#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226226.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_2226226
loop_
_publ_author_name
'Zhu, Hualing'
'Shi, Jun'
'Wei, Zhen'
'Dai, Ronghua'
'Zhang, Xin'
_publ_section_title
;
 Methyl
 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene]ethylamino}-3-phenylpropanoate
;
_journal_coeditor_code           LX2128
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1352
_journal_paper_doi               10.1107/S1600536810017241
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H23 N3 O3'
_chemical_formula_moiety         'C22 H23 N3 O3'
_chemical_formula_sum            'C22 H23 N3 O3'
_chemical_formula_weight         377.43
_chemical_name_systematic
;
Methyl 2-{1-[(Z)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-
4-ylidene]ethylamino}-3-phenylpropanoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.718(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9400(10)
_cell_length_b                   7.2105(7)
_cell_length_c                   12.8670(10)
_cell_measurement_reflns_used    1220
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.35
_cell_measurement_theta_min      3.17
_cell_volume                     1013.84(16)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6036
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000\\bbr00)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0409P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                1239
_reflns_number_total             2366
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2128.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2226226
_cod_database_fobs_code          2226226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O O1 0.69537(16) 0.7004(4) 0.63222(13) 0.0812(6) Uani d . 1 . .
O O2 0.9385(2) 0.5317(4) 0.4573(2) 0.0951(8) Uani d . 1 . .
O O3 0.9296(2) 0.4530(3) 0.28897(18) 0.0818(7) Uani d . 1 . .
N N1 0.49129(18) 0.7209(4) 0.67625(16) 0.0594(6) Uani d . 1 . .
N N2 0.37536(19) 0.7237(4) 0.62394(18) 0.0662(6) Uani d . 1 . .
N N3 0.7085(2) 0.6887(4) 0.42371(17) 0.0681(7) Uani d . 1 . .
H H3 0.7408 0.6814 0.4858 0.082 Uiso calc R 1 . .
C C1 0.3903(3) 0.7353(6) 0.8383(2) 0.0798(10) Uani d . 1 . .
H H1 0.3156 0.7472 0.8012 0.096 Uiso calc R 1 . .
C C2 0.3948(4) 0.7310(7) 0.9457(3) 0.1043(12) Uani d . 1 . .
H H2 0.3226 0.7392 0.9809 0.125 Uiso calc R 1 . .
C C3 0.5037(5) 0.7148(8) 1.0007(3) 0.1151(14) Uani d . 1 . .
H H3A 0.5060 0.7114 1.0730 0.138 Uiso calc R 1 . .
C C4 0.6103(3) 0.7035(8) 0.9487(2) 0.1075(13) Uani d . 1 . .
H H4 0.6849 0.6941 0.9860 0.129 Uiso calc R 1 . .
C C5 0.6072(3) 0.7060(6) 0.8416(2) 0.0853(10) Uani d . 1 . .
H H5 0.6794 0.6971 0.8066 0.102 Uiso calc R 1 . .
C C6 0.4968(3) 0.7219(5) 0.7866(2) 0.0626(7) Uani d . 1 . .
C C7 0.5836(2) 0.7091(5) 0.6073(2) 0.0608(7) Uani d . 1 . .
C C8 0.5237(2) 0.7100(5) 0.5063(2) 0.0534(6) Uani d . 1 . .
C C9 0.3959(2) 0.7185(5) 0.5250(2) 0.0595(7) Uani d . 1 . .
C C10 0.2866(2) 0.7155(6) 0.4494(2) 0.0834(10) Uani d . 1 . .
H H10A 0.2130 0.7153 0.4871 0.125 Uiso calc R 1 . .
H H10B 0.2892 0.6059 0.4072 0.125 Uiso calc R 1 . .
H H10C 0.2880 0.8233 0.4056 0.125 Uiso calc R 1 . .
C C11 0.5879(2) 0.7059(5) 0.4158(2) 0.0563(7) Uani d . 1 . .
C C12 0.5269(2) 0.7185(6) 0.3096(2) 0.0727(8) Uani d . 1 . .
H H12A 0.5209 0.5969 0.2794 0.109 Uiso calc R 1 . .
H H12B 0.5741 0.7971 0.2666 0.109 Uiso calc R 1 . .
H H12C 0.4463 0.7697 0.3146 0.109 Uiso calc R 1 . .
C C13 0.7929(2) 0.6804(5) 0.3398(2) 0.0646(8) Uani d . 1 . .
H H13 0.7495 0.6375 0.2759 0.077 Uiso calc R 1 . .
C C14 0.8937(3) 0.5450(5) 0.3710(3) 0.0677(9) Uani d . 1 . .
C C15 1.0389(3) 0.3383(6) 0.3056(3) 0.1081(14) Uani d . 1 . .
H H15A 1.0281 0.2559 0.3631 0.162 Uiso calc R 1 . .
H H15B 1.1086 0.4164 0.3206 0.162 Uiso calc R 1 . .
H H15C 1.0518 0.2670 0.2441 0.162 Uiso calc R 1 . .
C C16 0.8488(3) 0.8723(5) 0.3216(3) 0.0724(9) Uani d . 1 . .
H H16A 0.7833 0.9626 0.3131 0.087 Uiso calc R 1 . .
H H16B 0.8991 0.9071 0.3826 0.087 Uiso calc R 1 . .
C C17 0.9252(3) 0.8793(4) 0.2280(3) 0.0645(8) Uani d . 1 . .
C C18 1.0502(3) 0.8632(5) 0.2357(3) 0.0886(11) Uani d . 1 . .
H H18 1.0890 0.8466 0.3009 0.106 Uiso calc R 1 . .
C C19 1.1202(4) 0.8709(6) 0.1491(5) 0.1149(16) Uani d . 1 . .
H H19 1.2049 0.8596 0.1561 0.138 Uiso calc R 1 . .
C C20 1.0639(5) 0.8953(7) 0.0535(4) 0.1186(16) Uani d . 1 . .
H H20 1.1104 0.9008 -0.0051 0.142 Uiso calc R 1 . .
C C21 0.9411(5) 0.9114(7) 0.0431(3) 0.1104(14) Uani d . 1 . .
H H21 0.9030 0.9288 -0.0223 0.133 Uiso calc R 1 . .
C C22 0.8718(3) 0.9019(5) 0.1308(3) 0.0847(11) Uani d . 1 . .
H H22 0.7871 0.9111 0.1231 0.102 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'
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
C14 O3 C15 . . 116.0(3) ?
C7 N1 N2 . . 111.3(2) ?
C7 N1 C6 . . 130.4(2) ?
N2 N1 C6 . . 118.2(2) ?
C9 N2 N1 . . 105.9(2) ?
C11 N3 C13 . . 127.7(2) ?
C11 N3 H3 . . 116.1 ?
C13 N3 H3 . . 116.1 ?
C6 C1 C2 . . 119.5(3) ?
C6 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C3 C2 C1 . . 120.7(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C2 C3 C4 . . 119.6(3) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C3 C4 C5 . . 120.4(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 119.7(3) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C1 C6 C5 . . 120.1(3) ?
C1 C6 N1 . . 119.3(3) ?
C5 C6 N1 . . 120.6(3) ?
O1 C7 N1 . . 125.1(2) ?
O1 C7 C8 . . 129.4(2) ?
N1 C7 C8 . . 105.5(2) ?
C11 C8 C7 . . 122.3(2) ?
C11 C8 C9 . . 132.8(2) ?
C7 C8 C9 . . 104.9(2) ?
N2 C9 C8 . . 112.4(2) ?
N2 C9 C10 . . 117.6(2) ?
C8 C9 C10 . . 130.0(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N3 C11 C8 . . 118.6(2) ?
N3 C11 C12 . . 118.4(2) ?
C8 C11 C12 . . 122.9(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N3 C13 C14 . . 108.1(3) ?
N3 C13 C16 . . 110.4(3) ?
C14 C13 C16 . . 109.4(2) ?
N3 C13 H13 . . 109.7 ?
C14 C13 H13 . . 109.7 ?
C16 C13 H13 . . 109.7 ?
O2 C14 O3 . . 125.2(3) ?
O2 C14 C13 . . 124.0(3) ?
O3 C14 C13 . . 110.7(3) ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C13 . . 113.2(3) ?
C17 C16 H16A . . 108.9 ?
C13 C16 H16A . . 108.9 ?
C17 C16 H16B . . 108.9 ?
C13 C16 H16B . . 108.9 ?
H16A C16 H16B . . 107.7 ?
C22 C17 C18 . . 117.3(3) ?
C22 C17 C16 . . 120.6(3) ?
C18 C17 C16 . . 122.1(3) ?
C17 C18 C19 . . 121.8(4) ?
C17 C18 H18 . . 119.1 ?
C19 C18 H18 . . 119.1 ?
C20 C19 C18 . . 119.3(4) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
C21 C20 C19 . . 120.5(4) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C20 C21 C22 . . 119.6(4) ?
C20 C21 H21 . . 120.2 ?
C22 C21 H21 . . 120.2 ?
C17 C22 C21 . . 121.6(3) ?
C17 C22 H22 . . 119.2 ?
C21 C22 H22 . . 119.2 ?
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 C7 . 1.251(3) ?
O2 C14 . 1.197(4) ?
O3 C14 . 1.322(4) ?
O3 C15 . 1.462(4) ?
N1 C7 . 1.378(3) ?
N1 N2 . 1.407(3) ?
N1 C6 . 1.418(3) ?
N2 C9 . 1.304(3) ?
N3 C11 . 1.325(3) ?
N3 C13 . 1.454(3) ?
N3 H3 . 0.8600 ?
C1 C6 . 1.372(4) ?
C1 C2 . 1.382(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.362(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.374(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.376(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.427(3) ?
C8 C11 . 1.388(3) ?
C8 C9 . 1.431(3) ?
C9 C10 . 1.506(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.495(3) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.512(4) ?
C13 C16 . 1.535(4) ?
C13 H13 . 0.9800 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.499(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C22 . 1.365(4) ?
C17 C18 . 1.371(4) ?
C18 C19 . 1.382(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.361(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.349(5) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.390(5) ?
C21 H21 . 0.9300 ?
C22 H22 . 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
N3 H3 O1 . 0.86 1.98 2.695(3) 140.5
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
C7 N1 N2 C9 . . . . -1.6(4) ?
C6 N1 N2 C9 . . . . -178.8(3) ?
C6 C1 C2 C3 . . . . 0.4(7) ?
C1 C2 C3 C4 . . . . 0.3(9) ?
C2 C3 C4 C5 . . . . -0.8(9) ?
C3 C4 C5 C6 . . . . 0.6(8) ?
C2 C1 C6 C5 . . . . -0.6(6) ?
C2 C1 C6 N1 . . . . 178.2(4) ?
C4 C5 C6 C1 . . . . 0.1(7) ?
C4 C5 C6 N1 . . . . -178.7(4) ?
C7 N1 C6 C1 . . . . 179.9(4) ?
N2 N1 C6 C1 . . . . -3.4(5) ?
C7 N1 C6 C5 . . . . -1.2(6) ?
N2 N1 C6 C5 . . . . 175.4(3) ?
N2 N1 C7 O1 . . . . -178.4(3) ?
C6 N1 C7 O1 . . . . -1.7(6) ?
N2 N1 C7 C8 . . . . 1.8(4) ?
C6 N1 C7 C8 . . . . 178.6(3) ?
O1 C7 C8 C11 . . . . -1.9(6) ?
N1 C7 C8 C11 . . . . 177.8(3) ?
O1 C7 C8 C9 . . . . 179.0(4) ?
N1 C7 C8 C9 . . . . -1.3(4) ?
N1 N2 C9 C8 . . . . 0.7(4) ?
N1 N2 C9 C10 . . . . 178.6(3) ?
C11 C8 C9 N2 . . . . -178.6(4) ?
C7 C8 C9 N2 . . . . 0.4(4) ?
C11 C8 C9 C10 . . . . 3.8(7) ?
C7 C8 C9 C10 . . . . -177.3(4) ?
C13 N3 C11 C8 . . . . 179.6(3) ?
C13 N3 C11 C12 . . . . 0.2(5) ?
C7 C8 C11 N3 . . . . 4.4(5) ?
C9 C8 C11 N3 . . . . -176.7(3) ?
C7 C8 C11 C12 . . . . -176.1(3) ?
C9 C8 C11 C12 . . . . 2.7(6) ?
C11 N3 C13 C14 . . . . -143.2(3) ?
C11 N3 C13 C16 . . . . 97.2(4) ?
C15 O3 C14 O2 . . . . -5.2(5) ?
C15 O3 C14 C13 . . . . 171.1(3) ?
N3 C13 C14 O2 . . . . -39.0(4) ?
C16 C13 C14 O2 . . . . 81.2(4) ?
N3 C13 C14 O3 . . . . 144.8(3) ?
C16 C13 C14 O3 . . . . -95.1(3) ?
N3 C13 C16 C17 . . . . -173.2(3) ?
C14 C13 C16 C17 . . . . 68.1(4) ?
C13 C16 C17 C22 . . . . 82.0(4) ?
C13 C16 C17 C18 . . . . -97.8(4) ?
C22 C17 C18 C19 . . . . 0.6(5) ?
C16 C17 C18 C19 . . . . -179.6(4) ?
C17 C18 C19 C20 . . . . 0.0(7) ?
C18 C19 C20 C21 . . . . -0.1(7) ?
C19 C20 C21 C22 . . . . -0.4(7) ?
C18 C17 C22 C21 . . . . -1.1(6) ?
C16 C17 C22 C21 . . . . 179.1(4) ?
C20 C21 C22 C17 . . . . 1.0(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656092
2 PubChem 139078975
