2,4-Dichloro-<i>N</i>-(3,4-dichlorophenyl)benzenesulfonamide

Gowda, B.T.; Foro, Sabine; Nirmala, P.G.; Fueß, H.

doi:10.1107/s1600536809027883

Cited by 6 publications

(1 citation statement)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Series 1: 2,4-dichloro-N-(disubstituted phenyl)benzenesulfonamides consisting of eight compounds, namely 2,4-dichloro-N-(2,3-dichloro/3,4-dichloro/3,5-dichloro/2,4-dimethyl/ 2,5-dimethyl/2,6-dimethyl/3,4-dimethyl/3,5-dimethylphenyl)-benzenesulfonamides (Gowda et al, 2009a;Vinola et al, 2011a-g). …”

Section: å Which Is Very Close To the Observed H1á á áO1mentioning

confidence: 99%

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

Shakuntala¹,

Naveen

Lokanath

et al. 2017

Acta Crystallogr C

View full text Add to dashboard Cite

The synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety have attracted interest as these compounds are important pharmacophores. The crystal structures of three closely related N-aryl-2,5-dimethoxybenzenesulfonamides, namely N-(2,3-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C 14 H 13 Cl 2 NO 4 S, (I), N-(2,4-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C 14 H 13 Cl 2 NO 4 S, (II), and N-(2,4-dimethylphenyl)-2,5-dimethoxybenzenesulfonamide, C 16 H 19 NO 4 S, (III), are described. The asymmetric unit of (I) consists of two symmetry-independent molecules, while those of (II) and (III) contain one molecule each. The molecular conformations are stabilized by different intramolecular interactions, viz. C-HÁ Á ÁO interactions in (I), N-HÁ Á ÁCl and C-HÁ Á ÁO interactions in (II), and C-HÁ Á ÁO interactions in (III). The crystals of the three compounds display different supramolecular architectures built by various weak intermolecular interactions of the types C-HÁ Á ÁO, C-HÁ Á ÁCl, C-HÁ Á Á(aryl), (aryl)-(aryl) and ClÁ Á ÁCl. A detailed Hirshfeld surface analysis of these compounds has also been conducted in order to understand the relationship between the crystal structures. The d norm and shape-index surfaces of (I)-(III) support the presence of various intermolecular interactions in the three structures. Analysis of the fingerprint plots reveals that the greatest contribution to the Hirshfeld surfaces is from HÁ Á ÁH contacts, followed by HÁ Á ÁO/OÁ Á ÁH contacts. In addition, comparisons are made with the structures of some related compounds. Putative N-HÁ Á ÁO hydrogen bonds are observed in 29 of the 30 reported structures, wherein the N-HÁ Á ÁO hydrogen bonds form either C(4) chain motifs or R 2 2 (8) rings. Further comparison reveals that the characteristics of the N-HÁ Á ÁO hydrogen-bond motifs, the presence of other interactions and the resultant supramolecular architecture is largely decided by the position of the substituents on the benzenesulfonyl ring, with the nature and position of the substituents on the aniline ring exerting little effect. On the other hand, the crystal structures of (I)-(III) display several weak interactions other than the common N-HÁ Á ÁO hydrogen bonds, resulting in supramolecular architectures varying from one-to three-dimensional depending on the nature and position of the substituents on the aniline ring.

show abstract

Section: å Which Is Very Close To the Observed H1á á áO1mentioning

confidence: 99%

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

Shakuntala¹,

Naveen

Lokanath

et al. 2017

Acta Crystallogr C

View full text Add to dashboard Cite

show abstract

N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide

et al. 2009

Self Cite

View full text Add to dashboard Cite

In the crystal structure of the title compound, C14H13Cl2NO2S, the configurations of the N—C bond with respect to the S=O bonds are trans and gauche. The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of −69.7 (2)°. The conformation of the N—H bond is syn to the 3-chloro group in the substituted aniline ring. The two benzene rings are tilted with respect to each other by 82.4 (1)°. The presence of N—H⋯O(S) hydrogen bonding packs the molecules into supramolecular chains along the b axis.

show abstract

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

et al. 2009

Self Cite

View full text Add to dashboard Cite

Key indicators: single-crystal X-ray study; T = 299 K; mean (C-C) = 0.006 Å; disorder in main residue; R factor = 0.062; wR factor = 0.199; data-to-parameter ratio = 12.5.The title compound, C 13 H 11 Cl 2 NO 2 S, crystallizes with four independent molecules in the asymmetric unit. In each of the four molecules, the conformation of the N-C bond in the C-SO 2 -NH-C segment is gauche with respect to both S O bonds. The molecules are twisted at the S-N bonds with C-SO 2 -NH-C torsion angles of 60.6 (4), À59.7 (3), 63.9 (4) and 53.0 (4) . The benzene rings in two of the molecules are disordered with multiple positions resolved in each case. The crystal structure features inversion dimers linked by pairs of N-HÁ Á ÁO hydrogen bonds for each of the four molecules. Related literature ExperimentalCrystal data independent and constrained refinement Á max = 0.70 e Å À3

show abstract

2,4-Dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide

Cited by 6 publications

References 7 publications

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide

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

Contact Info

Product

Resources

About