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

In the title compound, C(12)H(10)N(2)S(6), all non-H atoms, except for those in the ethyl groups, lie in the same non-crystallographic plane, with a r.m.s. deviation of 0.0366 (5) Å. In the crystal structure, mol-ecules are linked through weak C-H⋯N hydrogen bonds between methyl and cyano groups, forming centrosymmetric dimers. The dimers are arranged along the a axis, due to inter-molecular N⋯S [3.337 (4) Å] inter-actions.

Related literature

For synthetic uses of dicyano-substituted tetra­thia­fulvalene derivatives, see: Chen et al. (2007 ▶); Leng et al. (2010 ▶). For a related structure, see: Jiang et al. (2010 ▶). For the synthesis of the title compound, see: Chen et al. (2005 ▶).

Experimental

Crystal data

C12H10N2S6

M = 374.58

Triclinic,

a = 7.8357 (16) Å

b = 8.9777 (18) Å

c = 12.618 (3) Å

α = 76.48 (3)°

β = 77.59 (3)°

γ = 73.20 (3)°

V = 815.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.83 mm−1

T = 293 K

0.15 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.886, T max = 0.907

8038 measured reflections

3689 independent reflections

3079 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.109

S = 1.15

3689 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.42 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536811028601/bh2367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028601/bh2367Isup2.hkl

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

C12H10N2S6	Z = 2
Mr = 374.58	F(000) = 384
Triclinic, P1	Dx = 1.525 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8357 (16) Å	Cell parameters from 3994 reflections
b = 8.9777 (18) Å	θ = 3.2–27.5°
c = 12.618 (3) Å	µ = 0.83 mm−1
α = 76.48 (3)°	T = 293 K
β = 77.59 (3)°	Block, black
γ = 73.20 (3)°	0.15 × 0.13 × 0.12 mm
V = 815.8 (3) Å3

Rigaku R-AXIS RAPID diffractometer	3689 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.886, Tmax = 0.907	k = −11→10
8038 measured reflections	l = −16→16

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) = 0.109	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.1175P] where P = (Fo2 + 2Fc2)/3
3689 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.42 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	1.3781 (3)	0.3004 (3)	1.17179 (18)	0.0471 (5)
C2	1.2353 (2)	0.2956 (2)	1.11964 (14)	0.0346 (4)
C3	1.0593 (2)	0.3581 (2)	1.15573 (14)	0.0325 (4)
C4	0.9973 (3)	0.4385 (2)	1.24706 (16)	0.0404 (4)
C5	1.0603 (2)	0.2358 (2)	0.99101 (14)	0.0312 (4)
C6	1.0078 (2)	0.1834 (2)	0.91471 (14)	0.0314 (4)
C7	0.8174 (3)	0.1324 (2)	0.78825 (14)	0.0362 (4)
C8	0.9902 (3)	0.0668 (2)	0.74847 (14)	0.0348 (4)
C9	1.2580 (3)	0.0150 (3)	0.56711 (17)	0.0514 (5)
H9A	1.3429	−0.0101	0.6183	0.062*
H9B	1.3115	−0.0489	0.5104	0.062*
C10	1.2308 (4)	0.1859 (3)	0.5143 (2)	0.0673 (7)
H10A	1.1425	0.2134	0.4662	0.101*
H10B	1.3430	0.2042	0.4725	0.101*
H10C	1.1895	0.2499	0.5705	0.101*
C11	0.5366 (3)	0.3331 (3)	0.6882 (2)	0.0658 (7)
H11A	0.4252	0.3457	0.6615	0.079*
H11B	0.5078	0.3900	0.7489	0.079*
C12	0.6628 (5)	0.4051 (4)	0.5971 (3)	0.1003 (13)
H12A	0.7769	0.3859	0.6210	0.150*
H12B	0.6122	0.5171	0.5789	0.150*
H12C	0.6801	0.3584	0.5333	0.150*
N1	1.4901 (3)	0.3032 (3)	1.21488 (19)	0.0733 (6)
N2	0.9451 (3)	0.5027 (2)	1.31940 (17)	0.0632 (5)
S1	1.28831 (6)	0.20402 (6)	1.00515 (4)	0.03914 (14)
S2	0.89965 (6)	0.33925 (6)	1.08715 (4)	0.03802 (14)
S3	0.77877 (6)	0.21620 (6)	0.90659 (4)	0.04141 (14)
S4	1.15711 (6)	0.07338 (6)	0.81983 (4)	0.03804 (14)
S5	0.62815 (7)	0.12625 (7)	0.73859 (4)	0.04650 (16)
S6	1.05259 (8)	−0.03845 (7)	0.64039 (4)	0.04750 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0377 (10)	0.0631 (13)	0.0461 (11)	−0.0110 (10)	−0.0063 (9)	−0.0232 (10)
C2	0.0360 (9)	0.0404 (9)	0.0320 (9)	−0.0122 (8)	−0.0083 (7)	−0.0094 (7)
C3	0.0369 (9)	0.0348 (9)	0.0290 (8)	−0.0107 (7)	−0.0058 (7)	−0.0090 (7)
C4	0.0420 (10)	0.0436 (10)	0.0369 (10)	−0.0073 (9)	−0.0071 (8)	−0.0136 (8)
C5	0.0324 (8)	0.0345 (9)	0.0288 (8)	−0.0090 (7)	−0.0058 (7)	−0.0081 (7)
C6	0.0341 (8)	0.0355 (9)	0.0274 (8)	−0.0107 (7)	−0.0068 (7)	−0.0070 (7)
C7	0.0404 (9)	0.0443 (10)	0.0301 (9)	−0.0177 (8)	−0.0111 (7)	−0.0050 (7)
C8	0.0434 (9)	0.0416 (9)	0.0255 (8)	−0.0183 (8)	−0.0084 (7)	−0.0060 (7)
C9	0.0471 (11)	0.0647 (14)	0.0430 (11)	−0.0095 (11)	0.0012 (9)	−0.0245 (10)
C10	0.0797 (18)	0.0730 (16)	0.0516 (14)	−0.0346 (14)	0.0086 (12)	−0.0144 (12)
C11	0.0585 (14)	0.0618 (15)	0.0846 (18)	−0.0060 (12)	−0.0410 (14)	−0.0121 (13)
C12	0.115 (3)	0.085 (2)	0.110 (3)	−0.050 (2)	−0.065 (2)	0.0395 (19)
N1	0.0473 (11)	0.1120 (18)	0.0767 (15)	−0.0167 (12)	−0.0174 (11)	−0.0453 (14)
N2	0.0704 (13)	0.0684 (13)	0.0527 (12)	−0.0068 (11)	−0.0075 (10)	−0.0303 (10)
S1	0.0314 (2)	0.0513 (3)	0.0399 (3)	−0.0088 (2)	−0.00407 (19)	−0.0216 (2)
S2	0.0303 (2)	0.0491 (3)	0.0386 (3)	−0.0089 (2)	−0.00466 (18)	−0.0176 (2)
S3	0.0336 (2)	0.0591 (3)	0.0365 (3)	−0.0109 (2)	−0.00710 (19)	−0.0180 (2)
S4	0.0348 (2)	0.0504 (3)	0.0336 (3)	−0.0103 (2)	−0.00648 (18)	−0.0162 (2)
S5	0.0454 (3)	0.0585 (3)	0.0465 (3)	−0.0236 (3)	−0.0173 (2)	−0.0084 (2)
S6	0.0633 (3)	0.0552 (3)	0.0346 (3)	−0.0267 (3)	−0.0028 (2)	−0.0185 (2)

C1—N1	1.136 (3)	C8—S4	1.7606 (18)
C1—C2	1.430 (3)	C9—C10	1.496 (3)
C2—C3	1.352 (3)	C9—S6	1.810 (2)
C2—S1	1.7423 (19)	C9—H9A	0.9700
C3—C4	1.425 (2)	C9—H9B	0.9700
C3—S2	1.7314 (18)	C10—H10A	0.9600
C4—N2	1.132 (3)	C10—H10B	0.9600
C5—C6	1.346 (2)	C10—H10C	0.9600
C5—S2	1.7646 (19)	C11—C12	1.500 (4)
C5—S1	1.7673 (18)	C11—S5	1.800 (3)
C6—S4	1.7495 (19)	C11—H11A	0.9700
C6—S3	1.7543 (18)	C11—H11B	0.9700
C7—C8	1.348 (3)	C12—H12A	0.9600
C7—S5	1.7483 (18)	C12—H12B	0.9600
C7—S3	1.7569 (19)	C12—H12C	0.9600
C8—S6	1.7439 (19)
N1—C1—C2	178.9 (3)	H9A—C9—H9B	107.7
C3—C2—C1	122.92 (17)	C9—C10—H10A	109.5
C3—C2—S1	117.99 (14)	C9—C10—H10B	109.5
C1—C2—S1	119.09 (15)	H10A—C10—H10B	109.5
C2—C3—C4	123.81 (17)	C9—C10—H10C	109.5
C2—C3—S2	118.14 (13)	H10A—C10—H10C	109.5
C4—C3—S2	118.05 (14)	H10B—C10—H10C	109.5
N2—C4—C3	178.8 (2)	C12—C11—S5	113.3 (2)
C6—C5—S2	120.78 (14)	C12—C11—H11A	108.9
C6—C5—S1	123.79 (15)	S5—C11—H11A	108.9
S2—C5—S1	115.42 (10)	C12—C11—H11B	108.9
C5—C6—S4	123.86 (14)	S5—C11—H11B	108.9
C5—C6—S3	121.49 (15)	H11A—C11—H11B	107.7
S4—C6—S3	114.62 (10)	C11—C12—H12A	109.5
C8—C7—S5	125.25 (15)	C11—C12—H12B	109.5
C8—C7—S3	117.19 (14)	H12A—C12—H12B	109.5
S5—C7—S3	117.34 (11)	C11—C12—H12C	109.5
C7—C8—S6	123.52 (14)	H12A—C12—H12C	109.5
C7—C8—S4	116.94 (14)	H12B—C12—H12C	109.5
S6—C8—S4	119.23 (11)	C2—S1—C5	94.04 (9)
C10—C9—S6	113.94 (17)	C3—S2—C5	94.40 (8)
C10—C9—H9A	108.8	C6—S3—C7	95.39 (9)
S6—C9—H9A	108.8	C6—S4—C8	95.48 (9)
C10—C9—H9B	108.8	C7—S5—C11	101.18 (10)
S6—C9—H9B	108.8	C8—S6—C9	102.91 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···N2i	0.96	2.73	3.659 (4)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯N2i	0.96	2.73	3.659 (4)	164

Symmetry code: (i) .