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N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide

In the title compound, C(21)H(20)N(2)O(3), the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 Å). The carboximide N atom and the five C atoms of the 2-methyl­prop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009 Å), which subtends an angle of 84...

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Detalles Bibliográficos
Autores principales: Hanton, Lyall R., Moratti, Stephen C., Shi, Zheng, Simpson, Jim
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979536/
https://www.ncbi.nlm.nih.gov/pubmed/21579543
http://dx.doi.org/10.1107/S1600536810018994
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author Hanton, Lyall R.
Moratti, Stephen C.
Shi, Zheng
Simpson, Jim
author_facet Hanton, Lyall R.
Moratti, Stephen C.
Shi, Zheng
Simpson, Jim
author_sort Hanton, Lyall R.
collection PubMed
description In the title compound, C(21)H(20)N(2)O(3), the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 Å). The carboximide N atom and the five C atoms of the 2-methyl­prop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009 Å), which subtends an angle of 84.34 (7)° to the naphthalamide plane. This orients the =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the mol­ecule an extended configuration. The piperidine ring adopts a chair conformation and there is evidence for some delocalization between the naphthalene and piperidine units, the C—N(pip) bond length being 1.404 (4) Å. In the crystal structure, π–π contacts with centroid–centroid distances of 3.5351 (18) and 3.7794 (18) Å supported by C—H⋯O hydrogen bonds link adjacent mol­ecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C—H⋯O contacts of varying strength, which stack the mol­ecules down the b axis.
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spelling pubmed-29795362010-12-30 N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide Hanton, Lyall R. Moratti, Stephen C. Shi, Zheng Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(21)H(20)N(2)O(3), the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 Å). The carboximide N atom and the five C atoms of the 2-methyl­prop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009 Å), which subtends an angle of 84.34 (7)° to the naphthalamide plane. This orients the =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the mol­ecule an extended configuration. The piperidine ring adopts a chair conformation and there is evidence for some delocalization between the naphthalene and piperidine units, the C—N(pip) bond length being 1.404 (4) Å. In the crystal structure, π–π contacts with centroid–centroid distances of 3.5351 (18) and 3.7794 (18) Å supported by C—H⋯O hydrogen bonds link adjacent mol­ecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C—H⋯O contacts of varying strength, which stack the mol­ecules down the b axis. International Union of Crystallography 2010-05-29 /pmc/articles/PMC2979536/ /pubmed/21579543 http://dx.doi.org/10.1107/S1600536810018994 Text en © Hanton et al. 2010 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
Hanton, Lyall R.
Moratti, Stephen C.
Shi, Zheng
Simpson, Jim
N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
title N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
title_full N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
title_fullStr N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
title_full_unstemmed N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
title_short N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
title_sort n-methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979536/
https://www.ncbi.nlm.nih.gov/pubmed/21579543
http://dx.doi.org/10.1107/S1600536810018994
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