#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225885.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_2225885
loop_
_publ_author_name
'Han, You-Yue'
'Li, Yong-Hong'
'Zhao, Qiu-Rong'
_publ_section_title
;
 2-Hydroxy-N'-(2-hydroxy-3-methoxy-5-nitrobenzylidene)-3-methylbenzohydrazide
;
_journal_coeditor_code           HG2671
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1084
_journal_paper_doi               10.1107/S1600536810012912
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H15 N3 O6'
_chemical_formula_moiety         'C16 H15 N3 O6'
_chemical_formula_sum            'C16 H15 N3 O6'
_chemical_formula_weight         345.31
_chemical_name_systematic
;
2-Hydroxy-N'-(2-hydroxy-3-methoxy-5-nitrobenzylidene)-
3-methylbenzohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4820(10)
_cell_length_b                   17.1580(10)
_cell_length_c                   12.2500(10)
_cell_measurement_reflns_used    6384
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.4
_cell_volume                     1572.0(3)
_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 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14545
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0371
_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)+(0.0597P)²+0.2485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2165
_reflns_number_total             2612
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2671.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225885
_cod_database_fobs_code          2225885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.91330(15) 0.99426(5) 0.21838(9) 0.0529(3) Uani d . 1 . .
H H1 0.8639 1.0075 0.1607 0.079 Uiso calc R 1 . .
O O2 1.05158(16) 0.93423(6) 0.39521(9) 0.0569(3) Uani d . 1 . .
O O3 0.67111(17) 1.11702(6) 0.00680(9) 0.0596(3) Uani d . 1 . .
O O4 0.55183(17) 1.23435(6) -0.09508(10) 0.0633(3) Uani d . 1 . .
H H4 0.5986 1.2096 -0.0447 0.095 Uiso calc R 1 . .
O O5 1.0371(2) 0.63937(6) 0.14205(11) 0.0805(4) Uani d . 1 . .
O O6 1.13335(17) 0.65067(6) 0.30689(10) 0.0654(4) Uani d . 1 . .
N N1 1.06881(16) 0.67848(7) 0.22311(11) 0.0481(3) Uani d . 1 . .
N N2 0.78019(15) 0.97366(7) 0.02075(10) 0.0428(3) Uani d . 1 . .
N N3 0.70013(16) 1.00078(6) -0.07337(10) 0.0434(3) Uani d D 1 . .
C C1 0.91165(17) 0.87130(8) 0.12358(11) 0.0391(3) Uani d . 1 . .
C C2 0.94794(18) 0.91768(8) 0.21567(12) 0.0397(3) Uani d . 1 . .
C C3 1.02423(19) 0.88404(8) 0.31098(12) 0.0422(3) Uani d . 1 . .
C C4 1.06361(18) 0.80575(8) 0.31361(12) 0.0425(4) Uani d . 1 . .
H H4A 1.1130 0.7830 0.3764 0.051 Uiso calc R 1 . .
C C5 1.02806(18) 0.76137(8) 0.22055(12) 0.0406(3) Uani d . 1 . .
C C6 0.95409(18) 0.79211(8) 0.12723(12) 0.0423(3) Uani d . 1 . .
H H6 0.9321 0.7606 0.0665 0.051 Uiso calc R 1 . .
C C7 1.1154(3) 0.90321(10) 0.49667(14) 0.0671(5) Uani d . 1 . .
H H7A 1.0319 0.8654 0.5224 0.101 Uiso calc R 1 . .
H H7B 1.1281 0.9445 0.5491 0.101 Uiso calc R 1 . .
H H7C 1.2293 0.8788 0.4870 0.101 Uiso calc R 1 . .
C C8 0.8290(2) 0.90257(8) 0.02500(12) 0.0444(4) Uani d . 1 . .
H H8 0.8113 0.8706 -0.0357 0.053 Uiso calc R 1 . .
C C9 0.64676(18) 1.07636(8) -0.07544(12) 0.0398(3) Uani d . 1 . .
C C10 0.56400(18) 1.10707(8) -0.17680(12) 0.0393(3) Uani d . 1 . .
C C11 0.52198(18) 1.18678(8) -0.18113(12) 0.0433(4) Uani d . 1 . .
C C12 0.44698(19) 1.22062(9) -0.27568(13) 0.0486(4) Uani d . 1 . .
C C13 0.4115(2) 1.17278(10) -0.36333(14) 0.0566(4) Uani d . 1 . .
H H13 0.3604 1.1941 -0.4266 0.068 Uiso calc R 1 . .
C C14 0.4493(2) 1.09387(10) -0.36069(14) 0.0587(4) Uani d . 1 . .
H H14 0.4230 1.0629 -0.4214 0.070 Uiso calc R 1 . .
C C15 0.5255(2) 1.06140(9) -0.26864(13) 0.0493(4) Uani d . 1 . .
H H15 0.5519 1.0084 -0.2673 0.059 Uiso calc R 1 . .
C C16 0.4079(2) 1.30676(10) -0.27722(16) 0.0659(5) Uani d . 1 . .
H H16A 0.3563 1.3210 -0.3470 0.099 Uiso calc R 1 . .
H H16B 0.5169 1.3352 -0.2646 0.099 Uiso calc R 1 . .
H H16C 0.3255 1.3190 -0.2210 0.099 Uiso calc R 1 . .
H H3 0.686(3) 0.9691(10) -0.1318(12) 0.080 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1 . . 109.5 ?
C3 O2 C7 . . 117.87(12) ?
C11 O4 H4 . . 109.5 ?
O5 N1 O6 . . 122.35(12) ?
O5 N1 C5 . . 119.05(12) ?
O6 N1 C5 . . 118.60(13) ?
C8 N2 N3 . . 118.63(13) ?
C9 N3 N2 . . 117.60(12) ?
C9 N3 H3 . . 122.2(13) ?
N2 N3 H3 . . 120.2(13) ?
C6 C1 C2 . . 119.23(13) ?
C6 C1 C8 . . 118.69(13) ?
C2 C1 C8 . . 122.08(12) ?
O1 C2 C1 . . 122.93(13) ?
O1 C2 C3 . . 117.09(13) ?
C1 C2 C3 . . 119.98(12) ?
O2 C3 C4 . . 125.10(14) ?
O2 C3 C2 . . 114.82(12) ?
C4 C3 C2 . . 120.07(13) ?
C3 C4 C5 . . 118.66(13) ?
C3 C4 H4A . . 120.7 ?
C5 C4 H4A . . 120.7 ?
C6 C5 C4 . . 122.69(12) ?
C6 C5 N1 . . 118.46(13) ?
C4 C5 N1 . . 118.84(13) ?
C5 C6 C1 . . 119.37(13) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
O2 C7 H7A . . 109.5 ?
O2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C1 . . 120.36(14) ?
N2 C8 H8 . . 119.8 ?
C1 C8 H8 . . 119.8 ?
O3 C9 N3 . . 119.19(13) ?
O3 C9 C10 . . 122.42(12) ?
N3 C9 C10 . . 118.38(13) ?
C15 C10 C11 . . 118.41(13) ?
C15 C10 C9 . . 123.57(12) ?
C11 C10 C9 . . 118.02(13) ?
O4 C11 C12 . . 116.78(13) ?
O4 C11 C10 . . 121.90(13) ?
C12 C11 C10 . . 121.31(14) ?
C13 C12 C11 . . 117.67(14) ?
C13 C12 C16 . . 122.95(15) ?
C11 C12 C16 . . 119.39(15) ?
C12 C13 C14 . . 122.16(15) ?
C12 C13 H13 . . 118.9 ?
C14 C13 H13 . . 118.9 ?
C15 C14 C13 . . 119.88(16) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C10 . . 120.55(14) ?
C14 C15 H15 . . 119.7 ?
C10 C15 H15 . . 119.7 ?
C12 C16 H16A . . 109.5 ?
C12 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C12 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 . 1.3399(16) ?
O1 H1 . 0.8200 ?
O2 C3 . 1.3553(17) ?
O2 C7 . 1.423(2) ?
O3 C9 . 1.2348(17) ?
O4 C11 . 1.3469(18) ?
O4 H4 . 0.8200 ?
O5 N1 . 1.2165(16) ?
O6 N1 . 1.2195(16) ?
N1 C5 . 1.4547(18) ?
N2 C8 . 1.2739(18) ?
N2 N3 . 1.3664(17) ?
N3 C9 . 1.3569(18) ?
N3 H3 . 0.903(9) ?
C1 C6 . 1.3958(18) ?
C1 C2 . 1.401(2) ?
C1 C8 . 1.445(2) ?
C2 C3 . 1.409(2) ?
C3 C4 . 1.3754(19) ?
C4 C5 . 1.391(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.363(2) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.470(2) ?
C10 C15 . 1.395(2) ?
C10 C11 . 1.4040(19) ?
C11 C12 . 1.399(2) ?
C12 C13 . 1.372(2) ?
C12 C16 . 1.507(2) ?
C13 C14 . 1.383(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.368(2) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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
N3 H3 O6 4_575 0.903(9) 2.219(13) 3.0190(17) 147.3(17)
O4 H4 O3 . 0.82 1.79 2.5192(15) 147.7
O1 H1 N2 . 0.82 1.90 2.6166(17) 145.3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744852
2 PubChem 139078806
