1-Benzyl­idene­amino-3-(4-methyl­phen­yl)thio­urea

Yan-Ling Zhang; Zhi-Hong Xu; Fu-Juan Zhang; Feng-Ling Yang

doi:10.1107/S160053681100198X

. 2011 Jan 22;67(Pt 2):o449. doi: 10.1107/S160053681100198X

1-Benzylideneamino-3-(4-methylphenyl)thiourea

Yan-Ling Zhang ^a, Zhi-Hong Xu ^a, Fu-Juan Zhang ^a, Feng-Ling Yang ^a,^*

PMCID: PMC3051669 PMID: 21523112

Abstract

In the title compound, C₁₅H₁₅N₃S, the almost planar 2-benzylidenehydrazinecarbothioamide unit (r.m.s. deviation = 0.0351 Å) is aligned at a dihedral angle of 64.42 (6)° with respect to the plane of the tolyl ring. The molecule exhibits an E configuration for the azomethine linkage. In the crystal, intermolecular N—H⋯S hydrogen bonds about centers of inversion lead to the formation of dimers.

Related literature

For biological applications of thiosemicarbazones, see: Hu et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₅N₃S
M _r = 269.36
Monoclinic,
a = 10.2359 (3) Å
b = 16.0648 (3) Å
c = 9.9703 (3) Å
β = 117.154 (4)°
V = 1458.81 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.88 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.603, T _max = 0.729
12637 measured reflections
2605 independent reflections
2253 reflections with I > 2σ(I)
R _int = 0.026
Standard reflections: 0

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.120
S = 1.05
2605 reflections
181 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100198X/ng5104sup1.cif

e-67-0o449-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100198X/ng5104Isup2.hkl

e-67-0o449-Isup2.hkl^{(128KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1ⁱ	0.88 (2)	2.48 (2)	3.3522 (15)	170.3 (17)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Natural Science Foundation of the Education Department of Henan Province (2010B150029), the Natural Science Foundation of Henan Province (082300420110) and the Scientific Research Foundation of Xuchang University of Henan Province (2009086) for supporting this work.

supplementary crystallographic information

Comment

Thiosemicarbazones have attracted our attention because of their biological applications (Hu et al., 2006). A few single-crystal reports about them are presented. Detailed information on their molecular and crystal structures is necessary to understand their anticancer activity. The molecular structure of (I) is shown in Fig 1. The molecules exhibit an E configuration.The thiosemicarbazide and benzaldehyde unit are located on opposite sides of the N1=C7 bond.The 2-benzylidenehydrazinecarbothioamide unit has a planar configuration and subtends an angle of 64.42 (6)° with respect to the plane of the tolyl ring.In the crystal structure of the title compound, there is N(2)—H(2)···S(1)#1 hydrogen-bond interactions in molecules which leads to a supramolecular architecture (Fig. 2).

Experimental

N-(p-Tolyl)hydrazinecarbothioamide (2.7 g,15 mmol) and benzaldehyde (1.6 g, 15 mmol) was dissolved in 95% ethanol (20 ml) and the solution was refluxed for 6.5 h. Fine colorless crystals appeared on cooling. They were filtered and washed by 95% ethanol to give 2.6 g of the title compound in 65% yield. Single crystals suitable for X-ray measurements were obtained from 2-propanol by slow evaporation at room temperature.