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Acta crystallographica. Section C, Crystal structure communications

Felodipine-diazabicyclo[2.2.2]octane-water (1/1/1).


PMID 23124462

Abstract

The title compound, C(18)H(19)Cl(2)NO(4)·C(6)H(12)N(2)·H(2)O, is a cocrystal hydrate containing the active pharmaceutical ingredient felodipine and diazabicyclo[2.2.2]octane (DABCO). The DABCO and water molecules are linked through O-H···N hydrogen bonds into chains around 2(1) screw axes, while the felodipine molecules form N-H···O hydrogen bonds to the water molecules. The felodipine molecules adopt centrosymmetric back-to-back arrangements that are similar to those present in all of its four reported polymorphs. The dichlorophenyl rings also form π-stacking interactions. The inclusion of water molecules in the cocrystal, rather than formation of N-H···N hydrogen bonds between felodipine and DABCO, may be associated with steric hindrance that would arise between DABCO and the methyl groups of felodipine if they were directly involved in hydrogen bonding.

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F9677
Felodipine, solid
C18H19NO4Cl2