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Volume 68 
Part 1 
Page o203  
January 2012  

Received 4 December 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.048
wR = 0.111
Data-to-parameter ratio = 17.2
Details
Open access

2-(4-Chloro-1H-indol-3-yl)acetonitrile

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: nantongpml@163.com

The title compound, C10H7ClN2, contains two approximately planar molecules, A and B (r.m.s. deviations = 0.039 and 0.064 Å, respectively) in the asymmetric unit. In the crystal, N-H...N hydrogen bonds link the molecules into C(7) chains of alternating A and B molecules propagating along the a-axis direction. The crystal used for the data collection was found to be a racemic twin.

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

  • Orthorhombic, P c a 21

  • a = 7.5091 (15) Å

  • b = 11.041 (2) Å

  • c = 21.380 (4) Å

  • V = 1772.6 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 293 K

  • 0.33 × 0.25 × 0.20 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.893, Tmax = 0.927

  • 17075 measured reflections

  • 4057 independent reflections

  • 2753 reflections with I > 2[sigma](I)

  • Rint = 0.058

  • 2 standard reflections every 150 reflections intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.111

  • S = 1.03

  • 4057 reflections

  • 236 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1968 Friedel pairs

  • Flack parameter: 0.66 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N4 0.86 2.42 3.089 (6) 135
N2-H2A...N3i 0.86 2.21 3.058 (6) 170
Symmetry code: (i) [x-{\script{1\over 2}}, -y+2, z].

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: HB6554 ).


Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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, o203  [ doi:10.1107/S1600536811054079 ]

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