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Synthesis and Crystal Structure of 4-Dichloroacetyl-3-phenyl-3,4-dihyro-2H-1,4-benzoxazine
Corresponding Author(s) : Fei Ye
Asian Journal of Chemistry,
Vol. 26 No. 10 (2014): Vol 26 Issue 10
Abstract
A new compound 4-dichloroacetyl-3-phenyl-3,4-dihyro-2H-1,4-benzoxazine with m.f. C16H13NO2Cl2 was synthesized and characterized. The crystal structure of the compound has been determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 15.105(3), b = 6.2685(13), c = 16.084(3) Å, a = 90°, b = 103.79(3)°, g = 90°, V = 1479.1(5)Å3, Z = 4, F(000) = 664, Dc = 1.447 g/cm3, μ = 0.442 mm-1, the final R1 = 0.0507 and wR2 = 0.1435 for 2417 observed reflections with I > 2s(I). A total of 13533 reflections were collected, of which 3362 were independent (Rint = 0.0307). Benzoxazine ring and the benzene plane were almost perpendicular with the dihedral angle of 91.7º with each other.
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- G. Caliendo, E. Perissutti, V. Santagada, F. Fiorino, B. Severino, D. Cirillo, R. d’Emmanuele diVilla Bianca, L. Lippolis, A. Pinto and R. Sorrentino, Eur. J. Med. Chem., 39, 815 (2004); doi:10.1016/j.ejmech.2004.05.003.
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- T. Matola and I. Jablonkai, Crop Prot., 26, 278 (2007); doi:10.1016/j.cropro.2005.07.015.
- S. Silva, S. Tardy, S. Routier, F. Suzenet, A. Tatibouët, A.P. Rauter and P. Rollin, Tetrahedron Lett., 49, 5583 (2008); doi:10.1016/j.tetlet.2008.07.023.
- G.P. Cao, W.J. Chen and X.B. Liu, Polym. Degrad. Stab., 93, 739 (2008); doi:10.1016/j.polymdegradstab.2007.10.002.
- Y. Fu, L.H. Qu, S.S. Zhang, F. Ye, L.X. Zhao, S. Gao and Z.Y. Xing, Heterocycl. Commun., 18, 143 (2012); doi:10.1515/hc-2012-0056.
- Y. Fu, S.S. Zhang and F. Ye, Indian J. Heterocycl. Chem., 20, 405 (2011).
- G.M. Sheldrick, SHELXS-97, Program for X-Ray Crystal Structure Solution, University of Göttingen, Göttingen, Germany (1997).
- G.M. Sheldrick, SHELXS-97, Program for X-Ray Crystal Structure Refinement, University of Göttingen, Göttingen, Germany (1997).
References
G. Caliendo, E. Perissutti, V. Santagada, F. Fiorino, B. Severino, D. Cirillo, R. d’Emmanuele diVilla Bianca, L. Lippolis, A. Pinto and R. Sorrentino, Eur. J. Med. Chem., 39, 815 (2004); doi:10.1016/j.ejmech.2004.05.003.
V.M. Ismailov, I.A. Mamedov and N.N. Yusubov, Russ. J. Org. Chem., 40, 284 (2004); doi:10.1023/B:RUJO.0000034957.86085.c2.
T. Matola and I. Jablonkai, Crop Prot., 26, 278 (2007); doi:10.1016/j.cropro.2005.07.015.
S. Silva, S. Tardy, S. Routier, F. Suzenet, A. Tatibouët, A.P. Rauter and P. Rollin, Tetrahedron Lett., 49, 5583 (2008); doi:10.1016/j.tetlet.2008.07.023.
G.P. Cao, W.J. Chen and X.B. Liu, Polym. Degrad. Stab., 93, 739 (2008); doi:10.1016/j.polymdegradstab.2007.10.002.
Y. Fu, L.H. Qu, S.S. Zhang, F. Ye, L.X. Zhao, S. Gao and Z.Y. Xing, Heterocycl. Commun., 18, 143 (2012); doi:10.1515/hc-2012-0056.
Y. Fu, S.S. Zhang and F. Ye, Indian J. Heterocycl. Chem., 20, 405 (2011).
G.M. Sheldrick, SHELXS-97, Program for X-Ray Crystal Structure Solution, University of Göttingen, Göttingen, Germany (1997).
G.M. Sheldrick, SHELXS-97, Program for X-Ray Crystal Structure Refinement, University of Göttingen, Göttingen, Germany (1997).