title: Novel pseudopolymorph of the active metabolite of perindopril.
abstract: The dimethyl sulfoxide hemisolvate of perindoprilat [systematic name: (1S)-2-((S)-{1-[(2S,3aS,7aS)-2-carboxyoctahydro-1H-indol-1-yl]-1-oxopropan-2-yl}azaniumyl)pentanoate dimethyl sulfoxide hemisolvate], C(17)H(28)N(2)O(5)·0.5C(2)H(6)OS, an active metabolite of perindopril, has been synthesized, structurally characterized by single-crystal X-ray diffraction and compared with its ethanol disolvate analogue [Pascard et al. (1991). J. Med. Chem. 34, 663-669]. Both compounds crystallize in the orthorhombic P2(1)2(1)2(1) space group in the same zwitterionic form, with a protonated alanine N atom and an anionic carboxylate group at the n-alkyl chain. The three structural units present in the unit cell (two zwitterions and the solvent molecule) are held together by a rich system of O-H···O, N-H···O and C-H···O hydrogen-bond 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: Andrzej
authors.initials: A
authors.lastname: Fruziński
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: D000838:Anions / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000838:Anions; D007211:Indoles; D012997:Solvents; C053500:perindoprilat