#------------------------------------------------------------------------------
#$Date: 2023-06-06 08:30:10 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284367 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312079.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_2312079
loop_
_publ_author_name
'Domasevitch, Kostiantyn V.'
'Senchyk, Ganna A.'
'Lysenko, Andrey B.'
'Rusanov, Eduard B.'
_publ_section_title
;
 Gradual evolution of hydrogen-bonding patterns with the
 carbamoylcyanonitrosomethanide anion in a series of aliphatic diammonium
 salts.
;
_journal_coeditor_code           JX3077
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              177
_journal_page_last               185
_journal_paper_doi               10.1107/S2053229623002747
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C4 H14 N2 2+, 2C3 H2 N3 O2 -'
_chemical_formula_moiety         'C4 H14 N2 2+, 2(C3 H2 N3 O2 -)'
_chemical_formula_sum            'C10 H18 N8 O4'
_chemical_formula_weight         314.32
_chemical_name_common
;
Butane-1,4-diammonium bis(nitrosocarbamoylcyanomethanide)
;
_chemical_name_systematic
;
Butane-1,4-bis(aminium) bis(nitrosocarbamoylcyanomethanide)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.556(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4095(5)
_cell_length_b                   6.7848(3)
_cell_length_c                   14.8471(5)
_cell_measurement_reflns_used    14141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.219
_cell_measurement_theta_min      2.775
_cell_volume                     1478.61(10)
_computing_cell_refinement
;
SAINT-NT (Bruker, 1999)
;
_computing_data_collection
;
SMART-NT (Bruker, 1998)
;
_computing_data_reduction
;
SAINT-NT (Bruker, 1999)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14141
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.219
_diffrn_reflns_theta_min         2.775
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0832P)²+2.1745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                1463
_reflns_number_total             1816
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3077sup1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 2312077--2312080.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2312079
_cod_database_fobs_code          2312079
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.24644(10) 0.2413(2) 0.12285(10) 0.0336(4) Uani d 1 . .
O O2 0.15729(10) 0.2978(2) 0.37397(11) 0.0331(4) Uani d 1 . .
N N1 0.26504(11) 0.2326(2) 0.21751(12) 0.0267(4) Uani d 1 . .
N N2 0.03694(12) 0.3635(3) 0.10843(14) 0.0369(5) Uani d 1 . .
N N3 0.30566(12) 0.2324(3) 0.41567(14) 0.0327(4) Uani d 1 . .
C C1 0.19907(12) 0.2707(3) 0.24185(14) 0.0233(4) Uani d 1 . .
C C2 0.10856(13) 0.3224(3) 0.16912(14) 0.0258(4) Uani d 1 . .
C C3 0.21926(13) 0.2679(3) 0.34960(15) 0.0260(4) Uani d 1 . .
N N4 0.38707(11) 0.1879(3) 0.07040(13) 0.0279(4) Uani d 1 . .
C C4 0.44979(15) 0.3611(4) 0.10384(16) 0.0365(5) Uani d 1 . .
C C5 0.52132(15) 0.3459(4) 0.21378(17) 0.0387(5) Uani d 1 . .
H H1 0.3189(18) 0.231(4) 0.4773(18) 0.039(7) Uiso d 1 . .
H H2 0.3399(18) 0.210(4) 0.390(2) 0.042(7) Uiso d 1 . .
H H3 0.344(2) 0.188(4) 0.097(2) 0.044(7) Uiso d 1 . .
H H4 0.3537(16) 0.188(4) 0.004(2) 0.030(6) Uiso d 1 . .
H H5 0.4172(19) 0.065(5) 0.087(2) 0.047(7) Uiso d 1 . .
H H4A 0.4095(17) 0.485(3) 0.089(2) 0.047(7) Uiso d 1 . .
H H4B 0.4828(17) 0.362(4) 0.0571(18) 0.048(7) Uiso d 1 . .
H H5A 0.5592(18) 0.214(3) 0.227(2) 0.047(8) Uiso d 1 . .
H H5B 0.569(2) 0.463(4) 0.236(3) 0.080(11) Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C1 . . 117.74(16) n
C3 N3 H1 . . 118.4(19) n
C3 N3 H2 . . 115(2) n
H1 N3 H2 . . 127(3) n
N1 C1 C2 . . 123.02(17) n
N1 C1 C3 . . 118.77(17) n
C2 C1 C3 . . 118.17(16) n
N2 C2 C1 . . 177.8(2) n
O2 C3 N3 . . 123.71(19) n
O2 C3 C1 . . 119.78(17) n
N3 C3 C1 . . 116.52(17) n
C4 N4 H3 . . 112.9(17) n
C4 N4 H4 . . 111.0(16) n
H3 N4 H4 . . 105(2) n
C4 N4 H5 . . 113.9(17) n
H3 N4 H5 . . 107(2) n
H4 N4 H5 . . 106(2) n
N4 C4 C5 . . 112.84(18) n
N4 C4 H4A . . 106.9(15) n
C5 C4 H4A . . 113.0(15) n
N4 C4 H4B . . 105.3(16) n
C5 C4 H4B . . 109.1(15) n
H4A C4 H4B . . 109(2) n
C5 C5 C4 2_655 . 112.2(2) n
C5 C5 H5A 2_655 . 106.6(16) n
C4 C5 H5A . . 111.4(16) n
C5 C5 H5B 2_655 . 106.9(19) n
C4 C5 H5B . . 112.9(19) n
H5A C5 H5B . . 107(3) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.299(2) n
O2 C3 . 1.239(2) n
N1 C1 . 1.311(2) n
N2 C2 . 1.151(3) n
N3 C3 . 1.337(3) n
N3 H1 . 0.84(2) n
N3 H2 . 0.82(2) n
C1 C2 . 1.436(3) n
C1 C3 . 1.482(3) n
N4 C4 . 1.493(3) n
N4 H3 . 0.95(3) n
N4 H4 . 0.89(3) n
N4 H5 . 0.94(3) n
C4 C5 . 1.530(3) n
C4 H4A . 1.033(19) n
C4 H4B . 1.055(19) n
C5 C5 2_655 1.523(5) n
C5 H5A . 1.054(19) n
C5 H5B . 1.06(2) n
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
N4 H3 O1 . 0.95(3) 1.84(3) 2.770(2) 164(2) yes
N4 H4 O1 7_555 0.89(3) 1.92(3) 2.765(2) 156(2) yes
N4 H5 N2 3_545 0.94(3) 2.29(3) 3.157(3) 152(2) yes
N4 H5 O2 4_545 0.94(3) 2.40(3) 2.959(2) 118(2) yes
N3 H1 O2 7_556 0.84(2) 2.07(2) 2.910(2) 174(3) yes
C4 H4A O2 4_555 1.033(19) 2.55(2) 3.535(3) 158(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C1 C2 . . . . -0.5(3) n
O1 N1 C1 C3 . . . . -178.10(17) n
N1 C1 C3 O2 . . . . -177.87(18) n
C2 C1 C3 O2 . . . . 4.4(3) n
N1 C1 C3 N3 . . . . 2.2(3) n
C2 C1 C3 N3 . . . . -175.57(18) n
N4 C4 C5 C5 . . . 2_655 -63.72(19) n
