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_1512573
_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_absolute_configuration ad
_chemical_formula_moiety         'C25 H24 I N3 O4 S'
_chemical_formula_sum            'C25 H24 I N3 O4 S'
_chemical_formula_weight         589.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 116.328(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7685(5)
_cell_length_b                   26.1496(11)
_cell_length_c                   10.6114(6)
_cell_measurement_reflns_used    6460
_cell_measurement_temperature    200.05(10)
_cell_measurement_theta_max      28.7080
_cell_measurement_theta_min      3.7700
_cell_volume                     2429.4(3)
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      200.05(10)
_diffrn_detector_area_resol_mean 10.4692
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details
;
  1 omega  -11.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -99.0000  -30.0000 30

  2 omega    6.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816   38.0000   90.0000 26

  3 omega  -77.00    6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.0816  -38.0000  -30.0000 83

  4 omega  -41.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.2378  -77.0000 -120.0000 87

  5 omega   35.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.2378  178.0000   90.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0035827000
_diffrn_orient_matrix_UB_12      -0.0029485000
_diffrn_orient_matrix_UB_13      -0.0648976000
_diffrn_orient_matrix_UB_21      0.0154522000
_diffrn_orient_matrix_UB_22      -0.0264535000
_diffrn_orient_matrix_UB_23      0.0139647000
_diffrn_orient_matrix_UB_31      -0.0794518000
_diffrn_orient_matrix_UB_32      -0.0052651000
_diffrn_orient_matrix_UB_33      -0.0339309000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15586
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.83
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86550
_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    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.028(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         8218
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0324P)^2^+0.6621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                7492
_reflns_number_total             8218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4023936_si_005.cif
_cod_data_source_block           g130428a
_cod_original_cell_volume        2429.4(2)
_cod_database_code               1512573
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.76
_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), C16(H16), C39(H39), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C20(H20),
 C21(H21), C23(H23), C24(H24), N1(H1), N2(H2), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C45(H45), C46(H46), C48(H48),
  C49(H49), N4(H4A), N5(H5A)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C43(H43A,H43B,H43C), C50(H50A,H50B,
 H50C)
;