Crystal structure of De-hydro-dieugenol B methyl ether, a neolignan from Nectandra leucantha Nees and Mart (Lauraceae)

Abstract

In the title compound, C₂₁H₂₄O₄ (systematic name: 4,5'-diallyl-2,2',3'-tri-meth-oxy-diphenyl ether), the aromatic rings lie almost perpendicular to each other [dihedral angle = 85.96 (2)°]. The allyl side chains show similar configurations, with C_ar-C-C=C (ar = aromatic) torsion angles of -123.62 (12) and -115.54 (12)°. A possible weak intra-molecular C-H⋯O inter-action is observed. In the crystal, mol-ecules are connected by two C-H⋯O hydrogen bonds, forming undulating layers lying parallel to the bc plane. Weak C-H⋯π and π-π stacking inter-actions also occur.

Keywords: crystal structure; eugenol; neolignan.

Figure 1

Structure of the title compound in the crystal. Displacement ellipsoids represent 50% probability levels. One hydrogen atom is obscured at each of the atoms C17 and C19.

Figure 2

Packing diagram of the title compound viewed perpendicular to the bc plane. For clarity, the allyl side chains and all hydrogen atoms not involved in hydrogen bonding (dashed lines, see Table 2 ▸) have been omitted.