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_1518138
_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 H22 N2 O3'
_chemical_formula_sum            'C22 H22 N2 O3'
_chemical_formula_weight         362.42
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4467(14)
_cell_length_b                   16.2308(15)
_cell_length_c                   7.0318(6)
_cell_measurement_reflns_used    2018
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      20.06
_cell_measurement_theta_min      2.51
_cell_volume                     1763.0(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.1166
_diffrn_reflns_av_sigmaI/netI    0.1228
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26636
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         1.25
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0605P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                2958
_reflns_number_total             5072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502820p_si_002.cif
_cod_data_source_block           16
_cod_depositor_comments
'Adding full bibliography for 1518137--1518138.cif.'
_cod_database_code               1518138