Benzyl (E)-3-(4-meth­oxy­benzyl­idene)dithio­carbazate

Zheng Fan; Yan-Lan Huang; Zhao Wang; Han-Qi Guo; Shang Shan

doi:10.1107/S1600536811042140

. 2011 Oct 22;67(Pt 11):o3011. doi: 10.1107/S1600536811042140

Benzyl (E)-3-(4-methoxybenzylidene)dithiocarbazate

Zheng Fan ^a, Yan-Lan Huang ^b, Zhao Wang ^b, Han-Qi Guo ^b, Shang Shan ^b,^*

PMCID: PMC3247410 PMID: 22220028

Abstract

The title compound, C₁₆H₁₆N₂OS₂, was obtained from a condensation reaction of benzyl dithiocarbazate and 4-methoxybenzaldehyde. In the molecule, the methoxyphenyl ring and dithiocarbazate fragment are located on opposite sides of the C=N double bond, showing an E configuration. The dithiocarbazate fragment is approximately planar (r.m.s. deviation = 0.0052 Å); its mean plane is oriented at dihedral angles of 8.19 (15) and 85.70 (13)°, respectively, to the methoxyphenyl and phenyl rings. Intermolecular N—H⋯S hydrogen bonds and weak C—H⋯π interactions are observed in the crystal structure.

Related literature

For applications of hydrazone and its derivatives in the biological field, see: Okabe et al. (1993 ▶); Hu et al. (2001 ▶). For related structures, see: Shan et al. (2008a ▶,b ▶). For the synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂OS₂
M _r = 316.43
Monoclinic,
a = 10.267 (5) Å
b = 5.150 (2) Å
c = 31.686 (11) Å
β = 97.141 (5)°
V = 1662.4 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 294 K
0.32 × 0.25 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.84, T _max = 0.92
6025 measured reflections
2982 independent reflections
1869 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.129
S = 1.04
2982 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042140/xu5352sup1.cif

e-67-o3011-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042140/xu5352Isup2.hkl

e-67-o3011-Isup2.hkl^{(143.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042140/xu5352Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1ⁱ	0.86	2.59	3.397 (4)	158
C16—H16C⋯Cgⁱⁱ	0.96	2.83	3.671 (5)	147

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).

supplementary crystallographic information

Comment

Hydrazone and its derivatives have shown the potential application in the biological field (Okabe et al., 1993; Hu et al., 2001). As part of the ongoing investigation on anti-cancer compounds, the title compound has recently been prepared in our laboratory and its crystal structure is presented here.

In the molecules, the methoxylphenyl ring and dithiocarbazate fragment are located on the opposite sides of the C═N double bond, showing the E-configuration. The dithiocarbazate fragment is approximately planar [r.m.s deviation 0.0052 Å]; the mean plane of dithiocarbazate is oriented with respect to the methoxylphenyl and phenyl rings at 8.19 (15) and 85.70 (13)°, similar to those found in related structures (Shan et al. 2008a,b). Intermolecular N—H···S hydrogen bonding and weak C—H···π interaction are observed in the crystal structure (Table 1).

Experimental

Benzyl dithiocarbazate was synthesized as described previously (Hu et al., 2001). Benzyl dithiocarbazate (0.40 g, 2 mmol) and 4-methoxybenzaldehyde (0.27 g, 2 mmol) were dissolved in ethanol (20 ml), then acetic acid (0.2 ml) was added to the ethanol solution with stirring. The mixture solution was refluxed for 6 h. After cooling to room temperature, microcrystals appeared. The microcrystals were separated from the solution and washed with cold water three times. Recrystallization was performed twice with absolute methanol to obtain colourless single crystals of the title compound.