2-{[2-(2-Hy­droxy-3-meth­oxy­benzyl­idene)hydrazin-1-yl­idene]meth­yl}-6-meth­oxy­phenol

Lu, R.; Wang, W.; Lü, X.; Zhao, S.

doi:10.1107/S1600536811036816

Volume 67
Part 10
Page o2702
October 2011

Received 17 July 2011
Accepted 10 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R = 0.061
wR = 0.186
Data-to-parameter ratio = 12.7
Details

2-{[2-(2-Hydroxy-3-methoxybenzylidene)hydrazin-1-ylidene]methyl}-6-methoxyphenol

Rong Lu,^a ^* Wenxia Wang,^a Xingqiang Lü ^a and Shunsheng Zhao ^b

^aCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xian University of Science and Technology, Xi'an 710054, Shaanxi, People's Republic of China
Correspondence e-mail: lu78441@yahoo.com.cn

The title compound, C₁₆H₁₆N₂O₄, was obtained from the reaction of hydrazine hydrate and o-vanilin in absolute ethanol. The molecule is almost planar (except for the methyl H atoms), with a mean deviation from the plane of 0.0259 Å. The molecular structure also exhibits an approximate non-crystallographic twofold axis. Intramolecular O-HN hydrogen bonds occur. In the crystal, intermolecular C-HO hydrogen bonds generate molecular zigzag sheets. The sheets stack through C-H [pi] interactions, leading to a three-dimensional-network.

Related literature

For the properties and applications of the title compound or similar structural compounds and their metal complexes, see: Lin et al. (2009); Davidson et al. (2006); Lin & Zeng (2006).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M_r = 300.31
Monoclinic, P 2₁ /c
a = 6.3095 (14) Å
b = 17.405 (4) Å
c = 13.606 (3) Å
= 95.590 (4)°
V = 1487.0 (6) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.858, T_max = 1.000
7393 measured reflections
2648 independent reflections
1133 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.186
S = 1.07
2648 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7 and C10-C15 rings, respectively.

D-HA	D-H	HA	DA	D-HA
O3-H3AN2	0.91 (5)	1.82 (5)	2.640 (4)	149 (4)
O2-H2AN1	0.88 (4)	1.82 (4)	2.636 (4)	153 (4)
C16-H16AO4ⁱ	0.96	2.55	3.279 (5)	133
C7-H7ACg2ⁱⁱ	0.93	2.90	3.694 (4)	144
C13-H13ACg1ⁱⁱⁱ	0.93	2.89	3.717 (4)	149
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2353 ).

Acknowledgements

This project was supported by the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2010JM2006, 2011JQ2011) and the Scientific Research Program funded by Shaanxi Provincial Education Department (Program No. 2008 J K440).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Davidson, M. G., Johnson, A. L., Jones, M. D., Lunn, M. D. & Mahon, M. F. (2006). Eur. J. Inorg. Chem. 21, 4449-4454.
Lin, P.-H., Burchell, T. J., Ungur, L., Chibotaru, L. F., Wernsdorfer, W. & Murugesu, M. (2009). Angew. Chem. Int. Ed. 48, 9489-9452.
Lin, Z.-D. & Zeng, W. (2006). Acta Cryst. E62, m1074-m1076.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds