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The crystals of two new salts, 2,6-di-amino-4-chloro-pyrimidin-1-ium 5-chloro-salicylate, C 4 H 6 ClN 4  + ·C 7 H 4 ClO 3  - , (I), and bis-(2,6-di-amino-4-chloro-pyrimidin-1-ium) naphthalene-1,5-di-sulfonate, 2C 4 H 6 ClN 4  + ·C 10 H 6 O 6 S 2  2- , (II), have been synthesized and characterized by single-crystal X-ray diffraction. In both compounds, the N atom of the pyrimidine group in between the amino substituents is protonated and the pyrimidinium cation forms a pair of N-H⋯O hydrogen bonds with the carboxyl-ate/sulfonate ion, leading to a robust R  2  2 (8) motif (supra-molecular heterosynthon). In compound (I), a self-complementary base pairing involving the other pyrimidinium ring nitro-gen atom and one of the amino groups via a pair of N-H⋯N hydrogen bonds [ R  2  2 (8) homosynthon] is also present. In compound (II), the crystallographic inversion centre coincides with the inversion centre of the naphthalene-1,5-di-sulfonate ion and all the sulfonate O atoms are hydrogen-bond acceptors, generating fused-ring motifs and a quadruple DDAA array. A halogen-bond (Cl⋯Cl) inter-action is present in (I) with a distance and angle of 3.3505 (12) Å and 151.37 (10)°, respectively. In addition, a C-Cl⋯π inter-action and a π-π inter-action in (I) and a π-π inter-action in (II) further stabilize these crystal structures.

acta crystallographica. section e, crystallographic communications

Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate