Bis[(1-methyl-1H-tetra-zol-5-yl)sulfan-yl]ethane.

The title compound, C(6)H(10)N(8)S(2), was prepared by the nucleophilic substitution reaction of 5-mercapto-1-methyl-tetra-zole and dichloro-ethane. In the crystal, the mol-ecule possesses an approximate non-crystallographic twofold symmetry axis. The crystal packing is stabilized by weak inter-molecular C-H⋯N and π-π inter-actions [centroid-centroid distances = 3.448 (6), 3.5085 (5) and 3.4591 (2) Å]. The two five-membered rings form a dihedral angle of 1.9 (2)°.

Related literature

For the synthesis and structures of closely related compounds, see: She et al. (2006 ▶); Wei et al. (2011 ▶). For the pharmacological activity of tetra­zole-containing compounds, see: Gilchrist (1992 ▶); Armour et al. (1996 ▶); Upadhayaya et al. (2004 ▶). For applications of tetra­zole derivatives in coordination chemistry and as energetic materials, see: Zhao et al. (2008 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

C6H10N8S2

M = 258.34

Triclinic,

a = 7.5905 (17) Å

b = 7.9958 (17) Å

c = 10.398 (2) Å

α = 95.206 (3)°

β = 92.922 (3)°

γ = 115.109 (2)°

V = 566.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 296 K

0.31 × 0.27 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.868, T max = 0.982

2874 measured reflections

1972 independent reflections

1454 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.39

1972 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.26 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021957/yk2010sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021957/yk2010Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021957/yk2010Isup3.cml

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

C6H10N8S2	Z = 2
Mr = 258.34	F(000) = 268
Triclinic, P1	Dx = 1.515 Mg m−3Dm = 1.515 Mg m−3Dm measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5905 (17) Å	Cell parameters from 816 reflections
b = 7.9958 (17) Å	θ = 3.0–24.3°
c = 10.398 (2) Å	µ = 0.46 mm−1
α = 95.206 (3)°	T = 296 K
β = 92.922 (3)°	Flake-like, colourless
γ = 115.109 (2)°	0.31 × 0.27 × 0.04 mm
V = 566.3 (2) Å3

Bruker APEXII CCD diffractometer	1972 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→9
Tmin = 0.868, Tmax = 0.982	k = −9→9
2874 measured reflections	l = −12→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.39	w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
1972 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 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	0.09578 (12)	0.84390 (12)	0.77838 (9)	0.0521 (3)
S2	0.09347 (12)	0.29485 (12)	0.68329 (10)	0.0556 (3)
C3	0.1006 (5)	0.5022 (4)	0.7748 (3)	0.0475 (8)
H3A	−0.0186	0.4695	0.8171	0.071*
H3B	0.2096	0.5507	0.8418	0.071*
C4	0.1213 (5)	0.6503 (4)	0.6906 (3)	0.0462 (8)
H4A	0.0224	0.5975	0.6169	0.069*
H4B	0.2485	0.6952	0.6576	0.069*
N8	0.4054 (4)	0.2801 (4)	0.5763 (3)	0.0453 (7)
N1	0.3945 (4)	1.1385 (4)	0.9194 (3)	0.0508 (7)
N7	0.6021 (4)	0.3722 (4)	0.5857 (3)	0.0553 (8)
C2	0.3378 (5)	0.3691 (4)	0.6618 (3)	0.0416 (8)
N4	0.4956 (4)	0.9965 (4)	0.7756 (3)	0.0593 (8)
N5	0.4887 (4)	0.5150 (4)	0.7245 (3)	0.0560 (8)
N3	0.6501 (4)	1.1452 (5)	0.8422 (3)	0.0673 (9)
C5	0.3392 (5)	0.9955 (5)	0.8249 (3)	0.0463 (8)
N6	0.6500 (4)	0.5133 (4)	0.6750 (3)	0.0611 (8)
C1	0.2987 (5)	0.1146 (5)	0.4834 (4)	0.0571 (10)
H1A	0.3772	0.1141	0.4140	0.086*
H1B	0.1791	0.1151	0.4489	0.086*
H1C	0.2693	0.0055	0.5260	0.086*
N2	0.5909 (5)	1.2321 (4)	0.9288 (3)	0.0664 (9)
C6	0.2779 (6)	1.1957 (6)	1.0046 (4)	0.0694 (12)
H6A	0.1958	1.2344	0.9540	0.104*
H6B	0.3631	1.2973	1.0675	0.104*
H6C	0.1981	1.0929	1.0482	0.104*

	U11	U22	U33	U12	U13	U23
S1	0.0445 (5)	0.0435 (5)	0.0671 (6)	0.0217 (4)	0.0033 (4)	−0.0113 (4)
S2	0.0421 (5)	0.0364 (5)	0.0800 (7)	0.0130 (4)	0.0051 (4)	−0.0121 (5)
C3	0.046 (2)	0.0407 (19)	0.054 (2)	0.0201 (16)	0.0055 (15)	−0.0083 (16)
C4	0.046 (2)	0.0393 (19)	0.0510 (19)	0.0189 (16)	0.0026 (15)	−0.0081 (16)
N8	0.0426 (16)	0.0439 (16)	0.0483 (16)	0.0188 (13)	0.0039 (13)	−0.0006 (13)
N1	0.0494 (18)	0.0460 (17)	0.0492 (16)	0.0150 (15)	0.0033 (13)	−0.0037 (14)
N7	0.0469 (18)	0.059 (2)	0.0606 (18)	0.0229 (16)	0.0091 (14)	0.0061 (16)
C2	0.0393 (18)	0.0323 (17)	0.0483 (18)	0.0128 (15)	−0.0012 (15)	−0.0021 (15)
N4	0.0489 (19)	0.057 (2)	0.067 (2)	0.0194 (16)	0.0076 (15)	−0.0027 (16)
N5	0.0457 (18)	0.0510 (18)	0.0647 (19)	0.0192 (15)	−0.0068 (15)	−0.0098 (15)
N3	0.0475 (19)	0.063 (2)	0.075 (2)	0.0088 (17)	0.0081 (17)	0.0056 (18)
C5	0.051 (2)	0.0419 (19)	0.0460 (19)	0.0220 (17)	−0.0010 (16)	−0.0004 (16)
N6	0.0456 (18)	0.055 (2)	0.074 (2)	0.0171 (15)	−0.0039 (16)	−0.0024 (17)
C1	0.064 (2)	0.0388 (19)	0.059 (2)	0.0167 (18)	0.0033 (18)	−0.0145 (17)
N2	0.057 (2)	0.057 (2)	0.069 (2)	0.0104 (17)	−0.0027 (17)	0.0026 (17)
C6	0.070 (3)	0.074 (3)	0.060 (2)	0.034 (2)	0.005 (2)	−0.023 (2)

S1—C5	1.738 (4)	N1—C6	1.457 (4)
S1—C4	1.812 (3)	N7—N6	1.302 (4)
S2—C2	1.724 (3)	C2—N5	1.323 (4)
S2—C3	1.814 (3)	N4—C5	1.314 (4)
C3—C4	1.496 (5)	N4—N3	1.362 (4)
C3—H3A	0.9700	N5—N6	1.357 (4)
C3—H3B	0.9700	N3—N2	1.299 (4)
C4—H4A	0.9700	C1—H1A	0.9600
C4—H4B	0.9700	C1—H1B	0.9600
N8—C2	1.342 (4)	C1—H1C	0.9600
N8—N7	1.349 (4)	C6—H6A	0.9600
N8—C1	1.456 (4)	C6—H6B	0.9600
N1—C5	1.340 (4)	C6—H6C	0.9600
N1—N2	1.348 (4)
C5—S1—C4	100.94 (15)	N5—C2—S2	128.0 (3)
C2—S2—C3	100.20 (15)	N8—C2—S2	123.6 (2)
C4—C3—S2	112.2 (2)	C5—N4—N3	105.8 (3)
C4—C3—H3A	109.2	C2—N5—N6	106.0 (3)
S2—C3—H3A	109.2	N2—N3—N4	110.7 (3)
C4—C3—H3B	109.2	N4—C5—N1	108.9 (3)
S2—C3—H3B	109.2	N4—C5—S1	128.2 (3)
H3A—C3—H3B	107.9	N1—C5—S1	122.9 (3)
C3—C4—S1	111.8 (2)	N7—N6—N5	110.8 (3)
C3—C4—H4A	109.3	N8—C1—H1A	109.5
S1—C4—H4A	109.3	N8—C1—H1B	109.5
C3—C4—H4B	109.3	H1A—C1—H1B	109.5
S1—C4—H4B	109.3	N8—C1—H1C	109.5
H4A—C4—H4B	107.9	H1A—C1—H1C	109.5
C2—N8—N7	108.6 (3)	H1B—C1—H1C	109.5
C2—N8—C1	129.7 (3)	N3—N2—N1	106.3 (3)
N7—N8—C1	121.7 (3)	N1—C6—H6A	109.5
C5—N1—N2	108.3 (3)	N1—C6—H6B	109.5
C5—N1—C6	130.2 (3)	H6A—C6—H6B	109.5
N2—N1—C6	121.5 (3)	N1—C6—H6C	109.5
N6—N7—N8	106.2 (2)	H6A—C6—H6C	109.5
N5—C2—N8	108.4 (3)	H6B—C6—H6C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N4i	0.96	2.49	3.413 (5)	161
C6—H6B···N5ii	0.96	2.43	3.355 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N4i	0.96	2.49	3.413 (5)	161
C6—H6B⋯N5ii	0.96	2.43	3.355 (5)	161

Symmetry codes: (i) ; (ii) .