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Volume 69 
Part 4 
Page o597  
April 2013  

Received 7 February 2013
Accepted 18 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.103
Data-to-parameter ratio = 16.7
Details
Open access

5-(3-Methoxyphenyl)-3-phenyl-1,2-oxazole

aDepartment of Physics, P.T. Lee Chengalvaraya Naicker College of Engineering and Technology, Kancheepuram 631 502, India,bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India, and cPostgraduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India
Correspondence e-mail: seshadri_pr@yahoo.com

In the title compound, C16H13NO2, the isoxazole ring makes dihedral angles of 17.1 (1)° with the 3-methoxyphenyl ring and 15.2 (1)° with the phenyl group. Centrosymmetric dimers that are realised by pairs of C-H...[pi] interactions are observed in the crystal structure.

Related literature

For general background to isoxazole derivaties, see: Sperry & Wright (2005[Sperry, J. & Wright, D. (2005). Curr. Opin. Drug Discov. Dev. 8, 723-740.]); Tanaka et al. (2007[Tanaka, M., Haino, T., Ideta, K., Kubo, K., Mori, A. & Fukazawa, Y. (2007). Tetrahedron, 63, 652-.]). For their biological activity, see: Stevens & Albizati (1984[Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.]). For related structures, see: Samshuddin et al. (2011[Samshuddin, S., Butcher, R. J., Akkurt, M., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1975-o1976.]); Balakrishnan et al. (2011[Balakrishnan, B., Praveen, C., Seshadri, P. R. & Perumal, P. T. (2011). Acta Cryst. E67, o1575.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13NO2

  • Mr = 251.27

  • Orthorhombic, P n a 21

  • a = 7.909 (2) Å

  • b = 27.239 (8) Å

  • c = 5.9652 (17) Å

  • V = 1285.1 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.35 × 0.30 × 0.30 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 6838 measured reflections

  • 2898 independent reflections

  • 2256 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

  • wR(F2) = 0.103

  • S = 1.03

  • 2898 reflections

  • 174 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C1-H1...Cgi 0.93 2.96 3.732 (2) 141
C4-H4...Cgii 0.93 3.06 3.768 (3) 134
Symmetry codes: (i) [-x+1, -y+2, z-{\script{1\over 2}}]; (ii) [-x, -y+2, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison. Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison. Wisconsin, 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: ZJ2101 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Balakrishnan, B., Praveen, C., Seshadri, P. R. & Perumal, P. T. (2011). Acta Cryst. E67, o1575.  [CrossRef] [details]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison. Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Samshuddin, S., Butcher, R. J., Akkurt, M., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1975-o1976.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sperry, J. & Wright, D. (2005). Curr. Opin. Drug Discov. Dev. 8, 723-740.  [ChemPort]
Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.  [CrossRef] [ChemPort] [ISI]
Tanaka, M., Haino, T., Ideta, K., Kubo, K., Mori, A. & Fukazawa, Y. (2007). Tetrahedron, 63, 652-.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o597  [ doi:10.1107/S160053681300740X ]

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