Inclusion compounds of hexakis(4-cyanophenyl)benzene: Open networks maintained by C-H⋯N interactions

Crystal Growth and Design

Volumn 6, Issue 2, 2006, Pages 461-466

  Maly, Kenneth E ^a   Maris, Thierry ^a   Gagnon, Eric ^a   Wuest, James D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 32644444725     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg050384a     Document Type: Article

References (40)

1. Fellow of the Natural Sciences and Engineering Research Council of Canada, 2003-2004.
2. Fellow of the Natural Sciences and Engineering Research Council of Canada, 2003.
3. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658.
4. Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426.
5. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
6. For recent references, see Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698.
7. Sauriat-Dorizon, H.; Maris, T.; Wuest, J. D.; Enright, G. D. J. Org. Chem. 2003, 68, 240-246.
8. Fournier, J.-H.; Maris, T.; Wuest, J. D.; Guo, W.; Galoppini, E. J. Am. Chem. Soc. 2003, 125, 1002-1006.
9. Fournier, J.-H.; Maris, T.; Simard, M.; Wuest, J. D. Cryst. Growth Des. 2003, 3, 535-540.
10. Laliberté, D.; Maris, T.; Sirois, A.; Wuest, J. D. Org. Lett. 2003, 5, 4787-4790.
11. Laliberté, D.; Maris, T.; Wuest, J. D. Can. J. Chem. 2004, 82, 386-398.
12. Laliberté, D.; Maris, T.; Wuest, J. D. J. Org. Chem. 2004, 69, 1776-1787.
13. Laliberté, D.; Maris, T.; Demers, E.; Helzy, F.; Arseneault, M.; Wuest, J. D. Cryst. Growth Des. 2005, 5, 1451-1456.
14. Demers, E.; Maris, T.; Wuest, J. D. Cryst. Growth Des. 2005, 5, 1227-1235.
15. Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem. 2004, 69, 1762-1775.
16. Bernstein, J. In Organic Solid State Chemistry; Desiraju, G. R., Ed.; Elsevier: Amsterdam, 1987; pp 471-518.
17. Byrn, M. P.; Curtis, C. J.; Khan, S. I.; Sawin, P. A.; Tsurumi, R.; Strouse, C. E. J. Am. Chem. Soc. 1990, 112, 1865-1874.
18. Nangia, A.; Desiraju, G. R. Chem. Commun. 1999, 605-606.
19. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
20. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565-573.
21. Basavoju, S.; Aitipamula, S.; Desiraju, G. R. CrystEngComm 2004, 6, 120-125.
22. Kumar, V. S. S.; Pigge, F. C.; Rath, N. P. Cryst. Growth Des. 2004, 4, 651-653.
23. Kumar, V. S. S.; Pigge, F. C.; Rath, N. Cryst. Growth Des. 2004, 4, 1217-1222.
24. Kumar, V. S. S.; Pigge, F. C.; Rath, N. P. New J. Chem. 2003, 27, 1554-1556.
25. Demers, E.; Maris, T.; Cabana, J.; Fournier, J.-H.; Wuest, J. D. Cryst. Growth Des. 2005, 5, 1237-1245.
26. Bart, J. C. J. Acta Crystallogr. 1968, B24, 1277-1287.
27. Larson, E. M.; Von Dreele, R. B.; Hanson, P.; Gust, J. D. Acta Crystallogr. 1990, C46, 784-788.
28. Kobayashi, K.; Shirasaka, T.; Sato, A.; Horn, E.; Furukawa, N. Angew. Chem., Int. Ed. 1999, 38, 3483-3486.
29. Kobayashi, K.; Shirasaka, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93.
30. Kobayashi, K.; Sato, A.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2003, 125, 3035-3045.
31. Kobayashi, K.; Kobayashi, N.; Ikuta, M.; Thierrien, B.; Sakamoto, S.; Yamaguchi, K. J. Org. Chem. 2005, 70, 749-752.
32. Sakon, Y.; Ohnuma, T.; Hashimoto, M.; Saito, S.; Tsutsui, T.; Adachi, C. U.S. Patent 5077142, 1991.
33. Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Lett. 2001, 3, 2887-2890.
34. Wu, J.; Watson, M. D.; Müllen, K. Angew. Chem., Int. Ed. 2003, 42, 5329-5333.
35. See Supporting Information for a more detailed description.
36. The percentage of volume accessible to guests was estimated by the PLATON program. PLATON calculates the accessible volume by allowing a spherical probe of variable radius to roll over the van der Waals surface of the network. PLATON uses a default value of 1.20 Å for the radius of the probe, which is an appropriate model for small guests such as water.
37. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2001.
38. van der Sluis, P.; Spek, A. L. Acta Crystallogr. 1990, A46, 194.
39. Representations of channels were generated by the Cavities option in the program ATOMS (ATOMS, Version 5.1; Shape Software: 521 Hidden Valley Road, Kingsport, TN 37663; www.shapesoftware.com).
40. Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures and SHELXL-97, Program for the Refinement of Crystal Structures; Universität Göttingen: Germany, 1997.