Skip to main content

Crystal Polymorphism and Multiple Crystal Forms

  • Chapter
  • First Online:
Molecular Networks

Part of the book series: Structure and Bonding ((STRUCTURE,volume 132))

Abstract

This chapter discusses the phenomenon of polymorphism in organic and organometallic compounds. Polymorphism is first introduced and then, to give the work some context, background information is given concerning properties and techniques for characterizing the solid phases. In particular, desolvation and interconverstion are examined, and the gas–solid reactions are presented as a successful route to obtaining new crystalline phases. Co-crystal definition is then described and the problem in distinguishing co-crystals and salts is evaluated.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Bernstein J (2002) Polymorphism in molecular crystals. Oxford University Press, Oxford, p 352

    Google Scholar 

  2. Dunitz JD, Bernstein J (1995) Acc Chem Res 28:193–200

    Article  CAS  Google Scholar 

  3. Klaproth MH (1798) Bergmannische J I:294–299

    Google Scholar 

  4. Mitscherlich E (1823) Abhl Akad Berlin 43

    Google Scholar 

  5. McCrone WC (1965) In: Fox D, Labes MM, Weissemberg A (eds) Polymorphism in physics and chemistry of the organic solid state, vol 2. Interscience, New York, p 726

    Google Scholar 

  6. Findlay AF (1951) The phase rule and its applications, 9th edn. Dover, New York, pp 7–16

    Google Scholar 

  7. Buerger MJ, Bloom MC (1937) Z Kristallogr 96:182–200

    CAS  Google Scholar 

  8. Sirota NN (1982) Cryst Res Technol 17:661–691

    Article  CAS  Google Scholar 

  9. Kuhnert-Brandstatter M (1965) Pure Appl Chem 10:133–144

    Article  CAS  Google Scholar 

  10. Kuhnert-Brandstatter M (1971) Thermomicroscopy in the analysis of pharmaceuticals. International series of monographs in analytical chemistry, vol 45. Pergamon, Oxford

    Google Scholar 

  11. Sarma JARP, Desiraju GR (1999) In: Seddon KR, Zaworotko M (eds) Crystal engineering: the design and application of functional solids. Kluwer, Dorderecht, pp 325–356

    Google Scholar 

  12. Griesser UJ (2002) Acta Crystallogr A 58(suppl):c241

    Article  Google Scholar 

  13. Gorbitz CH, Hersleth HP (2000) Acta Crystallogr B 56:526–534

    Article  Google Scholar 

  14. Griesser UJ, Burger A (1999) Acta Crystallogr A 55(suppl):400

    Google Scholar 

  15. Desiraju GR (1989) Crystal engineering: the design of organic solids. Elsevier, Amsterdam

    Google Scholar 

  16. Braga D, Grepioni F, Orpen AG (eds) (1999) Crystal engineering: from molecules and crystals to materials. In: Proceedings of the NATO Advanced Study Institute. 12–23 May 1999, Erice, Italy, p 500

    Google Scholar 

  17. Braga D, Grepioni F, Desiraju GR (1998) Chem Rev 98:1375–1405

    Article  CAS  Google Scholar 

  18. Blake AJ, Champness NR, Hubberstey P, Li W-S, Withersby MA, Schroder M (1999) Coord Chem Rev 183:117–138

    Article  CAS  Google Scholar 

  19. Moulton B, Zaworotko MJ (2001) Chem Rev 101:1629–1658

    Article  CAS  Google Scholar 

  20. Griesser UJ (2006) In: Hilfiker R (ed) The importance of solvates. Wiley, Weinheim, pp 211–233

    Google Scholar 

  21. Braga D, Maini L, de Sanctis G, Rubini K, Grepioni F, Chierotti MR, Gobetto R (2003) Chem Eur J 9:5538–5548

    Article  CAS  Google Scholar 

  22. Vishweshwar P, McMahon JA, Peterson ML, Hickey MB, Shattock TR, Zaworotko MJ (2005) Chem Commun, pp 4601–4603

    Google Scholar 

  23. Seddon KR (2004) Cryst Growth Des 4:1087–1087

    Article  CAS  Google Scholar 

  24. Bernstein J (2005) Chem Commun, pp 5007–5012

    Google Scholar 

  25. Nangia A (2006) Cryst Grow Des 6:2

    Article  CAS  Google Scholar 

  26. Burger A (1983) Topics in pharmaceutical sciences. Elsevier, Amsterdam, p 347

    Google Scholar 

  27. Cabri W, Ghetti P, Pozzi G, Alpegiani M (2007) Org Process Res Dev 11:64–72

    Article  CAS  Google Scholar 

  28. Lara-Ochoa F, Espinosa-Perez G (2007) Cryst Growth Des 7:1213– 1215

    Article  CAS  Google Scholar 

  29. Raw AS, Yu LX (2004) Adv Drug Delivery Rev 56:235–236

    Article  CAS  Google Scholar 

  30. Yu L, Stephenson GA, Mitchell CA, Bunnell CA, Snorek SV, Bowyer JJ, Borchardt TB, Stowell JG, Byrn SR (2000) J Am Chem Soc 122:585

    Article  CAS  Google Scholar 

  31. Chen S, Xi H, Yu L (2005) J Am Chem Soc 127:17439–17444

    Article  CAS  Google Scholar 

  32. Braga D, Bernstein J (2007) In: Dario B, Grepioni F (eds) Crystal polymorphism: challenges at crossroads of science and technology. Wiley, Weinheim, pp 293–314

    Google Scholar 

  33. Gobetto R (2007) In: Braga D, Grepioni F (eds) Solid state NMR. Wiley, Weinheim, pp 266–292

    Google Scholar 

  34. Grunenberg A, Henck JO, Siesler HW (1996) Int J Pharm 129:147–158

    Article  CAS  Google Scholar 

  35. Henck J-O, Kuhnert-Brandstatter M (1999) J Pharm Sci 88:103–108

    Article  CAS  Google Scholar 

  36. Almarsson O, Zaworotko MJ (2004) Chem Commun, p 1889

    Google Scholar 

  37. Aakeröy CB, Beatty AM, Helfrich BA (2001) Angew Chem Int Ed 40:3240–3242

    Article  Google Scholar 

  38. Price CP, Grzesiak AL, Matzger AJ (2005) J Am Chem Soc 127:5512–5517

    Article  CAS  Google Scholar 

  39. Morissette SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR (2004) Adv Drug Delivery Rev 56:275–300

    Article  CAS  Google Scholar 

  40. Braga D, Grepioni F (2005) Chem Commun, pp 3635–3645

    Google Scholar 

  41. Trask AV, Shan N, Motherwell WDS, Jones W, Feng S, Tan RBH, Carpenter KJ (2005) Chem Commun, pp 880–882

    Google Scholar 

  42. Braga D, Grepioni F (2004) Angew Chem Int Ed 43:4002–4011

    Article  CAS  Google Scholar 

  43. Griesser UJ, Burger A (1991) Eur J Pharm Biopharm 37:118

    Google Scholar 

  44. York P (2005) Chem World 2:50

    CAS  Google Scholar 

  45. Shekunov YB, York P (2001) J Cryst Growth 211:122

    Article  Google Scholar 

  46. Desiraju GR (2003) Crystal design: structure and function. Wiley, Chichester, p 420

    Google Scholar 

  47. Bauer J, Spanton S, Henry R, Quick J, Dziki W, Porter W, Morris J (2001) Pharm Res 18:859

    Article  CAS  Google Scholar 

  48. Kirpal A (1907) Monatsh Chem 28:439–445

    Article  CAS  Google Scholar 

  49. Tong ML, Wang J, Hu S (2005) J Solid State Chem 178:1518–1525

    Article  CAS  Google Scholar 

  50. Tong ML, Wang J, Hu S, Batten SR (2005) Inorg Chem Commun 8:48–51

    Article  CAS  Google Scholar 

  51. Senevirathna MKI, Pitigala P, Perera VPS, Tennakone K (2005) Langmuir 21:2997–3001

    Article  CAS  Google Scholar 

  52. International Centre for Diffraction Data (2005) Powder diffraction file PDF-2. ICDD, Newton Square, PA

    Google Scholar 

  53. Takusagawa F, Hirotsu K, Shimada A (1973) Bull Chem Soc Jpn 46:2669–2675

    Article  CAS  Google Scholar 

  54. Braga D, Maini L, Fagnano C, Taddei P, Chierotti MR, Gobetto R (2007) Chem Eur J 13:1222–1230

    Article  CAS  Google Scholar 

  55. Braga D, Maini L (2004) Chem Commun, pp 976–977

    Google Scholar 

  56. Braga D, Rubini K, Maini L (2004) Cryst Eng Commun 6:236–238

    CAS  Google Scholar 

  57. Braga D, Cojazzi G, Abati A, Maini L, Polito M, Scaccianoce L, Grepioni F (2000) J Chem Soc Dalton Trans, pp 3969–3975

    Google Scholar 

  58. Caira MR (1998) Top Curr Chem 198:163–208

    Article  CAS  Google Scholar 

  59. Caira MR, Nassimbeni LR, Timme M (1995) J Pharm Sci 84:884–888

    Article  CAS  Google Scholar 

  60. De Villiers MM, Van der Watt JG, Lotter AP (1991) Drug Dev Ind Pharm 17:1295–1303

    Article  CAS  Google Scholar 

  61. Braga D, Maini L, Grepioni F (1999) Chem Commun, pp 937–938

    Google Scholar 

  62. Chen X, Morris KR, Griesser UJ, Byrn SR, Stowell JG (2002) J Am Chem Soc 124:15012–15019

    Article  CAS  Google Scholar 

  63. Braga D, Cadoni M, Grepioni F, Maini L, Rubini K (2006) Cryst Eng Commun 8:756–763

    CAS  Google Scholar 

  64. Braga D, Grepioni F, Polito M, Chierotti MR, Ellena S, Gobetto R (2006) Organometallics 25:4627–4633

    Article  CAS  Google Scholar 

  65. Lewis TC, Tocher DA, Price SL (2004) Cryst Grow Des 4:979–987

    Article  CAS  Google Scholar 

  66. Bolton W (1963) Acta Cryst 16:166–173

    Article  CAS  Google Scholar 

  67. Jeffrey GA, Ghose S, Warwicker JO (1961) Acta Cryst 14:881–887

    Article  CAS  Google Scholar 

  68. Al-Karaghouli AR, Abdul-Wahab B, Ajaj E, Al-Asaff S (1977) Acta Crystallogr Sect B Struct Sci B33:1655–1660

    CAS  Google Scholar 

  69. Braga D, Cadoni M, Grepioni F, Maini L, Streek JVD (2007) New J Chem 11:1935–1940 doi: 10.1039/b704772j

    Article  Google Scholar 

  70. Etter MC, Reutzel SM, Choo CG (1993) J Am Chem Soc 115:4411–4412

    Article  CAS  Google Scholar 

  71. Zaworotko MJ (2007) Cryst Grow Des 7:4–9

    Article  CAS  Google Scholar 

  72. Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzman H, Remenar JF, Zhang Z, Tawa MD, Haley S, Zaworotko MJ, Almarsson O (2007) Eur J Pharm Biopharm 67:112–119

    Article  CAS  Google Scholar 

  73. Trask AV (2007) Mol Pharm 4:301–309

    Article  CAS  Google Scholar 

  74. Desiraju GR (2003) Cryst Eng Commun 5:466–467

    CAS  Google Scholar 

  75. Dunitz JD (2003) Cryst Eng Commun 5:506

    CAS  Google Scholar 

  76. Aakeroy CB, Salmon DJ (2005) Cryst Eng Commun 7:439

    Google Scholar 

  77. Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ (2006) J Pharm Sci 95:499–516

    Article  CAS  Google Scholar 

  78. Stahly GP (2007) Cryst Growth Des 7:1007–1026

    Article  CAS  Google Scholar 

  79. Bernstein J (2005) Cryst Growth Des 5:1661–1662

    Article  CAS  Google Scholar 

  80. Nangia A (2006) Cryst Growth Des 6:2–4

    Article  CAS  Google Scholar 

  81. Bond AD (2007) Cryst Eng Commun 9:833–834

    CAS  Google Scholar 

  82. Bock H, Holl S (2001) Z Naturforsch B 56:111

    CAS  Google Scholar 

  83. Hassel OJH (1954) Acta Chem Scand 8:873

    Article  CAS  Google Scholar 

  84. Hassel O, Stromme KO (1959) Acta Chem Scand 13:1775

    Article  CAS  Google Scholar 

  85. Bond AD (2003) Chem Commun, pp 250–251

    Google Scholar 

  86. Bond AD (2006) Cryst Eng Commun 8:333–337

    CAS  Google Scholar 

  87. Takayanagi H, Toubai Y, Goto M, Yamaguchi S, Ogura H (1991) Chem Pharm Bull 39:2491

    Article  CAS  Google Scholar 

  88. Banerjee A, Brown CJ (1985) Acta Crystallogr Sect C Cryst Struct Commun 41:82

    Article  Google Scholar 

  89. Herbstein FH, Kaftory M (1976) Acta Crystallogr Sect B Struct Sci 32:387

    Article  Google Scholar 

  90. Childs SL, Stahly GP, Park A (2007) Mol Pharm 4:323–338

    Article  CAS  Google Scholar 

  91. Wilson CC (2001) Acta Crystallogr Sect B Struct Sci B57:435–439

    Article  CAS  Google Scholar 

  92. Steiner T, Majerz I, Wilson CC (2001) Angew Chem Int Ed 40: 2651–2654

    Article  CAS  Google Scholar 

  93. Wiechert D, Mootz D (1999) Angew Chem Int Ed 38:1974–1976

    Article  CAS  Google Scholar 

  94. Braga D, Maini L, Polito M, Grepioni F (2004) Struct Bond 111:1– 32

    Article  CAS  Google Scholar 

  95. Gobetto R, Nervi C, Valfre E, Chierotti MR, Braga D, Maini L, Grepioni F, Harris RK, Ghi PY (2005) Chem Mater 17:1457– 1466

    Article  CAS  Google Scholar 

  96. Gobetto R, Nervi C, Chierotti MR, Braga D, Maini L, Grepioni F, Harris RK, Hodgkinson P (2005) Chem Eur J 11:7461–7471

    Article  CAS  Google Scholar 

  97. Sreekanth BR, Vishweshwar P, Vyas K (2007) Chem Commun, pp 2375–2377

    Google Scholar 

  98. Bucar D-K, Henry RF, Lou X, Borchardt TB, Zhang GGZ (2007) Chem Commun, pp 525–527

    Google Scholar 

  99. Zhang GGZ, Henry RF, Borchardt TB, Lou X (2007) J Pharm Sci 96:990–995

    Article  CAS  Google Scholar 

  100. Childs SL, Hardcastle KI (2007) Cryst Eng Commun 9:364–367

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dario Braga .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer-Verlag London

About this chapter

Cite this chapter

Braga, D., Grepioni, F., Maini, L., Polito, M. (2009). Crystal Polymorphism and Multiple Crystal Forms. In: Hosseini, M. (eds) Molecular Networks. Structure and Bonding, vol 132. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-01367-6_7

Download citation

Publish with us

Policies and ethics