#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567031.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_1567031
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             2020-10-02T14:45:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                89.017(10)
_cell_angle_beta                 83.589(12)
_cell_angle_gamma                68.340(17)
_cell_formula_units_Z            1
_cell_length_a                   7.1249(13)
_cell_length_b                   7.6572(13)
_cell_length_c                   14.4249(10)
_cell_measurement_reflns_used    2008
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.552
_cell_measurement_theta_min      6.17
_cell_volume                     726.6(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      100(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5931
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.08
_diffrn_reflns_theta_min         3.084
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.63298
_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    1.345
_exptl_crystal_description       prism
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.12
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.481
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.481
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.1281
_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         0.3816
_reflns_number_gt                2391
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_phen_100k
_cod_database_code               1567031
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 0.0486(5) 1.2187(5) 0.6994(2) 0.0497(8) Uani d 1 . . N
N2 0.4997(5) 0.5429(5) 0.2099(2) 0.0506(9) Uani d 1 . . N
N3 -0.0714(5) 0.7492(5) 0.8379(2) 0.0507(9) Uani d 1 . . N
N4 0.3905(5) 0.0828(5) 0.3580(2) 0.0473(8) Uani d 1 . . N
C1 0.0614(5) 1.0673(5) 0.6956(2) 0.0410(8) Uani d 1 . . C
C2 0.0732(5) 0.8770(5) 0.6907(2) 0.0417(8) Uani d 1 . . C
C3 0.1539(5) 0.7630(5) 0.6106(2) 0.0381(8) Uani d 1 . . C
C4 0.2285(5) 0.8330(5) 0.5266(2) 0.0393(8) Uani d 1 . . C
H4 0.228534 0.954426 0.526488 0.047 Uiso calc 1 . . H
C5 0.2983(5) 0.7241(5) 0.4483(2) 0.0406(8) Uani d 1 . . C
H5 0.343752 0.772694 0.394693 0.049 Uiso calc 1 . . H
C6 0.3039(4) 0.5352(5) 0.4460(2) 0.0378(8) Uani d 1 . . C
C7 0.3780(5) 0.4227(5) 0.3647(2) 0.0395(8) Uani d 1 . . C
C8 0.4430(5) 0.4919(5) 0.2793(2) 0.0423(8) Uani d 1 . . C
C9 -0.0053(5) 0.8069(5) 0.7727(2) 0.0426(8) Uani d 1 . . C
C10 0.1598(5) 0.5746(5) 0.6089(2) 0.0397(8) Uani d 1 . . C
H10 0.112896 0.526495 0.662313 0.048 Uiso calc 1 . . H
C11 0.2333(5) 0.4645(5) 0.5300(2) 0.0373(8) Uani d 1 . . C
H11 0.237742 0.34157 0.530659 0.045 Uiso calc 1 . . H
C12 0.3830(5) 0.2351(5) 0.3608(2) 0.0402(8) Uani d 1 . . C
N5 0.0661(5) 1.1910(5) 0.9383(2) 0.0441(8) Uani d 0.5 A 1 N
C16 0.2728(5) 0.8660(5) 0.9585(2) 0.0492(9) Uani d 0.5 A 1 C
N6 0.2728(5) 0.8660(5) 0.9585(2) 0.0492(9) Uani d 0.5 A 2 N
C18 0.0661(5) 1.1910(5) 0.9383(2) 0.0441(8) Uani d 0.5 A 2 C
C13 0.2303(6) 1.2150(6) 0.8876(2) 0.0488(9) Uani d 1 . . C
H13 0.21615 1.332124 0.863538 0.059 Uiso calc 1 A 1 H
C14 0.4143(6) 1.0688(7) 0.8721(3) 0.0522(10) Uani d 1 . . C
H14 0.524664 1.0853 0.837614 0.063 Uiso calc 1 . . H
C15 0.4320(6) 0.8944(7) 0.9094(3) 0.0540(10) Uani d 1 . . C
H15 0.55678 0.794969 0.900199 0.065 Uiso calc 1 A 1 H
C17 0.0868(6) 1.0152(6) 0.9733(2) 0.0463(9) Uani d 1 . . C
C19 0.2825(11) 0.6963(12) 0.9966(6) 0.0505(17) Uani d 0.5 . . C
H19 0.40864 0.598796 0.986881 0.061 Uiso calc 0.5 A 1 H
C20 -0.1224(7) 1.3502(8) 0.9504(4) 0.0263(11) Uani d 0.5 . . C
H20 -0.139736 1.468509 0.927079 0.032 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 178.8(4) . . ?
C3 C2 C1 122.8(3) . . ?
C3 C2 C9 120.5(3) . . ?
C1 C2 C9 116.8(3) . . ?
C2 C3 C10 120.6(3) . . ?
C2 C3 C4 121.2(3) . . ?
C10 C3 C4 118.2(3) . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 C11 121.1(3) . . ?
C5 C6 C11 117.8(3) . . ?
C6 C7 C12 121.9(3) . . ?
C6 C7 C8 122.1(3) . . ?
C12 C7 C8 115.9(3) . . ?
N2 C8 C7 178.1(4) . . ?
N3 C9 C2 178.5(4) . . ?
C11 C10 C3 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C3 C10 H10 119.6 . . ?
C10 C11 C6 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
N4 C12 C7 178.8(4) . . ?
C13 N5 C17 119.5(3) . . ?
C13 N5 C20 117.7(4) . . ?
C17 N5 C20 122.8(4) . . ?
C15 C16 C19 124.1(5) . . ?
C15 C16 C17 119.1(4) . . ?
C19 C16 C17 116.8(4) . . ?
C15 N6 C19 124.1(5) . . ?
C15 N6 C17 119.1(4) . . ?
C19 N6 C17 116.8(4) . . ?
C13 C18 C17 119.5(3) . . ?
C13 C18 C20 117.7(4) . . ?
C17 C18 C20 122.8(4) . . ?
C14 C13 N5 121.0(4) . . ?
C14 C13 C18 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
N5 C13 H13 119.5 . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
N6 C15 C14 121.9(4) . . ?
C16 C15 C14 121.9(4) . . ?
C16 C15 H15 119 . . ?
C14 C15 H15 119 . . ?
N6 C17 C18 120.1(3) . . ?
C16 C17 N5 120.1(3) . . ?
C16 C17 C17 119.2(5) . 2_577 ?
N5 C17 C17 120.6(5) . 2_577 ?
N6 C19 C20 128.8(6) . 2_577 ?
C16 C19 C20 128.8(6) . 2_577 ?
C16 C19 H19 115.6 . . ?
C20 C19 H19 115.6 2_577 . ?
N5 C20 C19 111.7(5) . 2_577 ?
N5 C20 H20 124.1 . . ?
C19 C20 H20 124.1 2_577 . ?
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 . 1.131(5) ?
N2 C8 . 1.154(5) ?
N3 C9 . 1.159(5) ?
N4 C12 . 1.149(5) ?
C1 C2 . 1.431(5) ?
C2 C3 . 1.394(5) ?
C2 C9 . 1.432(5) ?
C3 C10 . 1.429(5) ?
C3 C4 . 1.443(5) ?
C4 C5 . 1.349(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.433(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.398(5) ?
C6 C11 . 1.435(5) ?
C7 C12 . 1.426(5) ?
C7 C8 . 1.430(5) ?
C10 C11 . 1.361(5) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
N5 C13 . 1.379(5) ?
N5 C17 . 1.392(6) ?
N5 C20 . 1.438(6) ?
C16 C15 . 1.354(5) ?
C16 C19 . 1.383(10) ?
C16 C17 . 1.391(5) ?
N6 C15 . 1.354(5) ?
N6 C19 . 1.383(10) ?
N6 C17 . 1.391(5) ?
C18 C13 . 1.379(5) ?
C18 C17 . 1.392(6) ?
C18 C20 . 1.438(6) ?
C13 C14 . 1.372(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.398(7) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C17 C17 2_577 1.473(7) ?
C19 C20 2_577 1.452(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
C1 C2 C3 C10 -179.2(3) . . . . ?
C9 C2 C3 C10 0.0(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C9 C2 C3 C4 178.3(3) . . . . ?
C2 C3 C4 C5 -177.1(3) . . . . ?
C10 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C4 C5 C6 C11 -0.2(5) . . . . ?
C5 C6 C7 C12 -179.4(3) . . . . ?
C11 C6 C7 C12 1.4(5) . . . . ?
C5 C6 C7 C8 -2.9(5) . . . . ?
C11 C6 C7 C8 177.9(3) . . . . ?
C2 C3 C10 C11 178.1(3) . . . . ?
C4 C3 C10 C11 -0.2(5) . . . . ?
C3 C10 C11 C6 -1.0(5) . . . . ?
C7 C6 C11 C10 -179.6(3) . . . . ?
C5 C6 C11 C10 1.2(5) . . . . ?
C17 N5 C13 C14 -0.8(5) . . . . ?
C20 N5 C13 C14 -179.1(4) . . . . ?
C17 C18 C13 C14 -0.8(5) . . . . ?
C20 C18 C13 C14 -179.1(4) . . . . ?
N5 C13 C14 C15 -0.3(6) . . . . ?
C18 C13 C14 C15 -0.3(6) . . . . ?
C19 N6 C15 C14 179.8(5) . . . . ?
C17 N6 C15 C14 -0.7(6) . . . . ?
C19 C16 C15 C14 179.8(5) . . . . ?
C17 C16 C15 C14 -0.7(6) . . . . ?
C13 C14 C15 N6 1.1(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C15 N6 C17 C18 -0.4(5) . . . . ?
C19 N6 C17 C18 179.1(5) . . . . ?
C15 N6 C17 C17 180.0(4) . . . 2_577 ?
C19 N6 C17 C17 -0.5(7) . . . 2_577 ?
C15 C16 C17 N5 -0.4(5) . . . . ?
C19 C16 C17 N5 179.1(5) . . . . ?
C15 C16 C17 C17 180.0(4) . . . 2_577 ?
C19 C16 C17 C17 -0.5(7) . . . 2_577 ?
C13 C18 C17 N6 1.1(5) . . . . ?
C20 C18 C17 N6 179.4(3) . . . . ?
C13 C18 C17 C17 -179.3(3) . . . 2_577 ?
C20 C18 C17 C17 -1.0(6) . . . 2_577 ?
C13 N5 C17 C16 1.1(5) . . . . ?
C20 N5 C17 C16 179.4(3) . . . . ?
C13 N5 C17 C17 -179.3(3) . . . 2_577 ?
C20 N5 C17 C17 -1.0(6) . . . 2_577 ?
C15 N6 C19 C20 -179.6(6) . . . 2_577 ?
C17 N6 C19 C20 1.0(10) . . . 2_577 ?
C15 C16 C19 C20 -179.6(6) . . . 2_577 ?
C17 C16 C19 C20 1.0(10) . . . 2_577 ?
C13 C18 C20 C19 178.9(4) . . . 2_577 ?
C17 C18 C20 C19 0.6(7) . . . 2_577 ?
C13 N5 C20 C19 178.9(4) . . . 2_577 ?
C17 N5 C20 C19 0.6(7) . . . 2_577 ?
