[Journal logo]

Volume 69 
Part 8 
Page o1249  
August 2013  

Received 18 June 2013
Accepted 8 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.071
wR = 0.195
Data-to-parameter ratio = 29.9
Details
Open access

N'-(2,4-Dinitrophenyl)acetohydrazide monohydrate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and bChemistry Department, Faculty of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia
Correspondence e-mail: houda_marouani@voila.fr

In the crystal structure of the title compound, C8H8N4O5·H2O, the organic and lattice water molecules are linked together via N-H...O and O-H...O hydrogen bonds. A C-H...O interaction is also observed between the organic molecules. These hydrogen bonds and interactions lead to the formation of a three-dimensional network. An intramolecular N-H...O hydrogen bond also occurs. The dihedral angle between the acetyl group and the almost planar hydrazide moiety [maximum deviation from the least-squares plane is 0.209 (2) Å for one of the nitro O atoms] is 88.5 (3)°.

Related literature

For background to the biological activity of hydrazines and hydrazones, see: Zahid & Sherazi (1997[Zahid, H. C. & Sherazi, S. K. A. (1997). Met. Based Drugs, 4, 327-332.]); Monfared et al. (2007[Monfared, H. H., Pouralimardan, O. & Janiak, C. (2007). Z. Naturforsch. Teil B, 62, 717-720.]). For a related crystal structure, see: Okabe et al. (1993[Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., David, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8N4O5·H2O

  • Mr = 258.20

  • Monoclinic, P 21 /c

  • a = 7.702 (2) Å

  • b = 7.057 (3) Å

  • c = 21.550 (4) Å

  • [beta] = 109.044 (19)°

  • V = 1107.3 (6) Å3

  • Z = 4

  • Ag K[alpha] radiation

  • [lambda] = 0.56083 Å

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.5 × 0.4 × 0.3 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 7469 measured reflections

  • 5411 independent reflections

  • 2771 reflections with I > 2[sigma](I)

  • Rint = 0.064

  • 2 standard reflections every 120 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.195

  • S = 0.98

  • 5411 reflections

  • 181 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
OW-H1W...O5 0.86 (1) 1.91 (1) 2.759 (3) 175 (3)
OW-H2W...O4i 0.84 (1) 2.05 (1) 2.868 (3) 165 (3)
N1-H1N...OWii 0.88 (3) 2.04 (3) 2.883 (3) 160 (2)
N2-H2N...O1 0.90 (3) 1.96 (3) 2.607 (2) 128 (2)
N2-H2N...OWiii 0.90 (3) 2.15 (3) 2.910 (3) 142 (2)
C6-H6...O5iv 0.93 2.40 3.310 (3) 165
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y-1, z; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS86 (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 & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal impact GbR, Bonn, Germany.]); 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: PV2637 ).


Acknowledgements

This work was supported by the Tunisian Ministry of HEScR, and the Deanship of Scientific Research at King Saud University is also thanked for funding the paper through the Research Group Project No. RGP-VPP-089.

References

Bernstein, J., David, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal impact GbR, Bonn, Germany.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Monfared, H. H., Pouralimardan, O. & Janiak, C. (2007). Z. Naturforsch. Teil B, 62, 717-720.
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zahid, H. C. & Sherazi, S. K. A. (1997). Met. Based Drugs, 4, 327-332.  [PubMed]


Acta Cryst (2013). E69, o1249  [ doi:10.1107/S1600536813018916 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.