title: Perindoprilat monohydrate.
abstract: 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], C(17)H(28)N(2)O(5)·H(2)O, (I)·H(2)O, the active metabolite of the antihypertensive and cardiovascular drug perindopril, was obtained during polymorphism screening of perindoprilat. It crystallizes in the chiral orthorhombic space group P2(1)2(1)2(1), 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)·H(2)O contains one independent perindoprilat zwitterion and one water molecule. These interact via strong hydrogen bonds to give a cyclic R(2)(2)(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 the n-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)·H(2)O, 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.
authors.affiliation: Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Bojarska
authors.forename: Waldemar
authors.initials: W
authors.lastname: Maniukiewicz
authors.forename: Lesław
authors.initials: L
authors.lastname: Sieroń
authors.forename: Piotr
authors.initials: P
authors.lastname: Kopczacki
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Walczyński
authors.forename: Milan
authors.initials: M
authors.lastname: Remko
mesh_terms: D018360:Crystallography, X-Ray; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D007211:Indoles; C053500:perindoprilat; D004121:Dimethyl Sulfoxide