Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
Xiao-Feng Xia; Ning Wang; Lu-Lu Zhang; Xian-Rong Song; Xue-Yuan Liu; Yong-Min Liang; Journal of Organic Chemistry 77 (2012) 9163–9170; doi:10.1021/jo301741j

data_4027607
_publ_section_title
;
 Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of
 Alkynes for the Synthesis of Functionalized Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9163
_journal_page_last               9170
_journal_paper_doi               10.1021/jo301741j
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C24 H18 F N'
_chemical_formula_weight         339.39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.894(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.843(8)
_cell_length_b                   18.307(9)
_cell_length_c                   11.541(6)
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.22
_cell_volume                     3423(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10896
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0510P)^2^+1.7489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                1913
_reflns_number_total             3183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301741j_si_003.cif
_cod_data_source_block           c2c
_cod_original_cell_volume        3422(3)
_cod_database_code               4027607