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Synthesis and Structural Characterization of (E)-1-(4-Chlorobenzylidene)semicarbazide
Corresponding Author(s) : Jian Li
Asian Journal of Chemistry,
Vol. 25 No. 2 (2013): Vol 25 Issue 2
Abstract
The compound (E)-1-(4-chlorobenzylidene)semicarbazide (C8H8N3OCl, Mr = 197.62) was synthesized and characterized by elemental analysis, IR spectra, 1H NMR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c, with a = 17.081(5), b = 4.4508(13), c = 11.896(4) Å, b = 92.979(4)º, V = 903.2(5) Å3, Z = 4, Dc = 1.453 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.384 mm-1, F(000) = 408. The final refinement gave R = 0.0379, wR(F2) = 0.1000 for 1,585 observed reflections with I > 2s(I). X-ray diffraction analysis reveals that the title compound molecule adopts an E configuration about the C=N double bond. The dihedral angles between the semicarbazide group and the benzene ring is 17.4 (2)º. The crystal structure is stabilized by N–H...O hydrogen bonds.
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- M.F. Brana, A. Gradillas, A. Gomez, N. Acero, F. Llinares, D. MunozMingarrro, C. Abradelo, F. Rey-Stolle, M. Yuste, J. Campos, M.A. Gallo and A. Espinosa, J. Med. Chem., 47, 2236 (2004).
- S.M. Sondhi, R. Rani, P. Roy, S.K. Agrawal and A.K. Saxena, Bioorg. Med. Chem. Lett., 19, 1534 (2009).
- J. Kossakowski and M. Jarocka, Farmaco, 56, 785 (2001).
- L.P. Deng and Y.Z. Hu, J. Heterocycl. Chem., 44, 597 (2007).
- L.P. Deng, F.M. Liu and H.Y. Wang, J. Heterocycl. Chem., 42, 13 (2005).
- M.E. Hart,A.R. Chamberlin, C. Walkom, J.A. Sakoff and A. McCluskey, Bioorg. Med. Chem. Lett., 14, 969 (2004).
- G. Goksu, N. Ocal and D.E. Kaufmann, Molecules, 15, 1302 (2010).
- J. Li, Z.P. Liang and W.L. Zeng, Asian J. Chem., 23, 4918 (2011).
- Z.P. Liang and J. Li, Asian J. Chem., 23, 4918 (2011).
- Z.P. Liang and J. Li, Asian J. Chem., 25, 660 (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).
References
M.F. Brana, A. Gradillas, A. Gomez, N. Acero, F. Llinares, D. MunozMingarrro, C. Abradelo, F. Rey-Stolle, M. Yuste, J. Campos, M.A. Gallo and A. Espinosa, J. Med. Chem., 47, 2236 (2004).
S.M. Sondhi, R. Rani, P. Roy, S.K. Agrawal and A.K. Saxena, Bioorg. Med. Chem. Lett., 19, 1534 (2009).
J. Kossakowski and M. Jarocka, Farmaco, 56, 785 (2001).
L.P. Deng and Y.Z. Hu, J. Heterocycl. Chem., 44, 597 (2007).
L.P. Deng, F.M. Liu and H.Y. Wang, J. Heterocycl. Chem., 42, 13 (2005).
M.E. Hart,A.R. Chamberlin, C. Walkom, J.A. Sakoff and A. McCluskey, Bioorg. Med. Chem. Lett., 14, 969 (2004).
G. Goksu, N. Ocal and D.E. Kaufmann, Molecules, 15, 1302 (2010).
J. Li, Z.P. Liang and W.L. Zeng, Asian J. Chem., 23, 4918 (2011).
Z.P. Liang and J. Li, Asian J. Chem., 23, 4918 (2011).
Z.P. Liang and J. Li, Asian J. Chem., 25, 660 (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).