1-(1-Cyanocyclohexyl)-1-hydroxy-3-phenylurea

In the crystals of the title compound, C₁₄H₁₇N₃O₂, there are two molecules (A and B) in the asymmetric unit. The conformation of the hydroxamic acid moiety, O=C-N-O, is antiperiplanar for both molecules. The phenyl substituent is in a synperiplanar conformation, with O=C-N-C torsion angles of 1.8 (2) and 2.1 (2)° for A and B, respectively. The corresponding torsion angles of the cyclohexyl substituents are -32.0 (2) and -30.8 (2)°, respectively. The cyclohexyl ring adopts a chair conformation in both molecules A and B, with the hydroxamic acid moiety in an equatorial position and the cyano group in an axial position. The plane of the phenyl group is twisted with respect to the central urea plane [38.71 (7) and 43.08 (7)° for molecules A and B, respectively]. No other significant differences in bond lengths, angles or torsion angles between molecules A and B are observed. The crystal packing shows that the A and B molecules are interconnected by hydrogen bonds, OH...O and NH...N, in the direction of the a axis.

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