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_7247384
_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         'C25 H24 O3 S'
_chemical_formula_sum            'C25 H24 O3 S'
_chemical_formula_weight         404.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2023-06-10 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.284(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1955(11)
_cell_length_b                   11.0133(9)
_cell_length_c                   13.4688(10)
_cell_measurement_reflns_used    5787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1820
_cell_measurement_theta_min      2.3850
_cell_volume                     2078.1(3)
_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 0.890
_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      6.00  88.00   1.00   64.26    --   18.58  77.00  30.00   82
  2  \w     35.00  93.00   1.00   64.26    --   18.58 178.00-120.00   58
  3  \w      1.00  87.00   1.00   64.26    --   18.58  57.00-120.00   86
  4  \w      3.00  85.00   1.00   64.26    --   18.58  57.00 150.00   82
  5  \w     39.00  87.00   1.00   64.26    --   18.58  57.00 -60.00   48
  6  \w     -3.00  39.00   1.00   64.26    --  -18.74  77.00 -90.00   42
  7  \w    -44.00 -19.00   1.00   64.26    --  -18.74  77.00 -90.00   25
;
_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      -0.0182191000
_diffrn_orient_matrix_UB_12      0.0485806000
_diffrn_orient_matrix_UB_13      -0.0319632000
_diffrn_orient_matrix_UB_21      -0.0381563000
_diffrn_orient_matrix_UB_22      -0.0375045000
_diffrn_orient_matrix_UB_23      -0.0226968000
_diffrn_orient_matrix_UB_31      -0.0279655000
_diffrn_orient_matrix_UB_32      0.0194161000
_diffrn_orient_matrix_UB_33      0.0361489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.154
_diffrn_reflns_theta_min         2.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86118
_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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0451P)^2^+0.5128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3321
_reflns_number_total             4995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02128a2.cif
_cod_data_source_block           20230606-xw-1
_cod_depositor_comments
'Adding full bibliography for 7247383--7247384.cif.'
_cod_database_code               7247384
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O 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:
 C009(H00A,H00B), C00M(H00M,H00N), C00P(H00Q,H00R)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00G(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00N(H00O), C00O(H00P), C00Q(H00S), C00S(H00W), C00T(H00X)
2.c Idealised Me refined as rotating group:
 C00F(H00E,H00F,H00G), C00R(H00T,H00U,H00V)
;
_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 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.787