One-Pot Synthesis of Indole-Fused Scaffolds via Gold-Catalyzed Tandem Annulation Reactions of 1,2-Bis(alkynyl)-2-en-1-ones with Indoles
Xin Xie; Xiangwei Du; Yifeng Chen; Yuanhong Liu; Journal of Organic Chemistry 76 (2011) 9175–9181; doi:10.1021/jo2017668

data_4026719
_publ_section_title
;
 One-Pot Synthesis of Indole-Fused Scaffolds via Gold-Catalyzed Tandem
 Annulation Reactions of 1,2-Bis(alkynyl)-2-en-1-ones with Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9175
_journal_page_last               9181
_journal_paper_doi               10.1021/jo2017668
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C33 H23 N O3'
_chemical_formula_weight         481.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                63.084(2)
_cell_angle_beta                 81.883(3)
_cell_angle_gamma                81.254(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1943(13)
_cell_length_b                   11.9963(17)
_cell_length_c                   12.7403(19)
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.520
_cell_measurement_theta_min      5.440
_cell_volume                     1234.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6707
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67849
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                3463
_reflns_number_total             4753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2017668_si_003.cif
_cod_data_source_block           cd21106
_cod_database_code               4026719