Difluoro­[2-(quinolin-2-yl)phenolato]borane

Yang, X.; Xia, M.

doi:10.1107/S1600536811011895

Volume 67
Part 5
Page o1049
May 2011

Received 17 March 2011
Accepted 30 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.127
Data-to-parameter ratio = 11.9
Details

Difluoro[2-(quinolin-2-yl)phenolato]borane

Xi Yang ^a and Min Xia ^a ^*

^aDepartment of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China
Correspondence e-mail: xiamin@hzcnc.com

The title compound, C₁₅H₁₀BF₂NO, was synthesized by the reaction of 2-(quinolin-2-yl)phenol and boron trifluoride etherate. The quinoline ring system and the benzene ring are twisted, making a dihedral angle of 8.3 (2)°. In the crystal, [pi] - [pi] interactions between the aromatic rings [centroid-centroid distance = 3.638 (9) Å] link the molecules into chains propagating in [100].

Related literature

For the properties and the preparation of difluoroboron complexes, see: Loudet et al. (2007); Ulrich et al. (2008); Ono et al. (2009); Zhou et al. (2008); Xia et al. (2008).

Experimental

Crystal data

C₁₅H₁₀BF₂NO
M_r = 269.05
Triclinic, $[P \overline 1]$
a = 7.4660 (15) Å
b = 8.6300 (17) Å
c = 9.3420 (19) Å
= 97.71 (3)°
= 95.63 (3)°
= 92.61 (3)°
V = 592.5 (2) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 295 K
0.46 × 0.22 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.949, T_max = 0.984
4885 measured reflections
2169 independent reflections
1329 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.127
S = 1.13
2169 reflections
182 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.20 e Å^-3

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2346 ).

Acknowledgements

We are grateful for financial support by the Natural Science Foundation of Zhejiang Province (Y4100034) and the Innovation Fund Program for Graduate Students of Zhejiang Sci-Tech University (YCX-S10015).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Loudet, A. & Burgess, K. (2007). Chem. Rev. 107, 4891-4932.
Ono, K., Hashizume, J., Yamaguchi, H., Tomura, M., Nishida, J. & Yamashita, Y. (2009). Org. Lett. 11, 4326-4329.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Ulrich, G., Ziessel, R. & Harriman, A. (2008). Angew. Chem. Int. Ed. 47, 1184-1201.
Xia, M., Wu, B. & Xiang, G. F. (2008). J. Fluorine Chem. 129, 402-408.
Zhou, Y., Xiao, Y., Chi, X. M. & Qian, X. H. (2008). Org. Lett. 10, 633-636.

organic compounds