2,8-Dimesitylboranyl-6H,12H-5,11-methano­dibenzo[b,f][1,5]diazo­cine

Yuan, C.-X.

doi:10.1107/S1600536811051051

Volume 68
Part 1
Page o22
January 2012

Received 12 November 2011
Accepted 28 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.056
wR = 0.172
Data-to-parameter ratio = 16.8
Details

2,8-Dimesitylboranyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

Chun-Xue Yuan ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
Correspondence e-mail: chunxue1982@126.com

In the title compound, C₅₁H₅₆B₂N₂, a substituted Tröger's base, the dihedral angle between the two benzene rings constituting the Tröger's base framework is 104.42 (6)°. The crystal structure is stabilized by C-H [pi] and weak C-HN interactions.

Related literature

For the original Tröger's base, see: Tröger (1887). For the chemistry of Tröger's base, see: Valík et al. (2005); Dolenský et al. (2007); Sergeyev (2009). For optoelectric applications of Tröger's base, see: Yuan et al. (2011); Xin et al. (2008); Yuan et al. (2007). For applications of organic boron compounds with dimesitylboryl groups in organic optoelectronics, see: Shirota & Noda (1998); Zhao et al. (2006); Collings et al. (2009); Jäkle (2010).

Experimental

Crystal data

C₅₁H₅₆B₂N₂
M_r = 718.60
Triclinic, $[P \overline 1]$
a = 9.3565 (3) Å
b = 14.0077 (6) Å
c = 16.3650 (6) Å
= 86.079 (3)°
= 83.808 (3)°
= 88.377 (3)°
V = 2126.87 (14) Å³
Z = 2
Mo K radiation
= 0.06 mm^-1
T = 293 K
0.65 × 0.41 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.858, T_max = 1.000
25278 measured reflections
8341 independent reflections
6172 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.172
S = 1.02
8341 reflections
496 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg7 and Cg8 are the centroids of the C34-C37/C39/C40 and C43/C44/C46/C47/C49/C50 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C14-H14CN2ⁱ	0.96	2.64	3.448 (3)	141
C15-H15ACg7ⁱⁱ	0.93	2.94	3.844 (2)	166
C38-H40BCg8ⁱⁱⁱ	0.97	3.00	3.751 (3)	136
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: ZS2166 ).

References

Collings, J. C., Poon, S.-Y., Droumaguet, C. L., Charlot, M., Katan, C., Pålsson, L. O., Beeby, A., Mosely, J. A., Kaiser, H. M., Kaufmann, D., Wong, W.-Y., Blanchard-Desce, M. & Marder, T. B. (2009). Chem. Eur. J. 15, 198-208.
Dolenský, B., Elguero, J., Král, V., Pardo, C. & Valík, M. (2007). Adv. Heterocycl. Chem. 93, 1-56.
Jäkle, F. (2010). Chem. Rev. 110, 3985-4022.
Oxford Diffraction (2009). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sergeyev, S. (2009). Helv. Chim. Acta, 92, 415-444.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shirota, Y. & Noda, T. (1998). J. Am. Chem. Soc. 120, 9714-9715.
Tröger, J. (1887). J. Prakt. Chem. 36, 225-245.
Valík, M., Strongin, R. M. & Král, V. (2005). Supramol. Chem. 17, 347-367.
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Yuan, C. X., Tao, X. T., Ren, Y., Yang, J. X., Yu, W. T., Wang, L. & Jiang, M. H. (2007). J. Phys. Chem. C, 111, 12811-12816.
Yuan, C. X., Xin, Q., Liu, H. J., Wang, L., Jiang, M. H. & Tao, X. T. (2011). Sci. Chin. Chem. 54, 587-595.
Zhao, C. H., Wakamiya, A., Inukai, Y. & Yamaguchi, S. (2006). J. Am. Chem. Soc. 128, 15934-15935.

organic compounds