Metal-free synthesis of indole via NIS-mediated cascade C-N bond formation/aromatization.
Li, Yin-Long; Li, Jian; Ma, Ai-Lun; Huang, Ya-Nan; Deng, Jun; The Journal of organic chemistry 80 (2015) 3841–3851; doi:10.1021/acs.joc.5b00090

data_4036127
_publ_section_title
;
 Metal-free synthesis of indole via NIS-mediated cascade C-N bond
 formation/aromatization.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3841
_journal_page_last               3851
_journal_paper_doi               10.1021/acs.joc.5b00090
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C28 H23 N O3 S'
_chemical_formula_weight         453.53
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        '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                86.50(3)
_cell_angle_beta                 77.99(3)
_cell_angle_gamma                64.10(3)
_cell_formula_units_Z            2
_cell_length_a                   9.907(2)
_cell_length_b                   11.217(2)
_cell_length_c                   11.866(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1159.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9704
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9587
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.018(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   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                2788
_reflns_number_total             4312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00090_si_001.cif
_cod_data_source_block           b
_cod_original_cell_volume        1159.6(4)
_cod_database_code               4036127