NDLI: Perindoprilat monohydrate

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Perindoprilat monohydrate

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Bojarska, Joanna Maniukiewicz, Waldemar Sieron, Leslaw Kopczacki, Piotr Walczynski, Krzysztof Remko, Milan
Description	Country affiliation: Poland Author Affiliation: Bojarska J ( Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lódz, Poland.)
Abstract	The title compound [systematic name: (1 S)-2-(( S)-{1-[(2 S,3a S,7a S)-2-carboxyoctahydro-1 H-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, Sieron, Fruzinski, Kopczacki, Walczynski & Remko (2012). Acta Cryst. C 68, 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.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 11
Volume Number	68
Language	English
Publisher	IUCr/Wiley
Publisher Date	2012-11-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography Dimethyl Sulfoxide Chemistry Indoles Crystallography, X-ray Hydrogen Bonding Molecular Structure
Content Type	Text
Resource Type	Article

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