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The title compound {alternatively, 3-methyl-2-[oxido(oxo)hydrazono]-2,3-dihydro-1,3-thiazole}, C4H5N3O2S, was obtained by methyl­ation of N-(2-thia­zolyl)­nitr­amine. The molecule lies on a mirror plane and the thia­zole ring is planar, regular in shape and aromatic. The S atom participates in the aromatic sextet via an electron pair on the 3pz orbital. In the crystal, the mol­ecules are arranged in parallel layers, bound to each other by weak C—H...O and C—H...N hydrogen bonds and by S...O dipolar interactions, with an interlayer separation of 3.23 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011604/gd1113sup1.cif
Contains datablocks global, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011604/gd1113IIIsup2.hkl
Contains datablock III

CCDC reference: 153923

Computing details top

Cell refinement: Kuma Diffraction Software (Kuma, 1997); data reduction: Kuma Diffraction Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

2,3-Dihydro-3-methyl-2-nitriminothiazole top
Crystal data top
C4H5N3O2SF(000) = 164
Mr = 159.17Dx = 1.679 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 6.947 (2) ÅCell parameters from 27 reflections
b = 6.469 (3) Åθ = 9–14°
c = 7.478 (3) ŵ = 0.45 mm1
β = 110.51 (3)°T = 295 K
V = 314.8 (2) Å3Translucent, light orange
Z = 20.7 × 0.5 × 0.5 mm
Data collection top
Kuma KM4
diffractometer
Rint = 0.031
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 2.9°
Graphite monochromatorh = 99
ω scansk = 90
1958 measured reflectionsl = 910
994 independent reflections2 standard reflections every 50 reflections
940 reflections with I > 2σ(I) intensity decay: 0.3%
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097All H-atom parameters refined
S = 1.11Calculated w = 1/[σ2(Fo2) + (0.0563P)2 + 0.0468P]
where P = (Fo2 + 2Fc2)/3
994 reflections(Δ/σ)max < 0.001
74 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.26 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
S10.15659 (6)1/40.01599 (5)0.03453 (17)
C20.3189 (2)1/40.11204 (19)0.0265 (3)
N30.2129 (2)1/40.30017 (17)0.0305 (3)
C40.0023 (3)1/40.3449 (2)0.0374 (4)
C50.0536 (3)1/40.1916 (3)0.0402 (4)
N60.5259 (2)1/40.05619 (18)0.0299 (3)
N70.6240 (2)1/40.13224 (17)0.0306 (3)
O90.5327 (2)1/40.24842 (17)0.0425 (3)
O80.81546 (19)1/40.18608 (19)0.0466 (4)
C310.3109 (3)1/40.4439 (2)0.0427 (4)
H40.078 (4)1/40.471 (4)0.044 (6)*
H50.191 (4)1/40.199 (3)0.040 (6)*
H31A0.214 (5)1/40.557 (4)0.069 (9)*
H31B0.402 (2)0.140 (3)0.421 (2)0.056 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0291 (2)0.0483 (3)0.0284 (2)00.01276 (18)0
C20.0257 (6)0.0296 (6)0.0235 (6)00.0079 (5)0
N30.0273 (6)0.0402 (7)0.0224 (5)00.0068 (5)0
C40.0276 (7)0.0478 (9)0.0316 (7)00.0037 (6)0
C50.0250 (7)0.0539 (10)0.0398 (8)00.0090 (6)0
N60.0258 (6)0.0388 (7)0.0239 (6)00.0073 (5)0
N70.0289 (6)0.0346 (6)0.0252 (5)00.0056 (5)0
O90.0385 (6)0.0632 (8)0.0255 (5)00.0108 (5)0
O80.0262 (6)0.0709 (10)0.0361 (6)00.0026 (5)0
C310.0411 (9)0.0632 (12)0.0258 (7)00.0142 (7)0
Geometric parameters (Å, º) top
S1—C21.716 (2)N3—C311.460 (2)
S1—C51.718 (2)C4—C51.333 (2)
C2—N31.340 (2)N6—N71.333 (2)
C2—N61.349 (2)N7—O91.242 (2)
N3—C41.382 (2)N7—O81.247 (2)
C2—S1—C590.7 (1)C5—C4—N3113.2 (1)
N3—C2—N6117.3 (1)C4—C5—S1111.5 (1)
N3—C2—S1111.0 (1)N7—N6—C2115.0 (1)
N6—C2—S1131.6 (1)O9—N7—O8121.5 (1)
C2—N3—C4113.6 (1)O9—N7—N6122.8 (1)
C2—N3—C31123.1 (1)O8—N7—N6115.7 (1)
C4—N3—C31123.3 (1)
C5—S1—C2—N30.0C31—N3—C4—C5180.0
C5—S1—C2—N6180.0N3—C4—C5—S10.0
N6—C2—N3—C4180.0C2—S1—C5—C40.0
S1—C2—N3—C40.0N3—C2—N6—N7180.0
N6—C2—N3—C310.0S1—C2—N6—N70.0
S1—C2—N3—C31180.0C2—N6—N7—O90.0
C2—N3—C4—C50.0C2—N6—N7—O8180.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O8i0.91 (3)2.41 (3)3.286 (3)162 (2)
C5—H5···N6ii0.94 (2)2.55 (2)3.411 (2)154 (2)
Symmetry codes: (i) x1, y, z1; (ii) x1, y, z.
 

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