Halogen containing clusters N2Br2, N2Br4, S2Br4 and S2Br6 yield penannular inclusion compounds

Solhe F. Alshahateet; Mohan M. Bhadbhade; Roger Bishop; Donald C. Craig; Marcia L. Scudder

doi:10.1039/C5CE01838B

Halogen containing clusters N₂Br₂, N₂Br₄, S₂Br₄ and S₂Br₆ yield penannular inclusion compounds†

Solhe F. Alshahateet,

*^a Mohan M. Bhadbhade,^b Roger Bishop,^c Donald C. Craig ‡^c and Marcia L. Scudder^c

Author affiliations

* Corresponding authors

^a Department of Chemistry, Faculty of Science, Mutah University, P. O. Box 7, Mutah 61710, Karak, Jordan
E-mail: s_alshahateet@mutah.edu.jo

^b Mark Wainwright Analytical Centre, The University of New South Wales, UNSW Sydney, NSW 2052, Australia

^c School of Chemistry, The University of New South Wales, UNSW Sydney, NSW 2052, Australia

Abstract

Crystallisation of the tetrahaloaryl host 2,4,10,12-tetrabromo-6,7,14,15-tetrahydro-6,14-thiacycloocta[1,2-b:5,6-b′]diquinoline 7 from benzene, chloroform, 3-methylpyridine, 4-methylpyridine, 2-methylpyridine, or tert-butylcyclohexane, yields a series of closely related inclusion compounds (7)₂·(guest) in space group P [1 with combining macron] . Two host molecules surround a single guest to form a penannular repeat unit in each of these crystal structures. Structural variation arises from the differing guest sizes, shapes and interactions. The corners of four molecular pens are linked by utilising novel S/Br clusters as supramolecular synthons: S₂Br₄ for the first four compounds, and S₂Br₆ for the latter two cases. The aromatic faces of the repeat units associate through offset π⋯π interactions. Aromatic edge–edge linkage occurs in the former group of compounds by means of N₂Br₂ and N₂Br₄ clusters, but these are absent in the final two structures. Mesitylene (1,3,5-trimethylbenzene) is too wide for penannular inclusion. It yields an alternative layer structure, (7)·(mesitylene), also in P [1 with combining macron] . This compound is stabilised by means of host–guest C–H⋯π associations, plus host–host aromatic and S⋯Br⋯Br⋯N interactions.

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Article information

DOI: https://doi.org/10.1039/C5CE01838B
Article type: Paper
Submitted: 16 Sep 2015
Accepted: 27 Oct 2015
First published: 04 Nov 2015

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CrystEngComm, 2015,17, 9111-9122

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Halogen containing clusters N₂Br₂, N₂Br₄, S₂Br₄ and S₂Br₆ yield penannular inclusion compounds

S. F. Alshahateet, M. M. Bhadbhade, R. Bishop, D. C. Craig and M. L. Scudder, CrystEngComm, 2015, 17, 9111 DOI: 10.1039/C5CE01838B

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