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

Abstract

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.

Synthesis, crystal structure and studies on the interaction with albumin of a new silver(I) complex based on 2-(4-nitrobenzenesulfonamido)benzoic acid

“…The bond lengths of the sulfonamide group (formed by the N1, S1, O3, O4 and C8 atoms) do not change after complexation, similar to the bond lengths of the NO 2 group. In addition, both compounds show equivalent S O sulfonyl bond lengths, in good agreement with the literature (Shakuntala et al, 2017). The sulfonamide group presents a distorted tetrahedral arrangement around the S atom (Table 2).…”

New Approach to the Synthesis of 2‐Sulfonylaminosubstituted Imidazo[1,2‐a]pyridines via the Cascade Reaction of N‐(1‐aryl‐2,2,2‐trichloroethyl)sulfonamides with 2‐Aminopyridines

“…According to the data of X‐ray diffraction analysis, S2 sulfur atom adopts the conformation of a distorted tetrahedron. The valence angles within the experimental errors are close to the following values: O1 S1O2 120.4(1)°, O1 S1 C14 106.8(1)° ( 3 a ); O1 S1 N3106.4(1)°; O1 S1O2 120.7(2)°, O1 S1 C14 107.9(2)°, O1 S1 N3 106.8(2)° ( 3 j ); O1 S1O2 120.2(1)°, O1 S1 C14 108.4(1)°, O1 S1 N3 106.9(9)° ( 3 k ), which corresponds to compounds containing the sulfonamide group . The imidazole fragment has a planar structure; deviation of N1 and N2 heteroatoms from the C1 C2 C3 C5 C7 plane is 0.016 Å, 0.008 Å ( 3 a ); 0.011 Å, 0.058 Å ( 3 i ); 0.039 Å, 0.032 Å ( 3 k ).…”