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#$Date: 2025-08-19 22:00:13 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/10/2311095.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_2311095
loop_
_publ_author_name
'Tanaka, Kiyoaki'
_publ_section_title
;
 X-ray molecular orbital analysis. I. Quantum mechanical and
 crystallographic framework
;
_journal_coeditor_code           KX5062
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section A'
_journal_page_first              345
_journal_page_last               356
_journal_paper_doi               10.1107/S2053273318005478
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'N2 H4 C2 O2'
_chemical_formula_sum            'C2 H4 N2 O2'
_chemical_formula_weight         88.066
_chemical_name_common            diformohydrazide
_chemical_name_systematic        diformohydrazide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   other
_audit_creation_method           ????-??-??
_cell_angle_alpha                90.00
_cell_angle_beta                 112.190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9520(13)
_cell_length_b                   6.1946(5)
_cell_length_c                   3.4927(5)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      39.28
_cell_measurement_theta_min      35.80
_cell_volume                     179.34(4)
_computing_cell_refinement
;
RSLC-3 UNICS system (Sakurai, T. & Kobayashi, K. (1979), Rep. Inst. Phys. Chem.
Res. 55, 69-77)
;
_computing_data_collection
;
MXC (MAC Science) and a program IUANGLE by Tanaka
(Tanaka, K.,Kumazawa S., Tsubokawa, M., Maruno, S. &
Shirotani, I. (Acta Cryst., A50, 246-252(1994))
;
_computing_data_reduction        'RDEDIT (K. Tanaka)'
_computing_structure_refinement  'QNTMO (K. Tanaka, 2018)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean '1.25x1.25 degrees'
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.547
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'integrated intensities data from ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           ' Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0067
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4692
_diffrn_reflns_theta_full        15.00
_diffrn_reflns_theta_max         74.68
_diffrn_reflns_theta_min         4.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.1355
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Transmission cefficient for spheres tabulated in International Table
II(1972) Table 5.3.6B was interpolated with Lagrange's method (four point
interpolation)
;
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       sphere
_exptl_crystal_F_000             88
_exptl_crystal_size_rad          0.079
_refine_diff_density_max         0.002
_refine_diff_density_min         -0.076
_refine_ls_extinction_method     'B-C type 2 Gaussian anisotropic'
_refine_ls_goodness_of_fit_ref   0.8288
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     842
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0129
_refine_ls_shift/su_max          1.98
_refine_ls_shift/su_mean         0.403
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0114
_reflns_number_gt                3035
_reflns_number_total             2423
_reflns_threshold_expression     F>3.0σ(F)
_cod_data_source_file            kx5062sup1.cif
_cod_data_source_block           global
_cod_original_cell_volume        179.30(10)
_cod_original_sg_symbol_H-M      'P 21/a  (origin at the center of N-N bond)'
_cod_original_formula_sum        'N2 H4 C2 O2'
_cod_database_code               2311095
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2+x,1/2-y,z
1/2-x,1/2+y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
C C 0.138600(10) 0.218020(10) 0.10721(6) 1.0
N N 0.00323(2) 0.10455(2) -0.06475(6) 1.0
O O 0.261980(10) 0.14612(3) 0.38062(2) 1.0
H H(N) -0.0944(7) 0.1643(9) -0.2824(15) 1.0
H H(C) 0.1298(5) 0.3720(9) -0.0129(7) 1.0
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C carbon 0.002 0.002
;
Calculated for each molecular orbital with a program QNTMO
by Kiyoaki Tanaka (Acta Cryst. A. (2018);submitted)
;
N nitrogen 0.004 0.003
;
Calculated for each molecular orbital with a program QNTMO
by Kiyoaki Tanaka (Acta Cryst. A. (2018);submitted)
;
O oxygen 0.008 0.003
;
Calculated for each molecular orbital with a program QNTMO
by Kiyoaki Tanaka (Acta Cryst. A. (2018);submitted)
;
H hydrogen 0.000 0.006
;
Calculated for each molecular orbital with a program QNTMO
by Kiyoaki Tanaka (Acta Cryst. A. (2018);submitted)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 0
-1 -2 0
0 0 1
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C N N 1_555 1_555 3_555 119.410(10) n
N N H(N) 3_555 1_555 1_555 118.0(3) n
C N H(N) 1_555 1_555 1_555 122.6(3) n
N C O 1_555 1_555 1_555 123.550(10) n
N C H(C) 1_555 1_555 1_555 112.8(3) n
O C H(C) 1_555 1_555 1_555 123.7(3) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N N 1_555 2_555 1.3804(2) n
N C 1_555 1_555 1.3318(2) n
C O 1_555 1_555 1.2383(2) n
N H(N) 1_555 1_555 0.988(5) n
C H(C) 1_555 1_555 1.033(5) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
N H(N) O 1_555 1_555 3_454 0.988(5) 1.810(5) 2.7644(17) 161.4(4) n
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O C N N 1_555 1_555 1_555 2_555 0.31 n
O C N H(N) 1_555 1_555 1_555 1_555 179.86 n
C N N H(N) 2_555 2_555 1_555 1_555 0.43 n
H(C) C N N 1_555 1_555 1_555 2_555 -179.97 n
H(C) C N H(N) 1_555 1_555 1_555 1_555 -0.42 n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12342
