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Synthesis and Structural Characterization of (2E,3E)-N1,N2-Bis(4-chlorobenzylidene)ethane-1,2-diamine
Corresponding Author(s) : Zu-Pei Liang
Asian Journal of Chemistry,
Vol. 25 No. 2 (2013): Vol 25 Issue 2
Abstract
Present compound (2E,3E)-N1,N2-bis(4-chlorobenzylidene)ethane-1,2-diamine (C16H14Cl4N2, Mr = 305.19) was synthesized and characterized by elemental analysis, FT-IR, 1H NMR and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group Cc, with a = 10.166(2), b = 10.345(2), c = 26.650(5) Å, b = 91.91(3)º, V = 2801.1(10) Å3, Z = 8, Dc = 1.447 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.454 mm-1, F(000) = 1264. The final refinement gave R = 0.0652, wR(F2) = 0.1582 for 4,578 observed reflections with I > 2s(I). X-Ray diffraction analysis reveals that the asymmetric unit of the title compound consists of two independent molecules. Each independent molecule adopts an E configuration about the central C=N functional bond. The dihedral angles between the two benzene rings are 2.3(2) and 0.5(2)º, respectively in two independent molecules. The molecules are linked through C-H···Cl hydrogen bonds interactions.
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References
F.D. Karia and P.H. Parsania, Asian J. Chem., 11, 991 (1999).
P.G. More, R.B. Bhalvankar and S.C. Pattar, J. Indian Chem. Soc., 78, 474 (2001).
N.P. Singh, P. Kumar and J. Singh, Asian J. Chem., 24, 5719 (2012).
N. Wang, J.P. Li and Y.L. Pu, Chin. J. Struct Chem., 26, 547 (2007).
S.B. Desai, P.B. Desai and K.R. Desai, Heterocycl. Commun., 7, 83 (2001).
S. Samadhiya and A. Halve, Orient. J. Chem., 17, 119 (2001).
A. Balaban, N. Colak, H. Unver, B. Erk, T.N. Durlu and D.M. Zengin, J. Chem. Crystallogr., 38, 369 (2008).
C.G. Hamaker and B.P. Oberts, J. Chem. Crystallogr., 36, 735 (2006).
J. Chen, X.Y. Xu, J. Gao, Y.H. Li and G.X. Xu, Chin. J. Struct. Chem., 26, 632 (2007).
H.J. Kim, W. Kim, A.J. Lough, B.M. Kim and J.A. Chin, J. Am. Chem. Soc., 127, 16776 (2005).
J.P. May, R. Ting, L. Lermer, J.M. Thomas, Y. Roupioz and D.M. Perrin, J. Am. Chem. Soc., 126, 4145 (2004).
Z. Liu and F.C. Anson, Inorg. Chem., 40, 1329 (2001).
Z.P. Liang, J. Li, F.T. Kong, C.H. Lin and X.S. Tai, Chin. J. Struct. Chem., 28, 628 (2009).
J. Li, Z.P. Liang, F.T. Kong, H. Zhang and X.S. Tai, Chin. J. Struct. Chem., 28, 577 (2009).
N.P. Singh, Anu and J. Singh, Asian J. Chem., 25, 455 (2013).
G.M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Gottingen, Germany (1996).
G.M. Sheldrick, SHELXTL V 5.1 Software Reference Manual, Bruker AXS, Inc., Madison, Wisconsin, USA (1997).
Siemens, SMART and SAINT, Area Detector Control and Integration Software. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA (1996).
M.H. Habibi, K. Barati, M. Zendehdel, R. W. Harrington and W. Clegg, Anal. Sci., 23, x61 (2007).