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Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione

The title compound, C(20)H(21)NO(2), an example of a stable 1,2-naphtho­quinone, was determined by single-crystal X-ray diffraction analysis at 100 K. This structure illustrates steric buttressing of the adamantanyl group, forcing the N—H group into the coplanar aromatic C—H. The presence of strong...

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Autores principales: Lamoureux, Guy, Alvarado-Rojas, Mónica, Pineda, Leslie W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6323878/
https://www.ncbi.nlm.nih.gov/pubmed/30713743
http://dx.doi.org/10.1107/S2056989018017917
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author Lamoureux, Guy
Alvarado-Rojas, Mónica
Pineda, Leslie W.
author_facet Lamoureux, Guy
Alvarado-Rojas, Mónica
Pineda, Leslie W.
author_sort Lamoureux, Guy
collection PubMed
description The title compound, C(20)H(21)NO(2), an example of a stable 1,2-naphtho­quinone, was determined by single-crystal X-ray diffraction analysis at 100 K. This structure illustrates steric buttressing of the adamantanyl group, forcing the N—H group into the coplanar aromatic C—H. The presence of strong delocalization between the planar N atom at the 4-position and the carbonyl group at the 2-position is indicated. In the crystal, C—H⋯O and C—H⋯π inter­actions link the mol­ecules into a three-dimensional network.
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spelling pubmed-63238782019-02-01 Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione Lamoureux, Guy Alvarado-Rojas, Mónica Pineda, Leslie W. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(20)H(21)NO(2), an example of a stable 1,2-naphtho­quinone, was determined by single-crystal X-ray diffraction analysis at 100 K. This structure illustrates steric buttressing of the adamantanyl group, forcing the N—H group into the coplanar aromatic C—H. The presence of strong delocalization between the planar N atom at the 4-position and the carbonyl group at the 2-position is indicated. In the crystal, C—H⋯O and C—H⋯π inter­actions link the mol­ecules into a three-dimensional network. International Union of Crystallography 2019-01-01 /pmc/articles/PMC6323878/ /pubmed/30713743 http://dx.doi.org/10.1107/S2056989018017917 Text en © Lamoureux et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Lamoureux, Guy
Alvarado-Rojas, Mónica
Pineda, Leslie W.
Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
title Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
title_full Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
title_fullStr Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
title_full_unstemmed Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
title_short Crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
title_sort crystal structure of 4-[(adamantan-1-yl)amino]­naphthalene-1,2-dione
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6323878/
https://www.ncbi.nlm.nih.gov/pubmed/30713743
http://dx.doi.org/10.1107/S2056989018017917
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