(5E)-2-[4,5-Bis(methyl-sulfan-yl)-1,3-dithiol-2-yl-idene]-5-(4-iodo-1,3-dithiol-2-yl-idene)-1,3-dithio-lan-4-one.

The mol-ecular framework of the title compound, C(11)H(7)IOS(8), is almost planar [maximum deviation = 0.040 (4) Å], except for the two methyl-sulfanyl groups, which are twisted relative to the mol-ecular skeleton, making C-S-C-C torsion angles of 144.1 (8) and -141.3 (8)°. In the crystal, mol-ecules are stacked alternately in opposite orientations, forming a one-dimensional column parallel to [110]. The primary inter-actions between mol-ecules comprising the columns are of the S⋯S type [3.554 (1) Å]. Inter-actions between columns are of the S⋯S type [3.411 (1) along b and 3.444 (1) Å along c], as well as S⋯I contacts [3.435 (2) Å].

Related literature

For background to 2,5-di(1,3-dithiole-2-yl­idene)-1,3-dithio­lan-4-one derivatives, see: Iwamatsu et al. (1999 ▶); Matsumoto et al. (2002 ▶, 2003 ▶); Hiraoka et al. (2007 ▶); Ueda & Yoza (2009 ▶). For the synthesis, see: Ueda & Yoza (2009 ▶). For background to inter­molecular S⋯I contacts, see: Blake et al. (1997 ▶, 1998 ▶, 1999 ▶); Bricklebank et al. (2000 ▶); Ouvrard et al. (2003 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C11H7IOS8

M = 538.55

Triclinic,

a = 8.309 (3) Å

b = 8.344 (3) Å

c = 14.618 (7) Å

α = 90.851 (6)°

β = 105.132 (6)°

γ = 118.510 (4)°

V = 848.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.87 mm−1

T = 93 K

0.04 × 0.04 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.894, T max = 0.894

9773 measured reflections

3820 independent reflections

3065 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.161

S = 1.07

3820 reflections

190 parameters

H-atom parameters constrained

Δρmax = 2.34 e Å−3

Δρmin = −1.13 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: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: XCIF (Bruker, 2001 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044493/tk2559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044493/tk2559Isup2.hkl

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

C11H7IOS8	Z = 2
Mr = 538.55	F(000) = 524
Triclinic, P1	Dx = 2.109 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.309 (3) Å	Cell parameters from 2153 reflections
b = 8.344 (3) Å	θ = 2.8–25.3°
c = 14.618 (7) Å	µ = 2.87 mm−1
α = 90.851 (6)°	T = 93 K
β = 105.132 (6)°	Block, dark-red
γ = 118.510 (4)°	0.04 × 0.04 × 0.04 mm
V = 848.0 (6) Å3

Bruker APEXII CCD area-detector diffractometer	3820 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	3065 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.050
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.894, Tmax = 0.894	l = −18→18
9773 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0842P)2 + 3.4063P] where P = (Fo2 + 2Fc2)/3
3820 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 2.34 e Å−3
0 restraints	Δρmin = −1.13 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	0.7414 (11)	0.3494 (11)	1.2804 (5)	0.0208 (15)
C2	0.7832 (11)	0.2717 (10)	1.2163 (5)	0.0200 (15)
H2A	0.7957	0.1652	1.2252	0.024*
C3	0.7600 (10)	0.5445 (10)	1.1458 (5)	0.0171 (14)
C4	0.7523 (10)	0.6656 (10)	1.0854 (5)	0.0147 (14)
C5	0.7096 (11)	0.8045 (10)	1.1130 (5)	0.0176 (15)
C6	0.7518 (10)	0.8433 (10)	0.9411 (5)	0.0188 (15)
C7	0.7691 (10)	0.9104 (10)	0.8586 (5)	0.0168 (14)
C8	0.7811 (11)	1.1023 (10)	0.7195 (5)	0.0195 (15)
C9	0.8259 (11)	0.9774 (10)	0.6922 (6)	0.0227 (16)
C10	0.5811 (14)	1.2907 (13)	0.6735 (8)	0.040 (2)
H10A	0.5663	1.3860	0.6401	0.060*
H10B	0.6051	1.3221	0.7424	0.060*
H10C	0.4633	1.1708	0.6481	0.060*
C11	0.7773 (12)	0.7290 (12)	0.5471 (7)	0.0317 (19)
H11A	0.8072	0.7093	0.4888	0.048*
H11B	0.6381	0.6763	0.5324	0.048*
H11C	0.8218	0.6686	0.5964	0.048*
I1	0.72165 (7)	0.26967 (7)	1.41327 (4)	0.02158 (17)
O1	0.6819 (8)	0.8263 (7)	1.1898 (4)	0.0248 (12)
S2	0.6928 (3)	0.9427 (3)	1.02369 (13)	0.0204 (4)
S3	0.7856 (3)	0.6574 (3)	0.97138 (13)	0.0192 (4)
S4	0.7150 (3)	0.5414 (2)	1.25643 (13)	0.0180 (4)
S5	0.8134 (3)	0.3773 (3)	1.11542 (14)	0.0223 (4)
S6	0.7799 (3)	1.2779 (3)	0.65508 (14)	0.0222 (4)
S7	0.8283 (3)	0.8205 (3)	0.77148 (14)	0.0215 (4)
S8	0.7337 (3)	1.0982 (3)	0.83040 (14)	0.0212 (4)
S9	0.8974 (4)	0.9749 (3)	0.59090 (16)	0.0318 (5)

	U11	U22	U33	U12	U13	U23
C1	0.018 (4)	0.025 (4)	0.019 (4)	0.011 (3)	0.004 (3)	0.005 (3)
C2	0.029 (4)	0.017 (4)	0.018 (4)	0.015 (3)	0.008 (3)	0.006 (3)
C3	0.014 (3)	0.015 (3)	0.021 (4)	0.005 (3)	0.006 (3)	0.001 (3)
C4	0.018 (3)	0.014 (3)	0.016 (3)	0.010 (3)	0.006 (3)	0.004 (3)
C5	0.021 (4)	0.021 (4)	0.014 (3)	0.011 (3)	0.007 (3)	0.004 (3)
C6	0.019 (4)	0.020 (4)	0.018 (4)	0.010 (3)	0.006 (3)	0.003 (3)
C7	0.017 (3)	0.017 (4)	0.014 (3)	0.007 (3)	0.005 (3)	0.002 (3)
C8	0.022 (4)	0.021 (4)	0.014 (4)	0.008 (3)	0.010 (3)	0.005 (3)
C9	0.024 (4)	0.016 (4)	0.027 (4)	0.005 (3)	0.014 (3)	0.007 (3)
C10	0.045 (6)	0.035 (5)	0.062 (7)	0.028 (5)	0.032 (5)	0.027 (5)
C11	0.030 (4)	0.026 (4)	0.038 (5)	0.010 (4)	0.016 (4)	0.002 (4)
I1	0.0234 (3)	0.0216 (3)	0.0216 (3)	0.0115 (2)	0.0088 (2)	0.00788 (19)
O1	0.034 (3)	0.022 (3)	0.026 (3)	0.017 (3)	0.014 (3)	0.010 (2)
S2	0.0297 (10)	0.0244 (10)	0.0164 (9)	0.0194 (8)	0.0092 (8)	0.0063 (7)
S3	0.0267 (10)	0.0213 (9)	0.0160 (9)	0.0154 (8)	0.0094 (8)	0.0053 (7)
S4	0.0220 (9)	0.0180 (9)	0.0191 (9)	0.0113 (7)	0.0111 (7)	0.0063 (7)
S5	0.0311 (10)	0.0206 (9)	0.0213 (10)	0.0160 (8)	0.0110 (8)	0.0041 (7)
S6	0.0270 (10)	0.0246 (10)	0.0191 (9)	0.0134 (8)	0.0119 (8)	0.0101 (7)
S7	0.0282 (10)	0.0221 (9)	0.0194 (9)	0.0145 (8)	0.0113 (8)	0.0048 (7)
S8	0.0267 (10)	0.0261 (10)	0.0185 (9)	0.0169 (8)	0.0109 (8)	0.0084 (7)
S9	0.0504 (13)	0.0232 (10)	0.0270 (11)	0.0150 (10)	0.0265 (10)	0.0058 (8)

C1—C2	1.337 (11)	C7—S7	1.755 (7)
C1—S4	1.746 (8)	C7—S8	1.762 (8)
C1—I1	2.083 (8)	C8—C9	1.349 (11)
C2—S5	1.741 (8)	C8—S6	1.755 (8)
C2—H2A	0.9500	C8—S8	1.763 (7)
C3—C4	1.365 (10)	C9—S9	1.736 (8)
C3—S5	1.737 (7)	C9—S7	1.765 (8)
C3—S4	1.751 (8)	C10—S6	1.792 (9)
C4—C5	1.444 (10)	C10—H10A	0.9800
C4—S3	1.764 (7)	C10—H10B	0.9800
C5—O1	1.230 (9)	C10—H10C	0.9800
C5—S2	1.777 (8)	C11—S9	1.813 (9)
C6—C7	1.350 (10)	C11—H11A	0.9800
C6—S2	1.747 (8)	C11—H11B	0.9800
C6—S3	1.747 (8)	C11—H11C	0.9800
C2—C1—S4	118.7 (6)	C8—C9—S9	124.2 (6)
C2—C1—I1	124.9 (6)	C8—C9—S7	116.2 (6)
S4—C1—I1	116.2 (4)	S9—C9—S7	119.4 (5)
C1—C2—S5	116.1 (6)	S6—C10—H10A	109.5
C1—C2—H2A	122.0	S6—C10—H10B	109.5
S5—C2—H2A	122.0	H10A—C10—H10B	109.5
C4—C3—S5	121.0 (6)	S6—C10—H10C	109.5
C4—C3—S4	124.0 (6)	H10A—C10—H10C	109.5
S5—C3—S4	115.1 (4)	H10B—C10—H10C	109.5
C3—C4—C5	119.7 (7)	S9—C11—H11A	109.5
C3—C4—S3	122.9 (6)	S9—C11—H11B	109.5
C5—C4—S3	117.3 (5)	H11A—C11—H11B	109.5
O1—C5—C4	124.7 (7)	S9—C11—H11C	109.5
O1—C5—S2	121.3 (6)	H11A—C11—H11C	109.5
C4—C5—S2	113.9 (5)	H11B—C11—H11C	109.5
C7—C6—S2	120.1 (6)	C6—S2—C5	96.5 (4)
C7—C6—S3	123.1 (6)	C6—S3—C4	95.3 (3)
S2—C6—S3	116.8 (4)	C1—S4—C3	94.2 (4)
C6—C7—S7	123.5 (6)	C3—S5—C2	95.8 (4)
C6—C7—S8	121.9 (6)	C8—S6—C10	102.2 (4)
S7—C7—S8	114.6 (4)	C7—S7—C9	96.0 (4)
C9—C8—S6	124.3 (6)	C7—S8—C8	95.1 (4)
C9—C8—S8	118.1 (6)	C9—S9—C11	101.7 (4)
S6—C8—S8	117.4 (4)