BF3·OEt2-AgSCF3 Mediated Trifluoromethylthiolation/Cascade Cyclization of Propynols: Synthesis of 4-((Trifluoromethyl)thio)-2H-chromene and 4-((Trifluoromethyl)thio)-1,2-dihydroquinoline Derivatives.
Qiu, Yi-Feng; Song, Xian-Rong; Li, Ming; Zhu, Xin-Yu; Wang, An-Qi; Yang, Fang; Han, Ya-Ping; Zhang, Heng-Rui; Jin, Dong-Po; Li, Ying-Xiu; Liang, Yong-Min; Organic letters 18 (2016) 1514–1517; doi:10.1021/acs.orglett.6b00065

data_1543013
_publ_section_title
;
 BF3&#x00B7;OEt2-AgSCF3 Mediated Trifluoromethylthiolation/Cascade
 Cyclization of Propynols: Synthesis of
 4-((Trifluoromethyl)thio)-2H-chromene and
 4-((Trifluoromethyl)thio)-1,2-dihydroquinoline Derivatives.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1514
_journal_page_last               1517
_journal_paper_doi               10.1021/acs.orglett.6b00065
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C26 H17 F3 O S'
_chemical_formula_sum            'C26 H17 F3 O S'
_chemical_formula_weight         434.46
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.851(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.9922(6)
_cell_length_b                   34.479(2)
_cell_length_c                   11.1612(5)
_cell_measurement_reflns_used    2307
_cell_measurement_temperature    293.60(10)
_cell_measurement_theta_max      22.1100
_cell_measurement_theta_min      3.6610
_cell_volume                     4214.9(4)
_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      293.60(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   39.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   19.0000   60.0000 25

  2 omega   -6.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -30.0000 27

  3 omega  -51.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -150.0000 97

  4 omega  -20.00    5.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -180.0000 25

  5 omega   34.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000 -180.0000 63
;
_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      0.0615820000
_diffrn_orient_matrix_UB_12      -0.0062449000
_diffrn_orient_matrix_UB_13      0.0090158000
_diffrn_orient_matrix_UB_21      0.0196002000
_diffrn_orient_matrix_UB_22      0.0195953000
_diffrn_orient_matrix_UB_23      0.0026954000
_diffrn_orient_matrix_UB_31      -0.0040842000
_diffrn_orient_matrix_UB_32      0.0000520000
_diffrn_orient_matrix_UB_33      0.0631044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17521
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66892
_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    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         8293
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0714
_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^)+(0.0735P)^2^+1.0178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.2072
_reflns_number_gt                4188
_reflns_number_total             8293
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00065_si_004.cif
_cod_data_source_block           qiuyf_0121
_cod_database_code               1543013
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F5') \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6') \\sim Ueq, Uanis(F6)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F5(0.5) F6(0.5) F5'(0.5) F6'(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C38(H38),
 C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48), C49(H49),
  C50(H50), C51(H51), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25)
;
_olex2_date_sample_data_collection 2016-01-20
_olex2_submission_special_instructions 'No special instructions were received'