#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567036.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_1567036
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(C8 H8 N2)'
_chemical_formula_sum            'C16 H8 N5'
_chemical_formula_weight         270.27
_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   geom
_audit_creation_date             2020-10-02T13:07:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.618(8)
_cell_angle_beta                 90.811(6)
_cell_angle_gamma                115.727(8)
_cell_formula_units_Z            2
_cell_length_a                   7.5381(5)
_cell_length_b                   8.0130(7)
_cell_length_c                   13.3368(12)
_cell_measurement_reflns_used    1911
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.601
_cell_measurement_theta_min      3.421
_cell_volume                     699.07(12)
_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 0.940
_diffrn_measured_fraction_theta_max 0.889
_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  0.032
_diffrn_reflns_av_unetI/netI     0.041
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4489
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.0
_diffrn_reflns_theta_max         76.338
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.55242
_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    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0725
_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)+(0.1677P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2367
_reflns_number_gt                2083
_reflns_number_total             2612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_4damp_2
_cod_original_cell_volume        699.07(11)
_cod_database_code               1567036
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 0.7652(3) 1.0845(3) 1.17210(17) 0.0866(6) Uani d 1 . . N
N2 0.9609(3) 0.3834(4) 0.6613(2) 0.1014(8) Uani d 1 . . N
N3 0.1338(3) 0.7682(3) 1.07620(16) 0.0797(6) Uani d 1 . . N
N4 0.3218(4) 0.0383(4) 0.56784(18) 0.0943(7) Uani d 1 . . N
C1 0.6381(3) 0.9567(3) 1.11328(15) 0.0605(5) Uani d 1 . . C
C2 0.4798(2) 0.8016(3) 1.04068(14) 0.0542(5) Uani d 1 . . C
C3 0.5109(2) 0.6820(2) 0.95687(13) 0.0509(4) Uani d 1 . . C
C4 0.7081(2) 0.7081(3) 0.93879(14) 0.0559(5) Uani d 1 . . C
H4 0.816888 0.806551 0.984595 0.067 Uiso calc 1 . . H
C5 0.7380(2) 0.5922(3) 0.85650(15) 0.0566(5) Uani d 1 . . C
H5 0.867029 0.612627 0.846847 0.068 Uiso calc 1 . . H
C6 0.5757(2) 0.4388(3) 0.78392(14) 0.0528(4) Uani d 1 . . C
C7 0.6075(3) 0.3215(3) 0.69862(15) 0.0597(5) Uani d 1 . . C
C8 0.8038(3) 0.3547(4) 0.67725(17) 0.0712(6) Uani d 1 . . C
C9 0.2866(2) 0.7805(3) 1.05959(14) 0.0591(5) Uani d 1 . . C
C10 0.3482(2) 0.5278(3) 0.88327(14) 0.0538(4) Uani d 1 . . C
H10 0.218977 0.507946 0.892103 0.065 Uiso calc 1 . . H
C11 0.3788(2) 0.4119(3) 0.80202(14) 0.0559(5) Uani d 1 . . C
H11 0.270291 0.31228 0.756605 0.067 Uiso calc 1 . . H
C12 0.4488(3) 0.1648(3) 0.62631(15) 0.0672(5) Uani d 1 . . C
N5 0.3076(3) 0.2556(3) 0.38919(15) 0.0790(6) Uani d 1 . . N
C13 0.2338(6) 0.3414(7) 0.4667(4) 0.0711(10) Uani d 0.5 . . C
H13 0.098044 0.287212 0.470543 0.085 Uiso calc 0.5 . . H
C14 0.6383(3) 0.4908(4) 0.46057(17) 0.0690(5) Uani d 1 . . C
C15 0.4363(5) 0.4183(5) 0.4586(3) 0.0580(8) Uani d 0.5 . . C
C16 0.5006(8) 0.3209(8) 0.3897(3) 0.0749(11) Uani d 0.5 . . C
H16 0.547771 0.251565 0.340995 0.09 Uiso calc 0.5 . . H
C17 0.1563(11) 0.0739(9) 0.3156(6) 0.114(2) Uani d 0.5 . . C
H17A 0.041989 -0.037757 0.275429 0.171 Uiso calc 0.5 . . H
H17B 0.226135 0.152248 0.271055 0.171 Uiso calc 0.5 . . H
H17C 0.242493 0.03467 0.346456 0.171 Uiso calc 0.5 . . H
C18 0.0967(7) 0.1773(10) 0.3923(6) 0.111(2) Uani d 0.5 . . C
C19 0.3847(14) 0.1559(9) 0.3061(5) 0.109(2) Uani d 0.5 . . C
H19A 0.275255 0.049013 0.259472 0.163 Uiso calc 0.5 . . H
H19B 0.463831 0.243995 0.268091 0.163 Uiso calc 0.5 . . H
H19C 0.464743 0.110345 0.336884 0.163 Uiso calc 0.5 . . 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 178.9(2) . . ?
C3 C2 C1 122.65(15) . . ?
C3 C2 C9 122.52(16) . . ?
C1 C2 C9 114.83(16) . . ?
C2 C3 C10 121.61(14) . . ?
C2 C3 C4 121.38(15) . . ?
C10 C3 C4 117.00(15) . . ?
C5 C4 C3 121.21(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.53(14) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.26(15) . . ?
C7 C6 C11 121.36(16) . . ?
C5 C6 C11 117.38(16) . . ?
C6 C7 C12 122.57(16) . . ?
C6 C7 C8 121.43(19) . . ?
C12 C7 C8 115.99(18) . . ?
N2 C8 C7 179.1(3) . . ?
N3 C9 C2 178.3(2) . . ?
C11 C10 C3 121.47(14) . . ?
C11 C10 H10 119.3 . . ?
C3 C10 H10 119.3 . . ?
C10 C11 C6 121.40(16) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
N4 C12 C7 179.6(3) . . ?
C16 N5 C15 58.6(3) . . ?
C16 N5 C13 120.1(3) . . ?
C15 N5 C13 61.9(2) . . ?
C16 N5 C18 176.7(4) . . ?
C15 N5 C18 121.6(4) . . ?
C13 N5 C18 59.8(4) . . ?
C16 N5 C19 60.8(4) . . ?
C15 N5 C19 119.2(4) . . ?
C13 N5 C19 178.0(3) . . ?
C18 N5 C19 119.2(5) . . ?
C16 N5 C17 124.2(4) . . ?
C15 N5 C17 177.0(4) . . ?
C13 N5 C17 115.2(4) . . ?
C18 N5 C17 55.5(5) . . ?
C19 N5 C17 63.7(4) . . ?
N5 C13 C14 119.8(3) . 2_666 ?
N5 C13 H13 120.1 . . ?
C14 C13 H13 120.1 2_666 . ?
C15 C14 C13 121.1(3) . 2_666 ?
C15 C14 C16 56.0(3) . . ?
C13 C14 C16 177.0(3) 2_666 . ?
C15 C14 C15 61.8(3) . 2_666 ?
C13 C14 C15 59.6(2) 2_666 2_666 ?
C16 C14 C15 117.4(3) . 2_666 ?
N5 C15 C14 122.7(3) . . ?
N5 C15 C14 118.8(3) . 2_666 ?
C14 C15 C14 118.2(3) . 2_666 ?
N5 C15 C15 173.7(4) . 2_666 ?
C14 C15 C15 60.7(2) . 2_666 ?
C14 C15 C15 57.5(3) 2_666 2_666 ?
N5 C16 C14 122.7(3) . . ?
N5 C16 H16 118.7 . . ?
C14 C16 H16 118.7 . . ?
C18 C17 N5 60.2(3) . . ?
C18 C17 H17A 109.5 . . ?
N5 C17 H17A 169.6 . . ?
C18 C17 H17B 109.5 . . ?
N5 C17 H17B 75.9 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
N5 C17 H17C 75.9 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 C18 N5 64.4(4) . . ?
N5 C19 H19A 109.5 . . ?
N5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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(3) ?
N2 C8 . 1.137(3) ?
N3 C9 . 1.142(3) ?
N4 C12 . 1.148(3) ?
C1 C2 . 1.421(2) ?
C2 C3 . 1.386(3) ?
C2 C9 . 1.425(2) ?
C3 C10 . 1.440(2) ?
C3 C4 . 1.441(2) ?
C4 C5 . 1.352(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.430(2) ?
C5 H5 . 0.93 ?
C6 C7 . 1.391(3) ?
C6 C11 . 1.437(2) ?
C7 C12 . 1.425(3) ?
C7 C8 . 1.431(3) ?
C10 C11 . 1.345(3) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
N5 C16 . 1.314(5) ?
N5 C15 . 1.344(4) ?
N5 C13 . 1.366(5) ?
N5 C18 . 1.439(6) ?
N5 C19 . 1.486(7) ?
N5 C17 . 1.496(6) ?
C13 C14 2_666 1.383(5) ?
C13 H13 . 0.93 ?
C14 C15 . 1.371(4) ?
C14 C16 . 1.401(5) ?
C14 C15 2_666 1.418(4) ?
C15 C15 2_666 1.433(7) ?
C16 H16 . 0.93 ?
C17 C18 . 1.368(11) ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C17 H17A N1 0.96 3.09 3.535(7) 110 1_444 yes
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
C1 C2 C3 C10 -178.87(15) . . . . ?
C9 C2 C3 C10 0.0(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C9 C2 C3 C4 179.17(16) . . . . ?
C2 C3 C4 C5 -179.46(16) . . . . ?
C10 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 179.16(16) . . . . ?
C4 C5 C6 C11 -0.2(3) . . . . ?
C5 C6 C7 C12 178.52(16) . . . . ?
C11 C6 C7 C12 -2.1(3) . . . . ?
C5 C6 C7 C8 -2.9(3) . . . . ?
C11 C6 C7 C8 176.46(17) . . . . ?
C2 C3 C10 C11 -179.96(17) . . . . ?
C4 C3 C10 C11 0.8(3) . . . . ?
C3 C10 C11 C6 -1.1(3) . . . . ?
C7 C6 C11 C10 -178.57(17) . . . . ?
C5 C6 C11 C10 0.8(3) . . . . ?
C16 N5 C13 C14 6.9(5) . . . 2_666 ?
C15 N5 C13 C14 0.1(3) . . . 2_666 ?
C18 N5 C13 C14 -176.9(5) . . . 2_666 ?
C17 N5 C13 C14 179.4(4) . . . 2_666 ?
C16 N5 C15 C14 0.5(3) . . . . ?
C13 N5 C15 C14 173.7(4) . . . . ?
C18 N5 C15 C14 176.7(4) . . . . ?
C19 N5 C15 C14 -4.4(5) . . . . ?
C16 N5 C15 C14 -173.3(4) . . . 2_666 ?
C13 N5 C15 C14 -0.1(3) . . . 2_666 ?
C18 N5 C15 C14 2.9(5) . . . 2_666 ?
C19 N5 C15 C14 -178.2(3) . . . 2_666 ?
C13 C14 C15 N5 -179.9(3) 2_666 . . . ?
C16 C14 C15 N5 -0.5(3) . . . . ?
C15 C14 C15 N5 -173.9(5) 2_666 . . . ?
C13 C14 C15 C14 -6.1(4) 2_666 . . 2_666 ?
C16 C14 C15 C14 173.4(4) . . . 2_666 ?
C15 C14 C15 C14 -0.0020(10) 2_666 . . 2_666 ?
C13 C14 C15 C15 -6.1(4) 2_666 . . 2_666 ?
C16 C14 C15 C15 173.4(4) . . . 2_666 ?
C15 N5 C16 C14 -0.5(3) . . . . ?
C13 N5 C16 C14 -7.5(5) . . . . ?
C19 N5 C16 C14 174.6(5) . . . . ?
C17 N5 C16 C14 -179.3(4) . . . . ?
C15 C14 C16 N5 0.5(3) . . . . ?
C15 C14 C16 N5 7.1(5) 2_666 . . . ?
C16 N5 C17 C18 176.1(4) . . . . ?
C13 N5 C17 C18 3.9(5) . . . . ?
C19 N5 C17 C18 -178.0(5) . . . . ?
C15 N5 C18 C17 -179.0(4) . . . . ?
C13 N5 C18 C17 -175.9(5) . . . . ?
C19 N5 C18 C17 2.1(5) . . . . ?
