 | Acta Crystallographica Section E Acta Crystallographica Section E CRYSTALLOGRAPHIC COMMUNICATIONS |
journal menu
organic compounds
| CRYSTALLOGRAPHIC COMMUNICATIONS |
accessBis(furan-2-ylcarbonyl) diselenide
aSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: amzs@st-and.ac.uk
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![[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.]](../../../../../../logos/arrows/e_arr.gif "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.")
). For the structure of 1,8-diselenonaphthalene, see: Aucott et al. (2004).
![[Scheme 1]](lh5259scheme1.gif)
Experimental
Crystal data
|
Data collection: CrystalClear (Rigaku, 2009); cell 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.
Supporting information
contains datablocks global, I. DOI: 10.1107/S160053681102085X/lh5259sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S160053681102085X/lh5259Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681102085X/lh5259Isup3.cml
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]+.
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).
Data collection: CrystalClear (Rigaku, 2009); cell CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure 4.0 (Rigaku, 2010); software used to prepare material for publication: CrystalStructure 4.0 (Rigaku, 2010).
![[Figure 1]](./lh5259fig1thm.gif) | Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level (symmetry code: (A) -x, -y+1, z). |
| 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 | Absolute structure parameter: 0.03 (5) |
| Secondary atom site location: difference Fourier map |
| C10H6O4Se2 | V = 542.4 (9) Å3 |
| Mr = 348.07 | Z = 2 |
| Orthorhombic, P21212 | Mo Kα radiation |
| a = 9.615 (8) Å | µ = 6.81 mm−1 |
| b = 14.132 (14) Å | T = 125 K |
| c = 3.991 (4) Å | 0.18 × 0.12 × 0.03 mm |
| Rigaku Saturn70 diffractometer | 895 independent reflections |
| Absorption correction: multi-scan (REQAB; Rigaku, 1998) | 873 reflections with F2 > 2σ(F2) |
| Tmin = 0.384, Tmax = 0.815 | Rint = 0.057 |
| 1716 measured reflections |
| R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
| wR(F2) = 0.131 | Δρmax = 1.63 e Å−3 |
| S = 1.09 | Δρmin = −2.07 e Å−3 |
| 895 reflections | Absolute structure: Flack (1983), 322 Friedel pairs |
| 73 parameters | Absolute structure parameter: 0.03 (5) |
| 0 restraints |
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) |
| Symmetry code: (i) −x, −y+1, z. |
Experimental details
| Crystal data | |
| Chemical formula | C10H6O4Se2 |
| Mr | 348.07 |
| Crystal system, space group | Orthorhombic, P21212 |
| Temperature (K) | 125 |
| a, b, c (Å) | 9.615 (8), 14.132 (14), 3.991 (4) |
| V (Å3) | 542.4 (9) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 6.81 |
| Crystal size (mm) | 0.18 × 0.12 × 0.03 |
| Data collection | |
| Diffractometer | Rigaku Saturn70 diffractometer |
| Absorption correction | Multi-scan (REQAB; Rigaku, 1998) |
| Tmin, Tmax | 0.384, 0.815 |
| No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 1716, 895, 873 |
| Rint | 0.057 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.131, 1.09 |
| No. of reflections | 895 |
| No. of parameters | 73 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.63, −2.07 |
| Absolute structure | Flack (1983), 322 Friedel pairs |
| Absolute structure parameter | 0.03 (5) |
Computer programs: CrystalClear (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure 4.0 (Rigaku, 2010).
References
Aucott, S. M., Milton, H. L., Robertson, S. D., Slawin, A. M. Z. & Woollins, J. D. (2004). Heteroat. Chem. 15, 530–542. CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2009). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
| CRYSTALLOGRAPHIC COMMUNICATIONS |
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).