Different patterns of supra­molecular assembly in constitutionally similar 6-aryl­imidazo[2,1-b][1,3,4]thia­diazo­les

Praveen, A. S. and Yathirajan, H. S. and Kaur, Manpreet and Narayana, B. and Hosten, Eric C. and Betz, Richard and Glidewell, Christopher (2014) Different patterns of supra­molecular assembly in constitutionally similar 6-aryl­imidazo[2,1-b][1,3,4]thia­diazo­les. Acta Crystallographica Section C, 70 (9). pp. 920-926. ISSN 2053-2296

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Official URL: https://doi.org/10.1107/S2053229614018762

Abstract

Four imidazo[2,1-b][1,3,4]thia­diazo­les containing a simply-substituted 6-aryl group have been synthesized by reaction of 2-amino-1,3,4-thia­diazo­les with bromo­acetyl­arenes using micro­wave irradiation and brief reaction times. 6-(2-Chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole, C10H6ClN3S, (I), 6-(2-chloro­phen­yl)-2-methyl­imidazo[2,1-b][1,3,4]thia­diazole, C11H8ClN3S, (II), 6-(3,4-di­chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-meth­oxy­phen­yl)-2-methyl­imidazo[2,1-b][1,3,4]thia­diazole, C12H10FN3OS, (IV), crystallize with Z′ values of 2, 1, 1 and 2 res­pec­tively. The mol­ecular skeletons are all nearly planar and the dihedral angles between the imidazole and aryl rings are 1.51 (8) and 7.28 (8)° in (I), 9.65 (7)° in (II), 10.44 (8)° in (III), and 1.05 (8) and 7.21 (8)° in (IV). The mol­ecules in (I) are linked by three independent C—H⋯N hydrogen bonds to form ribbons containing alternating R22(8) and R44(18) rings, and these ribbons are linked into a three-dimensional array by three independent π-stacking inter­actions. Both (II) and (III) contain centrosymmetric dimers formed by π-stacking inter­actions but hydrogen bonds are absent, and the mol­ecules of (IV) are linked into centrosymmetric R22(8) dimers by C—H⋯N hydrogen bonds. Comparisons are made with a number of related compounds.

Item Type: Article
Uncontrolled Keywords: crystal structure, imidazo2,1-b1,3,4thiadiazoles, molecular conformation, supramolecular assembly, pharmaceutical compounds, hydrogen bonding
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: C Swapna Library Assistant
Date Deposited: 13 Nov 2019 05:46
Last Modified: 13 Nov 2019 05:46
URI: http://eprints.uni-mysore.ac.in/id/eprint/9999

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