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Volume 68 
Part 12 
Page o3255  
December 2012  

Received 5 October 2012
Accepted 10 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.124
Data-to-parameter ratio = 13.3
Details
Open access

N'-[(E)-2-Hydroxy-5-methoxybenzylidene]-2-methoxybenzohydrazide

aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E. Malaysia,bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Malaysia,cFaculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam, 42300, Selangor, Malaysia, and dH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

The molecule of the title compound, C16H16N2O4, adopts an E conformation about the azomethine C=N double bond. The dihedral angle formed by the benzene rings is 18.88 (9)°. The molecular conformation is stabilized by an intramolecular O-H...N hydrogen bond, which forms an S(6) ring. In the crystal, the molecules are linked into chains parallel to [001] by N-H...O hydrogen bonds. The chains are further connected into a three-dimensional network by [pi]-[pi] stacking interactions with centroid-centroid distances of 3.6538 (10) and 3.8995 (11) Å.

Related literature

For the applications and biological activity of Schiff bases, see: Panneerselvam et al. (2009[Panneerselvam, P., Rather, B. A., Reddy, D. R. S. & Kumar, R. N. (2009). Eur. J. Med. Chem. 44, 2328-2333.]); Khan et al. (2009[Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983-2988.]); Jarahpour et al. (2007[Jarahpour, A., Khalili, D., De Clercq, E., Salmi, C. & Brunel, J. M. (2007). Molecules, 12, 1720-1730.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & DeClercq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.]). For related structures, see: Taha et al. (2012a[Taha, M., Baharudin, M. S., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012a). Acta Cryst. E68, o3256.],b[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012b). Acta Cryst. E68, o2780.]); Lu et al. (2008[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008). Acta Cryst. E64, o1693.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O4

  • Mr = 300.31

  • Monoclinic, P 21 /c

  • a = 14.5775 (13) Å

  • b = 11.0798 (11) Å

  • c = 9.5893 (9) Å

  • [beta] = 99.872 (2)°

  • V = 1525.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 273 K

  • 0.59 × 0.45 × 0.39 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.964

  • 8886 measured reflections

  • 2767 independent reflections

  • 2210 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.124

  • S = 1.04

  • 2767 reflections

  • 208 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1 0.83 (2) 1.87 (2) 2.605 (2) 146.0 (19)
N2-H2A...O3i 0.835 (17) 2.051 (17) 2.8258 (17) 154.2 (15)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART 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, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5014 ).


References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jarahpour, A., Khalili, D., De Clercq, E., Salmi, C. & Brunel, J. M. (2007). Molecules, 12, 1720-1730.  [PubMed]
Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983-2988.  [CrossRef] [PubMed] [ChemPort]
Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008). Acta Cryst. E64, o1693.  [CSD] [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Pandeya, S. N., Sriram, D., Nath, G. & DeClercq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.  [ISI] [CrossRef] [PubMed] [ChemPort]
Panneerselvam, P., Rather, B. A., Reddy, D. R. S. & Kumar, R. N. (2009). Eur. J. Med. Chem. 44, 2328-2333.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Taha, M., Baharudin, M. S., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012a). Acta Cryst. E68, o3256.  [CrossRef] [details]
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012b). Acta Cryst. E68, o2780.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3255  [ doi:10.1107/S1600536812042389 ]

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