#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/53/2235331.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_2235331
loop_
_publ_author_name
'Xu, Li-Ying'
'Li, Ning'
'Li, Jia-Min'
'Zhang, Heng-Qiang'
'Sun, Zhen-Hai'
_publ_section_title
;
 (4Z)-4-[(2-Chloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           ZQ2164
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1843
_journal_paper_doi               10.1107/S1600536812020004
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C23 H18 Cl N3 O'
_chemical_formula_moiety         'C23 H18 Cl N3 O'
_chemical_formula_sum            'C23 H18 Cl N3 O'
_chemical_formula_weight         387.85
_chemical_name_systematic
;
(4Z)-4-[(2-Chloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-
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                 90.4230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0425(3)
_cell_length_b                   18.5180(7)
_cell_length_c                   11.1983(4)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      3.08
_cell_volume                     1875.09(12)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '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  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17018
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808.0
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_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)+(0.0482P)²+0.9306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                4251
_reflns_number_total             4637
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2164.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235331
_cod_database_fobs_code          2235331
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 0.86725(13) -0.06692(6) -0.09829(10) 0.0186(2) Uani d . 1 1
C C2 0.87873(15) -0.07367(7) -0.22145(11) 0.0238(2) Uani d . 1 1
H H2 0.8476 -0.0364 -0.2713 0.029 Uiso calc R 1 1
C C3 0.93725(15) -0.13668(7) -0.26969(12) 0.0271(3) Uani d . 1 1
H H3 0.9454 -0.1413 -0.3521 0.033 Uiso calc R 1 1
C C4 0.98343(14) -0.19250(7) -0.19629(12) 0.0253(3) Uani d . 1 1
H H4 1.0181 -0.2354 -0.2291 0.030 Uiso calc R 1 1
C C5 0.97757(15) -0.18398(7) -0.07385(12) 0.0284(3) Uani d . 1 1
H H5 1.0116 -0.2208 -0.0242 0.034 Uiso calc R 1 1
C C6 0.92153(15) -0.12112(7) -0.02397(11) 0.0260(3) Uani d . 1 1
H H6 0.9203 -0.1153 0.0585 0.031 Uiso calc R 1 1
C C7 0.70636(14) 0.10296(6) -0.05496(10) 0.0196(2) Uani d . 1 1
C C8 0.67068(17) 0.17489(7) -0.10804(11) 0.0269(3) Uani d . 1 1
H H8A 0.7155 0.1787 -0.1852 0.040 Uiso calc R 1 1
H H8B 0.7083 0.2124 -0.0570 0.040 Uiso calc R 1 1
H H8C 0.5654 0.1798 -0.1161 0.040 Uiso calc R 1 1
C C9 0.68060(13) 0.07593(6) 0.06368(10) 0.0187(2) Uani d . 1 1
C C10 0.74394(13) 0.00384(6) 0.06478(10) 0.0198(2) Uani d . 1 1
C C11 0.62430(12) 0.10790(6) 0.16590(10) 0.0164(2) Uani d . 1 1
C C12 0.56486(12) 0.18268(6) 0.16522(10) 0.0169(2) Uani d . 1 1
C C13 0.43881(14) 0.20000(7) 0.09874(11) 0.0234(2) Uani d . 1 1
H H13 0.3877 0.1641 0.0577 0.028 Uiso calc R 1 1
C C14 0.38969(16) 0.27111(8) 0.09393(13) 0.0326(3) Uani d . 1 1
H H14 0.3046 0.2826 0.0509 0.039 Uiso calc R 1 1
C C15 0.46709(18) 0.32468(7) 0.15296(14) 0.0359(3) Uani d . 1 1
H H15 0.4353 0.3723 0.1478 0.043 Uiso calc R 1 1
C C16 0.59174(17) 0.30782(7) 0.21975(13) 0.0318(3) Uani d . 1 1
H H16 0.6434 0.3442 0.2594 0.038 Uiso calc R 1 1
C C17 0.63988(14) 0.23657(7) 0.22775(11) 0.0225(2) Uani d . 1 1
H H17 0.7218 0.2250 0.2747 0.027 Uiso calc R 1 1
C C18 0.57642(12) 0.08798(6) 0.38216(9) 0.0161(2) Uani d . 1 1
C C19 0.43971(13) 0.12143(6) 0.39789(10) 0.0189(2) Uani d . 1 1
H H19 0.3851 0.1365 0.3317 0.023 Uiso calc R 1 1
C C20 0.38483(13) 0.13232(6) 0.51203(11) 0.0211(2) Uani d . 1 1
H H20 0.2938 0.1548 0.5218 0.025 Uiso calc R 1 1
C C21 0.46478(14) 0.10990(6) 0.61183(10) 0.0213(2) Uani d . 1 1
H H21 0.4270 0.1172 0.6879 0.026 Uiso calc R 1 1
C C22 0.60091(13) 0.07666(6) 0.59773(10) 0.0196(2) Uani d . 1 1
H H22 0.6550 0.0616 0.6642 0.024 Uiso calc R 1 1
C C23 0.65570(12) 0.06605(6) 0.48371(10) 0.0166(2) Uani d . 1 1
Cl Cl1 0.82565(3) 0.023579(16) 0.46642(3) 0.02280(9) Uani d . 1 1
H H3A 0.678(2) 0.0288(10) 0.2610(16) 0.034(5) Uiso d . 1 1
N N1 0.79928(12) -0.00523(5) -0.04860(8) 0.0200(2) Uani d . 1 1
N N2 0.77460(12) 0.05536(5) -0.12101(9) 0.0210(2) Uani d . 1 1
N N3 0.63332(12) 0.07069(6) 0.26879(8) 0.0194(2) Uani d . 1 1
O O1 0.74879(11) -0.04063(5) 0.14826(8) 0.0267(2) Uani d . 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 120.02(11)
C2 C1 N1 119.96(11)
C6 C1 N1 120.02(10)
C1 C2 C3 119.47(12)
C1 C2 H2 120.3
C3 C2 H2 120.3
C4 C3 C2 120.65(12)
C4 C3 H3 119.7
C2 C3 H3 119.7
C5 C4 C3 119.39(12)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 120.78(12)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 119.50(12)
C5 C6 H6 120.2
C1 C6 H6 120.2
N2 C7 C9 111.56(10)
N2 C7 C8 118.52(10)
C9 C7 C8 129.90(10)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C11 C9 C7 132.45(11)
C11 C9 C10 122.12(10)
C7 C9 C10 105.11(10)
O1 C10 N1 126.82(11)
O1 C10 C9 128.70(11)
N1 C10 C9 104.48(9)
N3 C11 C9 117.88(10)
N3 C11 C12 120.12(10)
C9 C11 C12 121.87(10)
C17 C12 C13 119.80(11)
C17 C12 C11 119.38(10)
C13 C12 C11 120.77(10)
C14 C13 C12 119.87(13)
C14 C13 H13 120.1
C12 C13 H13 120.1
C15 C14 C13 120.10(13)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C16 120.34(12)
C14 C15 H15 119.8
C16 C15 H15 119.8
C15 C16 C17 120.11(13)
C15 C16 H16 119.9
C17 C16 H16 119.9
C16 C17 C12 119.73(12)
C16 C17 H17 120.1
C12 C17 H17 120.1
C19 C18 C23 118.37(10)
C19 C18 N3 122.96(10)
C23 C18 N3 118.51(10)
C20 C19 C18 120.23(11)
C20 C19 H19 119.9
C18 C19 H19 119.9
C19 C20 C21 120.61(11)
C19 C20 H20 119.7
C21 C20 H20 119.7
C22 C21 C20 119.87(11)
C22 C21 H21 120.1
C20 C21 H21 120.1
C21 C22 C23 119.42(11)
C21 C22 H22 120.3
C23 C22 H22 120.3
C22 C23 C18 121.49(10)
C22 C23 Cl1 119.26(9)
C18 C23 Cl1 119.25(9)
C10 N1 N2 112.22(9)
C10 N1 C1 128.54(10)
N2 N1 C1 119.16(9)
C7 N2 N1 106.62(9)
C11 N3 C18 129.41(10)
C11 N3 H3A 113.1(12)
C18 N3 H3A 117.4(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3895(16)
C1 C6 1.3910(17)
C1 N1 1.4133(14)
C2 C3 1.3920(17)
C2 H2 0.9300
C3 C4 1.383(2)
C3 H3 0.9300
C4 C5 1.3816(19)
C4 H4 0.9300
C5 C6 1.3885(18)
C5 H5 0.9300
C6 H6 0.9300
C7 N2 1.3084(15)
C7 C9 1.4403(15)
C7 C8 1.4928(16)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C11 1.3887(15)
C9 C10 1.4526(16)
C10 O1 1.2464(14)
C10 N1 1.3784(14)
C11 N3 1.3445(14)
C11 C12 1.4855(15)
C12 C17 1.3925(16)
C12 C13 1.3941(16)
C13 C14 1.3906(18)
C13 H13 0.9300
C14 C15 1.380(2)
C14 H14 0.9300
C15 C16 1.384(2)
C15 H15 0.9300
C16 C17 1.3921(19)
C16 H16 0.9300
C17 H17 0.9300
C18 C19 1.3950(16)
C18 C23 1.4000(15)
C18 N3 1.4102(14)
C19 C20 1.3892(16)
C19 H19 0.9300
C20 C21 1.3900(18)
C20 H20 0.9300
C21 C22 1.3863(17)
C21 H21 0.9300
C22 C23 1.3870(15)
C22 H22 0.9300
C23 Cl1 1.7384(11)
N1 N2 1.4012(13)
N3 H3A 0.877(19)
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 H3A O1 . 0.879(18) 1.915(18) 2.6800(14) 144.5(16)
C6 H6 O1 . 0.93 2.31 2.9027(16) 121
C16 H16 O1 2_655 0.93 2.56 3.4797(17) 170
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 3.56(19)
N1 C1 C2 C3 -175.90(12)
C1 C2 C3 C4 0.2(2)
C2 C3 C4 C5 -3.0(2)
C3 C4 C5 C6 2.1(2)
C4 C5 C6 C1 1.6(2)
C2 C1 C6 C5 -4.49(19)
N1 C1 C6 C5 174.98(12)
N2 C7 C9 C11 174.02(13)
C8 C7 C9 C11 -4.3(2)
N2 C7 C9 C10 0.57(14)
C8 C7 C9 C10 -177.72(13)
C11 C9 C10 O1 5.5(2)
C7 C9 C10 O1 179.79(13)
C11 C9 C10 N1 -174.35(11)
C7 C9 C10 N1 -0.05(13)
C7 C9 C11 N3 -170.78(12)
C10 C9 C11 N3 1.74(17)
C7 C9 C11 C12 5.1(2)
C10 C9 C11 C12 177.64(11)
N3 C11 C12 C17 63.52(15)
C9 C11 C12 C17 -112.29(13)
N3 C11 C12 C13 -119.24(13)
C9 C11 C12 C13 64.95(15)
C17 C12 C13 C14 0.82(18)
C11 C12 C13 C14 -176.41(11)
C12 C13 C14 C15 1.23(19)
C13 C14 C15 C16 -1.7(2)
C14 C15 C16 C17 0.0(2)
C15 C16 C17 C12 2.03(18)
C13 C12 C17 C16 -2.44(17)
C11 C12 C17 C16 174.82(11)
C23 C18 C19 C20 -0.05(17)
N3 C18 C19 C20 175.29(11)
C18 C19 C20 C21 -0.23(18)
C19 C20 C21 C22 0.31(18)
C20 C21 C22 C23 -0.10(17)
C21 C22 C23 C18 -0.18(17)
C21 C22 C23 Cl1 -179.40(9)
C19 C18 C23 C22 0.26(17)
N3 C18 C23 C22 -175.30(10)
C19 C18 C23 Cl1 179.47(8)
N3 C18 C23 Cl1 3.92(14)
O1 C10 N1 N2 179.70(12)
C9 C10 N1 N2 -0.45(13)
O1 C10 N1 C1 3.2(2)
C9 C10 N1 C1 -176.98(11)
C2 C1 N1 C10 161.96(12)
C6 C1 N1 C10 -17.50(19)
C2 C1 N1 N2 -14.36(17)
C6 C1 N1 N2 166.17(11)
C9 C7 N2 N1 -0.83(14)
C8 C7 N2 N1 177.68(11)
C10 N1 N2 C7 0.81(14)
C1 N1 N2 C7 177.71(11)
C9 C11 N3 C18 -175.06(11)
C12 C11 N3 C18 8.97(18)
C19 C18 N3 C11 37.69(18)
C23 C18 N3 C11 -146.98(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657840
