(4E)-3-[(2-Chloro-4,5-di­hydro-1,3-thia­zol-5-yl)­methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (thia­methaxam)

Chopra, D.; Mohan, T.P.; Rao, K.S.; Guru Row, T.N.

doi:10.1107/S1600536804029812

(4E)-3-[(2-Chloro-4,5-dihydro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (thiamethaxam)

D. Chopra, T. P. Mohan, K. S. Rao and T. N. Guru Row

The title compound (also known as thiamethaxam), C₈H₁₀ClN₅O₃S, is a potent agrochemical exhibiting insecticidal activity. The crystal structure is stabilized by intermolecular C—H

N and C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029812/ob6439sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029812/ob6439Isup2.hkl Contains datablock I

CCDC reference: 243116

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.065
wR factor = 0.176
Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.42 Ratio
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C5      ..       3.00 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

(4E)-3-[(2-Chloro-4,5-dihydro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro- 1,3,5-oxadiazinan-4-imine top

Crystal data top

C₈H₁₀ClN₅O₃S	F(000) = 600
M_r = 291.73	D_x = 1.582 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 564 reflections
a = 6.493 (5) Å	θ = 1.5–26.4°
b = 28.74 (2) Å	µ = 0.49 mm⁻¹
c = 6.812 (5) Å	T = 293 K
β = 105.486 (12)°	Block, yellow
V = 1225.0 (16) Å³	0.31 × 0.27 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2370 independent reflections
Radiation source: fine-focus sealed tube	1970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 26.4°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.863, T_max = 0.908	k = −34→35
7937 measured reflections	l = −8→8

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	All H-atom parameters refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0829P)² + 1.5246P] where P = (F_o² + 2F_c²)/3
2370 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

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
S1	0.61397 (14)	0.02848 (3)	0.30760 (15)	0.0432 (3)
Cl1	0.5133 (2)	−0.07176 (4)	0.23011 (18)	0.0687 (4)
O1	0.8829 (4)	0.14936 (10)	−0.1633 (4)	0.0512 (7)
O2	0.3453 (5)	0.17328 (12)	0.4298 (6)	0.0713 (10)
O3	0.6102 (5)	0.21508 (10)	0.3942 (5)	0.0572 (8)
N1	0.8710 (6)	−0.03003 (11)	0.2151 (5)	0.0482 (8)
N2	0.8627 (4)	0.12828 (10)	0.1659 (4)	0.0367 (7)
N3	0.6590 (5)	0.18766 (10)	−0.0015 (5)	0.0432 (7)
N4	0.5498 (5)	0.14407 (10)	0.2519 (5)	0.0420 (7)
N5	0.4993 (5)	0.17879 (11)	0.3594 (5)	0.0423 (7)
C1	0.6854 (6)	−0.02576 (12)	0.2448 (5)	0.0423 (8)
C2	0.9708 (6)	0.01258 (14)	0.2449 (6)	0.0437 (9)
C3	0.8613 (5)	0.04827 (12)	0.2972 (5)	0.0344 (7)
C4	0.9355 (6)	0.09728 (13)	0.3435 (6)	0.0417 (8)
C5	0.4629 (9)	0.2151 (2)	−0.0670 (10)	0.0627 (13)
C6	0.6906 (5)	0.15541 (11)	0.1429 (5)	0.0334 (7)
C7	0.8220 (8)	0.19361 (14)	−0.1087 (8)	0.0531 (10)
C8	0.9853 (7)	0.12510 (16)	0.0133 (7)	0.0489 (10)
H2	1.126 (8)	0.0137 (16)	0.229 (7)	0.061 (13)*
H4A	0.882 (7)	0.1109 (15)	0.453 (7)	0.049 (11)*
H4B	1.086 (7)	0.0980 (13)	0.379 (6)	0.038 (10)*
H5A	0.424 (11)	0.216 (2)	−0.200 (12)	0.10 (2)*
H5B	0.491 (12)	0.249 (3)	−0.015 (13)	0.13 (3)*
H5C	0.367 (10)	0.203 (2)	−0.011 (10)	0.09 (2)*
H7A	0.955 (8)	0.2048 (16)	−0.011 (8)	0.059 (13)*
H7B	0.777 (8)	0.2124 (18)	−0.223 (8)	0.074 (15)*
H8A	1.122 (9)	0.1356 (18)	0.071 (8)	0.077 (16)*
H8B	0.998 (7)	0.0913 (18)	−0.021 (7)	0.067 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0340 (5)	0.0421 (5)	0.0539 (6)	−0.0010 (3)	0.0125 (4)	−0.0002 (4)
Cl1	0.0904 (9)	0.0516 (7)	0.0594 (7)	−0.0310 (6)	0.0119 (6)	−0.0059 (5)
O1	0.0562 (17)	0.0522 (17)	0.0503 (16)	0.0023 (13)	0.0233 (14)	0.0006 (12)
O2	0.063 (2)	0.084 (2)	0.083 (2)	−0.0134 (16)	0.0479 (19)	−0.0231 (18)
O3	0.0645 (18)	0.0413 (16)	0.0686 (19)	−0.0089 (13)	0.0230 (15)	−0.0157 (13)
N1	0.062 (2)	0.0363 (18)	0.0477 (19)	0.0051 (14)	0.0176 (17)	−0.0015 (13)
N2	0.0333 (15)	0.0347 (15)	0.0422 (16)	0.0008 (11)	0.0103 (13)	0.0009 (12)
N3	0.0453 (17)	0.0350 (16)	0.0529 (19)	0.0060 (12)	0.0192 (15)	0.0071 (13)
N4	0.0435 (17)	0.0344 (16)	0.0548 (19)	−0.0078 (12)	0.0250 (15)	−0.0069 (13)
N5	0.0353 (16)	0.0459 (18)	0.0483 (18)	−0.0021 (13)	0.0158 (14)	−0.0080 (13)
C1	0.055 (2)	0.0369 (19)	0.0316 (17)	−0.0065 (16)	0.0061 (16)	0.0005 (14)
C2	0.040 (2)	0.047 (2)	0.046 (2)	0.0048 (16)	0.0138 (17)	0.0012 (16)
C3	0.0282 (16)	0.0376 (18)	0.0354 (18)	0.0022 (13)	0.0051 (14)	0.0036 (13)
C4	0.038 (2)	0.038 (2)	0.042 (2)	0.0010 (15)	−0.0007 (16)	0.0033 (15)
C5	0.057 (3)	0.065 (3)	0.067 (3)	0.027 (2)	0.018 (3)	0.018 (3)
C6	0.0326 (17)	0.0262 (16)	0.0410 (18)	−0.0047 (12)	0.0090 (15)	−0.0039 (13)
C7	0.062 (3)	0.039 (2)	0.066 (3)	−0.0001 (19)	0.029 (2)	0.0074 (19)
C8	0.039 (2)	0.055 (3)	0.056 (2)	0.0061 (17)	0.0192 (19)	0.0045 (19)

Geometric parameters (Å, º) top

S1—C1	1.713 (4)	N5—O2	1.229 (4)
S1—C3	1.723 (4)	N5—N4	1.330 (4)
Cl1—C1	1.717 (4)	C3—C2	1.349 (5)
O3—N5	1.253 (4)	C3—C4	1.495 (5)
O1—C8	1.395 (5)	C2—H2	1.05 (5)
O1—C7	1.411 (5)	C4—H4B	0.94 (4)
N1—C1	1.280 (5)	C4—H4A	0.99 (4)
N1—C2	1.375 (5)	C8—H8A	0.92 (6)
N2—C6	1.337 (4)	C8—H8B	1.01 (5)
N2—C8	1.471 (5)	C7—H7A	0.99 (5)
N2—C4	1.475 (5)	C7—H7B	0.93 (6)
N3—C6	1.327 (5)	C5—H5A	0.87 (8)
N3—C7	1.447 (5)	C5—H5C	0.89 (7)
N3—C5	1.462 (5)	C5—H5B	1.02 (8)
N4—C6	1.362 (4)

C1—S1—C3	88.44 (18)	N2—C4—H4A	106 (2)
C8—O1—C7	109.0 (4)	C3—C4—H4A	112 (2)
C6—N2—C8	123.1 (3)	H4B—C4—H4A	110 (3)
C6—N2—C4	121.5 (3)	O1—C8—N2	110.8 (3)
C8—N2—C4	115.3 (3)	O1—C8—H8A	113 (3)
O2—N5—O3	121.3 (3)	N2—C8—H8A	109 (3)
O2—N5—N4	117.6 (3)	O1—C8—H8B	109 (3)
O3—N5—N4	121.0 (3)	N2—C8—H8B	109 (3)
C6—N3—C7	117.9 (3)	H8A—C8—H8B	107 (4)
C6—N3—C5	123.5 (4)	N1—C1—S1	117.1 (3)
C7—N3—C5	118.5 (4)	N1—C1—Cl1	122.9 (3)
N5—N4—C6	114.9 (3)	S1—C1—Cl1	120.0 (3)
C1—N1—C2	108.5 (3)	O1—C7—N3	108.7 (3)
C2—C3—C4	127.5 (3)	O1—C7—H7A	102 (3)
C2—C3—S1	108.8 (3)	N3—C7—H7A	109 (3)
C4—C3—S1	123.6 (3)	O1—C7—H7B	111 (3)
N3—C6—N2	117.0 (3)	N3—C7—H7B	112 (3)
N3—C6—N4	125.3 (3)	H7A—C7—H7B	113 (4)
N2—C6—N4	117.3 (3)	N3—C5—H5A	109 (4)
C3—C2—N1	117.1 (3)	N3—C5—H5C	108 (4)
C3—C2—H2	127 (3)	H5A—C5—H5C	115 (6)
N1—C2—H2	116 (3)	N3—C5—H5B	110 (4)
N2—C4—C3	112.4 (3)	H5A—C5—H5B	107 (6)
N2—C4—H4B	106 (2)	H5C—C5—H5B	108 (5)
C3—C4—H4B	109 (2)

C1—S1—C3—C2	0.9 (3)	C2—N1—C1—S1	0.5 (4)
C1—S1—C3—C4	−178.2 (3)	C2—N1—C1—Cl1	−177.9 (3)
C8—N2—C6—N3	−14.7 (5)	C3—S1—C1—N1	−0.9 (3)
C4—N2—C6—N3	168.7 (3)	C3—S1—C1—Cl1	177.6 (2)
C8—N2—C6—N4	157.6 (4)	C8—O1—C7—N3	−66.8 (5)
C4—N2—C6—N4	−18.9 (5)	C7—N3—C6—N2	−5.5 (5)
C4—C3—C2—N1	178.1 (3)	C5—N3—C6—N2	170.2 (4)
S1—C3—C2—N1	−0.9 (4)	C7—N3—C6—N4	−177.1 (4)
C1—N1—C2—C3	0.3 (5)	C5—N3—C6—N4	−1.4 (6)
C6—N2—C4—C3	98.3 (4)	C6—N3—C7—O1	45.9 (5)
C8—N2—C4—C3	−78.6 (4)	C5—N3—C7—O1	−130.0 (4)
C2—C3—C4—N2	96.7 (4)	N5—N4—C6—N3	−60.0 (5)
S1—C3—C4—N2	−84.3 (4)	N5—N4—C6—N2	128.4 (3)
C7—O1—C8—N2	47.2 (5)	O2—N5—N4—C6	166.8 (4)
C6—N2—C8—O1	−7.1 (5)	O3—N5—N4—C6	−15.9 (5)
C4—N2—C8—O1	169.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3ⁱ	1.02 (8)	2.60 (8)	3.003 (7)	106 (6)
C7—H7B···O3ⁱⁱ	0.93 (5)	2.54 (5)	3.354 (7)	146 (4)
C8—H8B···N1ⁱⁱⁱ	1.01 (5)	2.48 (5)	3.396 (6)	150 (4)

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

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(4E)-3-[(2-Chloro-4,5-di­hydro-1,3-thia­zol-5-yl)­methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (thia­methaxam)

Supporting information

Key indicators

checkCIF/PLATON results

(4E)-3-[(2-Chloro-4,5-dihydro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (thiamethaxam)