Novel supramolecular co-crystal of 3-aminobenzoic acid with 4-acetyl-pyridine: Synthesis, X-ray structure, DFT and Hirshfeld surface analysis

Abstract

A novel co-crystal of 3-aminobenzoic acid with 4-acetyl pyridine (ABA:AP) has been synthesized and its structure determined by single crystal X-ray diffraction (SCXRD) methods. It crystallizes in the monoclinic crystal system with space group P21/n and unit cell parameters a = 7.573(11) Å, b = 10.718(11) Å, c = 15.77(2) Å, β = 98.10(10)°, Z = 4. The co-crystal is stabilized by R22(8) ring motif, hydrogen bonding and π-π interactions. Density functional theory (DFT) and Hartree Fock (HF) methods with basis set of B3LYP/6-311+G(d,p) have been employed to obtain the optimized structural geometry, Mulliken charges, molecular electrostatic potential (MSP) and frontier molecular orbitals. The contribution of distinct interactions within the molecule and the strength of molecular packing in the co-crystal have been investigated by Hirshfeld surface (HS) analysis.