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_4038163
_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            'C33 H30 N2 O4 S2'
_chemical_formula_weight         582.71
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 106.7887(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7296(6)
_cell_length_b                   28.0212(17)
_cell_length_c                   10.7123(7)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.2218
_cell_measurement_theta_min      3.1542
_cell_volume                     2796.1(3)
_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_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40184
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.304
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+1.4606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                5005
_reflns_number_total             5044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03498_si_004.cif
_cod_data_source_block           I
_cod_database_code               4038163
_shelx_res_checksum              47804
_shelx_hkl_checksum              54527