[Journal logo]

Volume 69 
Part 5 
Page o648  
May 2013  

Received 15 March 2013
Accepted 21 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.120
Data-to-parameter ratio = 17.1
Details
Open access

(E)-6-(4-Chlorophenyl)-4-[(2-cyano-3-phenylallyl)sulfanyl]-2,2-difluoro-3-phenyl-1,3,2-oxazaborinin-3-ium-2-uide

aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
Correspondence e-mail: wenlirong@qust.edu.cn

In the title compound, C25H18BClF2N2OS, the characteristic B-N and B-O bond lengths are 1.571 (3) and 1.458 (3) Å, respectively. The phenyl rings form dihedral angles of 83.1 (1) and 64.6 (1)° with the chlorophenyl ring. In the crystal, weak C-H...N, C-H...F, C-H...[pi] and [pi]-[pi] interactions [centroid-centroid distances 3.877 (6) Å between the chlorophenyl rings of neighbouring molecules] held molecules together, forming ladders along the b axis.

Related literature

For background to thioacetanilides, see: Peruncheralathan et al. (2005[Peruncheralathan, S., Yadav, A. K., Ila, H. & Junjappa, H. (2005). J. Org. Chem. 70, 9644-9647.]); Li et al. (2010[Li, M., Hou, Y. L., Wen, L. R. & Gong, F. M. (2010). J. Org. Chem. 75, 8522-8532.]); Wu et al. (2009[Wu, L., Loudet, A., Barhoumi, R., Burghardt, R. & Burgess, K. (2009). J. Am. Chem. Soc. 131, 9156-9157.]); Erten-Ela et al. (2008[Erten-Ela, S., Yilmaz, D., Icli, B., Dede, Y., Icli, S. & Akkaya, U. E. (2008). Org. Lett. 10, 3299-3320.]); Tokoro et al. (2010[Tokoro, Y., Nagai, A. & Chujo, Y. (2010). Tetrahedron Lett. 51, 3451-3454.]); Lu et al. (2002[Lu, W., Mi, B. X., Chan, M. C. W., Hui, Z., Zhu, N., Lee, S. T. & Che, C. M. (2002). Chem. Commun. pp. 206-207.]); Tsuboyama et al. (2003[Tsuboyama, A., Iwawaki, H., Iwawaki, H., Furugori, M., Mukaide, T., Kamatani, J., Igawa, S., Moriyama, T., Miura, S., Takiguchi, T., Okada, S., Hoshino, M. & Ueno, K. (2003). J. Am. Chem. Soc. 125, 12971-12979.]); Zhang et al. (2006[Zhang, H., Huo, C., Zhang, J., Zhang, P., Tian, W. & Wang, Y. (2006). Chem. Commun. pp. 281-283.]). For the crystal structures of related compounds, see: Macedo et al. (2008[Macedo, F. P., Gwengo, C., Lindeman, S. V., Smith, M. D. & Gardinier, J. R. (2008). Eur. J. Inorg. Chem. pp. 3200-3211.]).

[Scheme 1]

Experimental

Crystal data
  • C25H18BClF2N2OS

  • Mr = 478.73

  • Monoclinic, P 21 /c

  • a = 9.6996 (19) Å

  • b = 16.290 (3) Å

  • c = 14.168 (3) Å

  • [beta] = 98.71 (3)°

  • V = 2212.9 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 173 K

  • 0.43 × 0.29 × 0.09 mm

Data collection
  • Rigaku MM007HF diffractometer with Saturn724+ CCD

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.685, Tmax = 1.000

  • 15558 measured reflections

  • 5081 independent reflections

  • 4491 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.120

  • S = 1.18

  • 5081 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C16-H16A...F1i 0.99 2.35 3.184 (3) 141
C21-H21...N1ii 0.95 2.55 3.434 (4) 156
C15-H15...Cg1iii 0.95 2.52 3.394 (5) 153
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z.

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: CV5394 ).


References

Erten-Ela, S., Yilmaz, D., Icli, B., Dede, Y., Icli, S. & Akkaya, U. E. (2008). Org. Lett. 10, 3299-3320.  [ISI] [PubMed] [ChemPort]
Li, M., Hou, Y. L., Wen, L. R. & Gong, F. M. (2010). J. Org. Chem. 75, 8522-8532.  [CSD] [CrossRef] [ChemPort] [PubMed]
Lu, W., Mi, B. X., Chan, M. C. W., Hui, Z., Zhu, N., Lee, S. T. & Che, C. M. (2002). Chem. Commun. pp. 206-207.  [CSD] [CrossRef]
Macedo, F. P., Gwengo, C., Lindeman, S. V., Smith, M. D. & Gardinier, J. R. (2008). Eur. J. Inorg. Chem. pp. 3200-3211.  [ISI] [CSD] [CrossRef]
Peruncheralathan, S., Yadav, A. K., Ila, H. & Junjappa, H. (2005). J. Org. Chem. 70, 9644-9647.  [CSD] [CrossRef] [PubMed] [ChemPort]
Rigaku/MSC (2008). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tokoro, Y., Nagai, A. & Chujo, Y. (2010). Tetrahedron Lett. 51, 3451-3454.  [ISI] [CrossRef] [ChemPort]
Tsuboyama, A., Iwawaki, H., Iwawaki, H., Furugori, M., Mukaide, T., Kamatani, J., Igawa, S., Moriyama, T., Miura, S., Takiguchi, T., Okada, S., Hoshino, M. & Ueno, K. (2003). J. Am. Chem. Soc. 125, 12971-12979.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Wu, L., Loudet, A., Barhoumi, R., Burghardt, R. & Burgess, K. (2009). J. Am. Chem. Soc. 131, 9156-9157.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhang, H., Huo, C., Zhang, J., Zhang, P., Tian, W. & Wang, Y. (2006). Chem. Commun. pp. 281-283.  [CSD] [CrossRef]


Acta Cryst (2013). E69, o648  [ doi:10.1107/S1600536813007800 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.