Polymorphic co-crystals from polymorphic co-crystal formers: Competition between carboxylic acid⋯pyridine and phenol⋯pyridine hydrogen bonds

Crystal Growth and Design

Volumn 13, Issue 9, 2013, Pages 3935-3952

  Lemmerer, Andreas ^a   Adsmond, Daniel A ^e   Esterhuysen, Catharine ^d   Bernstein, Joel ^b,c  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b NEW YORK UNIVERSITY ABU DHABI   (United Arab Emirates)

^c BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^d STELLENBOSCH UNIVERSITY   (South Africa)

^e FERRIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBENZOIC ACIDS; BONDED INTERACTIONS; CARBONYL ACCEPTORS; CONFORMATIONAL DIFFERENCES; CRYSTALLINE SOLIDS; HYDROGEN BOND DONORS; INDIVIDUAL COMPONENTS; MOLECULAR COMPLEXES;

AMIDES; CARBOXYLIC ACIDS; COMPLEXATION; PHENOLS; PYRIDINE;

HYDROGEN BONDS;

EID: 84883709126     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg4006357     Document Type: Article

References (173)

1. Almarsson, Ö.; Zaworotko, M. J. Chem.Commun. 2004, 1889-1896
2. Stahly, G. P. Cryst. Growth Des. 2007, 7, 1007-1026
3. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301-309
4. Shan, N.; Zaworotko, M. J. Drug Discovery Today 2008, 13, 440-446
5. Reddy, L. S.; Babu, N. J.; Nangia, A. Chem. Commun. 2006, 1369-1371
6. Weyna, D. R.; Shattock, T.; Vishweshwar, P.; Zaworotko, M. J. Cryst. Growth Des. 2009, 9, 1106-1123
7. Walsh, R. D. B.; Bradner, M. W.; Fleischmann, S.; Morales, L. A.; Moulton, B.; Rodríguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, 186-187
8. Aakeröy, C. B.; Forbes, S.; Desper, J. J. Am. Chem. Soc. 2009, 131, 17048-17049
9. Sekhon, B. S. Ars Pharm. 2009, 50, 99-117
10. Jones, W.; Motherweel, W. D. A.; Trask, A. V. MRS Bull. 2006, 31, 875-879
11. Mirza, S.; Miroshnyk, I.; Heinämäki, J.; Yliruusi, J. Dosis 2008, 24, 90-96
12. Brittain, H. G. Cryst. Growth Des. 2012, 12, 1046-1054
13. Brittain, H. G. Cryst. Growth Des. 2012, 12, 5823-5832
14. Pfeiffer, P. Organische Molekuulverbindungen; Verlag von Ferdinand Enke: Stuttgart, Germany, 1927.
15. For a review of earlier literature, see Herbstein, F. H. Perspectives in Structural Chemistry; Dunitz, J. D.; Ibers, J., Eds.; John Wiley & Sons: New York, 1971; Vol. 4, pp 166-395; especially references 4-26 therein.
16. Bernstein, J. Polymorphism in Molecular Crystals; Oxford Science Publications: Oxford, 2002.
17. Ahn, S.; Guo, F.; Kariuki, B. M.; Harris, K. D. M. J. Am. Chem. Soc. 2006, 128, 8441-8452
18. Llinàs, A.; Goodman, J. M. Drug Discovery Today 2008, 13, 198-210
19. Bernstein, J. Cryst. Growth Des. 2011, 11, 632-650
20. "This heterosynthon will provide a different set of molecules to answer the frequently-asked billion dollar question in pharmaceutical R&D: do API co-crystals tend to be less polymorphic than pure compounds?" Reddy, L. S.; Babu, N. J.; Nangia, A. Chem. Commun. 2006, 1369-1371
21. "Indeed, to our knowledge there have not yet been any examples of 'supramolecular isomerism' in co-crystals. If these observations hold true over a broader range of compounds it would suggest that co-crystals represent a desirable class of compound from the perspectives of both design and phase stability." Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 499-516
22. "This question will not have a direct answer, because to prove the absence of polymorphism is tantamount to 'proving the negative'. But if one considers the argument that compounds have a lower degree of self-complementarity than complementarity to a rationally selected co-crystal former, one might suspect that a compound polymorphic in the pure state could display a decreased tendency to polymorphism as a co-crystal relative to the pure phase." Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889-1896
23. Vishweshwar, P.; McMahon, J. A.; Peterson, M. L.; Hickey, M. B.; Shattock, T. R.; Zaworotko, M. J. Chem. Commun. 2005, 4601-4603
24. Bond, A. D. CrystEngComm 2007, 9, 833-834
25. Aakeröy, C. B.; Beatty, A. M. Aust. J. Chem. 2001, 54, 409-421
26. Aakeröy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439-448
27. Haller, T. M.; Rheingold, A. L.; Brill, T. B. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1983, 39, 1559-1563
28. Hostettler, M.; Birkedal, H.; Gardon, M.; Chapuis, G.; Schwarzenbach, D.; Bonin, M. Acta Crystallogr., Sect. B: Struct. Sci. 1999, 55, 448-458
29. Ahn, S.; Kariuki, B. M.; Harris, K. D. M. Cryst Growth Des. 2001, 1, 107-111
30. Gardon, M.; Schönleber, A.; Chapuis, G.; Hostettler, M.; Bonin, M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2001, 57, 936-938
31. Koshima, H.; Miyauchi, M. Cryst. Growth Des. 2001, 1, 355-357
32. Farrell, D. M. M.; Ferguson, G.; Lough, A. J.; Glidewell, C. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 530-544
33. Bowes, F. F.; Ferguson, G.; Lough, A. J.; Glidewell, C. Acta Crystallogr., Sect. B: Struct. Sci. 2003, 59, 277-286
34. Gardon, M.; Pinheiro, C. B.; Chapuis, G. Acta Crystallogr., Sect. B: Struct. Sci. 2003, 59, 527-536
35. Pinheiro, C. B.; Gardon, M.; Chapuis, G. Acta Crystallogr., Sect. B: Struct. Sci. 2003, 59, 414-427
36. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. 2004, 890-891
37. Trask, A. V.; van de Streek, J.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5, 2233-2241
38. Shattock, T. R.; Vishweshwar, P.; Wang, Z.; Zaworotko, M. J. Cryst. Growth Des. 2005, 5, 2046-2049
39. Bis, J. A.; Vishweshwar, P.; Middleton, R. A.; Zaworotko, M. J. Cryst. Growth Des. 2006, 6, 1048-1053
40. Drebushchak, T. N.; Mikheilenko, M. A.; Boldyreva, E. V.; Shakhtshneider, T. P. Acta Crystallogr., Sect E: Struct. Rep. 2006, 62, o2669-o2671
41. Drebushchak, T. N.; Mikheilenko, M. A.; Boldyreva, E. V.; Shakhtshneider, T. P. Acta Crystallogr., Sect E: Struct. Rep. 2006, 62, o2707-o2709
42. Sreekanth, B. R.; Vishweshwar, P.; Vyas, K. Chem. Commun. 2007, 2375-2377
43. Wang, J.; Ding, L.; Yang, C. CrystEngComm 2007, 9, 591-594
44. Childs, S. L.; Hardcastle, K. I. CrystEngComm 2007, 9, 364-367
45. Drebushchak, T. N.; Mikhailenko, M. A.; Drebushchak, V. A.; Boldyreva, E. V. Struct. Chem. 2007, 18, 449-456
46. Gryl, M.; Krawczuk, A.; Stadnicka, K. Acta Crystallogr., Sect. B: Struct. Sci. 2008, 64, 623-632
47. Braga, D.; Palladino, G.; Polito, M.; Rubini, K.; Grepioni, F.; Chierotti, M. R.; Gobetto, R. Chem.-Eur. J. 2008, 14, 10149-10159
48. Porter, W. W.; Elie, S. C.; Matzger, A. J. Cryst. Growth Des. 2008, 8, 14-16
49. ter Horst, J. H.; Cains, P. W. Cryst. Growth Des. 2008, 8, 2537-2542
50. Skovsgaard, S.; Bond, A. A. CrystEngComm 2009, 11, 444-453
51. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. CrystEngComm 2009, 11, 889-895
52. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. CrystEngComm 2009, 11, 1823-1827
53. Raatikainen, K.; Rissanen, K. CrystEngComm 2009, 11, 750-752
54. Du, M.; Jiang, X.-J.; Tan, X.; Zhang, Z.-H.; Cai, H. CrystEngComm 2009, 11, 454-462
55. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. Cryst. Growth Des. 2010, 10, 2229-2238
56. Schultheiss, N.; Bethune, S.; Hench, J.-O. CrystEngComm 2010, 12, 2436-2442
57. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. CrystEngComm 2010, 12, 3691-3697
58. Ye, H.-Y.; Ge, J.-Z.; Chen, F.; Xiong, R.-G. CrystEngComm 2010, 12, 1705-1708
59. Yu, Z. Q.; Chow, P. S.; Tan, R. B. H.; Ang, W. H. Cryst. Growth Des. 2011, 11, 4525-4532
60. Halasz, I.; Rubčić, M.; Užarević, K.; Dilović, I.; Meštrović, E. New J. Chem. 2011, 35, 24-27
61. Thomas, L. H.; Craig, G. A.; Gutmann, M. J.; Parkin, A.; Shankland, K.; Wilson, C. C. CrystEngComm 2011, 13, 3349-3354
62. Schultheiss, N.; Roe, M.; Boerrigter, X. M. CrystEngComm 2011, 13, 611-619
63. Bortel, G.; Pekker, S.; Kovats, E. Cryst. Growth Des. 2011, 11, 865-874
64. Ueto, T.; Takata, N.; Muroyama, N.; Nedu, A.; Sasaki, A.; Tanida, S.; Terada, K. Cryst. Growth Des. 2012, 12, 485-494
65. Lemmerer, A.; Bernstein, J.; Kahlenberg, V. Acta Crystallogr., Sect. E: Struct. Rep. 2012, 68, o190
66. Limwikrant, W.; Nagai, A.; Hagiwara, Y.; Higashi, K.; Yamamoto, K.; Moribe, K. Int. J. Pharm. 2012, 431, 237-240
67. Kaur, R.; Row, T. N. G. Cryst. Growth Des. 2012, 12, 2744-2747
68. Zhang, S.-W.; Guzei, I. A.; de Villiers, M. M.; Yu, L.; Krzyzaniak, J. F. Cryst. Growth. Des. 2012, 12, 4090-4097
69. Lemmerer, A.; Fernandes, M. A. New J. Chem. 2012, 36, 2242-2252
70. Martí-Rujas, J.; Kariuki, B. M.; Hughes, C. E.; Morte-Ródenas, A.; Guo, F.; Glavcheva-Laleva, Z.; Taştemür, K.; Ooi, L.; Yeo, L.; Harris, K. D. M. New J. Chem. 2011, 35, 1515-1521
71. Abourahma, H.; Cocuzza, D. S.; Melendez, J.; Urban, J. M. CrystEngComm 2011, 13, 6442-6450
72. Oliviera, M. A.; Peterson, M. L.; Klein, D. Cryst. Growth Des. 2008, 8, 4487-4493
73. Sarma, B.; Reddy, L. S.; Nangia, A. Cryst. Growth Des. 2008, 8, 4546-4552
74. Babu, N. J.; Reddy, L. S.; Aitipamula, S.; Nangia, A. Chem.-Asian J. 2008, 3, 1122-1133
75. Karki, S.; Friščić, T.; Jones, W. CrystEngComm 2009, 11, 470-481
76. Seaton, C. C.; Parkin, A.; Wilson, C. C.; Blagden, N. Cryst Growth Des. 2009, 9, 47-56
77. Jayasankar, A.; Reddy, L. S.; Bethune, S. J.; Rodríguez-Hornedo, N. Cryst. Growth Des. 2009, 9, 889-897
78. Trask, A. V.; van de Streek, J.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5, 2233-2241
79. Aakeröy, C. B.; Desper, J.; Elisabeth, E.; Helfrich, B. A.; Levin, B.; Urbina, J. F. Z. Kristallogr. 2005, 220, 325-332
80. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327
81. McMahon, J. A.; Bis, J. A.; Vishweshar, P.; Shattock, T. R.; McLaughlin, O. L.; Zaworotko, M. J. Z. Kristallogr. 2005, 220, 340-350
82. Aakeröy, C. B.; Schultheiss, N. Assembly of Molecular Solids via Non-covalent Interactions. In Making Crystals by Design; Braga, D.; Grepioni, F., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 209-240.
83. McMahon, J. A.; Bis, J. A.; Vishweshar, P.; Shattock, T. R.; McLaughlin, O. L.; Zaworotko, M. J. Z. Kristallogr. 2005, 220, 340-350
84. Lemmerer, A.; Adsmond, D. A.; Bernstein, J. Cryst. Growth Des. 2011, 11, 2011-2019
85. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126
86. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr., Sect. B: Struct. Sci. 1990, 46, 256-262
87. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573
88. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. J. Am. Chem. Soc. 2002, 124, 14425-14432
89. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242
90. Bhogala, B. R.; Basavoju, S.; Nangia, A. CrystEngComm 2005, 7, 551-562
91. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Cryst. Growth Des. 2003, 3, 159-165
92. Lemmerer, A.; Báthori, N. B.; Bourne, S. A. Acta Crystallogr. Sect., B: Struct. Sci. 2008, 64, 780-790
93. Vishweshwar, P.; Nangia, A.; Lynch, V. M. Cryst. Growth Des. 2003, 3, 783-790
94. Oliveira, M. A.; Peterson, M. L.; Klein, D. Cryst. Growth Des. 2008, 8, 4487-4493
95. Sarma, B.; Reddy, L. S.; Nangia, A. Cryst Growth Des. 2008, 8, 4546-4552
96. Vishweshwar, P.; Nangia, A.; Lynch, V. M. CrystEngComm 2003, 5, 164-168
97. Huang, K.-S.; Britton, D.; Etter, M. C.; Byrn, S. R. J. Mater. Chem. 1997, 7, 713-720
98. Bourne, S. A.; Nassimbeni, L. R.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1991, 1335-1341
99. Lough, A. J.; Gregson, R. M.; Ferguson, G.; Glidewell, C. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1999, 55, 1890-1892
100. Bourne, S. A.; Corin, K. C.; Nassimbeni, L. R.; Toda, F. Cryst. Growth Des. 2005, 5, 379-382
101. Nassimbeni, L. R.; Su, H.; Weber, E.; Skobridis, K. Cryst. Growth Des. 2004, 4, 85-88
102. Olenik, B.; Boese, R.; Sustmann, R. Cryst. Growth Des. 2003, 3, 175-181
103. Shattock, T. R.; Arora, K. K.; Vishweshwar, P.; Zaworotko, M. J. Cryst. Growth Des. 2008, 8, 4533-4545
104. Adsmond, D.; Lapidus, S. In preparation.
105. Nehm, S. J.; Rodríguez-Spong, B.; Rodríguez-Hornedo, N. Cryst. Growth Des. 2006, 6, 592-600
106. Bruker, SMART-NT, version 5.050; Bruker AXS Inc., Madison, Wisconsin, USA, 1999.
107. Bruker SAINT+, version 6.02 (includes XPREP and SADABS); Bruker AXS Inc., Madison, Wisconsin, USA, 1999.
108. Farrugia, L. J. WinGX J. Appl. Crystallogr. 1999, 32, 837-838
109. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112-122
110. Farrugia, L. J. ORTEP-3 J. Appl. Cryst. 1997, 30, 565
111. Spek, A. L Acta Crystallogr., Sect. D: Struct. Biol. 2009, 65, 148-155
112. Brandenburg, K. Diamond, version 2.1e.; Crystal Impact GbR, Bonn, Germany, 1999.
113. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
114. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
115. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
116. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
117. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261
118. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222
119. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 215-241
120. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
121. Ransil, B. J. J. Chem. Phys. 1961, 34, 2109-2118
122. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566
123. Version 5.33: Allen, F. H. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380-388
124. Leiserowitz, L. Acta Crystallogr., Sect. B: Struct. Sci. 1976, 32, 775-802
125. Das, D.; Desiraju, G. R. Chem.-Asian J. 2006, 1-2, 231-244
126. Das, D.; Desiraju, G. R. CrystEngComm 2006, 8, 674-679
127. Brock, C. P.; Duncan, L. L. Chem. Mater. 1994, 6, 1307-1312
128. Taylor, R.; Macrae, C. F. Acta Crystallogr., Sect. B: Struct. Sci. 2001, 57, 815-827
129. Gridunova, G. V.; Furmanova, N. G.; Struchkov, Yu. T.; Ezhova, Z. I.; Grigoreva, L. P.; Chayanov, B. A. Crystallogr. Rep. 1982, 27, 267-272
130. Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449
131. Schur, E.; Bernstein, J. (2013, manuscript in preparation.
132. Phillips, D. C. Acta Crystallogr. 1956, 9, 237-250
133. Mei, X.; Wolf, C. Cryst. Growth Des. 2004, 4, 1099-1103
134. Phillips, D. C.; Ahmed, F. R.; Barnes, W. H. Acta Crystallogr. 1960, 13, 365-377
135. Braga, D.; Grepioni, F.; Maini, L.; Mazzeo, P. P.; Rubini, K. Thermochim. Acta 2010, 507-508, 1-8
136. Herbstein, F. H.; Schmidt, G. M. J. Acta Crystallogr. 1955, 8, 399-405
137. Schur, E.; Bernstein, J.; Lemmerer, A.; Vainer, R. Acta Crystallogr., Sect. E: Struct. Rep. 2011, 67, o2761
138. Koshima, H.; Wang, Y.; Matsuura, T.; Miyahara, I.; Mizutani, H.; Hirotsu, K.; Asahi, T.; Masuhara, H. J. Chem. Soc., Perkin Trans. 2 1997, 2033-2038
139. Binder, W.; Karl, N. Acta Crystallogr., Sect. B: Struct. Sci. 1982, 38, 2919-2921
140. Binder, W.; Karl, N. Acta Crystallogr., Sect. B: Struct. Sci. 1982, 38, 2915-2916
141. http://www.zirchrom.com/organic.htm.
142. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324
143. Aakeröy, C. B.; Desper, J. C.; Smith, M. M. Chem. Commun. 2007, 3936-3938
144. Aakeröy, C. B.; Epa, K. Top. Curr. Chem. 2011, 10.1007/128-2011-155
145. Hino, T.; Ford, J. L.; Powell, M. W. Therm. Acta 2001, 374, 85-92
146. NICOAM01, NICOAM02, and NICOAM03: Bright, W. B.; King, G. S. D. Acta Crystallogr. 1954, 7, 283-288
147. NICOAM: Miwa, Y.; Mizuno, T.; Tsuchida, K.; Taga, T.; Iwata, Y. Acta Crystallogr., Sect. B: Struct. Sci. 1999, 55, 78-84
148. NICOAM04: Li, J.; Bourne, S. A.; Caira, M. Chem. Commun. 2011, 47, 1530-1532
149. Giacomello, G.; Liquori, A. M.; Ripamonti, A. Nature 1956, 177, 944-945
150. Braun, D. E.; Karamertzanis, P. G.; Arlin, J.-B.; Florence, A. J.; Kahlenberg, V.; Tocher, D. A.; Griesser, U. J.; Price, S. L. Cryst. Growth Des. 2011, 11, 210-220
151. Parkin, A.; Adam, M.; Cooper, R. I.; Middlemiss, D. S.; Wilson, C. C Acta Crystallogr., Sect. B: Struct. Sci. 2007, 63, 303-308
152. McMullan, R. K.; Klooster, W. T.; Weber, H.-P. Acta Crystallogr. Sect B: Struct. Sci. 2008, 64, 230-239
153. Jaganathan, N. R.; Rajan, S. S.; Subramanian, E. J. Chem. Crystallogr. 1994, 24, 75-78
154. Thalladi, R. R.; Nusse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236
155. Gopalan, R. S.; Kumaradhas, P.; Kulkarni, G. U.; Rao, C. N. R. J. Mol. Struct. 2000, 521, 97-106
156. Berry, D. J.; Seaton, C. C.; Clegg, W.; Harrington, R. W.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Storey, R.; Jones, W.; Frišč ić, T.; Blagden, N. Cryst. Growth Des. 2008, 8, 1697-1712
157. Amai, M.; Kamijo, M.; Nagase, H.; Endo, T.; Ueda, H. Anal. Sci.: X-Ray Struct. Anal. Online 2001, 21, x9-x10
158. Amai, M.; Kamijo, M.; Nagase, H.; Ogawaw, N.; Endo, T.; Ueda, H. Anal. Sci.: X-Ray Struct. Anal. Online 2006, 22, x121-x122
159. Amai, M.; Endo, T.; Nagase, H.; Ueda, H.; Nakagaki, M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, 54, 1367-1369
160. Chakrabarty, D.; Nagase, H.; Kamijo, M.; Endo, T.; Ueda, H. Anal. Sci.: X-Ray Struct. Anal. Online 2006, 22, x27-x28
161. Fleischman, S. G.; Kuduva, S. S.; McMahon, J. A.; Moulton, B.; Walsh, R. D. B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Cryst. Growth Des. 2003, 3, 909-919
162. Lemmerer, A.; Bernstein, J. CrystEngComm 2010, 12, 2029-2033
163. Báthori, N. B.; Lemmerer, A.; Venter, G. A.; Bourne, S. A.; Caira, M. R. Cryst. Growth Des. 2011, 11, 75-87
164. Wang, Z.-L.; Wei, L.-H.; Li, M.-X. Acta Crystallogr., Sect. E: Struct. Rep. 2006, 62, o3031-o3032
165. Bernstein, J.; Novoa, J. J.; Boese, R.; Cirkel, S. A. Chem.-Eur. J. 2010, 16, 9047-9055
166. Allen, F. H.; Motherwell, W. D. S.; Raithby, P. R.; Shields, G. P.; Taylor, R. New J. Chem. 1999, 23, 25-34
167. Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440-3461
168. Dunitz, J. D.; Bernstein, J. Acc. Chem. Res. 1995, 28, 193-200
169. Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 405-4507
170. Montzka, T. A.; Swaminathan, S.; Firestone, R. A. J. Phys. Chem. 1994, 98, 13171-13176
171. Sato, H.; Hirata, F. J. Mol. Struct.: Theochem 1999, 461-462, 113-120
172. Lemmerer, A.; Báthori, N. B.; Esterhuysen, C.; Bourne, S. A.; Caira, M. R. Cryst. Growth Des. 2009, 9, 2646-2655
173. Aitipamula, S.; Wong, A. B. H.; Chow, P. S.; Tan, R. B. H. CrystEngComm 2012, 14, 8193-8198