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

Wang, Q.; Shu, Y.; Hou, X.

doi:10.1107/S160053681104356X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3055

doi:10.1107/S160053681104356X

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

Qian Wang,^a ^* Youqin Shu ^b and Xuehui Hou ^b

^aRadio and TV University of Henan, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: muzhi527@163.com

(Received 10 October 2011; accepted 20 October 2011; online 29 October 2011)

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, P c c n
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[F² > 2σ(F²)] = 0.032
wR(F²) = 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

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) $[x+{\script{1\over 2}}, -y+1, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681104356X/rz2653sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681104356X/rz2653Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	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.

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

Crystal data top

C₁₀H₆O₄S₂	F(000) = 520
M_r = 254.29	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0569P)² + 0.4883P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
952 reflections	Δρ_max = 0.17 e Å⁻³
74 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₆O₄S₂	V = 1079.43 (18) Å³
M_r = 254.29	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 13.6900 (13) Å	µ = 0.49 mm⁻¹
b = 7.9611 (7) Å	T = 298 K
c = 9.9042 (10) Å	0.41 × 0.39 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	952 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	750 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.868	R_int = 0.028
3627 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
952 reflections	Δρ_min = −0.23 e Å⁻³
74 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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 code: (i) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₁₀H₆O₄S₂
M_r	254.29
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	298
a, b, c (Å)	13.6900 (13), 7.9611 (7), 9.9042 (10)
V (Å³)	1079.43 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.41 × 0.39 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.826, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	3627, 952, 750
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.103, 1.00
No. of reflections	952
No. of parameters	74
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.57	3.463 (3)	161.9

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

Acknowledgements

The authors gratefully acknowledge financial support from the Natural Scientific Research Programs of Henan Province (grant No. 2008138) and the Young Teachers Aid Programs of the College of Henan Province (grant No. 2009B150011).

References

Deshpande, P., Luthra, P. & Sathe, P. (2004). US Patent 6800756. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Stoll, M., Winter, M., Gautschi, F., Flament, I. & Willhalm, B. (1967). Helv. Chim. Acta, 50, 628–694. CrossRef CAS PubMed Web of Science Google Scholar