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_7245745
_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 H8 S, C12 H4 N4'
_chemical_formula_sum            'C24 H12 N4 S'
_chemical_formula_weight         388.44
_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             2022-01-26
_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                100.164(2)
_cell_angle_beta                 98.574(2)
_cell_angle_gamma                98.373(2)
_cell_formula_units_Z            2
_cell_length_a                   6.84060(10)
_cell_length_b                   8.9140(2)
_cell_length_c                   16.3304(3)
_cell_measurement_reflns_used    5351
_cell_measurement_temperature    295.07(17)
_cell_measurement_theta_max      78.7130
_cell_measurement_theta_min      5.0720
_cell_volume                     953.96(3)
_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      295.07(17)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_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    -25.00  24.00   0.50    0.50    --    0.00 -37.00   0.00   98
  2  \w    -63.00 -36.00   0.50    0.50    --    0.00 -37.00   0.00   54
  3  \w    -89.00 -42.00   0.50    0.50    --    0.00 -77.00-120.00   94
  4  \w    -29.00  68.00   0.50    0.50    --    0.00  37.00   0.00  194
  5  \w    -11.00  29.00   0.50    0.50    --    0.00 -77.00-120.00   80
  6  \w     44.00  85.00   0.50    2.90    --  106.20 -77.00 -60.00   82
  7  \w    158.00 184.00   0.50    2.90    --  106.20  82.00-120.00   52
  8  \w     72.00 130.00   0.50    2.90    --  106.20 -61.00 -30.00  116
  9  \w    144.00 196.00   0.50    2.90    --  106.20  30.00-150.00  104
 10  \w     93.00 140.00   0.50    2.90    --  106.20 -30.00 -60.00   94
 11  \w     80.00 112.00   0.50    2.90    --  106.20 -82.00 -60.00   64
 12  \w     19.00 143.00   0.50    2.90    --  106.20 -82.00 150.00  248
 13  \w    103.00 129.00   0.50    2.90    --  106.20  82.00-120.00   52
 14  \w     74.00  99.00   0.50    2.90    --  106.20  30.00 -90.00   50
 15  \w     45.00  73.00   0.50    2.90    --  106.20 -30.00 -60.00   56
 16  \w    109.00 183.00   0.50    2.90    --  106.20  30.00 -90.00  148
 17  \w     17.00 141.00   0.50    2.90    --  106.20 -82.00-120.00  248
 18  \w     17.00  60.00   0.50    2.90    --  106.20 -82.00  30.00   86
 19  \w     92.00 128.00   0.50    2.90    --  106.20 -82.00  30.00   72
 20  \w     93.00 119.00   0.50    2.90    --  106.20  30.00-150.00   52
 21  \w     81.00 196.00   0.50    2.90    --  106.20  30.00 -30.00  230
 22  \w     29.00  64.00   0.50    2.90    --  106.20 -45.00   0.00   70
 23  \w     31.00  57.00   0.50    2.90    --  106.20 -61.00 -30.00   52
 24  \w     27.00 142.00   0.50    2.90    --  106.20 -82.00   0.00  230
 25  \w     96.00 122.00   0.50    2.90    --  106.20 -82.00 120.00   52
 26  \w     41.00 100.00   0.50    2.90    --  106.20 -45.00  60.00  118
 27  \w     23.00 118.00   0.50    2.90    --  106.20 -61.00 150.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080360000
_diffrn_orient_matrix_UB_12      0.1558088000
_diffrn_orient_matrix_UB_13      0.0599940000
_diffrn_orient_matrix_UB_21      -0.0861458000
_diffrn_orient_matrix_UB_22      0.0671523000
_diffrn_orient_matrix_UB_23      -0.0755252000
_diffrn_orient_matrix_UB_31      -0.2146069000
_diffrn_orient_matrix_UB_32      -0.0550955000
_diffrn_orient_matrix_UB_33      0.0137103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10867
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.460
_diffrn_reflns_theta_min         5.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37990
_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    1.352
_exptl_crystal_description       acicular
_exptl_crystal_F_000             400
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0714
_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^)+(0.1211P)^2^+0.3232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3414
_reflns_number_total             4032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01232d2.cif
_cod_data_source_block
Dibenzothiophene_7-7-8-8-Tetracyanoquinodimethane
_cod_database_code               7245745
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 99.26
_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.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C19(H19), C20(H20), C8(H8), C5(H5), C9(H9), C11(H11),
 C10(H10), C4(H4), C2(H2), C3(H3)
;
_shelx_res_checksum              73283
_shelx_hkl_checksum              9550
_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 3.776
_oxdiff_exptl_absorpt_empirical_full_min 0.368