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2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile

The title compound, C(19)H(17)ClN(4), was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropyl­amide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The...

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Autores principales: Wolińska, Ewa, Karczmarzyk, Zbigniew, Rykowski, Andrzej, Urbańczyk-Lipkowska, Zofia, Kalicki, Przemysław
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379491/
https://www.ncbi.nlm.nih.gov/pubmed/22719689
http://dx.doi.org/10.1107/S1600536812023252
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author Wolińska, Ewa
Karczmarzyk, Zbigniew
Rykowski, Andrzej
Urbańczyk-Lipkowska, Zofia
Kalicki, Przemysław
author_facet Wolińska, Ewa
Karczmarzyk, Zbigniew
Rykowski, Andrzej
Urbańczyk-Lipkowska, Zofia
Kalicki, Przemysław
author_sort Wolińska, Ewa
collection PubMed
description The title compound, C(19)H(17)ClN(4), was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropyl­amide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intra­molecular C—H⋯N inter­actions occur. In the crystal, mol­ecules related by a c-glide plane are linked into zigzag chains along [001] by N—H⋯N hydrogen bonds.
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spelling pubmed-33794912012-06-20 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile Wolińska, Ewa Karczmarzyk, Zbigniew Rykowski, Andrzej Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(17)ClN(4), was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropyl­amide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intra­molecular C—H⋯N inter­actions occur. In the crystal, mol­ecules related by a c-glide plane are linked into zigzag chains along [001] by N—H⋯N hydrogen bonds. International Union of Crystallography 2012-05-31 /pmc/articles/PMC3379491/ /pubmed/22719689 http://dx.doi.org/10.1107/S1600536812023252 Text en © Wolińska et al. 2012 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
Wolińska, Ewa
Karczmarzyk, Zbigniew
Rykowski, Andrzej
Urbańczyk-Lipkowska, Zofia
Kalicki, Przemysław
2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
title 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
title_full 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
title_fullStr 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
title_full_unstemmed 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
title_short 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
title_sort 2-(3-chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379491/
https://www.ncbi.nlm.nih.gov/pubmed/22719689
http://dx.doi.org/10.1107/S1600536812023252
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