I2/TBHP-Catalyzed Chemoselective Amination of Indoles
Cai, Zhong-Jian; Wang, Shun-Yi; Ji, Shun-Jun; Organic Letters 15 (2013) 5226–; doi:10.1021/ol4023936

data_1512571
_publ_section_title
;
 I2/TBHP-Catalyzed Chemoselective Amination of Indoles
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              5226
_journal_paper_doi               10.1021/ol4023936
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C23 H23 N3, C4 H8 O2'
_chemical_formula_sum            'C27 H31 N3 O2'
_chemical_formula_weight         429.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.626(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.0116(14)
_cell_length_b                   11.7702(10)
_cell_length_c                   17.9128(10)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      27.3650
_cell_measurement_theta_min      3.8750
_cell_volume                     4846.6(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4692
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_details
;
  1 omega  -84.00   -4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -38.0000  -90.0000 80

  2 omega   -3.00   30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -99.0000 -120.0000 33

  3 omega  -88.00  -15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -38.0000    0.0000 73

  4 omega  -14.00   26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       12.2378   38.0000 -180.0000 40
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0034889000
_diffrn_orient_matrix_UB_12      0.0598005000
_diffrn_orient_matrix_UB_13      0.0014377000
_diffrn_orient_matrix_UB_21      0.0276753000
_diffrn_orient_matrix_UB_22      0.0050845000
_diffrn_orient_matrix_UB_23      0.0188331000
_diffrn_orient_matrix_UB_31      0.0132158000
_diffrn_orient_matrix_UB_32      0.0051691000
_diffrn_orient_matrix_UB_33      -0.0348510000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13983
_diffrn_reflns_theta_full        29.40
_diffrn_reflns_theta_max         29.40
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0579
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                3676
_reflns_number_total             5802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4023936_si_003.cif
_cod_data_source_block           g130511b
_cod_database_code               1512571
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C22(H22), C19(H19), C18(H18), C15(H15), C6(H6), C4(H4),
 C11(H11), C12(H12), C5(H5), C7(H7), C21(H21), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C29(H29A,H29B,H29C), C16(H16A,H16B,H16C), C23(H23A,H23B,
 H23C), C26(H26A,H26B,H26C)
;