#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567024.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_1567024
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), C7 H8 Br2 N'
_chemical_formula_sum            'C31 H16 Br2 N9'
_chemical_formula_weight         674.35
_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             2020-10-02T13:56:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.624(2)
_cell_angle_beta                 98.576(2)
_cell_angle_gamma                104.767(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0361(3)
_cell_length_b                   13.0398(3)
_cell_length_c                   14.2071(4)
_cell_measurement_reflns_used    8501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.809
_cell_measurement_theta_min      3.146
_cell_volume                     1418.00(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 0.996
_diffrn_measured_fraction_theta_max 0.985
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12861
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.157
_diffrn_reflns_theta_min         3.158
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.943
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.54258
_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    1.579
_exptl_crystal_description       plate
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.836
_refine_diff_density_min         -1.02
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.778
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.778
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0416
_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)+(0.0855P)²+2.5012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                5366
_reflns_number_total             5835
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_35bret
_cod_original_cell_volume        1418.00(7)
_cod_database_code               1567024
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
Br1 0.72222(3) 0.91221(2) 0.65465(2) 0.03351(10) Uani d 1 . . Br
Br2 0.37038(5) 0.47266(2) 0.60162(2) 0.04291(11) Uani d 1 . . Br
N5 0.2578(3) 0.73913(16) 0.50303(13) 0.0209(4) Uani d 1 . . N
C13 0.3980(3) 0.81944(18) 0.53890(16) 0.0217(4) Uani d 1 . . C
H13 0.401378 0.888992 0.525412 0.026 Uiso calc 1 . . H
C14 0.5367(3) 0.79733(19) 0.59598(16) 0.0238(4) Uani d 1 . . C
C15 0.5342(3) 0.6946(2) 0.61479(17) 0.0270(5) Uani d 1 . . C
H15 0.629022 0.67907 0.65166 0.032 Uiso calc 1 . . H
C16 0.3858(4) 0.61503(19) 0.57698(17) 0.0266(5) Uani d 1 . . C
C17 0.2476(3) 0.63849(18) 0.52078(16) 0.0235(4) Uani d 1 . . C
H17 0.148204 0.584671 0.495499 0.028 Uiso calc 1 . . H
C18 0.1071(3) 0.7638(2) 0.44254(18) 0.0304(5) Uani d 1 . . C
H18A 0.046245 0.703038 0.397363 0.036 Uiso calc 1 . . H
H18B 0.149171 0.823823 0.406607 0.036 Uiso calc 1 . . H
C19 -0.0173(4) 0.7899(3) 0.5039(2) 0.0381(6) Uani d 1 . . C
H19A -0.113529 0.805543 0.463991 0.057 Uiso calc 1 . . H
H19B -0.060124 0.73004 0.538776 0.057 Uiso calc 1 . . H
H19C 0.042615 0.850605 0.548003 0.057 Uiso calc 1 . . H
N1A 1.3909(3) 0.3800(2) 1.16972(16) 0.0339(5) Uani d 1 . . N
N2A 0.6354(3) 0.30165(19) 0.67969(15) 0.0333(5) Uani d 1 . . N
N3A 1.0343(3) 0.4558(2) 1.34768(16) 0.0364(5) Uani d 1 . . N
N4A 0.2662(3) 0.36503(17) 0.84928(16) 0.0288(4) Uani d 1 . . N
C1A 1.2534(3) 0.3903(2) 1.17385(16) 0.0264(5) Uani d 1 . . C
C2A 1.0847(3) 0.40287(18) 1.17936(16) 0.0234(4) Uani d 1 . . C
C3A 0.9566(3) 0.38753(17) 1.09751(16) 0.0201(4) Uani d 1 . . C
C4A 0.9953(3) 0.36020(17) 1.00553(16) 0.0209(4) Uani d 1 . . C
H4A 1.105021 0.351063 1.000988 0.025 Uiso calc 1 . . H
C5A 0.8748(3) 0.34753(17) 0.92537(15) 0.0203(4) Uani d 1 . . C
H5A 0.90291 0.330006 0.866618 0.024 Uiso calc 1 . . H
C6A 0.7038(3) 0.36087(16) 0.93008(15) 0.0195(4) Uani d 1 . . C
C7A 0.5784(3) 0.34737(17) 0.84837(16) 0.0207(4) Uani d 1 . . C
C8A 0.6127(3) 0.32187(18) 0.75550(16) 0.0233(5) Uani d 1 . . C
C9A 1.0541(3) 0.4318(2) 1.27230(17) 0.0269(5) Uani d 1 . . C
C10A 0.7867(3) 0.40079(17) 1.10215(16) 0.0214(4) Uani d 1 . . C
H10A 0.758838 0.418312 1.160959 0.026 Uiso calc 1 . . H
C11A 0.6657(3) 0.38822(17) 1.02217(16) 0.0213(4) Uani d 1 . . C
H11A 0.556208 0.397461 1.026956 0.026 Uiso calc 1 . . H
C12A 0.4067(3) 0.35878(17) 0.85021(16) 0.0222(4) Uani d 1 . . C
N1B 1.0697(3) 0.10913(19) 0.08899(16) 0.0317(5) Uani d 1 . . N
N2B 0.3339(3) 0.04668(18) -0.40494(15) 0.0324(5) Uani d 1 . . N
N3B 0.7238(3) 0.19482(18) 0.26325(15) 0.0303(5) Uani d 1 . . N
N4B -0.0399(3) 0.12220(18) -0.23740(15) 0.0299(4) Uani d 1 . . N
C1B 0.9343(3) 0.12297(18) 0.08992(15) 0.0228(4) Uani d 1 . . C
C2B 0.7665(3) 0.14082(17) 0.09337(15) 0.0194(4) Uani d 1 . . C
C3B 0.6413(3) 0.12847(16) 0.01180(15) 0.0182(4) Uani d 1 . . C
C4B 0.6779(3) 0.09883(17) -0.08011(15) 0.0194(4) Uani d 1 . . C
H4B 0.785583 0.086542 -0.084682 0.023 Uiso calc 1 . . H
C5B 0.5575(3) 0.08855(17) -0.16033(15) 0.0203(4) Uani d 1 . . C
H5B 0.584762 0.070264 -0.219096 0.024 Uiso calc 1 . . H
C6B 0.3894(3) 0.10529(16) -0.15617(15) 0.0194(4) Uani d 1 . . C
C7B 0.2656(3) 0.09403(17) -0.23919(16) 0.0214(4) Uani d 1 . . C
C8B 0.3032(3) 0.06748(18) -0.33081(16) 0.0238(5) Uani d 1 . . C
C9B 0.7389(3) 0.17077(18) 0.18681(16) 0.0213(4) Uani d 1 . . C
C10B 0.4713(3) 0.14434(16) 0.01618(15) 0.0187(4) Uani d 1 . . C
H10B 0.443735 0.162627 0.074868 0.022 Uiso calc 1 . . H
C11B 0.3512(3) 0.13296(17) -0.06413(16) 0.0196(4) Uani d 1 . . C
H11B 0.242172 0.143222 -0.059609 0.023 Uiso calc 1 . . H
C12B 0.0971(3) 0.10971(18) -0.23758(16) 0.0238(5) Uani d 1 . . 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C17 N5 C13 122.3(2) . . ?
C17 N5 C18 118.9(2) . . ?
C13 N5 C18 118.8(2) . . ?
N5 C13 C14 119.1(2) . . ?
N5 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 Br1 120.73(18) . . ?
C13 C14 Br1 118.25(18) . . ?
C14 C15 C16 117.7(2) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 Br2 118.98(19) . . ?
C15 C16 Br2 120.27(19) . . ?
N5 C17 C16 119.3(2) . . ?
N5 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
N5 C18 C19 110.5(2) . . ?
N5 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
N5 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1A C1A C2A 179.8(3) . . ?
C3A C2A C1A 121.2(2) . . ?
C3A C2A C9A 122.5(2) . . ?
C1A C2A C9A 116.3(2) . . ?
C2A C3A C10A 121.7(2) . . ?
C2A C3A C4A 120.2(2) . . ?
C10A C3A C4A 118.1(2) . . ?
C5A C4A C3A 121.1(2) . . ?
C5A C4A H4A 119.4 . . ?
C3A C4A H4A 119.4 . . ?
C4A C5A C6A 120.8(2) . . ?
C4A C5A H5A 119.6 . . ?
C6A C5A H5A 119.6 . . ?
C7A C6A C11A 120.8(2) . . ?
C7A C6A C5A 121.3(2) . . ?
C11A C6A C5A 117.9(2) . . ?
C6A C7A C12A 123.0(2) . . ?
C6A C7A C8A 122.2(2) . . ?
C12A C7A C8A 114.7(2) . . ?
N2A C8A C7A 177.9(3) . . ?
N3A C9A C2A 178.2(3) . . ?
C11A C10A C3A 121.0(2) . . ?
C11A C10A H10A 119.5 . . ?
C3A C10A H10A 119.5 . . ?
C10A C11A C6A 121.1(2) . . ?
C10A C11A H11A 119.4 . . ?
C6A C11A H11A 119.4 . . ?
N4A C12A C7A 177.6(3) . . ?
N1B C1B C2B 178.7(2) . . ?
C3B C2B C9B 123.4(2) . . ?
C3B C2B C1B 121.9(2) . . ?
C9B C2B C1B 114.64(19) . . ?
C2B C3B C4B 120.6(2) . . ?
C2B C3B C10B 121.58(19) . . ?
C4B C3B C10B 117.84(19) . . ?
C5B C4B C3B 120.9(2) . . ?
C5B C4B H4B 119.5 . . ?
C3B C4B H4B 119.5 . . ?
C4B C5B C6B 121.3(2) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B H5B 119.4 . . ?
C7B C6B C5B 120.9(2) . . ?
C7B C6B C11B 121.1(2) . . ?
C5B C6B C11B 118.0(2) . . ?
C6B C7B C12B 122.4(2) . . ?
C6B C7B C8B 121.4(2) . . ?
C12B C7B C8B 116.2(2) . . ?
N2B C8B C7B 179.6(2) . . ?
N3B C9B C2B 177.2(2) . . ?
C11B C10B C3B 120.88(19) . . ?
C11B C10B H10B 119.6 . . ?
C3B C10B H10B 119.6 . . ?
C10B C11B C6B 121.1(2) . . ?
C10B C11B H11B 119.4 . . ?
C6B C11B H11B 119.4 . . ?
N4B C12B C7B 179.2(3) . . ?
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
Br1 C14 . 1.881(2) ?
Br2 C16 . 1.881(2) ?
N5 C17 . 1.332(3) ?
N5 C13 . 1.343(3) ?
N5 C18 . 1.491(3) ?
C13 C14 . 1.378(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.374(3) ?
C15 C16 . 1.384(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.377(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.510(4) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
N1A C1A . 1.156(4) ?
N2A C8A . 1.149(3) ?
N3A C9A . 1.147(3) ?
N4A C12A . 1.150(3) ?
C1A C2A . 1.420(4) ?
C2A C3A . 1.403(3) ?
C2A C9A . 1.430(3) ?
C3A C10A . 1.430(3) ?
C3A C4A . 1.438(3) ?
C4A C5A . 1.354(3) ?
C4A H4A . 0.93 ?
C5A C6A . 1.440(3) ?
C5A H5A . 0.93 ?
C6A C7A . 1.391(3) ?
C6A C11A . 1.437(3) ?
C7A C12A . 1.429(3) ?
C7A C8A . 1.429(3) ?
C10A C11A . 1.355(3) ?
C10A H10A . 0.93 ?
C11A H11A . 0.93 ?
N1B C1B . 1.150(3) ?
N2B C8B . 1.153(3) ?
N3B C9B . 1.149(3) ?
N4B C12B . 1.153(3) ?
C1B C2B . 1.433(3) ?
C2B C3B . 1.390(3) ?
C2B C9B . 1.431(3) ?
C3B C4B . 1.438(3) ?
C3B C10B . 1.443(3) ?
C4B C5B . 1.358(3) ?
C4B H4B . 0.93 ?
C5B C6B . 1.431(3) ?
C5B H5B . 0.93 ?
C6B C7B . 1.401(3) ?
C6B C11B . 1.438(3) ?
C7B C12B . 1.423(3) ?
C7B C8B . 1.427(3) ?
C10B C11B . 1.356(3) ?
C10B H10B . 0.93 ?
C11B H11B . 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
C17 N5 C13 C14 0.1(3) . . . . ?
C18 N5 C13 C14 179.1(2) . . . . ?
N5 C13 C14 C15 1.3(3) . . . . ?
N5 C13 C14 Br1 -174.38(15) . . . . ?
C13 C14 C15 C16 -2.0(3) . . . . ?
Br1 C14 C15 C16 173.55(17) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C14 C15 C16 Br2 -178.71(17) . . . . ?
C13 N5 C17 C16 -0.7(3) . . . . ?
C18 N5 C17 C16 -179.7(2) . . . . ?
C15 C16 C17 N5 -0.1(3) . . . . ?
Br2 C16 C17 N5 -179.96(16) . . . . ?
C17 N5 C18 C19 91.2(3) . . . . ?
C13 N5 C18 C19 -87.8(3) . . . . ?
C1A C2A C3A C10A -179.5(2) . . . . ?
C9A C2A C3A C10A 0.4(3) . . . . ?
C1A C2A C3A C4A -1.0(3) . . . . ?
C9A C2A C3A C4A 179.0(2) . . . . ?
C2A C3A C4A C5A -178.4(2) . . . . ?
C10A C3A C4A C5A 0.1(3) . . . . ?
C3A C4A C5A C6A -0.2(3) . . . . ?
C4A C5A C6A C7A -179.6(2) . . . . ?
C4A C5A C6A C11A 0.2(3) . . . . ?
C11A C6A C7A C12A -0.4(3) . . . . ?
C5A C6A C7A C12A 179.3(2) . . . . ?
C11A C6A C7A C8A 179.0(2) . . . . ?
C5A C6A C7A C8A -1.3(3) . . . . ?
C2A C3A C10A C11A 178.4(2) . . . . ?
C4A C3A C10A C11A -0.1(3) . . . . ?
C3A C10A C11A C6A 0.2(3) . . . . ?
C7A C6A C11A C10A 179.5(2) . . . . ?
C5A C6A C11A C10A -0.2(3) . . . . ?
C9B C2B C3B C4B 179.6(2) . . . . ?
C1B C2B C3B C4B -1.1(3) . . . . ?
C9B C2B C3B C10B -0.6(3) . . . . ?
C1B C2B C3B C10B 178.63(19) . . . . ?
C2B C3B C4B C5B -178.8(2) . . . . ?
C10B C3B C4B C5B 1.5(3) . . . . ?
C3B C4B C5B C6B -0.9(3) . . . . ?
C4B C5B C6B C7B -179.7(2) . . . . ?
C4B C5B C6B C11B -0.3(3) . . . . ?
C5B C6B C7B C12B 179.8(2) . . . . ?
C11B C6B C7B C12B 0.4(3) . . . . ?
C5B C6B C7B C8B -1.2(3) . . . . ?
C11B C6B C7B C8B 179.5(2) . . . . ?
C2B C3B C10B C11B 179.4(2) . . . . ?
C4B C3B C10B C11B -0.8(3) . . . . ?
C3B C10B C11B C6B -0.3(3) . . . . ?
C7B C6B C11B C10B -179.7(2) . . . . ?
C5B C6B C11B C10B 0.9(3) . . . . ?
