Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029812/ob6439sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029812/ob6439Isup2.hkl
Contains datablock I

CCDC reference: 243116

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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
C8H10ClN5O3SF(000) = 600
Mr = 291.73Dx = 1.582 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 564 reflections
a = 6.493 (5) Åθ = 1.5–26.4°
b = 28.74 (2) ŵ = 0.49 mm1
c = 6.812 (5) ÅT = 293 K
β = 105.486 (12)°Block, yellow
V = 1225.0 (16) Å30.31 × 0.27 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2370 independent reflections
Radiation source: fine-focus sealed tube1970 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.863, Tmax = 0.908k = 3435
7937 measured reflectionsl = 88
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.0829P)2 + 1.5246P]
where P = (Fo2 + 2Fc2)/3
2370 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.45 e Å3
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
xyzUiso*/Ueq
S10.61397 (14)0.02848 (3)0.30760 (15)0.0432 (3)
Cl10.5133 (2)0.07176 (4)0.23011 (18)0.0687 (4)
O10.8829 (4)0.14936 (10)0.1633 (4)0.0512 (7)
O20.3453 (5)0.17328 (12)0.4298 (6)0.0713 (10)
O30.6102 (5)0.21508 (10)0.3942 (5)0.0572 (8)
N10.8710 (6)0.03003 (11)0.2151 (5)0.0482 (8)
N20.8627 (4)0.12828 (10)0.1659 (4)0.0367 (7)
N30.6590 (5)0.18766 (10)0.0015 (5)0.0432 (7)
N40.5498 (5)0.14407 (10)0.2519 (5)0.0420 (7)
N50.4993 (5)0.17879 (11)0.3594 (5)0.0423 (7)
C10.6854 (6)0.02576 (12)0.2448 (5)0.0423 (8)
C20.9708 (6)0.01258 (14)0.2449 (6)0.0437 (9)
C30.8613 (5)0.04827 (12)0.2972 (5)0.0344 (7)
C40.9355 (6)0.09728 (13)0.3435 (6)0.0417 (8)
C50.4629 (9)0.2151 (2)0.0670 (10)0.0627 (13)
C60.6906 (5)0.15541 (11)0.1429 (5)0.0334 (7)
C70.8220 (8)0.19361 (14)0.1087 (8)0.0531 (10)
C80.9853 (7)0.12510 (16)0.0133 (7)0.0489 (10)
H21.126 (8)0.0137 (16)0.229 (7)0.061 (13)*
H4A0.882 (7)0.1109 (15)0.453 (7)0.049 (11)*
H4B1.086 (7)0.0980 (13)0.379 (6)0.038 (10)*
H5A0.424 (11)0.216 (2)0.200 (12)0.10 (2)*
H5B0.491 (12)0.249 (3)0.015 (13)0.13 (3)*
H5C0.367 (10)0.203 (2)0.011 (10)0.09 (2)*
H7A0.955 (8)0.2048 (16)0.011 (8)0.059 (13)*
H7B0.777 (8)0.2124 (18)0.223 (8)0.074 (15)*
H8A1.122 (9)0.1356 (18)0.071 (8)0.077 (16)*
H8B0.998 (7)0.0913 (18)0.021 (7)0.067 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0340 (5)0.0421 (5)0.0539 (6)0.0010 (3)0.0125 (4)0.0002 (4)
Cl10.0904 (9)0.0516 (7)0.0594 (7)0.0310 (6)0.0119 (6)0.0059 (5)
O10.0562 (17)0.0522 (17)0.0503 (16)0.0023 (13)0.0233 (14)0.0006 (12)
O20.063 (2)0.084 (2)0.083 (2)0.0134 (16)0.0479 (19)0.0231 (18)
O30.0645 (18)0.0413 (16)0.0686 (19)0.0089 (13)0.0230 (15)0.0157 (13)
N10.062 (2)0.0363 (18)0.0477 (19)0.0051 (14)0.0176 (17)0.0015 (13)
N20.0333 (15)0.0347 (15)0.0422 (16)0.0008 (11)0.0103 (13)0.0009 (12)
N30.0453 (17)0.0350 (16)0.0529 (19)0.0060 (12)0.0192 (15)0.0071 (13)
N40.0435 (17)0.0344 (16)0.0548 (19)0.0078 (12)0.0250 (15)0.0069 (13)
N50.0353 (16)0.0459 (18)0.0483 (18)0.0021 (13)0.0158 (14)0.0080 (13)
C10.055 (2)0.0369 (19)0.0316 (17)0.0065 (16)0.0061 (16)0.0005 (14)
C20.040 (2)0.047 (2)0.046 (2)0.0048 (16)0.0138 (17)0.0012 (16)
C30.0282 (16)0.0376 (18)0.0354 (18)0.0022 (13)0.0051 (14)0.0036 (13)
C40.038 (2)0.038 (2)0.042 (2)0.0010 (15)0.0007 (16)0.0033 (15)
C50.057 (3)0.065 (3)0.067 (3)0.027 (2)0.018 (3)0.018 (3)
C60.0326 (17)0.0262 (16)0.0410 (18)0.0047 (12)0.0090 (15)0.0039 (13)
C70.062 (3)0.039 (2)0.066 (3)0.0001 (19)0.029 (2)0.0074 (19)
C80.039 (2)0.055 (3)0.056 (2)0.0061 (17)0.0192 (19)0.0045 (19)
Geometric parameters (Å, º) top
S1—C11.713 (4)N5—O21.229 (4)
S1—C31.723 (4)N5—N41.330 (4)
Cl1—C11.717 (4)C3—C21.349 (5)
O3—N51.253 (4)C3—C41.495 (5)
O1—C81.395 (5)C2—H21.05 (5)
O1—C71.411 (5)C4—H4B0.94 (4)
N1—C11.280 (5)C4—H4A0.99 (4)
N1—C21.375 (5)C8—H8A0.92 (6)
N2—C61.337 (4)C8—H8B1.01 (5)
N2—C81.471 (5)C7—H7A0.99 (5)
N2—C41.475 (5)C7—H7B0.93 (6)
N3—C61.327 (5)C5—H5A0.87 (8)
N3—C71.447 (5)C5—H5C0.89 (7)
N3—C51.462 (5)C5—H5B1.02 (8)
N4—C61.362 (4)
C1—S1—C388.44 (18)N2—C4—H4A106 (2)
C8—O1—C7109.0 (4)C3—C4—H4A112 (2)
C6—N2—C8123.1 (3)H4B—C4—H4A110 (3)
C6—N2—C4121.5 (3)O1—C8—N2110.8 (3)
C8—N2—C4115.3 (3)O1—C8—H8A113 (3)
O2—N5—O3121.3 (3)N2—C8—H8A109 (3)
O2—N5—N4117.6 (3)O1—C8—H8B109 (3)
O3—N5—N4121.0 (3)N2—C8—H8B109 (3)
C6—N3—C7117.9 (3)H8A—C8—H8B107 (4)
C6—N3—C5123.5 (4)N1—C1—S1117.1 (3)
C7—N3—C5118.5 (4)N1—C1—Cl1122.9 (3)
N5—N4—C6114.9 (3)S1—C1—Cl1120.0 (3)
C1—N1—C2108.5 (3)O1—C7—N3108.7 (3)
C2—C3—C4127.5 (3)O1—C7—H7A102 (3)
C2—C3—S1108.8 (3)N3—C7—H7A109 (3)
C4—C3—S1123.6 (3)O1—C7—H7B111 (3)
N3—C6—N2117.0 (3)N3—C7—H7B112 (3)
N3—C6—N4125.3 (3)H7A—C7—H7B113 (4)
N2—C6—N4117.3 (3)N3—C5—H5A109 (4)
C3—C2—N1117.1 (3)N3—C5—H5C108 (4)
C3—C2—H2127 (3)H5A—C5—H5C115 (6)
N1—C2—H2116 (3)N3—C5—H5B110 (4)
N2—C4—C3112.4 (3)H5A—C5—H5B107 (6)
N2—C4—H4B106 (2)H5C—C5—H5B108 (5)
C3—C4—H4B109 (2)
C1—S1—C3—C20.9 (3)C2—N1—C1—S10.5 (4)
C1—S1—C3—C4178.2 (3)C2—N1—C1—Cl1177.9 (3)
C8—N2—C6—N314.7 (5)C3—S1—C1—N10.9 (3)
C4—N2—C6—N3168.7 (3)C3—S1—C1—Cl1177.6 (2)
C8—N2—C6—N4157.6 (4)C8—O1—C7—N366.8 (5)
C4—N2—C6—N418.9 (5)C7—N3—C6—N25.5 (5)
C4—C3—C2—N1178.1 (3)C5—N3—C6—N2170.2 (4)
S1—C3—C2—N10.9 (4)C7—N3—C6—N4177.1 (4)
C1—N1—C2—C30.3 (5)C5—N3—C6—N41.4 (6)
C6—N2—C4—C398.3 (4)C6—N3—C7—O145.9 (5)
C8—N2—C4—C378.6 (4)C5—N3—C7—O1130.0 (4)
C2—C3—C4—N296.7 (4)N5—N4—C6—N360.0 (5)
S1—C3—C4—N284.3 (4)N5—N4—C6—N2128.4 (3)
C7—O1—C8—N247.2 (5)O2—N5—N4—C6166.8 (4)
C6—N2—C8—O17.1 (5)O3—N5—N4—C615.9 (5)
C4—N2—C8—O1169.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O3i1.02 (8)2.60 (8)3.003 (7)106 (6)
C7—H7B···O3ii0.93 (5)2.54 (5)3.354 (7)146 (4)
C8—H8B···N1iii1.01 (5)2.48 (5)3.396 (6)150 (4)
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y, z1; (iii) x+2, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds