(Z)-N-{3-[(6-Chloro­pyridin-3-yl)meth­yl]-1,3-thia­zolidin-2-yl­idene}cyanamide

Jin-Sheng Gao; Jun Qiao; Ying-Hui Yu; Guang-Feng Hou

doi:10.1107/S1600536811013316

. 2011 Apr 16;67(Pt 5):o1140. doi: 10.1107/S1600536811013316

(Z)-N-{3-[(6-Chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide

Jin-Sheng Gao ^a,^b,^*, Jun Qiao ^a, Ying-Hui Yu ^a, Guang-Feng Hou ^b

PMCID: PMC3089287 PMID: 21754449

Abstract

The asymmetric unit of the title compound, C₁₀H₉ClN₄S, common name thiacloprid, comprises two molecules. In both molecules, the thiazolidine rings are almost planar (with r.m.s. deviations of 0.016 and 0.065 Å) and form dihedral angles of 73.36 (6) and 70.25 (8)° with the 2-chloropyridine rings. In the crystal, intermolecular C—H⋯N hydrogen bonds links the molecules into chains propagating in [ Inline graphic 01].

Related literature

For background to the title compound, a member of the neonicotinoide class of insecticides, see Maienfisch et al. (2003 ▶). For the synthesis, see Ishimitsu et al., (1991 ▶)

Experimental

Crystal data

C₁₀H₉ClN₄S
M _r = 252.73
Monoclinic,
a = 7.1294 (14) Å
b = 35.469 (7) Å
c = 9.0211 (18) Å
β = 97.80 (3)°
V = 2260.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 K
0.31 × 0.29 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.863, T _max = 0.909
21869 measured reflections
5151 independent reflections
3505 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.137
S = 1.08
5151 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013316/kp2319sup1.cif

e-67-o1140-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013316/kp2319Isup2.hkl

e-67-o1140-Isup2.hkl^{(252.3KB, 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
C3—H3⋯N5ⁱ	0.93	2.55	3.459 (4)	167
C13—H13⋯N1ⁱⁱ	0.93	2.49	3.408 (4)	169

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

Acknowledgments

The authors thank the Special Funds for the Research of Scientific and Technological Innovative Talents of Harbin Municipal Science and Technology Bureau (2009RFXXG027), the Science and Technology Planning Project of Heilongjiang Province (GZ08A401) and Heilongjiang University for supporting this study.

supplementary crystallographic information

Comment

Thiacloprid is the common name of the title compound, which is neonicotinoide class of insecticide. High efficacy and flexible application methods make it well suited for modern integrated pest management programs in many cropping systems (Ishimitsu et al., 1991; Maienfisch et al., 2003). We report here the synthesis and crystal structure of thiacloprid.

The asymmetric unit comprises two molecules; the thiazolidine rings are almost planar, and form the dihedral angles with 2-chloropyridine rings of 73.36 (6) and 70.25 (8)°, respectively (Fig. 1).

In the crystal, the intermolecular C—H···N hydrogen bonds link the molecules to form a chain (Fig. 2, Table 1).

Experimental

The title compound was synthesised according the reference (Ishimitsu et al., 1991). A mixture of 2-cyanoiminothiazolidine (12.7 g, 0.1 mol), 2-chloro-5-pyridylmethyl-chloride (17.4 g, 0.1 mol), and K₂CO₃ (41.4 g, 0.3 mol) in 150 mL of DMF was heated to 323 K and kept stirring for 7 h. After filtered under reduced pressure, the DMF solution was distilled off. A total of 20.2 g (80.2%) title compound was obtained after the recrystallisation from ethyl acetate (15 mL). The suitable colourless block crystal was picked out for the single crystal X-ray diffaction measurement.