2-Chloro-N-(3-methylphenyl)benzamide

Abstract

In the structure of the title compound, C14H12ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N—H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1)°. The crystal structure is stabilized by N—H...O hydrogen bonds, which give rise to infinite chains running along the c axis

2-Chloro-N-(2-methylphenyl)benzamide

“…In the title compound, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, similar to that observed in 2-chloro-N-(3-methylphenyl)benzamide (I) (Rodrigues et al, 2012). The ortho-methyl group in the anilino ring is also positioned syn to the N-H bond, in contrast to the anti conformation observed between the meta-methyl group and the N -H bond in (I).…”

“…The amide and sulfonamide moieties are the constituents of many biologically important compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al, 2003;Gowda et al, 2000;Rodrigues et al, 2012;Saeed et al, 2010), N-chloroarylsulfonamides (Gowda & Rao, 1989;Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Gowda & Mahadevappa, 1983;Usha & Gowda, 2006), in the present work, the crystal structure of 2-chloro-N-(2-methylphenyl)benzamide has been determined ( Fig.1).…”

“…For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al (2003); Gowda et al (2000); Rodrigues et al (2012); Saeed et al (2010) of N-chloroarylamides, see: Gowda & Rao (1989); Jyothi & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).…”