Date Published: May 01, 2010
Publisher: International Union of Crystallography
Author(s): J. Duque, O. Estévez, V. Jancik, H. Yee-Madeira.
The title compound, C12H16N2O2S, was synthesized from furoyl isothiocyanate and cyclohexylamine in dry acetone, and the crystal structure redetermined. The thiourea group is in the thioamide form. The structure [Otazo-Sánchez et al. (2001 ▶). J. Chem. Soc. Perkin Trans. 2, pp. 2211–2218] has been redetermined in order to establish the intra- and intermolecular interactions. The trans–cis geometry of the thiourea group is stabilized by intramolecular hydrogen bonding between the carbonyl and cis-thioamide groups, resulting in a pseudo-S(6) planar ring which makes a dihedral angle of 3.24 (6)° with the 2-furoyl group and a torsion angle of −84.3 (2)° with the cyclohexyl group. There is also an intramolecular hydrogen bond between the furan O atom and the other thioamide H atom. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds, forming chains along .
For general background to the applications of aroylthioureas in coordination chemistry and molecular electronics, see: Aly et al. (2007 ▶); Koch (2001 ▶); Duque et al. (2009 ▶); Estévez-Hernández et al. (2006 ▶). For related structures, see: Estévez-Hernández et al. (2008 ▶). For the synthesis, see: Otazo-Sánchez et al. (2001 ▶).