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Synthesis, crystal structure, Hirshfeld surface and interaction energies analysis of 5-methyl-1,3-bis(3-nitrobenzyl)pyrimidine-2,4(1H,3H)-dione Etse, Koffi Senam Lamela, Laura Comeron Zaragoza, Guillermo Pirotte, Bernard Thymine Crystal structure Hirshfeld surfaces Hydrogen bonding Interaction energies 3-Nitrobenzylbromide The title compound 5-methyl-1,3-bis(3-nitrobenzyl)pyrimidine-2,4(1H,3H)-dione was obtained by reaction of thymine with 3-nitrobenzylbromide in the presence of cesium carbonate. Characterization of the product was achieved by NMR spectroscopy and its stability was probed in basic condition using UV-Visible analysis. Furthermore, the molecular structure was confirmed by X-ray diffraction analysis. The compound crystallizes in orthorhombic Pna21 space group with unit cell parameters a = 14.9594 (15) Å, b = 25.711 (3) Å, c = 4.5004 (4) Å, V = 1731.0 (3) Å3 and Z = 4. The crystal packing of the title compound is stabilized by intermolecular hydrogen bond, π···π and C−H···π stacking interactions. The intermolecular interactions were furthermore analyzed through the mapping of different Hirshfeld surfaces. The two-dimensional fingerprint revealed that the most important contributions to these surfaces come from O···H (37.1%), H···H (24%) and H···C/C···H (22.6%) interactions. The interaction energies stabilizing the crystal packing were calculated and were presented graphically as framework energy diagrams. Finally, the energy-framework analysis reveals that π···π and C−H···π interactions energies are mainly dispersive and are the most important forces in the crystal. Atlanta Publishing House LLC 2020-06-30 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf text/plain https://www.eurjchem.com/index.php/eurjchem/article/view/1973 10.5155/eurjchem.11.2.91-99.1973 European Journal of Chemistry; Vol. 11 No. 2 (2020): June 2020; 91-99 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/1973/pdf_1973 https://www.eurjchem.com/index.php/eurjchem/article/view/1973/2656 Copyright (c) 2020 Authors