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Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea

The title compound, C(12)H(16)N(2)O(2)S, 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...

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Autores principales: Duque, J., Estévez, O., Jancik, V., Yee-Madeira, H.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979067/
https://www.ncbi.nlm.nih.gov/pubmed/21579158
http://dx.doi.org/10.1107/S1600536810013693
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author Duque, J.
Estévez, O.
Jancik, V.
Yee-Madeira, H.
author_facet Duque, J.
Estévez, O.
Jancik, V.
Yee-Madeira, H.
author_sort Duque, J.
collection PubMed
description The title compound, C(12)H(16)N(2)O(2)S, 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].
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spelling pubmed-29790672010-12-30 Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea Duque, J. Estévez, O. Jancik, V. Yee-Madeira, H. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(12)H(16)N(2)O(2)S, 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]. International Union of Crystallography 2010-04-17 /pmc/articles/PMC2979067/ /pubmed/21579158 http://dx.doi.org/10.1107/S1600536810013693 Text en © Duque et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Duque, J.
Estévez, O.
Jancik, V.
Yee-Madeira, H.
Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
title Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
title_full Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
title_fullStr Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
title_full_unstemmed Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
title_short Redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
title_sort redetermination of 1-cyclo­hexyl-3-(2-furo­yl)thio­urea
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979067/
https://www.ncbi.nlm.nih.gov/pubmed/21579158
http://dx.doi.org/10.1107/S1600536810013693
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