Photo-induced radical trifluoromethylation/dearomatization of 3-substituted indoles.
Lv, Yuyu; Deng, Zhoubin; Zhu, Zhijun; Hai, Xiaopeng; Wang, Junjiao; Wang, Ke-Hu; Huang, Danfeng; Hu, Yulai; Organic & biomolecular chemistry 23 (2025) 9658–9667; doi:10.1039/d5ob01103e

data_7160785
_publ_section_title
;
 Photo-induced radical trifluoromethylation/dearomatization of
 3-substituted indoles.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9658
_journal_page_last               9667
_journal_paper_doi               10.1039/d5ob01103e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H15 F3 N2'
_chemical_formula_sum            'C19 H15 F3 N2'
_chemical_formula_weight         328.33
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lc3rv
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-25 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.59700(10)
_cell_length_b                   15.59700(10)
_cell_length_c                   26.0546(3)
_cell_measurement_reflns_used    16734
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.0670
_cell_measurement_theta_min      3.2860
_cell_volume                     6338.21(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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     39.00  64.00   0.50    0.16    --  111.16 -61.00-120.00   50
  2  \w     39.00  64.00   0.50    0.16    --  111.16 -61.00 -60.00   50
  3  \w     52.00  94.00   0.50    0.16    --  111.16 -77.00 -30.00   84
  4  \w     39.00  65.00   0.50    0.16    --  111.16 -61.00   0.00   52
  5  \w     42.00  67.00   0.50    0.16    --  111.16 -61.00 120.00   50
  6  \w    100.00 174.00   0.50    0.16    --  111.16  37.00 -57.00  148
  7  \w   -117.00 -26.00   0.50    0.16    --  -44.63 -37.00 146.00  182
  8  \w    -83.00 -49.00   0.50    0.16    -- -100.00 105.00 154.00   68
  9  \w    -90.00 -44.00   0.50    0.16    -- -100.00 125.00  30.00   92
 10  \w    -52.00 -26.00   0.50    0.16    -- -100.00  45.00 -30.00   52
 11  \w    -54.00 -25.00   0.50    0.16    -- -100.00  45.00   0.00   58
 12  \w    -54.00 -29.00   0.50    0.16    -- -100.00  45.00  30.00   50
 13  \w    -95.00 -64.00   0.50    0.16    --  -44.63-179.00 -60.00   62
 14  \w    -38.00  -6.00   0.50    0.16    --  -44.63 105.00 154.00   64
 15  \w    -67.00 -42.00   0.50    0.16    --  -44.63 105.00 154.00   50
 16  \w    -54.00 -28.00   0.50    0.16    --  -44.63 -57.00   0.00   52
 17  \w    -57.00 -25.00   0.50    0.16    --  -44.63 -37.00   0.00   64
 18  \w   -108.00 -25.00   0.50    0.16    --  -44.63 -57.00  90.00  166
 19  \w   -134.00 -77.00   0.50    0.16    -- -100.00 -67.00  30.68  114
 20  \w   -169.00-125.00   0.50    0.16    -- -100.00 -49.00  27.44   88
 21  \w   -120.00 -76.00   0.50    0.16    -- -100.00 -71.00  43.32   88
 22  \w    -98.00 -73.00   0.50    0.16    -- -100.00 -76.00  72.23   50
 23  \w   -114.00 -80.00   0.50    0.16    -- -100.00 -45.00  30.00   68
 24  \w    -73.00 -40.00   0.50    0.16    -- -100.00  61.00  60.00   66
 25  \w    -98.00 -73.00   0.50    0.16    -- -100.00 -77.00  60.00   50
 26  \w   -119.00 -82.00   0.50    0.16    -- -100.00 -46.00  43.38   74
 27  \w   -105.00 -80.00   0.50    0.16    -- -100.00 -43.00  44.31   50
 28  \w   -168.00-142.00   0.50    0.16    -- -100.00-125.00 -60.00   52
 29  \w   -107.00 -82.00   0.50    0.16    -- -100.00-125.00 -60.00   50
 30  \w    -98.00 -73.00   0.50    0.16    -- -100.00 -76.00  67.05   50
 31  \w   -161.00-135.00   0.50    0.16    -- -100.00 -76.00  72.23   52
 32  \w   -100.00 -75.00   0.50    0.16    -- -100.00 -74.00  50.07   50
 33  \w   -116.00 -79.00   0.50    0.16    -- -100.00 -48.00  54.51   74
 34  \w     39.00  64.00   0.50    0.16    --  111.16 -61.00-150.00   50
 35  \w     98.00 174.00   0.50    0.16    --  111.16  45.00 -30.00  152
 36  \w    119.00 166.00   0.50    0.16    --  111.16  92.00  64.00   94
 37  \w     48.00  73.00   0.50    0.16    --  111.16 -92.00 -48.00   50
 38  \w     39.00  65.00   0.50    0.16    --  111.16 -61.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0899681000
_diffrn_orient_matrix_UB_12      0.0236004000
_diffrn_orient_matrix_UB_13      0.0199027000
_diffrn_orient_matrix_UB_21      -0.0122557000
_diffrn_orient_matrix_UB_22      -0.0924772000
_diffrn_orient_matrix_UB_23      0.0194770000
_diffrn_orient_matrix_UB_31      0.0389154000
_diffrn_orient_matrix_UB_32      0.0254584000
_diffrn_orient_matrix_UB_33      0.0521466000
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.266
_diffrn_reflns_theta_min         3.302
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+4.7425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2901
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01103e2.cif
_cod_data_source_block           yyl-251_1025_auto
_cod_depositor_comments          'Adding full bibliography for 7160785.cif.'
_cod_original_cell_volume        6338.21(11)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7160785
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3B) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F2)
\\sim Ueq, Uanis(F2B) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.005
3. Others
 Fixed Sof: F1(0.7) F1B(0.3) F2(0.7) F2B(0.3) F3(0.7) F3B(0.3)
4.a Ternary CH refined with riding coordinates:
 C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C19(H19)
4.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              58897
_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.718