Nickel-catalyzed synthesis of diarylsulfides and sulfones via C-H bond functionalization of arylamides.
Reddy, Vutukuri Prakash; Qiu, Renhua; Iwasaki, Takanori; Kambe, Nobuaki; Organic & biomolecular chemistry 13 (2015) 6803–6813; doi:10.1039/c5ob00149h

data_7154498
_publ_section_title
;
 Nickel-catalyzed synthesis of diarylsulfides and sulfones via C-H bond
 functionalization of arylamides.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6803
_journal_page_last               6813
_journal_paper_doi               10.1039/c5ob00149h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C31 H26 N2 O5 S2'
_chemical_formula_sum            'C31 H26 N2 O5 S2'
_chemical_formula_weight         570.68
_chemical_melting_point          549
_chemical_name_systematic
2-(4-Methylbenzenesulfonyl)-6-methyl-N-(5-(4-methylbenzenesulfonyl)quinolin-8-yl)benzamide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2014-09-10 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                65.7836(10)
_cell_angle_beta                 78.6515(11)
_cell_angle_gamma                89.8471(12)
_cell_formula_units_Z            2
_cell_length_a                   10.24960(19)
_cell_length_b                   10.78136(19)
_cell_length_c                   13.5184(3)
_cell_measurement_reflns_used    21953
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.67
_cell_measurement_theta_min      3.67
_cell_volume                     1330.66(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30171
_diffrn_reflns_theta_full        71.74
_diffrn_reflns_theta_max         71.74
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5068
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.6269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                4382
_reflns_number_total             5068
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5ob00149h2.cif
_cod_data_source_block           (2-Ts-6-Me-benzoyl)-5-Ts-a
_cod_depositor_comments
'Adding full bibliography for 7154496--7154499.cif.'
_cod_database_code               7154498