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Acta Cryst. (2011). E67, o999    [ doi:10.1107/S1600536811011007 ]

Bis[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methane

W. Wei, Z. Xia, S. Chen and S. Gao

Abstract top

The molecule of the title compound, C5H8N8S2, lies on a twofold rotation axis that relates on 1-methyltetrazolyl group to the other; the five-membered rings are twisted by 53.1 (1)°.

Related literature top

For the synthesis and pharmacological activity of compounds containing tetrazole groups, see: Semenov (2002); Upadhayaya et al. (2004). For a related structure, see: Bronisz (2002).

Experimental top

Sodium hydroxide (1.7 g, 0.043 mol) was added to 5-mercapto-1-methyltetrazole (5 g, 0.043 mol) in dry dimethylsulfoxide (35 ml). The reaction mixture was stirred at 363 K for 1 h. Dichloromethane (3.1 ml, 0.0215 mol) was then added to the solution dropwise with the formation of a grey suspension. The suspension was stirred for 4 h, cooled to room temperature and filtered. The solvent was removed completely under reduced pressure. The residue was recrystallized from ethanol to give a white crystalline product (2.94 g; m.p. 353 - 354 K). Single crystals of the title compound suitable for X-ray diffraction analysis were isolated after a week from a solution in acetone.

Refinement top

All H atoms were positioned geometrically (C—H = 0.96 Å for aromatic CH3 and 0.97 Å for CH2 groups, respectively) and constrained to ride on their parent atoms with Uiso(H) values set to be -1.5 of the carrier atom.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of title compound.
[Figure 2] Fig. 2. The crystal packing of the title compound.
Bis[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methane top
Crystal data top
C5H8N8S2F(000) = 504
Mr = 244.31Dx = 1.558 Mg m−3
Dm = 1.558 Mg m−3
Dm measured by not measured
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 214 reflections
a = 6.415 (3) Åθ = 2.5–18.9°
b = 7.314 (3) ŵ = 0.49 mm−1
c = 22.204 (8) ÅT = 296 K
V = 1041.9 (7) Å3Flake-like, colourless
Z = 40.15 × 0.12 × 0.08 mm
Data collection top
CBruker SMART area-detector
diffractometer		936 independent reflections
Radiation source: fine-focus sealed tube482 reflections with I > 2σ(I)
graphiteRint = 0.118
φ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −7→7
Tmin = 0.930, Tmax = 0.962k = −8→4
4692 measured reflectionsl = −25→26
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.21 w = 1/[σ2(Fo2) + (0.P)2 + 0.7202P]
where P = (Fo2 + 2Fc2)/3
936 reflections(Δ/σ)max < 0.001
70 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C5H8N8S2V = 1041.9 (7) Å3
Mr = 244.31Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 6.415 (3) ŵ = 0.49 mm−1
b = 7.314 (3) ÅT = 296 K
c = 22.204 (8) Å0.15 × 0.12 × 0.08 mm
Data collection top
CBruker SMART area-detector
diffractometer		936 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		482 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.962Rint = 0.118
4692 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.108Δρmax = 0.34 e Å−3
S = 1.21Δρmin = −0.38 e Å−3
936 reflectionsAbsolute structure: ?
70 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S11.1330 (2)1.03366 (18)0.19301 (6)0.0521 (4)
N30.6134 (7)0.9428 (6)0.1121 (2)0.0590 (13)
C20.9188 (8)0.9782 (6)0.1491 (2)0.0391 (13)
N40.7207 (7)1.0077 (6)0.16107 (17)0.0498 (12)
N10.9358 (7)0.8966 (6)0.09509 (17)0.0463 (11)
C11.1179 (8)0.8355 (7)0.0621 (2)0.0617 (16)
H1A1.16920.93360.03750.093*
H1B1.08080.73380.03690.093*
H1C1.22420.79850.08990.093*
N20.7401 (8)0.8743 (6)0.07305 (18)0.0561 (13)
C31.00001.1654 (9)0.25000.050 (2)
H3A1.10111.24390.26970.074*0.50
H3B0.89891.24390.23030.074*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0481 (9)0.0665 (10)0.0418 (8)0.0008 (8)−0.0041 (7)−0.0064 (7)
N30.049 (3)0.061 (3)0.068 (3)−0.006 (3)−0.010 (3)0.001 (3)
C20.050 (4)0.034 (3)0.033 (3)−0.004 (3)−0.002 (2)0.004 (2)
N40.041 (3)0.061 (3)0.047 (3)0.002 (2)0.004 (2)0.004 (2)
N10.051 (3)0.053 (3)0.035 (2)−0.004 (2)−0.003 (2)−0.003 (2)
C10.062 (4)0.075 (4)0.049 (3)0.001 (3)0.004 (3)−0.012 (3)
N20.051 (3)0.068 (3)0.050 (3)−0.004 (3)−0.008 (3)0.000 (2)
C30.061 (6)0.054 (5)0.034 (4)0.000−0.012 (4)0.000
Geometric parameters (Å, °) top
S1—C21.734 (5)N1—C11.450 (6)
S1—C31.805 (4)C1—H1A0.9600
N3—N21.289 (5)C1—H1B0.9600
N3—N41.372 (5)C1—H1C0.9600
C2—N41.316 (6)C3—S1i1.805 (4)
C2—N11.343 (5)C3—H3A0.9700
N1—N21.357 (5)C3—H3B0.9700
C2—S1—C398.31 (19)H1A—C1—H1B109.5
N2—N3—N4110.6 (4)N1—C1—H1C109.5
N4—C2—N1109.4 (4)H1A—C1—H1C109.5
N4—C2—S1127.8 (4)H1B—C1—H1C109.5
N1—C2—S1122.8 (4)N3—N2—N1107.1 (4)
C2—N4—N3105.5 (4)S1i—C3—S1115.5 (4)
C2—N1—N2107.5 (4)S1i—C3—H3A108.4
C2—N1—C1130.8 (5)S1—C3—H3A108.4
N2—N1—C1121.7 (4)S1i—C3—H3B108.4
N1—C1—H1A109.5S1—C3—H3B108.4
N1—C1—H1B109.5H3A—C3—H3B107.5
Symmetry codes: (i) −x+2, y, −z+1/2.
Acknowledgements top

We gratefully acknowledge the National Science Foundation of China (No. 20873100) and the Natural Science Foundation of Shaanxi Province (No. SJ08B09).

references
References top

Bronisz. (2002). Inorg. Chim. Acta, 340, 215–220.

Bruker (2002). SADABS, SAINT and SMART. Bruker AXSInc., Madison,Wisconsin, USA.

Semenov, B. B. (2002). Russ. Chem. Bull. 51, 357–358.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Upadhayaya, R. S., Jain, S., Sinha, N., Kishore, N., Chandra, R. & Arora, S. K. (2004). Eur. J. Med. Chem. 39, 579–592.