#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/13/2201360.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_2201360
loop_
_publ_author_name
'Jin-Ling Wang'
'Shu-Ming Zhang'
'Fang-Ming Miao'
_publ_section_title
4-[(2-Hydroxyphenylamino)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3(4H)-one
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1365
_journal_page_last               o1366
_journal_paper_doi               10.1107/S1600536802020299
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C23 H19 N3 O2'
_chemical_formula_structural     'C23 H19 N3 O2'
_chemical_formula_sum            'C23 H19 N3 O2'
_chemical_formula_weight         369.41
_chemical_melting_point          .239E-237
_chemical_name_systematic
;
4-[(2-Hydroxyphenylamino)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3(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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.794(9)
_cell_angle_beta                 92.210(11)
_cell_angle_gamma                105.987(10)
_cell_formula_units_Z            2
_cell_length_a                   7.267(4)
_cell_length_b                   11.150(6)
_cell_length_c                   13.822(8)
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      1.69
_cell_volume                     987.2(10)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3405
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0697P)²+0.0157P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                1687
_reflns_number_total             2830
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6217.cif
_cod_data_source_block           I
_cod_database_code               2201360
_cod_database_fobs_code          2201360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
O1 0.0194(3) 0.6134(2) 0.72338(15) 0.0479(6) Uani d . 1 . . O
O2 0.0988(3) 0.3694(2) 0.45905(16) 0.0596(7) Uani d . 1 . . O
H2 0.0857 0.3606 0.3974 0.089 Uiso calc . 1 . . H
N1 -0.2391(4) 0.4939(3) 0.89890(19) 0.0480(7) Uani d . 1 . . N
N2 -0.1741(4) 0.5886(3) 0.85161(18) 0.0426(7) Uani d . 1 . . N
N3 0.1779(4) 0.4046(3) 0.65675(19) 0.0470(7) Uani d . 1 . . N
H3 0.1469 0.4714 0.6518 0.071 Uiso calc . 1 . . H
C1 -0.0494(4) 0.5515(3) 0.7818(2) 0.0386(8) Uani d . 1 . . C
C2 -0.0200(4) 0.4326(3) 0.7901(2) 0.0390(8) Uani d . 1 . . C
C3 -0.1449(4) 0.4038(3) 0.8632(2) 0.0436(8) Uani d . 1 . . C
C4 -0.1862(5) 0.2880(4) 0.8989(3) 0.0592(10) Uani d . 1 . . C
H4A -0.0810 0.3045 0.9512 0.089 Uiso calc . 1 . . H
H4B -0.2000 0.2047 0.8396 0.089 Uiso calc . 1 . . H
H4C -0.3040 0.2810 0.9286 0.089 Uiso calc . 1 . . H
C5 0.0970(4) 0.3621(3) 0.7285(2) 0.0393(8) Uani d . 1 . . C
C11 -0.2587(5) 0.6946(3) 0.8672(2) 0.0419(8) Uani d . 1 . . C
C12 -0.1411(5) 0.8204(4) 0.8751(3) 0.0552(9) Uani d . 1 . . C
H12 -0.0089 0.8360 0.8740 0.083 Uiso calc . 1 . . H
C13 -0.2220(6) 0.9233(4) 0.8844(3) 0.0640(10) Uani d . 1 . . C
H13 -0.1433 1.0074 0.8893 0.096 Uiso calc . 1 . . H
C14 -0.4176(6) 0.9016(4) 0.8865(3) 0.0657(11) Uani d . 1 . . C
H14 -0.4714 0.9698 0.8911 0.098 Uiso calc . 1 . . H
C15 -0.5333(5) 0.7775(4) 0.8818(3) 0.0659(11) Uani d . 1 . . C
H15 -0.6647 0.7633 0.8852 0.099 Uiso calc . 1 . . H
C16 -0.4541(5) 0.6723(3) 0.8719(2) 0.0537(9) Uani d . 1 . . C
H16 -0.5324 0.5889 0.8684 0.081 Uiso calc . 1 . . H
C21 0.1298(4) 0.2383(3) 0.7368(2) 0.0403(8) Uani d . 1 . . C
C22 0.2330(5) 0.2475(3) 0.8276(2) 0.0510(9) Uani d . 1 . . C
H22 0.2823 0.3308 0.8847 0.077 Uiso calc . 1 . . H
C23 0.2623(5) 0.1306(4) 0.8324(3) 0.0622(10) Uani d . 1 . . C
H23 0.3301 0.1362 0.8932 0.093 Uiso calc . 1 . . H
C24 0.1905(6) 0.0069(4) 0.7469(3) 0.0704(11) Uani d . 1 . . C
H24 0.2132 -0.0699 0.7499 0.106 Uiso calc . 1 . . H
C25 0.0863(7) -0.0033(4) 0.6578(3) 0.0801(13) Uani d . 1 . . C
H25 0.0359 -0.0872 0.6013 0.120 Uiso calc . 1 . . H
C26 0.0556(6) 0.1127(4) 0.6519(2) 0.0655(11) Uani d . 1 . . C
H26 -0.0143 0.1059 0.5913 0.098 Uiso calc . 1 . . H
C31 0.3075(4) 0.3579(3) 0.5865(2) 0.0408(8) Uani d . 1 . . C
C32 0.2665(4) 0.3454(3) 0.4826(2) 0.0425(8) Uani d . 1 . . C
C33 0.3932(5) 0.3112(3) 0.4130(2) 0.0530(9) Uani d . 1 . . C
H33 0.3679 0.3041 0.3442 0.080 Uiso calc . 1 . . H
C34 0.5586(5) 0.2874(4) 0.4453(3) 0.0663(11) Uani d . 1 . . C
H34 0.6425 0.2633 0.3977 0.099 Uiso calc . 1 . . H
C35 0.5990(5) 0.2992(4) 0.5476(3) 0.0666(11) Uani d . 1 . . C
H35 0.7100 0.2836 0.5689 0.100 Uiso calc . 1 . . H
C36 0.4734(5) 0.3344(4) 0.6184(2) 0.0576(10) Uani d . 1 . . C
H36 0.5002 0.3422 0.6872 0.086 Uiso calc . 1 . . H
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
_geom_angle_publ_flag
C32 O2 H2 109.5 ?
C3 N1 N2 105.6(2) yes
C1 N2 N1 111.9(2) yes
C1 N2 C11 127.3(2) ?
N1 N2 C11 120.2(2) ?
C5 N3 C31 131.2(2) ?
C5 N3 H3 114.4 ?
C31 N3 H3 114.4 ?
O1 C1 N2 124.7(3) ?
O1 C1 C2 129.8(3) ?
N2 C1 C2 105.5(2) yes
C5 C2 C1 122.7(3) ?
C5 C2 C3 132.1(3) ?
C1 C2 C3 105.0(2) yes
N1 C3 C2 111.8(3) yes
N1 C3 C4 118.0(3) ?
C2 C3 C4 130.1(3) ?
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 ?
N3 C5 C2 118.4(3) ?
N3 C5 C21 118.3(3) ?
C2 C5 C21 123.2(3) ?
C16 C11 C12 120.3(3) ?
C16 C11 N2 121.0(3) ?
C12 C11 N2 118.6(3) ?
C11 C12 C13 119.8(3) ?
C11 C12 H12 120.1 ?
C13 C12 H12 120.1 ?
C14 C13 C12 120.6(4) ?
C14 C13 H13 119.7 ?
C12 C13 H13 119.7 ?
C13 C14 C15 119.5(3) ?
C13 C14 H14 120.3 ?
C15 C14 H14 120.3 ?
C14 C15 C16 120.7(3) ?
C14 C15 H15 119.7 ?
C16 C15 H15 119.7 ?
C11 C16 C15 119.2(3) ?
C11 C16 H16 120.4 ?
C15 C16 H16 120.4 ?
C22 C21 C26 119.6(3) ?
C22 C21 C5 121.0(3) ?
C26 C21 C5 119.3(3) ?
C21 C22 C23 119.6(3) ?
C21 C22 H22 120.2 ?
C23 C22 H22 120.2 ?
C24 C23 C22 120.2(3) ?
C24 C23 H23 119.9 ?
C22 C23 H23 119.9 ?
C25 C24 C23 120.5(3) ?
C25 C24 H24 119.8 ?
C23 C24 H24 119.8 ?
C24 C25 C26 120.0(3) ?
C24 C25 H25 120.0 ?
C26 C25 H25 120.0 ?
C21 C26 C25 120.1(3) ?
C21 C26 H26 119.9 ?
C25 C26 H26 119.9 ?
C36 C31 C32 120.0(3) ?
C36 C31 N3 123.6(3) ?
C32 C31 N3 116.3(2) ?
O2 C32 C33 125.1(3) ?
O2 C32 C31 115.4(2) ?
C33 C32 C31 119.5(3) ?
C32 C33 C34 120.2(3) ?
C32 C33 H33 119.9 ?
C34 C33 H33 119.9 ?
C35 C34 C33 120.4(3) ?
C35 C34 H34 119.8 ?
C33 C34 H34 119.8 ?
C34 C35 C36 119.8(3) ?
C34 C35 H35 120.1 ?
C36 C35 H35 120.1 ?
C35 C36 C31 120.1(3) ?
C35 C36 H36 120.0 ?
C31 C36 H36 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.278(3) yes
O2 C32 . 1.370(3) ?
O2 H2 . 0.820 ?
N1 C3 . 1.326(4) yes
N1 N2 . 1.423(3) yes
N2 C1 . 1.379(3) yes
N2 C11 . 1.429(4) ?
N3 C5 . 1.340(4) yes
N3 C31 . 1.437(3) ?
N3 H3 . 0.860 ?
C1 C2 . 1.444(4) yes
C2 C5 . 1.411(4) yes
C2 C3 . 1.449(4) yes
C3 C4 . 1.507(4) ?
C4 H4A . 0.960 ?
C4 H4B . 0.960 ?
C4 H4C . 0.960 ?
C5 C21 . 1.507(4) ?
C11 C16 . 1.381(4) ?
C11 C12 . 1.389(5) ?
C12 C13 . 1.395(4) ?
C12 H12 . 0.930 ?
C13 C14 . 1.378(5) ?
C13 H13 . 0.930 ?
C14 C15 . 1.383(5) ?
C14 H14 . 0.930 ?
C15 C16 . 1.408(5) ?
C15 H15 . 0.930 ?
C16 H16 . 0.930 ?
C21 C22 . 1.391(4) ?
C21 C26 . 1.393(4) ?
C22 C23 . 1.402(4) ?
C22 H22 . 0.930 ?
C23 C24 . 1.385(5) ?
C23 H23 . 0.930 ?
C24 C25 . 1.370(5) ?
C24 H24 . 0.930 ?
C25 C26 . 1.402(5) ?
C25 H25 . 0.930 ?
C26 H26 . 0.930 ?
C31 C36 . 1.392(4) ?
C31 C32 . 1.402(4) ?
C32 C33 . 1.382(4) ?
C33 C34 . 1.392(4) ?
C33 H33 . 0.930 ?
C34 C35 . 1.382(5) ?
C34 H34 . 0.930 ?
C35 C36 . 1.388(4) ?
C35 H35 . 0.930 ?
C36 H36 . 0.930 ?
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
_geom_hbond_publ_flag
N3 H3 O1 . 0.86 2.01 2.750(3) 143 yes
O2 H2 O1 2_566 0.82 1.96 2.724(3) 155 yes
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
C3 N1 N2 C1 3.8(3)
C3 N1 N2 C11 175.3(3)
N1 N2 C1 O1 174.9(3)
C11 N2 C1 O1 4.2(5)
N1 N2 C1 C2 -4.5(3)
C11 N2 C1 C2 -175.2(3)
O1 C1 C2 C5 -0.8(5)
N2 C1 C2 C5 178.6(3)
O1 C1 C2 C3 -176.0(3)
N2 C1 C2 C3 3.3(3)
N2 N1 C3 C2 -1.5(3)
N2 N1 C3 C4 -179.1(3)
C5 C2 C3 N1 -175.7(3)
C1 C2 C3 N1 -1.1(3)
C5 C2 C3 C4 1.5(6)
C1 C2 C3 C4 176.2(3)
C31 N3 C5 C2 177.3(3)
C31 N3 C5 C21 -4.8(5)
C1 C2 C5 N3 -2.6(4)
C3 C2 C5 N3 171.2(3)
C1 C2 C5 C21 179.7(3)
C3 C2 C5 C21 -6.5(5)
C1 N2 C11 C16 133.0(3)
N1 N2 C11 C16 -37.0(4)
C1 N2 C11 C12 -45.3(4)
N1 N2 C11 C12 144.7(3)
C16 C11 C12 C13 -1.9(5)
N2 C11 C12 C13 176.4(3)
C11 C12 C13 C14 0.3(5)
C12 C13 C14 C15 1.5(5)
C13 C14 C15 C16 -1.8(5)
C12 C11 C16 C15 1.6(5)
N2 C11 C16 C15 -176.7(3)
C14 C15 C16 C11 0.2(5)
N3 C5 C21 C22 115.1(3)
C2 C5 C21 C22 -67.2(4)
N3 C5 C21 C26 -64.8(4)
C2 C5 C21 C26 113.0(4)
C26 C21 C22 C23 0.4(5)
C5 C21 C22 C23 -179.5(3)
C21 C22 C23 C24 0.6(5)
C22 C23 C24 C25 -1.6(6)
C23 C24 C25 C26 1.5(6)
C22 C21 C26 C25 -0.5(5)
C5 C21 C26 C25 179.4(3)
C24 C25 C26 C21 -0.5(6)
C5 N3 C31 C36 -47.9(5)
C5 N3 C31 C32 136.5(3)
C36 C31 C32 O2 179.4(3)
N3 C31 C32 O2 -4.8(4)
C36 C31 C32 C33 -0.8(5)
N3 C31 C32 C33 175.0(3)
O2 C32 C33 C34 -179.2(3)
C31 C32 C33 C34 1.0(5)
C32 C33 C34 C35 -0.8(6)
C33 C34 C35 C36 0.3(6)
C34 C35 C36 C31 -0.1(6)
C32 C31 C36 C35 0.3(5)
N3 C31 C36 C35 -175.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654668
