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Volume 69 
Part 12 
Page o1861  
December 2013  

Received 21 October 2013
Accepted 27 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.100
Data-to-parameter ratio = 15.9
Details
Open access

4-Hy­droxy-3-meth­oxy­benzaldehyde thio­semicarbazone

aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil, and bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany
Correspondence e-mail: adriano@daad-alumni.de

In the title compound, C9H11N3S, there is an intra­molecular O-H...O hydrogen bond involving the OH group and the adjacent methoxy O atom. The mol­ecule is essentially planar, with the maximum deviation from the mean plane of the non-H atoms being 0.1127 (14) Å for the methyl C atom. In the crystal, mol­ecules are connected via centrosymmetric pairs of N-H...S and O-H...O hydrogen bonds into a two-dimensional network parallel to (10-3).

Related literature

For the in vitro anti­malarial and anti­tubercular activity of hy­droxy-meth­oxy­benzaldehyde thio­semicarbazone derivatives, see: Khanye et al. (2011[Khanye, S. D., Wan, B., Franzblau, S. G., Gut, J., Rosenthal, P. J., Smith, G. S. & Chibale, K. (2011). J. Organomet. Chem. 696, 3392-3396.]). For the first report of the synthesis, see: Freund & Schander (1902[Freund, M. & Schander, A. (1902). Chem. Ber. 35, 2602-2606.]). For the synthesis and crystal structure of an isomer of the title compound, see: Hao (2010[Hao, Y.-M. (2010). Acta Cryst. E66, o2211.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11N3O2S

  • Mr = 225.27

  • Triclinic, [P \overline 1]

  • a = 4.5886 (5) Å

  • b = 8.5213 (11) Å

  • c = 13.9621 (15) Å

  • [alpha] = 75.898 (13)°

  • [beta] = 87.669 (13)°

  • [gamma] = 77.580 (14)°

  • V = 517.05 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 200 K

  • 0.4 × 0.3 × 0.2 mm

Data collection
  • Stoe IPDS-1 diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.865, Tmax = 0.982

  • 5179 measured reflections

  • 2211 independent reflections

  • 1829 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.100

  • S = 1.03

  • 2211 reflections

  • 139 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.84 2.24 2.6934 (16) 114
O1-H1...O2i 0.84 2.27 2.9153 (15) 134
N2-H2A...S1ii 0.88 2.59 3.4319 (14) 161
N3-H3B...S1iii 0.88 2.59 3.4540 (15) 169
Symmetry codes: (i) -x-1, -y+1, -z; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y+2, -z+1.

Data collection: X-AREA (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: FY2108 ).


Acknowledgements

We gratefully acknowledge financial support by the State of Schleswig-Holstein, Germany. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities. BRSF thanks CNPq/UFS for the award of a PIBIC scholarship and ABO acknowledges financial support through the FAPITEC/SE/FUNTEC/CNPq PPP 04/2011 program.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Freund, M. & Schander, A. (1902). Chem. Ber. 35, 2602-2606.  [ChemPort]
Hao, Y.-M. (2010). Acta Cryst. E66, o2211.  [CSD] [CrossRef] [IUCr Journals]
Khanye, S. D., Wan, B., Franzblau, S. G., Gut, J., Rosenthal, P. J., Smith, G. S. & Chibale, K. (2011). J. Organomet. Chem. 696, 3392-3396.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1861  [ doi:10.1107/S1600536813032303 ]

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