Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis

Lapachol acetate [systematic name: 3-(3-methyl­but-2-en­yl)-1,4-dioxonaph­thalen-2-yl acetate], C(17)H(16)O(4), was prepared using a modified high-yield procedure and its crystal structure is reported for the first time 80 years after its first synthesis. The full spectroscopic characterization of t...

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Autores principales: Martínez-Cabrera, Miguel A., Macías, Mario A., Ferreira, Francisco, Pandolfi, Enrique, Barúa, Javier, Suescun, Leopoldo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6727062/
https://www.ncbi.nlm.nih.gov/pubmed/31523467
http://dx.doi.org/10.1107/S2056989019011393
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author Martínez-Cabrera, Miguel A.
Macías, Mario A.
Ferreira, Francisco
Pandolfi, Enrique
Barúa, Javier
Suescun, Leopoldo
author_facet Martínez-Cabrera, Miguel A.
Macías, Mario A.
Ferreira, Francisco
Pandolfi, Enrique
Barúa, Javier
Suescun, Leopoldo
author_sort Martínez-Cabrera, Miguel A.
collection PubMed
description Lapachol acetate [systematic name: 3-(3-methyl­but-2-en­yl)-1,4-dioxonaph­thalen-2-yl acetate], C(17)H(16)O(4), was prepared using a modified high-yield procedure and its crystal structure is reported for the first time 80 years after its first synthesis. The full spectroscopic characterization of the mol­ecule is reported. The mol­ecular conformation shows little difference with other lapachol derivatives and lapachol itself. The packing is directed by inter­molecular π–π and C—H⋯O inter­actions, as described by Hirshfeld surface analysis. The former inter­actions make the largest contributions to the total packing energy in a ratio of 2:1 with respect to the latter.
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spelling pubmed-67270622019-09-13 Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis Martínez-Cabrera, Miguel A. Macías, Mario A. Ferreira, Francisco Pandolfi, Enrique Barúa, Javier Suescun, Leopoldo Acta Crystallogr E Crystallogr Commun Research Communications Lapachol acetate [systematic name: 3-(3-methyl­but-2-en­yl)-1,4-dioxonaph­thalen-2-yl acetate], C(17)H(16)O(4), was prepared using a modified high-yield procedure and its crystal structure is reported for the first time 80 years after its first synthesis. The full spectroscopic characterization of the mol­ecule is reported. The mol­ecular conformation shows little difference with other lapachol derivatives and lapachol itself. The packing is directed by inter­molecular π–π and C—H⋯O inter­actions, as described by Hirshfeld surface analysis. The former inter­actions make the largest contributions to the total packing energy in a ratio of 2:1 with respect to the latter. International Union of Crystallography 2019-08-19 /pmc/articles/PMC6727062/ /pubmed/31523467 http://dx.doi.org/10.1107/S2056989019011393 Text en © Martínez-Cabrera 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
Martínez-Cabrera, Miguel A.
Macías, Mario A.
Ferreira, Francisco
Pandolfi, Enrique
Barúa, Javier
Suescun, Leopoldo
Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
title Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
title_full Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
title_fullStr Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
title_short Crystal structure and Hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
title_sort crystal structure and hirshfeld surface analysis of lapachol acetate 80 years after its first synthesis
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6727062/
https://www.ncbi.nlm.nih.gov/pubmed/31523467
http://dx.doi.org/10.1107/S2056989019011393
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