Crystal packing analysis of 1-(3,4-dimethoxyphenyl)-3-(4-bromophenyl)prop-2-en-1-one exhibiting a putative halogen bond C[sbnd]Br⋯O

Abstract

The title compound, 1-(3,4-dimethoxyphenyl)-3-(4-bromophenyl) prop-2-en-1-one (1DBr) was synthesized and characterized based on spectroscopic analysis (MS, FT-IR, Elemental analysis, UV–visible, 1H NMR and 13C NMR) and finally the three-dimensional structure is confirmed using single crystal X-ray diffraction studies. The molecule is almost planar and the C---H⋯O intramolecular hydrogen bond closes the ring S(5). In the crystal structure, the molecules are connected through intermolecular hydrogen bond C---H⋯O (R22(14) ring motif) and intermolecular interactions (C---H⋯π and C---O⋯π). Hirshfeld surfaces computational method was employed to quantify the inter-contacts (2D Fingerprint plots) and calculate enrichment ratio (E). The highest value of E is calculated for the contact Br⋯O (1.65) followed by C⋯C (1.02) and have high propensity for forming contacts in the crystal. This provides the basis for the existence of putative halogen bond of the type C--Br⋯O. In addition, the Energy-framework analysis was used to analyze and visualize the 3D-topology of the crystal packing. The dispersion energy framework is dominated over the electrostatic energy-frameworks. The thermogravimetric analysis (TGA) provided the thermal degradation of the 1DBr to be from 230 to 320 °C.