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Zeitschrift für Kristallographie - Crystalline Materials

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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. Arman
  • 1 University of Texas at San Antonio, Department of Chemistry, San Antonio, Texas 78249-0689, U.S.A.
/ Trupta Kaulgud
  • 2 The University of Texas at San Antonio, Department of Chemistry, San Antonio, TX 78249-0698, U.S.A.
/ Tyler Miller
  • 3 The University of Texas at San Antonio, Department of Chemistry, San Antonio, TX 78249-0698, U.S.A.
/
Published Online: 2012-02-09 | DOI: https://doi.org/10.1524/zkri.2012.1482

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.

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

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

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


Published Online: 2012-02-09

Published in Print: 2012-04-01


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

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[1]
David Lüdeker and Gunther Brunklaus
Solid State Nuclear Magnetic Resonance, 2015, Volume 65, Page 29
[2]
Hadi D. Arman and Edward R. T. Tiekink
Acta Crystallographica Section E Structure Reports Online, 2013, Volume 69, Number 9, Page o1447
[3]
V. Nagarajan, Manishkumar R. Shimpi, and V.R. Pedireddi
Journal of Molecular Structure, 2013, Volume 1050, Page 216
[5]
Edward R. T. Tiekink, Tyler Miller, and Edward R. T. Tiekink
Zeitschrift für Kristallographie - Crystalline Materials, 2012, Volume 227, Number 12, Page 825
[6]
Hadi D. Arman, Trupta Kaulgud, and Edward R. T. Tiekink
Acta Crystallographica Section E Structure Reports Online, 2012, Volume 68, Number 9, Page o2662

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