#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567032.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_1567032
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 H8 N2, 2(C12 H4 N4)'
_chemical_formula_sum            'C36 H16 N10'
_chemical_formula_weight         588.59
_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             2020-10-02T14:53:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                89.176(10)
_cell_angle_beta                 82.570(9)
_cell_angle_gamma                69.284(14)
_cell_formula_units_Z            1
_cell_length_a                   7.2179(10)
_cell_length_b                   7.6887(14)
_cell_length_c                   14.5445(13)
_cell_measurement_reflns_used    2275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.721
_cell_measurement_theta_min      6.145
_cell_volume                     748.2(2)
_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 0.984
_diffrn_measured_fraction_theta_max 0.955
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.955
_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       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6183
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.117
_diffrn_reflns_theta_min         3.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.67569
_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    1.306
_exptl_crystal_description       prism
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.4
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.4
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.1078
_refine_ls_shift/su_max          0.001
_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         0.3477
_reflns_number_gt                2470
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_phen_1
_cod_database_code               1567032
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 0.0448(6) 1.2117(4) 0.6984(2) 0.0861(9) Uani d 1 . . N
N2 0.5031(6) 0.5333(5) 0.21299(19) 0.0890(9) Uani d 1 . . N
N3 -0.0731(5) 0.7475(5) 0.8374(2) 0.0873(9) Uani d 1 . . N
N4 0.3940(5) 0.0799(4) 0.3600(2) 0.0845(9) Uani d 1 . . N
C1 0.0568(4) 1.0608(4) 0.69478(18) 0.0642(7) Uani d 1 . . C
C2 0.0700(4) 0.8717(4) 0.69094(18) 0.0599(7) Uani d 1 . . C
C3 0.1522(4) 0.7577(4) 0.61071(17) 0.0563(6) Uani d 1 . . C
C4 0.2259(4) 0.8278(4) 0.52693(18) 0.0575(6) Uani d 1 . . C
H4 0.22311 0.949685 0.52641 0.069 Uiso calc 1 . . H
C5 0.2991(4) 0.7184(4) 0.44893(17) 0.0578(6) Uani d 1 . . C
H5 0.34653 0.76632 0.395716 0.069 Uiso calc 1 . . H
C6 0.3050(4) 0.5298(4) 0.44657(16) 0.0552(6) Uani d 1 . . C
C7 0.3791(4) 0.4183(4) 0.36604(17) 0.0585(6) Uani d 1 . . C
C8 0.4458(4) 0.4855(4) 0.28093(18) 0.0654(7) Uani d 1 . . C
C9 -0.0081(4) 0.8035(4) 0.77229(19) 0.0659(7) Uani d 1 . . C
C10 0.1592(4) 0.5699(4) 0.60904(18) 0.0588(7) Uani d 1 . . C
H10 0.112176 0.522043 0.662412 0.071 Uiso calc 1 . . H
C11 0.2335(4) 0.4595(4) 0.53063(17) 0.0582(6) Uani d 1 . . C
H11 0.23802 0.337095 0.531467 0.07 Uiso calc 1 . . H
C12 0.3867(4) 0.2308(4) 0.36301(18) 0.0623(7) Uani d 1 . . C
N5 0.0618(5) 1.1912(4) 0.93702(17) 0.0721(8) Uani d 0.5 A 1 N
C16 0.2710(5) 0.8730(5) 0.9597(2) 0.0812(9) Uani d 0.5 A 1 C
N6 0.2710(5) 0.8730(5) 0.9597(2) 0.0812(9) Uani d 0.5 A 2 N
C18 0.0618(5) 1.1912(4) 0.93702(17) 0.0721(8) Uani d 0.5 A 2 C
C13 0.2226(6) 1.2184(6) 0.8868(2) 0.0847(10) Uani d 1 . . C
H13 0.208335 1.334303 0.86249 0.102 Uiso calc 1 A 1 H
C14 0.4035(7) 1.0775(7) 0.8720(3) 0.0957(12) Uani d 1 . . C
H14 0.511757 1.096447 0.837128 0.115 Uiso calc 1 . . H
C15 0.4246(6) 0.9053(7) 0.9095(3) 0.0915(11) Uani d 1 . . C
H15 0.548552 0.809886 0.89963 0.11 Uiso calc 1 A 1 H
C17 0.0846(5) 1.0164(5) 0.97332(18) 0.0717(8) Uani d 1 . . C
C19 0.2743(12) 0.7075(10) 1.0002(6) 0.0859(18) Uani d 0.5 . . C
H19 0.399337 0.613306 0.992173 0.103 Uiso calc 0.5 A 1 H
C20 -0.1261(8) 1.3433(8) 0.9497(4) 0.0623(11) Uani d 0.5 . . C
H20 -0.145822 1.461315 0.927058 0.075 Uiso calc 0.5 A 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 179.3(3) . . ?
C3 C2 C9 120.9(3) . . ?
C3 C2 C1 122.3(2) . . ?
C9 C2 C1 116.8(2) . . ?
C2 C3 C10 120.6(2) . . ?
C2 C3 C4 121.2(2) . . ?
C10 C3 C4 118.1(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 C11 121.1(2) . . ?
C5 C6 C11 117.7(2) . . ?
C6 C7 C12 121.7(2) . . ?
C6 C7 C8 122.4(2) . . ?
C12 C7 C8 115.8(2) . . ?
N2 C8 C7 177.8(3) . . ?
N3 C9 C2 179.0(3) . . ?
C11 C10 C3 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C3 C10 H10 119.4 . . ?
C10 C11 C6 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
N4 C12 C7 179.4(3) . . ?
C13 N5 C17 119.3(3) . . ?
C13 N5 C20 118.6(3) . . ?
C17 N5 C20 122.1(3) . . ?
C15 C16 C19 126.9(4) . . ?
C15 C16 C17 118.7(3) . . ?
C19 C16 C17 114.4(4) . . ?
C15 N6 C19 126.9(4) . . ?
C15 N6 C17 118.7(3) . . ?
C19 N6 C17 114.4(4) . . ?
C13 C18 C17 119.3(3) . . ?
C13 C18 C20 118.6(3) . . ?
C17 C18 C20 122.1(3) . . ?
C14 C13 N5 120.7(4) . . ?
C14 C13 C18 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
N5 C13 H13 119.6 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N6 C15 C14 121.8(4) . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
N6 C17 C18 120.0(3) . . ?
C16 C17 N5 120.0(3) . . ?
C16 C17 C17 119.6(4) . 2_577 ?
N5 C17 C17 120.4(4) . 2_577 ?
C20 C19 C16 131.9(6) 2_577 . ?
C20 C19 N6 131.9(6) 2_577 . ?
C20 C19 H19 114.1 2_577 . ?
C16 C19 H19 114.1 . . ?
C19 C20 N5 111.6(5) 2_577 . ?
C19 C20 C18 111.6(5) 2_577 . ?
C19 C20 H20 124.2 2_577 . ?
N5 C20 H20 124.2 . . ?
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 . 1.134(4) ?
N2 C8 . 1.129(4) ?
N3 C9 . 1.148(4) ?
N4 C12 . 1.144(4) ?
C1 C2 . 1.424(4) ?
C2 C3 . 1.402(4) ?
C2 C9 . 1.418(4) ?
C3 C10 . 1.428(4) ?
C3 C4 . 1.440(3) ?
C4 C5 . 1.354(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.436(4) ?
C5 H5 . 0.93 ?
C6 C7 . 1.391(4) ?
C6 C11 . 1.438(3) ?
C7 C12 . 1.424(4) ?
C7 C8 . 1.426(4) ?
C10 C11 . 1.362(4) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
N5 C13 . 1.368(4) ?
N5 C17 . 1.399(4) ?
N5 C20 . 1.436(6) ?
C16 C15 . 1.343(5) ?
C16 C19 . 1.388(9) ?
C16 C17 . 1.398(5) ?
N6 C15 . 1.343(5) ?
N6 C19 . 1.388(9) ?
N6 C17 . 1.398(5) ?
C18 C13 . 1.368(4) ?
C18 C17 . 1.399(4) ?
C18 C20 . 1.436(6) ?
C13 C14 . 1.363(7) ?
C13 H13 . 0.93 ?
C14 C15 . 1.390(7) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C17 C17 2_577 1.458(6) ?
C19 C20 2_577 1.383(10) ?
C19 H19 . 0.93 ?
C20 H20 . 0.93 ?
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 C10 0.0(4) . . . . ?
C1 C2 C3 C10 -178.8(2) . . . . ?
C9 C2 C3 C4 178.0(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 -177.8(2) . . . . ?
C10 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 179.5(2) . . . . ?
C4 C5 C6 C11 -1.0(4) . . . . ?
C5 C6 C7 C12 179.7(2) . . . . ?
C11 C6 C7 C12 0.3(4) . . . . ?
C5 C6 C7 C8 -2.5(4) . . . . ?
C11 C6 C7 C8 178.2(2) . . . . ?
C2 C3 C10 C11 178.1(2) . . . . ?
C4 C3 C10 C11 0.1(4) . . . . ?
C3 C10 C11 C6 -0.8(4) . . . . ?
C7 C6 C11 C10 -179.3(2) . . . . ?
C5 C6 C11 C10 1.3(4) . . . . ?
C17 N5 C13 C14 0.0(5) . . . . ?
C20 N5 C13 C14 -179.2(4) . . . . ?
C17 C18 C13 C14 0.0(5) . . . . ?
C20 C18 C13 C14 -179.2(4) . . . . ?
N5 C13 C14 C15 -0.8(6) . . . . ?
C18 C13 C14 C15 -0.8(6) . . . . ?
C19 N6 C15 C14 179.9(5) . . . . ?
C17 N6 C15 C14 0.8(6) . . . . ?
C19 C16 C15 C14 179.9(5) . . . . ?
C17 C16 C15 C14 0.8(6) . . . . ?
C13 C14 C15 N6 0.5(6) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C15 N6 C17 C18 -1.6(5) . . . . ?
C19 N6 C17 C18 179.2(4) . . . . ?
C15 N6 C17 C17 179.3(3) . . . 2_577 ?
C19 N6 C17 C17 0.1(6) . . . 2_577 ?
C15 C16 C17 N5 -1.6(5) . . . . ?
C19 C16 C17 N5 179.2(4) . . . . ?
C15 C16 C17 C17 179.3(3) . . . 2_577 ?
C19 C16 C17 C17 0.1(6) . . . 2_577 ?
C13 C18 C17 N6 1.3(4) . . . . ?
C20 C18 C17 N6 -179.5(3) . . . . ?
C13 C18 C17 C17 -179.7(3) . . . 2_577 ?
C20 C18 C17 C17 -0.5(5) . . . 2_577 ?
C13 N5 C17 C16 1.3(4) . . . . ?
C20 N5 C17 C16 -179.5(3) . . . . ?
C13 N5 C17 C17 -179.7(3) . . . 2_577 ?
C20 N5 C17 C17 -0.5(5) . . . 2_577 ?
C15 C16 C19 C20 -177.7(7) . . . 2_577 ?
C17 C16 C19 C20 1.4(11) . . . 2_577 ?
C15 N6 C19 C20 -177.7(7) . . . 2_577 ?
C17 N6 C19 C20 1.4(11) . . . 2_577 ?
C13 N5 C20 C19 178.5(5) . . . 2_577 ?
C17 N5 C20 C19 -0.7(7) . . . 2_577 ?
C13 C18 C20 C19 178.5(5) . . . 2_577 ?
C17 C18 C20 C19 -0.7(7) . . . 2_577 ?
