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

Helliwell, M.; Baradarani, M.M.; Mohammadnejadaghdam, R.; Afghan, A.; Joule, J.A.

doi:10.1107/S1600536811053906

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 (C-C) = 0.003 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 13.4
Details

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

Madeleine Helliwell,^a Mehdi M. Baradarani,^b ^* Razieh Mohammadnejadaghdam,^b Arash Afghan ^c and John A. Joule ^a

^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-HO and C-HCl interactions occur. The geometry of the exocyclic double bond is Z. In the crystal, weak C-HN hydrogen bonds link the molecules into chains along [1 $[\overline1]$ 0].

Related literature

For related structures, see: Baradarani et al. (2006); Helliwell et al. (2010) Rashidi et al. (2009). For the chemistry of complexes of (2H-indol-2-ylidene)propanedials, see: Rashidi et al. (2011).

Experimental

Crystal data

C₁₃H₁₀Cl₂N₂O
M_r = 281.13
Triclinic, $[P \overline 1]$
a = 7.0535 (8) Å
b = 7.9455 (10) Å
c = 12.2883 (15) Å
= 105.151 (2)°
= 104.855 (2)°
= 95.296 (2)°
V = 633.09 (13) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.724, T_max = 1.000
3237 measured reflections
2268 independent reflections
2028 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(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
_max = 0.37 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N2ⁱ	0.93	2.56	3.256 (3)	132
C10-H10BCl2	0.96	2.83	3.473 (2)	125
N1-H1NO1	0.88 (3)	2.02 (3)	2.678 (3)	131 (2)
Symmetry code: (i) x+1, y-1, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
Rashidi, A., Afghan, A., Baradarani, M. M. & Joule, J. A. (2009). J. Heterocycl. Chem. 46, 428-431.
Rashidi, A., Baradarani, M. M. & Joule, J. A. (2011). Arkivoc, ii, 252-259.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds