Received 16 November 2012
The asymmetric unit of the title compound, C10H8O3, contains two independent molecules, both of which are almost planar (r.m.s deviations for all non-H atoms of 0.044 and 0.053 Å). The dihedral angles between the benzene ring and the prop-1-yne group are 3.47 (1) and 3.07 (1)° in the two molecules, and the prop-1-yne groups adopt extended conformations. In each molecule, an intramolecular O-HO hydrogen bond involving the OH and aldehyde substituents forms an S(6) ring. In the crystal, molecules are linked into cyclic centrosymmetric dimers via C-HO hydrogen bonds, generating R22(14) ring motifs. The crystal structure is further stabilized by aromatic - stacking interactions between the benzene rings [centroid-centroid distances = 3.813 (2) and 3.843 (2) Å]
For the biological activity of benzaldehyde derivatives, see: Zhao et al. (2007); Ley & Bertram (2001); Delogu et al. (2010). For a related structure see: Esakkiammal et al. (2012). For standard bond lengths, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5285 ).
VS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the UGC SAP for the facilities provided to the department.
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