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Volume 69 
Part 2 
Page o178  
February 2013  

Received 15 November 2012
Accepted 17 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 16.9
Details
Open access

Benzyl N-[(Z)-(1-methyl-2-sulfanylpropylidene)amino]carbamodithioate

aSchool of Pharmacy, University of Nottingham Malaysia Campus, Selangor, Malaysia, and bDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, Malaysia
Correspondence e-mail: tengjin.khoo@nottingham.edu.my

The title compound, C12H16N2S3, was obtained by the condensation reaction of S-benzyl dithiocarbazate and 3-mercaptobutan-2-one. The phenyl ring and thiol (SH) group are approximately perpendicular [S-C-C-C and N-C-C-S torsion angles = 67.8 (3) and 116.9 (2)°, respectively] to the rest of the molecule. In the crystal, molecules are linked by weak S-H...S and N-H...S hydrogen bonds, [pi]-[pi] interactions between the benzene rings [centroid-centroid distance = 3.823 (2) Å] and C-H...[pi] interactions.

Related literature

For biological applications of Schiff base ligands and complexes derived from S-benzyldithiocarbazate, see: Hossain et al. (1996[Hossain, E., Alam, M., Ali, M., Nazimuddin, M., Smith, E. & Hynes, C. (1996). Polyhedron, 15, 973-980.]); Tarafder et al. (2002[Tarafder, M., Khoo, T. J., Crouse, A., Ali, M., Yamin, B. & Fun, H. (2002). Polyhedron, 21, 2691-2698.]). For related structures derived from S-benzyldithiocarbazate, which exhibit a similar geometry to the title compound, see: Khoo et al. (2005[Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.]); How et al. (2007[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023-o3024.]); Shan et al. (2011[Shan, S., Huang, Y.-L., Guo, H.-Q., Li, D.-F. & Sun, J. (2011). Acta Cryst. E67, o2105.]). For the synthesis, see: Tarafder et al. (2002[Tarafder, M., Khoo, T. J., Crouse, A., Ali, M., Yamin, B. & Fun, H. (2002). Polyhedron, 21, 2691-2698.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16N2S3

  • Mr = 284.47

  • Monoclinic, P 21 /c

  • a = 16.3887 (4) Å

  • b = 8.3136 (2) Å

  • c = 10.1404 (3) Å

  • [beta] = 90.234 (2)°

  • V = 1381.61 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 4.73 mm-1

  • T = 100 K

  • 0.25 × 0.10 × 0.08 mm

Data collection
  • Oxford Diffraction Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]) Tmin = 0.31, Tmax = 0.68

  • 7359 measured reflections

  • 2615 independent reflections

  • 2374 reflections with I > 2[sigma](I)

  • Rint = 0.027

  • Standard reflections: 0

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.123

  • S = 0.99

  • 2605 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-H...A D-H H...A D...A D-H...A
S15-H151...S3i 1.38 2.96 4.186 (1) 146
N11-H111...S1ii 0.86 2.72 3.567 (2) 168
C7-H71...Cgiii 0.95 2.97 3.827 (3) 152
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+2, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); 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: NK2192 ).


Acknowledgements

The authors thank the Ministry of Higher Education Malaysia (MOHE) under FRGS (F0010.54.02) for providing a grant for this study.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [ISI] [CrossRef] [details]
Hossain, E., Alam, M., Ali, M., Nazimuddin, M., Smith, E. & Hynes, C. (1996). Polyhedron, 15, 973-980.  [CrossRef] [ChemPort] [ISI]
How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023-o3024.  [CSD] [CrossRef] [details]
Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Shan, S., Huang, Y.-L., Guo, H.-Q., Li, D.-F. & Sun, J. (2011). Acta Cryst. E67, o2105.  [CSD] [CrossRef] [details]
Tarafder, M., Khoo, T. J., Crouse, A., Ali, M., Yamin, B. & Fun, H. (2002). Polyhedron, 21, 2691-2698.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o178  [ doi:10.1107/S1600536812051008 ]

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