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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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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. |
format | Text |
id | pubmed-2979536 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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