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_1574916
_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, C10 H6'
_chemical_formula_sum            'C27 H10 F8 N2'
_chemical_formula_weight         514.37
_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     iterative
_audit_creation_date             2023-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-06-17 deposited with the CCDC.	2025-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                80.453(8)
_cell_angle_beta                 70.664(10)
_cell_angle_gamma                87.322(8)
_cell_formula_units_Z            2
_cell_length_a                   9.9143(10)
_cell_length_b                   10.2042(10)
_cell_length_c                   11.3792(12)
_cell_measurement_reflns_used    2056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.1960
_cell_measurement_theta_min      4.1560
_cell_volume                     1071.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -108.00 -35.00   1.00    1.50    --  -33.50 178.00 120.00   73
  2  \w   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00 -90.00   93
  3  \w    -56.00  37.00   1.00    1.50    --  -33.50  37.00  90.00   93
  4  \w    -62.00  36.00   1.00    1.50    --  -33.50  77.00-150.00   98
  5  \w   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00 120.00   93
  6  \w      1.00  76.00   1.00    1.50    --   36.47 -99.00 150.00   75
  7  \w     61.00 110.00   1.00    1.50    --   36.47 178.00-180.00   49
  8  \w      1.00  76.00   1.00    1.50    --   36.47 -99.00 -30.00   75
  9  \w     40.00 109.00   1.00    7.50    --  108.00-111.00-180.00   69
 10  \w     88.00 176.00   1.00    7.50    --  108.00  61.00  60.00   88
 11  \w     85.00 138.00   1.00    7.50    --  108.00  15.00 150.00   53
 12  \w    150.00 176.00   1.00    7.50    --  108.00  15.00 150.00   26
 13  \w     50.00 128.00   1.00    7.50    --  108.00 -45.00-120.00   78
 14  \w     44.00 102.00   1.00    7.50    --  108.00 -94.00-150.00   58
 15  \w     42.00 124.00   1.00    7.50    --  108.00 -61.00  30.00   82
 16  \w    101.00 174.00   1.00    7.50    --  108.00  77.00 -60.00   73
 17  \w    103.00 129.00   1.00    7.50    --  108.00  77.00   0.00   26
 18  \w     42.00 109.00   1.00    7.50    --  108.00-111.00 -60.00   67
 19  \w    146.00 177.00   1.00    7.50    --  108.00  77.00   0.00   31
 20  \w     69.00 121.00   1.00    7.50    --  108.00 -61.00 -60.00   52
 21  \w     88.00 147.00   1.00    7.50    --  108.00  61.00  30.00   59
 22  \w     73.00  99.00   1.00    7.50    --  108.00-111.00  60.00   26
 23  \w     74.00 101.00   1.00    7.50    --  108.00 -94.00 -60.00   27
 24  \w     83.00 109.00   1.00    7.50    --  108.00-111.00  90.00   26
 25  \w    102.00 168.00   1.00    7.50    --  108.00  61.00-120.00   66
 26  \w    110.00 145.00   1.00    7.50    --  108.00 111.00 -30.00   35
;
_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      -0.0538266000
_diffrn_orient_matrix_UB_12      0.1424033000
_diffrn_orient_matrix_UB_13      -0.0260000000
_diffrn_orient_matrix_UB_21      0.1529764000
_diffrn_orient_matrix_UB_22      0.0542932000
_diffrn_orient_matrix_UB_23      -0.0345111000
_diffrn_orient_matrix_UB_31      0.0286593000
_diffrn_orient_matrix_UB_32      -0.0146001000
_diffrn_orient_matrix_UB_33      -0.1387673000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7540
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.171
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (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    1.595
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0016(5)
_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   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0941P)^2^+0.0210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             3822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02837j2.cif
_cod_data_source_block           202309223_auto
_cod_depositor_comments
'Adding full bibliography for 1574914--1574918.cif.'
_cod_database_code               1574916
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N1F1
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.795
_reflns_odcompleteness_completeness 99.90
_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. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C23A)
Uanis(C22) = Uanis(C22A)
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
Uanis(C19) = Uanis(C19A)
Uanis(C18) = Uanis(C18A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
Uanis(C27) = Uanis(C27A)
3. Others
 Sof(C18A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=
 Sof(H22A)=Sof(C23A)=Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=
 Sof(C27A)=Sof(H27A)=1-FVAR(1)
 Sof(C18)=Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C23)=Sof(C24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22),
 C20A(H20A), C21A(H21A), C22A(H22A), C25(H25), C25A(H25A), C26(H26), C26A(H26A),
  C27(H27), C27A(H27A)
4.b Fitted hexagon refined as free rotating group:
 C18(C19,C20,C21,C22,C23), C18A(C19A,C20A,C21A,C22A,C23A)
;
_shelx_res_checksum              13261
_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 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.904