Date Published: May 01, 2010
Publisher: International Union of Crystallography
Author(s): Sohail Saeed, Naghmana Rashid, Wing-Tak Wong.
In the title compound, C14H17N3O3S, the nitro group is twisted slightly by 2.6 (3)° from the benzene ring plane and the thioureido group makes a dihedral angle of 52.06 (4)° with the benzene ring. The cyclohexyl ring displays a chair conformation. An intramolecular N—H⋯O interaction is present. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers. π–π interactions between inversion-related benzene rings (centroid–centroid distance = 4.044 Å) and C—H⋯π interactions (H⋯centroid distance = 3.116 Å) between one methylene cyclohexyl H atom and the benzene ring are also present.
For general background to the chemistry and biological activity of thiourea derivatives and their use as organic synthons or as complexing agents, see: Glasser & Doughty (1964 ▶); Jain & Rao (2003 ▶); Zeng et al. (2003 ▶); Xu et al. (2004 ▶); Zheng et al. (2004 ▶); D’hooghe et al. (2005 ▶); Saeed et al. (2008 ▶, 2009 ▶, 2010 ▶).