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

Break, M.K. bin; Mehta, S.; Tahir, M.I.M.; Crouse, K.A.; Khoo, T.-J.

doi:10.1107/S1600536812051008

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 (C-C) = 0.004 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 16.9
Details

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

Mohammed Khaled bin Break,^a Sachin Mehta,^a M. Ibrahim M. Tahir,^b Karen A. Crouse ^b and Teng-Jin Khoo ^a ^*

^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-HS and N-HS 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); Tarafder et al. (2002). For related structures derived from S-benzyldithiocarbazate, which exhibit a similar geometry to the title compound, see: Khoo et al. (2005); How et al. (2007); Shan et al. (2011). For the synthesis, see: Tarafder et al. (2002).

Experimental

Crystal data

C₁₂H₁₆N₂S₃
M_r = 284.47
Monoclinic, P 2₁ /c
a = 16.3887 (4) Å
b = 8.3136 (2) Å
c = 10.1404 (3) Å
= 90.234 (2)°
V = 1381.61 (6) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.31, T_max = 0.68
7359 measured reflections
2615 independent reflections
2374 reflections with I > 2(I)
R_int = 0.027
Standard reflections: 0

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.123
S = 0.99
2605 reflections
154 parameters
H-atom parameters constrained
_max = 0.55 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-HA	D-H	HA	DA	D-HA
S15-H151S3ⁱ	1.38	2.96	4.186 (1)	146
N11-H111S1ⁱⁱ	0.86	2.72	3.567 (2)	168
C7-H71Cgⁱⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
Hossain, E., Alam, M., Ali, M., Nazimuddin, M., Smith, E. & Hynes, C. (1996). Polyhedron, 15, 973-980.
How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023-o3024.
Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.
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.
Shan, S., Huang, Y.-L., Guo, H.-Q., Li, D.-F. & Sun, J. (2011). Acta Cryst. E67, o2105.
Tarafder, M., Khoo, T. J., Crouse, A., Ali, M., Yamin, B. & Fun, H. (2002). Polyhedron, 21, 2691-2698.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds