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

Abstract

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

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

Crystal data

• C₅H₈N₈S₂

• M _r = 244.31

• Orthorhombic,

• a = 6.415 (3) Å

• b = 7.314 (3) Å

• c = 22.204 (8) Å

• V = 1041.9 (7) ų

• Z = 4

• Mo Kα radiation

• μ = 0.49 mm⁻¹

• T = 296 K

• 0.15 × 0.12 × 0.08 mm

Data collection

• CBruker SMART area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.930, T _max = 0.962

• 4692 measured reflections

• 936 independent reflections

• 482 reflections with I > 2σ(I)

• R _int = 0.118

Refinement

• R[F ² > 2σ(F ²)] = 0.063

• wR(F ²) = 0.108

• S = 1.21

• 936 reflections

• 70 parameters

• H-atom parameters constrained

• Δρ_max = 0.34 e Å⁻³

• Δρ_min = −0.38 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

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

supplementary crystallographic information

Experimental

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

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 U_iso(H) values set to be -1.5 of the carrier atom.

Figures

Fig. 1.

A view of the molecular structure of title compound.

Fig. 2.

The crystal packing of the title compound.

Crystal data

C5H8N8S2	F(000) = 504
Mr = 244.31	Dx = 1.558 Mg m−3Dm = 1.558 Mg m−3Dm measured by not measured
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 214 reflections
a = 6.415 (3) Å	θ = 2.5–18.9°
b = 7.314 (3) Å	µ = 0.49 mm−1
c = 22.204 (8) Å	T = 296 K
V = 1041.9 (7) Å3	Flake-like, colourless
Z = 4	0.15 × 0.12 × 0.08 mm

Data collection

CBruker SMART area-detector diffractometer	936 independent reflections
Radiation source: fine-focus sealed tube	482 reflections with I > 2σ(I)
graphite	Rint = 0.118
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
Tmin = 0.930, Tmax = 0.962	k = −8→4
4692 measured reflections	l = −25→26

Refinement

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-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 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	1.1330 (2)	1.03366 (18)	0.19301 (6)	0.0521 (4)
N3	0.6134 (7)	0.9428 (6)	0.1121 (2)	0.0590 (13)
C2	0.9188 (8)	0.9782 (6)	0.1491 (2)	0.0391 (13)
N4	0.7207 (7)	1.0077 (6)	0.16107 (17)	0.0498 (12)
N1	0.9358 (7)	0.8966 (6)	0.09509 (17)	0.0463 (11)
C1	1.1179 (8)	0.8355 (7)	0.0621 (2)	0.0617 (16)
H1A	1.1692	0.9336	0.0375	0.093*
H1B	1.0808	0.7338	0.0369	0.093*
H1C	1.2242	0.7985	0.0899	0.093*
N2	0.7401 (8)	0.8743 (6)	0.07305 (18)	0.0561 (13)
C3	1.0000	1.1654 (9)	0.2500	0.050 (2)
H3A	1.1011	1.2439	0.2697	0.074*	0.50
H3B	0.8989	1.2439	0.2303	0.074*	0.50

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0481 (9)	0.0665 (10)	0.0418 (8)	0.0008 (8)	−0.0041 (7)	−0.0064 (7)
N3	0.049 (3)	0.061 (3)	0.068 (3)	−0.006 (3)	−0.010 (3)	0.001 (3)
C2	0.050 (4)	0.034 (3)	0.033 (3)	−0.004 (3)	−0.002 (2)	0.004 (2)
N4	0.041 (3)	0.061 (3)	0.047 (3)	0.002 (2)	0.004 (2)	0.004 (2)
N1	0.051 (3)	0.053 (3)	0.035 (2)	−0.004 (2)	−0.003 (2)	−0.003 (2)
C1	0.062 (4)	0.075 (4)	0.049 (3)	0.001 (3)	0.004 (3)	−0.012 (3)
N2	0.051 (3)	0.068 (3)	0.050 (3)	−0.004 (3)	−0.008 (3)	0.000 (2)
C3	0.061 (6)	0.054 (5)	0.034 (4)	0.000	−0.012 (4)	0.000

Geometric parameters (Å, °)

S1—C2	1.734 (5)	N1—C1	1.450 (6)
S1—C3	1.805 (4)	C1—H1A	0.9600
N3—N2	1.289 (5)	C1—H1B	0.9600
N3—N4	1.372 (5)	C1—H1C	0.9600
C2—N4	1.316 (6)	C3—S1i	1.805 (4)
C2—N1	1.343 (5)	C3—H3A	0.9700
N1—N2	1.357 (5)	C3—H3B	0.9700
C2—S1—C3	98.31 (19)	H1A—C1—H1B	109.5
N2—N3—N4	110.6 (4)	N1—C1—H1C	109.5
N4—C2—N1	109.4 (4)	H1A—C1—H1C	109.5
N4—C2—S1	127.8 (4)	H1B—C1—H1C	109.5
N1—C2—S1	122.8 (4)	N3—N2—N1	107.1 (4)
C2—N4—N3	105.5 (4)	S1i—C3—S1	115.5 (4)
C2—N1—N2	107.5 (4)	S1i—C3—H3A	108.4
C2—N1—C1	130.8 (5)	S1—C3—H3A	108.4
N2—N1—C1	121.7 (4)	S1i—C3—H3B	108.4
N1—C1—H1A	109.5	S1—C3—H3B	108.4
N1—C1—H1B	109.5	H3A—C3—H3B	107.5

Symmetry codes: (i) −x+2, y, −z+1/2.