Methidathion: S-(5-meth­oxy-2-oxo-2,3-dihydro-1,3,4-thia­diazol-3-yl)methyl O,O-dimethyl phospho­rodithio­ate

Hyunjee Kim; Yong Woon Shin; Ki-Min Park; Jineun Kim; Tae Ho Kim

doi:10.1107/S1600536811005241

. 2011 Feb 19;67(Pt 3):o653. doi: 10.1107/S1600536811005241

Methidathion: S-(5-methoxy-2-oxo-2,3-dihydro-1,3,4-thiadiazol-3-yl)methyl O,O-dimethyl phosphorodithioate

Hyunjee Kim ^a, Yong Woon Shin ^b, Ki-Min Park ^a,^*, Jineun Kim ^a, Tae Ho Kim ^a,^*

PMCID: PMC3052021 PMID: 21522405

Abstract

The title compound, C₆H₁₁N₂O₄PS₃, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the thiadiazole ring planes and the PS₂ planes of the phosphorodithioate group are 86.51 (5) and 56.33 (5)° in the two molecules. In the crystal, weak intermolecular S⋯S [3.570 (8) Å] interactions and C—H⋯O and C—H⋯N hydrogen bonds contribute to the stabilization of the packing.

Related literature

For the toxicity and insecticidal activity of the title compound, see: Altuntas et al. (2002 ▶). For related structures, see: Rohrbaugh et al. (1976 ▶).

Experimental

Crystal data

C₆H₁₁N₂O₄PS₃
M _r = 302.32
Monoclinic,
a = 12.3944 (2) Å
b = 10.8056 (1) Å
c = 19.3631 (3) Å
β = 102.815 (1)°
V = 2528.68 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 173 K
0.30 × 0.27 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.815, T _max = 0.877
20918 measured reflections
5513 independent reflections
4682 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.089
S = 1.07
5513 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005241/jh2268sup1.cif

e-67-0o653-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005241/jh2268Isup2.hkl

e-67-0o653-Isup2.hkl^{(269.9KB, 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
C1—H1A⋯O7ⁱ	0.98	2.53	3.464 (3)	159
C1—H1B⋯O5ⁱⁱ	0.98	2.53	3.484 (3)	164
C2—H2B⋯O6ⁱⁱⁱ	0.98	2.59	3.373 (3)	138
C3—H3A⋯N2ⁱ	0.99	2.56	3.506 (3)	161
C9—H9B⋯O3	0.99	2.42	3.246 (2)	140

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

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0009089).

supplementary crystallographic information

Comment

Methidathion (systematic name: S-2,3-dihydro-5-methoxy-2-oxo-1,3,4- thiadiazol-3-ylmethyl O,O-dimethyl phosphorodithioate), is one of the most widely used organophosphate insecticides in agriculture and public health programmes (Altuntas et al. 2002). However it's crystal structure has not been reported yet.

In the title compound (Scheme 1, Fig. 1), crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the thiadiazol ring planes and the PS₂ planes of the phosphorodithioate group are 86.51 (5)° and 56.33 (5)° in the two molecules. All bond lengths and bond angles are normal and comparable to those observed in similar structures (Rohrbaugh et al. 1976).

In the crystal structure, as shown in Fig. 2, weak intermolecular C—H···O, C—H···N hydrogen bonds (Table 1) and S···S interactions with 3.3372 (8) Å are observed (Table 1). These intermolecular interactions may be contribute to the stabilization of the packing.

Experimental

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.