Electrochemical synthesis of γ-keto sulfones containing a β-quaternary carbon center via 1,2-migration
Xia, Wen; Yang, Yawen; Zhang, Xiaohui; Hu, Liangzhen; Xiong, Yan; Green Chemistry 25 (2023) 8273–8279; doi:10.1039/D3GC02128A

data_7247383
_publ_section_title
;
 Electrochemical synthesis of \g-keto sulfones containing a \b-quaternary
 carbon center via 1,2-migration
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8273
_journal_page_last               8279
_journal_paper_doi               10.1039/D3GC02128A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-29
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2023-06-07 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                81.655(3)
_cell_angle_beta                 89.531(2)
_cell_angle_gamma                72.972(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9531(3)
_cell_length_b                   9.9751(3)
_cell_length_c                   11.6032(3)
_cell_measurement_reflns_used    8045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6640
_cell_measurement_theta_min      4.6730
_cell_volume                     979.70(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -18.00  25.00   1.00    1.00    --    0.00  57.00  30.00   43
  2  \w    -41.00  -1.00   1.00    1.00    --    0.00  19.00-120.00   40
  3  \w    -60.00 -33.00   1.00    1.00    --    0.00 -57.00-120.00   27
  4  \w     30.00  68.00   1.00    1.00    --    0.00  57.00  30.00   38
  5  \w    -31.00  17.00   1.00    1.00    --    0.00 -57.00-120.00   48
  6  \w     37.00  62.00   1.00    1.00    --    0.00  19.00-120.00   25
  7  \w    -26.00  -1.00   1.00    1.00    --   26.00 116.00  -3.08   25
  8  \w     -2.00  23.00   1.00    1.00    --   38.00  95.00 120.94   25
  9  \w     -1.00  26.00   1.00    1.00    --   38.00  94.00  27.90   27
 10  \w      5.00  30.00   1.00    1.00    --   42.00  90.00  90.76   25
 11  \w     12.00  37.00   1.00    1.00    --   46.00  84.00  11.54   25
 12  \w     12.00  37.00   1.00    1.00    --   46.00  84.00-156.67   25
 13  \w     13.00  38.00   1.00    1.00    --   46.00  82.00-114.96   25
 14  \w     19.00  44.00   1.00    1.00    --   50.00  78.00 151.44   25
 15  \w     18.00  43.00   1.00    1.00    --   50.00  80.00 116.66   25
 16  \w     18.00  43.00   1.00    1.00    --   50.00  80.00 -43.52   25
 17  \w     28.00 109.00   1.00    1.00    --   54.00-125.00  90.00   81
 18  \w     -8.00  68.00   1.00    1.00    --   54.00 -57.00 -90.00   76
 19  \w     26.00  54.00   1.00    1.00    --   54.00  77.00 -90.00   28
 20  \w      5.00  60.00   1.00    1.00    --   54.00 -99.00-120.00   55
 21  \w     27.00  54.00   1.00    1.00    --   54.00  77.00 -30.00   27
 22  \w     -5.00  79.00   1.00    1.00    --   54.00 -38.00  60.00   84
 23  \w     30.00  59.00   1.00    1.00    --   58.00  75.00  -3.53   29
 24  \w     31.00  58.00   1.00    1.00    --   58.00  75.00  74.95   27
 25  \w     30.00  55.00   1.00    1.00    --   58.00  76.00  35.93   25
 26  \w     29.00  66.00   1.00    1.00    --   58.00  75.00-142.57   37
 27  \w     70.00 128.00   1.00    1.00    --   58.00  75.00-142.57   58
 28  \w     30.00  57.00   1.00    1.00    --   58.00  76.00 -76.92   27
 29  \w     33.00  60.00   1.00    1.00    --   58.00  75.00-178.85   27
 30  \w     68.00 127.00   1.00    1.00    --   58.00  75.00  -3.53   59
 31  \w     99.00 126.00   1.00    1.00    --   62.00  71.00 109.63   27
 32  \w     35.00  79.00   1.00    1.00    --   62.00  71.00 109.63   44
 33  \w     39.00  69.00   1.00    1.00    --   66.00  77.00 135.00   30
 34  \w     47.00  72.00   1.00    1.00    --   66.00  58.00 -70.16   25
 35  \w     51.00  76.00   1.00    1.00    --   70.00  62.00 -56.40   25
 36  \w     53.00 125.00   1.00    1.00    --   70.00  63.00  80.06   72
 37  \w     54.00  93.00   1.00    1.00    --   74.00  50.00 165.25   39
 38  \w     47.00 144.00   1.00    1.00    --   74.00  76.00 157.56   97
 39  \w     47.00  73.00   1.00    1.00    --   74.00  76.00  13.55   26
 40  \w    111.00 141.00   1.00    1.00    --   78.00  74.00 -43.96   30
 41  \w     50.00 100.00   1.00    1.00    --   78.00  74.00 -43.96   50
 42  \w     94.00 129.00   1.00    1.00    --   78.00  77.00  33.56   35
 43  \w     56.00  83.00   1.00    1.00    --   78.00  50.00 -90.91   27
 44  \w     51.00  89.00   1.00    1.00    --   78.00  77.00  33.56   38
 45  \w     60.00  87.00   1.00    1.00    --   82.00  50.00-121.83   27
 46  \w     83.00 124.00   1.00    1.00    --  106.00  67.00-150.76   41
 47  \w     88.00 145.00   1.00    1.00    --  108.00  38.00 -30.00   57
 48  \w     78.00 105.00   1.00    1.00    --  108.00  77.00   0.00   27
 49  \w     91.00 130.00   1.00    1.00    --  108.00 -91.00  30.00   39
 50  \w     82.00 112.00   1.00    1.00    --  108.00 -63.00  30.00   30
 51  \w     42.00  75.00   1.00    1.00    --  108.00 -63.00  30.00   33
 52  \w     42.00  71.00   1.00    1.00    --  108.00 -91.00  30.00   29
 53  \w     78.00 129.00   1.00    1.00    --  108.00  77.00 -60.00   51
 54  \w     78.00 104.00   1.00    1.00    --  108.00  77.00  90.00   26
 55  \w     67.00 106.00   1.00    1.00    --  108.00-111.00-180.00   39
 56  \w     78.00 105.00   1.00    1.00    --  108.00  77.00 150.00   27
 57  \w    111.00 144.00   1.00    1.00    --  108.00  77.00 -30.00   33
 58  \w     82.00 161.00   1.00    1.00    --  108.00  38.00 -60.00   79
 59  \w     75.00 113.00   1.00    1.00    --  108.00-111.00  60.00   38
 60  \w     78.00 106.00   1.00    1.00    --  108.00  77.00 -30.00   28
 61  \w    110.00 175.00   1.00    1.00    --  108.00  77.00   0.00   65
 62  \w     79.00 148.00   1.00    1.00    --  108.00  77.00-120.00   69
 63  \w     37.00  63.00   1.00    1.00    --  108.00-111.00  60.00   26
 64  \w     79.00 112.00   1.00    1.00    --  108.00-111.00 -30.00   33
 65  \w     86.00 113.00   1.00    1.00    --  108.00  63.00-120.00   27
 66  \w     40.00 140.00   1.00    1.00    --  108.00 -25.00  30.00  100
 67  \w     67.00 118.00   1.00    1.00    --  108.00 -63.00 150.00   51
 68  \w     82.00 136.00   1.00    1.00    --  108.00  38.00  30.00   54
 69  \w     83.00 144.00   1.00    1.00    --  108.00  38.00-150.00   61
 70  \w     88.00 136.00   1.00    1.00    --  108.00  63.00 120.00   48
 71  \w     42.00 119.00   1.00    1.00    --  108.00 -50.00  90.00   77
 72  \w     79.00 174.00   1.00    1.00    --  108.00  77.00  60.00   95
 73  \w    120.00 166.00   1.00    1.00    --  108.00  77.00 120.00   46
 74  \w    115.00 140.00   1.00    1.00    --  108.00 -25.00-150.00   25
 75  \w     78.00 105.00   1.00    1.00    --  108.00  77.00 120.00   27
 76  \w     77.00 104.00   1.00    1.00    --  108.00 -25.00-150.00   27
 77  \w     39.00  70.00   1.00    1.00    --  108.00 -25.00-150.00   31
 78  \w     79.00 112.00   1.00    1.00    --  108.00-111.00-150.00   33
 79  \w    110.00 137.00   1.00    1.00    --  108.00 -77.00 -30.00   27
 80  \w    122.00 162.00   1.00    1.00    --  108.00  77.00-180.00   40
 81  \w     39.00  93.00   1.00    1.00    --  108.00 -77.00 -30.00   54
 82  \w    138.00 170.00   1.00    1.00    --  108.00  63.00 150.00   32
 83  \w     78.00 105.00   1.00    1.00    --  108.00  77.00-180.00   27
 84  \w     78.00 109.00   1.00    1.00    --  108.00  77.00 -90.00   31
 85  \w     88.00 133.00   1.00    1.00    --  108.00  63.00 150.00   45
 86  \w     92.00 121.00   1.00    1.00    --  108.00 -63.00-150.00   29
 87  \w    125.00 152.00   1.00    1.00    --  108.00  63.00  30.00   27
 88  \w    136.00 161.00   1.00    1.00    --  108.00  63.00 -90.00   25
 89  \w     92.00 117.00   1.00    1.00    --  108.00  63.00  30.00   25
 90  \w     89.00 120.00   1.00    1.00    --  108.00  63.00 -90.00   31
 91  \w     54.00 101.00   1.00    1.00    --  108.00-111.00 -60.00   47
 92  \w     87.00 114.00   1.00    1.00    --  108.00  63.00  60.00   27
 93  \w     55.00 107.00   1.00    1.00    --  108.00 -12.00-180.00   52
 94  \w    124.00 149.00   1.00    1.00    --  108.00 -12.00-180.00   25
 95  \w    149.00 174.00   1.00    1.00    --  108.00  38.00 120.00   25
 96  \w    119.00 174.00   1.00    1.00    --  108.00  77.00-150.00   55
 97  \w     79.00 106.00   1.00    1.00    --  108.00  77.00-150.00   27
 98  \w     83.00 139.00   1.00    1.00    --  108.00  38.00 120.00   56
 99  \w     86.00 148.00   1.00    1.00    --  108.00  63.00 -30.00   62
100  \w     80.00 174.00   1.00    1.00    --  108.00  77.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1485240000
_diffrn_orient_matrix_UB_12      0.0310355000
_diffrn_orient_matrix_UB_13      -0.0496979000
_diffrn_orient_matrix_UB_21      0.1005157000
_diffrn_orient_matrix_UB_22      -0.1436711000
_diffrn_orient_matrix_UB_23      0.0649031000
_diffrn_orient_matrix_UB_31      -0.0162816000
_diffrn_orient_matrix_UB_32      -0.0712707000
_diffrn_orient_matrix_UB_33      -0.1065298000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.538
_diffrn_reflns_theta_min         3.853
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0590P)^2^+0.2407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3219
_reflns_number_total             3728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02128a2.cif
_cod_data_source_block           20230526-xw-1
_cod_depositor_comments
'Adding full bibliography for 7247383--7247384.cif.'
_cod_database_code               7247383
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C11(H11), C7(H7), C15(H15), C12(H12), C23(H23),
 C19(H19), C22(H22), C21(H21), C13(H13), C14(H14), C20(H20)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 2.163
_oxdiff_exptl_absorpt_empirical_full_min 0.704