5-(4,5-Diiodo-1,3-dithiol-2-yl-idene)-4',5'-bis-(methyl-sulfan-yl)-2,2'-bi-1,3-dithiole-4(5H)-thione.

The mol-ecular skeleton of the title mol-ecule, C(11)H(6)I(2)S(9), is nearly planar [maximum deviation 0.052 (3) Å] except for the two methyl groups. In the crystal, mol-ecules related by translation along b axis are associated into columns through π-π inter-actions between the five-membered rings, with a centroid-centroid distance of 3.593 (5) Å. Inter-action between adjacent columns is accomplished by short S⋯I contacts of 3.2099 (4) Å.

Related literature

For background to tetra­thia­fulvalenothio­quinone-1,3-dithiol­emethide derivatives, see: Iwamatsu et al. (2000 ▶); Wang et al. (2005 ▶, 2007 ▶); Hiraoka et al. (2005 ▶); Fujiwara et al. (2006 ▶, 2007 ▶). For details of the synthesis, see Iwamatsu et al. (1999 ▶). For inter­molecular S⋯I contacts, see: Ahlsen & Strømme (1974 ▶); Herbstein & Schwortzer (1984 ▶); Freemanm et al. (1988 ▶); Bigoli et al. (1996 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C11H6I2S9

M = 680.50

Monoclinic,

a = 29.540 (7) Å

b = 5.3543 (13) Å

c = 25.163 (6) Å

β = 103.544 (3)°

V = 3869.2 (16) Å3

Z = 8

Mo Kα radiation

μ = 4.21 mm−1

T = 93 K

0.55 × 0.18 × 0.01 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.205, T max = 0.979

10568 measured reflections

4387 independent reflections

3536 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 1.07

4387 reflections

201 parameters

H-atom parameters constrained

Δρmax = 3.45 e Å−3

Δρmin = −2.31 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: XCIF (Bruker, 2001 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042573/cv2627sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042573/cv2627Isup2.hkl

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

C11H6I2S9	F(000) = 2576
Mr = 680.50	Dx = 2.336 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2871 reflections
a = 29.540 (7) Å	θ = 2.4–27.5°
b = 5.3543 (13) Å	µ = 4.21 mm−1
c = 25.163 (6) Å	T = 93 K
β = 103.544 (3)°	Needle, black
V = 3869.2 (16) Å3	0.55 × 0.18 × 0.01 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	4387 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	3536 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.040
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 1.4°
φ and ω scans	h = −38→36
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
Tmin = 0.205, Tmax = 0.979	l = −24→32
10568 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.028P)2 + 20.8292P] where P = (Fo2 + 2Fc2)/3
4387 reflections	(Δ/σ)max = 0.002
201 parameters	Δρmax = 3.45 e Å−3
0 restraints	Δρmin = −2.31 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
C1	1.01287 (15)	1.3727 (9)	0.35298 (19)	0.0158 (10)
C2	1.02057 (16)	1.2692 (10)	0.4024 (2)	0.0198 (11)
C3	0.94845 (15)	1.0393 (9)	0.34447 (18)	0.0150 (10)
C4	0.91248 (16)	0.8707 (9)	0.32900 (19)	0.0157 (10)
C5	0.88305 (16)	0.8507 (9)	0.27608 (19)	0.0152 (10)
C6	0.85596 (16)	0.5009 (9)	0.3338 (2)	0.0177 (10)
C7	0.83308 (16)	0.3149 (10)	0.35177 (19)	0.0180 (11)
C8	0.80459 (17)	−0.0037 (10)	0.4151 (2)	0.0213 (11)
C9	0.77585 (16)	−0.0346 (10)	0.3660 (2)	0.0197 (11)
C10	0.8099 (2)	0.0697 (12)	0.5245 (2)	0.0345 (14)
H10A	0.8431	0.1096	0.5359	0.052*
H10B	0.7988	0.0128	0.5562	0.052*
H10C	0.7925	0.2190	0.5090	0.052*
C11	0.68641 (17)	−0.0497 (11)	0.3739 (2)	0.0244 (12)
H11A	0.6975	−0.0211	0.4132	0.037*
H11B	0.6563	−0.1358	0.3667	0.037*
H11C	0.6828	0.1110	0.3547	0.037*
I1	1.052758 (10)	1.64937 (6)	0.326836 (12)	0.01695 (10)
I2	1.075939 (14)	1.33621 (9)	0.468614 (15)	0.04003 (14)
S1	0.96539 (4)	1.2618 (2)	0.30265 (5)	0.0163 (2)
S2	0.98132 (4)	1.0369 (3)	0.41150 (5)	0.0202 (3)
S3	0.88601 (4)	1.0394 (2)	0.22343 (5)	0.0186 (3)
S4	0.90284 (4)	0.6524 (2)	0.37793 (5)	0.0196 (3)
S5	0.84272 (4)	0.6130 (2)	0.26660 (5)	0.0194 (3)
S6	0.84983 (4)	0.2173 (3)	0.42068 (5)	0.0217 (3)
S7	0.78627 (4)	0.1484 (3)	0.31171 (5)	0.0200 (3)
S8	0.80104 (5)	−0.1743 (3)	0.47356 (5)	0.0231 (3)
S9	0.72837 (4)	−0.2411 (3)	0.34965 (5)	0.0200 (3)

	U11	U22	U33	U12	U13	U23
C1	0.013 (2)	0.020 (3)	0.015 (2)	−0.0029 (19)	0.0032 (18)	−0.002 (2)
C2	0.018 (2)	0.023 (3)	0.017 (2)	−0.004 (2)	−0.0002 (19)	0.002 (2)
C3	0.015 (2)	0.017 (3)	0.012 (2)	0.0032 (19)	0.0015 (18)	−0.0001 (19)
C4	0.015 (2)	0.015 (3)	0.017 (2)	0.0032 (19)	0.0038 (18)	0.004 (2)
C5	0.017 (2)	0.016 (3)	0.015 (2)	0.0061 (19)	0.0073 (18)	−0.0025 (19)
C6	0.017 (2)	0.015 (3)	0.020 (3)	−0.0027 (19)	0.0026 (19)	−0.004 (2)
C7	0.017 (2)	0.020 (3)	0.016 (2)	0.000 (2)	0.0033 (19)	−0.003 (2)
C8	0.018 (2)	0.020 (3)	0.026 (3)	−0.004 (2)	0.007 (2)	−0.001 (2)
C9	0.013 (2)	0.020 (3)	0.027 (3)	−0.002 (2)	0.0050 (19)	−0.004 (2)
C10	0.047 (4)	0.035 (4)	0.024 (3)	−0.007 (3)	0.015 (3)	−0.002 (3)
C11	0.018 (2)	0.029 (3)	0.026 (3)	−0.001 (2)	0.005 (2)	−0.004 (2)
I1	0.01587 (16)	0.01857 (18)	0.01695 (17)	−0.00209 (12)	0.00491 (12)	−0.00065 (13)
I2	0.0346 (2)	0.0579 (3)	0.0204 (2)	−0.0239 (2)	−0.00805 (16)	0.01043 (18)
S1	0.0161 (6)	0.0184 (6)	0.0143 (6)	−0.0014 (5)	0.0033 (4)	0.0016 (5)
S2	0.0195 (6)	0.0269 (7)	0.0133 (6)	−0.0053 (5)	0.0019 (5)	0.0029 (5)
S3	0.0198 (6)	0.0193 (7)	0.0160 (6)	0.0023 (5)	0.0027 (5)	0.0014 (5)
S4	0.0223 (6)	0.0212 (7)	0.0153 (6)	−0.0046 (5)	0.0046 (5)	0.0002 (5)
S5	0.0188 (6)	0.0194 (7)	0.0185 (6)	−0.0034 (5)	0.0014 (5)	−0.0020 (5)
S6	0.0208 (6)	0.0254 (8)	0.0182 (6)	−0.0065 (5)	0.0031 (5)	−0.0005 (5)
S7	0.0200 (6)	0.0215 (7)	0.0179 (6)	−0.0040 (5)	0.0033 (5)	−0.0012 (5)
S8	0.0254 (7)	0.0233 (7)	0.0202 (7)	−0.0050 (5)	0.0044 (5)	0.0014 (5)
S9	0.0182 (6)	0.0207 (7)	0.0214 (6)	−0.0037 (5)	0.0052 (5)	−0.0039 (5)

C1—C2	1.331 (7)	C7—S7	1.752 (5)
C1—S1	1.758 (5)	C7—S6	1.767 (5)
C1—I1	2.093 (5)	C8—C9	1.336 (7)
C2—S2	1.751 (5)	C8—S8	1.755 (5)
C2—I2	2.074 (5)	C8—S6	1.766 (5)
C3—C4	1.379 (7)	C9—S9	1.758 (5)
C3—S2	1.738 (4)	C9—S7	1.766 (5)
C3—S1	1.739 (5)	C10—S8	1.806 (6)
C4—C5	1.414 (6)	C10—H10A	0.9800
C4—S4	1.769 (5)	C10—H10B	0.9800
C5—S3	1.685 (5)	C10—H10C	0.9800
C5—S5	1.721 (5)	C11—S9	1.820 (5)
C6—C7	1.340 (7)	C11—H11A	0.9800
C6—S5	1.750 (5)	C11—H11B	0.9800
C6—S4	1.758 (5)	C11—H11C	0.9800
C2—C1—S1	117.7 (4)	C8—C9—S9	126.4 (4)
C2—C1—I1	127.1 (4)	C8—C9—S7	117.3 (4)
S1—C1—I1	115.2 (2)	S9—C9—S7	116.2 (3)
C1—C2—S2	116.4 (4)	S8—C10—H10A	109.5
C1—C2—I2	127.5 (4)	S8—C10—H10B	109.5
S2—C2—I2	116.1 (3)	H10A—C10—H10B	109.5
C4—C3—S2	119.2 (4)	S8—C10—H10C	109.5
C4—C3—S1	126.1 (4)	H10A—C10—H10C	109.5
S2—C3—S1	114.7 (3)	H10B—C10—H10C	109.5
C3—C4—C5	125.4 (5)	S9—C11—H11A	109.5
C3—C4—S4	118.4 (4)	S9—C11—H11B	109.5
C5—C4—S4	116.2 (4)	H11A—C11—H11B	109.5
C4—C5—S3	124.2 (4)	S9—C11—H11C	109.5
C4—C5—S5	116.1 (4)	H11A—C11—H11C	109.5
S3—C5—S5	119.8 (3)	H11B—C11—H11C	109.5
C7—C6—S5	124.4 (4)	C3—S1—C1	95.1 (2)
C7—C6—S4	121.0 (4)	C3—S2—C2	96.0 (2)
S5—C6—S4	114.6 (3)	C6—S4—C4	95.5 (2)
C6—C7—S7	125.2 (4)	C5—S5—C6	97.4 (2)
C6—C7—S6	120.2 (4)	C8—S6—C7	95.0 (2)
S7—C7—S6	114.6 (3)	C7—S7—C9	95.4 (2)
C9—C8—S8	124.1 (4)	C8—S8—C10	101.0 (3)
C9—C8—S6	117.5 (4)	C9—S9—C11	97.8 (2)
S8—C8—S6	118.4 (3)