[Journal logo]

Volume 64 
Part 7 
Page o1251  
July 2008  

Received 26 May 2008
Accepted 4 June 2008
Online 13 June 2008

[hg2407sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
R = 0.085
wR = 0.147
Data-to-parameter ratio = 16.4
Details
Open access

4-(4-Propoxybenzoyloxy)benzoic acid

Khushi Muhammad,a M. Khawar Rauf,a Masahiro Ebiharab and Shahid Hameeda*

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bDepartment of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
Correspondence e-mail: shameed@qau.edu.pk

The title compound, C17H16O5, is an important intermediate for the synthesis of side-chain ligands for polymeric liquid crystals. The propoxy and benzoic acid groups subtend dihedral angles of 4.36 (6) and 55.35 (6)°, respectively, with the central benzoyloxy unit. The crystal structure is stabilized by an intermolecular O-H...O hydrogen bond.

Related literature

For related literature, see: Ahmad et al. (2003[Ahmad, H. B., Rama, N. H., Hussain, M., Hussain, M. T., Qasim, M. M., Hameed, S., Malana, M. A. & Malik, A. (2003). Indian J. Chem. 42B, 611-615.]); Aranzazu et al. (2006[Aranzazu, M.-G., Ernesto, P. & Antonio, B. (2006). Polymer, 47, 2080-2090.]); Cady et al. (2002[Cady, A., Olson, D. A., Han, X. F., Nguyen, H. T. & Huang, C. C. (2002). Rapid Commun. Phys. Rev. E. 65, 030701.]); Hameed & Rama (2004[Hameed, S. & Rama, N. H. (2004). J. Chem. Soc. Pak. 26, 157-162.]); Hartung et al. (1997[Hartung, H., Hoffmann, F. & Weissflog, W. (1997). J. Mol. Struct. 415, 205-214.]); Hussain et al. (2003[Hussain, M., Hussain, M. T., Rama, N. H., Hameed, S., Malik, A. & Khan, K. M. (2003). Nat. Prod. Res. 17, 207-214.], 2005[Hussain, M. T., Rama, N. H., Hameed, S., Malik, A. & Khan, K. M. (2005). Nat. Prod. Res. 19, 41-51.]); Kong & Tang (1998[Kong, X. X. & Tang, B. Z. (1998). Chem. Mater. 10, 3352-3363.]); Nazir et al. (2008a[Nazir, S., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008b). Acta Cryst. E64, o423.],b[Nazir, S., Muhammad, K., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008a). Acta Cryst. E64, o1013.]); Ribeiro et al. (2008[Ribeiro, G., Benadiba, M., Colquhoun, A. & Silva, D. D. (2008). Polyhedron, 27, 1131-1137.]); Shafiq et al. (2003[Shafiq, Z., Arfan, M., Rama, N. H., Hussain, M. & Hameed, S. (2003). Indian J. Chem. 42B, 1523-1526.], 2005[Shafiq, Z., Arfan, M., Rama, N. H., Hameed, S., Abbas, G. & Hussain, M. T. (2005). Turk. J. Chem. 29, 321-325.]); Wu & Hsu (2007[Wu, S.-L. & Hsu, H.-N. (2007). Liq. Cryst. 34, 1159-1165.]); Wu & Lin (2007[Wu, S.-L. & Lin, C.-Y. (2007). Liq. Cryst. 34, 25-31.]).

[Scheme 1]

Experimental

Crystal data

  • C17H16O5

  • Mr = 300.30

  • Monoclinic, C 2/c

  • a = 21.063 (15) Å

  • b = 5.703 (4) Å

  • c = 24.437 (18) Å

  • [beta] = 99.790 (9)°

  • V = 2893 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 123 (2) K

  • 0.30 × 0.19 × 0.15 mm
Data collection

  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: empirical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.970, Tmax = 0.985

  • 11426 measured reflections

  • 3297 independent reflections

  • 2824 reflections with I > 2[sigma](I)

  • Rint = 0.051
Refinement

  • R[F2 > 2[sigma](F2)] = 0.084

  • wR(F2) = 0.146

  • S = 1.26

  • 3297 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3O...O4i 0.84 1.77 2.606 (3) 172
Symmetry code: (i) -x, -y+1, -z.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001[Molecular Structure Corporation & Rigaku (2001). Crystal Clear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004[Molecular Structure Corporation & Rigaku (2004). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tenessee, USA.]); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2407 ).

Acknowledgements

MKR is grateful to The Higher Education Commission of Pakistan for financial support under the International Support initiative program for Doctoral Fellowships in Gifu University, Japan.

References

Ahmad, H. B., Rama, N. H., Hussain, M., Hussain, M. T., Qasim, M. M., Hameed, S., Malana, M. A. & Malik, A. (2003). Indian J. Chem. 42B, 611-615.  [ChemPort]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Aranzazu, M.-G., Ernesto, P. & Antonio, B. (2006). Polymer, 47, 2080-2090.
Cady, A., Olson, D. A., Han, X. F., Nguyen, H. T. & Huang, C. C. (2002). Rapid Commun. Phys. Rev. E. 65, 030701.
Hameed, S. & Rama, N. H. (2004). J. Chem. Soc. Pak. 26, 157-162.  [ChemPort]
Hartung, H., Hoffmann, F. & Weissflog, W. (1997). J. Mol. Struct. 415, 205-214.  [CrossRef] [ChemPort] [ISI]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Hussain, M., Hussain, M. T., Rama, N. H., Hameed, S., Malik, A. & Khan, K. M. (2003). Nat. Prod. Res. 17, 207-214.  [CrossRef] [PubMed] [ChemPort]
Hussain, M. T., Rama, N. H., Hameed, S., Malik, A. & Khan, K. M. (2005). Nat. Prod. Res. 19, 41-51.  [ISI] [CrossRef] [PubMed] [ChemPort]
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tenessee, USA.
Kong, X. X. & Tang, B. Z. (1998). Chem. Mater. 10, 3352-3363.  [CrossRef] [ChemPort]
Molecular Structure Corporation & Rigaku (2001). Crystal Clear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Molecular Structure Corporation & Rigaku (2004). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Nazir, S., Muhammad, K., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008a). Acta Cryst. E64, o1013.  [CrossRef] [details]
Nazir, S., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008b). Acta Cryst. E64, o423.  [CrossRef] [details]
Ribeiro, G., Benadiba, M., Colquhoun, A. & Silva, D. D. (2008). Polyhedron, 27, 1131-1137.  [ISI] [CrossRef] [ChemPort]
Shafiq, Z., Arfan, M., Rama, N. H., Hameed, S., Abbas, G. & Hussain, M. T. (2005). Turk. J. Chem. 29, 321-325.  [ChemPort]
Shafiq, Z., Arfan, M., Rama, N. H., Hussain, M. & Hameed, S. (2003). Indian J. Chem. 42B, 1523-1526.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, S.-L. & Hsu, H.-N. (2007). Liq. Cryst. 34, 1159-1165.  [CrossRef] [ChemPort]
Wu, S.-L. & Lin, C.-Y. (2007). Liq. Cryst. 34, 25-31.  [CrossRef] [ChemPort]

Acta Cryst (2008). E64, o1251  [ doi:10.1107/S1600536808016942 ]

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.