The diep-oxy monomer, C13H16O4 {DGE-Eu; systematic name: 2-[3-meth-oxy-4-(oxiran-2-ylmeth-oxy)benz-yl]oxirane}, was synthesized from eugenol by a three-step reaction. It consists of a 1,2,4-tris-ubstituted benzene ring substituted by diglycidyl ether, a meth-oxy group and a methyl-oxirane group. The three-membered oxirane rings are inclined to the benzene ring by 61.0 (3) and 27.9 (3)°. The methyl-ene C atom of one of the two terminal epoxide rings is positionally disordered [refined occupancy ratio = 0.69 (1):0.31 (1)]. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers parallel to the ab plane. The layers are linked by C-H⋯π inter-actions, forming a three-dimensional network.
Keywords: bio-based molecule; crystal structure; epoxy thermoset prepolymer; eugenol derivative; hydrogen bonding; oxirane.