Structural and theoretical studies of 4-chloro-2-methyl-6-oxo-3,6-dideuteropyrimidin-1-ium chloride (d (6))

The title compound, C(5)D(6)ClN(2)O(+)·Cl(−), crystallizes in the ortho­rhom­bic space group, Pbcm, and consists of a 4-chloro-2-methyl-6-oxo-3,6-di­hydro­pyrimidin-1-ium cation and a chloride anion where both moieties lie on a crystallographic mirror. The cation is disordered and was refined as two equivalent forms with occupancies of 0.750 (4)/0.250 (4), while the chloride anion is triply disordered with occupancies of 0.774 (12), 0.12 (2), and 0.11 (2). Unusually, the bond angles around the C=O unit range from 127.2 (6) to 115.2 (3)° and similar angles have been found in other structures containing a 6-oxo-3,6-di­hydro­pyrimidin-1-ium cation, including the monclinic polymorph of the title compound, which crystallizes in the monoclinic space group P2(1)/c [Kawai et al. (1973 ▸). Cryst. Struct. Comm. 2, 663–666]. The cations and anions pack into sheets in the ab plane linked by N—H⋯Cl hydrogen bonds as well as C—H⋯O and Cl⋯O inter­actions. In graph-set notation, these form R (3) (3)(11) and R (3) (2)(9) rings. Theoretical calculations seem to indicate that the reason for the unusual angles at the sp (2) C is the electrostatic inter­action between the oxygen atom and the adjacent N—H hydrogen.