#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/51/2215129.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_2215129
loop_
_publ_author_name
'Yi-Feng Sun'
'Xin-Li Wang'
'Shi-Ying Ma'
'Zi-Ying Wang'
_publ_section_title
3-Methyl-1-phenyl-4-{phenyl[4-(trifluoromethyl)anilino]methylene}-1H-pyrazol-5(4H)-one
_journal_coeditor_code           HB2502
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3725
_journal_page_last               o3725
_journal_paper_doi               10.1107/S1600536807037993
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C24 H18 F3 N3 O'
_chemical_formula_moiety         'C24 H18 F3 N3 O'
_chemical_formula_sum            'C24 H18 F3 N3 O'
_chemical_formula_weight         421.41
_chemical_name_systematic        5(4H)-one
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.448(2)
_cell_angle_beta                 100.227(2)
_cell_angle_gamma                105.178(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6059(9)
_cell_length_b                   10.9913(12)
_cell_length_c                   13.8057(15)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.06
_cell_volume                     1013.0(2)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0108
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5150
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.395
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0552
_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/[σ²(Fo²)+(0.088P)²+0.5882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                3079
_reflns_number_total             3527
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2502.cif
_cod_data_source_block           I
_cod_database_code               2215129
_cod_database_fobs_code          2215129
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
F F1 1.2873(3) 0.7703(4) 0.52098(18) 0.1651(15) Uani d . 1
F F2 1.1537(3) 0.7329(3) 0.6340(3) 0.1570(13) Uani d . 1
F F3 1.2712(3) 0.9287(2) 0.64567(18) 0.1190(8) Uani d . 1
O O1 0.2518(2) 0.89023(15) 0.26159(13) 0.0553(4) Uani d . 1
N N1 -0.0459(2) 0.74140(17) 0.14646(14) 0.0452(4) Uani d . 1
N N2 -0.1474(3) 0.60170(17) 0.10526(14) 0.0481(5) Uani d . 1
N N3 0.4577(2) 0.74680(18) 0.32255(14) 0.0489(5) Uani d . 1
H H3 0.4386 0.8219 0.3269 0.059 Uiso calc R 1
C C1 0.1347(3) 0.7735(2) 0.20940(17) 0.0433(5) Uani d . 1
C C2 0.1515(3) 0.6428(2) 0.20245(16) 0.0418(5) Uani d . 1
C C3 -0.0321(3) 0.5436(2) 0.13746(17) 0.0445(5) Uani d . 1
C C4 -0.1047(4) 0.3929(2) 0.1069(2) 0.0617(7) Uani d . 1
H H4A -0.2385 0.3579 0.0713 0.093 Uiso calc R 1
H H4B -0.0832 0.3724 0.1697 0.093 Uiso calc R 1
H H4C -0.0393 0.3514 0.0599 0.093 Uiso calc R 1
C C5 -0.1398(3) 0.8326(2) 0.13113(16) 0.0446(5) Uani d . 1
C C6 -0.3329(3) 0.7998(3) 0.11965(19) 0.0545(6) Uani d . 1
H H6 -0.4027 0.7169 0.1203 0.065 Uiso calc R 1
C C7 -0.4214(4) 0.8914(3) 0.1072(2) 0.0634(7) Uani d . 1
H H7 -0.5509 0.8701 0.0998 0.076 Uiso calc R 1
C C8 -0.3185(4) 1.0139(3) 0.1055(2) 0.0668(7) Uani d . 1
H H8 -0.3780 1.0756 0.0978 0.080 Uiso calc R 1
C C9 -0.1283(4) 1.0441(3) 0.1152(2) 0.0692(7) Uani d . 1
H H9 -0.0592 1.1263 0.1133 0.083 Uiso calc R 1
C C10 -0.0376(4) 0.9544(2) 0.1279(2) 0.0583(6) Uani d . 1
H H10 0.0917 0.9759 0.1342 0.070 Uiso calc R 1
C C11 0.3135(3) 0.6321(2) 0.25890(16) 0.0418(5) Uani d . 1
C C12 0.6381(3) 0.7604(2) 0.38376(17) 0.0454(5) Uani d . 1
C C13 0.7166(3) 0.8622(2) 0.48522(18) 0.0504(5) Uani d . 1
H H13 0.6512 0.9199 0.5115 0.061 Uiso calc R 1
C C14 0.8908(3) 0.8778(2) 0.54689(18) 0.0551(6) Uani d . 1
H H14 0.9428 0.9462 0.6147 0.066 Uiso calc R 1
C C15 0.9884(3) 0.7923(3) 0.50833(18) 0.0523(6) Uani d . 1
C C16 0.9117(3) 0.6922(3) 0.40642(18) 0.0566(6) Uani d . 1
H H16 0.9775 0.6347 0.3802 0.068 Uiso calc R 1
C C17 0.7391(3) 0.6772(3) 0.34380(18) 0.0552(6) Uani d . 1
H H17 0.6902 0.6115 0.2748 0.066 Uiso calc R 1
C C18 1.1727(4) 0.8038(3) 0.5758(2) 0.0710(8) Uani d . 1
C C19 0.3297(3) 0.4991(2) 0.25615(16) 0.0433(5) Uani d . 1
C C20 0.3411(3) 0.4054(2) 0.16447(18) 0.0525(6) Uani d . 1
H H20 0.3318 0.4228 0.1024 0.063 Uiso calc R 1
C C21 0.3666(4) 0.2856(2) 0.1664(2) 0.0650(7) Uani d . 1
H H21 0.3753 0.2228 0.1054 0.078 Uiso calc R 1
C C22 0.3792(4) 0.2590(3) 0.2577(2) 0.0694(8) Uani d . 1
H H22 0.3982 0.1791 0.2586 0.083 Uiso calc R 1
C C23 0.3637(4) 0.3507(3) 0.3479(2) 0.0670(7) Uani d . 1
H H23 0.3692 0.3317 0.4091 0.080 Uiso calc R 1
C C24 0.3399(3) 0.4708(2) 0.34747(19) 0.0540(6) Uani d . 1
H H24 0.3307 0.5329 0.4086 0.065 Uiso calc R 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'
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'
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
C1 N1 N2 112.32(16) ?
C1 N1 C5 127.73(17) ?
N2 N1 C5 119.51(17) ?
C3 N2 N1 106.70(17) ?
C11 N3 C12 128.37(18) n
C11 N3 H3 115.8 ?
C12 N3 H3 115.8 ?
O1 C1 N1 126.24(19) ?
O1 C1 C2 129.26(19) n
N1 C1 C2 104.48(17) ?
C11 C2 C3 132.65(19) n
C11 C2 C1 122.13(19) n
C3 C2 C1 104.96(17) ?
N2 C3 C2 111.44(18) ?
N2 C3 C4 118.50(19) ?
C2 C3 C4 130.03(19) ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C10 C5 C6 120.1(2) ?
C10 C5 N1 119.7(2) ?
C6 C5 N1 120.2(2) ?
C5 C6 C7 119.4(2) ?
C5 C6 H6 120.3 ?
C7 C6 H6 120.3 ?
C8 C7 C6 120.4(2) ?
C8 C7 H7 119.8 ?
C6 C7 H7 119.8 ?
C9 C8 C7 119.5(2) ?
C9 C8 H8 120.3 ?
C7 C8 H8 120.3 ?
C8 C9 C10 121.0(3) ?
C8 C9 H9 119.5 ?
C10 C9 H9 119.5 ?
C9 C10 C5 119.6(2) ?
C9 C10 H10 120.2 ?
C5 C10 H10 120.2 ?
N3 C11 C2 118.67(18) n
N3 C11 C19 118.50(18) n
C2 C11 C19 122.75(18) n
C17 C12 C13 119.5(2) ?
C17 C12 N3 121.8(2) ?
C13 C12 N3 118.66(19) n
C14 C13 C12 120.2(2) ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C13 C14 C15 120.2(2) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C16 119.7(2) ?
C14 C15 C18 120.9(2) ?
C16 C15 C18 119.4(2) ?
C17 C16 C15 120.5(2) ?
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C16 C17 C12 119.9(2) ?
C16 C17 H17 120.1 ?
C12 C17 H17 120.1 ?
F2 C18 F1 108.1(3) ?
F2 C18 F3 103.3(3) ?
F1 C18 F3 104.5(3) ?
F2 C18 C15 113.4(2) ?
F1 C18 C15 113.1(2) ?
F3 C18 C15 113.5(3) ?
C24 C19 C20 119.8(2) ?
C24 C19 C11 119.31(19) ?
C20 C19 C11 120.87(19) ?
C21 C20 C19 119.4(2) ?
C21 C20 H20 120.3 ?
C19 C20 H20 120.3 ?
C22 C21 C20 120.5(2) ?
C22 C21 H21 119.8 ?
C20 C21 H21 119.8 ?
C21 C22 C23 120.0(2) ?
C21 C22 H22 120.0 ?
C23 C22 H22 120.0 ?
C22 C23 C24 120.1(2) ?
C22 C23 H23 119.9 ?
C24 C23 H23 119.9 ?
C23 C24 C19 120.2(2) ?
C23 C24 H24 119.9 ?
C19 C24 H24 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C18 1.301(3) ?
F2 C18 1.286(4) ?
F3 C18 1.321(4) ?
O1 C1 1.244(3) n
N1 C1 1.377(3) ?
N1 N2 1.396(2) ?
N1 C5 1.419(3) ?
N2 C3 1.307(3) n
N3 C11 1.340(3) n
N3 C12 1.421(3) n
N3 H3 0.8600 ?
C1 C2 1.451(3) n
C2 C11 1.390(3) n
C2 C3 1.442(3) ?
C3 C4 1.491(3) ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C5 C10 1.380(3) ?
C5 C6 1.385(3) ?
C6 C7 1.385(3) ?
C6 H6 0.9300 ?
C7 C8 1.379(4) ?
C7 H7 0.9300 ?
C8 C9 1.368(4) ?
C8 H8 0.9300 ?
C9 C10 1.379(3) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
C11 C19 1.488(3) n
C12 C17 1.389(3) ?
C12 C13 1.390(3) ?
C13 C14 1.378(3) ?
C13 H13 0.9300 ?
C14 C15 1.381(3) ?
C14 H14 0.9300 ?
C15 C16 1.387(3) ?
C15 C18 1.489(3) ?
C16 C17 1.375(3) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C19 C24 1.385(3) ?
C19 C20 1.390(3) ?
C20 C21 1.388(3) ?
C20 H20 0.9300 ?
C21 C22 1.375(4) ?
C21 H21 0.9300 ?
C22 C23 1.379(4) ?
C22 H22 0.9300 ?
C23 C24 1.380(3) ?
C23 H23 0.9300 ?
C24 H24 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O1 0.86 1.98 2.704(2) 141 y
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
C1 N1 N2 C3 -2.4(2)
C5 N1 N2 C3 -175.31(18)
N2 N1 C1 O1 -175.1(2)
C5 N1 C1 O1 -3.0(4)
N2 N1 C1 C2 3.3(2)
C5 N1 C1 C2 175.43(19)
O1 C1 C2 C11 0.6(4)
N1 C1 C2 C11 -177.68(19)
O1 C1 C2 C3 175.5(2)
N1 C1 C2 C3 -2.8(2)
N1 N2 C3 C2 0.5(2)
N1 N2 C3 C4 178.7(2)
C11 C2 C3 N2 175.6(2)
C1 C2 C3 N2 1.5(2)
C11 C2 C3 C4 -2.4(4)
C1 C2 C3 C4 -176.5(2)
C1 N1 C5 C10 36.3(3)
N2 N1 C5 C10 -152.0(2)
C1 N1 C5 C6 -143.6(2)
N2 N1 C5 C6 28.1(3)
C10 C5 C6 C7 -1.3(3)
N1 C5 C6 C7 178.6(2)
C5 C6 C7 C8 0.4(4)
C6 C7 C8 C9 0.6(4)
C7 C8 C9 C10 -0.7(4)
C8 C9 C10 C5 -0.2(4)
C6 C5 C10 C9 1.2(4)
N1 C5 C10 C9 -178.6(2)
C12 N3 C11 C2 -177.2(2)
C12 N3 C11 C19 6.0(3)
C3 C2 C11 N3 -172.6(2)
C1 C2 C11 N3 0.7(3)
C3 C2 C11 C19 4.0(4)
C1 C2 C11 C19 177.36(19)
C11 N3 C12 C17 41.3(3)
C11 N3 C12 C13 -140.4(2)
C17 C12 C13 C14 -1.9(3)
N3 C12 C13 C14 179.7(2)
C12 C13 C14 C15 -0.1(4)
C13 C14 C15 C16 1.2(4)
C13 C14 C15 C18 -177.2(2)
C14 C15 C16 C17 -0.2(4)
C18 C15 C16 C17 178.2(2)
C15 C16 C17 C12 -1.8(4)
C13 C12 C17 C16 2.9(4)
N3 C12 C17 C16 -178.8(2)
C14 C15 C18 F2 87.5(4)
C16 C15 C18 F2 -90.9(3)
C14 C15 C18 F1 -148.9(3)
C16 C15 C18 F1 32.7(4)
C14 C15 C18 F3 -30.0(4)
C16 C15 C18 F3 151.6(3)
N3 C11 C19 C24 64.0(3)
C2 C11 C19 C24 -112.7(2)
N3 C11 C19 C20 -113.8(2)
C2 C11 C19 C20 69.5(3)
C24 C19 C20 C21 -1.3(3)
C11 C19 C20 C21 176.5(2)
C19 C20 C21 C22 0.5(4)
C20 C21 C22 C23 1.0(4)
C21 C22 C23 C24 -1.5(4)
C22 C23 C24 C19 0.6(4)
C20 C19 C24 C23 0.8(4)
C11 C19 C24 C23 -177.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655312
2 PubChem 139072930
