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Volume 69 
Part 12 
Page o1745  
December 2013  

Received 4 October 2013
Accepted 28 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.110
Data-to-parameter ratio = 13.0
Details
Open access

Ethyl N-(3-cyano-1H-indol-2-yl)form­imidate

aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China
Correspondence e-mail: ouyangruchun@aliyun.com

In the title compound, C12H11N3O, the C=N imino bond is in an E conformation. In the crystal, adjacent mol­ecules are linked by N-H...Ncyano hydrogen bonds, forming a chain running along [110].

Related literature

The starting reactant was synthesized according to a literature method (Yang et al., 2010[Yang, X. B., Fu, H., Qiao, R. Z., Jiang, Y. Y. & Zhao, Y. F. (2010). Adv. Synth. Catal. 352, 1033-1038.]). Introduction of different groups into indole mol­ecules can generate a series of bioactive derivatives, which have been the subject of much attention as anti-cancer drugs (Laird et al., 2000[Laird, D., Vajkoczy, P., Shawver, L. K., Thurnher, A., Liang, C. X. & Mohammadi, M. (2000). Cancer Res. 60, 4152-4160.]; Li et al., 2005[Li, P.-K., Xiao, Z., Hu, Z., Pandit, B., Sun, Y., Sacket, D. L., Werbovetz, K., Lewis, A. & Johnsamuel, J. (2005). Bioorg. Med. Chem. Lett. 15, 5382-5385.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11N3O

  • Mr = 213.24

  • Monoclinic, C 2/c

  • a = 12.7884 (6) Å

  • b = 8.0546 (6) Å

  • c = 21.4116 (10) Å

  • [beta] = 94.069 (4)°

  • V = 2200.0 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.997, Tmax = 0.998

  • 14358 measured reflections

  • 1934 independent reflections

  • 1579 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.110

  • S = 1.12

  • 1934 reflections

  • 149 parameters

  • 379 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.87 (2) 2.12 (2) 2.9490 (19) 161 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5344 ).


Acknowledgements

This work was supported by the Science Fund of the Education Office of Jiangxi (GJJ12583) and the Bureau of Science and Technology of Nanchang City.

References

Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Laird, D., Vajkoczy, P., Shawver, L. K., Thurnher, A., Liang, C. X. & Mohammadi, M. (2000). Cancer Res. 60, 4152-4160.  [Web of Science] [PubMed] [ChemPort]
Li, P.-K., Xiao, Z., Hu, Z., Pandit, B., Sun, Y., Sacket, D. L., Werbovetz, K., Lewis, A. & Johnsamuel, J. (2005). Bioorg. Med. Chem. Lett. 15, 5382-5385.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Yang, X. B., Fu, H., Qiao, R. Z., Jiang, Y. Y. & Zhao, Y. F. (2010). Adv. Synth. Catal. 352, 1033-1038.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1745  [ doi:10.1107/S1600536813029589 ]

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