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Volume 69 
Part 5 
Page o781  
May 2013  

Received 2 April 2013
Accepted 16 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.119
Data-to-parameter ratio = 13.0
Details
Open access

12-Dimethylamino-2,2-difluoro-8-phenyl-1[lambda]5,3-diaza-2[lambda]4-boratricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium

aSchool of Chemistry and Material Science, Anhui Normal University, Wuhu, People's Republic of China
Correspondence e-mail: shine_zywang@yahoo.com.cn

In the title boron-dipyrromethene derivative, C17H16BF2N3, the benzene ring and the boron-dipyrromethene mean plane form a dihedral angle of 55.82 (8)°. In the crystal, pairs of C-H...F interactions link the molecules, forming inversion dimers. Further C-H...F interactions link the dimers into a three-dimensional network.

Related literature

For the synthesis and applications of related 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene derivatives, see: Trieflinger et al. (2005[Trieflinger, C., Rurack, K. & Daub, J. (2005). Angew. Chem. Int. Ed. 44, 2288-2291.]). For related structures, see: Jiao et al. (2011[Jiao, L. J., Pang, W. D., Zhou, J. Y., Wei, Y., Mu, X. L., Bai, G. F. & Hao, E. H. (2011). J. Org. Chem. 76, 9988-9996.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16BF2N3

  • Mr = 311.14

  • Monoclinic, P 21 /c

  • a = 7.8033 (6) Å

  • b = 25.524 (2) Å

  • c = 9.9776 (5) Å

  • [beta] = 128.671 (4)°

  • V = 1551.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.972, Tmax = 0.981

  • 11054 measured reflections

  • 2736 independent reflections

  • 2025 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.119

  • S = 1.03

  • 2736 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...F2i 0.93 2.51 3.291 (3) 142
C17-H17C...F2ii 0.96 2.49 3.282 (3) 140
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+2, -z+2.

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: RK2400 ).


Acknowledgements

This work was supported by the Research Culture Funds of Anhui Normal University (160-721137).

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jiao, L. J., Pang, W. D., Zhou, J. Y., Wei, Y., Mu, X. L., Bai, G. F. & Hao, E. H. (2011). J. Org. Chem. 76, 9988-9996.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Trieflinger, C., Rurack, K. & Daub, J. (2005). Angew. Chem. Int. Ed. 44, 2288-2291.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o781  [ doi:10.1107/S1600536813010404 ]

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