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

Acta Crystallogr E Crystallogr Commun. 2019 Aug 19;75(Pt 9):1362-1366. doi: 10.1107/S2056989019011393. eCollection 2019 Sep 1.

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 π-π 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.

Keywords: Hirshfeld analysis; crystal structure; lapachol acetate; naphtho­quinone; synthesis.