Synthesis and supramolecular interactions involved in the crystal structure of (2,4,10,12-tetrabromo-6,7,14,15-tetrahydro-6, 14-thiacycloocta[1,2-b:5,6-b’]diquinoline)₂·(1,1,2,2-tetrachloroethane) inclusion compound

Abstract

The tetrahalo aryl inclusion host 2,4,10,12-tetrabromo-6,7,14,15-tetrahydro-6,14-thiacycloocta[1,2-b:5,6-b’]diquinoline 3 was re-synthesized to explore its ability to trap toxic polychlorinated hydrocarbons such as 1,1,2,2-tetrachloroethane (TCE) in the form of host–guest compound. Host 3 crystallizes from a fresh sample of TCE to form an inclusion compound of the formula (3)₂·(TCE) in triclinic system, space group P-1, with a = 7.7732(16) Å, b = 10.739(2) Å, c = 14.816(3) Å, α = 97.329(4)°, β = 98.619(4)°, γ = 103.359(4)°, V = 1172.7(4) ų, and Z = 2. The X-ray crystal structure of the (3)₂·(1,1,2,2-TCE) is described and analyzed in terms of crystal engineering and supramolecular chemistry. The hosts assemble by means of different types of packing motifs. The included TCE molecules are enclosed within host molecular pens. Novel halogen···halogen intermolecular interactions as well as other non-covalent intermolecular interactions involved in the crystal structure are presented and proved to play an important role in linking these host–host, host–guest, and guest–guest building blocks.

Keywords:

• Halogen···halogen intermolecular interactions
• host–guest system
• non-covalent intermolecular interactions; 2; 4; 10
• 12-tetrabromo-6; 7; 14
• 15-tetrahydro-6
• 14-thiacycloocta[1;2-b:5
• 6-b’]diquinoline; 1; 1; 2
• 2-tetrachloroethane (TCE)
• X-ray single crystal structure

Acknowledgments

The author would like to thank Mutah University and National University of Singapore for technical support and assistance needed to finish and obtain this work in its current form.