Benzyl 3-[(E,E)-3-phenyl­prop-2-enyl­idene]dithio­carbazate

Tarafder, M.T.H.; Crouse, K.A.; Islam, M.T.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536808013354

Volume 64
Part 6
Pages o1042-o1043
June 2008

Received 3 May 2008
Accepted 6 May 2008
Online 10 May 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.093
Data-to-parameter ratio = 18.4
Details

Benzyl 3-[(E,E)-3-phenylprop-2-enylidene]dithiocarbazate

M. T. H. Tarafder,^a ^* K. A. Crouse,^b M. Toihidul Islam,^c Suchada Chantrapromma ^d ⁺ and Hoong-Kun Fun ^e ⁺⁺

^aDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh,^bDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia,^cDepartment of Chemistry, Rajshahi University of Engineering and Technology, Rajshahi 6205, Bangladesh,^dDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^eX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: ttofazzal@yahoo.com

The title compound, C₁₇H₁₆N₂S₂, a dithiocarbazate derivative, adopts an EE configuration with respect to the C=C and C=N double bonds of the propenylidine group. The 3-phenylprop-2-enylidene and dithiocarbazate fragments lie essentially in the same plane, with a maximum deviation from that plane of 0.074 (2) Å, while the dihedral angle between the 3-phenylprop-2-enylidene and the benzyl group is 77.78 (7)°. In the crystal structure, molecules are linked by an N-HS hydrogen bond and a weak C-HS interaction involving the terminal thione S atom, forming dimers that are arranged into sheets parallel to the bc plane. The crystal structure is also stabilized by C-H [pi] interactions.

Related literature

For information on values of bond lengths, see Allen et al. (1987). For related structures of dithiocarbazate derivatives, see, for example: Crouse et al. (2004); Fun et al. (2008); Shanmuga Sundara Raj et al. (2000). For applications and bioactivities of dithiocarbazate derivatives, see, for example: Ali & Tarafder (1977); Ali et al. (2001, 2002, 2008); Chan et al. (2008); Chew et al. (2004); Crouse et al. (2004); Tarafder et al. (1978, 1981, 2001, 2008).

Experimental

Crystal data

C₁₇H₁₆N₂S₂
M_r = 312.44
Triclinic, $[P \overline 1]$
a = 5.4350 (3) Å
b = 11.6333 (7) Å
c = 13.6289 (8) Å
= 66.869 (4)°
= 82.723 (4)°
= 87.520 (4)°
V = 786.04 (8) Å³
Z = 2
Mo K radiation
= 0.33 mm^-1
T = 100.0 (1) K
0.58 × 0.19 × 0.05 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.829, T_max = 0.982
16100 measured reflections
3570 independent reflections
2870 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.092
S = 1.07
3570 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1S2ⁱ	0.87 (2)	2.53 (2)	3.3714 (19)	165 (2)
C9-H9AS2ⁱ	0.93	2.93	3.7264 (18)	144
C15-H15ACg1ⁱⁱ	0.93	2.83	3.649 (2)	148
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+2. Cg1 is the centroid of the C1-C6 phenyl ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2494 ).

Acknowledgements

KAC thanks Universiti Putra Malaysia for financial help. MTHT thanks the University of Rajshahi for the provision of laboratory facilities. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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organic compounds