5-Isopropyl-idene-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione.

The title compound, C(7)H(6)S(5), contains a 5-yl-idene-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione framework, which is an important synthetic precursor of multi-dimensional organic superconductors and conductors. The mol-ecular framework is planar with an r.m.s. deviation of 0.012 Å for the non-H atoms. In the crystal structure, mol-ecules are linked by short inter-molecular S⋯S inter-actions [3.501 (5) and 3.581 (4) Å], constructing a zigzag mol-ecular tape network along the c axis.

Related literature

For general background, see: Williams et al. (1992 ▶); Ishiguro et al. (1998 ▶). For the synthesis of the title compound, see: Misaki et al. (1992 ▶). For related structures with a 5-yl­idene-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione framework, see: Bryce et al. (2000 ▶); Hock et al. (2002 ▶); Beck et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For values of van der Waals radii, see: Bondi (1964 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C7H6S5

M = 250.47

Triclinic,

a = 7.082 (6) Å

b = 7.126 (6) Å

c = 10.534 (10) Å

α = 86.12 (3)°

β = 84.77 (3)°

γ = 71.95 (2)°

V = 502.9 (8) Å3

Z = 2

Mo Kα radiation

μ = 1.09 mm−1

T = 291 K

0.09 × 0.02 × 0.01 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: none

4550 measured reflections

2643 independent reflections

785 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.246

S = 0.84

2643 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901335X/hg2498sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901335X/hg2498Isup2.hkl

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

C7H6S5	Z = 2
Mr = 250.47	F(000) = 256
Triclinic, P1	Dx = 1.654 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.082 (6) Å	Cell parameters from 843 reflections
b = 7.126 (6) Å	θ = 3.0–29.7°
c = 10.534 (10) Å	µ = 1.09 mm−1
α = 86.12 (3)°	T = 291 K
β = 84.77 (3)°	Needle, brown
γ = 71.95 (2)°	0.09 × 0.02 × 0.01 mm
V = 502.9 (8) Å3

Rigaku/MSC Mercury CCD diffractometer	785 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.117
Confocal	θmax = 31.1°, θmin = 3.0°
Detector resolution: 14.63 pixels mm-1	h = −9→9
φ and ω scans	k = −10→10
4550 measured reflections	l = −10→15
2643 independent reflections

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)] = 0.072	H-atom parameters constrained
wR(F2) = 0.246	w = 1/[σ2(Fo2) + (0.0747P)2] where P = (Fo2 + 2Fc2)/3
S = 0.84	(Δ/σ)max < 0.001
2643 reflections	Δρmax = 0.46 e Å−3
112 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.003 (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	0.1573 (3)	1.3556 (3)	−0.12379 (19)	0.0502 (6)
S2	0.2864 (3)	0.9827 (3)	−0.25144 (18)	0.0496 (6)
S3	0.1902 (3)	1.1364 (3)	0.13884 (18)	0.0452 (6)
S4	0.3259 (3)	0.7524 (3)	0.00739 (18)	0.0434 (6)
S5	0.1908 (4)	1.3598 (4)	−0.4066 (2)	0.0710 (9)
C1	0.2089 (11)	1.2401 (12)	−0.2662 (7)	0.048 (2)
C2	0.2080 (10)	1.1425 (11)	−0.0257 (7)	0.0427 (19)
C3	0.2706 (10)	0.8745 (11)	0.1547 (7)	0.0407 (18)
C4	0.2678 (9)	0.9729 (12)	−0.0871 (7)	0.0385 (17)
C5	0.2896 (10)	0.7741 (12)	0.2681 (8)	0.045 (2)
C6	0.2430 (11)	0.8811 (12)	0.3900 (7)	0.056 (2)
H6A	0.3602	0.8472	0.4365	0.084*
H6B	0.1395	0.8439	0.4405	0.084*
H6C	0.1994	1.0210	0.3711	0.084*
C7	0.3596 (11)	0.5529 (11)	0.2761 (7)	0.049 (2)
H7A	0.3818	0.5036	0.1917	0.073*
H7B	0.2603	0.5056	0.3239	0.073*
H7C	0.4816	0.5078	0.3179	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0512 (13)	0.0409 (13)	0.0522 (14)	−0.0080 (10)	−0.0035 (10)	0.0126 (10)
S2	0.0551 (14)	0.0473 (14)	0.0417 (12)	−0.0113 (11)	0.0001 (9)	0.0038 (10)
S3	0.0519 (13)	0.0337 (12)	0.0451 (12)	−0.0077 (10)	0.0010 (9)	−0.0006 (9)
S4	0.0513 (13)	0.0308 (12)	0.0429 (12)	−0.0058 (10)	−0.0014 (9)	0.0009 (9)
S5	0.0751 (18)	0.078 (2)	0.0561 (16)	−0.0221 (15)	−0.0135 (12)	0.0300 (13)
C1	0.049 (5)	0.044 (5)	0.047 (5)	−0.007 (4)	−0.011 (4)	0.012 (4)
C2	0.046 (5)	0.031 (5)	0.047 (5)	−0.008 (4)	−0.002 (4)	−0.003 (4)
C3	0.040 (4)	0.039 (5)	0.040 (4)	−0.010 (4)	0.004 (3)	−0.001 (3)
C4	0.032 (4)	0.038 (4)	0.040 (4)	−0.004 (3)	−0.006 (3)	0.006 (3)
C5	0.039 (4)	0.037 (5)	0.058 (5)	−0.014 (4)	0.013 (4)	−0.001 (4)
C6	0.066 (6)	0.050 (6)	0.051 (5)	−0.016 (5)	0.002 (4)	−0.005 (4)
C7	0.056 (5)	0.039 (5)	0.049 (5)	−0.016 (4)	0.002 (4)	0.014 (4)

S1—C1	1.716 (8)	C3—C5	1.346 (10)
S1—C2	1.738 (8)	C5—C6	1.496 (10)
S2—C4	1.723 (7)	C5—C7	1.497 (10)
S2—C1	1.744 (8)	C6—H6A	0.9600
S3—C2	1.725 (8)	C6—H6B	0.9600
S3—C3	1.775 (8)	C6—H6C	0.9600
S4—C4	1.758 (7)	C7—H7A	0.9600
S4—C3	1.783 (7)	C7—H7B	0.9600
S5—C1	1.652 (7)	C7—H7C	0.9600
C2—C4	1.341 (10)
S1···S1i	3.581 (4)	S5···S5ii	3.501 (5)
C1—S1—C2	96.7 (4)	C3—C5—C6	120.7 (8)
C4—S2—C1	94.9 (4)	C3—C5—C7	121.2 (7)
C2—S3—C3	94.4 (3)	C6—C5—C7	118.1 (7)
C4—S4—C3	94.3 (4)	C5—C6—H6A	109.5
S5—C1—S1	123.5 (5)	C5—C6—H6B	109.5
S5—C1—S2	122.1 (5)	H6A—C6—H6B	109.5
S1—C1—S2	114.4 (4)	C5—C6—H6C	109.5
C4—C2—S3	119.7 (6)	H6A—C6—H6C	109.5
C4—C2—S1	115.0 (6)	H6B—C6—H6C	109.5
S3—C2—S1	125.3 (5)	C5—C7—H7A	109.5
C5—C3—S3	123.3 (6)	C5—C7—H7B	109.5
C5—C3—S4	122.0 (6)	H7A—C7—H7B	109.5
S3—C3—S4	114.6 (4)	C5—C7—H7C	109.5
C2—C4—S2	118.9 (6)	H7A—C7—H7C	109.5
C2—C4—S4	117.0 (6)	H7B—C7—H7C	109.5
S2—C4—S4	124.1 (5)
C2—S1—C1—S5	180.0 (5)	S3—C2—C4—S2	−179.5 (4)
C2—S1—C1—S2	−0.9 (5)	S1—C2—C4—S2	−0.4 (8)
C4—S2—C1—S5	179.9 (5)	S3—C2—C4—S4	−0.3 (8)
C4—S2—C1—S1	0.8 (5)	S1—C2—C4—S4	178.8 (3)
C3—S3—C2—C4	0.3 (6)	C1—S2—C4—C2	−0.2 (6)
C3—S3—C2—S1	−178.7 (5)	C1—S2—C4—S4	−179.3 (5)
C1—S1—C2—C4	0.8 (6)	C3—S4—C4—C2	0.1 (6)
C1—S1—C2—S3	179.8 (5)	C3—S4—C4—S2	179.2 (4)
C2—S3—C3—C5	179.6 (7)	S3—C3—C5—C6	−0.2 (10)
C2—S3—C3—S4	−0.2 (4)	S4—C3—C5—C6	179.7 (5)
C4—S4—C3—C5	−179.8 (7)	S3—C3—C5—C7	−179.5 (5)
C4—S4—C3—S3	0.1 (4)	S4—C3—C5—C7	0.3 (10)