Hydrogen-bonded supramolecular motifs in 2-amino-4,6-dimethoxypyrimidinium picrate and pyrimethaminium picrate dimethyl sulfoxide solvate.
In the crystal structures of 2-amino-4,6-dimethoxypyrimidinium 2,4,6-trinitrophenolate (picrate), C(6)H(10)N(3)O(2)(+).C(6)H(2)N(3)O(7)(-), (I), and 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium (pyrimethaminium or PMN) picrate dimethyl sulfoxide solvate, C(12)H(14)ClN(4)(+).C(6)H(2)N(3)O(7)(-).C(2)H(6)OS, (II), the 2-amino-4,6-dimethoxypyrimidine and PMN cations are protonated at one of the pyrimidine N atoms. The picrate anion interacts with the protonated cations through bifurcated N-H...O hydrogen bonds, forming R(2)(1)(6) and R(1)(2)(6) ring motifs. In (I), Z' = 2. In (II), two inversion-related PMN cations are connected through a pair of N-H...N hydrogen bonds involving the 4-amino group and the uncharged N atom of the pyrimidine ring, forming a cyclic hydrogen-bonded R(2)(2)(8) motif. In addition to the pairing, the O atom of the dimethyl sulfoxide solvent molecule bridges the 2-amino and 4-amino groups on both sides of the paired bases, resulting in a self-complementary ...DADA... array of quadruple hydrogen-bonding patterns.
Thanigaimani
Kaliyaperumal
K
School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamil Nadu, India. tommtrichy@yahoo.co.in
Subashini
Annamalai
A
Muthiah
Packianathan Thomas
PT
Lynch
Daniel E
DE
Butcher
Ray J
RJ
D003461:Crystallography; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D010851:Picrates / Q000737:chemistry*; D011739:Pyrimethamine / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*
C464526:2-amino-4,6-dimethyl pyrimidine; D010851:Picrates; D011743:Pyrimidines; C518759:2-amino-4,6-dimethoxypyrimidine; D004121:Dimethyl Sulfoxide; D011739:Pyrimethamine