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_7154186
_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         'C14 H14 N4 O4'
_chemical_formula_sum            'C14 H14 N4 O4'
_chemical_formula_weight         302.29
_chemical_name_systematic        syn-5g
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                80.083(16)
_cell_angle_beta                 86.694(16)
_cell_angle_gamma                79.180(13)
_cell_formula_units_Z            4
_cell_length_a                   7.764(3)
_cell_length_b                   9.345(4)
_cell_length_c                   20.472(9)
_cell_measurement_reflns_used    4713
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4764
_cell_measurement_theta_min      2.0204
_cell_volume                     1436.6(10)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution
;
'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0287
_diffrn_orient_matrix_UB_12      0.0689
_diffrn_orient_matrix_UB_13      0.1078
_diffrn_orient_matrix_UB_21      -0.0005
_diffrn_orient_matrix_UB_22      0.0805
_diffrn_orient_matrix_UB_23      -0.0756
_diffrn_orient_matrix_UB_31      -0.0482
_diffrn_orient_matrix_UB_32      -0.0006
_diffrn_orient_matrix_UB_33      0.0116
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5105
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         1.010
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       Plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5105
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.1109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1509P)^2^+3.7230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3066
_refine_ls_wR_factor_ref         0.3194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4174
_reflns_number_total             5105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01549e2.cif
_cod_data_source_block           sa3259
_cod_depositor_comments
'Adding full bibliography for 7154184--7154188.cif.'
_cod_original_cell_volume        1436.7(11)
_cod_database_code               7154186
_shelxl_version_number           2013-4
_diffrn_number_total             6486
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N3B) \\sim Ueq, Uanis(N3A) \\sim Ueq, Uanis(N4A) \\sim Ueq, Uanis(N4B)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(N3B)=Sof(N4B)=1-FVAR(1)
 Sof(N3A)=Sof(N4A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C13A(H13A,H13B), C9(H9A,H9B), C10(H10C,H10D),
  C13(H13C,H13D)
4.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C5(H5), C6(H6), C7(H7), C8(H8)
4.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C14(H14D,H14E,H14F)
;
_shelx_res_checksum              1905