Abstract
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].
Highlights
Related literature 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); EstevezHernandez et al (2006)
The thiourea group is in the thioamide form
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 À84.3 (2) with the cyclohexyl group
Summary
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-Sanchez et al (2001). 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 À84.3 (2) with the cyclohexyl group. There is an intramolecular hydrogen bond between the furan O atom and the other thioamide H atom. Molecules are linked by intermolecular N—HÁ Á ÁO hydrogen bonds, forming chains along [010].
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