Polymorphism and hydrogen bonding in cinchomeronic acid: a variable temperature experimental and computational study

Evans, Ivana Radosavljevic; Howard, Judith A.K.; Evans, John S.O.; Postlethwaite, Stella R.; Johnson, Mark R.

Abstract

3,4-Pyridinedicarboxylic acid is a compound commonly used as a multifunctional ligand in coordination chemistry. The crystal structure of its orthorhombic Form I has been known for over 30 years, while a new Form II has only been reported recently as crystallizing in the monoclinic space groupC2/c. The present work shows that, in its entire temperature stability range, Form II is in fact primitive monoclinic, with space groupP21/c. At 120 K, the unit cell parameters are a = 7.594(1) Å, b = 7.332(1) Å, c = 12.113(2) Å, β = 104.339(4)° and V = 653.4(2) Å3. In order to characterize the temperature dependent behaviour of 3,4-pyridinedicarboxylic acid, both polymorphs were studied by single crystal X-ray diffraction at 120 and 400 K, variable temperature powder X-ray diffraction between room temperature and 600 K, solid state NMR and computational methods. Short O–H⋯O hydrogen bonds are found in both forms of 3,4-pyridinedicarboxylic acid, but there appears to be no temperature-induced proton migration along these bonds.

Citation

Evans, I. R., Howard, J. A., Evans, J. S., Postlethwaite, S. R., & Johnson, M. R. (2008). Polymorphism and hydrogen bonding in cinchomeronic acid: a variable temperature experimental and computational study. CrystEngComm, 10(10), 1404-1409. https://doi.org/10.1039/b807015f

• Journal Article Type: Article
• Acceptance Date: Jun 12, 2008
• Online Publication Date: Jul 31, 2008
• Publication Date: 2008
• Deposit Date: May 6, 2013
• Journal: CrystEngComm
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 10
• Issue: 10
• Pages: 1404-1409
• DOI: https://doi.org/10.1039/b807015f