Supramolecular co-crystal of 4-dimethyl aminopyridine with Picric acid (4DMAP: PA): Synthesis, single crystal investigation, HF/DFT inspection, Hirshfeld surface and antifungal activity

• Published in: Journal of molecular structure Vol. 1270; p. 133921
• Main Authors: Sharma, Ruchika, Srijana, Palthad Jayarama, Singh, Mulveer, Kamal, Narayana, Badiadka, Sarojini, Balladka Kunhanna, Likhitha, Ullal, Murugavel, Saminathan, Raj, Jayakumar Mohan, Kant, Rajni
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-12-2022
• Subjects: Antifungal activity; DFT; Hirshfeld analysis; Intermolecular interactions; Synthesis; Intermolecular interactions; Hirshfeld analysis; Antifungal activity; Synthesis; DFT
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.133921

•A novel 4DMAP:PA co-crystal has been synthesized and characterized using single crystal X-ray diffraction and quantum chemical techniques.•Intermolecular interactions has been analyzed using 3D Hirshfield surfaces and the corresponding 2D fingerprint plots.•The optimized geometric parameters obtained theoretically using HF/DFT techniques have been compared with the corresponding X-ray data.•The molecular geometry, HOMO-LUMO energies, Mulliken charges and MEP map have been obtained using DFT/HF methods and discussed in detail.•The co-crystal suggests antifungal activity against the fungal pathogens when compared with the standard antifungal drug fluconazole.
4-Dimethylaminopyridine-Picric acid (4DMAP:PA) co-crystals were synthesized by slow evaporation technique using C2H5OH as the solvent. The molecular structure has been characterized using spectroscopic and single crystal X-ray diffraction techniques. The molecule contains O–H…O, O–H…N, C–H…O and π…π interactions. The C12–H12…O4A and C12A–H12A…O4 forms a dimer with a R22(10) graph set motif. Few intermolecular C–H…O and O–H…N bonds result in the formation of a R22(9)ring motif. The structure has been theoretically optimized by using Hartree-Fock (HF) and density functional theory (DFT) approaches. The DFT calculation led to the investigation of FMO, MEP, Mulliken charges and HOMO – LUMO, energy gap. The Hirshfeld surface (HS) and fingerprint plots analysis provided an insight in the molecular shape and visual assessment of the intermolecular interactions in the crystal structure. The co-crystal suggests antifungal activity against the fungal pathogens when compared with the standard antifungal drug fluconazole.
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