1-(4-Chloro­phen­yl)-3-{5-[(E)-2-phenyl­ethen­yl]-1,3,4-thia­diazol-2-yl}urea

Xiu-Huan Zhan; Zi-Yun Wang

doi:10.1107/S1600536811002479

. 2011 Jan 29;67(Pt 2):o510. doi: 10.1107/S1600536811002479

1-(4-Chlorophenyl)-3-{5-[(E)-2-phenylethenyl]-1,3,4-thiadiazol-2-yl}urea

Xiu-Huan Zhan ^a, Zi-Yun Wang ^a,^*

PMCID: PMC3051607 PMID: 21523161

Abstract

In the title compound, C₁₇H₁₃ClN₄OS, the 1,3,4-thiadiazole ring makes dihedral angles of 9.70 (15) and 7.22 (10)° with the benzene and phenyl rings, respectively; the dihedral angle between these two rings is 6.37 (19)°. In the crystal, pairs of N—H⋯N and C—H⋯O hydrogen bonds between inversion-related molecules result in supramolecular ribbons displaying alternate R ₂ ²(8) and R ₂ ²(14) graph-set ring motifs.

Related literature

For the biological activity of urea derivatives, see: Abad et al. (2004 ▶); Chen et al. (2005 ▶); Yonova & Stoilkova (2005 ▶). For the biological activity of 1,3,4-thiadiazole derivatives, see: Guzeldemirci & Kucukbasmaci (2010 ▶); Song & Tan (2008 ▶); Zou et al. (2002 ▶). For the synthesis, see: Song et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₃ClN₄OS
M _r = 356.82
Monoclinic,
a = 11.2399 (6) Å
b = 4.1032 (2) Å
c = 35.2497 (16) Å
β = 91.525 (4)°
V = 1625.12 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 298 K
0.40 × 0.06 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer
10860 measured reflections
3708 independent reflections
2081 reflections with I > 2σ(I)
R _int = 0.091

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.154
S = 1.01
3708 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002479/is2664sup1.cif

e-67-0o510-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002479/is2664Isup2.hkl

e-67-0o510-Isup2.hkl^{(181.8KB, 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
C2—H2⋯O1ⁱ	0.93	2.55	3.432 (4)	159
N2—H2A⋯N3ⁱⁱ	0.82 (4)	2.03 (4)	2.848 (4)	174 (3)

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

Acknowledgments

The authors acknowledge financial support from the Scientific Research Fund of Henan Provincial Education Department, China (grant Nos. 2007150050 and 2009B150030).

supplementary crystallographic information

Comment

Urea derivatives have attracted much attention on the account of their interesting biological effects, such as insecticidal, fungicidal, herbicidal and plant-growth regulating activities (Abad et al., 2004; Chen et al., 2005), especially cytokinin acyivity (Yonova & Stoilkova, 2005). 1,3,4-Thiadiazole derivatives are known to exhibit a wide range of biological activities (Zou et al., 2002; Song & Tan, 2008; Guzeldemirci & Kucukbasmaci, 2010). In view of our extensive interest and as a continuing search for new urea-type cytokinins, we investigate the urea derivatives incorporating a 1,3,4-thiadiazole nucleus, including the title compound.

The crystal structure (Fig.1) revealed that the title molecule which consists of three rings is approximately planar, the dihedral angles formed by the thiadiazole ring with the chlorophenyl and vinylphenyl rings being only 9.70 (15) and 7.22 (10)°, respectively, and the styryl moiety assumes a trans-configuration about C10═C11 double bond of the vinyl moiety. All bond lengths and angles are as expected. In the crystal structure, intermolecular N—H···N and C—H···O hydrogen bonds occurring between centrosymmetrically related molecules result in the formation of ribbons displaying alternate rings of graph-set motifs R₂²(8) and R₂²(14), as shown in Fig. 2 and Table 1.

Experimental

The title compound was prepared according to the procedure of Song et al. (2007). Suitable crystals were obtained by vapor diffusion of methanol in DMF at room temperature (m.p. >573 K). Elemental analysis: analysis calculated for C₁₇H₁₃ClN₄OS: C 57.22, H 3.67, N 15.70%; found: C 57.45, H 3.56, N 15.82%.