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Volume 69 
Part 6 
Pages o921-o922  
June 2013  

Received 29 April 2013
Accepted 8 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.038
wR = 0.039
Data-to-parameter ratio = 12.9
Details
Open access

1-Ethyl-2-phenyl-3-[2-(trimethylsilyl)ethynyl]-1H-indole

aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska 64, 01033 Kyiv, Ukraine,bCNRS, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, F-31077 Toulouse, France, and cUniversite de Toulouse, UPS, INPT, LCC, F-31077 Toulouse, France
Correspondence e-mail: iaroslav.baglai@gmail.com

The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with trimethylsilylacetylene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C-H...[pi] interactions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the trimethylsilyl unit are equally disordered over two sets of sites.

Related literature

For background to indoles, see: Huang et al. (2004[Huang, X.-H., Zhang, Q.-F. & Sung, H. H. Y. (2004). Acta Cryst. E60, o488-o489.]); Seferoglu et al. (2007a[Seferoglu, Z., Hökelek, T., Sahin, E. & Ertan, N. (2007a). Acta Cryst. E63, o148-o150.],b[Seferoglu, Z., Hökelek, T., Sahin, E. & Ertan, N. (2007b). Acta Cryst. E63, o568-o570.]). For the synthesis and properties of indoles, see: Ruiz et al. (2012[Ruiz, M., Sánchez, J. D., López-Alvarado, P. & Menéndez, J. C. (2012). Tetrahedron, 68, 705-710.]); Shiri (2012[Shiri, M. (2012). Chem. Rev. 112, 3508-3549.]); Hussain et al. (2011[Hussain, M., Tengho Toguem, S.-M., Ahmad, R., Tùng, Đ. T., Knepper, I., Villinger, A. & Langer, P. (2011). Tetrahedron, 67, 5304-5318.]); Prateeptongkum et al. (2010[Prateeptongkum, S., Driller, K. M., Jackstell, R., Spannenberg, A. & Beller, M. (2010). Chem. Eur. J. 16, 9606-9615.]); Rives et al. (2012[Rives, A., Baglai, I., Malytskyi, V., Maraval, V., Saffon-Merceron, N., Voitenko, Z. & Chauvin, R. (2012). Chem. Commun. 48, 8763-8765.]).

[Scheme 1]

Experimental

Crystal data
  • C21H23NSi

  • Mr = 317.51

  • Monoclinic, P 21 /n

  • a = 12.6271 (6) Å

  • b = 9.3928 (5) Å

  • c = 16.6616 (8) Å

  • [beta] = 111.954 (2)°

  • V = 1832.83 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 100 K

  • 0.20 × 0.20 × 0.06 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.90, Tmax = 0.99

  • 26426 measured reflections

  • 4320 independent reflections

  • 3254 reflections with I > 2.0[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.039

  • S = 1.12

  • 3032 reflections

  • 235 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the pyrrole and benzene rings, respectively, of indole ring system.

D-H...A D-H H...A D...A D-H...A
C10-H102...Cg5i 0.98 2.66 3.3512 (18) 128
C16-H161...Cg5ii 0.95 2.79 3.5122 (17) 133
C17-H171...Cg4ii 0.95 2.81 3.4515 (17) 125
Symmetry codes: (i) [-x+{\script{5\over 2}}, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{5\over 2}}, y+{\script{5\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. 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: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5700 ).


Acknowledgements

The authors would like to thank Professor Z. V. Voitenko and Professor Yu. M. Volovenko for helpful discussions.

References

Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [ISI] [CrossRef] [details]
Bruker (2001). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.
Huang, X.-H., Zhang, Q.-F. & Sung, H. H. Y. (2004). Acta Cryst. E60, o488-o489.  [CSD] [CrossRef] [ChemPort] [details]
Hussain, M., Tengho Toguem, S.-M., Ahmad, R., Tùng, Đ. T., Knepper, I., Villinger, A. & Langer, P. (2011). Tetrahedron, 67, 5304-5318.  [ISI] [CrossRef] [ChemPort]
Prateeptongkum, S., Driller, K. M., Jackstell, R., Spannenberg, A. & Beller, M. (2010). Chem. Eur. J. 16, 9606-9615.  [CSD] [CrossRef] [ChemPort] [PubMed]
Rives, A., Baglai, I., Malytskyi, V., Maraval, V., Saffon-Merceron, N., Voitenko, Z. & Chauvin, R. (2012). Chem. Commun. 48, 8763-8765.  [CSD] [CrossRef] [ChemPort]
Ruiz, M., Sánchez, J. D., López-Alvarado, P. & Menéndez, J. C. (2012). Tetrahedron, 68, 705-710.  [ISI] [CrossRef] [ChemPort]
Seferoglu, Z., Hökelek, T., Sahin, E. & Ertan, N. (2007a). Acta Cryst. E63, o148-o150.  [CSD] [CrossRef] [details]
Seferoglu, Z., Hökelek, T., Sahin, E. & Ertan, N. (2007b). Acta Cryst. E63, o568-o570.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shiri, M. (2012). Chem. Rev. 112, 3508-3549.  [ISI] [CrossRef] [ChemPort] [PubMed]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.


Acta Cryst (2013). E69, o921-o922   [ doi:10.1107/S1600536813012671 ]

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