1-{2-Hydroxy-6-[3-(pyrrol-1-yl)propoxy]phenyl}ethanone

In the title compound, C15H17NO3, the mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7)°. The molecule contains an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯π interactions link the molecules into chains along [010].

In the title compound, C 15 H 17 NO 3 , the mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7) . The molecule contains an intramolecular O-HÁ Á ÁO hydrogen bond. In the crystal, weak C-HÁ Á Á interactions link the molecules into chains along [010].

Comment
The synthesis of new derivatives containing both a pyrrole ring and salicyaldehyde moiety is of a great interest since they are currently used as precursors for chelating agents especially those of Schiff bases (Wu et al., 2003;Saraswat et al., 2006) and oximes (Smith et al., 2003;Dong et al., 2010). These compounds may also be involved in the elaboration of modified electrodes by anodic (Deronzier & Moutet, 1996) or by chemical oxidation (MacDearmid et al., 2001). These types of materials can be applied in catalysis, electrocatalysis and sensors (Srinivasan et al., 1986;Coche-Guerente et al., 1995;Ourari et al., 2008). The synthesis of new salicylaldehyde derivatives containing electropolymerizable units can be considered as the main source of a functionalized conducting π-conjugated polymers such as as those of polypyrrole and polyaniline (Khedkar et al., 1997;Huo et al., 1999).
We report herein the crystal structure of the title compound. The molecular structure is shown in Fig. 1. The mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7)°. There is an intramolecular O-H···O hydrogen bond present. In the crystal, there are weak C-H···π interactions (Table 1)

Experimental
A solution of 152 mg (1 mmol) of 2,6-dihydroxyacetophenone was added to a solution containing 187 mg (1 mmol) of 1bromopropyl-3-N-pyrrol and 181 mg (1.7 mmol) of potassium carbonate under argon atmosphere. The mixture was refluxed for 45 h and was allowed to stand at room temperature. After extraction by dichloromethane and purification by chromatography on silica gel using dichloromethane as eluent. Thus, 153 mg of pure compound (I) was recovered, corresponding to the yield of 59%. The suitable single crystals were then obtained from dichloromethane solution by slow evaporation.

Refinement
H atoms were located in difference Fourier maps but introduced in calculated positions and treated as riding on their parent atoms (C) with C-H = 0.96 Å (methyl), 0.97 Å (methylene) or 0.93 Å (aromatic) with U iso (H) = 1.2U eq (C aromatic and C methylene ) or U iso (H) = 1.5U eq (C methyl ). Atom H3 was located in a difference Fourier map and refined with U iso (H) =  The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Figure 2
The packing showing weak C-H···π interactions involving the centroid (in pink) of the pyrrole ring as dashed lines.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.