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Volume 68 
Part 1 
Page o66  
January 2012  

Received 5 November 2011
Accepted 1 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.064
wR = 0.162
Data-to-parameter ratio = 17.0
Details
Open access

(5-Methoxy-1H-indol-3-yl)acetonitrile

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, C11H10N2O, the O atom and the C atom of the methylene group deviate only slightly [0.029 (3) and 0.055 (3) Å, respectively] from the approximately planar ring system (r.m.s. deviation = 0.013 Å). In the crystal, N-H...O hydrogen bonds link the molecules into zigzag chains running along the b axis.

Related literature

Indole-3-acetic acid is recognized as the key auxin in most plants, see: see: Woodward & Bartel (2005[Woodward, A. W. & Bartel, B. (2005). Ann. Bot. 95, 707-735.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N2O

  • Mr = 186.21

  • Monoclinic, P 21 /n

  • a = 8.9242 (18) Å

  • b = 11.461 (2) Å

  • c = 9.889 (2) Å

  • [beta] = 110.77 (3)°

  • V = 945.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.983, Tmax = 0.983

  • 9617 measured reflections

  • 2164 independent reflections

  • 1225 reflections with I > 2[sigma](I)

  • Rint = 0.085

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.162

  • S = 1.01

  • 2164 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.18 3.038 (3) 175
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\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: BT5708 ).


References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Woodward, A. W. & Bartel, B. (2005). Ann. Bot. 95, 707-735.  [PubMed] [ChemPort]


Acta Cryst (2012). E68, o66  [ doi:10.1107/S1600536811051762 ]

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