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

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

doi:10.1107/S1600536812050611

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.181
Data-to-parameter ratio = 14.1
Details

6,12-Bis(hexyloxy)-5H,11H-indolo[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, 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). For the Cadogan reaction, see: Cadogan (1962, 1969). For other approaches to Indolocarbazoles, see: Knölker & Reddy (2002); Katritzky et al. (1995). 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); Nissen & Detert (2011); Letessier & Detert (2012); Letessier et al. (2012). For conjugated oligomers see: Detert et al. (2010).

Experimental

Crystal data

C₃₀H₃₆N₂O₂
M_r = 456.61
Monoclinic, P 2₁ /c
a = 13.7136 (4) Å
b = 5.5026 (4) Å
c = 16.5563 (5) Å
= 92.665 (3)°
V = 1247.99 (10) Å³
Z = 2
Cu K radiation
= 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(I)
R_int = 0.052
3 standard reflections every 60 min intensity decay: 5%

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.181
S = 1.06
2363 reflections
168 parameters
Only H-atom displacement parameters refined
_max = 0.26 e Å^-3
_min = -0.29 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: 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

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organic compounds