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Volume 69 
Part 1 
Pages o116-o117  
January 2013  

Received 3 December 2012
Accepted 12 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.181
Data-to-parameter ratio = 14.1
Details
Open access

6,12-Bis(hexyloxy)-5H,11H-indolo[3,2-b]carbazole

aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany, and bLaboratoire de Chimie Moléculaire et Thio-organique, UMR 6507, ENSICAEN, 6 Boulevard Maréchal Juin, 14050 Caen, France
Correspondence e-mail: detert@uni-mainz.de

The title compound, C30H36N2O2, was prepared in a twofold Cadogan cyclization. The molecule is located about a center of inversion. The indolocarbazole skeleton is essentially planar [maximum deviation = 0.028 (2) Å], the C-N bond lengths are nearly identical and the C-C bond lengths of the pyrrole unit are significantly longer than those of the benzene subunits.

Related literature

For the synthesis and structure of the starting material, see: Wrobel et al. (2012[Wrobel, N., Schollmeyer, D. & Detert, H. (2012). Acta Cryst. E68, o1022.]). For the Cadogan reaction, see: Cadogan (1962[Cadogan, J. I. G. (1962). Q. Rev. 16, 208-239.], 1969[Cadogan, J. I. G. (1969). Synthesis, pp. 11-17.]). For other approaches to Indolocarbazoles, see: Knölker & Reddy (2002[Knölker, H.-J. & Reddy, K. R. (2002). Chem. Rev. 39, 6521-6527.]); Katritzky et al. (1995[Katritzky, A. R., Li, J. & Stevens, C. V. (1995). J. Org. Chem. 60, 3401-3404.]). For electronic properties of indolocarbazoles, see: Hu et al. (1999[Hu, N.-X., Xie, S., Popovic, Z., Ong, B. & Hor, A.-M. (1999). J. Am. Chem. Soc. 121, 5097-5098.]); Wakim et al. (2004[Wakim, S., Bouchard, J., Simard, M., Drolet, N., Tao, Y. & Leclerc, M. (2004). Chem. Mater. 16, 4386-4388.]); Nemkovich et al. (2009[Nemkovich, N. A., Kruchenok, Yu. V., Sobchuk, A. N., Detert, H., Wrobel, N. & Chernyavskii, E. A. (2009). Opt. Spectrosc. 107, 275-281.]). For heteroanalogous carbazoles, see: Dassonneville et al. (2011[Dassonneville, B., Witulski, B. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2836-2844.]); Nissen & Detert (2011[Nissen, F. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2845-2854.]); Letessier & Detert (2012[Letessier, J. & Detert, H. (2012). Synthesis, 44, 290-296.]); Letessier et al. (2012[Letessier, J., Detert, H., Götz, K. & Opatz, T. (2012). Synthesis, 44, 747-754.]). For conjugated oligomers see: Detert et al. (2010[Detert, H., Lehmann, M. & Meier, H. (2010). Materials, 3, 3218-3330.]).

[Scheme 1]

Experimental

Crystal data
  • C30H36N2O2

  • Mr = 456.61

  • Monoclinic, P 21 /c

  • a = 13.7136 (4) Å

  • b = 5.5026 (4) Å

  • c = 16.5563 (5) Å

  • [beta] = 92.665 (3)°

  • V = 1247.99 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 298 K

  • 0.48 × 0.26 × 0.18 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 2466 measured reflections

  • 2363 independent reflections

  • 1993 reflections with I > 2[sigma](I)

  • Rint = 0.052

  • 3 standard reflections every 60 min intensity decay: 5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.181

  • S = 1.06

  • 2363 reflections

  • 168 parameters

  • Only H-atom displacement parameters refined

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971[Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2301 ).


Acknowledgements

The authors are grateful to Heinz Kolshorn for helpful discussions.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Cadogan, J. I. G. (1962). Q. Rev. 16, 208-239.  [CrossRef] [ChemPort]
Cadogan, J. I. G. (1969). Synthesis, pp. 11-17.  [CrossRef]
Dassonneville, B., Witulski, B. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2836-2844.  [CSD] [CrossRef]
Detert, H., Lehmann, M. & Meier, H. (2010). Materials, 3, 3218-3330.  [CrossRef] [ChemPort]
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Hu, N.-X., Xie, S., Popovic, Z., Ong, B. & Hor, A.-M. (1999). J. Am. Chem. Soc. 121, 5097-5098.  [ISI] [CrossRef] [ChemPort]
Katritzky, A. R., Li, J. & Stevens, C. V. (1995). J. Org. Chem. 60, 3401-3404.  [CrossRef] [ChemPort]
Knölker, H.-J. & Reddy, K. R. (2002). Chem. Rev. 39, 6521-6527.
Letessier, J. & Detert, H. (2012). Synthesis, 44, 290-296.  [ChemPort]
Letessier, J., Detert, H., Götz, K. & Opatz, T. (2012). Synthesis, 44, 747-754.  [ChemPort]
Nemkovich, N. A., Kruchenok, Yu. V., Sobchuk, A. N., Detert, H., Wrobel, N. & Chernyavskii, E. A. (2009). Opt. Spectrosc. 107, 275-281.  [CrossRef] [ChemPort]
Nissen, F. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2845-2854.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wakim, S., Bouchard, J., Simard, M., Drolet, N., Tao, Y. & Leclerc, M. (2004). Chem. Mater. 16, 4386-4388.  [ISI] [CSD] [CrossRef] [ChemPort]
Wrobel, N., Schollmeyer, D. & Detert, H. (2012). Acta Cryst. E68, o1022.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o116-o117   [ doi:10.1107/S1600536812050611 ]

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