Crystal polymorphism

NATO Science for Peace and Security Series B: Physics and Biophysics

Volumn , Issue , 2008, Pages 87-109

  Bernstein, Joel ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

Concomitant polymorphism; Conformational polymorphism; Disappearing polymorphs; Growth conditions; Hydrates; Kinetic form; Polymorphism; Solvates; Stability; Structure property relationships; Thermodynamic form

Indexed keywords

EID: 77949436438     PISSN: 18746500     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4020-6823-2_5     Document Type: Article

References (74)

1. R. Hilfiker, ed. Polymorphism in the Pharmaceutical Industry (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006).
2. M.H. Klaproth, Bergmannische J. I, 294-9 (1798)
3. [cited in J.R. Partington, A History of Chemistry, Vol. 3, p. 203 (MacMillan & Co., London, 1964)].
4. E. Mitscherlich, Über die Körper, welche in zwei vershiedenen kristallisieren Formen [Considerering the materials which can crystallize in two different crystal forms]. Abhl. Akad. Berlin, 43-48 (1823).
5. R. Peschar, M.M. Pop, D.J.A. De Ridder, J.B. Van Mechele, R.A.J. Driessen and H. Schenk, Crystal structures of 1,3-distearoyl-2-oleoylglycerol and cocoa butter in the (V) phase reveal the driving force behind the occurrence of fat bloom on chocolate. J. Phys. Chem. B. 108, 15450-15453 (2004), and references therein.
6. D. Braga and F. Grepioni, eds. Making Crystals by Design: Methods, Techniques and Applications (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006)
7. W.C. McCrone, Polymorphism, in Physics and Chemistry of the Organic Solid State; edited by D. Fox, M. M. Labes and A. Weissenberg (Interscience, New York, 1965, vol. II, pp. 725-767.
8. J. Haleblian and W.C. McCrone, Pharmaceutical Applications of Polymorphism, J. Pharm. Sci. 64, 1269-1288 (1969).
9. W.C. McCrone, Fusion Methods in Chemical Microscopy (Interscience, New York, 1957).
10. J. Bernstein, Polymorphism in Molecular Crystals (Oxford University Press, Oxford, 2002).
11. nd edition (SSCI, West Lafayette, Indiana, 1999).
12. H.G. Brittain, ed., Drugs in the Pharmaceutical Sciences, J. Sarbrick, editor, Vol. 95, Polymorphism in Phamaceutical Solids (Marcel Dekker, New York, 1999).
13. H.G. Brittain, ed., Physical Characterization of Pharmaceutical Solids (Marcel Dekker, New York, 1995).
14. T. Threlfall, Analysis of Organic Polymorphs. A Review, The Analyst 120, 2435-2460 (1995).
15. M.R. Caira, Crystalline Polymorphism of Organic Compounds, Top. in Curr. Chem. 198, 163-208 (1998).
16. S. Datta and D.J.W. Grant, Crystal structures of drugs: Advances in determination, prediction and engineering. Nature Reviews/Drug Discovery 3, 42-57 (2004).
17. D. Braga, Crystal engineering, where from? Where to? Chem. Commun. 2751-2754 (2003).
18. J. Bernstein, R. Davey, and J.-O Henck, Concomitant Polymorphs. Angew. Chem. Int. Ed. Engl. 38, 3440-3461 (1999).
19. J.D. Dunitz, and J. Bernstein, Disappearing Polymorphs. Acc. Chem. Res. 28, 193-200 (1995)
20. A.F. Findlay, The Phase Rule and Its Applications, 9th ed. revised and rewritten by A.N. Campbell and N.O. Smith, (Dover Publications, New York, 1963).
21. E.F. Westrum and J.P. McCullough, Thermodynamics of crystals. Chapter 1 in Fox, D., Labes, M.M. and Weissberger, A. (eds.) Physics and Chemistry of the Organic Solid State, Vol. 1, (Wiley Interscience, New York, 1963) pp. 1-178.
22. A. Burger, Thermodynamic and other aspects of the polymorphism of drug substances. Pharm. Int. 3, 158-163(1982).
23. A. Burger and R. Ramberger, On the polymorphism of pharmaceutical and other molecular crystals. I Theory of thermodynamic rules. Mikrochim. Acta [Wien] 259-271 (1979).
24. A. Burger and R. Ramberger, On the polymorphism of pharmaceutical and other molecular crystals. II Applicability of thermodynamic rules. Mikrochim. Acta [Wien] 273-316 (1979).
25. A. Grunenberg, J.-O. Henck and H.W. Siesler, Theoretical derivation and practical applications of energy/temperature diagrams as an instrument in preformulation studies of drug substances. Int. J. Pharm., 129, 147-158 (1996).
26. B.D. Sharma, Allotropes and polymorphs. J. Chem. Educ. 64, 404-407 (1987).
27. M. J. Buerger, M. J Crystallographic aspects of phase transitions. Chapter 6 in Smoluchowski, R., Mayer, J.E. and Weyl, W.A. (eds.) Phase Transformations in Solids, (John Wiley & Sons, New York, 1951) pp. 183-211.
28. S. Lindeman and S.E. McGraw, Pharm. Manuf. Jan. 27-30 (1985).
29. See also Ref. 9, p. 111.
30. P.T. Cardew, and R.J. Davey, Kinetic factors in the appearance and transformation of metastable phases. J. Chem. Soc. Faraday Trans. 80, 659-668 (1984).
31. P.T. Cardew, and R.J. Davey, The kinetics of solvent-mediated phase transformations. Proc. Roy. Soc. London, A298, 415-428 (1985).
32. M. Volmer, Kinetik der Phasenbildung, (Steinkopf, Leipzig, 1939).
33. W. Ostwald, Studies on the formation and transformation of solid materials. Z. Phys. Chem. 289-330 (1897).
34. R.J. Davey, R.J. General discussion Faraday Disc. 95, 160-162 (1993).
35. P.T. Cardew and R. Davey, Tailoring of Crystal Growth, Institute of Chemical Engineers, North Western Branch, Symposium Papers, Number 2 (ISBN 090663623X) pp. 1.1-1.8 (1982).
36. M. Ciechanowicz, A.C. Skapski, and P.G.H. Troughton, The crystal structure of the orthorhombic form of hydridodicarbonylbis(triphenylphosphine) iridium(I): successful location of the hydride hydrogen atom from x-ray data. Acta Crystallogr. B32, 1673-1679 (1976).
37. R. Becker, and W. Doering, The kinetic treatment of nuclear formation in supersaturated vapors. Ann. Phys., 719-752 (1935).
38. I.N. Stranski, and D. Totomanov, Rate of formation of (crystal) nuclei and the Ostwald step rule. Z. Phys. Chem. A163, 399-408 (1933).
39. J. Bernstein and J.-O. Henck, Disappearing and reappearing polymorphs - An anathema to crystal engineering? Crystal Engineering 1, 119-128 (1998).
40. J.-O. Henck, J. Bernstein, A. Ellern, and R. Boese, Disappearing and reappearing polymorphs. The case of benzocaine:picric acid. J. Am. Chem. Soc. 123, 1834-1841 (2001).
41. S.R. Chemburkar, J. Bauer, K. Deming, H. Spiwek, K. Patel, J. Morris, R. Henry, S. Spanton, W. Dziki, W. Porter, J. Quick, P. Bauer, J. Donaubauer, B.A. Narayanan, M. Soldani, D. Riley, D. and K. McFarland, Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development. Org. Process Res. & Development 4, 413-417 (2000).
42. J. Bernstein, Conformational polymorphism. Chapter 14 in Desiraju, G.R. (ed.), Organic Solid State Chemistry, (Elsevier, Amsterdam, 1987) pp. 471-518.
43. J. Bernstein, and A.T. Hagler, Conformational polymorphism. The influence of crystal forces on molecular conformation. J. Am. Chem. Soc., 100, 673-681 (1978).
44. J.D. Dunitz, Phase changes and chemical reactions in molecular crystals. Acta Crystallogr. B51, 619-631 (1995).
45. S. Chen, Guzei and L. Yu, New polymorphs of ROY and new record for coexisting polymorphs of solved structures J. Am. Chem. Soc. 127, 9881-9885 (2005);
46. L. Yu, G.A. Stephenson, C.A. Mitchell, C.A. Bunnell, S.V. Snorek, J.J. Bowyer, T.B. Borchardt, J.G. Stowell and S.R. Byrn, Thermochemistry and conformational polymorphism of a hexamorphic crystal system. J. Am. Chem. Soc. 122, 585, 2000.
47. R.K. Merton and E. Barber, The travels and adventures of serendipity, (Princeton University Press: Princeton, 2004).
48. Many examples of the applications of these techniques can be found in references 1, 9-15.
49. J.A. Ibers, Gabapentin and gabapentin monohydrate, Acta Crystallogr. Sect. C, 57, 641-643 (2001).
50. J. Bernstein, Cultivating crystal forms, Chem. Commun., 5007-5012 (2005).
51. J.-O. Henck and M. Kuhnert-Brandstatter, Demonstration of the terms enantiotropy and monotropy in polymorphism research exemplified by flurbiprofen, J. Pharm. Sci. 88, 103-108 (1999).
52. 2 Acta Crystallogr. Sect. C. 41, 441-443 (1985);
53. G.E. Hardy, W.C. Kaska, B.P. Chandra and J.I. Zink, Triboluminescence- structure relationships in polymorphs of hexaphenylcarbodiphosphorane and anthranilic acid, molecular crystals, and salts, J. Am. Chem. Soc. 103, 1074-1079 (1981);
54. H. Takazawa, S. Ohba and Y. Saito, Structure of monoclinic o-aminobenzoic acid, Acta Crystallogr. Sect. C. 42, 1880-1 (1986);
55. T.-H. Lu, P. Chattopadhyay, F.-L. Liao and J.-M. Lo, Crystal structure of 2-aminobenzoic acid Anal Sci. 17, 905-906 (2001).
56. T.C. Lewis, D.A. Tocher and S.L. Price, An experimental and theoretical search for polymorphs of barbituric acid: The challenges of even limited conformational flexibility Cryst. Growth & Des. 4, 979-987 (2004);
57. W. Bolton, Acta Crystallogr. 16, 166-(1963);
58. G.A. Jeffrey, S. Ghose and J. O. Warwicker, Acta Crystallogr. 14, 881-(1961);
59. A.R. Al-Karaghouli, B. Abdul-Wahab, E. Ajaj and S. Asaff, Neutron diffraction study of barbituric-acid dihydrate, Acta Crystallogr. Sect. B. 33, 1655-1660 (1977);
60. G.S. Nichol and W. Clegg, A variable-temperature study of a phase transition in barbituric acid dihydrate Acta Crystallogr. Sect. B. 61, 464-472 (2005)
61. S.L. Morissette, S. Soukasenem, D. Levinson, M.J. Cima and Ö. Almarsson, Elucidation of crystal form diversity of the HIV protease inhibitor ritonavir by high-throughput crystallization Proc. Natl. Acad. Sci. U. S. A., 100, 2180-21 84 (2003).
62. G.R. Desiraju, ed., Crystal Design: Structure and Function, (Wiley: Chichester, 2003).
63. J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter and J. Morris, Ritonavir: An extraordinary example of conformational polymorphism, Pharm. Res. 18, 859-866 (2001).
64. W.I.F. David, K. Shankland, C.R. Pulham, N. Blagden, R. Davey and M. Song, Polymorphism in benzamide Angew. Chem., Int. Ed. 44, 7032-7035 (2005);
65. N. Blagden, R. Davey, G. Dent, M. Song, W.I.F. David, C.R. Pulham and K. Shankland, Woehler and Liebig revisited: A small molecule reveals its secrets - The crystal structure of the unstable polymorph of benzamide solved after 173 years, Cryst. Growth & Des. 5, 2218-2224 (2005).
66. (a) Ö. Almarsson and M.J. Zaworotko, Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? Chem. Commun. 1889-1896 (2004);
67. (b) C.B. Aakeröy, A.M. Beatty and B.A. Helfrich, "Total synthesis" supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules Angew. Chem., Int. Ed. 40, 3240-3241 (2001).
68. C.P. Price, A.L. Grzesiak and A.J. Matzger, Crystalline polymorph selection and discovery with polymer heteronuclei J. Am. Chem. Soc. 127, 5512-5517 (2005).
69. D. Braga and F. Grepioni, Making crystals from crystals: a green route to crystal engineering and polymorphism Chem. Commun. 3635-3645 (2005).
70. A.V. Trask, N. Shan, W.D.S. Motherwell, W. Jones, S. Feng, R.B.H. Tan and K.J. Carpenter, Selective polymorph transformation via solvent-drop grinding Chem. Commun. 880-882 (2005).
71. E.Y. Cheung, S.J. Kitchin, K.D.M. Harris, Y. Imai, N. Tajima and R. Kuroda, J. Am. Chem. Soc., Direct structure determination of a multicomponent molecular crystal prepared by a solid-state grinding procedure 125, 14658-14659 (2003).
72. A. Burger and U.J. Griesser, Physical stability, hygroscopicity and solubility of succinylsulfathiazole crystal forms - the polymorphic drug substances of the European Pharmacopoeia. 7. Eur. J. Pharm. Biopharm. 37 118-125 (1991).
73. P. York, Supercritical fluids: realising potential, Chem. World 2, 50-53 (2005);
74. B. Yu. Shekunov and P. York, Crystallization processes in pharmaceutical technology and drug delivery design J. Cryst. Growth 211, 122-136 (2001).