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_4034912
_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         'C20 H22 N2 O3 S'
_chemical_formula_sum            'C20 H22 N2 O3 S'
_chemical_formula_weight         370.45
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.6839(10)
_cell_length_b                   26.6839(10)
_cell_length_c                   10.2280(7)
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.3900
_cell_measurement_theta_min      4.1430
_cell_volume                     7282.6(6)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.885
_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    -17.00  27.00   1.00    7.50    --   11.74 -58.00 140.00   44
  2  \w    -59.00  40.00   1.00    7.50    --   11.74 -57.00 -60.00   99
  3  \w     -5.00  20.00   1.00    7.50    --   11.74 -99.00   0.00   25
;
_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      0.0212575000
_diffrn_orient_matrix_UB_12      0.0156946000
_diffrn_orient_matrix_UB_13      0.0079336000
_diffrn_orient_matrix_UB_21      -0.0034500000
_diffrn_orient_matrix_UB_22      0.0094486000
_diffrn_orient_matrix_UB_23      -0.0641901000
_diffrn_orient_matrix_UB_31      -0.0155837000
_diffrn_orient_matrix_UB_32      0.0192871000
_diffrn_orient_matrix_UB_33      0.0249588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15570
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.507
_diffrn_reflns_theta_min         3.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80983
_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    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0572P)^2^+7.1565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3292
_reflns_number_total             4489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00286_si_001.cif
_cod_data_source_block           exp_527
_cod_original_cell_volume        7282.6(7)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4034912
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.72
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C16(H16), C4(H4), C17(H17), C15(H15), C1(H1), C2(H2A),
 C3(H3)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_date_sample_data_collection 2017-05-15
_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.749