Acta Crystallographica Section B

Structural Science

Volume 59, Part 1 (February 2003)

research papers

Acta Cryst. (2003). B59, 118-131 [ doi:10.1107/S0108768102022358 ]

(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines

C. M. Zakaria, G. Ferguson, A. J. Lough and C. Glidewell

Abstract: (1R,3S)-Camphoric acid [(1R,3S)-1,2,2,-trimethylcyclopentane-1,3-dicarboxylic acid, C₁₀H₁₆O₄] forms adducts with a range of amines in which the acid component may be the neutral molecule, the mono-anion (C₁₀H₁₅O₄)^- or the di-anion (C₁₀H₁₄O₄)^2-. The structures generated by the hard hydrogen bonds take the form of chains in the 1:1 adducts (II) and (III) formed with 4,4'-bipyridyl and 1,2-bis(4-pyridyl)ethane. There are single sheets in the hydrated 1:1 adduct (IV) formed with 1,4-diazabicyclo[2.2.2]octane, and pairwise-interwoven sheets in the 2:1 adduct (V) formed with hexamethylenetetramine. Three-dimensional frameworks are present in the salt-like 1:1 adduct (VI) formed with piperazine and in the hydrated 3:1 adduct (VII) formed with N,N'-dimethylpiperazine. This latter adduct contains both neutral C₁₀H₁₆O₄ and anionic (C₁₀H₁₅O₄)^- units. In (II), (III) and (IV), the chain and sheet substructures are linked by C-HO hydrogen bonds to form three-dimensional frameworks. The monoclinic polymorph of camphoric acid itself (I) has been reinvestigated.

Keywords: camphoric acid; amines; hydrogen bonding.


	Structure factor file (CIF format) (128.1 kbytes) Contains datablock I

	Structure factor file (CIF format) (54.7 kbytes) Contains datablock II

	Structure factor file (CIF format) (550.5 kbytes) Contains datablock III

	Structure factor file (CIF format) (87.1 kbytes) Contains datablock IV

	Structure factor file (CIF format) (91.9 kbytes) Contains datablock V

	Structure factor file (CIF format) (87.5 kbytes) Contains datablock VI

	Structure factor file (CIF format) (103.1 kbytes) Contains datablock VII

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