Bis(ethyl-enedithio)tetra-thia-fulvalenium-tetra-chloridocobaltate(II) (3/2).

The structure of the electrochemically crystallized title compound, (C(10)H(8)S(8))(3)[CoCl(4)](2), consists of two types of bis-(ethyl-enedithio)tetra-thia-fulvalene (BEDT-TTF) radical cation stacks separated by sheets of tetra-hedral [CoCl(4)](2-) anions. One of the BEDT-TTF mol-ecules is generated by inversion. There are short S⋯S contacts between the stacks in the a direction and short C-H⋯Cl contacts between the radical cations and the anions.

Related literature

For related literature, see: Mori (1998 ▶, 1999 ▶); Mori et al. (1999 ▶, 2002 ▶); Shibaeva & Yagubskii (2004 ▶); Varma et al. (1987 ▶); Williams et al. (1984 ▶).

Experimental

Crystal data

(C10H8S8)3[CoCl4]2

M = 1555.39

Triclinic,

a = 6.7904 (19) Å

b = 9.6402 (18) Å

c = 20.499 (4) Å

α = 86.280 (14)°

β = 89.967 (19)°

γ = 78.456 (19)°

V = 1311.9 (5) Å3

Z = 1

Mo Kα radiation

μ = 2.03 mm−1

T = 293 (2) K

0.22 × 0.18 × 0.10 mm

Data collection

Bruker P4 diffractometer

Absorption correction: ψ scan (XSCANS; Bruker, 1996 ▶) T min = 0.652, T max = 0.816

6527 measured reflections

5159 independent reflections

1927 reflections with I > 2σ(I)

R int = 0.094

97 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.100

wR(F 2) = 0.281

S = 0.92

5159 reflections

289 parameters

8 restraints

H-atom parameters constrained

Δρmax = 0.91 e Å−3

Δρmin = −1.06 e Å−3

Data collection: XSCANS (Bruker, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033692/hb2784sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033692/hb2784Isup2.hkl

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

(C10H8S8)3[CoCl4]2	Z = 1
Mr = 1555.39	F000 = 778
Triclinic, P1	Dx = 1.969 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.7904 (19) Å	Cell parameters from 31 reflections
b = 9.6402 (18) Å	θ = 5.0–12.4º
c = 20.499 (4) Å	µ = 2.03 mm−1
α = 86.280 (14)º	T = 293 (2) K
β = 89.967 (19)º	Prism, black
γ = 78.456 (19)º	0.22 × 0.18 × 0.10 mm
V = 1311.9 (5) Å3

Bruker P4 diffractometer	Rint = 0.094
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.0º
T = 293(2) K	h = −8→1
/w scans	k = −11→11
Absorption correction: ψ scan(XSCANS; Bruker, 1996)	l = −25→25
Tmin = 0.652, Tmax = 0.816	97 standard reflections
6527 measured reflections	every 3 reflections
5159 independent reflections	intensity decay: 1%
1927 reflections with I > 2σ(I)

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)] = 0.100	H-atom parameters constrained
wR(F2) = 0.281	w = 1/[σ2(Fo2) + (0.1192P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
5159 reflections	Δρmax = 0.91 e Å−3
289 parameters	Δρmin = −1.06 e Å−3
8 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C11	0.271 (3)	0.0230 (19)	0.6376 (9)	0.068 (6)
H11A	0.2624	0.0986	0.6671	0.081*
H11B	0.1845	−0.0397	0.6542	0.081*
C12	0.487 (2)	−0.0600 (19)	0.6370 (11)	0.085 (7)
H12A	0.4917	−0.1379	0.6090	0.102*
H12B	0.5226	−0.1013	0.6809	0.102*
C1	0.557 (2)	0.4107 (18)	1.1811 (8)	0.051 (5)
H1A	0.6758	0.3413	1.1952	0.061*
H1B	0.5116	0.4665	1.2180	0.061*
C2	0.397 (2)	0.3341 (16)	1.1632 (8)	0.041 (4)
H2A	0.3816	0.2680	1.1997	0.049*
H2B	0.4443	0.2784	1.1265	0.049*
C3	0.397 (2)	0.5999 (16)	1.0767 (7)	0.035 (4)
C4	0.218 (2)	0.5659 (13)	1.0853 (7)	0.029 (3)
C5	0.161 (2)	0.7692 (15)	0.9978 (7)	0.035 (4)
C6	0.076 (2)	0.8723 (13)	0.9480 (7)	0.023 (3)
C7	0.023 (2)	1.0697 (16)	0.8548 (7)	0.035 (4)
C8	−0.155 (2)	1.0292 (14)	0.8635 (7)	0.034 (4)
C9	−0.106 (3)	1.2069 (19)	0.7415 (9)	0.061 (6)
H9A	−0.0977	1.2849	0.7099	0.073*
H9B	−0.0827	1.1209	0.7181	0.073*
C10	−0.304 (3)	1.228 (2)	0.7659 (9)	0.069 (6)
H10A	−0.3953	1.2454	0.7286	0.082*
H10B	−0.3260	1.3151	0.7888	0.082*
C13	0.350 (2)	0.2161 (15)	0.5480 (7)	0.035 (4)
C14	0.542 (2)	0.1863 (16)	0.5711 (8)	0.040 (4)
C15	0.485 (3)	0.4319 (15)	0.5147 (9)	0.045 (4)
Cl1	0.0026 (7)	0.7913 (4)	0.7470 (2)	0.0460 (11)
Cl2	−0.2946 (7)	0.5703 (5)	0.6666 (2)	0.0563 (13)
Cl3	0.0831 (8)	0.7338 (5)	0.5751 (2)	0.0546 (13)
Cl4	0.2378 (7)	0.4170 (4)	0.6910 (2)	0.0529 (12)
Co01	0.0140 (4)	0.6252 (2)	0.67099 (11)	0.0402 (6)
S1	0.6258 (6)	0.5265 (5)	1.1162 (2)	0.0508 (13)
S2	0.1496 (6)	0.4391 (4)	1.1417 (2)	0.0426 (11)
S3	0.4092 (6)	0.7397 (4)	1.0199 (2)	0.0373 (10)
S4	0.0217 (6)	0.6592 (4)	1.0356 (2)	0.0351 (10)
S5	0.2191 (6)	0.9787 (4)	0.9081 (2)	0.0371 (10)
S6	−0.1704 (6)	0.9004 (4)	0.9241 (2)	0.0370 (10)
S7	0.0938 (6)	1.1928 (4)	0.7998 (2)	0.0388 (11)
S8	−0.3763 (6)	1.0934 (5)	0.8193 (2)	0.0439 (11)
S9	0.1832 (8)	0.0971 (5)	0.5591 (2)	0.0572 (14)
S10	0.6771 (8)	0.0341 (5)	0.6107 (3)	0.0673 (16)
S11	0.2669 (7)	0.3772 (5)	0.5071 (2)	0.0536 (13)
S12	0.6655 (6)	0.3251 (4)	0.5600 (2)	0.0450 (12)

	U11	U22	U33	U12	U13	U23
C11	0.089 (17)	0.062 (13)	0.058 (13)	−0.042 (13)	0.003 (12)	0.028 (10)
C12	0.104 (18)	0.063 (13)	0.098 (17)	−0.053 (14)	−0.022 (14)	0.035 (12)
C1	0.038 (10)	0.046 (10)	0.060 (12)	0.004 (9)	−0.018 (9)	0.028 (9)
C2	0.028 (9)	0.030 (9)	0.060 (11)	−0.002 (7)	−0.011 (8)	0.018 (8)
C3	0.047 (10)	0.037 (9)	0.025 (8)	−0.024 (8)	−0.011 (8)	0.012 (7)
C4	0.039 (9)	0.014 (7)	0.031 (8)	−0.006 (7)	−0.001 (7)	0.011 (6)
C5	0.039 (10)	0.029 (8)	0.042 (9)	−0.023 (8)	−0.015 (8)	0.014 (7)
C6	0.024 (8)	0.017 (7)	0.028 (8)	−0.005 (6)	−0.003 (7)	−0.007 (6)
C7	0.027 (9)	0.032 (8)	0.040 (10)	0.007 (7)	0.007 (8)	0.008 (7)
C8	0.040 (10)	0.018 (7)	0.044 (10)	−0.008 (7)	−0.001 (8)	0.010 (7)
C9	0.065 (13)	0.054 (12)	0.074 (13)	−0.048 (11)	−0.022 (11)	0.025 (10)
C10	0.040 (12)	0.090 (16)	0.074 (14)	−0.023 (12)	−0.020 (11)	0.035 (12)
C13	0.041 (10)	0.029 (8)	0.036 (9)	−0.010 (8)	−0.013 (8)	0.013 (7)
C14	0.031 (9)	0.030 (8)	0.060 (11)	−0.016 (7)	−0.013 (8)	0.026 (8)
C15	0.043 (10)	0.021 (8)	0.069 (12)	−0.009 (8)	0.000 (9)	0.011 (8)
Cl1	0.058 (3)	0.028 (2)	0.053 (3)	−0.013 (2)	−0.001 (2)	0.0053 (18)
Cl2	0.053 (3)	0.047 (3)	0.071 (3)	−0.020 (2)	−0.004 (3)	0.013 (2)
Cl3	0.071 (3)	0.045 (3)	0.050 (3)	−0.021 (2)	0.003 (2)	0.013 (2)
Cl4	0.047 (3)	0.031 (2)	0.077 (3)	−0.006 (2)	−0.002 (2)	0.016 (2)
Co01	0.0444 (15)	0.0261 (11)	0.0492 (14)	−0.0093 (11)	−0.0038 (12)	0.0124 (10)
S1	0.030 (2)	0.044 (3)	0.076 (3)	−0.011 (2)	−0.013 (2)	0.028 (2)
S2	0.035 (2)	0.032 (2)	0.060 (3)	−0.014 (2)	−0.002 (2)	0.024 (2)
S3	0.032 (2)	0.038 (2)	0.044 (2)	−0.0170 (19)	−0.005 (2)	0.0166 (18)
S4	0.030 (2)	0.027 (2)	0.048 (3)	−0.0129 (18)	−0.0060 (19)	0.0179 (17)
S5	0.030 (2)	0.031 (2)	0.050 (3)	−0.0120 (18)	−0.004 (2)	0.0195 (18)
S6	0.030 (2)	0.030 (2)	0.053 (3)	−0.0170 (18)	−0.007 (2)	0.0143 (18)
S7	0.033 (2)	0.035 (2)	0.047 (3)	−0.011 (2)	−0.002 (2)	0.0167 (19)
S8	0.034 (2)	0.043 (2)	0.053 (3)	−0.012 (2)	−0.010 (2)	0.019 (2)
S9	0.060 (3)	0.052 (3)	0.065 (3)	−0.034 (3)	−0.014 (3)	0.030 (2)
S10	0.058 (3)	0.030 (2)	0.105 (4)	0.003 (2)	−0.008 (3)	0.030 (3)
S11	0.041 (3)	0.044 (3)	0.075 (3)	−0.019 (2)	−0.015 (2)	0.031 (2)
S12	0.035 (2)	0.038 (2)	0.062 (3)	−0.015 (2)	−0.009 (2)	0.018 (2)

C11—C12	1.527 (10)	C7—C8	1.35 (2)
C11—S9	1.772 (17)	C7—S7	1.723 (14)
C11—H11A	0.9700	C7—S5	1.774 (15)
C11—H11B	0.9700	C8—S6	1.717 (14)
C12—S10	1.782 (9)	C8—S8	1.735 (16)
C12—H12A	0.9700	C9—C10	1.42 (2)
C12—H12B	0.9700	C9—S7	1.786 (17)
C1—C2	1.49 (2)	C9—H9A	0.9700
C1—S1	1.803 (16)	C9—H9B	0.9700
C1—H1A	0.9700	C10—S8	1.791 (17)
C1—H1B	0.9700	C10—H10A	0.9700
C2—S2	1.818 (15)	C10—H10B	0.9700
C2—H2A	0.9700	C13—C14	1.36 (2)
C2—H2B	0.9700	C13—S11	1.708 (14)
C3—C4	1.333 (19)	C13—S9	1.771 (15)
C3—S3	1.738 (14)	C14—S12	1.719 (14)
C3—S1	1.747 (16)	C14—S10	1.720 (15)
C4—S4	1.739 (14)	C15—C15i	1.46 (3)
C4—S2	1.756 (13)	C15—S12	1.672 (17)
C5—C6	1.416 (18)	C15—S11	1.679 (16)
C5—S3	1.708 (15)	Co1—Cl1	2.296 (5)
C5—S4	1.708 (13)	Co1—Cl2	2.265 (5)
C6—S6	1.706 (14)	Co1—Cl3	2.259 (5)
C6—S5	1.720 (13)	Co1—Cl4	2.276 (5)
C12—C11—S9	112.6 (14)	S6—C8—S8	115.0 (9)
C12—C11—H11A	109.1	C10—C9—S7	117.0 (15)
S9—C11—H11A	109.1	C10—C9—H9A	108.0
C12—C11—H11B	109.1	S7—C9—H9A	108.0
S9—C11—H11B	109.1	C10—C9—H9B	108.0
H11A—C11—H11B	107.8	S7—C9—H9B	108.0
C11—C12—S10	117.6 (12)	H9A—C9—H9B	107.3
C11—C12—H12A	107.9	C9—C10—S8	119.3 (14)
S10—C12—H12A	107.9	C9—C10—H10A	107.5
C11—C12—H12B	107.9	S8—C10—H10A	107.5
S10—C12—H12B	107.9	C9—C10—H10B	107.5
H12A—C12—H12B	107.2	S8—C10—H10B	107.5
C2—C1—S1	114.6 (12)	H10A—C10—H10B	107.0
C2—C1—H1A	108.6	C14—C13—S11	117.8 (11)
S1—C1—H1A	108.6	C14—C13—S9	123.2 (11)
C2—C1—H1B	108.6	S11—C13—S9	119.0 (9)
S1—C1—H1B	108.6	C13—C14—S12	113.9 (11)
H1A—C1—H1B	107.6	C13—C14—S10	130.2 (11)
C1—C2—S2	117.9 (11)	S12—C14—S10	115.8 (9)
C1—C2—H2A	107.8	C15i—C15—S12	121.2 (17)
S2—C2—H2A	107.8	C15i—C15—S11	122.1 (17)
C1—C2—H2B	107.8	S12—C15—S11	116.7 (8)
S2—C2—H2B	107.8	Cl3—Co01—Cl2	110.4 (2)
H2A—C2—H2B	107.2	Cl3—Co01—Cl4	110.28 (19)
C4—C3—S3	116.7 (12)	Cl2—Co01—Cl4	106.69 (18)
C4—C3—S1	129.2 (11)	Cl3—Co01—Cl1	105.49 (17)
S3—C3—S1	114.1 (8)	Cl2—Co01—Cl1	107.4 (2)
C3—C4—S4	116.9 (10)	Cl4—Co01—Cl1	116.55 (19)
C3—C4—S2	128.5 (12)	C3—S1—C1	103.6 (7)
S4—C4—S2	114.6 (8)	C4—S2—C2	99.8 (7)
C6—C5—S3	122.8 (10)	C5—S3—C3	95.1 (7)
C6—C5—S4	120.8 (11)	C5—S4—C4	95.0 (7)
S3—C5—S4	116.3 (8)	C6—S5—C7	95.2 (7)
C5—C6—S6	123.3 (10)	C6—S6—C8	96.0 (7)
C5—C6—S5	120.7 (11)	C7—S7—C9	98.3 (8)
S6—C6—S5	116.0 (8)	C8—S8—C10	101.3 (8)
C8—C7—S7	131.0 (12)	C13—S9—C11	97.4 (8)
C8—C7—S5	114.8 (11)	C14—S10—C12	103.2 (8)
S7—C7—S5	114.2 (9)	C15—S11—C13	94.8 (7)
C7—C8—S6	118.0 (12)	C15—S12—C14	96.2 (7)
C7—C8—S8	127.0 (11)
S9—C11—C12—S10	61 (2)	C3—C4—S4—C5	−3.4 (14)
S1—C1—C2—S2	−63.6 (17)	S2—C4—S4—C5	175.8 (9)
S3—C3—C4—S4	3.4 (18)	C5—C6—S5—C7	178.4 (12)
S1—C3—C4—S4	−178.5 (10)	S6—C6—S5—C7	−2.0 (9)
S3—C3—C4—S2	−175.7 (9)	C8—C7—S5—C6	0.7 (14)
S1—C3—C4—S2	2(2)	S7—C7—S5—C6	−178.4 (9)
S3—C5—C6—S6	178.5 (9)	C5—C6—S6—C8	−178.0 (13)
S4—C5—C6—S6	2.7 (19)	S5—C6—S6—C8	2.4 (9)
S3—C5—C6—S5	−1.9 (18)	C7—C8—S6—C6	−2.0 (14)
S4—C5—C6—S5	−177.7 (8)	S8—C8—S6—C6	177.8 (9)
S7—C7—C8—S6	179.7 (10)	C8—C7—S7—C9	−18.6 (19)
S5—C7—C8—S6	0.9 (18)	S5—C7—S7—C9	160.3 (10)
S7—C7—C8—S8	0(3)	C10—C9—S7—C7	49.3 (16)
S5—C7—C8—S8	−178.9 (9)	C7—C8—S8—C10	−3.3 (18)
S7—C9—C10—S8	−64 (2)	S6—C8—S8—C10	176.9 (10)
S11—C13—C14—S12	4.6 (19)	C9—C10—S8—C8	35.6 (19)
S9—C13—C14—S12	−174.7 (9)	C14—C13—S9—C11	34.6 (17)
S11—C13—C14—S10	−176.7 (11)	S11—C13—S9—C11	−144.8 (10)
S9—C13—C14—S10	4(3)	C12—C11—S9—C13	−64.9 (14)
C4—C3—S1—C1	−8.6 (18)	C13—C14—S10—C12	−17 (2)
S3—C3—S1—C1	169.6 (9)	S12—C14—S10—C12	161.7 (11)
C2—C1—S1—C3	37.9 (15)	C11—C12—S10—C14	−17 (2)
C3—C4—S2—C2	−17.8 (17)	C15i—C15—S11—C13	177 (2)
S4—C4—S2—C2	163.1 (9)	S12—C15—S11—C13	−5.1 (12)
C1—C2—S2—C4	49.0 (14)	C14—C13—S11—C15	0.1 (15)
C6—C5—S3—C3	−176.9 (13)	S9—C13—S11—C15	179.5 (11)
S4—C5—S3—C3	−0.9 (11)	C15i—C15—S12—C14	−175 (2)
C4—C3—S3—C5	−1.4 (14)	S11—C15—S12—C14	7.2 (12)
S1—C3—S3—C5	−179.9 (9)	C13—C14—S12—C15	−6.9 (15)
C6—C5—S4—C4	178.4 (13)	S10—C14—S12—C15	174.3 (11)
S3—C5—S4—C4	2.3 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1ii	0.97	2.55	3.494 (16)	165
C1—H1B···Cl2iii	0.97	2.83	3.591 (16)	136
C10—H10A···Cl4iv	0.97	2.78	3.57 (2)	139

Table 1

Selected bond lengths (Å)

Co1—Cl1	2.296 (5)
Co1—Cl2	2.265 (5)
Co1—Cl3	2.259 (5)
Co1—Cl4	2.276 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl1i	0.97	2.55	3.494 (16)	165
C1—H1B⋯Cl2ii	0.97	2.83	3.591 (16)	136
C10—H10A⋯Cl4iii	0.97	2.78	3.57 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) .