2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide

Helliwell, M.; Baradarani, M.M.; Alyari, M.; Afghan, A.; Joule, J.A.

doi:10.1107/S1600536811053918

Volume 68
Part 1
Page o234
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) = 0.006 Å
R = 0.065
wR = 0.132
Data-to-parameter ratio = 12.8
Details

2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)-2-cyanoacetamide

Madeleine Helliwell,^a Mehdi M. Baradarani,^b ^* Maryam Alyari,^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

Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)propanedial with hydroxylamine gives the title compound, C₁₄H₁₄ClN₃O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyanoacrylamide unit. The orientation of the acetamide group arises from intramolecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-HO hydrogen-bonded dimers in graph-set R₂²(8) motifs, whilst dimers are also formed by pairs of amine-nitrile N-HN hydrogen bonds in R₂²(12) motifs. These interactions together generate ribbons that propagate along the b-axis direction.

Related literature

For background information on the chemistry of related compounds, see: Baradarani et al. (2006); Rashidi et al. (2009, 2011). For related structures, see: Helliwell et al. (2010, 2012). For graph-set notation, see: Etter et al. (1990).

Experimental

Crystal data

C₁₄H₁₄ClN₃O
M_r = 275.73
Triclinic, $[P \overline 1]$
a = 8.226 (2) Å
b = 9.282 (3) Å
c = 9.744 (3) Å
= 92.124 (5)°
= 104.766 (5)°
= 105.294 (4)°
V = 689.5 (3) Å³
Z = 2
Mo K radiation
= 0.27 mm^-1
T = 100 K
0.58 × 0.22 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
3384 measured reflections
2389 independent reflections
1549 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.132
S = 1.01
2389 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.45 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1	0.93 (5)	1.89 (5)	2.610 (4)	132 (4)
N3-H3MO1ⁱ	0.83 (5)	2.11 (5)	2.931 (5)	176 (5)
N3-H3NN2ⁱⁱ	0.85 (4)	2.24 (4)	3.065 (5)	163 (3)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -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: XP in 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: PK2373 ).

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.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Helliwell, M., Afghan, A., Keshvari, F., Baradarani, M. M. & Joule, J. A. (2010). Acta Cryst. E66, o112.
Helliwell, M., Baradarani, M. M., Mohammadnejadaghdam, R., Afghan, A., & Joule, J. A. (2012). Acta Cryst. E68, o233.
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