5-Amino-1,3,4-thia-diazol-2(3H)-one.

The asymmetric unit of the title compound, C(2)H(3)N(3)OS, contains three independent mol-ecules which are essentially planar, with r.m.s. deviations of 0.011 (2)-0.027 (2) Å from the mean plane defined by the seven non-H atoms. In the crystal, N-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a sheet parallel to the (111) plane.

Related literature

For the structures and reactivity of thia­diazole derivatives, see: Parkanyi et al. (1989 ▶); Cho, Cho et al. (1996 ▶); Cho, Ra et al. (1996 ▶). For the biological activity of thia­diazole derivatives, see: Castro et al. (2008 ▶); Ra, Cho & Cho (1998 ▶); Ra, Cho, Moon & Kang (1998 ▶).

Experimental

Crystal data

C2H3N3OS

M = 117.13

Triclinic,

a = 7.2860 (2) Å

b = 10.2982 (3) Å

c = 10.7727 (3) Å

α = 63.721 (3)°

β = 73.122 (2)°

γ = 76.737 (2)°

V = 688.74 (3) Å3

Z = 6

Mo Kα radiation

μ = 0.57 mm−1

T = 296 K

0.15 × 0.1 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.93, T max = 0.97

23857 measured reflections

3433 independent reflections

2526 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 0.94

3433 reflections

226 parameters

All H-atom parameters refined

Δρmax = 0.30 e Å−3

Δρmin = −0.26 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/S1600536812012433/is5096sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012433/is5096Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012433/is5096Isup3.cml

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

C2H3N3OS	Z = 6
Mr = 117.13	F(000) = 360
Triclinic, P1	Dx = 1.694 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2860 (2) Å	Cell parameters from 5437 reflections
b = 10.2982 (3) Å	θ = 2.2–26.1°
c = 10.7727 (3) Å	µ = 0.57 mm−1
α = 63.721 (3)°	T = 296 K
β = 73.122 (2)°	Block, colourless
γ = 76.737 (2)°	0.15 × 0.1 × 0.05 mm
V = 688.74 (3) Å3

Bruker SMART CCD area-detector diffractometer	2526 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.93, Tmax = 0.97	k = −13→13
23857 measured reflections	l = −14→14
3433 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	All H-atom parameters refined
S = 0.94	w = 1/[σ2(Fo2) + (0.0423P)2] where P = (Fo2 + 2Fc2)/3
3433 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.86165 (6)	−0.07773 (5)	−0.06572 (4)	0.03647 (13)
C2	0.7587 (2)	0.10880 (18)	−0.13554 (16)	0.0339 (4)
N3	0.6466 (2)	0.13649 (15)	−0.02585 (14)	0.0329 (3)
H3	0.580 (3)	0.219 (2)	−0.0362 (19)	0.044 (5)*
N4	0.62764 (19)	0.02538 (14)	0.10886 (13)	0.0303 (3)
C5	0.7333 (2)	−0.09181 (17)	0.10313 (16)	0.0289 (3)
O6	0.7853 (2)	0.19397 (15)	−0.26078 (12)	0.0517 (4)
N7	0.7416 (3)	−0.21857 (17)	0.21825 (17)	0.0472 (4)
H7A	0.825 (3)	−0.291 (3)	0.210 (2)	0.072 (7)*
H7B	0.672 (3)	−0.224 (2)	0.297 (2)	0.052 (6)*
S8	0.15828 (7)	0.02436 (5)	0.59226 (4)	0.03889 (13)
C9	0.3260 (2)	−0.05097 (18)	0.47618 (16)	0.0338 (4)
N10	0.3484 (2)	0.05559 (15)	0.34594 (14)	0.0353 (3)
H10	0.439 (3)	0.047 (2)	0.262 (2)	0.065 (6)*
N11	0.2481 (2)	0.19183 (14)	0.32756 (13)	0.0354 (3)
C12	0.1437 (2)	0.19073 (18)	0.44702 (16)	0.0348 (4)
O13	0.40594 (19)	−0.17651 (13)	0.51031 (13)	0.0485 (3)
N14	0.0375 (3)	0.3114 (2)	0.4619 (2)	0.0592 (5)
H14A	−0.048 (3)	0.297 (2)	0.536 (3)	0.070 (7)*
H14B	0.019 (3)	0.387 (2)	0.386 (2)	0.050 (6)*
S15	0.23799 (7)	0.66689 (5)	−0.15169 (5)	0.04302 (14)
C16	0.1723 (2)	0.55543 (18)	0.03347 (17)	0.0363 (4)
N17	0.2688 (2)	0.42407 (15)	0.05437 (15)	0.0353 (3)
H17	0.262 (3)	0.352 (2)	0.138 (2)	0.053 (6)*
N18	0.3933 (2)	0.40035 (14)	−0.06009 (13)	0.0354 (3)
C19	0.3895 (2)	0.51734 (17)	−0.17336 (17)	0.0356 (4)
O20	0.0594 (2)	0.59341 (14)	0.12439 (14)	0.0537 (4)
N21	0.4930 (3)	0.5249 (2)	−0.30232 (18)	0.0651 (6)
H21A	0.492 (4)	0.606 (3)	−0.363 (3)	0.081 (8)*
H21B	0.566 (3)	0.455 (3)	−0.304 (2)	0.071 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0365 (2)	0.0374 (2)	0.0315 (2)	0.00386 (18)	0.00096 (17)	−0.01947 (18)
C2	0.0319 (9)	0.0371 (9)	0.0289 (8)	−0.0040 (7)	−0.0003 (7)	−0.0139 (7)
N3	0.0386 (8)	0.0250 (7)	0.0254 (6)	0.0032 (6)	−0.0008 (6)	−0.0089 (6)
N4	0.0345 (7)	0.0262 (7)	0.0233 (6)	0.0000 (6)	−0.0004 (5)	−0.0091 (5)
C5	0.0290 (8)	0.0292 (8)	0.0274 (7)	−0.0007 (7)	−0.0024 (6)	−0.0139 (7)
O6	0.0631 (9)	0.0485 (8)	0.0246 (6)	−0.0049 (7)	0.0027 (6)	−0.0064 (6)
N7	0.0625 (12)	0.0306 (9)	0.0324 (8)	0.0104 (8)	−0.0046 (8)	−0.0096 (7)
S8	0.0458 (3)	0.0368 (2)	0.02102 (19)	−0.00454 (19)	0.00086 (17)	−0.00531 (17)
C9	0.0375 (9)	0.0317 (9)	0.0270 (8)	−0.0028 (7)	−0.0059 (7)	−0.0084 (7)
N10	0.0412 (8)	0.0293 (7)	0.0241 (6)	0.0039 (6)	−0.0013 (6)	−0.0080 (6)
N11	0.0412 (8)	0.0276 (7)	0.0224 (6)	0.0029 (6)	0.0011 (6)	−0.0052 (6)
C12	0.0366 (9)	0.0310 (9)	0.0261 (8)	−0.0022 (7)	0.0009 (7)	−0.0078 (7)
O13	0.0601 (9)	0.0290 (7)	0.0423 (7)	0.0049 (6)	−0.0128 (6)	−0.0056 (6)
N14	0.0692 (13)	0.0386 (10)	0.0393 (10)	0.0088 (9)	0.0126 (9)	−0.0111 (8)
S15	0.0533 (3)	0.0232 (2)	0.0365 (2)	0.00734 (19)	−0.0052 (2)	−0.00628 (18)
C16	0.0386 (10)	0.0298 (9)	0.0342 (9)	0.0008 (7)	−0.0040 (7)	−0.0121 (7)
N17	0.0417 (9)	0.0258 (7)	0.0255 (7)	0.0029 (6)	−0.0009 (6)	−0.0061 (6)
N18	0.0423 (8)	0.0241 (7)	0.0267 (7)	0.0036 (6)	0.0006 (6)	−0.0074 (6)
C19	0.0428 (10)	0.0240 (8)	0.0305 (8)	0.0000 (7)	−0.0020 (7)	−0.0083 (7)
O20	0.0561 (9)	0.0453 (8)	0.0474 (7)	0.0072 (6)	0.0046 (6)	−0.0238 (6)
N21	0.0938 (16)	0.0328 (10)	0.0314 (9)	0.0067 (10)	0.0134 (9)	−0.0036 (8)

S1—C5	1.7449 (15)	N10—H10	0.98 (2)
S1—C2	1.7905 (17)	N11—C12	1.2874 (19)
C2—O6	1.2270 (19)	C12—N14	1.354 (2)
C2—N3	1.333 (2)	N14—H14A	0.83 (2)
N3—N4	1.3857 (18)	N14—H14B	0.86 (2)
N3—H3	0.854 (19)	S15—C19	1.7419 (17)
N4—C5	1.2905 (19)	S15—C16	1.7876 (17)
C5—N7	1.349 (2)	C16—O20	1.2298 (19)
N7—H7A	0.87 (2)	C16—N17	1.327 (2)
N7—H7B	0.84 (2)	N17—N18	1.3853 (18)
S8—C12	1.7419 (16)	N17—H17	0.88 (2)
S8—C9	1.7874 (17)	N18—C19	1.2821 (19)
C9—O13	1.2264 (19)	C19—N21	1.352 (2)
C9—N10	1.336 (2)	N21—H21A	0.80 (3)
N10—N11	1.3817 (18)	N21—H21B	0.79 (2)
C5—S1—C2	88.70 (7)	C12—N11—N10	110.16 (13)
O6—C2—N3	126.79 (16)	N11—C12—N14	123.00 (15)
O6—C2—S1	126.30 (13)	N11—C12—S8	115.37 (12)
N3—C2—S1	106.90 (12)	N14—C12—S8	121.53 (13)
C2—N3—N4	119.16 (14)	C12—N14—H14A	116.1 (16)
C2—N3—H3	122.2 (13)	C12—N14—H14B	117.8 (13)
N4—N3—H3	118.5 (13)	H14A—N14—H14B	118 (2)
C5—N4—N3	109.74 (12)	C19—S15—C16	88.49 (8)
N4—C5—N7	122.96 (15)	O20—C16—N17	126.47 (16)
N4—C5—S1	115.48 (12)	O20—C16—S15	126.48 (13)
N7—C5—S1	121.54 (12)	N17—C16—S15	107.05 (12)
C5—N7—H7A	118.8 (15)	C16—N17—N18	119.02 (14)
C5—N7—H7B	119.4 (14)	C16—N17—H17	122.9 (13)
H7A—N7—H7B	122 (2)	N18—N17—H17	118.0 (13)
C12—S8—C9	88.73 (7)	C19—N18—N17	109.75 (13)
O13—C9—N10	126.70 (16)	N18—C19—N21	122.74 (16)
O13—C9—S8	126.29 (13)	N18—C19—S15	115.68 (12)
N10—C9—S8	107.01 (12)	N21—C19—S15	121.57 (13)
C9—N10—N11	118.72 (13)	C19—N21—H21A	113.9 (17)
C9—N10—H10	125.0 (12)	C19—N21—H21B	116.2 (17)
N11—N10—H10	116.1 (12)	H21A—N21—H21B	128 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N18	0.854 (19)	2.004 (19)	2.8516 (19)	171.9 (18)
N7—H7A···O20i	0.87 (2)	2.07 (2)	2.907 (2)	160 (2)
N10—H10···N4	0.98 (2)	1.88 (2)	2.8558 (19)	175.7 (18)
N14—H14A···O6ii	0.83 (2)	2.10 (2)	2.897 (2)	162 (2)
N17—H17···N11	0.88 (2)	1.97 (2)	2.8424 (18)	179 (4)
N21—H21A···O13iii	0.80 (3)	2.10 (3)	2.878 (2)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N18	0.854 (19)	2.004 (19)	2.8516 (19)	171.9 (18)
N7—H7A⋯O20i	0.87 (2)	2.07 (2)	2.907 (2)	160 (2)
N10—H10⋯N4	0.98 (2)	1.88 (2)	2.8558 (19)	175.7 (18)
N14—H14A⋯O6ii	0.83 (2)	2.10 (2)	2.897 (2)	162 (2)
N17—H17⋯N11	0.88 (2)	1.97 (2)	2.8424 (18)	179 (4)
N21—H21A⋯O13iii	0.80 (3)	2.10 (3)	2.878 (2)	163 (2)

Symmetry codes: (i) ; (ii) ; (iii) .