#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/22/4002216.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4002216
loop_
_publ_author_name
'Yokokura, Seiya'
'Takahashi, Yukihiro'
'Nonaka, Hiroki'
'Hasegawa, Hiroyuki'
'Harada, Jun'
'Inabe, Tamotsu'
'Kumai, Reiji'
'Okamoto, Hiroshi'
'Matsushita, Michio M.'
'Awaga, Kunio'
_publ_section_title
;
 Switching of Transfer Characteristics of an Organic Field-Effect
 Transistor by Phase Transitions: Sensitive Response to Molecular Dynamics
 and Charge Fluctuation
;
_journal_issue                   12
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4441
_journal_paper_doi               10.1021/acs.chemmater.5b01383
_journal_volume                  27
_journal_year                    2015
_chemical_formula_moiety         '2(C6 H2 N2), 2(C7 H5)'
_chemical_formula_sum            'C26 H14 N4'
_chemical_formula_weight         382.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.884(4)
_cell_angle_beta                 107.171(4)
_cell_angle_gamma                94.998(4)
_cell_formula_units_Z            2
_cell_length_a                   11.370(3)
_cell_length_b                   12.818(3)
_cell_length_c                   6.9180(17)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.093
_cell_measurement_theta_min      2.349
_cell_volume                     958.7(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            18238
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.213
_diffrn_reflns_theta_min         1.596
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.887626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0592 before and 0.0221 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0715 before and 0.0204 after correction.
 The Ratio of minimum to maximum transmission is 0.89.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 18238 reflections, Rint = 0.0312
 (11630 with I > 3sig(I), Rint = 0.0273)
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         7657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0600P)²+0.2508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6628
_reflns_number_total             7657
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm5b01383_si_004.cif
_cod_data_source_block           AN_TCNQ_100K
_cod_original_cell_volume        958.8(4)
_cod_database_code               4002216
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5058(11) 0.4942(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
N1 N 0.09776(13) 0.33035(11) 0.2948(2) 0.0281(3) Uani 1 1 d .
N2 N 0.13043(13) 0.66824(11) 0.3716(2) 0.0271(3) Uani 1 1 d .
C1 C 0.37045(14) 0.50108(11) 0.4431(2) 0.0150(3) Uani 1 1 d .
C2 C 0.42612(14) 0.40435(11) 0.4385(2) 0.0166(3) Uani 1 1 d .
H2 H 0.3747 0.3406 0.3966 0.020 Uiso 1 1 calc R
C3 C 0.45016(15) 0.59681(11) 0.5073(2) 0.0164(3) Uani 1 1 d .
H3 H 0.4152 0.6612 0.5114 0.020 Uiso 1 1 calc R
C4 C 0.24362(15) 0.50121(11) 0.3883(2) 0.0168(3) Uani 1 1 d .
C5 C 0.16276(14) 0.40626(12) 0.3346(2) 0.0194(3) Uani 1 1 d .
C6 C 0.18308(14) 0.59520(12) 0.3822(2) 0.0192(3) Uani 1 1 d .
N3 N 0.40366(13) 0.16700(11) 0.6245(2) 0.0263(3) Uani 1 1 d .
N4 N 0.36816(13) -0.16908(11) 0.6620(2) 0.0258(3) Uani 1 1 d .
C7 C 0.12948(14) -0.00082(11) 0.5478(2) 0.0151(3) Uani 1 1 d .
C8 C 0.07200(14) 0.09536(11) 0.5012(2) 0.0162(3) Uani 1 1 d .
H8 H 0.1220 0.1589 0.5024 0.019 Uiso 1 1 calc R
C9 C 0.05106(15) -0.09641(11) 0.5438(2) 0.0159(3) Uani 1 1 d .
H9 H 0.0871 -0.1607 0.5734 0.019 Uiso 1 1 calc R
C10 C 0.25555(14) -0.00114(11) 0.5947(2) 0.0161(3) Uani 1 1 d .
C11 C 0.33626(14) 0.09297(11) 0.6084(2) 0.0185(3) Uani 1 1 d .
C12 C 0.31652(14) -0.09538(12) 0.6329(2) 0.0184(3) Uani 1 1 d .
C13 C 0.41913(15) 0.57797(12) -0.0046(2) 0.0186(3) Uani 1 1 d .
C14 C 0.33431(16) 0.65462(13) -0.0130(2) 0.0235(3) Uani 1 1 d .
H14 H 0.3651 0.7252 0.0294 0.028 Uiso 1 1 calc R
C15 C 0.21044(17) 0.62855(14) -0.0806(3) 0.0272(4) Uani 1 1 d .
H15 H 0.1554 0.6809 -0.0863 0.033 Uiso 1 1 calc R
C16 C 0.16254(16) 0.52302(15) -0.1430(3) 0.0266(4) Uani 1 1 d .
H16 H 0.0756 0.5053 -0.1892 0.032 Uiso 1 1 calc R
C17 C 0.23997(16) 0.44746(13) -0.1370(2) 0.0226(3) Uani 1 1 d .
H17 H 0.2064 0.3774 -0.1792 0.027 Uiso 1 1 calc R
C18 C 0.37112(15) 0.47159(13) -0.0684(2) 0.0192(3) Uani 1 1 d .
C19 C 0.45329(15) 0.39640(11) -0.0625(2) 0.0196(3) Uani 1 1 d .
H19 H 0.4217 0.3260 -0.1051 0.023 Uiso 1 1 calc R
C20 C 0.11930(14) -0.03479(12) 0.0568(2) 0.0179(3) Uani 1 1 d .
C21 C 0.24182(15) -0.06596(13) 0.1139(2) 0.0222(3) Uani 1 1 d .
H21 H 0.2544 -0.1374 0.1392 0.027 Uiso 1 1 calc R
C22 C 0.34117(16) 0.00523(15) 0.1325(3) 0.0264(4) Uani 1 1 d .
H22 H 0.4220 -0.0172 0.1704 0.032 Uiso 1 1 calc R
C23 C 0.32534(16) 0.11246(15) 0.0959(3) 0.0265(4) Uani 1 1 d .
H23 H 0.3954 0.1614 0.1103 0.032 Uiso 1 1 calc R
C24 C 0.21015(16) 0.14506(13) 0.0404(2) 0.0229(3) Uani 1 1 d .
H24 H 0.2006 0.2170 0.0158 0.027 Uiso 1 1 calc R
C25 C 0.10339(15) 0.07377(12) 0.0183(2) 0.0183(3) Uani 1 1 d .
C26 C -0.01592(15) 0.10561(12) -0.0382(2) 0.0191(3) Uani 1 1 d .
H26 H -0.0269 0.1772 -0.0645 0.023 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C3 C1 C2 118.63(13) . .
C4 C1 C2 120.42(13) . .
C4 C1 C3 120.95(13) . .
C1 C2 H2 119.5 . .
C3 C2 C1 120.95(14) 2_666 .
C3 C2 H2 119.5 2_666 .
C1 C3 H3 119.8 . .
C2 C3 C1 120.42(13) 2_666 .
C2 C3 H3 119.8 2_666 .
C1 C4 C5 121.89(13) . .
C1 C4 C6 122.91(13) . .
C5 C4 C6 115.20(14) . .
N1 C5 C4 178.86(17) . .
N2 C6 C4 177.16(17) . .
C8 C7 C9 118.30(14) . .
C10 C7 C8 120.59(13) . .
C10 C7 C9 121.10(13) . .
C7 C8 H8 119.5 . .
C9 C8 C7 120.95(13) 2_556 .
C9 C8 H8 119.5 2_556 .
C7 C9 H9 119.6 . .
C8 C9 C7 120.75(13) 2_556 .
C8 C9 H9 119.6 2_556 .
C7 C10 C11 122.43(13) . .
C7 C10 C12 122.67(13) . .
C12 C10 C11 114.90(13) . .
N3 C11 C10 177.76(17) . .
N4 C12 C10 177.92(16) . .
C14 C13 C18 118.76(15) . .
C19 C13 C14 121.89(14) 2_665 .
C19 C13 C18 119.35(14) 2_665 .
C13 C14 H14 119.4 . .
C15 C14 C13 121.12(16) . .
C15 C14 H14 119.4 . .
C14 C15 H15 119.9 . .
C14 C15 C16 120.25(16) . .
C16 C15 H15 119.9 . .
C15 C16 H16 119.7 . .
C17 C16 C15 120.59(16) . .
C17 C16 H16 119.7 . .
C16 C17 H17 119.5 . .
C16 C17 C18 121.04(16) . .
C18 C17 H17 119.5 . .
C17 C18 C13 118.24(14) . .
C19 C18 C13 119.15(15) . .
C19 C18 C17 122.61(15) . .
C13 C19 H19 119.3 2_665 .
C18 C19 C13 121.50(14) . 2_665
C18 C19 H19 119.3 . .
C21 C20 C25 118.17(15) . .
C26 C20 C21 122.28(14) 2 .
C26 C20 C25 119.55(14) 2 .
C20 C21 H21 119.5 . .
C22 C21 C20 120.95(15) . .
C22 C21 H21 119.5 . .
C21 C22 H22 119.6 . .
C21 C22 C23 120.79(16) . .
C23 C22 H22 119.6 . .
C22 C23 H23 120.0 . .
C24 C23 C22 120.00(17) . .
C24 C23 H23 120.0 . .
C23 C24 H24 119.3 . .
C23 C24 C25 121.38(16) . .
C25 C24 H24 119.3 . .
C24 C25 C20 118.71(14) . .
C26 C25 C20 118.94(15) . .
C26 C25 C24 122.36(14) . .
C20 C26 C25 121.52(14) 2 .
C20 C26 H26 119.2 2 .
C25 C26 H26 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.147(2) .
N2 C6 1.146(2) .
C1 C2 1.4445(19) .
C1 C3 1.441(2) .
C1 C4 1.379(2) .
C2 H2 0.9500 .
C2 C3 1.346(2) 2_666
C3 C2 1.346(2) 2_666
C3 H3 0.9500 .
C4 C5 1.433(2) .
C4 C6 1.434(2) .
N3 C11 1.149(2) .
N4 C12 1.145(2) .
C7 C8 1.4419(19) .
C7 C9 1.446(2) .
C7 C10 1.374(2) .
C8 H8 0.9500 .
C8 C9 1.342(2) 2_556
C9 C8 1.342(2) 2_556
C9 H9 0.9500 .
C10 C11 1.435(2) .
C10 C12 1.434(2) .
C13 C14 1.426(2) .
C13 C18 1.436(2) .
C13 C19 1.394(2) 2_665
C14 H14 0.9500 .
C14 C15 1.356(3) .
C15 H15 0.9500 .
C15 C16 1.424(3) .
C16 H16 0.9500 .
C16 C17 1.358(2) .
C17 H17 0.9500 .
C17 C18 1.429(2) .
C18 C19 1.392(2) .
C19 C13 1.394(2) 2_665
C19 H19 0.9500 .
C20 C21 1.426(2) .
C20 C25 1.438(2) .
C20 C26 1.394(2) 2
C21 H21 0.9500 .
C21 C22 1.362(2) .
C22 H22 0.9500 .
C22 C23 1.419(3) .
C23 H23 0.9500 .
C23 C24 1.357(2) .
C24 H24 0.9500 .
C24 C25 1.423(2) .
C25 C26 1.396(2) .
C26 C20 1.394(2) 2
C26 H26 0.9500 .
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_4
C2 C1 C3 C2 0.1(2) . 2_666
C2 C1 C4 C5 3.1(2) . .
C2 C1 C4 C6 -177.48(14) . .
C3 C1 C2 C3 -0.1(2) . 2_666
C3 C1 C4 C5 -176.51(14) . .
C3 C1 C4 C6 3.0(2) . .
C4 C1 C2 C3 -179.65(14) . 2_666
C4 C1 C3 C2 179.65(14) . 2_666
C8 C7 C9 C8 -0.3(2) . 2_556
C8 C7 C10 C11 2.7(2) . .
C8 C7 C10 C12 -177.04(14) . .
C9 C7 C8 C9 0.3(2) . 2_556
C9 C7 C10 C11 -177.27(13) . .
C9 C7 C10 C12 3.0(2) . .
C10 C7 C8 C9 -179.64(14) . 2_556
C10 C7 C9 C8 179.64(14) . 2_556
C13 C14 C15 C16 0.6(2) . .
C13 C18 C19 C13 0.2(2) . 2_665
C14 C13 C18 C17 -0.2(2) . .
C14 C13 C18 C19 179.39(13) . .
C14 C15 C16 C17 -0.4(3) . .
C15 C16 C17 C18 0.0(2) . .
C16 C17 C18 C13 0.3(2) . .
C16 C17 C18 C19 -179.22(15) . .
C17 C18 C19 C13 179.79(14) . 2_665
C18 C13 C14 C15 -0.3(2) . .
C19 C13 C14 C15 179.33(15) 2_665 .
C19 C13 C18 C17 -179.81(13) 2_665 .
C19 C13 C18 C19 -0.2(2) 2_665 .
C20 C21 C22 C23 0.1(2) . .
C20 C25 C26 C20 0.3(2) . 2
C21 C20 C25 C24 -0.5(2) . .
C21 C20 C25 C26 179.85(13) . .
C21 C22 C23 C24 -0.4(3) . .
C22 C23 C24 C25 0.2(2) . .
C23 C24 C25 C20 0.2(2) . .
C23 C24 C25 C26 179.84(15) . .
C24 C25 C26 C20 -179.26(14) . 2
C25 C20 C21 C22 0.4(2) . .
C26 C20 C21 C22 -179.45(15) 2 .
C26 C20 C25 C24 179.29(13) 2 .
C26 C20 C25 C26 -0.3(2) 2 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5058(11)
2 0.4942(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139089361
