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_7160947
_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         'C15 H18 F3 N O S'
_chemical_formula_sum            'C15 H18 F3 N O S'
_chemical_formula_weight         317.36
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2nxl4b
_audit_creation_date             2025-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-08-27 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                75.592(5)
_cell_angle_beta                 69.758(5)
_cell_angle_gamma                64.633(6)
_cell_formula_units_Z            4
_cell_length_a                   10.9931(6)
_cell_length_b                   11.7901(8)
_cell_length_c                   15.1378(7)
_cell_measurement_reflns_used    5236
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0870
_cell_measurement_theta_min      2.3540
_cell_volume                     1651.59(19)
_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 0.999
_diffrn_measured_fraction_theta_max 0.835
_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    -15.00  75.00   0.50    3.20    --   -9.40  55.00-180.00  180
  2  \w    -82.00 -55.00   0.50    3.20    --   -9.40  55.00  60.00   54
  3  \w    -25.00  79.00   0.50    3.20    --   -9.40  55.00  60.00  208
  4  \w    -25.00  74.00   0.50    3.20    --   -9.40  55.00 -60.00  198
  5  \w    -86.00 -61.00   0.50    3.20    --   -9.40  43.00  90.00   50
  6  \w    -46.00  55.00   0.50    3.20    --   -9.40  43.00  90.00  202
  7  \w    -10.00  74.00   0.50    3.20    --   -9.40  29.00 -60.00  168
;
_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      -0.0495343000
_diffrn_orient_matrix_UB_12      -0.0292456000
_diffrn_orient_matrix_UB_13      0.0210679000
_diffrn_orient_matrix_UB_21      0.0104916000
_diffrn_orient_matrix_UB_22      -0.0062427000
_diffrn_orient_matrix_UB_23      0.0449157000
_diffrn_orient_matrix_UB_31      -0.0542925000
_diffrn_orient_matrix_UB_32      0.0600167000
_diffrn_orient_matrix_UB_33      0.0082703000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.556
_diffrn_reflns_theta_min         2.132
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54800
_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    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       0.022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7728
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0751
_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^)+(0.1757P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2284
_refine_ls_wR_factor_ref         0.2830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3930
_reflns_number_total             7728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01913c2.cif
_cod_data_source_block           20250226-44-2
_cod_depositor_comments
'Adding full bibliography for 7160944--7160947.cif.'
_cod_database_code               7160947
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.989
_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. Uiso/Uaniso restraints and constraints
Uanis(C012) \\sim Ueq, Uanis(C013) \\sim Ueq, Uanis(C015) \\sim Ueq,
Uanis(C016) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C010) \\sim Ueq, Uanis(C011) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00Q(H00Q), C00V(H00V)
3.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00O(H00O), C00R(H00R),
 C00S(H00S), C00T(H00T)
3.c Idealised Me refined as rotating group:
 C00Z(H00A,H00B,H00C), C010(H01M,H01N,H01O), C011(H01A,H01B,H01C), C012(H01P,
 H01Q,H01R), C013(H01S,H01T,H01U), C014(H01D,H01E,H01F), C015(H01G,H01H,H01I),
 C016(H01J,H01K,H01L)
;
_shelx_res_checksum              9369
_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.883