Abstract
We report a novel three-component condensation of benzalacetophenone, ethyl acetoacetate, and malonodinitrile in a 1:1:1 molar ratio respectively, involving an equimolar amount of morpholine acetate to form ethyl-4,6(R,S)-diphenyl-2-dicyanomethylenecyclohex-3-ene-1(R,S)-carboxylate whose crystal structure is determined by single crystal XRD. The intermolecular interaction is analyzed using an atomatom potential model, and infinite chains of energetically tightly coupled molecules in the crystal structure are identified and described. A weak hydrogen bond of the CAr–H…O type is found.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R. V. A. Orru and M. de Greef. Synthesis, 2003, (10), 1471.
A. Carlone, S. Cabrera, M. Marigo, et al. Chem. Int. Ed., 2007, 46, 1101.
H. Hugel. Molecules, 2009, 14(12), 4936.
H. Eckert. Molecules, 2012, 17(9), 1074.
Y. Gu. Green Chem., 2012, 14, 2091.
C. Simon, T. Constantieux, and J. Rodriguez. Eur. J. Org. Chem., 2004, 4957.
A. M. Shestopalov, A. A. Shestopalov, and L. A. Rodinovskaya. Synthesis, 2008, (1), 1.
G. M. Sheldrick. Acta Crystallogr., 2008, A64(1), 112–122.
F. H. Allen, D. G. Watson, L. Brammer, et al. Internat. Tables for Crystallography, 2006, Vol. C, Chapter 9.5, 790–811.
D. Cremer and J. A. Pople. J. Am. Chem. Soc., 1975, 97(6), 1354.
D. E. Williams and D. J. Houpt. Acta Crystallogr., 1986, B42, 286.
A. V. Maleev, A. A. Gevorgyan, and K. A. Potekhin. J. Struct. Chem., 2018, 59(2), 455–462.
Yu. V. Zefirov and P. M. Zorkii. Usp. Khim., 1989, 58(5), 713.
P. M. Zorkii and O. N. Zorkaya. J. Struct. Chem., 1998, 39(1), 103–124.
G. R. Desiraju and T. Steiner. The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford: Oxford University Press, 1999.
B. K. Vainshtein. Modern Crystallography, Vol. 1. Fundamentals of Crystals. Symmetry, and Methods of Structural Crystallography. Springer–Verlag Berlin. 2nd enlarged edition, 1994.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © 2018 A. I. Ismiev, K. A. Potekhin, A. V. Maleev, R. K. Askerov, A. M. Maharramov.
Translated from Zhurnal Strukturnoi Khimii, Vol. 59, No. 8, pp. 1975–1981, November-December, 2018.
Rights and permissions
About this article
Cite this article
Ismiev, A.I., Potekhin, K.A., Maleev, A.V. et al. Synthesis, Molecular and Crystal Structure of Ethyl-4,6(R,S)-Diphenyl-2-Dicyanomethylenecyclohex-3-Ene-1(R,S)-Carboxylate. J Struct Chem 59, 1911–1917 (2018). https://doi.org/10.1134/S0022476618080206
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476618080206