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

Abstract

The title compounds, C12H12ClN5OS, (I), and C12H12ClN5OS, (II), are 2-[(diaminopyrimidin-2-yl)sulfanyl]acetamides. Compound (II), crystallizes with two independent molecules (A and B) in the asymmetric unit. In each of the molecules, in both (I) and (II), an intramolecular N—H...N hydrogen bond forms an S(7) ring motif. The pyrimidine ring is inclined to the benzene ring by 42.25 (14)° in (I), and by 59.70 (16) and 62.18 (15)° in molecules A and B, respectively, of compound (II). In the crystal of (I), molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via bifurcated N—H...O and C—H...O hydrogen bonds, forming corrugated layers parallel to the ac plane. In the crystal of (II), the A molecules are linked through N—H...O and N—H...Cl hydrogen bonds, forming layers parallel to (100). The B molecules are also linked by N—H...O and N—H...Cl hydrogen bonds, also forming layers parallel to (100). The parallel layers of A and B molecules are linked via N—H...N hydrogen bonds, forming a three-dimensional structure.

Keywords

• crystal structure
• diaminopyrimidin(2-yl) derivatives
• thioacteamide
• hydrogen bonding
• C—H...π interactions
• offset π–π interactions