N-(3-Chloro-4-methylphenyl)succinamic acid

Abstract

Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.007 Å; R factor = 0.083; wR factor = 0.159; data-to-parameter ratio = 13.4.In the crystal structure of the title compound, C 11 H 12 ClNO 3 , the asymmetric unit contains two independent molecules. The N-H bond in the amide segment is anti to the meta-Cl atom in the benzene ring, in both molecules. The amide and carboxyl C O bonds are also anti to each other and anti to the H atoms on the adjacent -CH 2 groups. Furthermore, the C O and O-H bonds of the acid group are in syn positions with respect to each other. The dihedral angles between the benzene ring and the amide group are 40.6 (2) and 44.9 (3) in the two independent molecules. In the crystal, molecules are packed into sheets parallel to the (113) plane through O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds. Related literature ExperimentalCrystal data

N-(3-Chloro-2-methylphenyl)succinamic acid

“…1). The conformation of the N-H bond in the amide segment is syn to the ortho-methyl and meta-Cl in the benzene ring, in contrast to the anti conformation observed between the N-H bond and the meta-Cl in N-(3-chloro-4-methylphenyl)-succinamic acid (I) (Chaithanya et al, 2012).…”

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