Visible-light-induced radical trifluoromethylation/cyclization of alkynes: synthesis of CF<sub>3</sub>-containing dioxodibenzothiazepines.
Chen, Xiaoyu; Geng, Yang; Liu, Pan; Wu, Zhiyong; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Organic & biomolecular chemistry 23 (2025) 10474–10478; doi:10.1039/d5ob01520k

data_7160841
_publ_section_title
;
 Visible-light-induced radical trifluoromethylation/cyclization of
 alkynes: synthesis of CF<sub>3</sub>-containing dioxodibenzothiazepines.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10474
_journal_page_last               10478
_journal_paper_doi               10.1039/d5ob01520k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 F3 N O2 S'
_chemical_formula_sum            'C17 H14 F3 N O2 S'
_chemical_formula_weight         353.35
_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     dual
_audit_creation_date             2025-01-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.279(4)
_cell_angle_beta                 101.789(5)
_cell_angle_gamma                106.790(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8410(4)
_cell_length_b                   9.9763(5)
_cell_length_c                   10.8160(6)
_cell_measurement_reflns_used    5860
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.6920
_cell_measurement_theta_min      2.7490
_cell_volume                     791.07(8)
_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  (Sheldrick, 2015)'
_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 0.999
_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    -12.00  56.00   0.50    0.70    --   -4.09  57.00 -60.00  136
  2  \w    -18.00  65.00   0.50    0.70    --   -4.09  33.00  59.00  166
  3  \w      7.00  34.00   0.50    0.70    --    6.28 -99.00 -60.00   54
  4  \w     -6.00  39.00   0.50    0.70    --    6.28 -99.00-120.00   90
  5  \w    -18.00  23.00   0.50    0.70    --   -4.09 -99.00 -90.00   82
  6  \w    -39.00  10.00   0.50    0.70    --   -4.09 -33.00 -98.00   98
  7  \w    -72.00 -46.00   0.50    0.70    --   -4.09 -33.00 -98.00   52
  8  \w    -17.00  24.00   0.50    0.70    --   -4.09 -99.00  90.00   82
;
_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      0.0582940000
_diffrn_orient_matrix_UB_12      -0.0287297000
_diffrn_orient_matrix_UB_13      -0.0266774000
_diffrn_orient_matrix_UB_21      0.0671794000
_diffrn_orient_matrix_UB_22      0.0664621000
_diffrn_orient_matrix_UB_23      0.0094217000
_diffrn_orient_matrix_UB_31      0.0380670000
_diffrn_orient_matrix_UB_32      -0.0172735000
_diffrn_orient_matrix_UB_33      0.0608968000
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9555
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.778
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80224
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0495P)^2^+0.3354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2675
_reflns_number_total             3238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01520k2.cif
_cod_data_source_block           202501zy11_auto
_cod_depositor_comments          'Adding full bibliography for 7160841.cif.'
_cod_database_code               7160841
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         CHNOSF
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              97145
_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 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.819