Crystal structure and Hirshfeld surface analysis of 4-allyl-2-meth-oxy-6-nitro-phenol.

Abstract

The title compound, synthesized by nitration of eugenol (4-allyl-2-methoxyphenol) using a nitric acid/sulfuric acid mixture, has an asymmetric unit comprising three geometrically similar independent molecules. Intramolecular hydrogen bonding between the hydroxyl and nitro groups generates an S(6) ring motif in each molecule. Crystal cohesion is maintained through intermolecular C-H···O hydrogen bonds and π-π stacking interactions between aromatic rings, with centroid-to-centroid distances ranging from 3.6583(17) to 4.0624(16) Å. Hirshfeld surface analysis combined with two-dimensional fingerprint plots identifies H···H (39.6%), O···H/H···O (37.7%), C···H/H···C (12.5%), and C···C (4.0%) contacts as the dominant contributors to crystal packing.