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

Ge, Y.-H.; Li, J.-F.; Luo, Y.-H.

doi:10.1107/S1600536811051762

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 (C-C) = 0.003 Å
R = 0.064
wR = 0.162
Data-to-parameter ratio = 17.0
Details

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

Yu-Hua Ge,^a ^* Jin-Feng Li ^a and Yang-Hui Luo ^a

^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-HO 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).

Experimental

Crystal data

C₁₁H₁₀N₂O
M_r = 186.21
Monoclinic, P 2₁ /n
a = 8.9242 (18) Å
b = 11.461 (2) Å
c = 9.889 (2) Å
= 110.77 (3)°
V = 945.7 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.983, T_max = 0.983
9617 measured reflections
2164 independent reflections
1225 reflections with I > 2(I)
R_int = 0.085

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.162
S = 1.01
2164 reflections
127 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	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); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); 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.
Woodward, A. W. & Bartel, B. (2005). Ann. Bot. 95, 707-735.

organic compounds