Facile generation and reaction of densely trifluoromethylated alkyl radicals by dual photoredox and acid catalysis
Koike, Takashi; Taguchi, Hina; Hirota, Kaori; Kiyatake, Shota; Tatara, Naohiro; Kayaki, Yoshihito; Yamaguchi, Airi; Yajima, Tomoko; Chemical Communications  (2026) –; doi:10.1039/D6CC00475J

data_7135604
_publ_section_title
;
 Facile generation and reaction of densely trifluoromethylated alkyl
 radicals by dual photoredox and acid catalysis.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7319
_journal_page_last               7323
_journal_paper_doi               10.1039/d6cc00475j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C12 H5 Cl F9 N'
_chemical_formula_sum            'C12 H5 Cl F9 N'
_chemical_formula_weight         369.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-12-17
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-30 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.310(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5848(3)
_cell_length_b                   7.2834(2)
_cell_length_c                   32.0201(8)
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    223.15
_cell_measurement_theta_max      72.7840
_cell_measurement_theta_min      5.3200
_cell_volume                     2685.38(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      223.15
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_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     13.00  39.00   0.50    8.70    -------------------------------------   45.70 -64.00  23.00   52
  2  \w     69.00 116.00   0.50    8.70    -   45.70  64.00 160.00   94
  3  \w    125.00 186.00   0.50   34.80    -  101.80  64.00 160.00  122
  4  \w     71.00 117.00   0.50   34.80    -  101.80 -64.00  23.00   92
  5  \w      5.00 134.00   0.50    8.70    -   45.70  57.00  90.00  258
  6  \w     25.00  52.00   0.50    8.70    -   45.70  38.00   0.00   54
  7  \w      5.00 135.00   0.50    8.70    -   45.70  57.00-150.00  260
  8  \w     62.00  93.00   0.50   34.80    -  101.80  45.00-120.00   62
  9  \w     74.00 100.00   0.50   34.80    -  101.80  82.00-120.00   52
 10  \w    121.00 147.00   0.50   34.80    -  101.80  82.00-120.00   52
 11  \w     78.00 116.00   0.50   34.80    -  101.80 -61.00 150.00   76
 12  \w     72.00 147.00   0.50   34.80    -  101.80 -82.00  30.00  150
 13  \w    100.00 190.00   0.50   34.80    -  101.80  45.00-120.00  180
 14  \w     79.00 191.00   0.50   34.80    -  101.80  61.00-180.00  224
 15  \w     56.00 172.00   0.50   34.80    -  101.80  45.00 -90.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14724
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.259
_diffrn_reflns_theta_min         5.350
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'micromax 003'
_exptl_absorpt_coefficient_mu    3.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
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    1.828
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0751
_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^)+(0.1126P)^2^+4.3585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2268
_refine_ls_wR_factor_ref         0.2333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4349
_reflns_number_total             5223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00475j2.cif
_cod_data_source_block           251202_5aa
_cod_depositor_comments          'Adding full bibliography for 7135604.cif.'
_cod_database_code               7135604
_shelx_shelxl_version_number     2019/3
_cell_oxdiff_angle_alpha         89.881(3)
_cell_oxdiff_angle_beta          96.361(2)
_cell_oxdiff_angle_gamma         90.023(3)
_cell_oxdiff_length_a            11.5810(3)
_cell_oxdiff_length_b            7.2854(4)
_cell_oxdiff_length_c            32.0249(10)
_cell_oxdiff_measurement_reflns_used 5245
_cell_oxdiff_volume              2685.38(19)
_diffrn_oxdiff_digest_hkl
;
015ad40cc29b7a23348f743ab263130ae4d1a5
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C14(H14), C8(H8), C20(H20), C18(H18), C5(H5),
 C17(H17), C6(H6)
;
_shelx_res_checksum              42600
_shelx_hkl_checksum              23927
_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.678