#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102723.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102723
loop_
_publ_author_name
'Hai-Yun Zhu'
'Ya-Ning Guo'
'De-Suo Yang'
_publ_contact_author
;
Prof. Ya-Ning Guo 
Department of Chemistry, 
Baoji University of Arts and Sciences,
Baoji, Shaanxi  721013
People's Republic of China
;
_publ_section_title
;
 Crystal structure of
 (Z)-1-(2,4-dinitrophenyl)-2-(3-methyl-2-nitrocyclohex-2-enylidene)hydrazine,
 C13H13N5O6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              359
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C13 H13 N5 O6'
_chemical_formula_weight         335.28
_chemical_name_systematic
; 
(Z)-1-(2,4-dinitrophenyl)-2-(3-methyl-2-
nitrocyclohex-2-enylidene)hydrazine, C₁₃H₁₃N₅O₆
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-04-01 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.913(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.501(2)
_cell_length_b                   6.362(1)
_cell_length_c                   17.166(2)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.33
_cell_measurement_theta_min      4.58
_cell_volume                     1479.3(4)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3177
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        6.04
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0136(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0342
_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)+(0.0503P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                1893
_reflns_number_total             2681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3005.cff
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1479.3(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8102723
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21423(9) 0.2481(2) 0.38156(8) 0.0390(3) Uani 1 1 d . . .
N2 N 0.30641(9) 0.3240(2) 0.39278(8) 0.0423(3) Uani 1 1 d . . .
H2N H 0.3579 0.2578 0.4244 0.051 Uiso 1 1 calc R . .
N3 N 0.03224(10) 0.0980(2) 0.34267(8) 0.0435(3) Uani 1 1 d . . .
N4 N 0.50127(10) 0.4768(2) 0.40628(8) 0.0459(4) Uani 1 1 d . . .
N5 N 0.34298(12) 1.0829(2) 0.24048(9) 0.0515(4) Uani 1 1 d . . .
O1 O -0.02228(9) 0.2147(2) 0.36234(8) 0.0675(4) Uani 1 1 d . . .
O2 O 0.02274(9) 0.0574(2) 0.27128(7) 0.0638(4) Uani 1 1 d . . .
O3 O 0.49790(8) 0.3096(2) 0.44239(7) 0.0551(3) Uani 1 1 d . . .
O4 O 0.57955(8) 0.5541(2) 0.40899(8) 0.0658(4) Uani 1 1 d . . .
O5 O 0.42502(10) 1.1644(2) 0.26088(8) 0.0659(4) Uani 1 1 d . . .
O6 O 0.26835(11) 1.1611(2) 0.19113(9) 0.0759(4) Uani 1 1 d . . .
C1 C 0.29474(12) -0.0134(3) 0.49457(10) 0.0516(5) Uani 1 1 d . . .
H1A H 0.3438 0.0916 0.5226 0.062 Uiso 1 1 calc R . .
H1B H 0.3255 -0.1153 0.4695 0.062 Uiso 1 1 calc R . .
C2 C 0.26034(14) -0.1234(3) 0.55812(11) 0.0581(5) Uani 1 1 d . . .
H2A H 0.3151 -0.2010 0.5970 0.070 Uiso 1 1 calc R . .
H2B H 0.2396 -0.0188 0.5895 0.070 Uiso 1 1 calc R . .
C3 C 0.17573(13) -0.2728(3) 0.51700(11) 0.0574(5) Uani 1 1 d . . .
H3A H 0.2002 -0.3925 0.4952 0.069 Uiso 1 1 calc R . .
H3B H 0.1504 -0.3244 0.5586 0.069 Uiso 1 1 calc R . .
C4 C 0.09295(13) -0.1718(3) 0.44727(10) 0.0453(4) Uani 1 1 d . . .
C5 C 0.11350(11) -0.0024(2) 0.41067(9) 0.0382(4) Uani 1 1 d . . .
C6 C 0.21026(11) 0.0904(2) 0.42736(9) 0.0385(4) Uani 1 1 d . . .
C7 C 0.31659(11) 0.5033(2) 0.35419(9) 0.0366(4) Uani 1 1 d . . .
C8 C 0.23313(11) 0.6199(3) 0.30581(9) 0.0409(4) Uani 1 1 d . . .
H8 H 0.1706 0.5696 0.2991 0.049 Uiso 1 1 calc R . .
C9 C 0.24149(12) 0.8035(3) 0.26869(9) 0.0416(4) Uani 1 1 d . . .
H9 H 0.1852 0.8768 0.2368 0.050 Uiso 1 1 calc R . .
C10 C 0.33453(11) 0.8819(3) 0.27841(9) 0.0400(4) Uani 1 1 d . . .
C11 C 0.41866(11) 0.7746(3) 0.32366(9) 0.0406(4) Uani 1 1 d . . .
H11 H 0.4805 0.8281 0.3296 0.049 Uiso 1 1 calc R . .
C12 C 0.41023(11) 0.5849(3) 0.36052(9) 0.0371(4) Uani 1 1 d . . .
C13 C -0.00687(14) -0.2691(3) 0.42225(12) 0.0625(5) Uani 1 1 d . . .
H13A H -0.0331 -0.2486 0.4657 0.075 Uiso 1 1 calc R . .
H13B H -0.0020 -0.4168 0.4131 0.075 Uiso 1 1 calc R . .
H13C H -0.0498 -0.2045 0.3718 0.075 Uiso 1 1 calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 N2 116.30(13) . . ?
C7 N2 N1 120.02(12) . . ?
C7 N2 H2N 120.0 . . ?
N1 N2 H2N 120.0 . . ?
O2 N3 O1 124.08(14) . . ?
O2 N3 C5 118.58(14) . . ?
O1 N3 C5 117.33(13) . . ?
O4 N4 O3 121.83(14) . . ?
O4 N4 C12 118.97(15) . . ?
O3 N4 C12 119.19(13) . . ?
O6 N5 O5 123.74(16) . . ?
O6 N5 C10 118.24(15) . . ?
O5 N5 C10 118.01(15) . . ?
C6 C1 C2 111.50(14) . . ?
C6 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C6 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 111.90(14) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 112.76(15) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C13 123.87(16) . . ?
C5 C4 C3 118.12(15) . . ?
C13 C4 C3 118.00(15) . . ?
C4 C5 C6 126.71(15) . . ?
C4 C5 N3 118.23(14) . . ?
C6 C5 N3 114.97(13) . . ?
N1 C6 C5 116.51(14) . . ?
N1 C6 C1 127.51(15) . . ?
C5 C6 C1 115.95(14) . . ?
N2 C7 C8 120.75(14) . . ?
N2 C7 C12 122.59(14) . . ?
C8 C7 C12 116.65(14) . . ?
C9 C8 C7 121.88(15) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.85(15) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 121.17(15) . . ?
C11 C10 N5 119.30(15) . . ?
C9 C10 N5 119.53(15) . . ?
C10 C11 C12 119.06(15) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 121.33(14) . . ?
C11 C12 N4 116.68(14) . . ?
C7 C12 N4 121.99(14) . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.2884(19) . ?
N1 N2 1.3686(17) . ?
N2 C7 1.353(2) . ?
N2 H2N 0.8600 . ?
N3 O2 1.2111(16) . ?
N3 O1 1.2169(17) . ?
N3 C5 1.4757(19) . ?
N4 O4 1.2227(17) . ?
N4 O3 1.2409(17) . ?
N4 C12 1.447(2) . ?
N5 O6 1.2174(18) . ?
N5 O5 1.2287(18) . ?
N5 C10 1.460(2) . ?
C1 C6 1.503(2) . ?
C1 C2 1.522(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.504(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.334(2) . ?
C4 C13 1.490(2) . ?
C5 C6 1.454(2) . ?
C7 C8 1.410(2) . ?
C7 C12 1.421(2) . ?
C8 C9 1.356(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O3 0.86 1.97 2.5993(17) 129.1 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C7 -172.56(13) . . . . ?
C6 C1 C2 C3 52.8(2) . . . . ?
C1 C2 C3 C4 -51.0(2) . . . . ?
C2 C3 C4 C5 22.6(2) . . . . ?
C2 C3 C4 C13 -158.34(16) . . . . ?
C13 C4 C5 C6 -174.74(15) . . . . ?
C3 C4 C5 C6 4.2(2) . . . . ?
C13 C4 C5 N3 1.5(2) . . . . ?
C3 C4 C5 N3 -179.53(14) . . . . ?
O2 N3 C5 C4 -98.49(18) . . . . ?
O1 N3 C5 C4 80.34(19) . . . . ?
O2 N3 C5 C6 78.21(18) . . . . ?
O1 N3 C5 C6 -102.96(16) . . . . ?
N2 N1 C6 C5 -174.80(13) . . . . ?
N2 N1 C6 C1 3.2(2) . . . . ?
C4 C5 C6 N1 176.43(15) . . . . ?
N3 C5 C6 N1 0.1(2) . . . . ?
C4 C5 C6 C1 -1.8(2) . . . . ?
N3 C5 C6 C1 -178.15(13) . . . . ?
C2 C1 C6 N1 155.12(16) . . . . ?
C2 C1 C6 C5 -26.9(2) . . . . ?
N1 N2 C7 C8 3.4(2) . . . . ?
N1 N2 C7 C12 -177.21(13) . . . . ?
N2 C7 C8 C9 177.88(14) . . . . ?
C12 C7 C8 C9 -1.5(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C8 C9 C10 N5 -178.06(13) . . . . ?
O6 N5 C10 C11 169.77(15) . . . . ?
O5 N5 C10 C11 -10.9(2) . . . . ?
O6 N5 C10 C9 -10.8(2) . . . . ?
O5 N5 C10 C9 168.51(14) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
N5 C10 C11 C12 179.16(13) . . . . ?
C10 C11 C12 C7 -1.8(2) . . . . ?
C10 C11 C12 N4 178.97(13) . . . . ?
N2 C7 C12 C11 -176.77(14) . . . . ?
C8 C7 C12 C11 2.6(2) . . . . ?
N2 C7 C12 N4 2.5(2) . . . . ?
C8 C7 C12 N4 -178.15(14) . . . . ?
O4 N4 C12 C11 -1.3(2) . . . . ?
O3 N4 C12 C11 177.97(13) . . . . ?
O4 N4 C12 C7 179.47(14) . . . . ?
O3 N4 C12 C7 -1.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139207280
