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Volume 69 
Part 7 
Page o1085  
July 2013  

Received 31 May 2013
Accepted 3 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.010 Å
R = 0.095
wR = 0.229
Data-to-parameter ratio = 12.8
Details
Open access

2-{(E)-[(2-Methyl-3-nitrophenyl)imino]methyl}-4-nitrophenol

aDepartment of Physics, Faculty of Arts & Science, Amasya University, Ipekkoy-Amasya, Turkey,bDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayis University, TR-55139, Kurupelit-Samsun, Turkey, and cFaculty of Technology, Amasya University, TR-05100 Amasya, Turkey
Correspondence e-mail: myavuz@omu.edu.tr

The title compound, C14H11N3O5, is a Schiff base that adopts the enol-imine tautomeric form in the solid state. The dihedral angle between the aromatic rings is 37.4 (3)° and the dihedral angles between the nitro groups and their attached rings are 4.0 (6) and 46.2 (8)°. The molecular structure is stabilized by an intramolecular O-H...N hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by C-H...O interactions, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological properties of Schiff bases, see: Aydogan et al. (2001[Aydogan, F., Öcal, N., Turgut, Z. & Yolaçan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.]); Taggi et al. (2002[Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.]); Barton & Ollis (1979[Barton, D. & Ollis, W. D. (1979). Comprehensive Organic Chemistry, vol 2. Oxford: Pergamon.]); Layer (1963[Layer, R. W. (1963). Chem. Rev. 63, 489-510.]); Ingold (1969[Ingold, C. K. (1969). Structure and Mechanism in Organic Chemistry, 2nd ed. Ithaca: Cornell University Press.]); Cohen et al. (1964[Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041-2051.]); Moustakali-Mavridis et al. (1978[Moustakali-Mavridis, I., Hadjoudis, E. & Mavridis, A. (1978). Acta Cryst. B34, 3709-3715.]). For tautomeric forms of Schiff base compounds, see: Tanak et al. (2010[Tanak, H., Agar, A. & Yavuz, M. (2010). J. Mol. Model. 16, 577-587.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a related structure, see: Tanak (2011[Tanak, H. (2011). J. Phys. Chem. A, 115, 13865-13876.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11N3O5

  • Mr = 301.26

  • Monoclinic, P 21 /c

  • a = 3.754 (5) Å

  • b = 15.696 (5) Å

  • c = 23.149 (5) Å

  • [beta] = 93.491 (5)°

  • V = 1361.5 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.46 × 0.20 × 0.05 mm

Data collection
  • Stoe IPDS II diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.600, Tmax = 0.976

  • 7609 measured reflections

  • 2538 independent reflections

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

  • Rint = 0.181

Refinement
  • R[F2 > 2[sigma](F2)] = 0.095

  • wR(F2) = 0.229

  • S = 0.97

  • 2538 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H2...N2 0.82 1.85 2.589 (8) 149
C6-H6...O2i 0.93 2.50 3.333 (9) 149
C4-H4...O4ii 0.93 2.59 3.274 (9) 131
Symmetry codes: (i) -x, -y, -z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6911 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

Aydogan, F., Öcal, N., Turgut, Z. & Yolaçan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.  [ChemPort]
Barton, D. & Ollis, W. D. (1979). Comprehensive Organic Chemistry, vol 2. Oxford: Pergamon.
Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041-2051.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ingold, C. K. (1969). Structure and Mechanism in Organic Chemistry, 2nd ed. Ithaca: Cornell University Press.
Layer, R. W. (1963). Chem. Rev. 63, 489-510.  [CrossRef] [ChemPort] [Web of Science]
Moustakali-Mavridis, I., Hadjoudis, E. & Mavridis, A. (1978). Acta Cryst. B34, 3709-3715.  [CrossRef] [IUCr Journals] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Tanak, H. (2011). J. Phys. Chem. A, 115, 13865-13876.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Tanak, H., Agar, A. & Yavuz, M. (2010). J. Mol. Model. 16, 577-587.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1085  [ doi:10.1107/S1600536813015407 ]

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