#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/49/1574929.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_1574929
loop_
_publ_author_name
'Guseinov, Firudin I.'
'Samigullina, Aida I.'
'Hökelek, Tuncer'
'Hamidov, Sahil Z.'
'Lasri, Jamal'
'Hasanov, Khudayar I.'
'Javadzade, Tahir A.'
'Belay, Alebel N.'
_publ_section_title
;
 1-[(2-Bromophenyl)diphenylmethyl]-3-(trifluoromethyl)-1H-pyrazole--1-(triphenylmethyl)-3-(trifluoromethyl)-1H-pyrazole
 (0.638:0.362)
;
_journal_coeditor_code           HB4519
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x250466
_journal_paper_doi               10.1107/S2414314625004663
_journal_volume                  10
_journal_year                    2025
_chemical_formula_iupac
'0.64(C23 H16 Br1 F3 N2), 0.36(C23 H17 F3 N2)'
_chemical_formula_moiety
'C14.72 H10.24 Br0.64 F1.92 N1.28, C8.28 H6.12 F1.08 N0.72'
_chemical_formula_sum            'C23 H16.36 Br0.64 F3 N2'
_chemical_formula_weight         428.88
_chemical_name_systematic
;
1-[(2-Bromophenyl)diphenylmethyl]-3-(trifluoromethyl)-1H-pyrazole;
1-(triphenylmethyl)-3-(trifluoromethyl)-1H-pyrazole
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/2
_cell_angle_alpha                95.3496(16)
_cell_angle_beta                 91.0661(16)
_cell_angle_gamma                103.5919(17)
_cell_formula_units_Z            2
_cell_length_a                   8.84082(17)
_cell_length_b                   9.48683(18)
_cell_length_c                   11.6797(2)
_cell_measurement_reflns_used    14043
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      80.3540
_cell_measurement_theta_min      3.7950
_cell_volume                     947.18(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2024)
;
_computing_data_reduction
;
CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21061
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.633
_diffrn_reflns_theta_min         3.804
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2024)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0432P)²+0.8880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                4012
_reflns_number_total             4105
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4519.cif
_cod_data_source_block           I
_cod_database_code               1574929
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.402
_shelx_estimated_absorpt_t_max   0.698
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.04169(3) 0.46569(3) 0.70061(3) 0.02635(12) Uani d 0.6380(14) . .
F F1 0.11203(14) 0.91657(15) 0.49575(12) 0.0398(3) Uani d 1 . .
F F2 0.26791(17) 0.89368(14) 0.36004(10) 0.0393(3) Uani d 1 . .
F F3 0.35009(15) 1.03658(13) 0.51449(11) 0.0356(3) Uani d 1 . .
N N1 0.32218(16) 0.78802(16) 0.63930(12) 0.0195(3) Uani d 1 . .
N N2 0.35135(16) 0.65782(15) 0.65518(12) 0.0176(3) Uani d 1 . .
C C3 0.3493(2) 0.57369(19) 0.55393(15) 0.0222(3) Uani d 1 . .
H H3 0.367687 0.478646 0.544845 0.027 Uiso calc 1 . .
C C4 0.3158(2) 0.6514(2) 0.46736(15) 0.0237(4) Uani d 1 . .
H H4 0.305721 0.622763 0.386909 0.028 Uiso calc 1 . .
C C5 0.2998(2) 0.7824(2) 0.52534(15) 0.0225(3) Uani d 1 . .
C C6 0.40061(18) 0.62246(17) 0.76976(14) 0.0167(3) Uani d 1 . .
C C7 0.32585(18) 0.69732(18) 0.86925(14) 0.0177(3) Uani d 1 . .
C C8 0.36095(19) 0.84936(19) 0.88728(15) 0.0203(3) Uani d 1 . .
H H8 0.425545 0.905119 0.835485 0.024 Uiso calc 1 . .
C C9 0.3028(2) 0.9205(2) 0.97994(16) 0.0247(4) Uani d 1 . .
H H9 0.325160 1.023968 0.989494 0.030 Uiso calc 1 . .
C C10 0.2121(2) 0.8406(2) 1.05844(16) 0.0273(4) Uani d 1 . .
H H10 0.172152 0.888721 1.121707 0.033 Uiso calc 1 . .
C C11 0.1807(2) 0.6893(2) 1.04331(16) 0.0267(4) Uani d 1 . .
H H11 0.120369 0.633808 1.097367 0.032 Uiso calc 1 . .
C C12 0.2369(2) 0.6185(2) 0.94940(15) 0.0219(3) Uani d 1 . .
H H12 0.214206 0.514998 0.939985 0.026 Uiso calc 1 . .
C C13 0.35039(19) 0.45490(18) 0.76648(14) 0.0186(3) Uani d 1 . .
C C15 0.1532(2) 0.2253(2) 0.73370(16) 0.0260(4) Uani d 1 . .
H H15 0.048461 0.175161 0.713620 0.031 Uiso calc 1 . .
C C16 0.2626(2) 0.14738(19) 0.75887(16) 0.0273(4) Uani d 1 . .
H H16 0.233156 0.044104 0.756042 0.033 Uiso calc 1 . .
C C17 0.4146(2) 0.22167(19) 0.78807(16) 0.0245(4) Uani d 1 . .
H H17 0.489986 0.169482 0.805959 0.029 Uiso calc 1 . .
C C18 0.4572(2) 0.37302(18) 0.79125(14) 0.0200(3) Uani d 1 . .
H H18 0.562283 0.422246 0.810911 0.024 Uiso calc 1 . .
C C19 0.57896(19) 0.67975(17) 0.78538(15) 0.0183(3) Uani d 1 . .
C C20 0.6721(2) 0.7239(2) 0.69431(16) 0.0234(4) Uani d 1 . .
H H20 0.625359 0.721401 0.620015 0.028 Uiso calc 1 . .
C C21 0.8338(2) 0.7717(2) 0.71114(18) 0.0300(4) Uani d 1 . .
H H21 0.896109 0.801274 0.648266 0.036 Uiso calc 1 . .
C C22 0.9034(2) 0.7763(2) 0.81901(18) 0.0286(4) Uani d 1 . .
H H22 1.013382 0.807270 0.830068 0.034 Uiso calc 1 . .
C C23 0.8114(2) 0.7352(2) 0.91089(17) 0.0256(4) Uani d 1 . .
H H23 0.858441 0.739789 0.985367 0.031 Uiso calc 1 . .
C C24 0.6510(2) 0.68749(19) 0.89435(15) 0.0216(3) Uani d 1 . .
H H24 0.589149 0.659670 0.957855 0.026 Uiso calc 1 . .
C C25 0.2586(2) 0.9072(2) 0.47476(16) 0.0269(4) Uani d 1 . .
C C14 0.1967(2) 0.37605(19) 0.73785(15) 0.0214(3) Uani d 1 . .
H H14 0.120377 0.427587 0.720820 0.026 Uiso calc 0.3620(14) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 N2 . . 103.84(14) ?
N1 N2 C3 . . 112.03(14) ?
N1 N2 C6 . . 122.28(13) ?
C3 N2 C6 . . 125.20(14) ?
N2 C3 C4 . . 107.44(15) ?
N2 C3 H3 . . 126.3 ?
C4 C3 H3 . . 126.3 ?
C3 C4 C5 . . 103.74(16) ?
C3 C4 H4 . . 128.1 ?
C5 C4 H4 . . 128.1 ?
N1 C5 C4 . . 112.94(16) ?
N1 C5 C25 . . 119.50(16) ?
C4 C5 C25 . . 127.54(16) ?
N2 C6 C13 . . 105.75(13) ?
N2 C6 C19 . . 108.08(13) ?
C13 C6 C19 . . 112.04(13) ?
N2 C6 C7 . . 111.89(12) ?
C13 C6 C7 . . 111.37(13) ?
C19 C6 C7 . . 107.72(13) ?
C12 C7 C8 . . 118.19(15) ?
C12 C7 C6 . . 122.00(15) ?
C8 C7 C6 . . 119.47(14) ?
C9 C8 C7 . . 121.07(16) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C10 C9 C8 . . 120.16(17) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C9 C10 C11 . . 119.21(17) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 120.46(17) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C7 C12 C11 . . 120.86(17) ?
C7 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C18 C13 C14 . . 116.31(15) ?
C18 C13 C6 . . 121.25(15) ?
C14 C13 C6 . . 122.44(14) ?
C14 C15 C16 . . 120.11(17) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.36(17) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C16 C17 C18 . . 120.02(16) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C17 C18 C13 . . 122.20(16) ?
C17 C18 H18 . . 118.9 ?
C13 C18 H18 . . 118.9 ?
C20 C19 C24 . . 118.32(16) ?
C20 C19 C6 . . 122.24(15) ?
C24 C19 C6 . . 119.44(15) ?
C19 C20 C21 . . 120.63(17) ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
C22 C21 C20 . . 120.31(17) ?
C22 C21 H21 . . 119.8 ?
C20 C21 H21 . . 119.8 ?
C21 C22 C23 . . 119.54(17) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.24(17) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C19 . . 120.94(16) ?
C23 C24 H24 . . 119.5 ?
C19 C24 H24 . . 119.5 ?
F3 C25 F2 . . 107.32(15) ?
F3 C25 F1 . . 105.90(16) ?
F2 C25 F1 . . 106.31(15) ?
F3 C25 C5 . . 113.50(15) ?
F2 C25 C5 . . 110.83(16) ?
F1 C25 C5 . . 112.53(15) ?
C15 C14 C13 . . 122.00(16) ?
C15 C14 Br1 . . 115.78(13) ?
C13 C14 Br1 . . 122.21(13) ?
C15 C14 H14 . . 119.0 ?
C13 C14 H14 . . 119.0 ?
Br1 C14 H14 . . 3.4 ?
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
Br1 C14 . 1.8400(17) ?
F1 C25 . 1.345(2) ?
F2 C25 . 1.340(2) ?
F3 C25 . 1.338(2) ?
N1 C5 . 1.336(2) ?
N1 N2 . 1.3481(19) ?
N2 C3 . 1.361(2) ?
N2 C6 . 1.491(2) ?
C3 C4 . 1.372(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.397(3) ?
C4 H4 . 0.9500 ?
C5 C25 . 1.487(2) ?
C6 C13 . 1.543(2) ?
C6 C19 . 1.544(2) ?
C6 C7 . 1.545(2) ?
C7 C12 . 1.391(2) ?
C7 C8 . 1.397(2) ?
C8 C9 . 1.392(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.390(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.393(3) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C18 . 1.398(2) ?
C13 C14 . 1.406(2) ?
C15 C14 . 1.387(2) ?
C15 C16 . 1.391(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.383(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.393(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 C20 . 1.392(2) ?
C19 C24 . 1.400(2) ?
C20 C21 . 1.399(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.384(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.388(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.388(2) ?
C23 H23 . 0.9500 ?
C24 H24 . 0.9500 ?
C14 H14 . 0.9500 ?
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
C11 H11 Br1 2_567 0.95 2.90 3.8277(19) 165 yes
C22 H22 Cg2 1_455 0.95 2.85 3.648(2) 143 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C3 . . . . 0.76(18) ?
C5 N1 N2 C6 . . . . 173.14(14) ?
N1 N2 C3 C4 . . . . -0.6(2) ?
C6 N2 C3 C4 . . . . -172.71(15) ?
N2 C3 C4 C5 . . . . 0.17(19) ?
N2 N1 C5 C4 . . . . -0.65(19) ?
N2 N1 C5 C25 . . . . 177.85(15) ?
C3 C4 C5 N1 . . . . 0.3(2) ?
C3 C4 C5 C25 . . . . -178.05(17) ?
N1 N2 C6 C13 . . . . 154.86(14) ?
C3 N2 C6 C13 . . . . -33.8(2) ?
N1 N2 C6 C19 . . . . -85.00(17) ?
C3 N2 C6 C19 . . . . 86.35(18) ?
N1 N2 C6 C7 . . . . 33.4(2) ?
C3 N2 C6 C7 . . . . -155.22(15) ?
N2 C6 C7 C12 . . . . 123.47(16) ?
C13 C6 C7 C12 . . . . 5.3(2) ?
C19 C6 C7 C12 . . . . -117.88(16) ?
N2 C6 C7 C8 . . . . -63.35(19) ?
C13 C6 C7 C8 . . . . 178.53(14) ?
C19 C6 C7 C8 . . . . 55.31(18) ?
C12 C7 C8 C9 . . . . -2.9(2) ?
C6 C7 C8 C9 . . . . -176.34(15) ?
C7 C8 C9 C10 . . . . 2.0(3) ?
C8 C9 C10 C11 . . . . 0.1(3) ?
C9 C10 C11 C12 . . . . -1.2(3) ?
C8 C7 C12 C11 . . . . 1.8(2) ?
C6 C7 C12 C11 . . . . 175.07(15) ?
C10 C11 C12 C7 . . . . 0.2(3) ?
N2 C6 C13 C18 . . . . 125.63(16) ?
C19 C6 C13 C18 . . . . 8.1(2) ?
C7 C6 C13 C18 . . . . -112.61(17) ?
N2 C6 C13 C14 . . . . -53.84(19) ?
C19 C6 C13 C14 . . . . -171.36(15) ?
C7 C6 C13 C14 . . . . 67.9(2) ?
C14 C15 C16 C17 . . . . 0.1(3) ?
C15 C16 C17 C18 . . . . -0.5(3) ?
C16 C17 C18 C13 . . . . 0.5(3) ?
C14 C13 C18 C17 . . . . -0.1(3) ?
C6 C13 C18 C17 . . . . -179.57(15) ?
N2 C6 C19 C20 . . . . -13.3(2) ?
C13 C6 C19 C20 . . . . 102.79(18) ?
C7 C6 C19 C20 . . . . -134.39(16) ?
N2 C6 C19 C24 . . . . 166.99(14) ?
C13 C6 C19 C24 . . . . -76.89(18) ?
C7 C6 C19 C24 . . . . 45.93(19) ?
C24 C19 C20 C21 . . . . 1.3(3) ?
C6 C19 C20 C21 . . . . -178.38(16) ?
C19 C20 C21 C22 . . . . -0.2(3) ?
C20 C21 C22 C23 . . . . -1.0(3) ?
C21 C22 C23 C24 . . . . 1.1(3) ?
C22 C23 C24 C19 . . . . 0.0(3) ?
C20 C19 C24 C23 . . . . -1.2(3) ?
C6 C19 C24 C23 . . . . 178.47(15) ?
N1 C5 C25 F3 . . . . 48.2(2) ?
C4 C5 C25 F3 . . . . -133.53(19) ?
N1 C5 C25 F2 . . . . 169.06(16) ?
C4 C5 C25 F2 . . . . -12.7(3) ?
N1 C5 C25 F1 . . . . -72.0(2) ?
C4 C5 C25 F1 . . . . 106.2(2) ?
C16 C15 C14 C13 . . . . 0.4(3) ?
C16 C15 C14 Br1 . . . . 179.13(15) ?
C18 C13 C14 C15 . . . . -0.3(3) ?
C6 C13 C14 C15 . . . . 179.15(16) ?
C18 C13 C14 Br1 . . . . -179.04(13) ?
C6 C13 C14 Br1 . . . . 0.5(2) ?
