d . 1 C C7 0.6291(4) 0.3172(4) 0.19877(12) 0.0552(10) Uani d . 1 H H7 0.6557 0.2934 0.2233 0.066 Uiso calc R 1 C C8 0.7399(5) 0.0671(4) 0.02214(12) 0.0581(11) Uani d . 1 C C9 0.7597(4) 0.1600(3) 0.04885(11) 0.0474(9) Uani d . 1 C C10 0.8695(4) 0.2339(3) 0.05139(11) 0.0475(9) Uani d . 1 C C11 0.8445(4) 0.3047(3) 0.08248(11) 0.0446(9) Uani d . 1 C C12 0.9998(4) 0.4510(4) 0.08793(12) 0.0483(9) Uani d . 1 H H12 1.0163 0.4440 0.0615 0.058 Uiso calc R 1 C C13 1.0769(4) 0.5334(3) 0.11074(11) 0.0425(8) Uani d . 1 C C14 1.1751(5) 0.5990(4) 0.09282(13) 0.0585(11) Uani d . 1 H H14 1.1897 0.5908 0.0663 0.070 Uiso calc R 1 C C15 1.2515(5) 0.6764(4) 0.11383(14) 0.0642(12) Uani d . 1 H H15 1.3170 0.7203 0.1017 0.077 Uiso calc R 1 C C16 1.2289(4) 0.6867(3) 0.15246(12) 0.0501(9) Uani d . 1 C C17 1.1317(4) 0.6240(3) 0.17108(12) 0.0503(9) Uani d . 1 H H17 1.1176 0.6331 0.1975 0.060 Uiso calc R 1 C C18 1.0557(4) 0.5480(3) 0.15006(11) 0.0468(9) Uani d . 1 H H18 0.9892 0.5058 0.1624 0.056 Uiso calc R 1 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 Br1 0.0779(4) 0.0866(4) 0.0696(4) -0.0145(3) 0.0327(3) -0.0231(3) Cl1 0.0865(9) 0.0873(9) 0.0450(6) 0.0215(7) 0.0038(5) 0.0120(6) Cl2 0.0807(9) 0.1045(11) 0.0831(9) 0.0444(9) -0.0068(7) 0.0048(8) Cl3 0.0756(9) 0.0734(9) 0.0922(10) -0.0251(7) -0.0067(7) -0.0206(7) F1 0.191(5) 0.163(4) 0.097(3) 0.050(4) 0.084(3) 0.037(3) F2 0.137(4) 0.185(4) 0.066(2) 0.092(3) 0.009(2) -0.021(2) F3 0.128(4) 0.342(9) 0.130(4) -0.077(4) 0.041(3) -0.163(6) N1 0.0422(18) 0.0493(19) 0.0507(19) -0.0050(15) 0.0045(14) -0.0097(15) N2 0.050(2) 0.0506(19) 0.058(2) -0.0075(16) -0.0029(16) -0.0093(17) N3 0.107(4) 0.076(3) 0.065(3) -0.003(3) -0.011(2) -0.028(2) N4 0.0471(19) 0.0453(18) 0.0487(18) -0.0064(15) 0.0043(14) -0.0071(15) C1 0.063(3) 0.087(4) 0.041(2) 0.003(3) 0.003(2) -0.011(2) C2 0.043(2) 0.056(2) 0.047(2) -0.0071(18) 0.0034(16) -0.0035(18) C3 0.043(2) 0.051(2) 0.049(2) 0.0034(18) 0.0023(16) 0.0014(18) C4 0.046(2) 0.048(2) 0.0394(19) -0.0045(17) -0.0002(16) 0.0034(16) C5 0.040(2) 0.044(2) 0.046(2) -0.0082(17) 0.0037(16) -0.0053(17) C6 0.043(2) 0.056(3) 0.059(2) 0.0049(19) -0.0029(18) -0.001(2) C7 0.050(2) 0.071(3) 0.045(2) -0.001(2) -0.0079(18) 0.004(2) C8 0.068(3) 0.058(3) 0.048(2) 0.000(2) -0.009(2) -0.006(2) C9 0.054(2) 0.046(2) 0.043(2) 0.0008(18) -0.0038(18) -0.0032(17) C10 0.051(2) 0.050(2) 0.042(2) -0.0013(18) 0.0088(17) 0.0000(17) C11 0.044(2) 0.044(2) 0.046(2) -0.0024(17) 0.0006(16) -0.0012(17) C12 0.051(2) 0.049(2) 0.045(2) -0.0043(18) 0.0032(17) -0.0042(18) C13 0.039(2) 0.0398(19) 0.049(2) 0.0019(16) 0.0013(16) -0.0016(16) C14 0.062(3) 0.063(3) 0.051(2) -0.013(2) 0.016(2) -0.008(2) C15 0.061(3) 0.059(3) 0.072(3) -0.022(2) 0.018(2) -0.006(2) C16 0.046(2) 0.043(2) 0.061(2) -0.0036(18) -0.0032(18) -0.0066(19) C17 0.057(2) 0.044(2) 0.049(2) -0.0011(19) 0.0013(18) -0.0017(18) C18 0.046(2) 0.045(2) 0.049(2) -0.0031(17) 0.0067(17) 0.0029(17) 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' 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' Br Br -0.2901 2.4595 '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 N2 N1 C11 113.9(3) yes N2 N1 C5 119.5(3) yes C11 N1 C5 126.6(3) yes C9 N2 N1 103.3(3) yes C12 N4 C11 120.9(3) yes F3 C1 F2 109.1(6) ? F3 C1 F1 103.4(6) yes F2 C1 F1 104.2(5) ? F3 C1 C2 112.2(4) ? F2 C1 C2 115.0(4) ? F1 C1 C2 112.0(5) ? C7 C2 C3 121.9(4) ? C7 C2 C1 118.7(4) ? C3 C2 C1 119.4(4) ? C2 C3 C4 118.4(4) ? C2 C3 H3 120.8 ? C4 C3 H3 120.8 ? C5 C4 C3 120.8(4) ? C5 C4 Cl1 119.6(3) ? C3 C4 Cl1 119.6(3) ? C4 C5 C6 119.0(4) ? C4 C5 N1 121.3(4) ? C6 C5 N1 119.7(4) ? C7 C6 C5 120.4(4) ? C7 C6 Cl2 120.3(3) ? C5 C6 Cl2 119.3(3) ? C2 C7 C6 119.5(4) ? C2 C7 H7 120.3 ? C6 C7 H7 120.3 ? N3 C8 C9 178.4(5) ? N2 C9 C10 112.4(3) yes N2 C9 C8 120.0(4) yes C10 C9 C8 127.6(4) yes C11 C10 C9 105.7(3) yes C11 C10 Br1 129.6(3) yes C9 C10 Br1 124.6(3) yes C10 C11 N1 104.7(3) yes C10 C11 N4 138.1(4) yes N1 C11 N4 116.9(3) yes N4 C12 C13 121.2(4) ? N4 C12 H12 119.4 ? C13 C12 H12 119.4 ? C18 C13 C14 118.6(4) ? C18 C13 C12 121.8(4) ? C14 C13 C12 119.6(4) ? C15 C14 C13 120.9(4) ? C15 C14 H14 119.5 ? C13 C14 H14 119.5 ? C16 C15 C14 118.6(4) ? C16 C15 H15 120.7 ? C14 C15 H15 120.7 ? C15 C16 C17 122.0(4) ? C15 C16 Cl3 119.1(3) ? C17 C16 Cl3 118.9(3) ? C18 C17 C16 119.1(4) ? C18 C17 H17 120.5 ? C16 C17 H17 120.5 ? C17 C18 C13 120.8(4) ? C17 C18 H18 119.6 ? C13 C18 H18 119.6 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C10 1.854(4) yes Cl1 C4 1.722(4) ? Cl2 C6 1.717(4) ? Cl3 C16 1.735(4) ? F1 C1 1.305(7) ? F2 C1 1.283(6) ? F3 C1 1.273(6) yes N1 N2 1.343(5) yes N1 C11 1.376(5) yes N1 C5 1.427(5) yes N2 C9 1.335(5) yes N3 C8 1.138(5) yes N4 C12 1.276(5) yes N4 C11 1.380(5) yes C1 C2 1.498(6) ? C2 C7 1.365(6) ? C2 C3 1.380(6) ? C3 C4 1.388(6) ? C3 H3 0.9300 ? C4 C5 1.383(6) ? C5 C6 1.392(6) ? C6 C7 1.377(6) ? C7 H7 0.9300 ? C8 C9 1.431(6) yes C9 C10 1.398(6) yes C10 C11 1.373(5) yes C12 C13 1.459(5) ? C12 H12 0.9300 ? C13 C18 1.383(5) ? C13 C14 1.390(6) ? C14 C15 1.384(6) ? C14 H14 0.9300 ? C15 C16 1.357(6) ? C15 H15 0.9300 ? C16 C17 1.376(6) ? C17 C18 1.372(6) ? C17 H17 0.9300 ? C18 H18 0.9300 ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655276 2 PubChem 139072558