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], 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 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. [ABSTRACT FROM AUTHOR]