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

Kim, H.; Shin, Y.W.; Park, K.-M.; Kim, J.; Kim, T.H.

doi:10.1107/S1600536811005241

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o653

doi:10.1107/S1600536811005241

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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 and Tae Ho Kim ^a ^*

^aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and ^bTest & Analytical Laboratory, Korea Food & Drug Administration, 123-7 Yongdang-dong, Busan 608-829, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr, thkim@gnu.ac.kr

(Received 10 February 2011; accepted 12 February 2011; online 19 February 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.033
wR(F²) = 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

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
Symmetry codes: (i) -x, -y, -z; (ii) x-1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Crystal packing of the title compound with intermolecular C—H···O, C—H···N hydrogen bonds and S···S interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. [Symmetry codes: (i) -x, -y, -z; (ii) x + 1, y, z; (iii) -x + 1, -y, -z; (iv) -x + 1, -y + 1, -z; (v) -x, -y + 1, -z.]

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

Crystal data top

C₆H₁₁N₂O₄PS₃	F(000) = 1248
M_r = 302.32	D_x = 1.588 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9930 reflections
a = 12.3944 (2) Å	θ = 2.5–28.2°
b = 10.8056 (1) Å	µ = 0.71 mm⁻¹
c = 19.3631 (3) Å	T = 173 K
β = 102.815 (1)°	Block, colourless
V = 2528.68 (6) Å³	0.30 × 0.27 × 0.19 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	5513 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→11
T_min = 0.815, T_max = 0.877	k = −11→13
20918 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0424P)² + 1.2139P] where P = (F_o² + 2F_c²)/3
5513 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₆H₁₁N₂O₄PS₃	V = 2528.68 (6) Å³
M_r = 302.32	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3944 (2) Å	µ = 0.71 mm⁻¹
b = 10.8056 (1) Å	T = 173 K
c = 19.3631 (3) Å	0.30 × 0.27 × 0.19 mm
β = 102.815 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5513 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4682 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.877	R_int = 0.024
20918 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.07	Δρ_max = 0.98 e Å⁻³
5513 reflections	Δρ_min = −0.55 e Å⁻³
289 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.02509 (4)	0.14885 (4)	0.16800 (3)	0.02754 (12)
P2	0.60901 (4)	−0.02370 (5)	0.25072 (3)	0.02917 (13)
S1	0.01168 (5)	0.17732 (6)	0.26343 (3)	0.04165 (15)
S2	0.15513 (4)	0.02823 (5)	0.16946 (3)	0.03550 (14)
S3	0.16030 (4)	−0.35504 (4)	0.03186 (3)	0.03270 (13)
S4	0.57301 (6)	−0.06480 (7)	0.33906 (3)	0.05122 (17)
S5	0.46376 (4)	0.01769 (5)	0.17901 (3)	0.03259 (13)
S6	0.48755 (4)	0.34626 (5)	−0.00393 (3)	0.03301 (13)
O1	−0.07804 (11)	0.09769 (14)	0.11286 (7)	0.0355 (3)
O2	0.04167 (15)	0.26370 (13)	0.12160 (8)	0.0459 (4)
O3	0.31042 (11)	−0.17257 (13)	0.05006 (8)	0.0363 (3)
O4	−0.05059 (11)	−0.37521 (12)	0.03211 (8)	0.0338 (3)
O5	0.69519 (11)	0.08288 (13)	0.25149 (7)	0.0326 (3)
O6	0.67189 (12)	−0.12180 (13)	0.21387 (8)	0.0347 (3)
O7	0.35232 (12)	0.15068 (14)	−0.01300 (8)	0.0412 (4)
O8	0.67746 (11)	0.41371 (13)	0.07718 (8)	0.0351 (3)
N1	0.13193 (12)	−0.12835 (14)	0.05709 (8)	0.0243 (3)
N2	0.02836 (13)	−0.18037 (14)	0.05340 (9)	0.0263 (3)
N3	0.51734 (13)	0.14990 (15)	0.06949 (9)	0.0283 (4)
N4	0.60999 (13)	0.22068 (15)	0.09789 (8)	0.0269 (3)
C1	−0.14361 (19)	−0.0019 (2)	0.13290 (14)	0.0459 (6)
H1A	−0.2042	−0.0227	0.0927	0.069*
H1B	−0.1742	0.0246	0.1730	0.069*
H1C	−0.0967	−0.0748	0.1465	0.069*
C2	0.1050 (3)	0.3680 (3)	0.14990 (15)	0.0700 (9)
H2A	0.1047	0.4285	0.1122	0.105*
H2B	0.1813	0.3423	0.1703	0.105*
H2C	0.0731	0.4055	0.1869	0.105*
C3	0.14752 (16)	0.00052 (17)	0.07483 (10)	0.0273 (4)
H3A	0.0853	0.0487	0.0464	0.033*
H3B	0.2167	0.0298	0.0626	0.033*
C4	0.21602 (15)	−0.20269 (17)	0.04761 (10)	0.0259 (4)
C5	0.03364 (15)	−0.29610 (17)	0.04052 (10)	0.0263 (4)
C6	−0.15623 (17)	−0.31980 (19)	0.03375 (14)	0.0383 (5)
H6A	−0.2133	−0.3842	0.0272	0.057*
H6B	−0.1755	−0.2586	−0.0043	0.057*
H6C	−0.1515	−0.2791	0.0795	0.057*
C7	0.6764 (2)	0.2031 (2)	0.27938 (12)	0.0426 (5)
H7A	0.7376	0.2585	0.2760	0.064*
H7B	0.6721	0.1949	0.3291	0.064*
H7C	0.6069	0.2375	0.2520	0.064*
C8	0.6314 (2)	−0.2470 (2)	0.20117 (15)	0.0536 (7)
H8A	0.6811	−0.2940	0.1780	0.080*
H8B	0.5570	−0.2456	0.1705	0.080*
H8C	0.6287	−0.2864	0.2464	0.080*
C9	0.50949 (17)	0.02671 (18)	0.09544 (10)	0.0291 (4)
H9A	0.5829	−0.0133	0.1020	0.035*
H9B	0.4572	−0.0210	0.0591	0.035*
C10	0.43898 (16)	0.19916 (19)	0.01633 (11)	0.0305 (4)
C11	0.60347 (16)	0.32287 (18)	0.06415 (10)	0.0275 (4)
C12	0.7657 (2)	0.3958 (2)	0.13932 (13)	0.0494 (6)
H12A	0.8163	0.4666	0.1448	0.074*
H12B	0.8063	0.3199	0.1339	0.074*
H12C	0.7342	0.3887	0.1813	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0317 (3)	0.0231 (2)	0.0290 (3)	0.00059 (19)	0.0094 (2)	−0.0009 (2)
P2	0.0291 (3)	0.0324 (3)	0.0282 (3)	−0.0032 (2)	0.0112 (2)	0.0027 (2)
S1	0.0511 (4)	0.0445 (3)	0.0318 (3)	−0.0008 (3)	0.0143 (3)	−0.0075 (2)
S2	0.0322 (3)	0.0394 (3)	0.0307 (3)	0.0102 (2)	−0.0021 (2)	−0.0081 (2)
S3	0.0272 (3)	0.0230 (2)	0.0480 (3)	0.00344 (19)	0.0086 (2)	−0.0059 (2)
S4	0.0610 (4)	0.0630 (4)	0.0361 (3)	−0.0113 (3)	0.0247 (3)	0.0075 (3)
S5	0.0229 (2)	0.0389 (3)	0.0378 (3)	−0.0022 (2)	0.0106 (2)	−0.0046 (2)
S6	0.0327 (3)	0.0342 (3)	0.0299 (3)	0.0100 (2)	0.0021 (2)	0.0020 (2)
O1	0.0268 (7)	0.0473 (9)	0.0317 (8)	0.0021 (6)	0.0051 (6)	0.0004 (7)
O2	0.0710 (11)	0.0257 (7)	0.0442 (9)	−0.0051 (7)	0.0200 (8)	0.0005 (7)
O3	0.0253 (7)	0.0347 (8)	0.0505 (9)	−0.0015 (6)	0.0119 (7)	−0.0092 (7)
O4	0.0269 (7)	0.0220 (6)	0.0529 (9)	−0.0008 (5)	0.0098 (7)	−0.0015 (6)
O5	0.0290 (7)	0.0361 (8)	0.0335 (8)	−0.0074 (6)	0.0089 (6)	−0.0008 (6)
O6	0.0360 (8)	0.0310 (7)	0.0394 (8)	0.0035 (6)	0.0131 (7)	0.0057 (6)
O7	0.0283 (8)	0.0419 (9)	0.0463 (9)	0.0062 (7)	−0.0068 (7)	−0.0131 (7)
O8	0.0297 (7)	0.0351 (8)	0.0396 (8)	−0.0035 (6)	0.0054 (6)	0.0071 (7)
N1	0.0219 (8)	0.0211 (7)	0.0304 (8)	−0.0001 (6)	0.0067 (7)	−0.0015 (6)
N2	0.0240 (8)	0.0231 (8)	0.0321 (9)	−0.0004 (6)	0.0071 (7)	−0.0003 (7)
N3	0.0264 (8)	0.0274 (8)	0.0283 (9)	0.0007 (6)	0.0002 (7)	−0.0022 (7)
N4	0.0238 (8)	0.0301 (8)	0.0262 (8)	0.0000 (6)	0.0041 (7)	−0.0002 (7)
C1	0.0336 (12)	0.0538 (14)	0.0530 (15)	−0.0132 (10)	0.0157 (11)	−0.0132 (12)
C2	0.098 (2)	0.0519 (16)	0.0517 (16)	−0.0435 (16)	−0.0026 (16)	0.0031 (13)
C3	0.0284 (10)	0.0230 (9)	0.0306 (10)	−0.0004 (8)	0.0069 (8)	−0.0014 (8)
C4	0.0275 (10)	0.0241 (9)	0.0261 (9)	0.0023 (7)	0.0057 (8)	−0.0020 (8)
C5	0.0256 (10)	0.0239 (9)	0.0292 (10)	0.0028 (7)	0.0056 (8)	0.0007 (8)
C6	0.0264 (11)	0.0295 (10)	0.0604 (15)	−0.0019 (8)	0.0127 (10)	−0.0041 (10)
C7	0.0519 (14)	0.0384 (12)	0.0360 (12)	−0.0105 (10)	0.0069 (11)	−0.0075 (10)
C8	0.0713 (18)	0.0287 (12)	0.0661 (17)	−0.0002 (11)	0.0269 (15)	0.0012 (11)
C9	0.0292 (10)	0.0279 (10)	0.0300 (10)	0.0007 (8)	0.0065 (8)	−0.0053 (8)
C10	0.0274 (10)	0.0327 (10)	0.0299 (10)	0.0088 (8)	0.0031 (9)	−0.0074 (8)
C11	0.0240 (9)	0.0324 (10)	0.0263 (10)	0.0050 (8)	0.0063 (8)	0.0003 (8)
C12	0.0428 (14)	0.0520 (14)	0.0460 (14)	−0.0172 (11)	−0.0056 (11)	0.0082 (12)

Geometric parameters (Å, º) top

P1—O2	1.5720 (15)	N2—C5	1.280 (2)
P1—O1	1.5730 (15)	N3—C10	1.357 (3)
P1—S1	1.9166 (7)	N3—N4	1.388 (2)
P1—S2	2.0681 (7)	N3—C9	1.434 (2)
P2—O5	1.5685 (14)	N4—C11	1.277 (2)
P2—O6	1.5770 (15)	C1—H1A	0.9800
P2—S4	1.9135 (7)	C1—H1B	0.9800
P2—S5	2.0640 (8)	C1—H1C	0.9800
S2—C3	1.838 (2)	C2—H2A	0.9800
S3—C5	1.7363 (19)	C2—H2B	0.9800
S3—C4	1.7852 (19)	C2—H2C	0.9800
S5—C9	1.832 (2)	C3—H3A	0.9900
S6—C11	1.739 (2)	C3—H3B	0.9900
S6—C10	1.774 (2)	C6—H6A	0.9800
O1—C1	1.452 (3)	C6—H6B	0.9800
O2—C2	1.413 (3)	C6—H6C	0.9800
O3—C4	1.205 (2)	C7—H7A	0.9800
O4—C5	1.331 (2)	C7—H7B	0.9800
O4—C6	1.446 (2)	C7—H7C	0.9800
O5—C7	1.446 (3)	C8—H8A	0.9800
O6—C8	1.445 (3)	C8—H8B	0.9800
O7—C10	1.217 (2)	C8—H8C	0.9800
O8—C11	1.329 (2)	C9—H9A	0.9900
O8—C12	1.448 (3)	C9—H9B	0.9900
N1—C4	1.360 (2)	C12—H12A	0.9800
N1—N2	1.389 (2)	C12—H12B	0.9800
N1—C3	1.437 (2)	C12—H12C	0.9800

O2—P1—O1	94.54 (9)	N1—C3—H3B	109.3
O2—P1—S1	118.33 (6)	S2—C3—H3B	109.3
O1—P1—S1	118.66 (6)	H3A—C3—H3B	107.9
O2—P1—S2	107.77 (7)	O3—C4—N1	126.98 (18)
O1—P1—S2	107.54 (6)	O3—C4—S3	126.24 (15)
S1—P1—S2	108.78 (3)	N1—C4—S3	106.78 (13)
O5—P2—O6	95.40 (8)	N2—C5—O4	125.36 (17)
O5—P2—S4	117.08 (6)	N2—C5—S3	117.62 (15)
O6—P2—S4	119.02 (6)	O4—C5—S3	117.00 (13)
O5—P2—S5	109.75 (6)	O4—C6—H6A	109.5
O6—P2—S5	106.63 (6)	O4—C6—H6B	109.5
S4—P2—S5	108.07 (3)	H6A—C6—H6B	109.5
C3—S2—P1	102.80 (7)	O4—C6—H6C	109.5
C5—S3—C4	88.23 (9)	H6A—C6—H6C	109.5
C9—S5—P2	102.19 (7)	H6B—C6—H6C	109.5
C11—S6—C10	88.05 (9)	O5—C7—H7A	109.5
C1—O1—P1	119.85 (14)	O5—C7—H7B	109.5
C2—O2—P1	122.67 (16)	H7A—C7—H7B	109.5
C5—O4—C6	114.88 (15)	O5—C7—H7C	109.5
C7—O5—P2	119.87 (13)	H7A—C7—H7C	109.5
C8—O6—P2	121.24 (14)	H7B—C7—H7C	109.5
C11—O8—C12	114.92 (16)	O6—C8—H8A	109.5
C4—N1—N2	118.77 (15)	O6—C8—H8B	109.5
C4—N1—C3	122.56 (16)	H8A—C8—H8B	109.5
N2—N1—C3	118.57 (14)	O6—C8—H8C	109.5
C5—N2—N1	108.60 (15)	H8A—C8—H8C	109.5
C10—N3—N4	118.32 (16)	H8B—C8—H8C	109.5
C10—N3—C9	122.48 (17)	N3—C9—S5	114.67 (13)
N4—N3—C9	119.16 (16)	N3—C9—H9A	108.6
C11—N4—N3	108.72 (16)	S5—C9—H9A	108.6
O1—C1—H1A	109.5	N3—C9—H9B	108.6
O1—C1—H1B	109.5	S5—C9—H9B	108.6
H1A—C1—H1B	109.5	H9A—C9—H9B	107.6
O1—C1—H1C	109.5	O7—C10—N3	126.5 (2)
H1A—C1—H1C	109.5	O7—C10—S6	126.18 (16)
H1B—C1—H1C	109.5	N3—C10—S6	107.35 (14)
O2—C2—H2A	109.5	N4—C11—O8	125.39 (18)
O2—C2—H2B	109.5	N4—C11—S6	117.48 (15)
H2A—C2—H2B	109.5	O8—C11—S6	117.12 (14)
O2—C2—H2C	109.5	O8—C12—H12A	109.5
H2A—C2—H2C	109.5	O8—C12—H12B	109.5
H2B—C2—H2C	109.5	H12A—C12—H12B	109.5
N1—C3—S2	111.76 (13)	O8—C12—H12C	109.5
N1—C3—H3A	109.3	H12A—C12—H12C	109.5
S2—C3—H3A	109.3	H12B—C12—H12C	109.5

O2—P1—S2—C3	−55.63 (9)	C3—N1—C4—O3	−2.7 (3)
O1—P1—S2—C3	45.23 (9)	N2—N1—C4—S3	0.3 (2)
S1—P1—S2—C3	174.93 (7)	C3—N1—C4—S3	176.58 (14)
O5—P2—S5—C9	61.04 (9)	C5—S3—C4—O3	179.15 (19)
O6—P2—S5—C9	−41.17 (9)	C5—S3—C4—N1	−0.10 (14)
S4—P2—S5—C9	−170.21 (7)	N1—N2—C5—O4	−178.69 (17)
O2—P1—O1—C1	−169.51 (15)	N1—N2—C5—S3	0.2 (2)
S1—P1—O1—C1	−43.64 (17)	C6—O4—C5—N2	4.0 (3)
S2—P1—O1—C1	80.24 (15)	C6—O4—C5—S3	−174.91 (15)
O1—P1—O2—C2	162.2 (2)	C4—S3—C5—N2	−0.09 (17)
S1—P1—O2—C2	36.1 (2)	C4—S3—C5—O4	178.94 (16)
S2—P1—O2—C2	−87.7 (2)	C10—N3—C9—S5	−101.82 (19)
O6—P2—O5—C7	178.26 (15)	N4—N3—C9—S5	80.34 (19)
S4—P2—O5—C7	−55.19 (16)	P2—S5—C9—N3	−105.14 (14)
S5—P2—O5—C7	68.42 (15)	N4—N3—C10—O7	−178.22 (18)
O5—P2—O6—C8	177.37 (18)	C9—N3—C10—O7	3.9 (3)
S4—P2—O6—C8	52.25 (19)	N4—N3—C10—S6	3.0 (2)
S5—P2—O6—C8	−70.14 (18)	C9—N3—C10—S6	−174.84 (14)
C4—N1—N2—C5	−0.3 (2)	C11—S6—C10—O7	179.08 (19)
C3—N1—N2—C5	−176.80 (17)	C11—S6—C10—N3	−2.15 (14)
C10—N3—N4—C11	−2.3 (2)	N3—N4—C11—O8	179.59 (17)
C9—N3—N4—C11	175.65 (16)	N3—N4—C11—S6	0.3 (2)
C4—N1—C3—S2	−101.78 (18)	C12—O8—C11—N4	−6.0 (3)
N2—N1—C3—S2	74.52 (18)	C12—O8—C11—S6	173.21 (16)
P1—S2—C3—N1	−120.69 (12)	C10—S6—C11—N4	1.10 (16)
N2—N1—C4—O3	−178.97 (19)	C10—S6—C11—O8	−178.22 (15)

Hydrogen-bond geometry (Å, º) top

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
C6—H6B···O7ⁱ	0.98	2.57	2.996 (2)	106
C9—H9B···O3	0.99	2.42	3.246 (2)	140

Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₆H₁₁N₂O₄PS₃
M_r	302.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.3944 (2), 10.8056 (1), 19.3631 (3)
β (°)	102.815 (1)
V (Å³)	2528.68 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.30 × 0.27 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.815, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	20918, 5513, 4682
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.089, 1.07
No. of reflections	5513
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.55

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

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).

References

Altuntas, I., Delibas, N., Demirci, M., Kilinc, I. & Tamer, N. (2002). Arch. Toxicol. 76, 470–473. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rohrbaugh, W. J., Meyers, E. K. & Jacobson, R. A. (1976). J. Agric. Food Chem. 24, 713–717. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o653

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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