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_7128681
_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         'C22 H17 F3 O'
_chemical_formula_sum            'C22 H17 F3 O'
_chemical_formula_weight         354.35
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_date             2020-02-10T16:04:58-00:00
_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                99.278(3)
_cell_angle_beta                 94.538(3)
_cell_angle_gamma                113.082(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7235(4)
_cell_length_b                   9.8806(3)
_cell_length_c                   10.7952(4)
_cell_measurement_reflns_used    4689
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.326
_cell_measurement_theta_min      4.962
_cell_volume                     834.34(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 0.986
_diffrn_measured_fraction_theta_max 0.985
_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    -62.00 -32.00   1.00    1.00    --  -42.13  38.00 -30.00   30
  2  \w    -30.00  -3.00   1.00    1.00    --  -42.13  38.00 -30.00   27
  3  \w     18.00 112.00   1.00    1.00    --   42.13  38.00 150.00   94
  4  \w    -32.00  63.00   1.00    1.00    --   42.13 -38.00 -30.00   95
  5  \w      5.00  97.00   1.00    1.00    --   42.13-125.00 -90.00   92
  6  \w     36.00  68.00   1.00    1.00    --  107.93 -45.00  30.00   32
  7  \w     32.00  61.00   1.00    1.00    --  107.93 -30.00 -60.00   29
  8  \w     35.00  63.00   1.00    1.00    --  107.93 -45.00  90.00   28
  9  \w     50.00  76.00   1.00    1.00    --  107.93 -45.00-180.00   26
 10  \w     37.00 104.00   1.00    1.00    --  107.93-125.00 150.00   67
 11  \w    107.00 134.00   1.00    1.00    --  107.93 -77.00-180.00   27
 12  \w     38.00  65.00   1.00    1.00    --  107.93 -45.00   0.00   27
 13  \w     38.00  65.00   1.00    1.00    --  107.93 -30.00-150.00   27
 14  \w     30.00  94.00   1.00    1.00    --  107.93 -94.00  30.00   64
 15  \w     36.00 118.00   1.00    1.00    --  107.93-125.00-150.00   82
 16  \w     32.00  65.00   1.00    1.00    --  107.93 -77.00-180.00   33
 17  \w     35.00  85.00   1.00    1.00    --  107.93-104.00  -8.00   50
 18  \w     26.00  52.00   1.00    1.00    --  107.93 -94.00-120.00   26
 19  \w     55.00 109.00   1.00    1.00    --  107.93 -94.00-120.00   54
 20  \w     87.00 157.00   1.00    1.00    --  107.93  30.00 -30.00   70
 21  \w     25.00 158.00   1.00    1.00    --  107.93   0.00 -60.00  133
;
_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      0.1445279
_diffrn_orient_matrix_UB_12      0.0235626
_diffrn_orient_matrix_UB_13      0.1043515
_diffrn_orient_matrix_UB_21      -0.1258945
_diffrn_orient_matrix_UB_22      -0.0402548
_diffrn_orient_matrix_UB_23      0.0946068
_diffrn_orient_matrix_UB_31      -0.0322835
_diffrn_orient_matrix_UB_32      -0.1669436
_diffrn_orient_matrix_UB_33      -0.0399505
_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  0.0141
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5454
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.996
_diffrn_reflns_theta_min         4.976
_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    0.909
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.698
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.336
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.2674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0
_reflns_number_gt                2879
_reflns_number_total             3047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03161a2.cif
_cod_data_source_block           a20180220_as551
_cod_depositor_comments
'Adding full bibliography for 7128680--7128681.cif.'
_cod_database_code               7128681