Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 10-benzyl-9-(4-hydroxy-3-methoxyphenyl)-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 molecule, C31H35NO4, the conformation of the central dihydropyridine ring is intermediate between boat and envelope with the N and the opposite C atoms lying out of the basal plane. The conformations of terminal rings are close to envelope, with the atoms substituted by two methyl groups as the flaps. In the crystal, the molecules are linked by O—H...O hydrogen bonds into helical chains. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (63.2%), O...H/H...O (20.1%) and C...H/H...C (14.4%) contacts. Quantum chemical calculations of the frontier molecular orbitals were carried out to characterize the chemical reactivity of the title compound.

Keywords

• crystal structure
• benzylamine
• acridinedione
• hydrogen bonding
• hirshfeld analysis
• frontier orbitals