4-Chloro-N-(2,4-dimethylphenyl)-2-methylbenzenesulfonamide

Abstract

In the title compound, C15H16ClNO2S, the C—SO2—NH—C torsion angle is 67.45 (17)°. The two aromatic rings are tilted relative to each other by 44.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds..

2,4-Dichloro-N-(2,4-dimethylphenyl)benzenesulfonamide

“…The molecule is bent at the S atom with C-SO 2 -NH-C torsion angle of -71.38 (39)°, compared to the value of 67.45 (17)° in 4-chloro-2-methyl-N-(2,4-dimethylphenyl)benzenesulfonamide (II) (Rodrigues et al, 2011). The sulfonyl and the aniline benzene rings are tilted relative to each other by 44.6 (1)°, compared to the value of 44.5 (1)° in (II).…”

“…For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)amides, see: Arjunan et al (2004); Gowda et al (2000), on N-(aryl)-methanesulfonamides, see: Gowda et al (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al (2007); Perlovich et al (2006); Gowda et al (2005); Rodrigues et al (2011).…”

“…(Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al, 2004;Gowda et al, 2000), N-(aryl)-methanesulfonamides (Gowda et al, 2007) and N-(aryl)-arylsulfonamides (Gowda et al, 2005;Rodrigues et al, 2011), in the present work, the crystal structure of 2,4-dichloro-N-(2,4-dimethylphenyl)-benzenesulfonamide (I) has been determined ( Fig. 1).…”

“…The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006).…”

4-Chloro-N-(3,4-dimethylphenyl)-2-methylbenzenesulfonamide

“…The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al, 2007a), N-(aryl)-methanesulfonamides (Gowda et al, 2007b), N-(aryl)-arylsulfonamides (Rodrigues et al, 2011;Shetty & Gowda, 2005) and N-(chloro)-arylsulfonamides (Gowda et al, 2003), in the present work, the crystal structure of 4-Chloro-2-methyl-N-(3,4-dimethylphenyl)benzenesulfonamide (I) has been determined ( Fig. 1).…”