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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 [sigma](C-C) = 0.003 Å
R = 0.056
wR = 0.172
Data-to-parameter ratio = 16.8
Details
Open access

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

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-H...N interactions.

Related literature

For the original Tröger's base, see: Tröger (1887[Tröger, J. (1887). J. Prakt. Chem. 36, 225-245.]). For the chemistry of Tröger's base, see: Valík et al. (2005[Valík, M., Strongin, R. M. & Král, V. (2005). Supramol. Chem. 17, 347-367.]); Dolenský et al. (2007[Dolenský, B., Elguero, J., Král, V., Pardo, C. & Valík, M. (2007). Adv. Heterocycl. Chem. 93, 1-56.]); Sergeyev (2009[Sergeyev, S. (2009). Helv. Chim. Acta, 92, 415-444.]). For optoelectric applications of Tröger's base, see: Yuan et al. (2011[Yuan, C. X., Xin, Q., Liu, H. J., Wang, L., Jiang, M. H. & Tao, X. T. (2011). Sci. Chin. Chem. 54, 587-595.]); Xin et al. (2008[Xin, Q., Tao, X. T., Wang, F. Z., Sun, J. L., Zou, D. C., Wang, F. J., Liu, H. J., Liu, Z. & Jiang, M. H. (2008). Org. Electron. 9, 1076-1086.]); Yuan et al. (2007[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.]). For applications of organic boron compounds with dimesitylboryl groups in organic optoelectronics, see: Shirota & Noda (1998[Shirota, Y. & Noda, T. (1998). J. Am. Chem. Soc. 120, 9714-9715.]); Zhao et al. (2006[Zhao, C. H., Wakamiya, A., Inukai, Y. & Yamaguchi, S. (2006). J. Am. Chem. Soc. 128, 15934-15935.]); Collings et al. (2009[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.]); Jäkle (2010[Jäkle, F. (2010). Chem. Rev. 110, 3985-4022.]).

[Scheme 1]

Experimental

Crystal data
  • C51H56B2N2

  • Mr = 718.60

  • Triclinic, [P \overline 1]

  • a = 9.3565 (3) Å

  • b = 14.0077 (6) Å

  • c = 16.3650 (6) Å

  • [alpha] = 86.079 (3)°

  • [beta] = 83.808 (3)°

  • [gamma] = 88.377 (3)°

  • V = 2126.87 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.858, Tmax = 1.000

  • 25278 measured reflections

  • 8341 independent reflections

  • 6172 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.172

  • S = 1.02

  • 8341 reflections

  • 496 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C14-H14C...N2i 0.96 2.64 3.448 (3) 141
C15-H15A...Cg7ii 0.93 2.94 3.844 (2) 166
C38-H40B...Cg8iii 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [PubMed]
Oxford Diffraction (2009). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sergeyev, S. (2009). Helv. Chim. Acta, 92, 415-444.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shirota, Y. & Noda, T. (1998). J. Am. Chem. Soc. 120, 9714-9715.
Tröger, J. (1887). J. Prakt. Chem. 36, 225-245.  [CrossRef]
Valík, M., Strongin, R. M. & Král, V. (2005). Supramol. Chem. 17, 347-367.
Xin, Q., Tao, X. T., Wang, F. Z., Sun, J. L., Zou, D. C., Wang, F. J., Liu, H. J., Liu, Z. & Jiang, M. H. (2008). Org. Electron. 9, 1076-1086.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [CSD] [CrossRef] [ChemPort]
Yuan, C. X., Xin, Q., Liu, H. J., Wang, L., Jiang, M. H. & Tao, X. T. (2011). Sci. Chin. Chem. 54, 587-595.  [CrossRef] [ChemPort]
Zhao, C. H., Wakamiya, A., Inukai, Y. & Yamaguchi, S. (2006). J. Am. Chem. Soc. 128, 15934-15935.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o22  [ doi:10.1107/S1600536811051051 ]

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