Crystal structure prediction could have helped the experimentalists with polymorphism in benzamide

Molecular Simulation

Volumn 34, Issue 10-15, 2008, Pages 1359-1370

  Thun, Juergen ^a   Schoeffel, Markus ^a   Breu, Josef ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Benzamide, polymorphism; Crystal structure prediction; Density functional theory; Point charges

Indexed keywords

AMIDES; DENSITY FUNCTIONAL THEORY; FORECASTING; POLYMORPHISM; POWDERS;

BENZAMIDE; BENZAMIDE, POLYMORPHISM; CHARACTERISATION; CRYSTAL STRUCTURE PREDICTION; CRYSTAL STRUCTURE PREDICTIONS; LOW ENERGIES; METASTABLE FORMS; MOLECULAR MATERIALS; PEAK OVERLAPS; POINT CHARGES; STATE OF THE ARTS;

CRYSTAL STRUCTURE;

EID: 56749097886     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020802208943     Document Type: Article

References (34)

1. J. Bernstein, Polymorphism, in Molecular Crystals, Oxford University Press, Oxford, 2002.
2. S.R. Chemburkar, J. Bauer, K. Deming, H. Spiwek, K. Patel, J. Morris, R. Henry, S. Spanton, W. Dziki, W. Porter et al., Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development, Org. Process Res. Dev. 4 (2000), pp. 413-417.
3. H. Nowell and S. L. Price, Validation of a search technique for crystal structure prediction of flexible molecules by application to piracetam, Acta Crystallogr. B 61 (2005), pp. 558-568.
4. M.U. Schmidt, C. Buchsbaum, J.M. Schnorr, D.W.M. Hofmann, and M. Ermrich, Pigment-Orange-5: crystal structure determination from a non-indexed X-ray powder diagram, Z. Kristallogr. 222 '(2007), pp. 30-33.
5. M.U. Schmidt, R.E. Dinnebier, and H. Kalkhof, Crystal engineering on industrial diaryl pigments using lattice energy minimizations and X-ray powder diffraction, J. Phys. Chem. B 111 (2007), pp. 9722-9732.
6. G.M. Day, W.D.S. Motherwell, H.L. Ammon, S.X.M. Boerrigter, R.G. Delia Valle, E. Venuti, A. Dzyabchenko, J.D. Dunitz, B. Schweizer, B.P. van Eijck et al., A third blind test of crystal structure prediction, Acta Crystallogr. B 61 (2005), pp. 511 -527.
7. J.P.M. Lommerse, W.D.S. Motherwell, H.L. Ammon, J.D. Dunitz, A. Gavezzotti, D.W.M. Hofmann, F.JJ. Leusen, W.T.M. Mooij, S.L. Price, B. Schweizer et al., A test of crystal structure prediction of small organic molecules, Acta Crystallogr. B 56 (2000), pp. 697-714.
8. W.D.S. Motherwell, H.L. Ammon, J.D. Dunitz, A. Dzyabchenko, P. Erk, A. Gavezzotti, D.W.M. Hofmann, FJ.J. Leusen, J.P.M. Lommerse, W.T.M. Mooij et al., Crystal structure prediction of small organic molecules: a second blind test, Acta Crystallogr. B 58(2002), pp. 647-661.
9. U. Koch and A.J. Stone, Conformational dependence of the molecular charge distribution and its influence on intermolecular interactions, J. Chem. Soc. Faraday Trans. 92 (1996), pp. 1701-1708.
10. A.J. Stone and M. Alderton, Distributed multipole analysis - methods and applications, (Reprinted from Molecular Physics, vol 56, pg 1047-1064, 1985) Mol. Phys. 100 (2002), pp. 221-233.
11. A.J. Stone, Distributed multipole analysis or how to describe a olecular clarge-distribution, Chem. Phys. Lett. 83 (1981), pp. 233-239.
12. G.M. Day, W.D.S. Motherwell, and W. Jones. A strategy for predicting the crystal structures of flexible molecules: the polymorphism of phénobarbital, Phys. Chem. Chem. Phys. 9 (2007), pp. 1693-1704.
13. J. Thun. L. Seyfarth, J. Senker, R.E. Dinnebier. and J. Breu, Polymorphism in benzamide: Solving a 175-year-old riddle, Angew. Chem. Int. Ed. Engl. 46 (2007), pp. 6729-6731.
14. 2, Release 4.9, Accelrys Software, Inc, San Diego, 2003.
15. Accerlys Material Studio, Release 4.0, Accelrys Software, Inc, San Diego, 2006.
16. N. Blagden, R. Davey, G. Dent, M. Song, W.I.F. David, C.R. Pulham, and K. Shankland, Woehler and Liebig revisited: A mall molecule reveals its secrets - the crystal structure of the unstable polymorph of henzamide solved after 173 years, Cryst. Growth Des. 5 (2005)', pp. 2218-2224.
17. W.I.F. David, K. Shankland, C.R. Pulham, N. Blagden, R.J. Davey, and M. Song, Polymorphism in henzamide, Angew. Chem. Int. Ed. 44 (2005), pp. 7032-7035.
18. J. Gasteiger and M. Marsili, Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 36 (1980), pp. 3219-3228.
19. S.L. Mayo, B.D. Olafson, and W. A. Goddard, Dreiding - a generic orce-field for molecular simulations, J. Phys. Chem. 94 (1990), pp. 8897-8909.
20. B. Delley, An all-electron numerical-method for solving the local ensity functional for polyatomic-molecules, J.Chem.Phys. 92 (1990), pp. 508-517.
21. G. Fitzgerald, B. Delley and J.W. Andzelm, DFT: Prom molecules to solids using LCAO numerical orbitals, Abstracts Of Papers Of The American Chemical Society 220 (2000), p. U187
22. B.H. Besler, K.M. Merz, and P.A. Kollman, Atomic charges derived from semiempirical methods, J. Comput. Chem. 11 (1990), pp. 431-439.
23. U.C. Singh and P.A. Kollman, An approach to computing electrostatic charges for molecules, J. Comput. Chem. 5 (1984), pp. 129-145.
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr, T. Vreven, K.N. Kudin, J.C Burant et al. Gaussian 03, Revision C.02, Gaussian, Inc, Wallingford CT, 2004.
25. J.P. Perdew, K. Burke, and M. Ernzerhof, Generalized gradient approximation made simple, Phys. Rev. Lett. 77 (1996) pp. 3865-3868.
26. A.D. Becke, Density-functional thermochemistry.3. The role of exact exchange, J. Chem. Phys. 98 (1993), pp. 5648-5652.
27. A.D. Becke, A new mixing of Hartree-Fock and local density-functional theories, J. Chem. Phys. 98 (1993), pp. 1372-1377.
28. H.R. Karfunkel and R.J. Gdanitz, Ab initio prediction of possible crystal-structures for general organic-molecules, J. Comp. Chem. 13 (1992), pp. 1171-1183.
29. H.R. Karfunkel, F.JJ. Leusen, and R.J. Gdanitz, The ab initio prediction of yet unknown molecular crystal structures by solving the crystal packing problem, J. Comput Aided Mater. Design 1 (1994), pp. 177-185.
30. R.J. Gdanitz, Prediction of molecular-crystal structures by Monte-Carlo simulated annealing without reference to diffraction data, Chem. Phys. Lett. 190 ( 1992), pp. 391 -396.
31. P. Verwerand F.J.J. Leusen, Computer simulation to predict possible crystal polymorphs, Rev. Comput. Chem. (1998), pp. 327-365.
32. A.L. Spek, Single-crystal structure validation with the program PLATON, J. Appl. Cryst. 36 (2003), pp. 7-13.
33. P.G. Karamertzanis, and S. L. Price, Energy minimization of crystal structures containing flexible molecules, J. Chem. Theory Comput. 2 (2006), pp. 1184-1199.
34. G.R. Desiraju, The Crystal as a Supramolecular Entity, John Wiley & Sons Ltd, Chichester, 1996.