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Zeitschrift für Kristallographie - Crystalline Materials

Ed. by Antipov, Evgeny / Bismayer, Ulrich / Huppertz, Hubert / Petrícek, Václav / Pöttgen, Rainer / Schmahl, Wolfgang / Tiekink, E. R. T. / Zou, Xiaodong

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Persistence of the {…HOCO…HCN} heterosynthon in the co-crystals formed between anthranilic acid and three bipyridine-containing molecules

Hadi D. Arman1 / Trupta Kaulgud2 / Tyler Miller3 /

1 University of Texas at San Antonio, Department of Chemistry, San Antonio, Texas 78249-0689, U.S.A.

2 The University of Texas at San Antonio, Department of Chemistry, San Antonio, TX 78249-0698, U.S.A.

3 The University of Texas at San Antonio, Department of Chemistry, San Antonio, TX 78249-0698, U.S.A.

* Correspondence address: University of Malaya, Department of Chemistry, 50603 Kuala Lumpur, Malaysia,

Citation Information: Zeitschrift für Kristallographie Crystalline Materials. Volume 227, Issue 4, Pages 227–232, ISSN (Print) 0044-2968, DOI: 10.1524/zkri.2012.1482, February 2012

Publication History

Published Online:
2012-02-09

This article offers supplementary material which is provided at the end of the article.

Abstract

Co-crystals formed between anthranilic acid and each of 4,4′-bipyridine (1), 1,2-trans-1,2-bis(4-pyridyl)ethene (2) and 1,2-bis(4-pyridyl)ethane (3) have been formed from solutions containing 2:1 stoichiometric quantities of the reagents. Each structure features a centrosymmetric three-molecule aggregate mediated by O—H…N(pyridyl) hydrogen bonds indicating the robustness of the seven-membered {…HOCO…HCN} heterosynthon. The structures of (1)–(3) are isomorphous whereby the three-molecule aggregates are connected into flattened helical chains by amino-N—H…O(carbonyl) hydrogen bonds; the chains are consolidated into the three-dimensional structure by π…π interactions. The magnitude of the O—H…N hydrogen bonds in (1)–(3) are correlated with the basicity of the pyridine residue.

Keywords: Co-crystal; Carboxylic acid; Hydrogen bond strength; Crystal structure analysis; X-ray diffraction

Supplementary Article Materials

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