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Volume 68 
Part 1 
Page o144  
January 2012  

Received 5 December 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.110
wR = 0.312
Data-to-parameter ratio = 18.0
Details
Open access

2-(6-Chloro-1H-indol-3-yl)acetonitrile

aKey Laboratory of Urban and Architectural Heritage Conservation, (Southeast University), Ministry of Education, Nanjing 210096, People's Republic of China, and, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: chmsunbw@seu.edu.cn

In the title compound, C10H7ClN2, the carbonitrile group is twisted away from the plane of the indole ring system [Ccy-Cme-Car-Car = -44.7 (8)°; cy = cyanide, me = methylene and ar = aromatic]. In the crystal, N-H...N hydrogen bonds link the molecules into C(7) chains propagating in [010]. Aromatic [pi]-[pi] stacking interactions [minimum centroid-centroid separation = 3.663 (3) Å] are also observed.

Related literature

For a related structure, see: Ge et al. (2012[Ge, Y.-H., Pan, M.-L., Xu, J. & Luo, Y.-H. (2012). Acta Cryst. E68, o141.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7ClN2

  • Mr = 190.63

  • Monoclinic, P 21 /c

  • a = 9.761 (2) Å

  • b = 11.205 (2) Å

  • c = 8.7791 (18) Å

  • [beta] = 100.39 (3)°

  • V = 944.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 293 K

  • 0.20 × 0.12 × 0.10 mm

Data collection
  • Rigaku SCXmini CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.950, Tmax = 0.965

  • 8938 measured reflections

  • 2122 independent reflections

  • 1247 reflections with I > 2[sigma](I)

  • Rint = 0.134

Refinement
  • R[F2 > 2[sigma](F2)] = 0.110

  • wR(F2) = 0.312

  • S = 1.05

  • 2122 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H4A...N1i 0.86 2.23 3.016 (6) 151
Symmetry code: (i) [-x+2, y-{\script{1\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: HB6557 ).


Acknowledgements

We thank Southeast University for support.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Ge, Y.-H., Pan, M.-L., Xu, J. & Luo, Y.-H. (2012). Acta Cryst. E68, o141.  [CrossRef] [details]
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o144  [ doi:10.1107/S1600536811053372 ]

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