#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227002.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_2227002
loop_
_publ_author_name
'Liu, Shan-Bin'
'Bi, Cai-Feng'
'Fan, Yu-Hua'
'Zhang, Xia'
'Zhang, Dong-Mei'
_publ_section_title
;
 1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           LH5091
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2149
_journal_paper_doi               10.1107/S160053681002934X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H23 N3 O4'
_chemical_formula_moiety         'C21 H23 N3 O4'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42
_chemical_name_systematic
;
1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}-
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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.46800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3644(12)
_cell_length_b                   14.0075(16)
_cell_length_c                   11.2682(11)
_cell_measurement_reflns_used    2128
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.298
_cell_measurement_theta_min      2.205
_cell_volume                     1939.2(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART 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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10089
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0420
_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)+(0.0390P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2084
_reflns_number_total             3422
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5091.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227002
_cod_database_fobs_code          2227002
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.58862(12) 0.17160(11) 0.75617(14) 0.0483(4) Uani d . 1 . .
N N2 0.55362(12) 0.07674(11) 0.73659(14) 0.0488(4) Uani d . 1 . .
N N3 0.38480(12) 0.18932(11) 0.49987(13) 0.0456(4) Uani d . 1 . .
O O1 0.56035(11) 0.31372(9) 0.65254(13) 0.0616(4) Uani d . 1 . .
O O2 0.14379(11) 0.51801(9) 0.24428(12) 0.0597(4) Uani d . 1 . .
O O3 0.06093(10) 0.38623(9) 0.08868(12) 0.0555(4) Uani d . 1 . .
O O4 0.12137(12) 0.20441(10) 0.10776(12) 0.0641(4) Uani d . 1 . .
C C1 0.53561(15) 0.22988(14) 0.66664(17) 0.0451(5) Uani d . 1 . .
C C2 0.45678(14) 0.16819(13) 0.60050(16) 0.0415(5) Uani d . 1 . .
C C3 0.46934(14) 0.07841(13) 0.64717(17) 0.0425(5) Uani d . 1 . .
C C4 0.40708(16) -0.00978(13) 0.61267(19) 0.0568(6) Uani d . 1 . .
H H4A 0.4568 -0.0613 0.6042 0.085 Uiso calc R 1 . .
H H4B 0.3628 0.0004 0.5382 0.085 Uiso calc R 1 . .
H H4C 0.3614 -0.0255 0.6733 0.085 Uiso calc R 1 . .
C C5 0.55506(17) 0.01888(15) 0.8440(2) 0.0682(7) Uani d . 1 . .
H H5A 0.5077 0.0468 0.8963 0.102 Uiso calc R 1 . .
H H5B 0.6278 0.0162 0.8838 0.102 Uiso calc R 1 . .
H H5C 0.5306 -0.0445 0.8227 0.102 Uiso calc R 1 . .
C C6 0.70012(16) 0.18510(13) 0.80311(17) 0.0460(5) Uani d . 1 . .
C C7 0.72641(19) 0.24765(15) 0.89492(19) 0.0645(6) Uani d . 1 . .
H H7 0.6722 0.2807 0.9286 0.077 Uiso calc R 1 . .
C C8 0.8353(2) 0.26125(18) 0.9374(2) 0.0788(8) Uani d . 1 . .
H H8 0.8544 0.3047 0.9985 0.095 Uiso calc R 1 . .
C C9 0.9143(2) 0.2109(2) 0.8894(3) 0.0798(8) Uani d . 1 . .
H H9 0.9871 0.2200 0.9182 0.096 Uiso calc R 1 . .
C C10 0.88698(18) 0.14758(18) 0.7999(2) 0.0765(7) Uani d . 1 . .
H H10 0.9411 0.1129 0.7683 0.092 Uiso calc R 1 . .
C C11 0.78040(17) 0.13441(15) 0.7557(2) 0.0613(6) Uani d . 1 . .
H H11 0.7622 0.0913 0.6939 0.074 Uiso calc R 1 . .
C C12 0.36413(15) 0.27582(14) 0.47241(17) 0.0478(5) Uani d . 1 . .
H H12 0.3986 0.3235 0.5201 0.057 Uiso calc R 1 . .
C C13 0.28837(15) 0.30404(13) 0.36894(16) 0.0429(5) Uani d . 1 . .
C C14 0.25703(15) 0.39875(13) 0.35636(17) 0.0463(5) Uani d . 1 . .
H H14 0.2868 0.4437 0.4114 0.056 Uiso calc R 1 . .
C C15 0.18193(15) 0.42704(13) 0.26269(17) 0.0439(5) Uani d . 1 . .
C C16 0.13902(15) 0.36017(14) 0.17957(17) 0.0446(5) Uani d . 1 . .
C C17 0.17022(15) 0.26509(14) 0.19268(16) 0.0460(5) Uani d . 1 . .
C C18 0.24460(15) 0.23685(14) 0.28662(16) 0.0461(5) Uani d . 1 . .
H H18 0.2653 0.1731 0.2947 0.055 Uiso calc R 1 . .
C C19 0.17650(18) 0.58758(14) 0.33332(19) 0.0658(6) Uani d . 1 . .
H H19A 0.1578 0.5659 0.4092 0.099 Uiso calc R 1 . .
H H19B 0.1400 0.6468 0.3129 0.099 Uiso calc R 1 . .
H H19C 0.2538 0.5970 0.3379 0.099 Uiso calc R 1 . .
C C20 0.10337(18) 0.41981(17) -0.01563(19) 0.0735(7) Uani d . 1 . .
H H20A 0.1388 0.4801 0.0009 0.110 Uiso calc R 1 . .
H H20B 0.0450 0.4275 -0.0787 0.110 Uiso calc R 1 . .
H H20C 0.1549 0.3745 -0.0396 0.110 Uiso calc R 1 . .
C C21 0.12836(19) 0.10573(14) 0.1296(2) 0.0703(7) Uani d . 1 . .
H H21A 0.2030 0.0859 0.1341 0.105 Uiso calc R 1 . .
H H21B 0.0864 0.0722 0.0660 0.105 Uiso calc R 1 . .
H H21C 0.1005 0.0917 0.2038 0.105 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 109.06(15) ?
C1 N1 C6 . . 122.78(15) ?
N2 N1 C6 . . 116.67(14) ?
C3 N2 N1 . . 107.16(14) ?
C3 N2 C5 . . 124.06(15) ?
N1 N2 C5 . . 114.90(16) ?
C12 N3 C2 . . 119.61(16) n
C15 O2 C19 . . 117.73(15) ?
C16 O3 C20 . . 114.23(15) ?
C17 O4 C21 . . 118.35(16) ?
O1 C1 N1 . . 123.15(18) ?
O1 C1 C2 . . 131.93(18) ?
N1 C1 C2 . . 104.86(16) ?
C3 C2 N3 . . 122.96(17) ?
C3 C2 C1 . . 108.14(16) ?
N3 C2 C1 . . 128.69(17) ?
C2 C3 N2 . . 110.13(16) ?
C2 C3 C4 . . 129.25(18) ?
N2 C3 C4 . . 120.61(17) ?
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 ?
N2 C5 H5A . . 109.5 ?
N2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C11 . . 120.3(2) ?
C7 C6 N1 . . 120.07(19) ?
C11 C6 N1 . . 119.66(18) ?
C6 C7 C8 . . 119.1(2) ?
C6 C7 H7 . . 120.4 ?
C8 C7 H7 . . 120.4 ?
C9 C8 C7 . . 120.1(2) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C8 . . 120.2(2) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C9 C10 C11 . . 120.5(2) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C6 . . 119.8(2) ?
C10 C11 H11 . . 120.1 ?
C6 C11 H11 . . 120.1 ?
N3 C12 C13 . . 122.99(18) n
N3 C12 H12 . . 118.5 ?
C13 C12 H12 . . 118.5 ?
C14 C13 C18 . . 119.85(18) ?
C14 C13 C12 . . 119.09(18) ?
C18 C13 C12 . . 121.01(17) ?
C15 C14 C13 . . 120.58(18) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
O2 C15 C14 . . 125.01(18) ?
O2 C15 C16 . . 115.34(17) ?
C14 C15 C16 . . 119.65(17) ?
O3 C16 C15 . . 120.43(17) ?
O3 C16 C17 . . 119.79(18) ?
C15 C16 C17 . . 119.65(18) ?
O4 C17 C18 . . 124.20(18) ?
O4 C17 C16 . . 115.18(17) ?
C18 C17 C16 . . 120.62(18) ?
C17 C18 C13 . . 119.64(18) ?
C17 C18 H18 . . 120.2 ?
C13 C18 H18 . . 120.2 ?
O2 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O2 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O3 C20 H20A . . 109.5 ?
O3 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O3 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O4 C21 H21A . . 109.5 ?
O4 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O4 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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
N1 C1 . 1.402(2) ?
N1 N2 . 1.407(2) ?
N1 C6 . 1.432(2) ?
N2 C3 . 1.366(2) ?
N2 C5 . 1.455(2) ?
N3 C12 . 1.269(2) n
N3 C2 . 1.392(2) n
O1 C1 . 1.228(2) ?
O2 C15 . 1.367(2) ?
O2 C19 . 1.424(2) ?
O3 C16 . 1.375(2) ?
O3 C20 . 1.420(2) ?
O4 C17 . 1.368(2) ?
O4 C21 . 1.405(2) ?
C1 C2 . 1.445(3) n
C2 C3 . 1.365(2) n
C3 C4 . 1.484(2) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.367(3) ?
C6 C11 . 1.376(3) ?
C7 C8 . 1.391(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.364(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.357(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.368(3) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.465(3) n
C12 H12 . 0.9300 ?
C13 C14 . 1.385(2) n
C13 C18 . 1.388(2) ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.387(3) ?
C16 C17 . 1.390(3) ?
C17 C18 . 1.380(2) ?
C18 H18 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
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
C5 H5C O1 2_646 0.96 2.31 3.211(2) 155
C9 H9 O4 1_656 0.93 2.56 3.346(3) 142
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C3 . . . . -8.40(19) ?
C6 N1 N2 C3 . . . . -152.94(16) ?
C1 N1 N2 C5 . . . . -150.54(16) ?
C6 N1 N2 C5 . . . . 64.9(2) ?
N2 N1 C1 O1 . . . . -170.55(17) ?
C6 N1 C1 O1 . . . . -28.6(3) ?
N2 N1 C1 C2 . . . . 6.95(19) ?
C6 N1 C1 C2 . . . . 148.88(17) ?
C12 N3 C2 C3 . . . . 168.73(17) ?
C12 N3 C2 C1 . . . . -17.2(3) ?
O1 C1 C2 C3 . . . . 174.1(2) ?
N1 C1 C2 C3 . . . . -3.0(2) ?
O1 C1 C2 N3 . . . . -0.6(3) ?
N1 C1 C2 N3 . . . . -177.84(17) ?
N3 C2 C3 N2 . . . . 173.05(16) ?
C1 C2 C3 N2 . . . . -2.1(2) ?
N3 C2 C3 C4 . . . . -6.2(3) ?
C1 C2 C3 C4 . . . . 178.61(18) ?
N1 N2 C3 C2 . . . . 6.4(2) ?
C5 N2 C3 C2 . . . . 144.21(18) ?
N1 N2 C3 C4 . . . . -174.22(15) ?
C5 N2 C3 C4 . . . . -36.4(3) ?
C1 N1 C6 C7 . . . . 86.2(2) ?
N2 N1 C6 C7 . . . . -134.48(18) ?
C1 N1 C6 C11 . . . . -94.1(2) ?
N2 N1 C6 C11 . . . . 45.2(2) ?
C11 C6 C7 C8 . . . . 1.8(3) ?
N1 C6 C7 C8 . . . . -178.59(18) ?
C6 C7 C8 C9 . . . . -1.5(3) ?
C7 C8 C9 C10 . . . . 0.2(4) ?
C8 C9 C10 C11 . . . . 0.9(4) ?
C9 C10 C11 C6 . . . . -0.6(4) ?
C7 C6 C11 C10 . . . . -0.8(3) ?
N1 C6 C11 C10 . . . . 179.61(18) ?
C2 N3 C12 C13 . . . . -179.20(16) ?
N3 C12 C13 C14 . . . . 169.61(17) ?
N3 C12 C13 C18 . . . . -7.8(3) ?
C18 C13 C14 C15 . . . . 0.3(3) ?
C12 C13 C14 C15 . . . . -177.09(17) ?
C19 O2 C15 C14 . . . . -5.6(3) ?
C19 O2 C15 C16 . . . . 173.74(17) ?
C13 C14 C15 O2 . . . . 178.25(17) ?
C13 C14 C15 C16 . . . . -1.1(3) ?
C20 O3 C16 C15 . . . . 88.4(2) ?
C20 O3 C16 C17 . . . . -95.6(2) ?
O2 C15 C16 O3 . . . . -2.1(3) ?
C14 C15 C16 O3 . . . . 177.30(16) ?
O2 C15 C16 C17 . . . . -178.04(16) ?
C14 C15 C16 C17 . . . . 1.3(3) ?
C21 O4 C17 C18 . . . . 14.1(3) ?
C21 O4 C17 C16 . . . . -165.26(17) ?
O3 C16 C17 O4 . . . . 2.5(3) ?
C15 C16 C17 O4 . . . . 178.47(17) ?
O3 C16 C17 C18 . . . . -176.90(16) ?
C15 C16 C17 C18 . . . . -0.9(3) ?
O4 C17 C18 C13 . . . . -179.14(17) ?
C16 C17 C18 C13 . . . . 0.2(3) ?
C14 C13 C18 C17 . . . . 0.1(3) ?
C12 C13 C18 C17 . . . . 177.48(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 356984
2 PubChem 402960
