Polymorphic Packing Arrangements in a Class of Engineered Organic Crystals

Chemistry of Materials

Volumn 9, Issue 9, 1997, Pages 1933-1941

  Zerkowski, Jonathan A ^a   MacDonald, John C ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000128649     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm9505660     Document Type: Article

References (51)

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20. For food behavior, see: (a) Walstra, P. In Food Structure and Behavior; Blanshard, J. M. V., Lillford, P., Eds.; Academic Press: London; 1987. (b) Craig, S. R.; Roberts, K. J.; Sherwood, J. N.; Sato, K.; Hayashi, Y.; Iwahashi, M.; Cernik, R. J. J. Cryst. Growth 1993, 128, 1263. (c) Davey, R. J.; Richards, J. J. Cryst. Growth 1985, 71, 597.
21. For food behavior, see: (a) Walstra, P. In Food Structure and Behavior; Blanshard, J. M. V., Lillford, P., Eds.; Academic Press: London; 1987. (b) Craig, S. R.; Roberts, K. J.; Sherwood, J. N.; Sato, K.; Hayashi, Y.; Iwahashi, M.; Cernik, R. J. J. Cryst. Growth 1993, 128, 1263. (c) Davey, R. J.; Richards, J. J. Cryst. Growth 1985, 71, 597.
22. For polymorphism of clathrate lattices, see: Weber, E.; Skobridis, K.; Wierig, A.; Nassimbeni, L. R.; Johnson, L. J. Chem. Soc., Perkin Trans. 2 1992, 2123.
23. For polymorphism in organic conductors, see: Shibaeva, R. P.; Kaminskii, V. F.; Yagubskii, E. B. Mol. Cryst. Liq. Cryst. 1985, 119, 361.
24. A number of techniques can be employed, such as vapor diffusion, sublimation, or melt crystallization. Experimental conditions such as temperature or rate of evaporation of the solvent can also be varied. Historically, attempts to crystallize neutral organic compounds have relied most frequently on changes of solvent. Ellern, A.; Bernstein, J.; Becker, J. Y.; Zamir, S.; Shahal, L.; Cohen, S. Chem. Mater. 1994, 6, 1378.
25. Inasmuch as these factors do affect the observed reflection data in single-crystal studies, they will also make a contribution to a calculated powder trace based on those data. It is unknown, however, whether they would affect experimental powder diffraction data to the same extent.
26. For an overview of "disappearing polymorphs", see: Dunitz, J. D.; Bernstein, J. Acc. Chem. Res 1995, 28, 193.
27. Modern Powder Diffraction; Bish, D. L., Post, J. E., Eds.; Mineralogical Society of America: Washington, DC, 1989.
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31. Klug, H. P.; Alexander, L. E. X-ray Diffraction Procedures for Polycrystalline and Amorphous Materials, 2nd ed.; Wiley: New York, 1974.
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33. (b) Nakata, K.; Takaki, Y. Bull. Chem. Soc. Jpn. 1987, 60, 1168.
34. 28
35. The sample for this experiment was ground for 5-8 min in an agate mortar and pestle. This method was the one we commonly used to prepare all our powdered samples, so we believe that this search for preferred orientation is based on a representative class of powders.
36. Note, however, that by rotating the sample and sample holder only around one axis, we would only be able to detect preferred orientation in one plane (the plane of the sample holder). Tilting the sample holder (which is essentially impossible in our diffractometer) should also be performed to test for a horizontal packing of needle-shaped crystallites.
37. 23 We speculate that some of the peaks in the X = I complex (Figure 2b) could arise in this manner.
38. For a demonstration that differences in crystallite size and shape can lead to powder diffraction traces that can be mistakenly interpreted as arising from different polymorphs, see: Potts, G. D.; Jones, W.; Bullock, J. F.; Andrews, S. J.; Maginn, S. J. J. Chem. Soc., Chem. Commun. 1994, 2565.
39. Other problems associated with the setup of the diffractometer, e.g., inconsistent filling of the sample holder, could also make a contribution. Furthermore, the very act of grinding a sample could generate enough heat or mechanical stress to initiate a polymorphic phase transition. There seem to be few ways around this dilemma, except perhaps by employing a gradual increase in grinding time or vigor while remaining aware of the problems mentioned in footnotes 32 and 33.
40. (35) For studies that demonstrate the difficulty of reproducing peak intensities exactly, see: (a) Chrzanowski, F. A.; Fegely, B. J.; Sisco, W. R.; Newton, M. P. J. Pharm. Sci 1984, 73, 1448. (b) Kidd, W. C.; Varlashkin, P.; Li, C. Powder Diffraction 1993, 8, 180. (c) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Plowman, R.; Rout, J. E.; Stanley, D. R.; Taylor, A. J. Chem. Soc., Faraday Trans. 1994, 90, 1003. (d) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N. Mol. Cryst. Liq. Cryst. 1994, 242, 79. These last two papers demonstrate an important but subtle point: different polymorphs may have XPD patterns that appear virtually indistinguishable from each other.
41. For studies that demonstrate the difficulty of reproducing peak intensities exactly, see: (a) Chrzanowski, F. A.; Fegely, B. J.; Sisco, W. R.; Newton, M. P. J. Pharm. Sci 1984, 73, 1448. (b) Kidd, W. C.; Varlashkin, P.; Li, C. Powder Diffraction 1993, 8, 180. (c) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Plowman, R.; Rout, J. E.; Stanley, D. R.; Taylor, A. J. Chem. Soc., Faraday Trans. 1994, 90, 1003. (d) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N. Mol. Cryst. Liq. Cryst. 1994, 242, 79. These last two papers demonstrate an important but subtle point: different polymorphs may have XPD patterns that appear virtually indistinguishable from each other.
42. For studies that demonstrate the difficulty of reproducing peak intensities exactly, see: (a) Chrzanowski, F. A.; Fegely, B. J.; Sisco, W. R.; Newton, M. P. J. Pharm. Sci 1984, 73, 1448. (b) Kidd, W. C.; Varlashkin, P.; Li, C. Powder Diffraction 1993, 8, 180. (c) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Plowman, R.; Rout, J. E.; Stanley, D. R.; Taylor, A. J. Chem. Soc., Faraday Trans. 1994, 90, 1003. (d) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N. Mol. Cryst. Liq. Cryst. 1994, 242, 79. These last two papers demonstrate an important but subtle point: different polymorphs may have XPD patterns that appear virtually indistinguishable from each other.
43. For studies that demonstrate the difficulty of reproducing peak intensities exactly, see: (a) Chrzanowski, F. A.; Fegely, B. J.; Sisco, W. R.; Newton, M. P. J. Pharm. Sci 1984, 73, 1448. (b) Kidd, W. C.; Varlashkin, P.; Li, C. Powder Diffraction 1993, 8, 180. (c) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N.; Buckley, A. M.; Cottier, D.; Dempsey, P.; Plowman, R.; Rout, J. E.; Stanley, D. R.; Taylor, A. J. Chem. Soc., Faraday Trans. 1994, 90, 1003. (d) Davey, R. J.; Maginn, S. J.; Andrews, S. F.; Black, S. N. Mol. Cryst. Liq. Cryst. 1994, 242, 79. These last two papers demonstrate an important but subtle point: different polymorphs may have XPD patterns that appear virtually indistinguishable from each other.
44. Burger, A.; Ramberger, R. Mikrochim. Acta (Wien) II 1979, 259.
45. 36 The fact that the thermally produced samples of form II did not revert to their initial identity (forms I and III, respectively) is not proof that form II is the thermodynamically stable polymorph at room temperature. Metastable phases can be trapped well below the temperature of phase transition: (a) Yang, Q.-C.; Richardson, M. F.; Dunitz, J. D. Acta Crystallogr. 1989, B45, 312. (b) Richardson, M. F.; Yang, Q.-C.; Novotny-Bregger, E.; Dunitz, J. D. Acta Crystallogr. 1990, B46, 653.
46. 36 The fact that the thermally produced samples of form II did not revert to their initial identity (forms I and III, respectively) is not proof that form II is the thermodynamically stable polymorph at room temperature. Metastable phases can be trapped well below the temperature of phase transition: (a) Yang, Q.-C.; Richardson, M. F.; Dunitz, J. D. Acta Crystallogr. 1989, B45, 312. (b) Richardson, M. F.; Yang, Q.-C.; Novotny-Bregger, E.; Dunitz, J. D. Acta Crystallogr. 1990, B46, 653.
47. Changes in van der Waals contacts, charge-transfer interactions, ionic field effects, or dipolar interactions that arise from alternative packing arrangements can lead to differences between solution-phase and solid-phase chemical shift values of up to 3 ppm. Larger differences of up to 10 ppm are likely to be associated with changes in molecular conformation from solution to solid.
48. For solid-state studies using sophisticated NMR techniques, see: Edwards, A. J.; Burke, N. J.; Dobson, C. M.; Prout, K.; Heyes, S. J. J. Am. Chem. Soc. 1995, 117, 4637.
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51. Schwiebert, K.; Chin, D.; Whitesides, G. M. Unpublished data.