Double C–H Functionalization of Indoles via Three-Component Reactions/CuCl2-Catalyzed Aerobic Dehydrogenative Coupling for the Synthesis of Polyfunctional Cyclopenta[b]indoles
Jiang, Liqin; Jin, Weifeng; Hu, Wenhao; ACS Catalysis 6 (2016) 6146–; doi:10.1021/acscatal.6b01946

data_4513935
_publ_section_title
;
 Double C--H Functionalization of Indoles via Three-Component
 Reactions/CuCl2-Catalyzed Aerobic Dehydrogenative Coupling for the
 Synthesis of Polyfunctional Cyclopenta[b]indoles
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              6146
_journal_paper_doi               10.1021/acscatal.6b01946
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C29 H25 N O5'
_chemical_formula_weight         467.50
_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                75.2300(10)
_cell_angle_beta                 88.2750(10)
_cell_angle_gamma                69.4610(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2103(4)
_cell_length_b                   9.7574(4)
_cell_length_c                   14.5275(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1179.64(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13887
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0715P)^2^+0.4663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                2920
_reflns_number_total             4126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b01946_si_003.cif
_cod_data_source_block           z
_cod_depositor_comments          'Adding full bibliography for 4513935.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513935