3-[(Cyclo­hexyl­idene)amino]-1-(4-methyl­phen­yl)thio­urea

Yan-Ling Zhang; Xiao-Wei Zhang; Fu-Juan Zhang

doi:10.1107/S1600536811015510

. 2011 Apr 29;67(Pt 5):o1268. doi: 10.1107/S1600536811015510

3-[(Cyclohexylidene)amino]-1-(4-methylphenyl)thiourea

Yan-Ling Zhang ^a,^*, Xiao-Wei Zhang ^a, Fu-Juan Zhang ^a

PMCID: PMC3089110 PMID: 21754554

Abstract

In the title compound, C₁₄H₁₉N₃S, the cyclohexane ring has a chair conformation. The almost planar aminothiourea unit (r.m.s. deviation = 0.0062 Å) is aligned at a dihedral angle of 45.23 (8)° with respect to the benzene ring. Intermolecular N—H⋯N and N—H⋯S hydrogen bonding stabilizes the crystal structure.

Related literature

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

Experimental

Crystal data

C₁₄H₁₉N₃S
M _r = 261.38
Orthorhombic,
a = 14.9151 (4) Å
b = 22.5593 (5) Å
c = 17.1642 (3) Å
V = 5775.3 (2) Å³
Z = 16
Cu Kα radiation
μ = 1.87 mm⁻¹
T = 291 K
0.40 × 0.25 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.521, T _max = 0.652
7202 measured reflections
2583 independent reflections
2024 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.162
S = 1.02
2583 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015510/xu5197sup1.cif

e-67-o1268-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015510/xu5197Isup2.hkl

e-67-o1268-Isup2.hkl^{(127.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811015510/xu5197Isup3.cml

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
N1—H1⋯N3ⁱ	0.89 (3)	2.48 (3)	3.268 (3)	148 (2)
N2—H2⋯S1ⁱⁱ	0.86 (3)	2.70 (3)	3.531 (2)	164 (3)

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

Acknowledgments

The authors thank the Natural Science Foundation of the Education Department of Henan Province, China (2010B150029), the Natural Science Foundation of Henan Province, China (112102310538, 082300420110) and the Scientific Research Foundation of Xuchang University, China (2009086) for supporting this work.

supplementary crystallographic information

Comment

Thiosemicarbazones have attracted much attention as they show potential application in the biological field (Hu et al., 2006). There are a few single-crystal reports about them. 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 cyclohexane ring adopts a chair conformation. The almost planar aminothiourea unit (r.m.s. deviation = 0.0062 Å) is aligned at a dihedral angle of 45.23 (8)° with respect to the plane of the benzene ring. In the crystal structure of the title compound, there are N—H···N an N—H···S hydrogen-bond interactions (Table 1).

Experimental

N-(p-Tolyl)thiosemicarbazide (1.8 g, 10 mmol) and cyclohexanone (0.98 g, 10 mmol) was dissolved in 95% ethanol (15 ml) and the solution was refluxed for 0.5 h. Fine colorless crystals appeared on cooling. They were filtered and washed by 95% ethanol to give 1.6 g of the title compound in 61.5% yield. Single crystals suitable for X-ray measurements were obtained from methanol by slow evaporation at room temperature.