A Cu-promoted reaction of β-keto trifluoromethyl amines enabling stereoselective synthesis of trifluoromethylated aziridines.
Wang, Nana; Du, Youlong; Mei, Haibo; Escorihuela, Jorge; Han, Jianlin; Organic & biomolecular chemistry 21 (2023) 4988–4992; doi:10.1039/d3ob00714f

data_7159389
_publ_section_title
;
 A Cu-promoted reaction of &#x3b2;-keto trifluoromethyl amines enabling
 stereoselective synthesis of trifluoromethylated aziridines.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4988
_journal_page_last               4992
_journal_paper_doi               10.1039/d3ob00714f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C10 H8 F3 N O'
_chemical_formula_sum            'C10 H8 F3 N O'
_chemical_formula_weight         215.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-10-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.534(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5623(11)
_cell_length_b                   18.321(3)
_cell_length_c                   9.2234(17)
_cell_measurement_reflns_used    2079
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.4750
_cell_measurement_theta_min      2.4620
_cell_volume                     939.6(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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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 0.860
_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    -52.00  65.00   1.00    3.00    --  -11.27  19.00   0.00  117
  2  \w    -55.00  -7.00   1.00    3.00    --   11.90 -38.00-180.00   48
  3  \w    -90.00 -63.00   1.00    3.00    --  -11.27 -19.00  30.00   27
  4  \w     60.00  92.00   1.00    3.00    --   11.90-178.00   0.00   32
  5  \w    -19.00  -4.00   1.00    5.00    --  -11.43 -99.00  30.00   15
;
_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      0.0596061000
_diffrn_orient_matrix_UB_12      0.0108761000
_diffrn_orient_matrix_UB_13      0.0655426000
_diffrn_orient_matrix_UB_21      -0.0310557000
_diffrn_orient_matrix_UB_22      -0.0337048000
_diffrn_orient_matrix_UB_23      0.0321679000
_diffrn_orient_matrix_UB_31      0.1084626000
_diffrn_orient_matrix_UB_32      -0.0155685000
_diffrn_orient_matrix_UB_33      -0.0243440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.1000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3421
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.683
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.449
_diffrn_reflns_theta_min         2.209
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73842
_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            'light colourless'
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0903
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1643P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2458
_refine_ls_wR_factor_ref         0.2699
_reflns_Friedel_coverage         0.544
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.496
_reflns_number_gt                2472
_reflns_number_total             3421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00714f2.cif
_cod_data_source_block           wnn-3
_cod_depositor_comments          'Adding full bibliography for 7159389.cif.'
_cod_database_code               7159389
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.799(3)
 0.201(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Restrained distances
 N2-H2A
 0.86 with sigma of 0.01
4.a Riding coordinates:
 N1(H1)
4.b Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C13(H13)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              81279
_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 2.515
_oxdiff_exptl_absorpt_empirical_full_min 0.553