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, C14H13Cl2NO4S, (I), N-(2,4-dichlorophenyl)-
2,5-dimethoxybenzenesulfonamide, C14H13Cl2NO4S, (II), and N-(2,4-dimethylphenyl)-
2,5-dimethoxybenzenesulfonamide, C16H19NO4S, (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—
H  O interactions in (I), N—H  Cl and C—H  O interactions in (II), and
C—H  O interactions in (III). The crystals of the three compounds display
different supramolecular architectures built by various weak intermolecular
interactions of the types C—H  O, C—H  Cl, C—H  (aryl), (aryl)–
(aryl) and Cl  Cl. A detailed Hirshfeld surface analysis of these compounds
has also been conducted in order to understand the relationship between the
crystal structures. The dnorm 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 H  H contacts, followed by H  O/O  H contacts. In addition,
comparisons are made with the structures of some related compounds. Putative
N—H  O hydrogen bonds are observed in 29 of the 30 reported structures,
wherein the N—H  O hydrogen bonds form either C(4) chain motifs or R2
2(8)
rings. Further comparison reveals that the characteristics of the N—H  O
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—H  O
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.

Title

Acta Cryst. C,

Publisher

University of Delaware, USA

Publisher Country

United States of America

Indexing

Scopus

Impact Factor

None

Publication Type

Both (Printed and Online)

Volume

73

Year

2017

Pages

833–844