2,3-Bis(methyl-sulfan-yl)-1,4,5,8-tetra-thia-fulvalene.

In the title compound, C(8)H(8)S(6), the five-membered rings form a dihedral angle of 25.06 (9)°. In the absence of short inter-molecular contacts, the mol-ecules are packed by van der Waals forces in the crystal.

Related literature

For applications of tetra­thia­fulvalenes, see: Wudl et al. (1972 ▶); Jørgensen et al. (1994 ▶). For details of the synthesis, see: Fourmingué et al. (1993 ▶). For a related structure, see: Hou et al. (2010 ▶).

Experimental

Crystal data

C8H8S6

M = 296.50

Monoclinic,

a = 19.368 (11) Å

b = 7.703 (4) Å

c = 17.150 (8) Å

β = 108.59 (2)°

V = 2425 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.09 mm−1

T = 291 K

0.12 × 0.10 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.881, T max = 0.909

11301 measured reflections

2773 independent reflections

2480 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.03

2773 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.66 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048580/ng5069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048580/ng5069Isup2.hkl

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

C8H8S6	F(000) = 1216
Mr = 296.50	Dx = 1.624 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9674 reflections
a = 19.368 (11) Å	θ = 3.3–27.6°
b = 7.703 (4) Å	µ = 1.09 mm−1
c = 17.150 (8) Å	T = 291 K
β = 108.59 (2)°	Block, yellow
V = 2425 (2) Å3	0.12 × 0.10 × 0.09 mm
Z = 8

Rigaku R-AXIS RAPID diffractometer	2773 independent reflections
Radiation source: fine-focus sealed tube	2480 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −25→25
Tmin = 0.881, Tmax = 0.909	k = −10→9
11301 measured reflections	l = −21→22

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.043P)2 + 2.0438P] where P = (Fo2 + 2Fc2)/3
2773 reflections	(Δ/σ)max = 0.006
129 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

Experimental. (See detailed section in the paper)

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	0.02208 (11)	0.7309 (3)	1.15260 (11)	0.0490 (5)
H1	−0.0004	0.7911	1.1849	0.059*
C2	0.06543 (12)	0.5980 (3)	1.18273 (11)	0.0494 (5)
H2	0.0744	0.5615	1.2368	0.059*
C3	0.07086 (9)	0.6402 (2)	1.03633 (10)	0.0331 (3)
C4	0.09038 (9)	0.6398 (2)	0.96816 (10)	0.0348 (3)
C5	0.12943 (10)	0.7609 (2)	0.84888 (10)	0.0375 (4)
C6	0.17548 (9)	0.6286 (2)	0.87949 (10)	0.0381 (4)
C7	0.18062 (13)	1.0834 (3)	0.83038 (14)	0.0552 (5)
H7A	0.1538	1.1248	0.8651	0.083*
H7B	0.1850	1.1747	0.7941	0.083*
H7C	0.2283	1.0472	0.8638	0.083*
C8	0.30945 (12)	0.4634 (3)	0.92717 (15)	0.0608 (6)
H8A	0.3209	0.5384	0.9743	0.091*
H8B	0.3531	0.4385	0.9141	0.091*
H8C	0.2890	0.3571	0.9391	0.091*
S1	0.00813 (3)	0.79005 (6)	1.05124 (3)	0.04253 (13)
S2	0.10518 (3)	0.49359 (6)	1.11799 (3)	0.04402 (13)
S3	0.05498 (2)	0.78415 (6)	0.88578 (3)	0.04151 (13)
S4	0.15503 (3)	0.49566 (6)	0.95261 (3)	0.04458 (14)
S5	0.13348 (3)	0.90281 (7)	0.77079 (3)	0.05321 (15)
S6	0.24524 (3)	0.56800 (10)	0.84168 (4)	0.06234 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0601 (12)	0.0557 (12)	0.0353 (9)	0.0035 (9)	0.0211 (8)	−0.0054 (8)
C2	0.0591 (11)	0.0599 (13)	0.0293 (9)	0.0019 (10)	0.0142 (8)	0.0037 (8)
C3	0.0323 (7)	0.0330 (8)	0.0354 (8)	0.0023 (6)	0.0127 (6)	0.0048 (6)
C4	0.0353 (8)	0.0347 (9)	0.0377 (8)	0.0030 (6)	0.0160 (7)	0.0063 (6)
C5	0.0468 (9)	0.0376 (9)	0.0311 (8)	−0.0072 (7)	0.0166 (7)	0.0002 (6)
C6	0.0405 (8)	0.0442 (10)	0.0343 (8)	−0.0055 (7)	0.0185 (7)	−0.0019 (7)
C7	0.0602 (12)	0.0458 (12)	0.0593 (13)	−0.0100 (10)	0.0187 (10)	0.0034 (9)
C8	0.0425 (11)	0.0773 (16)	0.0651 (14)	0.0057 (10)	0.0206 (10)	−0.0037 (12)
S1	0.0492 (3)	0.0424 (3)	0.0420 (2)	0.01172 (19)	0.0229 (2)	0.00695 (18)
S2	0.0462 (3)	0.0476 (3)	0.0400 (2)	0.01051 (19)	0.0161 (2)	0.01361 (18)
S3	0.0447 (2)	0.0423 (3)	0.0404 (2)	0.00839 (19)	0.01765 (19)	0.01208 (18)
S4	0.0482 (3)	0.0449 (3)	0.0505 (3)	0.0142 (2)	0.0295 (2)	0.01503 (19)
S5	0.0789 (4)	0.0510 (3)	0.0320 (2)	−0.0161 (3)	0.0210 (2)	0.00457 (19)
S6	0.0543 (3)	0.0919 (5)	0.0539 (3)	0.0106 (3)	0.0356 (3)	0.0085 (3)

C1—C2	1.321 (3)	C5—S3	1.759 (2)
C1—S1	1.733 (2)	C6—S6	1.7386 (19)
C1—H1	0.9300	C6—S4	1.7591 (18)
C2—S2	1.737 (2)	C7—S5	1.794 (2)
C2—H2	0.9300	C7—H7A	0.9600
C3—C4	1.339 (2)	C7—H7B	0.9600
C3—S1	1.7525 (18)	C7—H7C	0.9600
C3—S2	1.7565 (17)	C8—S6	1.784 (2)
C4—S3	1.7565 (18)	C8—H8A	0.9600
C4—S4	1.7562 (18)	C8—H8B	0.9600
C5—C6	1.346 (3)	C8—H8C	0.9600
C5—S5	1.7498 (18)
C2—C1—S1	118.21 (15)	S5—C7—H7A	109.5
C2—C1—H1	120.9	S5—C7—H7B	109.5
S1—C1—H1	120.9	H7A—C7—H7B	109.5
C1—C2—S2	117.70 (15)	S5—C7—H7C	109.5
C1—C2—H2	121.1	H7A—C7—H7C	109.5
S2—C2—H2	121.1	H7B—C7—H7C	109.5
C4—C3—S1	122.09 (13)	S6—C8—H8A	109.5
C4—C3—S2	123.66 (14)	S6—C8—H8B	109.5
S1—C3—S2	114.26 (9)	H8A—C8—H8B	109.5
C3—C4—S3	123.67 (14)	S6—C8—H8C	109.5
C3—C4—S4	123.23 (13)	H8A—C8—H8C	109.5
S3—C4—S4	113.10 (10)	H8B—C8—H8C	109.5
C6—C5—S5	125.86 (14)	C1—S1—C3	94.57 (9)
C6—C5—S3	117.01 (13)	C2—S2—C3	94.58 (10)
S5—C5—S3	116.99 (11)	C4—S3—C5	94.04 (8)
C5—C6—S6	123.71 (14)	C4—S4—C6	94.24 (9)
C5—C6—S4	116.55 (14)	C5—S5—C7	100.79 (10)
S6—C6—S4	119.21 (11)	C6—S6—C8	103.63 (10)