3-(2-Thioxo-1,3-dithiol-4-ylsulfan-yl)-propane-nitrile.

The title compound, C(6)H(5)NS(4), consists of a planar 2-thioxo-1,3-dithiol-4-ylsulfanyl unit [maximum deviation from the ring plane = 0.0325 (2) Å], with a cyano-ethyl-sulfanyl substituent in the 4-position. In the crystal structure, weak inter-molecular C-H⋯S hydrogen bonds together with S⋯N inter-actions [3.260 (5) Å] form two-dimensional layers in the bc plane.

Related literature

For background to the chemistry of dithiole-2-thio­nes and tetra­thia­fulvenes, see: Chen et al. (2005 ▶); Fabre (2004 ▶); Segura & Martin (2001 ▶). For the preparation of the title compound, see: Liu et al. (2002 ▶). For a related structure, see: Jia et al. (2001 ▶).

Experimental

Crystal data

C6H5NS4

M = 219.35

Monoclinic,

a = 5.2961 (9) Å

b = 10.8917 (19) Å

c = 16.031 (3) Å

β = 97.302 (2)°

V = 917.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 295 (2) K

0.35 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.728, T max = 0.808

6626 measured reflections

1710 independent reflections

1525 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.07

1710 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031711/sj2541sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031711/sj2541Isup2.hkl

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

C6H5NS4	F(000) = 448
Mr = 219.35	Dx = 1.588 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3529 reflections
a = 5.2961 (9) Å	θ = 2.6–27.9°
b = 10.8917 (19) Å	µ = 0.97 mm−1
c = 16.031 (3) Å	T = 295 K
β = 97.302 (2)°	Block, yellow
V = 917.2 (3) Å3	0.35 × 0.27 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1710 independent reflections
Radiation source: fine-focus sealed tube	1525 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.728, Tmax = 0.808	k = −12→13
6626 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.3313P] where P = (Fo2 + 2Fc2)/3
1710 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.34 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	0.21596 (10)	1.03249 (5)	0.12572 (3)	0.05315 (17)
S2	0.34613 (11)	0.99269 (5)	0.30276 (3)	0.05650 (17)
S3	−0.06717 (11)	1.17189 (6)	0.24268 (4)	0.05929 (17)
S4	0.60268 (9)	0.85154 (5)	0.07595 (3)	0.05352 (16)
N1	−0.1988 (4)	0.62697 (19)	−0.06631 (14)	0.0688 (5)
C1	0.1519 (3)	1.07055 (18)	0.22542 (12)	0.0433 (4)
C2	0.4470 (3)	0.92099 (17)	0.15433 (12)	0.0422 (4)
C3	0.5061 (4)	0.90441 (19)	0.23696 (12)	0.0493 (5)
H3	0.6287	0.8476	0.2583	0.059*
C4	0.3347 (4)	0.79990 (19)	0.00199 (12)	0.0486 (5)
H4A	0.2071	0.8642	−0.0051	0.058*
H4B	0.3921	0.7852	−0.0522	0.058*
C5	0.2159 (4)	0.6842 (2)	0.03091 (14)	0.0573 (5)
H5A	0.3375	0.6174	0.0321	0.069*
H5B	0.1748	0.6959	0.0876	0.069*
C6	−0.0165 (4)	0.65095 (19)	−0.02465 (14)	0.0531 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0531 (3)	0.0661 (3)	0.0389 (3)	0.0149 (2)	0.0007 (2)	0.0015 (2)
S2	0.0672 (4)	0.0630 (3)	0.0382 (3)	0.0049 (3)	0.0027 (2)	0.0019 (2)
S3	0.0548 (3)	0.0623 (4)	0.0621 (3)	0.0057 (2)	0.0123 (3)	−0.0081 (3)
S4	0.0401 (3)	0.0667 (3)	0.0525 (3)	0.0006 (2)	0.0008 (2)	−0.0142 (2)
N1	0.0643 (12)	0.0674 (12)	0.0708 (13)	−0.0096 (10)	−0.0057 (10)	−0.0105 (10)
C1	0.0420 (10)	0.0451 (10)	0.0424 (10)	−0.0085 (8)	0.0044 (8)	−0.0009 (8)
C2	0.0372 (9)	0.0432 (10)	0.0444 (10)	−0.0041 (7)	−0.0018 (7)	−0.0035 (8)
C3	0.0510 (11)	0.0464 (11)	0.0487 (11)	0.0034 (9)	−0.0009 (9)	0.0016 (9)
C4	0.0529 (11)	0.0505 (11)	0.0402 (10)	0.0001 (9)	−0.0022 (8)	−0.0024 (8)
C5	0.0569 (12)	0.0593 (13)	0.0531 (12)	−0.0052 (10)	−0.0030 (10)	0.0069 (10)
C6	0.0549 (12)	0.0503 (12)	0.0541 (12)	−0.0041 (9)	0.0070 (10)	−0.0044 (9)

S1—C1	1.7262 (19)	C2—C3	1.334 (3)
S1—C2	1.7435 (19)	C3—H3	0.9300
S2—C3	1.727 (2)	C4—C5	1.508 (3)
S2—C1	1.729 (2)	C4—H4A	0.9700
S3—C1	1.650 (2)	C4—H4B	0.9700
S4—C2	1.759 (2)	C5—C6	1.470 (3)
S4—C4	1.8191 (19)	C5—H5A	0.9700
N1—C6	1.133 (3)	C5—H5B	0.9700
C1—S1—C2	97.91 (9)	C5—C4—H4A	109.1
C3—S2—C1	97.39 (9)	S4—C4—H4A	109.1
C2—S4—C4	101.59 (9)	C5—C4—H4B	109.1
S3—C1—S1	122.76 (12)	S4—C4—H4B	109.1
S3—C1—S2	125.08 (12)	H4A—C4—H4B	107.9
S1—C1—S2	112.15 (11)	C6—C5—C4	111.69 (18)
C3—C2—S1	115.08 (15)	C6—C5—H5A	109.3
C3—C2—S4	125.36 (15)	C4—C5—H5A	109.3
S1—C2—S4	119.25 (11)	C6—C5—H5B	109.3
C2—C3—S2	117.36 (16)	C4—C5—H5B	109.3
C2—C3—H3	121.3	H5A—C5—H5B	107.9
S2—C3—H3	121.3	N1—C6—C5	178.4 (2)
C5—C4—S4	112.31 (14)
C2—S1—C1—S2	3.39 (12)	C4—S4—C2—S1	−52.73 (13)
C3—S2—C1—S3	178.04 (13)	S1—C2—C3—S2	0.7 (2)
C3—S2—C1—S1	−3.08 (12)	S4—C2—C3—S2	174.29 (11)
C1—S1—C2—C3	−2.54 (17)	C1—S2—C3—C2	1.47 (18)
C1—S1—C2—S4	−176.53 (11)	C2—S4—C4—C5	−78.01 (17)
C4—S4—C2—C3	133.94 (18)	S4—C4—C5—C6	173.85 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···S3i	0.97	2.86	3.813 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯S3i	0.97	2.86	3.813 (2)	167

Symmetry code: (i) .