Direct C-H Bond Arylation of Thienyl Thioamides Catalyzed by Pd-Phenanthroline Complexes.
Yamauchi, Takayuki; Shibahara, Fumitoshi; Murai, Toshiaki; Organic letters 17 (2015) 5392–5395; doi:10.1021/acs.orglett.5b02742

data_1555390
_publ_section_title
;
 Direct C-H Bond Arylation of Thienyl Thioamides Catalyzed by
 Pd-Phenanthroline Complexes.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5392
_journal_page_last               5395
_journal_paper_doi               10.1021/acs.orglett.5b02742
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C23 H25 N S2'
_chemical_formula_sum            'C23 H25 N S2'
_chemical_formula_weight         379.56
_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_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.639(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4977(14)
_cell_length_b                   11.606(2)
_cell_length_c                   23.037(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2003.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0892
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16661
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+13.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                2977
_reflns_number_total             4587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02742_si_002.cif
_cod_data_source_block           ty0916
_cod_original_cell_volume        2003.7(7)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1555390