#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225857.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_2225857
loop_
_publ_author_name
'Han, You-Yue'
'Zhao, Qiu-Rong'
_publ_section_title
;
 N'-(2,3-Dimethoxybenzylidene)-2-hydroxy-3-methylbenzohydrazide
;
_journal_coeditor_code           HB5386
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1026
_journal_paper_doi               10.1107/S1600536810012122
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H18 N2 O4'
_chemical_formula_moiety         'C17 H18 N2 O4'
_chemical_formula_sum            'C17 H18 N2 O4'
_chemical_formula_weight         314.33
_chemical_name_systematic
;
N'-(2,3-Dimethoxybenzylidene)-2-hydroxy-3-methylbenzohydrazide
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.923(3)
_cell_length_b                   24.329(5)
_cell_length_c                   8.7422(17)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      2.7
_cell_volume                     3174.0(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (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  'Bruker SMART CCD'
_diffrn_measurement_method       '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  0.2225
_diffrn_reflns_av_sigmaI/netI    0.1223
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17128
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0674
_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)+(0.0754P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                1998
_reflns_number_total             3461
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5386.cif
_cod_data_source_block           I
_cod_database_code               2225857
_cod_database_fobs_code          2225857
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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
O O1 0.42606(9) 0.10101(6) 0.37153(16) 0.0482(4) Uani d . 1 . .
O O2 0.28300(9) 0.06224(8) 0.52262(16) 0.0602(5) Uani d . 1 . .
O O3 0.84543(10) 0.11847(7) 0.62612(16) 0.0586(5) Uani d . 1 . .
O O4 1.01095(9) 0.13449(7) 0.53290(16) 0.0601(5) Uani d . 1 . .
H H4 0.9716 0.1232 0.5903 0.072 Uiso d R 1 . .
N N1 0.67827(11) 0.09279(7) 0.53655(18) 0.0464(5) Uani d . 1 . .
N N2 0.74005(11) 0.11742(7) 0.44045(19) 0.0474(5) Uani d . 1 . .
H H2A 0.7274 0.1235 0.3411 0.057 Uiso d R 1 . .
C C1 0.52468(13) 0.06866(8) 0.5673(2) 0.0402(5) Uani d . 1 . .
C C2 0.43791(13) 0.07538(9) 0.5098(2) 0.0396(5) Uani d . 1 . .
C C3 0.36482(13) 0.05310(9) 0.5889(2) 0.0443(5) Uani d . 1 . .
C C4 0.37887(16) 0.02333(10) 0.7208(2) 0.0521(6) Uani d . 1 . .
H H4A 0.3306 0.0079 0.7727 0.063 Uiso calc R 1 . .
C C5 0.46507(16) 0.01651(10) 0.7758(2) 0.0536(6) Uani d . 1 . .
H H5 0.4743 -0.0036 0.8649 0.064 Uiso calc R 1 . .
C C6 0.53705(15) 0.03885(9) 0.7014(2) 0.0473(5) Uani d . 1 . .
H H6 0.5945 0.0341 0.7406 0.057 Uiso calc R 1 . .
C C7 0.38589(19) 0.15360(11) 0.3766(3) 0.0724(8) Uani d . 1 . .
H H7A 0.3336 0.1523 0.4405 0.109 Uiso calc R 1 . .
H H7B 0.3690 0.1646 0.2751 0.109 Uiso calc R 1 . .
H H7C 0.4278 0.1797 0.4178 0.109 Uiso calc R 1 . .
C C8 0.20603(16) 0.04196(12) 0.6008(3) 0.0701(8) Uani d . 1 . .
H H8A 0.2071 0.0025 0.6009 0.105 Uiso calc R 1 . .
H H8B 0.1529 0.0546 0.5500 0.105 Uiso calc R 1 . .
H H8C 0.2063 0.0551 0.7043 0.105 Uiso calc R 1 . .
C C9 0.59903(13) 0.09237(9) 0.4826(2) 0.0445(5) Uani d . 1 . .
H H9 0.5885 0.1076 0.3867 0.053 Uiso calc R 1 . .
C C10 0.82117(13) 0.13106(9) 0.4951(2) 0.0428(5) Uani d . 1 . .
C C11 0.88015(14) 0.16270(8) 0.3910(2) 0.0421(5) Uani d . 1 . .
C C12 0.97309(14) 0.16251(8) 0.4165(2) 0.0456(5) Uani d . 1 . .
C C13 1.03102(15) 0.19180(10) 0.3209(3) 0.0532(6) Uani d . 1 . .
C C14 0.99399(18) 0.22279(10) 0.2061(3) 0.0650(7) Uani d . 1 . .
H H14 1.0318 0.2430 0.1429 0.078 Uiso calc R 1 . .
C C15 0.90212(19) 0.22521(11) 0.1802(3) 0.0671(7) Uani d . 1 . .
H H15 0.8789 0.2469 0.1021 0.081 Uiso calc R 1 . .
C C16 0.84659(15) 0.19497(9) 0.2724(2) 0.0538(6) Uani d . 1 . .
H H16 0.7851 0.1960 0.2554 0.065 Uiso calc R 1 . .
C C17 1.13038(15) 0.18931(13) 0.3465(3) 0.0768(8) Uani d . 1 . .
H H17A 1.1502 0.1519 0.3392 0.115 Uiso calc R 1 . .
H H17B 1.1442 0.2034 0.4464 0.115 Uiso calc R 1 . .
H H17C 1.1603 0.2111 0.2705 0.115 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
C2 O1 C7 . . 115.99(16) ?
C3 O2 C8 . . 117.34(18) ?
C12 O4 H4 . . 109.3 ?
C9 N1 N2 . . 113.41(17) ?
C10 N2 N1 . . 119.45(17) ?
C10 N2 H2A . . 119.4 ?
N1 N2 H2A . . 121.1 ?
C6 C1 C2 . . 119.12(18) ?
C6 C1 C9 . . 122.34(18) ?
C2 C1 C9 . . 118.53(18) ?
O1 C2 C1 . . 119.28(17) ?
O1 C2 C3 . . 120.71(17) ?
C1 C2 C3 . . 119.90(18) ?
O2 C3 C4 . . 125.12(18) ?
O2 C3 C2 . . 114.99(18) ?
C4 C3 C2 . . 119.87(19) ?
C3 C4 C5 . . 119.7(2) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C6 C5 C4 . . 121.1(2) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 120.25(19) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C1 . . 121.57(19) ?
N1 C9 H9 . . 119.2 ?
C1 C9 H9 . . 119.2 ?
O3 C10 N2 . . 122.05(19) ?
O3 C10 C11 . . 121.49(18) ?
N2 C10 C11 . . 116.46(17) ?
C16 C11 C12 . . 118.3(2) ?
C16 C11 C10 . . 122.42(19) ?
C12 C11 C10 . . 119.17(18) ?
O4 C12 C13 . . 116.7(2) ?
O4 C12 C11 . . 122.34(19) ?
C13 C12 C11 . . 120.9(2) ?
C14 C13 C12 . . 117.9(2) ?
C14 C13 C17 . . 122.0(2) ?
C12 C13 C17 . . 120.1(2) ?
C13 C14 C15 . . 122.6(2) ?
C13 C14 H14 . . 118.7 ?
C15 C14 H14 . . 118.7 ?
C16 C15 C14 . . 118.6(2) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C15 C16 C11 . . 121.5(2) ?
C15 C16 H16 . . 119.2 ?
C11 C16 H16 . . 119.2 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
O1 C2 . 1.372(2) ?
O1 C7 . 1.414(3) ?
O2 C3 . 1.370(2) ?
O2 C8 . 1.425(3) ?
O3 C10 . 1.240(2) ?
O4 C12 . 1.349(2) ?
O4 H4 . 0.8195 ?
N1 C9 . 1.273(3) ?
N1 N2 . 1.384(2) ?
N2 C10 . 1.343(2) ?
N2 H2A . 0.9005 ?
C1 C6 . 1.391(3) ?
C1 C2 . 1.398(3) ?
C1 C9 . 1.453(3) ?
C2 C3 . 1.401(3) ?
C3 C4 . 1.378(3) ?
C4 C5 . 1.383(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.368(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.482(3) ?
C11 C16 . 1.394(3) ?
C11 C12 . 1.405(3) ?
C12 C13 . 1.398(3) ?
C13 C14 . 1.372(3) ?
C13 C17 . 1.501(3) ?
C14 C15 . 1.391(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.370(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 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
O4 H4 O3 . 0.82 1.91 2.630(2) 146
N2 H2A O3 7_755 0.90 2.17 3.030(2) 158
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656071
2 PubChem 139078787
