Synthesis and photophysical properties of charge transfer cocrystals based on TCNB and fluorene and its derivatives
Yao, Wenxiu; Wu, Pengfei; Xie, Yidan; Shen, Xinyu; Xia, Shuwei; Yu, Liangmin; CrystEngComm 26 (2024) 2155–2165; doi:10.1039/D3CE01208E

data_7248294
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0655P)^2^+0.2748P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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'