Synthesis of CF<sub>3</sub>CH<sub>2</sub>-Containing Indolines by Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes.
Liang, Deqiang; Dong, Qishan; Xu, Penghui; Dong, Ying; Li, Weili; Ma, Yinhai; The Journal of organic chemistry 83 (2018) 11978–11986; doi:10.1021/acs.joc.8b01861

data_4035194
_publ_section_title
;
 Synthesis of CF<sub>3</sub>CH<sub>2</sub>-Containing Indolines by
 Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11978
_journal_page_last               11986
_journal_paper_doi               10.1021/acs.joc.8b01861
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H16 F3 N O2 S'
_chemical_formula_sum            'C17 H16 F3 N O2 S'
_chemical_formula_weight         355.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-05
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                94.560(15)
_cell_angle_beta                 105.319(17)
_cell_angle_gamma                101.949(16)
_cell_formula_units_Z            2
_cell_length_a                   8.2932(16)
_cell_length_b                   9.6779(17)
_cell_length_c                   10.890(2)
_cell_measurement_reflns_used    1364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8270
_cell_measurement_theta_min      4.7250
_cell_volume                     816.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9790
_diffrn_measured_fraction_theta_max 0.9508
_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     28.00  69.00   1.00    1.00    --    0.00  57.00 -60.00   41
  2  \w     46.00 117.00   1.00    2.48    --   54.00  57.00 -90.00   71
  3  \w    135.00 177.00   1.00    2.48    --  108.00  37.00   0.00   42
  4  \w    141.00 169.00   1.00    2.48    --  108.00  37.00  60.00   28
  5  \w    102.00 170.00   1.00    2.48    --  108.00  63.00 150.00   68
  6  \w     88.00 137.00   1.00    2.48    --  108.00  37.00  60.00   49
  7  \w     84.00 110.00   1.00    2.48    --  108.00  37.00   0.00   26
  8  \w    116.00 142.00   1.00    2.48    --  108.00 111.00 -90.00   26
  9  \w     75.00 140.00   1.00    2.48    --  108.00 -25.00-180.00   65
 10  \w     71.00 107.00   1.00    2.48    --  108.00-111.00   0.00   36
 11  \w     58.00 127.00   1.00    2.48    --  108.00 -50.00  60.00   69
 12  \w     51.00 138.00   1.00    2.48    --  108.00 -91.00  60.00   87
 13  \w     49.00 128.00   1.00    2.48    --  108.00 -37.00   0.00   79
 14  \w     46.00 113.00   1.00    2.48    --   54.00  57.00 150.00   67
 15  \w     40.00 112.00   1.00    2.48    --  108.00 -63.00 -60.00   72
 16  \w     45.00 110.00   1.00    2.48    --  108.00 -63.00-150.00   65
 17  \w     39.00 110.00   1.00    2.48    --   54.00-125.00-120.00   71
 18  \w     32.00  60.00   1.00    2.48    --   54.00 -37.00-120.00   28
 19  \w     35.00  68.00   1.00    2.48    --  108.00 -25.00-180.00   33
 20  \w     40.00 115.00   1.00    2.48    --   54.00  57.00-150.00   75
 21  \w     -2.00  46.00   1.00    2.48    --   54.00 -57.00 -30.00   48
 22  \w     36.00 111.00   1.00    2.48    --  108.00-111.00-120.00   75
 23  \w     -9.00  69.00   1.00    2.48    --   54.00 -77.00  60.00   78
 24  \w     -9.00  18.00   1.00    1.00    --    0.00 -57.00 150.00   27
 25  \w    -52.00 -27.00   1.00    1.00    --    0.00 -57.00 150.00   25
 26  \w    -16.00  22.00   1.00    1.00    --    0.00  57.00 -60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0790204000
_diffrn_orient_matrix_UB_12      -0.0936402000
_diffrn_orient_matrix_UB_13      0.0957575000
_diffrn_orient_matrix_UB_21      -0.1650370000
_diffrn_orient_matrix_UB_22      -0.0308373000
_diffrn_orient_matrix_UB_23      0.0429968000
_diffrn_orient_matrix_UB_31      -0.0763348000
_diffrn_orient_matrix_UB_32      -0.1315357000
_diffrn_orient_matrix_UB_33      -0.1045884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4456
_diffrn_reflns_theta_full        63.64
_diffrn_reflns_theta_max         63.64
_diffrn_reflns_theta_min         4.25
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.9348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                1792
_reflns_number_total             2590
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01861_si_002.cif
_cod_data_source_block           exp_2846
_cod_original_cell_volume        816.4(3)
_cod_database_code               4035194
_reflns_odcompleteness_completeness 97.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.637