N-(5-Methyl-sulfanyl-1,3,4-thia-diazol-2-yl)acetamide.

In the title compound, C(5)H(7)N(3)OS(2), inversion dimers linked by pairs of N-H⋯N hydrogen bonds occur, forming R(2) (2)(8) ring motifs. These dimers are arranged into chains via inter-molecular C-H⋯O hydrogen bonds between the methylsulfanyl groups and the O atoms of the carbonyl groups. The acetamido-1,3,4-thio-diazole unit is essentially planar [r.m.s. deviation 0.045 (8) Å].

Related literature

For the applications of 1,3,4-thio­diazole and its derivatives in anti­microbial drugs and in the construction of metal-organic frameworks, see: Gardinier et al. (2007 ▶); Mrozek et al. (2000 ▶); Xue et al. (2008 ▶). For the synthesis, see: Clerici & Pocar (2001 ▶).

Experimental

Crystal data

C5H7N3OS2

M = 189.26

Triclinic,

a = 5.0797 (10) Å

b = 7.9894 (16) Å

c = 10.081 (2) Å

α = 91.96 (3)°

β = 90.94 (3)°

γ = 105.27 (3)°

V = 394.32 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.62 mm−1

T = 293 K

0.30 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.836, T max = 0.941

3437 measured reflections

1382 independent reflections

1259 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.07

1382 reflections

106 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030554/bq2155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030554/bq2155Isup2.hkl

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

C5H7N3OS2	Z = 2
Mr = 189.26	F(000) = 196
Triclinic, P1	Dx = 1.594 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0797 (10) Å	Cell parameters from 3437 reflections
b = 7.9894 (16) Å	θ = 3.3–27.6°
c = 10.081 (2) Å	µ = 0.62 mm−1
α = 91.96 (3)°	T = 293 K
β = 90.94 (3)°	Block, yellow
γ = 105.27 (3)°	0.30 × 0.30 × 0.10 mm
V = 394.32 (14) Å3

Rigaku R-AXIS RAPID-S diffractometer	1382 independent reflections
Radiation source: fine-focus sealed tube	1259 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −6→6
Tmin = 0.836, Tmax = 0.941	k = −9→9
3437 measured reflections	l = −11→11

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.1675P] where P = (Fo2 + 2Fc2)/3
1382 reflections	(Δ/σ)max = 0.001
106 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
C1	0.8654 (4)	0.6728 (3)	0.3920 (2)	0.0434 (5)
H1A	0.8055	0.5632	0.4333	0.065*
H1B	0.9004	0.6534	0.3002	0.065*
H1C	0.7261	0.7336	0.3984	0.065*
C2	1.0570 (4)	0.8285 (2)	0.63353 (18)	0.0267 (4)
C3	0.8380 (4)	0.8321 (2)	0.83774 (18)	0.0260 (4)
C4	0.4332 (4)	0.6973 (2)	0.95823 (19)	0.0282 (4)
C5	0.2992 (4)	0.7042 (3)	1.0889 (2)	0.0358 (5)
H5A	0.1062	0.6539	1.0780	0.054*
H5B	0.3327	0.8229	1.1205	0.054*
H5C	0.3730	0.6404	1.1521	0.054*
H3	0.732 (5)	0.878 (3)	1.008 (2)	0.039 (7)*
N1	1.2055 (3)	0.9415 (2)	0.71786 (16)	0.0324 (4)
N2	1.0764 (3)	0.9425 (2)	0.83800 (16)	0.0312 (4)
N3	0.6785 (3)	0.8170 (2)	0.94718 (17)	0.0300 (4)
O1	0.3383 (3)	0.59336 (19)	0.86769 (14)	0.0406 (4)
S1	1.17277 (10)	0.80015 (7)	0.47435 (5)	0.03824 (18)
S2	0.74395 (9)	0.71212 (6)	0.69103 (5)	0.02978 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0426 (13)	0.0547 (14)	0.0290 (11)	0.0073 (11)	−0.0009 (9)	−0.0095 (10)
C2	0.0247 (9)	0.0298 (10)	0.0247 (9)	0.0057 (7)	0.0016 (7)	0.0004 (7)
C3	0.0256 (10)	0.0268 (9)	0.0237 (10)	0.0041 (8)	0.0004 (7)	−0.0039 (7)
C4	0.0253 (10)	0.0280 (10)	0.0298 (10)	0.0046 (8)	0.0011 (8)	−0.0005 (8)
C5	0.0328 (11)	0.0379 (11)	0.0336 (11)	0.0036 (9)	0.0085 (9)	0.0009 (9)
N1	0.0286 (9)	0.0358 (9)	0.0290 (9)	0.0021 (7)	0.0051 (7)	−0.0041 (7)
N2	0.0264 (9)	0.0336 (9)	0.0279 (9)	−0.0012 (7)	0.0038 (7)	−0.0062 (7)
N3	0.0266 (9)	0.0327 (9)	0.0246 (9)	−0.0017 (7)	0.0023 (7)	−0.0087 (7)
O1	0.0339 (8)	0.0409 (8)	0.0369 (8)	−0.0064 (6)	0.0029 (6)	−0.0117 (7)
S1	0.0323 (3)	0.0532 (4)	0.0271 (3)	0.0080 (2)	0.0066 (2)	−0.0043 (2)
S2	0.0256 (3)	0.0336 (3)	0.0247 (3)	−0.0007 (2)	0.00124 (19)	−0.00701 (19)

C1—S1	1.796 (2)	C3—S2	1.7244 (19)
C1—H1A	0.9600	C4—O1	1.216 (2)
C1—H1B	0.9600	C4—N3	1.365 (3)
C1—H1C	0.9600	C4—C5	1.499 (3)
C2—N1	1.294 (3)	C5—H5A	0.9600
C2—S2	1.737 (2)	C5—H5B	0.9600
C2—S1	1.7457 (19)	C5—H5C	0.9600
C3—N2	1.297 (2)	N1—N2	1.387 (2)
C3—N3	1.369 (3)	N3—H3	0.77 (2)
S1—C1—H1A	109.5	N3—C4—C5	114.83 (17)
S1—C1—H1B	109.5	C4—C5—H5A	109.5
H1A—C1—H1B	109.5	C4—C5—H5B	109.5
S1—C1—H1C	109.5	H5A—C5—H5B	109.5
H1A—C1—H1C	109.5	C4—C5—H5C	109.5
H1B—C1—H1C	109.5	H5A—C5—H5C	109.5
N1—C2—S2	115.25 (14)	H5B—C5—H5C	109.5
N1—C2—S1	120.67 (15)	C2—N1—N2	111.35 (16)
S2—C2—S1	124.08 (11)	C3—N2—N1	112.70 (15)
N2—C3—N3	120.95 (17)	C4—N3—C3	124.71 (17)
N2—C3—S2	114.78 (14)	C4—N3—H3	117.4 (18)
N3—C3—S2	124.27 (14)	C3—N3—H3	117.8 (18)
O1—C4—N3	121.00 (18)	C2—S1—C1	101.30 (10)
O1—C4—C5	124.16 (18)	C3—S2—C2	85.91 (9)
S2—C2—N1—N2	0.3 (2)	S2—C3—N3—C4	4.8 (3)
S1—C2—N1—N2	−179.74 (13)	N1—C2—S1—C1	−166.91 (17)
N3—C3—N2—N1	−178.87 (17)	S2—C2—S1—C1	13.04 (15)
S2—C3—N2—N1	0.6 (2)	N2—C3—S2—C2	−0.35 (15)
C2—N1—N2—C3	−0.6 (2)	N3—C3—S2—C2	179.09 (17)
O1—C4—N3—C3	−0.2 (3)	N1—C2—S2—C3	0.01 (16)
C5—C4—N3—C3	178.85 (18)	S1—C2—S2—C3	−179.95 (13)
N2—C3—N3—C4	−175.77 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	0.77 (2)	2.12 (2)	2.881 (2)	173 (2)
C1—H1B···O1ii	0.96	2.58	3.289 (3)	131 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	0.77 (2)	2.12 (2)	2.881 (2)	173 (2)
C1—H1B⋯O1ii	0.96	2.58	3.289 (3)	131 (2)

Symmetry codes: (i) ; (ii) .