A molecular picture of the problems in ensuring structural purity of tazofelone

Journal of Molecular Structure

Volumn 1078, Issue , 2014, Pages 26-42

  Price, Louise S ^a   McMahon, Jennifer A ^b   Lingireddy, Sreenivas R ^b   Lau, Suk Fai ^b   Diseroad, Benjamin A ^b   Price, Sarah L ^a   Reutzel Edens, Susan M ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Crystal structure prediction; Disorder; Polymorphism; Solid form screening; Structural purity; Tazofelone

Indexed keywords

CRYSTAL STRUCTURE PREDICTION; DISORDER; SOLID FORMS; STRUCTURAL PURITY; TAZOFELONE;

POLYMORPHISM;

EID: 84908378118     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2014.01.014     Document Type: Article

References (77)

1. G. Coquerel, Chem. Eng. Process. 45 (2006) 857-862.
2. A.D. Bond, R. Boese, G.R. Desiraju, Angew. Chem., Int. Ed. 46 (2007) 618-622.
3. G.M. Day, Crystallogr. Rev. 17 (2011) 3-52.
4. S.L. Price, Chem. Soc. Rev. (2014), http://dx.doi.org/10.1039/C3CS60279F.
5. S.L. Price, Acc. Chem. Res. 42 (2009) 117-126.
6. M. Habgood, Cryst. Growth Des. 11 (2011) 3600-3608.
7. D.A. Bardwell, C.S. Adjiman, Y.A. Arnautova, E. Bartashevich, S.X. Boerrigter, D.E. Braun, A.J. Cruz-Cabeza, G.M. Day, R.G. la Valle, G.R. Desiraju, B.P. van Eijck, J.C. Facelli, M.B. Ferraro, D. Grillo, M. Habgood, D.W. Hofmann, F. Hofmann, K.V. Jose, P.G. Karamertzanis, A.V. Kazantsev, J. Kendrick, L.N. Kuleshova, F.J. Leusen, A.V. Maleev, A.J. Misquitta, S. Mohamed, R.J. Needs, M.A. Neumann, D. Nikylov, A.M. Orendt, R. Pal, C.C. Pantelides, C.J. Pickard, L.S. Price, S.L. Price, H.A. Scheraga, J. van de Streek, T.S. Thakur, S. Tiwari, E. Venuti, I.K. Zhitkov, Acta Crystallogr., Sect. B 67 (2011) 535-551.
8. A.V. Kazantsev, P.G. Karamertzanis, C.S. Adjiman, C.C. Pantelides, S.L. Price, P.T. Galek, G.M. Day, A.J. Cruz-Cabeza, Int. J. Pharm. 418 (2011) 168-178.
9. S.Z. Ismail, C.L. Anderton, R.C. Copley, L.S. Price, S.L. Price, Cryst. Growth Des. 13 (2013) 2396-2406.
10. R.M. Bhardwaj, L.S. Price, S.L. Price, S.M. Reutzel-Edens, G.J. Miller, I.D.H. Oswald, B. Johnston, A.J. Florence, Cryst. Growth Des. 13 (2013) 1602-1617.
11. J. Kendrick, G.A. Stephenson, M.A. Neumann, F.J. Leusen, Cryst. Growth Des. 13 (2013) 581-589.
12. J.A. Panetta, J.K. Shadle, M.L. Phillips, D.N. Benslay, P.P.K. Ho, Ann. N. Y Acad. Sci. (1993) 415-416.
13. S.M. Reutzel-Edens, V.A. Russell, L. Yu, J. Chem. Soc. Perkin Trans. 2 (5) (2000) 913-924.
14. J. Huang, S. Chen, I.A. Guzei, L. Yu, J. Am. Chem. Soc. 128 (2006) 11985-11992.
15. L. Yu, J. Am. Chem. Soc. 125 (2003) 6380-6381.
16. S.A. Chen, H.M. Xi, L. Yu, J. Am. Chem. Soc. 127 (2005) 17439-17444.
17. C. Stoica, P. Tinnemans, H. Meekes, E. Vlieg, Cryst. Growth Des. 5 (2005) 975-981.
18. H.H. Tung, Org. Process Res. Dev. 17 (2013) 445-454.
19. C.C. Sun, J. Pharm. Sci. 98 (2009) 1744-1749.
20. L. Yu, J. Huang, K.J. Jones, J. Phys. Chem. B 109 (2005) 19915-19922.
21. T. Gelbrich, D.E. Braun, A. Ellern, U.J. Griesser, Cryst. Growth Des. 13 (2013) 1206-1217.
22. Y.A. Abramov, J. Phys. Chem. A 115 (2011) 12809-12817.
23. A. Otero-de-la-Roza, E.R. Johnson, J. Chem. Phys. 137 (2012) 054103.
24. D.E. Braun, M. Ardid-Candel, E. D'Oria, P.G. Karamertzanis, J.B. Arlin, A.J. Florence, A.G. Jones, S.L. Price, Cryst. Growth Des. 11 (2011) 5659-5669.
25. Bruker AXS Inc. SAINT. [8.32b], Madison, Wisconsin, USA, 2013.
26. G. Sheldrick, Acta Crystallogr. Sect. A 46 (1990) 467-473.
27. G.M. Sheldrick, SHELXTL [6.2], University of Gottingen, Germany, 2013.
28. Bruker AXS Inc., SADABS: Area-Detector Absorption Correction [2012/1], Bruker AXS Inc., Madison, Wisconsin, USA, 2012.
29. A.L. Spek, Acta Crystallogr. Sect. D 65 (2009) 148-155.
30. B.M. Fung, A.K. Khitrin, K. Ermolaev, J. Magn. Reson. 142 (2000) 97-101.
31. O.N. Antzutkin, Prog. Nucl. Magn. Reson. Spectrosc. 35 (1999) 203-266.
32. G. Metz, X.L. Wu, S.O. Smith, J. Magn. Reson. Ser. A 110 (1994) 219-227.
33. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Gaussian Inc., Wallingford, CT, 2004.
34. A.J. Stone, J. Chem. Theory Comput. 1 (2005) 1128-1132.
35. A.J. Stone, A Program for Performing Distributed Multipole Analysis of Wave Functions Calculated Using the Gaussian Program System [2.2], University of Cambridge, Cambridge, United Kingdom, 2010.
36. D.E. Williams, S.R. Cox, Acta Crystallogr., Sect. B 40 (1984) 404-417.
37. D.S. Coombes, S.L. Price, D.J. Willock, M. Leslie, J. Phys. Chem. 100 (1996) 7352-7360.
38. G.M. Day, T.G. Cooper, A.J. Cruz-Cabeza, K.E. Hejczyk, H.L. Ammon, S.X.M. Boerrigter, J. Tan, R.G. Della Valle, E. Venuti, J. Jose, S.R. Gadre, G.R. Desiraju, T.S. Thakur, B.P. van Eijck, J.C. Facelli, V.E. Bazterra, M.B. Ferraro, D.W.M. Hofmann, M. Neumann, F.J.J. Leusen, J. Kendrick, S.L. Price, A.J. Misquitta, P.G. Karamertzanis, G.W.A. Welch, H.A. Scheraga, Y.A. Arnautova, M.U. Schmidt, J. van de Streek, A. Wolf, B. Schweizer, Acta Crystallogr., Sect. B 65 (2009) 107-125.
39. J.P.M. Lommerse, W.D.S. Motherwell, H.L. Ammon, J.D. Dunitz, A. Gavezzotti, D.W.M. Hofmann, F.J.J. Leusen, W.T.M. Mooij, S.L. Price, B. Schweizer, M.U. Schmidt, B.P. van Eijck, P. Verwer, D.E. Williams, Acta Crystallogr., Sect. B 56 (2000) 697-714.
40. T.A. Halgren, J. Am. Chem. Soc. 114 (1992) 7827-7843.
41. S.L. Price, M. Leslie, G.W.A. Welch, M. Habgood, L.S. Price, P.G. Karamertzanis, G.M. Day, Phys. Chem. Chem. Phys. 12 (2010) 8478-8490.
42. A.V. Kazantsev, P.G. Karamertzanis, C.S. Adjiman, C.C. Pantelides, J. Chem. Theory Comput. 7 (2011) 1998-2016.
43. T.G. Cooper, K.E. Hejczyk, W. Jones, G.M. Day, J. Chem. Theory Comput. 4 (2008) 1795-1805.
44. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P.A. Wood, J. Appl. Crystallogr. 41 (2008) 466-470.
45. P.T.A. Galek, L. Fabian, W.D.S. Motherwell, F.H. Allen, N. Feeder, Acta Crystallogr., Sect. B 63 (2007) 768-782.
46. P.A. Wood, T.S. Olsson, J.C. Cole, S.J. Cottrell, N. Feeder, P.T. Galek, C.R. Groom, E. Pidcock, CrystEngCommun 15 (2013) 65-72.
47. C. Gervais, G. Coquerel, Acta Crystallogr., Sect. B 58 (2002) 662-672.
48. A.D. Bond, CrystEngCommun 14 (2012) 2363-2366.
49. A. Gavezzotti, J. Pharm. Sci. 96 (2007) 2232-2241.
50. R. Herbst-Irmer, G.M. Sheldrick, Acta Crystallogr. Sect. B-Struct. Sci. 54 (1998) 443-449.
51. T. van Mourik, P.G. Karamertzanis, S.L. Price, J. Phys. Chem. A 110 (2006) 8-12.
52. O.G. Uzoh, A.J. Cruz-Cabeza, S.L. Price, Cryst. Growth Des. 12 (2012) 4230-4239.
53. RCI is P21/c and the pseudo inversion centre is at approximately (0.25, 0.25, 0.25) which does not correspond to any space group. RCIII is triclinic, but with a pseudo screw axis, yet neither of the triclinic space groups have screw axes.
54. H. Wu, M. Habgood, J.E. Parker, N. Reeves-McLaren, J.K. Cockcroft, M. Vickers, A.R. West, A.G. Jones, CrystEngCommun 15 (2013) 1853-1859.
55. A.J. Florence, J. Bardin, B. Johnston, N. Shankland, T.A.N. Griffin, K. Shankland, Z. Kristallogr. (2009) 215-220.
56. V.L. Deringer, V. Hoepfner, R. Dronskowski, Cryst. Growth Des. 12 (2012) 1014-1021.
57. R.J. Davey, S.L. Schroeder, J.H. ter Horst, Angew. Chem., Int. Ed. 52 (2013) 2166-2179.
58. J.B. Arlin, L.S. Price, S.L. Price, A.J. Florence, Chem. Commun. 47 (2011) 7074-7076.
59. T. Friscic, L.R. MacGillivray, Chem. Commun. (2009) 773-775.
60. D.K. Bucar, G.M. Day, I. Halasz, G.G.Z. Zhang, J.R.G. Sander, D.G. Reid, L.R. MacGillivray, M.J. Duer, W. Jones, Chem. Sci. 4 (2013) 4417-4425.
61. A. Schoenleber, Z. Kristallogr. 226 (2011) 499-517.
62. S.L. Price, Acta Crystallogr., Sect. B 69 (2013) 313-328.
63. M.C. Etter, Acc. Chem. Res. 23 (1990) 120-126.
64. A.T. Anghel, G.M. Day, S.L. Price, CrystEngCommun 4 (2002) 348-355.
65. G.M. Day, S.L. Price, M. Leslie, J. Phys. Chem. B 107 (2003) 10919-10933.
66. A.E. Gray, G.M. Day, M. Leslie, S.L. Price, Mol. Phys. 102 (2004) 1067-1083.
67. M. Urbanova, A. Sturcova, J. Brus, H. Benes, E. Skorepova, B. Kratochvil, J. Cejka, I. Sedenkova, L. Kobera, O. Policianova, A. Sturc, J. Pharm. Sci. 102 (2013) 1235-1248.
68. E. Skorepova, J. Cejka, M. Husak, V.A. Eigner, J. Rohlicek, A. Sturc, B. Kratochvil, Cryst. Growth Des. 13 (2013) 5193-5203.
69. G. Borodi, M.M. Pop, O. Onija, X. Filip, Cryst. Growth Des. 12 (2012) 5846-5851.
70. C. Brandel, Y. Amharar, J.M. Rollinger, U.J. Griesser, Y. Cartigny, S. Petit, G. Coquerel, Mol. Pharm. 10 (2013) 3850-3861.
71. F.G. Vogt, R.C. Copley, R.L. Mueller, G.P. Spoors, T.N. Cacchio, R.A. Carlton, L.M. Katrincic, J.M. Kennady, S. Parsons, O.V. Chetina, Cryst. Growth Des. 10 (2010) 2713-2733.
72. R.W. Lancaster, L.D. Harris, D. Pearson, CrystEngCommun 13 (2011) 1775-1777.
73. R.C.B. Copley, S.A. Barnett, P.G. Karamertzanis, K.D.M. Harris, B.M. Kariuki, M.C. Xu, E.A. Nickels, R.W. Lancaster, S.L. Price, Cryst. Growth Des. 8 (2008) 3474-3481.
74. D.E. Braun, D.A. Tocher, S.L. Price, U.J. Griesser, J. Phys. Chem. B 116 (2012) 3961-3972.
75. M. Tremayne, L. Grice, J.C. Pyatt, C.C. Seaton, B.M. Kariuki, H.H.Y. Tsui, S.L. Price, J.C. Cherryman, J. Am. Chem. Soc. 126 (2004) 7071-7081.
76. M.M. Hansen, A.R. Harkness, V.V. Khau, M.J. Martinelli, J.B. Deeter, Tetrahedron-Asymmetry 7 (1996) 2515-2518.
77. E. D'Oria, P.G. Karamertzanis, S.L. Price, Cryst. Growth Des. 10 (2010) 1749-1756.