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Volume 69 
Part 9 
Pages o1394-o1395  
September 2013  

Received 27 July 2013
Accepted 1 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.154
Data-to-parameter ratio = 16.0
Details
Open access

1,2-Bis(2-hydroxy-5-methylbenzylidene)hydrazine

aCentre for Research and Development, PRIST University, Vallam, Thanjavur 613 403, India,bDepartment of Chemistry, DDE, Alagappa University, Karaikudi 630 003, India, and cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, crystallography2010@gmail.com

The molecular structure of the title compound, C16H16N2O2, is stabilized by intramolecular O-H...N hydrogen bonds with S(6) graph-set motifs, so that the molecule is almost planar, with a C=N-N=C torsion angle of -179.7 (2)° and a dihedral angle of 1.82 (12)° between the aromatic rings. In the crystal, weak C-H...[pi] interactions lead to the formation of a three-dimensional network.

Related literature

For the biological activity of Schiff base ligands, see: Kelley et al. (1995[Kelley, J. L., Linn, J. A., Bankston, D. D., Burchall, C. J., Soroko, F. E. & Cooper, B. R. (1995). J. Med. Chem. 38, 3676-3679.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Pharm. Acta Helv. 74, 11-17.]); Singh & Dash (1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]); Tarafder et al. (2002[Tarafder, M. T. H., Kasbollah, A., Saravanan, N., Crouse, K. A., Ali, A. M. & Khor, T. O. (2002). J. Biochem. Mol. Biol. Biophys. 6, 85-91.]). 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.]). For related strucutures, see: Chantrapromma et al. (2010[Chantrapromma, S., Jansrisewangwong, P. & Fun, H.-K. (2010). Acta Cryst. E66, o2994-o2995.]); Fun et al. (2010[Fun, H.-K., Jansrisewangwong, P. & Chantrapromma, S. (2010). Acta Cryst. E66, o2401-o2402.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O2

  • Mr = 268.31

  • Orthorhombic, P 21 21 21

  • a = 6.0108 (5) Å

  • b = 7.3394 (5) Å

  • c = 31.674 (2) Å

  • V = 1397.32 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.22 × 0.18 × 0.16 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.982, Tmax = 0.987

  • 5699 measured reflections

  • 2952 independent reflections

  • 1780 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.154

  • S = 1.02

  • 2952 reflections

  • 185 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C10-C15 rings, respectively.

D-H...A D-H H...A D...A D-H...A
O2-H2A...N2 0.82 1.91 2.635 (3) 146
O1-H1...N1 0.82 1.93 2.646 (3) 145
C5-H5...Cg1i 0.93 2.84 3.519 (3) 130
C14-H14...Cg2ii 0.93 2.85 3.519 (3) 130
Symmetry codes: (i) [-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5296 ).


Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Jansrisewangwong, P. & Fun, H.-K. (2010). Acta Cryst. E66, o2994-o2995.  [CSD] [CrossRef] [ChemPort] [details]
Fun, H.-K., Jansrisewangwong, P. & Chantrapromma, S. (2010). Acta Cryst. E66, o2401-o2402.  [CSD] [CrossRef] [ChemPort] [details]
Kelley, J. L., Linn, J. A., Bankston, D. D., Burchall, C. J., Soroko, F. E. & Cooper, B. R. (1995). J. Med. Chem. 38, 3676-3679.  [CrossRef] [ChemPort] [PubMed] [ISI]
Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Pharm. Acta Helv. 74, 11-17.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Tarafder, M. T. H., Kasbollah, A., Saravanan, N., Crouse, K. A., Ali, A. M. & Khor, T. O. (2002). J. Biochem. Mol. Biol. Biophys. 6, 85-91.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1394-o1395   [ doi:10.1107/S160053681302148X ]

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