5-Eth-oxy-1,3,4-thia-diazole-2(3H)-thione.

In the title compound, C(4)H(6)N(2)OS(2), the dihedral angle between the five-membered heterocyclic ring and the plane of the eth-oxy group is 4.9 (2)°. The 1,3,4-thiadiazole-2-thione unit is planar, with an r.m.s. deviation of 0.011 Å from the corresponding squares plane defined by the seven constituent atoms. In the crystal, pairs of N-H⋯S hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For the synthesis and reactivity of thia­diazole derivatives, see: Hildebrandt et al. (2011 ▶); Zhan et al. (2009 ▶); Cho et al. (1998 ▶); Squillacote & Felippis (1994 ▶); Antolini et al. (1993 ▶).

Experimental

Crystal data

C4H6N2OS2

M = 162.23

Triclinic,

a = 6.0308 (12) Å

b = 8.1171 (16) Å

c = 8.7616 (18) Å

α = 116.55 (4)°

β = 93.70 (3)°

γ = 106.10 (3)°

V = 359.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.66 mm−1

T = 296 K

0.16 × 0.12 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.905, T max = 0.951

10973 measured reflections

1329 independent reflections

1020 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.106

S = 1.03

1329 reflections

86 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002024/is5053sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002024/is5053Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002024/is5053Isup3.cml

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

C4H6N2OS2	Z = 2
Mr = 162.23	F(000) = 168
Triclinic, P1	Dx = 1.498 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0308 (12) Å	Cell parameters from 3632 reflections
b = 8.1171 (16) Å	θ = 2.9–24.6°
c = 8.7616 (18) Å	µ = 0.66 mm−1
α = 116.55 (4)°	T = 296 K
β = 93.70 (3)°	Block, colourless
γ = 106.10 (3)°	0.16 × 0.12 × 0.08 mm
V = 359.7 (2) Å3

Bruker SMART CCD area-detector diffractometer	1020 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
Tmin = 0.905, Tmax = 0.951	k = −9→9
10973 measured reflections	l = −10→10
1329 independent reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3
1329 reflections	(Δ/σ)max < 0.001
86 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.25 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
S1	0.58072 (11)	0.69466 (8)	0.86851 (8)	0.0633 (3)
C2	0.3257 (4)	0.6379 (3)	0.7233 (3)	0.0478 (5)
N3	0.2660 (4)	0.4510 (3)	0.6039 (3)	0.0522 (5)
H3	0.158 (4)	0.408 (4)	0.531 (3)	0.055 (8)*
N4	0.3981 (3)	0.3405 (3)	0.6130 (3)	0.0523 (5)
C5	0.5704 (4)	0.4537 (3)	0.7487 (3)	0.0500 (6)
S6	0.18884 (11)	0.79469 (9)	0.73697 (8)	0.0591 (3)
O7	0.7344 (3)	0.4010 (2)	0.8031 (2)	0.0623 (5)
C8	0.7080 (5)	0.1955 (3)	0.7051 (3)	0.0572 (6)
H8A	0.7218	0.1607	0.5857	0.069*
H8B	0.5544	0.1142	0.7027	0.069*
C9	0.9014 (5)	0.1656 (4)	0.7956 (4)	0.0711 (7)
H9A	0.89	0.0306	0.7338	0.107*
H9B	0.8853	0.1999	0.9133	0.107*
H9C	1.0524	0.2471	0.7974	0.107*

	U11	U22	U33	U12	U13	U23
S1	0.0619 (4)	0.0459 (4)	0.0679 (4)	0.0255 (3)	−0.0096 (3)	0.0151 (3)
C2	0.0472 (12)	0.0499 (13)	0.0521 (12)	0.0229 (10)	0.0101 (10)	0.0260 (10)
N3	0.0476 (11)	0.0498 (11)	0.0560 (12)	0.0221 (9)	−0.0011 (10)	0.0215 (9)
N4	0.0525 (11)	0.0445 (10)	0.0592 (11)	0.0241 (9)	0.0025 (9)	0.0216 (9)
C5	0.0480 (13)	0.0453 (12)	0.0593 (14)	0.0223 (10)	0.0042 (11)	0.0249 (11)
S6	0.0597 (4)	0.0531 (4)	0.0668 (4)	0.0319 (3)	0.0059 (3)	0.0248 (3)
O7	0.0583 (10)	0.0458 (9)	0.0739 (11)	0.0241 (8)	−0.0102 (8)	0.0214 (8)
C8	0.0620 (15)	0.0471 (13)	0.0634 (14)	0.0263 (11)	0.0047 (11)	0.0243 (11)
C9	0.0803 (19)	0.0673 (17)	0.0799 (18)	0.0429 (14)	0.0091 (14)	0.0382 (14)

S1—C5	1.738 (2)	O7—C8	1.449 (3)
S1—C2	1.740 (2)	C8—C9	1.502 (3)
C2—N3	1.325 (3)	C8—H8A	0.97
C2—S6	1.665 (2)	C8—H8B	0.97
N3—N4	1.377 (3)	C9—H9A	0.96
N3—H3	0.76 (2)	C9—H9B	0.96
N4—C5	1.293 (3)	C9—H9C	0.96
C5—O7	1.321 (2)
C5—S1—C2	89.00 (11)	O7—C8—C9	107.07 (19)
N3—C2—S6	127.91 (18)	O7—C8—H8A	110.3
N3—C2—S1	107.12 (17)	C9—C8—H8A	110.3
S6—C2—S1	124.97 (15)	O7—C8—H8B	110.3
C2—N3—N4	120.52 (19)	C9—C8—H8B	110.3
C2—N3—H3	118 (2)	H8A—C8—H8B	108.6
N4—N3—H3	121 (2)	C8—C9—H9A	109.5
C5—N4—N3	107.33 (18)	C8—C9—H9B	109.5
N4—C5—O7	125.7 (2)	H9A—C9—H9B	109.5
N4—C5—S1	116.01 (17)	C8—C9—H9C	109.5
O7—C5—S1	118.33 (16)	H9A—C9—H9C	109.5
C5—O7—C8	115.95 (17)	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S6i	0.76 (2)	2.57 (2)	3.317 (3)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S6i	0.76 (2)	2.57 (2)	3.317 (3)	170 (3)

Symmetry code: (i) .