Photochemical cyclization of α-amino esters to access 3-azetidinones.
Hwang, Meemie U.; Gogoi, Achyut; Scurria, Matthew; Gutierrez, Osvaldo; Scheidt, Karl A.; Chemical science 17 (2026) 6766–6772; doi:10.1039/d5sc09994c

data_1576448
_publ_section_title
;
 Photochemical cyclization of &#x3b1;-amino esters to access
 3-azetidinones.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              6766
_journal_page_last               6772
_journal_paper_doi               10.1039/d5sc09994c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C12 H15 N O3 S'
_chemical_formula_sum            'C12 H15 N O3 S'
_chemical_formula_weight         253.31
_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   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2nnxx5
_audit_creation_date             2024-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2025-06-09 deposited with the CCDC.	2026-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.5151(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.69645(13)
_cell_length_b                   5.25071(5)
_cell_length_c                   18.54221(17)
_cell_measurement_reflns_used    12943
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.4530
_cell_measurement_theta_min      4.0660
_cell_volume                     1232.29(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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    'SHELXS  (Sheldrick, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.976
_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    -75.00 -33.00   0.50    0.43    -- -106.00  61.00 120.00   84
  2  \w    -75.00 -33.00   0.50    0.43    -- -106.00  61.00  90.00   84
  3  \w    -75.00 -33.00   0.50    0.43    -- -106.00  61.00  60.00   84
  4  \w    -75.00 -33.00   0.50    0.43    -- -106.00  61.00   0.00   84
  5  \w    -75.00 -33.00   0.50    0.43    -- -106.00  61.00 -30.00   84
  6  \w    -75.00 -33.00   0.50    0.43    -- -106.00  61.00 -90.00   84
  7  \w    -42.00  26.00   0.50    0.11    --  -47.49  37.00-120.00  136
  8  \w   -119.00 -77.00   0.50    0.11    --  -47.49   0.00 -90.00   84
  9  \w   -119.00 -25.00   0.50    0.11    --  -47.49 -77.00 -90.00  188
 10  \w   -119.00 -25.00   0.50    0.11    --  -47.49 -77.00   0.00  188
 11  \w   -119.00 -77.00   0.50    0.11    --  -47.49   0.00  30.00   84
 12  \w   -119.00 -51.00   0.50    0.11    --  -47.49 -77.00 150.00  136
 13  \w     42.00 106.00   0.50    0.43    --  113.25 -94.00 -90.00  128
 14  \w     42.00 106.00   0.50    0.43    --  113.25 -94.00-180.00  128
 15  \w     44.00 111.00   0.50    0.43    --  113.25-125.00-180.00  134
 16  \w     42.00 106.00   0.50    0.43    --  113.25 -94.00 -60.00  128
 17  \w     43.00 106.00   0.50    0.43    --  113.25-101.00   1.00  126
 18  \w     42.00 106.00   0.50    0.43    --  113.25 -94.00  30.00  128
 19  \w    -18.00  81.00   0.50    0.11    --   47.49-101.00   1.00  198
 20  \w    -27.00  17.00   0.50    0.11    --   47.49 -19.00   0.00   88
 21  \w     42.00  71.00   0.50    0.43    --  113.25 -61.00 150.00   58
 22  \w     42.00  71.00   0.50    0.43    --  113.25 -61.00 -30.00   58
 23  \w     42.00  71.00   0.50    0.43    --  113.25 -61.00-180.00   58
 24  \w     33.00 119.00   0.50    0.11    --   47.49  57.00-150.00  172
 25  \w     85.00 178.00   0.50    0.43    --  113.25 101.00 105.00  186
 26  \w     25.00 119.00   0.50    0.11    --   47.49  77.00  90.00  188
 27  \w   -177.00 -85.00   0.50    0.43    -- -106.00-101.00   1.00  184
 28  \w   -177.00 -81.00   0.50    0.43    -- -106.00 -81.00  70.67  192
 29  \w   -177.00 -93.00   0.50    0.43    -- -106.00 -30.00 120.00  168
 30  \w   -177.00 -86.00   0.50    0.43    -- -106.00 -69.00  37.75  182
 31  \w   -177.00 -86.00   0.50    0.43    -- -106.00 -69.00  46.14  182
 32  \w   -177.00 -86.00   0.50    0.43    -- -106.00 -69.00  46.14  182
 33  \w   -177.00 -84.00   0.50    0.43    -- -106.00 -74.00-107.65  186
 34  \w   -177.00 -93.00   0.50    0.43    -- -106.00 -45.00 -90.00  168
 35  \w   -177.00 -92.00   0.50    0.43    -- -106.00 -50.00 -67.70  170
 36  \w   -177.00 -93.00   0.50    0.43    -- -106.00 -30.00 120.00  168
 37  \w   -106.00 -35.00   0.50    0.43    -- -106.00 101.00 105.00  142
 38  \w   -107.00 -36.00   0.50    0.43    -- -106.00 107.00 143.66  142
 39  \w   -108.00 -37.00   0.50    0.43    -- -106.00 112.00   4.89  142
 40  \w    -81.00  18.00   0.50    0.11    --  -47.49 101.00 105.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0996724000
_diffrn_orient_matrix_UB_12      0.1662167000
_diffrn_orient_matrix_UB_13      0.0130542000
_diffrn_orient_matrix_UB_21      -0.0689130000
_diffrn_orient_matrix_UB_22      0.2259474000
_diffrn_orient_matrix_UB_23      0.0208208000
_diffrn_orient_matrix_UB_31      0.0117119000
_diffrn_orient_matrix_UB_32      -0.0861893000
_diffrn_orient_matrix_UB_33      0.0796070000
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.555
_diffrn_reflns_theta_min         4.075
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
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    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0385P)^2^+0.6175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2384
_reflns_number_total             2617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09994c1.cif
_cod_data_source_block           cry0045_auto
_cod_depositor_comments
'Adding full bibliography for 1576448--1576450.cif.'
_cod_database_code               1576448
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H15NO3S
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.654
_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:
 C6(H6A,H6B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C16(H16)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              24608
_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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.660