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_1575773
_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 H17 F4.717 N2 O, 0.428(F3)'
_chemical_formula_sum            'C28 H17 F6 N2 O'
_chemical_formula_weight         511.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 97.815(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1816(3)
_cell_length_b                   9.6057(2)
_cell_length_c                   14.0760(3)
_cell_measurement_reflns_used    6277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8510
_cell_measurement_theta_min      3.1590
_cell_volume                     1229.91(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 0.997
_diffrn_measured_fraction_theta_max 0.994
_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    -59.00  27.00   0.50    0.38    --  -40.83  52.00 137.00  172
  2  \w   -107.00 -21.00   0.50    0.38    --  -40.83 -52.00  -7.00  172
  3  \w     21.00 109.00   0.50    0.38    --   40.83  52.00 137.00  176
  4  \w   -150.00 -63.00   0.50    1.50    --  -82.50 -52.00  -7.00  174
  5  \w    -59.00 -15.00   0.50    1.50    --  -82.50  52.00 137.00   88
  6  \w     76.00 163.00   0.50    1.50    --   96.04  52.00 137.00  174
  7  \w     28.00  59.00   0.50    1.50    --   96.04 -52.00  -7.00   62
  8  \w   -117.00  -4.00   0.50    0.38    --  -40.83 -11.00-180.00  226
  9  \w     18.00  78.00   0.50    0.38    --   40.83-104.00-180.00  120
 10  \w    -26.00  59.00   0.50    0.38    --   40.83 -52.00  -7.00  170
 11  \w    -25.00  48.00   0.50    0.38    --   40.83 -43.00-120.00  146
 12  \w    -35.00  24.00   0.50    0.38    --   40.83 -11.00-120.00  118
 13  \w    -84.00 -18.00   0.50    1.50    --  -82.50 117.00 -60.00  132
 14  \w    -57.00 -16.00   0.50    1.50    --  -82.50  50.00 -90.00   82
 15  \w     79.00 162.00   0.50    1.50    --   96.04  42.00  90.00  166
 16  \w     29.00  57.00   0.50    1.50    --   96.04 -50.00 120.00   56
 17  \w     28.00  68.00   0.50    1.50    --   96.04 -59.00 -30.00   80
 18  \w     82.00 164.00   0.50    1.50    --   96.04  33.00-120.00  164
 19  \w     28.00  83.00   0.50    1.50    --   96.04 -68.00-150.00  110
 20  \w     77.00 163.00   0.50    1.50    --   96.04  50.00-180.00  172
 21  \w     28.00  83.00   0.50    1.50    --   96.04 -68.00 -60.00  110
 22  \w     28.00  68.00   0.50    1.50    --   96.04 -59.00-150.00   80
 23  \w     28.00  68.00   0.50    1.50    --   96.04 -59.00 150.00   80
 24  \w     28.00  68.00   0.50    1.50    --   96.04 -59.00  30.00   80
 25  \w     44.00 127.00   0.50    1.50    --   96.04-145.00-120.00  166
 26  \w     28.00  68.00   0.50    1.50    --   96.04 -59.00  90.00   80
 27  \w     29.00  57.00   0.50    1.50    --   96.04 -50.00-120.00   56
 28  \w     99.00 160.00   0.50    1.50    --   96.04 117.00-180.00  122
 29  \w     71.00 169.00   0.50    1.50    --   96.04  17.00  60.00  196
 30  \w     82.00 164.00   0.50    1.50    --   96.04  33.00 -90.00  164
 31  \w     29.00  57.00   0.50    1.50    --   96.04 -50.00  60.00   56
 32  \w     28.00  83.00   0.50    1.50    --   96.04 -68.00-120.00  110
 33  \w   -109.00 -14.00   0.50    0.38    --  -40.83 -77.00 -30.00  190
 34  \w   -109.00 -14.00   0.50    0.38    --  -40.83 -77.00  60.00  190
 35  \w     14.00 110.00   0.50    0.38    --   40.83  77.00-120.00  192
 36  \w     18.00 109.00   0.50    0.38    --   40.83  65.00-150.00  182
 37  \w     14.00 110.00   0.50    0.38    --   40.83  77.00 -60.00  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      -0.1466804000
_diffrn_orient_matrix_UB_12      -0.0415359000
_diffrn_orient_matrix_UB_13      0.0338409000
_diffrn_orient_matrix_UB_21      0.0837001000
_diffrn_orient_matrix_UB_22      -0.0916552000
_diffrn_orient_matrix_UB_23      0.0791251000
_diffrn_orient_matrix_UB_31      0.0128608000
_diffrn_orient_matrix_UB_32      0.1249175000
_diffrn_orient_matrix_UB_33      0.0692380000
_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  0.0515
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11054
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         3.169
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49488
_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    1.381
_exptl_crystal_F_000             522
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0939P)^2^+0.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1862
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.791
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                3113
_reflns_number_total             4021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc03481g2.cif
_cod_data_source_block           1a-abl(pcf3)_auto
_cod_depositor_comments
'Adding full bibliography for 1575773--1575774.cif.'
_cod_database_code               1575773
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N F'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4(4)
 0.6(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C2-F5 \\sim C2-F2
 with sigma of 0.04
 C2-F4 \\sim C2-F1
 with sigma of 0.04
 C2-F3 \\sim C2-F6
 with sigma of 0.04
 F5-F4 \\sim F2-F1
 with sigma of 0.04
 F5-F3 \\sim F2-F6
 with sigma of 0.04
 F4-F3 \\sim F1-F6
 with sigma of 0.04
 C28-F7 \\sim C28-F12
 with sigma of 0.02
 C28-F11 \\sim C28-F10
 with sigma of 0.02
 C28-F9 \\sim C28-F8
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(F3) = Uanis(F2) = Uanis(F1) = Uanis(F6) = Uanis(F4)
Uanis(F4) = Uanis(F5) = Uanis(F6) = Uanis(F1) = Uanis(F2) = Uanis(F3)
5. Rigid body (RIGU) restrains
 C1, F5, F4, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F1, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2)=Sof(F6)=Sof(F1)=1-FVAR(1)
 Sof(F5)=Sof(F4)=Sof(F3)=FVAR(1)
 Sof(F8)=Sof(F12)=Sof(F10)=1-FVAR(2)
 Sof(F7)=Sof(F11)=Sof(F9)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C27(H27), C23(H23), C4(H4), C17(H17), C21(H21), C3(H3), C24(H24),
 C26(H26), C6(H6), C20(H20), C19(H19), C11(H11), C12(H12), C15(H15), C13(H13),
 C14(H14)
;
_shelx_res_checksum              22988
_shelx_hkl_checksum              63762
_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.732