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Volume 68 
Part 11 
Page o3215  
November 2012  

Received 9 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 19.2
Details
Open access

3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole

aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C15H12ClNO, the isoxazoline ring adopts an envelope conformation with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16 (7)°. The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93 (7)°. In the crystal, weak C-H...O, C-H...N and C-H...[pi] interactions connect the molecules into layers perpendicular to the a axis.

Related literature

For the biological and medicinal importance of isoxazole compounds, see: Miller et al. (2009[Miller, J. J., Rajaram, S., Pfaffenroth, C. & Sigman, M. S. (2009). Tetrahedron, 65, 3110-3119.]); Prasad et al. (2007[Prasad, Y. R., Kumar, P. R. & Ramesh, B. (2007). Int. J. Chem. Sci. 5, 542-548.]). For their use in ring-opening polymerizations, see: Wiesbrock et al. (2005[Wiesbrock, F., Hoogenboom, R., Leenen, M. A. M., Meier, M. A. R. & Schubert, U. S. (2005). Macromolecules, 38, 5025-5034.]). For the puckering analysis of five-membered rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12ClNO

  • Mr = 257.71

  • Monoclinic, C 2/c

  • a = 29.797 (5) Å

  • b = 10.717 (5) Å

  • c = 8.086 (5) Å

  • [beta] = 103.088 (5)°

  • V = 2515 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 200 K

  • 0.58 × 0.42 × 0.21 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.850, Tmax = 0.943

  • 11843 measured reflections

  • 3132 independent reflections

  • 2637 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.103

  • S = 1.03

  • 3132 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12...N1i 0.95 2.74 3.657 (2) 163
C12-H12...O1i 0.95 2.65 3.390 (2) 135
C2-H2B...O1ii 0.99 2.67 3.466 (2) 138
C26-H26...O1ii 0.95 2.70 3.431 (2) 134
C22-H22...Cgiii 0.95 2.81 3.721 (3) 162
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2526 ).


Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Miller, J. J., Rajaram, S., Pfaffenroth, C. & Sigman, M. S. (2009). Tetrahedron, 65, 3110-3119.  [ISI] [CrossRef] [ChemPort]
Prasad, Y. R., Kumar, P. R. & Ramesh, B. (2007). Int. J. Chem. Sci. 5, 542-548.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wiesbrock, F., Hoogenboom, R., Leenen, M. A. M., Meier, M. A. R. & Schubert, U. S. (2005). Macromolecules, 38, 5025-5034.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3215  [ doi:10.1107/S1600536812043711 ]

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