Received 8 July 2013
The phenyl and tert-butyl groups of the title compound, C27H25NO3, exhibit a trans configuration in agreement with the stereochemistry of the Z phenyl-N-tert-butylnitrone starting material. The attached carbonyl groups are not coplanar with the neighboring dihydroisoxazole ring and the phenyl rings they are bonded to, with torsion angles of 59.26 (8), 17.53 (11), 16.52 (12) and 52.86 (7)°. The dihedral angle between the dihydroisoxazole ring and the directly attached phenyl group is 86.86 (8)°. There are two nonclassical intermolecular C-HO hydrogen-bonding interactions that operate together with an intermolecular C-H interaction to form a supramolecular architecture in the crystal system.
For background to isoxazoline derivatives and their applications, see: Kiss et al. (2009); Velikorodov & Sukhenko (2003); Shi et al. (2012); Khan & Lee (2006). For the mechanism of the 1,3-dipolar cycloaddition of nitrones with alkynes, see: Eberson et al. (1998). For the synthesis of related compounds, see: Chakraborty et al. (2012).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2560 ).
RS is grateful to the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of a Senior Research Fellowship. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for single-crystal X-ray diffraction measurements.
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakraborty, B., Sharma, P. K. & Samanta, A. (2012). Indian J. Chem. Sect. B, 51, 1180-1185.
Eberson, L., McCullough, J. P., Hartshorn, C. M. & Hartshorn, M. P. J. (1998). J. Chem. Soc. Perkin. Trans. 2, pp. 41-47.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Khan, O. F. & Lee, H. J. (2006). Steroids, 71, 183-188.
Kiss, L., Nonn, M., Forro, E., Sillanpaa, R. & Fulop, F. (2009). Tetrahedron Lett. 50, 2605-2608
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, L., Hu, R., Wei, Y., Liang, Y., Yang, Z. & Ke, S. (2012). Eur. J. Med. Chem. 54, 549-556.
Velikorodov, A. V. & Sukhenko, L. T. (2003). Pharm. Chem. J. 37, 24-26.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.