9-[(E)-2-(4,4,5,5-Tetra­methyl-1,3,2-dioxa­borolan-2-yl)ethen­yl]-9H-carbazole

Hatayama, Y.; Okuno, T.

doi:10.1107/S1600536811052470

Volume 68
Part 1
Page o84
January 2012

Received 30 November 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.004 Å
R = 0.053
wR = 0.137
Data-to-parameter ratio = 14.8
Details

9-[(E)-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-9H-carbazole

Yuki Hatayama ^a and Tsunehisa Okuno ^a ^*

^aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

The title compound, C₂₀H₂₂BNO₂, is a simple olefinic compound which carries both B and N atoms that are trans to one another. The [pi] -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^-.

Related literature

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).

Experimental

Crystal data

C₂₀H₂₂BNO₂
M_r = 319.21
Triclinic, $[P \overline 1]$
a = 11.616 (3) Å
b = 12.962 (3) Å
c = 12.990 (3) Å
= 83.620 (11)°
= 85.632 (11)°
= 64.647 (6)°
V = 1755.6 (8) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 93 K
0.19 × 0.07 × 0.03 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999) T_min = 0.990, T_max = 0.998
12732 measured reflections
6408 independent reflections
4117 reflections with F² > 2(F²)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.137
S = 1.01
6406 reflections
433 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.22 e Å^-3

Table 1
Selected bond lengths (Å)

B1-C14	1.537 (3)
B2-C34	1.537 (4)
N1-C13	1.396 (3)
N2-C33	1.392 (3)
C13-C14	1.336 (4)
C33-C34	1.334 (4)

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 ).

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency (JST).

References

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.

organic compounds