Crystal structure, Hirshfeld surface and frontier mol-ecular orbital analysis of 10-benzyl-9-(4-hydroxy-3-meth-oxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2 H,5 H)-dione

V Sughanya; B Loganathan; D Praveenkumar; J Ayyappan; M L Sundararajan; A Prabhakaran; A Dhandapani; N Suresh Babu

doi:10.1107/S2056989022006557

Crystal structure, Hirshfeld surface and frontier mol-ecular orbital analysis of 10-benzyl-9-(4-hydroxy-3-meth-oxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2 H,5 H)-dione

Acta Crystallogr E Crystallogr Commun. 2022 Jul 14;78(Pt 8):789-793. doi: 10.1107/S2056989022006557. eCollection 2022 Aug 1.

Authors

V Sughanya¹, B Loganathan², D Praveenkumar³, J Ayyappan⁴, M L Sundararajan⁵, A Prabhakaran⁶, A Dhandapani⁶, N Suresh Babu⁷

Affiliations

¹ Department of Chemistry, Periyar Government Arts College, Cuddalore-607 001, Tamil Nadu, India.
² Department of Chemistry (Science and Humanities), Dr. N.G.P. Institute of Technology, Coimbatore-641 048, Tamil Nadu, India.
³ Department of Chemistry, Swami Vivekananda Arts and Science College, Orathur-605 601, Tamil Nadu, India.
⁴ Department of Physics, Government College of Engineering-Sengipatti, Thanjavur-613 402, Tamil Nadu, India.
⁵ Department of Chemistry, Annamalai University, Annamalai Nagar-608 002, Tamil Nadu, India.
⁶ Department of Chemistry, CK College of Engineering and Technology, Chellangkuppam, Cuddalore-607003, Tamil Nadu, India.
⁷ Department of Chemistry, Government College of Engineering-Sengipatti, Thanjavur-613 402, Tamil Nadu, India.

Abstract

In the fused ring system of the title mol-ecule, C₃₁H₃₅NO₄, the conformation of the central di-hydro-pyridine ring is inter-mediate 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 mol-ecules 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 mol-ecular orbitals were carried out to characterize the chemical reactivity of the title compound.

Keywords: Hirshfeld analysis; acridinedione; benzylamine; crystal structure; frontier orbitals; hydrogen bonding.