Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo-phen-yl)-1-(4-iodo-phen-yl)prop-2-en-1-one

Kieran J Spruce; Charlie L Hall; Jason Potticary; Natalie E Pridmore; Matthew E Cremeens; Gemma D D'ambruoso; Masaomi Matsumoto; Gabrielle I Warren; Stephen D Warren; Simon R Hall

doi:10.1107/S2056989019016402

Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo-phen-yl)-1-(4-iodo-phen-yl)prop-2-en-1-one

Acta Crystallogr E Crystallogr Commun. 2020 Jan 1;76(Pt 1):72-76. doi: 10.1107/S2056989019016402.

Affiliations

¹ School of Chemistry, University of Bristol, Cantock's Close, Bristol, England, BS8 1TS, England.
² Department of Chemistry & Biochemistry, Gonzaga University, 502 E Boone Ave, Spokane, WA 99258, USA.

Abstract

The title compound, C₁₅H₁₀I₂O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. In the mol-ecule, the mean planes of the 3-iodo-phenyl and the 4-iodo-phenyl groups are twisted by 46.51 (15)°. The calculated electrostatic potential surfaces show the presence of σ-holes on both substituted iodines. In the crystal, the mol-ecules are linked through type II halogen bonds, forming a sheet structure parallel to the bc plane. Between the sheets, weak inter-molecular C-H⋯π inter-actions are observed. Hirshfeld surface analysis showed that the most significant contacts in the structure are C⋯H/H⋯C (31.9%), followed by H⋯H (21.4%), I⋯H/H⋯I (18.4%). I⋯I (14.5%) and O⋯H/H⋯O (8.1%).

Keywords: (E)-3-(3-iodophenyl)-1-(4-iodophenyl)prop-2-en-1-one; E configuration; chalcone; crystal structure; iodophenyl ring.

Grants and funding

This work was funded by Engineering and Physical Sciences Research Council UK grant EP/L015544/1 to Charlie L. Hall. MagnaPharm grant 736899 to Simon R. Hall and Jason Potticary.