Alternative hydrogen bonding modes employed by a helical tubuland diol host molecule

Yue, Weimin, Nakano, Kazunori, Bishop, Roger, Craig, Donald C., Harris, Kenneth David Maclean ORCID: https://orcid.org/0000-0001-7855-8598 and Scudder, Marcia L. 2006. Alternative hydrogen bonding modes employed by a helical tubuland diol host molecule. CrystEngComm 8 (3) , pp. 250-256. 10.1039/b600651e

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Abstract

The racemic alicyclic diol 3 yields different types of hydrogen bonded inclusion structures depending on the recrystallisation solvent used. Non-protic guests are enclosed within parallel tubes through formation of the helical tubuland structure in chiral space group P3121 (or P3221). This arrangement contains the molecules of 3 surrounding threefold screw axes. Racemic hydrogen bonded 1 ∶ 1 co-crystalline adducts are formed in space group P21/c on crystallisation of 3 from mono-functional alcohols or carboxylic acids. In these, the alcohol molecules contribute one hydroxy group to an intermolecular pseudo-threefold screw arrangement with a O–HO–HO–H hydrogen bonded repeat unit, while the carboxylic acid groups participate in the closely-related O–HOC(R)–O–HO–H repeat unit. The carboxylic acid functionality thus behaves like an extended alcohol hydroxy group in these compounds. In contrast, crystallisation of 3 from ethane-1,2-diol yields a novel 4 ∶ 3 network compound in space group P. This material assembles using hydroxy group hydrogen bonded ladders and (O–H)6 cycles. The X-ray structures of these various materials are described and compared in crystal engineering terms.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1466-8033
Last Modified:	18 Oct 2022 13:25
URI:	https://orca.cardiff.ac.uk/id/eprint/13836

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