Synthesis of the Reported Pyranonaphthoquinone Structure of the Indoleamine-2,3-dioxygenase Inhibitor Annulin B by Regioselective Diels-Alder Reaction.
Inman, Martyn; Carvalho, Catarina; Lewis, William; Moody, Christopher J.; The Journal of organic chemistry 81 (2016) 7924–7930; doi:10.1021/acs.joc.6b01622

data_4037161
_publ_section_title
;
 Synthesis of the Reported Pyranonaphthoquinone Structure of the
 Indoleamine-2,3-dioxygenase Inhibitor Annulin B by Regioselective
 Diels-Alder Reaction.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7924
_journal_page_last               7930
_journal_paper_doi               10.1021/acs.joc.6b01622
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C14 H13 Br O6'
_chemical_formula_sum            'C14 H13 Br O6'
_chemical_formula_weight         357.15
_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'
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Olex2 1.2
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_cell_measurement_reflns_used    6110
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
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  1 omega   -9.00   27.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -43.00   21.00   2.0000    2.0000
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  3 omega  -48.00   30.00   2.0000    2.0000
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  4 omega   20.00   96.00   2.0000    2.0000
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  5 omega   26.00  106.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   26.00   96.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   33.00   77.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   43.00   97.00   2.0000    4.0000
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  9 omega   41.00   79.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   64.00  110.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   26.00  116.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega  142.00  170.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega   53.00   81.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   95.00  121.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega  102.00  136.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000    0.0000 17

 16 omega   40.00  108.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -180.0000 34

 17 omega   41.00   89.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  150.0000 24

 18 omega   33.00   75.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  150.0000 21

 19 omega   40.00  132.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000 -120.0000 46

 20 omega   27.00  133.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   18.00  110.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   57.0000   30.0000 46

 22 omega   18.00  110.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7573   57.0000  -60.0000 46
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_diffrn_source                   'microfocus sealed tube'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
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Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear yellow'
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_cod_data_source_file            jo6b01622_si_003.cif
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_cod_database_code               4037161
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_nottingham_internal_coll_number 13872
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_nottingham_internal_coll_frame_time '2.0000, 4.0000'
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_chemical_oxdiff_formula         'C14 H13 Br O6'
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'MICJMM #13872 GVA-357 IN FOMBLIN FILM ON A MICROMOUNT FOR MI/CJM'
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_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:
 C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
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