Bis(4H-1,2,4-triazol-3-yl)disulfane.

The title compound, C(4)H(4)N(6)S(2), was synthesized by the reaction of 3-mercapto-1H-1,2,4-triazole with sodium hydrox-ide in ethanol. The mol-ecule possesses a crystallographically imposed twofold axis. Inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into chains along the c axis.

Related literature

For related literature, see: De Luca (2006 ▶); Di Santo, Tafi, Costi, Botta, Artico, Corelli, Forte, Caporuscio, Angiolella & Palamara (2005 ▶); Fringuelli et al. (2005 ▶); Menozzi et al. (2004 ▶).

Experimental

Crystal data

C4H4N6S2

M = 200.25

Monoclinic,

a = 14.052 (3) Å

b = 6.4044 (13) Å

c = 9.928 (2) Å

β = 122.18 (3)°

V = 756.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 293 (2) K

0.12 × 0.09 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.932, T max = 0.962

3518 measured reflections

859 independent reflections

742 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.081

S = 1.09

859 reflections

63 parameters

All H-atom parameters refined

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO (Rigaku, 1998 ▶); data reduction: RAPID-AUTO (Rigaku, 1998 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 1993 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick,1997 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065452/rz2177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065452/rz2177Isup2.hkl

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

C4H4N6S2	F000 = 408
Mr = 200.25	Dx = 1.759 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 14.052 (3) Å	θ = 12–18º
b = 6.4044 (13) Å	µ = 0.65 mm−1
c = 9.928 (2) Å	T = 293 (2) K
β = 122.18 (3)º	Block, colourless
V = 756.2 (4) Å3	0.12 × 0.09 × 0.06 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	859 independent reflections
Radiation source: fine-focus sealed tube	742 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 293(2) K	θmax = 27.5º
Oscillation scans	θmin = 3.4º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −18→18
Tmin = 0.932, Tmax = 0.962	k = −8→7
3518 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	All H-atom parameters refined
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0491P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
859 reflections	Δρmax = 0.25 e Å−3
63 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.08684 (3)	0.07452 (6)	−0.17828 (4)	0.03333 (18)
N1	0.13246 (12)	0.4379 (2)	0.15290 (16)	0.0330 (3)
N2	0.11117 (12)	0.2436 (2)	0.08916 (15)	0.0350 (3)
N3	0.13151 (11)	0.4757 (2)	−0.06502 (15)	0.0315 (3)
C1	0.11097 (11)	0.2743 (2)	−0.04273 (16)	0.0275 (3)
C2	0.14361 (13)	0.5723 (3)	0.06089 (18)	0.0331 (4)
H1	0.1365 (17)	0.462 (4)	0.244 (3)	0.053 (6)*
H2	0.1600 (16)	0.725 (3)	0.083 (2)	0.042 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0383 (3)	0.0327 (3)	0.0299 (3)	0.00536 (14)	0.0188 (2)	−0.00149 (13)
N1	0.0378 (7)	0.0423 (8)	0.0238 (7)	0.0035 (5)	0.0197 (6)	−0.0008 (5)
N2	0.0434 (7)	0.0387 (8)	0.0284 (7)	0.0037 (5)	0.0228 (6)	0.0035 (5)
N3	0.0383 (7)	0.0365 (7)	0.0258 (7)	−0.0025 (5)	0.0212 (6)	−0.0017 (5)
C1	0.0280 (7)	0.0346 (8)	0.0215 (7)	0.0031 (5)	0.0143 (6)	0.0022 (5)
C2	0.0357 (8)	0.0387 (9)	0.0270 (8)	−0.0029 (6)	0.0181 (7)	−0.0034 (6)

S1—C1	1.7541 (15)	N2—C1	1.3225 (19)
S1—S1i	2.0693 (11)	N3—C2	1.322 (2)
N1—C2	1.324 (2)	N3—C1	1.3653 (19)
N1—N2	1.3549 (18)	C2—H2	1.004 (19)
N1—H1	0.89 (2)
C1—S1—S1i	101.72 (5)	N2—C1—N3	114.30 (13)
C2—N1—N2	110.63 (13)	N2—C1—S1	123.30 (12)
C2—N1—H1	128.6 (15)	N3—C1—S1	122.40 (11)
N2—N1—H1	120.8 (15)	N3—C2—N1	110.21 (15)
C1—N2—N1	102.11 (13)	N3—C2—H2	124.4 (12)
C2—N3—C1	102.74 (13)	N1—C2—H2	125.4 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ii	0.89 (2)	1.97 (2)	2.8617 (19)	174.9 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.89 (2)	1.97 (2)	2.8617 (19)	174.9 (19)

Symmetry code: (i) .