(E)-2-(2,4-Dihydroxy­benzyl­ideneamino)benzonitrile

Liu, T.

doi:10.1107/S1600536809020182

Volume 65
Part 7
Page o1502
July 2009

Received 22 May 2009
Accepted 27 May 2009
Online 6 June 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.059
wR = 0.153
Data-to-parameter ratio = 16.1
Details

(E)-2-(2,4-Dihydroxybenzylideneamino)benzonitrile

Ting Liu ^a ^*

^aBiology and Chemistry Department, Nanchang University College of Science and Technology, Nanchang 330029, People's Republic of China
Correspondence e-mail: liuting_ncu@yahoo.cn

The molecule of the title compound, C₁₄H₁₀N₂O₂, adopts the phenol-imine tautomeric form. The dihedral angle between the planes of the two benzene rings is 13.84 (13)°. A strong intramolecular O-HN hydrogen-bonding interaction stabilizes the molecular conformation. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C-HO and O-HN hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Cheng et al. (2006); Xia et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₁₀N₂O₂
M_r = 238.24
Monoclinic, P 2₁ /c
a = 13.322 (3) Å
b = 5.7505 (12) Å
c = 16.132 (3) Å
= 108.97 (3)°
V = 1168.7 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.973, T_max = 0.979
11536 measured reflections
2683 independent reflections
1394 reflections with I > 2(I)
R_int = 0.073

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.153
S = 1.01
2683 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN2	0.95 (3)	1.70 (3)	2.581 (2)	152 (3)
O2-H2AN1ⁱ	0.82	2.03	2.835 (3)	166
C11-H11AO1ⁱ	0.93	2.56	3.386 (3)	148
Symmetry code: (i) -x+1, -y+1, -z.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2327 ).

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.
Cheng, K., Zhu, H.-L., Li, Z.-B. & Yan, Z. (2006). Acta Cryst. E62, o2417-o2418.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xia, R., Xu, H.-J. & Gong, X.-X. (2008). Acta Cryst. E64, o1047.

organic compounds