C-H Sulfonylation via 1,3-Rearrangement of Sulfonyl Group in N-protected 3-Bissulfonimidoindole Derivatives Using Fluorine Reagent.
Watanabe, Kazuhiro; Moriyama, Katsuhiko; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03498

data_4038162
_publ_section_title
;
 C-H Sulfonylation via 1,3-Rearrangement of Sulfonyl Group in N-protected
 3-Bissulfonimidoindole Derivatives Using Fluorine Reagent.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03498
_journal_year                    2020
_chemical_formula_sum            'C22 H20 N2 O4 S2'
_chemical_formula_weight         440.54
_chemical_name_common            u180316mor1
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 114.780(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.963(3)
_cell_length_b                   8.7052(9)
_cell_length_c                   15.5575(15)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      2.95
_cell_volume                     4053.2(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13824
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.302
_diffrn_reflns_theta_min         5.292
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.663
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0566P)^2^+3.6684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                3563
_reflns_number_total             3709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03498_si_002.cif
_cod_data_source_block           I
_cod_database_code               4038162
_shelx_res_checksum              8970
_shelx_hkl_checksum              83192