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Volume 69 
Part 2 
Page o255  
February 2013  

Received 14 January 2013
Accepted 15 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.152
Data-to-parameter ratio = 13.4
Details
Open access

5,11-Dimethyl-6,12-dimethoxyindolo[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, C22H20N2O2, was prepared in a twofold Cadogan cyclization followed by double N-methylation. The crystal structure is characterized by a zigzag arrangement of centrosymmetric molecules. The indolocarbazole framework is essentially planar [maximum deviation = 0.028 (2) Å] and the methoxy groups are orthogonal to this plane [C-C-O-C torsion angle = -88.2 (2)°]. The lengths of the C-N bonds are nearly identical and all C-C bonds of the pyrrole subunit are significantly longer than the C-C bonds in the benzene rings.

Related literature

For the synthesis of 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.]); Peng et al. (2011[Peng, H., Chen, X., Chen, Y., He, Q., Xie, Y. & Yang, C. (2011). Tetrahedron, 67, 5725-5731.]). 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 the structure of N-unsubstituted indolocarbazole, see: Wrobel et al. (2013[Wrobel, N., Witulski, B., Schollmeyer, D. & Detert, H. (2013). Acta Cryst. E69, o116-o117.]). 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.]); Letessier & Detert (2012[Letessier, J. & Detert, H. (2012). Synthesis, 44, 290-296.]); Nissen & Detert (2011[Nissen, F. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2845-2854.]); 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
  • C22H20N2O2

  • Mr = 344.40

  • Monoclinic, P 21 /c

  • a = 11.229 (4) Å

  • b = 7.8561 (7) Å

  • c = 9.668 (3) Å

  • [beta] = 94.790 (17)°

  • V = 849.9 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.69 mm-1

  • T = 193 K

  • 0.30 × 0.30 × 0.18 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 1716 measured reflections

  • 1612 independent reflections

  • 1410 reflections with I > 2[sigma](I)

  • Rint = 0.029

  • 3 standard reflections every 60 min intensity decay: 4%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.152

  • S = 1.10

  • 1612 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.27 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: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6882 ).


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]
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]
Peng, H., Chen, X., Chen, Y., He, Q., Xie, Y. & Yang, C. (2011). Tetrahedron, 67, 5725-5731.  [ISI] [CrossRef] [ChemPort]
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]
Wrobel, N., Witulski, B., Schollmeyer, D. & Detert, H. (2013). Acta Cryst. E69, o116-o117.  [CrossRef] [details]


Acta Cryst (2013). E69, o255  [ doi:10.1107/S1600536813001463 ]

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