2,3-Bis[(2-cyano-eth-yl)sulfan-yl]-1,4,5,8-tetra-thia-fulvalene-6,7-dicarbonitrile.

In the title compound, C(14)H(8)N(4)S(6), the two five-membered rings lie in the same plane with an r.m.s. deviation of 0.0334 (5) Å. The crystal structure features inter-molecular S⋯N inter-actions of 3.295 (4) Å.

Related literature

For background to the electrical properties of tetra­thia­fulvalene derivatives, see: Fabre (2000 ▶); Batail (2004 ▶). For the synthesis, see Chen et al. (2005 ▶). For a related structure, see: Hou et al. (2010 ▶).

Experimental

Crystal data

C14H8N4S6

M = 424.66

Triclinic,

a = 7.3055 (15) Å

b = 8.5193 (17) Å

c = 15.386 (3) Å

α = 82.52 (3)°

β = 76.97 (3)°

γ = 72.43 (3)°

V = 887.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 290 K

0.13 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.906, T max = 0.920

8751 measured reflections

4020 independent reflections

3415 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.072

S = 1.09

4020 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.20 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/S1600536810028473/ng2799sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028473/ng2799Isup2.hkl

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

C14H8N4S6	Z = 2
Mr = 424.66	F(000) = 432
Triclinic, P1	Dx = 1.589 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3055 (15) Å	Cell parameters from 7465 reflections
b = 8.5193 (17) Å	θ = 3.0–27.5°
c = 15.386 (3) Å	µ = 0.77 mm−1
α = 82.52 (3)°	T = 290 K
β = 76.97 (3)°	Block, black
γ = 72.43 (3)°	0.13 × 0.12 × 0.11 mm
V = 887.4 (3) Å3

Rigaku R-AXIS RAPID diffractometer	4020 independent reflections
Radiation source: fine-focus sealed tube	3415 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.906, Tmax = 0.920	k = −11→9
8751 measured reflections	l = −19→19

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
4020 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.20 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	−0.3844 (2)	0.29787 (18)	−0.14033 (10)	0.0352 (3)
C2	−0.2172 (2)	0.25475 (16)	−0.09903 (9)	0.0298 (3)
C3	−0.0448 (2)	0.14665 (16)	−0.13307 (9)	0.0292 (3)
C4	−0.0139 (2)	0.06331 (18)	−0.21181 (10)	0.0343 (3)
C5	0.01227 (19)	0.24707 (15)	0.00609 (9)	0.0275 (3)
C6	0.09080 (19)	0.27024 (15)	0.07290 (9)	0.0276 (3)
C7	0.3151 (2)	0.25405 (16)	0.18511 (9)	0.0292 (3)
C8	0.14603 (19)	0.36850 (16)	0.21550 (8)	0.0277 (3)
C9	0.4763 (2)	0.01342 (18)	0.30608 (10)	0.0420 (4)
H9A	0.4424	−0.0567	0.2711	0.050*
H9B	0.5960	−0.0498	0.3258	0.050*
C10	0.3135 (2)	0.05787 (19)	0.38801 (10)	0.0428 (4)
H10A	0.1927	0.1205	0.3690	0.051*
H10B	0.2928	−0.0424	0.4210	0.051*
C11	0.3623 (2)	0.1552 (2)	0.44647 (10)	0.0433 (4)
C12	−0.1478 (2)	0.56270 (19)	0.33796 (10)	0.0423 (4)
H12A	−0.1782	0.6517	0.3770	0.051*
H12B	−0.2004	0.6090	0.2847	0.051*
C13	−0.2516 (3)	0.4360 (2)	0.38520 (11)	0.0539 (4)
H13A	−0.3915	0.4887	0.3985	0.065*
H13B	−0.2281	0.3495	0.3454	0.065*
C14	−0.1865 (3)	0.3618 (2)	0.46835 (13)	0.0552 (4)
N1	−0.5150 (2)	0.33249 (19)	−0.17432 (10)	0.0528 (4)
N2	0.0141 (2)	−0.00538 (19)	−0.27451 (10)	0.0527 (4)
N3	0.4075 (2)	0.22886 (19)	0.49019 (10)	0.0591 (4)
N4	−0.1328 (3)	0.3044 (2)	0.53217 (12)	0.0805 (6)
S1	−0.23311 (5)	0.34738 (4)	−0.00256 (2)	0.03481 (10)
S2	0.14881 (5)	0.11197 (4)	−0.07788 (2)	0.03252 (10)
S3	−0.04110 (5)	0.40991 (4)	0.15451 (2)	0.03209 (10)
S4	0.33230 (5)	0.16723 (4)	0.08462 (2)	0.03296 (10)
S5	0.11523 (6)	0.48537 (4)	0.30581 (2)	0.03523 (10)
S6	0.52255 (5)	0.19092 (5)	0.23438 (2)	0.03667 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0287 (7)	0.0404 (7)	0.0378 (8)	−0.0074 (6)	−0.0108 (6)	−0.0051 (6)
C2	0.0279 (7)	0.0340 (7)	0.0304 (7)	−0.0099 (5)	−0.0106 (5)	−0.0011 (5)
C3	0.0290 (7)	0.0339 (7)	0.0276 (7)	−0.0101 (5)	−0.0094 (5)	−0.0024 (5)
C4	0.0298 (7)	0.0405 (7)	0.0339 (8)	−0.0080 (6)	−0.0107 (6)	−0.0040 (6)
C5	0.0256 (6)	0.0296 (6)	0.0279 (6)	−0.0058 (5)	−0.0082 (5)	−0.0033 (5)
C6	0.0266 (7)	0.0298 (6)	0.0265 (6)	−0.0061 (5)	−0.0071 (5)	−0.0036 (5)
C7	0.0284 (7)	0.0358 (7)	0.0247 (6)	−0.0073 (5)	−0.0090 (5)	−0.0039 (5)
C8	0.0299 (7)	0.0316 (7)	0.0232 (6)	−0.0087 (5)	−0.0079 (5)	−0.0026 (5)
C9	0.0485 (9)	0.0365 (8)	0.0406 (8)	−0.0009 (6)	−0.0209 (7)	−0.0058 (6)
C10	0.0468 (9)	0.0429 (8)	0.0410 (8)	−0.0129 (7)	−0.0177 (7)	0.0061 (7)
C11	0.0442 (9)	0.0469 (9)	0.0318 (8)	−0.0025 (7)	−0.0095 (7)	0.0002 (7)
C12	0.0417 (9)	0.0431 (8)	0.0338 (8)	0.0021 (6)	−0.0044 (6)	−0.0126 (6)
C13	0.0451 (10)	0.0769 (12)	0.0416 (9)	−0.0216 (9)	0.0003 (8)	−0.0158 (8)
C14	0.0595 (12)	0.0595 (11)	0.0473 (10)	−0.0259 (9)	0.0031 (9)	−0.0079 (9)
N1	0.0366 (8)	0.0634 (9)	0.0596 (9)	−0.0057 (6)	−0.0221 (7)	−0.0064 (7)
N2	0.0516 (9)	0.0652 (9)	0.0444 (8)	−0.0106 (7)	−0.0157 (7)	−0.0181 (7)
N3	0.0653 (11)	0.0632 (9)	0.0453 (8)	−0.0030 (8)	−0.0172 (8)	−0.0165 (7)
N4	0.1064 (17)	0.0812 (13)	0.0587 (11)	−0.0397 (12)	−0.0161 (11)	0.0099 (10)
S1	0.02631 (18)	0.0407 (2)	0.0367 (2)	−0.00195 (14)	−0.01004 (15)	−0.01111 (15)
S2	0.02509 (18)	0.03996 (19)	0.03258 (19)	−0.00337 (14)	−0.00934 (14)	−0.01026 (15)
S3	0.02685 (18)	0.03621 (19)	0.03086 (18)	−0.00055 (13)	−0.00891 (14)	−0.00827 (14)
S4	0.02534 (18)	0.0421 (2)	0.02945 (18)	−0.00093 (14)	−0.00827 (14)	−0.01089 (14)
S5	0.0400 (2)	0.03828 (19)	0.02918 (18)	−0.01030 (15)	−0.00711 (15)	−0.00961 (14)
S6	0.02798 (19)	0.0510 (2)	0.03197 (19)	−0.00714 (15)	−0.01181 (15)	−0.00518 (16)

C1—N1	1.1341 (19)	C9—C10	1.524 (2)
C1—C2	1.4316 (19)	C9—S6	1.8232 (17)
C2—C3	1.355 (2)	C9—H9A	0.9700
C2—S1	1.7352 (15)	C9—H9B	0.9700
C3—C4	1.424 (2)	C10—C11	1.464 (2)
C3—S2	1.7417 (14)	C10—H10A	0.9700
C4—N2	1.1404 (19)	C10—H10B	0.9700
C5—C6	1.3462 (19)	C11—N3	1.136 (2)
C5—S2	1.7611 (15)	C12—C13	1.520 (2)
C5—S1	1.7648 (14)	C12—S5	1.8066 (17)
C6—S3	1.7527 (15)	C12—H12A	0.9700
C6—S4	1.7558 (14)	C12—H12B	0.9700
C7—C8	1.351 (2)	C13—C14	1.465 (3)
C7—S6	1.7553 (14)	C13—H13A	0.9700
C7—S4	1.7628 (14)	C13—H13B	0.9700
C8—S5	1.7483 (14)	C14—N4	1.136 (2)
C8—S3	1.7536 (14)
N1—C1—C2	178.90 (18)	C11—C10—C9	111.21 (14)
C3—C2—C1	122.75 (13)	C11—C10—H10A	109.4
C3—C2—S1	118.32 (11)	C9—C10—H10A	109.4
C1—C2—S1	118.92 (11)	C11—C10—H10B	109.4
C2—C3—C4	123.46 (13)	C9—C10—H10B	109.4
C2—C3—S2	117.65 (11)	H10A—C10—H10B	108.0
C4—C3—S2	118.88 (10)	N3—C11—C10	177.38 (19)
N2—C4—C3	178.71 (16)	C13—C12—S5	115.32 (11)
C6—C5—S2	121.71 (11)	C13—C12—H12A	108.4
C6—C5—S1	122.52 (11)	S5—C12—H12A	108.4
S2—C5—S1	115.77 (8)	C13—C12—H12B	108.4
C5—C6—S3	122.05 (11)	S5—C12—H12B	108.4
C5—C6—S4	123.27 (11)	H12A—C12—H12B	107.5
S3—C6—S4	114.67 (8)	C14—C13—C12	112.75 (15)
C8—C7—S6	125.66 (11)	C14—C13—H13A	109.0
C8—C7—S4	117.08 (10)	C12—C13—H13A	109.0
S6—C7—S4	117.20 (8)	C14—C13—H13B	109.0
C7—C8—S5	123.02 (11)	C12—C13—H13B	109.0
C7—C8—S3	117.09 (10)	H13A—C13—H13B	107.8
S5—C8—S3	119.69 (8)	N4—C14—C13	178.8 (2)
C10—C9—S6	114.19 (10)	C2—S1—C5	94.05 (7)
C10—C9—H9A	108.7	C3—S2—C5	94.21 (7)
S6—C9—H9A	108.7	C6—S3—C8	95.71 (7)
C10—C9—H9B	108.7	C6—S4—C7	95.29 (7)
S6—C9—H9B	108.7	C8—S5—C12	102.98 (7)
H9A—C9—H9B	107.6	C7—S6—C9	100.68 (7)
N1—C1—C2—C3	−50 (9)	C1—C2—S1—C5	−178.05 (12)
N1—C1—C2—S1	129 (9)	C6—C5—S1—C2	−179.46 (12)
C1—C2—C3—C4	−1.2 (2)	S2—C5—S1—C2	−0.12 (8)
S1—C2—C3—C4	−179.88 (11)	C2—C3—S2—C5	0.78 (12)
C1—C2—C3—S2	177.64 (11)	C4—C3—S2—C5	179.67 (11)
S1—C2—C3—S2	−1.04 (16)	C6—C5—S2—C3	179.05 (12)
C2—C3—C4—N2	−168 (8)	S1—C5—S2—C3	−0.29 (9)
S2—C3—C4—N2	14 (8)	C5—C6—S3—C8	178.64 (12)
S2—C5—C6—S3	177.67 (7)	S4—C6—S3—C8	−2.39 (9)
S1—C5—C6—S3	−3.04 (18)	C7—C8—S3—C6	−0.40 (12)
S2—C5—C6—S4	−1.21 (18)	S5—C8—S3—C6	174.61 (8)
S1—C5—C6—S4	178.08 (7)	C5—C6—S4—C7	−177.40 (12)
S6—C7—C8—S5	5.36 (19)	S3—C6—S4—C7	3.65 (9)
S4—C7—C8—S5	−171.73 (7)	C8—C7—S4—C6	−4.05 (12)
S6—C7—C8—S3	−179.81 (8)	S6—C7—S4—C6	178.61 (8)
S4—C7—C8—S3	3.10 (16)	C7—C8—S5—C12	−162.25 (12)
S6—C9—C10—C11	−62.05 (14)	S3—C8—S5—C12	23.05 (10)
C9—C10—C11—N3	−17 (4)	C13—C12—S5—C8	73.13 (13)
S5—C12—C13—C14	59.88 (18)	C8—C7—S6—C9	93.08 (14)
C12—C13—C14—N4	−35 (11)	S4—C7—S6—C9	−89.84 (9)
C3—C2—S1—C5	0.68 (12)	C10—C9—S6—C7	−72.76 (12)