Self-assembling of dihydroxypropyl 5,6-dihydrothymine derivatives

(R, S)-1-(2′,3′-Dibenzoyloxypropyl)-5,6-dihydrothymine (2) was synthesized from (R, S)-1-(2′,3′-dihydroxypropyl)-5,6-dihydrothymine and its structure has been analyzed by X-ray diffraction, NMR and FTIR spectroscopic methods. The molecular structure and supramolecular assembling of 2 is compared with the structure of its dimesyloxypropyl analogue (1). Compound 1 crystallizes as cocrystal of two diastereoisomers, while 2 crystallizes as a racemic mixture. Main hydrogen-bonded motif in both compounds is dimer formed by pair of NH···O(C) hydrogen bonds, which are further linked by CH···O hydrogen bonds. Phenyl rings of dibenzoyl-dihydropyrimidine moieties of 2 participate also in supramolecular aggregation via three CH···π interactions. Hydrogen bonding as driving force of 2 self-assembly was proving by the NMR and FTIR spectroscopy.