Journal
CRYSTAL GROWTH & DESIGN
Volume 13, Issue 4, Pages 1464-1472Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cg301561J
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Funding
- University of Birmingham
- EPSRC UK National Crystallography Service
- Advantage West Midlands (AWM)
- European Regional Development Fund (ERDF)
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The powerful hydrogen bonding capability of adenine makes it a key component of the DNA double helix, while as a crystalline molecular material, these hydrogen bond donors and acceptors make it a good potential cocrystal component possessing distinct physical properties. Here, we report the preparation and structure determination of four adenine-based multicomponent adducts formed with a number of dicarboxylic acids: an anhydrous cocrystal with succinic acid (1), anhydrous salts with fumaric acid (2) and maleic acid (3), and a methanolated salt with maleic acid (4). The supramolecular behavior of adenine in these materials is discussed in terms of strong hydrogen-bonded bidentate motifs formed between the adenine and acid components and the homomeric adenine synthons retained in these structures. The additional formation of a CH center dot center dot center dot N interaction on the Watson-Crick site in (3) enables the stabilization of the unusual 3H,7H adeninium tautomer within a purely molecular material.
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