Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo2,1-b1,3,4thiadiazoles

Praveen, A. S. and Yathirajan, H. S. and Kaur, M. and Narayana, B. and Hosten, E. C. and Betz, Richard and Glidewell, Christopher (2014) Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo2,1-b1,3,4thiadiazoles. Acta Crystallographica Section C: Structural Chemistry, 70. pp. 920-926. ISSN 2053-2296

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Abstract

Four imidazo2,1-b1,3,4thiadiazoles 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)imidazo2,1-b1,3,4thiadiazole, C10H6ClN3S, (I), 6-(2-chlorophenyl)-2-methylimidazo2,1-b1,3,4thiadiazole, C11H8ClN3S, (II), 6-(3,4-dichlorophenyl)imidazo2,1-b1,3,4thiadiazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-methoxyphenyl)-2-methylimidazo2,1-b1,3,4thiadiazole, 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 R 2 2 (8) and R 4 4 (18) rings, and these ribbons are linked into a three-dimensional array by three independent �-stacking interactions. Both (II) and (III) contain centrosymmetric dimers formed by �-stacking interactions but hydrogen bonds are absent, and the molecules of (IV) are linked into centrosymmetric R 2 2 (8) dimers by C - H�N hydrogen bonds. Comparisons are made with a number of related compounds.

Item Type:	Article
Uncontrolled Keywords:	3, Crystal structure, Hydrogen bonds, Dihedral angle, Molecules, chemical structure, chemistry, Molecular Structure, imidazole derivative, Imidazoles, Crystallography, hydrogen bond, Hydrogen Bonding, X ray crystallography, X-Ray, Molecular conformation, Supramolecular assemblies, Supramolecular chemistry, Complexation, Dimers, Related compounds, Organic compounds, imidazole, 1-b)(1, 4-dichlorophenyl)imidazo(2, 4)thiadiazole, 6-(2-chlorophenyl)-2-methylimidazo(2, 6-(2-chlorophenyl)imidazo(2, 6-(3, Centrosymmetric dimers, Microwave irradiation, Molecular skeleton, Pharmaceutical compounds, thiadiazole derivative, Thiadiazoles, Three dimensional arrays
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	31 Aug 2019 05:56
Last Modified:	21 Jul 2022 10:16
URI:	http://eprints.uni-mysore.ac.in/id/eprint/4297

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