Crystal engineering of some 2,4,6-triaryloxy-1,3,5-triazines: Octupolar nonlinear materials

Journal of the American Chemical Society

Volumn 120, Issue 11, 1998, Pages 2563-2577

  Thalladi, Venkat R ^a   Brasselet, Sophie ^b,e   Weiss, Hans Christoph ^c   Bläser, Dieter ^c   Katz, Amy K ^d   Carrell, H L ^d   Boese, Roland ^c   Zyss, Joseph ^b,e   Nangia, Ashwini ^a   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b ORANGE LABS   (France)

^c UNIVERSITY OF DUISBURG ESSEN   (Germany)

^d FOX CHASE CANCER CENTER   (United States)

^e LABORATOIRE DE PHOTONIQUE QUANTIQUE ET MOLÉCULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL SYMMETRY; LIGHT SCATTERING; MOLECULAR CRYSTALS; MOLECULAR DYNAMICS; NONLINEAR OPTICS; OPTICAL MATERIALS; OPTIMIZATION; ORGANIC COMPOUNDS;

CRYSTAL ENGINEERING; OCTUPOLAR NONLINEAR MATERIALS; TRIARYLOXY TRIAZINES;

CRYSTAL STRUCTURE;

TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL ENGINEERING; CRYSTAL STRUCTURE; HYDROGEN BOND; LIGHT SCATTERING;

EID: 0032565077     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972830r     Document Type: Article

References (115)

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11. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
12. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
13. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
14. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
15. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
16. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
17. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
18. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
19. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
20. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
21. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
22. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
23. Some very recent papers in the area of crystal engineering include the following: (a) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575. (b) Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477. (c) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (e) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 102. (f) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765. (h) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. Z.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 213. (i) Lewis, F. D.; Yang, J.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 12029. (j) Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096. (k) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1690. (l) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492. (m) Kräutler, B.; Müller, T.; Maynollo, J.; Gruber, K.; Kratky, C.; Ochsenbein, P.; Schwarzenbach, D.; Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1204. (n) Glidewell, C.; Ferguson, G. Acta Crystallogr. 1996, C52, 2528.
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101. A similar situation is observed in the structure of hexaphenylmelamine (Lindeman, S. V.; Shklover, V. E.; Struchkov, Yu. T.; Kuznetsov, S. N.; Pankratov, V. A. Kristallografiya 1982, 27, 65).
102. Based on similar arguments Schwiebert et. al. have suggested in a recent paper (ref 2b) that chloro, bromo, and methyl derivatives of 2-benzimidazolones show offset stacking of tapes as opposed to perfect stacking of tapes in the unsubstituted hydrogen compound.
103. Sarma, J. A. R. P.; Desiraju, G. R. Acc. Chem. Res. 1986, 19, 222.
104. The corresponding fluoro triazine could not be crystallized for single-crystal X-ray analysis. Based on the powder X-ray spectrum of the material it was not possible to distinguish between noncentrosymmetric 1 and centrosymmetric 2. However, the absence of a powder SHG signal suggests that it adopts a centrosymmetric structure.
105. Desiraju, G. R.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111, 8725.
106. Desiraju, G. R.; Sarma, J. A. R. P. Proc. Ind. Acad. Sci. (Chem. Sci.) 1986, 96, 599.
107. (a) Jones, W.; Theocharis, C. R.; Thomas, J. M.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1983, 1443.
108. (b) Theocharis, C. R.; Desiraju, G. R.; Jones, W. J. Am. Chem. Soc. 1984, 106, 3606.
109. Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2353.
110. 2 = 0.3172, GOF = 1.280, C, N, O, Cl anisotropic, H isotropic.
111. Ermer, O.; Röbke, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1755.
112. Sakurai, T.; Sundaralingam, M.; Jeffrey, G. A. Acta Crystallogr. 1963, 16, 354.
113. 3 synthons equivalent to those found in 8 are seen in BROFRM03 (Myers, R.; Torrie, B. H.; Powell, B. M. J. Chem. Phys. 1983, 79, 1495) and JUHJIF (Tebbe, F. N.; Harlow, R. L.; Chase, D. B.; Thorn, D. L.; Campbell, G. C., Jr.; Calabrese, J. C.; Herron, N.; Young, R. J., Jr.; Wasserman, E. Science 1992, 256, 822).
114. 3 synthons equivalent to those found in 8 are seen in BROFRM03 (Myers, R.; Torrie, B. H.; Powell, B. M. J. Chem. Phys. 1983, 79, 1495) and JUHJIF (Tebbe, F. N.; Harlow, R. L.; Chase, D. B.; Thorn, D. L.; Campbell, G. C., Jr.; Calabrese, J. C.; Herron, N.; Young, R. J., Jr.; Wasserman, E. Science 1992, 256, 822).
115. 3 synthons equivalent to those found in 8 are seen in BROFRM03 (Myers, R.; Torrie, B. H.; Powell, B. M. J. Chem. Phys. 1983, 79, 1495) and JUHJIF (Tebbe, F. N.; Harlow, R. L.; Chase, D. B.; Thorn, D. L.; Campbell, G. C., Jr.; Calabrese, J. C.; Herron, N.; Young, R. J., Jr.; Wasserman, E. Science 1992, 256, 822).