Supramolecular architectures in N-(4-bromobenzoyl)-arylsulfonamides: crystal structures and Hirshfeld surface analysis

Shivalingegowda Naveen; Achar Gurumurthy Sudha; Erachikkaiah Suresha; Neratur Krishnappagowda Lokanath; Parameshwar Adimule Suchetan

doi:10.1515/zkri-2016-2008

Published by De Gruyter (O) May 23, 2017

Supramolecular architectures in N-(4-bromobenzoyl)-arylsulfonamides: crystal structures and Hirshfeld surface analysis

Shivalingegowda Naveen , Achar Gurumurthy Sudha , Erachikkaiah Suresha , Neratur Krishnappagowda Lokanath and Parameshwar Adimule Suchetan

From the journal Zeitschrift für Kristallographie - Crystalline Materials

https://doi.org/10.1515/zkri-2016-2008

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Abstract

A detailed analysis of the molecular packing of five N-(4-bromobenzoyl)-substituted benzenesulfonamides, i-X~4-Br (1–5) [i-X=H, 2-CH₃, 4-CH₃, 2-Cl, 4-Cl] is presented. The intermolecular interactions and the packing patterns are evaluated along with an analysis of their Hirshfeld surfaces and fingerprint plots (FP). The crystals feature molecular self-assembly through N–H···O hydrogen-bonds forming three types of supramolecular synthon: C11(4) chain, R44(16) tetramer and R22(8) ring. These molecular assemblies extend to form one-dimensional (1D), 2D or 3D supramolecular architectures via diverse intermolecular interactions. A study of 33 i-X~4-Y (Y=H, CH₃, OCH₃, NO₂, F, Cl, Br) structures shows the substituent on the sulfonamide ring modulates the intermolecular interactions and the subsequent supramolecular architectures drastically, with the fluoro- and bromo-substituted analogues providing distinctive self-assemblies. The R44(16) synthon produced by N–H···O hydrogen-bonds in the 4-CH₃~4-Br derivative is a rare phenomenon amongst a set of 74 i-X~j-Y structures.

Keywords: crystal structure analysis; Hirshfeld surface; hydrogen-bonding; sulfonamides; X-ray diffraction

Acknowledgments

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Manasagangotri, Mysore, for providing the single-crystal X-ray diffraction data.

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Supplemental Material:

The online version of this article (DOI: https://doi.org/10.1515/zkri-2016-2008) offers supplementary material, available to authorized users.

Received: 2016-9-22

Accepted: 2017-4-14

Published Online: 2017-5-23

Published in Print: 2017-10-26

Supramolecular architectures in N-(4-bromobenzoyl)-arylsulfonamides: crystal structures and Hirshfeld surface analysis

Abstract

Acknowledgments

References

Supplemental Material:

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