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

Ge, Y.-H.; Wu, D.-E.; Luo, Y.-H.

doi:10.1107/S1600536811054225

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.127
Data-to-parameter ratio = 13.2
Details

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

Yu-Hua Ge,^a ^* Dong-En Wu ^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, 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-HN [triple bond] C hydrogen bonds form zigzag chains in the a-axis direction augmented by weak C-HNC contacts.

Related literature

For indole derivatives as drug intermediates, see: Kunzer & Wendt (2011).

Experimental

Crystal data

C₁₇H₁₂N₂
M_r = 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 radiation
= 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) T_min = 0.985, T_max = 0.985
16536 measured reflections
2263 independent reflections
1867 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.127
S = 1.16
2263 reflections
172 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.90	2.19	3.043 (3)	158
C5-H5AN2ⁱⁱ	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); 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: GG2065 ).

References

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

organic compounds