Synthesis, crystal structure, crystal supramolecularity and Hirshfeld surface analysis of (E)-1-(2,5-dichlorothiophen-3-yl)-3-o-tolylprop-2-en-1-one

Abstract The asymmetric unit of, C14H10Cl2OS, I, consists of one independent molecule with E configuration about the C C bond. The molecular structure composed of two aromatic rings, the 2,5-dichlorothiophenyl and the tolyl that are linked by the central –CO—CH CH– unit. The molecule is planar as indicated by the dihedral angle [4.27°] between the aromatic rings. The molecular structure is stabilized by two C—H•••O and one C—H•••Cl intramolecular hydrogen bonds forming S(5)S(5)S(6) ring motifs. In the crystal, the molecules are connected by C—H•••O/Cl, Cl•••Cl and S•••Cl interactions into a 3-dimensional supramolecular array. The Hirshfeld surface analysis revealed that the most significant interactions are: H•••H (25.7%), Cl•••H/H•••Cl (15.6%), C•••H/H•••C (15.3%), O•••H/H•••O (9.9%), C•••C (9.5%), amongst others. The calculated interaction energies indicate that the dispersion energy contributions are the most important in stabilizing the crystal structure.