Crystal structure and Hirshfeld surface analysis of a bromo-chalcone: (E)-1-(3-bromo-phen-yl)-3-(2,6-di-chloro-phen-yl)prop-2-en-1-one

S Bindya; C S Chidan Kumar; S Naveen; B P Siddaraju; Ching Kheng Quah; Md Abu Raihan

doi:10.1107/S205698901900104X

Crystal structure and Hirshfeld surface analysis of a bromo-chalcone: (E)-1-(3-bromo-phen-yl)-3-(2,6-di-chloro-phen-yl)prop-2-en-1-one

Acta Crystallogr E Crystallogr Commun. 2019 Jan 25;75(Pt 2):264-267. doi: 10.1107/S205698901900104X. eCollection 2019 Feb 1.

Authors

S Bindya¹, C S Chidan Kumar², S Naveen³, B P Siddaraju⁴, Ching Kheng Quah⁵, Md Abu Raihan⁶

Affiliations

¹ Department of Chemistry, Sri Jayachamarajendra College of Engineering, JSS Science and Technology University, Mysuru 570 006, Karnataka, India.
² Department of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahally, Mysuru 570 028, India.
³ Department of Physics, School of Engineering and Technology, Jain University, Bangalore 562 112, India.
⁴ Department of Chemistry, Cauvery Institute of Technology, Mandya 571 402, Karnataka, India.
⁵ X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
⁶ Head of TVE Department, Islamic University of Technology (IUT), Gazipur 1704, Bangladesh.

Abstract

In the title chalcone derivative, C₁₅H₉BrCl₂O, the aryl rings are inclined to each by 14.49 (17)°, and the configuration about the C=C bond is E. There is a short intra-molecular C-H⋯Cl contact present resulting in the formation of an S(6) ring motif. In the crystal, the shortest inter-molecular contacts are Cl⋯O contacts [3.173 (3) Å] that link the mol-ecules to form a 2₁ helix propagating along the b-axis direction. The helices stack up the short crystallographic a axis, and are linked by offset π-π inter-actions [inter-centroid distance = 3.983 (1) Å], forming layers lying parallel to the ab plane. A qu-anti-fication of the inter-molecular contacts in the crystal were estimated using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Keywords: Cl⋯O contact; E configuration; Hirshfeld surface analysis; chalcone; crystal structure; enone bridge; fingerprint plots; offset π–π interactions.