Quantitative Crystal Structure Analysis of A Selected Spirohydantoin Derivative

Abstract

An analysis of structural features of new compounds with multiple hydrogen-bond donating and accepting groups can enhance our understanding of development of supramolecular assemblies with potential for application in life sciences. Using the quantum chemical calculations, formation of the crystal structure of cyclohexane-5-spirohydantoin bearing a 4-tert-butylbenzoyl group (Fig. 1) was analysed in terms of a number of dimeric motifs associated with intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N‒H‧‧‧O hydrogen bonds [1]. This motif is involved in two types of double chains, which further form a layer. Together with the dispersion interactions (π‒π and hydrophobic), C‒H‧‧‧O interactions act as the source of attraction between the layers. Intermolecular interactions were also investigated using the Hirschfield surface analysis, enabling to additionally estimate quantitative contributions of intermolecular interactions to the crystal packing.