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_7245743
_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, C13 H10'
_chemical_formula_sum            'C25 H14 N4'
_chemical_formula_weight         370.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2b039s
_audit_creation_date             2021-12-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.571(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0146(6)
_cell_length_b                   13.1035(6)
_cell_length_c                   6.7957(4)
_cell_measurement_reflns_used    1120
_cell_measurement_temperature    295.10(10)
_cell_measurement_theta_max      76.8480
_cell_measurement_theta_min      5.3020
_cell_volume                     953.44(9)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_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     63.00  89.00   0.50    0.50    --    0.00  57.00  90.00   52
  2  \w     59.00  84.00   0.50    0.50    --    0.00  57.00-120.00   50
  3  \w    -27.00  42.00   0.50    0.50    --    0.00  57.00-120.00  138
  4  \w      4.00  29.00   0.50    0.50    --    0.00  57.00  90.00   50
  5  \w     88.00 114.00   0.50    2.00    --  106.20  77.00 -60.00   52
  6  \w     47.00 139.00   0.50    2.00    --  106.20 -77.00   0.00  184
  7  \w    109.00 140.00   0.50    2.00    --  106.20 -82.00 120.00   62
  8  \w     17.00 101.00   0.50    2.00    --  106.20 -82.00 120.00  168
  9  \w     78.00 182.00   0.50    2.00    --  106.20  45.00  60.00  208
 10  \w     25.00  97.00   0.50    2.00    --  106.20 -30.00 -90.00  144
 11  \w    147.00 196.00   0.50    2.00    --  106.20  77.00 -60.00   98
 12  \w    161.00 187.00   0.50    2.00    --  106.20  82.00-150.00   52
 13  \w    101.00 130.00   0.50    2.00    --  106.20 -82.00  90.00   58
 14  \w    104.00 137.00   0.50    2.00    --  106.20  82.00-150.00   66
;
_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      -0.0414166000
_diffrn_orient_matrix_UB_12      0.0211799000
_diffrn_orient_matrix_UB_13      -0.2290326000
_diffrn_orient_matrix_UB_21      0.1372951000
_diffrn_orient_matrix_UB_22      -0.0032086000
_diffrn_orient_matrix_UB_23      -0.0151706000
_diffrn_orient_matrix_UB_31      -0.0115722000
_diffrn_orient_matrix_UB_32      -0.1155836000
_diffrn_orient_matrix_UB_33      -0.0416187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2504
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.023
_diffrn_reflns_theta_min         5.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56253
_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    1.290
_exptl_crystal_description       acicular
_exptl_crystal_F_000             384
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1051
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0643P)^2^+0.1021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.000
_reflns_number_gt                844
_reflns_number_total             1051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01232d2.cif
_cod_data_source_block           Fluorene_7-7-8-8-Tetracyanoquinodimethane
_cod_database_code               7245743
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C16-C2 \\sim C16-C14 \\sim C5-C14 \\sim C5-C11 \\sim C2-C11
 with sigma of 0.01
 C11-C16 \\sim C16-C5
 with sigma of 0.01
3. Restrained planarity
 C10, C14, C16, C9, C5, C11, C7, C17, C12, C13, C15, C2, C3
 with sigma of 0.01
4. Rigid body (RIGU) restrains
 C10, C12, C14, C16, C17, C9, C5, C11, C3, C13, C7, C15, C2
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
5. Others
 Fixed Sof: C10(0.25) H10(0.25) C12(0.25) H12(0.25) C14(0.25) C16(0.25)
 C17(0.25) H17(0.25) C9(0.25) H9(0.25) C5(0.25) H5A(0.25) H5B(0.25) C11(0.25)
 C3(0.25) H3(0.25) C13(0.25) H13(0.25) C7(0.25) H7(0.25) C15(0.25) H15(0.25)
 C2(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C12(H12), C17(H17), C9(H9), C3(H3), C13(H13), C7(H7),
 C15(H15)
6.c Fitted hexagon refined as free rotating group:
 C10(C12,C14,C16,C17,C9), C11(C3,C13,C7,C15,C2)
;
_shelx_res_checksum              55259
_shelx_hkl_checksum              26921
_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 1.842
_oxdiff_exptl_absorpt_empirical_full_min 0.611