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Synthesis and Crystal Structure of 1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino}phenyl)ethanone Oxime
Corresponding Author(s) : Li Zhao
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
The title compound, 1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino}phenyl)ethanone oxime, was synthesized by the reaction of 3,5-dibromosalicylaldehyde with 4-amino-phenylethanone oxime in ethanol. The molecule crystallizes in the triclinic system, space group P21/c, with four crystallographically independent molecules in the unit cell. The two benzene rings form a dihedral angle of 21.63º. In the crystal structure, there are a strong intramolecular O2-H2···N2 hydrogen bond between the hydroxyl (O2-H2) group and the Schiff base nitrogen (N2) atom, with the distance between N2 and O2 is 2.580(4) Å. Moreover, a dimer is formed with another adjacent molecule by two pairs of intermolecular O1-H1···N1 hydrogen bonds.
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References
S.S. Sun, C.L. Stern and S.T. Nguyen, J. Am. Chem. Soc., 126, 6314 (2004).
W.K. Dong, J.G. Duan, Y.H. Guan, J.Y. Shi and C.Y. Zhao,Inorg. Chim. Acta, 362, 1129 (2009).
S. Akine, T. Taniguchi and T. Nabeshima, Angew. Chem. Int. Ed., 41, 4670 (2002).
D.A. Atwood and M.J. Harvey, Chem. Rev., 101, 37 (2001).
W.K. Dong, G. Wang, S.S. Gong, J.F. Tong, Y.X. Sun and X.H. Gao, Transition Met. Chem., 37, 271 (2012).
W.K. Dong, X.N. He, H.B. Yan, Z.W. Lv, X. Chen, C.Y. Zhao and X.L. Tang, Polyhedron, 28, 1419 (2009).
W.K. Dong, Y.X. Sun, Y.P. Zhang, L. Li, X.N. He and X.L. Tang, Inorg. Chim. Acta, 362, 117 (2009).
L. Zhao and S.W. Ng, Acta Cryst., E66, o2474 (2010).
L. Zhao and S.W. Ng, Acta Cryst., E66, o2473 (2010).
H.L. Wu, F. Jia, F. Kou, B. Liu, J.K. Yuan and Y. Bai, Transition Met. Chem., 36, 847 (2011).
W.K. Dong, Y.X. Sun, C.Y. Zhao, X.Y. Dong and L. Xu, Polyhedron, 29, 2087 (2010).
H.L. Wu, K.T. Wang, F. Kou, F. Jia, B. Liu, J.K. Yuan and Y. Bai, J. Coord. Chem., 64, 2676 (2010).