Pi-halogen dimer interactions and the inclusion chemistry of a new tetrahalo aryl host

Organic and Biomolecular Chemistry

Volumn 2, Issue 2, 2004, Pages 175-182

  Rahman, A Noman M M ^a   Bishop, Roger ^a   Craig, Donald C ^a   Scudder, Marcia L ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CRYSTAL LATTICES; CRYSTALLIZATION; DIMERS; HALOGEN ELEMENTS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; TOLUENE;

INCLUSION CHEMISTRY; PACKING ENERGY; X-RAY STRUCTURES;

SYNTHESIS (CHEMICAL);

EID: 0942279293     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310638a     Document Type: Article

References (34)

1. C. E. Marjo, A. N. M. M. Rahman, R. Bishop, M. L. Scudder and D. C. Craig, Tetrahedron, 2001, 57, 6289-6293.
2. Inclusion Compounds, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, vol. 1-3, Academic Press: London, 1984; Inclusion Compounds, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, vol. 4-5, Oxford University Press: Oxford, 1991.
3. Inclusion Compounds, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, vol. 1-3, Academic Press: London, 1984; Inclusion Compounds, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, vol. 4-5, Oxford University Press: Oxford, 1991.
4. Comprehensive Supramolecular Chemistry, eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, vol. 1-11, Pergamon: Oxford, 1996.
5. K. Tanaka, D. Fujimoto, A. Altreuther, T. Oeser, H. Irngartinger and F. Toda, J. Chem. Soc., Perkin Trans. 2, 2000, 2115-2120.
6. K. Tanaka, D. Fujimoto and F. Toda, Tetrahedron Lett., 2000, 41, 6095-6099.
7. K. Tanaka, D. Fujimoto, T. Oeser, H. Irngartinger and F. Toda, Chem. Commun., 2000, 413-414.
8. A. N. M. M. Rahman, R. Bishop, D. C. Craig, C. E. Marjo and M. L. Scudder, Cryst. Growth Des., 2002, 2, 421-426.
9. C. E. Marjo, R. Bishop, D. C. Craig, A. O'Brien and M. L. Scudder, J. Chem. Soc., Chem. Commun., 1994, 2513-2514.
10. A. N. M. M. Rahman, R. Bishop, D. C. Craig and M. L. Scudder, Eur. J. Org. Chem., 2003, 72-81.
11. P. B. D. de la Mare, M. Kiamud-din and J. H. Ridd, Chem. Ind. (London), 1958, 361.
12. P. B. D. de la Mare, M. Kiamud-din and J. H. Ridd, J. Chem. Soc., 1960, 561-565.
13. Compound (6),·(1,2,3-trichloropropane): P1, a 14.639, b 14.749, c 15.022 Å, a 69.18, 62.96, γ 61.50°. Two crystallographically independent guest molecules are present in this staircase structure, and the disorder of one of these prevented refinement to acceptable limits.
14. A. N. M. M. Rahman, R. Bishop, D. C. Craig and M. L. Scudder, CrystEngComm, 2002, 4(84), 510-513.
15. G. R. Desiraju and A. Gavezzotti, Acta Crystallogr., Sect. B, 1989, 45, 473-482.
16. C. A. Hunter, K. R. Lawson, J. Perkins and C. J. Urch, J. Chem. Soc., Perkin Trans. 2, 2001, 651-669.
17. R. K. R. Jetti, A. Nangia, F. Xue and T. C. W. Mak, Chem. Commun., 2001, 919-920.
18. A preliminary account of the allyl cyanide and carbon tetrachloride structures (CSD refcodes HUKPIM and HUKPOS) appears in ref. 13. Our report of a short Cl ⋯ Cl contact of 2.8 Å in the latter structure is wrong. When the correct guest disorder components are chosen, the value is an unremarkable 3.66 Å.
19. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989.
20. A. N. M. M. Rahman, R. Bishop, D. C. Craig and M. L. Scudder, CrystEngComm, 2002, 4(101), 605-609.
21. A preliminary account of the toluene and solvent free structures (CSD refcodes WUHNES and WUHNAO) appears in ref. 19.
22. A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973.
23. H. Suezawa, T. Yoshida, M. Hirota, H. Takahashi, Y. Umezawa, K. Honda, S. Tsuboyama and M. Nishio, J. Chem. Soc., Perkin Trans. 2, 2001, 2053-2058.
24. C. E. Marjo, M. L. Scudder, D. C. Craig and R. Bishop, J. Chem. Soc., Perkin Trans. 2, 1997, 2099-2104.
25. S. F. Alshahateet, R. Bishop, D. C. Craig and M. L. Scudder, CrystEngComm, 2001, 3(48), 225-229.
26. B. S. Green and G. M. J. Schmidt, Tetrahedron Lett., 1970, 4249-4252.
27. A. Elgavi, B. S. Green and G. M. J. Schmidt, J. Am. Chem. Soc., 1973, 95, 2058-2059.
28. J. D. Dunitz, G. Filippini and A. Gavezzotti, Tetrahedron, 2000, 56, 6595-6601.
29. 2 ® version 3.8. http://www.accelrys.com.
30. J. De Meulenaer and M. Tompa, Acta Crystallogr., 1965, 19, 1014-1018.
31. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Crystallogr., 1994, 27, 435.
32. A. D. Rae, RAELS. A Comprehensive Constrained Least Squares Refinement Program, Australian National University, Canberra, Australia, 2000.
33. International Tables for X-Ray Crystallography, Vol. 4 (Eds.: J. A. Ibers, W. C. Hamilton), Kynoch Press, Birmingham, 1974.
34. A. K. Rappe and W. A. Goddard, J. Phys. Chem., 1991, 95, 3358-3363.