2,3-Dihydro-3-methyl-2-nitrimino-1,3-thiazole

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 3p_z 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.

Computing details

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

Crystal data

C4H5N3O2S	F(000) = 164
Mr = 159.17	Dx = 1.679 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 6.947 (2) Å	Cell parameters from 27 reflections
b = 6.469 (3) Å	θ = 9–14°
c = 7.478 (3) Å	µ = 0.45 mm^−1
β = 110.51 (3)°	T = 295 K
V = 314.8 (2) Å^3	Translucent, light orange
Z = 2	0.7 × 0.5 × 0.5 mm

Data collection

Kuma KM4 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 30.1°, θmin = 2.9°
Graphite monochromator	h = −9→9
ω scans	k = −9→0
1958 measured reflections	l = −9→10
994 independent reflections	2 standard reflections every 50 reflections
940 reflections with I > 2σ(I)	intensity decay: 0.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	All H-atom parameters refined
S = 1.11	Calculated w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 0.0468P] where P = (Fo^2 + 2Fc^2)/3
994 reflections	(Δ/σ)max < 0.001
74 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.15659 (6)	1/4	0.01599 (5)	0.03453 (17)
C2	0.3189 (2)	1/4	−0.11204 (19)	0.0265 (3)
N3	0.2129 (2)	1/4	−0.30017 (17)	0.0305 (3)
C4	0.0023 (3)	1/4	−0.3449 (2)	0.0374 (4)
C5	−0.0536 (3)	1/4	−0.1916 (3)	0.0402 (4)
N6	0.5259 (2)	1/4	−0.05619 (18)	0.0299 (3)
N7	0.6240 (2)	1/4	0.13224 (17)	0.0306 (3)
O9	0.5327 (2)	1/4	0.24842 (17)	0.0425 (3)
O8	0.81546 (19)	1/4	0.18608 (19)	0.0466 (4)
C31	0.3109 (3)	1/4	−0.4439 (2)	0.0427 (4)
H4	−0.078 (4)	1/4	−0.471 (4)	0.044 (6)*
H5	−0.191 (4)	1/4	−0.199 (3)	0.040 (6)*
H31A	0.214 (5)	1/4	−0.557 (4)	0.069 (9)*
H31B	0.402 (2)	0.140 (3)	−0.421 (2)	0.056 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0291 (2)	0.0483 (3)	0.0284 (2)	0	0.01276 (18)	0
C2	0.0257 (6)	0.0296 (6)	0.0235 (6)	0	0.0079 (5)	0
N3	0.0273 (6)	0.0402 (7)	0.0224 (5)	0	0.0068 (5)	0
C4	0.0276 (7)	0.0478 (9)	0.0316 (7)	0	0.0037 (6)	0
C5	0.0250 (7)	0.0539 (10)	0.0398 (8)	0	0.0090 (6)	0
N6	0.0258 (6)	0.0388 (7)	0.0239 (6)	0	0.0073 (5)	0
N7	0.0289 (6)	0.0346 (6)	0.0252 (5)	0	0.0056 (5)	0
O9	0.0385 (6)	0.0632 (8)	0.0255 (5)	0	0.0108 (5)	0
O8	0.0262 (6)	0.0709 (10)	0.0361 (6)	0	0.0026 (5)	0
C31	0.0411 (9)	0.0632 (12)	0.0258 (7)	0	0.0142 (7)	0

Geometric parameters (Å, º)

S1—C2	1.716 (2)	N3—C31	1.460 (2)
S1—C5	1.718 (2)	C4—C5	1.333 (2)
C2—N3	1.340 (2)	N6—N7	1.333 (2)
C2—N6	1.349 (2)	N7—O9	1.242 (2)
N3—C4	1.382 (2)	N7—O8	1.247 (2)
C2—S1—C5	90.7 (1)	C5—C4—N3	113.2 (1)
N3—C2—N6	117.3 (1)	C4—C5—S1	111.5 (1)
N3—C2—S1	111.0 (1)	N7—N6—C2	115.0 (1)
N6—C2—S1	131.6 (1)	O9—N7—O8	121.5 (1)
C2—N3—C4	113.6 (1)	O9—N7—N6	122.8 (1)
C2—N3—C31	123.1 (1)	O8—N7—N6	115.7 (1)
C4—N3—C31	123.3 (1)
C5—S1—C2—N3	0.0	C31—N3—C4—C5	180.0
C5—S1—C2—N6	180.0	N3—C4—C5—S1	0.0
N6—C2—N3—C4	180.0	C2—S1—C5—C4	0.0
S1—C2—N3—C4	0.0	N3—C2—N6—N7	180.0
N6—C2—N3—C31	0.0	S1—C2—N6—N7	0.0
S1—C2—N3—C31	180.0	C2—N6—N7—O9	0.0
C2—N3—C4—C5	0.0	C2—N6—N7—O8	180.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O8^i	0.91 (3)	2.41 (3)	3.286 (3)	162 (2)
C5—H5···N6^ii	0.94 (2)	2.55 (2)	3.411 (2)	154 (2)

Symmetry codes: (i) x−1, y, z−1; (ii) x−1, y, z.