5,11-Dimethyl-6,12-dimeth­oxy­indolo[3,2-b]carbazole

Wrobel, N.; Witulski, B.; Schollmeyer, D.; Detert, H.

doi:10.1107/S1600536813001463

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 (C-C) = 0.003 Å
R = 0.049
wR = 0.152
Data-to-parameter ratio = 13.4
Details

5,11-Dimethyl-6,12-dimethoxyindolo[3,2-b]carbazole

Norma Wrobel,^a Bernhard Witulski,^b Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^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). For the Cadogan reaction, see: Cadogan (1962); Peng et al. (2011). For other approaches to indolocarbazoles, see: Knölker & Reddy (2002); Katritzky et al. (1995). For the structure of N-unsubstituted indolocarbazole, see: Wrobel et al. (2013). For electronic properties of indolocarbazoles, see: Hu et al. (1999); Wakim et al. (2004); Nemkovich et al. (2009). For heteroanalogous carbazoles, see: Dassonneville et al. (2011); Letessier & Detert (2012); Nissen & Detert (2011); Letessier et al. (2012). For conjugated oligomers, see: Detert et al. (2010).

Experimental

Crystal data

C₂₂H₂₀N₂O₂
M_r = 344.40
Monoclinic, P 2₁ /c
a = 11.229 (4) Å
b = 7.8561 (7) Å
c = 9.668 (3) Å
= 94.790 (17)°
V = 849.9 (4) Å³
Z = 2
Cu K radiation
= 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(I)
R_int = 0.029
3 standard reflections every 60 min intensity decay: 4%

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.152
S = 1.10
1612 reflections
120 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.27 e Å^-3

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
Cadogan, J. I. G. (1962). Q. Rev. 16, 208-239.
Dassonneville, B., Witulski, B. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2836-2844.
Detert, H., Lehmann, M. & Meier, H. (2010). Materials, 3, 3218-3330.
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.
Katritzky, A. R., Li, J. & Stevens, C. V. (1995). J. Org. Chem. 60, 3401-3404.
Knölker, H.-J. & Reddy, K. R. (2002). Chem. Rev. 39, 6521-6527.
Letessier, J. & Detert, H. (2012). Synthesis, 44, 290-296.
Letessier, J., Detert, H., Götz, K. & Opatz, T. (2012). Synthesis, 44, 747-754.
Nemkovich, N. A., Kruchenok, Yu. V., Sobchuk, A. N., Detert, H., Wrobel, N. & Chernyavskii, E. A. (2009). Opt. Spectrosc. 107, 275-281.
Nissen, F. & Detert, H. (2011). Eur. J. Org. Chem. pp. 2845-2854.
Peng, H., Chen, X., Chen, Y., He, Q., Xie, Y. & Yang, C. (2011). Tetrahedron, 67, 5725-5731.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wakim, S., Bouchard, J., Simard, M., Drolet, N., Tao, Y. & Leclerc, M. (2004). Chem. Mater. 16, 4386-4388.
Wrobel, N., Schollmeyer, D. & Detert, H. (2012). Acta Cryst. E68, o1022.
Wrobel, N., Witulski, B., Schollmeyer, D. & Detert, H. (2013). Acta Cryst. E69, o116-o117.

organic compounds