#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/54/2235432.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_2235432
loop_
_publ_author_name
'Zhi, Li-Hua'
'Wang, Yuan'
_publ_section_title
;
 3-Methyl-1-phenyl-4-[(Z)-phenyl(4-acetamidoanilino)methylidene]-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           GK2501
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2132
_journal_paper_doi               10.1107/S1600536812026840
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C25 H22 N4 O2'
_chemical_formula_moiety         'C25 H22 N4 O2'
_chemical_formula_sum            'C25 H22 N4 O2'
_chemical_formula_weight         410.47
_chemical_melting_point          567(9)
_chemical_name_systematic
;
3-Methyl-1-phenyl-4-[(Z)-phenyl(4-acetamidoanilino)methylidene]-
1H-pyrazol-5(4H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.138(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1800(4)
_cell_length_b                   11.0562(7)
_cell_length_c                   27.3932(16)
_cell_measurement_reflns_used    3801
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.15
_cell_measurement_theta_min      2.37
_cell_volume                     2165.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ 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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19323
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.49
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0526
_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)+(0.0834P)²+0.3021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1693
_reflns_number_gt                3047
_reflns_number_total             5168
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2501.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235432
_cod_database_fobs_code          2235432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_symmetry_multiplicity
C C1 1.1453(4) 0.8096(3) 0.15116(9) 0.0775(7) Uani d . 1 1
H H1A 1.2285 0.8712 0.1610 0.093 Uiso calc R 1 1
C C2 0.9601(4) 0.8167(2) 0.16072(10) 0.0790(7) Uani d . 1 1
H H2B 0.9189 0.8829 0.1777 0.095 Uiso calc R 1 1
C C3 0.8358(3) 0.7268(2) 0.14534(8) 0.0648(6) Uani d . 1 1
H H3B 0.7110 0.7325 0.1517 0.078 Uiso calc R 1 1
C C4 0.8971(3) 0.62867(18) 0.12057(7) 0.0485(5) Uani d . 1 1
C C5 1.0823(3) 0.6204(2) 0.11169(8) 0.0600(6) Uani d . 1 1
H H5A 1.1247 0.5535 0.0953 0.072 Uiso calc R 1 1
C C6 1.2045(3) 0.7111(2) 0.12710(9) 0.0718(7) Uani d . 1 1
H H6A 1.3295 0.7051 0.1210 0.086 Uiso calc R 1 1
C C7 0.6243(3) 0.48691(17) 0.12369(7) 0.0464(5) Uani d . 1 1
C C8 0.5483(3) 0.39817(17) 0.08929(6) 0.0441(5) Uani d . 1 1
C C9 0.6660(3) 0.40227(18) 0.04957(7) 0.0498(5) Uani d . 1 1
C C10 0.6607(4) 0.3296(2) 0.00387(8) 0.0725(7) Uani d . 1 1
H H10A 0.7596 0.3552 -0.0151 0.109 Uiso calc R 1 1
H H10B 0.5424 0.3410 -0.0148 0.109 Uiso calc R 1 1
H H10C 0.6766 0.2456 0.0121 0.109 Uiso calc R 1 1
C C11 0.4038(3) 0.31978(17) 0.09954(6) 0.0447(4) Uani d . 1 1
C C12 0.3277(3) 0.22780(18) 0.06380(6) 0.0456(5) Uani d . 1 1
C C13 0.3630(3) 0.10682(19) 0.07272(8) 0.0581(6) Uani d . 1 1
H H13A 0.4253 0.0827 0.1023 0.070 Uiso calc R 1 1
C C14 0.3063(4) 0.0220(2) 0.03798(9) 0.0746(7) Uani d . 1 1
H H14A 0.3336 -0.0593 0.0438 0.090 Uiso calc R 1 1
C C15 0.2096(4) 0.0564(3) -0.00520(9) 0.0771(7) Uani d . 1 1
H H15A 0.1720 -0.0014 -0.0287 0.092 Uiso calc R 1 1
C C16 0.1685(4) 0.1755(3) -0.01361(8) 0.0719(7) Uani d . 1 1
H H16A 0.0998 0.1984 -0.0425 0.086 Uiso calc R 1 1
C C17 0.2282(3) 0.2620(2) 0.02036(7) 0.0617(6) Uani d . 1 1
H H17A 0.2018 0.3432 0.0142 0.074 Uiso calc R 1 1
C C18 0.1978(3) 0.25908(17) 0.16386(7) 0.0463(5) Uani d . 1 1
C C19 0.2328(3) 0.21907(19) 0.21160(7) 0.0498(5) Uani d . 1 1
H H19A 0.3489 0.2333 0.2285 0.060 Uiso calc R 1 1
C C20 0.0977(3) 0.15856(18) 0.23422(7) 0.0491(5) Uani d . 1 1
H H20A 0.1231 0.1323 0.2664 0.059 Uiso calc R 1 1
C C21 -0.0763(3) 0.13596(17) 0.20977(6) 0.0443(4) Uani d . 1 1
C C22 -0.1115(3) 0.17695(19) 0.16203(7) 0.0549(5) Uani d . 1 1
H H22A -0.2276 0.1631 0.1451 0.066 Uiso calc R 1 1
C C23 0.0252(3) 0.2384(2) 0.13947(7) 0.0550(5) Uani d . 1 1
H H23A -0.0001 0.2660 0.1075 0.066 Uiso calc R 1 1
C C24 -0.3715(3) 0.02447(19) 0.21917(8) 0.0542(5) Uani d . 1 1
C C25 -0.4773(3) -0.0323(2) 0.25790(9) 0.0727(7) Uani d . 1 1
H H25A -0.5909 -0.0673 0.2430 0.109 Uiso calc R 1 1
H H25B -0.5068 0.0283 0.2811 0.109 Uiso calc R 1 1
H H25C -0.4021 -0.0942 0.2744 0.109 Uiso calc R 1 1
O O1 0.57427(19) 0.51393(13) 0.16510(5) 0.0552(4) Uani d . 1 1
O O2 -0.4273(2) 0.02170(19) 0.17623(6) 0.0864(6) Uani d . 1 1
N N1 0.7704(2) 0.53743(15) 0.10245(6) 0.0514(4) Uani d . 1 1
N N2 0.7976(2) 0.48311(15) 0.05741(6) 0.0551(5) Uani d . 1 1
N N3 0.3406(2) 0.32684(15) 0.14348(5) 0.0518(4) Uani d . 1 1
H H3A 0.3941 0.3806 0.1626 0.062 Uiso calc R 1 1
N N4 -0.2087(2) 0.07663(15) 0.23616(5) 0.0512(4) Uani d . 1 1
H H4A -0.1822 0.0732 0.2674 0.061 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 119.0(2)
C6 C1 H1A 120.5
C2 C1 H1A 120.5
C3 C2 C1 120.7(2)
C3 C2 H2B 119.7
C1 C2 H2B 119.7
C2 C3 C4 119.6(2)
C2 C3 H3B 120.2
C4 C3 H3B 120.2
C3 C4 C5 119.8(2)
C3 C4 N1 120.75(18)
C5 C4 N1 119.38(18)
C4 C5 C6 119.8(2)
C4 C5 H5A 120.1
C6 C5 H5A 120.1
C1 C6 C5 121.0(2)
C1 C6 H6A 119.5
C5 C6 H6A 119.5
O1 C7 N1 125.51(18)
O1 C7 C8 129.31(17)
N1 C7 C8 105.17(15)
C11 C8 C7 122.49(15)
C11 C8 C9 131.94(17)
C7 C8 C9 105.13(16)
N2 C9 C8 111.31(16)
N2 C9 C10 118.23(16)
C8 C9 C10 130.45(19)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 C8 117.75(17)
N3 C11 C12 120.29(16)
C8 C11 C12 121.91(15)
C13 C12 C17 119.33(19)
C13 C12 C11 119.85(18)
C17 C12 C11 120.75(18)
C14 C13 C12 120.1(2)
C14 C13 H13A 119.9
C12 C13 H13A 119.9
C15 C14 C13 120.3(2)
C15 C14 H14A 119.8
C13 C14 H14A 119.8
C16 C15 C14 119.9(2)
C16 C15 H15A 120.1
C14 C15 H15A 120.1
C15 C16 C17 120.5(2)
C15 C16 H16A 119.8
C17 C16 H16A 119.8
C16 C17 C12 119.8(2)
C16 C17 H17A 120.1
C12 C17 H17A 120.1
C23 C18 C19 119.12(17)
C23 C18 N3 123.15(17)
C19 C18 N3 117.60(18)
C20 C19 C18 120.51(19)
C20 C19 H19A 119.7
C18 C19 H19A 119.7
C19 C20 C21 120.86(17)
C19 C20 H20A 119.6
C21 C20 H20A 119.6
C22 C21 C20 118.52(17)
C22 C21 N4 124.24(18)
C20 C21 N4 117.18(16)
C21 C22 C23 120.34(19)
C21 C22 H22A 119.8
C23 C22 H22A 119.8
C18 C23 C22 120.64(18)
C18 C23 H23A 119.7
C22 C23 H23A 119.7
O2 C24 N4 123.28(18)
O2 C24 C25 122.3(2)
N4 C24 C25 114.45(18)
C24 C25 H25A 109.5
C24 C25 H25B 109.5
H25A C25 H25B 109.5
C24 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C7 N1 N2 111.92(15)
C7 N1 C4 129.48(15)
N2 N1 C4 118.51(14)
C9 N2 N1 106.42(14)
C11 N3 C18 129.94(17)
C11 N3 H3A 115.0
C18 N3 H3A 115.0
C24 N4 C21 128.81(16)
C24 N4 H4A 115.6
C21 N4 H4A 115.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.361(4)
C1 C2 1.380(4)
C1 H1A 0.9300
C2 C3 1.376(3)
C2 H2B 0.9300
C3 C4 1.373(3)
C3 H3B 0.9300
C4 C5 1.376(3)
C4 N1 1.418(2)
C5 C6 1.374(3)
C5 H5A 0.9300
C6 H6A 0.9300
C7 O1 1.256(2)
C7 N1 1.364(2)
C7 C8 1.434(3)
C8 C11 1.399(3)
C8 C9 1.437(2)
C9 N2 1.304(3)
C9 C10 1.485(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 N3 1.326(2)
C11 C12 1.482(3)
C12 C13 1.379(3)
C12 C17 1.385(3)
C13 C14 1.372(3)
C13 H13A 0.9300
C14 C15 1.371(4)
C14 H14A 0.9300
C15 C16 1.365(4)
C15 H15A 0.9300
C16 C17 1.376(3)
C16 H16A 0.9300
C17 H17A 0.9300
C18 C23 1.374(3)
C18 C19 1.382(3)
C18 N3 1.424(2)
C19 C20 1.371(3)
C19 H19A 0.9300
C20 C21 1.386(3)
C20 H20A 0.9300
C21 C22 1.386(3)
C21 N4 1.407(2)
C22 C23 1.384(3)
C22 H22A 0.9300
C23 H23A 0.9300
C24 O2 1.209(3)
C24 N4 1.348(3)
C24 C25 1.497(3)
C25 H25A 0.9600
C25 H25B 0.9600
C25 H25C 0.9600
N1 N2 1.401(2)
N3 H3A 0.8600
N4 H4A 0.8600
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
N4 H4A O1 2_545 0.86 2.05 2.874(2) 161
N3 H3A O1 . 0.86 1.96 2.696(2) 143
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 -1.3(4)
C1 C2 C3 C4 0.5(4)
C2 C3 C4 C5 0.6(3)
C2 C3 C4 N1 -177.2(2)
C3 C4 C5 C6 -0.8(3)
N1 C4 C5 C6 176.98(19)
C2 C1 C6 C5 1.0(4)
C4 C5 C6 C1 0.1(4)
O1 C7 C8 C11 -3.9(3)
N1 C7 C8 C11 174.95(18)
O1 C7 C8 C9 -177.1(2)
N1 C7 C8 C9 1.7(2)
C11 C8 C9 N2 -172.8(2)
C7 C8 C9 N2 -0.5(2)
C11 C8 C9 C10 6.0(4)
C7 C8 C9 C10 178.3(2)
C7 C8 C11 N3 -2.1(3)
C9 C8 C11 N3 169.1(2)
C7 C8 C11 C12 -179.45(18)
C9 C8 C11 C12 -8.3(3)
N3 C11 C12 C13 -67.8(3)
C8 C11 C12 C13 109.5(2)
N3 C11 C12 C17 115.0(2)
C8 C11 C12 C17 -67.7(3)
C17 C12 C13 C14 2.6(3)
C11 C12 C13 C14 -174.6(2)
C12 C13 C14 C15 -1.9(4)
C13 C14 C15 C16 -0.3(4)
C14 C15 C16 C17 1.9(4)
C15 C16 C17 C12 -1.2(4)
C13 C12 C17 C16 -1.1(3)
C11 C12 C17 C16 176.10(19)
C23 C18 C19 C20 0.6(3)
N3 C18 C19 C20 176.74(17)
C18 C19 C20 C21 0.2(3)
C19 C20 C21 C22 -0.6(3)
C19 C20 C21 N4 -178.09(18)
C20 C21 C22 C23 0.3(3)
N4 C21 C22 C23 177.62(18)
C19 C18 C23 C22 -0.9(3)
N3 C18 C23 C22 -176.79(18)
C21 C22 C23 C18 0.4(3)
O1 C7 N1 N2 176.45(19)
C8 C7 N1 N2 -2.4(2)
O1 C7 N1 C4 0.0(3)
C8 C7 N1 C4 -178.89(19)
C3 C4 N1 C7 -40.4(3)
C5 C4 N1 C7 141.8(2)
C3 C4 N1 N2 143.3(2)
C5 C4 N1 N2 -34.5(3)
C8 C9 N2 N1 -1.0(2)
C10 C9 N2 N1 -179.88(19)
C7 N1 N2 C9 2.2(2)
C4 N1 N2 C9 179.07(18)
C8 C11 N3 C18 -179.58(19)
C12 C11 N3 C18 -2.2(3)
C23 C18 N3 C11 -47.3(3)
C19 C18 N3 C11 136.7(2)
O2 C24 N4 C21 0.3(4)
C25 C24 N4 C21 179.2(2)
C22 C21 N4 C24 16.4(3)
C20 C21 N4 C24 -166.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657865
