Methidathion: S-(5-meth-oxy-2-oxo-2,3-dihydro-1,3,4-thia-diazol-3-yl)methyl O,O-dimethyl phospho-rodithio-ate.

The title compound, C(6)H(11)N(2)O(4)PS(3), crystallizes with two independent mol-ecules in the asymmetric unit. The dihedral angles between the thia-diazole ring planes and the PS(2) planes of the phospho-rodithio-ate group are 86.51 (5) and 56.33 (5)° in the two mol-ecules. In the crystal, weak inter-molecular S⋯S [3.570 (8) Å] inter-actions 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 = 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

Δρmax = 0.98 e Å−3

Δρmin = −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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H11N2O4PS3	F(000) = 1248
Mr = 302.32	Dx = 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

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

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(Fo2) + (0.0424P)2 + 1.2139P] where P = (Fo2 + 2Fc2)/3
5513 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.98 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .