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_1512572
_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 H22 Br N3 O2 S'
_chemical_formula_sum            'C23 H22 Br N3 O2 S'
_chemical_formula_weight         484.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2013-04-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:16:32, GUI svn.r4446)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.905(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1909(10)
_cell_length_b                   29.712(3)
_cell_length_c                   8.0681(8)
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    179.7(5)
_cell_measurement_theta_max      29.2030
_cell_measurement_theta_min      3.5810
_cell_volume                     2096.5(4)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      179.7(5)
_diffrn_detector_area_resol_mean 10.4692
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_details
;
  1 omega -101.00  -61.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816 -178.0000  120.0000 50

  2 omega  -11.00   29.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -99.0000  -90.0000 50

  3 omega  -71.00  -39.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -38.0000  -90.0000 40

  4 omega   41.00   98.60   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       12.2378  178.0000 -120.0000 72

  5 omega   34.00   83.60   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       12.2378 -178.0000  120.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0465073000
_diffrn_orient_matrix_UB_12      0.0171157000
_diffrn_orient_matrix_UB_13      0.0183982000
_diffrn_orient_matrix_UB_21      -0.0143304000
_diffrn_orient_matrix_UB_22      0.0086726000
_diffrn_orient_matrix_UB_23      -0.0854610000
_diffrn_orient_matrix_UB_31      -0.0648116000
_diffrn_orient_matrix_UB_32      -0.0142192000
_diffrn_orient_matrix_UB_33      -0.0299293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11760
_diffrn_reflns_theta_full        29.39
_diffrn_reflns_theta_max         29.39
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47374
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0372P)^2^+1.0910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                3808
_reflns_number_total             4988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4023936_si_004.cif
_cod_data_source_block           g130410b
_cod_database_code               1512572
_reflns_odcompleteness_completeness 99.70
_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 Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10),
 C11(H11), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;