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3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione
The title compound, C(11)H(13)N(3)S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3569223/ https://www.ncbi.nlm.nih.gov/pubmed/23424446 http://dx.doi.org/10.1107/S1600536812051276 |
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author | Karczmarzyk, Zbigniew Pitucha, Monika Wysocki, Waldemar Pachuta-Stec, Anna Stańczuk, Andrzej |
author_facet | Karczmarzyk, Zbigniew Pitucha, Monika Wysocki, Waldemar Pachuta-Stec, Anna Stańczuk, Andrzej |
author_sort | Karczmarzyk, Zbigniew |
collection | PubMed |
description | The title compound, C(11)H(13)N(3)S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intramolecular C—H⋯S contact. In the crystal, pairs of N—H⋯S hydrogen bonds link molecules into inversion dimers. π–π interactions are observed between the triazole and benzene rings, with centroid–centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively. |
format | Online Article Text |
id | pubmed-3569223 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35692232013-02-19 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione Karczmarzyk, Zbigniew Pitucha, Monika Wysocki, Waldemar Pachuta-Stec, Anna Stańczuk, Andrzej Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(11)H(13)N(3)S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intramolecular C—H⋯S contact. In the crystal, pairs of N—H⋯S hydrogen bonds link molecules into inversion dimers. π–π interactions are observed between the triazole and benzene rings, with centroid–centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively. International Union of Crystallography 2013-01-04 /pmc/articles/PMC3569223/ /pubmed/23424446 http://dx.doi.org/10.1107/S1600536812051276 Text en © Karczmarzyk et al. 2013 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 Karczmarzyk, Zbigniew Pitucha, Monika Wysocki, Waldemar Pachuta-Stec, Anna Stańczuk, Andrzej 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione |
title | 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione |
title_full | 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione |
title_fullStr | 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione |
title_full_unstemmed | 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione |
title_short | 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione |
title_sort | 3-benzyl-4-ethyl-1h-1,2,4-triazole-5(4h)-thione |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3569223/ https://www.ncbi.nlm.nih.gov/pubmed/23424446 http://dx.doi.org/10.1107/S1600536812051276 |
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