Benzyl N′-(2-chloro­benzyl­idene)hydrazinecarbodithio­ate

Shi, Z.-Q.; Ji, N.-N.; Ji, Q.-Q.

doi:10.1107/S1600536808034892

Volume 64
Part 12
Page o2249
December 2008

Received 20 September 2008
Accepted 27 October 2008
Online 8 November 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 15.3
Details

Benzyl N'-(2-chlorobenzylidene)hydrazinecarbodithioate

Zhi-Qiang Shi,^a ^* Ning-Ning Ji ^b and Qin-Qin Ji ^c

^aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China,^bDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^cDepartment of Chemical Engineering and Technology, School of Chemical Engineering and Technology, China University of Mining and Technology, 221116 Xuzhou, Jiangsu, People's Republic of China
Correspondence e-mail: kobeecho@163.com

The asymmetric unit of the title compound, C₁₅H₁₃ClN₂S₂, contains two independent molecules, which are linked into a pseudo-centrosymmetric dimer by intermolecular N-HS hydrogen bonds. The aromatic rings form dihedral angles of 67.06 (3) and 81.85 (2)° in the two independent molecules.

Related literature

For the biomedical properties of ligands derived from S-benzyldithiocarbazate, see: Ali et al. (2001, 2002); Tarafder et al. (2001, 2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₃ClN₂S₂
M_r = 320.84
Triclinic, $[P \overline 1]$
a = 11.877 (2) Å
b = 11.906 (2) Å
c = 12.623 (3) Å
= 68.242 (3)°
= 71.116 (4)°
= 82.335 (4)°
V = 1568.4 (5) Å³
Z = 4
Mo K radiation
= 0.50 mm^-1
T = 295 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.942, T_max = 0.971
8397 measured reflections
5524 independent reflections
3436 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.127
S = 0.97
5524 reflections
361 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S4	0.86	2.56	3.405 (3)	166
N3-H3AS2	0.86	2.60	3.451 (3)	169

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 and SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL .

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2453 ).

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06-2-08).

References

Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Ali, A. M. & Manaf, A. (2001). Inorg. Chim. Acta, 320, 1-6.
Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B., Ali, A. M. & &Manaf, A. (2002). J. Inorg. Biochem. 92, 141-148.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tarafder, M. T. H., Islam, M. T., Islam, M. A. A. A. A., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, m416-m417.
Tarafder, M. T. H., Kasbollah, A., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2001). Polyhedron, 20, 2363-2370.

organic compounds