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Synthesis and Crystal Structure of 2,2'-[Ethylenedioxybis(nitrilomethylidyne)]dinaphthalene
Corresponding Author(s) : Yin-Xia Sun
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
A novel Schiff-base bisoxime compound, with the molecular formula C24H20N2O2, has been synthesized and characterized by elemental analysis, IR, 1H NMR and X-ray single-crystal diffraction. Structural analysis revealed that 2,2'-[ethylenedioxybis(nitrilomethylidyne)]dinaphthalene lies across a crystallographic inversion centre (symmetry code: -x, -y, -z) and adopts an E configuration with respect to the azomethine C=N bond. Within the molecule, the naphthalene units are parallel, but extend in opposite directions from the dimethylene bridge. In the crystal structure, weak intermolecular C-H···N hydrogen bonds and C-H···p stacking interactions link molecules into infinite three-dimensional supramolecular network structure.
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References
E.J. Campbell and S.T. Nguyen, Tetrahedron. Lett., 42, 1221 (2001).
L. Rousso, N. Friedman, M. Sheves and M. Ottolenghi, Biochemistry, 34, 12059 (1995).
C. Unaleroglu, B. Temelli and J. Hokelek, J. Mol. Struct., 570, 90 (2001).
A.A. Aly and K.M. EI-Shaieb, Tetrahedron, 60, 3797 (2004).
W.K. Dong and J.G. Duan, J. Coord. Chem., 61, 781 (2008).
W.K. Dong, J.G. Duan and G.L. Liu, Transition Met. Chem., 32, 702 (2007).
W.K. Dong, J.Y. Shi, J.K. Zhong, Y.Q. Tian and J.G. Duan, Chin. J. Inorg. Chem., 28, 10 (2008).
W.K. Dong, J.G. Duan, H.L. Wu, J.Y. Shi and T.Z. Yu, Z. Kristallogr. NCS, 221, 555 (2006).
G.M. Sheldrick, SHELXTL97, Program for the Refinement of Crystal Structure, University of Göttingen, Germany (1997).
L. Janusz, Z. Janusz and J. Iwona, Coord. Chem. Rev., 249, 1185 (2005).