Self-complementary hydrogen bonding of 1,1'-bicyclohexylidene-4,4'-dione dioxime. Formation of a non-covalent polymer

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1773-1784

  Hoogesteger, Frans J ^a   Jenneskens, Leonardus W ^a   Kooijman, Huub ^b   Veldman, Nora ^b   Spek, Anthony L ^b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030065720     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01012-2     Document Type: Article

References (45)

1. Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304 and references cited.
2. Valiyaveettil, S.; Enkelmann, V.; Müllen, K. J. Chem. Soc., Chem. Commun. 1994, 2097. Hosseini, M. W.; Ruppert, R.; Schaeffer, P.; De Cian, A.; Kyritsakas, N.; Fischer, J. J. Chem. Soc., Chem. Commun. 1994, 2135.
3. Valiyaveettil, S.; Enkelmann, V.; Müllen, K. J. Chem. Soc., Chem. Commun. 1994, 2097. Hosseini, M. W.; Ruppert, R.; Schaeffer, P.; De Cian, A.; Kyritsakas, N.; Fischer, J. J. Chem. Soc., Chem. Commun. 1994, 2135.
4. For examples see: Keegstra, E. M. D.; Huisman, B.-H.; Paardekoper, E. M.; Hoogesteger, F. J.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Scheuten, A.; Veldman, N.; Spek, A. L. J Chem. Soc., Perkin Trans. 2 1995, in press. Keegstra, E. M. D.; Spek, A. L.; Zwikker, J. W.; Jenneskens, L. W. J. Chem. Soc., Chem. Commun. 1994, 1633. Allen, F. H.; Goud, B. S.; Hoy, V. J.; Howard, J. A. K.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1994, 2729. Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495.
5. For examples see: Keegstra, E. M. D.; Huisman, B.-H.; Paardekoper, E. M.; Hoogesteger, F. J.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Scheuten, A.; Veldman, N.; Spek, A. L. J Chem. Soc., Perkin Trans. 2 1995, in press. Keegstra, E. M. D.; Spek, A. L.; Zwikker, J. W.; Jenneskens, L. W. J. Chem. Soc., Chem. Commun. 1994, 1633. Allen, F. H.; Goud, B. S.; Hoy, V. J.; Howard, J. A. K.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1994, 2729. Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495.
6. For examples see: Keegstra, E. M. D.; Huisman, B.-H.; Paardekoper, E. M.; Hoogesteger, F. J.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Scheuten, A.; Veldman, N.; Spek, A. L. J Chem. Soc., Perkin Trans. 2 1995, in press. Keegstra, E. M. D.; Spek, A. L.; Zwikker, J. W.; Jenneskens, L. W. J. Chem. Soc., Chem. Commun. 1994, 1633. Allen, F. H.; Goud, B. S.; Hoy, V. J.; Howard, J. A. K.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1994, 2729. Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495.
7. For examples see: Keegstra, E. M. D.; Huisman, B.-H.; Paardekoper, E. M.; Hoogesteger, F. J.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Scheuten, A.; Veldman, N.; Spek, A. L. J Chem. Soc., Perkin Trans. 2 1995, in press. Keegstra, E. M. D.; Spek, A. L.; Zwikker, J. W.; Jenneskens, L. W. J. Chem. Soc., Chem. Commun. 1994, 1633. Allen, F. H.; Goud, B. S.; Hoy, V. J.; Howard, J. A. K.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1994, 2729. Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495.
8. Lehn, J.-M.; Mascal, M.; DeCian, A.; Fischer, J. J. Chem. Soc., Perkin Trans. 2 1992, 461. Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. Tetrahedron 1995, 51, 1953.
9. Lehn, J.-M.; Mascal, M.; DeCian, A.; Fischer, J. J. Chem. Soc., Perkin Trans. 2 1992, 461. Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. Tetrahedron 1995, 51, 1953.
10. For a recent review see: MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383. Cf. also Chem. Mat. 1994, 6, special issue: Structure and Chemistry of the Organic Solid State.
11. For a recent review see: MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383. Cf. also Chem. Mat. 1994, 6, special issue: Structure and Chemistry of the Organic Solid State.
12. Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. Reddy, D. S.; Craig, D. C; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737.
13. Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. Reddy, D. S.; Craig, D. C; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737.
14. Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. Reddy, D. S.; Craig, D. C; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737.
15. Bertolasi, V.; Gilli, G; Veronese, A. C. Acta Crystallogr. 1982, B38, 502.
16. Chertanova, L.; Pascard, C.; Sheremetev, A. Acta Crystallogr. 1994, B50, 708.
17. Hoogesteger, F. J.; Havenith, R. W. A.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Veldman, N.; Spek, A. L. J. Org. Chem. 1995, 60, 4375.
18. Veldman, N.; Spek, A. L.; Hoogesteger, F. J.; Zwikker, J. W.; Jenneskens, L. W. Acta Crystallogr. 1994, C50, 742.
19. Kitaigorodsky, A. I. Molecular Crystals and Molecules; Academic Press: New York, 1973.
20. Spek, A. L. Acta Crystallogr. 1990, A46, C34.
21. Bondi, A. J. Phys. Chem. 1964, 68, 441.
22. Jeffrey, G. A.; Maluszynska, H.; Mitra, J. Int. J. Biol. Macromol. 1985, 7, 336.
23. Okaya, Y.; Shimada, A.; Nitta, I. Bull. Chem. Soc. Jpn. 1956, 29, 210.
24. Bierlein, T. K.; Lingafelter, E. C. Acta Crystallogr. 1951, 4, 450.
25. Hesse, M.; Meier, H.; Zeeh, B. Spektroskopischen Methoden in der organischen Chemie, 4. Aufl.; Thieme: Stuttgart, 1991.
26. Steinwender, E.; Lutz, E. T. G.; van der Maas, J. H.; Kanters, J. A. Vib. Spectrosc. 1993, 4, 217.
27. Groth, P. Acta. Chem. Scand. 1968, 22, 128.
28. Winkler, F. K.; Seiler, P.; Chesick, J. P.; J. D. Dunitz Helv. Chim. Act. 1976, 59, 1417
29. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988.
30. Bach, R. D.; Wolber, G. J. J. Org. Chem. 1982, 47, 245, and references cited.
31. s[C(7) - C(S)] = 1.4(9)°). The ordered six-membered ring containing C(13) is in a chair conformation with all relevant asymmetry parameters less then 9.0°. Selected bond lengths (Å): C(4)-C(4a) 1.296(5); C(10)-C(16) 1.329(5); C(1)-O(1) 1.203(6); O(2)-C(7) 1.191(6); O(3)-C(13) 1.202(5).
32. Duax, W. L.; Norton, D. A. Atlas of Steroid Structure; IFI/Plenum Data Company: New York, 1975, vol. 1, pp. 16-22.
33. West, A. R. Basic Solid State Chemistry; John Wiley and Sons: New York, 1988.
34. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F., Stewart, J. J. P. J. Am. Chem. Soc. 1985, 707, 3902.
35. MOPAC 6.0, Stewart, J. J. P. Quant. Chem. Prog. Exchange, QCPE No. 504, Bloomington, IN, USA 1990.
36. Atomic coordinates (including calculated H atom coordinates), thermal parameters, bond lengths and valence angles for the crystal structure determination of compounds 1, 2+2DMSO and 8 have been deposited at the Cambridge Crystallographic Data Centre. They can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 IEZ, UK.
37. Spek, A. L. J. Appl. Crystallogr. 1988, 21, 578.
38. McCandlish, L. E.; Stout, G. H.; Andrews, L. C. Acta Crystallogr. 1975, A31, 245.
39. Sheldrick, G. M. SHELXS86, Program for crystal structure determination: University of Göttingen: Göttingen, Germany, 1986.
40. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
41. Sheldrick, G. M. SHELXL-93, Program for crystal structure refinement; University of Göttingen: Göttingen, Germany, 1993.
42. Sheldrick, G. M. SHELX76 Program for crystal structure determination; University of Cambridge: Cambridge, England, 1976.
43. International Tables for Crystallography, Volume C; Wilson, A. J. C. Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
44. Cromer, D. T.; Mann, J. B. Acta Crystallogr. 1968, A24, 321.
45. Cromer, D. T.; Liberman, D. J. Chem. Phys. 1970, 53, 1891.