Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation.
Yan, Qiaozhi; Xiao, Guiying; Wang, Ying; Zi, Guofu; Zhang, Zhanbin; Hou, Guohua; Journal of the American Chemical Society 141 (2019) 1749–1756; doi:10.1021/jacs.8b12657

data_4128057
_publ_section_title
;
 Highly Efficient Enantioselective Synthesis of Chiral Sulfones by
 Rh-Catalyzed Asymmetric Hydrogenation.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1749
_journal_page_last               1756
_journal_paper_doi               10.1021/jacs.8b12657
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 O2 S'
_chemical_formula_sum            'C22 H22 O2 S'
_chemical_formula_weight         350.45
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.016(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6684(2)
_cell_length_b                   15.2524(3)
_cell_length_c                   10.6654(3)
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.9280
_cell_measurement_theta_min      5.0390
_cell_volume                     921.52(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -47.00 -20.00   1.00    1.41    --  -39.74 -37.00 -90.00   27
  2  \w    -48.00 -17.00   1.00    1.41    --  -39.74 -37.00 -60.00   31
  3  \w    -48.00  33.00   1.00    1.41    --  -39.74  57.00  60.00   81
  4  \w   -110.00 -26.00   1.00    1.41    --  -39.74 -57.00 -90.00   84
  5  \w      8.00 114.00   1.00    1.41    --   39.74  19.00-150.00  106
  6  \w     84.00 124.00   1.00    1.41    --   39.74 178.00   0.00   40
  7  \w     96.00 177.00   1.00    2.00    --  104.69 125.00 -60.00   81
  8  \w     82.00 109.00   1.00    2.00    --  104.69  45.00 -30.00   27
  9  \w     73.00 113.00   1.00    2.00    --  104.69  77.00 -30.00   40
 10  \w    123.00 150.00   1.00    2.00    --  104.69  77.00 -60.00   27
 11  \w     72.00  98.00   1.00    2.00    --  104.69  77.00 -60.00   26
 12  \w     73.00 101.00   1.00    2.00    --  104.69  77.00-120.00   28
 13  \w    114.00 143.00   1.00    2.00    --  104.69  77.00-120.00   29
 14  \w     73.00  98.00   1.00    2.00    --  104.69  77.00 -90.00   25
 15  \w     32.00 108.00   1.00    2.00    --  104.69-125.00  90.00   76
 16  \w     77.00 119.00   1.00    2.00    --  104.69  61.00 -30.00   42
 17  \w     80.00 107.00   1.00    2.00    --  104.69  61.00 -60.00   27
 18  \w    119.00 178.00   1.00    2.00    --  104.69 125.00  90.00   59
 19  \w    115.00 178.00   1.00    2.00    --  104.69  77.00 -90.00   63
 20  \w     80.00 105.00   1.00    2.00    --  104.69  45.00 -60.00   25
 21  \w     79.00 161.00   1.00    2.00    --  104.69  61.00   0.00   82
 22  \w     77.00 104.00   1.00    2.00    --  104.69  61.00 -90.00   27
 23  \w     28.00  95.00   1.00    2.00    --  104.69 -94.00-120.00   67
 24  \w     58.00 173.00   1.00    2.00    --  104.69  15.00 120.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0104250000
_diffrn_orient_matrix_UB_12      0.0377931000
_diffrn_orient_matrix_UB_13      -0.1336087000
_diffrn_orient_matrix_UB_21      -0.2506258000
_diffrn_orient_matrix_UB_22      -0.0349099000
_diffrn_orient_matrix_UB_23      -0.0305023000
_diffrn_orient_matrix_UB_31      -0.1053524000
_diffrn_orient_matrix_UB_32      0.0869001000
_diffrn_orient_matrix_UB_33      0.0458093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6699
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.047
_diffrn_reflns_theta_min         4.148
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.1772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3299
_reflns_number_total             3461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12657_si_002.cif
_cod_data_source_block           20180918d
_cod_database_code               4128057
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1O1S1
_reflns_odcompleteness_completeness 99.94
_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:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              95323
_shelx_hkl_checksum              38871
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.753