Article
CrystEngComm 2002, 4, 271. (d) Atwood, J. L.; Barbour, L. J.; Jerga,
A.; Schottel, B. L. Science 2002, 298, 1000. (e) Saha, B. K.; Nangia, A.
CrystEngComm 2006, 8, 440.
(4) Steed, J. W. CrystEngComm 2003, 5, 169.
(5) (a) Lehmler, H.-J.; Robertson, L. W.; Parkin, S.; Brock, C. P. Acta
Crystallogr. 2002, B58, 140. (b) Brock, C. P. Acta Crystallogr. 2002,
B58, 1025. (c) Brock, C. P.; Duncan, L. L. Chem. Mater. 1994, 6, 1307.
(6) (a) Jetti, R. K. R.; Boese, R.; Sarma, J. A. R. P.; Reddy, L. S.;
Vishweshwar, P.; Desiraju, G. R. Angew. Chem., Int. Ed. 2003, 42,
1963. (b) Sreekanth, B. R.; Vishweshwar, P.; Vyas, K. Chem. Commun.
2007, 2375. (c) Babu, N. J.; Reddy, L. S.; Aitipamula, S.; Nangia, A.
Chem.;Asian J. 2008, 3, 1122.
Crystal Growth & Design, Vol. 10, No. 5, 2010 2399
(16) (a) The COOH dimer is a common synthon in carboxylic acids.
Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311. (b)
Other motifs are also possible. Kolotuchin, S. V.; Fenlon, E. E.; Wilson,
S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl.
1995, 34, 2654.
(17) In general, the high Z0 polymorph structure has shorter hydrogen
bonds. Babu, N. J.; Nangia, A. CrystEngComm 2007, 9, 980.
(18) Gaussian 03 is the latest in the series of electronic structure and
(19) (a) Bernstein, J.; Davey, R. J.; Henck, J. Angew. Chem., Int. Ed.
1999, 38, 3440. (b) Roy, S.; Banerjee, R.; Nangia, A.; Kruger, G. J.
Chem.;Eur. J. 2006, 12, 3777.
(7) 2,5-DHBA: (a) Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.;
Okazaki, S.; Shibagaki, M. Acta Crystallogr. 1982, B38, 1480
(BESKAL). (b) Cohen, D. E.; Benedict, J. B.; Morlan, B.; Chiu, D.
T.; Kahr, B. Cryst. Growth Des. 2007, 7, 492 (BESKAL02).
(8) 2,6-DHBA: (a) Gdaniec, M.; Gilski, M.; Denisov, G. S. Acta
Crystallogr. 1994, C50, 1622 (LEZJAB). (b) MacGillivray, L. R.;
Zaworotko, M. J. J. Chem. Cryst. 1994, 24, 703 (LEZJAB01).
(9) 2,3-DHBA: Okabe, N.; Kyoyama, H. Acta Crystallogr. 2001, E57,
o1224 (CACDAM).
(10) 2,4-DHBA: (a) Parkin, A.; Adam, M.; Cooper, R. I.; Middlemiss,
D. S.; Wilson, C. C. Acta Crystallogr. 2007, B63, 303 (X-ray,
ZZZEEU01). (b) Adam, M. S.; Gutmann, M. J.; Leech, C. K.;
Middlesmiss, D. S.; Parkin, A.; Thomas, L. H.; Wilson, C. C. New J.
Chem. 2010, 34, 85 (neutron).
(20) Cell parameters of 3,4-DHBA monohydrate in CSD. BIJDON03,
˚
˚
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a = 8.045(2) A, b = 8.134(2) A, c = 12.692(4) A, R = 71.58ꢀ, β =
3
˚
˚
76.79ꢀ, γ = 72.17ꢀ, V = 742.114 A . BIJDON, a = 9.926(9) A, b =
˚
˚
9.532(9) A, c=8.138(8) A, R=100.8(1)ꢀ, β=90.7(1)ꢀ, γ=102.40(1)ꢀ,
V=736.953 A . BIJDON02, a=12.32(1) A, b = 3.64(1) A, 17.6(2)
A, R=90ꢀ, β=107.70(20)ꢀ, γ = 90ꢀ, V = 751.906 A .
(21) For example, 2,6-DHBA monohydrate, LEZJEF, a = 6.778(1) A,
3
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˚
˚
3
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˚
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b = 9.411(1) A, c = 11.890(2) A, R = β = γ = 90ꢀ, V = 758.436
A ; and 2,4-DHBA hemihydrate, QIVTUK, a=7.026(2) A, b=
9.547(3) A, c = 11.199(4) A, R=96.78ꢀ, β = 104.34ꢀ, γ = 98.85ꢀ,
V = 709.496 A .
3
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3
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(22) (a) Derissen, J. L.; Smit, P. H. Acta Crystallogr. 1974, B30, 2240.
(b) Benghiat, V.; Leiserowitz, L. J. Chem. Soc., Perkin Trans. 2 1972,
1763.
(11) The unit cell of 2,4-DHBA was reported over 50 years ago but
without solving the space group: Giacomello, A. Nature (London)
1956, 177, 944 (ZZZEEU). a = 9.670 Å, b = 11.560 Å, c = 7.050 Å, R =
105.63ꢀ, β = 91.72ꢀ, γ = 79.92ꢀ, V = 747.107 Å3. A possible error in the
composition of this structure is discussed at the end of this paper.
(12) Cambridge Structural Database, ver. 5.30, ConQuest1.11, November
(13) (a) Brouwer, E. B.; Enright, G. D.; Udachin, K. A.; Lang, S.;
Ooms, K. J.; Haulchuk, P. A.; Ripmeester, J. A. Chem. Commun.
2003, 1416. (b) Mcgrady, G. S.; Odlyha, M.; Prince, P. D.; Steed, J. W.
CrystEngComm 2002, 4, 271. (c) Nagel, N.; Bock, H.; Eller, P. Acta
Crystallogr. 2002, B56, 234.
(14) (a) Wheatley, P. S.; Lough, A. J.; Ferguson, G.; Glidewell, C. Acta
Crystallogr. 1999, C55, 1489. (b) Varughese, S; Pedireddi, V. R.
Chem.;Eur. J. 2006, 12, 1597. (c) Liao, X.; Gautam, M.; Grill, A.;
Zhu, H. J. J. Pharm. Sci. 2010, 99, 246. (d) Sarma, B.; Nath, N. K.;
Bhogala, B. R.; Nangia, A. Cryst. Growth Des. 2009, 9, 1546.
(15) Metal-DHB complexes: (a) Kula, A.; Rzaczynska, Z.; Mazur, L.
J. Chem. Cryst. 2008, 38, 723. (b) Bandoli, G.; Dolmella, A.; Gerber,
T. I. A.; Perils, J.; du Preez, J. G. H. Inorg. Chim. Acta 1999, 294, 114–
118. (c) Aletras, V.; Hadjiliadis, N.; Stabaki, D.; Karaliota, A.; Kamar-
iotaki, M.; Butler, I.; Plakatouras, J. C.; Perlepes, S. Polyhedron 1997,
16, 1399. (d) He, H. Y.; Zhou, Y. L.; Chen, Y. N.; Zhu, L. G. Z.
Kristallogr., New Cryst. Struct. 2005, 220, 448. (e) Yang, Q.; Nie,
J. J.; Xu, D. J. Acta Crystallogr. 2008, E64, m757.
(23) (a) Parveen, S.; Davey, R. J.; Dent, G.; Pritchard, R. G. Chem.
Commun. 2005, 1531. (b) Gavezzotti, A.; Filippini, G.; Kroon, J.; van
Eijck, B. P.; Klewinghaus, P. Chem.;Eur. J. 1997, 3, 894.
(24) (a) Kumar, V. S. S.; Addlagatta, A.; Nangia, A.; Robinson, W. T.;
Broder, C. K.; Mondal, R.; Evans, I. R.; Howard, J. A. K.; Allen,
F. H. Angew. Chem., Int. Ed. 2002, 41, 3848. (b) Das, D.; Banerjee,
R.; Mondal, R.; Howard, J. A. K.; Boese, R.; Desiraju, G. R. Chem.
Commun. 2006, 555. (c) Desiraju, G. R. CrystEngComm 2007, 9, 91.
(d) Anderson, K. M.; Steed, J. W. CrystEngComm 2007, 9, 328. (e)
Nichol, G. S.; Clegg, W. CrystEngComm 2007, 9, 959. (f) Bernstein, J.;
Dunitz, J, D.; Gavezzoti, A. Cryst. Growth Des. 2008, 8, 2011.
(25) SAINT-Plus, version 6.45; Bruker AXS Inc.: Madison, WI, 2003.
(26) Sheldrick, G. M. SADABS, Program for Empirical Absorption
€
Correction of Area Detector Data; University of Gottingen, Germany,
1997.
(27) (a) SMART (Version 5.625) and SHELX-TL (Version 6.12); Bruker
AXS Inc.: Madison, WI, 2000. (b) Sheldrick, G. M. SHELXS-97 and
€
SHELXL-97; University of Gottingen: Germany, 1997.
(28) Barbour, L. J. X-Seed, Graphical Interface to SHELX-97 and POV-
Ray; University of Missouri;Columbia: 1999.
(29) Spek, A. L. PLATON, A Multipurpose Crystallographic Tool;
Utrecht University: Utrecht, The Netherlands, 2002. Spek, A. L.
J. Appl. Crystallogr. 2003, 36, 7.
(30) Powder Cell for structure visualization, powder pattern calculation