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Volume 68 
Part 12 
Page o3256  
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 = 0.042
wR = 0.115
Data-to-parameter ratio = 12.7
Details
Open access

N'-[(E)-2,3-Dihydroxybenzylidene]-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 title compound, C15H14N2O4 adopts an E conformation about the azomethine double bond. Intramolecular N-H...O and O-H...N hydrogen bonds generate S(6) rings and help to establish the molecular conformation. The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, molecules are linked by O-H...O and C-H...O hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.

Related literature

For applications and the 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., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.]); Jarahpour et al. (2007[Jarahpour, A., Khalili, D., De Clercq, E., Salmi, C. & Brunel, J. M. (2007). Molecules. 12, 1720-1730.]). For related structures, see: Baharudin et al. (2012[Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255.]); Taha et al. (2012[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.]); Promdet et al. (2011[Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O4

  • Mr = 286.28

  • Orthorhombic, P b c a

  • a = 14.1479 (17) Å

  • b = 8.6567 (11) Å

  • c = 22.570 (3) Å

  • V = 2764.2 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 273 K

  • 0.56 × 0.18 × 0.04 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 = 0.945, Tmax = 0.996

  • 15288 measured reflections

  • 2574 independent reflections

  • 1658 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.115

  • S = 1.03

  • 2574 reflections

  • 203 parameters

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

  • [Delta][rho]max = 0.14 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
N1-H1A...O2 0.91 (2) 1.90 (2) 2.608 (2) 133 (2)
O3-H3A...O1i 0.90 (3) 1.75 (3) 2.631 (2) 167 (2)
O4-H4A...N2 0.85 (2) 1.89 (2) 2.658 (2) 151 (2)
C8-H8A...O3ii 0.93 2.33 3.189 (2) 153
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, y, -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: PV2594 ).


References

Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255.  [CrossRef] [details]
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., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.  [CrossRef] [PubMed] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Panneerselvam, P., Rather, B. A., Reddy, D. R. S. & Kumar, R. N. (2009). Eur. J. Med. Chem. 44, 2328-2333.  [ISI] [CrossRef] [PubMed] [ChemPort]
Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224.  [CSD] [CrossRef] [details]
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., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3256  [ doi:10.1107/S1600536812042390 ]

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