Cu-Catalyzed Enantioconvergent Oxygen-Centered Radical Cyclization
Li, Zhen-Yu; Huang, Chun-Dong; Guan, Chun-Yan; Guo, Hui-Min; Liu, Ling-Min; Xiao, Xiao; Gao, Beiling; Ni, Shaofei; Mei, Guang-Jian; Chemical Science  (2025) –; doi:10.1039/D5SC07101A

data_1576194
_publ_section_title
;
 Cu-Catalyzed Enantioconvergent Oxygen-Centered Radical Cyclization
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07101A
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H25 N O5'
_chemical_formula_sum            'C30 H25 N O5'
_chemical_formula_weight         479.51
_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             2024-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-27 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1684(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8748(2)
_cell_length_b                   7.8411(2)
_cell_length_c                   32.5589(6)
_cell_measurement_reflns_used    9186
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6860
_cell_measurement_theta_min      4.0570
_cell_volume                     2519.21(9)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -55.00 -16.00   1.00    1.00    --  -33.50 -37.00 150.00   39
  2  \w    -60.00 -28.00   1.00    1.00    --  -33.50  77.00  60.00   32
  3  \w     12.00  40.00   1.00    1.00    --   36.47  82.00 -85.30   28
  4  \w     24.00  53.00   1.00    1.00    --   36.47  57.00 -60.00   29
  5  \w    -32.00  29.00   1.00    1.00    --   36.47 -57.00   0.00   61
  6  \w     63.00 109.00   1.00    1.00    --   36.47 178.00-120.00   46
  7  \w      0.00  25.00   1.00    1.00    --   36.47  91.00  70.22   25
  8  \w     14.00  70.00   1.00    1.00    --   36.47  37.00-180.00   56
  9  \w     64.00 104.00   1.00    1.00    --   36.47  57.00 -60.00   40
 10  \w      6.00  35.00   1.00    1.00    --   36.47  89.00  -4.76   29
 11  \w     12.00  38.00   1.00    1.00    --   36.47  81.00  97.65   26
 12  \w     64.00  90.00   1.00    1.00    --   36.47  57.00 -90.00   26
 13  \w     23.00  73.00   1.00    1.00    --   36.47  71.00 169.50   50
 14  \w     75.00 101.00   1.00    1.00    --   36.47  67.00-178.86   26
 15  \w     72.00  97.00   1.00    1.00    --   36.47  57.00 120.00   25
 16  \w     -1.00  24.00   1.00    1.00    --   36.47  95.00  80.09   25
 17  \w     -4.00  42.00   1.00    1.00    --   36.47 -37.00  30.00   46
 18  \w     65.00 103.00   1.00    1.00    --   36.47  57.00-150.00   38
 19  \w     12.00  64.00   1.00    1.00    --   36.47 -77.00 -60.00   52
 20  \w    -24.00  37.00   1.00    1.00    --   36.47 -37.00-120.00   61
 21  \w      2.00  66.00   1.00    1.00    --   36.47 -99.00 -60.00   64
 22  \w     24.00  64.00   1.00    1.00    --   36.47  57.00  30.00   40
 23  \w    -28.00  27.00   1.00    1.00    --   36.47 -57.00  30.00   55
 24  \w     96.00 127.00   1.00   10.00    --  108.00 -61.00-150.00   31
 25  \w    130.00 156.00   1.00   10.00    --  108.00  61.00 120.00   26
 26  \w     88.00 144.00   1.00   10.00    --  108.00  45.00-150.00   56
 27  \w     78.00 104.00   1.00   10.00    --  108.00-111.00-120.00   26
 28  \w     82.00 110.00   1.00   10.00    --  108.00  30.00 120.00   28
 29  \w     64.00 112.00   1.00   10.00    --  108.00 -61.00 -60.00   48
 30  \w     42.00 106.00   1.00   10.00    --  108.00 -94.00-120.00   64
 31  \w     88.00 113.00   1.00   10.00    --  108.00  61.00 120.00   25
 32  \w     88.00 114.00   1.00   10.00    --  108.00  61.00-150.00   26
 33  \w    127.00 172.00   1.00   10.00    --  108.00  30.00 150.00   45
 34  \w    145.00 171.00   1.00   10.00    --  108.00  61.00 150.00   26
 35  \w     88.00 114.00   1.00   10.00    --  108.00  61.00 150.00   26
 36  \w     83.00 112.00   1.00   10.00    --  108.00  30.00 150.00   29
 37  \w     84.00 109.00   1.00   10.00    --  108.00  69.00  75.19   25
 38  \w     88.00 118.00   1.00   10.00    --  108.00  61.00-180.00   30
 39  \w     39.00  69.00   1.00   10.00    --  108.00 -45.00 -90.00   30
 40  \w     88.00 113.00   1.00   10.00    --  108.00  45.00 150.00   25
 41  \w     86.00 112.00   1.00   10.00    --  108.00  30.00-150.00   26
 42  \w     88.00 176.00   1.00   10.00    --  108.00  61.00  90.00   88
 43  \w    138.00 164.00   1.00   10.00    --  108.00  30.00-120.00   26
 44  \w     93.00 119.00   1.00   10.00    --  108.00 -45.00 -90.00   26
 45  \w     84.00 120.00   1.00   10.00    --  108.00  30.00  90.00   36
 46  \w     43.00  68.00   1.00   10.00    --  108.00 -94.00 -60.00   25
 47  \w    140.00 166.00   1.00   10.00    --  108.00  61.00  60.00   26
 48  \w     49.00 116.00   1.00   10.00    --  108.00  -8.00 -77.40   67
 49  \w     84.00 109.00   1.00   10.00    --  108.00  30.00-120.00   25
 50  \w     88.00 159.00   1.00   10.00    --  108.00  45.00 -30.00   71
 51  \w     86.00 114.00   1.00   10.00    --  108.00 -77.00-120.00   28
 52  \w     90.00 116.00   1.00   10.00    --  108.00  61.00  60.00   26
 53  \w     83.00 120.00   1.00   10.00    --  108.00  30.00-180.00   37
 54  \w    114.00 139.00   1.00   10.00    --  108.00 -15.00 120.00   25
 55  \w     51.00 103.00   1.00   10.00    --  108.00 -94.00   0.00   52
 56  \w     93.00 119.00   1.00   10.00    --  108.00  45.00-120.00   26
 57  \w     96.00 121.00   1.00   10.00    --  108.00 -45.00  90.00   25
 58  \w     88.00 114.00   1.00   10.00    --  108.00  45.00 120.00   26
 59  \w     81.00 107.00   1.00   10.00    --  108.00 -77.00  60.00   26
 60  \w     69.00  95.00   1.00   10.00    --  108.00 -15.00-180.00   26
 61  \w    105.00 131.00   1.00   10.00    --  108.00 -15.00-180.00   26
 62  \w     36.00 138.00   1.00   10.00    --  108.00 -15.00 -30.00  102
 63  \w    112.00 138.00   1.00   10.00    --  108.00  77.00  60.00   26
 64  \w     41.00  82.00   1.00   10.00    --  108.00 -94.00  60.00   41
 65  \w     88.00 145.00   1.00   10.00    --  108.00  45.00-180.00   57
 66  \w    136.00 162.00   1.00   10.00    --  108.00 111.00-120.00   26
 67  \w     64.00  90.00   1.00   10.00    --  108.00-111.00  90.00   26
 68  \w     61.00 109.00   1.00   10.00    --  108.00 178.00-180.00   48
 69  \w     54.00  92.00   1.00   10.00    --  108.00-111.00-180.00   38
 70  \w     60.00 105.00   1.00   10.00    --  108.00 -94.00-180.00   45
 71  \w     88.00 120.00   1.00   10.00    --  108.00  45.00  90.00   32
 72  \w    128.00 154.00   1.00   10.00    --  108.00  77.00 120.00   26
 73  \w     39.00  65.00   1.00   10.00    --  108.00 -30.00 -30.00   26
 74  \w     72.00  98.00   1.00   10.00    --  108.00 -30.00 -30.00   26
 75  \w    149.00 175.00   1.00   10.00    --  108.00  69.00  75.19   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      -0.0203233000
_diffrn_orient_matrix_UB_12      -0.0444703000
_diffrn_orient_matrix_UB_13      -0.0459181000
_diffrn_orient_matrix_UB_21      -0.1537891000
_diffrn_orient_matrix_UB_22      0.0272835000
_diffrn_orient_matrix_UB_23      0.0029800000
_diffrn_orient_matrix_UB_31      0.0174304000
_diffrn_orient_matrix_UB_32      0.1894141000
_diffrn_orient_matrix_UB_33      -0.0111949000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            31695
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.991
_diffrn_reflns_theta_min         4.076
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93728
_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    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2281 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         8754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+0.0739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1501
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.793
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                6869
_reflns_number_total             8754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07101a2.cif
_cod_data_source_block           202410342a_auto
_cod_original_cell_volume        2519.22(10)
_cod_database_code               1576194
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C12H22O5N1
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.879
_reflns_odcompleteness_completeness 87.73
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C24(H24A,H24B), C2'(H2'A,H2'B), C11'(H11C,H11D),
 C24'(H24C,H24D)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C20(H20),
 C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C5'(H5'), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'), C16'(H16'), C17'(H17'),
 C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23'), C26'(H26'), C27'(H27'),
 C28'(H28'), C29'(H29'), C30'(H30')
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12'(H12D,H12E,H12F)
;
_shelx_res_checksum              78955
_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 1.110
_oxdiff_exptl_absorpt_empirical_full_min 0.866