Iodine-Induced Regioselective C-C and C-N Bonds Formation of N-Protected Indoles
Ying-Xiu Li; Ke-Gong Ji; Hai-Xi Wang; Shaukat Ali; Yong-Min Liang; Journal of Organic Chemistry 76 (2011) 744–747; doi:10.1021/jo1023014

data_4026001
_publ_section_title
;
 Iodine-Induced Regioselective C-C and C-N Bonds Formation of N-Protected
 Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              744
_journal_page_last               747
_journal_paper_doi               10.1021/jo1023014
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.33
_space_group_IT_number           14
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.463(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2936(15)
_cell_length_b                   7.2657(10)
_cell_length_c                   17.145(2)
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.80
_cell_volume                     1397.9(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7500
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0658P)^2^+0.1396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2076
_reflns_number_total             2723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1023014_si_002.cif
_cod_data_source_block           p-1
_cod_original_sg_symbol_H-M      'P -1'
_cod_database_code               4026001