4-(Tetrahydro-4H-thiopyran-1-oxide-4-ylidene)-cyclohexanone oxime in the solid-state. A two-dimensional network of enantiomorphous chains interconnected by weak hydrogen bonds

Organic and Biomolecular Chemistry

Volumn 3, Issue 8, 2005, Pages 1402-1409

  Marsman, Albert W ^a   Van Poecke, Bart L A ^a   Jenneskens, Leonardus W ^a   Spek, Anthony L ^b   Luitz, Egbertus T G ^c   Van Der Maas, Joop H ^c  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDROGEN BONDS; MOLECULAR STRUCTURE; RAMAN SCATTERING; SINGLE CRYSTALS; SOLVENTS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CARBON BONDING; ENANTIOMORPHOUS CHAINS; MOIETY; TWO-DIMENSIONAL NETWORKS;

AROMATIC COMPOUNDS;

EID: 18444366170     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500527b     Document Type: Article

References (43)

1. (a) For general reviews: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995;
2. (b) G. R. Desiraju, The Crystal as a Supramolecular Entity, Wiley, New York, 1996;
3. (c) E. Fan, C. Vicent, S. J. Geib and A. D. Hamilton, Chem. Mater., 1994, 6, 1113-1117;
4. (d) D. Shekhar Reddy, Y. E. Ovchinnikkov, O. V. Shishkin, Y. T. Struchkov and G. R. Desiraju, J. Am. Chem. Soc., 1996, 118, 4085-4089 and references cited;
5. (e) see the special issue on molecular networks in New J. Chem., 1998, 87-210.
6. F. J. Hoogesteger, R. W. A. Havenith, J. W. Zwikker, L. W. Jenneskens, H. Kooijman, N. Veldman and A. L. Spek, J. Org. Chem., 1995, 60, 4375-4384.
7. (a) F. J. Hoogesteger, J. M. Kroon, L. W. Jenneskens, E. J. R. Sudhölter, T. J. M. de Bruin, J. W. Zwikker, E. ten Grotenhuis, C. H. M. Mareé, N. Veldman and A. L. Spek, Langmuir, 1996, 12, 4760-4367;
8. (b) E. ten Grotenhuis, A. W. Marsman, F. J. Hoogesteger, J. C. van Miltenburg, J. P. van der Eerden, L. W. Jenneskens, W. J. J. Smeets and A. L. Spek, J. Cryst. Growth, 1998, 191, 834-845 and references cited;
9. (c) F. J. Hoogesteger, L. W. Jenneskens, H. Kooijman, N. Veldman and A. L. Spek, Tetrahedron, 1996, 52, 1773-1784;
10. (d) A. W. Marsman, E. D. Leusink, J. W. Zwikker, L. W. Jenneskens, W. J. J. Smeets and A. L. Spek, Chem. Mater., 1999, 11, 1484-1491;
11. (e) E. A. Bruton, L. Brammer, F. C. Pigge, C. B. Aakeröy and D. S. Leinen, New, J. Chem., 2003, 7, 1084 1094;
12. (f) see also; M. Lutz, A. L. Spek, R. Dabirian, C. A. van Walree and L. W. Jenneskens, Acta Cryst., 2004, C60, o127-o129.
13. A survey of single crystal X-ray structural data of 231 oxime derivatives in the Cambridge Crystallographic Database revealed that 54% gave this dimeric hydrogen bonding motif in the solid-state; V. Bertolasi, G. Gilli and A. C. Veronese. Acta Cryst., 1982, B38, 502-511;
14. L. Chertanova, C. Pascard and A. Sheremetev, Acta Cryst. 1994, B50, 708-716.
15. M. C. Etter, Acc. Chem. Res., 1990, 23, 120-126;
16. M. C. Etter, J. Phys. Chem., 1991, 95, 4601-4610.
17. M. Raban, D. Kost, W. B. Jennings and V. E. Wilson, in Acyclic Organonitrogen Stereodynamics, ed. J. B. Lambert and Y. Y. Takeuchi, VCH, Weinheim, 1991, pp. 57-88 and 177-193.
18. N. J. Leonard and C. R. Johnson, J. Org. Chem., 1962, 27, 282-284.
19. F. J. Hoogesteger, D. M. Grove, L. W. Jenneskens, T. J. M. de Bruin and B. A. J. Jansen, J. Chem. Soc., Perkin Trans. 2, 1996, 2327-2334.
20. N. S. Isaacs, Physical Organic Chemistry, Longman Group Limited, Essex, 1995. ch. 8. p. 351-368 and references cited.
21. E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, John Wiley and Sons, Inc., New York, 1994, ch. 14, p. 1119-1190.
22. The absolute configuration of an enantiomer of 1 (1-R/1-S) was determined by the relative orientation ofthe lone pairs and oxygen atoms of the nitrogen and sulfur atoms, respectively, from a Fisher projection along the chiral axis. For its configurational assignment sec reference 4.
23. R. J. Abraham, L. Pollock and F. Sancassan, J. Chem. Soc., Perkin Trans. 2, 1994, 2329-2336 and references cited.
24. MOPAC 7.0, J. J. P. Stewart, 1993, PM3;
25. J. J. P. Stewart, J. Comp. Chem., 1989, 10, 209-220.
26. R. W. A. Havenith, L. W. Jenneskens and J. H. van Lenthe, Chem. Phys. Lett., 1998, 282, 39-48.
27. A. Bondi, J. Phys. Chem., 1964, 68, 441-451.
28. For both contact distances: d(D⋯A) < R(D) + R(A) + 0.50 Å, d(H⋯A) < R(H) + R(A) - 0.12 Å and D-H⋯A> 100.0°, where R(x) are the van der Waals radii of the donor (D) and acceptor (A) atoms, respectively.
29. Weak C-H⋯O hydrogen bonds have been reported to be important and sometimes even dominant secondary interactions in, amongst others, molecular recognition processes, the determination of crystal packing and molecular conformations; T. Steiner. Chem. Commun., 1997, 727-734 and references cited.
30. H. M. M. Shearer, J. Chem. Soc., 1959, 1394-1397.
31. For the identification of the O-H group vibrations partially O-deuterated compounds were used (see Experimental).
32. For a general review: D. Lin-Vien, N. B. Colthup, W. G. Fateley and J. G. Grasselli, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press, San Diego, 1991.
33. O-H is the only active vibration of the O-H groups.
34. 20.
35. -1). Cf., For a general review: F. R. Dolish, W. G. Fateley and F. F. Bentley, Characteristic Raman Frequencies of Organic Compounds, John Wiley and Sons, Inc., New York, 1974.
36. -1) absorption patterns.
37. 4.
38. W. Luck, Z. Elektrochem., 1961, 65, 355-362.
39. M. Tamres and S. Searles, J. Am. Chem. Soc., 1959, 81, 2100-2104.
40. H. Saitô, K. Nukada and M. Ohno, Tetrahedron Lett., 1964, 5, 2124-2129. protonation of oximes preferably occurs at the nitrogen position.
41. A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Cryst., 1993, 26, 343-350.
42. G. M. Sheldrick, SHELXL-97, Program for refinement of crystal structures, University of Göttingen, Germany, 1997.
43. A. L. Spek, J. Appl. Cryst., 2003, 36, 7-13 and references cited.