Crystal structure of 1,3-bis-(1,3-dioxoisoindolin-1-yl)urea dihydrate: a urea-based anion receptor

Acta Crystallogr Sect E Struct Rep Online. 2014 Oct 24;70(Pt 11):373-5. doi: 10.1107/S1600536814022144. eCollection 2014 Nov 1.

Abstract

The whole mol-ecule of the title compound, C17H10N4O5·2H2O, is generated by twofold rotation symmetry and it crystallized as a dihydrate. The planes of the phthalimide moieties and the urea unit are almost normal to one another, with a dihedral angle of 78.62 (9)°. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional framework structure. The crystal packing also features C-H⋯O hydrogen bonds and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6746 (15) Å] involving the benzene rings of neighbouring phthalimide moieties.

Keywords: crystal structure; isoindoline; phthalimides; protection of primary amines; urea; urea-based anion receptor.