Bioinspired direct access to benzofuroindolines by oxidative [3 + 2] annulation of phenols and indoles.
Denizot, Natacha; Pouilhès, Annie; Cucca, Mélissa; Beaud, Rodolphe; Guillot, Régis; Kouklovsky, Cyrille; Vincent, Guillaume; Organic letters 16 (2014) 5752–5755; doi:10.1021/ol502820p

data_1518137
_publ_section_title
;
 Bioinspired direct access to benzofuroindolines by oxidative [3 + 2]
 annulation of phenols and indoles.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5752
_journal_page_last               5755
_journal_paper_doi               10.1021/ol502820p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C22 H25 N O4 '
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.3190(10)
_cell_angle_beta                 81.2570(10)
_cell_angle_gamma                75.3850(10)
_cell_formula_units_Z            4
_cell_length_a                   7.6526(2)
_cell_length_b                   14.3216(4)
_cell_length_c                   17.7284(5)
_cell_measurement_reflns_used    7770
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.72
_cell_measurement_theta_min      2.33
_cell_volume                     1852.08(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30259
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.85
_diffrn_reflns_theta_min         1.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         13253
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.5119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                8928
_reflns_number_total             13253
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502820p_si_002.cif
_cod_data_source_block           12u
_cod_depositor_comments
'Adding full bibliography for 1518137--1518138.cif.'
_cod_original_formula_sum        'C22 H25 N O4 '
_cod_database_code               1518137