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_1529878
_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         'C16 H15 F3 O3 S'
_chemical_formula_sum            'C16 H15 F3 O3 S'
_chemical_formula_weight         344.34
_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             2015-06-05
_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                 106.109(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9242(4)
_cell_length_b                   15.9342(6)
_cell_length_c                   10.0614(4)
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.7580
_cell_measurement_theta_min      4.2360
_cell_volume                     1528.58(11)
_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      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega   47.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000 -150.0000 44

  2 omega    1.00   51.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   30.0000 50

  3 omega   12.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000 -180.0000 54

  4 omega   -5.00   21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  -30.0000 26

  5 omega   57.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  -30.0000 27

  6 omega   -2.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  120.0000 50
;
_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      -0.0367543000
_diffrn_orient_matrix_UB_12      -0.0386009000
_diffrn_orient_matrix_UB_13      -0.0143097000
_diffrn_orient_matrix_UB_21      -0.0638340000
_diffrn_orient_matrix_UB_22      0.0211755000
_diffrn_orient_matrix_UB_23      -0.0041643000
_diffrn_orient_matrix_UB_31      -0.0100455000
_diffrn_orient_matrix_UB_32      0.0064289000
_diffrn_orient_matrix_UB_33      -0.0719312000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6502
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85050
_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    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0369P)^2^+0.8392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2276
_reflns_number_total             2937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01657_si_004.cif
_cod_data_source_block           qiuyf_0605
_cod_original_cell_volume        1528.57(10)
_cod_database_code               1529878
_reflns_odcompleteness_completeness 96.34
_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:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2015-06-05
_olex2_submission_special_instructions 'No special instructions were received'