#------------------------------------------------------------------------------
#$Date: 2024-05-05 05:17:20 +0300 (Sun, 05 May 2024) $
#$Revision: 291596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/82/7248294.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_7248294
loop_
_publ_author_name
'Yao, Wenxiu'
'Wu, Pengfei'
'Xie, Yidan'
'Shen, Xinyu'
'Xia, Shuwei'
'Yu, Liangmin'
_publ_section_title
;
 Synthesis and photophysical properties of charge transfer cocrystals
 based on TCNB and fluorene and its derivatives
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2155
_journal_page_last               2165
_journal_paper_doi               10.1039/D3CE01208E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C10 H2 N4, C12 H9 N'
_chemical_formula_sum            'C22 H11 N5'
_chemical_formula_weight         345.36
_chemical_name_systematic        1,2,4,5-Tetracyanobenzene-Carbazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                73.722(3)
_cell_angle_beta                 88.510(3)
_cell_angle_gamma                84.102(3)
_cell_formula_units_Z            1
_cell_length_a                   7.0300(5)
_cell_length_b                   7.8302(6)
_cell_length_c                   7.8567(7)
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.91
_cell_volume                     412.95(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_number            1679
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.701
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.8562
_exptl_absorpt_correction_T_min  0.5623
_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 0.1134 before and 0.0622 after correction.
 
For component 2:
 wR2(int) was 0.1081 before and 0.0609 after correction.
 The Ratio of minimum to maximum transmission is 0.68.

Final HKLF 4 output contains 7497 reflections, Rint = 0.0609
 (5000 with I > 3sig(I), Rint = 0.0563)
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             178
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1679
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0646
_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)+(0.0655P)²+0.2748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1304
_reflns_number_total             1679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01208e2.cif
_cod_data_source_block           tcnbk_0m_4
_cod_depositor_comments
'Adding full bibliography for 7248291--7248294.cif.'
_cod_database_code               7248294
_shelx_shelxl_version_number     2019/2
_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   0.993
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
4. Others
 Fixed Sof: C8(0.5) H8(0.5) C7(0.5) H7(0.5) C6(0.5) H6(0.5) C11(0.5) C10(0.5)
 C9(0.5) H9(0.5) C12(0.5) C17(0.5) N1(0.5) H1(0.5) C13(0.5) H13(0.5) C14(0.5)
 H14(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C7(H7), C6(H6), C9(H9), N1(H1), C13(H13), C14(H14), C15(H15),
 C16(H16)
5.b Fitted hexagon refined as free rotating group:
 C8(C7,C6,C11,C10,C9)
;
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.6557(3) 0.3008(2) 1.0063(2) 0.0349(5) Uani 1 1 d . U . . .
N2 N 0.3414(3) 1.0204(2) 0.3137(3) 0.0389(5) Uani 1 1 d . U . . .
C4 C 0.4477(3) 0.6825(2) 0.4344(3) 0.0233(5) Uani 1 1 d . U . . .
C2 C 0.5561(3) 0.4300(3) 0.6764(2) 0.0227(5) Uani 1 1 d . U . . .
C3 C 0.5040(3) 0.6124(3) 0.6104(3) 0.0248(5) Uani 1 1 d . U . . .
H3 H 0.506876 0.688651 0.685256 0.030 Uiso 1 1 calc R U . . .
C1 C 0.6124(3) 0.3573(3) 0.8600(3) 0.0270(5) Uani 1 1 d . U . . .
C5 C 0.3904(3) 0.8710(3) 0.3661(3) 0.0277(5) Uani 1 1 d . U . . .
C8 C -0.1608(7) 0.7982(7) 0.1243(4) 0.0363(14) Uani 0.5 1 d G U P A -1
H8 H -0.205838 0.865808 0.009835 0.044 Uiso 0.5 1 calc R U P A -1
C7 C -0.1397(7) 0.8830(4) 0.2552(6) 0.0357(14) Uani 0.5 1 d G U P A -1
H7 H -0.170276 1.008637 0.230179 0.043 Uiso 0.5 1 calc R U P A -1
C6 C -0.0738(5) 0.7841(6) 0.4226(5) 0.0299(10) Uani 0.5 1 d G U P A -1
H6 H -0.059391 0.842091 0.512085 0.036 Uiso 0.5 1 calc R U P A -1
C11 C -0.0291(5) 0.6003(6) 0.4592(4) 0.0266(9) Uani 0.5 1 d G U P A -1
C10 C -0.0502(6) 0.5155(4) 0.3283(6) 0.0297(12) Uani 0.5 1 d G U P A -1
C9 C -0.1161(6) 0.6144(7) 0.1609(5) 0.0358(11) Uani 0.5 1 d G U P A -1
H9 H -0.130511 0.556427 0.071401 0.043 Uiso 0.5 1 calc R U P A -1
C12 C 0.0409(8) 0.4615(7) 0.6196(8) 0.0259(10) Uani 0.5 1 d . U P A -1
C17 C 0.0578(7) 0.3058(8) 0.5683(7) 0.0298(10) Uani 0.5 1 d . U P A -1
N1 N 0.0018(5) 0.3361(5) 0.3968(5) 0.0332(8) Uani 0.5 1 d . U P A -1
H1 H -0.000600 0.254417 0.339756 0.040 Uiso 0.5 1 calc R U P A -1
C13 C 0.0896(8) 0.4670(7) 0.7880(8) 0.0314(10) Uani 0.5 1 d . U P A -1
H13 H 0.079556 0.575500 0.820717 0.038 Uiso 0.5 1 calc R U P A -1
C14 C 0.1545(7) 0.3028(9) 0.9067(7) 0.0351(10) Uani 0.5 1 d . U P A -1
H14 H 0.189554 0.299012 1.023741 0.042 Uiso 0.5 1 calc R U P A -1
C15 C 0.1689(10) 0.1442(8) 0.8561(10) 0.0372(13) Uani 0.5 1 d . U P A -1
H15 H 0.212789 0.035397 0.940695 0.045 Uiso 0.5 1 calc R U P A -1
C16 C 0.1221(10) 0.1400(8) 0.6899(10) 0.0343(12) Uani 0.5 1 d . U P A -1
H16 H 0.132089 0.031341 0.657346 0.041 Uiso 0.5 1 calc R U P A -1
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
_geom_angle_publ_flag
C2 C4 C5 119.92(17) 2_666 . ?
C3 C4 C2 120.25(18) . 2_666 ?
C3 C4 C5 119.83(18) . . ?
C4 C2 C1 120.41(17) 2_666 . ?
C3 C2 C4 120.18(18) . 2_666 ?
C3 C2 C1 119.41(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.58(18) . . ?
C2 C3 H3 120.2 . . ?
N3 C1 C2 179.3(2) . . ?
N2 C5 C4 178.6(2) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C11 120.0 . . ?
C11 C6 H6 120.0 . . ?
C6 C11 C12 132.9(5) . . ?
C10 C11 C6 120.0 . . ?
C10 C11 C12 107.1(5) . . ?
C11 C10 C9 120.0 . . ?
N1 C10 C11 108.8(4) . . ?
N1 C10 C9 131.2(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C17 C12 C11 104.0(6) . . ?
C17 C12 C13 123.0(5) . . ?
C13 C12 C11 133.0(7) . . ?
C12 C17 C16 120.7(5) . . ?
N1 C17 C12 111.6(5) . . ?
N1 C17 C16 127.7(6) . . ?
C10 N1 H1 125.8 . . ?
C17 N1 C10 108.4(3) . . ?
C17 N1 H1 125.8 . . ?
C12 C13 H13 122.0 . . ?
C12 C13 C14 116.0(6) . . ?
C14 C13 H13 122.0 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.3(6) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 118.7 . . ?
C16 C15 C14 122.5(6) . . ?
C16 C15 H15 118.7 . . ?
C17 C16 H16 121.7 . . ?
C15 C16 C17 116.6(5) . . ?
C15 C16 H16 121.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C1 1.146(3) . ?
N2 C5 1.145(3) . ?
C4 C2 1.404(3) 2_666 ?
C4 C3 1.389(3) . ?
C4 C5 1.440(3) . ?
C2 C3 1.389(3) . ?
C2 C1 1.444(3) . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.3900 . ?
C8 C9 1.3900 . ?
C7 H7 0.9500 . ?
C7 C6 1.3900 . ?
C6 H6 0.9500 . ?
C6 C11 1.3900 . ?
C11 C10 1.3900 . ?
C11 C12 1.472(5) . ?
C10 C9 1.3900 . ?
C10 N1 1.370(5) . ?
C9 H9 0.9500 . ?
C12 C17 1.381(8) . ?
C12 C13 1.389(8) . ?
C17 N1 1.362(6) . ?
C17 C16 1.417(8) . ?
N1 H1 0.8800 . ?
C13 H13 0.9500 . ?
C13 C14 1.399(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.365(9) . ?
C16 H16 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C2 C3 C4 0.2(3) 2_666 . . . ?
C2 C4 C3 C2 -0.2(3) 2_666 . . . ?
C1 C2 C3 C4 -179.30(18) . . . . ?
C5 C4 C3 C2 178.91(18) . . . . ?
C8 C7 C6 C11 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
C7 C6 C11 C12 -179.5(4) . . . . ?
C6 C11 C10 C9 0.0 . . . . ?
C6 C11 C10 N1 -179.7(4) . . . . ?
C6 C11 C12 C17 -179.6(4) . . . . ?
C6 C11 C12 C13 -1.5(7) . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C11 C10 N1 C17 -0.7(4) . . . . ?
C11 C12 C17 N1 -1.3(6) . . . . ?
C11 C12 C17 C16 -179.8(4) . . . . ?
C11 C12 C13 C14 -179.1(5) . . . . ?
C10 C11 C12 C17 0.9(5) . . . . ?
C10 C11 C12 C13 179.0(5) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C9 C10 N1 C17 179.6(3) . . . . ?
C12 C11 C10 C9 179.6(3) . . . . ?
C12 C11 C10 N1 -0.1(4) . . . . ?
C12 C17 N1 C10 1.4(5) . . . . ?
C12 C17 C16 C15 -1.3(8) . . . . ?
C12 C13 C14 C15 0.1(9) . . . . ?
C17 C12 C13 C14 -1.2(8) . . . . ?
N1 C10 C9 C8 179.6(5) . . . . ?
N1 C17 C16 C15 -179.4(5) . . . . ?
C13 C12 C17 N1 -179.7(5) . . . . ?
C13 C12 C17 C16 1.9(8) . . . . ?
C13 C14 C15 C16 0.4(10) . . . . ?
C14 C15 C16 C17 0.2(9) . . . . ?
C16 C17 N1 C10 179.6(5) . . . . ?
