Photoredox catalyzed three-component tandem cyclization of 1,5-dienes with α-keto acids and water to access pyrrolidinones
Sui, Kaixia; Jiang, Shiliang; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Chemical Communications 61 (2025) 9456–9459; doi:10.1039/D5CC01171J

data_7134585
_publ_section_title
;
 Photoredox catalyzed three-component tandem cyclization of 1,5-dienes
 with \a-keto acids and water to access pyrrolidinones
;
_journal_issue                   52
_journal_name_full               'Chemical Communications'
_journal_page_first              9456
_journal_page_last               9459
_journal_paper_doi               10.1039/D5CC01171J
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_chemical_name_systematic        SKX-JSL-3aa
_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     direct
_audit_creation_date             2025-04-29
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-04-29 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.653(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.22346(18)
_cell_length_b                   22.0539(8)
_cell_length_c                   13.8854(4)
_cell_measurement_reflns_used    7621
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9080
_cell_measurement_theta_min      3.8080
_cell_volume                     1866.51(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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     -9.00  20.00   1.00    1.00    --    0.00 -77.00   0.00   29
  2  \w    -58.00 -32.00   1.00    3.00    --  -33.50 -64.00  27.42   26
  3  \w     -5.00  35.00   1.00    3.00    --  -33.50  57.00 150.00   40
  4  \w     -5.00  33.00   1.00    3.00    --  -33.50  57.00-150.00   38
  5  \w    -48.00 -12.00   1.00    3.00    --  -33.50  57.00 150.00   36
  6  \w     21.00  57.00   1.00    3.00    --   36.47  37.00  30.00   36
  7  \w     -1.00  24.00   1.00    3.00    --   36.47  94.00 -85.93   25
  8  \w     52.00  78.00   1.00    3.00    --   36.47  57.00 -30.00   26
  9  \w      1.00  26.00   1.00    3.00    --   36.47  93.00 -48.82   25
 10  \w     66.00 110.00   1.00    3.00    --   36.47 178.00 -30.00   44
 11  \w      1.00  43.00   1.00    3.00    --   36.47 -99.00 -30.00   42
 12  \w     16.00  47.00   1.00    3.00    --   36.47  37.00 -60.00   31
 13  \w     35.00  62.00   1.00    3.00    --   36.47 -77.00 150.00   27
 14  \w     31.00  73.00   1.00    3.00    --   36.47 -19.00 -30.00   42
 15  \w     63.00 106.00   1.00    3.00    --   36.47  37.00 -60.00   43
 16  \w     16.00  43.00   1.00    3.00    --   36.47  37.00-180.00   27
 17  \w     33.00  59.00   1.00    3.00    --   36.47  19.00 -60.00   26
 18  \w     -1.00  24.00   1.00    3.00    --   36.47  93.00-151.10   25
 19  \w      0.00  25.00   1.00    3.00    --   36.47  92.00-100.86   25
 20  \w     61.00 108.00   1.00    3.00    --   36.47  19.00  60.00   47
 21  \w      7.00  33.00   1.00    3.00    --   36.47  89.00  -4.62   26
 22  \w     34.00  60.00   1.00    3.00    --   36.47  73.00 -49.58   26
 23  \w     31.00  57.00   1.00    3.00    --   36.47  57.00  60.00   26
 24  \w     50.00  76.00   1.00    3.00    --   36.47 -99.00 -30.00   26
 25  \w     72.00 104.00   1.00    3.00    --   36.47  19.00 -90.00   32
 26  \w      1.00  59.00   1.00    3.00    --   36.47  19.00 -90.00   58
 27  \w     12.00  38.00   1.00    3.00    --   36.47  76.00 112.07   26
 28  \w    -17.00   8.00   1.00    3.00    --   36.47 -77.00 150.00   25
 29  \w    -13.00  13.00   1.00    3.00    --   36.47 -19.00 -30.00   26
 30  \w     79.00 107.00   1.00   15.00    --  108.00 -94.00-150.00   28
 31  \w    117.00 175.00   1.00   15.00    --  108.00  61.00 120.00   58
 32  \w     98.00 126.00   1.00   15.00    --  108.00 -61.00 -30.00   28
 33  \w     43.00 100.00   1.00   15.00    --  108.00 -94.00-180.00   57
 34  \w    127.00 176.00   1.00   15.00    --  108.00  61.00 -90.00   49
 35  \w     66.00  94.00   1.00   15.00    --  108.00 -61.00 -30.00   28
 36  \w    107.00 136.00   1.00   15.00    --  108.00 -80.00 136.28   29
 37  \w     88.00 114.00   1.00   15.00    --  108.00  61.00 -90.00   26
 38  \w    139.00 165.00   1.00   15.00    --  108.00  30.00-150.00   26
 39  \w     83.00 112.00   1.00   15.00    --  108.00  30.00-150.00   29
 40  \w     42.00 106.00   1.00   15.00    --  108.00 -94.00 120.00   64
 41  \w     82.00 117.00   1.00   15.00    --  108.00  30.00 -60.00   35
 42  \w     88.00 113.00   1.00   15.00    --  108.00  61.00-180.00   25
 43  \w     88.00 135.00   1.00   15.00    --  108.00  61.00 -60.00   47
 44  \w     41.00  90.00   1.00   15.00    --  108.00 -80.00 136.28   49
 45  \w     88.00 114.00   1.00   15.00    --  108.00  45.00-120.00   26
 46  \w    152.00 177.00   1.00   15.00    --  108.00  30.00 -30.00   25
 47  \w     83.00 108.00   1.00   15.00    --  108.00  30.00 -30.00   25
 48  \w     88.00 118.00   1.00   15.00    --  108.00  45.00 -60.00   30
 49  \w    117.00 174.00   1.00   15.00    --  108.00  77.00-150.00   57
 50  \w     83.00 108.00   1.00   15.00    --  108.00  30.00 -90.00   25
 51  \w    149.00 178.00   1.00   15.00    --  108.00  45.00 -30.00   29
 52  \w     43.00  93.00   1.00   15.00    --  108.00 -45.00 -60.00   50
 53  \w     83.00 108.00   1.00   15.00    --  108.00  30.00   0.00   25
 54  \w     89.00 115.00   1.00   15.00    --  108.00  45.00 -30.00   26
 55  \w     40.00  65.00   1.00   15.00    --  108.00 -61.00-150.00   25
 56  \w     67.00 106.00   1.00   15.00    --  108.00 -61.00-150.00   39
 57  \w     89.00 115.00   1.00   15.00    --  108.00  45.00 -90.00   26
 58  \w    153.00 178.00   1.00   15.00    --  108.00  27.00  14.42   25
 59  \w    125.00 178.00   1.00   15.00    --  108.00  45.00   0.00   53
 60  \w     66.00  92.00   1.00   15.00    --  108.00  15.00-120.00   26
 61  \w     89.00 115.00   1.00   15.00    --  108.00  45.00   0.00   26
 62  \w     40.00  66.00   1.00   15.00    --  108.00-111.00  90.00   26
 63  \w     88.00 114.00   1.00   15.00    --  108.00  45.00-150.00   26
 64  \w     88.00 114.00   1.00   15.00    --  108.00  45.00  30.00   26
 65  \w    117.00 143.00   1.00   15.00    --  108.00  61.00  90.00   26
 66  \w     88.00 114.00   1.00   15.00    --  108.00  61.00-150.00   26
 67  \w     74.00 104.00   1.00   15.00    --  108.00-111.00 -60.00   30
 68  \w     66.00  92.00   1.00   15.00    --  108.00 178.00  30.00   26
 69  \w     88.00 139.00   1.00   15.00    --  108.00  61.00 -30.00   51
 70  \w    124.00 151.00   1.00   15.00    --  108.00  30.00-120.00   27
 71  \w    115.00 141.00   1.00   15.00    --  108.00  77.00-180.00   26
 72  \w    111.00 137.00   1.00   15.00    --  108.00 111.00 -30.00   26
 73  \w     94.00 120.00   1.00   15.00    --  108.00  45.00 120.00   26
 74  \w    126.00 175.00   1.00   15.00    --  108.00  61.00-120.00   49
 75  \w     88.00 114.00   1.00   15.00    --  108.00  61.00-120.00   26
 76  \w     88.00 114.00   1.00   15.00    --  108.00  30.00-120.00   26
 77  \w     66.00  91.00   1.00   15.00    --  108.00  15.00  30.00   25
 78  \w    117.00 143.00   1.00   15.00    --  108.00  15.00  60.00   26
 79  \w     80.00 106.00   1.00   15.00    --  108.00  27.00  14.42   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0510078000
_diffrn_orient_matrix_UB_12      0.0001212000
_diffrn_orient_matrix_UB_13      -0.1132755000
_diffrn_orient_matrix_UB_21      0.2457615000
_diffrn_orient_matrix_UB_22      0.0084008000
_diffrn_orient_matrix_UB_23      0.0000551000
_diffrn_orient_matrix_UB_31      0.0297336000
_diffrn_orient_matrix_UB_32      -0.0693522000
_diffrn_orient_matrix_UB_33      -0.0002153000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21216
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.953
_diffrn_reflns_theta_min         3.819
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0778P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.759
_reflns_Friedel_fraction_max     0.750
_reflns_number_gt                5488
_reflns_number_total             6314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01171j2.cif
_cod_data_source_block           202504122_auto
_cod_depositor_comments          'Adding full bibliography for 7134585.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7134585
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C21H17o5
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.902
_reflns_odcompleteness_completeness 22.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C3'(H3'A,H3'B), C12'(H12C,H12D)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10'),
 C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C19'(H19')
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C11'(H11D,H11E,H11F), C21'(H21D,
 H21E,H21F)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2'(H2')
;
_shelx_res_checksum              13245
_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 3.006
_oxdiff_exptl_absorpt_empirical_full_min 0.833