Electrochemical trifluoroalkylation/annulation for the synthesis of CF<sub>3</sub>-functionalized tetrahydroquinolines and dihydroquinolinones.
Wu, Hao-Zeng; Teng, Zhong-Shan; Ke, Yu-Xin; Zou, Yu; Gao, Ping; Li, Yue; Zhou, Cheng-He; Zang, Zhong-Lin; Organic & biomolecular chemistry 21 (2023) 8579–8583; doi:10.1039/d3ob00987d

data_7159591
_publ_section_title
;
 Electrochemical trifluoroalkylation/annulation for the synthesis of
 CF<sub>3</sub>-functionalized tetrahydroquinolines and
 dihydroquinolinones.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8579
_journal_page_last               8583
_journal_paper_doi               10.1039/d3ob00987d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H20 F3 N O2 S'
_chemical_formula_sum            'C23 H20 F3 N O2 S'
_chemical_formula_weight         431.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.01(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6163(17)
_cell_length_b                   9.1345(7)
_cell_length_c                   17.600(5)
_cell_measurement_reflns_used    5762
_cell_measurement_temperature    291.5(4)
_cell_measurement_theta_max      70.8030
_cell_measurement_theta_min      4.8390
_cell_volume                     2081.8(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      air
_diffrn_ambient_temperature      291.5(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.861
_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    -53.00  31.00   1.00    2.26    --  -35.97  57.00 -30.00   84
  2  \w   -103.00 -19.00   1.00    2.26    --  -35.97 -57.00   0.00   84
  3  \w     28.00  90.00   1.00    2.26    --   35.97-126.00  30.00   62
  4  \w      6.00  75.00   1.00    2.26    --   35.97 -99.00-120.00   69
  5  \w     19.00 103.00   1.00    2.26    --   35.97  57.00-180.00   84
  6  \w    103.00 176.00   1.00    9.03    --  107.97  77.00 -30.00   73
  7  \w    104.00 178.00   1.00    9.03    --  107.97 112.00-120.00   74
  8  \w     39.00 106.00   1.00    9.03    --  107.97 -95.00   0.00   67
  9  \w     61.00 146.00   1.00    9.03    --  107.97 178.00-120.00   85
 10  \w     38.00 129.00   1.00    9.03    --  107.97 -30.00 -30.00   91
 11  \w     41.00 126.00   1.00    9.03    --  107.97 -61.00-180.00   85
 12  \w    104.00 178.00   1.00    9.03    --  107.97 112.00  30.00   74
 13  \w     39.00 106.00   1.00    9.03    --  107.97 -95.00-180.00   67
 14  \w     91.00 176.00   1.00    9.03    --  107.97  45.00 -60.00   85
 15  \w    -53.00  31.00   1.00    2.26    --  -35.97  57.00  60.00   84
 16  \w    -53.00  31.00   1.00    2.26    --  -35.97  57.00 150.00   84
 17  \w   -105.00 -17.00   1.00    2.26    --  -35.97 -38.00-120.00   88
 18  \w     19.00 103.00   1.00    2.26    --   35.97  57.00  90.00   84
 19  \w     87.00 178.00   1.00    9.03    --  107.97  30.00  60.00   91
 20  \w     70.00 178.00   1.00    9.03    --  107.97  15.00-120.00  108
 21  \w     87.00 178.00   1.00    9.03    --  107.97  30.00 150.00   91
 22  \w     87.00 178.00   1.00    9.03    --  107.97  30.00   0.00   91
 23  \w     41.00 126.00   1.00    9.03    --  107.97 -61.00 -60.00   85
 24  \w     87.00 178.00   1.00    9.03    --  107.97  30.00 -90.00   91
 25  \w     90.00 175.00   1.00    9.03    --  107.97  61.00  90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0741776000
_diffrn_orient_matrix_UB_12      -0.0479157000
_diffrn_orient_matrix_UB_13      0.0815496000
_diffrn_orient_matrix_UB_21      -0.0896557000
_diffrn_orient_matrix_UB_22      -0.0800534000
_diffrn_orient_matrix_UB_23      0.0187689000
_diffrn_orient_matrix_UB_31      0.0254199000
_diffrn_orient_matrix_UB_32      -0.1404100000
_diffrn_orient_matrix_UB_33      -0.0382186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18425
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.197
_diffrn_reflns_theta_min         3.613
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         1.280
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       0.0017(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.635
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.635
_refine_ls_R_factor_all          0.1919
_refine_ls_R_factor_gt           0.1724
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4238
_refine_ls_wR_factor_ref         0.4494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3086
_reflns_number_total             4052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00987d2.cif
_cod_data_source_block           whzl-1
_cod_depositor_comments          'Adding full bibliography for 7159591.cif.'
_cod_database_code               7159591
_shelxl_version_number           2014-1
_chemical_oxdiff_usercomment     'C1 H1 N1 O1 F1 S1'
_shelx_estimated_absorpt_t_max   0.565
_shelx_estimated_absorpt_t_min   0.520
_reflns_odcompleteness_completeness 99.97
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.322
_oxdiff_exptl_absorpt_empirical_full_min 0.473