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Issue 3, 2006
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Alternative hydrogen bonding modes employed by a helical tubuland diol host molecule

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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–H⋯O–H⋯O–H⋯ hydrogen bonded repeat unit, while the carboxylic acid groups participate in the closely-related ⋯O–H⋯O[double bond, length as m-dash]C(R)–O–H⋯O–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[1 with combining macron]. 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.

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

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Publication details

The article was received on 16 Jan 2006, accepted on 20 Feb 2006 and first published on 24 Feb 2006


Article type: Paper
DOI: 10.1039/B600651E
Citation: CrystEngComm, 2006,8, 250-256

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

    W. Yue, K. Nakano, R. Bishop, D. C. Craig, K. D. M. Harris and M. L. Scudder, CrystEngComm, 2006, 8, 250
    DOI: 10.1039/B600651E

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