#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208212.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_2208212
loop_
_publ_author_name
'Guo, Min-Jie'
'Sun, Jia-Cui'
'Jing, Zuo-Liang'
'Yu, Ming'
'Chen, Xin'
_publ_section_title
;
 3-Nitrobenzaldehyde isonicotinoylhydrazone monohydrate
;
_journal_coeditor_code           WW6473
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o820
_journal_page_last               o821
_journal_paper_doi               10.1107/S1600536806002509
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H10 N4 O3, H2 O'
_chemical_formula_moiety         'C13 H10 N4 O3, H2 O'
_chemical_formula_sum            'C13 H12 N4 O4'
_chemical_formula_weight         288.27
_chemical_name_systematic
;
3-Nitrobenzaldehyde isonicotinoylhydrazone monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   13.374(5)
_cell_length_b                   13.040(5)
_cell_length_c                   15.742(6)
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.54
_cell_volume                     2745.4(18)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13799
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0416
_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)+(0.0683P)²+0.4518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                1848
_reflns_number_total             2430
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6473.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2745.5(17)
_cod_database_code               2208212
_cod_database_fobs_code          2208212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_type_symbol
O1 0.40797(8) 0.46555(10) 0.25113(8) 0.0572(4) Uani d . 1 O
O2 0.18837(10) 0.30805(13) 0.55993(14) 0.0866(5) Uani d . 1 O
O3 0.19816(12) 0.27992(16) 0.69386(13) 0.1075(7) Uani d . 1 O
N1 0.68113(12) 0.55279(14) 0.04601(10) 0.0653(5) Uani d . 1 N
N2 0.54651(10) 0.43675(11) 0.33008(8) 0.0448(4) Uani d . 1 N
H2 0.6155(15) 0.4439(13) 0.3366(12) 0.056(5) Uiso d . 1 H
N3 0.49113(10) 0.40286(11) 0.39870(8) 0.0454(4) Uani d . 1 N
N4 0.23636(13) 0.29636(13) 0.62491(14) 0.0686(5) Uani d . 1 N
C1 0.66399(13) 0.46434(14) 0.17829(11) 0.0516(4) Uani d . 1 C
H1 0.6931 0.4230 0.2196 0.062 Uiso calc R 1 H
C2 0.71817(14) 0.49501(17) 0.10805(12) 0.0608(5) Uani d . 1 C
H2A 0.7844 0.4740 0.1039 0.073 Uiso calc R 1 H
C3 0.58636(15) 0.58293(16) 0.05464(13) 0.0643(5) Uani d . 1 C
H3 0.5588 0.6235 0.0121 0.077 Uiso calc R 1 H
C4 0.52698(13) 0.55750(14) 0.12290(12) 0.0549(5) Uani d . 1 C
H4 0.4616 0.5814 0.1263 0.066 Uiso calc R 1 H
C5 0.56581(12) 0.49594(13) 0.18625(10) 0.0430(4) Uani d . 1 C
C6 0.49889(12) 0.46511(12) 0.25825(10) 0.0430(4) Uani d . 1 C
C7 0.54131(11) 0.37867(12) 0.46405(10) 0.0451(4) Uani d . 1 C
H7 0.6106 0.3844 0.4629 0.054 Uiso calc R 1 H
C8 0.49212(11) 0.34204(12) 0.54118(10) 0.0418(4) Uani d . 1 C
C9 0.38857(12) 0.33443(12) 0.54605(11) 0.0459(4) Uani d . 1 C
H9 0.3489 0.3510 0.4995 0.055 Uiso calc R 1 H
C10 0.34606(13) 0.30209(13) 0.62051(12) 0.0494(4) Uani d . 1 C
C11 0.40113(15) 0.27592(14) 0.69118(12) 0.0581(5) Uani d . 1 C
H11 0.3700 0.2547 0.7410 0.070 Uiso calc R 1 H
C12 0.50331(14) 0.28211(14) 0.68593(12) 0.0594(5) Uani d . 1 C
H12 0.5424 0.2640 0.7324 0.071 Uiso calc R 1 H
C13 0.54844(13) 0.31524(14) 0.61177(12) 0.0514(4) Uani d . 1 C
H13 0.6178 0.3196 0.6092 0.062 Uiso calc R 1 H
O4 0.75555(10) 0.45365(12) 0.37152(10) 0.0645(4) Uani d . 1 O
H4A 0.8069(18) 0.4586(17) 0.3410(16) 0.084(8) Uiso d . 1 H
H4B 0.7763(17) 0.4489(18) 0.4233(17) 0.082(8) 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 0.0016 '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
_geom_angle_publ_flag
C2 N1 C3 116.50(16) ?
C6 N2 N3 119.31(13) yes
C6 N2 H2 122.2(12) ?
N3 N2 H2 118.4(12) ?
C7 N3 N2 115.46(13) yes
O2 N4 O3 123.3(2) yes
O2 N4 C10 118.69(17) ?
O3 N4 C10 118.0(2) ?
C2 C1 C5 118.99(17) ?
C2 C1 H1 120.5 ?
C5 C1 H1 120.5 ?
N1 C2 C1 123.84(17) ?
N1 C2 H2A 118.1 ?
C1 C2 H2A 118.1 ?
N1 C3 C4 123.82(18) ?
N1 C3 H3 118.1 ?
C4 C3 H3 118.1 ?
C3 C4 C5 119.12(17) ?
C3 C4 H4 120.4 ?
C5 C4 H4 120.4 ?
C4 C5 C1 117.71(16) ?
C4 C5 C6 118.50(15) ?
C1 C5 C6 123.77(15) ?
O1 C6 N2 123.24(15) yes
O1 C6 C5 121.59(15) yes
N2 C6 C5 115.17(14) ?
N3 C7 C8 121.14(14) yes
N3 C7 H7 119.4 ?
C8 C7 H7 119.4 ?
C13 C8 C9 118.60(15) ?
C13 C8 C7 120.23(14) yes
C9 C8 C7 121.16(15) yes
C10 C9 C8 118.85(16) ?
C10 C9 H9 120.6 ?
C8 C9 H9 120.6 ?
C9 C10 C11 123.08(16) ?
C9 C10 N4 118.04(17) ?
C11 C10 N4 118.87(17) ?
C12 C11 C10 118.01(17) ?
C12 C11 H11 121.0 ?
C10 C11 H11 121.0 ?
C11 C12 C13 120.26(17) ?
C11 C12 H12 119.9 ?
C13 C12 H12 119.9 ?
C12 C13 C8 121.18(16) ?
C12 C13 H13 119.4 ?
C8 C13 H13 119.4 ?
H4A O4 H4B 106(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 1.221(2) yes
O2 N4 1.217(2) yes
O3 N4 1.219(2) yes
N1 C2 1.329(2) ?
N1 C3 1.334(3) ?
N2 C6 1.349(2) yes
N2 N3 1.3823(18) yes
N2 H2 0.933(19) ?
N3 C7 1.268(2) yes
N4 C10 1.471(3) ?
C1 C2 1.381(2) ?
C1 C5 1.382(2) ?
C1 H1 0.9300 ?
C2 H2A 0.9300 ?
C3 C4 1.377(3) ?
C3 H3 0.9300 ?
C4 C5 1.382(2) ?
C4 H4 0.9300 ?
C5 C6 1.499(2) yes
C7 C8 1.461(2) yes
C7 H7 0.9300 ?
C8 C13 1.387(2) yes
C8 C9 1.391(2) yes
C9 C10 1.369(2) ?
C9 H9 0.9300 ?
C10 C11 1.377(3) ?
C11 C12 1.372(3) ?
C11 H11 0.9300 ?
C12 C13 1.383(3) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
O4 H4A 0.84(3) ?
O4 H4B 0.86(3) ?
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
N2 H2 O4 . 0.93(2) 1.96(2) 2.879(2) 170(2) yes
O4 H4A O1 6_656 0.84(3) 1.98(3) 2.812(2) 168(2) yes
O4 H4B N1 2_665 0.86(3) 2.01(3) 2.876(2) 176(2) yes
C1 H1 O4 . 0.93 2.56 3.282(3) 134 yes
C7 H7 O4 . 0.93 2.58 3.360(2) 142 yes
C12 H12 O3 6_657 0.93 2.39 3.221(3) 148 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
C6 N2 N3 C7 -179.29(14)
C3 N1 C2 C1 1.1(3)
C5 C1 C2 N1 -0.9(3)
C2 N1 C3 C4 -0.1(3)
N1 C3 C4 C5 -1.0(3)
C3 C4 C5 C1 1.1(3)
C3 C4 C5 C6 -177.36(17)
C2 C1 C5 C4 -0.2(3)
C2 C1 C5 C6 178.18(16)
N3 N2 C6 O1 2.4(2)
N3 N2 C6 C5 -177.25(13)
C4 C5 C6 O1 22.2(2)
C1 C5 C6 O1 -156.24(17)
C4 C5 C6 N2 -158.23(15)
C1 C5 C6 N2 23.4(2)
N2 N3 C7 C8 179.76(14)
N3 C7 C8 C13 179.51(15)
N3 C7 C8 C9 -1.3(2)
C13 C8 C9 C10 0.8(2)
C7 C8 C9 C10 -178.38(15)
C8 C9 C10 C11 -0.4(3)
C8 C9 C10 N4 178.90(15)
O2 N4 C10 C9 9.0(3)
O3 N4 C10 C9 -171.13(18)
O2 N4 C10 C11 -171.70(18)
O3 N4 C10 C11 8.2(3)
C9 C10 C11 C12 -0.5(3)
N4 C10 C11 C12 -179.78(16)
C10 C11 C12 C13 0.9(3)
C11 C12 C13 C8 -0.5(3)
C9 C8 C13 C12 -0.4(3)
C7 C8 C13 C12 178.85(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179718
2 PubChem 139060039
