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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...

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Autores principales: Karczmarzyk, Zbigniew, Pitucha, Monika, Wysocki, Waldemar, Pachuta-Stec, Anna, Stańczuk, Andrzej
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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