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

Abstract

The torsion angle of the C—SO2—NH—C moiety in the title compound, C13H10Cl3NO2S, is 50.4 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, linking the mol­ecules into zigzag chains parallel to the b axis.

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

“…Further, the sulfonyl group orients itself away from the ortho-methyl groups in both the rings. The molecule is bent at the S atom with the C-SO 2 -NH-C torsion angle of 67.5 (2), compared to the values of -66.8 (3)° and 70.3 (3)° in the two independent molecules of 4- (Rodrigues et al, 2011), and -61.9 (4)° and 69.7 (4)° in the two molecules of 4-chloro-2-methyl-N-(phenyl)-benzenesulfonamide (III) and -76.5 (5)° and -48.3 (4)° in 4-chloro-2methyl-N-(4-methylphenyl)-benzenesulfonamide (IV) (Gowda et al, 2010).…”

“…For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For studies of 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); Gowda et al (2010); Perlovich et al (2006); Rodrigues et al (2011).…”

“…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 (Arjunan et al, 2004;Gowda et al, 2000), N-(aryl)methanesulfonamides (Gowda et al, 2007) and N-(aryl)-arylsulfonamides (Gowda et al, 2010;Rodrigues et al, 2011), in the present work, the crystal structure of 4-Chloro-2-methyl-N-(2,4-dimethylphenyl)benzenesulfonamide (I) has been determined ( Fig. 1).…”

Bis(pyridyl)-disulfonamides: structural comparison with their carboxamidic analogues and the effect of molecular geometry and supramolecular assembly on their photophysical properties

“…Phenyl derivatives such as 1,2,3,4-tetraphenyl and 1,2,3,4,5-pentaphenyl benzene show AIEE. 7 In these compounds, unique molecular packing resulted in AIEE in their aggregated states. Intermolecular hydrogen bonding interactions in 2,7-bis(4-( tert -butylthio)-phenyl)fluorenone lead to the dimer formation in the ground state and it turned into an excimer without adjustment, and when the excimer decays back to the dimer, there is no repulsive interaction, which resulted in reduced non-radiative decay pathways and enhanced aggregation induced emission (AIE).…”