#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/98/2209863.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_2209863
loop_
_publ_author_name
'Hu, Rong-Hua'
'Fang, Xiao-Niu'
'Sui, Yan'
'Luo, Qiu-Yan'
'Zou, Meng-Qiang'
_publ_section_title
;(E)-2-[2-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yliminomethyl)phenoxy]acetic
 acid monohydrate
;
_journal_coeditor_code           HG2063
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3558
_journal_page_last               o3560
_journal_paper_doi               10.1107/S1600536806028352
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H19 N3 O4, H2 O'
_chemical_formula_moiety         'C20 H19 N3 O4, H2 O'
_chemical_formula_sum            'C20 H21 N3 O5'
_chemical_formula_weight         383.40
_chemical_melting_point          466.5(3)
_chemical_name_systematic
;
{(E)-2-[2-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-
yliminomethyl)phenoxy]acetic acid monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.518(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.0213(15)
_cell_length_b                   6.8755(6)
_cell_length_c                   30.352(3)
_cell_measurement_reflns_used    1657
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.27
_cell_volume                     3749.1(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    APEX2
_computing_publication_material  APEX2
_computing_structure_refinement  APEX2
_computing_structure_solution    APEX2
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10093
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.177
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     APEX2
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0516
_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)+(0.0499P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                1522
_reflns_number_total             3231
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2063.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '466.2-466.9' was changed to
'466.5(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '466.2-466.9' was changed to
'466.5(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209863
_cod_database_fobs_code          2209863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 -0.00791(11) 0.6046(3) 0.87063(7) 0.0610(6) Uani d . 1
O O2 0.18056(11) 0.8674(3) 0.94052(7) 0.0574(6) Uani d . 1
O O3 0.05648(12) 1.0462(4) 0.95971(8) 0.0841(8) Uani d . 1
O O4 0.12074(13) 1.2879(4) 0.99355(9) 0.0860(8) Uani d . 1
H H4A 0.0792 1.3259 0.9987 0.129 Uiso calc R 1
O O5 0.00245(16) 0.6615(5) 0.96328(10) 0.0902(8) Uani d D 1
N N1 -0.05004(12) 0.3334(3) 0.83101(8) 0.0489(7) Uani d . 1
N N2 -0.01738(13) 0.1641(4) 0.81545(8) 0.0492(6) Uani d . 1
N N3 0.14185(12) 0.3618(4) 0.87651(7) 0.0487(6) Uani d . 1
C C1 0.15482(16) 0.5224(5) 0.89700(9) 0.0497(8) Uani d . 1
H H1 0.1150 0.6028 0.9024 0.060 Uiso calc R 1
C C2 0.23058(15) 0.5836(4) 0.91218(9) 0.0449(8) Uani d . 1
C C3 0.24315(16) 0.7617(5) 0.93360(9) 0.0492(8) Uani d . 1
C C4 0.31477(17) 0.8228(5) 0.94696(10) 0.0574(9) Uani d . 1
H H4 0.3225 0.9411 0.9615 0.069 Uiso calc R 1
C C5 0.37456(18) 0.7064(6) 0.93853(11) 0.0668(10) Uani d . 1
H H5 0.4227 0.7480 0.9469 0.080 Uiso calc R 1
C C6 0.36338(17) 0.5296(5) 0.91789(10) 0.0672(10) Uani d . 1
H H6 0.4038 0.4507 0.9129 0.081 Uiso calc R 1
C C7 0.29245(16) 0.4699(5) 0.90473(10) 0.0591(9) Uani d . 1
H H7 0.2854 0.3508 0.8905 0.071 Uiso calc R 1
C C8 0.18960(16) 1.0448(4) 0.96428(9) 0.0531(8) Uani d . 1
H H8A 0.2168 1.1374 0.9476 0.064 Uiso calc R 1
H H8B 0.2176 1.0223 0.9924 0.064 Uiso calc R 1
C C9 0.11482(19) 1.1230(5) 0.97158(11) 0.0601(9) Uani d . 1
C C10 0.00416(16) 0.4392(5) 0.85674(9) 0.0479(8) Uani d . 1
C C11 0.06979(16) 0.3183(4) 0.85914(9) 0.0437(8) Uani d . 1
C C12 0.05254(16) 0.1511(4) 0.83597(9) 0.0465(8) Uani d . 1
C C13 0.09902(16) -0.0241(4) 0.83191(10) 0.0640(9) Uani d . 1
H H13A 0.1462 -0.0057 0.8484 0.096 Uiso calc R 1
H H13B 0.1068 -0.0456 0.8014 0.096 Uiso calc R 1
H H13C 0.0743 -0.1347 0.8433 0.096 Uiso calc R 1
C C14 -0.06675(17) -0.0012(4) 0.80614(10) 0.0636(9) Uani d . 1
H H14A -0.0792 -0.0584 0.8334 0.095 Uiso calc R 1
H H14B -0.0422 -0.0960 0.7892 0.095 Uiso calc R 1
H H14C -0.1114 0.0420 0.7897 0.095 Uiso calc R 1
C C15 -0.10746(15) 0.4290(4) 0.80384(9) 0.0440(8) Uani d . 1
C C16 -0.10647(15) 0.4333(4) 0.75853(10) 0.0492(8) Uani d . 1
H H16 -0.0699 0.3658 0.7448 0.059 Uiso calc R 1
C C17 -0.16005(16) 0.5383(5) 0.73342(10) 0.0560(9) Uani d . 1
H H17 -0.1601 0.5393 0.7028 0.067 Uiso calc R 1
C C18 -0.21312(16) 0.6412(4) 0.75379(11) 0.0562(9) Uani d . 1
H H18 -0.2483 0.7148 0.7370 0.067 Uiso calc R 1
C C19 -0.21403(16) 0.6349(4) 0.79913(11) 0.0581(9) Uani d . 1
H H19 -0.2502 0.7037 0.8129 0.070 Uiso calc R 1
C C20 -0.16193(16) 0.5276(4) 0.82428(10) 0.0551(9) Uani d . 1
H H20 -0.1634 0.5217 0.8548 0.066 Uiso calc R 1
H H5A 0.023(2) 0.779(3) 0.9636(12) 0.106(17) Uiso d D 1
H H5B -0.004(3) 0.624(7) 0.9351(9) 0.25(4) Uiso d 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'
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
C3 O2 C8 118.0(2) ?
C9 O4 H4A 109.5 ?
H5A O5 H5B 108(3) ?
N2 N1 C10 109.0(2) y
N2 N1 C15 119.4(2) y
C10 N1 C15 121.4(2) y
C12 N2 N1 107.3(2) y
C12 N2 C14 124.5(3) y
N1 N2 C14 116.5(2) y
C1 N3 C11 119.9(3) y
N3 C1 C2 122.0(3) y
N3 C1 H1 119.0 ?
C2 C1 H1 119.0 ?
C7 C2 C3 117.7(3) ?
C7 C2 C1 121.6(3) ?
C3 C2 C1 120.7(3) ?
O2 C3 C4 123.5(3) ?
O2 C3 C2 115.5(3) ?
C4 C3 C2 121.0(3) ?
C5 C4 C3 119.4(3) ?
C5 C4 H4 120.3 ?
C3 C4 H4 120.3 ?
C6 C5 C4 120.5(3) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C7 C6 C5 119.8(3) ?
C7 C6 H6 120.1 ?
C5 C6 H6 120.1 ?
C6 C7 C2 121.6(3) ?
C6 C7 H7 119.2 ?
C2 C7 H7 119.2 ?
O2 C8 C9 108.6(3) ?
O2 C8 H8A 110.0 ?
C9 C8 H8A 110.0 ?
O2 C8 H8B 110.0 ?
C9 C8 H8B 110.0 ?
H8A C8 H8B 108.4 ?
O3 C9 O4 124.3(3) ?
O3 C9 C8 125.2(3) ?
O4 C9 C8 110.5(3) ?
O1 C10 N1 122.1(3) y
O1 C10 C11 132.6(3) y
N1 C10 C11 105.1(3) ?
C12 C11 N3 122.7(3) ?
C12 C11 C10 107.8(3) ?
N3 C11 C10 129.1(3) ?
N2 C12 C11 110.1(3) ?
N2 C12 C13 121.6(3) ?
C11 C12 C13 128.3(3) ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
N2 C14 H14A 109.5 ?
N2 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
N2 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C16 C15 C20 120.3(3) ?
C16 C15 N1 121.3(3) ?
C20 C15 N1 118.3(3) ?
C15 C16 C17 119.8(3) ?
C15 C16 H16 120.1 ?
C17 C16 H16 120.1 ?
C18 C17 C16 120.0(3) ?
C18 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C17 C18 C19 119.8(3) ?
C17 C18 H18 120.1 ?
C19 C18 H18 120.1 ?
C20 C19 C18 120.6(3) ?
C20 C19 H19 119.7 ?
C18 C19 H19 119.7 ?
C19 C20 C15 119.5(3) ?
C19 C20 H20 120.3 ?
C15 C20 H20 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.238(3) y
O2 C3 1.372(3) ?
O2 C8 1.420(3) ?
O3 C9 1.206(4) ?
O4 C9 1.315(4) ?
O4 H4A 0.8200 ?
O5 H5A 0.883(18) ?
O5 H5B 0.892(19) ?
N1 N2 1.403(3) y
N1 C10 1.405(3) y
N1 C15 1.432(3) y
N2 C12 1.364(3) y
N2 C14 1.457(3) y
N3 C1 1.280(3) y
N3 C11 1.395(3) y
C1 C2 1.468(4) y
C1 H1 0.9300 ?
C2 C7 1.395(4) ?
C2 C3 1.396(4) ?
C3 C4 1.387(4) ?
C4 C5 1.382(4) ?
C4 H4 0.9300 ?
C5 C6 1.375(4) ?
C5 H5 0.9300 ?
C6 C7 1.372(4) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.484(4) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C10 C11 1.443(4) ?
C11 C12 1.370(4) y
C12 C13 1.478(4) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 C16 1.377(4) ?
C15 C20 1.380(4) ?
C16 C17 1.385(4) ?
C16 H16 0.9300 ?
C17 C18 1.375(4) ?
C17 H17 0.9300 ?
C18 C19 1.378(4) ?
C18 H18 0.9300 ?
C19 C20 1.377(4) ?
C19 H19 0.9300 ?
C20 H20 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
O4 H4A O5 5_577 0.82 1.94 2.688(4) 151.0 yes
O5 H5B O1 ? 0.89(2) 1.96(3) 2.831(4) 166(4) yes
O5 H5A O3 ? 0.88(2) 1.95(3) 2.823(4) 173(4) yes
C4 H4 O4 7_577 0.93 2.48 3.383(4) 163.0 yes
C13 H13C O1 1_545 0.96 2.51 3.459(4) 171.5 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655014
2 PubChem 139070005
