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Volume 68 
Part 1 
Page o207  
January 2012  

Received 5 November 2011
Accepted 16 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.127
Data-to-parameter ratio = 13.2
Details
Open access

3-[(E)-2-Phenylethenyl]-1H-indole-6-carbonitrile

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, C17H12N2, the interplanar angle between the indole mean plane [max.deviation 0.030 (1) Å] and the phenyl ring is 24.32 (7)°. In the crystal, intermolecular N-H...N[triple bond]C hydrogen bonds form zigzag chains in the a-axis direction augmented by weak C-H...N[triple bond]C contacts.

Related literature

For indole derivatives as drug intermediates, see: Kunzer & Wendt (2011[Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12N2

  • Mr = 244.29

  • Orthorhombic, P b c a

  • a = 9.689 (8) Å

  • b = 7.440 (6) Å

  • c = 35.53 (3) Å

  • V = 2561 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 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 = 0.985, Tmax = 0.985

  • 16536 measured reflections

  • 2263 independent reflections

  • 1867 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.127

  • S = 1.16

  • 2263 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.90 2.19 3.043 (3) 158
C5-H5A...N2ii 0.93 2.66 3.416 (4) 138
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (ii) -x, -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: GG2065 ).


References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.  [ChemPort]
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o207  [ doi:10.1107/S1600536811054225 ]

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