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_1543011
_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         'C22 H15 F3 O S'
_chemical_formula_sum            'C22 H15 F3 O S'
_chemical_formula_weight         384.40
_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             2015-11-16
_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                 94.431(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2577(3)
_cell_length_b                   12.2802(4)
_cell_length_c                   22.5646(5)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2640
_cell_measurement_theta_min      3.7310
_cell_volume                     3662.70(17)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_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  -47.00    1.00   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  -60.0000 40

  2 omega  -14.00   42.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -77.0000   60.0000 47

  3 omega   22.00   83.20   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -120.0000 51

  4 omega    0.00   75.60   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -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      -0.0526525000
_diffrn_orient_matrix_UB_12      0.0109491000
_diffrn_orient_matrix_UB_13      -0.0037915000
_diffrn_orient_matrix_UB_21      0.0015135000
_diffrn_orient_matrix_UB_22      0.0209532000
_diffrn_orient_matrix_UB_23      0.0293384000
_diffrn_orient_matrix_UB_31      0.0103422000
_diffrn_orient_matrix_UB_32      0.0526848000
_diffrn_orient_matrix_UB_33      -0.0108974000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15643
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93271
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0389P)^2^+1.0747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                4497
_reflns_number_total             7208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00065_si_002.cif
_cod_data_source_block           qiuyf1116
_cod_database_code               1543011
_reflns_odcompleteness_completeness 99.72
_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.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
  C2(H2), C5(H5), C5AA(H5AA), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_date_sample_data_collection 2015-11-16
_olex2_submission_special_instructions 'No special instructions were received'