A novel saturated hydrogen bridge architecture in supraminols

Crystal Growth and Design

Volumn 4, Issue 4, 2004, Pages 647-649

  Bhogala, Balakrishna R ^a   Vangala, Venu R ^a   Smith, Philip S ^b   Howard, Judith A K ^b   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPHENOL DERIVATIVE; HYDROGEN; ZEOLITE;

ARTICLE; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; LOW TEMPERATURE; STRUCTURE ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 4143058237     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg049916y     Document Type: Article

References (29)

1. Desiraju, G. R. Crystal Engineering. The Design of Organic Solids; Elsevier: Amsterdam, 1989.
2. Ermer, O.; Eling, A. J. Chem. Soc., Perkin Trans. 2 1994, 925-944.
3. (a) Roelens, S.; Dapporto, P.; Paoli, P. Can. J. Chem. 2000, 78, 723-731.
4. (b) Dapporto, P.; Paoli, P.; Roelens, S. J. Org. Chem. 2001, 66, 4930-4933.
5. (c) Hanessian, S.; Saladino, R. in Crystal Design. Structure and Function. Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: New York, 2003; Vol. 7, pp 77-151.
6. (a) 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, 3477-3480.
7. (b) Vangala, V. R.; Bhogala, B. R.; Dey, A.; Desiraju, G. R.; Broder, C. K.; Smith, P. S.; Mondal, R.; Howard, J. A. K.; Wilson, C. C. J. Am. Chem. Soc. 2003, 125, 14495-14509.
8. Loehlin, J. H.; Franz, K. J.; Gist, L.; Moore, R. H. Acta Crystallogr. 1998, B54, 695-704.
9. (a) β-As sheet: AMPHOL01, HIBFUT, NISMAD, PITYAS, PITYEW, PITYIA, PITYOG, PITZAT, SARDAQ, SARDIY, SARDOE, SARJUQ, ZAPFAX, ZAPFEB, and six β-As structures reported by us previously: see ref 4b and compounds 2, 4, 2a, 2b, 2d, and 1b of that paper.
10. (b) Black-P sheet: JAKKEL
11. (c) SHB ladder: GUCQUQ, GUCREB, GUCRIF, HYDETH, ZAVXAV.
12. (d) SHB ladder in unsaturated supraminols include: PIWXOI, PIWXUO.
13. 2 with SHELXTL programs. The hydroxy and amine hydrogen atoms were located in difference Fourier maps and refined isotropically. The other hydrogen atoms were fixed in geometrically sensible positions.
14. (a) Lowdin, P.-O. J. Chem. Phys. 1950, 18, 365-375.
15. (b) Fábián, L.; Kálmán, A. Acta Crystallogr. 1999, B55, 1099-1108.
16. Pertinent hydrogen bridges for 2: O-H⋯N (1.75 Å, 167.5°; 1.82 Å, 173.4°), N-H⋯O (2.01 Å, 157.6°; 2.15 Å, 154.8°; 2.18 Å, 152.9°; 2.28 Å, 139.7°).
17. (a) Peacor, D. R.; Buerger, M. J. Am. Mineral. 1962, 47, 539-556.
18. (b) Ribeiro, F. R.; Rodrigues, A. E.; Rollmann, L. D.; Naccache, C. Zeolites: Science and Technology; E80, NATO ASI Series: Boston, 1984.
19. Reddy, D. S.; Craig, D. C.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1995, 339-340.
20. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
21. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
22. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
23. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
24. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
25. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
26. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
27. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
28. Selected references that describe network structures include: (a) Wells, A. F. Structural Inorganic Chemsitry, 5th ed.; Oxford University Press: Oxford, 1984. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (c) Desiraju, G. R. Chem. Commun. 1997, 1475-1482. (d) Batten, S. R.; Robson, R. Angew. Chem., Int, Ed. 1998, 37, 1460-1494. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908. (f) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658. (g) Biradha, K. CrystEngComm 2003, 5, 374-384. (h) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714. (i) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1-11.
29. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.