Received 21 May 2013
In the title compound, C35H32N4, the C-N bond lengths in the guanidine part are 1.286 (3), 1.387 (2) and 1.414 (2) Å, indicating double- and single-bond character. The N-C-N angles are 114.48 (17), 118.78 (17) and 126.72 (17)°, showing a deviation of the CN3 plane from an ideal trigonal-planar geometry. The carbazole ring system is almost planar (r.m.s. deviation = 0.002 Å). In the crystal, molecules are connected by weak C-HN hydrogen bonds, generating a zigzag chain along the ac plane. Weak - interactions [centroid-centroid distance = 3.785 (1) Å] between two phenyl rings of the guanidine moiety are also present.
For synthesis and characterization of carbazole-based compounds for blue OLEDs, see: Agarwal et al. (2011). For the crystal structure of 9-(4-nitrophenyl)-9H-carbazole, see: Chen et al. (2005). For the crystal structure of carbazole, see: Gerkin & Reppart (1986). For synthesis and characterization of light-emitting carbazole derivatives, see: Thomas et al. (2001). For the crystal structure of N,N,N',N'-tetramethyl-N''-[2-(N',N',N'',N''-tetramethylguanidino)ethyl]guanidine, see: Tiritiris & Kantlehner (2012).
Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2551 ).
The authors thank Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for measuring of the crystal data and Dr B. Iliev (IoLiTec GmbH) for the synthesis of the title compound.
Agarwal, N., Nayak, P. K., Ali, F., Patankar, M. P., Narasimhan, K. L. & Periasamy, N. (2011). Synth. Met. 161, 466-473.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chen, L.-Q., Yang, C.-L., Meng, X.-G. & Qin, J.-G. (2005). Acta Cryst. E61, o3073-o3075.
Gerkin, R. E. & Reppart, W. J. (1986). Acta Cryst. C42, 480-482.
Hooft, R. W. W. (2004). COLLECT. Bruker-Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Thomas, K. R. J., Lin, J. T., Tao, Y. T. & Ko, C. (2001). J. Am. Chem. Soc. 123, 9404-9411.
Tiritiris, I. & Kantlehner, W. (2012). Acta Cryst. E68, o2161.