3-(3-Cyanophenyl)-N-phenyloxirane-2-carboxamide

In the title compound, C16H12N2O2, both terminal benzene rings are located at the same side of the central epoxide ring, showing a cis conformation. The epoxide ring makes dihedral angles of 76.59 (10) and 62.40 (11)° with the phenyl and cyanophenyl rings, respectively. Intermolecular N—H⋯O and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Selective ring opening reactions of oxiranes also provide powerful and efficient routes to a variety of useful compounds including 2,3-epoxyketone (Meth-Cohn et al., 1999), aziridinecarboxylate (Thijs et al., 1990). Various effective systems have been developed over the years for the preparation of chiral epoxides. As a part of our interest in the synthsis of epoxides ring systems (Chen & Kang, 2009a,b;He, 2009, He et al. (2009), we synthesis the title compound by using Darzens reaction.
We report herein the crystal structure of the title compound.
The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The cyanophenyl ring and N-phenylformamide units adopts a cis conformation with respect to the epoxides ring, the dihedral angle between the two phenyl ring is 84.75 (6)°. Epoxide ring makes dihedral angles of 76.59 (10)° and 62.40 (11)° with phenyl rings C1-C6 and C10-C15, respectively. The crystal packing is stabilized by C-H···O and N-H···O hydrogen bonding (Table 1).
Experimental 2-Chloro-N-phenylacetamide (0.17 g, 1.0 mmol) and sodium ethanolate (0.14 g, 2.0 mmol) were dissolved in acetonitrile (2 ml). To the solution was added 3-formylbenzonitrile (0.131 g, 1.0 mmol) at 298 K, the solution was stirred for 60 min and removal of solvent under reduced pressure, the residue was purified through column chromatography on silica gel to give compound (I). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.02 g) in ethyl acetate (2 ml) and evaporating the solvent slowly at room temperature for about 1 d.

Refinement
H atoms were placed in calculated positions, with C-H = 0.93-0.98 Å, and N-H = 0.86 Å, and refined using a riding model with U iso (H) = 1.2U eq (C,N). As no significant anomalous scattering, Friedel pairs were merged. Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).