Abstract
The organic carbonitrile namely methyl (6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-4H-pyran)- 3-carboxylate is synthesized via one-pot multi-component reaction at room temperature using commercially available urea as inexpensive and environmentally benign organo-catalyst and its crystal structure is determined by X-ray technique. The crystals are monoclinic, sp. gr. C2/c, a = 12.3069(8) Å, b = 9.7023(7) Å, c = 24.812(2) Å, β = 94.862(6)°, Z = 8. The dihedral angle between pyran and phenyl rings is 87.8(1)°; the pyran ring is almost planar The dihedral angle between the mean planes of phenyl ring and nitro group is 44.4(2)°. The crystal structure is stabilized by N−H···N and N−H···O hydrogen bonds. In addition, C−H···π interactions are also observed in the crystal structure.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. Feuer, Prog. Med. Chem. 10, 85 (1974).
F. M. Dean, Naturally Occurring Oxygen Ring Compounds (Butterworth-Heinemann, London, 1963), p. 176.
A. Goel and V. J. Ram, Tetrahedron 65, 7825 (2009).
J. Y. C. Wu, W. F. Fong, et al., Eur. J. Pharmacol. 9, 473 (2003).
T. Raj, R. K. Bhatia, et al., Eur. J. Med. Chem. 45, 790 (2010).
M. Rueping and E. Sugiono, Chem. Eur. J. 14, 6329 (2008).
L. Hanna, BETA 12, 8 (1999).
M. T. Flavin, J. D. Rizzo, et al., J. Med. Chem. 39, 1303 (1996).
D. O. Moon, K. C. Kim, et al., Int. Immunopharmacol. 7, 222 (2007).
V. F. De Andrade-Neto, M. O. Goulart, et al., Bioorg. Med. Chem. Lett. 14, 1145 (2004).
P. S. Elisa, E. B. Ana, et al., Chem. Biodiversity 2, 264 (2005).
G. Brahmachari and B. Banerjee, ACS Sustainable Chem. Eng. 2, 411 (2014).
G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).
L. J. Farrugia, J. Appl. Crystallogr. 30, 565 (1997).
L. J. Farrugia, J. Appl Crystallogr. 32, 837 (1999).
M. Nardelli, J. Appl. Crystallogr. 28, 659 (1995).
A. L. Spek, Acta Crystallogr. D 65, 148 (2009).
Y. Li, X. Wang, et al., Acta Crystallogr. E 61, o1115 (2005).
F. H. Allen, O. Kennard, D. G. Watson, et al., J. Chem. Soc. Perkin Trans. 2, S1–S19 (1987).
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
Sharma, S., Banerjee, B., Brahmachari, G. et al. X-ray crystallography of methyl (6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-4H-pyran)-3-carboxylate. Crystallogr. Rep. 61, 1051–1054 (2016). https://doi.org/10.1134/S1063774516070105
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1063774516070105