Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides.
Guo, Yu-Jing; Lu, Shuai; Tian, Lu-Lu; Huang, En-Ling; Hao, Xin-Qi; Zhu, Xinju; Shao, Tian; Song, Mao-Ping; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02734

data_4033295
_publ_section_title
;
 Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium
 Sulfinates: Synthesis of Sulfones and Sulfides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02734
_journal_year                    2017
_chemical_formula_moiety         'C19 H14 N2 O2 S'
_chemical_formula_sum            'C19 H14 N2 O2 S'
_chemical_formula_weight         334.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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Olex2 1.2
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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;
  1 omega -107.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -47.00   34.00   1.0000    1.0000
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  3 omega  -65.00  -35.00   1.0000    1.0000
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omega____ theta____ kappa____ phi______ frames
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  5 omega  -27.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   59.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 26

  8 omega  -33.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 64

  9 omega   -2.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 41

 10 omega   75.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 35

 11 omega   65.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

 12 omega   18.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 43

 13 omega   63.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 35

 14 omega   13.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 41

 15 omega   39.00   64.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 25

 16 omega   37.00   91.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 54

 17 omega  102.00  165.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   92.0000  101.0000 63

 18 omega   67.00   98.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 31

 19 omega   68.00   95.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 27

 20 omega   43.00   91.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 48

 21 omega   41.00   98.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 57

 22 omega   37.00   79.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 42

 23 omega   40.00   88.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 48

 24 omega   51.00  107.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 56

 25 omega   43.00  153.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -90.0000 110
;
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_limit_h_min       -8
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_diffrn_reflns_limit_k_min       -11
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+0.8415P] where P=(Fo^2^+2Fc^2^)/3'
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C1'(H1'), C2'(H2'),
  C3'(H3'), C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12'), C13'(H13'),
 C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C19'(H19')
;
_olex2_submission_special_instructions 'No special instructions were received'