#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567028.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_1567028
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 H6 Br2 N'
_chemical_formula_sum            'C30 H14 Br2 N9'
_chemical_formula_weight         660.32
_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             2020-10-02T14:03:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                97.673(2)
_cell_angle_beta                 90.168(2)
_cell_angle_gamma                108.973(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6911(2)
_cell_length_b                   7.8201(3)
_cell_length_c                   27.6491(6)
_cell_measurement_reflns_used    6687
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.294
_cell_measurement_theta_min      3.213
_cell_volume                     1354.23(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 0.998
_diffrn_measured_fraction_theta_max 0.981
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11901
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.473
_diffrn_reflns_theta_min         3.23
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.115
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.56283
_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    1.619
_exptl_crystal_description       plate
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0434
_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)+(0.0711P)²+0.6968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                5100
_reflns_number_total             5582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_35brme
_cod_original_cell_volume        1354.24(8)
_cod_database_code               1567028
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 0.96358(4) -0.03531(4) 0.20508(2) 0.02977(11) Uani d 1 . . Br
Br2 0.30401(5) 0.05369(4) 0.32482(2) 0.03150(11) Uani d 1 . . Br
N5 0.4141(3) -0.3825(3) 0.24558(7) 0.0224(4) Uani d 1 . . N
C13 0.6004(4) -0.3134(3) 0.22598(8) 0.0227(5) Uani d 1 . . C
H13 0.658769 -0.39 0.206647 0.027 Uiso calc 1 . . H
C14 0.7055(4) -0.1280(3) 0.23457(8) 0.0224(5) Uani d 1 . . C
C15 0.6219(4) -0.0116(3) 0.26385(7) 0.0232(5) Uani d 1 . . C
H15 0.692374 0.113638 0.269877 0.028 Uiso calc 1 . . H
C16 0.4283(4) -0.0905(4) 0.28375(8) 0.0243(5) Uani d 1 . . C
C17 0.3237(4) -0.2765(4) 0.27380(8) 0.0239(5) Uani d 1 . . C
H17 0.192436 -0.327917 0.286425 0.029 Uiso calc 1 . . H
C18 0.3043(4) -0.5829(4) 0.23776(10) 0.0300(5) Uani d 1 . . C
H18A 0.17343 -0.610465 0.25406 0.045 Uiso calc 1 . . H
H18B 0.275795 -0.624952 0.203401 0.045 Uiso calc 1 . . H
H18C 0.392526 -0.642841 0.250752 0.045 Uiso calc 1 . . H
N1A 0.7125(4) 0.0081(3) 0.54910(8) 0.0297(5) Uani d 1 . . N
N2A 0.7891(4) 0.4755(3) 0.29460(8) 0.0300(5) Uani d 1 . . N
N3A 0.7381(4) 0.5184(3) 0.63798(8) 0.0299(5) Uani d 1 . . N
N4A 0.7914(5) 0.9919(4) 0.37778(9) 0.0361(5) Uani d 1 . . N
C1A 0.7233(4) 0.1587(4) 0.55031(8) 0.0228(5) Uani d 1 . . C
C2A 0.7392(4) 0.3459(3) 0.55176(8) 0.0204(4) Uani d 1 . . C
C3A 0.7524(3) 0.4260(3) 0.50915(8) 0.0206(5) Uani d 1 . . C
C4A 0.7492(4) 0.3210(3) 0.46235(8) 0.0205(4) Uani d 1 . . C
H4A 0.737846 0.198586 0.460519 0.025 Uiso calc 1 . . H
C5A 0.7623(4) 0.3973(4) 0.42058(8) 0.0217(5) Uani d 1 . . C
H5A 0.760027 0.326424 0.390636 0.026 Uiso calc 1 . . H
C6A 0.7796(3) 0.5847(3) 0.42202(8) 0.0203(4) Uani d 1 . . C
C7A 0.7900(4) 0.6627(4) 0.37889(8) 0.0225(5) Uani d 1 . . C
C8A 0.7892(4) 0.5593(4) 0.33232(9) 0.0242(5) Uani d 1 . . C
C9A 0.7390(4) 0.4441(4) 0.59927(9) 0.0229(5) Uani d 1 . . C
C10A 0.7684(4) 0.6139(3) 0.51078(8) 0.0212(4) Uani d 1 . . C
H10A 0.769589 0.684363 0.540727 0.025 Uiso calc 1 . . H
C11A 0.7818(4) 0.6905(3) 0.46885(8) 0.0210(4) Uani d 1 . . C
H11A 0.792532 0.812736 0.470592 0.025 Uiso calc 1 . . H
C12A 0.7930(4) 0.8456(4) 0.37885(8) 0.0264(5) Uani d 1 . . C
N1B 0.4952(4) -0.4401(4) 0.10323(9) 0.0357(5) Uani d 1 . . N
N3B 0.4306(4) 0.0781(4) 0.17008(8) 0.0357(5) Uani d 1 . . N
C1B 0.4856(4) -0.2986(4) 0.09823(9) 0.0280(5) Uani d 1 . . C
C2B 0.4719(4) -0.1250(4) 0.09221(8) 0.0252(5) Uani d 1 . . C
C3B 0.4859(4) -0.0624(4) 0.04625(8) 0.0242(5) Uani d 1 . . C
C4B 0.5087(4) -0.1744(4) 0.00295(9) 0.0251(5) Uani d 1 . . C
H4B 0.514623 -0.290406 0.004974 0.03 Uiso calc 1 . . H
C9B 0.4485(4) -0.0132(4) 0.13551(9) 0.0275(5) Uani d 1 . . C
C10B 0.4779(4) 0.1140(4) 0.04160(8) 0.0243(5) Uani d 1 . . C
H10B 0.463231 0.18985 0.069302 0.029 Uiso calc 1 . . H
N1C 1.0064(4) 0.0206(3) 0.08490(8) 0.0284(5) Uani d 1 . . N
N3C 0.9561(5) 0.5129(4) 0.17100(8) 0.0378(6) Uani d 1 . . N
C1C 0.9974(4) 0.1650(4) 0.08525(8) 0.0231(5) Uani d 1 . . C
C2C 0.9838(4) 0.3443(4) 0.08579(8) 0.0220(5) Uani d 1 . . C
C3C 0.9907(4) 0.4218(4) 0.04347(8) 0.0214(5) Uani d 1 . . C
C4C 1.0152(4) 0.3239(4) -0.00298(8) 0.0225(5) Uani d 1 . . C
H4C 1.024349 0.207208 -0.004311 0.027 Uiso calc 1 . . H
C9C 0.9657(4) 0.4384(4) 0.13287(9) 0.0266(5) Uani d 1 . . C
C10C 0.9750(4) 0.6011(4) 0.04459(8) 0.0223(5) Uani d 1 . . C
H10C 0.958021 0.666039 0.074125 0.027 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 0.0181 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
C13 N5 C17 122.2(2) . . ?
C13 N5 C18 119.6(2) . . ?
C17 N5 C18 118.2(2) . . ?
N5 C13 C14 119.6(2) . . ?
N5 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 Br1 118.34(18) . . ?
C15 C14 Br1 120.61(19) . . ?
C14 C15 C16 117.2(2) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 H15 121.4 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 Br2 118.64(19) . . ?
C15 C16 Br2 120.62(19) . . ?
N5 C17 C16 119.3(2) . . ?
N5 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
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 . . ?
N1A C1A C2A 179.3(3) . . ?
C3A C2A C1A 121.6(2) . . ?
C3A C2A C9A 122.6(2) . . ?
C1A C2A C9A 115.8(2) . . ?
C2A C3A C10A 121.4(2) . . ?
C2A C3A C4A 120.5(2) . . ?
C10A C3A C4A 118.2(2) . . ?
C5A C4A C3A 121.1(2) . . ?
C5A C4A H4A 119.4 . . ?
C3A C4A H4A 119.4 . . ?
C4A C5A C6A 120.9(2) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
C7A C6A C5A 120.9(2) . . ?
C7A C6A C11A 120.9(2) . . ?
C5A C6A C11A 118.2(2) . . ?
C6A C7A C12A 122.3(2) . . ?
C6A C7A C8A 121.3(2) . . ?
C12A C7A C8A 116.4(2) . . ?
N2A C8A C7A 179.8(3) . . ?
N3A C9A C2A 178.0(3) . . ?
C11A C10A C3A 120.7(2) . . ?
C11A C10A H10A 119.7 . . ?
C3A C10A H10A 119.7 . . ?
C10A C11A C6A 120.9(2) . . ?
C10A C11A H11A 119.6 . . ?
C6A C11A H11A 119.6 . . ?
N4A C12A C7A 178.2(3) . . ?
N1B C1B C2B 179.5(3) . . ?
C3B C2B C1B 122.6(2) . . ?
C3B C2B C9B 121.1(2) . . ?
C1B C2B C9B 116.3(2) . . ?
C2B C3B C10B 121.3(2) . . ?
C2B C3B C4B 121.1(2) . . ?
C10B C3B C4B 117.7(2) . . ?
C10B C4B C3B 121.1(3) 2_655 . ?
C10B C4B H4B 119.4 2_655 . ?
C3B C4B H4B 119.4 . . ?
N3B C9B C2B 179.3(3) . . ?
C4B C10B C3B 121.2(2) 2_655 . ?
C4B C10B H10B 119.4 2_655 . ?
C3B C10B H10B 119.4 . . ?
N1C C1C C2C 179.4(3) . . ?
C3C C2C C1C 121.8(2) . . ?
C3C C2C C9C 122.4(2) . . ?
C1C C2C C9C 115.8(2) . . ?
C2C C3C C10C 121.1(2) . . ?
C2C C3C C4C 120.5(2) . . ?
C10C C3C C4C 118.5(2) . . ?
C10C C4C C3C 121.1(2) 2_765 . ?
C10C C4C H4C 119.4 2_765 . ?
C3C C4C H4C 119.4 . . ?
N3C C9C C2C 178.1(3) . . ?
C4C C10C C3C 120.4(2) 2_765 . ?
C4C C10C H10C 119.8 2_765 . ?
C3C C10C H10C 119.8 . . ?
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 . 1.877(2) ?
Br2 C16 . 1.878(3) ?
N5 C13 . 1.336(3) ?
N5 C17 . 1.348(3) ?
N5 C18 . 1.484(3) ?
C13 C14 . 1.377(4) ?
C13 H13 . 0.93 ?
C14 C15 . 1.391(3) ?
C15 C16 . 1.392(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.382(4) ?
C17 H17 . 0.93 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
N1A C1A . 1.152(4) ?
N2A C8A . 1.155(4) ?
N3A C9A . 1.149(4) ?
N4A C12A . 1.152(4) ?
C1A C2A . 1.428(4) ?
C2A C3A . 1.397(3) ?
C2A C9A . 1.431(3) ?
C3A C10A . 1.432(4) ?
C3A C4A . 1.433(3) ?
C4A C5A . 1.360(3) ?
C4A H4A . 0.93 ?
C5A C6A . 1.427(4) ?
C5A H5A . 0.93 ?
C6A C7A . 1.402(3) ?
C6A C11A . 1.438(3) ?
C7A C12A . 1.424(4) ?
C7A C8A . 1.425(3) ?
C10A C11A . 1.364(3) ?
C10A H10A . 0.93 ?
C11A H11A . 0.93 ?
N1B C1B . 1.155(4) ?
N3B C9B . 1.145(4) ?
C1B C2B . 1.422(4) ?
C2B C3B . 1.414(3) ?
C2B C9B . 1.426(4) ?
C3B C10B . 1.420(4) ?
C3B C4B . 1.425(3) ?
C4B C10B 2_655 1.370(3) ?
C4B H4B . 0.93 ?
C10B H10B . 0.93 ?
N1C C1C . 1.149(4) ?
N3C C9C . 1.147(4) ?
C1C C2C . 1.432(4) ?
C2C C3C . 1.382(3) ?
C2C C9C . 1.433(3) ?
C3C C10C . 1.436(4) ?
C3C C4C . 1.443(3) ?
C4C C10C 2_765 1.352(3) ?
C4C H4C . 0.93 ?
C10C H10C . 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 0.0(3) . . . . ?
C18 N5 C13 C14 -177.9(2) . . . . ?
N5 C13 C14 C15 0.8(3) . . . . ?
N5 C13 C14 Br1 -178.45(16) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
Br1 C14 C15 C16 178.99(16) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C14 C15 C16 Br2 178.77(16) . . . . ?
C13 N5 C17 C16 -1.3(3) . . . . ?
C18 N5 C17 C16 176.6(2) . . . . ?
C15 C16 C17 N5 1.9(3) . . . . ?
Br2 C16 C17 N5 -177.99(17) . . . . ?
C1A C2A C3A C10A 180.0(2) . . . . ?
C9A C2A C3A C10A 0.5(3) . . . . ?
C1A C2A C3A C4A 0.3(3) . . . . ?
C9A C2A C3A C4A -179.2(2) . . . . ?
C2A C3A C4A C5A -179.8(2) . . . . ?
C10A C3A C4A C5A 0.5(3) . . . . ?
C3A C4A C5A C6A -0.1(4) . . . . ?
C4A C5A C6A C7A -179.0(2) . . . . ?
C4A C5A C6A C11A -0.3(3) . . . . ?
C5A C6A C7A C12A 175.7(2) . . . . ?
C11A C6A C7A C12A -3.0(4) . . . . ?
C5A C6A C7A C8A -1.7(4) . . . . ?
C11A C6A C7A C8A 179.6(2) . . . . ?
C2A C3A C10A C11A 179.8(2) . . . . ?
C4A C3A C10A C11A -0.5(3) . . . . ?
C3A C10A C11A C6A 0.2(3) . . . . ?
C7A C6A C11A C10A 179.0(2) . . . . ?
C5A C6A C11A C10A 0.2(3) . . . . ?
C1B C2B C3B C10B -178.2(2) . . . . ?
C9B C2B C3B C10B 0.2(4) . . . . ?
C1B C2B C3B C4B 1.8(4) . . . . ?
C9B C2B C3B C4B -179.8(2) . . . . ?
C2B C3B C4B C10B 179.9(2) . . . 2_655 ?
C10B C3B C4B C10B -0.1(4) . . . 2_655 ?
C2B C3B C10B C4B -179.9(2) . . . 2_655 ?
C4B C3B C10B C4B 0.1(4) . . . 2_655 ?
C1C C2C C3C C10C 179.5(2) . . . . ?
C9C C2C C3C C10C -1.4(4) . . . . ?
C1C C2C C3C C4C -0.9(4) . . . . ?
C9C C2C C3C C4C 178.2(2) . . . . ?
C2C C3C C4C C10C -179.1(2) . . . 2_765 ?
C10C C3C C4C C10C 0.5(4) . . . 2_765 ?
C2C C3C C10C C4C 179.1(2) . . . 2_765 ?
C4C C3C C10C C4C -0.5(4) . . . 2_765 ?
