#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/21/2202147.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_2202147
loop_
_publ_author_name
'Shang Shan'
'Duan-Jun Xu'
'Jing-Yun Wu'
'Michael Y. Chiang'
_publ_section_title
;
 Salicylaldehyde 4-nitrophenylhydrazone
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o342
_journal_page_last               o343
_journal_paper_doi               10.1107/S1600536803003350
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C13 H11 N3 O3'
_chemical_formula_moiety         'C13 H11 N3 O3'
_chemical_formula_sum            'C13 H11 N3 O3'
_chemical_formula_weight         257.25
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 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                 92.199(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0052(11)
_cell_length_b                   9.9004(16)
_cell_length_c                   12.1749(12)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.2
_cell_measurement_theta_min      8.6
_cell_volume                     602.86(17)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       ω/2θ
_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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1328
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        1.9
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1190
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.073
_refine_ls_R_factor_gt           0.032
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0473P)²+0.0138P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.076
_refine_ls_wR_factor_ref         0.091
_reflns_number_gt                774
_reflns_number_total             1190
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6130.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2202147
_cod_database_fobs_code          2202147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
loop_
_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
_atom_site_type_symbol
O1 1.1219(6) 0.0500(3) 0.5900(2) 0.0774(8) Uani d . 1 . . O
O2 1.1702(6) -0.1120(3) 0.4758(3) 0.0880(10) Uani d . 1 . . O
O3 -0.0249(5) 0.5120(2) 0.3978(2) 0.0635(7) Uani d . 1 . . O
N1 1.0663(6) -0.0053(3) 0.5016(3) 0.0576(8) Uani d . 1 . . N
N2 0.2966(5) 0.2283(3) 0.2189(2) 0.0479(7) Uani d . 1 . . N
H1 0.2781 0.1981 0.1528 0.057 Uiso calc R 1 . . H
N3 0.1378(5) 0.3308(2) 0.2531(2) 0.0446(6) Uani d . 1 . . N
C1 0.4849(6) 0.1739(3) 0.2897(3) 0.0417(7) Uani d . 1 . . C
C2 0.6294(7) 0.0607(3) 0.2557(3) 0.0515(8) Uani d . 1 . . C
H2 0.5952 0.0251 0.1859 0.062 Uiso calc R 1 . . H
C3 0.8191(6) 0.0024(3) 0.3237(3) 0.0529(9) Uani d . 1 . . C
H3 0.9124 -0.0730 0.3006 0.063 Uiso calc R 1 . . H
C4 0.8723(7) 0.0565(3) 0.4277(3) 0.0454(7) Uani d . 1 . . C
C5 0.7345(6) 0.1688(4) 0.4615(3) 0.0509(8) Uani d . 1 . . C
H5 0.7724 0.2051 0.5308 0.061 Uiso calc R 1 . . H
C6 0.5424(6) 0.2272(3) 0.3939(3) 0.0481(8) Uani d . 1 . . C
H6 0.4500 0.3027 0.4176 0.058 Uiso calc R 1 . . H
C7 -0.0384(6) 0.3772(3) 0.1848(3) 0.0475(8) Uani d . 1 . . C
H7 -0.0531 0.3402 0.1146 0.057 Uiso calc R 1 . . H
C8 -0.2189(6) 0.4873(3) 0.2140(3) 0.0464(8) Uani d . 1 . . C
C9 -0.2040(6) 0.5500(3) 0.3169(3) 0.0505(8) Uani d . 1 . . C
C10 -0.3793(8) 0.6534(4) 0.3392(4) 0.0656(11) Uani d . 1 . . C
H10 -0.3685 0.6961 0.4072 0.079 Uiso calc R 1 . . H
C11 -0.5690(7) 0.6935(4) 0.2618(4) 0.0690(11) Uani d . 1 . . C
H11 -0.6864 0.7627 0.2784 0.083 Uiso calc R 1 . . H
C12 -0.5887(7) 0.6337(4) 0.1604(3) 0.0619(10) Uani d . 1 . . C
H12 -0.7185 0.6617 0.1086 0.074 Uiso calc R 1 . . H
C13 -0.4131(7) 0.5312(3) 0.1361(3) 0.0555(9) Uani d . 1 . . C
H13 -0.4241 0.4908 0.0672 0.067 Uiso calc R 1 . . H
H9 0.0943 0.4491 0.3658 0.080 Uiso d . 1 . . H
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_geom_angle_publ_flag
C9 O3 H9 106.8 ?
O2 N1 O1 121.7(3) ?
O2 N1 C4 119.4(3) ?
O1 N1 C4 118.9(3) ?
C1 N2 N3 119.9(3) yes
C1 N2 H1 120.1 ?
N3 N2 H1 120.1 ?
C7 N3 N2 117.7(3) yes
N2 C1 C6 122.6(3) ?
N2 C1 C2 118.7(3) ?
C6 C1 C2 118.7(3) ?
C3 C2 C1 120.9(3) ?
C3 C2 H2 119.6 ?
C1 C2 H2 119.6 ?
C2 C3 C4 119.6(3) ?
C2 C3 H3 120.2 ?
C4 C3 H3 120.2 ?
C5 C4 C3 120.1(3) ?
C5 C4 N1 119.4(3) ?
C3 C4 N1 120.5(3) ?
C6 C5 C4 120.6(3) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C5 C6 C1 120.1(3) ?
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
N3 C7 C8 121.8(3) ?
N3 C7 H7 119.1 ?
C8 C7 H7 119.1 ?
C9 C8 C13 118.7(3) ?
C9 C8 C7 122.3(3) ?
C13 C8 C7 118.9(3) ?
O3 C9 C10 118.0(3) ?
O3 C9 C8 122.5(3) ?
C10 C9 C8 119.5(3) ?
C11 C10 C9 120.6(4) ?
C11 C10 H10 119.7 ?
C9 C10 H10 119.7 ?
C12 C11 C10 121.2(4) ?
C12 C11 H11 119.4 ?
C10 C11 H11 119.4 ?
C11 C12 C13 119.1(4) ?
C11 C12 H12 120.5 ?
C13 C12 H12 120.5 ?
C12 C13 C8 120.9(4) ?
C12 C13 H13 119.6 ?
C8 C13 H13 119.6 ?
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 N1 . 1.229(4) yes
O2 N1 . 1.224(4) yes
O3 C9 . 1.359(4) yes
O3 H9 . 0.956 ?
N1 C4 . 1.436(4) yes
N2 C1 . 1.364(4) yes
N2 N3 . 1.364(3) yes
N2 H1 . 0.860 ?
N3 C7 . 1.274(4) yes
C1 C6 . 1.394(4) ?
C1 C2 . 1.404(5) ?
C2 C3 . 1.364(5) ?
C2 H2 . 0.930 ?
C3 C4 . 1.391(5) ?
C3 H3 . 0.930 ?
C4 C5 . 1.379(5) ?
C5 C6 . 1.370(5) ?
C5 H5 . 0.930 ?
C6 H6 . 0.930 ?
C7 C8 . 1.468(4) yes
C7 H7 . 0.930 ?
C8 C9 . 1.398(4) ?
C8 C13 . 1.401(5) ?
C9 C10 . 1.382(5) ?
C10 C11 . 1.371(5) ?
C10 H10 . 0.930 ?
C11 C12 . 1.368(6) ?
C11 H11 . 0.930 ?
C12 C13 . 1.382(5) ?
C12 H12 . 0.930 ?
C13 H13 . 0.930 ?
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
_geom_hbond_publ_flag
O3 H9 N3 . 0.956 1.823 2.664(3) 145 yes
N2 H1 O2 2_454 0.860 2.360 3.215(4) 173 yes
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
C1 N2 N3 C7 -178.8(3)
N3 N2 C1 C6 -6.6(4)
N3 N2 C1 C2 174.4(3)
N2 C1 C2 C3 -179.8(3)
C6 C1 C2 C3 1.1(5)
C1 C2 C3 C4 -0.7(5)
C2 C3 C4 C5 -0.3(5)
C2 C3 C4 N1 178.4(3)
O2 N1 C4 C5 173.1(3)
O1 N1 C4 C5 -6.2(5)
O2 N1 C4 C3 -5.5(5)
O1 N1 C4 C3 175.1(3)
C3 C4 C5 C6 0.7(5)
N1 C4 C5 C6 -177.9(3)
C4 C5 C6 C1 -0.3(5)
N2 C1 C6 C5 -179.7(3)
C2 C1 C6 C5 -0.7(4)
N2 N3 C7 C8 179.9(2)
N3 C7 C8 C9 1.7(4)
N3 C7 C8 C13 -178.3(3)
C13 C8 C9 O3 178.8(3)
C7 C8 C9 O3 -1.2(5)
C13 C8 C9 C10 -0.2(4)
C7 C8 C9 C10 179.8(3)
O3 C9 C10 C11 -178.3(3)
C8 C9 C10 C11 0.8(5)
C9 C10 C11 C12 -0.6(6)
C10 C11 C12 C13 -0.2(5)
C11 C12 C13 C8 0.7(5)
C9 C8 C13 C12 -0.5(5)
C7 C8 C13 C12 179.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12549131
2 PubChem 135509553
