#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:43:12 +0300 (Sat, 06 May 2023) $
#$Revision: 283572 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022701.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_2022701
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 H7 N3'
_chemical_formula_moiety         'C4 H7 N3'
_chemical_formula_sum            'C4 H7 N3'
_chemical_formula_weight         97.13
_chemical_name_systematic
;
2-Imino-3,4-dihydro-2H-pyrrol-5-amine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_cell_angle_alpha                101.641(4)
_cell_angle_beta                 104.225(6)
_cell_angle_gamma                111.425(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9577(4)
_cell_length_b                   6.7494(5)
_cell_length_c                   6.8249(5)
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    100.02
_cell_measurement_theta_max      72.207
_cell_measurement_theta_min      7.073
_cell_volume                     234.36(3)
_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
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       '0.60\ ω and 0.6\ 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  0.0191
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3673
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.200
_diffrn_reflns_theta_min         7.073
_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    0.754
_exptl_absorpt_correction_T_max  0.9009
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             104
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0342
_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)+(0.0588P)²+0.0676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                833
_reflns_number_total             892
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ep3031sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2022700--2022704.cif.'
_cod_database_code               2022701
_cod_database_fobs_code          2022701
_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   0.920
_shelx_estimated_absorpt_t_max   0.928
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.48601(19) 0.24030(16) 0.74167(16) 0.0172(3) Uani d 1 . .
N N2 0.68866(18) 0.34098(16) 0.50208(16) 0.0139(3) Uani d 1 . .
N N3 0.7801(2) 0.38375(17) 0.19741(18) 0.0162(3) Uani d 1 . .
C C1 0.4720(2) 0.23523(18) 0.55105(19) 0.0139(3) Uani d 1 . .
C C2 0.2300(2) 0.11734(19) 0.35125(19) 0.0149(3) Uani d 1 . .
H H2A 0.1018 0.1747 0.3654 0.018 Uiso calc 1 . .
H H2B 0.1508 -0.0473 0.3228 0.018 Uiso calc 1 . .
C C3 0.3297(2) 0.17603(19) 0.17466(19) 0.0151(3) Uani d 1 . .
H H3C 0.2900 0.0390 0.0601 0.018 Uiso calc 1 . .
H H3D 0.2563 0.2685 0.1118 0.018 Uiso calc 1 . .
C C4 0.6171(2) 0.30852(18) 0.29488(19) 0.0134(3) Uani d 1 . .
H H3A 0.946(3) 0.471(3) 0.274(3) 0.022(4) Uiso d 1 . .
H H1 0.329(4) 0.168(3) 0.741(3) 0.032(4) Uiso d 1 . .
H H3B 0.723(3) 0.362(3) 0.061(3) 0.025(4) 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 0.0181 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'
N N 0.0311 0.0180 '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
C1 N1 H1 . . 108.4(12) ?
C4 N2 C1 . . 108.59(10) ?
C4 N3 H3A . . 119.6(11) ?
C4 N3 H3B . . 119.8(11) ?
H3A N3 H3B . . 120.1(15) ?
N1 C1 N2 . . 121.78(11) ?
N1 C1 C2 . . 127.03(10) ?
N2 C1 C2 . . 111.20(10) ?
C1 C2 H2A . . 111.1 ?
C1 C2 H2B . . 111.1 ?
C1 C2 C3 . . 103.42(9) ?
H2A C2 H2B . . 109.0 ?
C3 C2 H2A . . 111.1 ?
C3 C2 H2B . . 111.1 ?
C2 C3 H3C . . 111.4 ?
C2 C3 H3D . . 111.4 ?
H3C C3 H3D . . 109.2 ?
C4 C3 C2 . . 101.95(9) ?
C4 C3 H3C . . 111.4 ?
C4 C3 H3D . . 111.4 ?
N2 C4 C3 . . 114.74(10) ?
N3 C4 N2 . . 123.35(11) ?
N3 C4 C3 . . 121.91(11) ?
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 C1 . 1.2756(15) ?
N1 H1 . 0.88(2) ?
N2 C1 . 1.3865(15) ?
N2 C4 . 1.3191(16) ?
N3 C4 . 1.3177(16) ?
N3 H3A . 0.890(18) ?
N3 H3B . 0.868(19) ?
C1 C2 . 1.5260(16) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.5279(16) ?
C3 H3C . 0.9900 ?
C3 H3D . 0.9900 ?
C3 C4 . 1.5164(16) ?
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
N3 H3A N2 2_766 0.890(18) 2.061(18) 2.9414(15) 169.6(15)
N3 H3B N1 1_554 0.868(19) 2.083(19) 2.9238(16) 162.6(15)
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 . . . . 178.09(11) ?
N2 C1 C2 C3 . . . . -2.51(12) ?
C1 N2 C4 N3 . . . . -178.30(10) ?
C1 N2 C4 C3 . . . . 1.57(13) ?
C1 C2 C3 C4 . . . . 3.04(11) ?
C2 C3 C4 N2 . . . . -3.05(13) ?
C2 C3 C4 N3 . . . . 176.82(10) ?
C4 N2 C1 N1 . . . . -179.87(10) ?
C4 N2 C1 C2 . . . . 0.68(13) ?
