2-[(1H-Imidazol-2-yl)disulfan-yl]-1H-imidazole.

In the title molecule, C(6)H(6)N(4)S(2), a twofold rotation axis passes through the mid-point of the S-S bond. The C-S-S-C torsion angle is 83.62 (17)°. π-π stacking between imidazole rings of adjacent mol-ecules is observed in the crystal structure, the centroid-centroid distance being 3.447 (2) Å. Inter-molecular N-H⋯S hydrogen bonding results in the formation of a linear chain in the c-axis direction.

Related literature

For related imidazole disulfide compounds, see: Robina et al. (1990 ▶); Figueroa et al. (2007 ▶); Chernovyants et al. (2008 ▶).

Experimental

Crystal data

C6H6N4S2

M = 198.29

Monoclinic,

a = 14.083 (3) Å

b = 6.3928 (13) Å

c = 9.922 (2) Å

β = 122.29 (3)°

V = 755.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 298 K

0.45 × 0.25 × 0.15 mm

Data collection

STOE IPDS II diffractometer

Absorption correction: multi-scan (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.823, T max = 0.906

4116 measured reflections

1007 independent reflections

948 reflections with I > 2σ(I)

R int = 0.112

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.185

S = 1.18

1007 reflections

56 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.56 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036014/xu5318sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036014/xu5318Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036014/xu5318Isup3.cml

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

C6H6N4S2	F(000) = 408
Mr = 198.29	Dx = 1.744 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1007 reflections
a = 14.083 (3) Å	θ = 3.4–23°
b = 6.3928 (13) Å	µ = 0.64 mm−1
c = 9.922 (2) Å	T = 298 K
β = 122.29 (3)°	Prism, colorless
V = 755.1 (4) Å3	0.45 × 0.25 × 0.15 mm
Z = 4

STOE IPDS II diffractometer	1007 independent reflections
graphite	948 reflections with I > 2σ(I)
Detector resolution: 0.15 pixels mm-1	Rint = 0.112
rotation method scans	θmax = 29.2°, θmin = 3.4°
Absorption correction: multi-scan (X-RED and X-SHAPE; Stoe & Cie, 2005)	h = −19→19
Tmin = 0.823, Tmax = 0.906	k = −8→6
4116 measured reflections	l = −13→13

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.185	w = 1/[σ2(Fo2) + (0.1134P)2 + 0.6898P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
1007 reflections	Δρmax = 0.82 e Å−3
56 parameters	Δρmin = −0.56 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.11 (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	0.08686 (5)	0.07449 (9)	0.32168 (6)	0.0337 (4)
N1	0.13136 (17)	0.4761 (4)	0.4347 (2)	0.0319 (5)
N2	0.11134 (18)	0.2432 (4)	0.5892 (2)	0.0350 (6)
H2A	0.1006	0.129	0.625	0.042*
C1	0.11109 (17)	0.2743 (4)	0.4570 (2)	0.0281 (5)
C2	0.1440 (2)	0.5734 (4)	0.5611 (3)	0.0335 (6)
H2	0.1585	0.7155	0.5821	0.04*
C3	0.13289 (18)	0.4382 (4)	0.6536 (2)	0.0280 (5)
H3	0.139	0.4723	0.7491	0.034*

	U11	U22	U33	U12	U13	U23
S1	0.0385 (5)	0.0326 (5)	0.0294 (5)	0.00531 (19)	0.0178 (4)	−0.00166 (17)
N1	0.0407 (10)	0.0348 (11)	0.0256 (9)	−0.0026 (8)	0.0213 (7)	−0.0020 (7)
N2	0.0451 (11)	0.0375 (11)	0.0271 (10)	0.0024 (8)	0.0226 (8)	0.0042 (7)
C1	0.0300 (10)	0.0334 (11)	0.0222 (10)	0.0028 (8)	0.0147 (8)	0.0011 (7)
C2	0.0382 (12)	0.0369 (14)	0.0260 (11)	−0.0032 (8)	0.0175 (9)	−0.0040 (7)
C3	0.0316 (10)	0.0373 (13)	0.0180 (9)	0.0023 (7)	0.0151 (8)	−0.0010 (7)

S1—C1	1.750 (2)	N2—C3	1.359 (3)
S1—S1i	2.0713 (14)	N2—H2A	0.86
N1—C2	1.324 (3)	C2—C3	1.329 (3)
N1—C1	1.364 (3)	C2—H2	0.93
N2—C1	1.324 (3)	C3—H3	0.93
C1—S1—S1i	101.62 (7)	N1—C1—S1	122.51 (16)
C2—N1—C1	102.96 (19)	N1—C2—C3	110.0 (2)
C1—N2—C3	102.12 (19)	N1—C2—H2	125
C1—N2—H2A	128.9	C3—C2—H2	125
C3—N2—H2A	128.9	C2—C3—N2	110.52 (19)
N2—C1—N1	114.4 (2)	C2—C3—H3	124.7
N2—C1—S1	123.13 (18)	N2—C3—H3	124.7
C3—N2—C1—N1	0.1 (3)	S1i—S1—C1—N1	−93.68 (18)
C3—N2—C1—S1	−179.85 (15)	C1—N1—C2—C3	0.5 (3)
C2—N1—C1—N2	−0.4 (3)	N1—C2—C3—N2	−0.4 (3)
C2—N1—C1—S1	179.60 (17)	C1—N2—C3—C2	0.2 (3)
S1i—S1—C1—N2	86.31 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1ii	0.86	2.44	3.227 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.44	3.227 (3)	153

Symmetry code: (i) .