#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:43:12 +0300 (Sat, 06 May 2023) $
#$Revision: 283572 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022700.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_2022700
loop_
_publ_author_name
'Aristov, Michael M.'
'Geng, Han'
'Harris, James W.'
'Berry, John F.'
_publ_section_title
;
 Clarifying the structures of imidines: using crystallographic
 characterization to identify tautomers and localized systems of
 π-bonding.
;
_journal_coeditor_code           EP3031
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              133
_journal_page_last               141
_journal_paper_doi               10.1107/S2053229623002036
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C4 H8 N3 +, Cl -, C4 H7 N3, H2 O'
_chemical_formula_moiety         'C4 H8 N3 +, Cl -, C4 H7 N3, H2 O'
_chemical_formula_sum            'C8 H17 Cl N6 O'
_chemical_formula_weight         248.72
_chemical_name_systematic
;
5-Amino-3,4-dihydro-2H-pyrrol-2-iminium chloride;
2-imino-3,4-dihydro-2H-pyrrol-5-amine monohydrate
;
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.570(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.294(3)
_cell_length_b                   9.4173(8)
_cell_length_c                   13.7430(12)
_cell_measurement_reflns_used    3499
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      72.641
_cell_measurement_theta_min      5.283
_cell_volume                     2367.1(5)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       '0.5\ ω and 0.5\ φ scans'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19987
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         73.376
_diffrn_reflns_theta_min         4.836
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.28
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.809
_exptl_absorpt_correction_T_max  0.9465
_exptl_absorpt_correction_T_min  0.8524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0435
_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)+(0.0607P)²+3.8293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1934
_reflns_number_total             2322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ep3031sup1.cif
_cod_data_source_block           1HCl
_cod_depositor_comments
'Adding full bibliography for 2022700--2022704.cif.'
_cod_original_cell_volume        2367.0(5)
_cod_database_code               2022700
_cod_database_fobs_code          2022700
_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   0.786
_shelx_estimated_absorpt_t_max   0.896
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
Cl Cl1 0.37230(3) 0.13946(5) 0.64679(4) 0.02616(18) Uani d 1 . .
O O1 0.52636(10) 0.20000(19) 0.62586(13) 0.0323(4) Uani d 1 . .
H H1C 0.554123 0.178738 0.687537 0.048 Uiso d 1 . .
H H1D 0.482073 0.195192 0.628768 0.048 Uiso d 1 . .
N N1 0.89152(10) -0.01953(19) 0.63459(14) 0.0213(4) Uani d 1 . .
H H1A 0.933610 0.020351 0.638718 0.026 Uiso calc 1 . .
H H1B 0.887512 -0.112645 0.633330 0.026 Uiso calc 1 . .
N N2 0.83658(9) 0.20054(18) 0.63183(13) 0.0177(4) Uani d 1 . .
N N3 0.74838(10) 0.3797(2) 0.62504(15) 0.0209(4) Uani d 1 . .
H H3 0.7811(15) 0.432(3) 0.6270(19) 0.025 Uiso d 1 . .
C C1 0.83466(11) 0.0600(2) 0.63030(16) 0.0181(4) Uani d 1 . .
C C2 0.76165(11) -0.0043(2) 0.62353(17) 0.0216(5) Uani d 1 . .
H H2A 0.765060 -0.063498 0.684413 0.026 Uiso calc 1 . .
H H2B 0.742135 -0.062511 0.560730 0.026 Uiso calc 1 . .
C C3 0.71463(12) 0.1278(2) 0.61988(18) 0.0227(5) Uani d 1 . .
H H3A 0.672930 0.131175 0.555355 0.027 Uiso calc 1 . .
H H3B 0.695671 0.129967 0.678861 0.027 Uiso calc 1 . .
C C4 0.76720(11) 0.2500(2) 0.62531(16) 0.0186(4) Uani d 1 . .
N N4 0.60620(10) 0.45993(19) 0.61180(14) 0.0203(4) Uani d 1 . .
H H4A 0.574901 0.392743 0.613477 0.024 Uiso calc 1 . .
H H4B 0.649751 0.437282 0.608902 0.024 Uiso calc 1 . .
N N5 0.52247(9) 0.63443(18) 0.61803(14) 0.0187(4) Uani d 1 . .
N N6 0.46620(10) 0.84956(19) 0.62318(14) 0.0212(4) Uani d 1 . .
H H6A 0.426125 0.805334 0.623645 0.025 Uiso calc 1 . .
H H6B 0.467938 0.942936 0.624638 0.025 Uiso calc 1 . .
C C5 0.58819(11) 0.5920(2) 0.61361(16) 0.0180(4) Uani d 1 . .
C C6 0.63821(12) 0.7130(2) 0.60916(17) 0.0211(5) Uani d 1 . .
H H6C 0.648152 0.714642 0.542801 0.025 Uiso calc 1 . .
H H6D 0.685130 0.707256 0.665851 0.025 Uiso calc 1 . .
C C7 0.59372(12) 0.8428(2) 0.62085(17) 0.0218(5) Uani d 1 . .
H H7A 0.617624 0.893340 0.686113 0.026 Uiso calc 1 . .
H H7B 0.586458 0.909687 0.562868 0.026 Uiso calc 1 . .
C C8 0.52279(11) 0.7770(2) 0.62033(16) 0.0181(4) Uani 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1C O1 H1D . . 104.6 ?
H1A N1 H1B . . 120.0 ?
C1 N1 H1A . . 120.0 ?
C1 N1 H1B . . 120.0 ?
C1 N2 C4 . . 108.14(17) ?
C4 N3 H3 . . 112(2) ?
N1 C1 N2 . . 123.37(19) ?
N1 C1 C2 . . 121.61(19) ?
N2 C1 C2 . . 115.02(18) ?
C1 C2 H2A . . 111.4 ?
C1 C2 H2B . . 111.4 ?
C1 C2 C3 . . 102.00(17) ?
H2A C2 H2B . . 109.2 ?
C3 C2 H2A . . 111.4 ?
C3 C2 H2B . . 111.4 ?
C2 C3 H3A . . 111.1 ?
C2 C3 H3B . . 111.1 ?
H3A C3 H3B . . 109.0 ?
C4 C3 C2 . . 103.54(17) ?
C4 C3 H3A . . 111.1 ?
C4 C3 H3B . . 111.1 ?
N2 C4 C3 . . 111.29(18) ?
N3 C4 N2 . . 125.99(19) ?
N3 C4 C3 . . 122.71(19) ?
H4A N4 H4B . . 120.0 ?
C5 N4 H4A . . 120.0 ?
C5 N4 H4B . . 120.0 ?
C8 N5 C5 . . 107.43(18) ?
H6A N6 H6B . . 120.0 ?
C8 N6 H6A . . 120.0 ?
C8 N6 H6B . . 120.0 ?
N4 C5 N5 . . 123.19(19) ?
N4 C5 C6 . . 123.14(19) ?
N5 C5 C6 . . 113.67(19) ?
C5 C6 H6C . . 111.3 ?
C5 C6 H6D . . 111.3 ?
C5 C6 C7 . . 102.22(17) ?
H6C C6 H6D . . 109.2 ?
C7 C6 H6C . . 111.3 ?
C7 C6 H6D . . 111.3 ?
C6 C7 H7A . . 111.3 ?
C6 C7 H7B . . 111.3 ?
H7A C7 H7B . . 109.2 ?
C8 C7 C6 . . 102.16(17) ?
C8 C7 H7A . . 111.3 ?
C8 C7 H7B . . 111.3 ?
N5 C8 C7 . . 114.24(19) ?
N6 C8 N5 . . 121.94(19) ?
N6 C8 C7 . . 123.82(19) ?
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 H1C . 0.8697 ?
O1 H1D . 0.8693 ?
N1 H1A . 0.8800 ?
N1 H1B . 0.8800 ?
N1 C1 . 1.314(3) ?
N2 C1 . 1.324(3) ?
N2 C4 . 1.393(3) ?
N3 H3 . 0.79(3) ?
N3 C4 . 1.274(3) ?
C1 C2 . 1.508(3) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.531(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C3 C4 . 1.520(3) ?
N4 H4A . 0.8800 ?
N4 H4B . 0.8800 ?
N4 C5 . 1.294(3) ?
N5 C5 . 1.349(3) ?
N5 C8 . 1.343(3) ?
N6 H6A . 0.8800 ?
N6 H6B . 0.8800 ?
N6 C8 . 1.299(3) ?
C5 C6 . 1.507(3) ?
C6 H6C . 0.9900 ?
C6 H6D . 0.9900 ?
C6 C7 . 1.531(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C7 C8 . 1.500(3) ?
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
N1 H1A N5 3_545 0.88 2.12 2.984(3) 167.9 yes
N1 H1B Cl1 3_545 0.88 2.37 3.2432(18) 173.4 yes
N3 H3 Cl1 3 0.79(3) 2.59(3) 3.367(2) 168(3) yes
N4 H4A O1 . 0.88 2.07 2.931(3) 164.3 yes
N4 H4B N3 . 0.88 1.92 2.795(3) 170.9 yes
N6 H6A N2 3_455 0.88 2.02 2.903(3) 177.2 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
N1 C1 C2 C3 . . . . -179.69(19) ?
N2 C1 C2 C3 . . . . 0.5(2) ?
C1 N2 C4 N3 . . . . 179.7(2) ?
C1 N2 C4 C3 . . . . 0.6(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C2 C3 C4 N2 . . . . -0.2(2) ?
C2 C3 C4 N3 . . . . -179.4(2) ?
C4 N2 C1 N1 . . . . 179.5(2) ?
C4 N2 C1 C2 . . . . -0.7(3) ?
N4 C5 C6 C7 . . . . -176.4(2) ?
N5 C5 C6 C7 . . . . 4.6(2) ?
C5 N5 C8 N6 . . . . 179.0(2) ?
C5 N5 C8 C7 . . . . -1.9(2) ?
C5 C6 C7 C8 . . . . -5.0(2) ?
C6 C7 C8 N5 . . . . 4.6(2) ?
C6 C7 C8 N6 . . . . -176.2(2) ?
C8 N5 C5 N4 . . . . 179.1(2) ?
C8 N5 C5 C6 . . . . -1.9(2) ?
