Sulfoximine-Assisted Unsymmetrical Twofold C-H Functionalization of Arenes.
Ghosh, Koushik; Ghosh, Arghadip; Mukherjee, Kallol; Rit, Raja K.; Sahoo, Akhila K.; The Journal of organic chemistry 85 (2020) 8618–8626; doi:10.1021/acs.joc.0c01010

data_4038505
_publ_section_title
;
 Sulfoximine-Assisted Unsymmetrical Twofold C-H Functionalization of
 Arenes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8618
_journal_page_last               8626
_journal_paper_doi               10.1021/acs.joc.0c01010
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C20 H21 N O6 S'
_chemical_formula_sum            'C20 H21 N O6 S'
_chemical_formula_weight         403.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.396(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4889(5)
_cell_length_b                   23.1788(13)
_cell_length_c                   10.7372(6)
_cell_measurement_reflns_used    6490
_cell_measurement_temperature    237(190)
_cell_measurement_theta_max      24.9020
_cell_measurement_theta_min      2.1720
_cell_volume                     2004.7(2)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      237(190)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_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    -10.00  47.00   0.50    8.38    --   16.22  30.00   0.00  114
  2  \w     64.00  90.00   0.50    8.38    --   16.22  30.00   0.00   52
  3  \w     24.00  49.00   0.50    8.38    --  -14.97  45.00   0.00   50
  4  \w     -6.00  24.00   0.50    8.38    --   16.22  61.00  60.00   60
  5  \w     30.00  82.00   0.50    8.38    --   16.22  61.00  60.00  104
  6  \w     29.00  57.00   0.50    8.38    --  -14.97  30.00  90.00   56
  7  \w    -37.00   9.00   0.50    8.38    --  -14.97 -94.00  30.00   92
  8  \w     28.00  53.00   0.50    8.38    --   16.22-136.00 -35.00   50
  9  \w    -24.00  10.00   0.50    8.38    --  -14.97 -30.00 -90.00   68
 10  \w    -21.00  14.00   0.50    8.38    --  -14.97 -94.00-120.00   70
 11  \w    -34.00  16.00   0.50    8.38    --  -14.97 -94.00 -60.00  100
 12  \w    -86.00 -27.00   0.50    8.38    --  -14.97 -30.00 -90.00  118
 13  \w      5.00  30.00   0.50    8.38    --   16.22  45.00 -90.00   50
 14  \w     39.00  84.00   0.50    8.38    --   16.22  45.00 -90.00   90
 15  \w    -40.00 -13.00   0.50    8.38    --   16.22 130.00 -15.57   54
 16  \w    -52.00 -27.00   0.50    8.38    --  -14.97 136.00  29.00   50
 17  \w    -27.00   5.00   0.50    8.38    --  -14.97  30.00  90.00   64
 18  \w    -20.00   6.00   0.50    8.38    --  -14.97 -94.00 120.00   52
 19  \w     19.00  75.00   0.50    8.38    --   16.22-133.00 142.00  112
 20  \w    -68.00 -43.00   0.50    8.38    --  -14.97 133.00-149.00   50
;
_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      -0.0040189000
_diffrn_orient_matrix_UB_12      0.0305636000
_diffrn_orient_matrix_UB_13      0.0009442000
_diffrn_orient_matrix_UB_21      -0.0615627000
_diffrn_orient_matrix_UB_22      -0.0015908000
_diffrn_orient_matrix_UB_23      0.0317386000
_diffrn_orient_matrix_UB_31      0.0628765000
_diffrn_orient_matrix_UB_32      0.0003347000
_diffrn_orient_matrix_UB_33      0.0619162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.941
_diffrn_reflns_theta_min         2.183
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50966
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0609P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2655
_reflns_number_total             4198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01010_si_003.cif
_cod_data_source_block           aks58
_cod_depositor_comments
'Adding full bibliography for 4038505--4038506.cif.'
_cod_database_code               4038505
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 N008(H008), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00N(H00N),
 C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00Q(H00G,H00I,H00L), C00R(H00M,H00O,H00Q), C00S(H00R,
 H00S,H00T)
;
_shelx_res_checksum              2175
_shelx_hkl_checksum              32124
_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 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.557