Iodine-Catalyzed C-H Amidation and Imination at the 2α-Position of 2,3-Disubstituted Indoles with Chloramine Salts.
Liu, Xiaozu; Zhou, Yuxiang; Yang, Zhongqin; Li, Qin; Zhao, Liang; Liu, Peijun; The Journal of organic chemistry 83 (2018) 4665–4673; doi:10.1021/acs.joc.8b00286

data_4034913
_publ_section_title
;
 Iodine-Catalyzed C-H Amidation and Imination at the 2\a-Position of
 2,3-Disubstituted Indoles with Chloramine Salts.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4665
_journal_page_last               4673
_journal_paper_doi               10.1021/acs.joc.8b00286
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H20 N2 O2 S'
_chemical_formula_sum            'C19 H20 N2 O2 S'
_chemical_formula_weight         340.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                108.640(7)
_cell_angle_beta                 105.947(8)
_cell_angle_gamma                102.109(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6536(7)
_cell_length_b                   10.6513(8)
_cell_length_c                   11.9897(11)
_cell_measurement_reflns_used    3669
_cell_measurement_temperature    138(50)
_cell_measurement_theta_max      28.8020
_cell_measurement_theta_min      4.3120
_cell_volume                     841.66(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      138(50)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -13.00  85.00   1.00    1.97    --   11.74  57.00   0.00   98
  2  \w     37.00  63.00   1.00    1.97    --   11.74 178.00-180.00   26
  3  \w    -12.00  75.00   1.00    1.97    --   11.74  77.00 120.00   87
  4  \w    -54.00  36.00   1.00    1.97    --   11.74 -57.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684363000
_diffrn_orient_matrix_UB_12      -0.0246355000
_diffrn_orient_matrix_UB_13      0.0242968000
_diffrn_orient_matrix_UB_21      0.0461283000
_diffrn_orient_matrix_UB_22      -0.0485831000
_diffrn_orient_matrix_UB_23      0.0107066000
_diffrn_orient_matrix_UB_31      0.0599031000
_diffrn_orient_matrix_UB_32      0.0506148000
_diffrn_orient_matrix_UB_33      0.0617027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6363
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.415
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.088
_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     220
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0764P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2888
_reflns_number_total             3868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00286_si_002.cif
_cod_data_source_block           exp_714
_cod_original_cell_volume        841.64(13)
_cod_database_code               4034913
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C15(H15), C12(H12), C13(H13), C5(H5), C4(H4), C14(H14), C11(H11),
 C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2017-07-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 11.606
_oxdiff_exptl_absorpt_empirical_full_min 0.582