4-(Pyridin-2-yl)-1,3-dithiol-2-one.

In the title compound, C(8)H(5)NOS(2), the non-H atoms are approximately coplanar [maxium deviation = 0.060 (3) Å]. The dihedral angle between the least-squares planes of the pyridine and 1,3-dithiol-2-one rings is 5.96 (17)°. The crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen bonds and by an S⋯S close contact [3.510 (5) Å].

Related literature

For background to the chemistry of pyridine-based tetra­thia­fulvalenes, see: Fabre (2004 ▶); Zhu et al. (2010 ▶). For the preparation and crystal structures of related compounds, see: Zhu et al. (2010 ▶); Han et al. (2007 ▶).

Experimental

Crystal data

C8H5NOS2

M = 195.27

Orthorhombic,

a = 11.157 (2) Å

b = 5.3216 (10) Å

c = 13.689 (3) Å

V = 812.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.60 mm−1

T = 223 K

0.60 × 0.25 × 0.20 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.564, T max = 0.887

2825 measured reflections

1215 independent reflections

1144 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.081

S = 1.10

1215 reflections

110 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 430 Friedel pairs

Flack parameter: −0.09 (11)

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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001407/pk2379sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001407/pk2379Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001407/pk2379Isup3.cml

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

C8H5NOS2	F(000) = 400
Mr = 195.27	Dx = 1.596 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2n	Cell parameters from 2396 reflections
a = 11.157 (2) Å	θ = 3.5–27.5°
b = 5.3216 (10) Å	µ = 0.60 mm−1
c = 13.689 (3) Å	T = 223 K
V = 812.8 (3) Å3	Block, colorless
Z = 4	0.60 × 0.25 × 0.20 mm

Rigaku Saturn CCD diffractometer	1215 independent reflections
Radiation source: fine-focus sealed tube	1144 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.9°
ω scans	h = −10→13
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −6→5
Tmin = 0.564, Tmax = 0.887	l = −15→16
2825 measured 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.0545P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
1215 reflections	Δρmax = 0.18 e Å−3
110 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 430 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (11)

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	0.29937 (7)	1.06740 (15)	0.65200 (6)	0.0415 (2)
S2	0.53107 (7)	1.18329 (17)	0.55954 (7)	0.0439 (2)
O1	0.3307 (3)	1.4374 (5)	0.52711 (19)	0.0562 (7)
N1	0.2818 (2)	0.6783 (5)	0.7860 (2)	0.0407 (7)
C3	0.4232 (3)	0.8896 (6)	0.6876 (2)	0.0329 (7)
C4	0.3981 (3)	0.6970 (6)	0.7623 (2)	0.0328 (7)
C8	0.2525 (4)	0.5068 (7)	0.8529 (3)	0.0482 (9)
H8	0.1713	0.4931	0.8704	0.058*
C7	0.3323 (4)	0.3487 (7)	0.8980 (3)	0.0474 (9)
H7	0.3068	0.2274	0.9434	0.057*
C6	0.4513 (4)	0.3754 (7)	0.8740 (3)	0.0443 (8)
H6	0.5091	0.2738	0.9047	0.053*
C5	0.4867 (3)	0.5504 (6)	0.8052 (3)	0.0380 (8)
H5	0.5678	0.5695	0.7880	0.046*
C2	0.5273 (3)	0.9427 (6)	0.6451 (2)	0.0349 (7)
H2	0.5970	0.8523	0.6609	0.042*
C1	0.3772 (3)	1.2650 (6)	0.5707 (2)	0.0414 (8)

	U11	U22	U33	U12	U13	U23
S1	0.0314 (4)	0.0446 (5)	0.0484 (5)	0.0045 (3)	−0.0023 (4)	0.0054 (5)
S2	0.0388 (5)	0.0469 (5)	0.0459 (4)	−0.0031 (4)	−0.0006 (4)	0.0105 (4)
O1	0.0569 (16)	0.0481 (15)	0.0636 (18)	0.0060 (12)	−0.0125 (14)	0.0169 (13)
N1	0.0335 (15)	0.0428 (17)	0.0456 (16)	−0.0022 (13)	0.0034 (13)	0.0024 (15)
C3	0.0306 (17)	0.0326 (16)	0.0354 (16)	−0.0010 (14)	−0.0022 (13)	−0.0021 (14)
C4	0.0295 (16)	0.0326 (17)	0.0362 (16)	0.0008 (14)	−0.0022 (14)	−0.0008 (14)
C8	0.0369 (18)	0.057 (2)	0.051 (2)	−0.0075 (19)	0.0089 (17)	−0.001 (2)
C7	0.057 (2)	0.0413 (19)	0.044 (2)	−0.0030 (19)	0.0045 (17)	0.0009 (17)
C6	0.051 (2)	0.0404 (18)	0.0418 (18)	0.0073 (17)	−0.0046 (16)	0.0032 (17)
C5	0.0345 (18)	0.041 (2)	0.0383 (18)	−0.0006 (17)	0.0015 (14)	−0.0001 (16)
C2	0.0292 (15)	0.0358 (16)	0.0397 (18)	0.0020 (13)	−0.0029 (17)	0.0013 (15)
C1	0.0367 (17)	0.0442 (18)	0.0433 (18)	−0.0036 (15)	−0.0062 (17)	−0.0061 (18)

S1—C3	1.744 (3)	C4—C5	1.390 (5)
S1—C1	1.760 (4)	C8—C7	1.372 (5)
S2—C2	1.736 (3)	C8—H8	0.9400
S2—C1	1.778 (4)	C7—C6	1.375 (6)
O1—C1	1.211 (4)	C7—H7	0.9400
N1—C8	1.334 (5)	C6—C5	1.382 (5)
N1—C4	1.342 (4)	C6—H6	0.9400
C3—C2	1.329 (5)	C5—H5	0.9400
C3—C4	1.474 (4)	C2—H2	0.9400
C3—S1—C1	96.32 (17)	C6—C7—H7	121.4
C2—S2—C1	95.66 (16)	C7—C6—C5	120.5 (4)
C8—N1—C4	117.0 (3)	C7—C6—H6	119.7
C2—C3—C4	128.1 (3)	C5—C6—H6	119.7
C2—C3—S1	117.0 (2)	C6—C5—C4	117.6 (3)
C4—C3—S1	114.8 (2)	C6—C5—H5	121.2
N1—C4—C5	123.0 (3)	C4—C5—H5	121.2
N1—C4—C3	113.8 (3)	C3—C2—S2	118.3 (2)
C5—C4—C3	123.2 (3)	C3—C2—H2	120.9
N1—C8—C7	124.7 (4)	S2—C2—H2	120.9
N1—C8—H8	117.6	O1—C1—S1	123.6 (3)
C7—C8—H8	117.6	O1—C1—S2	123.8 (3)
C8—C7—C6	117.1 (4)	S1—C1—S2	112.63 (19)
C8—C7—H7	121.4
C1—S1—C3—C2	−2.3 (3)	C7—C6—C5—C4	0.3 (6)
C1—S1—C3—C4	177.7 (2)	N1—C4—C5—C6	1.2 (5)
C8—N1—C4—C5	−1.1 (5)	C3—C4—C5—C6	−179.7 (3)
C8—N1—C4—C3	179.7 (3)	C4—C3—C2—S2	−179.5 (2)
C2—C3—C4—N1	−175.8 (3)	S1—C3—C2—S2	0.5 (4)
S1—C3—C4—N1	4.3 (4)	C1—S2—C2—C3	1.5 (3)
C2—C3—C4—C5	5.1 (5)	C3—S1—C1—O1	−177.0 (3)
S1—C3—C4—C5	−174.9 (3)	C3—S1—C1—S2	3.1 (2)
C4—N1—C8—C7	−0.4 (5)	C2—S2—C1—O1	177.2 (3)
N1—C8—C7—C6	1.9 (6)	C2—S2—C1—S1	−2.9 (2)
C8—C7—C6—C5	−1.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.94	2.46	3.3486	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.94	2.46	3.3486	158

Symmetry code: (i) .