#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567033.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_1567033
loop_
_publ_author_name
'Molčanov, Krešimir'
'Milašinović, Valentina'
'Kojić-Prodić, Biserka'
'Maltar-Strmečki, Nadica'
'You, Jiangyang'
'Šantić, Ana'
'Kanižaj, Lidija'
'Stilinović, Vladimir'
'Fotović, Luka'
_publ_section_title
;
 Semiconductive 2D arrays of pancake-bonded oligomers of partially charged
 TCNQ radicals
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252522004717
_journal_volume                  9
_journal_year                    2022
_chemical_formula_moiety         'C12 H4 N4, 0.5(C6 H10 N2)'
_chemical_formula_sum            'C15 H9 N5'
_chemical_formula_weight         259.27
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-10-02T13:25:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                73.628(5)
_cell_angle_beta                 89.550(5)
_cell_angle_gamma                67.258(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0634(4)
_cell_length_b                   7.8154(5)
_cell_length_c                   13.4680(8)
_cell_measurement_reflns_used    3009
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.922
_cell_measurement_theta_min      3.418
_cell_volume                     653.56(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4851
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.211
_diffrn_reflns_theta_min         3.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.65779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1254P)²+0.1608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                2343
_reflns_number_total             2657
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_4pic_100k
_cod_original_cell_volume        653.56(7)
_cod_database_code               1567033
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_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
_atom_site_type_symbol
N1 0.5875(3) 0.5127(2) 0.37441(11) 0.0395(4) Uani d 1 . . N
N2 0.1206(2) 1.4828(2) -0.14850(11) 0.0331(4) Uani d 1 . . N
N3 0.4212(2) 0.1646(2) 0.21465(11) 0.0349(4) Uani d 1 . . N
N4 0.0032(3) 1.1402(3) -0.32539(11) 0.0425(4) Uani d 1 . . N
C1 0.5139(3) 0.5043(2) 0.30076(12) 0.0292(4) Uani d 1 . . C
C2 0.4234(2) 0.4965(2) 0.20843(12) 0.0262(3) Uani d 1 . . C
C3 0.3462(2) 0.6587(2) 0.12084(11) 0.0246(3) Uani d 1 . . C
C4 0.3452(2) 0.8424(2) 0.12179(12) 0.0252(3) Uani d 1 . . C
H4 0.393733 0.853543 0.182661 0.03 Uiso calc 1 . . H
C5 0.2748(2) 0.9997(2) 0.03582(11) 0.0245(3) Uani d 1 . . C
H5 0.275637 1.116913 0.038767 0.029 Uiso calc 1 . . H
C6 0.1987(2) 0.9887(2) -0.06039(11) 0.0242(3) Uani d 1 . . C
C7 0.1296(2) 1.1502(2) -0.14854(11) 0.0257(3) Uani d 1 . . C
C8 0.1256(2) 1.3341(2) -0.14850(11) 0.0265(4) Uani d 1 . . C
C9 0.4225(2) 0.3132(2) 0.21160(11) 0.0278(4) Uani d 1 . . C
C10 0.2671(2) 0.6486(2) 0.02525(11) 0.0252(3) Uani d 1 . . C
H10 0.262962 0.532379 0.022762 0.03 Uiso calc 1 . . H
C11 0.1987(2) 0.8055(2) -0.06095(12) 0.0252(3) Uani d 1 . . C
H11 0.15058 0.794224 -0.121878 0.03 Uiso calc 1 . . H
C12 0.0600(3) 1.1431(2) -0.24636(12) 0.0297(4) Uani d 1 . . C
N5 0.7039(2) -0.1076(2) 0.54078(10) 0.0317(4) Uani d 0.5 . . N
N6 0.9238(3) -0.2242(3) 0.58524(14) 0.0481(5) Uani d 0.5 . . N
C13 0.4006(3) 0.1840(2) 0.50635(12) 0.0337(4) Uani d 1 . . C
H13 0.333425 0.309354 0.511202 0.04 Uiso calc 1 . . H
C14 0.6038(3) 0.0773(3) 0.54656(12) 0.0339(4) Uani d 1 . . C
H14 0.673824 0.131092 0.577962 0.041 Uiso calc 1 . . H
C15 0.7039(2) -0.1076(2) 0.54078(10) 0.0317(4) Uani d 0.5 . . C
C16 0.9238(3) -0.2242(3) 0.58524(14) 0.0481(5) Uani d 0.5 . . C
H16A 0.940(5) -0.365(3) 0.615(2) 0.072 Uiso d 1 . . H
H16C 1.012(4) -0.247(4) 0.5306(18) 0.072 Uiso d 1 . . H
H16B 0.967(5) -0.207(4) 0.6485(17) 0.072 Uiso d 1 . . H
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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
N1 C1 C2 179.07(17) . . ?
C3 C2 C9 122.85(13) . . ?
C3 C2 C1 121.08(13) . . ?
C9 C2 C1 116.05(13) . . ?
C2 C3 C4 121.08(13) . . ?
C2 C3 C10 121.40(14) . . ?
C4 C3 C10 117.52(13) . . ?
C5 C4 C3 121.30(13) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.16(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C11 121.86(13) . . ?
C7 C6 C5 120.70(13) . . ?
C11 C6 C5 117.43(13) . . ?
C6 C7 C8 122.39(13) . . ?
C6 C7 C12 122.33(14) . . ?
C8 C7 C12 115.27(13) . . ?
N2 C8 C7 179.38(17) . . ?
N3 C9 C2 179.62(17) . . ?
C11 C10 C3 121.11(13) . . ?
C11 C10 H10 119.4 . . ?
C3 C10 H10 119.4 . . ?
C10 C11 C6 121.47(13) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
N4 C12 C7 179.01(17) . . ?
N5 C13 C14 120.48(16) 2_656 . ?
N5 C13 H13 119.8 2_656 . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.41(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C15 C14 119.11(16) 2_656 . ?
H16A C16 H16C 95(2) . . ?
H16A C16 H16B 98.4(18) . . ?
H16C C16 H16B 123(2) . . ?
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 . 1.153(2) ?
N2 C8 . 1.148(2) ?
N3 C9 . 1.154(2) ?
N4 C12 . 1.150(2) ?
C1 C2 . 1.430(2) ?
C2 C3 . 1.389(2) ?
C2 C9 . 1.424(2) ?
C3 C4 . 1.437(2) ?
C3 C10 . 1.442(2) ?
C4 C5 . 1.354(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.4441(19) ?
C5 H5 . 0.93 ?
C6 C7 . 1.389(2) ?
C6 C11 . 1.434(2) ?
C7 C8 . 1.427(2) ?
C7 C12 . 1.433(2) ?
C10 C11 . 1.354(2) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C13 C14 . 1.372(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.366(2) ?
C14 H14 . 0.93 ?
C16 H16A . 1.023(16) ?
C16 H16C . 0.972(17) ?
C16 H16B . 0.968(16) ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C2 C3 C4 178.36(13) . . . . ?
C1 C2 C3 C4 -3.2(2) . . . . ?
C9 C2 C3 C10 -2.6(2) . . . . ?
C1 C2 C3 C10 175.89(13) . . . . ?
C2 C3 C4 C5 178.31(14) . . . . ?
C10 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 -179.10(14) . . . . ?
C4 C5 C6 C11 0.6(2) . . . . ?
C11 C6 C7 C8 178.95(13) . . . . ?
C5 C6 C7 C8 -1.4(2) . . . . ?
C11 C6 C7 C12 -2.0(2) . . . . ?
C5 C6 C7 C12 177.65(14) . . . . ?
C2 C3 C10 C11 -177.67(14) . . . . ?
C4 C3 C10 C11 1.4(2) . . . . ?
C3 C10 C11 C6 -1.1(2) . . . . ?
C7 C6 C11 C10 179.73(14) . . . . ?
C5 C6 C11 C10 0.1(2) . . . . ?
N5 C13 C14 C15 -0.5(3) 2_656 . . . ?
C13 C14 C15 C13 0.5(3) . . . 2_656 ?
