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accessRedermination of 9,9′-bianthracene-10,10′(9H,9′H)-dione
aDepartment of Chemistry and Chemical Engineering, Qiannan Normal College for Nationalities, Duyun, Guizhou 558000, People's Republic of China, and bDepartment of Chemistry and Biology, Qinzhou University, Qinzhou, Guangxi 535000, People's Republic of China
*Correspondence e-mail: ljmmarise@163.com
The of the title compound, C28H18O2, was originally determined by Ehrenberg [(1967![[Ehrenberg, M. (1967). Acta Cryst. 22, 482-487.]](../../../../../../logos/arrows/e_arr.gif "Ehrenberg, M. (1967). Acta Cryst. 22, 482-487.")
). Acta Cryst. 22, 482–487] using intensity data obtained from Weissenberg photographs. The current determination provides a crystal and molecular structure with a significantly higher precision and presents standard uncertainties on geometric parameters which are not available from the original work. The molecule lies on a crystallographic twofold rotation axis which bisects the C—C bond [1.603 (3) Å] which joins the two anthracen-9(10H)-one units.
Related literature
For general background, see: Li et al. (2002); Shi et al. (2004); Müller et al. (1996, 1998, 2001); Prinz, Burgemeister & Wiegrebe (1996); Prinz, Wiegrebe & Müller (1996). For related structures, see: Ehrenberg (1967).
![[Scheme 1]](lh2689scheme1.gif)
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2003); cell SAINT (Bruker, 2003); 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
contains datablocks global, I. DOI: 10.1107/S1600536808028833/lh2689sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808028833/lh2689Isup2.hkl
Reagents and solvents used were of commercially available quality. The title complex (I) was synthesized according to the method of Shi et al. (2004) and Li et al. (2002). CF3COOH (40 ml) was added dropwise with stirring to a solution of anthracene-9,10-dione (5.0 mmol) in 15 ml of anhydrous CH2Cl2. The mixture was then placed in an ice bath and NaBH4 (0.95 g, 25 mmol) was added in portions. The resulting mixture was stirred for 24 h at room temperature. The reaction mixture was poured into 200 ml ice-water. The organic layer was extracted with CH2Cl2, dried over Na2SO4 and evaporated in vacuo. The crude product was recrystallized from toluene twice to give the main product 9,9'-bianthracene-10,10'(9H,9'H)-dione.
H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2 times Ueq(C).
Data collection: SMART (Bruker, 2003); cell SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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).
![[Figure 1]](./lh2689fig1thm.gif) | Fig. 1. The molecular structure with displacement ellipsoids at the 30% probability level [symmetry code: (A) -x+2, y, -z+1/2]. |
| C28H18O2 | F(000) = 808 |
| Mr = 386.42 | Dx = 1.363 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 1069 reflections |
| a = 22.295 (4) Å | θ = 2.9–24.7° |
| b = 7.7297 (12) Å | µ = 0.09 mm−1 |
| c = 13.643 (2) Å | T = 273 K |
| β = 126.768 (2)° | Block, yellow |
| V = 1883.4 (5) Å3 | 0.22 × 0.18 × 0.15 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 1669 independent reflections |
| Radiation source: fine-focus sealed tube | 1172 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.025 |
| ϕ and ω scans | θmax = 25.1°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→26 |
| Tmin = 0.982, Tmax = 0.987 | k = −9→9 |
| 4785 measured reflections | l = −16→8 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.106 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4019P] where P = (Fo2 + 2Fc2)/3 |
| 1669 reflections | (Δ/σ)max = 0.001 |
| 136 parameters | Δρmax = 0.12 e Å−3 |
| 0 restraints | Δρmin = −0.17 e Å−3 |
| C28H18O2 | V = 1883.4 (5) Å3 |
| Mr = 386.42 | Z = 4 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 22.295 (4) Å | µ = 0.09 mm−1 |
| b = 7.7297 (12) Å | T = 273 K |
| c = 13.643 (2) Å | 0.22 × 0.18 × 0.15 mm |
| β = 126.768 (2)° |
| Bruker SMART CCD diffractometer | 1669 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1172 reflections with I > 2σ(I) |
| Tmin = 0.982, Tmax = 0.987 | Rint = 0.025 |
| 4785 measured reflections |
| R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
| wR(F2) = 0.106 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.12 e Å−3 |
| 1669 reflections | Δρmin = −0.17 e Å−3 |
| 136 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.86707 (8) | −0.25682 (16) | 0.29866 (15) | 0.0855 (5) | |
| C1 | 0.90675 (10) | −0.1382 (2) | 0.30813 (16) | 0.0503 (4) | |
| C2 | 0.98793 (9) | −0.16248 (19) | 0.37296 (14) | 0.0423 (4) | |
| C3 | 1.02019 (10) | −0.3196 (2) | 0.43139 (15) | 0.0546 (5) | |
| H3 | 0.9900 | −0.4083 | 0.4254 | 0.066* | |
| C4 | 1.09595 (11) | −0.3451 (2) | 0.49762 (16) | 0.0616 (5) | |
| H4 | 1.1169 | −0.4513 | 0.5346 | 0.074* | |
| C5 | 1.14056 (10) | −0.2121 (2) | 0.50886 (15) | 0.0572 (5) | |
| H5 | 1.1921 | −0.2277 | 0.5553 | 0.069* | |
| C6 | 1.10969 (8) | −0.0560 (2) | 0.45207 (13) | 0.0457 (4) | |
| H6 | 1.1408 | 0.0332 | 0.4616 | 0.055* | |
| C7 | 1.03286 (8) | −0.02957 (19) | 0.38070 (13) | 0.0379 (4) | |
| C8 | 0.99831 (8) | 0.13334 (18) | 0.30704 (13) | 0.0370 (4) | |
| H8 | 1.0288 | 0.2306 | 0.3599 | 0.044* | |
| C9 | 0.91944 (8) | 0.16565 (19) | 0.26300 (13) | 0.0393 (4) | |
| C10 | 0.88717 (9) | 0.3276 (2) | 0.21705 (15) | 0.0491 (4) | |
| H10 | 0.9158 | 0.4170 | 0.2191 | 0.059* | |
| C11 | 0.81329 (10) | 0.3570 (2) | 0.16860 (16) | 0.0591 (5) | |
| H11 | 0.7926 | 0.4660 | 0.1382 | 0.071* | |
| C12 | 0.76987 (10) | 0.2268 (3) | 0.16480 (16) | 0.0589 (5) | |
| H12 | 0.7199 | 0.2471 | 0.1314 | 0.071* | |
| C13 | 0.80076 (9) | 0.0673 (2) | 0.21051 (15) | 0.0535 (5) | |
| H13 | 0.7716 | −0.0207 | 0.2086 | 0.064* | |
| C14 | 0.87527 (8) | 0.0352 (2) | 0.25983 (14) | 0.0426 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0740 (10) | 0.0554 (8) | 0.1455 (14) | −0.0116 (7) | 0.0756 (10) | 0.0060 (8) |
| C1 | 0.0571 (11) | 0.0449 (10) | 0.0648 (11) | −0.0082 (8) | 0.0450 (9) | −0.0049 (8) |
| C2 | 0.0527 (10) | 0.0383 (9) | 0.0436 (9) | −0.0017 (7) | 0.0331 (8) | −0.0012 (7) |
| C3 | 0.0705 (13) | 0.0430 (10) | 0.0553 (11) | −0.0008 (9) | 0.0403 (10) | 0.0061 (8) |
| C4 | 0.0735 (14) | 0.0512 (11) | 0.0535 (11) | 0.0147 (10) | 0.0344 (10) | 0.0138 (9) |
| C5 | 0.0496 (11) | 0.0651 (12) | 0.0458 (10) | 0.0120 (9) | 0.0227 (8) | 0.0111 (9) |
| C6 | 0.0446 (10) | 0.0512 (10) | 0.0392 (9) | 0.0003 (8) | 0.0240 (8) | 0.0024 (8) |
| C7 | 0.0447 (9) | 0.0388 (9) | 0.0327 (8) | 0.0000 (7) | 0.0245 (7) | −0.0022 (7) |
| C8 | 0.0394 (9) | 0.0327 (8) | 0.0406 (9) | −0.0041 (6) | 0.0247 (7) | −0.0050 (7) |
| C9 | 0.0427 (9) | 0.0384 (8) | 0.0414 (9) | −0.0003 (7) | 0.0276 (7) | −0.0074 (7) |
| C10 | 0.0502 (11) | 0.0421 (9) | 0.0571 (11) | 0.0027 (8) | 0.0333 (9) | −0.0037 (8) |
| C11 | 0.0568 (12) | 0.0566 (11) | 0.0606 (12) | 0.0179 (9) | 0.0333 (9) | 0.0026 (9) |
| C12 | 0.0414 (10) | 0.0781 (14) | 0.0570 (11) | 0.0074 (9) | 0.0293 (9) | −0.0030 (10) |
| C13 | 0.0464 (10) | 0.0645 (12) | 0.0558 (11) | −0.0060 (9) | 0.0339 (9) | −0.0081 (9) |
| C14 | 0.0429 (9) | 0.0472 (9) | 0.0451 (9) | −0.0033 (7) | 0.0303 (8) | −0.0070 (7) |
| O1—C1 | 1.2260 (18) | C8—C9 | 1.500 (2) |
| C1—C14 | 1.473 (2) | C8—C8i | 1.603 (3) |
| C1—C2 | 1.475 (2) | C8—H8 | 0.9800 |
| C2—C3 | 1.393 (2) | C9—C10 | 1.392 (2) |
| C2—C7 | 1.394 (2) | C9—C14 | 1.392 (2) |
| C3—C4 | 1.372 (2) | C10—C11 | 1.378 (2) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.374 (2) | C11—C12 | 1.376 (3) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.375 (2) | C12—C13 | 1.367 (2) |
| C5—H5 | 0.9300 | C12—H12 | 0.9300 |
| C6—C7 | 1.388 (2) | C13—C14 | 1.391 (2) |
| C6—H6 | 0.9300 | C13—H13 | 0.9300 |
| C7—C8 | 1.504 (2) | ||
| O1—C1—C14 | 120.85 (16) | C7—C8—C8i | 110.23 (10) |
| O1—C1—C2 | 121.12 (16) | C9—C8—H8 | 107.4 |
| C14—C1—C2 | 117.97 (14) | C7—C8—H8 | 107.4 |
| C3—C2—C7 | 119.84 (16) | C8i—C8—H8 | 107.4 |
| C3—C2—C1 | 118.80 (15) | C10—C9—C14 | 118.18 (15) |
| C7—C2—C1 | 121.31 (14) | C10—C9—C8 | 119.74 (14) |
| C4—C3—C2 | 120.84 (17) | C14—C9—C8 | 121.98 (13) |
| C4—C3—H3 | 119.6 | C11—C10—C9 | 120.78 (16) |
| C2—C3—H3 | 119.6 | C11—C10—H10 | 119.6 |
| C3—C4—C5 | 119.33 (17) | C9—C10—H10 | 119.6 |
| C3—C4—H4 | 120.3 | C12—C11—C10 | 120.62 (17) |
| C5—C4—H4 | 120.3 | C12—C11—H11 | 119.7 |
| C4—C5—C6 | 120.59 (17) | C10—C11—H11 | 119.7 |
| C4—C5—H5 | 119.7 | C13—C12—C11 | 119.45 (17) |
| C6—C5—H5 | 119.7 | C13—C12—H12 | 120.3 |
| C5—C6—C7 | 121.03 (16) | C11—C12—H12 | 120.3 |
| C5—C6—H6 | 119.5 | C12—C13—C14 | 120.73 (17) |
| C7—C6—H6 | 119.5 | C12—C13—H13 | 119.6 |
| C6—C7—C2 | 118.28 (14) | C14—C13—H13 | 119.6 |
| C6—C7—C8 | 121.01 (14) | C13—C14—C9 | 120.23 (15) |
| C2—C7—C8 | 120.59 (14) | C13—C14—C1 | 119.33 (15) |
| C9—C8—C7 | 114.57 (13) | C9—C14—C1 | 120.43 (14) |
| C9—C8—C8i | 109.65 (14) | ||
| O1—C1—C2—C3 | −4.6 (2) | C7—C8—C9—C10 | 166.38 (13) |
| C14—C1—C2—C3 | 172.72 (15) | C8i—C8—C9—C10 | −69.07 (14) |
| O1—C1—C2—C7 | 178.00 (16) | C7—C8—C9—C14 | −17.4 (2) |
| C14—C1—C2—C7 | −4.7 (2) | C8i—C8—C9—C14 | 107.14 (13) |
| C7—C2—C3—C4 | 0.6 (2) | C14—C9—C10—C11 | −0.7 (2) |
| C1—C2—C3—C4 | −176.90 (15) | C8—C9—C10—C11 | 175.66 (14) |
| C2—C3—C4—C5 | 1.7 (3) | C9—C10—C11—C12 | 0.1 (3) |
| C3—C4—C5—C6 | −1.5 (3) | C10—C11—C12—C13 | 0.5 (3) |
| C4—C5—C6—C7 | −1.0 (3) | C11—C12—C13—C14 | −0.5 (3) |
| C5—C6—C7—C2 | 3.2 (2) | C12—C13—C14—C9 | −0.1 (2) |
| C5—C6—C7—C8 | −172.91 (15) | C12—C13—C14—C1 | −179.91 (16) |
| C3—C2—C7—C6 | −3.0 (2) | C10—C9—C14—C13 | 0.7 (2) |
| C1—C2—C7—C6 | 174.42 (14) | C8—C9—C14—C13 | −175.56 (13) |
| C3—C2—C7—C8 | 173.14 (14) | C10—C9—C14—C1 | −179.51 (14) |
| C1—C2—C7—C8 | −9.5 (2) | C8—C9—C14—C1 | 4.2 (2) |
| C6—C7—C8—C9 | −164.09 (13) | O1—C1—C14—C13 | 4.5 (3) |
| C2—C7—C8—C9 | 19.91 (19) | C2—C1—C14—C13 | −172.84 (14) |
| C6—C7—C8—C8i | 71.68 (18) | O1—C1—C14—C9 | −175.31 (16) |
| C2—C7—C8—C8i | −104.32 (17) | C2—C1—C14—C9 | 7.4 (2) |
| Symmetry code: (i) −x+2, y, −z+1/2. |
Experimental details
| Crystal data | |
| Chemical formula | C28H18O2 |
| Mr | 386.42 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 273 |
| a, b, c (Å) | 22.295 (4), 7.7297 (12), 13.643 (2) |
| β (°) | 126.768 (2) |
| V (Å3) | 1883.4 (5) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.09 |
| Crystal size (mm) | 0.22 × 0.18 × 0.15 |
| Data collection | |
| Diffractometer | Bruker SMART CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.982, 0.987 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 4785, 1669, 1172 |
| Rint | 0.025 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.106, 1.03 |
| No. of reflections | 1669 |
| No. of parameters | 136 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.12, −0.17 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by a key grant from Qiannan Normal College for Nationalities Foundation of Guizhou Province (grant No. 2007Z15) and the Qinzhou University Foundation of Guangxi Zhuang Autonomous Region of the People's Republic of China (grant No. 2008XJKY-10B).
References
Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ehrenberg, M. (1967). Acta Cryst. 22, 482–487. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Li, P. C., Wang, T. S., Lee, G. H., Liu, Y. H., Wang, Y., Chen, C. T. & Chao, I. (2002). J. Org. Chem. 67, 8002–8009. Web of Science CSD CrossRef PubMed CAS Google Scholar
Müller, K., Altmann, R. & Prinz, H. (1998). Eur. J. Med. Chem. 33, 209–214. Web of Science CrossRef CAS Google Scholar
Müller, K., Breu, K. & Reindl, H. (2001). Eur. J. Med. Chem. 36, 179–184. Web of Science CrossRef PubMed CAS Google Scholar
Müller, K., Huang, H. S. & Wiegrebe, W. (1996). J. Med. Chem. 39, 3132–3128. PubMed Web of Science Google Scholar
Prinz, H., Burgemeister, T. & Wiegrebe, W. (1996). J. Org. Chem. 61, 2857–2860. CrossRef PubMed CAS Web of Science Google Scholar
Prinz, H., Wiegrebe, W. & Müller, K. (1996). J. Org. Chem. 61, 2853–2856. CrossRef PubMed CAS Web of Science 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
Shi, Z.-W., Li, Y.-Z., Li, Y., Lu, G.-Y. & Liu, S.-H. (2004). Acta Cryst. E60, o2275–o2277. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Synthesis of anthracenone derivatives have attracted great interest due to their interesting biological activities (Müller et al., 1996, 1998, 2001; Prinz, Burgemeister & Wiegrebe, 1996; Prinz, Wiegrebe & Müller, 1996). Herein, we present a redetermination of the crystal structure of the title compound (I) which was originally refined in the non-conventional space group setting I2/a with unit cell parameters; a = 13.68 (4), b = 7.751 (3), c = 17.92 (4), β = 91.1 (3) (Ehrenberg, 1967). The current structure is of significantly higher precision than the orginal determination which was refined using intensity data obtained from Weissenberg photographs. The molecular structure of (I) is shown in Fig. 1. The molecule consists of two anthracen-9(10H)-one moieties linked together by a C—C [1.603 (3) Å] bond. A crystallographic twofold rotation axis bisects this bond.