Base mediated aza-[2 + 1] annulation and regioselective aziridine ring-opening cascade: mild synthesis of functionalized β-amino ketones from cyclic N-sulfonyl aldimines and α-carbonyl sulfonium salts
Lei, Xiaoqiang; Sun, Yanyan; Guo, Qinglan; Shi, Jiangong; RSC Advances 14 (2024) 17178–17183; doi:10.1039/D4RA02817A

data_7248732
_publ_section_title
;
 Base mediated aza-[2 + 1] annulation and regioselective aziridine
 ring-opening cascade: mild synthesis of functionalized \b-amino ketones
 from cyclic N-sulfonyl aldimines and \a-carbonyl sulfonium salts
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              17178
_journal_page_last               17183
_journal_paper_doi               10.1039/D4RA02817A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H11 N O4 S'
_chemical_formula_sum            'C15 H11 N O4 S'
_chemical_formula_weight         301.31
_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             2022-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.188(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0912(3)
_cell_length_b                   5.88627(10)
_cell_length_c                   13.7901(3)
_cell_measurement_reflns_used    10171
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3440
_cell_measurement_theta_min      5.4110
_cell_volume                     1310.26(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9797
_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     40.00 120.00   0.50    0.05    --   47.63  57.00 -90.00  160
  2  \w    149.00 175.00   0.50    0.05    --  106.81  45.00-120.00   52
  3  \w     94.00 178.00   0.50    0.05    --  106.81  15.00-150.00  168
  4  \w    102.00 141.00   0.50    0.05    --  106.81  30.00-120.00   78
  5  \w    133.00 170.00   0.50    0.05    --  106.81  15.00-180.00   74
  6  \w    103.00 146.00   0.50    0.05    --  106.81  45.00-120.00   86
  7  \w    117.00 173.00   0.50    0.05    --  106.81  15.00 -90.00  112
  8  \w     94.00 132.00   0.50    0.05    --  106.81  45.00  60.00   76
  9  \w    150.00 175.00   0.50    0.05    --  106.81  45.00  60.00   50
 10  \w    132.00 165.00   0.50    0.05    --  106.81  81.00 108.00   66
 11  \w    -16.00  22.00   0.50    0.05    --   47.63 -19.00 -30.00   76
 12  \w     35.00  67.00   0.50    0.05    --  106.81 -61.00   0.00   64
 13  \w     35.00  75.00   0.50    0.05    --  106.81 -61.00  30.00   80
 14  \w     34.00  69.00   0.50    0.05    --  106.81 -61.00  90.00   70
 15  \w     39.00  64.00   0.50    0.05    --  106.81 -61.00 120.00   50
 16  \w     82.00 109.00   0.50    0.05    --  106.81-125.00 120.00   54
 17  \w     34.00  68.00   0.50    0.05    --  106.81-125.00 120.00   68
 18  \w     74.00 101.00   0.50    0.05    --  106.81 -81.00 -13.00   54
 19  \w     37.00  92.00   0.50    0.05    --  106.81 -94.00 -60.00  110
 20  \w     34.00  68.00   0.50    0.05    --  106.81 -94.00 -90.00   68
 21  \w     70.00 102.00   0.50    0.05    --  106.81 -94.00 -90.00   64
 22  \w     27.00  64.00   0.50    0.05    --   47.63 -81.00 -13.00   74
 23  \w    -20.00   5.00   0.50    0.05    --   47.63 -81.00 -13.00   50
 24  \w    -11.00  15.00   0.50    0.05    --  -47.63  19.00-180.00   52
 25  \w    -21.00  26.00   0.50    0.05    --  -47.63  19.00-120.00   94
 26  \w    -68.00 -32.00   0.50    0.05    -- -104.50  61.00 -90.00   72
 27  \w    -64.00 -34.00   0.50    0.05    -- -104.50  61.00 -30.00   60
 28  \w     -8.00  19.00   0.50    0.05    --  -47.63  19.00  90.00   54
 29  \w   -115.00 -74.00   0.50    0.05    --  -47.63-125.00  60.00   82
 30  \w   -119.00 -76.00   0.50    0.05    --  -47.63-125.00-180.00   86
 31  \w   -174.00 -84.00   0.50    0.05    -- -104.50 -94.00-150.00  180
 32  \w   -156.00 -80.00   0.50    0.05    -- -104.50 -81.00 -13.00  152
 33  \w   -151.00-124.00   0.50    0.05    -- -104.50 -61.00  60.00   54
 34  \w   -174.00-139.00   0.50    0.05    -- -104.50 -15.00  60.00   70
 35  \w   -113.00 -88.00   0.50    0.05    -- -104.50 -61.00  60.00   50
 36  \w   -117.00 -78.00   0.50    0.05    -- -104.50  81.00 108.00   78
 37  \w    -74.00 -35.00   0.50    0.05    -- -104.50  81.00 108.00   78
 38  \w    -99.00 -32.00   0.50    0.05    -- -104.50 125.00 120.00  134
 39  \w   -110.00 -39.00   0.50    0.05    -- -104.50 125.00 -30.00  142
 40  \w    -63.00  24.00   0.50    0.05    --  -47.63  81.00 108.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0659234000
_diffrn_orient_matrix_UB_12      -0.1537793000
_diffrn_orient_matrix_UB_13      0.0739342000
_diffrn_orient_matrix_UB_21      -0.0069226000
_diffrn_orient_matrix_UB_22      -0.1664954000
_diffrn_orient_matrix_UB_23      -0.0886862000
_diffrn_orient_matrix_UB_31      0.0686463000
_diffrn_orient_matrix_UB_32      0.1307519000
_diffrn_orient_matrix_UB_33      -0.0258900000
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.022
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
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    1.527
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.069
_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     190
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0620P)^2^+0.9173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2539
_reflns_number_total             2713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02817a2.cif
_cod_data_source_block           lxq_40_auto
_cod_database_code               7248732
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.765
_diffrn_oxdiff_digest_frames
;
01e58982ecd00190dde62ab305001052c2000430f84
;
_diffrn_oxdiff_digest_hkl
;
01a684d81c563587069cff539ef53ad2dffc8e
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C18(H18), C7(H7), C23(H23), C22(H22), C6(H6), C20(H20), C8(H8),
 C21(H21)
;
_shelx_res_checksum              56885
_shelx_hkl_checksum              40507
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.769