Photocatalytic cyclization reaction of 2-vinylarylamines with CF<sub>3</sub>SO<sub>2</sub>Na and arylaldehydes to access 3-(2,2,2-trifluoroethyl)-3<i>H</i>-indoles.
Song, Mengda; Leng, Yuting; Xu, Zhiwei; Wu, Yusheng; Wu, Yangjie; Chemical communications (Cambridge, England) 61 (2025) 15626–15629; doi:10.1039/d5cc03496e

data_7134948
_publ_section_title
;
 Photocatalytic cyclization reaction of 2-vinylarylamines with
 CF<sub>3</sub>SO<sub>2</sub>Na and arylaldehydes to access
 3-(2,2,2-trifluoroethyl)-3<i>H</i>-indoles.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15626
_journal_page_last               15629
_journal_paper_doi               10.1039/d5cc03496e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C25 H19 F6 N O2'
_chemical_formula_sum            'C25 H19 F6 N O2'
_chemical_formula_weight         479.41
_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     dual
_audit_creation_date             2024-12-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.262(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2122(5)
_cell_length_b                   13.7141(4)
_cell_length_c                   14.0849(6)
_cell_measurement_reflns_used    8727
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.8000
_cell_measurement_theta_min      2.3910
_cell_volume                     2183.10(16)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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 0.801
_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    -27.00  10.00   0.50    2.00    --    6.28 -41.00 156.00   74
  2  \w    -65.00 -39.00   0.50    2.00    --    6.28 -41.00 156.00   52
  3  \w    -17.00  24.00   0.50    2.00    --   -4.09 -99.00 150.00   82
  4  \w    -18.00  32.00   0.50    2.00    --    6.28 -99.00 -30.00  100
  5  \w     -8.00  17.00   0.50    2.00    --    6.28  57.00  60.00   50
  6  \w     18.00  44.00   0.50    2.00    --    6.28  57.00  60.00   52
  7  \w     -2.00  73.00   0.50    2.00    --    6.28  41.00 -50.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344572000
_diffrn_orient_matrix_UB_12      -0.0160469000
_diffrn_orient_matrix_UB_13      -0.0277656000
_diffrn_orient_matrix_UB_21      0.0411087000
_diffrn_orient_matrix_UB_22      -0.0214768000
_diffrn_orient_matrix_UB_23      0.0452840000
_diffrn_orient_matrix_UB_31      -0.0325046000
_diffrn_orient_matrix_UB_32      -0.0442297000
_diffrn_orient_matrix_UB_33      -0.0119704000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.801
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21078
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.863
_diffrn_reflns_theta_min         2.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
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    1.459
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0498P)^2^+0.6779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4380
_reflns_number_total             5514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03496e2.cif
_cod_data_source_block           20241209lyt_auto
_cod_depositor_comments
'Adding full bibliography for 7134947--7134948.cif.'
_cod_database_code               7134948
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.985
_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.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              99262
_shelx_hkl_checksum              80160
_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 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.611