3-[(2-Chloro-1,3-thia-zol-5-yl)meth-yl]-5-methyl-1,3,5-oxadiazinan-4-one.

In the title compound, C(8)H(10)ClN(3)O(2)S, the oxadiazinane ring is in a sofa conformation with the ring O atom deviating from the best plane of the remaining five atoms by 0.636 (2) Å. A short intra-molecular C-S⋯O=C contact [S⋯O 3.122 (2) Å, C-S⋯O 80.0 (2)°] is observed between the two mol-ecular fragments bridged by the methyl-ene group. In the crystal, C-H⋯O hydrogen bonds link mol-ecules, forming chains along the b axis.

Related literature

For the biological activity of thia­methoxam, see: Maienfisch et al. (2001 ▶, 2006 ▶); Suchail et al. (2001 ▶); Ford & Casida (2006 ▶). For the structure of thia­methoxam, see: Chopra et al. (2004 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C8H10ClN3O2S

M = 247.70

Orthorhombic,

a = 4.6141 (2) Å

b = 11.7335 (4) Å

c = 20.1460 (8) Å

V = 1090.70 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.925, T max = 1.000

22323 measured reflections

2147 independent reflections

1974 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.07

2147 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 856 Friedel pairs

Flack parameter: 0.04 (9)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042031/gk2519sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042031/gk2519Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042031/gk2519Isup3.cml

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

C8H10ClN3O2S	F(000) = 512
Mr = 247.70	Dx = 1.508 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11280 reflections
a = 4.6141 (2) Å	θ = 3.5–29.0°
b = 11.7335 (4) Å	µ = 0.53 mm−1
c = 20.1460 (8) Å	T = 293 K
V = 1090.70 (7) Å3	Needle, white
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2147 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.925, Tmax = 1.000	l = −24→24
22323 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.2799P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2147 reflections	Δρmax = 0.22 e Å−3
137 parameters	Δρmin = −0.16 e Å−3
0 restraints	Absolute structure: Flack (1983), 856 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (9)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.29172 (13)	0.85031 (5)	0.83926 (3)	0.04611 (15)
Cl1	0.64157 (15)	0.83860 (6)	0.96232 (3)	0.0642 (2)
O1	0.4809 (4)	1.08899 (16)	0.64448 (10)	0.0653 (5)
C2	0.2262 (7)	1.1021 (2)	0.68003 (16)	0.0668 (8)
H2A	0.0844	1.1412	0.6527	0.080*
H2B	0.2630	1.1487	0.7189	0.080*
N3	0.1108 (5)	0.99332 (17)	0.70052 (10)	0.0512 (5)
C4	0.1836 (6)	0.8940 (2)	0.67011 (12)	0.0516 (6)
N5	0.3433 (6)	0.90503 (19)	0.61443 (11)	0.0640 (6)
C6	0.4364 (9)	1.0158 (3)	0.59173 (14)	0.0778 (9)
H6A	0.6149	1.0079	0.5667	0.093*
H6B	0.2905	1.0475	0.5624	0.093*
C7	−0.0657 (6)	0.9905 (3)	0.76014 (14)	0.0613 (7)
H7A	−0.2048	0.9289	0.7564	0.074*
H7B	−0.1734	1.0613	0.7634	0.074*
O7	0.1066 (5)	0.80128 (15)	0.69297 (10)	0.0744 (6)
C8	0.4470 (9)	0.8075 (3)	0.57872 (19)	0.0975 (12)
H8A	0.3872	0.7392	0.6012	0.146*
H8B	0.6547	0.8098	0.5765	0.146*
H8C	0.3684	0.8080	0.5346	0.146*
C9	0.1052 (5)	0.9747 (2)	0.82176 (12)	0.0494 (6)
C10	0.4123 (5)	0.9127 (2)	0.91085 (12)	0.0484 (6)
N11	0.3276 (6)	1.01443 (19)	0.92255 (12)	0.0692 (7)
C12	0.1516 (7)	1.0488 (2)	0.87096 (15)	0.0680 (8)
H12	0.0683	1.1210	0.8704	0.082*

	U11	U22	U33	U12	U13	U23
S1	0.0529 (3)	0.0353 (2)	0.0501 (3)	0.0000 (2)	0.0022 (2)	0.0000 (2)
Cl1	0.0651 (4)	0.0728 (4)	0.0546 (4)	−0.0027 (4)	−0.0063 (3)	0.0091 (3)
O1	0.0633 (11)	0.0579 (11)	0.0748 (12)	−0.0128 (9)	−0.0003 (10)	0.0120 (10)
C2	0.0732 (18)	0.0395 (12)	0.088 (2)	0.0011 (13)	0.0047 (16)	0.0129 (13)
N3	0.0552 (12)	0.0421 (10)	0.0563 (12)	−0.0002 (9)	0.0042 (10)	0.0105 (9)
C4	0.0570 (13)	0.0446 (11)	0.0533 (14)	−0.0083 (11)	−0.0123 (13)	0.0084 (11)
N5	0.0871 (17)	0.0551 (13)	0.0499 (12)	−0.0056 (13)	0.0064 (12)	−0.0020 (10)
C6	0.102 (3)	0.079 (2)	0.0529 (17)	−0.0165 (19)	0.0084 (16)	0.0135 (15)
C7	0.0480 (14)	0.0691 (16)	0.0669 (17)	0.0082 (13)	0.0019 (12)	0.0110 (14)
O7	0.1021 (17)	0.0435 (9)	0.0775 (13)	−0.0221 (11)	−0.0017 (13)	0.0082 (9)
C8	0.121 (3)	0.089 (2)	0.083 (2)	0.003 (2)	0.011 (2)	−0.025 (2)
C9	0.0472 (13)	0.0450 (12)	0.0561 (14)	0.0058 (10)	0.0112 (11)	0.0061 (11)
C10	0.0505 (13)	0.0459 (13)	0.0487 (13)	−0.0061 (11)	0.0058 (11)	0.0009 (10)
N11	0.0892 (19)	0.0501 (12)	0.0683 (15)	0.0053 (13)	0.0002 (14)	−0.0144 (11)
C12	0.087 (2)	0.0429 (14)	0.0741 (19)	0.0176 (14)	0.0026 (17)	−0.0061 (12)

S1—C10	1.710 (2)	N5—C6	1.443 (4)
S1—C9	1.731 (2)	C6—H6A	0.9700
Cl1—C10	1.718 (3)	C6—H6B	0.9700
O1—C6	1.382 (4)	C7—C9	1.482 (4)
O1—C2	1.385 (4)	C7—H7A	0.9700
C2—N3	1.443 (3)	C7—H7B	0.9700
C2—H2A	0.9700	C8—H8A	0.9600
C2—H2B	0.9700	C8—H8B	0.9600
N3—C4	1.359 (3)	C8—H8C	0.9600
N3—C7	1.452 (3)	C9—C12	1.336 (4)
C4—O7	1.233 (3)	C10—N11	1.278 (3)
C4—N5	1.348 (3)	N11—C12	1.379 (4)
N5—C8	1.434 (4)	C12—H12	0.9300
C10—S1—C9	88.42 (12)	N3—C7—C9	113.4 (2)
C6—O1—C2	109.9 (2)	N3—C7—H7A	108.9
O1—C2—N3	111.3 (2)	C9—C7—H7A	108.9
O1—C2—H2A	109.4	N3—C7—H7B	108.9
N3—C2—H2A	109.4	C9—C7—H7B	108.9
O1—C2—H2B	109.4	H7A—C7—H7B	107.7
N3—C2—H2B	109.4	N5—C8—H8A	109.5
H2A—C2—H2B	108.0	N5—C8—H8B	109.5
C4—N3—C2	122.6 (2)	H8A—C8—H8B	109.5
C4—N3—C7	119.5 (2)	N5—C8—H8C	109.5
C2—N3—C7	117.6 (2)	H8A—C8—H8C	109.5
O7—C4—N5	123.6 (2)	H8B—C8—H8C	109.5
O7—C4—N3	121.1 (2)	C12—C9—C7	128.7 (2)
N5—C4—N3	115.3 (2)	C12—C9—S1	108.5 (2)
C4—N5—C8	121.5 (3)	C7—C9—S1	122.7 (2)
C4—N5—C6	120.9 (2)	N11—C10—S1	117.1 (2)
C8—N5—C6	117.4 (3)	N11—C10—Cl1	123.4 (2)
O1—C6—N5	111.1 (2)	S1—C10—Cl1	119.52 (14)
O1—C6—H6A	109.4	C10—N11—C12	108.3 (2)
N5—C6—H6A	109.4	C9—C12—N11	117.6 (2)
O1—C6—H6B	109.4	C9—C12—H12	121.2
N5—C6—H6B	109.4	N11—C12—H12	121.2
H6A—C6—H6B	108.0
C6—O1—C2—N3	54.5 (3)	C4—N3—C7—C9	85.9 (3)
O1—C2—N3—C4	−20.9 (4)	C2—N3—C7—C9	−87.9 (3)
O1—C2—N3—C7	152.7 (2)	N3—C7—C9—C12	111.4 (3)
C2—N3—C4—O7	172.1 (3)	N3—C7—C9—S1	−66.6 (3)
C7—N3—C4—O7	−1.3 (4)	C10—S1—C9—C12	−0.2 (2)
C2—N3—C4—N5	−7.7 (4)	C10—S1—C9—C7	178.1 (2)
C7—N3—C4—N5	178.8 (2)	C9—S1—C10—N11	0.3 (2)
O7—C4—N5—C8	−2.7 (5)	C9—S1—C10—Cl1	−178.75 (16)
N3—C4—N5—C8	177.2 (3)	S1—C10—N11—C12	−0.2 (3)
O7—C4—N5—C6	−177.5 (3)	Cl1—C10—N11—C12	178.8 (2)
N3—C4—N5—C6	2.4 (4)	C7—C9—C12—N11	−178.0 (3)
C2—O1—C6—N5	−59.9 (4)	S1—C9—C12—N11	0.2 (4)
C4—N5—C6—O1	31.4 (4)	C10—N11—C12—C9	0.0 (4)
C8—N5—C6—O1	−143.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O7i	0.93	2.60	3.443 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O7i	0.93	2.60	3.443 (3)	151

Symmetry code: (i) .