Synthesis of α-trifluoromethyl-β-lactams <i>via</i> a copper-catalyzed Kinugasa reaction of nitrones with 3,3,3-trifluoropropyne and their defluorination.
Chen, Shouxiong; Yang, Peiqi; Hong, Biqiong; Yang, Fafu; Weng, Zhiqiang; Organic & biomolecular chemistry 24 (2026) 1908–1914; doi:10.1039/d5ob01913c

data_7160945
_publ_section_title
;
 Synthesis of &#x3b1;-trifluoromethyl-&#x3b2;-lactams <i>via</i> a
 copper-catalyzed Kinugasa reaction of nitrones with
 3,3,3-trifluoropropyne and their defluorination.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1908
_journal_page_last               1914
_journal_paper_doi               10.1039/d5ob01913c
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C28 H24 F N5 O'
_chemical_formula_sum            'C28 H24 F N5 O'
_chemical_formula_weight         465.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-10-30 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.810(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2997(10)
_cell_length_b                   11.4114(9)
_cell_length_c                   19.4488(14)
_cell_measurement_reflns_used    6710
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3150
_cell_measurement_theta_min      2.8490
_cell_volume                     2400.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_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    -76.00 -49.00   0.50   67.90    --   -8.70  10.00 138.00   54
  2  \w    -67.00 -41.00   0.50   67.90    --    5.00  55.00-120.00   52
  3  \w     13.00  39.00   0.50   67.90    --    5.00  55.00-120.00   52
  4  \w    -98.00  22.00   0.50   67.90    --   -8.70  55.00-150.00  240
  5  \w     36.00  79.00   0.50   67.90    --   -8.70  55.00-150.00   86
  6  \w    -32.00  -7.00   0.50   67.90    --   -8.70  10.00 138.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0030673000
_diffrn_orient_matrix_UB_12      -0.0077182000
_diffrn_orient_matrix_UB_13      -0.0356212000
_diffrn_orient_matrix_UB_21      -0.0650671000
_diffrn_orient_matrix_UB_22      -0.0076663000
_diffrn_orient_matrix_UB_23      -0.0120896000
_diffrn_orient_matrix_UB_31      -0.0076630000
_diffrn_orient_matrix_UB_32      0.0611900000
_diffrn_orient_matrix_UB_33      -0.0060158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14033
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.594
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.1017
_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^)+(0.1888P)^2^+2.9601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3018
_refine_ls_wR_factor_ref         0.3163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2958
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01913c2.cif
_cod_data_source_block           kt1-ysh-3-20251021
_cod_depositor_comments
'Adding full bibliography for 7160944--7160947.cif.'
_cod_database_code               7160945
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.993
_reflns_odcompleteness_completeness 97.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C9(H9), C2(H2), C7(H7), C14(H14), C11(H11), C23(H23), C13(H13),
 C12(H12), C20(H20), C21(H21), C5(H5), C4(H4), C6(H6)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              93452
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.697