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Volume 68 
Part 1 
Page o153  
January 2012  

Received 9 December 2011
Accepted 13 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.141
Data-to-parameter ratio = 17.0
Details
Open access

4-(Furan-2-ylmethoxy)benzene-1,2-dicarbonitrile

aFirat University, Department of Chemistry, 23169 Elazig, Turkey, and bHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C13H8N2O2, prepared from furfuryl alcohol and 4-nitrophthalonitrile in the presence of potassium carbonate in dimethylformamide, the furan and benzene rings are oriented at a dihedral angle of 53.45 (9)°. In the crystal, weak C-H...O and C-H...N hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For the use of phthalonitriles in the preparation of symmetrically and unsymmetrically substituted phthalocyanine complexes, see: Leznoff & Lever (1996[Leznoff, C. C. & Lever, A. B. P. (1996). Editors. Phthalocyanines: Properties and Applications, Vols. 1-4. Weinheim: VHC.]). For the fundamental optical and electronic properties of phthalocyanines and their applications, see: McKeown (1998[McKeown, N. B. (1998). Phthalocyanine Materials: Synthesis, Structure and Function. Cambridge University Press.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8N2O2

  • Mr = 224.21

  • Orthorhombic, P 21 21 21

  • a = 3.9681 (2) Å

  • b = 14.3029 (3) Å

  • c = 19.2100 (5) Å

  • V = 1090.27 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.15 × 0.08 × 0.06 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.986, Tmax = 0.994

  • 6208 measured reflections

  • 2615 independent reflections

  • 1709 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.141

  • S = 1.06

  • 2615 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...N1i 0.95 2.45 3.369 (4) 162
C10-H10...O2ii 0.95 2.42 3.233 (3) 144
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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, 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.]) 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: BQ2327 ).


Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of the diffractometer.

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.
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Leznoff, C. C. & Lever, A. B. P. (1996). Editors. Phthalocyanines: Properties and Applications, Vols. 1-4. Weinheim: VHC.
McKeown, N. B. (1998). Phthalocyanine Materials: Synthesis, Structure and Function. Cambridge University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o153  [ doi:10.1107/S1600536811053669 ]

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