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Volume 69 
Part 6 
Page o881  
June 2013  

Received 14 April 2013
Accepted 6 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 8.0
Details
Open access

N'-[(E)-2-Hydroxy-5-methoxybenzylidene]pyridine-4-carbohydrazide monohydrate

aDepartment of Chemistry and Research Centre, PRNSS College, Mattanur 670 702, Kannur, Kerala, India,bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
Correspondence e-mail: eesans@yahoo.com

The title compound, C14H13N3O3·H2O, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. An intramolecular O-H...N hydrogen bond occurs. In the crystal, the lattice water molecule plays a major role in the supramolecular architecture by interconnecting adjacent molecules into a three-dimensional netwrok by means of O-H...O, O-H...N and N-H...O hydrogen-bonding interactions. The structure also features two non-classical C-H...O interactions.

Related literature

For properties of carbohydrazide and its derivatives, see: Mangalam & Kurup (2011[Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 76, 22-28.]). For molecular sensing of metals, see: Bakir & Brown (2002[Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129-136.]). For related structures and background references, see: Kargar et al. (2010[Kargar, H., Kia, R., Akkurt, M. & Büyükgüngör, O. (2010). Acta Cryst. E66, o2982.]); Shafiq et al. (2009[Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2899.]); Sithambaresan & Kurup (2011[Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o2972.]). For the synthesis, see: Mangalam et al. (2009[Mangalam, N. A., Sivakumar, S., Sheeja, S. R., Kurup, M. R. P. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 4191-4197.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N3O3·H2O

  • Mr = 289.29

  • Orthorhombic, P n a 21

  • a = 12.6455 (16) Å

  • b = 12.7423 (16) Å

  • c = 8.9306 (9) Å

  • V = 1439.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.40 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.976

  • 10294 measured reflections

  • 1668 independent reflections

  • 1134 reflections with I > 2[sigma](I)

  • Rint = 0.056

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.00

  • 1668 reflections

  • 208 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.17 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
N2-H2'...O1Si 0.89 (1) 1.91 (1) 2.784 (4) 168 (4)
O1S-H1A...O3ii 0.86 (1) 1.92 (2) 2.764 (4) 170 (4)
O1S-H1B...N3iii 0.86 (1) 2.05 (2) 2.874 (5) 160 (4)
O2-H2A...N1 0.85 (1) 1.89 (3) 2.642 (4) 147 (4)
C11-H11...O1iv 0.93 2.46 3.370 (5) 164
C14-H14C...O3v 0.96 2.58 3.425 (5) 147
Symmetry codes: (i) x-1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iii) [-x+1, -y, z-{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{3\over 2}}]; (v) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2628 ).


Acknowledgements

MKP thanks the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK thanks the UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the data collection.

References

Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129-136.  [ISI] [CrossRef] [ChemPort]
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kargar, H., Kia, R., Akkurt, M. & Büyükgüngör, O. (2010). Acta Cryst. E66, o2982.  [CSD] [CrossRef] [details]
Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 76, 22-28.
Mangalam, N. A., Sivakumar, S., Sheeja, S. R., Kurup, M. R. P. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 4191-4197.  [ISI] [CSD] [CrossRef] [ChemPort]
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2899.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o2972.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o881  [ doi:10.1107/S160053681301235X ]

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