Skip to main content
SpringerLink
Log in

Crystal engineering: A brief overview

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Crystal structures of organic and metal-organic compounds have been determined in enormous numbers over the past century, and at the time of writing this review, the Cambridge Structural Database has just crossed the half million mark. The possibility of designing a particular crystal packing is, however, of more recent origin and the subject of crystal engineering has addressed this possibility, more or less systematically, during the past 30 years. Crystal engineering demands a detailed and thorough knowledge of intermolecular interactions, which act as the supramolecular glue that binds molecules into crystals. It also requires systematic strategies for the design of a crystal, the architectural blueprint as it were. Finally, this enterprise needs to be geared towards a useful property in that the crystal that is being designed is a functional one. All these features of the subject are directly or indirectly connected with the fact that there is a very large database of known crystal structures that is available to the crystal engineer. This review attempts to briefly survey the current scenario in this expanding subject.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Desiraju G R 1989 Crystal engineering: The design of organic solids (Amsterdam: Elsevier)

    Google Scholar 

  2. Desiraju G R (ed.) 2003 Crystal engineering. Structure and function. Perspectives in supramolecular chemistry (Chichester: Wiley)

    Google Scholar 

  3. Tiekink E R and Vittal J J (eds) 2005 Frontiers in crystal engineering (Chichester: Wiley)

    Google Scholar 

  4. Braga D, Grepioni F and Orpen A G (eds) 1999 Crystal engineering. From molecules to crystals to materials (Dordrecht: Kluwer)

    Google Scholar 

  5. For some representative reviews, see: (a) Aakeröy C B 1997 Acta Crystallogr. Sect. B 53 569

    Article  Google Scholar 

  6. Goldberg I 2005 Chem. Commun. 1243

  7. Bishop R 1999 Synlett. 1351

  8. Biradha K 2003 Cryst. Eng. Comm. 5 374

    CAS  Google Scholar 

  9. Aakeröy C B, Champness N R and Janiak C 2010 Cryst. Eng. Comm. 12 22

    Google Scholar 

  10. Dastidar P 2008 Chem. Soc. Ev. 37 2699

    Article  CAS  Google Scholar 

  11. Glaser R 2007 Acc. Chem. Res. 40 9

    Article  CAS  Google Scholar 

  12. Braga D and Grepioni F 2005 Chem. Commun. 3635

  13. Braga D, Brammer L and Champness N R 2005 Cryst. Eng. Comm. 7 1; Erk P, Hengelsberg H, Haddow M F and van Gelder R 2004 Cryst. Eng. Comm. 6 474

    CAS  Google Scholar 

  14. Bragg W H 1921 Proc. Phys. Soc. (London) 34 33

    Article  CAS  Google Scholar 

  15. Sharma C V K 2002 Cryst. Growth Des. 2 465

    Article  CAS  Google Scholar 

  16. Robertson J M 1951 Proc. R. Soc. (London) Ser. A 207 101

    Article  CAS  Google Scholar 

  17. Desiraju G R 2003 Nature 423 485

    Article  CAS  Google Scholar 

  18. Ganguly P and Desiraju G R 2010 Cryst. Eng. Comm. 12 817

    CAS  Google Scholar 

  19. Davey R J, Dent G, Mughal R K and Parveen S 2006 Cryst. Growth Des. 6 1788

    Article  CAS  Google Scholar 

  20. Mondal R, Howard J A K, Banerjee R and Desiraju G R 2006 Cryst. Growth Des. 6 2507

    Article  CAS  Google Scholar 

  21. Banerjee R, Bhatt P M, Kirchner M T and Desiraju G R 2005 Angew. Chem. Int. Ed. 44 2515

    Article  CAS  Google Scholar 

  22. Gantenberg M and Sander W 2005 Spectrochimica Acta A 902

  23. Cohen M D and Schmidt G M J 1964 J. Chem. Soc. 1996 and the three succeeding papers

  24. Pepinsky R 1955 Phys. Rev. 100 971

    CAS  Google Scholar 

  25. Cohen M D 1987 Tetrahedron 43 1211

    Article  CAS  Google Scholar 

  26. Herbstein F H 2005 Crystalline molecular complexes and compounds (Oxford: OUP)

    Book  Google Scholar 

  27. Addadi L and Lahav M 1978 J. Am. Chem. Soc. 100 2838

    Article  CAS  Google Scholar 

  28. Leiserowitz L 1976 Acta Crystallogr. Sect. B 32 127

    Article  Google Scholar 

  29. Paul I C and Curtin D Y 1973 Acc. Chem. Res. 6 217

    Article  CAS  Google Scholar 

  30. Curtin D Y and Paul I C 1981 Chem. Rev. 81 525

    Article  CAS  Google Scholar 

  31. Paul I C and Curtin D Y 1975 Science 187 19

    Article  CAS  Google Scholar 

  32. Wegner G 1969 Z. Naturforsch. 24 824

    CAS  Google Scholar 

  33. Thomas J M 1981 Nature 289 633

    Article  Google Scholar 

  34. Cohen M D, Ludmer Z, Thomas J M and Williams J O 1971 Proc. R. Soc. London Ser. A 324 459

    Article  CAS  Google Scholar 

  35. Ermer O 1988 J. Am. Chem. Soc. 110 3747

    Article  CAS  Google Scholar 

  36. Hoskins B F and Robson R 1990 J. Am. Chem. Soc. 112 1546

    Article  CAS  Google Scholar 

  37. Eddaoudi M, Moler D B, Li H L, Chen B L, Reinecke T M, O’Keeffe M and Yaghi O M 2001 Acc. Chem. Res. 34 319

    Article  CAS  Google Scholar 

  38. Natarajan S and Mandal S 2004 Angew. Chem. Int. Ed. 43 4798

    Google Scholar 

  39. Zhang Z P, Huang X C and Chen X M 2009 Chem. Soc. Rev. 38 2385

    Article  CAS  Google Scholar 

  40. Biradha K, Sarkar M and Rajput L 2006 Chem. Commun. 4169

  41. Baburin I A, Blatov V A, Carlucci L, Ciani G and Proserpio D M 2008 Cryst. Eng. Comm. 10 1822

    CAS  Google Scholar 

  42. Desiraju G R and Gavezzotti A 1989 J. Chem. Soc. Chem. Commun. 621

  43. Desiraju G R 2007 Angew. Chem. Int. Ed. 46 8342

    Article  CAS  Google Scholar 

  44. Dunitz J D 1991 Pure Appl. Chem. 63 177

    Article  CAS  Google Scholar 

  45. Lehn J-M 1988 Angew. Chem. Int. Ed. Engl. 27 89

    Article  Google Scholar 

  46. Desiraju G R 1995 Angew. Chem. Int. Ed. Engl. 34 2311

    Article  CAS  Google Scholar 

  47. Moulton B and Zaworotko M J 2001 Chem. Rev. 101 1629

    Article  CAS  Google Scholar 

  48. Whitesides G M, Simanek E E, Mathias J P, Seto C T, Chin D N, Mammen M and Gordon D M, 1995 Acc. Chem. Res. 28 37

    Article  CAS  Google Scholar 

  49. Fyfe M C T and Stoddart J F 1997 Acc. Chem. Res. 30 393

    Article  CAS  Google Scholar 

  50. Chichak K S, Cantrill S J, Pease A R, Chiu S H, Cave G W V, Atwood J L and Stoddart J F 2004 Science 304 5675

    Article  Google Scholar 

  51. Mahapatra S, Azim Y and Desiraju G R 2010 J. Mol. Str. 976 200

    Article  CAS  Google Scholar 

  52. Dulmage W J and Lipscomb W N 1951 Acta Crystallogr. 5 260

    Article  Google Scholar 

  53. Gavezzotti A 1991 J. Am. Chem. Soc. 113 4622

    Article  CAS  Google Scholar 

  54. Etter M C 1990 Acc. Chem. Res. 23 120

    Article  CAS  Google Scholar 

  55. Jeffrey G A 1997 An introduction to hydrogen bonding (Oxford: OUP)

    Google Scholar 

  56. Desiraju G R and Steiner T 1999 The weak hydrogen bond in structural chemistry and biology (Oxford: OUP)

    Google Scholar 

  57. Metrangolo P, Neukirch H, Pilati T and Resnati G 2005 Acc. Chem. Res. 38 386

    Article  CAS  Google Scholar 

  58. Pedireddi V R, Reddy D S, Goud B S, Craig D C, Rae A D and Desiraju G R 1994 J. Chem. Soc. Perkin Trans. 2 2353

    Google Scholar 

  59. Bui T T T, Dahaoui S, Lecomte C, Desiraju G R and Espinosa E 2009 Angew. Chem. Int. Ed. 48 3838

    Article  CAS  Google Scholar 

  60. Brammer L, Espallargas G M and Libri S 2008 Cryst. Eng. Comm. 10 1335

    Google Scholar 

  61. Leznoff D B, Xue B Y, Batchelor R J, Einstein F W B and Patrick B O 2001 Inorg. Chem. 40 6026

    Article  CAS  Google Scholar 

  62. Simanek E E, Mammen M, Gordon D M, Chin D, Mathias J P, Seto C T and Whitesides G M 1995 Tetrahedron 51 607

    Article  CAS  Google Scholar 

  63. Tiekink E R T and Zukerman-Schpector J 2009 Cryst. Eng. Comm. 11 1176

    CAS  Google Scholar 

  64. Metrangolo P, Pilati T, Terraneo G, Biella S and Resnati G 2009 ibid 11 1187

    CAS  Google Scholar 

  65. Hosseinzadeh R, Lasemi Z, Seichter W and Weber E 2009 ibid 11 1331

    CAS  Google Scholar 

  66. Podsiado M and Katrusiak A 2009 ibid 11 1391

    Google Scholar 

  67. Santos-Contreras R J, Martinez-Martinez J, Mancilla-Margalli A, Peraza-Campos A L, Morin-Sanchez L M, Garcia-Baez E V and Padilla-Martinez I 2009 ibid 11 1451

    CAS  Google Scholar 

  68. Banerjee R, Mondal R, Howard J A K and Desiraju G R 2006 Cryst. Growth Des. 6 999

    Article  CAS  Google Scholar 

  69. Threlfall T L 1995 Analyst 120 2435

    Article  CAS  Google Scholar 

  70. Desiraju G R 2002 Nature Mater. 1 77

    Article  CAS  Google Scholar 

  71. Price S L 2009 Acc. Chem. Res. 42 117

    Article  CAS  Google Scholar 

  72. Sarma J A R P and Desiraju G R 2002 Cryst. Growth Des. 2 93

    Article  CAS  Google Scholar 

  73. Day G M et al 2009 Acta Crystallogr. Sect. B 65 107

    Article  Google Scholar 

  74. Neumann M A, Leusen F J J and Kendrick J 2008 Angew. Chem. Int. Ed. 47 2427

    Article  CAS  Google Scholar 

  75. Bond A D 2007 Cryst. Eng. Comm. 9 833

    CAS  Google Scholar 

  76. Desiraju G R, 2003 Cryst. Eng. Comm. 5 466

    CAS  Google Scholar 

  77. Dunitz J D 2003 Cryst. Eng. Comm. 5 506

    CAS  Google Scholar 

  78. Aakeröy C B, Fasulo M E and Desper J 2007 Mol. Pharm. 4 317

    Article  Google Scholar 

  79. Almarsson Ö and Zaworotko M J 2004 Chem. Commun. 1889

  80. Vishweshwar P, McMahon J A, Bis J A and Zaworotko M J 2006 J. Pharm. Sci. 95 499

    Article  CAS  Google Scholar 

  81. Childs S L and Zaworotko M J 2009 Cryst. Growth Des. 9 4208

    Article  CAS  Google Scholar 

  82. Schultheiss N and Newman A 2009 Cryst. Growth Des. 9 2950

    Article  CAS  Google Scholar 

  83. Trask A V 2007 Mol. Pharm. 4 301

    Article  CAS  Google Scholar 

  84. Stahly G P 2006 Cryst. Growth Des. 6 925

    Article  CAS  Google Scholar 

  85. Chow K, Tong H H Y, Lum S and Chow A H L 2008 J. Pharm. Sci. 97 2855

    Article  CAS  Google Scholar 

  86. Aakeröy C B, Forbes S and Desper J 2009 J. Am. Chem. Soc. 131 17048

    Article  Google Scholar 

  87. Martins F T, Paparidis N, Doriguetto A C and Ellena J 2009 Cryst. Growth Des. 9 5283

    Article  CAS  Google Scholar 

  88. Marivel S, Suresh E and Pedireddi V R 2008 Tetrahedron Lett. 49 3666

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, 560 012, India

    Gautam R. Desiraju

Authors
  1. Gautam R. Desiraju
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gautam R. Desiraju.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Desiraju, G.R. Crystal engineering: A brief overview. J Chem Sci 122, 667–675 (2010). https://doi.org/10.1007/s12039-010-0055-2

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-010-0055-2

Keywords

Search

Navigation