Catalytic enantioselective synthesis of α-C chiral sulfones enabled by merging photoactive electron donor-acceptor complexes with nickel catalysis.
Lai, Ze-Min; Xie, Ying; Huang, Le-Le; Guo, Jing; Lu, Gui; Chemical science 16 (2025) 4352–4359; doi:10.1039/d4sc07264b

data_1573759
_publ_section_title
;
 Catalytic enantioselective synthesis of &#x3b1;-C chiral sulfones enabled
 by merging photoactive electron donor-acceptor complexes with nickel
 catalysis.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              4352
_journal_page_last               4359
_journal_paper_doi               10.1039/d4sc07264b
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C21 H22 N2 O3 S'
_chemical_formula_sum            'C21 H22 N2 O3 S'
_chemical_formula_weight         382.46
_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             2023-01-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-23 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.1070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.07520(10)
_cell_length_b                   20.3258(2)
_cell_length_c                   11.22890(10)
_cell_measurement_reflns_used    11260
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3610
_cell_measurement_theta_min      2.1500
_cell_volume                     1932.33(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.951
_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    -77.00   3.00   0.50    0.05    --  -44.84  90.00  81.00  160
  2  \w    -99.00 -29.00   0.50    0.05    -- -100.00  90.00  81.00  140
  3  \w    -69.00 -44.00   0.50    0.05    -- -100.00  61.00  90.00   50
  4  \w    -55.00 -30.00   0.50    0.05    -- -100.00  61.00  30.00   50
  5  \w    -65.00 -39.00   0.50    0.05    -- -100.00  61.00 -60.00   52
  6  \w    -64.00 -30.00   0.50    0.05    -- -100.00  61.00 -90.00   68
  7  \w    -67.00 -27.00   0.50    0.05    -- -100.00  61.00-150.00   80
  8  \w    -63.00 -38.00   0.50    0.05    -- -100.00  61.00-180.00   50
  9  \w   -174.00 -83.00   0.50    0.05    -- -100.00 -45.00   0.00  182
 10  \w   -162.00-136.00   0.50    0.05    -- -100.00 -90.00 -32.00   52
 11  \w   -117.00 -74.00   0.50    0.05    --  -44.84-125.00-150.00   86
 12  \w   -118.00 -75.00   0.50    0.05    --  -44.84-125.00  30.00   86
 13  \w   -118.00 -74.00   0.50    0.05    --  -44.84-125.00  60.00   88
 14  \w   -118.00 -75.00   0.50    0.05    --  -44.84-125.00 120.00   86
 15  \w     38.00  63.00   0.50    0.05    --  105.85 -61.00  90.00   50
 16  \w     41.00  67.00   0.50    0.05    --  105.85 -94.00 150.00   52
 17  \w     36.00  85.00   0.50    0.05    --  105.85 -94.00   0.00   98
 18  \w     76.00 105.00   0.50    0.05    --  105.85 -94.00 150.00   58
 19  \w    -20.00  38.00   0.50    0.05    --   44.84 -90.00 -32.00  116
 20  \w     35.00 108.00   0.50    0.05    --  105.85-125.00-180.00  146
 21  \w     33.00  95.00   0.50    0.05    --  105.85 -77.00-180.00  124
 22  \w     40.00  75.00   0.50    0.05    --  105.85 -90.00 -32.00   70
 23  \w     85.00 166.00   0.50    0.05    --  105.85  90.00  81.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0907668000
_diffrn_orient_matrix_UB_12      0.0628531000
_diffrn_orient_matrix_UB_13      0.0081572000
_diffrn_orient_matrix_UB_21      0.0306130000
_diffrn_orient_matrix_UB_22      0.0286211000
_diffrn_orient_matrix_UB_23      -0.1159866000
_diffrn_orient_matrix_UB_31      -0.1547146000
_diffrn_orient_matrix_UB_32      -0.0312351000
_diffrn_orient_matrix_UB_33      -0.0900314000
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13042
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.495
_diffrn_reflns_theta_min         4.350
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0457P)^2^+0.7832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3627
_reflns_number_total             3812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07264b2.cif
_cod_data_source_block           laizm_230113_auto
_cod_depositor_comments          'Adding full bibliography for 1573759.cif.'
_cod_database_code               1573759
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOS
_shelx_estimated_absorpt_t_max   0.730
_shelx_estimated_absorpt_t_min   0.678
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C19(H19), C2(H2), C18(H18), C23(H23), C6(H6), C5(H5),
 C3(H3), C17(H17)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              36350
_shelx_hkl_checksum              41695
_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.834