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Volume 68 
Part 1 
Page o73  
January 2012  

Received 7 November 2011
Accepted 1 December 2011
Online 10 December 2011

[zs2163sup1]
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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 12.7
Details
Open access

6-[(E)-2-Phenylvinyl]-1H-indole

Yu-Hua Ge,a* Chen-Guang Zhanga and Yang-Hui Luoa

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

The title compound, C16H13N, is essentially planar [maximum deviation from the least-squares plane = 0.081 (3) Å], with a dihedral angle of 1.65 (13)° between the planes of the indole and benzene rings. In the crystal, there are no significant intermolecular [pi]-[pi] interactions [minimum ring centroid-centroid separation = 4.217 (5) Å].

Related literature

For background information on 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

  • C16H13N

  • Mr = 219.29

  • Orthorhombic, P n a 21

  • a = 8.254 (8) Å

  • b = 5.626 (6) Å

  • c = 25.74 (3) Å

  • V = 1195 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.10 mm
Data collection

  • Rigaku SCXmini CCD-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.993

  • 7653 measured reflections

  • 1954 independent reflections

  • 1627 reflections with I > 2[sigma](I)

  • Rint = 0.022
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.132

  • S = 1.08

  • 1954 reflections

  • 154 parameters

  • 19 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2163 ).

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]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2012). E68, o73  [ doi:10.1107/S1600536811051750 ]

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