Abstract
The title compound, C30H24N2O4, 3,3′-[1,2-ethanediyl-bis(oxy-2,1-phenylene)]bis[1-(2-pyridyl)-2-propen-1-one] was synthesized and characterized by elemental analysis, FT-IR spectra, 1H NMR, and X-ray single-crystal diffraction. In the molecule, the pyridine plane and the adjacent phenyl plane are almost coplanar with the dihedral angle of 3.07°, while the dihedral angle between the mean planes of the two asymmetric units is 67.56°. The crystal packing is stabilized by weak intermolecular C-H...N and C-H...O hydrogen bonds, C-H...π and π...π stacking interactions.
Similar content being viewed by others
References
D. N. Dhar, The Chemistry of Chalcones and Related Compounds (Wiley, New York, 1981).
P. M. Dey and J. B. Harborne, Methods in Plant Biochemistry, Ed. by B. A. Bohm (Academic Press, London, 1989), Vol. 1, pp. 237–282.
G. Kaupp, M. Reza Naimi-Jamal, and J. Schmeyers, Tetrahedron 59, 3753 (2003).
B. M. Trost, I. Fleming, and M. F. Semmelhack, Comprehensive Organic Synthesis, Ed. by V. J. Lee (Pergamon Press, Oxford, 1991), Vol. 4, pp. 139–168.
J. Clayden, N. Greeves, S. Warren, and P. Wothers, Organic Chemistry (Oxford University Press, Oxford, 2001).
C. Gwengo, R. Iyer, and M. Raja, Cryst. Growth Des. 12, 49–53 (2011).
Y.-Q. Lan, S.-L. Li, J.-S. Qin, et al., Inorg. Chem. 47, 10600 (2008).
A. Rajput and R. Mukherjee, Coord. Chem. Rev. 257, 350 (2013).
F. A. Cotton and T. R. Felthouse, Inorg. Chem. 19, 328 (1980).
C. Cremer and P. Burger, Chem.-Eur. J. 9, 3583 (2003).
F. A. Cotton, C. A. Murillo, X. Wang, et al., Inorg. Chem. 43, 8394 (2004).
V. J. Catalano, M. A. Malwitz, and A. O. Etogo, Inorg. Chem. 43, 5714 (2004).
F. F. Barsoum, H. M. Hosni, and A. S. Girgis, Bioorg. Med. Chem. 14, 3929 (2006).
N. V. Mayekar, S. Chattopadhyay, and S. K. Nayak, Synthesis, 2041 (2003).
G. M. Sheldrick, Program for Multi-Scan Absorption Correction (University of Göttingen, Germany, 2000).
P. T. Beurskens, G. Admiraal, G. Beurskens, et al., The DIRDIF Program System (technical report of the crystallography laboratory, University of Nijmegen, The Netherlands, 1992).
G. M. Sheldrick, Program for Crystal Structure Solution and Refinement (University of Göttingen, Germany, 2000).
P. Wang, C. N. Moorefield, and G. R. Newkome, Org. Lett. 6, 1197 (2004).
F. R. Cibin, N. Di Bello, G. Doddi, et al., Tetrahedron 59, 9971 (2003).
P. S. Patil, J. B.-J. Teh, H.-K. Fun, et al., Acta. Crystallogr. E62, o896 (2006).
X.-H. Yang, M.-C. Wu, W.-D. Zou, et al., Acta. Crystallogr. E62, o3117 (2006).
S. F. Alshahateet, R. Bishop, D. C. Craig, et al., Cryst. Growth Des. 4, 837 (2004).
Y.-Y. Zhu, G.-T. Wang, R.-X. Wang, et al., Cryst. Growth Des. 9, 4778 (2009).
G. Mehta and R.J. Vidya, Org. Chem. 65, 3497 (2000).
C. A. Hunter, Chem. Soc. Rev. 23, 101 (1994).
R. R. Choudhury and R. Chitra, Cryst. Eng. Comm. 12, 2113 (2010).
C. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc. 112, 5525 (1990).
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Wang, G.F., Gong, Q.J., Sun, H. et al. Synthesis and crystal structure of α,β-unsaturated ketone: 3,3′-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[1-(2-pyridyl)-2-propen-1-one]. Crystallogr. Rep. 58, 1113–1116 (2013). https://doi.org/10.1134/S1063774513080105
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1063774513080105