Publication Date:
2012-10-18
Description:
The title compound [systematic name: (1S)-2-((S)-{1-[(2S,3aS,7aS)-2-carboxyoctahydro-1H-indol-1-yl]-1-oxopropan-2-yl}azaniumyl)pentanoate monohydrate], C17H28N2O5·H2O, (I)·H2O, the active metabolite of the antihypertensive and cardiovascular drug perindopril, was obtained during polymorphism screening of perindoprilat. It crystallizes in the chiral orthorhombic space groupP212121, the same as the previously reported ethanol disolvate [Pascard, Guilhem, Vincent, Remond, Portevin & Laubie (1991).J. Med. Chem.34, 663–669] and dimethyl sulfoxide hemisolvate [Bojarska, Maniukiewicz, Sieroń, Fruziński, Kopczacki, Walczyński & Remko (2012).Acta Cryst.C68, o341–o343]. The asymmetric unit of (I)·H2O contains one independent perindoprilat zwitterion and one water molecule. These interactviastrong hydrogen bonds to give a cyclicR22(7) synthon, which provides a rigid molecular conformation. The geometric parameters of all three forms are similar. The conformations of the perhydroindole group are almost identical, but then-alkyl chain has conformational freedom. A three-dimensional hydrogen-bonding network of O—H...O and N—H...O interactions is observed in the crystal structure of (I)·H2O, similar to the other two solvates, but because of the presence of different solvents the three crystal structures have diverse packing motifs. All three solvatomorphs are additionally stabilized by nonclassical weak C—H...O contacts.
Print ISSN:
0108-2701
Electronic ISSN:
1600-5759
Topics:
Chemistry and Pharmacology
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Geosciences
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Physics
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