#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226682.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_2226682
loop_
_publ_author_name
'Liu, Shi-Yong'
'Wang, Xiaoling'
_publ_section_title
;
 (E)-N'-(5-Bromo-2-hydroxybenzylidene)-3-methoxybenzohydrazide
;
_journal_coeditor_code           SJ5025
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1805
_journal_paper_doi               10.1107/S1600536810024001
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 Br N2 O3'
_chemical_formula_moiety         'C15 H13 Br N2 O3'
_chemical_formula_sum            'C15 H13 Br N2 O3'
_chemical_formula_weight         349.18
_chemical_name_systematic
;
(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3-methoxybenzohydrazide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.437(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.865(2)
_cell_length_b                   30.726(3)
_cell_length_c                   7.257(2)
_cell_measurement_reflns_used    2100
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     1482.4(6)
_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 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8593
_diffrn_reflns_theta_full        26.83
_diffrn_reflns_theta_max         26.83
_diffrn_reflns_theta_min         1.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  0.5668
_exptl_absorpt_correction_T_min  0.5202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.452
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                1832
_reflns_number_total             3079
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5025.cif
_cod_data_source_block           I
_cod_original_cell_volume        1482.2(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226682
_cod_database_fobs_code          2226682
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
Br Br1 -0.14621(6) 0.006913(10) 0.72146(5) 0.08082(18) Uani d . 1 . .
N N1 -0.0463(3) 0.21192(6) 0.5786(3) 0.0474(5) Uani d . 1 . .
N N2 0.1078(3) 0.24188(7) 0.6071(3) 0.0486(6) Uani d D 1 . .
O O1 -0.4272(3) 0.18973(6) 0.5066(3) 0.0620(5) Uani d . 1 . .
H H1 -0.3314 0.2060 0.5117 0.093 Uiso calc R 1 . .
O O2 -0.0895(3) 0.29146(5) 0.4185(3) 0.0522(5) Uani d . 1 . .
O O3 0.3228(3) 0.43040(6) 0.6485(3) 0.0755(6) Uani d . 1 . .
C C1 -0.1528(4) 0.14004(8) 0.6243(3) 0.0415(6) Uani d . 1 . .
C C2 -0.3592(4) 0.14938(8) 0.5621(4) 0.0458(6) Uani d . 1 . .
C C3 -0.4970(4) 0.11647(10) 0.5578(4) 0.0568(7) Uani d . 1 . .
H H3 -0.6336 0.1229 0.5227 0.068 Uiso calc R 1 . .
C C4 -0.4370(5) 0.07446(9) 0.6041(4) 0.0599(8) Uani d . 1 . .
H H4 -0.5324 0.0526 0.5971 0.072 Uiso calc R 1 . .
C C5 -0.2338(5) 0.06462(8) 0.6614(4) 0.0524(7) Uani d . 1 . .
C C6 -0.0948(4) 0.09725(8) 0.6719(4) 0.0481(7) Uani d . 1 . .
H H6 0.0414 0.0906 0.7119 0.058 Uiso calc R 1 . .
C C7 0.0005(4) 0.17332(8) 0.6411(4) 0.0457(7) Uani d . 1 . .
H H7 0.1341 0.1666 0.6979 0.055 Uiso calc R 1 . .
C C8 0.0728(4) 0.28138(8) 0.5248(4) 0.0419(6) Uani d . 1 . .
C C9 0.2439(4) 0.31261(8) 0.5746(3) 0.0400(6) Uani d . 1 . .
C C10 0.1979(4) 0.35642(8) 0.5838(3) 0.0423(6) Uani d . 1 . .
H H10 0.0642 0.3652 0.5579 0.051 Uiso calc R 1 . .
C C11 0.3486(4) 0.38683(8) 0.6308(4) 0.0502(7) Uani d . 1 . .
C C12 0.5471(5) 0.37320(10) 0.6659(4) 0.0631(8) Uani d . 1 . .
H H12 0.6500 0.3936 0.6975 0.076 Uiso calc R 1 . .
C C13 0.5937(4) 0.33037(10) 0.6550(4) 0.0621(8) Uani d . 1 . .
H H13 0.7276 0.3219 0.6773 0.074 Uiso calc R 1 . .
C C14 0.4423(4) 0.29916(9) 0.6106(4) 0.0507(7) Uani d . 1 . .
H H14 0.4738 0.2698 0.6053 0.061 Uiso calc R 1 . .
C C15 0.1241(6) 0.44666(9) 0.6235(5) 0.0788(10) Uani d . 1 . .
H H15A 0.0484 0.4413 0.4953 0.118 Uiso calc R 1 . .
H H15B 0.1290 0.4774 0.6477 0.118 Uiso calc R 1 . .
H H15C 0.0605 0.4323 0.7106 0.118 Uiso calc R 1 . .
H H2 0.218(3) 0.2361(10) 0.700(3) 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'
Br Br -0.2901 2.4595 '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
C7 N1 N2 . . 116.7(2) ?
C8 N2 N1 . . 119.3(2) ?
C8 N2 H2 . . 122.3(19) ?
N1 N2 H2 . . 117.0(19) ?
C2 O1 H1 . . 109.5 ?
C11 O3 C15 . . 118.5(2) ?
C6 C1 C2 . . 118.4(2) ?
C6 C1 C7 . . 119.2(2) ?
C2 C1 C7 . . 122.4(2) ?
O1 C2 C3 . . 118.8(2) ?
O1 C2 C1 . . 122.0(2) ?
C3 C2 C1 . . 119.2(2) ?
C4 C3 C2 . . 121.5(3) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 119.8(3) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C6 C5 C4 . . 119.4(3) ?
C6 C5 Br1 . . 119.7(2) ?
C4 C5 Br1 . . 120.9(2) ?
C5 C6 C1 . . 121.6(3) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
N1 C7 C1 . . 120.6(2) ?
N1 C7 H7 . . 119.7 ?
C1 C7 H7 . . 119.7 ?
O2 C8 N2 . . 122.7(2) ?
O2 C8 C9 . . 121.9(2) ?
N2 C8 C9 . . 115.5(2) ?
C14 C9 C10 . . 120.3(2) ?
C14 C9 C8 . . 122.2(2) ?
C10 C9 C8 . . 117.5(2) ?
C11 C10 C9 . . 120.4(2) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
O3 C11 C10 . . 125.8(3) ?
O3 C11 C12 . . 115.1(2) ?
C10 C11 C12 . . 119.0(3) ?
C13 C12 C11 . . 121.0(3) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C14 . . 120.5(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C9 C14 C13 . . 118.7(3) ?
C9 C14 H14 . . 120.6 ?
C13 C14 H14 . . 120.6 ?
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 ?
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
Br1 C5 . 1.888(3) ?
N1 C7 . 1.282(3) ?
N1 N2 . 1.379(3) ?
N2 C8 . 1.347(3) ?
N2 H2 . 0.898(10) ?
O1 C2 . 1.350(3) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.226(3) ?
O3 C11 . 1.361(3) ?
O3 C15 . 1.421(4) ?
C1 C6 . 1.392(3) ?
C1 C2 . 1.405(3) ?
C1 C7 . 1.451(3) ?
C2 C3 . 1.380(4) ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.373(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.490(3) ?
C9 C14 . 1.384(3) ?
C9 C10 . 1.388(3) ?
C10 C11 . 1.373(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(4) ?
C12 C13 . 1.361(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.392(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
O1 H1 N1 . 0.82 1.90 2.625(3) 146
N2 H2 O2 4_666 0.898(10) 1.983(13) 2.852(3) 163(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12669415
2 PubChem 135615174
