Perfluoroarene-arene interaction cocrystal of perfluorocarbazoles toward IEF-enhanced photocatalysis.
Hu, Wenbo; Li, Heng; Yuan, Bingxin; Chemical science 16 (2025) 13794–13806; doi:10.1039/d5sc02837j

data_1574914
_publ_section_title
;
 Perfluoroarene-arene interaction cocrystal of perfluorocarbazoles toward
 IEF-enhanced photocatalysis.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              13794
_journal_page_last               13806
_journal_paper_doi               10.1039/d5sc02837j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C17 H4 F8 N2, C18 H12'
_chemical_formula_sum            'C35 H16 F8 N2'
_chemical_formula_weight         616.50
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2mf77k
_audit_creation_date             2024-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                84.896(4)
_cell_angle_beta                 89.124(4)
_cell_angle_gamma                87.160(4)
_cell_formula_units_Z            4
_cell_length_a                   9.6606(4)
_cell_length_b                   15.0395(7)
_cell_length_c                   18.4900(9)
_cell_measurement_reflns_used    5645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6380
_cell_measurement_theta_min      3.9710
_cell_volume                     2672.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      1.00  36.00   1.00    1.00    --  -33.50  77.00  90.00   35
  2  \w    -62.00 -23.00   1.00    1.00    --  -33.50  77.00-180.00   39
  3  \w    -54.00 -21.00   1.00    1.00    --  -33.50 -70.00  51.13   33
  4  \w    -78.00 -35.00   1.00    1.00    --  -33.50 178.00 -30.00   43
  5  \w    -10.00  34.00   1.00    1.00    --  -33.50  77.00-180.00   44
  6  \w     28.00  53.00   1.00    1.00    --   36.47  57.00 -60.00   25
  7  \w     41.00 103.00   1.00    1.00    --   36.47  73.00-132.93   62
  8  \w     12.00  59.00   1.00    1.00    --   36.47 -37.00   0.00   47
  9  \w    -32.00   5.00   1.00    1.00    --   36.47 -37.00   0.00   37
 10  \w     50.00 106.00   1.00    1.00    --   36.47  37.00-180.00   56
 11  \w      1.00  26.00   1.00    1.00    --   36.47  89.00 -35.91   25
 12  \w     55.00  98.00   1.00    1.00    --   36.47  57.00 -60.00   43
 13  \w      0.00  25.00   1.00    1.00    --   36.47  95.00  69.67   25
 14  \w    -17.00  51.00   1.00    1.00    --   36.47 -57.00  90.00   68
 15  \w     77.00 105.00   1.00    1.00    --   36.47  57.00   0.00   28
 16  \w     12.00  38.00   1.00    1.00    --   36.47-109.00 -77.00   26
 17  \w     44.00  73.00   1.00    1.00    --   36.47-109.00 -77.00   29
 18  \w     12.00  49.00   1.00    1.00    --   36.47 -57.00 120.00   37
 19  \w      3.00  34.00   1.00    1.00    --   36.47  89.00-119.35   31
 20  \w      6.00  42.00   1.00    1.00    --   36.47  81.00  13.20   36
 21  \w     29.00  69.00   1.00    1.00    --   36.47  57.00   0.00   40
 22  \w     44.00 128.00   1.00   10.00    --  108.00 -45.00  60.00   84
 23  \w     44.00 128.00   1.00   10.00    --  108.00 -45.00 150.00   84
 24  \w    104.00 149.00   1.00   10.00    --  108.00 111.00  60.00   45
 25  \w     55.00 107.00   1.00   10.00    --  108.00 -94.00  60.00   52
 26  \w     91.00 174.00   1.00   10.00    --  108.00  45.00-120.00   83
 27  \w    101.00 137.00   1.00   10.00    --  108.00 -77.00  90.00   36
 28  \w    133.00 172.00   1.00   10.00    --  108.00  30.00 120.00   39
 29  \w    103.00 170.00   1.00   10.00    --  108.00  61.00 150.00   67
 30  \w     93.00 119.00   1.00   10.00    --  108.00 -45.00 -90.00   26
 31  \w     38.00 107.00   1.00   10.00    --  108.00 -94.00   0.00   69
 32  \w    101.00 175.00   1.00   10.00    --  108.00  77.00-180.00   74
 33  \w     39.00  64.00   1.00   10.00    --  108.00 -45.00 -90.00   25
 34  \w     68.00 107.00   1.00   10.00    --  108.00 -94.00 120.00   39
 35  \w    121.00 172.00   1.00   10.00    --  108.00 111.00-150.00   51
 36  \w    139.00 168.00   1.00   10.00    --  108.00  61.00 120.00   29
 37  \w     94.00 120.00   1.00   10.00    --  108.00  61.00 120.00   26
 38  \w     58.00 108.00   1.00   10.00    --  108.00-111.00 -30.00   50
 39  \w     68.00 107.00   1.00   10.00    --  108.00-111.00-120.00   39
 40  \w    103.00 129.00   1.00   10.00    --  108.00  77.00  30.00   26
 41  \w     51.00  78.00   1.00   10.00    --  108.00 -94.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0225293000
_diffrn_orient_matrix_UB_12      0.0595565000
_diffrn_orient_matrix_UB_13      -0.0714377000
_diffrn_orient_matrix_UB_21      -0.1017440000
_diffrn_orient_matrix_UB_22      0.0620011000
_diffrn_orient_matrix_UB_23      0.0393606000
_diffrn_orient_matrix_UB_31      0.1209814000
_diffrn_orient_matrix_UB_32      0.0566587000
_diffrn_orient_matrix_UB_33      0.0185912000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.638
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00058(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     812
_refine_ls_number_reflns         9530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1073P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.2065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5802
_reflns_number_total             9530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02837j2.cif
_cod_data_source_block           202406210_auto
_cod_depositor_comments
'Adding full bibliography for 1574914--1574918.cif.'
_cod_database_code               1574914
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H2N1O4F8
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.799
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16), C17(H17), C13'(H13'), C15'(H15'), C16'(H16'),
 C17'(H17'), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26),
 C27(H27), C28(H28), C32(H32), C33(H33), C34(H34), C35(H35), C18'(H18'),
 C19'(H19'), C20'(H20'), C21'(H21'), C25'(H25'), C26'(H26'), C27'(H27'),
 C28'(H28'), C32'(H32'), C33'(H33'), C34'(H34'), C35'(H35')
;
_shelx_res_checksum              5831
_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 1.106
_oxdiff_exptl_absorpt_empirical_full_min 0.919