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

• Crystal and molecular structure of ( E )−1-(2,5-dichlorothiophen-3-yl)−3-o-tolylprop-2-en-1-one. • 3D framework structure. • C–H•••O and C–H•••Cl, Cl•••Cl and S•••Cl interactions and crystal packing. • Hirshfeld surface analysis. • Energy frameworks analysis. • Dispersion energy contributions are the most important in stabilizing the crystal structure. The asymmetric unit of, C 14 H 10 Cl 2 OS, 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. Crystal and molecular structure of ( E )-1-(2,5-dichlorothiophen-3-yl)-3-o-tolylprop-2-en-1-one are reported. Hirshfeld surface analysis and energy framework simulations are discussed.