Crystal structures of isomeric 3,5-di­chloro-N-(2,3-di­methyl­phen­yl)benzene­sulfonamide, 3,5-di­chloro-N-(2,6-di­methyl­phen­yl)benzene­sulfonamide and 3,5-di­chloro-N-(3,5-di­methyl­phen­yl)benzene­sulfonamide

Shakuntala, K. and Naveen, S. and Lokanath, N. K. and Suchetan, P. A. (2017) Crystal structures of isomeric 3,5-di­chloro-N-(2,3-di­methyl­phen­yl)benzene­sulfonamide, 3,5-di­chloro-N-(2,6-di­methyl­phen­yl)benzene­sulfonamide and 3,5-di­chloro-N-(3,5-di­methyl­phen­yl)benzene­sulfonamide. Acta Crystallographica Section E, 73 (5). pp. 673-677. ISSN 2056-9890

Text (Full Text) Crystal structures of isomeric 3,5-di­chloro-N-(2,3-di­methyl­phen­yl)benzene­sulfonamide.pdf - Published Version Download (1MB)

Abstract

The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di­chloro-N-(2,3-di­methyl­phen­yl)-benzene­sulfonamide (I), 3,5-di­chloro-N-(2,6-di­methyl­phen­yl)benzene­sulfonamide (II) and 3,5-di­chloro-N-(3,5-di­methyl­phen­yl)benzene­sulfonamide (III) are described. The mol­ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol­ecular conformation of (II) is stabilized by intra­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions. The crystal structure of (I) features N—H⋯O hydrogen-bonded R22(8) loops inter­connected via C(7) chains of C—H⋯O inter­actions, forming a three-dimensional architecture. The structure also features π–π inter­actions [Cg⋯Cg = 3.6970 (14) Å]. In (II), N—H⋯O hydrogen-bonded R22(8) loops are inter­connected via π–π inter­actions [inter­centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N—H⋯O hydrogen-bonded mol­ecules running parallel to [010] are connected via C—H⋯π inter­actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π–π inter­actions [inter­centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

Item Type:	Article
Uncontrolled Keywords:	crystal structure, sulfonamides, N-H...O hydrogen bonds, C-H...O interactions, C-H...pi interactions, pi-pi interactions
Subjects:	D Physical Science > Physics
Divisions:	Department of > Institution of Excellence Department of > Physics
Depositing User:	C Swapna Library Assistant
Date Deposited:	05 Jul 2019 05:15
Last Modified:	05 Jul 2019 05:15
URI:	http://eprints.uni-mysore.ac.in/id/eprint/4611

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