Photoredox catalyzed synthesis of β-trifluoromethyl β-aminoketones from <i>N</i>-trifluoroethyl hydroxylamine reagent and silyl enol ethers.
Feng, Yuxi; Liu, Shuai; Meng, Weidong; Huang, Yangen; Organic & biomolecular chemistry  (2025) –; doi:10.1039/d5ob01591j

data_7160866
_publ_section_title
;
 Photoredox catalyzed synthesis of &#x3b2;-trifluoromethyl
 &#x3b2;-aminoketones from <i>N</i>-trifluoroethyl hydroxylamine reagent
 and silyl enol ethers.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d5ob01591j
_journal_year                    2025
_chemical_formula_moiety         'C19 H18 F3 N O4'
_chemical_formula_sum            'C19 H18 F3 N O4'
_chemical_formula_weight         381.34
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2nzpt5
_audit_creation_date             2025-05-12
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-07-13 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.714(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1227(12)
_cell_length_b                   4.9556(4)
_cell_length_c                   25.231(3)
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      72.1690
_cell_measurement_theta_min      3.4770
_cell_volume                     1753.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_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     26.00  62.00   1.00    3.00    --   41.11  38.00 120.00   36
  2  \w     31.00 133.00   1.00    8.00    --  107.58 -77.00 150.00  102
  3  \w     47.00 135.00   1.00    8.00    --  107.58 -30.00 -60.00   88
  4  \w     90.00 177.00   1.00    8.00    --  107.58  61.00 -90.00   87
  5  \w     59.00 114.00   1.00    8.00    --  107.58 -61.00 -90.00   55
  6  \w     36.00  69.00   1.00    8.00    --  107.58 -94.00-150.00   33
  7  \w    -96.00 -45.00   1.00    3.00    --  -41.11 125.00  90.00   51
  8  \w    -99.00 -58.00   1.00    3.00    --  -41.11-155.00 121.00   41
  9  \w   -117.00 -14.00   1.00    3.00    --  -41.11 -19.00  90.00  103
 10  \w     78.00 104.00   1.00   15.00    --  107.58 -94.00 -90.00   26
 11  \w    -18.00  14.00   1.00   12.00    --   41.23 -57.00  30.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0392718000
_diffrn_orient_matrix_UB_12      -0.1401160000
_diffrn_orient_matrix_UB_13      0.0473673000
_diffrn_orient_matrix_UB_21      -0.0808851000
_diffrn_orient_matrix_UB_22      -0.1250593000
_diffrn_orient_matrix_UB_23      -0.0385036000
_diffrn_orient_matrix_UB_31      0.0631095000
_diffrn_orient_matrix_UB_32      -0.2475939000
_diffrn_orient_matrix_UB_33      -0.0073876000
_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  0.0822
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6098
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.671
_diffrn_reflns_theta_min         3.426
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0901P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.2283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2133
_reflns_number_total             3416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01591j2.cif
_cod_data_source_block           exp_5930
_cod_database_code               7160866
_shelx_shelxl_version_number     2018/3
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              17052
_olex2_date_sample_data_collection 2025-05-12
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.502
_oxdiff_exptl_absorpt_empirical_full_min 0.538