5-Acetyl-4-(2-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Abstract

In the title mol­ecule, C13H13ClN2O2, the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms making a dihedral angle of 89.16 (5)° with the benzene ring, which adopts an axial orientation. The carbonyl, acetyl and methyl groups each have an equatorial orientation. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds lead to a tape motif. The H atoms of the methyl group at position 6 are disordered over two positions of opposite orientation.

1-(6-Methyl-4-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone

“…For chemical and biological applications of dihydropyrimidinone derivatives, see: Chitra et al (2010). For their applications and for related structures, see: Anuradha et al (2008Anuradha et al ( , 2009a. Table 1 Hydrogen-bond geometry (Å , ).…”

“…Dihydropyrimidinone derivatives exhibit a wide range of biological effects such as antibacterial and antifungal activities (Chitra et al, 2010). The crystal structures of four very closely related compounds have recently been reported [Anuradha et al, (2008[Anuradha et al, ( , 2009a]. This study of the title compound, was undertaken to compare the biological activity and structure of dihydropyrimidin-2(1H)-thione and its corresponding 2(1H)-one (Anuradha et al, 2008).…”

5-Acetyl-4-(2-chlorophenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione

“…For chemical and biological applications of dihydropyrimidinones, see: Atwal et al (1990); Kappe (1993Kappe ( , 2000; Kappe et al (2000); Rovnyak et al (1995); Sadanandam et al (1992). For related crystal structures, see: Anuradha et al (2008Anuradha et al ( , 2009; Chitra et al (2009). supporting information Acta Cryst.…”

“…More recently they have emerged as integral backbones of several calcium blockers, antihypertensive agents, α-1a-antagonists and neuropeptide Y (NPY) antagonists (Atwal et al, 1990;Rovnyak et al, 1995). The crystal structures of three very closely related compounds have recently been reported [Anuradha et al, (2008[Anuradha et al, ( , 2009; Chitra et al, (2009)]. This study of the title compound, was undertaken to compare the biological activity and structure of dihydropyrimidin-2(1H)-thione and its corresponding 2(1H)-one (Anuradha et al, 2008).…”