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Volume 69 
Part 8 
Pages o1284-o1285  
August 2013  

Received 8 July 2013
Accepted 15 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.094
Data-to-parameter ratio = 10.5
Details
Open access

(2-tert-Butyl-3-phenyl-2,3-dihydroisoxazole-4,5-diyl)bis(phenylmethanone)

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
Correspondence e-mail: eesans@yahoo.com

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-H...O hydrogen-bonding interactions that operate together with an intermolecular C-H...[pi] interaction to form a supramolecular architecture in the crystal system.

Related literature

For background to isoxazoline derivatives and their applications, see: Kiss et al. (2009[Kiss, L., Nonn, M., Forro, E., Sillanpaa, R. & Fulop, F. (2009). Tetrahedron Lett. 50, 2605-2608]); Velikorodov & Sukhenko (2003[Velikorodov, A. V. & Sukhenko, L. T. (2003). Pharm. Chem. J. 37, 24-26.]); Shi et al. (2012[Shi, L., Hu, R., Wei, Y., Liang, Y., Yang, Z. & Ke, S. (2012). Eur. J. Med. Chem. 54, 549-556.]); Khan & Lee (2006[Khan, O. F. & Lee, H. J. (2006). Steroids, 71, 183-188.]). For the mechanism of the 1,3-dipolar cycloaddition of nitrones with alkynes, see: Eberson et al. (1998[Eberson, L., McCullough, J. P., Hartshorn, C. M. & Hartshorn, M. P. J. (1998). J. Chem. Soc. Perkin. Trans. 2, pp. 41-47.]). For the synthesis of related compounds, see: Chakraborty et al. (2012[Chakraborty, B., Sharma, P. K. & Samanta, A. (2012). Indian J. Chem. Sect. B, 51, 1180-1185.]).

[Scheme 1]

Experimental

Crystal data
  • C27H25NO3

  • Mr = 411.48

  • Orthorhombic, P n a 21

  • a = 20.1034 (12) Å

  • b = 17.799 (1) Å

  • c = 6.1366 (3) Å

  • V = 2195.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.984

  • 20181 measured reflections

  • 2967 independent reflections

  • 2422 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.094

  • S = 1.05

  • 2967 reflections

  • 283 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18-C23 ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...O3i 0.93 2.51 3.203 (3) 131
C25-H25A...O1ii 0.96 2.59 3.483 (3) 155
C2-H2...Cg1i 0.93 2.70 3.490 (3) 143
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2560 ).


Acknowledgements

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.

References

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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Khan, O. F. & Lee, H. J. (2006). Steroids, 71, 183-188.  [CrossRef] [PubMed]
Kiss, L., Nonn, M., Forro, E., Sillanpaa, R. & Fulop, F. (2009). Tetrahedron Lett. 50, 2605-2608  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shi, L., Hu, R., Wei, Y., Liang, Y., Yang, Z. & Ke, S. (2012). Eur. J. Med. Chem. 54, 549-556.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Velikorodov, A. V. & Sukhenko, L. T. (2003). Pharm. Chem. J. 37, 24-26.  [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1284-o1285   [ doi:10.1107/S1600536813019508 ]

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