Crystal structures of 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(2,4-dimethylphenyl)acetamide and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(3-methoxyphenyl)acetamide

Abstract

In the title compounds, C14H17N5OS (I) and C13H15N5O2S (II), the dihedral angle between the pyrimidine and benzene rings is 58.64 (8)° in (I) and 78.33 (9)° in (II). In both compounds, there is an intramolecular C—H...O hydrogen bond, and in (II) there is also an intramolecular N—H...N hydrogen bond present. In the crystals of both compounds, a pair of N—H...N hydrogen bonds links the individual molecules to form inversion dimers with R22(8) ring motifs. In (I), the dimers are linked by N—H...O and C—H...O hydrogen bonds, enclosing R21(14), R21(11) and R21(7) ring motifs, forming layers parallel to the (100) plane. There is also an N—H...π interaction present within the layer. In (II), the inversion dimers are linked by N—H...O hydrogen bonds enclosing an R44(18) ring motif. The presence of N—H...O and C—H...O hydrogen bonds generate an R21(6) ring motif. The combination of these various hydrogen bonds results in the formation of layers parallel to the (1-11) plane.

Keywords

• crystal structure
• diaminopyrimidine
• pharmacological properties
• hydrogen bonding