AgSCF3-Mediated Oxidative Trifluoromethythiolation of Alkynes with Dearomatization to Synthesize SCF3-Substituted Spiro[4,5]trienones.
Jin, Dong-Po; Gao, Pin; Chen, Dao-Qian; Chen, Si; Wang, Jia; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 18 (2016) 3486–3489; doi:10.1021/acs.orglett.6b01702

data_1543572
_publ_section_title
;
 AgSCF3-Mediated Oxidative Trifluoromethythiolation of Alkynes with
 Dearomatization to Synthesize SCF3-Substituted Spiro[4,5]trienones.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3486
_journal_page_last               3489
_journal_paper_doi               10.1021/acs.orglett.6b01702
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C22 H24 F3 N O3 S'
_chemical_formula_sum            'C22 H24 F3 N O3 S'
_chemical_formula_weight         439.48
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.076(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2909(8)
_cell_length_b                   12.7985(11)
_cell_length_c                   14.5821(9)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    291.23(10)
_cell_measurement_theta_max      68.1790
_cell_measurement_theta_min      5.2140
_cell_volume                     2251.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  143.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   60.0000 33

  2 omega   88.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 26

  3 omega   82.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 29

  4 omega   52.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 40

  5 omega   49.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 63

  6 omega   35.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 50

  7 omega   36.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 53

  8 omega   41.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   30.0000 89

  9 omega   82.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   60.0000 36

 10 omega   63.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 38

 11 omega   47.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 28

 12 omega   50.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 33

 13 omega   37.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   60.0000 42

 14 omega   25.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  -60.0000 58

 15 omega   24.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 46

 16 omega   23.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 37

 17 omega  -10.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 27

 18 omega   59.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 64

 19 omega    2.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -150.0000 85

 20 omega  -14.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1192748000
_diffrn_orient_matrix_UB_12      0.0427058000
_diffrn_orient_matrix_UB_13      0.0244874000
_diffrn_orient_matrix_UB_21      0.0457556000
_diffrn_orient_matrix_UB_22      -0.1119728000
_diffrn_orient_matrix_UB_23      -0.0008669000
_diffrn_orient_matrix_UB_31      0.0024030000
_diffrn_orient_matrix_UB_32      0.0110722000
_diffrn_orient_matrix_UB_33      -0.1047813000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8622
_diffrn_reflns_theta_full        69.74
_diffrn_reflns_theta_max         69.74
_diffrn_reflns_theta_min         4.32
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1270P)^2^+0.7116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2260
_reflns_number_gt                2945
_reflns_number_total             4176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01702_si_003.cif
_cod_data_source_block           jdp_25_1
_cod_depositor_comments          'Adding full bibliography for 1543572.cif.'
_cod_database_code               1543572
_chemical_oxdiff_formula         'C138 O12 S8'
_reflns_odcompleteness_completeness 99.76
_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:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_olex2_date_sample_data_collection 2016-04-15
_olex2_submission_special_instructions 'No special instructions were received'