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_7248291
_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         'C13 H9 Br, C10 H2 N4'
_chemical_formula_sum            'C23 H11 Br N4'
_chemical_formula_weight         423.27
_chemical_name_systematic        1,2,4,5-Tetracyanobenzene-2-Bromofluorene
_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             2023-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-19 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                85.443(12)
_cell_angle_beta                 76.787(11)
_cell_angle_gamma                74.123(11)
_cell_formula_units_Z            1
_cell_length_a                   7.455(3)
_cell_length_b                   7.934(3)
_cell_length_c                   8.270(3)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.422
_cell_measurement_theta_min      2.530
_cell_volume                     458.0(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.479
_diffrn_reflns_theta_min         2.530
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.260
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1268 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.7620.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     260
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0927
_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^)+3.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1375
_reflns_number_total             1864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01208e2.cif
_cod_data_source_block           312nb_0m
_cod_depositor_comments
'Adding full bibliography for 7248291--7248294.cif.'
_cod_database_code               7248291
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
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
Uanis(C6) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.007 and
sigma for terminal atoms of 0.014
4. Others
 Fixed Sof: Br1(0.5) C13(0.5) H13(0.5) C9(0.5) H9A(0.5) H9B(0.5) C14(0.5)
 H14(0.5) C10(0.5) C15(0.5) C11(0.5) H11(0.5) C12(0.5) C17(0.5) H17(0.5)
 C18(0.5) H18(0.5) C16(0.5) C8(0.5) C7(0.5) H7(0.5) C6(0.5) H6(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C14(H14), C11(H11), C17(H17), C18(H18), C7(H7), C6(H6)
5.c Fitted hexagon refined as free rotating group:
 C17(C18,C16,C8,C7,C6)
;
_olex2_submission_special_instructions 'No special instructions were received'