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

ABSTRACT: Lapachol acetate [systematic name: 3-(3-methyl-but-2-en-yl)-1,4-dioxonaph-thalen-2-yl acetate], C₁₇H₁₆O₄, 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 mol-ecule is reported. The mol-ecular conformation shows little difference with other lapachol derivatives and lapachol itself. The packing is directed by inter-molecular ?-? and C-H?O inter-actions, as described by Hirshfeld surface analysis. The former inter-actions make the largest contributions to the total packing energy in a ratio of 2:1 with respect to the latter.

SUBMITTER: Martinez-Cabrera MA

PROVIDER: S-EPMC6727062 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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

Martínez-Cabrera Miguel A MA Macías Mario A MA Ferreira Francisco F Pandolfi Enrique E Barúa Javier J Suescun Leopoldo L

Acta crystallographica. Section E, Crystallographic communications 20190819 Pt 9

Lapachol acetate [systematic name: 3-(3-methyl-but-2-en-yl)-1,4-dioxonaph-thalen-2-yl acetate], C17H16O4, 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 mol-ecule is reported. The mol-ecular conformation shows little difference with other lapachol derivatives and lapachol itself. The packing is directed by inter-molecular ...[more]

PMID: 31523467

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