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Volume 69 
Part 9 
Page o1469  
September 2013  

Received 6 August 2013
Accepted 14 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.083
Data-to-parameter ratio = 15.0
Details
Open access

(E)-2-[(1H-Imidazol-4-yl)methylidene]hydrazinecarbothioamide monohydrate

aLaboratoire de Chimie Inorganique et Environnement, Université de Tlemcen, BP 119, 13000, Tlemcen, Algeria,bCentre de Diffractométrie X, UMR 6226 CNRS, Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France, and cUSMBA, FSDM, Département de Chimie, BP 1796 Fès - Atlas, Morocco
Correspondence e-mail: samhibi1@yahoo.fr

In the title compound, C5H7N5S·H2O, the main molecule is approximately planar, with a maximum deviation from the mean plane through the non-H atoms of 0.1478 (12) Å for the amine N atom. In the crystal, the components are connected via N-H...O, N-H...S and O-H...N hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of thiosimecarbazone derivatives, see: Finch et al. (2000[Finch, R. A., Liu, M., Grill, S. P., Rose, W. C., Loomis, R., Vasquez, K. M., Cheng, Y. & Sartorelli, A. C. (2000). Biochem. Pharmacol. 59, 983-991.]). For the crystal structures of related compounds, see: Alomar et al. (2013[Alomar, K., Landreau, A., Allain, M., Bouet, G. & Larcher, G. (2013). J. of Inorg. Biochem. 126, 76-83.]).

[Scheme 1]

Experimental

Crystal data
  • C5H7N5S·H2O

  • Mr = 187.23

  • Monoclinic, P 21 /c

  • a = 10.8734 (5) Å

  • b = 11.2416 (5) Å

  • c = 7.0822 (3) Å

  • [beta] = 75.601 (2)°

  • V = 838.50 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 150 K

  • 0.4 × 0.23 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 6537 measured reflections

  • 1903 independent reflections

  • 1726 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.06

  • 1903 reflections

  • 127 parameters

  • H-atom parameters not refined

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O21 0.92 (2) 2.34 (2) 3.2325 (16) 163.2 (18)
N8-H8...S1i 0.90 (2) 2.51 (2) 3.3334 (13) 153.0 (18)
O21-H21B...N10 0.87 (2) 2.17 (2) 3.0399 (15) 172 (2)
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CRYSCAL (T. Roisnel, local program).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5642 ).


Acknowledgements

The authors gratefully acknowledge the support of the Algerian Ministry of Higher Education and Scientific Research.

References

Alomar, K., Landreau, A., Allain, M., Bouet, G. & Larcher, G. (2013). J. of Inorg. Biochem. 126, 76-83.  [CSD] [CrossRef] [ChemPort]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Finch, R. A., Liu, M., Grill, S. P., Rose, W. C., Loomis, R., Vasquez, K. M., Cheng, Y. & Sartorelli, A. C. (2000). Biochem. Pharmacol. 59, 983-991.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1469  [ doi:10.1107/S1600536813022927 ]

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