#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226654.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_2226654
loop_
_publ_author_name
'Hang, Zhi-Xi'
_publ_section_title
;
 N'-(2-Hydroxy-1-naphthylmethylidene)-3-methoxybenzohydrazide
;
_journal_coeditor_code           RZ2461
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1650
_journal_paper_doi               10.1107/S1600536810022026
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H16 N2 O3'
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_chemical_name_systematic
;
N'-(2-Hydroxy-1-naphthylmethylidene)-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                 109.746(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1700(15)
_cell_length_b                   31.174(7)
_cell_length_c                   7.4669(16)
_cell_measurement_reflns_used    1460
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.0
_cell_measurement_theta_min      2.5
_cell_volume                     1570.8(6)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0929
_diffrn_reflns_av_sigmaI/netI    0.1012
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9232
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0481
_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)+(0.0597P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                1839
_reflns_number_total             3405
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2461.cif
_cod_data_source_block           I
_cod_original_cell_volume        1570.9(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226654
_cod_database_fobs_code          2226654
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
N N1 0.9564(3) 0.21280(5) 0.6283(3) 0.0368(5) Uani d . 1 . .
N N2 0.9265(3) 0.24056(6) 0.4765(3) 0.0377(5) Uani d D 1 . .
O O1 1.0227(3) 0.19610(5) 0.9820(2) 0.0522(5) Uani d . 1 . .
H H1 1.0193 0.2108 0.8900 0.078 Uiso calc R 1 . .
O O2 1.1086(2) 0.29306(4) 0.6668(2) 0.0446(4) Uani d . 1 . .
O O3 0.8581(3) 0.42263(5) 0.2180(3) 0.0610(5) Uani d . 1 . .
C C1 0.9067(3) 0.14315(6) 0.7351(3) 0.0325(5) Uani d . 1 . .
C C2 0.9652(3) 0.15572(7) 0.9238(3) 0.0374(5) Uani d . 1 . .
C C3 0.9684(4) 0.12616(8) 1.0675(3) 0.0448(6) Uani d . 1 . .
H H3 1.0045 0.1353 1.1932 0.054 Uiso calc R 1 . .
C C4 0.9194(4) 0.08463(8) 1.0244(4) 0.0465(6) Uani d . 1 . .
H H4 0.9231 0.0656 1.1215 0.056 Uiso calc R 1 . .
C C5 0.8625(3) 0.06948(7) 0.8351(3) 0.0385(6) Uani d . 1 . .
C C6 0.8142(4) 0.02588(8) 0.7898(4) 0.0512(7) Uani d . 1 . .
H H6 0.8181 0.0068 0.8867 0.061 Uiso calc R 1 . .
C C7 0.7624(4) 0.01126(8) 0.6091(5) 0.0632(8) Uani d . 1 . .
H H7 0.7330 -0.0176 0.5820 0.076 Uiso calc R 1 . .
C C8 0.7539(5) 0.04030(8) 0.4638(4) 0.0667(8) Uani d . 1 . .
H H8 0.7171 0.0305 0.3390 0.080 Uiso calc R 1 . .
C C9 0.7981(4) 0.08248(8) 0.5010(4) 0.0521(7) Uani d . 1 . .
H H9 0.7913 0.1009 0.4010 0.063 Uiso calc R 1 . .
C C10 0.8543(3) 0.09898(7) 0.6881(3) 0.0351(5) Uani d . 1 . .
C C11 0.8922(3) 0.17435(7) 0.5871(3) 0.0358(5) Uani d . 1 . .
H H11 0.8354 0.1664 0.4601 0.043 Uiso calc R 1 . .
C C12 1.0051(3) 0.28023(7) 0.5079(3) 0.0330(5) Uani d . 1 . .
C C13 0.9564(3) 0.30824(7) 0.3373(3) 0.0324(5) Uani d . 1 . .
C C14 0.9349(3) 0.35181(7) 0.3628(3) 0.0363(5) Uani d . 1 . .
H H14 0.9528 0.3624 0.4839 0.044 Uiso calc R 1 . .
C C15 0.8871(3) 0.37955(7) 0.2097(4) 0.0417(6) Uani d . 1 . .
C C16 0.8640(4) 0.36340(9) 0.0300(4) 0.0530(7) Uani d . 1 . .
H H16 0.8325 0.3819 -0.0736 0.064 Uiso calc R 1 . .
C C17 0.8871(4) 0.32039(9) 0.0040(4) 0.0535(7) Uani d . 1 . .
H H17 0.8726 0.3100 -0.1167 0.064 Uiso calc R 1 . .
C C18 0.9320(3) 0.29230(7) 0.1567(3) 0.0417(6) Uani d . 1 . .
H H18 0.9457 0.2631 0.1387 0.050 Uiso calc R 1 . .
C C19 0.8793(5) 0.44027(8) 0.3982(5) 0.0690(9) Uani d . 1 . .
H H19A 0.7877 0.4266 0.4486 0.104 Uiso calc R 1 . .
H H19B 0.8525 0.4705 0.3853 0.104 Uiso calc R 1 . .
H H19C 1.0122 0.4357 0.4830 0.104 Uiso calc R 1 . .
H H2 0.836(3) 0.2332(9) 0.363(2) 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
C11 N1 N2 . . 116.33(18) ?
C12 N2 N1 . . 119.46(18) ?
C12 N2 H2 . . 121.4(18) ?
N1 N2 H2 . . 118.1(18) ?
C2 O1 H1 . . 109.5 ?
C15 O3 C19 . . 117.2(2) ?
C2 C1 C10 . . 118.92(19) ?
C2 C1 C11 . . 120.4(2) ?
C10 C1 C11 . . 120.69(19) ?
O1 C2 C1 . . 123.1(2) ?
O1 C2 C3 . . 116.1(2) ?
C1 C2 C3 . . 120.8(2) ?
C4 C3 C2 . . 120.6(2) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 121.5(2) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 121.6(2) ?
C4 C5 C10 . . 118.7(2) ?
C6 C5 C10 . . 119.7(2) ?
C7 C6 C5 . . 121.7(2) ?
C7 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C6 C7 C8 . . 118.8(2) ?
C6 C7 H7 . . 120.6 ?
C8 C7 H7 . . 120.6 ?
C9 C8 C7 . . 121.5(3) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C8 C9 C10 . . 121.5(2) ?
C8 C9 H9 . . 119.2 ?
C10 C9 H9 . . 119.2 ?
C9 C10 C5 . . 116.9(2) ?
C9 C10 C1 . . 123.6(2) ?
C5 C10 C1 . . 119.5(2) ?
N1 C11 C1 . . 121.1(2) ?
N1 C11 H11 . . 119.5 ?
C1 C11 H11 . . 119.5 ?
O2 C12 N2 . . 123.04(19) ?
O2 C12 C13 . . 121.64(19) ?
N2 C12 C13 . . 115.32(19) ?
C14 C13 C18 . . 120.0(2) ?
C14 C13 C12 . . 117.57(19) ?
C18 C13 C12 . . 122.48(19) ?
C15 C14 C13 . . 120.5(2) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
O3 C15 C14 . . 125.3(2) ?
O3 C15 C16 . . 115.5(2) ?
C14 C15 C16 . . 119.2(2) ?
C17 C16 C15 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 120.4(2) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C13 . . 119.3(2) ?
C17 C18 H18 . . 120.4 ?
C13 C18 H18 . . 120.4 ?
O3 C19 H19A . . 109.5 ?
O3 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O3 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 C11 . 1.284(3) ?
N1 N2 . 1.384(2) ?
N2 C12 . 1.346(3) ?
N2 H2 . 0.905(10) ?
O1 C2 . 1.350(2) ?
O1 H1 . 0.8200 ?
O2 C12 . 1.235(3) ?
O3 C15 . 1.364(3) ?
O3 C19 . 1.413(3) ?
C1 C2 . 1.384(3) ?
C1 C10 . 1.439(3) ?
C1 C11 . 1.450(3) ?
C2 C3 . 1.408(3) ?
C3 C4 . 1.351(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.414(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.415(3) ?
C5 C10 . 1.418(3) ?
C6 C7 . 1.351(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.398(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.359(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.414(3) ?
C9 H9 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.485(3) ?
C13 C14 . 1.387(3) ?
C13 C18 . 1.391(3) ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.390(3) ?
C16 C17 . 1.373(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.387(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 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
N2 H2 O2 4_565 0.905(10) 1.965(13) 2.842(3) 163(2)
O1 H1 N1 . 0.82 1.85 2.574(2) 146.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745285
2 PubChem 135684361
