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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/49/7224981.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7224981
loop_
_publ_author_name
'Hornung, Julius'
'Hübner, Olaf'
'Kaifer, Elisabeth'
'Himmel, Hans-Jörg'
_publ_section_title
;
 Bent and twisted: the electronic structure of 2-azapropenylium ions
 obtained by guanidine oxidation
;
_journal_issue                   45
_journal_name_full               'RSC Adv.'
_journal_page_first              39323
_journal_paper_doi               10.1039/C6RA04494H
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C16 H28 N6'
_chemical_formula_weight         304.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-19 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                110.90(3)
_cell_angle_beta                 97.94(3)
_cell_angle_gamma                111.50(3)
_cell_formula_units_Z            1
_cell_length_a                   6.9120(14)
_cell_length_b                   8.3560(17)
_cell_length_c                   8.8440(18)
_cell_measurement_reflns_used    4364
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.59
_cell_volume                     422.2(2)
_computing_cell_refinement       'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_data_collection       'COLLECT (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4364
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.052
_diffrn_reflns_theta_min         2.592
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'box shaped'
_exptl_crystal_F_000             166
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0463
_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)+(0.0586P)²+0.1176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1800
_reflns_number_total             2451
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra04494h2.cif
_cod_data_source_block           juh004
_cod_original_cell_volume        422.20(19)
_cod_database_code               7224981
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.03046(16) 0.73351(15) 0.82948(13) 0.0166(2) Uani 1 1 d . .
N2 N 0.30490(17) 0.69239(15) 0.70448(14) 0.0182(2) Uani 1 1 d . .
N3 N 0.23876(17) 0.95681(15) 0.74915(13) 0.0166(2) Uani 1 1 d . .
C1 C 0.02129(19) 0.61423(17) 0.91039(15) 0.0150(3) Uani 1 1 d . .
C2 C -0.18281(19) 0.47351(17) 0.88918(16) 0.0166(3) Uani 1 1 d . .
H2 H -0.3072 0.4547 0.8151 0.020 Uiso 1 1 calc R U
C3 C -0.20455(19) 0.36123(17) 0.97567(15) 0.0167(3) Uani 1 1 d . .
H3 H -0.3425 0.2684 0.9579 0.020 Uiso 1 1 calc R U
C4 C 0.18599(19) 0.78825(17) 0.76511(15) 0.0153(2) Uani 1 1 d . .
C5 C 0.5354(2) 0.7895(2) 0.72245(19) 0.0243(3) Uani 1 1 d . .
H5A H 0.5528 0.7688 0.6122 0.036 Uiso 1 1 calc R U
H5B H 0.6146 0.7394 0.7743 0.036 Uiso 1 1 calc R U
H5C H 0.5911 0.9245 0.7926 0.036 Uiso 1 1 calc R U
C6 C 0.2136(2) 0.48607(18) 0.63928(17) 0.0224(3) Uani 1 1 d . .
H6A H 0.2779 0.4548 0.7211 0.034 Uiso 1 1 calc R U
H6B H 0.2440 0.4338 0.5348 0.034 Uiso 1 1 calc R U
H6C H 0.0583 0.4328 0.6186 0.034 Uiso 1 1 calc R U
C7 C 0.2839(2) 0.97043(19) 0.59715(17) 0.0214(3) Uani 1 1 d . .
H7A H 0.3027 0.8612 0.5304 0.032 Uiso 1 1 calc R U
H7B H 0.4150 1.0856 0.6295 0.032 Uiso 1 1 calc R U
H7C H 0.1638 0.9735 0.5313 0.032 Uiso 1 1 calc R U
C8 C 0.1478(2) 1.08303(19) 0.83326(17) 0.0206(3) Uani 1 1 d . .
H8A H 0.0044 1.0415 0.7615 0.031 Uiso 1 1 calc R U
H8B H 0.2406 1.2118 0.8545 0.031 Uiso 1 1 calc R U
H8C H 0.1383 1.0790 0.9392 0.031 Uiso 1 1 calc R U
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 C1 121.63(11) . .
C4 N2 C6 121.04(11) . .
C4 N2 C5 123.22(11) . .
C6 N2 C5 115.21(11) . .
C4 N3 C7 121.18(11) . .
C4 N3 C8 118.60(10) . .
C7 N3 C8 113.50(10) . .
C2 C1 C3 117.22(11) . 2_567
C2 C1 N1 118.98(11) . .
C3 C1 N1 123.56(11) 2_567 .
C3 C2 C1 121.81(11) . .
C3 C2 H2 119.1 . .
C1 C2 H2 119.1 . .
C2 C3 C1 120.97(11) . 2_567
C2 C3 H3 119.5 . .
C1 C3 H3 119.5 2_567 .
N1 C4 N2 126.69(11) . .
N1 C4 N3 118.59(11) . .
N2 C4 N3 114.69(11) . .
N2 C5 H5A 109.5 . .
N2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N3 C7 H7A 109.5 . .
N3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N3 C8 H8A 109.5 . .
N3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.2975(16) .
N1 C1 1.4087(15) .
N2 C4 1.3794(16) .
N2 C6 1.4476(17) .
N2 C5 1.4535(17) .
N3 C4 1.3843(16) .
N3 C7 1.4549(16) .
N3 C8 1.4550(16) .
C1 C2 1.4006(17) .
C1 C3 1.4040(18) 2_567
C2 C3 1.3886(17) .
C2 H2 0.9300 .
C3 C1 1.4040(18) 2_567
C3 H3 0.9300 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 N1 C1 C2 -142.75(12) . .
C4 N1 C1 C3 43.10(18) . 2_567
C3 C1 C2 C3 -0.5(2) 2_567 .
N1 C1 C2 C3 -175.00(11) . .
C1 C2 C3 C1 0.5(2) . 2_567
C1 N1 C4 N2 27.10(19) . .
C1 N1 C4 N3 -154.84(11) . .
C6 N2 C4 N1 26.74(19) . .
C5 N2 C4 N1 -144.50(13) . .
C6 N2 C4 N3 -151.38(11) . .
C5 N2 C4 N3 37.38(16) . .
C7 N3 C4 N1 -138.06(13) . .
C8 N3 C4 N1 11.35(17) . .
C7 N3 C4 N2 40.22(16) . .
C8 N3 C4 N2 -170.37(10) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 69612423
