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Volume 69 
Part 8 
Page o1260  
August 2013  

Received 9 July 2013
Accepted 10 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.101
Data-to-parameter ratio = 16.3
Details
Open access

2,2'-[Ethane-1,2-diylbis(oxy)]dibenzaldehyde

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,cChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt,dSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England,eChemistry Department, Faculty of Science, Sohag University, 82524-Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C16H14O4, the benzene rings are inclined at a dihedral angle of 75.14 (9)°. The torsion angle of the bridging O-C-C-O group is -76.50 (11)°. In the crystal, molecules are linked by C-H...O hydrogen bonds, forming C(6) chains along [100]. Furthermore, C-H...[pi] interactions and [pi]-[pi] stacking interactions [centroid-centroid distances = 3.6957 (7) and 3.6735 (8) Å] contribute to the stability of the crystal packing.

Related literature

For the synthesis and utlization of bis-funtionalized compounds, see: Holland et al. (2007[Holland, J. P., Aigbirhio, F. I., Betts, H. M., Bonnitcha, P. D., Burke, P., Christlieb, M., Churchill, G. C., Cowley, A. R., Dilworth, J. R., Donnelly, P. S., Green, J. C., Peach, J. M., Vasudevan, S. R. & Warren, J. E. (2007). Inorg. Chem. 46, 465-485.]); Pedras et al. (2010[Pedras, B., Gallego, D., Figueiredo, P., Nunes-Miranda, J. D., Capelo, J. L. & Lodeiro, C. (2010). Molbank, 2, M683.]); Mabkhot et al. (2012[Mabkhot, Y. N., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.]); Gavrilova & Bosnich (2004[Gavrilova, A. L. & Bosnich, B. (2004). Chem. Rev. 104, 349-383.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For graph-set theory, 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
  • C16H14O4

  • Mr = 270.27

  • Triclinic, [P \overline 1]

  • a = 7.7571 (1) Å

  • b = 8.3277 (1) Å

  • c = 11.2965 (1) Å

  • [alpha] = 82.283 (7)°

  • [beta] = 75.839 (7)°

  • [gamma] = 66.823 (6)°

  • V = 649.87 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 120 K

  • 0.62 × 0.44 × 0.22 mm

Data collection
  • Rigaku R-AXIS conversion diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.878, Tmax = 1.000

  • 9715 measured reflections

  • 2969 independent reflections

  • 2862 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.101

  • S = 1.07

  • 2969 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3-C8 and C10-C15 benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
C8-H8...O3i 0.95 2.44 3.2508 (17) 144
C2-H2A...Cg1ii 0.99 2.68 3.4220 (12) 132
C2-H2B...Cg2iii 0.99 2.70 3.5964 (14) 151
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1; (iii) -x, -y+1, -z.

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: BT6920 ).


Acknowledgements

Manchester Metropolitan University and Erciyes University are gratefully acknowledged for supporting this study.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gavrilova, A. L. & Bosnich, B. (2004). Chem. Rev. 104, 349-383.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Holland, J. P., Aigbirhio, F. I., Betts, H. M., Bonnitcha, P. D., Burke, P., Christlieb, M., Churchill, G. C., Cowley, A. R., Dilworth, J. R., Donnelly, P. S., Green, J. C., Peach, J. M., Vasudevan, S. R. & Warren, J. E. (2007). Inorg. Chem. 46, 465-485.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.  [CrossRef] [ChemPort] [PubMed]
Pedras, B., Gallego, D., Figueiredo, P., Nunes-Miranda, J. D., Capelo, J. L. & Lodeiro, C. (2010). Molbank, 2, M683.
Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1260  [ doi:10.1107/S1600536813019156 ]

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