Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads.
Mikhailov, Kirill I.; Galenko, Ekaterina E.; Galenko, Alexey V.; Novikov, Mikhail S.; Ivanov, Alexander Yu; Starova, Galina L.; Khlebnikov, Alexander F.; The Journal of organic chemistry 83 (2018) 3177–3187; doi:10.1021/acs.joc.8b00069

data_4033521
_publ_section_title
;
 Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2
 H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of
 Pyrazole-Nitrogen Heterocycle Dyads.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3177
_journal_page_last               3187
_journal_paper_doi               10.1021/acs.joc.8b00069
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 N3 O3'
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Olex2 1.2
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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  1 omega -113.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  3 omega  -37.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -48.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   62.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   28.00   84.00   1.0000    1.0000
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  7 omega   47.00   97.00   1.0000    1.5000
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  8 omega  144.00  173.00   1.0000    1.5000
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  9 omega   52.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 51

 10 omega   52.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 11 omega   68.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 40

 12 omega   36.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 36

 13 omega   35.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 56

 14 omega   31.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 15 omega   69.00  115.00   1.0000    1.5000
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 16 omega   46.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 34

 17 omega  125.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 18 omega   29.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 72

 19 omega   64.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 20 omega   65.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 21 omega   56.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 35

 22 omega  141.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 37

 23 omega   58.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 24 omega   97.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 25 omega   43.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.1916P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_data_source_block           1728
_cod_depositor_comments
;
Adding full bibliography for 4033521--4033522.cif.

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1572.07(14)
_cod_original_formula_moiety     '2(C18 H17 N3 O3)'
_cod_original_formula_sum        'C5 H0 N29 O14'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     690.34
_cod_database_code               4033521
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'c18 h13 n3 o2'
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_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 Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C1Q(H1QA,H1QB)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C1A(H1A), C1E(H1E), C1H(H1H), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26),
  C27(H27), C1P(H1P)
2.c Idealised Me refined as rotating group:
 C1B(H1BA,H1BB,H1BC), C1N(H1NA,H1NB,H1NC), C1O(H1OA,H1OB,H1OC), C1S(H1SA,H1SB,
 H1SC)
;
_shelx_res_checksum              36920
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_olex2_submission_special_instructions 'No special instructions were received'