A facile approach to spirocyclic 2-azido indolines via azidation of indoles with ceric ammonium nitrate.
Li, Jing; Liu, Mao; Li, Qi; Tian, Hua; Shi, Yian; Organic & biomolecular chemistry 12 (2014) 9769–9772; doi:10.1039/c4ob01549e

data_7154188
_publ_section_title
;
 A facile approach to spirocyclic 2-azido indolines via azidation of
 indoles with ceric ammonium nitrate.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9769
_journal_page_last               9772
_journal_paper_doi               10.1039/c4ob01549e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C21 H23 N5 O4 S'
_chemical_formula_sum            'C21 H23 N5 O4 S'
_chemical_formula_weight         441.50
_chemical_name_systematic        anti-5a
_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                 95.045(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.126(5)
_cell_length_b                   14.074(4)
_cell_length_c                   16.468(6)
_cell_measurement_reflns_used    12773
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.24
_cell_volume                     4185(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30549
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+4.2874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                8420
_reflns_number_total             9533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01549e2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7154184--7154188.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154188