Thermal conversion of a helical coil into a three-dimensional chiral framework

Angewandte Chemie - International Edition

Volumn 38, Issue 23, 1999, Pages 3498-3501

  Ranford, John D ^a   Vittal, Jagadese J ^a   Wu, Daqing ^a   Yang, Xiandong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Chirality; Copper; Crystal engineering; Helical structures; Supramolecular chemistry

Indexed keywords

COPPER;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; DEHYDRATION; HYDROGEN BOND; SOLID STATE; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 0033521212     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3498::AID-ANIE3498>3.0.CO;2-F     Document Type: Article

References (38)

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2. See, for example, a) G. R. Desiraju, Chem. Commun. 1997, 1475- 1482; b) Crystal Engineering: The Design of Organic Solids, Materials Science Monographs 54, Elsevier, Amsterdam, 1989; c) J. J. Wolff, Angew. Chem. 1996, 108, 2339-2341; Angew. Chem. Int. Ed. Engl. 1996, 35, 2195-2197; d) G. R. Desiraju, J. Mol. Struct. 1996, 374, 191- 198; e) M. E. Davis, Chem. Eur. J. 1997, 3, 1745-1750.
3. See, for example, a) G. R. Desiraju, Chem. Commun. 1997, 1475- 1482; b) Crystal Engineering: The Design of Organic Solids, Materials Science Monographs 54, Elsevier, Amsterdam, 1989; c) J. J. Wolff, Angew. Chem. 1996, 108, 2339-2341; Angew. Chem. Int. Ed. Engl. 1996, 35, 2195-2197; d) G. R. Desiraju, J. Mol. Struct. 1996, 374, 191- 198; e) M. E. Davis, Chem. Eur. J. 1997, 3, 1745-1750.
4. See, for example, a) G. R. Desiraju, Chem. Commun. 1997, 1475- 1482; b) Crystal Engineering: The Design of Organic Solids, Materials Science Monographs 54, Elsevier, Amsterdam, 1989; c) J. J. Wolff, Angew. Chem. 1996, 108, 2339-2341; Angew. Chem. Int. Ed. Engl. 1996, 35, 2195-2197; d) G. R. Desiraju, J. Mol. Struct. 1996, 374, 191- 198; e) M. E. Davis, Chem. Eur. J. 1997, 3, 1745-1750.
5. See, for example, a) G. R. Desiraju, Chem. Commun. 1997, 1475- 1482; b) Crystal Engineering: The Design of Organic Solids, Materials Science Monographs 54, Elsevier, Amsterdam, 1989; c) J. J. Wolff, Angew. Chem. 1996, 108, 2339-2341; Angew. Chem. Int. Ed. Engl. 1996, 35, 2195-2197; d) G. R. Desiraju, J. Mol. Struct. 1996, 374, 191-198; e) M. E. Davis, Chem. Eur. J. 1997, 3, 1745-1750.
6. See, for example, a) G. R. Desiraju, Chem. Commun. 1997, 1475- 1482; b) Crystal Engineering: The Design of Organic Solids, Materials Science Monographs 54, Elsevier, Amsterdam, 1989; c) J. J. Wolff, Angew. Chem. 1996, 108, 2339-2341; Angew. Chem. Int. Ed. Engl. 1996, 35, 2195-2197; d) G. R. Desiraju, J. Mol. Struct. 1996, 374, 191- 198; e) M. E. Davis, Chem. Eur. J. 1997, 3, 1745-1750.
7. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
8. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
9. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
10. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
11. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357-401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
12. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
13. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117-138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
14. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
15. See, for example, a) R. Robson in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle, J. M. Lehn), Pergamon, Oxford, 1996, chap. 22, pp. 733-755; b) S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595; Angew. Chem. Int. Ed. 1998, 37, 1460-1494; c) M. Munakata, L. P. Wu, T. Kuroda-Sowa, Adv. Inorg. Chem. 1999, 46, 173-303; d) S. Subramanian, M. J. Zaworotko, Coord. Chem. Rev. 1994, 137, 357- 401; e) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405; f) A. J. Blake, N. R. Champness, P. Hubberstey, W. S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev. 1999, 183, 117- 138; g) M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288; h) R. Robson, B. F. Abrahams, S. R. Batten, R. W. Gable, B. F. Hoskins, J. Liu, Supramolecular Architecture, ACS, Washington DC, 1992, pp. 256-273.
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17. K. Biradha, C. Seward, M. J. Zaworotko, Angew. Chem. 1999, 111, 584-587; Angew. Chem. Int. Ed. 1999, 38, 492-495.
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19. a) J. D. Ranford, J. J. Vittal, D. Wu, Angew. Chem. 1998, 110, 1159- 1162; Angew. Chem. Int. Ed. 1998, 37, 1114-1116;
20. highlight: b) M. J. Zaworotko, Angew. Chem. 1998, 110, 1269- 1171; Angew. Chem. Int. Ed. 1998, 37, 1211-1213.
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29. Kα radiation using a sealed tube (2.4 kW) at 23°C. Absorption corrections were made with the program SADABS (G. M. Sheldrick, Göttingen, 1996), and the crystallographic software package SHELXTL (SHELXTL Reference Manual. Version 5.03, Wisconsin, 1996) was used for all calculations. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-133087 (1) and -133088 (3). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
30. L. L. Koh, J. D. Ranford, W. T. Robinson, J. O. Svensson, L. C. Tan, D. Wu, Inorg. Chem. 1996, 35, 6466-6472.
31. 2sala have also been solved. For the laller the compound is the enantiomer of 1: J. D. Ranford, W. T. Robinson, J. O. Svensson, J. J. Vittal, D. Wu, X. Yang, unpublished results.
32. ii 143(5); the N1-H1, N2-H2, O4-H4A, and O4-H4B distances are 0.75(4), 0.93(4), 0.74(3), and 0.74(3) Å, respectively. The H4A-O4-H4B angle is 100(6) . Operators for generating equivalent atoms: i : x + 1/2 - y + 1/2 + 1: ii: - x + 1, y + 1/2, z + 1/2.
33. See, for example, H. Lodish, D. Baltimore, A. Berk, S. L. Zipursky, P. Matsudaira, J. Darnell, Molecular Cell Biology, 3rd ed., Scientific American Books, New York, 1996.
34. Thermogravimetric analysis of 1 indicated a weight loss of 3.7 % in the temperature range 70-90°C, corresponding to the loss of one molecule of water per dimer (expected weight loss 3.4%) and the formation of the anhydrous compound 3. The X-ray powder pattern of this anhydrous material was the same as that of 3. Species 1 and 3 show the same decomposition pattern, which starts at about 240 C. The structures of the hulk materials for 1 and 3 were confirmed by matching their X-ray powder patterns with those generated from the corresponding singles. Compound 3 was also prepared independently. The crystal structure was carried out on the single crystal grown during the synthesis (see the Experimental Section).
35. [1b]
36. i 164(2) . Operator for generating equivalent atoms: i: x + 0.5, - y + 0.5, - z + 0.25.
37. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
38. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.