[Journal logo]

Volume 68 
Part 1 
Page o141  
January 2012  

Received 1 December 2011
Accepted 12 December 2011
Online 17 December 2011

[hb6546sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.154
Data-to-parameter ratio = 18.3
Details
Open access

2-(7-Methyl-1H-indol-3-yl)acetonitrile

Yu-Hua Ge,a* Mei-Ling Pan,a Jian Xua and Yang-Hui Luoa

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: peluoyh@sina.com

In the title compound, C11H10N2, the carbonitrile group is twisted away from the indole plane [Ccy-Cme-Car-Car = 66.6 (2)°; cy = cyanide, me = methylene and ar = aromatic]. In the crystal, N-H...N hydrogen bonds link the molecules into C(7) chains propagating in the [001] direction.

Related literature

For background to indole derivatives as pharmaceuticals, see: Kunzer & Wendt (2011[Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.]).

[Scheme 1]

Experimental

Crystal data

  • C11H10N2

  • Mr = 170.21

  • Monoclinic, P 21 /c

  • a = 6.9962 (14) Å

  • b = 8.9445 (18) Å

  • c = 15.406 (3) Å

  • [beta] = 97.97 (3)°

  • V = 954.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.26 × 0.24 × 0.15 mm
Data collection

  • Rigaku SCXmini CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.989

  • 9402 measured reflections

  • 2160 independent reflections

  • 1418 reflections with I > 2[sigma](I)

  • Rint = 0.058
Refinement

  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.154

  • S = 1.05

  • 2160 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.86 2.24 3.022 (2) 151
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6546 ).

Acknowledgements

We thank Southeast University for support.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.  [ChemPort]
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o141  [ doi:10.1107/S1600536811053396 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.