Oxidative Furan-to-Indole Rearrangement. Synthesis of 2-(2-Acylvinyl)indoles and Flinderole C Analogues.
Makarov, Anton S.; Merkushev, Anton A.; Uchuskin, Maxim G.; Trushkov, Igor V.; Organic letters 18 (2016) 2192–2195; doi:10.1021/acs.orglett.6b00805

data_1555548
_publ_section_title
;
 Oxidative Furan-to-Indole Rearrangement. Synthesis of
 2-(2-Acylvinyl)indoles and Flinderole C Analogues.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2192
_journal_page_last               2195
_journal_paper_doi               10.1021/acs.orglett.6b00805
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C25 H23 N O4 S'
_chemical_formula_sum            'C26 H25 Cl2 N O4 S'
_chemical_formula_weight         518.43
_chemical_melting_point          395
_chemical_name_systematic
5-methyl-3'-phenyl-1'-tosyl-5H-spiro[furan-2,2'-indolin]-5-ol
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                92.489(10)
_cell_angle_beta                 106.194(13)
_cell_angle_gamma                96.538(12)
_cell_formula_units_Z            2
_cell_length_a                   9.9795(17)
_cell_length_b                   10.2314(13)
_cell_length_c                   12.8722(13)
_cell_measurement_reflns_used    3160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6720
_cell_measurement_theta_min      3.8230
_cell_volume                     1250.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4752
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10007
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             540
_exptl_crystal_recrystallization_method DCM
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5803
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1072P)^2^+0.2743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                4528
_reflns_number_total             5803
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol6b00805_si_002.cif
_cod_data_source_block           psu-80(am)
_cod_database_code               1555548