Bis(furan-2-ylcarbon-yl) diselenide.

The title mol-ecule, C(10)H(6)O(4)Se(2), lies on a twofold rotation axis. The Se-Se bond length of 2.305 (3) Å is similar to that in diphenyl diselenide [2.3066 (7) and 2.3073 (10) Å for the P and M isomers, respectively] and longer than that in 1,8-diseleno-naph-thalene [2.0879 (8) Å]. The mol-ecule adopts a gauche conformation with respect to the C=O groups.

Related literature

For background information and the structure of diphenyl diselenide, see: Fuller et al. (2010 ▶). For the structure of 1,8-diselenona­phthalene, see: Aucott et al. (2004 ▶).

Experimental

Crystal data

C10H6O4Se2

M = 348.07

Orthorhombic,

a = 9.615 (8) Å

b = 14.132 (14) Å

c = 3.991 (4) Å

V = 542.4 (9) Å3

Z = 2

Mo Kα radiation

μ = 6.81 mm−1

T = 125 K

0.18 × 0.12 × 0.03 mm

Data collection

Rigaku Saturn70 diffractometer

Absorption correction: multi-scan (REQAB; Rigaku, 1998 ▶) T min = 0.384, T max = 0.815

1716 measured reflections

895 independent reflections

873 reflections with F 2 > 2σ(F 2)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.131

S = 1.09

895 reflections

73 parameters

H-atom parameters constrained

Δρmax = 1.63 e Å−3

Δρmin = −2.07 e Å−3

Absolute structure: Flack (1983 ▶), 322 Friedel pairs

Flack parameter: 0.03 (5)

Data collection: CrystalClear (Rigaku, 2009 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102085X/lh5259sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102085X/lh5259Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102085X/lh5259Isup3.cml

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

C10H6O4Se2	F(000) = 332.00
Mr = 348.07	Dx = 2.131 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2 2ab	Cell parameters from 1723 reflections
a = 9.615 (8) Å	θ = 2.1–26.4°
b = 14.132 (14) Å	µ = 6.81 mm−1
c = 3.991 (4) Å	T = 125 K
V = 542.4 (9) Å3	Prism, colourless
Z = 2	0.18 × 0.12 × 0.03 mm

Rigaku Saturn70 diffractometer	873 reflections with F2 > 2σ(F2)
Detector resolution: 14.629 pixels mm-1	Rint = 0.057
ω scans	θmax = 25.0°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −9→11
Tmin = 0.384, Tmax = 0.815	k = −12→16
1716 measured reflections	l = −4→4
895 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0809P)2 + 2.1662P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
895 reflections	Δρmax = 1.63 e Å−3
73 parameters	Δρmin = −2.07 e Å−3
0 restraints	Absolute structure: Flack (1983), 322 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (5)
Secondary atom site location: difference Fourier map

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Se(1)	−0.03886 (8)	0.42284 (5)	−0.0428 (2)	0.0223 (4)
O(1)	0.2214 (7)	0.4163 (5)	0.2824 (18)	0.0307 (15)
O(3)	−0.0133 (6)	0.2267 (4)	0.1408 (17)	0.0245 (14)
C(1)	0.1221 (8)	0.3698 (6)	0.202 (3)	0.0220 (19)
C(2)	0.1076 (9)	0.2689 (6)	0.257 (3)	0.0221 (18)
C(4)	−0.0020 (10)	0.1321 (6)	0.230 (3)	0.029 (3)
C(5)	0.1174 (9)	0.1177 (6)	0.407 (3)	0.030 (2)
C(6)	0.1870 (9)	0.2064 (6)	0.420 (3)	0.029 (2)
H(4)	−0.0677	0.0843	0.1754	0.0354*
H(5)	0.1481	0.0598	0.5026	0.0358*
H(6)	0.2737	0.2190	0.5251	0.0346*

	U11	U22	U33	U12	U13	U23
Se(1)	0.0186 (5)	0.0255 (5)	0.0228 (5)	−0.0008 (4)	−0.0037 (4)	−0.0008 (4)
O(1)	0.019 (3)	0.029 (3)	0.044 (4)	−0.003 (3)	−0.004 (3)	−0.003 (4)
O(3)	0.017 (3)	0.023 (3)	0.033 (4)	−0.002 (3)	0.000 (3)	0.001 (3)
C(1)	0.011 (4)	0.039 (5)	0.016 (5)	0.002 (4)	−0.002 (4)	−0.006 (4)
C(2)	0.016 (4)	0.031 (4)	0.019 (5)	0.001 (4)	0.006 (4)	−0.008 (4)
C(4)	0.030 (5)	0.021 (4)	0.038 (6)	−0.004 (4)	0.004 (4)	−0.002 (4)
C(5)	0.024 (4)	0.025 (4)	0.041 (6)	0.007 (4)	0.003 (5)	0.006 (5)
C(6)	0.011 (4)	0.039 (5)	0.037 (6)	0.007 (4)	−0.007 (4)	−0.004 (5)

Se(1)—Se(1)i	2.305 (3)	C(2)—C(6)	1.337 (13)
Se(1)—C(1)	1.977 (9)	C(4)—C(5)	1.363 (14)
O(1)—C(1)	1.203 (11)	C(5)—C(6)	1.422 (12)
O(3)—C(2)	1.386 (11)	C(4)—H(4)	0.950
O(3)—C(4)	1.388 (10)	C(5)—H(5)	0.950
C(1)—C(2)	1.449 (12)	C(6)—H(6)	0.950
Se(1)i—Se(1)—C(1)	96.0 (3)	C(4)—C(5)—C(6)	106.5 (8)
C(2)—O(3)—C(4)	105.3 (7)	C(2)—C(6)—C(5)	107.2 (8)
Se(1)—C(1)—O(1)	123.1 (7)	O(3)—C(4)—H(4)	125.009
Se(1)—C(1)—C(2)	111.9 (6)	C(5)—C(4)—H(4)	125.002
O(1)—C(1)—C(2)	125.0 (8)	C(4)—C(5)—H(5)	126.736
O(3)—C(2)—C(1)	117.0 (8)	C(6)—C(5)—H(5)	126.737
O(3)—C(2)—C(6)	110.9 (8)	C(2)—C(6)—H(6)	126.404
C(1)—C(2)—C(6)	132.0 (9)	C(5)—C(6)—H(6)	126.395
O(3)—C(4)—C(5)	110.0 (8)
Se(1)i—Se(1)—C(1)—O(1)	−3.6 (7)	Se(1)—C(1)—C(2)—C(6)	−176.7 (7)
Se(1)i—Se(1)—C(1)—C(2)	178.9 (5)	O(1)—C(1)—C(2)—O(3)	−178.8 (8)
C(1)—Se(1)—Se(1)i—C(1)i	−120.5 (3)	O(1)—C(1)—C(2)—C(6)	5.7 (16)
C(2)—O(3)—C(4)—C(5)	2.9 (10)	O(3)—C(2)—C(6)—C(5)	1.3 (11)
C(4)—O(3)—C(2)—C(1)	−178.9 (7)	C(1)—C(2)—C(6)—C(5)	176.9 (9)
C(4)—O(3)—C(2)—C(6)	−2.5 (9)	O(3)—C(4)—C(5)—C(6)	−2.1 (11)
Se(1)—C(1)—C(2)—O(3)	−1.3 (10)	C(4)—C(5)—C(6)—C(2)	0.5 (11)