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Volume 68 
Part 1 
Page o233  
January 2012  

Received 29 November 2011
Accepted 14 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 13.4
Details
Open access

2-[(Z)-4,7-Dichloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene]-3-oxopropanenitrile

aThe School of Chemistry, The University of Manchester, Manchester M13 9PL, England,bDepartment of Chemistry, Faculty of Science, University of Urmia, Urmia 57153-165, Iran, and cDepartment of Chemical Engineering, University of Urmia, Urmia 57153-165, Iran
Correspondence e-mail: mmbaradarani@yahoo.com

In the title compound, C13H10Cl2N2O, the ring N atom and its three attached atoms are essentially coplanar with angles adding to 359.8°, indicating conjugation with the 2-formylacrylonitrile subunit. The aldehyde group is oriented to place the carbonyl O atom 2.02 (3) Å from the N-H hydrogen atom. Intramolecular N-H...O and C-H...Cl interactions occur. The geometry of the exocyclic double bond is Z. In the crystal, weak C-H...N hydrogen bonds link the molecules into chains along [1[\overline1]0].

Related literature

For related structures, see: Baradarani et al. (2006[Baradarani, M. M., Afghan, A., Zebarjadi, F., Hasanzadeh, K. & Joule, J. A. (2006). J. Heterocycl. Chem. 43, 1591-1596.]); Helliwell et al. (2010[Helliwell, M., Afghan, A., Keshvari, F., Baradarani, M. M. & Joule, J. A. (2010). Acta Cryst. E66, o112.]) Rashidi et al. (2009[Rashidi, A., Afghan, A., Baradarani, M. M. & Joule, J. A. (2009). J. Heterocycl. Chem. 46, 428-431.]). For the chemistry of complexes of (2H-indol-2-ylidene)propanedials, see: Rashidi et al. (2011[Rashidi, A., Baradarani, M. M. & Joule, J. A. (2011). Arkivoc, ii, 252-259.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10Cl2N2O

  • Mr = 281.13

  • Triclinic, [P \overline 1]

  • a = 7.0535 (8) Å

  • b = 7.9455 (10) Å

  • c = 12.2883 (15) Å

  • [alpha] = 105.151 (2)°

  • [beta] = 104.855 (2)°

  • [gamma] = 95.296 (2)°

  • V = 633.09 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 100 K

  • 0.60 × 0.60 × 0.40 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.724, Tmax = 1.000

  • 3237 measured reflections

  • 2268 independent reflections

  • 2028 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.127

  • S = 1.05

  • 2268 reflections

  • 169 parameters

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

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N2i 0.93 2.56 3.256 (3) 132
C10-H10B...Cl2 0.96 2.83 3.473 (2) 125
N1-H1N...O1 0.88 (3) 2.02 (3) 2.678 (3) 131 (2)
Symmetry code: (i) x+1, y-1, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT. 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: ZQ2144 ).


Acknowledgements

The authors are grateful to the University of Urmia for financial support of this work.

References

Baradarani, M. M., Afghan, A., Zebarjadi, F., Hasanzadeh, K. & Joule, J. A. (2006). J. Heterocycl. Chem. 43, 1591-1596.  [CrossRef] [ChemPort]
Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Helliwell, M., Afghan, A., Keshvari, F., Baradarani, M. M. & Joule, J. A. (2010). Acta Cryst. E66, o112.  [CrossRef] [details]
Rashidi, A., Afghan, A., Baradarani, M. M. & Joule, J. A. (2009). J. Heterocycl. Chem. 46, 428-431.  [CrossRef] [ChemPort]
Rashidi, A., Baradarani, M. M. & Joule, J. A. (2011). Arkivoc, ii, 252-259.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o233  [ doi:10.1107/S1600536811053906 ]

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