4 A. Kalman, Acta Crystallogr., Sect. B, 2005, 61, 536.
5 In Polymorphism in the Pharmaceutical Industry, ed. R. Hilfiker,
Wiley-VCH, Weinheim, 2006.
6 (a) H. Karfunkel, H. Wilts, Z. Hao, A. Iqbal, J. Mizuguchi and Z.
Wu, Acta Crystallogr., Sect. B, 1999, 55, 1075; (b) N. J. Babu and
A. Nangia, Cryst. Growth Des., 2006, 6, 1753.
868; (i) E. Bosch and C. L. Barnes, Cryst. Growth Des., 2002, 2,
299; (j) V. R. Pedireddi, D. S. Reddy, B. S. Goud, D. C. Craig, A.
D. Rae and G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 1994,
2353.
12 (a) A. Anthony, M. Jaskolski, A. Nangia and G. R. Desiraju,
Chem. Commun., 1998, 2537; (b) F. C. Pigge, V. R. Vangala and D.
C. Swenson, Chem. Commun., 2006, 2123.
13 L. Fabian and A. Kalman, Acta Crystallogr., Sect. B, 2004, 60,
547.
14 (a) C. M. Reddy, M. T. Kirchner, R. C. Gundakaram, K. A.
Padmanabhan and G. R. Desiraju, Chem. Eur. J, 2006, 12, 2222;
(b) A. C. B. Lucassen, A. Karton, G. Leitus, L. J. W. Shimon, J. M.
L. Martin and M. E. van der Boom, Cryst. Growth Des., 2007, 7,
386.
7 Some examples of polymorphs7a,b,e and isostructural7a,c,d cases
from our group. (a) S. Aitipamula and A. Nangia, Chem. Com-
mun., 2005, 3159; (b) S. Roy, R. Banerjee, A. Nangia and G. J.
Kruger, Chem. Eur. J., 2006, 12, 3777; (c) S. Aitipamula and A.
Nangia, Chem. Eur. J., 2005, 11, 6727; (d) B. K. Saha and A.
Nangia, Heteroat. Chem., 2007, 18, 185; (e) S. K. Chandra, N. K.
Nath, S. Roy and A. Nangia, Cryst. Growth Des., 2008, 8, 140.
ary/Isostructural_crystals.
15 G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological
Structures, Springer-Verlag, Berlin, 1991, p. 24.
9 The chloro and bromo phloroglucinols form hydrates. (a) B. K.
Saha and A. Nangia, Chem. Commun., 2005, 3024; (b) B. K. Saha
and A. Nangia, Chem. Commun., 2006, 1825.
16 U. C. Singh and P. A. Kollman, J. Chem. Phys., 1985, 83, 4033.
17 (a) D. Margraf and J. W. Bats, Acta Crystallogr., Sect. E, 2006, 62,
o502; (b) H. J. Milledge and L. M. Pant, Acta Crystallogr., 1960,
13, 285; (c) P. Kirsop, J. M. D. Storey and W. T. A. Harrison, Acta
Crystallogr., Sect. E, 2004, 60, o222; (d) A. T. Christensen and K.
O. Strømme, Acta Crystallogr., Sect. B, 1969, 25, 657; (e) G.
Ferguson, J. N. Low, G. H. Penner and J. L. Wardell, Acta
Crystallogr., Sect. C, 1998, 54, 1974.
18 SAINT-Plus, version 6.45, Brucker AXS Inc., Madison, WI, 2003.
19 G. M. Sheldrick, SHELX-97: Program for the Solution and Re-
finement of Crystal Structures, University of Gottingen, Germany,
1997.
10 F. L. Weitl, J. Org. Chem., 1976, 41, 2044.
11 (a) B. K. Saha, R. K. R. Jetti, L. S. Reddy, S. Aitipamula and A.
Nangia, Cryst. Growth Des., 2005, 5, 887; (b) B. K. Saha, A.
Nangia and J.-F. Nicoud, Cryst. Growth Des., 2006, 6, 1278; (c) R.
Paulini, K. Muller and F. Diederich, Angew. Chem., Int. Ed., 2005,
44, 1788; (d) F. Zordan, L. Brammer and P. Sherwood, J. Am.
Chem. Soc., 2005, 127, 5979; (e) C. B. Aakeroy, M. Fasulo, N.
Schultheiss, J. Desper and C. Moore, J. Am. Chem. Soc., 2007, 129,
13772; (f) J. N. Moorthy, P. Venkatakrishnan, P. Mal, S. Dixit and
P. Venugopalan, Cryst. Growth Des., 2003, 3, 581; (g) R. G.
Gonnade, M. M. Bhadbhade, M. S. Shashidhar and A. K. Sanki,
Chem. Commun., 2005, 5870; (h) D. Chopra, V. Thiruvenkatam, S.
G. Manjunath and T. N. Guru Row, Cryst. Growth Des., 2007, 7,
20 (a) G. M. Sheldrick, SADABS: Program for Empirical Absorption of
Area Detector Data, University of Gottingen, Germany, 1996; (b) G.
M. Sheldrick, Program for Multi-scan Absorption Correction of Area
Detector Data, version 2.10, University of Gottingen, Germany, 2003.
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