Rh(iii)-catalyzed direct ortho-C–H diarylation of arylsulfoximines with arylsilanes
Zhang, Xiuqi; Zhang, Jie; Li, Lin; Zhang, Fukuan; Luo, Xuzhong; Luo, Haiqing; New Journal of Chemistry 47 (2023) 6536–6539; doi:10.1039/D2NJ06303D

data_7062382
_publ_section_title
;
 Rh(iii)-catalyzed direct ortho-C--H diarylation of arylsulfoximines with
 arylsilanes
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6536
_journal_page_last               6539
_journal_paper_doi               10.1039/D2NJ06303D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C21 H21 N O3 S'
_chemical_formula_sum            'C21 H21 N O3 S'
_chemical_formula_weight         367.45
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-03-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                73.245(3)
_cell_angle_beta                 83.671(3)
_cell_angle_gamma                84.492(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0766(3)
_cell_length_b                   9.3193(3)
_cell_length_c                   11.4115(4)
_cell_measurement_reflns_used    8563
_cell_measurement_temperature    294.67(12)
_cell_measurement_theta_max      75.4000
_cell_measurement_theta_min      4.0500
_cell_volume                     916.57(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.67(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.942
_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     89.00 165.00   0.50    0.95    --  109.26  45.00   0.00  152
  2  \w    149.00 177.00   0.50    0.95    --  109.26  30.00  90.00   56
  3  \w    117.00 177.00   0.50    0.95    --  109.26  45.00 120.00  120
  4  \w     88.00 133.00   0.50    0.95    --  109.26  30.00  90.00   90
  5  \w    151.00 178.00   0.50    0.95    --  109.26  15.00-150.00   54
  6  \w    120.00 145.00   0.50    0.95    --  109.26  15.00-150.00   50
  7  \w    -27.00  38.00   0.50    0.30    --  -43.18  19.00-150.00  130
  8  \w    -47.00 -14.00   0.50    0.95    --  -90.25  45.00-180.00   66
  9  \w    -50.00 -23.00   0.50    0.95    --  -90.25  45.00 -30.00   54
 10  \w    -50.00 -20.00   0.50    0.95    --  -90.25  45.00   0.00   60
 11  \w    -51.00 -25.00   0.50    0.95    --  -90.25  45.00  60.00   52
 12  \w    -50.00 -15.00   0.50    0.95    --  -90.25  45.00 150.00   70
 13  \w    -42.00  34.00   0.50    0.30    --  -43.18  37.00 -60.00  152
 14  \w     40.00 103.00   0.50    0.30    --   43.18-135.00 -49.00  126
 15  \w     36.00  73.00   0.50    0.95    --  109.26-125.00-180.00   74
 16  \w     62.00 111.00   0.50    0.95    --  109.26-125.00 -90.00   98
 17  \w     80.00 111.00   0.50    0.95    --  109.26-125.00-180.00   62
 18  \w     40.00 119.00   0.50    0.95    --  109.26-135.00 -49.00  158
 19  \w     78.00 111.00   0.50    0.95    --  109.26-125.00 -30.00   66
 20  \w     48.00  93.00   0.50    0.95    --  109.26 -94.00   0.00   90
 21  \w     60.00  86.00   0.50    0.95    --  109.26 -94.00  30.00   52
 22  \w     39.00 118.00   0.50    0.95    --  109.26-133.00 130.00  158
 23  \w     77.00 102.00   0.50    0.95    --  109.26 -94.00 150.00   50
 24  \w     43.00  73.00   0.50    0.95    --  109.26 -94.00 150.00   60
 25  \w     39.00 101.00   0.50    0.30    --   43.18-133.00 130.00  124
 26  \w     76.00 104.00   0.50    0.95    --  109.26 -94.00 -60.00   56
 27  \w     38.00  64.00   0.50    0.95    --  109.26 -94.00 -60.00   52
 28  \w     37.00  66.00   0.50    0.95    --  109.26 -61.00   0.00   58
 29  \w     36.00  70.00   0.50    0.95    --  109.26 -61.00 150.00   68
 30  \w     40.00  70.00   0.50    0.95    --  109.26 -61.00 -30.00   60
 31  \w     42.00  67.00   0.50    0.95    --  109.26 -61.00 -90.00   50
 32  \w     38.00  71.00   0.50    0.95    --  109.26 -61.00-180.00   66
 33  \w     89.00 178.00   0.50    0.95    --  109.26 135.00  16.00  178
 34  \w     90.00 178.00   0.50    0.95    --  109.26 133.00-162.00  176
 35  \w     -8.00  22.00   0.50    0.30    --   43.18 -19.00-180.00   60
 36  \w    -92.00 -17.00   0.50    0.30    --  -43.18 133.00-162.00  150
 37  \w    -91.00 -17.00   0.50    0.95    --  -90.25 133.00-162.00  148
 38  \w    -93.00 -18.00   0.50    0.30    --  -43.18 135.00  16.00  150
 39  \w   -120.00 -20.00   0.50    0.30    --  -43.18 -37.00 -30.00  200
 40  \w   -117.00 -68.00   0.50    0.30    --  -43.18-133.00 130.00   98
 41  \w   -117.00 -67.00   0.50    0.30    --  -43.18-135.00 -49.00  100
 42  \w   -144.00 -68.00   0.50    0.95    --  -90.25 -45.00-180.00  152
 43  \w   -160.00 -67.00   0.50    0.95    --  -90.25-135.00 -49.00  186
 44  \w   -120.00 -74.00   0.50    0.95    --  -90.25-125.00 -30.00   92
 45  \w   -157.00-127.00   0.50    0.95    --  -90.25-125.00 -30.00   60
 46  \w   -115.00 -90.00   0.50    0.95    --  -90.25-133.00 130.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0098652000
_diffrn_orient_matrix_UB_12      0.0094598000
_diffrn_orient_matrix_UB_13      -0.1359633000
_diffrn_orient_matrix_UB_21      -0.0907772000
_diffrn_orient_matrix_UB_22      -0.1401491000
_diffrn_orient_matrix_UB_23      0.0392508000
_diffrn_orient_matrix_UB_31      -0.1447687000
_diffrn_orient_matrix_UB_32      0.1010386000
_diffrn_orient_matrix_UB_33      -0.0008542000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11838
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.391
_diffrn_reflns_theta_min         4.061
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0685P)^2^+0.2039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3151
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj06303d2.cif
_cod_data_source_block           2a-p-ome
_cod_depositor_comments          'Adding full bibliography for 7062382.cif.'
_cod_database_code               7062382
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.769
_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. Restrained distances
 N1-H1
 0.84 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              1525
_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 2.978
_oxdiff_exptl_absorpt_empirical_full_min 0.406