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_7154499
_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         'C18 H16 N2 O S'
_chemical_formula_sum            'C18 H16 N2 O S'
_chemical_formula_weight         308.40
_chemical_melting_point          369
_chemical_name_systematic
6-Methyl-2-(methylsulfanyl)-N-(quinolin-8-yl)benzamide
_space_group_IT_number           14
_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
_audit_update_record
;
2014-10-21 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.8321(17)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.2995(4)
_cell_length_b                   8.9313(4)
_cell_length_c                   23.2132(12)
_cell_measurement_reflns_used    11322
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.32
_cell_volume                     1513.20(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14456
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.4540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                3052
_reflns_number_total             3457
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5ob00149h2.cif
_cod_data_source_block           2-methylthio-6-methylbenzo
_cod_depositor_comments
'Adding full bibliography for 7154496--7154499.cif.'
_cod_original_cell_volume        1513.20(14)
_cod_database_code               7154499