Received 15 December 2009
The title compound, C10H8O3, has been synthesized as part of our investigations into the generation of new antibacterial agents and serves as a building block for the synthesis of compound libraries. The compound crystallizes with two independent molecules in the asymmetric unit. The transoid propynyl ester groups are coplanar with the 2-hydroxybenzoate group with maximum deviations of -0.3507 (3) and 0.1591 (3) Å for the terminal carbons, with intramolecular O-HO hydrogen bonding providing rigidity to the structure and ensuring that the reactivity of the alkyne is not compromised by steric factors. The propynyl group forms intermolecular C-HO interactions with the phenolic O atom. Supramolecular chains along the b axis are found for both molecules with links by weak O-HO intermolecular interactions in the first independent molecule and C-HO interactions in the second.
For background to Cu(I)-mediated azide-alkyne cycloadditions, see: Houston et al. (2008); Wilkinson et al. (2009). For the biological use of salicylates, see: Sox & Olson (1989). For background to boric acid-mediated esterification, see: Houston et al. (2004, 2007); Levonis et al. (2007). For stereochemistry, see: Wilkinson et al. (2006); Wiberg & Laidig (1987). For previous synthesis of the title compound and its anti-tumour activity, see: Jung et al. (1997).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2601 ).
We acknowledge support of this work by Griffith University, the Queensland University of Technology, the Eskitis Institute for Cell and Molecular Therapies, and the Institute for Glycomics.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Houston, T. A., Levonis, S. M. & Kiefel, M. J. (2007). Aust. J. Chem. 60, 811-815.
Houston, T. A., Quader, S., Boyd, S. E., Jenkins, I. D. & Healy, P. C. (2008). Acta Cryst. E64, o1738.
Houston, T. A., Wilkinson, B. L. & Blanchfield, J. T. (2004). Org. Lett. 6, 678-681.
Jung, M., Kerr, D. E. & Senter, P. D. (1997). Archiv. Der Pharm. 330, 173-176.
Levonis, S. M., Bornaghi, L. F. & Houston, T. A. (2007). Aust. J. Chem. 60, 821-823.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sox, T. E. & Olson, C. A. (1989). Antimicrob. Agents Chemother. 33, 2075-2082.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). publCIF. In preparation.
Wiberg, K. B. & Laidig, K. E. (1987). J. Am. Chem. Soc. 109, 5935-5943.
Wilkinson, B. L., Bornaghi, L. F., Houston, T. A. & Poulsen, S.-A. (2009). Click Chemistry in Carbohydrate Based Drug Development and Glycobiology: An Update in Glycobiology Research Trends, edited by G. Powell & O. McCabe, pp. 127-172. New York: Nova Science Publishers.
Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Poulsen, S.-A. & White, A. R. (2006). Acta Cryst. E62, o5065-o5067.