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Volume 69 
Part 3 
Page o448  
March 2013  

Received 11 February 2013
Accepted 20 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.092
Data-to-parameter ratio = 14.1
Details
Open access

{[(1Z)-3-Chloro-1H-isoindol-1-ylidene]methyl}dimethylamine

aSchool of Chemistry and Material Science, Anhui Normal University, Wuhu, People's Republic of China
Correspondence e-mail: shine_zywang@yahoo.com.cn

The asymmetric unit of the title compound, C11H11ClN2, contains two almost-planar independent molecules: the isoindole and dimethylaminomethylene mean planes in the two molecules form dihedral angles of 5.45 (8) and 1.34 (8)°. The crystal packing exhibits no short intermolecular contacts, except for a relatively short Cl...Cl distance of 3.4907 (7) Å.

Related literature

For applications of related isoindole derivatives, see: Jiao et al. (2010[Jiao, L. J., Yu, C. J., Liu, M. M., Wu, Y. C., Cong, K. B., Meng, T., Wang, Y. Q. & Hao, E. H. (2010). J. Org. Chem. 75, 6035-6038.]). For details of the synthesis, see: von Doheneck et al. (1969[Doheneck, H. von, Reinhard, H., Deuhel, H. & Wolkenstein, D. (1969). Chem. Ber. 102, 1357-1362.]). For the crystal structure of the related compound 4,5,6,7-tetrafluoro-1-(N,N-dimethylaminomethylene)-1H-isoindole, see: Uno et al. (2007[Uno, H., Masuda, G., Tukiji, M., Nishioka, Y. & Iida, T. (2007). Tetrahedron Lett. 48, 7512-7515.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11ClN2

  • Mr = 206.67

  • Monoclinic, P 21 /c

  • a = 12.1588 (9) Å

  • b = 10.4087 (8) Å

  • c = 16.3165 (12) Å

  • [beta] = 92.720 (1)°

  • V = 2062.6 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.908, Tmax = 0.937

  • 14393 measured reflections

  • 3628 independent reflections

  • 3175 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.092

  • S = 1.02

  • 3628 reflections

  • 257 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5388 ).


Acknowledgements

This work was supported by the Research Culture Funds of Anhui Normal University (grant No. 160-721137).

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Doheneck, H. von, Reinhard, H., Deuhel, H. & Wolkenstein, D. (1969). Chem. Ber. 102, 1357-1362.
Jiao, L. J., Yu, C. J., Liu, M. M., Wu, Y. C., Cong, K. B., Meng, T., Wang, Y. Q. & Hao, E. H. (2010). J. Org. Chem. 75, 6035-6038.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Uno, H., Masuda, G., Tukiji, M., Nishioka, Y. & Iida, T. (2007). Tetrahedron Lett. 48, 7512-7515.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o448  [ doi:10.1107/S160053681300500X ]

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