Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chloro-phen-yl)-1-(2,5-di-chloro-thio-phen-3-yl)prop-2-en-1-one

T N Sanjeeva Murthy; Zeliha Atioğlu; Mehmet Akkurt; M K Veeraiah; Ching Kheng Quah; C S Chidan Kumar; B P Siddaraju

doi:10.1107/S2056989018018066

Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chloro-phen-yl)-1-(2,5-di-chloro-thio-phen-3-yl)prop-2-en-1-one

Acta Crystallogr E Crystallogr Commun. 2019 Jan 4;75(Pt 2):124-128. doi: 10.1107/S2056989018018066. eCollection 2019 Feb 1.

Authors

T N Sanjeeva Murthy¹, Zeliha Atioğlu², Mehmet Akkurt³, M K Veeraiah⁴, Ching Kheng Quah⁵, C S Chidan Kumar⁶, B P Siddaraju⁷

Affiliations

¹ Department of Chemistry, Sri Siddhartha Academy of Higher Education, Tumkur 572 107, Karnataka, India.
² İlke Education and Health Foundation, Cappadocia University, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey.
³ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁴ Department of Chemistry, Sri Siddhartha Institute of Technology, Tumkur 572 105, Karnataka, India.
⁵ X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
⁶ Department of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570028, Karnataka, India.
⁷ Department of Chemistry, Cauvery Institute of Technology, Mandya 571 402, Karnataka, India.

Abstract

The mol-ecular structure of the title compound, C₁₃H₇Cl₃OS, consists of a 2,5- di-chloro-thio-phene ring and a 2-chloro-phenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-di-chloro-thio-phene and 2-chloro-phenyl rings is 9.69 (12)°. The mol-ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The mol-ecular conformation is stabilized by two intra-molecular C-H⋯Cl contacts and one intra-molecular C-H⋯O contact, forming S(5)S(5)S(6) ring motifs. In the crystal, the mol-ecules 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 thio-phene rings and between the benzene rings of neighbouring mol-ecules, forming corrugated sheets lying parallel to the bc plane. The inter-molecular inter-actions 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: 2,5- dichlorothiophene ring; 2-chlorophenyl ring; E configuration; Hirshfeld surface analysis; crystal structure.