Halogen trimer-mediated hexagonal host framework of 2,4,6-tris(4- halophenoxy)-1,3,5-triazine. Supramolecular isomerism from hexagonal channel (X = Cl, Br) to cage structure (X = I)

Crystal Growth and Design

Volumn 5, Issue 3, 2005, Pages 887-899

  Saha, Binoy K ^a   Jetti, Ram K R ^a   Reddy, L Sreenivas ^a   Aitipamula, Srinivasulu ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLNAPHTHALENE; 1,3,5 TRIMETHYLBENZENE; BROMIDE; CHLORIDE; COLLIDINE; HALOGEN; HEXACHLOROBENZENE; HEXAFLUOROBENZENE; TRIAZINE DERIVATIVE;

ARTICLE; ATOM; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; ISOMERISM; MOLECULAR INTERACTION; MOLECULE; POLARIZATION; SOLID; SUPRAMOLECULAR CHEMISTRY; TEMPERATURE; THERMOGRAVIMETRY; X RAY ANALYSIS;

EID: 19944412224     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg049691r     Document Type: Article

References (89)

1. (a) MacNicol, D. D., Toda, F., Bishop, R., Eds. Comprehensive Supramolecular Chemistry, Vol. 6, Solid-State Supramolecular Chemistry, Crystal Engineering; Oxford, Pergamon: 1996.
2. (b) Bishop, R. Synlett 1999, 9, 1351-1358.
3. (c) Nangia, A. Curr. Opin. Solid State Mater. Sci. 2001, 5, 115-122.
4. (d) Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118.
5. (e) Nassimbeni, L. R. Acc. Chem. Res. 2003, 36, 631-637.
6. (f) Atwood, J. L., Steed, J. W., Eds. Encyclopedia of Supramolecular Chemistry; Marcel Dekker: New York, 2004.
7. (a) Hollingsworth, M. D. Science 2002, 295, 2410-2413.
8. (b) Atwood, J. L.; Barbour, L. J.; Jerga, A. Science 2002, 296, 2367-2369.
9. (a) Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657.
10. (b) Sharma, C. V. K.; Clearfield, A. J. Am. Chem. Soc. 2000, 122, 4394-4402.
11. (c) Plaut, D. J.; Lund, K. M.; Ward, M. D. Chem. Commun. 2000, 769-770.
12. (d) Zaworotko, M. J. Chem. Commun. 2001, 1-9.
13. (e) Hertzsch, T.; Budde, F.; Weber, E.; Hulliger, J. Angew. Chem., Int. Ed. 2002, 41, 2282-2284.
14. (f) Su, C.-Y.; Cai, Y.-P.; Chen, C.-L.; Lissner, F.; Kang, B.-S.; Kaim, W. Angew. Chem., Int. Ed. 2002, 41, 3371-3375.
15. (g) Ma, B.-Q.; Coppens, P. Chem. Commun. 2003, 2290-2291.
16. (a) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4698.
17. (b) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119-12120.
18. (c) Guo, W.; Galoppini, E.; Gilardi, R.; Rydja, G. I.; Chen, Y.-H. Cryst. Growth Des. 2001, 1, 231-237.
19. (d) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432-4445.
20. (e) Fournier, J. H.; Maris, T.; Wuest, J. D.; Guo, W. Z.; Galoppini, E. J. Am. Chem. Soc. 2003, 125, 1002-1006.
21. (f) Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem. 2004, 69, 1762-1775.
22. (a) Jetti, R. K. R.; Xue, F.; Mak, T. C. W.; Nangia, A. Cryst. Eng. 1999, 2, 215-224.
23. (b) Jetti, R. K. R.; Thallapally, P. K.; Xue, F.; Mak, T. C. W.; Nangia, A. Tetrahedron 2000, 56, 6707-6719.
24. (c) Jetti, R. K. R.; Nangia, A.; Xue, F.; Mak, T. C. W. Chem. Commun. 2001, 919-920.
25. (d) Broder, C. K.; Howard, J. A. K. H.; Keen, D. A.; Wilson, C. C.; Allen, F. H.; Jetti, R. K. R.; Nangia, A.; Desiraju, G. R. Acta Crystallogr., Section B 2000, 56, 1080-1084.
26. (e) Jetti, R. K. R.; Thallapally, P. K.; Nangia, A.; Lam, C.-K.; Mak, T. C. W. Chem. Commun. 2002, 952-953.
27. (f) Saha, B. K.; Aitipamula, S.; Banerjee, R.; Nangia, A.; Jetti, R. K. R.; Boese, R.; Lam, C.-K.; Mak, T. C. W. Mol. Cryst. Liq. Cryst., in press.
28. (a) Mann, S. Nature 1993, 365, 499-505.
29. (b) Jouaiti, A.; Hosseini, M. W.; Kyritsakas, N. Chem. Commun. 2003, 472-473.
30. (a) Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327.
31. (b) Nangia, A.; Desiraju, G. R. Top. Curr. Chem. 1998, 98, 57-95.
32. Angeloni, A.; Crawford, P. C.; Orpen, A. G.; Podesta, T. J.; Shore, B. J. Chem. Eur. J. 2004, 10, 3783-3791.
33. (a) Brammer, L.; Espallargas, G. M.; Adams, H. CrystEngComm 2003, 5, 343-345.
34. (b) Logothetis, T. A.; Meyer, F.; Metrangolo, P.; Pilati, T.; Resnati, G. New J. Chem. 2004, 28, 760-763.
35. Caira, M. R. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Eds.; Marcel Dekker: New York, 2004; pp 767-775.
36. Brock, C. P.; Dunitz, J. D. Chem. Mater. 1994, 6, 1118-1127.
37. Yao, J. W.; Cole, J. C.; Pidcock, E.; Allen, F. H.; Howard, J. A. K.; Motherwell, W. D. S. Acta Crysallogr., Sect. B 2002, 58, 640-646.
38. (a) Tanaka, K.; Fujimoto, D.; Oeser, T.; Irngartinger, H.; Toda, F. Chem. Commun. 2000, 413.
39. (b) Kumar, V. S. S.; Nangia, A. Chem. Commun. 2001, 2392-2393.
40. (c) Apel, A.; Lennartz, M.; Nassimbeni, L. R.; Weber, E. Chem. Eur. J. 2002, 8, 3678-3686.
41. (d) Rahman, A. N. M. M.; Bishop, R.; Craig, D. C.; Scudder, M. L. Org. Biol. Chem. 2003, 1, 1435-1441.
42. (e) Kumar, V. S. S.; Pigge, C. F.; Rath, N. P. Cryst. Growth Des. 2004, 4, 651-653.
43. (f) Alshahateet, S. F.; Bishop, R.; Craig, D. C.; Scudder, M. L. Cryst. Growth. Des. 2004, 4, 837-844.
44. (g) Kumar, V. S. S.; Pigge, F. C.; Rath, N. P. CrystEngComm 2004, 6, 531.
45. (a) Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308-4314.
46. (b) Desiraju, G. R.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111, 8725-8726.
47. (c) Price, S. L.; Stone, A. J.; Lucas, J.; Rowland, R. L.; Thornley, A. E. J. Am. Chem. Soc. 1994, 116, 4910-4918.
48. (d) Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Rae, D. C.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2353-2360.
49. (e) Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108-3116.
50. (a) Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469.
51. (b) Bosch, E.; Barnes, C. L. Cryst. Growth Des. 2002, 2, 299-302.
52. (c) Zaman, M. B.; Udachin, K. A.; Ripmeester, J. A. Cryst. Growth Des. 2004, 4, 585-589.
53. (a) Metrangolo, P.; Resnati, G. Chem. Eur. J. 2001, 7, 2511-2519.
54. (b) Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2004, 126, 4500-4501.
55. (c) Moorthy, J. N.; Vankatakrishnan, P.; Mal, P.; Dixit, S.; Venugopalan, P. Cryst. Growth. Des. 2003, 4, 581-585.
56. (a) Jessiman, A. S.; MacNicol, D. D.; Malinson, P. R.; Vallance, I. J. Chem. Soc., Chem. Commun. 1990, 1619-1621.
57. (b) Fábián, L.; Bombiez, P.; Czugler, M.; Kálmán, A.; Weber, E.; Hecker, M. Supramol. Chem. 1999, 11, 151-167.
58. (c) Thalladi, V. R.; Brasselet, S.; Weiss, H.-C.; Blaser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563-2577.
59. (d) Czugler, M.; Weber, E.; Párkányi, L.; Korkas, P. P.; Bombicz, P. Chem. Eur. J. 2003, 9, 3741-3747.
60. (a) Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
61. (b) Nyburg, S. C.; Faerman, C. H. Acta Crysallogr. Sect. B 1985, 41, 274-279.
62. Pogliani, L. New J. Chem. 2003, 27, 919-927.
63. (a) Desiraju, G. R.; Steiner, T. The Weak Hydrogen bond in Structural Chemistry and Biology; OUP: Oxford, 1999.
64. (b) Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565-573.
65. (a) Swift, J. A.; Pivovar, A. M.; Reynolds, A. M.; Ward, M. D. J. Am. Chem. Soc. 1998, 120, 5887-5994.
66. (b) Jetti, R. K. R.; Xue, F.; Mak, T. C. W.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232.
67. (c) Uemura, K.; Kitagawa, S.; Kondo, M.; Fukui, K.; Kituara, R.; Chang, H.-C.; Mizutani, T. Chem. Eur. J. 2002, 8, 3587-3600.
68. (d) Horn, C.; Berben, L.; Chow, H.; Scudder, M.; Dance, I. CrystEngComm 2002, 4, 7-12.
69. (e) Kobayashi, K.; Sato, A.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2003, 125, 3035-3045.
70. 2 using Dreiding2.21 force field. www.accelrys.com.
71. Reichenbächer, K.; Süss, H. I.; Stoeckli-Evans, H.; Bracco, S.; Sozzani, P.; Weber, E.; Hulliger, J. New. J. Chem. 2004, 28, 393-397.
72. Pidcock, E.; Motherwell, W. D. S.; Cole, J. C. Acta Crystallogr. Sect. B 2003, 59, 634-640.
73. Ohkita, M.; Kawano, M.; Suzuki, T.; Tsuji, T. Chem. Commun. 2002, 3054-3055.
74. Xu, K.; Ho, D. M.; Pascal, R. A. J. Am. Chem. Soc. 1994, 116, 105-110.
75. (a) Dance, I.; Scudder, M. New. J. Chem. 2001, 25, 1500-1509.
76. (b) Scudder, M.; Dance, I. Chem. Eur. J. 2002, 8, 5456-5468.
77. Boese, R.; Desiraju, G. R.; Jetti, R. K. R.; Kirchner, M. T.; Ledoux, I.; Thalladi, V. R.; Zyss, J. Struct. Chem. 2002, 13, 321-328.
78. (a) Desiraju, G. R. In Comprehensive Supramolecular Chemistry, Vol. 6, Solid-State Supramolecular Chemistry, Crystal Engineering; MacNicol, D. D., Toda, F., Bishop, R., Eds.; Oxford: Pergamon, 1996; pp 1-22.
79. (b) Thallapally, P. K.; Chakraborty, K.; Katz, A. K.; Carrell, H. L.; Kotha, S.; Desiraju, G. R. CrystEngComm 2001, 31, 1-3.
80. 1/c; QODSAD, C2/c; SAQZOY, P1; SAQZOY01, P1; EJERAM, P1. www.ccdc.cam.ac.uk.
81. George, S.; Nangia, A.; Lam, C.-K.; Mak, T. C. W.; Nicoud, J.-F. Chem. Commun. 2004, 1202-1203.
82. Complete structural and thermochemical characterization of disordered guest species in ethynyl-POT host is currently in progress. Details will be reported in a forthcoming paper.
83. Nassimbeni, L. R. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Eds.; Marcel Dekker: New York, 2004; pp 696-704.
84. Dey, A.; Jetti, R. K. R.; Boese, R.; Desiraju, G. R. CrystEngComm 2003, 5, 248-252.
85. (a) Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen, Germany, 1996.
86. (b) Sheldrick, G. M. Program for Multi-scan Absorption Correction of Area Detector Data, Version 2.10, University of Göttingen, Germany, 2003.
87. (a) Sheldrick, G. M. SHELXS-97: Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.
88. (b) Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
89. SHELXTL, Version 6.14, Bruker AXS, Program for the Solution and Refinement of Crystal Structures, Wisconsin, USA, 2000.