Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ii)–MPAA catalyzed C–H arylation and olefination
Mukherjee, Kallol; Grimblat, Nicolas; Sau, Somratan; Ghosh, Koushik; Shankar, Majji; Gandon, Vincent; Sahoo, Akhila K.; Chemical Science  (2021) –; doi:10.1039/D1SC04299H

data_1565107
_publ_section_title
;
 Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ii)--MPAA
 catalyzed C--H arylation and olefination
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04299H
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H32 N2 O5 S'
_chemical_formula_sum            'C25 H32 N2 O5 S'
_chemical_formula_weight         472.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc28st1y
_audit_creation_date             2021-09-11
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2021-09-11 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2225(2)
_cell_length_b                   15.1104(3)
_cell_length_c                   18.1484(4)
_cell_measurement_reflns_used    14452
_cell_measurement_temperature    111(15)
_cell_measurement_theta_max      26.7550
_cell_measurement_theta_min      2.2360
_cell_volume                     2529.08(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9850
_diffrn_measured_fraction_theta_max 0.9850
_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    -35.00   4.00   0.50   25.00    --  -14.97 -94.00  60.00   78
  2  \w    -53.00  43.00   0.50   25.00    --   16.22 -61.00  60.00  192
  3  \w    -34.00  13.00   0.50   25.00    --  -14.97 -94.00 120.00   94
  4  \w     43.00  80.00   0.50   25.00    --   16.22  35.00 142.00   74
  5  \w    -60.00   2.00   0.50   25.00    --  -14.97 110.00  -4.00  124
  6  \w    -51.00  44.00   0.50   25.00    --  -14.97  92.00 -90.00  190
  7  \w    -35.00  14.00   0.50   25.00    --   16.22 -94.00   0.00   98
  8  \w    -44.00  38.00   0.50   25.00    --   16.22 -45.00-150.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0466965000
_diffrn_orient_matrix_UB_12      -0.0093118000
_diffrn_orient_matrix_UB_13      -0.0301022000
_diffrn_orient_matrix_UB_21      -0.0589591000
_diffrn_orient_matrix_UB_22      -0.0187498000
_diffrn_orient_matrix_UB_23      -0.0196079000
_diffrn_orient_matrix_UB_31      -0.0161501000
_diffrn_orient_matrix_UB_32      0.0419916000
_diffrn_orient_matrix_UB_33      -0.0154140000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17182
_diffrn_reflns_theta_full        26.3699
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.2411
_exptl_crystal_description       block
_exptl_crystal_F_000             1008.9858
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3602
_refine_diff_density_min         -0.2472
_refine_diff_density_rms         0.0382
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             9.0742
_refine_ls_goodness_of_fit_ref   1.0345
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0345
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.5513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.972
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                4889
_reflns_number_total             5105
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1sc04299h2.cif
_cod_data_source_block           AKS95
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1565107
_chemical_oxdiff_formula         'C H N O S'
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C2(H2), C3(H3), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C23(H23a,H23b,H23c), C25(H25a,H25b,H25c), C24(H24a,H24b,
 H24c), C10(H10a,H10b,H10c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,
 H14b,H14c)
;
_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.741