Naveen, S. and Sudha, A. and Suresha, E. and Lokanath, N. K. and Suchetan, P. A. (2017) Supramolecular architectures in N-(4-bromobenzoyl)-arylsulfonamides: crystal structures and Hirshfeld surface analysis. Zeitschrift für Kristallographie-Crystalline Materials, 232 (11). pp. 767-780. ISSN 0044-2968
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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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | crystal structure analysis; Hirshfeld surface; hydrogen-bonding; sulfonamides; X-ray diffraction |
| Subjects: | C Chemical Science > Chemistry D Physical Science > Physics |
| Divisions: | Department of > Chemistry Department of > Physics |
| Depositing User: | C Swapna Library Assistant |
| Date Deposited: | 30 May 2019 09:59 |
| Last Modified: | 30 May 2019 09:59 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/689 |
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