4-(2-Cyano-ethyl-sulfan-yl)-5'-(pyridin-4-yl)tetra-thia-fulvalene.

In the title compound, C(14)H(10)N(2)S(5) [systematic name; 3-({2-[4-(pyridin-4-yl)-2H-1,3-dithiol-2-yl-idene]-2H-1,3-dithiol-4-yl}sul-fan-yl)propane-nitrile], all of the non-H atoms except for the cyano-ethyl-sulfanyl group, are approximately coplanar [maxium deviation = 0.090 (3) Å]. The two five-membered 1,3-dithiole rings are twisted by 2.6 (2)°. Weak inter-molecular S⋯S inter-actions occur [3.586 (4) and 3.530 (4) Å].

Related literature

For background to the chemistry of prridine-based tetra­thia­fulvalenes, see: Fabre (2004 ▶); Zhu et al. (2007 ▶). For the preparation of the title compound, see: Jia et al. (2001 ▶); Zhu et al. (2010 ▶). For related structures, see: Han et al. (2007 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

C14H10N2S5

M = 366.54

Monoclinic,

a = 14.6231 (18) Å

b = 10.7197 (12) Å

c = 9.9211 (12) Å

β = 94.775 (4)°

V = 1549.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 223 K

0.50 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.613, T max = 0.856

7658 measured reflections

2869 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.126

S = 1.11

2869 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2005) ▶; cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018800/ng5167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018800/ng5167Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018800/ng5167Isup3.cml

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

C14H10N2S5	F(000) = 752
Mr = 366.54	Dx = 1.571 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 5787 reflections
a = 14.6231 (18) Å	θ = 3.1–27.5°
b = 10.7197 (12) Å	µ = 0.74 mm−1
c = 9.9211 (12) Å	T = 223 K
β = 94.775 (4)°	Block, red
V = 1549.8 (3) Å3	0.50 × 0.20 × 0.20 mm
Z = 4

Rigaku Saturn diffractometer	2869 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.1°
ω scans	h = −17→16
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→12
Tmin = 0.613, Tmax = 0.856	l = −12→9
7658 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0484P)2 + 1.3388P] where P = (Fo2 + 2Fc2)/3
2869 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.32 e Å−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	0.45140 (7)	0.17432 (9)	0.11234 (11)	0.0324 (3)
S2	0.57042 (7)	−0.02950 (10)	0.22543 (11)	0.0362 (3)
S3	0.61033 (7)	0.25532 (10)	−0.08148 (12)	0.0377 (3)
S4	0.72869 (7)	0.05022 (10)	0.03146 (11)	0.0361 (3)
S5	0.87437 (8)	0.10167 (11)	−0.16139 (12)	0.0438 (3)
N1	0.1558 (3)	0.1902 (4)	0.3981 (5)	0.0555 (11)
N2	0.9396 (3)	0.4512 (4)	−0.1998 (5)	0.0619 (12)
C1	0.1881 (3)	0.2455 (5)	0.2923 (6)	0.0601 (14)
H1	0.1532	0.3107	0.2508	0.072*
C2	0.2690 (3)	0.2145 (4)	0.2386 (5)	0.0459 (12)
H2	0.2865	0.2562	0.1615	0.055*
C3	0.3240 (3)	0.1224 (4)	0.2984 (4)	0.0323 (9)
C4	0.2907 (3)	0.0618 (4)	0.4090 (5)	0.0451 (12)
H4	0.3242	−0.0035	0.4528	0.054*
C5	0.2082 (3)	0.0989 (5)	0.4532 (5)	0.0529 (14)
H5	0.1873	0.0568	0.5278	0.063*
C6	0.4131 (3)	0.0883 (4)	0.2484 (4)	0.0321 (9)
C7	0.4680 (3)	−0.0036 (4)	0.2963 (4)	0.0345 (10)
H7	0.4512	−0.0538	0.3680	0.041*
C8	0.5581 (2)	0.0973 (3)	0.1123 (4)	0.0284 (9)
C9	0.6232 (3)	0.1293 (4)	0.0326 (4)	0.0298 (9)
C10	0.7170 (3)	0.2350 (4)	−0.1449 (4)	0.0348 (10)
H10	0.7363	0.2886	−0.2120	0.042*
C11	0.7705 (3)	0.1427 (4)	−0.0967 (4)	0.0350 (10)
C12	0.9586 (3)	0.1601 (5)	−0.0324 (5)	0.0484 (12)
H12A	0.9549	0.1103	0.0498	0.058*
H12B	1.0199	0.1478	−0.0632	0.058*
C13	0.9480 (3)	0.2965 (5)	0.0034 (5)	0.0511 (13)
H13A	0.8915	0.3064	0.0491	0.061*
H13B	0.9995	0.3207	0.0676	0.061*
C14	0.9445 (3)	0.3823 (5)	−0.1136 (5)	0.0458 (12)

	U11	U22	U33	U12	U13	U23
S1	0.0303 (5)	0.0311 (5)	0.0363 (6)	0.0025 (4)	0.0064 (4)	0.0022 (4)
S2	0.0359 (6)	0.0343 (6)	0.0396 (7)	0.0060 (5)	0.0090 (5)	0.0060 (5)
S3	0.0350 (6)	0.0345 (6)	0.0439 (7)	0.0004 (5)	0.0048 (5)	0.0076 (5)
S4	0.0306 (5)	0.0372 (6)	0.0413 (7)	0.0026 (5)	0.0079 (5)	0.0050 (5)
S5	0.0359 (6)	0.0507 (7)	0.0469 (8)	−0.0030 (5)	0.0165 (5)	−0.0037 (6)
N1	0.036 (2)	0.063 (3)	0.070 (3)	−0.005 (2)	0.020 (2)	−0.014 (2)
N2	0.069 (3)	0.056 (3)	0.062 (3)	0.004 (2)	0.014 (2)	0.003 (2)
C1	0.036 (3)	0.066 (3)	0.080 (4)	0.007 (2)	0.011 (3)	0.004 (3)
C2	0.037 (2)	0.051 (3)	0.051 (3)	0.003 (2)	0.010 (2)	0.010 (2)
C3	0.027 (2)	0.032 (2)	0.037 (3)	−0.0060 (17)	0.0039 (18)	−0.0083 (18)
C4	0.044 (3)	0.042 (3)	0.051 (3)	0.000 (2)	0.017 (2)	0.002 (2)
C5	0.047 (3)	0.056 (3)	0.060 (3)	−0.013 (3)	0.025 (3)	−0.007 (3)
C6	0.031 (2)	0.030 (2)	0.036 (2)	−0.0051 (18)	0.0087 (18)	−0.0032 (18)
C7	0.037 (2)	0.038 (2)	0.030 (2)	−0.0037 (19)	0.0103 (18)	0.0014 (19)
C8	0.0252 (19)	0.027 (2)	0.033 (2)	−0.0019 (16)	−0.0001 (17)	−0.0029 (17)
C9	0.030 (2)	0.030 (2)	0.030 (2)	−0.0032 (17)	0.0018 (17)	−0.0028 (17)
C10	0.036 (2)	0.039 (2)	0.030 (2)	−0.0086 (19)	0.0072 (19)	0.0033 (19)
C11	0.031 (2)	0.039 (2)	0.036 (3)	−0.0080 (19)	0.0085 (19)	0.000 (2)
C12	0.031 (2)	0.063 (3)	0.052 (3)	0.000 (2)	0.009 (2)	0.007 (3)
C13	0.041 (3)	0.069 (3)	0.043 (3)	−0.010 (2)	0.007 (2)	−0.007 (3)
C14	0.039 (3)	0.050 (3)	0.049 (3)	−0.003 (2)	0.010 (2)	−0.013 (3)

S1—C6	1.764 (4)	C3—C4	1.398 (6)
S1—C8	1.765 (4)	C3—C6	1.478 (5)
S2—C7	1.729 (4)	C4—C5	1.376 (6)
S2—C8	1.762 (4)	C4—H4	0.9400
S3—C10	1.744 (4)	C5—H5	0.9400
S3—C9	1.762 (4)	C6—C7	1.333 (6)
S4—C9	1.761 (4)	C7—H7	0.9400
S4—C11	1.761 (4)	C8—C9	1.333 (5)
S5—C11	1.753 (4)	C10—C11	1.326 (6)
S5—C12	1.812 (5)	C10—H10	0.9400
N1—C1	1.327 (7)	C12—C13	1.515 (6)
N1—C5	1.331 (7)	C12—H12A	0.9800
N2—C14	1.128 (6)	C12—H12B	0.9800
C1—C2	1.377 (6)	C13—C14	1.479 (7)
C1—H1	0.9400	C13—H13A	0.9800
C2—C3	1.377 (6)	C13—H13B	0.9800
C2—H2	0.9400
C6—S1—C8	95.29 (18)	S2—C7—H7	120.3
C7—S2—C8	95.10 (19)	C9—C8—S2	122.4 (3)
C10—S3—C9	94.88 (19)	C9—C8—S1	123.7 (3)
C9—S4—C11	95.20 (19)	S2—C8—S1	113.8 (2)
C11—S5—C12	102.3 (2)	C8—C9—S4	123.3 (3)
C1—N1—C5	115.0 (4)	C8—C9—S3	122.3 (3)
N1—C1—C2	124.8 (5)	S4—C9—S3	114.3 (2)
N1—C1—H1	117.6	C11—C10—S3	118.8 (3)
C2—C1—H1	117.6	C11—C10—H10	120.6
C3—C2—C1	119.8 (4)	S3—C10—H10	120.6
C3—C2—H2	120.1	C10—C11—S5	123.9 (3)
C1—C2—H2	120.1	C10—C11—S4	116.8 (3)
C2—C3—C4	116.2 (4)	S5—C11—S4	119.1 (2)
C2—C3—C6	122.2 (4)	C13—C12—S5	115.0 (3)
C4—C3—C6	121.6 (4)	C13—C12—H12A	108.5
C5—C4—C3	119.2 (4)	S5—C12—H12A	108.5
C5—C4—H4	120.4	C13—C12—H12B	108.5
C3—C4—H4	120.4	S5—C12—H12B	108.5
N1—C5—C4	124.9 (5)	H12A—C12—H12B	107.5
N1—C5—H5	117.6	C14—C13—C12	114.5 (4)
C4—C5—H5	117.6	C14—C13—H13A	108.6
C7—C6—C3	125.8 (4)	C12—C13—H13A	108.6
C7—C6—S1	116.0 (3)	C14—C13—H13B	108.6
C3—C6—S1	118.2 (3)	C12—C13—H13B	108.6
C6—C7—S2	119.3 (3)	H13A—C13—H13B	107.6
C6—C7—H7	120.3	N2—C14—C13	177.0 (5)
C5—N1—C1—C2	0.3 (8)	C6—S1—C8—S2	6.1 (2)
N1—C1—C2—C3	−2.1 (8)	S2—C8—C9—S4	−0.5 (5)
C1—C2—C3—C4	2.7 (7)	S1—C8—C9—S4	−178.9 (2)
C1—C2—C3—C6	−177.7 (4)	S2—C8—C9—S3	179.4 (2)
C2—C3—C4—C5	−1.7 (6)	S1—C8—C9—S3	1.0 (5)
C6—C3—C4—C5	178.7 (4)	C11—S4—C9—C8	178.6 (4)
C1—N1—C5—C4	0.7 (8)	C11—S4—C9—S3	−1.4 (3)
C3—C4—C5—N1	0.0 (8)	C10—S3—C9—C8	−179.1 (4)
C2—C3—C6—C7	−176.5 (4)	C10—S3—C9—S4	0.8 (3)
C4—C3—C6—C7	3.1 (7)	C9—S3—C10—C11	0.3 (4)
C2—C3—C6—S1	2.9 (6)	S3—C10—C11—S5	173.8 (2)
C4—C3—C6—S1	−177.5 (3)	S3—C10—C11—S4	−1.4 (5)
C8—S1—C6—C7	−4.2 (4)	C12—S5—C11—C10	106.0 (4)
C8—S1—C6—C3	176.3 (3)	C12—S5—C11—S4	−79.0 (3)
C3—C6—C7—S2	−179.7 (3)	C9—S4—C11—C10	1.6 (4)
S1—C6—C7—S2	0.9 (5)	C9—S4—C11—S5	−173.7 (3)
C8—S2—C7—C6	3.0 (4)	C11—S5—C12—C13	−53.5 (4)
C7—S2—C8—C9	175.7 (4)	S5—C12—C13—C14	−53.5 (5)
C7—S2—C8—S1	−5.7 (3)	C12—C13—C14—N2	152 (11)
C6—S1—C8—C9	−175.4 (4)