AgSCF3-Mediated Trifluoromethylthiolation/Radical Cascade Cyclization of 1,6-Enynes.
Qiu, Yi-Feng; Zhu, Xin-Yu; Li, Ying-Xiu; He, Yu-Tao; Yang, Fang; Wang, Jia; Hua, Hui-Liang; Zheng, Lan; Wang, Li-Chen; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 17 (2015) 3694–3697; doi:10.1021/acs.orglett.5b01657

data_1529877
_publ_section_title
;
 AgSCF3-Mediated Trifluoromethylthiolation/Radical Cascade Cyclization of
 1,6-Enynes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3694
_journal_page_last               3697
_journal_paper_doi               10.1021/acs.orglett.5b01657
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C22 H21 Cl F3 N O2 S2'
_chemical_formula_sum            'C22 H21 Cl F3 N O2 S2'
_chemical_formula_weight         487.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.871(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4961(5)
_cell_length_b                   23.7140(19)
_cell_length_c                   17.6522(13)
_cell_measurement_reflns_used    677
_cell_measurement_temperature    295.35(10)
_cell_measurement_theta_max      18.2920
_cell_measurement_theta_min      3.6220
_cell_volume                     2284.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -23.00   31.00   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  -30.0000 36

  2 omega  -36.00   72.00   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -150.0000 72

  3 omega   69.00   97.50   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000 -180.0000 19

  4 omega  -17.00   10.00   1.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  120.0000 18
;
_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      0.1132813000
_diffrn_orient_matrix_UB_12      -0.0015536000
_diffrn_orient_matrix_UB_13      0.0238383000
_diffrn_orient_matrix_UB_21      0.0270237000
_diffrn_orient_matrix_UB_22      -0.0257707000
_diffrn_orient_matrix_UB_23      -0.0176110000
_diffrn_orient_matrix_UB_31      0.0578175000
_diffrn_orient_matrix_UB_32      0.0150963000
_diffrn_orient_matrix_UB_33      -0.0275552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.1995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8712
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.2562
_refine_ls_R_factor_gt           0.0820
_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^)+(0.0716P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.2684
_reflns_number_gt                1355
_reflns_number_total             4489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01657_si_003.cif
_cod_data_source_block           qiuyf0511
_cod_database_code               1529877
_chemical_oxdiff_formula         'C19 N1 H12 S13'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C5(H5a,H5b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
;
_olex2_date_sample_data_collection 2015-05-11
_olex2_submission_special_instructions 'No special instructions were received'