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Volume 69 
Part 11 
Page o1678  
November 2013  

Received 8 September 2013
Accepted 14 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.114
Data-to-parameter ratio = 14.1
Details
Open access

N,N,N'-Tris[(1H-indol-3-yl)meth­yl]ethane-1,2-di­amine

aWuhan University of Science and Technology, Hubei, Wuhan 430081, People's Republic of China
Correspondence e-mail: yanwatercn@wust.edu.cn

In the title mol­ecule, C29H29N5, the indole ring systems are essentially planar, with maximum deviations of 0.020 (2), 0.023 (2) and 0.016 (2) Å. The dihedral angles formed between the mean planes of the three indole ring systems are 38.08 (7), 89.64 (8) and 58.28 (8)°. In the crystal, mol­ecules are connected by N-H...N hydrogen bonds, forming inversion dimers. An intra­molecular N-H...N hydrogen bond is also observed.

Related literature

For applications of indole compounds and for related structures, see: Shimazaki et al.(2009[Shimazaki, Y., Yajima, T., Takani, M. & Yamauchi, O. (2009). Coord. Chem. Rev. 253, 479-492.]); Takani et al. (2006[Takani, M., Takeda, T., Yajima, T. & Yamauchi, O. (2006). Inorg. Chem. 45, 5938-5946.]); Munjal et al. (2010[Munjal, M. & Gupta, R. (2010). Inorg. Chim. Acta, 363, 2734-2742.]); Zhu et al. (2012[Zhu, X., Zhou, S., Wang, S., Wei, Y., Zhang, L., Wang, F., Wang, S. & Feng, Z. (2012). Chem. Commun. 48. 12020-12022.]).

[Scheme 1]

Experimental

Crystal data
  • C29H29N5

  • Mr = 447.57

  • Monoclinic, P 21 /c

  • a = 13.769 (3) Å

  • b = 10.832 (2) Å

  • c = 16.910 (3) Å

  • [beta] = 106.512 (3)°

  • V = 2418.2 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 298 K

  • 0.16 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.988, Tmax = 0.993

  • 12582 measured reflections

  • 4486 independent reflections

  • 2785 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.114

  • S = 0.99

  • 4486 reflections

  • 319 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...N2i 0.92 (2) 2.03 (2) 2.953 (3) 176 (2)
N2-H2...N1 0.83 (2) 2.45 (2) 2.889 (2) 114 (2)
Symmetry code: (i) -x, -y, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: 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: LH5652 ).


Acknowledgements

This work was supported by the Wuhan University of Science and Technology.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Munjal, M. & Gupta, R. (2010). Inorg. Chim. Acta, 363, 2734-2742.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shimazaki, Y., Yajima, T., Takani, M. & Yamauchi, O. (2009). Coord. Chem. Rev. 253, 479-492.  [Web of Science] [CrossRef] [ChemPort]
Takani, M., Takeda, T., Yajima, T. & Yamauchi, O. (2006). Inorg. Chem. 45, 5938-5946.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhu, X., Zhou, S., Wang, S., Wei, Y., Zhang, L., Wang, F., Wang, S. & Feng, Z. (2012). Chem. Commun. 48. 12020-12022.


Acta Cryst (2013). E69, o1678  [ doi:10.1107/S1600536813028225 ]

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