(E)-3-(2-Furyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

In the title molecule, C13H10O3, an intramolecular O—H⋯O hydrogen bond influences the molecular conformation, and the benzene and furan rings form a dihedral angle of 8.35 (7)°. Weak intermolecular C—H⋯O hydrogen bonds link molecules into sheets parallel to the bc plane.

In the title molecule, C 13 H 10 O 3 , an intramolecular O-HÁ Á ÁO hydrogen bond influences the molecular conformation, and the benzene and furan rings form a dihedral angle of 8.35 (7) . Weak intermolecular C-HÁ Á ÁO hydrogen bonds link molecules into sheets parallel to the bc plane.

Related literature
For a related crystal structure, see: Li et al. (1992).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis, we describe in this paper a user-friendly, solvent-free protocol for the synthesis of chalcones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, which can be considered as a a general method for the synthesis of chalcones, we obtained the title compound, (I). We present here its crystal structure.
In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in related compound (Li et al., 1992). The benzene and furan rings form a dihedral angle of 8.35 (7)°. In the crystal, weak intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to bc plane.

S3. Refinement
All H atoms were placed in geometrically idealized positions (O-H 0.85 Å, C-H 0.93 Å) and treated as riding, with The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.

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.