(Furan-2-yl)[(furan-2-yl)carbonyl­disul­fanyl]methanone

Abstract

The mol­ecule of the title compound, C₁₀H₆O₄S₂, has crystallographically imposed twofold symmetry. The dihedral angle formed by the furan rings is 80.90 (8)°. In the crystal, mol­ecules 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 _r = 254.29

• Orthorhombic,

• a = 13.6900 (13) Å

• b = 7.9611 (7) Å

• c = 9.9042 (10) Å

• V = 1079.43 (18) ų

• 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

• Δρ_max = 0.17 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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

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) .

supplementary crystallographic information

Comment

The title compound is a dimeric form of furan-2-carbothioic-S-acid, which has a broad spectrum of applications in the fields of medicinal chemistry (Deshpande et al., 2004) and food additives (Stoll et al., 1967). As a contribution in this field, we report here the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The molecule has crystallographically imposed twofold axis. The furan rings are oriented to form a dihedral angle of 80.90 (8)°. In the crystal structure (Fig. 2), molecules are linked by weak intermolecular C—H···O hydrogen bonds (Table 1) forming chains parallel to the a axis.

Experimental

To a solution of furan-2-carboxylic acid (11.2 g, 0.10 mol) in dioxane, NaHS (11.2 g, 0.20 mol) was added. The mixture was stirred at 50°C for 4 h. Then mixture was concentrated and purified by crystallization from ethyl acetate. Colourless crystals suitable for X-ray analysis were obtained on slow evaporation of the solvent.

Refinement

All H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93–0.96 Å and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C) for methyl H atoms.

Figures

Fig. 1.

The molecular structure of the title compound, with 50% probability displacement ellipsoids.

Fig. 2.

Crystal packing of the title compound viewed along the a axis. INtermolecular hydrogen bonds are shown as dashed lines.

Crystal data

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

Data collection

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

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)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

Symmetry codes: (i) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, °)

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

Symmetry codes: (ii) x+1/2, −y+1, −z+1/2.