814
H. Dal et al. / Spectrochimica Acta Part A 67 (2007) 808–814
the formation of keto-imine tautomer. The compound 6 has
[9] A. Elmalı, M. Kabak, E. Kavlako
207.
[10] M. Yıldız, Z. Kılıc¸, T. Ho¨kelek, J. Mol. Struct. 441 (1998) 1.
g˘lu, Y. Elerman, J. Mol. Struct. 510 (2000)
0.820, H10· · ·N1; 1.873, N1· · ·O1; 2.600(4) A, N1· · ·H10-O1
¨
[11] H. Nazır, M. Yıldız, H. Yılmaz, M.N. Tahir, D. Ulku¨, J. Mol. Struct. 524
147.1(4)◦] which means that it is in enol-imine form. In addition
˚
C5–O1 bond length [1.344(4) A] is comparable to the single
[12] T. Ho¨kelek, N. Akduran, M. Yıldız, Z. Kılıc¸, Anal. Sci. 16 (2000) 553.
˚
¨
¨
bond values in enols [1.333(7) A] [33]. In the structure of 1-{(4-
[13] H. Unver, M. Yıldız, D.M. Zengin, S. Ozbey, E. Kendi, J. Chem. Crystallogr.
31 (4) (2002) 211.
methylphenyl-imino)methyl}-2-hydroxy-3-methoxyphenol
and 1-{(4-methylphenylimino)-methyl}-2-hydroxyphenol [26]
the O–H· · ·N hydrogen bonds are established as 2.611(6) and
[14] M. Galvanic, B. Kaitner, E. Mestrovic, J. Chem. Crystallogr. 26 (1996) 23.
¨
[15] H. Unver, D.M. Zengin, K. Gu¨ven, J. Chem. Crystallogr. 30 (5) (2000)
359.
˚
2.624(4) A, respectively.
[16] Bruker Program 1D WIN-NMR (release 6.0) and 2D WIN-NMR (release
6.1).
[17] L.F. Capitan-Vallvey, F. Salinas, C. Jimenez, L. Cuadros, Can. J. Chem. 60
(1982) 1706.
[18] H. Dal, S. Safran, Y. Su¨zen, T. Ho¨kelek, Z. Kılıc¸, J. Mol. Struct. 753 (2005)
84.
[19] Rigaku/MSC Inc., 9009 new Trails Drive, The Woodlands, TX 77381.
[20] M.C. Burla, G. Cascarano, C. Giacovazzo, Acta Cryst. A 48 (1992) 906.
[21] G.H. Sheldrick, SHELXS-97 and SHELXL-97, University of Go¨ttingen,
Germany, 1997.
For compound 6 maximum deviation from mean plane
C7/C6/C5/O1/H is 0.003 A for atom O1. The N1–C7 bond of
˚
1.283(4) A for compound 6 is estimated to have remarkable
double bond character similar as in the Car–C N–Car moiety
˚
[1.279(5) A] [33].
Acknowledgements
[22] L.F. Capitan-Vallvey, F. Salinas, C. Jimenez, L. Cuadros, Can. J. Chem. 60
(1982) 1706.
[23] T. Ho¨kelek, M. Is¸ıklan, Z. Kılıc¸, Anal. Sci. 16 (2000) 99.
[24] J. Costamagna, J. Vargas, R. Latorre, A. Alvarado, G. Mena, Coord. Chem.
Rev. 119 (1992) 67.
The authors wish to acknowledge financial support of this
work under grants Commission of Scientific Research Projects
(grant no. 031032) Anadolu University and Medicinal Plants
and Medicine Research Centre of Anadolu University Eskis¸ehir
(Turkey).
[25] Z. Hayvalı, M. Hayvalı, Z. Kılıc¸, T. Ho¨kelek, E.J. Weber, Incl. Phenom.
Macrocycl. Chem. 45 (2003) 285.
[26] G.-Y. Yeap, S.-T. Ha, N. Ishizawa, K. Suda, P.-L. Boey, W.A.K. Mahmood,
J. Mol. Struct. 658 (2003) 87.
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