Abstract
The title compounds, 2-(4-nitrophenyl)-2-(phenylamino)propanenitrile (C15H13N3O2) (1) and 2-(4-fluorophenylamino)-2-(4-nitrophenyl)propanenitrile, (C15H12FN3O2) (2), were synthesized and characterized by spectral analysis and X-ray diffraction studies. Crystals 1 are trigonal, sp. gr. P61, Z = 6, a = 9.4638(9) Å, c = 26.877(3) Å, R = 0.0567; crystals 2 are monoclinic, sp. gr. C2/c, Z = 8, a = 16.9640(12) Å, b = 5.9812(5) Å, c = 27.460(2) Å, β = 91.57(7)°. R = 0.0498. The dihedral angle between the planes of nitrophenyl and phenylamino rings in 1 is 83.55(20)°; the dihedral angle between the planes of flourophenylamino and nitrophenyl rings in 2 is 80.59(7)°. The crystal structure of 1 is stabilized by N-H⋯O hydrogen bonds, whereas N-H⋯N and C-H⋯F inter- and C-H⋯N intramolecular interactions are observed in crystal 2.
Similar content being viewed by others
References
Y. M. Shafran, V. A. Bakulev, and V. S. Mokrushin, Russ. Chem. Rev. 58, 148 (1989).
D. Enders and J. P. Shilvock, Chem. Soc. Rev. 29, 359 (2000).
H. Gröger, Chem. Rev. 103, 2795 (2003).
A. G. Myers and D. W. Kung, Org. Lett. 2, 3019 (2000).
M. Brandon, N. K. Fetterly, and J. G. Verkade, Tetrahedron 62, 440 (2006).
T. Opatz, Synthesis 1941 (2009).
G. K. S. Prakash, T. Mathew, C. Panja, S. Alconcel, H. Vaghoo, and C. Do, Pro. Natl. Acad. Sci. 104, 3703 (2007).
A. Strecker, Liebigs Ann. Chim. 75, 27 (1850).
G. Brahmachari and B. Banerjee, Asian J. Org. Chem. 1, 251 (2012).
G. M. Sheldrick, Acta Crystallogr. A 64(1), 112 (2008).
L. J. Farrugia, J. Appl. Crystallogr. 30, 567 (1997).
A. L. Spek, Acta Crystallogr. D 65, 148 (2009).
M. Nardelli, J. Appl. Crystallogr. 28, 659 (1995).
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. II S1 (1987).
R. J. Gillespie, J. Chem. Educ. 40, 295 (1963).
R. J. Gillespie, Chem. Soc. Rev. 21, 59 (1992).
D. Bandyopadhyay, J. M. Velazquez, and B. K. Banik, Org. Med. Chem. Lett. 1, 1 (2010).
N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, S. Singh, Suresh, E. R. V. Jasra, Tetrahedron Lett. 49, 640 (2008).
M. M. Mojtahedi, M. S. Abaee, and T. Alishiri, Tetrahedron Lett. 50, 2322 (2009).
M. Shekouhy, Catal. Sci. Technol. 2, 1010 (2012).
G.-W. Zhang, D.-H. Zheng, J. Nie, T. Wang, and J.-A. Ma, Org. Biomol. Chem. 8, 1399 (2010).
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., Laskar, S., Banerjee, B. et al. Crystal structure of 2-(4-nitrophenyl)-2-(phenylamino)propanenitrile and 2-(4-fluorophenylamino)-2-(4-nitrophenyl)propanenitrile. Crystallogr. Rep. 59, 1037–1041 (2014). https://doi.org/10.1134/S106377451406025X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S106377451406025X