#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151647.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_7151647
loop_
_publ_author_name
'Čížková, Martina'
'Kolivoška, Viliam'
'Císařová, Ivana'
'Šaman, David'
'Pospíšil, Lubomír'
'Teplý, Filip'
_publ_section_title
;
 Nitrogen heteroaromatic cations by [2+2+2] cycloaddition.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              450
_journal_page_last               462
_journal_paper_doi               10.1039/C0OB00507J
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C12 H8 N2'
_chemical_formula_sum            'C12 H8 N2'
_chemical_formula_weight         180.20
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.3925(2)
_cell_length_b                   6.2169(4)
_cell_length_c                   13.0456(8)
_cell_measurement_reflns_used    2189
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.
_cell_measurement_theta_min      1
_cell_volume                     1897.21(17)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25711
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.2683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                2484
_reflns_number_total             3505
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            C0OB00507J.TXT
_cod_data_source_block           mc253-1-teply-uochb
_cod_database_code               7151647
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.37632(11) 1.0994(4) 0.1352(2) 0.0352(6) Uani 1 1 d . . .
N12 N 0.36248(11) 1.3064(4) 0.1286(2) 0.0431(6) Uani 1 1 d . . .
C13 C 0.40073(14) 1.4338(5) 0.0818(2) 0.0502(8) Uani 1 1 d . . .
H13 H 0.3927 1.5831 0.0760 0.060 Uiso 1 1 calc R . .
C14 C 0.45090(13) 1.3563(5) 0.0422(2) 0.0477(8) Uani 1 1 d . . .
H14 H 0.4779 1.4487 0.0101 0.057 Uiso 1 1 calc R . .
C15 C 0.46036(13) 1.1413(5) 0.0507(2) 0.0480(8) Uani 1 1 d . . .
H15 H 0.4945 1.0830 0.0226 0.058 Uiso 1 1 calc R . .
N16 N 0.42339(10) 1.0081(4) 0.09724(19) 0.0453(6) Uani 1 1 d . . .
C17 C 0.33692(12) 0.9620(4) 0.1884(2) 0.0379(6) Uani 1 1 d . . .
C18 C 0.30390(13) 0.8480(4) 0.2338(2) 0.0389(7) Uani 1 1 d . . .
C19 C 0.26379(13) 0.7155(4) 0.2873(2) 0.0345(6) Uani 1 1 d . . .
C21 C 0.36871(11) -0.0296(4) 0.4834(2) 0.0361(6) Uani 1 1 d . . .
N22 N 0.37958(11) -0.2398(3) 0.4826(2) 0.0419(6) Uani 1 1 d . . .
C23 C 0.33949(13) -0.3643(5) 0.5269(2) 0.0467(8) Uani 1 1 d . . .
H23 H 0.3450 -0.5156 0.5279 0.056 Uiso 1 1 calc R . .
C24 C 0.29111(13) -0.2808(5) 0.5704(3) 0.0450(8) Uani 1 1 d . . .
H24 H 0.2631 -0.3708 0.6011 0.054 Uiso 1 1 calc R . .
C25 C 0.28480(13) -0.0624(5) 0.5678(2) 0.0465(7) Uani 1 1 d . . .
H25 H 0.2516 -0.0010 0.5978 0.056 Uiso 1 1 calc R . .
N26 N 0.32324(10) 0.0686(4) 0.52512(19) 0.0436(6) Uani 1 1 d . . .
C27 C 0.40932(12) 0.1062(4) 0.4323(2) 0.0404(7) Uani 1 1 d . . .
C28 C 0.44286(12) 0.2172(4) 0.3864(2) 0.0388(7) Uani 1 1 d . . .
C29 C 0.48380(12) 0.3397(4) 0.3291(2) 0.0365(7) Uani 1 1 d . . .
C110 C 0.27851(13) 0.5047(4) 0.3158(2) 0.0413(7) Uani 1 1 d . . .
H110 H 0.3155 0.4506 0.3003 0.050 Uiso 1 1 calc R . .
C111 C 0.23969(13) 0.3761(4) 0.3659(2) 0.0440(7) Uani 1 1 d . . .
H111 H 0.2500 0.2336 0.3846 0.053 Uiso 1 1 calc R . .
C112 C 0.18575(14) 0.4527(5) 0.3893(2) 0.0477(8) Uani 1 1 d . . .
H112 H 0.1592 0.3641 0.4248 0.057 Uiso 1 1 calc R . .
C113 C 0.17062(13) 0.6596(5) 0.3605(3) 0.0502(8) Uani 1 1 d . . .
H113 H 0.1335 0.7129 0.3760 0.060 Uiso 1 1 calc R . .
C114 C 0.20920(12) 0.7878(4) 0.3098(3) 0.0405(7) Uani 1 1 d . . .
H114 H 0.1982 0.9288 0.2897 0.049 Uiso 1 1 calc R . .
C210 C 0.47130(12) 0.5488(4) 0.2977(2) 0.0419(7) Uani 1 1 d . . .
H210 H 0.4358 0.6127 0.3156 0.050 Uiso 1 1 calc R . .
C211 C 0.51078(14) 0.6630(5) 0.2405(2) 0.0460(7) Uani 1 1 d . . .
H211 H 0.5021 0.8050 0.2187 0.055 Uiso 1 1 calc R . .
C212 C 0.56225(14) 0.5730(5) 0.2152(2) 0.0503(8) Uani 1 1 d . . .
H212 H 0.5890 0.6523 0.1754 0.060 Uiso 1 1 calc R . .
C213 C 0.57553(13) 0.3665(5) 0.2474(3) 0.0498(8) Uani 1 1 d . . .
H213 H 0.6115 0.3049 0.2306 0.060 Uiso 1 1 calc R . .
C214 C 0.53661(13) 0.2511(4) 0.3037(3) 0.0415(7) Uani 1 1 d . . .
H214 H 0.5458 0.1096 0.3256 0.050 Uiso 1 1 calc R . .
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
_geom_angle_publ_flag
N12 C11 N16 126.1(3) . . ?
N12 C11 C17 116.8(2) . . ?
N16 C11 C17 117.1(2) . . ?
C11 N12 C13 116.0(3) . . ?
N12 C13 C14 122.4(3) . . ?
N12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 117.0(3) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 H14 121.5 . . ?
N16 C15 C14 122.6(3) . . ?
N16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C11 N16 C15 115.9(2) . . ?
C18 C17 C11 179.4(3) . . ?
C17 C18 C19 178.9(3) . . ?
C114 C19 C110 118.2(3) . . ?
C114 C19 C18 121.4(3) . . ?
C110 C19 C18 120.4(3) . . ?
N22 C21 N26 127.0(2) . . ?
N22 C21 C27 116.6(3) . . ?
N26 C21 C27 116.5(2) . . ?
C21 N22 C23 115.3(3) . . ?
N22 C23 C24 122.4(3) . . ?
N22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C25 C24 C23 117.1(3) . . ?
C25 C24 H24 121.4 . . ?
C23 C24 H24 121.4 . . ?
N26 C25 C24 122.9(3) . . ?
N26 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
C25 N26 C21 115.2(2) . . ?
C28 C27 C21 177.8(3) . . ?
C27 C28 C29 177.1(3) . . ?
C214 C29 C210 119.0(3) . . ?
C214 C29 C28 120.4(2) . . ?
C210 C29 C28 120.5(3) . . ?
C111 C110 C19 120.4(3) . . ?
C111 C110 H110 119.8 . . ?
C19 C110 H110 119.8 . . ?
C110 C111 C112 120.5(3) . . ?
C110 C111 H111 119.8 . . ?
C112 C111 H111 119.8 . . ?
C111 C112 C113 119.5(3) . . ?
C111 C112 H112 120.2 . . ?
C113 C112 H112 120.2 . . ?
C114 C113 C112 120.1(3) . . ?
C114 C113 H113 120.0 . . ?
C112 C113 H113 120.0 . . ?
C113 C114 C19 121.3(3) . . ?
C113 C114 H114 119.4 . . ?
C19 C114 H114 119.4 . . ?
C211 C210 C29 119.8(3) . . ?
C211 C210 H210 120.1 . . ?
C29 C210 H210 120.1 . . ?
C212 C211 C210 120.5(3) . . ?
C212 C211 H211 119.7 . . ?
C210 C211 H211 119.7 . . ?
C211 C212 C213 120.2(3) . . ?
C211 C212 H212 119.9 . . ?
C213 C212 H212 119.9 . . ?
C214 C213 C212 119.8(3) . . ?
C214 C213 H213 120.1 . . ?
C212 C213 H213 120.1 . . ?
C213 C214 C29 120.6(3) . . ?
C213 C214 H214 119.7 . . ?
C29 C214 H214 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 N12 1.330(3) . ?
C11 N16 1.334(3) . ?
C11 C17 1.436(4) . ?
N12 C13 1.342(4) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.360(4) . ?
C14 H14 0.9500 . ?
C15 N16 1.343(4) . ?
C15 H15 0.9500 . ?
C17 C18 1.204(4) . ?
C18 C19 1.430(4) . ?
C19 C114 1.385(4) . ?
C19 C110 1.405(4) . ?
C21 N22 1.331(3) . ?
C21 N26 1.342(3) . ?
C21 C27 1.435(4) . ?
N22 C23 1.346(4) . ?
C23 C24 1.369(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.366(4) . ?
C24 H24 0.9500 . ?
C25 N26 1.335(4) . ?
C25 H25 0.9500 . ?
C27 C28 1.204(4) . ?
C28 C29 1.434(4) . ?
C29 C214 1.392(4) . ?
C29 C210 1.394(4) . ?
C110 C111 1.375(4) . ?
C110 H110 0.9500 . ?
C111 C112 1.383(4) . ?
C111 H111 0.9500 . ?
C112 C113 1.386(4) . ?
C112 H112 0.9500 . ?
C113 C114 1.374(4) . ?
C113 H113 0.9500 . ?
C114 H114 0.9500 . ?
C210 C211 1.383(4) . ?
C210 H210 0.9500 . ?
C211 C212 1.368(5) . ?
C211 H211 0.9500 . ?
C212 C213 1.386(4) . ?
C212 H212 0.9500 . ?
C213 C214 1.372(4) . ?
C213 H213 0.9500 . ?
C214 H214 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190560
