Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-bromo-4-fluoro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one.

S N Sheshadri,Zeliha Atioğlu,B P Siddaraju,C S Chidan Kumar,Ching Kheng Quah,M K Veeraiah,Mehmet Akkurt

doi:10.1107/s2056989018009416

Abstract

In the mol-ecule of the title compound, C17H14BrFO3, the aromatic rings are tilted with respect to the enone bridge by 13.63 (14) and 4.27 (15)°, and form a dihedral angle 17.91 (17)°. In the crystal, centrosymmetrically related mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into dimeric units, forming rings of R22(14) graph-set motif. The dimers are further connected by weak C-H⋯O hydrogen inter-actions, forming layers parallel to (10). Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 29.7% of the surface.

Highlights

In the molecule of the title compound, C17H14BrFO3, the aromatic rings are tilted with respect to the enone bridge by 13.63 (14) and 4.27 (15), and form a dihedral angle 17.91 (17)
Centrosymmetrically related molecules are linked by pairs of C—HÁ Á ÁO hydrogen bonds into dimeric units, forming rings of R22(14) graph-set motif
Hirshfeld surface analysis shows that van der Waals interactions constitute the major contribution to the intermolecular interactions, with HÁ Á ÁH contacts accounting for 29.7% of the surface

Summary

Chemical context

Natural products are important sources to search for new agents for cancer therapies with minimal side effects. Chalcones, which are considered to be the precursors of flavonoids and isoflavonoids, are abundant in edible plants. They consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon ,-unsaturated carbonyl system. These are coloured compounds because of the presence of the –CO—CH CH– chromophore, the colour depending on the presence of other auxochromes. In view of the above and in a continuation of our previous work on 3,4-dimethoxy chalcones (Sheshadri et al, 2018), we report the crystal and molecular structures of the title compound. Symmetry codes: (i) Àx þ 32; y À 12; Àz þ 12; (ii) Àx þ 1; Ày þ 2; Àz

Structural commentary

Hirshfeld Surface Analysis

Supramolecular features

Findings

Synthesis and crystallization