Synthesis of 3-Acyl-2-arylindole via Palladium-catalyzed Isocyanide Insertion and Oxypalladation of Alkyne
Nanjo, Takeshi; Yamamoto, Sho; Tsukano, Chihiro; Takemoto, Yoshiji; Organic Letters 15 (2013) 3754–; doi:10.1021/ol4016699

data_1512201
_publ_section_title
;
 Synthesis of 3-Acyl-2-arylindole via Palladium-catalyzed Isocyanide
 Insertion and Oxypalladation of Alkyne
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3754
_journal_paper_doi               10.1021/ol4016699
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C47 H29 Cl3 N4'
_chemical_formula_sum            'C47 H29 Cl3 N4'
_chemical_formula_weight         756.13
_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
_cell_angle_alpha                64.891(4)
_cell_angle_beta                 81.409(4)
_cell_angle_gamma                78.963(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3660(12)
_cell_length_b                   16.750(3)
_cell_length_c                   17.108(3)
_cell_measurement_reflns_used    6597
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.02
_cell_volume                     1870.5(6)
_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    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.1109
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17899
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             780.00
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.430
_refine_ls_extinction_coef       0.0089(17)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7745
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0838
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0907P)^2^+1.1274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2326
_reflns_number_gt                3896
_reflns_number_total             8434
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol4016699_si_002.cif
_cod_data_source_block           yamamoto130422
_cod_original_cell_volume        1870.4(5)
_cod_database_code               1512201