Regioselective access to CF3S-substituted dihydrofurans from homopropargylic alcohols with trifluoromethanesulfenamide
Dao-Qian Chen; Pin Gao; Ping-Xin Zhou; Xian-Rong Song; Yi-Feng Qiu; Xue-Yuan Liu; Yong-Min Liang; Chem.Commun. 51 (2015) 6637–; doi:10.1039/C5cc00669D

data_7116906
_publ_section_title
;
 Regioselective access to CF3S-substituted dihydrofurans from
 homopropargylic alcohols with trifluoromethanesulfenamide
;
_journal_name_full               Chem.Commun.
_journal_page_first              6637
_journal_paper_doi               10.1039/C5cc00669D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C23 H17 F3 O S'
_chemical_formula_sum            'C23 H17 F3 O S'
_chemical_formula_weight         398.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-01-14 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                79.807(13)
_cell_angle_beta                 74.337(16)
_cell_angle_gamma                82.314(11)
_cell_formula_units_Z            2
_cell_length_a                   9.4049(15)
_cell_length_b                   10.3048(12)
_cell_length_c                   10.563(2)
_cell_measurement_reflns_used    1465
_cell_measurement_temperature    294.58(10)
_cell_measurement_theta_max      24.5140
_cell_measurement_theta_min      3.9010
_cell_volume                     966.1(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      294.58(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   -9.00   25.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  150.0000 17

  2 omega  -20.00   54.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  120.0000 37

  3 omega  -36.00   34.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000    0.0000 35

  4 omega  -13.00   23.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 18

  5 omega  -52.00   34.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000  120.0000 43

  6 omega  -46.00   36.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000 -120.0000 41
;
_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      0.0654946000
_diffrn_orient_matrix_UB_12      -0.0358743000
_diffrn_orient_matrix_UB_13      -0.0323710000
_diffrn_orient_matrix_UB_21      0.0304491000
_diffrn_orient_matrix_UB_22      -0.0010107000
_diffrn_orient_matrix_UB_23      0.0547498000
_diffrn_orient_matrix_UB_31      -0.0311333000
_diffrn_orient_matrix_UB_32      -0.0603622000
_diffrn_orient_matrix_UB_33      0.0304307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6518
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85822
_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    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0604P)^2^+0.1261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                2393
_reflns_number_total             3781
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00669d2.cif
_cod_data_source_block           liangym0106
_cod_original_cell_volume        966.2(3)
_cod_database_code               7116906
_reflns_odcompleteness_completeness 99.54
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_olex2_date_sample_data_collection 2015-01-07
_olex2_submission_special_instructions 'No special instructions were received'