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_4129804
_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         'C21 H18 N2 O S'
_chemical_formula_sum            'C21 H18 N2 O S'
_chemical_formula_weight         346.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   14.654(3)
_cell_length_b                   7.559(2)
_cell_length_c                   31.389(5)
_cell_measurement_reflns_used    389
_cell_measurement_temperature    296
_cell_measurement_theta_max      69.94
_cell_measurement_theta_min      6.75
_cell_volume                     3476.9(13)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            25564
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.170
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         4.128
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.730
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456.00
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                2043
_reflns_number_total             3165
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja5b10557_si_004.cif
_cod_data_source_block           hosoya150424
_cod_original_cell_volume        3476.7(13)
_cod_database_code               4129804