#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/46/2214664.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_2214664
loop_
_publ_author_name
Hong-Li
_publ_section_title
;
 3-(4-Bromophenyl)-5-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
;
_journal_coeditor_code           GK2085
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3499
_journal_page_last               o3499
_journal_paper_doi               10.1107/S1600536807033120
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H16 Br F N2'
_chemical_formula_moiety         'C21 H16 Br F N2'
_chemical_formula_sum            'C21 H16 Br F N2'
_chemical_formula_weight         395.27
_chemical_name_systematic
;
3-(4-Bromophenyl)-5-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.321(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.271(3)
_cell_length_b                   11.245(2)
_cell_length_c                   10.727(2)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.55
_cell_measurement_theta_min      2.29
_cell_volume                     1748.7(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'π and ω 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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7203
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  0.8153
_exptl_absorpt_correction_T_min  0.4915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.634
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0435
_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/[σ²(Fo²)+(0.0175P)²+1.2354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                1957
_reflns_number_total             3096
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2085.cif
_cod_data_source_block           I
_cod_original_cell_volume        1748.8(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214664
_cod_database_fobs_code          2214664
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.7173(3) 0.3506(4) 0.5661(4) 0.0687(10) Uani d . 1
H H1 0.7611 0.3543 0.6489 0.082 Uiso calc R 1
C C2 0.6527(3) 0.4398(4) 0.5276(4) 0.0749(11) Uani d . 1
H H2 0.6525 0.5035 0.5828 0.090 Uiso calc R 1
C C3 0.5896(3) 0.4319(4) 0.4071(5) 0.0738(11) Uani d . 1
C C4 0.5879(3) 0.3412(4) 0.3239(4) 0.0792(12) Uani d . 1
H H4 0.5437 0.3386 0.2413 0.095 Uiso calc R 1
C C5 0.6531(3) 0.2524(4) 0.3638(4) 0.0740(11) Uani d . 1
H H5 0.6524 0.1891 0.3078 0.089 Uiso calc R 1
C C6 0.7190(2) 0.2564(3) 0.4854(3) 0.0598(9) Uani d . 1
C C7 0.7940(3) 0.1637(3) 0.5307(4) 0.0715(10) Uani d . 1
H H7 0.8071 0.1486 0.6247 0.086 Uiso calc R 1
C C8 0.8841(3) 0.1979(4) 0.5025(4) 0.0820(12) Uani d . 1
H H8A 0.8796 0.2763 0.4635 0.098 Uiso calc R 1
H H8B 0.9366 0.1959 0.5821 0.098 Uiso calc R 1
C C9 0.8916(3) 0.1039(3) 0.4082(3) 0.0633(9) Uani d . 1
C C10 0.9613(2) 0.0970(3) 0.3421(4) 0.0611(9) Uani d . 1
C C11 1.0370(3) 0.1734(3) 0.3722(4) 0.0723(11) Uani d . 1
H H11 1.0435 0.2310 0.4367 0.087 Uiso calc R 1
C C12 1.1024(3) 0.1657(4) 0.3085(4) 0.0762(12) Uani d . 1
H H12 1.1523 0.2176 0.3298 0.091 Uiso calc R 1
C C13 1.0933(2) 0.0813(4) 0.2141(4) 0.0723(11) Uani d . 1
C C14 1.0200(3) 0.0046(4) 0.1822(4) 0.0785(11) Uani d . 1
H H14 1.0143 -0.0530 0.1178 0.094 Uiso calc R 1
C C15 0.9549(3) 0.0129(4) 0.2456(4) 0.0753(11) Uani d . 1
H H15 0.9051 -0.0393 0.2231 0.090 Uiso calc R 1
C C16 0.7075(3) -0.0327(3) 0.4722(4) 0.0658(10) Uani d . 1
C C17 0.6978(3) -0.1413(4) 0.4081(4) 0.0710(10) Uani d . 1
H H17 0.7320 -0.1576 0.3521 0.085 Uiso calc R 1
C C18 0.6379(3) -0.2246(4) 0.4273(4) 0.0801(12) Uani d . 1
H H18 0.6315 -0.2969 0.3832 0.096 Uiso calc R 1
C C19 0.5869(3) -0.2037(4) 0.5102(4) 0.0831(12) Uani d . 1
H H19 0.5475 -0.2617 0.5238 0.100 Uiso calc R 1
C C20 0.5951(3) -0.0962(4) 0.5724(4) 0.0834(12) Uani d . 1
H H20 0.5604 -0.0808 0.6279 0.100 Uiso calc R 1
C C21 0.6544(3) -0.0102(4) 0.5535(4) 0.0770(11) Uani d . 1
H H21 0.6588 0.0630 0.5954 0.092 Uiso calc R 1
Br Br1 1.18176(3) 0.06824(5) 0.12420(5) 0.0946(2) Uani d . 1
F F1 0.52413(17) 0.5188(2) 0.3673(3) 0.1060(8) Uani d . 1
N N1 0.8282(2) 0.0237(3) 0.3876(3) 0.0656(8) Uani d . 1
N N2 0.7700(2) 0.0519(3) 0.4573(3) 0.0780(9) Uani d . 1
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 121.8(4)
C6 C1 H1 119.1
C2 C1 H1 119.1
C3 C2 C1 117.9(4)
C3 C2 H2 121.0
C1 C2 H2 121.0
C4 C3 C2 122.8(4)
C4 C3 F1 118.3(4)
C2 C3 F1 118.9(4)
C3 C4 C5 118.7(4)
C3 C4 H4 120.7
C5 C4 H4 120.7
C6 C5 C4 120.9(4)
C6 C5 H5 119.6
C4 C5 H5 119.6
C1 C6 C5 118.0(4)
C1 C6 C7 119.4(3)
C5 C6 C7 122.6(3)
N2 C7 C6 112.4(3)
N2 C7 C8 101.3(3)
C6 C7 C8 113.4(3)
N2 C7 H7 109.8
C6 C7 H7 109.8
C8 C7 H7 109.8
C9 C8 C7 102.6(3)
C9 C8 H8A 111.2
C7 C8 H8A 111.2
C9 C8 H8B 111.2
C7 C8 H8B 111.2
H8A C8 H8B 109.2
N1 C9 C10 120.2(4)
N1 C9 C8 113.5(3)
C10 C9 C8 126.2(3)
C15 C10 C11 117.0(4)
C15 C10 C9 120.7(3)
C11 C10 C9 122.3(4)
C12 C11 C10 121.5(4)
C12 C11 H11 119.2
C10 C11 H11 119.2
C13 C12 C11 119.5(4)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 120.6(4)
C12 C13 Br1 120.6(3)
C14 C13 Br1 118.8(4)
C13 C14 C15 119.7(4)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C10 121.7(4)
C14 C15 H15 119.2
C10 C15 H15 119.2
C17 C16 C21 118.7(4)
C17 C16 N2 121.0(4)
C21 C16 N2 120.3(4)
C18 C17 C16 120.0(4)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 121.4(4)
C17 C18 H18 119.3
C19 C18 H18 119.3
C20 C19 C18 118.9(4)
C20 C19 H19 120.5
C18 C19 H19 120.5
C19 C20 C21 120.7(4)
C19 C20 H20 119.7
C21 C20 H20 119.7
C20 C21 C16 120.2(4)
C20 C21 H21 119.9
C16 C21 H21 119.9
C9 N1 N2 109.0(3)
N1 N2 C16 119.4(3)
N1 N2 C7 113.4(3)
C16 N2 C7 126.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.374(5)
C1 C2 1.376(5)
C1 H1 0.9300
C2 C3 1.351(6)
C2 H2 0.9300
C3 C4 1.350(6)
C3 F1 1.367(5)
C4 C5 1.379(6)
C4 H4 0.9300
C5 C6 1.376(5)
C5 H5 0.9300
C6 C7 1.511(5)
C7 N2 1.468(5)
C7 C8 1.547(5)
C7 H7 0.9800
C8 C9 1.492(5)
C8 H8A 0.9700
C8 H8B 0.9700
C9 N1 1.290(4)
C9 C10 1.456(5)
C10 C15 1.382(5)
C10 C11 1.394(5)
C11 C12 1.378(5)
C11 H11 0.9300
C12 C13 1.363(5)
C12 H12 0.9300
C13 C14 1.369(5)
C13 Br1 1.897(4)
C14 C15 1.374(5)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.386(5)
C16 C21 1.388(5)
C16 N2 1.392(5)
C17 C18 1.370(5)
C17 H17 0.9300
C18 C19 1.374(5)
C18 H18 0.9300
C19 C20 1.367(6)
C19 H19 0.9300
C20 C21 1.383(6)
C20 H20 0.9300
C21 H21 0.9300
N1 N2 1.367(4)
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
C6 C1 C2 C3 0.5(6)
C1 C2 C3 C4 -0.3(6)
C1 C2 C3 F1 179.3(3)
C2 C3 C4 C5 0.4(6)
F1 C3 C4 C5 -179.3(3)
C3 C4 C5 C6 -0.6(6)
C2 C1 C6 C5 -0.7(6)
C2 C1 C6 C7 177.5(3)
C4 C5 C6 C1 0.7(6)
C4 C5 C6 C7 -177.4(4)
C1 C6 C7 N2 160.8(3)
C5 C6 C7 N2 -21.1(5)
C1 C6 C7 C8 -85.0(4)
C5 C6 C7 C8 93.0(4)
N2 C7 C8 C9 4.5(4)
C6 C7 C8 C9 -116.2(3)
C7 C8 C9 N1 -4.2(4)
C7 C8 C9 C10 175.8(3)
N1 C9 C10 C15 7.4(5)
C8 C9 C10 C15 -172.7(4)
N1 C9 C10 C11 -172.6(3)
C8 C9 C10 C11 7.4(6)
C15 C10 C11 C12 0.1(5)
C9 C10 C11 C12 -180.0(3)
C10 C11 C12 C13 -0.2(6)
C11 C12 C13 C14 0.0(6)
C11 C12 C13 Br1 179.9(3)
C12 C13 C14 C15 0.2(6)
Br1 C13 C14 C15 -179.6(3)
C13 C14 C15 C10 -0.3(6)
C11 C10 C15 C14 0.1(6)
C9 C10 C15 C14 -179.8(4)
C21 C16 C17 C18 -1.1(6)
N2 C16 C17 C18 178.1(4)
C16 C17 C18 C19 -0.5(6)
C17 C18 C19 C20 1.4(6)
C18 C19 C20 C21 -0.7(6)
C19 C20 C21 C16 -0.8(6)
C17 C16 C21 C20 1.7(6)
N2 C16 C21 C20 -177.4(4)
C10 C9 N1 N2 -178.1(3)
C8 C9 N1 N2 1.9(4)
C9 N1 N2 C16 -167.0(3)
C9 N1 N2 C7 1.5(4)
C17 C16 N2 N1 -5.7(5)
C21 C16 N2 N1 173.4(3)
C17 C16 N2 C7 -172.7(3)
C21 C16 N2 C7 6.5(6)
C6 C7 N2 N1 117.4(3)
C8 C7 N2 N1 -3.9(4)
C6 C7 N2 C16 -75.0(5)
C8 C7 N2 C16 163.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2366379
2 PubChem 7263590
