6-Amino-2-iminiumyl-4-oxo-1,2,3,4-tetrahydropyrimidin-5-aminium sulfate monohydrate

  • The title compound, C4H9N5O2+·SO42−·H2O, is the monohydrate of the commercially available compound `C4H7N5O·H2SO4·xH2O'. It is obtained by reprecipitation of C4H7N5O·H2SO4·xH2O from dilute sodium hydroxide solution with dilute sulfuric acid. The crystal structure of anhydrous 2,4,5-tri­amino-1,6-di­hydro­pyrimidin-6-one sulfate is known, although called by the authors 5-amminium-6-amino-isocytosinium sulfate [Bieri et al. (1993[Bieri, J. H., Prewo, R. & Linden, A. (1993). Private communication (refcode HACDEU). CCDC, Cambridge, England]). Private communication (refcode HACDEU). CCDC, Cambridge, England]. In the structure, the sulfate group is deprotonated, whereas one of the amino groups is protonated (R2C—NH3+) and one is rearranged to a protonated imine group (R2C=NH2+). This arrangement is very similar to the known crystal structure of the anhydrate. Several tautomeric forms of the investigated mol­ecule are possible, which leads to questionable proton attributions. The measured data allowed the location of all hydrogen atoms from the residual electron density. In the crystal, ions and water mol­ecules are linked into a three-dimensional network by N—H⋯O and O—H⋯O hydrogen bonds.

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Author:Lukas TapmeyerORCiDGND, Dragica PrillGND
Parent Title (English):IUCrData
Publisher:International Union of Crystallography
Place of publication:Chester
Document Type:Article
Year of Completion:2019
Year of first Publication:2019
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2023/09/18
Tag:crystal structure; hydrogen bonds; triaminodihydropyrimidinone
Issue:5, x190689
Page Number:7
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - CC BY - Namensnennung 4.0 International