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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 4;67(Pt 7):o1586. doi: 10.1107/S160053681102085X

Bis(furan-2-ylcarbon­yl) diselenide

David B Cordes a, Guoxiong Hua a, Alexandra M Z Slawin a,*, J Derek Woollins a
PMCID: PMC3152040  PMID: 21836995

Abstract

The title mol­ecule, C10H6O4Se2, 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-diseleno­naph­thalene [2.0879 (8) Å]. The mol­ecule 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 ▶).graphic file with name e-67-o1586-scheme1.jpg

Experimental

Crystal data

  • C10H6O4Se2

  • M r = 348.07

  • Orthorhombic, Inline graphic

  • 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.

Supplementary Material

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

e-67-o1586-sup1.cif (11.8KB, cif)

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

e-67-o1586-Isup2.hkl (44.5KB, hkl)

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

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

supplementary crystallographic information

Comment

We have recently reported (Fuller et al., 2010) on the crystallization of Ph-Se-Se-Ph as one isomer. We were interested to see if this homocrystallization occurs for other diselenides. In the title compound, we observe a single isomer in the crystal rather than a mixture of P and M isomers. The Se—Se bond length of 2.305 (3)Å is similar to that in diphenyldiselenide (2.3066 (7) and 2.3073 (10) Å for P and M isomers, respectively, Fuller et al., 2010) and longer than that in 1,8-diselenonaphthalene (2.0879 (8)Å, Aucott et al., 2004).

Experimental

N-(furan-2-carbonyl)furan-2-carboxamide (0.205 g, 1.0 mmol) and Woollins reagent (0.54 g, 1.0 mmol) in 20 ml of dry toluene was refluxed for 10 h. Upon cooling to room temperature and removing toluene in vacuum the residue was purified by silica gel column (eluented by 1: 1 hexane / dichloromethane) to give 0.213 g of 1 as a pale yellow solid in 61% yield. Crystals for X-ray data collection were obtained by diffusion of hexane into a dichloromethane solution of (I). 1H NMR (CD2Cl2, δ), 8.01 (d, J(H,H) = 8.2 Hz, 2H), 7.54 (d, J(H,H) = 8.2 Hz, 2H), 6.90–6.84 (m, 2H) p.p.m.. 13C NMR (CD2Cl2, δ), 179.1 (C=O), 154.1, 148.1, 125.0, 117.1 p.p.m.. 77Se NMR (CD2Cl2, δ), 624.5 p.p.m.. MS (CI+, m/z), 351 [M+H]+.

Refinement

The partial completeness of ca 95% data may affect the precision of the structure. All H atoms were included in calculated positions with C—H = 0.95Å and were refined as riding atoms with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level (symmetry code: (A) -x, -y+1, z).

Crystal data

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
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Data collection

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
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Refinement

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
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Special details

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).
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Symmetry codes: (i) −x, −y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5259).

References

  1. Aucott, S. M., Milton, H. L., Robertson, S. D., Slawin, A. M. Z. & Woollins, J. D. (2004). Heteroat. Chem. 15, 530–542.
  2. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  3. Fuller, A. L., Scott-Hayward, L. A. S., Li, Y., Bühl, M., Slawin, A. M. Z. & Woollins, J. D. (2010). J. Am. Chem. Soc. 132, 5799–5802. [DOI] [PubMed]
  4. Rigaku (1998). REQAB Rigaku Corporation, Tokyo, Japan.
  5. Rigaku (2009). CrystalClear Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  6. Rigaku (2010). CrystalStructure Rigaku Corporation, Tokyo, Japan.
  7. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-67-o1586-sup1.cif (11.8KB, cif)

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

e-67-o1586-Isup2.hkl (44.5KB, hkl)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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