[Journal logo]

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 [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.140
Data-to-parameter ratio = 14.5
Details
Open access

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

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-H...N 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[Javiya, J., Godvani, N., Baluja, S., Parekh, J. & Chanda, S. (2008). Acta Cienc. Indica Chem. 34, 413-417.]); Cordano et al. (2002[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.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O4

  • Mr = 300.31

  • Monoclinic, P 21 /c

  • a = 8.616 (9) Å

  • b = 9.690 (11) Å

  • c = 18.29 (2) Å

  • [beta] = 97.631 (11)°

  • V = 1513 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.989

  • 8085 measured reflections

  • 2935 independent reflections

  • 1699 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.140

  • S = 1.04

  • 2935 reflections

  • 203 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N2i 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
Javiya, J., Godvani, N., Baluja, S., Parekh, J. & Chanda, S. (2008). Acta Cienc. Indica Chem. 34, 413-417.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o220  [ doi:10.1107/S1600536811054407 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.