Visible light-driven modular synthesis of aza-β-lactams via a dual photochemical cascade
Ahmed, Imtiaz; Gupta, Nikita; Sarma, Plaban Jyoti; Neog, Shilpa; Das, Vijay Kumar; Green Chemistry 27 (2025) 12472–12482; doi:10.1039/D5GC03481G

data_1575774
_publ_section_title
;
 Visible light-driven modular synthesis of aza-\b-lactams via a dual
 photochemical cascade
;
_journal_issue                   39
_journal_name_full               'Green Chemistry'
_journal_page_first              12472
_journal_page_last               12482
_journal_paper_doi               10.1039/D5GC03481G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C28 H24 N2 O'
_chemical_formula_sum            'C28 H24 N2 O'
_chemical_formula_weight         404.49
_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     dual
_audit_creation_date             2025-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_audit_update_record
;
2025-06-30 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6236(2)
_cell_length_b                   10.04030(10)
_cell_length_c                   15.0628(2)
_cell_measurement_reflns_used    13364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9520
_cell_measurement_theta_min      2.8950
_cell_volume                     2209.66(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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   -108.00 -18.00   0.50    0.42    --  -40.83 -64.00 164.00  180
  2  \w    -64.00  27.00   0.50    0.42    --  -40.83  64.00 -59.00  182
  3  \w    -26.00  64.00   0.50    0.42    --   40.83 -64.00 164.00  180
  4  \w     18.00 108.00   0.50    0.42    --   40.83  64.00 -59.00  180
  5  \w    -76.00 -15.00   0.50    1.68    --  -82.50  64.00 -59.00  122
  6  \w     73.00 164.00   0.50    1.68    --   96.04  64.00 -59.00  182
  7  \w     29.00  76.00   0.50    1.68    --   96.04 -64.00 164.00   94
  8  \w    -24.00  35.00   0.50    0.42    --  -40.83  11.00  30.00  118
  9  \w   -109.00 -28.00   0.50    0.42    --  -40.83 -32.00  60.00  162
 10  \w    -28.00  31.00   0.50    0.42    --  -40.83  21.00 -90.00  118
 11  \w    -37.00  27.00   0.50    0.42    --  -40.83  32.00  60.00  128
 12  \w     18.00  78.00   0.50    0.42    --   40.83-104.00  30.00  120
 13  \w     18.00  78.00   0.50    0.42    --   40.83-104.00   0.00  120
 14  \w    -47.00 -15.00   0.50    1.68    --  -82.50  42.00 120.00   64
 15  \w    -47.00 -15.00   0.50    1.68    --  -82.50  42.00-180.00   64
 16  \w   -150.00 -59.00   0.50    1.68    --  -82.50 -64.00 164.00  182
 17  \w     99.00 160.00   0.50    1.68    --   96.04 117.00   0.00  122
 18  \w     28.00  68.00   0.50    1.68    --   96.04 -59.00  30.00   80
 19  \w    105.00 170.00   0.50    1.68    --   96.04  96.00-150.00  130
 20  \w     27.00 105.00   0.50    1.68    --   96.04 -77.00 -30.00  156
 21  \w     32.00 110.00   0.50    1.68    --   96.04-117.00 150.00  156
 22  \w     29.00  57.00   0.50    1.68    --   96.04 -50.00 120.00   56
 23  \w     79.00 162.00   0.50    1.68    --   96.04  42.00 -90.00  166
 24  \w     28.00  68.00   0.50    1.68    --   96.04 -59.00 120.00   80
 25  \w     72.00 164.00   0.50    1.68    --   96.04  68.00 -90.00  184
 26  \w     28.00  68.00   0.50    1.68    --   96.04 -59.00-180.00   80
 27  \w     29.00  57.00   0.50    1.68    --   96.04 -50.00   0.00   56
 28  \w     29.00  57.00   0.50    1.68    --   96.04 -50.00-120.00   56
 29  \w     29.00  57.00   0.50    1.68    --   96.04 -50.00  60.00   56
 30  \w     29.00  57.00   0.50    1.68    --   96.04 -50.00 150.00   56
 31  \w     23.00 106.00   0.50    1.68    --   96.04 -96.00 150.00  166
 32  \w     27.00 105.00   0.50    1.68    --   96.04 -77.00-120.00  156
 33  \w     81.00 166.00   0.50    1.68    --   96.04  25.00  60.00  170
 34  \w   -109.00 -14.00   0.50    0.42    --  -40.83 -77.00  30.00  190
 35  \w   -109.00 -14.00   0.50    0.42    --  -40.83 -77.00 -30.00  190
 36  \w   -109.00 -14.00   0.50    0.42    --  -40.83 -77.00  90.00  190
 37  \w   -109.00 -28.00   0.50    0.42    --  -40.83 -32.00-150.00  162
 38  \w     14.00  91.00   0.50    0.42    --   40.83  77.00-180.00  154
 39  \w     14.00 110.00   0.50    0.42    --   40.83  77.00-120.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0539290000
_diffrn_orient_matrix_UB_12      0.0686883000
_diffrn_orient_matrix_UB_13      0.0772247000
_diffrn_orient_matrix_UB_21      0.0454837000
_diffrn_orient_matrix_UB_22      0.0927185000
_diffrn_orient_matrix_UB_23      -0.0666473000
_diffrn_orient_matrix_UB_31      -0.0783566000
_diffrn_orient_matrix_UB_32      0.1011189000
_diffrn_orient_matrix_UB_33      0.0086965000
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18779
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.093
_diffrn_reflns_theta_min         4.128
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             856
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0467P)^2^+0.7001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3402
_reflns_number_total             4005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc03481g2.cif
_cod_data_source_block           1a-abl-p-me_auto
_cod_depositor_comments
'Adding full bibliography for 1575773--1575774.cif.'
_cod_database_code               1575774
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N O'
_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 Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C10(H10), C27(H27), C17(H17), C19(H19), C23(H23),
 C26(H26), C24(H24), C14(H14), C8(H8), C11(H11), C4(H4), C12(H12), C7(H7),
 C13(H13), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              62773
_shelx_hkl_checksum              66330
_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 3.039
_oxdiff_exptl_absorpt_empirical_full_min 0.753