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Volume 65 
Part 9 
Page o2233  
September 2009  

Received 17 July 2009
Accepted 19 August 2009
Online 26 August 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 13.3
Details
Open access

4,4'-(Propane-1,3-diyl)dibenzoic acid

aState Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: huajia@jlu.edu.cn

The complete molecule of the title compound, C17H16O4, is generated by crystallographic twofold symmetry, with the central C atom lying on the rotation axis and a dihedral angle between the benzene rings of 81.9 (2)°. In the crystal, molecules are linked by O-H...O hydrogen bonding between carboxyl groups, forming one-dimensional supramolecular chains.

Related literature

For general background, see: Bradshaw et al. (2005[Bradshaw, D., Claridge, J. B., Cussen, E. J., Prior, T. J. & Rosseinsky, M. J. (2005). Acc. Chem. Res. 38, 273-282.]); Eddaoudi et al. (2001[Eddaoudi, M., Moler, D. B., Li, H.-L., Chen, B.-L., Reineke, T. N., O'Keeffe, M. & Yaghi, O. M. (2001). Acc. Chem. Res. 34, 319-330.]); Heo et al. (2007[Heo, J., Jeon, Y. M. & Mirkin, C. A. (2007). J. Am. Chem. Soc. 129, 7712-7713.]); Kesanli & Lin (2003[Kesanli, B. & Lin, W.-B. (2003). Coord. Chem. Rev. 246, 305-326.]). For related structures, see: Dai et al. (2005[Dai, Y.-M., Shen, H.-Y. & Huang, J.-F. (2005). Acta Cryst. E61, o3410-o3411.]); Li et al. (2007[Li, W., Shao, M., Liu, H.-J. & Li, M.-X. (2007). Acta Cryst. E63, o3224.]); Ma et al. (2006[Ma, Z.-C., Ma, A.-Q. & Wang, G.-P. (2006). Acta Cryst. E62, o1165-o1166.]). For the synthesis, see: Cram & Steinberg (1951[Cram, D. J. & Steinberg, H. (1951). J. Am. Chem. Soc. 73, 5691-5704.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16O4

  • Mr = 284.30

  • Monoclinic, C 2/c

  • a = 14.569 (3) Å

  • b = 4.7337 (6) Å

  • c = 21.463 (3) Å

  • [beta] = 102.722 (10)°

  • V = 1443.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.48 × 0.20 × 0.16 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.947, Tmax = 0.989

  • 3830 measured reflections

  • 1276 independent reflections

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

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 0.94

  • 1276 reflections

  • 96 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.82 1.84 2.642 (2) 168
Symmetry code: (i) [-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2559 ).


Acknowledgements

We thank the National Natural Science Foundation of China.

References

Bradshaw, D., Claridge, J. B., Cussen, E. J., Prior, T. J. & Rosseinsky, M. J. (2005). Acc. Chem. Res. 38, 273-282.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Cram, D. J. & Steinberg, H. (1951). J. Am. Chem. Soc. 73, 5691-5704.  [CrossRef] [ChemPort] [ISI]
Dai, Y.-M., Shen, H.-Y. & Huang, J.-F. (2005). Acta Cryst. E61, o3410-o3411.  [CSD] [CrossRef] [details]
Eddaoudi, M., Moler, D. B., Li, H.-L., Chen, B.-L., Reineke, T. N., O'Keeffe, M. & Yaghi, O. M. (2001). Acc. Chem. Res. 34, 319-330.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Heo, J., Jeon, Y. M. & Mirkin, C. A. (2007). J. Am. Chem. Soc. 129, 7712-7713.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Kesanli, B. & Lin, W.-B. (2003). Coord. Chem. Rev. 246, 305-326.  [ISI] [CrossRef] [ChemPort]
Li, W., Shao, M., Liu, H.-J. & Li, M.-X. (2007). Acta Cryst. E63, o3224.  [CSD] [CrossRef] [details]
Ma, Z.-C., Ma, A.-Q. & Wang, G.-P. (2006). Acta Cryst. E62, o1165-o1166.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2009). E65, o2233  [ doi:10.1107/S1600536809033005 ]

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