Thermal single crystal to single crystal transformation among crystal polymorphs in 2-dimethylamino-5,7-bis(trifluoromethyl)-1,8-naphthyridine and in a 1-quinoline analogue

Crystal Growth and Design

Volumn 13, Issue 11, 2013, Pages 4705-4713

  Harada, Naomi ^a   Karasawa, Satoru ^a   Matsumoto, Taisuke ^a   Koga, Noboru ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL PHASE TRANSITION; CRYSTAL POLYMORPH; ENDOTHERMIC PEAKS; HIGH TEMPERATURE; LOW TEMPERATURE REGIONS; MOLECULAR ARRANGEMENTS; REVERSIBLE TRANSFORMATION; SINGLE CRYSTAL-TO-SINGLE-CRYSTAL TRANSFORMATION;

TEMPERATURE; X RAY CRYSTALLOGRAPHY;

SINGLE CRYSTALS;

EID: 84887797221     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg401386b     Document Type: Article

References (52)

1. Kitamura, M. CrystEngComm 2009, 11, 949-964
2. Otsuka, M.; Matsumoto, T.; Kaneniwa, N. Chem. Pharm. Bull. 1956, 34, 1784-1793
3. Haleblian, J.; McCrone, W. J. Pharm. Sci. 1969, 58, 911-929
4. Chiavaro, E. Eur. J. Liquid Sci. Technol. 2013, 115, 267-269
5. Craven, R. J.; Lencki, R. W. Food Funct. 2012, 3, 228-233
6. Tamada, Y. Biomacromolecules 2005, 6, 3110-3106
7. Zhang, Y.-Q.; Shen, W.-D.; Xiang, R.-L.; Zhuge, L.-J.; Gao, W.-J.; Wang, W.-B. J. Nanopart. Res. 2007, 9, 885-900
8. Bernstein, J. Cryst. Growth Des. 2011, 11, 632-650
9. Gavezzotti, A. J. Pharm. Sci. 2004, 96, 2232-2240
10. Zeidan, T. A.; Trotta, J. T.; Chiarella, R. A.; Oliveira, M. A.; Hickey, M. B.; Almarsson, Ö.; Remenar, J. F. Cryst. Growth Des. 2013, 13, 2036-2046
11. López-Mejías, V.; Kampf, J. W.; Matzger, A. J. J. Am. Chem. Soc. 2012, 134, 9872-9875
12. Reany, O.; Kapon, M.; Botoshansky, M.; Keinan, E. Cryst. Growth Des. 2009, 9, 3661-3670
13. Braum, D. E.; Gelbrich, T.; Kahlenberg, V.; Tessadri, R.; Wieser, J.; Griesser, U. J. J. Pharm. Sci. 2009, 98, 2010-2026
14. Zhang, G.; Lu, J.; Sabat, M.; Frazer, C. L. J. Am. Chem. Soc. 2010, 132, 2160-2162
15. Ito, H.; Saito, T.; Oshima, N.; Kitamura, N.; Ishizuka, S.; Hinatsu, Y.; Wakeshima, M.; Kato, M.; Tsuge, K.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 10044-10045
16. Gu, X.; Yao, J.; Zhang, G.; Yan, Y.; Zhang, C.; Peng, Q.; Liao, Q.; Wu, Y.; Xu, Z.; Zhao, Y.; Fu, H.; Zhang, D. Adv. Funct. Mater. 2012, 22, 4862-4872
17. Luo, X.; Li, J.; Li, C.; Heng, L.; Dong, Y. Q.; Liu, Z.; Bo, Z.; Tang, B. Z. Adv. Mater. 2011, 23, 3261-3265
18. Mutai, T.; Satou, H.; Araki, K. Nat. Mater. 2005, 4, 658-687
19. Abe, Y.; Karasawa, S.; Koga, N. Chem.-Eur. J. 2012, 18, 15038-15048
20. Harada, N.; Abe, Y.; Karasawa, S.; Koga, N. Org. Lett. 2012, 14, 6282-6285
21. SIR 2004: Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 2005, 38, 381-388
22. SIR 92: Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435
23. SHELX97: Scheldrick, G. M.; Schneider, T. R. Methods Enzymol 1997, 276, 319-343
24. Crystal Structure 3.5.2: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC, 2000-2003, 9009 NewTrails Dr. The Woodlands TX 77381 USA.
25. Mekki, S.; Rolland, V.; Bellahouel, S.; van der Lee, A.; Rolland, M. Acta Crystallogr. 2001, C67, o-301-o305
26. Bernstein, J.; Dunitz, J. D.; Gavezzotti, A. Cryst. Growth Des. 2008, 8, 2011-2018
27. Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309-314
28. Gavezzotti, A.; Filippini, G. J. Phys. Chem. 1994, 98, 4831-4837
29. Bakavoli, M.; Rahimizadeh, M.; Feizyzadeh, B.; Kaju, A. A.; Takjoo, R. J. Chem. Crystallogr. 2010, 40, 746-752
30. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11, 19-32
31. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr. 2004, B60, 627-668
32. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. Appl. Crystallogr. 2008, 41, 466-470
33. Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Javatilaka, D.; Spackman, M. Crystal Explorer 2.0; University of Western Australia: Perth, Australia, 2007.
34. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669
35. Gavezzotti, A.; Desiraju, G. R. Acta Crystallogr. 1989, B45, 473-482
36. Wang, Y.-L.; Feng, M.; Tao, X.; Tang, Q.-Y.; Shen, Y.-Z. Acta Crystallogr. 2013, C69, 25-28
37. Fukumoto, S.; Nakashima, T.; Kawai, T. Dyes Pigm. 2012, 92, 868-871
38. Nishio, M. Phys. Chem. Chem. Phys. 2011, 13, 13873-13900
39. Tárkanyi, G.; Király, P.; Varga, S.; Vakulya, B.; Soós, T. Chem.-Eur. J. 2008, 14, 6078-6086
40. Cheon, J.-D.; Mutai, T.; Araki, K. Org. Biomol. Chem. 2007, 5, 2762-2766
41. Nad, S.; Pal, H. J. Phys. Chem. A 2001, 105, 1097-1106
42. Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470
43. Lippert, E. Z. Naturforsch. 1955, 10A, 541-545
44. Han, F.; Chi, L.; Wu, W.; Liang, X.; Fu, M.; Zhao, J. J. Photochem. Photobiol. A 2008, 196, 10-23
45. Nad, S.; Pal, H. J. Phys. Chem. A 2001, 105, 1097-1106
46. Soujanya, T.; Fessenden, R. W.; Samanta, A. J. Phys. Chem. 1996, 100, 3507-3512
47. Hisaki, I.; Hiraishi, E.; Sasaki, T.; Orita, H.; Tsuzuki, S.; Tohnai, N.; Miyata, M. Chem.-Asian J. 2012, 7, 2607-2614
48. Hinoue, T.; Shigenoi, Y.; Sugino, M.; Mizobe, Y.; Hisaki, I.; Miyata, M.; Tohnai, N. Chem.-Eur. J. 2012, 18, 4634-4643
49. Bruni, G.; Gozzo, F.; Capsoni, D.; Bini, M.; Macchi, P.; Simoncic, P.; Berbenni, V.; Milanese, C.; Girella, A.; Ferrari, S.; Marini, A. J. Pharm. Sci. 2011, 100, 2321-2332
50. Gill, P. S.; Sauerbrunn, S. R.; Reading, M. J. Therm. Anal. 1993, 40, 931-939
51. Rice, A. P.; Tham, F. S.; Chronister, E. L. J. Chem. Crystallogr. 2013, 43, 14-15
52. Mehta, G.; Sen, S. Chem. Commun. 2009, 5981-5983