Dimer or Catemer? Low-Energy Crystal Packings for Small Carboxylic Acids

Journal of Physical Chemistry B

Volumn 104, Issue 12, 2000, Pages 2647-2655

  Beyer, Theresa ^a   Price, Sarah L ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034732190     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9941413     Document Type: Article

References (65)

1. Nangia, A.; Desiraju, G. R. Top. Curr. Chem. 1998, 198, 57.
2. Allen, F. H.; Motherwell, W. D. S.; Raithby, P. R.; Shields, G. P.; Taylor, R. New J. Chem. 1999, 25.
3. Gavezzotti, A.; Filippini, G. J. Phys. Chem. 1994, 98, 4831.
4. Shimoni, L.; Glusker, J. P.; Bock, C. W. J. Phys. Chem. 1996, 100, 2957.
5. Aakeroy, C. B. Acta Crystallogr. 1997, B53, 569.
6. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
7. Leiserowitz, L. Acta Crystallogr. 1976, B32, 775.
8. Derissen, J. L.; Smit, P. H. Acta Crystallogr. 1977, A33, 230.
9. Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052.
10. Hagler, A. T.; Dauber, P.; Lifson, S. J. Am. Chem. Soc. 1979, 101, 5131.
11. Mooij, W. T. M.; van Eijck, B. P.; Price, S. L.; Verwer, P.; Kroon, J. J. Comput. Chem. 1998, 19, 459.
12. Payne, R. S.; Roberts, R. J.; Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1.
13. Verwer, P.; Leusen, F. J. J. Computer Simulation to Predict Possible Crystal Polymorphs. In Reviews of Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; John Wiley and Sons: New York, 1998; p 327.
14. van Eijck, B. P.; Kroon, J. J. Comput. Chem. 1999, 20, 799.
15. Perlstein, J. Chem. Mater. 1994, 6, 319.
16. Chaka, A. M.; Zaniewski, R.; Youngs, W.; Tessier, C.; Klopman, G. Acta Crystallogr. 1996, B52, 165.
17. Holden, J. R.; Du, Z.; Ammon, H. L. J. Comput. Chem. 1993, 14, 422.
18. Belsky, V. K.; Zorkaya, O. N.; Zorky, P. M. Acta Crystallogr. 1995, A51, 473.
19. Gavezzotti, A. PROMET 5.3, A Program for the Generation of Possible Crystal Structures from the Molecular Structure of Organic Compounds, University of Milan, Italy, 1997.
20. Williams, D. E. Program MPA/mpg, Molecular Packing Analysis/ Molecular Packing Graphics, Department of Chemistry, University of Louisville, Louisville, Kentucky, 1999.
21. Gavezzotti, A. Energetic Aspects of Crystal Packing. In Theoretical Aspects of Computer Modelling of the Molecular Solid State; Gavezzotti, A., Ed.; Wiley & Sons: Chichester, UK, 1997; p 97.
22. Lommerse, J. P. M.; Motherwell, W. D. S.; Ammon, H. L.; Dunitz, J. D.; Gavezzotti, A.; Hofmann, D. W. M.; Leusen, F. J. J.; Mooij, W. T. M.; Price, S. L.; Schweizer, B.; Schmidt, M. U.; van Eijck, B. P.; Verwer, P.; Williams, D. E. Acta Crystallogr. B, submitted for publication.
23. Price, S. L.; Wibley, K. S. J. Phys. Chem. A 1997, 101, 2198.
24. Nahringbauer, I. Acta Crystallogr. 1978, B34, 315.
25. Davis, R. E.; Bernstein, J. Trans. ACA 1998, 33, 7.
26. Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. Z. Kristallogr. 1981, 157, 215.
27. Benghiat, V.; Leiserowitz, L. J. Chem. Soc. 1972, 1763.
28. Stone, A. J.; Alderton, M. Mol. Phys. 1985, 56, 1047.
29. Amos, R. D.; Alberts, I. L.; Andrews, J. S.; Colwell, S. M.; Handy, N. C.; Jayatilaka, D.; Knowles, P. J.; Kobayashi, R.; Koga, N.; Laidig, K. E.; Laming, G.; Lee, A.; Maslen, P. E.; Murray, C. W.; Rice, J. E.; Sanz, J.; Simandiras, E. D.; Stone, A. J.; Su, M. D.; Tozer, D. J. CADPAC6: The Cambridge Analytical Derivatives Package, Issue 6; Cambridge University, Cambridge, UK, 1995.
30. Cox, S. R.; Hsu, L.-Y.; Williams, D. E. Acta Crystallogr. 1981, A37, 293.
31. Coombes, D. S.; Price, S. L.; Willock, D. J.; Leslie, M. J. Phys. Chem. 1996, 100, 7352.
32. Nahringbauer, I. Acta Chem. Scand. 1970, 24, 453.
33. Brown, C. J. Acta Crystallogr. 1966, 21, 1.
34. Bednowitz, A. L.; Post, B. Acta Crystallogr. 1966, 21, 566.
35. Derissen, J. L.; Smit, P. H. Acta Crystallogr. 1974, B30, 2240.
36. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 1987, 2, S1.
37. PLUTO program, CCDC, 12 Union Road, Cambridge CB1 2EZ, Cambridge, 1998 (download as RPLUTO available from www.ccdc.ca-m.ac.uk) .
38. Willock, D. J.; Price, S. L.; Leslie, M.; Catlow, C. R. J. Comput. Chem. 1995, 16, 628.
39. Lifson, S.; Hagler. A. T.; Dauber, P. J. Am. Chem. Soc. 1979, 101, 5111.
40. Smit, P. H.; Derissen, J. L.; van Duijneveldt, F. B. Mol. Phys. 1979, 37, 521.
41. Nobeli, I.; Price, S. L. J. Phys. Chem. A 1999, 103, 6448.
42. Nagaoka, S.; Terao, T.; Imashiro, F.; Saika, A.; Hirota, N.; Hayashi, S. Chem. Phys. Lett. 1981, 80, 580.
43. Stoeckli, A.; Meier, B. H.; Kreis, R.; Meyer, R.; Ernst, R. R. J. Chem. Phys. 1990, 93, 1502.
44. Meier, B. H.; Graf, F.; Ernst, R. R. J. Chem. Phys. 1982, 76, 767.
45. Zelsmann, H. R.; Mielke, Z. Chem. Phys. Lett. 1991, 186, 501.
46. Skinner, J. L.; Trommsdorff, H. P. J. Chem. Phys. 1988, 89, 897.
47. Frankenbach, G. M.; Etter, M. C. Chem. Mater. 1992, 4, 272.
48. Kaduk, J. A.; Golab, J. T.; Leusen, F. J. J. Cryst. Eng. 1998, 1, 277.
49. Pertsin, A. J.; Kitaigorodsky, A. I. The Atom-Atom Potential Method. Applications to Organic Molecular Solids; Springer-Verlag: Berlin, 1987; Vol. 47.
50. van Eijck, B. P.; Mooij, W. T. M.; Kroon, J. Acta Crystallogr. 1995, B51, 99.
51. Price, S. L.; Beyer, T. Trans. ACA 1998, 33, 23.
52. Potter, B. S.; Palmer, R. A.; Withnall, R.; Chowdhry, B. Z.; Price, S. L. J. Mol. Struct. 1999, 485-486, 349.
53. Coombes, D. S.; Nagi, G. K.; Price, S. L. Chem. Phys. Lett. 1997, 265, 532.
54. Payne, R. S.; Rowe, R. C.; Roberts, R. J.; Charlton, M. H.; Docherty, R. J. Comput. Chem. 1999, 20, 262.
55. Shoda, T.; Williams, D. E. J. Mol. Struct. 1995, 357, 1.
56. Filippini, G.; Gavezzotti, A.; Novoa, J. J. Acta Crystallogr. 1999, B55, 543.
57. Allan, D. R.; Clark, S. J. Phys. Rev. Lett. 1999, 82, 3464.
58. Allan, D. R.; Clark, S. J. Phys. Rev. B 1999, 60, 6328.
59. Gavezzotti, A. Chem. Eur. J. 1999, 5, 567.
60. Gavezzotti, A.; Filippini, G.; Kroon, J.; van Eijck, B. P.; Klewinghaus, P. Chem. Eur. J. 1997, 3, 893.
61. Lommerse, J. P. M.; Motherwell, W. D. S., manuscript in preparation.
62. Motherwell, W. D. S. Nova Acta Leopold. NF 1999, 79, 89.
63. Cerius2, Version 3.5; Molecular Simulations Inc.: San Diego, CA, 1997.
64. Krivy, I.; Gruber, B. Acta Crystallogr. 1976, A32, 297.
65. Reference for the experimental heats of sublimation: NIST Chemistry Webbook (http://webbook.nist.gov/chemistry).