Isostructuralism among 'bridge-flipped' isomeric benzylideneanilines and phenylhydrazones

Acta Crystallographica Section B: Structural Science

Volumn 63, Issue 3, 2007, Pages 485-496

  Ojala, William H ^a   Smieja, Jonathan M ^a   Spude, Jill M ^a   Arola, Trina M ^a   Kuspa, Marika K ^a   Herrera, Nell ^a   Ojala, Charles R ^b  

^a UNIVERSITY OF ST THOMAS   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

'Bridge flipped' isomers; Benzylideneanilines; Isostructuralism; Packing; Phenylhydrazones

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLIZATION; CRYSTALLOGRAPHY; HYDROGEN BONDS; KETONES; SUBSTITUTION REACTIONS;

BENZYLIDENEANILINES; ISOSTRUCTURALISM; PHENYLHYDRAZONES;

ISOMERS;

EID: 34249104147     PISSN: 01087681     EISSN: 01087681     Source Type: Journal    
DOI: 10.1107/S0108768107018034     Document Type: Article

References (66)

1. Adamson, A. J., Archambeau, Y., Banks, R. E., Beagley, B., Helliwell, M., Pritchard, R. G. & Tipping, A. E. (1994). Acta Cryst. C50, 967-971.
2. Allaway, C. L., Daly, M., Nieuwenhuyzen, M. & Saunders, G. C. (2002). J. Fluorine Chem. 115, 91-99.
3. Allen, F. H. (2002). Acta Cryst. B58, 380-388.
4. Bar, I. & Bernstein, J. (1983). Acta Cryst. B39, 266-272.
5. Bar, I. & Bernstein, J. (1987). Tetrahedron, 43, 1299-1305.
6. Bernstein, J. & Bar, I. (1980). Eur. Cryst. Meet. 6, 21.
7. Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
8. Bouwstra, J. A., Schouten, A., Kroon, J. & Helmholdt, R. B. (1985). Acta Cryst. C41, 420-426.
9. Bryan, R. F., Forcier, P. & Miller, R. W. (1978). J. Chem. Soc. Perkin Trans. 2, pp. 368-372.
10. Bruker (2000). SADABS, Version 2.03, and SHELXTL, Version 6.12. Bruker Analytical X-ray Instruments, Madison, Wisconsin, USA.
11. Bruker (2001). SMART, Version 5.054. Bruker Analytical X-ray Instruments, Madison, Wisconsin, USA.
12. Bruker (2003). SAINT-Plus, Version 6.45. Bruker Analytical X-ray Instruments, Madison, Wisconsin, USA.
13. Bürgi, H. B. & Dunitz, J. D. (1970). Helv. Chim. Acta, 53, 1747-1764.
14. Bürgi, H. B., Dunitz, J. D. & Züst, C. (1968). Acta Cryst. B24, 463-464.
15. Chakraborty, S., Laye, R. H., Paul, R. L., Gonnade, R. G., Puranik, V. G., Ward, M. D. & Lahiri, G. K. (2002). J. Chem. Soc. Dalton Trans. pp. 1172-1179.
16. Clegg, W, Elsegood, M. R. J., Heath, S. L., Houlton, A. & Shipman, M. A. (1996). Acta Cryst. C52, 2548-2552.
17. Cole, J. M., Howard, J. A. K. & McIntyre, G. J. (2001). Acta Cryst. B57, 410-414.
18. Ferguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o613-o616.
19. Filipenko, O. S., Ponomarev, V. I. & Atovmyan, L. O. (1976). Dokl. Akad. Nauk SSSR, 229, 1113-1116.
20. Filipenko, O. S., Shigorin, V. D., Ponomarev, V. I., Atovmyan, L. O., Safina, Z. Sh. & Tarnopol'skii, B. L. (1977). Kristaltografiya, 22, 534-541.
21. Flack, H. D. (1983). Acta Cryst. A39, 876-881.
22. Glidewell, C, Howie, R. A., Low, J. N., Skakle, J. M. S., Wardell, S. M. S. V. & Wardell, J. L. (2002). Acta Cryst. B58, 864-876.
23. Haller, K. J., Rae, A. D., Heerdegen, A. P., Hockless, D. C. R. & Welberry, T. R. (1995). Acta Cryst. B51, 187-197.
24. Harada, J., Harakawa, M. & Ogawa, K. (2004a). Acta Cryst. B60, 578-588.
25. Harada, J., Harakawa, M. & Ogawa, K. (2004b). Acta Cryst. B60, 589-597.
26. He, X., Stowell, J. G., Morris, K. R., Pfeiffer, R. R., Li, H., Stahly, G. P. & Byrn, S. R. (2001). Cryst. Growth Des. 1, 305-312.
27. Hoshino, N., Inabe, T., Mitani, T. & Maruyama, Y. (1988). Bull. Chem. Soc. Jpn, 61, 4207-4214.
28. Hursthouse, M. B. & Karaulov, A. (2003). Private communication.
29. Inabe, T., Hoshino, N., Mitani, T. & Maruyama, Y. (1989). Bull. Chem. Soc. Jpn, 62, 2245-2251.
30. Jiao, Y.-H., Zhang, Q. & Ng, S. W. (2006). Acta Cryst. E62, o3614-o3615.
31. Kamwaya, M. E. & Khoo, L. E. (1985). J. Fiz. Malays. 6, 135-140.
32. Karakas, A., Elmali, A., Unver, H. & Svoboda, I. (2004). J. Mol. Struct. 702, 103-110.
33. Li, A., Bin, X., Zhu, S.-Z., Huang, Q.-C. & Liu, J.-S. (1994). J. Fluorine Chem. 68, 145-148.
34. Lindeman, S. V., Andrianov, V. G., Kravcheni, S. G., Potapov, V. M., Potekhin, K. A. & Struchkov, Y. T. (1981). Zh. Strukt. Khim. 22, 123-131.
35. Lindeman, S. V., Shklover, V. E. & Struchkov, Y. T. (1981). Acta Cryst. A37, C87.
36. Lindeman, S. V., Shklover, V. E., Struchkov, Y. T., Kravcheni, S. G. & Potapov, V. M. (19820). Cryst. Struct. Commun. 11, 43-47.
37. Lindeman, S. V., Shklover, V. E., Struchkov, Y. T., Kravcheni, S. G. & Potapov, V. M. (1982b). Cryst. Struct. Commun. 11, 49-52.
38. Meunier-Piret, J., Germain, G., Declercq, J. P. & van Meerssche, M. (1982a). Bull Soc. Chim. Belg. 91, 89-90.
39. Meunier-Piret, J., Germain, G., Declercq, J. P. & van Meerssche, M. (1982b). Bull. Soc. Chim. Belg. 91, 93-94.
40. Meunier-Piret, J., Piret, P., Germain, G. & van Meerssche, M. (1972). Bull. Soc. Chim. Belg. 81, 533-538.
41. Morimoto, M., Kobatake, S. & Irie, M. (2003). J. Am. Chem. Soc. 125, 11080-11087.
42. Moustakali-Mavridis, I., Hadjoudis, E. & Mavridis, A. (1978). Acta Cryst. B34, 3709-3715.
43. Nakai, H., Ezumi, K. & Shiro, M. (1981). Acta Cryst. B37, 193-197.
44. Nakai, H., Shiro, M., Ezumi, K., Sakata, S. & Kubota, T. (1976). Acta Cryst. B32, 1827-1833.
45. Navon, O. & Bernstein, J. (1997). Struct. Chem. 8, 3-11.
46. Ojala, C. R., Ojala, W. H., Gleason, W. B. & Britton, D. (1999). J. Chem. Cryst. 29, 27-32.
47. Ojala, C. R., Ojala, W. H., Gleason, W. B. & Britton, D. (2001). J. Chem. Cryst. 31, 377-386.
48. Orr, L. B., Jr, Parsons, E. J. & Pennington, W. T. (1992). Acta Cryst. C48, 2042-2043.
49. Patani, G. A. & LaVoie, E. J. (1996). Chem. Rev. 96, 3147-3176.
50. Ponomarev, V. I., Filipenko, O. S., Atovmyan, L. O., Grazhulene, S. S., Lempert, S. A. & Shigorin, V. D. (1977). Kristallografiya (Russ.) (Crystallogr. Rep.) 22, 394-396.
51. Shan, S., Wang, X.-J., Hu, W.-X. & Xu, D.-J. (2004). Acta Cryst. E60, o1954-o1956.
52. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473.
53. Sheldrick, G. M. (1997). SHELXL and SHELXS97. University of Göttingen, Germany.
54. Silverman, R. B. (2004). The Organic Chemistry of Drug Design and Drug Action, 2nd ed. pp. 29-34. New York: Elsevier, Inc.
55. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
56. Tanaka, M., Imai, T., Goto, T., Taka, J.-I., Akamatsu, M., Kashino, S. & Mogi, K. (1998). Bull. Chem. Soc. Jpn, 71, 2561-2571.
57. Tbnc, T., Tezcan, H., Sari, M., Buyukgungor, O. & Yagbasan, R. (2003). Acta Cryst. C59, o528-o529.
58. Velavan, R., Sivakumar, K. & Anbu, M. (1995). Acta Cryst. C51, 1227-1229.
59. Vickery, B., Willey, G. R. & Drew, M. G. B. (1985). Acta Cryst. C41, 1072-1075.
60. Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o10-o14.
61. Wardell, J. L., Wardell, S. M. S. V., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2002). Acta Cryst. C58, o428-o430.
62. Welberry, T. R., Butler, B. D. & Heerdegen, A. P. (1993). Acta Chim. Hung. 130, 327-345.
63. Whitney, J. F. & Corvin, I. (1949). Anal. Chem. 21, 306-307.
64. Yeap, G.-Y., Fun, H.-K., Teoh, S.-G., Teo, S.-B., Chinnakali, K. & Yip, B.-C. (1992). Acta Cryst. C48, 2257-2258.
65. Yin, Z.-G., Qian, H.-Y., Jia, J., Zhou, N. & Feng, L.-Q. Acta Cryst. E62, o4913-o4914.
66. Zamir, S. & Bernstein, J. (1993). Acta Chim. Hung. 130, 301-325.