(E)-4-[(3,5-Dimethyl­phen­yl)imino­meth­yl]-2-meth­oxy-3-nitro­phenol

Yang, Z.-M.; Su, D.-C.; Zhu, H.-L.

doi:10.1107/S1600536811054407

Volume 68
Part 1
Page o220
January 2012

Received 14 December 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.140
Data-to-parameter ratio = 14.5
Details

(E)-4-[(3,5-Dimethylphenyl)iminomethyl]-2-methoxy-3-nitrophenol

Zhong-Ming Yang,^a ^* Deng-Cheng Su ^a and Hai-Liang Zhu ^a

^aSchool of Life Sciences, Shangdong University of Technology, Zibo 255000, People's Republic of China
Correspondence e-mail: hailiang_zhu@163.com

The molecule of the title compound, C₁₆H₁₆N₂O₄, exists in the E configuration with respect to the central C=N double bond. The dihedral angle between the two benzene rings is 2.17 (9) Å. In the crystal, molecules are linked via O-HN hydrogen bonds into chains that propagate along the b-axis direction. There is also [pi] - [pi] stacking of inversion-related molecules, with interplanar spacings of 3.479 (5) Å and ring centroid-centroid distances of 3.876 (4) Å.

Related literature

The title compound is an imine derivative of 4-hydroxy-3-methoxy-2-nitrobenzaldehyde, a vanillin-like compound. For background to the biological activity of vanillin derivatives, see: Javiya et al. (2008); Cordano et al. (2002). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M_r = 300.31
Monoclinic, P 2₁ /c
a = 8.616 (9) Å
b = 9.690 (11) Å
c = 18.29 (2) Å
= 97.631 (11)°
V = 1513 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.23 × 0.21 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.978, T_max = 0.989
8085 measured reflections
2935 independent reflections
1699 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.140
S = 1.04
2935 reflections
203 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N2ⁱ	0.82	1.95	2.755 (3)	169
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: PK2377 ).

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.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cordano, G., Pezoa, J., Munoz, S., Rivera, E., Medina, J., Nunez-Vergara, L. J., Pavani, M., Guerrero, A. & Ferreira, J. (2002). Eur. J. Pharm. Sci. 16, 255-263.
Javiya, J., Godvani, N., Baluja, S., Parekh, J. & Chanda, S. (2008). Acta Cienc. Indica Chem. 34, 413-417.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds