Colored polymorphs: Thermochemical and structural features of N-picryl-p-toluidine polymorphs and solvates

Crystal Growth and Design

Volumn 8, Issue 6, 2008, Pages 1977-1989

  Braun, Doris E ^a   Gelbrich, Thomas ^a   Jetti, Ram K R ^a   Kahlenberg, Volker ^a   Price, Sarah L ^b   Griesser, Ulrich J ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 52649155303     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg8000224     Document Type: Article

References (50)

1. Yu, L. J. Phys. Chem. A 2002, 206, 544-550.
2. (a) This list represents only a selection of references on color polymorphism. Curtin, D. Y.; Byrn, S. R. J Am. Chem. Soc. 1969, 91, 6102-6106.
3. (b) Fletton, R. A.; Lancaster, R. W.; Harris, R. K.; Kenwright, A, M.; Packer, K. J.; Waters, D, N.; Yeadon, A. J. Chem. Soc. Perkin Trans. 2 1986, 170, 5-1709.
4. (c) Stephenson, G. A.; Borchardt, T. B.; Byrn, S. R.; Bowyer, J.; Bunnell, C. A.; Snorek, S. V.; Yu, A. L. J. Pharm. Sci. 1995, 84, 1385-1386.
5. (d) Bernstein, J.; Schmidt, G. M. J. J. Chem. Soc., Perkin Trans. 1972, 2, 951-955.
6. (e) Bernstein, J.; Izak, I. J. Cryst. Mol Struct 1975, 5, 257-266.
7. (f) He, X.; Griesser, U. J.; Stowell, J. G.; Borchardt, T. B.; Byrn, S. R. J. Pharm. Sci. 2001, 37, 1-388.
8. (g) Li, H.; Stowell, J. G.; Borchardt, T. B.; Byrn, S. R. Cryst. Growth Des. 6 2006, 246, 9-2474.
9. Hantzsch, A. Angew. Chem. 1908, 20, 1889.
10. Klebe, B.; Graser, F.; Hädicke, E.; Berndt, J. Acta Crystallogr. 1989, B45, 69-77.
11. Cullinane, N. M.; Embrey, O. E.; Davies, D. R. J Phys. Chem. 1932, 36, 1434-1448.
12. Egiazaryan, G. A.; Petrov, L. A.; Perelyaeva, L. A.; Galyaminskikh, V. D.; Manannikov, B. P.; Chirkov, A. K.; Matevosyan, R. O. Dokl. Akad. Nauk SSSR 1972, 206, 355-358.
13. Matevosyan, R. O.; Donskikh, I. B.; Donskikh, O. B.; Manannikov, B. P. Armyanskii Khim. Zh. 1978, 31, 450-451.
14. Yasui, M.; Taguchi, K.; Iwasaki, F. Mol. Cryst. Liq. Cryst. 1996, 277, 527-536.
15. Ilyina, I. G.; Mikhalev, O. V.; Butin, K. P.; Tarasevich, B. N.; Uzhinov, B. M. Synth. Met. 2001, 120, 1067-1068.
16. Wood, R. G.; Ayliffe, S. H.; Cullinane, N. M. Philos. Mag. 1935, 19, 405-416.
17. (a) Yatsenko, A. V.; Paseshnichenko, K. A. Chem. Phys. 2000, 262, 293-301.
18. (b) Yatsenko, A. V. J. Mol. Modell. 2003, 9, 207-216.
19. (a) Allen, F. H. Acta Crystallogr. B 2002, 58, 380-388.
20. (b) All CSD searches were performed using Conquest version 1.8 (November 2005. 353518 entries) with the following filters used: 3D coordinates determined, not disordered, R-factor less than 10%, no errors, not polymeric and only organics.
21. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
22. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. SIR97: A New Program for Solving and Refining Crystal Structures; Bari, Italy, 1997.
23. Sheldrick, G. SHELXL-97, Program for Crystal Structure Refinement; Institüt für Anorganische Chemie der Universität: Gottingen, Germany, 1997.
24. (a) Burger, A.; Ramberger, R. Mikrochim. Acta 1979, 2, 273-316.
25. (b) Burger, A.; Ramberger, R. Mikrochim. Ada 1979, 2, 259-271.
26. (c) Yu, L. J. Pharm. Sci. 1995, 84, 966-974.
27. Ullmann, F.; Nadai, G. Ber. - Dtsch. Chem. Ges. 1908, 41, 1870-1878.
28. Busch, M.; Pungs, E. J Praia. Chem. 1910, 79, 546-555.
29. Hantzsch, A. Ber. - Dtsch. Chem. Ges. 1910, 3, 1615-1662.
30. James, T. C.; Jones, J. I. M.; Lewis, R. I. J. Chem. Soc. 1920, 117, 1273-1280.
31. Sekiguchi, S.; Ishikura, H.; Hirosawa, Y.; Ono, N. Tetrahedron 1990, 46, 5567-5578.
32. Gu, C.-H.; Grant, D. J. W. J. Pharm. Sci. 2001, 90, 1277-1287.
33. Davey, R. J.; Cardew, P. T.; McEwan, D.; Sadler, D. E. J. Cryst. Growth 1986, 79, 648-653.
34. Kumar, K.; Carey, P. J. Chem. Phys. 1975, 63, 3697.
35. Stockton, G. W.; Godfrey, R.; Hitchcock, P.; Mendelsohn, R.; Mowery, P. C.; Rajan, S.; Walker, A. F. J Chem. Soc. Perkin Trans. 2 1998, 2061-2072.
36. Onagi, H.; Carrozzini, B.; Cascarano, G. L.; Easton, C. J.; Edwards, A. J.; Lincoln, S. F.; Rae, A. D. Chem.-Eur. J. 2003, 9, 5971.
37. Gridunova, G. V.; Shklover, V. E.; Struchkov, Y. T.; Il'ina, I. G.; Mikhalev, O. V.; Potapov, V. I. Kristallografiya (Russ.) (Crystallogr. Rep.) 1989, 34, 87.
38. Divjakovic, V.; Nowacki, W.; Edenharter, A.; Engel, P.; Ribar, B.; Halasi, R. Cryst. Struct. Commun. 1973, 2, 411.
39. Gridunova, G. V.; Petrov, V. N.; Struchkov, Y. T.; Il'ina, I. G.; Mikhalev, O. V. Kristallografiya (Russ.) (Crystallogr. Rep.). 1990, 35, 54.
40. (a) Gelbrich, T.; Hursthouse, M. B. CrystEngComm 2005, 7, 324-336.
41. (b) Gelbrich, T.; Hursthouse, M. B. CrystEngComm 2006, 8, 448-460.
42. Kitaigorodskii, A. I. Organic Chemical Crystallography; Consultants Bureau: New York, 1961.
43. Speck, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.
44. (a) Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129-38.
45. (b) McKinnon, J, J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr. 2004, B60, 627-668.
46. (c) Wolff, S. K.; Grimwood, D.; McKinnon, J.; Jayatilaka, D.; Spackman, M. Crystal Explorer, Version 2.0 beta; University of Western Australia: Perth, 2007.
47. (d) McKinnon, J. J.; Jayatilaka, D.; Spackman, M. Chem. Comm. 2007, 37, 3814-3816.
48. Williams, D. E. J. Comput. Chem. 2001, 22, 1154-1166.
49. Karamertzanis, P. G.; Price, S. L. J. Chem. Theory Comput. 2006, 2, 1184-1199.
50. Coombes, D. S.; Price, S. L.; Willock, D. J.; Leslie, M. J. Phys. Chem. 1996, 100, 7352-7360.