Iridium-Catalyzed Direct C-H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature.
Pi, Chao; Cui, Xiuling; Wu, Yangjie; The Journal of organic chemistry 80 (2015) 7333–7339; doi:10.1021/acs.joc.5b01377

data_4031315
_publ_section_title
;
 Iridium-Catalyzed Direct C-H Sulfamidation of Aryl Nitrones with Sulfonyl
 Azides at Room Temperature.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7333
_journal_page_last               7339
_journal_paper_doi               10.1021/acs.joc.5b01377
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H22 N2 O3 S'
_chemical_formula_sum            'C18 H22 N2 O3 S'
_chemical_formula_weight         346.44
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.590(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1197(3)
_cell_length_b                   10.3678(3)
_cell_length_c                   17.2578(5)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.9900
_cell_measurement_theta_min      4.2720
_cell_volume                     1767.13(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -16.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 40

  2 omega  -75.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 38

  3 omega  -72.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 27

  4 omega   40.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 29

  5 omega   36.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -120.0000 45

  6 omega   43.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  120.0000 84

  7 omega  -13.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  -30.0000 99

  8 omega   57.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -90.0000 31

  9 omega   42.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 48

 10 omega   91.00  156.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 65

 11 omega   48.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 50

 12 omega   46.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 43

 13 omega   91.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 51

 14 omega   51.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 29

 15 omega   49.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 59

 16 omega   51.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 39

 17 omega   96.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 81

 18 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 45

 19 omega  -70.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000    0.0000 100

 20 omega   30.00   64.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000   30.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1088562000
_diffrn_orient_matrix_UB_12      -0.0592968000
_diffrn_orient_matrix_UB_13      0.0669823000
_diffrn_orient_matrix_UB_21      0.0521510000
_diffrn_orient_matrix_UB_22      -0.0820796000
_diffrn_orient_matrix_UB_23      -0.0614745000
_diffrn_orient_matrix_UB_31      0.0987925000
_diffrn_orient_matrix_UB_32      0.1087438000
_diffrn_orient_matrix_UB_33      -0.0099631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6462
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.67
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+0.2901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                2632
_reflns_number_total             3141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01377_si_002.cif
_cod_data_source_block           201410202
_cod_depositor_comments          'Adding full bibliography for 4031315.cif.'
_cod_database_code               4031315
_chemical_oxdiff_formula         C20H20N4O4S1
_reflns_odcompleteness_completeness 99.70
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'