Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels-Alder adducts derived from diarylfulvenes and N-arylimides

Journal of Fluorine Chemistry

Volumn 131, Issue 3, 2010, Pages 345-356

  Schwarzer, Anke ^a   Bombicz, Petra ^b   Weber, Edwin ^a  

^a TU BERGAKADEMIE FREIBERG   (Germany)

^b CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Fluorinated Diels Alder adducts; Fluorine involved contacts; Isostructurality calculations; Supramolecular interactions; X ray crystal structures

Indexed keywords

EID: 76749155437     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.11.013     Document Type: Article

References (79)

1. In: Vittal J., and Tieking E.R.T. (Eds). Frontiers in Crystal Engineering (2006), Wiley, Hoboken
2. In: Desiraju G.R. (Ed). Crystal Design: Structure and Function (Perspectives in Supramolecular Chemistry, vol. 7) (2003), Wiley, Chichester
3. Desiraju G.R. Crystal Engineering: The Design of Organic Solids (1989), Elsevier, Amsterdam
4. In: Weber E. (Ed). Design of Organic Solids (Topics in Current Chemistry, vol. 198) (1998), Springer, Berlin/Heidelberg
5. In: Mingos D.M.P. (Ed). Supramolecular Assembly via Hydrogen Bonds I and II (Structure and Bonding, vols. 108 and 111) (2004), Springer, Berlin/Heidelberg
6. Chin D.N., Zerkovski J.A., MacDonald J.C., and Whitesides G.M. In: Whitesell J.K. (Ed). Organised Molecular Assemblies in the Solid State (1999), Wiley, Chichester 188-253
7. Desiraju G.R. Angew. Chem. Int. Ed. 34 (1995) 2311-2327
8. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond (1999), Oxford University Press, New York
9. Nishio M. CrystEngComm 6 (2004) 130-158
10. James S.L. In: Atwood J.L., and Steed J.W. (Eds). Encyclopedia of Supramolecular Chemistry (2004), CRC Press, Boca Raton, FL 1093-1099
11. Dunitz J.D., and Taylor R. Chem. Eur. J. 3 (1997) 89-98
12. Thalladi V.R., Weiss H.-C., Bläser D., Boese R., Nangia A., and Desiraju G.R. J. Am. Chem. Soc. 120 (1998) 8702-8710
13. Dunitz J.-D., and Schweizer B. Chem. Eur. J. 12 (2006) 6804-6815
14. Caminati W., Melandri S., Maris A., and Ottavini P. Angew. Chem. Int. Ed. 45 (2006) 2438-2442
15. Li C., Zhu Y.-Y., Yi H.-P., Li C.-Z., Jiang X.-R., Li Z.T., and Yu Y.-H. Chem. Eur. J. 13 (2007) 9990-9998
16. Kirsch P. Modern Fluoroorganic Chemistry (2004), Wiley-VCH, Weinheim
17. In: Filler R., Kobayashi Y., and Yagupolskii L.M. (Eds). Biomedicinal Aspects of Fluorine Chemistry (1993), Elsevier, Amsterdam
18. In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). Biomedical Frontiers of Fluorine Chemistry (American Chemical Society Symposium Series 639) (1996), American Chemical Society, Washington, DC
19. Jones K., and Stead G. Fluorine Chem. 104 (2000) 5-18
20. Reddy R.A., and Sadashiva B.K. J. Mater. Chem. 14 (2004) 1936-1947
21. Matsuda K., and Irie M. In: Müller T.J.J., and Bunz U.H.F. (Eds). Functional Organic Materials (2007), Wiley-VCH, Weinheim 329-351
22. Haufe G., Rosen T.C., Meyer O.G.J., Fröhlich R., and Rissanen K. J. Fluorine Chem. 114 (2002) 189-198
23. Reichenbächer K., Süss H.J., Stoeckli-Evans H., Bracco S., Sozzani P., Weber E., and Hulliger J. New J. Chem. 28 (2004) 393-397
24. Yano M., Taketsugu T., Hori K., Okamoto H., and Takenaka S. Chem. Eur. J. 10 (2004) 3991-3999
25. Fröhlich R., Rosen T.C., Meyer O.G.J., Rissanen K., and Haufe G. J. Mol. Struct. 787 (2006) 50-62
26. Abad A., Agulló C., Cuñat A.C., Vilanova C., and Ramirez de Arellano M.C. Cryst. Growth Des. 6 (2006) 46-57
27. Coates G.W., Dunn A.R., Henling L.M., Dougherty D.A., and Grubbs R.H. Angew. Chem. Int. Ed. 36 (1997) 248-251
28. Vishnumurthy K., Guru Row T.N., and Venkatesan K. Photochem. Photobiol. Sci. 1 (2002) 427-430
29. Reichenbächer K., Stoeckli-Evans H., Weber E., and Hulliger J. J. Fluorine Chem. 127 (2006) 270-276
30. Reichenbächer K., Neels A., Stoeckli-Evans H., Balasubramaniyan P., Müller K., Matsuo Y., Nakamura E., Weber E., and Hulliger J. Cryst. Growth Des. 7 (2007) 1399-1405
31. Kasai K., and Fujita M. Chem. Eur. J. 13 (2007) 3089-3105
32. Reichenbächer K., Süss H.J., and Hulliger J. Chem. Soc. Rev. 34 (2005) 22-30
33. Zahn A., Brotschi C., and Leumann C.J. Chem. Eur. J. 11 (2005) 2125-2129
34. El-azizi Y., Schmitzer A., and Collins S.K. Angew. Chem. Int. Ed. 45 (2006) 968-973
35. Bacchi S., Benaglia M., Cozzi F., Demartin F., Filippini G., and Gavezzotti A. Chem. Eur. J. 12 (2006) 3538-3546
36. Kishikawa K., Oda K., Aikyo S., and Kohmoto S. Angew. Chem. Int. Ed. 46 (2007) 764-768
37. Ponzini F., Zagha R., Hardcastle K., and Siegel J.S. Angew. Chem. Int. Ed. 39 (2000) 2323-2325
38. Mountford A.J., Hughes D.L., and Lancaster S.J. Chem. Commun. (2003) 2148-2149
39. Choudbury A.R., Nagarajan K., and Guru Row T.N. Cryst. Eng. 6 (2003) 145-152
40. Hyla-Kryspin I., Haufe G., and Grimme S. Chem. Eur. J. 10 (2004) 3411-3422
41. Zhu S., Zhu S., Jin G., and Li Z. Tetrahedron Lett. 46 (2005) 2713-2716
42. Dautel O.J., and Fourmigué M. J. Org. Chem. 65 (2000) 6479-6486
43. Madhavi N.N.L., Desiraju G.R., Bilton C., Howard J.A.K., and Allen F.H. Acta Crystallogr. B 56 (2000) 1063-1070
44. Prasanna M.D., and Guru Row T.N. Cryst. Eng. 3 (2000) 135-154
45. Schwarzer A., Seichter W., Weber E., Stoeckli-Evans H., Losada M., and Hulliger J. CrystEngComm 6 (2004) 567-572
46. Dunitz J.D., and Schweizer W.B. Chem. Eur. J. 12 (2006) 6804-6815
47. Ramasubbu N., Parthasarathy R., and Murray-Rust P. J. Am. Chem. Soc. 108 (1986) 4308-4314
48. Reddy C.M., Kirchner M.T., Gundakaram R.C., Padmanabhan K.A., and Desiraju G.R. Chem. Eur. J. 12 (2006) 2222-2234
49. Awwadi F.F., Willett R.D., Peterson K.A., and Twamley B. Chem. Eur. J. 12 (2006) 8952-8960
50. Schwarzer A., and Weber E. Cryst. Growth Des. 8 (2008) 2862-2874
51. Fringuelli F., and Taticchi A. Dienes in the Diels-Alder Reaction (1990), Wiley, New York
52. Kloetzel M.C. Org. React. 4 (1948) 1-59
53. Martin J.G., and Hill R.K. Chem. Rev. 61 (1961) 537-562
54. López S.N., Sortino M., Escalante A., de Campos F., Corrêa R., Filho V.C., Nunes R.J., and Zacchino S.A. Arzneim. Forsch. 58 (2003) 280-288
55. Cava M.P., Deana A.A., Muth K., and Mitchell M.J. Org. Synth. 41 (1961) 93-95
56. Thiele J. Ber. Dtsch. Chem. Ges. 33 (1900) 666-673
57. Alper H., and Laycock D.E. Tetrahedron Lett. 22 (1981) 33-34
58. Kresze G., Rau S., Sabelus G., and Goetz H. Liebigs Ann. Chem. 648 (1961) 51-56
59. Bergmann E.D. Chem. Rev. 68 (1968) 41-84
60. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C. 02 (2004), Gaussian, Inc., Wallingford, CT, USA
61. Weber E. In: Atwood J.L., Davies J.E.D., MacNicol D.D., and Vögtle F. (Eds). Comprehensive Supramolecular Chemistry vol. 6 (1996), Elsevier Science, Oxford 535-592
62. Weber E. In: Atwood J.L., Davies J.E.D., and MacNicol D.D. (Eds). Inclusion Compounds vol. 4 (1991), Oxford University Press, Oxford 188-262
63. Bondi A. J. Phys. Chem. 68 (1964) 441-451
64. Parrish D.A., Deschamps J.R., Gilardi R.D., and Butcher R.J. Cryst. Growth Des. 8 (2008) 57-62
65. Metrangolo P., Meyer F., Pilati T., Resnati G., and Terraneo G. Angew. Chem. 120 (2008) 6206-6220
66. Metrangolo P., Neukirch H., Pilati T., and Resnati G. Acc. Chem. Res. 38 (2005) 386-395
67. Metrangolo P., and Resnati G. Chem. Eur. J. 7 (2001) 2511-2519
68. Rissanen K. CrystEngComm 10 (2008) 1107-1113
69. Brammer L., Espallargas G.M., and Libri S. CrystEngComm 10 (2008) 1712-1727
70. Metrangolo P., Pilati T., Terraneo G., Biella S., and Resnati G. CrystEngComm 11 (2009) 1187-1196
71. Karpfen A. In: Cetrangolo P., and Resnati G. (Eds). Halogen Bonding: Fundamentals and Applications (2008), Springer, Berlin 1-16
72. Kálmán A., Párkányi L., and Argay G. Acta Crystallogr. B 49 (1993) 1039-1049
73. Kálmán A., and Fárbián L. Acta Crystallogr. B 63 (2007) 411-417
74. Gruber T., Peukert M., Schindler D., Seichter W., Weber E., and Bombicz P. J. Inc. Phenom. Macrocycl. Chem. 62 (2008) 311-322
75. Kálmán A., and Párkányi L. In: Hargittai M., and Hargittai I. (Eds). Isostructurality of Organic Crystals in Advances in Molecular Structure Research vol. 3 (1997), JAI Press Inc. 189-226
76. Bruker. SMART (Version 5.628), SAINT (Version 6. 45a) and SAINTPLUS (2004), Bruker AXS Inc., Madison, WI, USA
77. Sheldrick G.M. SHELXS-97. Program for Crystal Structure Solution (1997), University of Göttingen, Germany
78. Sheldrick G.M. SHELXL-97. Program for Crystal Structure Refinement (1997), University of Göttingen, Germany
79. Sheldrick G.M. SADABS (1996), University of Göttingen, Germany