Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[ b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines.
Capretz Agy, André; Rodrigues, Jr, Manoel T; Zeoly, Lucas A.; Simoni, Deborah A.; Coelho, Fernando; The Journal of organic chemistry 84 (2019) 5564–5581; doi:10.1021/acs.joc.9b00505

data_4034303
_publ_section_title
;
 Palladium-Mediated Oxidative Annulation of \d-Indolyl-\a,\b-Unsaturated
 Compounds toward the Synthesis of Cyclopenta[ b]indoles and Heterogeneous
 Hydrogenation To Access Fused Indolines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5564
_journal_page_last               5581
_journal_paper_doi               10.1021/acs.joc.9b00505
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-12-04 # Formatted by publCIF

;
_cell_angle_alpha                95.778(2)
_cell_angle_beta                 94.944(2)
_cell_angle_gamma                110.914(2)
_cell_formula_units_Z            4
_cell_length_a                   8.5840(6)
_cell_length_b                   8.6172(6)
_cell_length_c                   14.5365(11)
_cell_measurement_reflns_used    131
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      3.23
_cell_volume                     990.66(12)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2010)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2010)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34213
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_min         1.420
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       irregular
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.2738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4334
_reflns_number_total             5307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00505_si_002.cif
_cod_data_source_block           ACA-440
_cod_database_code               4034303
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              14402
_shelx_hkl_checksum              95095