Paper
CrystEngComm
essentially identical. The results of a series of crystal growth
experiments suggest that pH and solvent play important roles
in the formation of these polymorphs. The possible hydrogen-
bonding sites in the crystals can be well predicted by analyzing
the site-specific reactivity of atoms in 2-ODHPCA via the con-
densed Fukui function and the dual descriptor. Lattice energy
calculations by DFT and thermal study by DSC provided clues
to the relative stability of four forms. HSM revealed solid–solid
phase transitions from form II to I, forms III and IV to II.
Conformational search did not suggest possible conforma-
tional polymorphs. Meanwhile, similar compounds such as
4-hydroxynicotinic acid and 6-hydroxynicotinic acid also
exist in the ketonic form in the solid state,40 yet no crystal
structure of 5-hydroxynicotinic acid is reported. And neither
4-hydroxynicotinic acid nor 6-hydroxynicotinic acid is poly-
morphic although 4-hydroxynicotinic acid does have a hemi-
hydrate form reported.41 Whether it is due to a lack of effort of
polymorph screening or unique molecular properties remains
to be explored.
and R. M. Sweet, Academic Press, New York, 1997, vol. 276,
pp. 307–326.
13 G. M. Sheldrick, SHELXL97 and SHELXS97, University of
Gottingen, 1997.
14 P. W. Ayers and M. Levy, Theor. Chem. Acc., 2000, 103,
353–360.
15 R. G. Parr and W. Yang, J. Am. Chem. Soc., 1984, 106,
4049–4050.
16 W. Yang and R. G. Parr, Proc. Natl. Acad. Sci. U. S. A., 1985,
82, 6723–6726.
17 C. Morell, A. Grand and A. Toro-Labbe, J. Phys. Chem. A,
2005, 109, 205–212.
18 P. Geerlings, F. D. Proft and W. Langenaeker, Chem. Rev.,
2003, 103, 1793–1874.
19 S. B. Liu, Wuli Huaxue Xuebao, 2009, 25, 590–600.
20 A. D. Becke, J. Chem. Phys., 1993, 98, 5648–5652.
21 C. Lee, W. Yang and R. G. Parr, Phys. Rev. B: Condens. Matter
Mater. Phys., 1988, 37, 785–789.
22 A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988,
88, 899–926.
23 J. P. Foster and F. Weinhold, J. Am. Chem. Soc., 1980, 102,
7211–7218.
Acknowledgements
SL thanks Natural Science Foundation of Hubei Province
for financial support (2014CFB787). PZ thanks the financial
support by the National Natural Science Foundation of China
(grant no. 21403097) and the Fundamental Research Funds
for the Central Universities (lzujbky-2014-182). TL thanks NSF
for financial support (DMR-1006364). The authors are also
grateful to Dr. Sean Parkin for providing laboratory facilities
and helpful discussion.
24 T. Li and S. Feng, Pharm. Res., 2006, 23, 2326–2332.
25 S. Feng and T. Li, J. Chem. Theory Comput., 2006, 2, 149–156.
26 R. Dovesi, R. Orlando, B. Civalleri, C. Roetti, V. R. Saunders
and C. M. Zicovich-Wilson, Z. Kristallogr., 2005, 220,
571–573.
27 S. F. Boys and F. Bernardi, Mol. Phys., 1970, 19, 553–566.
28 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,
M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone,
B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato,
X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng,
J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda,
J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,
H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta,
F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin,
V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari,
A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi,
N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross,
V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts,
R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi,
C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma,
V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg,
S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz,
J. Cioslowski and D. J. Fox, Gaussian 09, Revision, A. 02,
Gaussian, Inc., Wallingford CT, 2009.
References
1 O. N. Miller, Ger. Pat., DE 2157333, 1972.
2 A. Tinschert, A. Kiener, K. Heinzmann and A. Tscherch,
Arch. Microbiol., 1997, 168, 355–361.
3 R. Weyer, V. Hitzel and E. Granzer, Ger. Pat., DE 2637477,
1978.
4 S. M. O. Quintal, H. I. S. Nogueira, V. Felix and
M. G. B. Drew, Polyhedron, 2002, 21, 2783–2791.
5 Y.-F. Yue, W. Sun, E.-Q. Gao, C.-J. Fang, S. Xu and C.-H. Yan,
Inorg. Chim. Acta, 2007, 360, 1466–1473.
6 A. Boulton and A. McKillop, Comprehensive Heterocyclic
Chemistry: the Structure, Reactions, Synthesis and Uses of
Heterocyclic Compounds, Pergamon, Oxford, 1984.
7 M. S. Saleh, K. A. Idriss, M. S. Abu-Bakr and E. Y. Hashem,
Analyst, 1992, 117, 1003–1007.
8 S. K. Dogra, J. Mol. Struct., 2005, 737, 189–199.
9 S. Long, M. Siegler and T. Li, Acta Crystallogr., Sect. E: Struct.
Rep. Online, 2006, 62, O5664–O5665.
29 M. Fujinaga and M. N. G. James, Acta Crystallogr., Sect. B:
Struct. Crystallogr. Cryst. Chem., 1980, 36, 3196–3199.
30 L. Leiserowitz, Acta Crystallogr., Sect. B: Struct. Crystallogr.
Cryst. Chem., 1976, 32, 775–802.
10 R. C. Santos, R. M. B. B. M. Figueira, M. F. M. Piedade,
H. P. Diogo and M. E. M. da Piedade, J. Phys. Chem. B, 2009,
14291–14309.
31 J. Dunitz and J. Berstein, Acc. Chem. Res., 1995, 28, 193–200.
32 I. S. Lee, K. T. Kim, A. Y. Lee and A. S. Myerson, Cryst.
Growth Des., 2008, 8, 108–113.
11 Nonius, Collect, Nonius BV, Delft, the Netherlands, 2002.
12 Z. Otwinowski and W. Minor, in Methods in Enzymology:
Macromolecular Crystallography, Part A, ed. C. W. Carter Jr.
33 C. S. Towler, R. J. Davey, R. W. Lancaster and C. J. Price,
J. Am. Chem. Soc., 2004, 126, 13347–13353.
34 L. Yu and K. Ng, J. Pharm. Sci., 2002, 91, 2367–2375.
CrystEngComm
This journal is © The Royal Society of Chemistry 2015