[Journal logo]

Volume 69 
Part 4 
Page o543  
April 2013  

Received 26 February 2013
Accepted 12 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.005 Å
R = 0.068
wR = 0.191
Data-to-parameter ratio = 14.3
Details
Open access

4-[5-(4-Benzoyloxyphenyl)-1,2,4-oxadiazol-3-yl]phenyl benzoate

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India, and bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore, 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C28H18N2O5, the dihedral angle between the terminal benzoate rings is 20.67 (12)°. The central oxadiazole ring is almost coplanar with its two benzene ring substituents, making dihedral angles of 4.80 (16) and 5.82 (16)°. In the crystal, pairs of C-H...O hydrogen bonds form inversion dimers with R22(40) ring motifs. The structure also features C-H...O, C-H...[pi] and [pi]-[pi] interactions [centroid-centroid separation = 3.695 (4) Å].

Related literature

For the use of oxadiazole derivatives as antimicrobial agents, see: Dhol et al. (2005[Dhol, S. R., Bhimani, A. S., Khunt, R. C. & Parik, A. R. (2005). Indian J. Heterocycl. Chem. 15, 63-64.]) and for a related structure, see: Emmerling et al. (2006[Emmerling, F., Orgzall, I., Reck, G., Schulz, B. W., Stackhause, S. & Schulz, B. (2006). J. Mol. Struct. 800, 74-84.]). For hydrogen-bond motifs, see: 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
  • C28H18N2O5

  • Mr = 462.44

  • Monoclinic, P 21 /c

  • a = 21.069 (18) Å

  • b = 6.063 (5) Å

  • c = 18.727 (16) Å

  • [beta] = 107.159 (13)°

  • V = 2286 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 300 K

  • 0.23 × 0.23 × 0.22 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 21331 measured reflections

  • 4513 independent reflections

  • 2518 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.191

  • S = 1.03

  • 4513 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10-C15 ring.

D-H...A D-H H...A D...A D-H...A
C18-H18...O5i 0.93 2.57 3.407 (5) 150
C25-H25...O3ii 0.93 2.34 3.222 (6) 158
C28-H28...Cg3iii 0.93 2.96 3.678 (5) 135
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z+1; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 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 Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5303 ).


Acknowledgements

MKS thanks theUGC-BRS and the UoM for the award of a fellowship, and MPS gratefully acknowledges financial support (grant F. No. 37-456/2009[SR]) from the UGC, India.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Dhol, S. R., Bhimani, A. S., Khunt, R. C. & Parik, A. R. (2005). Indian J. Heterocycl. Chem. 15, 63-64.  [ChemPort]
Emmerling, F., Orgzall, I., Reck, G., Schulz, B. W., Stackhause, S. & Schulz, B. (2006). J. Mol. Struct. 800, 74-84.  [ISI] [CSD] [CrossRef] [ChemPort]
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]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o543  [ doi:10.1107/S1600536813006922 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.