2-Eth­oxy-4-[2-(3-nitro­phen­yl)­hydrazono­meth­yl]phenol

Chen, J.-Q.; Jiang, L.; Li, S.-M.; Chen, Y.-Z.

doi:10.1107/S1600536809037908

Volume 65
Part 10
Page o2536
October 2009

Received 11 September 2009
Accepted 18 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.077
Data-to-parameter ratio = 14.0
Details

2-Ethoxy-4-[2-(3-nitrophenyl)hydrazonomethyl]phenol

Jun-Qiang Chen,^a ^* Ling Jiang,^b Shu-Mian Li ^b and Yu-Zhen Chen ^b

^aEnergy Research Institute Co. Ltd, Henan Academy of Sciences, Zhengzhou 450000, People's Republic of China, and ^bKey Laboratory of Surface and Interface Science of Henan, School of Materials and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
Correspondence e-mail: junqiangchen2009@126.com

The title Schiff base compound, C₁₅H₁₅N₃O₄, was prepared from a condensation reaction of 3-ethoxy-4-hydroxybenzaldehyde and 3-nitrophenylhydrazine. The molecule is nearly planar; the dihedral angle between the hydroxybenzene ring and the nitrobenzene ring is 6.57 (7)°. O-HO, O-HN and C-HO hydrogen bonding helps to stabilize the crystal structure.

Related literature

For applications of Schiff base compounds, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental

Crystal data

C₁₅H₁₅N₃O₄
M_r = 301.30
Monoclinic, P 2₁ /n
a = 12.4160 (6) Å
b = 7.7429 (4) Å
c = 16.2249 (9) Å
= 110.497 (6)°
V = 1461.04 (13) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.20 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.979, T_max = 0.982
5606 measured reflections
2835 independent reflections
1558 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.077
S = 0.80
2835 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.13 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1	0.89 (2)	2.14 (2)	2.6582 (16)	116.7 (18)
O2-H2AN1ⁱ	0.89 (2)	2.32 (2)	3.0345 (19)	137.0 (15)
C11-H11AO2ⁱⁱ	0.93	2.56	3.340 (2)	141
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2611 ).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179-185.
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds