#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/92/2209278.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_2209278
loop_
_publ_author_name
'Hu, Tuo-Ping'
_publ_section_title
(E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
_journal_coeditor_code           OM2017
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2270
_journal_page_last               o2271
_journal_paper_doi               10.1107/S1600536806016801
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C25 H22 Cl N3 O2'
_chemical_formula_moiety         'C25 H22 Cl N3 O2'
_chemical_formula_sum            'C25 H22 Cl N3 O2'
_chemical_formula_weight         431.91
_chemical_name_systematic
;
(E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5-dimethyl-2-phenyl-
1H-pyrazol-3(2H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.597(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.038(6)
_cell_length_b                   6.916(2)
_cell_length_c                   19.160(6)
_cell_measurement_reflns_used    2085
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      2.29
_cell_volume                     2226.1(12)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12103
_diffrn_reflns_theta_full        26.56
_diffrn_reflns_theta_max         26.56
_diffrn_reflns_theta_min         1.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.222
_refine_ls_extinction_coef       0.0116(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0424
_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)+(0.0266P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2209
_reflns_number_total             4572
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2017.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2226.0(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209278
_cod_database_fobs_code          2209278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl Cl1 1.47258(3) 0.70901(10) 1.04163(3) 0.0765(3) Uani d . 1
O O1 1.16590(7) 0.5835(2) 0.77754(7) 0.0597(5) Uani d . 1
O O2 0.74676(8) 0.6841(2) 0.47100(7) 0.0588(4) Uani d . 1
N N1 0.88934(9) 0.3938(3) 0.51734(8) 0.0466(5) Uani d . 1
N N2 0.74246(9) 0.2698(2) 0.36860(8) 0.0436(4) Uani d . 1
N N3 0.70736(9) 0.4398(2) 0.39003(8) 0.0434(4) Uani d . 1
C C1 1.30131(13) 0.8729(4) 0.88487(11) 0.0645(7) Uani d . 1
H H1 1.2899 0.9801 0.8556 0.077 Uiso calc R 1
C C2 1.37113(13) 0.8691(4) 0.93457(12) 0.0642(7) Uani d . 1
H H2 1.4062 0.9732 0.9387 0.077 Uiso calc R 1
C C3 1.38739(11) 0.7104(3) 0.97709(10) 0.0481(6) Uani d . 1
C C4 1.33677(12) 0.5545(3) 0.97069(11) 0.0558(6) Uani d . 1
H H4 1.3487 0.4462 0.9993 0.067 Uiso calc R 1
C C5 1.26765(12) 0.5606(4) 0.92110(11) 0.0580(6) Uani d . 1
H H5 1.2333 0.4553 0.9165 0.070 Uiso calc R 1
C C6 1.24901(12) 0.7195(4) 0.87862(11) 0.0503(6) Uani d . 1
C C7 1.17092(12) 0.7343(4) 0.82863(11) 0.0676(7) Uani d . 1
H H7A 1.1271 0.7237 0.8549 0.081 Uiso calc R 1
H H7B 1.1672 0.8589 0.8050 0.081 Uiso calc R 1
C C8 1.09953(11) 0.5827(3) 0.72537(10) 0.0479(6) Uani d . 1
C C9 1.09657(11) 0.4347(3) 0.67648(10) 0.0527(6) Uani d . 1
H H9 1.1378 0.3451 0.6803 0.063 Uiso calc R 1
C C10 1.03259(11) 0.4196(3) 0.62199(10) 0.0505(6) Uani d . 1
H H10 1.0307 0.3184 0.5898 0.061 Uiso calc R 1
C C11 0.97077(11) 0.5546(3) 0.61462(10) 0.0454(6) Uani d . 1
C C12 0.97591(12) 0.7023(3) 0.66376(11) 0.0602(7) Uani d . 1
H H12 0.9356 0.7944 0.6595 0.072 Uiso calc R 1
C C13 1.03926(12) 0.7176(3) 0.71917(10) 0.0596(7) Uani d . 1
H H13 1.0411 0.8177 0.7518 0.072 Uiso calc R 1
C C14 0.90153(11) 0.5414(3) 0.55795(10) 0.0516(6) Uani d . 1
H H14 0.8654 0.6433 0.5514 0.062 Uiso calc R 1
C C15 0.85526(12) 0.0533(3) 0.41690(11) 0.0616(7) Uani d . 1
H H15A 0.9030 0.0620 0.4513 0.092 Uiso calc R 1
H H15B 0.8689 0.0357 0.3707 0.092 Uiso calc R 1
H H15C 0.8241 -0.0547 0.4280 0.092 Uiso calc R 1
C C16 0.80826(11) 0.2346(3) 0.41805(10) 0.0412(5) Uani d . 1
C C17 0.82201(11) 0.3849(3) 0.46479(10) 0.0396(5) Uani d . 1
C C18 0.75865(11) 0.5231(3) 0.44719(10) 0.0418(5) Uani d . 1
C C19 0.68859(12) 0.1196(3) 0.33516(11) 0.0617(7) Uani d . 1
H H19A 0.7190 0.0090 0.3252 0.092 Uiso calc R 1
H H19B 0.6587 0.1683 0.2918 0.092 Uiso calc R 1
H H19C 0.6527 0.0828 0.3665 0.092 Uiso calc R 1
C C20 0.65264(11) 0.5481(3) 0.34052(10) 0.0388(5) Uani d . 1
C C21 0.66043(12) 0.5580(3) 0.27002(11) 0.0505(6) Uani d . 1
H H21 0.7013 0.4923 0.2536 0.061 Uiso calc R 1
C C22 0.60618(13) 0.6676(3) 0.22393(12) 0.0600(7) Uani d . 1
H H22 0.6106 0.6741 0.1763 0.072 Uiso calc R 1
C C23 0.54629(13) 0.7662(3) 0.24811(13) 0.0627(7) Uani d . 1
H H23 0.5104 0.8395 0.2170 0.075 Uiso calc R 1
C C24 0.53930(13) 0.7566(3) 0.31862(13) 0.0603(7) Uani d . 1
H H24 0.4991 0.8249 0.3352 0.072 Uiso calc R 1
C C25 0.59179(12) 0.6461(3) 0.36472(11) 0.0496(6) Uani d . 1
H H25 0.5862 0.6376 0.4121 0.059 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'
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
_geom_angle_publ_flag
C8 O1 C7 116.73(16) yes
C14 N1 C17 120.30(18) yes
C16 N2 N3 106.62(15) yes
C16 N2 C19 124.11(17) yes
N3 N2 C19 117.03(15) yes
C18 N3 N2 109.23(15) yes
C18 N3 C20 123.76(16) yes
N2 N3 C20 120.37(15) yes
C6 C1 C2 120.7(2) ?
C6 C1 H1 119.6 ?
C2 C1 H1 119.6 ?
C3 C2 C1 119.1(2) ?
C3 C2 H2 120.4 ?
C1 C2 H2 120.4 ?
C2 C3 C4 121.01(19) ?
C2 C3 Cl1 119.29(18) yes
C4 C3 Cl1 119.68(18) yes
C3 C4 C5 119.1(2) ?
C3 C4 H4 120.4 ?
C5 C4 H4 120.4 ?
C6 C5 C4 121.2(2) ?
C6 C5 H5 119.4 ?
C4 C5 H5 119.4 ?
C5 C6 C1 118.8(2) ?
C5 C6 C7 121.6(2) ?
C1 C6 C7 119.5(2) ?
O1 C7 C6 109.42(18) yes
O1 C7 H7A 109.8 ?
C6 C7 H7A 109.8 ?
O1 C7 H7B 109.8 ?
C6 C7 H7B 109.8 ?
H7A C7 H7B 108.2 ?
C13 C8 O1 124.67(19) yes
C13 C8 C9 120.02(18) ?
O1 C8 C9 115.30(19) yes
C10 C9 C8 120.2(2) ?
C10 C9 H9 119.9 ?
C8 C9 H9 119.9 ?
C9 C10 C11 120.8(2) ?
C9 C10 H10 119.6 ?
C11 C10 H10 119.6 ?
C12 C11 C10 117.64(18) ?
C12 C11 C14 120.1(2) ?
C10 C11 C14 122.2(2) ?
C11 C12 C13 122.1(2) ?
C11 C12 H12 119.0 ?
C13 C12 H12 119.0 ?
C8 C13 C12 119.2(2) ?
C8 C13 H13 120.4 ?
C12 C13 H13 120.4 ?
N1 C14 C11 121.9(2) y
N1 C14 H14 119.0 ?
C11 C14 H14 119.0 ?
C16 C15 H15A 109.5 ?
C16 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C16 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N2 C16 C17 110.52(18) yes
N2 C16 C15 121.45(18) yes
C17 C16 C15 128.02(18) ?
C16 C17 N1 122.47(19) yes
C16 C17 C18 108.15(16) ?
N1 C17 C18 129.34(19) yes
O2 C18 N3 122.62(18) yes
O2 C18 C17 132.54(18) yes
N3 C18 C17 104.80(17) yes
N2 C19 H19A 109.5 ?
N2 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
N2 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C21 C20 C25 120.25(19) ?
C21 C20 N3 121.18(19) yes
C25 C20 N3 118.56(18) yes
C20 C21 C22 119.1(2) ?
C20 C21 H21 120.5 ?
C22 C21 H21 120.5 ?
C23 C22 C21 120.7(2) ?
C23 C22 H22 119.7 ?
C21 C22 H22 119.7 ?
C22 C23 C24 119.9(2) ?
C22 C23 H23 120.1 ?
C24 C23 H23 120.1 ?
C23 C24 C25 120.1(2) ?
C23 C24 H24 119.9 ?
C25 C24 H24 119.9 ?
C24 C25 C20 120.0(2) ?
C24 C25 H25 120.0 ?
C20 C25 H25 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.7428(19) yes
O1 C8 1.379(2) yes
O1 C7 1.423(2) yes
O2 C18 1.233(2) yes
N1 C14 1.279(2) yes
N1 C17 1.396(2) yes
N2 C16 1.364(2) yes
N2 N3 1.411(2) yes
N2 C19 1.462(2) yes
N3 C18 1.405(2) yes
N3 C20 1.426(2) yes
C1 C6 1.378(3) ?
C1 C2 1.395(3) ?
C1 H1 0.9300 ?
C2 C3 1.367(3) ?
C2 H2 0.9300 ?
C3 C4 1.374(3) ?
C4 C5 1.385(2) ?
C4 H4 0.9300 ?
C5 C6 1.373(3) ?
C5 H5 0.9300 ?
C6 C7 1.508(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C13 1.378(3) ?
C8 C9 1.382(3) ?
C9 C10 1.382(2) ?
C9 H9 0.9300 ?
C10 C11 1.397(3) ?
C10 H10 0.9300 ?
C11 C12 1.382(3) ?
C11 C14 1.467(2) ?
C12 C13 1.386(3) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 C16 1.490(3) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 C17 1.367(3) ?
C17 C18 1.439(3) ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 C21 1.381(3) ?
C20 C25 1.382(3) ?
C21 C22 1.392(3) ?
C21 H21 0.9300 ?
C22 C23 1.371(3) ?
C22 H22 0.9300 ?
C23 C24 1.377(3) ?
C23 H23 0.9300 ?
C24 C25 1.379(3) ?
C24 H24 0.9300 ?
C25 H25 0.9300 ?
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
C21 H21 O1 3_766 0.93 2.49 3.383(3) 161.1 yes
C4 H4 O2 2_746 0.93 2.56 3.220(3) 128.0 yes
C15 H15C O2 1_545 0.96 2.46 3.413(3) 173.1 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
C16 N2 N3 C18 8.5(2)
C19 N2 N3 C18 152.56(16)
C16 N2 N3 C20 160.99(16)
C19 N2 N3 C20 -55.0(2)
C6 C1 C2 C3 0.2(3)
C1 C2 C3 C4 1.1(3)
C1 C2 C3 Cl1 -177.49(17)
C2 C3 C4 C5 -1.1(3)
Cl1 C3 C4 C5 177.43(16)
C3 C4 C5 C6 -0.1(3)
C4 C5 C6 C1 1.4(3)
C4 C5 C6 C7 -175.0(2)
C2 C1 C6 C5 -1.5(3)
C2 C1 C6 C7 175.04(19)
C8 O1 C7 C6 -176.71(18)
C5 C6 C7 O1 -62.5(3)
C1 C6 C7 O1 121.1(2)
C7 O1 C8 C13 0.8(3)
C7 O1 C8 C9 179.82(19)
C13 C8 C9 C10 -1.1(3)
O1 C8 C9 C10 179.82(18)
C8 C9 C10 C11 1.1(3)
C9 C10 C11 C12 -0.2(3)
C9 C10 C11 C14 -179.21(19)
C10 C11 C12 C13 -0.6(3)
C14 C11 C12 C13 178.4(2)
O1 C8 C13 C12 179.24(19)
C9 C8 C13 C12 0.3(3)
C11 C12 C13 C8 0.6(4)
C17 N1 C14 C11 178.84(17)
C12 C11 C14 N1 -170.5(2)
C10 C11 C14 N1 8.4(3)
N3 N2 C16 C17 -7.2(2)
C19 N2 C16 C17 -148.05(18)
N3 N2 C16 C15 172.99(18)
C19 N2 C16 C15 32.2(3)
N2 C16 C17 N1 -174.56(17)
C15 C16 C17 N1 5.2(3)
N2 C16 C17 C18 3.3(2)
C15 C16 C17 C18 -177.0(2)
C14 N1 C17 C16 176.91(19)
C14 N1 C17 C18 -0.4(3)
N2 N3 C18 O2 171.55(19)
C20 N3 C18 O2 20.2(3)
N2 N3 C18 C17 -6.4(2)
C20 N3 C18 C17 -157.78(17)
C16 C17 C18 O2 -175.7(2)
N1 C17 C18 O2 2.0(4)
C16 C17 C18 N3 2.0(2)
N1 C17 C18 N3 179.69(18)
C18 N3 C20 C21 115.4(2)
N2 N3 C20 C21 -32.9(3)
C18 N3 C20 C25 -63.6(3)
N2 N3 C20 C25 148.04(18)
C25 C20 C21 C22 -0.1(3)
N3 C20 C21 C22 -179.12(18)
C20 C21 C22 C23 0.7(3)
C21 C22 C23 C24 -0.2(3)
C22 C23 C24 C25 -0.8(3)
C23 C24 C25 C20 1.4(3)
C21 C20 C25 C24 -1.0(3)
N3 C20 C25 C24 178.11(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654970
2 PubChem 92664419
