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_4026003
_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            'C13 H18 N2 O'
_chemical_formula_weight         218.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 94.73(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.30(2)
_cell_length_b                   17.24(4)
_cell_length_c                   8.57(2)
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      2.36
_cell_volume                     1222(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6414
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.015(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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0751P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                1478
_reflns_number_total             2259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1023014_si_004.cif
_cod_data_source_block           p21c
_cod_database_code               4026003