##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section A. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section A, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2020-11-30
_journal_date_accepted     2021-06-21
_journal_name_full     'Acta Crystallographica, Section A'
_journal_year     2021
_journal_volume     77
_journal_issue      6
_journal_page_first     593
_journal_page_last     610
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053273321006495
_journal_coeditor_code     PL5011
_publ_contact_author_name     'Kiyoaki Tanaka'
_publ_contact_author_address
;
Research Division
Nagoya Industrial Science Research Institute
Yotsuya-toori, 1-13,Chikusa-ku
Nagoya 466-0819
Japan
;
_publ_contact_author_email     Tanaka.kiyoaki@nisri.jp
_publ_contact_author_fax     '81 52 781 1884'
_publ_contact_author_phone     '81 6 7493 6370'
_publ_section_title
;
X-ray molecular orbital analysis II. Application to diformohydrazide, (NHCHO)2
;
_publ_section_title_footnote
; ?
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tanaka, Kiyoaki'
;
Also at Nagoya Insitute of Technology
;
;
Yotsuya toori 1-13, Chikusa-ku
Nagota, 464-0819
Japan
;
    'Wasada-Tsutsui, Yuko'
;
;
;
Life Science and Applied Chemistry
Nagoya Institute of Technology
Gokiso-cho, Showa-ku
Nagoya, 466-8555
Japan
;
_publ_section_synopsis
; ?
;
data_I
_chemical_name_systematic     'diformohydrazide'
_chemical_name_common     'diformohydrazide'
_chemical_formula_moiety     'C2 H4 N2 O2'
_chemical_formula_sum     'C2 H4 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     ?
_chemical_formula_weight     88.066
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/a 1'
_symmetry_space_group_name_Hall     ?
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'
_cell_length_a     8.9520(13)
_cell_length_b     6.1946(5)
_cell_length_c     3.4927(5)
_cell_angle_alpha     90
_cell_angle_beta     112.1902(2)
_cell_angle_gamma     90
_cell_volume     179.34(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     24
_cell_measurement_theta_min     48.327
_cell_measurement_theta_max     73.708
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     sphere
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     ?
_exptl_crystal_size_mid     ?
_exptl_crystal_size_min     ?
_exptl_crystal_size_rad     0.0793
_exptl_crystal_density_diffrn     1.631
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     92.
_exptl_absorpt_coefficient_mu     0.1355
_exptl_absorpt_correction_type     sphere
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     0.98402
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
The crystal was shaped into a sphere of the averaged radius of 0.0793 mm by
rolling it manually on a wet filter paper.  The difference between the longest
and the shortest diameters is less than 4 % of the longest one, which can be
neglected since the linear absorption coefficient m=0.1355 mm-1 is small.
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     ' Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'four-circle diffractometer'
_diffrn_measurement_method     'integrated intensities data from ω/2θ scans'
_diffrn_detector_area_resol_mean     '1.25x1.25 degrees'
_diffrn_reflns_number     5510
_diffrn_reflns_av_R_equivalents     0.01498
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     4.11
_diffrn_reflns_theta_max     73.71
_diffrn_reflns_theta_full     15.0
_diffrn_measured_fraction_theta_max     0.7981
_diffrn_measured_fraction_theta_full     0.3016
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     8
_diffrn_reflns_reduction_process
;
When \w and \c angles of the four-circle diffractometer deviate from the
previous ones by 0.13\% and 0.10\%, respectively, the orientation matrix was
automatically measured again repeating the previous block of 30 reflections.
To avoid multiple diffraction, 1747 reflections were measured with \y rotation
(Program IUANGLE by K. T.). When there is no space for a reflection to avoid
the multiple diffraction with \y-rotation, the other equivalent reflections are
checked.  Threfore, one of the equivalents ((h,k,l), (-h,-k,-l), (h,-k,l) and
(-h,k,-l) are scattered in the measured reflections.
;
_diffrn_standards_number     3
_diffrn_standards_interval_count     30
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
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
_refine_special_details
;
Molecular orbitals were refined & determined by the XMO analysis.
(K. Tanaka, Acta Cryst.(2018). A74, 345-356.)
Among 788 MO coefficients, 692 of them are larger than their e.s.d.'s, 637 of
which have shift/su < 1.0 and mean value of shift/su is 0.49. The largest
shift/su = 7.53 listed below is the ratio of significant MO coefficient
a14,106 = -0.124(4) with shift = -0.031. When the max of the shift/su is
limited to those of atomic parameters, scales and extinction parameters, the
largest one is 1.11 for the extinction parameter G22. When only G22 is refined,
the ratio and its e.s.d. are reduced to 0.666 and 75, respectively, though this
is not a valid refinement defined in the above paper. For G22, see the second
parameter below.
B-C anisotropic type 2 extinction parameters
B-C anisotropic extinction parameters are as follows
 572(15)   1252(119)    833(40)      0(21)   -596(16)    123(41)
;
_reflns_number_total     4692
_reflns_number_gt     3036
_reflns_threshold_expression     F>3.0σ(F)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     ?
_refine_ls_R_factor_gt     0.01237
_refine_ls_wR_factor_all     ?
_refine_ls_wR_factor_gt     0.01092
_refine_ls_wR_factor_ref     ?
_refine_ls_goodness_of_fit_all     ?
_refine_ls_goodness_of_fit_ref     ?
_refine_ls_goodness_of_fit_gt     0.77704
_refine_ls_restrained_S_all     ?
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     2423
_refine_ls_number_parameters     842
_refine_ls_number_restraints     ?
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     w=1/u(F)
_refine_ls_shift/su_max     7.53
_refine_ls_shift/su_mean     0.22
_refine_diff_density_max     0.1270
_refine_diff_density_min     -0.1252
_refine_ls_extinction_method     'B-C type 2 Gaussian anisotropic'
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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
;
International Tables for X-ray Crystallography (1974,
Vol. IV, Table 2.3.1)
;
    N 'nitrogen' 0.004 0.003
;
International Tables for X-ray Crystallography (1974,
Vol. IV, Table 2.3.1)
;
    O 'oxygen' 0.008 0.006
;
International Tables for X-ray Crystallography (1974,
Vol. IV, Table 2.3.1)
;
    H 'hydrogen' 0.000 0.000
;
International Tables for X-ray Crystallography (1974,
Vol. IV, Table 2.3.1)
;
_computing_data_collection
;
MXC(MAC Science) and a program IUANGLE by Tanaka for avoidance of multiple
diffraction (Tanaka, K.,Kumazawa S., Tsubokawa, M., Maruno, S. &
Shirotani, I. (Acta Cryst. A50, 246-252 (1994))
;
_computing_cell_refinement
;
RSLC-3 UNICS system (Sakurai, T. & Kobayashi, K. (1979), Rep. Inst. Phys. Chem.
Res. 55, 69-77)
;
_computing_data_reduction     'RDEDIT (K. Tanaka)'
_computing_structure_solution     ?
_computing_structure_refinement
;
QNTMO (Tanaka, K. (2018). Acta Cryst. A74, 345-356.
;
_computing_molecular_graphics     ?
_computing_publication_material     ?
loop_
    _atom_site_type_symbol
    _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_calc_attached_atom
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C 0.138610(10)
                   0.21801(2) 0.10724(4) 0.00974(2) Uani d ? ? ? ? ?
    N N 0.003220(10)
                   0.10457(2) -0.06478(4) 0.00939(2) Uani d ? ? ? ? ?
    O O 0.261973(8) 0.146120(10)
                               0.38059(3) 0.01222(2) Uani d ? ? ? ? ?
    H HC 0.1300(3) 0.3720(3) -0.0122(6) 0.0320(10)
                                                 Uani d ? ? ? ? ?
    H HN -0.0993(4) 0.1660(6) -0.29180(10)
                                         0.0130(10)
                                                  Uani d ? ? ? ? ?
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    _atom_site_aniso_type_symbol
    C 0.00820(2) 0.00811(2) 0.01056(3) -0.00093(3) 0.00088(2) -0.00008(2) C
    N 0.00714(2) 0.00858(2) 0.00985(3) -0.00029(2) 0.00027(2) 0.00046(3) N
    O 0.00844(2) 0.01056(2) 0.01325(3) -0.00102(2) -0.00092(2) -0.00073(3) O
    HC 0.0290(10)
                0.024(2) 0.0370(10)
                                  -0.0060(10)
                                            0.0048(9) 0.0050(10)
                                                               H
    HN 0.010(2) 0.007(2) 0.015(2) -0.0020(10)
                                            -0.0030(10)
                                                      0.0030(10)
                                                               H
_geom_special_details     ?
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
    C N 1_555 1_555 1.33180(10)
                              y
    C O 1_555 1_555 1.23810(10)
                              y
    N N 2_555 1_555 1.3806(2) y
    C HC 1_555 1_555 1.032(2) y
    N HN 1_555 1_555 1.033(3) y
    HN O 1_555 2_555 2.369(3) y
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    HN O 1.770(3) 1_555 3_454 y
    N O 2.7640(10)
                 1_555 3_454 y
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
    O C N 1_555 1_555 1_555 123.562(8) y
    C N N 1_555 1_555 2_555 119.388(9) y
    O C HC 1_555 1_555 1_555 123.60(10)
                                      y
    N C HC 1_555 1_555 1_555 112.90(10)
                                      y
    C N HN 1_555 1_555 1_555 123.1(2) y
    N N HN 2_555 1_555 1_555 117.5(2) y
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 HN O 1_555 1_555 3_454 1.033(3) 1.770(3) 2.7640(10)
                                                        160.4(3) y
