Skip to main content

Research Repository

Advanced Search

Insights into the Crystallisation Process from Anhydrous, Hydrated and Solvated Crystal Forms of Diatrizoic Acid

Fucke, Katharina; McIntyre, Garry J.; Lemee-Cailleay, Marie-Helene; Wilkinson, Clive; Edwards, Alison J.; Howard, Judith A.K.; Steed, Jonathan W.

Insights into the Crystallisation Process from Anhydrous, Hydrated and Solvated Crystal Forms of Diatrizoic Acid Thumbnail


Authors

Katharina Fucke

Garry J. McIntyre

Marie-Helene Lemee-Cailleay

Clive Wilkinson

Alison J. Edwards

Judith A.K. Howard



Contributors

K Edkins (nee Fucke) kdht75@durham.ac.uk
Other

Abstract

Diatrizoic acid (DTA), a clinically used X-ray contrast agent, crystallises in two hydrated, three anhydrous and nine solvated solid forms, all of which have been characterised by X-ray crystallography. Single-crystal neutron structures of DTA dihydrate and monosodium DTA tetrahydrate have been determined. All of the solid-state structures have been analysed using partial atomic charges and hardness algorithm (PACHA) calculations. Even though in general all DTA crystal forms reveal similar intermolecular interactions, the overall crystal packing differs considerably from form to form. The water of the dihydrate is encapsulated between a pair of host molecules, which calculations reveal to be an extraordinarily stable motif. DTA presents functionalities that enable hydrogen and halogen bonding, and whilst an extended hydrogen-bonding network is realised in all crystal forms, halogen bonding is not present in the hydrated crystal forms. This is due to the formation of a hydrogen-bonding network based on individual enclosed water squares, which is not amenable to the concomitant formation of halogen bonds. The main interaction in the solvates involves the carboxylic acid, which corroborates the hypothesis that this strong interaction is the last one to be broken during the crystal desolvation and nucleation process.

Citation

Fucke, K., McIntyre, G. J., Lemee-Cailleay, M., Wilkinson, C., Edwards, A. J., Howard, J. A., & Steed, J. W. (2015). Insights into the Crystallisation Process from Anhydrous, Hydrated and Solvated Crystal Forms of Diatrizoic Acid. Chemistry - A European Journal, 21(3), 1036-1047. https://doi.org/10.1002/chem.201404693

Journal Article Type Article
Acceptance Date Nov 4, 2014
Online Publication Date Nov 4, 2014
Publication Date Jan 12, 2015
Deposit Date Dec 16, 2014
Publicly Available Date Mar 28, 2024
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 21
Issue 3
Pages 1036-1047
DOI https://doi.org/10.1002/chem.201404693
Keywords Crystallography, Halogen bonds, Lattice energy calculation, Neutron diffraction, Polymorphism.

Files

Accepted Journal Article (600 Kb)
PDF

Copyright Statement
This is the peer reviewed version of the following article: Fucke, K., McIntyre, G. J., Lemée-Cailleau, M.-H., Wilkinson, C., Edwards, A. J., Howard, J. A. K. and Steed, J. W. (2014), Insights into the Crystallisation Process from Anhydrous, Hydrated and Solvated Crystal Forms of Diatrizoic Acid. Chemistry - A European Journal, 21 (3): 1036-1047, which has been published in final form at http://dx.doi.org/10.1002/chem.201404693. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.





You might also like



Downloadable Citations