Title of article :
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
Author/Authors :
Subasri, S. Centre of Advanced Study in Crystallography and Biophysics - University of Madras, India , Kumar, Timiri Ajay Department of Pharmaceutical Sciences & Technology - Birla Institute of Technology, India , Sinha, Barij Nayan Department of Pharmaceutical Sciences & Technology - Birla Institute of Technology, India , Jayaprakash, Venkatesan Department of Pharmaceutical Sciences & Technology - Birla Institute of Technology, India , Viswanathan, Vijayan Centre of Advanced Study in Crystallography and Biophysics - University of Madras, India , Velmurugan, Devadasan Centre of Advanced Study in Crystallography and Biophysics - University of Madras, India
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
Journal title :
Acta Crystallographica Section E: Crystallographic Communications