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Volume 69 
Part 5 
Page o644  
May 2013  

Received 5 March 2013
Accepted 26 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.107
Data-to-parameter ratio = 15.7
Details
Open access

1-(2H-1,3-Benzodioxol-5-yl)ethanone thiosemicarbazone

aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil,bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany, and cEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96201-900, Rio Grande-RS, Brazil
Correspondence e-mail: adriano@daad-alumni.de

In the title compound, C10H11N3O2S, the 1,3-benzodioxole and hydrazinecarbothioamide fragments are nearly planar [(mean deviations from planarity for non-H atoms of 0.0325 (12) Å and 0.0707 (10) Å, respectively] and subtend a dihedral angle of 29.06 (5)°. In the crystal, molecules are linked by pairs of almost linear N-H...S hydrogen bonds, forming inversion dimers. These dimers are additionally connected by weaker and strongly bent N-H...S interactions into chains along [101]. There is one additional weak N-H...O contact which, if considered as an interaction, leads to the formation of a three-dimensional network.

Related literature

For the adapted synthesis of the title compound, see: de Oliveira et al. (2012[Oliveira, A. B. de, Silva, C. S., Feitosa, B. R. S., Näther, C. & Jess, I. (2012). Acta Cryst. E68, o2581.]). For the pharmacological activity of 3',4'-(methylenedioxy)acetophenone thiosimecarbazone derivatives, see: Silva et al. (1998[Silva, M. J., Alves, A. J. & Nascimento, S. C. (1998). Il Farmaco, 53, 241-243.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11N3O2S

  • Mr = 237.28

  • Monoclinic, P 21 /c

  • a = 6.1423 (12) Å

  • b = 26.065 (5) Å

  • c = 7.1289 (14) Å

  • [beta] = 109.07 (3)°

  • V = 1078.7 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 200 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Stoe IPDS-1 diffractometer

  • 12310 measured reflections

  • 2315 independent reflections

  • 2018 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.107

  • S = 1.04

  • 2315 reflections

  • 147 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1i 0.88 2.66 3.2207 (17) 123
N1-H2N1...S1ii 0.88 2.53 3.4100 (18) 175
N2-H1N2...S1iii 0.88 2.84 3.5048 (15) 134
Symmetry codes: (i) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA and X-RED32. 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, 2011[Brandenburg, K. (2011). 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: QK2055 ).


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. ABO acknowledges financial support through the FAPITEC/SE/FUNTEC/CNPq PPP 04/2011 program.

References

Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Oliveira, A. B. de, Silva, C. S., Feitosa, B. R. S., Näther, C. & Jess, I. (2012). Acta Cryst. E68, o2581.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Silva, M. J., Alves, A. J. & Nascimento, S. C. (1998). Il Farmaco, 53, 241-243.  [PubMed]
Stoe & Cie (2008). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o644  [ doi:10.1107/S1600536813008398 ]

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