Photophysics of charge transfer cocrystals composed of fluorene and its heterocyclic analogues as donors and TCNQ as an acceptor
Liu, Xiao-Xu; Shi, Pan; Dai, Xia-Lin; Huang, Yong-Liang; Lu, Tongbu; Chen, Jia-Mei; CrystEngComm  (2022) –; doi:10.1039/D2CE01232D

data_7245744
_publ_section_title
;
 Photophysics of charge transfer cocrystals composed of fluorene and its
 heterocyclic analogues as donors and TCNQ as an acceptor
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01232D
_journal_year                    2022
_chemical_formula_moiety         'C12 H4 N4, C12 H8 O'
_chemical_formula_sum            'C24 H12 N4 O'
_chemical_formula_weight         372.38
_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             2022-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                99.642(13)
_cell_angle_beta                 97.616(11)
_cell_angle_gamma                100.727(15)
_cell_formula_units_Z            1
_cell_length_a                   6.7631(11)
_cell_length_b                   8.0049(16)
_cell_length_c                   9.0066(11)
_cell_measurement_reflns_used    2389
_cell_measurement_temperature    293.39(10)
_cell_measurement_theta_max      78.3750
_cell_measurement_theta_min      6.6930
_cell_volume                     465.52(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     35.00  88.00   0.50    0.50    --    0.00  57.00   0.00  106
  2  \w     28.00  55.00   0.50    0.50    --    0.00  57.00-120.00   54
  3  \w    -26.00  30.00   0.50    0.50    --    0.00  57.00   0.00  112
  4  \w     39.00  85.00   0.50    0.50    --    0.00  57.00  90.00   92
  5  \w    -24.00  21.00   0.50    0.50    --    0.00  57.00-120.00   90
  6  \w     20.00 134.00   0.50    4.60    --  106.20 -82.00 120.00  228
  7  \w    116.00 165.00   0.50    4.60    --  106.20  30.00 -60.00   98
  8  \w     48.00  91.00   0.50    4.60    --  106.20 -30.00 -30.00   86
  9  \w     41.00  67.00   0.50    4.60    --  106.20 -82.00 -90.00   52
 10  \w     80.00 142.00   0.50    4.60    --  106.20 -82.00-180.00  124
 11  \w     91.00 128.00   0.50    4.60    --  106.20 -82.00 -90.00   74
 12  \w     80.00 110.00   0.50    4.60    --  106.20  30.00-120.00   60
 13  \w    126.00 179.00   0.50    4.60    --  106.20  30.00-120.00  106
 14  \w     38.00  78.00   0.50    4.60    --  106.20 -82.00   0.00   80
 15  \w     76.00 112.00   0.50    4.60    --  106.20  30.00 -60.00   72
 16  \w    109.00 187.00   0.50    4.60    --  106.20  30.00 -30.00  156
 17  \w     78.00 103.00   0.50    4.60    --  106.20  30.00 -30.00   50
 18  \w     88.00 128.00   0.50    4.60    --  106.20 -82.00   0.00   80
 19  \w     76.00 189.00   0.50    4.60    --  106.20  30.00   0.00  226
 20  \w     97.00 137.00   0.50    4.60    --  106.20 -30.00 -30.00   80
 21  \w    145.00 190.00   0.50    4.60    --  106.20  30.00-150.00   90
 22  \w     78.00 104.00   0.50    4.60    --  106.20 -61.00   0.00   52
 23  \w     53.00 138.00   0.50    4.60    --  106.20 -82.00 -60.00  170
 24  \w     32.00 136.00   0.50    4.60    --  106.20 -61.00 120.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0709244000
_diffrn_orient_matrix_UB_12      0.1617170000
_diffrn_orient_matrix_UB_13      -0.0395719000
_diffrn_orient_matrix_UB_21      -0.1137459000
_diffrn_orient_matrix_UB_22      -0.1069701000
_diffrn_orient_matrix_UB_23      -0.1564278000
_diffrn_orient_matrix_UB_31      -0.1932935000
_diffrn_orient_matrix_UB_32      -0.0482294000
_diffrn_orient_matrix_UB_33      0.0703658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4446
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.322
_diffrn_reflns_theta_min         5.054
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       acicular
_exptl_crystal_F_000             192
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0814P)^2^+0.0419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1630
_reflns_number_total             1932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01232d2.cif
_cod_data_source_block           Dibenzofuran_7-7-8-8-Tetracyanoquinodimethane
_cod_database_code               7245744
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 98.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C3(0.5) H3(0.5) C2(0.5) H2(0.5) C1(0.5) C6(0.5) C5(0.5) H5(0.5)
 C4(0.5) H4(0.5) O1(0.5) C10(0.5) H10(0.5) C9(0.5) H9(0.5) C8(0.5) H8(0.5)
 C7(0.5) C12(0.5) C11(0.5) H11(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C3(H3), C2(H2), C5(H5), C4(H4), C10(H10), C9(H9), C8(H8),
 C11(H11)
3.b Fitted hexagon refined as free rotating group:
 C3(C2,C1,C6,C5,C4), C10(C9,C8,C7,C12,C11)
;
_shelx_res_checksum              73375
_shelx_hkl_checksum              65591
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.879
_oxdiff_exptl_absorpt_empirical_full_min 0.557