9-Phenyl-3,6-bis­(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Wu, W.; Tang, J.

doi:10.1107/S1600536811025645

Volume 67
Part 8
Page o1919
August 2011

Received 28 June 2011
Accepted 29 June 2011
Online 6 July 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.093
wR = 0.242
Data-to-parameter ratio = 19.2
Details

9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Weibing Wu ^a ^* and Jinan Tang ^b

^aJiangsu Provincial Key Laboratory of Pulp & Paper Science & Technology, College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: wbwu@yahoo.cn

In the title compound, C₃₀H₃₅B₂NO₄, the carbazole skeleton is essentially planar (r.m.s. deviation for all non-H atoms = 0.035 Å), and is oriented at a dihedral angle of 65.0 (3)° with respect to the adjacent phenyl ring.

Related literature

The title compound is an intermediate in the synthesis of 9-phenylcarbazole-based optical materials, see: Oliveira et al. (2005). For the synthesis of the title compound, see: Wong et al. (2005, 2006); Rashidnadimi et al. (2008). For related structures, see: Xu et al. (2010); Cui et al. (2009); Saeed et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₃₀H₃₅B₂NO₄
M_r = 495.21
Orthorhombic, P b c a
a = 13.974 (6) Å
b = 11.935 (5) Å
c = 34.494 (14) Å
V = 5753 (4) Å³
Z = 8
Mo K radiation
= 0.07 mm^-1
T = 298 K
0.3 × 0.2 × 0.1 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.9, T_max = 1
49645 measured reflections
6553 independent reflections
5170 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.093
wR(F²) = 0.242
S = 1.16
6553 reflections
342 parameters
15 restraints
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.52 e Å^-3

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2305 ).

Acknowledgements

The authors are grateful for financial support from the National Natural Science Foundation of China (No. 30972321) and the Basic Research Project of the Natural Science Foundation of Jiangsu Provincial Universities (10KJB53007).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Cui, J., Duan, M. & Cai, L. (2009). Acta Cryst. E65, o215.
Oliveira, M. M., Salvador, M. A., Coelho, P. J. & Carvalho, L. M. (2005). Tetrahedron, 61, 1681-1691.
Rashidnadimi, S., Hung, T. H., Wong, K.-T. & Bard, A. J. (2008). J. Am. Chem. Soc. 130, 634-639.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Saeed, A., Kazmi, M., Ameen Samra, S., Irfan, M. & Bolte, M. (2010). Acta Cryst. E66, o2118.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wong, K.-T., Chao, T.-C., Chi, L.-C., Chu, Y.-Y., Balaiah, A., Chiu, S.-F., Liu, Y.-H. & Wang, Y. (2006). Org. Lett. 8, 5033-5036.
Wong, K.-T., Hung, T.-H., Chao, T.-C. & Ho, T.-I. (2005). Tetrahedron Lett. 46, 855-858.
Xu, G.-Y., Geng, W.-Q. & Zhou, H.-P. (2010). Acta Cryst. E66, o571.

organic compounds