Crystal structure of 2-cyano-N-(furan-2-ylmethyl)-3-(3-nitrophenyl)propanamide

In the title compound, C15H11N3O4, the acetamide group is inclined to the furan ring by 66.5 (1)°. The dihedral angle between the furan ring and the benzene ring is 66.8 (1)°. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(12) ring motif. The dimers are linked via two pairs of C—H⋯O hydrogen bonds to the same acceptor oxygen atom, enclosing R 2 1(6) ring motifs, forming chains along the [101] direction.


S1. Comment
Furan is one of the most important five-membered heterocyclic ring systems and its derivatives are well known to possess various biological properties, such as antibacterial, antitumor, anti-inflammatory, antifungal, anticonvulsant, and analgesic (Anupam et al., 2011). Acetamide derivatives possess a wide range of pharmacological properties (Fallah-Tafti et al., 2011;Shams et al., 2011). In view of the biological importance of furan and acetamide derivatives, we have synthesized the title compound and report herein on its crystal structure.
In the crystal (Table 1 and

S2. Experimental
An equimolar mixture of furfuryl amine and ethyl cyano acetate was mixed in a conical flask and the mixture was heated under microwave irradiation at 700 W for 3 min with an interval of 20 s each time. The mixture was then poured into a beaker and cooled giving a solid that was washed with ethanol. The furfuryl cyano acetamide product so obtained was treated with an equi-molar ratio of 3-nitro benzaldehyde in the presence of glacial acetic acid and refluxed for 3 h. On cooling, colourless crystals of the title compound were obtained.

S3. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

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.