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

The mol-ecular framework of the title compound, C(11)H(6)I(2)OS(8), is almost planar [maximum deviation = 0.057 (5) Å] except for the two methyl-sulfanyl groups, which are twisted relative to the mol-ecular skeleton, with C-C-S-C torsion angles of 49.74 (22) and 82.91 (21)°. In the crystal, mol-ecules are stacked alternately in opposite orientations, forming a one-dimensional column along the b axis. The inter-action between adjacent columns is accomplished through S⋯S [3.4289 (5) Å], S⋯I [3.4498 (4) Å] and O⋯I [2.812 (2) Å] contacts.

Related literature

For background to tetra­thia­fulvalenoquinone-1,3-dithiol­emethide derivatives, see: Matsumoto et al. (2002a ▶,b ▶; 2003 ▶); Hiraoka et al. (2007 ▶); Sugimoto (2008 ▶). For the synthesis, see: Iwamatsu et al. (1999 ▶). For background to inter­molecular I⋯O contacts, see: Etter (1976a ▶,b ▶); Groth & Hassel (1965 ▶); Leser & Rabinovich (1978 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C11H6I2OS8

M = 664.44

Monoclinic,

a = 7.7642 (14) Å

b = 17.652 (3) Å

c = 14.124 (3) Å

β = 98.188 (2)°

V = 1916.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 4.15 mm−1

T = 93 K

0.10 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.682, T max = 0.886

11092 measured reflections

4403 independent reflections

3764 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.051

S = 0.99

4403 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHEL (Bruker, 2002 ▶); software used to prepare material for publication: XCIF (Bruker, 2001 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904032X/tk2544sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904032X/tk2544Isup2.hkl

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

C11H6I2OS8	F(000) = 1256
Mr = 664.44	Dx = 2.303 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7642 (14) Å	Cell parameters from 3988 reflections
b = 17.652 (3) Å	θ = 2.3–27.5°
c = 14.124 (3) Å	µ = 4.15 mm−1
β = 98.188 (2)°	T = 93 K
V = 1916.0 (6) Å3	Plate, dark-red
Z = 4	0.10 × 0.07 × 0.03 mm

Bruker APEXII CCD area-detector diffractometer	4403 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	3764 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.030
Detector resolution: 8.333 pixels mm-1	θmax = 27.6°, θmin = 1.9°
φ and ω scans	h = −6→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −22→22
Tmin = 0.682, Tmax = 0.886	l = −18→15
11092 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.019P)2] where P = (Fo2 + 2Fc2)/3
4403 reflections	(Δ/σ)max = 0.006
201 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.56 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
I2	−0.12578 (3)	0.013561 (12)	0.111820 (14)	0.01793 (6)
I1	−0.15011 (3)	−0.203405 (12)	0.164968 (14)	0.01569 (6)
C9	0.6068 (4)	0.19937 (18)	0.7771 (2)	0.0152 (7)
C1	−0.0462 (4)	−0.11760 (18)	0.2570 (2)	0.0149 (7)
C6	0.4087 (4)	0.01803 (18)	0.6428 (2)	0.0136 (6)
C4	0.2274 (4)	−0.04697 (17)	0.4954 (2)	0.0120 (6)
C8	0.6498 (4)	0.14725 (18)	0.8460 (2)	0.0154 (7)
C2	−0.0379 (4)	−0.04383 (18)	0.2381 (2)	0.0143 (7)
C3	0.1281 (4)	−0.06019 (17)	0.4091 (2)	0.0123 (6)
C7	0.4882 (4)	0.07062 (18)	0.7018 (2)	0.0142 (7)
C5	0.2707 (4)	−0.10758 (18)	0.5631 (2)	0.0142 (6)
S6	0.49464 (10)	0.16647 (5)	0.66722 (6)	0.01662 (17)
S4	0.30314 (10)	0.04434 (4)	0.52857 (5)	0.01454 (16)
S2	0.06947 (10)	0.01342 (4)	0.32957 (5)	0.01350 (16)
S7	0.75758 (11)	0.16499 (5)	0.96192 (6)	0.02020 (18)
S5	0.59033 (10)	0.05246 (5)	0.81921 (6)	0.01688 (17)
S3	0.39758 (10)	−0.07854 (5)	0.67194 (6)	0.01666 (17)
S1	0.05054 (10)	−0.14886 (4)	0.36963 (6)	0.01449 (17)
S8	0.63332 (11)	0.29739 (5)	0.79188 (6)	0.02255 (19)
O1	0.2235 (3)	−0.17383 (12)	0.54846 (15)	0.0180 (5)
C11	0.7178 (5)	0.3241 (2)	0.6839 (3)	0.0263 (8)
H13A	0.8305	0.2994	0.6825	0.039*
H13B	0.7326	0.3792	0.6825	0.039*
H13C	0.6362	0.3081	0.6280	0.039*
C10	0.5747 (5)	0.1720 (2)	1.0279 (2)	0.0303 (9)
H12A	0.5026	0.2156	1.0045	0.045*
H12B	0.6174	0.1787	1.0960	0.045*
H12C	0.5051	0.1256	1.0187	0.045*

	U11	U22	U33	U12	U13	U23
I2	0.01932 (12)	0.02057 (12)	0.01307 (11)	0.00006 (9)	−0.00063 (8)	0.00219 (8)
I1	0.01529 (11)	0.01492 (11)	0.01614 (11)	−0.00063 (8)	−0.00027 (8)	−0.00382 (8)
C9	0.0150 (16)	0.0153 (17)	0.0153 (16)	−0.0013 (13)	0.0020 (12)	−0.0021 (13)
C1	0.0128 (15)	0.0164 (17)	0.0153 (16)	−0.0002 (13)	0.0014 (12)	−0.0051 (13)
C6	0.0140 (15)	0.0145 (17)	0.0117 (15)	0.0028 (13)	−0.0003 (12)	0.0016 (12)
C4	0.0151 (15)	0.0091 (16)	0.0122 (15)	0.0011 (12)	0.0028 (12)	−0.0019 (12)
C8	0.0142 (16)	0.0163 (17)	0.0156 (17)	−0.0025 (13)	0.0019 (13)	−0.0050 (13)
C2	0.0120 (15)	0.0183 (18)	0.0118 (16)	−0.0014 (13)	−0.0016 (12)	0.0003 (13)
C3	0.0119 (15)	0.0114 (16)	0.0141 (16)	0.0013 (12)	0.0038 (12)	0.0009 (12)
C7	0.0119 (15)	0.0174 (17)	0.0136 (16)	−0.0007 (12)	0.0029 (12)	−0.0011 (13)
C5	0.0103 (15)	0.0164 (17)	0.0165 (16)	0.0033 (12)	0.0037 (12)	0.0009 (13)
S6	0.0201 (4)	0.0142 (4)	0.0148 (4)	−0.0009 (3)	0.0000 (3)	−0.0002 (3)
S4	0.0172 (4)	0.0111 (4)	0.0143 (4)	−0.0004 (3)	−0.0011 (3)	−0.0005 (3)
S2	0.0170 (4)	0.0104 (4)	0.0123 (4)	−0.0004 (3)	−0.0005 (3)	0.0008 (3)
S7	0.0217 (4)	0.0225 (5)	0.0151 (4)	−0.0016 (4)	−0.0021 (3)	−0.0028 (3)
S5	0.0198 (4)	0.0152 (4)	0.0149 (4)	−0.0016 (3)	−0.0003 (3)	−0.0011 (3)
S3	0.0206 (4)	0.0137 (4)	0.0143 (4)	−0.0007 (3)	−0.0023 (3)	0.0011 (3)
S1	0.0175 (4)	0.0101 (4)	0.0150 (4)	0.0002 (3)	−0.0009 (3)	−0.0004 (3)
S8	0.0317 (5)	0.0141 (4)	0.0218 (5)	−0.0030 (4)	0.0036 (4)	−0.0037 (3)
O1	0.0220 (12)	0.0136 (12)	0.0170 (12)	−0.0005 (10)	−0.0016 (9)	0.0008 (9)
C11	0.032 (2)	0.0164 (19)	0.031 (2)	−0.0020 (15)	0.0087 (16)	0.0030 (15)
C10	0.036 (2)	0.036 (2)	0.0183 (19)	0.0172 (18)	0.0010 (15)	−0.0053 (16)

I2—C2	2.080 (3)	C2—S2	1.755 (3)
I1—C1	2.082 (3)	C3—S2	1.736 (3)
C9—C8	1.347 (4)	C3—S1	1.740 (3)
C9—S8	1.751 (3)	C7—S6	1.764 (3)
C9—S6	1.766 (3)	C7—S5	1.763 (3)
C1—C2	1.333 (4)	C5—O1	1.234 (4)
C1—S1	1.749 (3)	C5—S3	1.780 (3)
C6—C7	1.338 (4)	S7—C10	1.810 (4)
C6—S3	1.759 (3)	S8—C11	1.807 (4)
C6—S4	1.765 (3)	C11—H13A	0.9800
C4—C3	1.366 (4)	C11—H13B	0.9800
C4—C5	1.442 (4)	C11—H13C	0.9800
C4—S4	1.756 (3)	C10—H12A	0.9800
C8—S7	1.757 (3)	C10—H12B	0.9800
C8—S5	1.763 (3)	C10—H12C	0.9800
C8—C9—S8	125.2 (2)	O1—C5—C4	123.8 (3)
C8—C9—S6	116.8 (2)	O1—C5—S3	122.1 (2)
S8—C9—S6	117.69 (18)	C4—C5—S3	114.0 (2)
C2—C1—S1	117.6 (2)	C7—S6—C9	95.85 (15)
C2—C1—I1	127.7 (2)	C4—S4—C6	95.57 (15)
S1—C1—I1	114.61 (17)	C3—S2—C2	95.67 (15)
C7—C6—S3	124.1 (2)	C8—S7—C10	100.80 (15)
C7—C6—S4	120.0 (2)	C8—S5—C7	95.65 (15)
S3—C6—S4	115.91 (17)	C6—S3—C5	96.70 (15)
C3—C4—C5	120.9 (3)	C3—S1—C1	95.27 (14)
C3—C4—S4	121.3 (2)	C9—S8—C11	101.97 (16)
C5—C4—S4	117.8 (2)	S8—C11—H13A	109.5
C9—C8—S7	126.0 (3)	S8—C11—H13B	109.5
C9—C8—S5	117.6 (2)	H13A—C11—H13B	109.5
S7—C8—S5	116.41 (18)	S8—C11—H13C	109.5
C1—C2—S2	116.5 (2)	H13A—C11—H13C	109.5
C1—C2—I2	128.9 (2)	H13B—C11—H13C	109.5
S2—C2—I2	114.47 (17)	S7—C10—H12A	109.5
C4—C3—S2	120.8 (2)	S7—C10—H12B	109.5
C4—C3—S1	124.4 (2)	H12A—C10—H12B	109.5
S2—C3—S1	114.77 (16)	S7—C10—H12C	109.5
C6—C7—S6	121.5 (2)	H12A—C10—H12C	109.5
C6—C7—S5	124.4 (3)	H12B—C10—H12C	109.5
S6—C7—S5	114.10 (17)