Infinite, undulating chains of intermolecularly hydrogen bonded (E,E)-2,2-dimethylcyclohexane-1,3-dione dioximes in the solid state. A single crystal X-ray, charge density distribution and spectroscopic study

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 2000, Pages 501-510

  Marsman, Albert W ^a   Van Walree, Cornelis A ^a   Havenith, Remco W A ^a   Jenneskens, Leonardus W ^a   Lutz, Martin ^a   Spek, Anthony L ^a   Lutz, Egbertus T G ^a   Van der Maas, Joop H ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL SYMMETRY; HYDROGEN BONDS; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAMAN SPECTROSCOPY; SINGLE CRYSTALS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CHARGE DENSITY DISTRIBUTION; COVALENT BONDING; DIMETHYLCYCLOHEXANEDIONE DIOXIMES; STEREOISOMERISM;

ORGANIC COMPOUNDS;

EID: 0034160975     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908335i     Document Type: Article

References (67)

1. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995
2. G. R. Desiraju, The Crystal as a Supramolecular Entity, Wiley, 1996.
3. M. C. Etter, J. Phys. Chem., 1991, 95, 4601
4. E. Fan, C. Vincent, S. J. Geib and A. D. Hamilton, Chem. Mater., 1994, 6, 1113
5. J. C. MacDonald and G. M. Whitesides, Chem. Rev., 1994, 94, 2383
6. J. C. MacDonald and G. M. Whitesides, See also the special issue on molecular networks; New J. Chem., 1998, 87.
7. V. Bertolasi, G. Gilli and A. C. Veronese, Acta Crystallogr., Sect. B, 1982, 38, 502
8. L. Chertanova, C. Pascard and A. Sheremetev, Acta Crystallogr., Sect. B, 1994, 50, 708.
9. 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.
10. (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
11. (b) E. ten Grotenhuis, A. W. Marsman, F. J. Hoogesteger, J. V. van Miltenburg, J. P. van der Eerden, L. W. Jenneskens, W. J. J. Smeets and A. L. Spek, J. Cryst. Growth, 1998, 191, 834 and references cited
12. (c) F. J. Hoogesteger, L. W. Jenneskens, H. Kooijman, N. Veldman and A. L. Spek, Tetrahedron, 1996, 52, 1773
13. (d) A. W. Marsman, E. D. Leusink, J. W. Zwikker, L. W. Jenneskens, W. J. J. Smeets, N. Veldman and A. L. Spek, Chem. Mater., 1999, 11, 1484.
14. C. B. Aakeröy, A. M. Beatty and D. S. Leinen, J. Am. Chem. Soc., 1998; 120, 7383.
15. M. Raban, D. Kost, W. B. Jennings and V. E. Wilson, in Acyclic Organonitrogen Stereodynamics, eds. J. B. Lambert and Y. Takeuchi, VCH, Weinheim, 1991, pp. 57-88 and 177-193.
16. M. E. Jung, P. A. Blair and J. W. Lowe, Tetrahedron Lett., 1976, 18, 1439 and references cited therein.
17. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Clarendon Press, Oxford, 1990.
18. J. March, Advanced Organic Chemistry, 3rd edn., Wiley, New York, 1985, p. 805.
19. H. Saitô and K. Nukada, Tetrahedron Lett., 1965, 25, 2117.
20. A. Kotali, V. P. Papageorgiou and P. G. Tsoungas, Org. Mass. Spectrom., 1987, 22, 373.
21. A. J. Bondi, J. Phys. Chem., 1964, 68, 441.
22. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.
23. A. I. Kitaigorodski, Molecular Crystals and Molecules, Academic Press, New York, 1973.
24. M.-J. Brienne, J. Gabard, M. Leclerq, L.-M. Lehn, M. Cesario, C. Pascard, M. Chevé and G. Gutruc-Rosset, Tetrahedron Lett., 1994, 35, 8157.
25. R. F. W. Bader, P. Lode, A. Popelier and T. A. Keith, Angew. Chem., Int. Ed. Eng., 1994, 106, 620.
26. T. Koritsánszky, R. Flaig, D. Zobel, H.-G. Krane, W. Morgenroth and P. Luger, Science, 1998, 279, 356
27. R. Flaig, T. Koritsánsky, J. Janczak, H.-G. Krane, W. Morgenroth and P. Luger, Angew. Chem., Int. Ed. Engl., 1999, 38, 1397.
28. N. K. Hansen and P. Coppens, Acta Crystallogr., Sect. A, 1978, 34, 909.
29. V. Tsirelson, Y. Abramov, V. Zavodnik, A. Stash, E. Belokoneva, J. Stahn, U. Pietsch and D. Feil, Struct. Chem., 1998, 9, 249 and references cited therein
30. M. Souhassou and R.H. Blessing, J. Appl. Crystallogr., 1999, 32, 210.
31. E. Espinosa, E. Molins and C. Lecomte, Chem. Phys. Lett., 1998, 285, 170.
32. R. Glaser and A. Streitwieser, J. Am. Chem. Soc., 1989, 111, 7340.
33. D. Cremer and E. Kraka, Croat. Chem. Acta, 1984, 57, 1259.
34. S. Ohba, K. Toriumi, S. Sato and Y. Saito, Acta Crystallogr., Sect. B, 1978, 34, 3535.
35. G. de With, S. Harkema and D. Feil, Acta Crystallogr., Sect. A, 1975, 31, S227.
36. K. Iijima, M. Suzuki, T. Sakaizumi and O. Ohashi, J. Mol. Struct., 413-414, 327.
37. J. D. Dunitz, V. Schomaker and K. N. Trueblood, J. Phys. Chem., 1988, 92, 856.
38. Y. A. Abramov, Acta Crystallogr., Sect. A, 1997, 53, 264.
39. M. C. Etter, S. M. Reutzel and G. M. Vojta, J. Mol. Struct., 1990, 237, 165
40. A. Naito, S. Ganapathy and C. A. Mc Dowell, J. Magn. Reson., 1982, 48, 367.
41. R. Sangill, N. Rastrup-Andersen, H. Bildsøe, H. J. Jakobsen and N. C. Nielsen, J. Magn. Reson. A, 1994, 107, 67.
42. H. Paulsen, K. Todt and H. Rippenberger, Chem. Ber., 1968, 101, 3365
43. 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.
44. Y. Okaya, A. Shimada and I. Nitta, Bull. Chem. Soc. Jpn., 1956, 29, 210
45. T. K. Bierlein and E. C. Lingafelter, Acta Crystallogr., 1951, 4, 450.
46. (a) H. Saitô, K. Nukada and M. Ohno, Tetrahedron Lett., 1964, 31, 2124 and references cited therein
47. (b) W. C. Harris and S. F. Bush, J. Chem. Phys., 1972, 56, 6147 and references cited therein.
48. 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, ch. 9.
49. F. A. Cotton, Chemical Applications of Group Theory, 3rd edn., Wiley, New York, 1990, pp. 338-347.
50. W. L. Earl and D. L. Vanderhart, J. Magn. Reson., 1982, 48, 35.
51. W. T. Dixon, J. Magn. Reson., 1981, 44, 220.
52. B. M. Jacobson, P. Soleropoulos and S. Bahadori, J. Org. Chem., 1988, 53, 3247.
53. K. Mori and H. Mori, Org. Synth., 1990, 68, 56.
54. T. W. Theobald, Tetrahedron, 1978, 34, 1567.
55. F. E. King, T. J. King and J. G. Topliss, J. Chem. Soc., 1957, 919.
56. S. Horvat, P. Karallas and J. M. White, J. Chem. Soc., Perkin Trans. 2, 1998, 2151.
57. G. Just and L. S. Ng, Can. J. Chem., 1968, 46, 3381.
58. G. M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, University of Göttingen, Germany, 1997.
59. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
60. Z. Otwinowski and W. Minor, Methods Enzymol., vol. 276: Macromolecular Crystallography, part A, eds. C. W. Carter, Jr. and R. M. Sweets, Academic Press, 1997, 307.
61. A. L. Spek, A Multipurpose Crystallographic Tool, Utrecht University, The Netherlands 1998.
62. R. H. Blessing, J. Appl. Crystallogr., 1997, 30, 421.
63. T. Koritsánszky, S. Howard, P. R. Mallison, Z. Su, T. Richter and N. K. Hansen, A Computer Program Package for Multipole Refinement and Analysis of Electron Densities form Diffraction Data, Free University of Berlin, Germany, 1995.
64. A. Eriksson and K. Hermansson, Acta Crystallogr., Sect. B, 1983, 39, 703.
65. GAMESS-UK is package of ab initio programs written by: M. F. Guest, J. V. van Lenthe, J. Kendrick, K. Schoffel, P. Sherwood and R. J. Harrison with contributions from: R. D. Amos, R. J. Buenker, M. Dupuis, N. C. Handy, I. H. Miller, P. J. Knowles, V. Bonacic-Koutecky, W. von Niessen, V. R. Saunders and A. J. Stone. The package is derived from the original GAMESS code due to M. Dupuis, D. Spangler and J. Wendolowski, NRCC Software Catalog, 1980, vol. 1, Program No. QG01 (GAMESS).
66. J. Cioslowski and B. B. Stefanov, Mol. Phys., 1995, 84, 707.
67. Gaussian 98, Revision A.6, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scusera, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian, Inc., Pittsburg, PA, 1998.