(S)-2-(1H-Imidazol-1-yl)-3-phenylpropanol

In the title compound, C12H14N2O, the middle C atom in the propanol chain is a chiral center and possesses an S absolute configuration, according to the synthesis. In the crystal structure, intermolecular O—H⋯N hydrogen bonds link the molecules into a chain along the b axis.

In the title compound, C 12 H 14 N 2 O, the middle C atom in the propanol chain is a chiral center and possesses an S absolute configuration, according to the synthesis. In the crystal structure, intermolecular O-HÁ Á ÁN hydrogen bonds link the molecules into a chain along the b axis.   Table 1 Hydrogen-bond geometry (Å , ).

Comment
Imidazoles are an important group in biological systems, and their derivatives have attracted widespread interest due to their application as precursors for imidazolium-based ionic liquids (Baudequin et al., 2003), N-heterocyclic carbenes (Nair et al., 2004) and molecular sensors (Sambrook et al., 2005). We have focused our interest on the synthesis and applications of imidazole derivatives (Lan et al., 2004;Wang et al., 2007) and have reported several chiral cyclophanes and chiral molecular tweezers containing imidazole residues as receptors for the enantioselective recognition of amino acids or their derivatives (You et al., 2001). Here, we report the crystal structure of the title compound, (I), which is a basic unit in the construction of chiral receptors and could be applied in the preparation of chair heterocyclic carbenes and ionic liquids.
In the structure of (I), the hydroxyl group and the imidazol-1-yl nitrogen atom are hydrogen bonded via an intermolecular O-H···N hydrogen bond as illustrated in Table 1 to result in the formation of a helical chain.

Experimental
Since enantiopure amines are easily available and the chiral carbon has little risk of the racemization, they are usually applied for the preparation of chiral imidazole derivatives by cyclocondensation of ring fragments (Matsuoka et al., 2006).

Refinement
All H atoms were positioned geometrically and refined in the riding model approximation with C-H = 0.93, 0.97 Å and O-H = 0.82 Å. Since there is no atom heavier than oxygen it was not possible to determine the absolute structure exactly.
However, the chiral carbon does not directly participate in the cyclocondensation in this reaction (Matsuoka et al., 2006).

Special details
Experimental. In the crystal structure, there is not any heavy atom than silicon, so we can't get the absolute structure exactly.