Copper-Assisted Trifluoromethylthiolation/Radical Cascade Cyclization of Alkynes to Construct SCF3-Containing Dioxodibenzothiazepines
Chen, Xiaoyu; Pei, Congcong; Liu, Bo; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Chemical Communications  (2022) –; doi:10.1039/D2CC02171D

data_7130329
_publ_section_title
;
 Copper-Assisted Trifluoromethylthiolation/Radical Cascade Cyclization of
 Alkynes to Construct SCF3-Containing Dioxodibenzothiazepines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02171D
_journal_year                    2022
_chemical_formula_moiety         'C17 H14 F3 N O2 S2'
_chemical_formula_sum            'C17 H14 F3 N O2 S2'
_chemical_formula_weight         385.41
_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     direct
_audit_creation_date             2021-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-22 deposited with the CCDC.	2022-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                82.722(7)
_cell_angle_beta                 74.531(8)
_cell_angle_gamma                73.505(8)
_cell_formula_units_Z            2
_cell_length_a                   9.4571(9)
_cell_length_b                   9.5073(8)
_cell_length_c                   10.3091(9)
_cell_measurement_reflns_used    2258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0330
_cell_measurement_theta_min      4.4460
_cell_volume                     855.26(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00   0.00   93
  2  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -90.00   93
  3  \w   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 -90.00   87
  4  \w    -34.00  59.00   1.00    1.00    --   36.47 -37.00  60.00   93
  5  \w    -32.00  55.00   1.00    1.00    --   36.47 -57.00 150.00   87
  6  \w     -4.00  77.00   1.00    1.00    --   36.47 -99.00-180.00   81
  7  \w     -1.00 109.00   1.00    1.00    --   36.47  19.00 -90.00  110
  8  \w     57.00 107.00   1.00    1.00    --   36.47 178.00-120.00   50
  9  \w     21.00  77.00   1.00    1.00    --   36.47 -99.00 -60.00   56
 10  \w     18.00  62.00   1.00    1.00    --   36.47  57.00 -60.00   44
 11  \w     65.00 103.00   1.00    1.00    --   36.47  77.00  60.00   38
 12  \w      8.00  53.00   1.00    1.00    --   36.47  77.00  60.00   45
 13  \w     40.00 128.00   1.00    1.25    --  108.00 -45.00  60.00   88
 14  \w     56.00 110.00   1.00    1.25    --  108.00 -94.00  60.00   54
 15  \w     41.00 124.00   1.00    1.25    --  108.00 -45.00-150.00   83
 16  \w    120.00 146.00   1.00    1.25    --  108.00 111.00 150.00   26
 17  \w     61.00 136.00   1.00    1.25    --  108.00 -77.00 120.00   75
 18  \w     80.00 112.00   1.00    1.25    --  108.00-111.00-120.00   32
 19  \w     89.00 172.00   1.00    1.25    --  108.00  61.00-150.00   83
 20  \w     75.00 122.00   1.00    1.25    --  108.00 -45.00 120.00   47
 21  \w     93.00 135.00   1.00    1.25    --  108.00 178.00  30.00   42
 22  \w     40.00  71.00   1.00    1.25    --  108.00 -61.00  60.00   31
 23  \w     44.00 119.00   1.00    1.25    --  108.00 -45.00 -60.00   75
 24  \w     44.00 110.00   1.00    1.25    --  108.00 -94.00 -30.00   66
 25  \w     37.00 175.00   1.00    1.25    --  108.00   0.00-180.00  138
;
_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      0.0419263000
_diffrn_orient_matrix_UB_12      0.0949573000
_diffrn_orient_matrix_UB_13      0.0869372000
_diffrn_orient_matrix_UB_21      -0.1475810000
_diffrn_orient_matrix_UB_22      -0.0006368000
_diffrn_orient_matrix_UB_23      0.1087535000
_diffrn_orient_matrix_UB_31      0.0844428000
_diffrn_orient_matrix_UB_32      -0.1401030000
_diffrn_orient_matrix_UB_33      0.0687710000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6069
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.457
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0672P)^2^+0.0905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2292
_reflns_number_total             3063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02171d2.cif
_cod_data_source_block           202110279
_cod_original_cell_volume        855.27(14)
_cod_database_code               7130329
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3N1O4S1F3
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.739
_shelx_estimated_absorpt_t_min   0.611
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              76823
_shelx_hkl_checksum              90598
_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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.904