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Volume 68 
Part 1 
Page o222  
January 2012  

Received 12 December 2011
Accepted 19 December 2011
Online 23 December 2011

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.118
Data-to-parameter ratio = 14.1
Details
Open access

4-(2,2-Difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile

Fan-Wei Meng,a Guang-Feng Hou,a Ying-Hui Yua and Jin-Sheng Gaoa*

aEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China, and College of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hgf1000@163.com

In the title compound, C12H6F2N2O2, the 2,2-difluoro-1,3-benzodioxole ring system is approximately planar [maximum deviation = 0.012 (2) Å] and its mean plane is twisted with respect to the pyrrole ring, making a dihedral angle of 2.51 (9)°. In the crystal, N-H...N hydrogen bonds link the molecules into chains running along the a axis. [pi]-[pi] stacking is also observed between parallel benzene rings of adjacent molecules, the centroid-centroid distance being 3.7527 (13) Å.

Related literature

For background to the title compound, see: Li et al. (2009[Li, C., Miu, H.-D., Zeng, Z.-W., Wang, M.-J., Wu, Z.-X., Yang, F. & Shi, W.-J. (2009). Modern Agrochem. 8, 19-24.]); Pfluger et al. (1990[Pfluger, R. W., Indermühle, J. & Felix, F. (1990). Switzerland Patent No. EP0378046. ]). For the synthesis, see: Nyfeler & Ehrenfreund (1986[Nyfeler, R. & Ehrenfreund, J. (1986). Switzerland Patent No. EP0206999.]).

[Scheme 1]

Experimental

Crystal data

  • C12H6F2N2O2

  • Mr = 248.19

  • Triclinic, [P \overline 1]

  • a = 7.5726 (15) Å

  • b = 7.8114 (16) Å

  • c = 8.9785 (18) Å

  • [alpha] = 93.58 (3)°

  • [beta] = 94.65 (3)°

  • [gamma] = 97.47 (3)°

  • V = 523.42 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.39 × 0.32 × 0.15 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.950, Tmax = 0.980

  • 5120 measured reflections

  • 2359 independent reflections

  • 1485 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.118

  • S = 1.04

  • 2359 reflections

  • 167 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H101...N2i 0.89 (1) 2.15 (1) 3.034 (2) 169 (2)
Symmetry code: (i) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5407 ).

Acknowledgements

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University, China, for supporting the work.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Li, C., Miu, H.-D., Zeng, Z.-W., Wang, M.-J., Wu, Z.-X., Yang, F. & Shi, W.-J. (2009). Modern Agrochem. 8, 19-24.  [ChemPort]
Nyfeler, R. & Ehrenfreund, J. (1986). Switzerland Patent No. EP0206999.
Pfluger, R. W., Indermühle, J. & Felix, F. (1990). Switzerland Patent No. EP0378046.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o222  [ doi:10.1107/S1600536811054523 ]

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