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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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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]. |
format | Text |
id | pubmed-2979067 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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