The supramolecular effect of aromaticity on the crystal packing of furan/thiophene carboxamide compounds

N-2-pyrazinyl-2-furancarboxamide (I) and N-2-pyrazinyl-2-thiophenecarboxamide (II) are compounds containing different five-membered heteroaromatic rings, furan and thiophene, respectively. They were designed and synthesized to examine the effect of an increase in aromaticity from furan to thiophene on the crystal packing. In order to explore the various features of the crystal packing motifs in more detail, single crystal X-ray diffraction, Hirshfeld surface analysis and theoretical calculations were carried out on the two compounds. The results clearly show that the heteroatom substitution of O to S in five-membered rings led to an increase in the effectiveness of π-based interactions in II, whereas hydrogen bond interactions play a more important role in the stabilization of the supramolecular architecture of I.