Iodine-mediated regioselective C2-amination of indoles and a concise total synthesis of (+/-)-folicanthine
Ying-Xiu Li; Hai-Xi Wang; Shaukat Ali; Xiao-Feng Xia; Yong-Ming Liang; Chem.Commun. 48 (2012) 2343–; doi:10.1039/c2cc16637b

data_7107383
_publ_section_title
;
 Iodine-mediated regioselective C2-amination of indoles and a concise
 total synthesis of (+/-)-folicanthine
;
_journal_name_full               Chem.Commun.
_journal_page_first              2343
_journal_paper_doi               10.1039/c2cc16637b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C36 H38 N4 O4 S2'
_chemical_formula_weight         654.82
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 102.099(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.563(7)
_cell_length_b                   12.194(3)
_cell_length_c                   19.897(4)
_cell_measurement_reflns_used    3579
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.79
_cell_measurement_theta_min      2.59
_cell_volume                     7488(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16221
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_platon_squeeze_details
;
;
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0653
_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^)+(0.1100P)^2^+0.2109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1777
_refine_ls_wR_factor_ref         0.2020
_reflns_number_gt                3339
_reflns_number_total             6776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc16637b.txt
_cod_data_source_block           c2c
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7107383