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2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine

In the title compound, C(15)H(15)N(5)O, the benzene and pyridine rings make a dihedral angle of 30.86 (7)°. In the crystal, chains of mol­ecules are wrapped around the screw axes into compressed helices, through hydrogen bonding between the hy­droxy and cyano groups. The chains are linked by weak C—...

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Detalles Bibliográficos
Autores principales: Centore, Roberto, Piccialli, Vincenzo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515185/
https://www.ncbi.nlm.nih.gov/pubmed/23284412
http://dx.doi.org/10.1107/S1600536812041396
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author Centore, Roberto
Piccialli, Vincenzo
author_facet Centore, Roberto
Piccialli, Vincenzo
author_sort Centore, Roberto
collection PubMed
description In the title compound, C(15)H(15)N(5)O, the benzene and pyridine rings make a dihedral angle of 30.86 (7)°. In the crystal, chains of mol­ecules are wrapped around the screw axes into compressed helices, through hydrogen bonding between the hy­droxy and cyano groups. The chains are linked by weak C—H⋯N and C—H⋯O inter­actions. The π conjugated unit of the mol­ecule is almost perpendicular to the helix axis, and the formation of the helix is allowed by a gauche-type torsion angle in the hy­droxy­ethyl tail. In this way, consecutive chromophore units along the chain are placed in a strict anti­parallel arrangement, and this is energetically favoured because of the high dipole moment of the mol­ecule.
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spelling pubmed-35151852013-01-02 2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine Centore, Roberto Piccialli, Vincenzo Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(15)H(15)N(5)O, the benzene and pyridine rings make a dihedral angle of 30.86 (7)°. In the crystal, chains of mol­ecules are wrapped around the screw axes into compressed helices, through hydrogen bonding between the hy­droxy and cyano groups. The chains are linked by weak C—H⋯N and C—H⋯O inter­actions. The π conjugated unit of the mol­ecule is almost perpendicular to the helix axis, and the formation of the helix is allowed by a gauche-type torsion angle in the hy­droxy­ethyl tail. In this way, consecutive chromophore units along the chain are placed in a strict anti­parallel arrangement, and this is energetically favoured because of the high dipole moment of the mol­ecule. International Union of Crystallography 2012-10-06 /pmc/articles/PMC3515185/ /pubmed/23284412 http://dx.doi.org/10.1107/S1600536812041396 Text en © Centore and Piccialli 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
Centore, Roberto
Piccialli, Vincenzo
2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
title 2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
title_full 2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
title_fullStr 2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
title_full_unstemmed 2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
title_short 2-Cyano-5-({4-[N-methyl-N-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
title_sort 2-cyano-5-({4-[n-methyl-n-(2-hy­droxy­eth­yl)amino] phen­yl}diazen­yl)pyridine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515185/
https://www.ncbi.nlm.nih.gov/pubmed/23284412
http://dx.doi.org/10.1107/S1600536812041396
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