2-(2-Hydroxy­benzyl­ideneamino)benzonitrile

Xia, R.; Xu, H.-J.; Gong, X.-X.

doi:10.1107/S160053680801163X

Volume 64
Part 6
Page o1047
June 2008

Received 26 March 2008
Accepted 23 April 2008
Online 10 May 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R = 0.061
wR = 0.136
Data-to-parameter ratio = 7.7
Details

2-(2-Hydroxybenzylideneamino)benzonitrile

Rong Xia,^a Hai-Jun Xu ^a ^* and Xing-Xuan Gong ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: xuhj@seu.edu.cn

The molecule of the title compound, C₁₄H₁₀N₂O, displays a trans configuration with respect to the C=N double bond. The molecule is roughly planar; the two aromatic rings make a dihedral angle of 9.3 (3)°. Such a planar conformation is induced by the strong intramolecular O-HN hydrogen bond between the imine and hydroxyl groups.

Related literature

For the structures of similar Schiff base compounds, see: Cheng et al. (2005, 2006). For related literature, see: Chen et al. (2008); Elmah et al. (1999); May et al. (2004); Weber et al. (2007); Xu et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Monoclinic, P 2₁
a = 4.7667 (10) Å
b = 16.190 (3) Å
c = 7.6714 (15) Å
= 93.30 (3)°
V = 591.0 (2) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.20 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.981, T_max = 1.00 (expected range = 0.977-0.996)
5470 measured reflections
1201 independent reflections
633 reflections with I > 2(I)
R_int = 0.105

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.136
S = 1.03
1201 reflections
155 parameters
1 restraint
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.92	2.651 (6)	147

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2331 ).

Acknowledgements

HJX acknowledges a Start-up Grant from Southeast University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170-2171.
Cheng, K., You, Z.-L., Li, Y.-G. & Zhu, H.-L. (2005). Acta Cryst. E61, o1137-o1138.
Cheng, K., Zhu, H.-L., Li, Z.-B. & Yan, Z. (2006). Acta Cryst. E62, o2417-o2418.
Elmah, A., Kabak, M. & Elerman, Y. (1999). J. Mol. Struct. 484, 229-234.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145-4156.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159-1162.
Xu, H.-J., Gong, X.-X. & Wang, H. (2008). Acta Cryst. E64, o638.

organic compounds