Crystal structures of (E)-3-(4-hy-droxy-benzyl-idene)chroman-4-one and (E)-3-(3-hy-droxy-benzyl-idene)-2-phenyl-chroman-4-one

Kamil Suchojad; Anna Dołęga; Angelika Adamus-Grabicka; Elżbieta Budzisz; Magdalena Małecka

doi:10.1107/S2056989019015639

Crystal structures of (E)-3-(4-hy-droxy-benzyl-idene)chroman-4-one and (E)-3-(3-hy-droxy-benzyl-idene)-2-phenyl-chroman-4-one

Acta Crystallogr E Crystallogr Commun. 2019 Nov 22;75(Pt 12):1907-1913. doi: 10.1107/S2056989019015639. eCollection 2019 Dec 1.

Authors

Kamil Suchojad¹, Anna Dołęga², Angelika Adamus-Grabicka³, Elżbieta Budzisz³, Magdalena Małecka¹

Affiliations

¹ Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Łódź, Poland.
² Department of Inorganic Chemistry, Gdańsk University of Technology, G. Narutowicza 11/12., 80-233 Gdańsk, Poland.
³ Department of Cosmetic Raw Materials Chemistry, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Łódź, Poland.

Abstract

The synthesis and crystal structures of (E)-3-(4-hy-droxy-benzyl-idene)chroman-4-one, C₁₆H₁₂O₃, I, and (E)-3-(3-hy-droxy-benzyl-idene)-2-phenyl-chroman-4-one, C₂₂H₁₆O₃, II, are reported. These compounds are of inter-est with respect to biological activity. Both structures display inter-molecular C-H⋯O and O-H⋯O hydrogen bonding, forming layers in the crystal lattice. The crystal structure of compound I is consolidated by π-π inter-actions. The lipophilicity (logP) was determined as it is one of the parameters qualifying compounds as potential drugs. The logP value for compound I is associated with a larger contribution of C⋯H inter-action in the Hirshfeld surface.

Keywords: Hirshfeld surface analysis; chromanone derivative; crystal structure; flavanone derivative; lipophilicity index.

Grants and funding

This work was funded by Uniwesytet Łódzki, Uniwersytet Medyczny w Łodzi grants SGB_148_Suchojad_Kamil and 502-03/3-066-02/502-34-118.