#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/00/2210049.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_2210049
loop_
_publ_author_name
'Hai-Zhen Xu'
'You-Quan Zhu'
'Hai-Bin Song'
_publ_section_title
(4Z)-3-Methyl-1-phenyl-4-{(phenyl)[4-(trifluoromethoxy)anilino]methylene}-1H-pyrazol-5(4H)-one
_journal_coeditor_code           AT2067
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3678
_journal_page_last               o3680
_journal_paper_doi               10.1107/S1600536806029655
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C24 H18 F3 N3 O2'
_chemical_formula_moiety         'C24 H18 F3 N3 O2'
_chemical_formula_sum            'C24 H18 F3 N3 O2'
_chemical_formula_weight         437.41
_chemical_name_systematic
;
(4Z)-3-Methyl-1-phenyl-4-{(phenyl)[4-(trifluoromethoxy)anilino]methylene}-
1H-pyrazol-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                106.698(4)
_cell_angle_beta                 99.688(5)
_cell_angle_gamma                108.459(9)
_cell_formula_units_Z            2
_cell_length_a                   8.0696(9)
_cell_length_b                   11.0945(12)
_cell_length_c                   13.1253(14)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_cell_volume                     1023.2(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2004)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9409
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.284
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4770
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                2854
_reflns_number_total             4770
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2067.cif
_cod_data_source_block           I
_cod_database_code               2210049
_cod_database_fobs_code          2210049
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.75299(16) 0.61087(13) 0.75314(11) 0.0270(3) Uani d . 1 . .
N N1 1.0507(2) 0.76483(16) 0.85706(12) 0.0234(4) Uani d . 1 . .
N N2 1.1526(2) 0.90516(16) 0.89128(13) 0.0260(4) Uani d . 1 . .
N N3 0.5576(2) 0.74522(17) 0.68609(13) 0.0255(4) Uani d . 1 . .
C C1 0.8722(2) 0.72936(19) 0.79899(15) 0.0230(4) Uani d . 1 . .
C C2 0.8595(2) 0.85739(19) 0.80125(15) 0.0231(4) Uani d . 1 . .
C C3 1.0399(2) 0.9593(2) 0.85964(15) 0.0248(4) Uani d . 1 . .
C C4 1.1115(3) 1.10967(19) 0.88521(17) 0.0315(5) Uani d . 1 . .
H H4A 1.2444 1.1481 0.9159 0.047 Uiso calc R 1 . .
H H4B 1.0578 1.1523 0.9395 0.047 Uiso calc R 1 . .
H H4C 1.0794 1.1272 0.8170 0.047 Uiso calc R 1 . .
C C5 1.1405(2) 0.67718(19) 0.87229(15) 0.0225(4) Uani d . 1 . .
C C6 1.3272(2) 0.7184(2) 0.88455(15) 0.0264(4) Uani d . 1 . .
H H6 1.3951 0.8056 0.8843 0.032 Uiso calc R 1 . .
C C7 1.4128(3) 0.6309(2) 0.89710(16) 0.0304(5) Uani d . 1 . .
H H7 1.5396 0.6581 0.9045 0.036 Uiso calc R 1 . .
C C8 1.3152(3) 0.5043(2) 0.89891(16) 0.0320(5) Uani d . 1 . .
H H8 1.3747 0.4448 0.9072 0.038 Uiso calc R 1 . .
C C9 1.1305(3) 0.4651(2) 0.88854(16) 0.0330(5) Uani d . 1 . .
H H9 1.0634 0.3786 0.8903 0.040 Uiso calc R 1 . .
C C10 1.0423(3) 0.5514(2) 0.87561(16) 0.0280(4) Uani d . 1 . .
H H10 0.9158 0.5244 0.8691 0.034 Uiso calc R 1 . .
C C11 0.7013(2) 0.86304(19) 0.74477(15) 0.0230(4) Uani d . 1 . .
C C12 0.6887(2) 0.99317(19) 0.74178(15) 0.0222(4) Uani d . 1 . .
C C13 0.6850(2) 1.0887(2) 0.83605(16) 0.0262(4) Uani d . 1 . .
H H13 0.6937 1.0727 0.9037 0.031 Uiso calc R 1 . .
C C14 0.6686(2) 1.2076(2) 0.83042(16) 0.0284(5) Uani d . 1 . .
H H14 0.6647 1.2727 0.8944 0.034 Uiso calc R 1 . .
C C15 0.6576(2) 1.2319(2) 0.73190(17) 0.0289(5) Uani d . 1 . .
H H15 0.6480 1.3140 0.7288 0.035 Uiso calc R 1 . .
C C16 0.6608(2) 1.1359(2) 0.63806(16) 0.0285(5) Uani d . 1 . .
H H16 0.6526 1.1521 0.5705 0.034 Uiso calc R 1 . .
C C17 0.6759(2) 1.0167(2) 0.64273(16) 0.0259(4) Uani d . 1 . .
H H17 0.6775 0.9509 0.5783 0.031 Uiso calc R 1 . .
C C18 0.3868(2) 0.72462(19) 0.61816(15) 0.0235(4) Uani d . 1 . .
C C19 0.2873(2) 0.8028(2) 0.65143(15) 0.0251(4) Uani d . 1 . .
H H19 0.3344 0.8746 0.7220 0.030 Uiso calc R 1 . .
C C20 0.1192(2) 0.7767(2) 0.58221(16) 0.0264(4) Uani d . 1 . .
H H20 0.0507 0.8299 0.6048 0.032 Uiso calc R 1 . .
C C21 0.0539(2) 0.6720(2) 0.48025(15) 0.0254(4) Uani d . 1 A .
C C22 0.1491(2) 0.5916(2) 0.44563(16) 0.0259(4) Uani d . 1 . .
H H22 0.1007 0.5191 0.3755 0.031 Uiso calc R 1 . .
C C23 0.3160(2) 0.61886(19) 0.51503(15) 0.0243(4) Uani d . 1 . .
H H23 0.3834 0.5648 0.4921 0.029 Uiso calc R 1 . .
O O2 -0.11392(18) 0.63400(15) 0.40217(12) 0.0386(4) Uani d D 1 . .
F F1 -0.26439(18) 0.7258(2) 0.50398(12) 0.0570(6) Uani d PDU 0.921(3) A 1
F F2 -0.1170(2) 0.83808(19) 0.41867(18) 0.0663(7) Uani d PDU 0.921(3) A 1
F F3 -0.3549(3) 0.6536(3) 0.3282(2) 0.0758(9) Uani d PDU 0.921(3) A 1
C C24 -0.2077(3) 0.7120(3) 0.4127(2) 0.0391(7) Uani d PDU 0.921(3) A 1
C C24' -0.187(2) 0.7195(14) 0.3866(15) 0.059(5) Uani d PDU 0.079(3) A 2
F F1' -0.195(3) 0.807(2) 0.4780(17) 0.075(5) Uani d PDU 0.079(3) A 2
F F2' -0.081(3) 0.7895(19) 0.3384(17) 0.073(6) Uani d PDU 0.079(3) A 2
F F3' -0.356(2) 0.653(3) 0.318(2) 0.063(7) Uani d PDU 0.079(3) A 2
H H3 0.581(3) 0.671(3) 0.6833(19) 0.061(8) Uiso 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'
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 111.85(14) n
C1 N1 C5 128.24(16) n
N2 N1 C5 119.42(14) n
C3 N2 N1 106.66(15) n
C11 N3 C18 128.61(17) n
C11 N3 H3 113.5(15) n
C18 N3 H3 117.3(15) n
O1 C1 N1 126.04(17) n
O1 C1 C2 129.19(16) n
N1 C1 C2 104.74(15) n
C11 C2 C3 132.47(18) n
C11 C2 C1 122.00(17) n
C3 C2 C1 105.20(15) n
N2 C3 C2 111.48(17) n
N2 C3 C4 118.65(17) n
C2 C3 C4 129.85(16) n
C3 C4 H4A 109.5 n
C3 C4 H4B 109.5 n
H4A C4 H4B 109.5 n
C3 C4 H4C 109.5 n
H4A C4 H4C 109.5 n
H4B C4 H4C 109.5 n
C10 C5 C6 120.29(17) n
C10 C5 N1 119.86(16) n
C6 C5 N1 119.85(17) n
C7 C6 C5 119.35(19) n
C7 C6 H6 120.3 n
C5 C6 H6 120.3 n
C8 C7 C6 120.71(18) n
C8 C7 H7 119.6 n
C6 C7 H7 119.6 n
C9 C8 C7 119.56(18) n
C9 C8 H8 120.2 n
C7 C8 H8 120.2 n
C8 C9 C10 120.5(2) n
C8 C9 H9 119.7 n
C10 C9 H9 119.7 n
C5 C10 C9 119.55(18) n
C5 C10 H10 120.2 n
C9 C10 H10 120.2 n
N3 C11 C2 118.34(17) n
N3 C11 C12 118.86(15) n
C2 C11 C12 122.71(16) n
C13 C12 C17 120.22(17) n
C13 C12 C11 120.49(16) n
C17 C12 C11 119.27(16) n
C14 C13 C12 119.40(17) n
C14 C13 H13 120.3 n
C12 C13 H13 120.3 n
C13 C14 C15 120.45(18) n
C13 C14 H14 119.8 n
C15 C14 H14 119.8 n
C16 C15 C14 119.82(18) n
C16 C15 H15 120.1 n
C14 C15 H15 120.1 n
C17 C16 C15 120.11(18) n
C17 C16 H16 119.9 n
C15 C16 H16 119.9 n
C16 C17 C12 119.99(18) n
C16 C17 H17 120.0 n
C12 C17 H17 120.0 n
C19 C18 C23 119.37(16) n
C19 C18 N3 122.90(17) n
C23 C18 N3 117.71(16) n
C18 C19 C20 120.48(17) n
C18 C19 H19 119.8 n
C20 C19 H19 119.8 n
C21 C20 C19 118.65(16) n
C21 C20 H20 120.7 n
C19 C20 H20 120.7 n
C20 C21 C22 122.06(16) n
C20 C21 O2 124.74(16) n
C22 C21 O2 113.20(16) n
C23 C22 C21 118.70(18) n
C23 C22 H22 120.6 n
C21 C22 H22 120.6 n
C22 C23 C18 120.73(16) n
C22 C23 H23 119.6 n
C18 C23 H23 119.6 n
C24' O2 C24 18.6(8) n
C24' O2 C21 124.4(8) n
C24 O2 C21 121.31(17) n
F3 C24 O2 108.4(2) n
F3 C24 F2 109.2(2) n
O2 C24 F2 114.4(2) n
F3 C24 F1 106.4(2) n
O2 C24 F1 112.3(2) n
F2 C24 F1 105.9(2) n
O2 C24' F2' 104.5(10) n
O2 C24' F1' 115.7(11) n
F2' C24' F1' 109.1(11) n
O2 C24' F3' 110.8(13) n
F2' C24' F3' 108.9(12) n
F1' C24' F3' 107.6(12) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.251(2) y
N1 C1 1.382(2) n
N1 N2 1.402(2) n
N1 C5 1.421(2) n
N2 C3 1.313(2) n
N3 C11 1.344(2) y
N3 C18 1.420(2) n
N3 H3 0.90(2) n
C1 C2 1.448(2) y
C2 C11 1.394(2) y
C2 C3 1.438(3) n
C3 C4 1.494(3) n
C4 H4A 0.9800 n
C4 H4B 0.9800 n
C4 H4C 0.9800 n
C5 C10 1.387(3) n
C5 C6 1.394(2) n
C6 C7 1.388(3) n
C6 H6 0.9500 n
C7 C8 1.384(3) n
C7 H7 0.9500 n
C8 C9 1.384(3) n
C8 H8 0.9500 n
C9 C10 1.392(3) n
C9 H9 0.9500 n
C10 H10 0.9500 n
C11 C12 1.490(2) n
C12 C13 1.390(2) n
C12 C17 1.392(3) n
C13 C14 1.388(3) n
C13 H13 0.9500 n
C14 C15 1.389(3) n
C14 H14 0.9500 n
C15 C16 1.388(3) n
C15 H15 0.9500 n
C16 C17 1.383(3) n
C16 H16 0.9500 n
C17 H17 0.9500 n
C18 C19 1.389(2) n
C18 C23 1.392(2) n
C19 C20 1.391(2) n
C19 H19 0.9500 n
C20 C21 1.378(2) n
C20 H20 0.9500 n
C21 C22 1.382(2) n
C21 O2 1.409(2) n
C22 C23 1.381(2) n
C22 H22 0.9500 n
C23 H23 0.9500 n
O2 C24' 1.308(6) n
O2 C24 1.312(2) n
F1 C24 1.338(3) n
F2 C24 1.330(3) n
F3 C24 1.311(3) n
C24' F2' 1.333(10) n
C24' F1' 1.334(10) n
C24' F3' 1.337(10) n
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
N3 H3 O1 . 0.90(2) 1.92(2) 2.6938(19) 143(2)
C20 H20 F1 . 0.95 2.38 2.906(2) 114.3
C10 H10 O1 . 0.95 2.43 2.965(2) 115.1
C15 H15 F3 2_576. 0.95 2.53 3.178(2) 125.9
C22 H22 O1 2_666. 0.95 2.58 3.306(2) 133.1
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
C1 N1 N2 C3 2.4(2) n
C5 N1 N2 C3 175.02(15) n
N2 N1 C1 O1 175.70(17) n
C5 N1 C1 O1 3.9(3) n
N2 N1 C1 C2 -2.61(19) n
C5 N1 C1 C2 -174.40(16) n
O1 C1 C2 C11 -2.3(3) n
N1 C1 C2 C11 175.93(16) n
O1 C1 C2 C3 -176.45(18) n
N1 C1 C2 C3 1.80(19) n
N1 N2 C3 C2 -1.1(2) n
N1 N2 C3 C4 -179.99(16) n
C11 C2 C3 N2 -173.66(19) n
C1 C2 C3 N2 -0.4(2) n
C11 C2 C3 C4 5.0(3) n
C1 C2 C3 C4 178.27(19) n
C1 N1 C5 C10 -30.8(3) n
N2 N1 C5 C10 157.91(17) n
C1 N1 C5 C6 149.57(18) n
N2 N1 C5 C6 -21.7(2) n
C10 C5 C6 C7 1.7(3) n
N1 C5 C6 C7 -178.69(16) n
C5 C6 C7 C8 -0.8(3) n
C6 C7 C8 C9 -0.3(3) n
C7 C8 C9 C10 0.4(3) n
C6 C5 C10 C9 -1.6(3) n
N1 C5 C10 C9 178.85(16) n
C8 C9 C10 C5 0.5(3) n
C18 N3 C11 C2 -176.67(17) n
C18 N3 C11 C12 0.0(3) n
C3 C2 C11 N3 171.82(18) n
C1 C2 C11 N3 -0.5(3) n
C3 C2 C11 C12 -4.7(3) n
C1 C2 C11 C12 -177.03(16) n
N3 C11 C12 C13 112.2(2) n
C2 C11 C12 C13 -71.3(2) n
N3 C11 C12 C17 -66.2(2) n
C2 C11 C12 C17 110.3(2) n
C17 C12 C13 C14 0.0(3) n
C11 C12 C13 C14 -178.38(16) n
C12 C13 C14 C15 -0.6(3) n
C13 C14 C15 C16 0.8(3) n
C14 C15 C16 C17 -0.4(3) n
C15 C16 C17 C12 -0.3(3) n
C13 C12 C17 C16 0.5(3) n
C11 C12 C17 C16 178.86(16) n
C11 N3 C18 C19 -46.2(3) n
C11 N3 C18 C23 135.4(2) n
C23 C18 C19 C20 -0.5(3) n
N3 C18 C19 C20 -178.93(18) n
C18 C19 C20 C21 -0.1(3) n
C19 C20 C21 C22 0.8(3) n
C19 C20 C21 O2 179.75(18) n
C20 C21 C22 C23 -1.0(3) n
O2 C21 C22 C23 179.99(17) n
C21 C22 C23 C18 0.4(3) n
C19 C18 C23 C22 0.4(3) n
N3 C18 C23 C22 178.86(17) n
C20 C21 O2 C24' 34.3(10) n
C22 C21 O2 C24' -146.7(10) n
C20 C21 O2 C24 12.4(3) n
C22 C21 O2 C24 -168.6(2) n
C24' O2 C24 F3 73(2) n
C21 O2 C24 F3 178.8(2) n
C24' O2 C24 F2 -49(2) n
C21 O2 C24 F2 56.7(3) n
C24' O2 C24 F1 -169(3) n
C21 O2 C24 F1 -63.9(3) n
C24 O2 C24' F2' 157(3) n
C21 O2 C24' F2' 70.6(14) n
C24 O2 C24' F1' 37(2) n
C21 O2 C24' F1' -49.4(16) n
C24 O2 C24' F3' -86(3) n
C21 O2 C24' F3' -172.2(14) n
