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.
Highlights
The whole molecule of the title compound, C17H10N4O52H2O, is generated by twofold rotation symmetry and it crystallized as a dihydrate
It has been shown that the efficiency of urea as a receptor subunit depends on the presence of two proximate polarised N—H fragments, capable of (i) chelating a spherical anion or (ii) donating two parallel hydrogen bonds to the O atoms of a carboxylate or of an inorganic oxoanion
In our ongoing research on 1,3-dioxoisoindolines as anion receptors (Lujano, 2012), we report on the synthesis and crystal structure of the title ureabased anion receptor
Summary
Hydrogen bonding and – interactions are two of the principal forces which determine structure, self-assembly and recognition in some chemical and biological systems (Lehn, 1990). A variety of urea-based anion receptors of varying complexity and sophistication have been synthesised (Amendola et al, 2010). It has been shown that the efficiency of urea as a receptor subunit depends on the presence of two proximate polarised N—H fragments, capable of (i) chelating a spherical anion or (ii) donating two parallel hydrogen bonds to the O atoms of a carboxylate or of an inorganic oxoanion. Phthalimides and isoindolines have been shown to possess photophysical properties and have applications as colourimetric and other types of anion sensors In our ongoing research on 1,3-dioxoisoindolines as anion receptors (Lujano, 2012), we report on the synthesis and crystal structure of the title ureabased anion receptor
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