##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2021-10-12
_journal_date_accepted     2021-10-20
_journal_name_full     'IUCrData'
_journal_year     2021
_journal_volume     6
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314621010981
_journal_coeditor_code     BT4118
_publ_contact_author_name     'Ray J. Butcher'
_publ_contact_author_address
;
Department of Chemistry
Howard University
525 College Street NW
Washington DC 20059
USA
;
_publ_contact_author_email     'rbutcher99@yahoo.com'
_publ_contact_author_fax     '202-806-5442'
_publ_contact_author_phone     '703-585-6631'
_publ_section_title
;
Tetramethylammonium (Z)-N'-cyanocarbamimidate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Butcher, Ray J.' .
;
Department of Chemistry
Howard University
525 College Street NW
Washington DC 20059
USA
;
    'Purdy, Andrew P.' .
;
Chemistry Division, Code 6123
Naval Research Laboratory
4555 Overlook Av, SW
Washington DC 20375-5342
USA
;
_publ_section_synopsis
;
The structure of the tetramethylammonium salt of cyanourea is reported.
;
_chemical_name_systematic
;
Tetramethylammonium (Z)-N'-cyanocarbamimidate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H12 N +, C2 H2 N3 O -'
_chemical_formula_sum     'C6 H14 N4 O'
_chemical_formula_iupac     'C4 H12 N +, C2 H2 N3 O -'
_chemical_formula_weight     158.21
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.8120(4)
_cell_length_b     8.7561(4)
_cell_length_c     12.1093(6)
_cell_angle_alpha     90
_cell_angle_beta     110.897(2)
_cell_angle_gamma     90
_cell_volume     872.88(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3088
_cell_measurement_theta_min     2.94
_cell_measurement_theta_max     36.01
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.204
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     344
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(Sadabs; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.6510
_exptl_absorpt_correction_T_max     0.7471
_diffrn_ambient_temperature     100(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17548
_diffrn_reflns_av_R_equivalents     0.1560
_diffrn_reflns_av_unetI/netI     0.1280
_diffrn_reflns_theta_min     2.942
_diffrn_reflns_theta_max     36.432
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
 Refined as a 2-component twin.
The structure was solved using SHELXT (Sheldrick,
2015a) and refined with SHELXL2018 (Sheldrick, 2015b).
The locations of all hydrogen atoms for the major component were located in
difference Fourier maps and refined in idealized position using a riding model
with atomic displacement parameters of Uiso(H) = 1.2Ueq(C,
N) [1.5Ueq(C) for CH₃], with N---H distance of 0.88 Å and C---H
distances ranging from 0.95 to 0.99 Å, respectively.
;
_reflns_number_total     4340
_reflns_number_gt     2752
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1437
_refine_ls_R_factor_gt     0.0810
_refine_ls_wR_factor_gt     0.1487
_refine_ls_wR_factor_ref     0.1739
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     4340
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0640P)²+0.1366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.442
_refine_diff_density_min     -0.272
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick 2008)
;
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
    N N1 0.52001(13) 0.39529(14) 0.77065(11) 0.0155(2) Uani d 1 . .
    C C1 0.65132(18) 0.3158(2) 0.86761(18) 0.0271(3) Uani d 1 . .
    H H1A 0.717795 0.391510 0.923711 0.041 Uiso calc 1 . .
    H H1B 0.719731 0.257919 0.834033 0.041 Uiso calc 1 . .
    H H1C 0.602538 0.245780 0.908689 0.041 Uiso calc 1 . .
    C C2 0.4173(2) 0.2805(2) 0.68548(17) 0.0289(3) Uani d 1 . .
    H H2A 0.367659 0.211613 0.726730 0.043 Uiso calc 1 . .
    H H2B 0.484911 0.221365 0.651990 0.043 Uiso calc 1 . .
    H H2C 0.331794 0.333191 0.621804 0.043 Uiso calc 1 . .
    C C3 0.41712(17) 0.4843(2) 0.82257(14) 0.0215(3) Uani d 1 . .
    H H3A 0.484635 0.559198 0.878912 0.032 Uiso calc 1 . .
    H H3B 0.367829 0.414567 0.863515 0.032 Uiso calc 1 . .
    H H3C 0.331387 0.537379 0.759369 0.032 Uiso calc 1 . .
    C C4 0.5940(2) 0.5019(2) 0.70750(15) 0.0238(3) Uani d 1 . .
    H H4A 0.666165 0.573678 0.764306 0.036 Uiso calc 1 . .
    H H4B 0.507855 0.558664 0.647290 0.036 Uiso calc 1 . .
    H H4C 0.656586 0.443175 0.669525 0.036 Uiso calc 1 . .
    O O1 0.16653(13) 0.63130(14) 0.57913(9) 0.0193(2) Uani d 1 . .
    N N2 0.04603(16) 0.59992(17) 0.38199(11) 0.0232(3) Uani d 1 . .
    H H2D -0.024142 0.534851 0.391904 0.028 Uiso calc 1 . .
    H H2E 0.041806 0.623148 0.310245 0.028 Uiso calc 1 . .
    N N3 0.26105(14) 0.76503(15) 0.45058(11) 0.0172(2) Uani d 1 . .
    N N4 0.46972(16) 0.89392(18) 0.61890(12) 0.0230(3) Uani d 1 . .
    C C5 0.15986(15) 0.66395(15) 0.47658(12) 0.0139(2) Uani d 1 . .
    C C6 0.36986(15) 0.82986(16) 0.54310(12) 0.0150(2) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C2 . 1.492(2) ?
    N1 C3 . 1.4937(17) ?
    N1 C1 . 1.494(2) ?
    N1 C4 . 1.4958(19) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 H2A . 0.9800 ?
    C2 H2B . 0.9800 ?
    C2 H2C . 0.9800 ?
    C3 H3A . 0.9800 ?
    C3 H3B . 0.9800 ?
    C3 H3C . 0.9800 ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    O1 C5 . 1.2550(16) y
    N2 C5 . 1.3464(18) y
    N2 H2D . 0.8800 ?
    N2 H2E . 0.8800 ?
    N3 C6 . 1.3155(19) y
    N3 C5 . 1.3703(17) y
    N4 C6 . 1.1641(18) 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_3
    _geom_angle
    _geom_angle_publ_flag
    C2 N1 C3 . . 109.42(12) ?
    C2 N1 C1 . . 109.76(14) ?
    C3 N1 C1 . . 109.17(12) ?
    C2 N1 C4 . . 109.55(13) ?
    C3 N1 C4 . . 109.31(12) ?
    C1 N1 C4 . . 109.62(12) ?
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 H2A . . 109.5 ?
    N1 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    N1 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    N1 C3 H3A . . 109.5 ?
    N1 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    N1 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    N1 C4 H4A . . 109.5 ?
    N1 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    N1 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C5 N2 H2D . . 120.0 ?
    C5 N2 H2E . . 120.0 ?
    H2D N2 H2E . . 120.0 ?
    C6 N3 C5 . . 114.79(12) y
    O1 C5 N2 . . 120.31(12) y
    O1 C5 N3 . . 124.73(13) y
    N2 C5 N3 . . 114.95(12) y
    N4 C6 N3 . . 174.73(15) y
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
    C6 N3 C5 O1 . . . . -0.5(2) ?
    C6 N3 C5 N2 . . . . 178.60(13) ?
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
    C1 H1C O1 2_546 0.98 2.63 3.487(2) 146.7 yes
    C2 H2A O1 2_546 0.98 2.57 3.447(2) 148.5 yes
    C3 H3B O1 2_546 0.98 2.62 3.484(2) 146.8 yes
    C3 H3C O1 . 0.98 2.30 3.253(2) 163.9 yes
    C4 H4A N3 4_676 0.98 2.54 3.450(2) 155.1 yes
    C4 H4C N3 3_666 0.98 2.59 3.536(2) 161.7 yes
    N2 H2D O1 3_566 0.88 2.03 2.9084(16) 174.0 yes
    N2 H2E N4 4_575 0.88 2.18 3.0126(19) 158.1 yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
