(Furan-2-yl)[(furan-2-yl)carbonyl-disul-fanyl]methanone.

The mol-ecule of the title compound, C(10)H(6)O(4)S(2), has crystallographically imposed twofold symmetry. The dihedral angle formed by the furan rings is 80.90 (8)°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into chains running parallel to the a axis [C-S-S-C torsion angle = 82.04 (11)°].

Related literature

For the applications of furan-2-carbothioic-S-acid, see: Deshpande et al. (2004 ▶); Stoll et al. (1967 ▶).

Experimental

Crystal data

C10H6O4S2

M = 254.29

Orthorhombic,

a = 13.6900 (13) Å

b = 7.9611 (7) Å

c = 9.9042 (10) Å

V = 1079.43 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 298 K

0.41 × 0.39 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.826, T max = 0.868

3627 measured reflections

952 independent reflections

750 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.103

S = 1.00

952 reflections

74 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 datablock(s) I, global. DOI: 10.1107/S160053681104356X/rz2653sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104356X/rz2653Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104356X/rz2653Isup3.cml

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

C10H6O4S2	F(000) = 520
Mr = 254.29	Dx = 1.565 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1606 reflections
a = 13.6900 (13) Å	θ = 2.6–25.7°
b = 7.9611 (7) Å	µ = 0.49 mm−1
c = 9.9042 (10) Å	T = 298 K
V = 1079.43 (18) Å3	Block, colourless
Z = 4	0.41 × 0.39 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	952 independent reflections
Radiation source: fine-focus sealed tube	750 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→9
Tmin = 0.826, Tmax = 0.868	k = −7→9
3627 measured reflections	l = −11→11

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) = 0.103	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.4883P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
952 reflections	Δρmax = 0.17 e Å−3
74 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (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	0.32229 (4)	0.22302 (9)	0.54908 (7)	0.0562 (3)
O1	0.51977 (13)	0.2344 (2)	0.46510 (19)	0.0596 (5)
O2	0.30932 (12)	0.4503 (2)	0.35136 (19)	0.0651 (6)
C1	0.36270 (17)	0.3584 (3)	0.4132 (2)	0.0483 (6)
C3	0.5256 (2)	0.4169 (3)	0.2957 (3)	0.0621 (7)
H3	0.5075	0.4955	0.2308	0.074*
C2	0.46678 (16)	0.3429 (3)	0.3863 (2)	0.0478 (6)
C4	0.6204 (2)	0.3519 (4)	0.3184 (3)	0.0683 (8)
H4	0.6769	0.3799	0.2713	0.082*
C5	0.6134 (2)	0.2437 (4)	0.4195 (3)	0.0676 (8)
H5	0.6654	0.1823	0.4545	0.081*

	U11	U22	U33	U12	U13	U23
S1	0.0521 (4)	0.0597 (5)	0.0569 (5)	−0.0007 (3)	−0.0038 (3)	0.0117 (3)
O1	0.0531 (10)	0.0581 (11)	0.0676 (12)	0.0036 (8)	−0.0012 (8)	0.0087 (8)
O2	0.0632 (11)	0.0682 (12)	0.0640 (11)	0.0093 (9)	−0.0095 (9)	0.0170 (9)
C1	0.0548 (13)	0.0449 (13)	0.0452 (12)	−0.0018 (11)	−0.0073 (11)	−0.0034 (10)
C3	0.0696 (17)	0.0600 (15)	0.0566 (15)	−0.0131 (13)	−0.0038 (13)	0.0064 (12)
C2	0.0516 (13)	0.0438 (13)	0.0479 (13)	−0.0037 (11)	−0.0064 (11)	−0.0034 (10)
C4	0.0555 (16)	0.0747 (19)	0.0747 (19)	−0.0175 (14)	0.0093 (14)	−0.0103 (16)
C5	0.0477 (14)	0.0661 (17)	0.089 (2)	0.0021 (12)	−0.0003 (15)	−0.0066 (16)

S1—C1	1.811 (2)	C3—C2	1.341 (3)
S1—S1i	2.0254 (12)	C3—C4	1.416 (4)
O1—C5	1.361 (3)	C3—H3	0.9300
O1—C2	1.372 (3)	C4—C5	1.324 (4)
O2—C1	1.202 (3)	C4—H4	0.9300
C1—C2	1.455 (3)	C5—H5	0.9300
C1—S1—S1i	99.92 (8)	C3—C2—C1	132.3 (2)
C5—O1—C2	106.0 (2)	O1—C2—C1	117.8 (2)
O2—C1—C2	123.6 (2)	C5—C4—C3	106.9 (3)
O2—C1—S1	123.74 (19)	C5—C4—H4	126.5
C2—C1—S1	112.64 (17)	C3—C4—H4	126.5
C2—C3—C4	106.5 (2)	C4—C5—O1	110.8 (3)
C2—C3—H3	126.8	C4—C5—H5	124.6
C4—C3—H3	126.8	O1—C5—H5	124.6
C3—C2—O1	109.9 (2)
S1i—S1—C1—O2	1.2 (2)	S1—C1—C2—C3	179.3 (2)
S1i—S1—C1—C2	−178.38 (15)	O2—C1—C2—O1	179.5 (2)
C4—C3—C2—O1	0.0 (3)	S1—C1—C2—O1	−1.0 (3)
C4—C3—C2—C1	179.7 (2)	C2—C3—C4—C5	0.2 (3)
C5—O1—C2—C3	−0.2 (3)	C3—C4—C5—O1	−0.4 (3)
C5—O1—C2—C1	180.0 (2)	C2—O1—C5—C4	0.4 (3)
O2—C1—C2—C3	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ii	0.93	2.57	3.463 (3)	162.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.57	3.463 (3)	162

Symmetry code: (i) .