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  • Crystallographic characterization of the first reported crystalline form of the potent hallucinogen (R)-2-amino-1-(8-bromobenzo[1,2-b;5,4-b']difuran-4-yl)propane or `bromodragonfly': the 1:1 anhydrous proton-transfer compound with 3,5-dinitrosalicylic acid

    File version
    Accepted Manuscript (AM)
    Author(s)
    Smith, Graham
    Cotton, Marcus S
    Wermuth, Urs D
    Boyd, Sue E
    Griffith University Author(s)
    Boyd, Sue E.
    Wermuth, Urs D.
    Year published
    2010
    Metadata
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    Abstract
    The 1:1 proton-transfer compound of the potent substituted amphetamine hallucinogen (R)-2-amino-1-(8-bromo­benzo[1,2-b;5,4-b']difuran-4-yl)propane (common trivial name `bromo­dragonfly') with 3,5-dinitro­salicylic acid, namely 1-(8-bromo­benzo[1,2-b;5,4-b']difuran-4-yl)propan-2-aminium 2-carb­oxy-4,6-dinitro­phenolate, C13H13BrNO2+·C7H3N2O7-, forms hydrogen-bonded cation-anion chain substructures comprising undulating head-to-tail anion chains formed through C(8) carboxyl-nitro O-H...O associations and incorporating the aminium groups of the cations. The intra­chain cation-anion hydrogen-bonding associations feature proximal ...
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    The 1:1 proton-transfer compound of the potent substituted amphetamine hallucinogen (R)-2-amino-1-(8-bromo­benzo[1,2-b;5,4-b']difuran-4-yl)propane (common trivial name `bromo­dragonfly') with 3,5-dinitro­salicylic acid, namely 1-(8-bromo­benzo[1,2-b;5,4-b']difuran-4-yl)propan-2-aminium 2-carb­oxy-4,6-dinitro­phenolate, C13H13BrNO2+·C7H3N2O7-, forms hydrogen-bonded cation-anion chain substructures comprising undulating head-to-tail anion chains formed through C(8) carboxyl-nitro O-H...O associations and incorporating the aminium groups of the cations. The intra­chain cation-anion hydrogen-bonding associations feature proximal cyclic R33(8) inter­actions involving both an N+-H...Ophenolate and the carboxyl-nitro O-H...O associations and aromatic [pi]-[pi] ring inter­actions [minimum ring centroid separation = 3.566 (2) Å]. A lateral hydrogen-bonding inter­action between the third aminium H atom and a carboxyl O-atom acceptor links the chain substructures, giving a two-dimensional sheet structure. This determination represents the first of any form of this compound and is in the (R) absolute configuration. The atypical crystal stability is attributed both to the hydrogen-bonded chain substructures provided by the anions, which accommodate the aminium proton-donor groups of the cations and give crosslinking, and to the presence of the cation-anion aromatic ring [pi]-[pi] inter­actions.
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    Journal Title
    Acta Crystallographica. Section C, Crystal Structure Communications
    Volume
    66
    Issue
    5
    DOI
    https://doi.org/10.1107/S0108270110012850
    Subject
    Inorganic chemistry
    Physical chemistry
    Other chemical sciences
    Other chemical sciences not elsewhere classified
    Publication URI
    http://hdl.handle.net/10072/36882
    Collection
    • Journal articles

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