Regioselective C–H sulfenylation of N-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles
Hu, Jingyan; Ji, Xiaoming; Hao, Shuai; Zhao, Mingqin; Lai, Miao; Ren, Tianbao; Xi, Gaolei; Wang, Erbin; Wang, Juanjuan; Wu, Zhiyong; RSC Advances 10 (2020) 31819–31823; doi:10.1039/D0RA06635D

data_7241143
_publ_section_title
;
 Regioselective C--H sulfenylation of N-sulfonyl protected 7-azaindoles
 promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles
;
_journal_issue                   53
_journal_name_full               'RSC Advances'
_journal_page_first              31819
_journal_page_last               31823
_journal_paper_doi               10.1039/D0RA06635D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 N2 O S'
_chemical_formula_sum            'C14 H12 N2 O S'
_chemical_formula_weight         256.32
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-23 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.533(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7203(9)
_cell_length_b                   5.3408(3)
_cell_length_c                   16.4985(9)
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6360
_cell_measurement_theta_min      5.5710
_cell_volume                     1243.46(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -103.00  -5.00   1.00    1.00    --  -33.50 -77.00  60.00   98
  2  \w    -52.00  35.00   1.00    1.00    --  -33.50  57.00   0.00   87
  3  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   53
  4  \w     -4.00  77.00   1.00    1.00    --   36.47 -99.00-120.00   81
  5  \w    -32.00  55.00   1.00    1.00    --   36.47 -57.00 -90.00   87
  6  \w     -4.00  57.00   1.00    1.00    --   36.47 -37.00-180.00   61
  7  \w    -25.00  52.00   1.00    1.00    --   36.47 -37.00 -60.00   77
  8  \w     40.00  71.00   1.00    1.50    --  108.00 -94.00 -60.00   31
  9  \w     70.00 171.00   1.00    1.50    --  108.00  15.00 120.00  101
 10  \w     67.00 112.00   1.00    1.50    --  108.00 -30.00-120.00   45
 11  \w     85.00 137.00   1.00    1.50    --  108.00 -77.00  30.00   52
 12  \w     62.00 109.00   1.00    1.50    --  108.00-111.00 150.00   47
 13  \w    109.00 168.00   1.00    1.50    --  108.00  61.00   0.00   59
 14  \w     88.00 115.00   1.00    1.50    --  108.00  45.00  60.00   27
 15  \w     46.00 128.00   1.00    1.50    --  108.00 -61.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0996591000
_diffrn_orient_matrix_UB_12      -0.0158966000
_diffrn_orient_matrix_UB_13      -0.0124596000
_diffrn_orient_matrix_UB_21      -0.0430878000
_diffrn_orient_matrix_UB_22      0.0357054000
_diffrn_orient_matrix_UB_23      -0.0959618000
_diffrn_orient_matrix_UB_31      0.0110012000
_diffrn_orient_matrix_UB_32      0.2857625000
_diffrn_orient_matrix_UB_33      0.0112868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4561
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         5.581
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.3496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1695
_reflns_number_total             2222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06635d2.cif
_cod_data_source_block           20200771
_cod_depositor_comments          'Adding full bibliography for 7241143.cif.'
_cod_database_code               7241143
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4
_shelx_estimated_absorpt_t_max   0.826
_shelx_estimated_absorpt_t_min   0.732
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              45659
_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 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.840