#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003579.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_2003579
loop_
_publ_author_name
'Velavan, R.'
'Sivakumar, K.'
'Anbu, M.'
_publ_section_title
;
 (<i>E</i>)-4-Nitrobenzaldehyde Phenylhydrazone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1227
_journal_page_last               1229
_journal_paper_doi               10.1107/S0108270194012606
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_chemical_name_systematic
;
4-Nitrobenzaldehydephenylhydrazone
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.059(1)
_cell_length_b                   11.598(2)
_cell_length_c                   17.253(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      25
_cell_volume                     1212.4(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'author's own'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf Nonius CAD-4 diffractometer'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0075
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1198
_diffrn_reflns_theta_max         64.88
_diffrn_reflns_theta_min         4.59
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       Needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.111
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.01(66)
_refine_ls_extinction_coef       '\c = 0.0094(13)'
_refine_ls_extinction_method
'F~c~^*^ = kF~c~[1 + 0.001\cF~c~^2^\l^3^/sin(2\'
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_obs   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_restrained_S_obs      1.099
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_obs          0.0368
_refine_ls_shift/esd_max         -0.087
_refine_ls_shift/esd_mean        0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[\s^2^(F~o~^2^) + (0.0643P)^2^ + 0.1528P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1097
_refine_ls_wR_factor_obs         0.1074
_reflns_number_observed          1087
_reflns_number_total             1198
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            li1127.cif
_cod_data_source_block           an3
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2003579
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
C1 0.078(2) 0.004(2) 0.009(2) 0.075(2) -0.0021(14) 0.073(2)
C2 0.085(2) -0.010(2) 0.012(2) 0.081(2) -0.009(2) 0.106(2)
C3 0.078(2) -0.007(2) -0.010(2) 0.088(2) -0.019(2) 0.118(3)
C4 0.095(2) 0.006(2) -0.019(2) 0.091(2) -0.010(2) 0.086(2)
C5 0.077(2) 0.001(2) -0.0010(15) 0.088(2) -0.0018(15) 0.072(2)
C6 0.0584(14) 0.0062(13) 0.0049(12) 0.0744(15) -0.0040(12) 0.0681(14)
N7 0.0673(14) -0.0125(15) 0.0000(12) 0.110(2) 0.0110(13) 0.0690(13)
N8 0.0638(13) 0.0027(12) 0.0002(11) 0.0816(14) 0.0029(11) 0.0677(13)
C9 0.0600(15) 0.002(2) 0.0049(14) 0.082(2) 0.0050(14) 0.075(2)
C10 0.0597(14) 0.0033(13) 0.0046(13) 0.0694(14) -0.0026(13) 0.0742(15)
C11 0.0616(14) -0.0060(14) 0.0028(15) 0.076(2) 0.0019(13) 0.079(2)
C12 0.072(2) -0.006(2) 0.0009(15) 0.080(2) 0.0033(14) 0.073(2)
C13 0.068(2) 0.001(2) -0.0079(15) 0.076(2) -0.0130(14) 0.082(2)
C14 0.058(2) -0.009(2) 0.002(2) 0.089(2) -0.019(2) 0.102(2)
C15 0.062(2) -0.006(2) 0.010(2) 0.091(2) -0.005(2) 0.083(2)
N16 0.087(2) -0.002(2) -0.017(2) 0.091(2) -0.017(2) 0.096(2)
O17 0.130(2) -0.024(2) -0.017(2) 0.126(2) 0.0027(14) 0.0848(15)
O18 0.089(2) -0.015(2) -0.022(2) 0.172(3) -0.045(2) 0.120(2)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
C1 1 0.5723(5) -0.2300(3) -0.2271(2) 0.0755(8) Uani d C
C2 1 0.7647(6) -0.1775(3) -0.2015(2) 0.0909(10) Uani d C
C3 1 0.8446(6) -0.1960(3) -0.1280(2) 0.0945(10) Uani d C
C4 1 0.7324(6) -0.2702(3) -0.0797(2) 0.0907(10) Uani d C
C5 1 0.5433(5) -0.3241(3) -0.1041(2) 0.0790(8) Uani d C
C6 1 0.4619(4) -0.3048(2) -0.1782(2) 0.0670(7) Uani d C
N7 1 0.2713(4) -0.3617(3) -0.2001(1) 0.0822(7) Uani d N
N8 1 0.1912(4) -0.3559(2) -0.2734(1) 0.0711(6) Uani d N
C9 1 0.0005(5) -0.4027(3) -0.2841(2) 0.0724(7) Uani d C
C10 1 -0.1000(5) -0.4069(2) -0.3601(2) 0.0678(7) Uani d C
C11 1 0.0070(5) -0.3645(2) -0.4269(2) 0.0722(7) Uani d C
C12 1 -0.0906(5) -0.3737(3) -0.4983(2) 0.0751(8) Uani d C
C13 1 -0.2965(5) -0.4247(3) -0.5038(2) 0.0755(8) Uani d C
C14 1 -0.4054(6) -0.4658(3) -0.4397(2) 0.0831(9) Uani d C
C15 1 -0.3058(5) -0.4573(3) -0.3685(2) 0.0789(8) Uani d C
N16 1 -0.4001(5) -0.4353(2) -0.5795(2) 0.0911(8) Uani d N
O17 1 -0.2933(5) -0.4091(3) -0.6377(2) 0.1136(9) Uani d O
O18 1 -0.5900(5) -0.4696(3) -0.5831(2) 0.1270(11) Uani d O
H1 1 0.5177(55) -0.2217(25) -0.2753(18) 0.088(10) Uiso d H
H2 1 0.8736(63) -0.1351(30) -0.2372(20) 0.112(12) Uiso d H
H3 1 0.9994(76) -0.1590(32) -0.1108(22) 0.124(12) Uiso d H
H4 1 0.7768(63) -0.2775(32) -0.0343(20) 0.103(12) Uiso d H
H5 1 0.4660(57) -0.3700(25) -0.0657(18) 0.094(10) Uiso d H
H7 1 0.2049(71) -0.4105(34) -0.1565(22) 0.130(14) Uiso d H
H9 1 -0.0830(56) -0.4411(26) -0.2395(17) 0.084(9) Uiso d H
H11 1 0.1732(60) -0.3381(29) -0.4181(18) 0.093(10) Uiso d H
H12 1 -0.0312(50) -0.3456(22) -0.5442(16) 0.071(8) Uiso d H
H14 1 -0.5271(68) -0.4911(30) -0.4481(19) 0.095(11) Uiso d H
H15 1 -0.3775(62) -0.4834(30) -0.3232(18) 0.103(11) Uiso d H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0181 0.009
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0311 0.018
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.032
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
C6 C1 C2 119.2(3) yes
C3 C2 C1 121.4(4) yes
C2 C3 C4 118.8(3) yes
C5 C4 C3 120.7(3) yes
C4 C5 C6 120.4(3) yes
C1 C6 N7 122.5(3) yes
C1 C6 C5 119.4(3) yes
N7 C6 C5 118.1(3) yes
N8 N7 C6 122.0(2) yes
C9 N8 N7 115.7(2) yes
N8 C9 C10 121.4(3) yes
C15 C10 C11 118.4(3) yes
C15 C10 C9 119.2(3) yes
C11 C10 C9 122.3(3) yes
C12 C11 C10 120.6(3) yes
C11 C12 C13 119.0(3) yes
C14 C13 C12 121.7(3) yes
C14 C13 N16 119.1(3) yes
C12 C13 N16 119.2(3) yes
C13 C14 C15 119.0(3) yes
C14 C15 C10 121.3(3) yes
O18 N16 O17 122.4(3) yes
O18 N16 C13 118.7(3) yes
O17 N16 C13 118.9(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.382(4) yes
C1 C2 1.388(4) yes
C2 C3 1.374(5) yes
C3 C4 1.378(5) yes
C4 C5 1.371(5) yes
C5 C6 1.389(4) yes
C6 N7 1.382(4) yes
N7 N8 1.356(3) yes
N8 C9 1.290(4) yes
C9 C10 1.448(4) yes
C10 C15 1.385(4) yes
C10 C11 1.411(4) yes
C11 C12 1.370(4) yes
C12 C13 1.384(4) yes
C13 C14 1.373(4) yes
C13 N16 1.454(4) yes
C14 C15 1.373(5) yes
N16 O18 1.219(4) yes
N16 O17 1.233(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7858651
2 PubChem 9584504