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

Tuncer, H.; Görgülü, A.O.; Hökelek, T.

doi:10.1107/S1600536811053669

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 (C-C) = 0.004 Å
R = 0.048
wR = 0.141
Data-to-parameter ratio = 17.0
Details

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

Hülya Tuncer,^a Ahmet Orhan Görgülü ^a and Tuncer Hökelek ^b ^*

^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-HO and C-HN 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). For the fundamental optical and electronic properties of phthalocyanines and their applications, see: McKeown (1998). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₈N₂O₂
M_r = 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 radiation
= 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) T_min = 0.986, T_max = 0.994
6208 measured reflections
2615 independent reflections
1709 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.141
S = 1.06
2615 reflections
154 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7N1ⁱ	0.95	2.45	3.369 (4)	162
C10-H10O2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds