2-(1H-indol-3-ylcarbon­yl)acetonitrile

Ramesh, P.; Subbiahpandi, A.; Thirumurugan, P.; Perumal, P.T.; Ponnuswamy, M.N.

doi:10.1107/S1600536809001342

Volume 65
Part 3
Page o447
March 2009

Received 17 December 2008
Accepted 12 January 2009
Online 4 February 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 12.9
Details

2-(1H-indol-3-ylcarbonyl)acetonitrile

P. Ramesh,^a A. Subbiahpandi,^a P. Thirumurugan,^b Paramasivan T. Perumal ^b and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: mnpsy2004@yahoo.com

The title compound, C₁₁H₈N₂O, crystallizes with two crystallographically independent molecules in the asymmetric unit which are approximately perpendicular to each other [79.97 (6)°]. The indole ring system is planar [r.m.s. deviation = 0.010 (1) Å]. The crystal structure is stabilized by intermolecular C-HN and N-HO interactions.

Related literature

For the use of indole derivatives as bioactive drugs, see: Stevenson et al. (2000). For their biological properties, see: Harris & Uhle (1960); Ho et al. (1986). For their high aldose reductase inhibitory activity, see: Rajeswaran et al. (1999). For a related structure, see: Ramesh et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₈N₂O
M_r = 184.19
Triclinic, $[P \overline 1]$
a = 7.3439 (2) Å
b = 7.3534 (2) Å
c = 18.2475 (5) Å
= 83.402 (2)°
= 78.890 (2)°
= 73.501 (1)°
V = 925.23 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.974, T_max = 0.983
18838 measured reflections
3253 independent reflections
2717 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.100
S = 1.06
3253 reflections
253 parameters
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	1.98	2.8146 (18)	163
C2-H2N13ⁱ	0.93	2.59	3.236 (2)	127
N1'-H1'O1'ⁱⁱ	0.86	2.00	2.8166 (15)	158
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2839 ).

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harris, L. S. & Uhle, F. C. (1960). J. Pharmacol. Exp. Ther. 128, 353-363.
Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118-121.
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369-1371.
Ramesh, P., Subbiahpandi, A., Thirumurugan, P., Perumal, P. T. & Ponnuswamy, M. N. (2008). Acta Cryst. E64, o1892.
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stevenson, G. I., Smith, A. L., Lewis, S. G., Neduvelil, J. G., Patel, S., Marwood, R. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697-2704.

organic compounds