#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567030.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_1567030
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         '2(C12 H4 N4), C5 N'
_chemical_formula_sum            'C29 H8 N9'
_chemical_formula_weight         482.44
_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   geom
_audit_creation_date             2020-10-02T14:31:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.616(5)
_cell_angle_beta                 103.414(5)
_cell_angle_gamma                113.979(6)
_cell_formula_units_Z            1
_cell_length_a                   7.2867(5)
_cell_length_b                   7.7545(4)
_cell_length_c                   13.1305(7)
_cell_measurement_reflns_used    1771
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.071
_cell_measurement_theta_min      6.308
_cell_volume                     651.19(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      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.963
_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  0.021
_diffrn_reflns_av_unetI/netI     0.036
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4998
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.19
_diffrn_reflns_theta_min         3.504
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.74498
_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    1.230
_exptl_crystal_description       prism
_exptl_crystal_F_000             245
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.558
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.641
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.1198
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3926
_reflns_number_gt                1975
_reflns_number_total             2624
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_nmepy_2
_cod_original_cell_volume        651.18(7)
_cod_database_code               1567030
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 0.2913(8) 0.1578(8) 0.1180(3) 0.1212(15) Uani d 1 . . N
N2 0.2562(6) 0.6469(5) 0.2725(3) 0.1022(11) Uani d 1 . . N
N3 0.2350(6) -0.3528(5) 0.6584(3) 0.0925(10) Uani d 1 . . N
N4 0.2602(8) 0.1464(6) 0.8285(3) 0.1117(13) Uani d 1 . . N
C1 0.2520(4) 0.2344(4) 0.3749(2) 0.0608(7) Uani d 1 . . C
C2 0.2493(4) 0.3294(4) 0.4704(2) 0.0638(7) Uani d 1 . . C
H2 0.249581 0.449516 0.471271 0.077 Uiso calc 1 . . H
C3 0.2463(4) 0.2479(4) 0.5591(2) 0.0633(7) Uani d 1 . . C
H3 0.244883 0.313102 0.619906 0.076 Uiso calc 1 . . H
C4 0.2452(4) 0.0626(4) 0.5612(2) 0.0590(7) Uani d 1 . . C
C5 0.2442(4) -0.0335(4) 0.4652(2) 0.0621(7) Uani d 1 . . C
H5 0.241086 -0.154724 0.463765 0.074 Uiso calc 1 . . H
C6 0.2478(4) 0.0493(4) 0.3763(2) 0.0637(7) Uani d 1 . . C
H6 0.247507 -0.016138 0.315038 0.076 Uiso calc 1 . . H
C7 0.2609(4) 0.3210(5) 0.2839(2) 0.0701(8) Uani d 1 . . C
C8 0.2774(6) 0.2308(6) 0.1919(3) 0.0827(9) Uani d 1 . . C
C9 0.2592(5) 0.5018(5) 0.2779(3) 0.0783(9) Uani d 1 . . C
C10 0.2445(4) -0.0209(4) 0.6526(2) 0.0639(7) Uani d 1 . . C
C11 0.2396(4) -0.2053(4) 0.6554(2) 0.0691(8) Uani d 1 . . C
C12 0.2539(5) 0.0735(5) 0.7501(2) 0.0754(9) Uani d 1 . . C
N5 0.0802(9) 0.5508(11) -0.0118(5) 0.1458(18) Uani d 0.5 . . N
C13 -0.0224(13) 0.6312(9) 0.0310(5) 0.0817(16) Uani d 0.5 . . C
C14 0.149(2) 0.7467(19) 0.0000(8) 0.139(3) Uani d 0.5 . . C
C15 0.2573(15) 0.685(2) -0.0427(8) 0.130(3) Uani d 0.5 . . C
C16 0.191(2) 0.496(2) -0.0575(10) 0.166(5) Uani d 0.5 . . C
C17 0.0802(9) 0.5508(11) -0.0118(5) 0.1458(18) Uani d 0.5 . . C
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
C7 C1 C6 121.1(3) . . ?
C7 C1 C2 121.3(3) . . ?
C6 C1 C2 117.7(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C10 C4 C5 121.2(3) . . ?
C10 C4 C3 121.4(3) . . ?
C5 C4 C3 117.4(2) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C1 C7 C9 123.1(3) . . ?
C1 C7 C8 120.8(3) . . ?
C9 C7 C8 116.2(3) . . ?
N1 C8 C7 179.7(4) . . ?
N2 C9 C7 179.5(4) . . ?
C4 C10 C11 122.1(3) . . ?
C4 C10 C12 122.6(3) . . ?
C11 C10 C12 115.2(3) . . ?
N3 C11 C10 179.4(3) . . ?
N4 C12 C10 179.0(4) . . ?
N5 C13 C17 55.8(5) 2_565 . ?
N5 C13 C16 58.4(6) 2_565 2_565 ?
C17 C13 C16 114.1(7) . 2_565 ?
N5 C13 C14 116.8(9) 2_565 . ?
C17 C13 C14 61.1(7) . . ?
C16 C13 C14 175.2(9) 2_565 . ?
C15 C14 C13 124.3(12) . . ?
C15 C14 C17 65.9(8) . . ?
C13 C14 C17 58.4(7) . . ?
C14 C15 C16 115.4(11) . . ?
C14 C15 C17 60.2(8) . . ?
C16 C15 C17 55.2(8) . . ?
C17 C16 C15 67.0(8) . . ?
C17 C16 C13 58.1(8) . 2_565 ?
C15 C16 C13 125.1(11) . 2_565 ?
N5 C17 C13 64.2(8) 2_565 2_565 ?
N5 C17 C16 127.6(13) 2_565 . ?
C13 C17 C16 63.5(8) 2_565 . ?
N5 C17 C13 60.0(7) 2_565 . ?
C13 C17 C13 124.2(5) 2_565 . ?
C16 C17 C13 171.9(9) . . ?
N5 C17 C14 120.4(12) 2_565 . ?
C13 C17 C14 174.4(8) 2_565 . ?
C16 C17 C14 111.6(9) . . ?
C13 C17 C14 60.5(7) . . ?
N5 C17 C15 173.3(12) 2_565 . ?
C13 C17 C15 121.3(9) 2_565 . ?
C16 C17 C15 57.8(7) . . ?
C13 C17 C15 114.4(9) . . ?
C14 C17 C15 53.9(6) . . ?
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 C8 . 1.146(6) ?
N2 C9 . 1.139(5) ?
N3 C11 . 1.133(4) ?
N4 C12 . 1.134(5) ?
C1 C7 . 1.399(4) ?
C1 C6 . 1.424(4) ?
C1 C2 . 1.433(4) ?
C2 C3 . 1.350(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.436(4) ?
C3 H3 . 0.93 ?
C4 C10 . 1.390(4) ?
C4 C5 . 1.431(4) ?
C5 C6 . 1.359(4) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 C9 . 1.413(5) ?
C7 C8 . 1.422(5) ?
C10 C11 . 1.418(4) ?
C10 C12 . 1.419(4) ?
C13 C17 . 1.343(10) ?
C13 C16 2_565 1.362(15) ?
C13 C14 . 1.373(14) ?
C14 C15 . 1.285(14) ?
C14 C17 . 1.380(15) ?
C15 C16 . 1.334(14) ?
C15 C17 . 1.452(11) ?
C16 C17 . 1.296(14) ?
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
C7 C1 C2 C3 -178.2(2) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C10 179.3(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C10 C4 C5 C6 -179.1(2) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C7 C1 C6 C5 178.4(2) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C6 C1 C7 C9 178.1(2) . . . . ?
C2 C1 C7 C9 -2.7(5) . . . . ?
C6 C1 C7 C8 -3.4(4) . . . . ?
C2 C1 C7 C8 175.9(3) . . . . ?
C5 C4 C10 C11 -0.9(4) . . . . ?
C3 C4 C10 C11 178.8(2) . . . . ?
C5 C4 C10 C12 177.4(2) . . . . ?
C3 C4 C10 C12 -2.9(5) . . . . ?
N5 C13 C14 C15 -2.6(14) 2_565 . . . ?
C17 C13 C14 C15 0.8(10) . . . . ?
N5 C13 C14 C17 -3.4(8) 2_565 . . . ?
C13 C14 C15 C16 0.9(17) . . . . ?
C17 C14 C15 C16 1.6(10) . . . . ?
C13 C14 C15 C17 -0.7(9) . . . . ?
C14 C15 C16 C17 -1.7(11) . . . . ?
C14 C15 C16 C13 -0.1(18) . . . 2_565 ?
C17 C15 C16 C13 1.6(9) . . . 2_565 ?
C15 C16 C17 N5 175.1(11) . . . 2_565 ?
C13 C16 C17 N5 -3.4(10) 2_565 . . 2_565 ?
C15 C16 C17 C13 178.4(8) . . . 2_565 ?
C15 C16 C17 C14 1.6(10) . . . . ?
C13 C16 C17 C14 -176.9(8) 2_565 . . . ?
C13 C16 C17 C15 -178.4(8) 2_565 . . . ?
C16 C13 C17 N5 2.8(9) 2_565 . . 2_565 ?
C14 C13 C17 N5 -176.4(8) . . . 2_565 ?
N5 C13 C17 C13 0.0010(10) 2_565 . . 2_565 ?
C16 C13 C17 C13 2.8(9) 2_565 . . 2_565 ?
C14 C13 C17 C13 -176.4(8) . . . 2_565 ?
N5 C13 C17 C14 176.4(8) 2_565 . . . ?
C16 C13 C17 C14 179.1(9) 2_565 . . . ?
N5 C13 C17 C15 175.8(9) 2_565 . . . ?
C16 C13 C17 C15 178.5(8) 2_565 . . . ?
C14 C13 C17 C15 -0.6(8) . . . . ?
C15 C14 C17 N5 -175.7(10) . . . 2_565 ?
C13 C14 C17 N5 3.6(8) . . . 2_565 ?
C15 C14 C17 C16 -1.6(10) . . . . ?
C13 C14 C17 C16 177.7(8) . . . . ?
C15 C14 C17 C13 -179.3(9) . . . . ?
C13 C14 C17 C15 179.3(9) . . . . ?
C14 C15 C17 C13 176.6(9) . . . 2_565 ?
C16 C15 C17 C13 -1.6(9) . . . 2_565 ?
C14 C15 C17 C16 178.2(11) . . . . ?
C14 C15 C17 C13 0.7(8) . . . . ?
C16 C15 C17 C13 -177.5(9) . . . . ?
C16 C15 C17 C14 -178.2(11) . . . . ?
