Received 30 November 2011
The title compound, C20H22BNO2, is a simple olefinic compound which carries both B and N atoms that are trans to one another. The -conjugated system of the compound is considered to be isoelectronic with 1,3-butadiene. There are two independent molecules in the asymmetric unit in which the environments around the boron atoms are essentially planar (r.m.s. deviations of 0.0032 and 0.0021 Å for the BO2C planes). The dihedral angles of the olefinic planes with the boron planes are 5.70 (11) and 9.74 (9)°, respectively, while the dihedral angles of the olefinic planes with the carbazole planes are 19.37 (3) and 10.74 (6)°. These dihedral angles are consistent with those in 9-ethenylcarbazole and an ethenylboronic ester derivative. The N-Csp2, B-Csp2 and C=C bond lengths suggest that the contribution of the canonical structure can be described as N+=C-C=B-.
For the related structure of 9-ethenylcarbazole, see: Tsutsui et al. (1976); Tian et al. (2006). For the related structure of a ethenyl-boronic ester derivative, see: Clark et al. (2004). For the preparation of the title compound, see: Geier et al. (2009).
Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2046 ).
This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency (JST).
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Clark, J. S., Freeman, R. P., Cacho, M., Thomas, A. W., Swallow, S. & Wilson, C. (2004). Tetrahedron Lett. 45, 8639-8642.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Geier, M. J., Vogels, C. M., Decken, A. & Westcott, S. A. (2009). J. Organomet. Chem. 694, 3154-3159.
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tian, X., Shi, W., Shen, K., Li, C., Lin, J., Che, Y. & Zhang, P. (2006). J. Organomet. Chem. 691, 994-1006.
Tsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049-3053.