Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one

Abstract

The molecular structure of the title compound, C13H7Cl3OS, consists of a 2,5- dichlorothiophene ring and a 2-chlorophenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-dichlorothiophene and 2-chlorophenyl rings is 9.69 (12)°. The molecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The molecular conformation is stabilized by two intramolecular C—H...Cl contacts and one intramolecular C—H...O contact, forming S(5)S(5)S(6) ring motifs. In the crystal, the molecules are linked along the a-axis direction through van der Waals forces and along the b axis by face-to-face π-stacking between the thiophene rings and between the benzene rings of neighbouring molecules, forming corrugated sheets lying parallel to the bc plane. The intermolecular interactions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are Cl...H/ H...Cl (28.6%), followed by C...H/H...C (11.9%), C...C (11.1%), H...H (11.0%), Cl...Cl (8.1%), O...H/H...O (8.0%) and S...H/H...S (6.6%).

Keywords

• crystal structure
• 2,5- dichlorothiophene ring
• 2-chlorophenyl ring
• E configuration
• Hirshfeld surface analysis
• crystal structure