Research Article: Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea

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 [010].

Partial Text

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 ▶).




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