Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 10-benzyl-9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

Abstract

In the fused ring system of the title compound, C32H37NO4, the central dihydropyridine ring adopts a flattened boat conformation, the mean and maximum deviations of the dihydropyridine ring being 0.1429 (2) and 0.2621 (2) Å, respectively. The two cyclohexenone rings adopt envelope conformations with the tetrasubstituted C atoms as flap atoms. The benzene and phenyl rings form dihedral angles of 85.81 (2) and 88.90 (2)°, respectively, with the mean plane of the dihydropyridine ring. In the crystal, molecules are linked via an O—H...O hydrogen bond, forming a helical chain along the b-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (65.2%), O...H/H...O (18.8%) and C...H/H...C (13.9%) contacts. Quantum chemical calculations for the frontier molecular orbitals were undertake to determine the chemical reactivity of the title compound.

Keywords

• crystal structure
• dimedone
• benzylamine
• acridinedione