Direct thioamination of arynes via reaction with sulfilimines and migratory N-arylation.
Yoshida, Suguru; Yano, Takahisa; Misawa, Yoshihiro; Sugimura, Yasuyuki; Igawa, Kazunobu; Shimizu, Shigeomi; Tomooka, Katsuhiko; Hosoya, Takamitsu; Journal of the American Chemical Society 137 (2015) 14071–14074; doi:10.1021/jacs.5b10557

data_4129805
_publ_section_title
;
 Direct thioamination of arynes via reaction with sulfilimines and
 migratory N-arylation.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14071
_journal_page_last               14074
_journal_paper_doi               10.1021/jacs.5b10557
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C19 H17 N O S'
_chemical_formula_sum            'C19 H17 N O S'
_chemical_formula_weight         307.41
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.087(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.0234(8)
_cell_length_b                   25.185(4)
_cell_length_c                   10.5237(14)
_cell_measurement_reflns_used    5321
_cell_measurement_temperature    143
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1596.4(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      143
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24530
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3653
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.6237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                3384
_reflns_number_total             3653
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja5b10557_si_002.cif
_cod_data_source_block           TY-3402-1-1
_cod_database_code               4129805