Unexpected metal-free synthesis of trifluoromethyl arenes <i>via</i> tandem coupling of dicyanoalkenes and conjugated fluorinated sulfinyl imines.
Sanz-Vidal, Alvaro; Gaviña, Daniel; Sotorríos, Lia; Gómez-Bengoa, Enrique; López Ortiz, Fernando; Sánchez-Roselló, María; Del Pozo, Carlos; Chemical communications (Cambridge, England) 57 (2021) 8023–8026; doi:10.1039/d1cc03161a

data_7128680
_publ_section_title
;
 Unexpected metal-free synthesis of trifluoromethyl arenes <i>via</i>
 tandem coupling of dicyanoalkenes and conjugated fluorinated sulfinyl
 imines.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8023
_journal_page_last               8026
_journal_paper_doi               10.1039/d1cc03161a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C20 H13 F3 O'
_chemical_formula_sum            'C20 H13 F3 O'
_chemical_formula_weight         326.3
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-02-11T11:42:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-03-12 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1749(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5329(2)
_cell_length_b                   17.6088(2)
_cell_length_c                   9.47700(11)
_cell_measurement_reflns_used    7218
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.291
_cell_measurement_theta_min      3.49
_cell_volume                     3023.18(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      8.00  34.00   1.00    1.00    --  -42.13  77.00 150.00   26
  2  \w    -68.00 -38.00   1.00    1.00    --  -42.13  77.00 150.00   30
  3  \w      5.00  67.00   1.00    1.00    --   42.13-125.00  60.00   62
  4  \w     20.00 115.00   1.00    1.00    --   42.13  57.00  60.00   95
  5  \w     26.00  71.00   1.00    1.00    --   42.13  38.00 -90.00   45
  6  \w     18.00 112.00   1.00    1.00    --   42.13  38.00-180.00   94
  7  \w     86.00 149.00   1.00    1.00    --  107.93  45.00-180.00   63
  8  \w     36.00  65.00   1.00    1.00    --  107.93 -30.00  90.00   29
  9  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00-120.00   37
 10  \w     35.00 114.00   1.00    1.00    --  107.93-125.00  60.00   79
 11  \w     34.00  64.00   1.00    1.00    --  107.93 -30.00 150.00   30
 12  \w     44.00  70.00   1.00    1.00    --  107.93-125.00 -60.00   26
 13  \w     92.00 117.00   1.00    1.00    --  107.93-125.00 -60.00   25
 14  \w     86.00 129.00   1.00    1.00    --  107.93 -77.00   0.00   43
 15  \w     38.00 127.00   1.00    1.00    --  107.93 -77.00-180.00   89
 16  \w     40.00  67.00   1.00    1.00    --  107.93 -30.00   0.00   27
 17  \w    110.00 157.00   1.00    1.00    --  107.93  45.00-150.00   47
 18  \w     32.00  60.00   1.00    1.00    --  107.93 -30.00-180.00   28
 19  \w     36.00  68.00   1.00    1.00    --  107.93 -30.00 120.00   32
 20  \w     35.00  67.00   1.00    1.00    --  107.93 -30.00  60.00   32
 21  \w     27.00  86.00   1.00    1.00    --  107.93 -94.00 -30.00   59
 22  \w     58.00 114.00   1.00    1.00    --  107.93-125.00-180.00   56
 23  \w     78.00 145.00   1.00    1.00    --  107.93 125.00-150.00   67
 24  \w     36.00  65.00   1.00    1.00    --  107.93 -45.00   0.00   29
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0705629
_diffrn_orient_matrix_UB_12      0.0389783
_diffrn_orient_matrix_UB_13      -0.0255561
_diffrn_orient_matrix_UB_21      -0.0253944
_diffrn_orient_matrix_UB_22      0.0755261
_diffrn_orient_matrix_UB_23      0.0557085
_diffrn_orient_matrix_UB_31      0.0400979
_diffrn_orient_matrix_UB_32      -0.0207956
_diffrn_orient_matrix_UB_33      0.1545614
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10049
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.982
_diffrn_reflns_theta_min         3.5
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+2.2739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0
_reflns_number_gt                2579
_reflns_number_total             2784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03161a2.cif
_cod_data_source_block           a20180274_as552
_cod_depositor_comments
'Adding full bibliography for 7128680--7128681.cif.'
_cod_database_code               7128680