Palladium-catalyzed peri-selective chalcogenation of naphthylamines with diaryl disulfides and diselenides via C-H bond cleavage.
Iwasaki, Masayuki; Kaneshika, Wataru; Tsuchiya, Yuta; Nakajima, Kiyohiko; Nishihara, Yasushi; The Journal of organic chemistry 79 (2014) 11330–11338; doi:10.1021/jo502274t

data_4030233
_publ_section_title
;
 Palladium-catalyzed peri-selective chalcogenation of naphthylamines with
 diaryl disulfides and diselenides via C-H bond cleavage.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11330
_journal_page_last               11338
_journal_paper_doi               10.1021/jo502274t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C22 H16 N2 O S'
_chemical_formula_sum            'C22 H16 N2 O S'
_chemical_formula_weight         356.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.23(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.699(5)
_cell_length_b                   28.969(13)
_cell_length_c                   8.335(5)
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_cell_measurement_temperature    298
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.11
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_computing_cell_refinement       'RAPID AUTO'
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_computing_publication_material  'CrystalStructure 4.0'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71075
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_diffrn_reflns_limit_k_min       -37
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_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.199
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_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
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_refine_ls_number_reflns         3970
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_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0865P)^2^+0.1304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502274t_si_001.cif
_cod_data_source_block           yn40
_cod_depositor_comments          'Adding full bibliography for 4030233.cif.'
_cod_original_cell_volume        1744.4(16)
_cod_database_code               4030233