#------------------------------------------------------------------------------
#$Date: 2022-05-28 05:04:34 +0300 (Sat, 28 May 2022) $
#$Revision: 275679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567034.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_1567034
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 H4 N4, 0.5(C6 H10 N2)'
_chemical_formula_sum            'C15 H9 N5'
_chemical_formula_weight         259.27
_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   mixed
_audit_creation_date             2020-10-02T13:41:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                106.174(6)
_cell_angle_beta                 90.739(4)
_cell_angle_gamma                112.525(5)
_cell_formula_units_Z            2
_cell_length_a                   7.1924(3)
_cell_length_b                   7.8489(5)
_cell_length_c                   13.6170(9)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.848
_cell_measurement_theta_min      6.271
_cell_volume                     675.74(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 0.987
_diffrn_measured_fraction_theta_max 0.964
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5385
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.054
_diffrn_reflns_theta_min         3.411
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.47668
_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    1.274
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0589
_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)+(0.1372P)²+0.0307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.193
_reflns_number_gt                2333
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5043.cif
_cod_data_source_block           tcnq_4pic_1
_cod_original_cell_volume        675.74(7)
_cod_database_code               1567034
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 0.5900(3) 0.4903(3) 0.87114(13) 0.0892(5) Uani d 1 . . N
N2 0.1195(3) -0.4775(2) 0.35130(13) 0.0741(4) Uani d 1 . . N
N3 0.4239(3) 0.8328(2) 0.71277(13) 0.0789(5) Uani d 1 . . N
N4 -0.0006(3) -0.1364(3) 0.17785(13) 0.0962(6) Uani d 1 . . N
C1 0.5169(3) 0.4972(2) 0.79853(12) 0.0632(4) Uani d 1 . . C
C2 0.4262(2) 0.5039(2) 0.70676(11) 0.0539(4) Uani d 1 . . C
C3 0.34700(19) 0.34177(19) 0.61936(11) 0.0495(3) Uani d 1 . . C
C4 0.3468(2) 0.15895(19) 0.62008(11) 0.0505(3) Uani d 1 . . C
H4 0.39736 0.148148 0.680238 0.061 Uiso calc 1 . . H
C5 0.27444(19) 0.00218(19) 0.53470(11) 0.0500(3) Uani d 1 . . C
H5 0.274536 -0.11476 0.537625 0.06 Uiso calc 1 . . H
C6 0.19768(18) 0.01275(19) 0.43997(11) 0.0485(3) Uani d 1 . . C
C7 0.1268(2) -0.1476(2) 0.35213(11) 0.0524(3) Uani d 1 . . C
C8 0.1242(2) -0.3304(2) 0.35195(11) 0.0558(4) Uani d 1 . . C
C9 0.4247(2) 0.6860(2) 0.70923(12) 0.0596(4) Uani d 1 . . C
C10 0.2671(2) 0.35155(19) 0.52524(11) 0.0513(3) Uani d 1 . . C
H10 0.264127 0.467787 0.522922 0.062 Uiso calc 1 . . H
C11 0.1958(2) 0.1954(2) 0.43947(11) 0.0517(3) Uani d 1 . . C
H11 0.144919 0.206299 0.379422 0.062 Uiso calc 1 . . H
C12 0.0566(3) -0.1406(2) 0.25563(12) 0.0642(4) Uani d 1 . . C
N5 0.3009(3) 0.8891(3) 0.96056(12) 0.0767(5) Uani d 0.5 . . N
N6 0.0829(5) 0.7700(5) 0.9162(2) 0.1262(10) Uani d 0.5 . . N
C13 0.4088(4) 0.8204(3) 1.00807(15) 0.0813(5) Uani d 1 . . C
H13 0.346653 0.696371 1.013937 0.098 Uiso calc 1 . . H
C14 0.3951(4) 1.0716(3) 0.95292(15) 0.0833(6) Uani d 1 . . C
H14 0.322951 1.1216 0.920452 0.1 Uiso calc 1 . . H
C15 0.3009(3) 0.8891(3) 0.96056(12) 0.0767(5) Uani d 0.5 . . C
C16 0.0829(5) 0.7700(5) 0.9162(2) 0.1262(10) Uani d 0.5 . . C
H16C 0.113(7) 0.652(5) 0.923(3) 0.189 Uiso d 1 . . H
H16A -0.039(4) 0.704(6) 0.947(3) 0.189 Uiso d 1 . . H
H16B 0.034(6) 0.731(6) 0.8434(15) 0.189 Uiso d 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'
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 179.22(19) . . ?
C3 C2 C9 122.28(13) . . ?
C3 C2 C1 121.56(13) . . ?
C9 C2 C1 116.15(13) . . ?
C2 C3 C10 121.56(12) . . ?
C2 C3 C4 120.91(13) . . ?
C10 C3 C4 117.52(12) . . ?
C5 C4 C3 121.15(12) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.35(12) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.14(12) . . ?
C7 C6 C11 121.33(12) . . ?
C5 C6 C11 117.53(12) . . ?
C6 C7 C12 122.72(13) . . ?
C6 C7 C8 121.97(13) . . ?
C12 C7 C8 115.30(13) . . ?
N2 C8 C7 179.12(17) . . ?
N3 C9 C2 178.99(17) . . ?
C11 C10 C3 121.52(12) . . ?
C11 C10 H10 119.2 . . ?
C3 C10 H10 119.2 . . ?
C10 C11 C6 120.92(12) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
N4 C12 C7 179.5(2) . . ?
C13 N5 N6 121.5(2) . . ?
N5 N6 H16C 85(3) . . ?
N5 N6 H16A 132(2) . . ?
H16C N6 H16A 80(2) . . ?
N5 N6 H16B 123(3) . . ?
H16C N6 H16B 103(3) . . ?
H16A N6 H16B 105(2) . . ?
C14 C13 N5 120.98(19) 2_677 . ?
C14 C13 H13 119.5 2_677 . ?
N5 C13 H13 119.5 . . ?
C13 C14 H14 119.8 2_677 . ?
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 . 1.138(2) ?
N2 C8 . 1.140(2) ?
N3 C9 . 1.143(2) ?
N4 C12 . 1.145(2) ?
C1 C2 . 1.426(2) ?
C2 C3 . 1.394(2) ?
C2 C9 . 1.424(2) ?
C3 C10 . 1.4311(19) ?
C3 C4 . 1.4373(17) ?
C4 C5 . 1.354(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.4325(18) ?
C5 H5 . 0.93 ?
C6 C7 . 1.389(2) ?
C6 C11 . 1.4410(18) ?
C7 C12 . 1.424(2) ?
C7 C8 . 1.4274(19) ?
C10 C11 . 1.354(2) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
N5 C13 . 1.347(3) ?
N5 N6 . 1.495(3) ?
N6 H16C . 1.062(18) ?
N6 H16A . 0.998(17) ?
N6 H16B . 0.968(18) ?
C13 C14 2_677 1.343(3) ?
C13 H13 . 0.93 ?
C14 H14 . 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 2.7(2) . . . . ?
C1 C2 C3 C10 -176.14(13) . . . . ?
C9 C2 C3 C4 -178.65(12) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C2 C3 C4 C5 -178.46(12) . . . . ?
C10 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C7 178.89(12) . . . . ?
C4 C5 C6 C11 -1.4(2) . . . . ?
C5 C6 C7 C12 -177.56(12) . . . . ?
C11 C6 C7 C12 2.8(2) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C11 C6 C7 C8 -178.82(11) . . . . ?
C2 C3 C10 C11 178.00(12) . . . . ?
C4 C3 C10 C11 -0.7(2) . . . . ?
C3 C10 C11 C6 0.1(2) . . . . ?
C7 C6 C11 C10 -179.34(12) . . . . ?
C5 C6 C11 C10 1.0(2) . . . . ?
N6 N5 C13 C14 179.6(2) . . . 2_677 ?
