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5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole

The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal­ysed azide–alkyne cyclo­addition (CuAAC) from the corres­ponding n-octyne and 4-azido­benzoxadiazole. The benz­oxa­diazole and triazole rings show a roughly planar orien...

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Autores principales: Key, Jessie A., Cairo, Christopher W., Ferguson, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515233/
https://www.ncbi.nlm.nih.gov/pubmed/23284453
http://dx.doi.org/10.1107/S1600536812041815
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author Key, Jessie A.
Cairo, Christopher W.
Ferguson, Michael J.
author_facet Key, Jessie A.
Cairo, Christopher W.
Ferguson, Michael J.
author_sort Key, Jessie A.
collection PubMed
description The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal­ysed azide–alkyne cyclo­addition (CuAAC) from the corres­ponding n-octyne and 4-azido­benzoxadiazole. The benz­oxa­diazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C—H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking inter­actions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid–centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å.
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spelling pubmed-35152332013-01-02 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole Key, Jessie A. Cairo, Christopher W. Ferguson, Michael J. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal­ysed azide–alkyne cyclo­addition (CuAAC) from the corres­ponding n-octyne and 4-azido­benzoxadiazole. The benz­oxa­diazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C—H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking inter­actions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid–centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å. International Union of Crystallography 2012-10-13 /pmc/articles/PMC3515233/ /pubmed/23284453 http://dx.doi.org/10.1107/S1600536812041815 Text en © Key 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
Key, Jessie A.
Cairo, Christopher W.
Ferguson, Michael J.
5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
title 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
title_full 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
title_fullStr 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
title_full_unstemmed 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
title_short 5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
title_sort 5-(4-hexyl-1h-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515233/
https://www.ncbi.nlm.nih.gov/pubmed/23284453
http://dx.doi.org/10.1107/S1600536812041815
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