#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567029.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_1567029
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), C6 H8 N'
_chemical_formula_sum            'C30 H16 N9'
_chemical_formula_weight         502.52
_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             2020-10-02T14:39:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                99.902(4)
_cell_angle_beta                 106.251(5)
_cell_angle_gamma                97.225(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7274(4)
_cell_length_b                   13.1422(6)
_cell_length_c                   13.3145(6)
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.207
_cell_measurement_theta_min      3.466
_cell_volume                     1256.99(11)
_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 0.965
_diffrn_measured_fraction_theta_max 0.93
_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  0.0708
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.93
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8993
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.93
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.672
_diffrn_reflns_theta_min         3.473
_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  0.35443
_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    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.699
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.699
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0815
_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)+(0.0800P)²+0.0841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.238
_reflns_number_gt                4067
_reflns_number_total             4926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_nmepy_100k_2
_cod_original_cell_volume        1257.00(11)
_cod_database_code               1567029
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
N1A 0.6623(3) 1.02060(18) 1.32911(17) 0.0444(5) Uani d 1 . . N
N2A 0.8690(3) 0.74490(16) 0.75826(16) 0.0392(5) Uani d 1 . . N
N3A 0.0818(3) 0.96471(17) 1.14969(17) 0.0418(5) Uani d 1 . . N
N4A 0.2723(3) 0.66432(17) 0.60476(16) 0.0422(5) Uani d 1 . . N
C1A 0.5512(3) 0.98820(17) 1.24761(18) 0.0343(5) Uani d 1 . . C
C2A 0.4111(3) 0.94931(16) 1.14681(17) 0.0306(4) Uani d 1 . . C
C3A 0.4462(3) 0.90448(15) 1.05491(17) 0.0292(4) Uani d 1 . . C
C4A 0.6289(3) 0.89609(15) 1.05256(16) 0.0296(4) Uani d 1 . . C
H4A 0.726948 0.922366 1.11484 0.036 Uiso calc 1 . . H
C5A 0.6617(3) 0.85107(15) 0.96237(17) 0.0300(4) Uani d 1 . . C
H5A 0.781898 0.848035 0.963624 0.036 Uiso calc 1 . . H
C6A 0.5146(3) 0.80758(15) 0.86410(16) 0.0301(4) Uani d 1 . . C
C7A 0.5451(3) 0.75718(16) 0.77219(17) 0.0315(5) Uani d 1 . . C
C8A 0.7247(3) 0.75019(16) 0.76483(17) 0.0328(5) Uani d 1 . . C
C9A 0.2285(3) 0.95776(16) 1.14907(17) 0.0321(5) Uani d 1 . . C
C10A 0.2992(3) 0.86325(15) 0.95568(16) 0.0300(4) Uani d 1 . . C
H10A 0.179619 0.868839 0.953735 0.036 Uiso calc 1 . . H
C11A 0.3315(3) 0.81683(15) 0.86578(17) 0.0307(4) Uani d 1 . . C
H11A 0.233423 0.790242 0.803565 0.037 Uiso calc 1 . . H
C12A 0.3950(3) 0.70588(17) 0.67839(18) 0.0346(5) Uani d 1 . . C
N1B 0.2272(3) 0.54299(17) 0.33710(17) 0.0444(5) Uani d 1 . . N
N2B 0.4564(3) 0.27919(16) -0.21957(16) 0.0408(5) Uani d 1 . . N
N3B -0.3610(3) 0.45662(15) 0.17094(16) 0.0373(4) Uani d 1 . . N
N4B -0.1294(3) 0.16750(17) -0.37628(17) 0.0441(5) Uani d 1 . . N
C1B 0.1112(3) 0.50494(17) 0.25938(18) 0.0341(5) Uani d 1 . . C
C2B -0.0316(3) 0.45641(15) 0.16156(17) 0.0296(4) Uani d 1 . . C
C3B 0.0059(3) 0.41171(15) 0.07002(16) 0.0285(4) Uani d 1 . . C
C4B 0.1927(3) 0.41746(15) 0.06784(16) 0.0290(4) Uani d 1 . . C
H4B 0.288472 0.452138 0.128707 0.035 Uiso calc 1 . . H
C5B 0.2304(3) 0.37354(15) -0.02067(16) 0.0292(4) Uani d 1 . . C
H5B 0.352114 0.37907 -0.019672 0.035 Uiso calc 1 . . H
C6B 0.0879(3) 0.31817(15) -0.11698(17) 0.0296(4) Uani d 1 . . C
C7B 0.1273(3) 0.27125(16) -0.20694(17) 0.0307(4) Uani d 1 . . C
C8B 0.3096(3) 0.27592(16) -0.21307(17) 0.0334(5) Uani d 1 . . C
C9B -0.2153(3) 0.45531(15) 0.16628(16) 0.0310(5) Uani d 1 . . C
C10B -0.1369(3) 0.35747(15) -0.02605(16) 0.0286(4) Uani d 1 . . C
H10B -0.258591 0.352949 -0.027357 0.034 Uiso calc 1 . . H
C11B -0.0984(3) 0.31286(15) -0.11458(17) 0.0297(4) Uani d 1 . . C
H11B -0.194198 0.277934 -0.175354 0.036 Uiso calc 1 . . H
C12B -0.0148(3) 0.21314(17) -0.30093(18) 0.0338(5) Uani d 1 . . C
N5 0.7639(3) 0.71377(17) 0.49261(15) 0.0415(5) Uani d 1 . . N
C13 0.5917(3) 0.7310(2) 0.47847(18) 0.0423(6) Uani d 1 . . C
H13 0.493222 0.675425 0.447088 0.051 Uiso calc 1 . . H
C14 0.5605(3) 0.8299(2) 0.50994(19) 0.0437(6) Uani d 1 . . C
H14 0.441355 0.841483 0.5009 0.052 Uiso calc 1 . . H
C15 0.7069(4) 0.9122(2) 0.5552(2) 0.0455(6) Uani d 1 . . C
H15 0.687126 0.979842 0.576357 0.055 Uiso calc 1 . . H
C16 0.8822(4) 0.8937(2) 0.5687(2) 0.0474(6) Uani d 1 . . C
H16 0.981694 0.948958 0.598479 0.057 Uiso calc 1 . . H
C17 0.9098(3) 0.7942(2) 0.5384(2) 0.0445(6) Uani d 1 . . C
H17 1.028396 0.781118 0.549002 0.053 Uiso calc 1 . . H
C18 0.7967(6) 0.6064(2) 0.4596(2) 0.0634(8) Uani d 1 . . C
H18A 0.926137 0.607839 0.475135 0.095 Uiso calc 1 . . H
H18B 0.747949 0.560814 0.498082 0.095 Uiso calc 1 . . H
H18C 0.737331 0.580975 0.384017 0.095 Uiso calc 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 0.018 0.009 '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 0.031 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
N1A C1A C2A 178.9(3) . . ?
C3A C2A C1A 123.1(2) . . ?
C3A C2A C9A 122.13(19) . . ?
C1A C2A C9A 114.79(19) . . ?
C2A C3A C4A 122.16(19) . . ?
C2A C3A C10A 121.0(2) . . ?
C4A C3A C10A 116.83(19) . . ?
C5A C4A C3A 121.71(19) . . ?
C5A C4A H4A 119.1 . . ?
C3A C4A H4A 119.1 . . ?
C4A C5A C6A 121.4(2) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C7A C6A C5A 122.2(2) . . ?
C7A C6A C11A 120.80(19) . . ?
C5A C6A C11A 117.03(19) . . ?
C6A C7A C8A 123.0(2) . . ?
C6A C7A C12A 121.1(2) . . ?
C8A C7A C12A 115.93(19) . . ?
N2A C8A C7A 179.5(2) . . ?
N3A C9A C2A 179.2(2) . . ?
C11A C10A C3A 121.6(2) . . ?
C11A C10A H10A 119.2 . . ?
C3A C10A H10A 119.2 . . ?
C10A C11A C6A 121.42(19) . . ?
C10A C11A H11A 119.3 . . ?
C6A C11A H11A 119.3 . . ?
N4A C12A C7A 178.4(2) . . ?
N1B C1B C2B 179.0(3) . . ?
C3B C2B C1B 122.0(2) . . ?
C3B C2B C9B 122.60(18) . . ?
C1B C2B C9B 115.41(19) . . ?
C2B C3B C10B 122.01(19) . . ?
C2B C3B C4B 120.76(18) . . ?
C10B C3B C4B 117.23(19) . . ?
C5B C4B C3B 121.15(18) . . ?
C5B C4B H4B 119.4 . . ?
C3B C4B H4B 119.4 . . ?
C4B C5B C6B 121.9(2) . . ?
C4B C5B H5B 119.1 . . ?
C6B C5B H5B 119.1 . . ?
C7B C6B C5B 121.7(2) . . ?
C7B C6B C11B 121.46(19) . . ?
C5B C6B C11B 116.79(19) . . ?
C6B C7B C8B 123.18(19) . . ?
C6B C7B C12B 121.4(2) . . ?
C8B C7B C12B 115.43(19) . . ?
N2B C8B C7B 179.0(2) . . ?
N3B C9B C2B 178.6(2) . . ?
C11B C10B C3B 121.47(19) . . ?
C11B C10B H10B 119.3 . . ?
C3B C10B H10B 119.3 . . ?
C10B C11B C6B 121.47(19) . . ?
C10B C11B H11B 119.3 . . ?
C6B C11B H11B 119.3 . . ?
N4B C12B C7B 179.3(3) . . ?
C13 N5 C17 120.7(2) . . ?
C13 N5 C18 120.1(2) . . ?
C17 N5 C18 119.2(3) . . ?
N5 C13 C14 120.4(2) . . ?
N5 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N5 C17 C16 120.1(2) . . ?
N5 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N1A C1A . 1.151(3) ?
N2A C8A . 1.153(3) ?
N3A C9A . 1.151(3) ?
N4A C12A . 1.151(3) ?
C1A C2A . 1.430(3) ?
C2A C3A . 1.377(3) ?
C2A C9A . 1.437(3) ?
C3A C4A . 1.438(3) ?
C3A C10A . 1.445(3) ?
C4A C5A . 1.349(3) ?
C4A H4A . 0.93 ?
C5A C6A . 1.442(3) ?
C5A H5A . 0.93 ?
C6A C7A . 1.383(3) ?
C6A C11A . 1.442(3) ?
C7A C8A . 1.431(3) ?
C7A C12A . 1.436(3) ?
C10A C11A . 1.349(3) ?
C10A H10A . 0.93 ?
C11A H11A . 0.93 ?
N1B C1B . 1.147(3) ?
N2B C8B . 1.158(3) ?
N3B C9B . 1.147(3) ?
N4B C12B . 1.145(3) ?
C1B C2B . 1.433(3) ?
C2B C3B . 1.382(3) ?
C2B C9B . 1.437(3) ?
C3B C10B . 1.435(3) ?
C3B C4B . 1.444(3) ?
C4B C5B . 1.345(3) ?
C4B H4B . 0.93 ?
C5B C6B . 1.440(3) ?
C5B H5B . 0.93 ?
C6B C7B . 1.380(3) ?
C6B C11B . 1.442(3) ?
C7B C8B . 1.428(3) ?
C7B C12B . 1.431(3) ?
C10B C11B . 1.350(3) ?
C10B H10B . 0.93 ?
C11B H11B . 0.93 ?
N5 C13 . 1.345(3) ?
N5 C17 . 1.361(4) ?
N5 C18 . 1.479(3) ?
C13 C14 . 1.367(4) ?
C13 H13 . 0.93 ?
C14 C15 . 1.378(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.374(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.363(4) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
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
C1A C2A C3A C4A -1.9(3) . . . . ?
C9A C2A C3A C4A 179.94(18) . . . . ?
C1A C2A C3A C10A 177.99(18) . . . . ?
C9A C2A C3A C10A -0.2(3) . . . . ?
C2A C3A C4A C5A 179.32(18) . . . . ?
C10A C3A C4A C5A -0.6(3) . . . . ?
C3A C4A C5A C6A -1.0(3) . . . . ?
C4A C5A C6A C7A -177.18(19) . . . . ?
C4A C5A C6A C11A 1.6(3) . . . . ?
C5A C6A C7A C8A -4.3(3) . . . . ?
C11A C6A C7A C8A 176.99(18) . . . . ?
C5A C6A C7A C12A 174.06(18) . . . . ?
C11A C6A C7A C12A -4.7(3) . . . . ?
C2A C3A C10A C11A -178.34(19) . . . . ?
C4A C3A C10A C11A 1.5(3) . . . . ?
C3A C10A C11A C6A -0.9(3) . . . . ?
C7A C6A C11A C10A 178.17(18) . . . . ?
C5A C6A C11A C10A -0.6(3) . . . . ?
C1B C2B C3B C10B 176.13(17) . . . . ?
C9B C2B C3B C10B -2.3(3) . . . . ?
C1B C2B C3B C4B -3.5(3) . . . . ?
C9B C2B C3B C4B 178.07(17) . . . . ?
C2B C3B C4B C5B 179.53(18) . . . . ?
C10B C3B C4B C5B -0.1(3) . . . . ?
C3B C4B C5B C6B -0.5(3) . . . . ?
C4B C5B C6B C7B -178.59(18) . . . . ?
C4B C5B C6B C11B 0.6(3) . . . . ?
C5B C6B C7B C8B -1.7(3) . . . . ?
C11B C6B C7B C8B 179.11(18) . . . . ?
C5B C6B C7B C12B 177.69(18) . . . . ?
C11B C6B C7B C12B -1.5(3) . . . . ?
C2B C3B C10B C11B -179.09(18) . . . . ?
C4B C3B C10B C11B 0.5(3) . . . . ?
C3B C10B C11B C6B -0.4(3) . . . . ?
C7B C6B C11B C10B 179.03(18) . . . . ?
C5B C6B C11B C10B -0.2(3) . . . . ?
C17 N5 C13 C14 0.0(3) . . . . ?
C18 N5 C13 C14 179.3(2) . . . . ?
N5 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C13 N5 C17 C16 -1.2(3) . . . . ?
C18 N5 C17 C16 179.6(2) . . . . ?
C15 C16 C17 N5 1.5(4) . . . . ?
