Crystal engineering: A holistic view

Angewandte Chemie - International Edition

Volumn 46, Issue 44, 2007, Pages 8342-8356

  Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Crystal engineering; Hydrogen bonds; Intermolecular interactions; Polymorphism; Supramolecular chemistry

Indexed keywords

CRYSTAL ENGINEERING; HYDROGEN BONDS; MOLECULAR INTERACTIONS; POLYMORPHISM; SUPRAMOLECULAR CHEMISTRY; X RAY CRYSTALLOGRAPHY;

COORDINATION BONDS; INTERMOLECULAR INTERACTIONS; SUBSTRUCTURAL PATTERNS;

MOLECULAR STRUCTURE;

EID: 36148966165     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700534     Document Type: Review

References (135)

1. G. R. Desiraju, Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989.
2. Solid State Photochemistry. A Collection of Papers by G. M. J. Schmidt and his Collaborators (Monographs in Modern Chemistry, Vol. 8) (Ed.: D. Ginsburg), Verlag Chemie, Weinheim, 1976.
3. A. I. Kitaigorodskii, Molecular Crystals and Molecules, Academic Press, New York, 1973.
4. J. M. Thomas, Nature 1981, 289, 633-634.
5. L. Addadi, M. Lahav, Pure Appl. Chem. 1979, 51, 1269-1284.
6. G. Wegner, Z. Naturforsch. B 1969, 24, 824-832.
7. Crystal Engineering. From Molecules and Crystals to Materials (Eds.: D. Braga, F. Grepioni, A. G. Orpen), Kluwer, Dordrecht, 1999.
8. Frontiers in Crystal Engineering (Eds.: E. R. Tiekink, J. J. Vittal), Wiley, Chichester, 2005.
9. Crystal Design. Structure and Function. Perspectives in Supramolecular Chemistry (Ed.: G. R. Desiraju), Wiley, Chichester, 2003.
10. M. Eddaoudi, D. B. Moler, H. L. Li, B. L. Chen, T. M. Reinecke, M. O'Keeffe, O. M. Yaghi, Acc. Chem. Res. 2001, 34, 319-330.
11. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629-1658.
12. A. Nangia, G. R. Desiraju, Acta Crystallogr. Sect. A 1998, 54, 934-944.
13. C. B. Aakeroy, Acta Crystallogr. Sect. B 1997, 53, 569-586.
14. M. W. Hosseini, Acc. Chem. Res, 2005, 38, 313-323.
15. O. R. Evans, W. B. Lin, Acc. Chem. Res. 2002, 35, 511-522.
16. I. Goldberg, Chem. Commun. 2005, 1243-1254.
17. J. D. Wuest, Chem. Commun. 2005, 5830-5837.
18. M. D. Ward, Chem. Commun. 2005, 5838-5842.
19. C. V. K. Sharma, Cryst. Growth Des. 2002, 2, 465-474.
20. D. Braga, F. Grepioni, Chem. Commun. 2005, 3635-3645.
21. A. D. Burrows, Encyclopedia of Supramolecular Chemistry, Vol. 1 (Eds.: J. Atwood, J. Steed), Marcel Dekker, New York, 2004, pp. 319-325.
22. P. Coppens, S. L. Zheng, M. Gembicky, M. Messerschmidt, P. M. Dominiak, CrystEngComm 2006, 8, 735-741.
23. R. Bishop, Synlett 1999, 1351-1358.
24. K. Biradha, CrystEngComm 2003, 5, 374-384.
25. S. A. Dalrymple, G. K. H. Shimizu, J. Mol. Struct. 2006, 796, 95-106.
26. P. Erk, H. Hengelsberg, M. F. Haddow, R. van Gelder, CrystEngComm 2004, 6, 474-483.
27. J. M. Lehn, Angew. Chem. 1988, 100, 91-116;
28. Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112.
29. J. D. Dunitz, Pure Appl. Chem. 1991, 63, 177-185.
30. G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44.
31. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558;
32. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
33. The less valid this assumption, the less useful is the concept of the supramolecular synthon in crystal engineering. It is recognized that any crystal structure is complex, and that its analysis into smaller units is, of necessity, a simplification. The question, however, is whether or not a particular simplification affects one's comprehension of a structure to such an extent that one is unable to go back in a synthetic step and regenerate a crystal structure of a related molecule. Alternatively, if the simplification is very slight, there is no real advantage gained in invoking the synthon. Accordingly, the supramolecular synthon approach to crystal engineering hinges on whether or not a particular simplification (structure to synthon) is substantial enough to allow its easy use in a subsequent synthetic step (synthon to structure), but not so excessive that essential attributes of a structure are lost in the process of simplification, rendering subsequent crystal engineering unreliable.
34. M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401.
35. N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796.
36. V. Maurizot, M. Yoshizawa, M. Kawano, M. Fujita, Dalton Trans. 2006, 2750-2756.
37. S. R. Seidel, P. J. Stang, Acc. Chem. Res. 2002, 35, 972-983.
38. D. L. Caulder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982.
39. B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076-2097;
40. Angew. Chem. Int. Ed. 2001, 40, 2022-2043.
41. A. R. Williams, B. H. Northrop, T. Chang, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2006, 118, 6817-6821;
42. Angew. Chem. Int. Ed. 2006, 45, 6665-6669.
43. G. R. Desiraju, Curr. Sci. 2005, 88, 374-380.
44. D. Das, G. R. Desiraju, Chem. Asian J. 2006, 1, 231-244.
45. S. S. Kuduva, D. C. Craig, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1999, 121, 1936-1944.
46. J. Bernstein, Polymorphism in Molecular Crystals, Clarendon, Oxford, 2002.
47. J. Bernstein, Chem. Commun. 2005, 5007-5012.
48. S. Datta, D. J. W. Grant, Nat. Rev. Drug Discovery 2004, 3, 42- 57.
49. Ö. Almarsson, M. J. Zaworotko, Chem. Commun. 2004, 1889-1896.
50. O. Ermer, J. Am. Chem. Soc. 1988, 110, 3747-3754.
51. S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595;
52. Angew. Chem. Int. Ed. 1998, 37, 1460-1494.
53. R. Thaimattam, C. V. K. Sharma, A. Clearfield, G. R. Desiraju, Cryst. Growth Des. 2001, 1, 103-106.
54. R. Banerjee, R. Mondal, J. A. K. Howard, G. R. Desiraju, Cryst. Growth Des. 2006, 6, 999-1009.
55. S. Kitagawa, R. Kitaura, S. Noro, Angew. Chem. 2004, 116, 2388-2430;
56. Angew. Chem. Int. Ed. 2004, 43, 2334-2375.
57. L. Carlucci, G. Ciani, D. M. Proserpio, Coord. Chem. Rev. 2003, 246, 247-289.
58. G. Férey, C. Mellot-Draznieks, C. Serre, F. Millange, Acc. Chem. Res. 2005, 38, 217-225.
59. N. R. Champness, Dalton Trans. 2005, 877-880.
60. B. F. Hoskins, R. Robson, J. Am. Chem. Soc. 1990, 112, 1546-1554.
61. O. M. Yaghi, M. O'Keeffe, N. W. Ockwig, H. K. Chae, M. Eddaoudi, J. Kim, Nature 2003, 423, 705-714.
62. J. L. C. Rowsell, O. M. Yaghi, Angew. Chem. 2005, 117, 4748-4758;
63. Angew. Chem. Int. Ed. 2005, 44, 4670-4679.
64. R. Matsuda, R. Kitaura, S. Kitagawa, Y. Kubota, R. V. Belosludov, T. C. Kobayashi, H. Sakamoto, T. Chiba, M. Takata, Y. Kawazoe, Y. Mita, Nature 2005, 436, 238-241.
65. Y. Kubota, M. Takata, R. Matsuda, R. Kitaura, S. Kitagawa, T. C. Kobayashi, Angew. Chem. 2006, 118, 5054-5058;
66. Angew. Chem. Int. Ed. 2006, 45, 4932-4936.
67. G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, OUP, Oxford, 1999.
68. T. Steiner, Angew. Chem. 2002, 14, 50-80;
69. Angew. Chem. Int. Ed. 2002, 41, 48-76.
70. J. D. Dunitz, A. Gavezzotti, Angew. Chem. 2005, 117, 1796-1819;
71. Angew. Chem. Int. Ed. 2005, 44, 1766-1787.
72. J. M. Robertson, Organic Crystals and Molecules, Cornell University, Ithaca, 1953, p 239. "Another generalization derived from a study of these various crystal structures is what might be termed the principle of maximum hydrogen bonding. All available hydrogen atoms, attached to the electro-negative groups, are generally employed in hydrogen bond formation".
73. T. Steiner, G. Koellner, J. Mol. Biol. 2001, 305, 535-557.
74. G. A. Jeffrey, Introduction to Hydrogen Bonding, OUP, Oxford, 1997.
75. D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405.
76. L. Brammer, Chem. Soc. Rev. 2004, 33, 476-489.
77. P. Vishweshwar, N. J. Babu, A. Nangia, S. A. Mason, H. Puschmann, R. Mondai, J. A. K. Howard, J. Phys. Chem. 2004, 108, 9406-9416.
78. W. Zierkiewicz, P. Jurecka, P. Hobza, ChemPhysChem 2005, 6, 609-617.
79. A. Angeloni, P. C. Crawford, A. G. Orpen, T. J. Podesta, B. J. Shore, Chem. Eur. J. 2004, 10, 3783-3791.
80. D. B. Leznoff, B. Y. Xue, R. J. Batchelor, F. W. B. Einstein, B. O. Patrick, Inorg. Chem. 2001, 40, 6026-6034.
81. A. A. Borkowski, C. L. Cahill, Cryst. Growth Des. 2006, 6, 2241-2247, and the succeeding paper.
82. Z. F. Zhou, K. D. M. Harris, ChemPhysChem 2006, 7, 1649-1653.
83. J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89-98.
84. V. R. Thalladi, H. C. Weiss, D. Bläser, R. Boese, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 8702-8710.
85. I. Hyla-Kryspin, G. Haufe, S. Grimme, Chem. Eur. J. 2004, 10, 3411-3422.
86. K. Reichenbächer, H. I. Suss, J. Hulliger, Chem. Soc. Rev. 2005, 34, 22-30.
87. O. Jeannin, M. Fourmigué, Chem. Eur. J. 2006, 12, 2994-3005.
88. J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
89. P. Ganguly, J. Am. Chem. Soc. 1993, 115, 9287-9288.
90. S. C. F. Kui, N. Y. Zhu, M. C. W. Chan, Angew. Chem. 2003, 115, 1666-1670;
91. Angew. Chem. Int. Ed. 2003, 42, 1628-1632.
92. F. Hof, F. Diederich, Chem. Commun. 2004, 484-487.
93. J. D. Dunitz, A. Gavezzotti, Acc. Chem. Res. 1999, 32, 677-684.
94. F. Demartin, G. Filippini, A. Gavezzotti, S. Rizzato, Acta Crystallogr. Sect B 2004, 60, 609-620.
95. J. D. Dunitz, A. Gavezzotti, Cryst. Growth Des. 2005, 5, 2180-2189.
96. J. D. Dunitz, B. Schweizer, CrystEngComm 2007, 9, 266-269.
97. In his book (reference [3], p. 85), Kitaigorodskii writes that "so far only one significant conclusion suggests itself: The formation of hydrogen bonds does not handicap the layout of molecules in conformity with the general [geometrical] rules of the packing of crystals". About molecular compounds (cocrystals in modern-day parlance) he says "the formation of such a crystal does not necessarily point to some kind of specific forces between the 'compound' molecules". This is all he is willing to concede!
98. T. Steiner, G. R. Desiraju, Chem. Commun. 1998, 891-892.
99. A. J. Pertsin, A. I. Kitaigorodskii, The Atom-Atom Potential Method, Springer, Berlin, 1987, p. 3.
100. M. C. Etter, Acc. Chem. Res. 1990, 23, 120-126.
101. C. B. Aakeröy, D. J. Salmon, CrystEngComm 2005, 7, 439-448, and references therein.
102. P. Vishweshwar, A. Nangia, V. M. Lynch, Cryst. Growth Des. 2003, 3, 783-790.
103. P.W. Baures, J. R. Rush, A. V. Wiznycia, J. Desper, A. A. Helfrich, A. M. Beatty, Cryst. Growth Des. 2002, 2, 653-664.
104. J. F. Remenar, S. L. Morissette, M. L. Peterson, B. Moulton, J. M. MacPhee, H. R. Guzman, Ö. Almarsson, J. Am. Chem. Soc. 2003, 125, 8456-8457.
105. By "directionality" in this context is meant any kind of spatial or chemical anisotropy in the crystal structure.
106. G. R. Desiraju, Nat. Mater. 2002, 1, 77-79.
107. It is unfortunate that McCrone's dictum has been overused to the point where some chemists believe that any organic compound will give (ambient-pressure) polymorphs, provided enough time and money is spent in this enterprise. See, W. C. McCrone, Physics and Chemistry of the Organic Solid State, Vol. 2 (Eds.: D. Fox, M. M. Labes, A. Weissberger), Wiley Interscience, New York, 1965, pp. 725-767. "It is at least this author's opinion that every compound has different polymorphic forms and that, in general, the number of forms known for a given compound is proportional to the time and money spent in research on that compound". I would like to suggest that this dictum is true only in those cases where the kinetic outcome of crystallization is distinct from the thermodynamic one.
108. S. Roy, A. Nangia, Cryst. Growth Des. 2007, 7, DOI: 10.1021/cg070542t.
109. A. Dey, G. R. Desiraju, CrystEngComm 2006, 8, 478-482.
110. A. Dey, M. T. Kirchner, V. R. Vangala, G. R. Desiraju, R. Mondai, J. A. K. Howard, J. Am. Chem. Soc. 2005, 127, 10545-10559.
111. K. Müller, F. Diederich, R. Paulini, Angew. Chem. 2005, 117, 1820-1839;
112. Angew. Chem. Int. Ed. 2005, 44, 1788-1805.
113. G. R. Desiraju, CrystEngComm 2002, 4, 499.
114. P. K. Thallapally, R. K. R. Jetti, A. K. Katz, H. L. Carrell, K. Singh, K. Lahiri, S. R. Kotha, R. Boese, G. R. Desiraju, Angew. Chem. 2004, 116, 1169-1175;
115. Angew. Chem. Int. Ed. 2004, 43, 1149-1155.
116. T. Gelbrich, M. B. Hursthouse, CrystEngComm 2005, 7, 324-336. These authors distinguish between supramolecular synthons and their so-called "supramolecular constructs" and state that synthons contain well-defined directional interactions as opposed to constructs. My original definition of the term "supramolecular synthon" (reference [30]) neither contains nor implies any such limitation. The term "synthon" includes all types of molecular recognition. Given in my 1995 review are examples of synthons which contain only van der Waals and other largely nondirectional interactions (phenyl⋯phenyl herringbone and stacking, alkyl⋯alkyl),
117. J. D. Dunitz, Chem. Commun. 2003, 545-548.
118. A. R. Oganov, C. W. Glass, J. Chem. Phys. 2006, 124, 244704.
119. P. Raiteri, R. Martonak, M. Parrinello, Angew. Chem. 2005, 117, 3835-3839;
120. Angew. Chem. Int. Ed. 2005, 44, 3769-3773.
121. G. M. Day, W. D. S. Motherwell, H. L. Ammon, S. X. M. Boerrigter, R. G. Della Valle, E. Venuti, A. Dzyabchenko, J. D. Dunitz, B. Schweizer, B. P. van Eijk, P. Erk, J. C. Facelli, V. E. Bazterra, M. B. Ferraro, D. W. M. Hofmann, F. J. J. Leusen, C. Liang, C. C. Pantelides, P. G. Karamertzanis, S. L. Price, T. C. Lewis, H. Nowell, A. Torrisi, H. A. Scheraga, Y. A. Arnautova, M. U. Schmidt, P. Verwer, Acta Crystallogr. Sect. B 2005, 61, 511-527.
122. J. A. R. P. Sarma, G. R. Desiraju, Cryst. Growth Des. 2002, 2, 93-100.
123. A. Dey, N. N. Pati, G. R. Desiraju, CrystEngComm 2006, 8, 751-755.
124. C. Ouvrard, S. L. Price, Cryst. Growth Des. 2004, 4, 1119-1127.
125. G. R. Desiraju, CrystEngComm 2007, 9, 91-92.
126. J. W. Steed, CrystEngComm 2003, 5, 169-179.
127. V. S. S. Kumar, A. Addlagatta, A. Nangia, W. T. Robinson, C. K. Broder, R. Mondal, I. R. Evans, J. A. K. Howard, F. H. Allen, Angew. Chem. 2002, 114, 4004- 4007;
128. Angew. Chem. Int. Ed. 2002, 41, 3848-3851.
129. D. Das, R. Banerjee, R. Mondal, J. A. K. Howard, R. Boese, G. R. Desiraju, Chem. Commun. 2006, 555-557;
130. see also: M. Gdaniec, CrystEngComm 2007, 9, 286-288. However, we stand by our result on the isolated trimer polymorph of pentafluorophenol, and will submit our rebuttal shortly (D. Bläser, M. T. Kirchner, R. Boese, G. R. Desiraju, in preparation).
131. R. J. Davey, G. Dent, R. K. Mughal, S. Parveen, Cryst. Growth Des. 2006, 6, 1788-1796.
132. R. Mondal, J. A. K. Howard, R. Banerjee, G. R. Desiraju, Cryst. Growth Des. 2006, 6, 2507-2516.
133. R. Banerjee, P. M. Bhatt, M. T. Kirchner, G. R. Desiraju, Angew. Chem. 2005, 117, 2571-2576;
134. Angew. Chem. Int. Ed. 2005, 44, 2515-2520.
135. A. Nangia, G. R. Desiraju, Chem. Commun. 1999, 605-606.