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organic compounds
The title compound, 1,1',8,8'-tetramethoxy-9,9'-bianthracene-10,10'(9H,9'H)-dione, C32H26O6, was obtained by the reduction of 1,8-dimethoxyanthraquinone with sodium borohydride and trifluoroacetic acid. In the anthrone dimers, the methoxy and carbonyl groups are attached to opposite sides of the anthracene rings. In the solid state, the molecule has a crystallographically imposed centre of symmetry located at the mid-point of the C-C bond linking the two anthracene systems.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028168/cv6407sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028168/cv6407Isup2.hkl |
CCDC reference: 238534
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.003 Å - R factor = 0.059
- wR factor = 0.115
- Data-to-parameter ratio = 13.8
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.003 ÅcheckCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1,1',8,8'-tetramethoxy-9,9'-bianthracene-10,10'(9H,9'H)-dione top
Crystal data top
| C32H26O6 | Z = 1 |
| Mr = 506.53 | F(000) = 266 |
| Triclinic, P1 | Dx = 1.387 Mg m−3 |
| Hall symbol: -P 1 | Melting point = 232–234 K |
| a = 7.585 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.443 (2) Å | Cell parameters from 523 reflections |
| c = 10.631 (3) Å | θ = 2.6–25.9° |
| α = 67.801 (4)° | µ = 0.10 mm−1 |
| β = 74.187 (4)° | T = 293 K |
| γ = 85.328 (5)° | Block, white |
| V = 606.3 (3) Å3 | 0.32 × 0.26 × 0.24 mm |
Data collection top
| Bruker SMART APEX CCD area-detector diffractometer | 2392 independent reflections |
| Radiation source: sealed tube | 1381 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.048 |
| φ and ω scans | θmax = 26.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −8→9 |
| Tmin = 0.97, Tmax = 0.98 | k = −9→10 |
| 4784 measured reflections | l = −11→13 |
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)] = 0.059 | H-atom parameters constrained |
| wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.038 |
| 2392 reflections | Δρmax = 0.19 e Å−3 |
| 173 parameters | Δρmin = −0.19 e Å−3 |
| 0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.027 (4) |
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 | Uiso*/Ueq | ||
| O1 | 0.3711 (3) | −0.1898 (2) | 0.71932 (18) | 0.0679 (5) | |
| O3 | 0.0207 (2) | 0.39447 (16) | 0.86225 (15) | 0.0494 (4) | |
| O4 | 0.17835 (19) | −0.02600 (18) | 1.23353 (13) | 0.0483 (4) | |
| C1 | 0.2722 (2) | −0.1191 (2) | 1.15674 (18) | 0.0371 (4) | |
| C2 | 0.3197 (3) | −0.1023 (2) | 0.7915 (2) | 0.0435 (5) | |
| C3 | −0.0320 (4) | 0.5676 (3) | 0.8113 (3) | 0.0654 (7) | |
| H3A | −0.0948 | 0.5997 | 0.8893 | 0.098* | |
| H3B | −0.1120 | 0.5804 | 0.7521 | 0.098* | |
| H3C | 0.0751 | 0.6398 | 0.7580 | 0.098* | |
| C4 | 0.3386 (2) | −0.1581 (2) | 0.93691 (19) | 0.0378 (4) | |
| C6 | 0.2385 (2) | −0.0762 (2) | 1.02504 (17) | 0.0320 (4) | |
| C7 | 0.3934 (3) | −0.2462 (2) | 1.2007 (2) | 0.0483 (5) | |
| H7A | 0.4124 | −0.2761 | 1.2896 | 0.058* | |
| C8 | 0.1539 (2) | 0.1518 (2) | 0.82388 (17) | 0.0328 (4) | |
| C10 | 0.1113 (2) | 0.3233 (2) | 0.7672 (2) | 0.0408 (4) | |
| C13 | 0.0951 (2) | 0.04904 (19) | 0.97971 (16) | 0.0295 (3) | |
| H13A | 0.0786 | 0.1279 | 1.0298 | 0.035* | |
| C14 | 0.4608 (3) | −0.2847 (2) | 0.9817 (2) | 0.0502 (5) | |
| H14A | 0.5254 | −0.3396 | 0.9226 | 0.060* | |
| C17 | 0.2534 (2) | 0.0732 (2) | 0.73307 (18) | 0.0393 (4) | |
| C18 | 0.4860 (3) | −0.3285 (3) | 1.1136 (3) | 0.0537 (5) | |
| H18A | 0.5664 | −0.4147 | 1.1443 | 0.064* | |
| C21 | 0.2608 (3) | 0.3308 (3) | 0.5345 (2) | 0.0640 (6) | |
| H21A | 0.2950 | 0.3910 | 0.4378 | 0.077* | |
| C23 | 0.1979 (4) | −0.0634 (4) | 1.3697 (2) | 0.0661 (7) | |
| H23A | 0.1239 | 0.0121 | 1.4100 | 0.099* | |
| H23B | 0.3241 | −0.0481 | 1.3645 | 0.099* | |
| H23C | 0.1591 | −0.1798 | 1.4275 | 0.099* | |
| C29 | 0.3045 (3) | 0.1649 (3) | 0.5872 (2) | 0.0512 (5) | |
| H29A | 0.3685 | 0.1113 | 0.5269 | 0.061* | |
| C31 | 0.1653 (3) | 0.4128 (3) | 0.6233 (2) | 0.0597 (6) | |
| H31A | 0.1378 | 0.5278 | 0.5860 | 0.072* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0795 (11) | 0.0700 (11) | 0.0599 (10) | 0.0020 (8) | 0.0029 (8) | −0.0449 (8) |
| O3 | 0.0604 (9) | 0.0333 (7) | 0.0491 (8) | 0.0056 (6) | −0.0112 (7) | −0.0122 (5) |
| O4 | 0.0558 (9) | 0.0574 (9) | 0.0365 (7) | 0.0072 (6) | −0.0156 (6) | −0.0216 (6) |
| C1 | 0.0350 (9) | 0.0354 (8) | 0.0408 (9) | −0.0068 (7) | −0.0086 (7) | −0.0135 (7) |
| C2 | 0.0380 (9) | 0.0494 (11) | 0.0452 (10) | −0.0081 (8) | 0.0032 (8) | −0.0277 (9) |
| C3 | 0.0799 (16) | 0.0333 (10) | 0.0829 (17) | 0.0113 (10) | −0.0308 (14) | −0.0169 (11) |
| C4 | 0.0297 (8) | 0.0343 (9) | 0.0467 (10) | −0.0037 (6) | −0.0029 (7) | −0.0162 (7) |
| C6 | 0.0299 (8) | 0.0284 (8) | 0.0338 (8) | −0.0059 (6) | −0.0030 (6) | −0.0097 (6) |
| C7 | 0.0500 (11) | 0.0404 (10) | 0.0544 (12) | −0.0033 (8) | −0.0268 (9) | −0.0076 (9) |
| C8 | 0.0291 (8) | 0.0365 (8) | 0.0306 (8) | −0.0082 (6) | −0.0036 (6) | −0.0112 (6) |
| C10 | 0.0371 (9) | 0.0388 (9) | 0.0430 (10) | −0.0049 (7) | −0.0111 (8) | −0.0098 (8) |
| C13 | 0.0329 (8) | 0.0279 (7) | 0.0279 (8) | −0.0001 (6) | −0.0068 (6) | −0.0112 (6) |
| C14 | 0.0401 (10) | 0.0360 (9) | 0.0758 (14) | 0.0026 (7) | −0.0092 (10) | −0.0266 (9) |
| C17 | 0.0313 (8) | 0.0521 (11) | 0.0342 (9) | −0.0105 (8) | −0.0026 (7) | −0.0174 (8) |
| C18 | 0.0457 (11) | 0.0370 (10) | 0.0813 (15) | 0.0085 (8) | −0.0297 (11) | −0.0175 (10) |
| C21 | 0.0675 (14) | 0.0776 (16) | 0.0296 (10) | −0.0153 (12) | −0.0089 (10) | 0.0000 (10) |
| C23 | 0.0670 (15) | 0.0970 (19) | 0.0402 (11) | 0.0031 (13) | −0.0174 (10) | −0.0298 (12) |
| C29 | 0.0465 (11) | 0.0751 (14) | 0.0320 (9) | −0.0120 (10) | −0.0041 (8) | −0.0215 (9) |
| C31 | 0.0663 (14) | 0.0504 (12) | 0.0466 (12) | −0.0052 (10) | −0.0184 (10) | 0.0031 (9) |
Geometric parameters (Å, º) top
| O1—C2 | 1.227 (2) | C8—C17 | 1.396 (2) |
| O3—C10 | 1.367 (2) | C8—C13 | 1.507 (2) |
| O3—C3 | 1.419 (2) | C10—C31 | 1.383 (3) |
| O4—C1 | 1.367 (2) | C13—C13i | 1.594 (3) |
| O4—C23 | 1.407 (2) | C13—H13A | 0.9800 |
| C1—C7 | 1.382 (3) | C14—C18 | 1.372 (3) |
| C1—C6 | 1.397 (2) | C14—H14A | 0.9300 |
| C2—C17 | 1.479 (3) | C17—C29 | 1.403 (3) |
| C2—C4 | 1.480 (3) | C18—H18A | 0.9300 |
| C3—H3A | 0.9600 | C21—C29 | 1.348 (3) |
| C3—H3B | 0.9600 | C21—C31 | 1.391 (4) |
| C3—H3C | 0.9600 | C21—H21A | 0.9300 |
| C4—C14 | 1.387 (3) | C23—H23A | 0.9600 |
| C4—C6 | 1.396 (2) | C23—H23B | 0.9600 |
| C6—C13 | 1.499 (2) | C23—H23C | 0.9600 |
| C7—C18 | 1.373 (3) | C29—H29A | 0.9300 |
| C7—H7A | 0.9300 | C31—H31A | 0.9300 |
| C8—C10 | 1.391 (3) | ||
| C10—O3—C3 | 118.67 (17) | C6—C13—C13i | 110.09 (15) |
| C1—O4—C23 | 119.26 (17) | C8—C13—C13i | 110.61 (15) |
| O4—C1—C7 | 124.64 (17) | C6—C13—H13A | 108.4 |
| O4—C1—C6 | 114.85 (15) | C8—C13—H13A | 108.4 |
| C7—C1—C6 | 120.50 (17) | C13i—C13—H13A | 108.4 |
| O1—C2—C17 | 121.71 (19) | C18—C14—C4 | 119.7 (2) |
| O1—C2—C4 | 122.1 (2) | C18—C14—H14A | 120.2 |
| C17—C2—C4 | 115.85 (15) | C4—C14—H14A | 120.2 |
| O3—C3—H3A | 109.5 | C8—C17—C29 | 120.30 (18) |
| O3—C3—H3B | 109.5 | C8—C17—C2 | 119.77 (16) |
| H3A—C3—H3B | 109.5 | C29—C17—C2 | 119.69 (18) |
| O3—C3—H3C | 109.5 | C14—C18—C7 | 120.58 (19) |
| H3A—C3—H3C | 109.5 | C14—C18—H18A | 119.7 |
| H3B—C3—H3C | 109.5 | C7—C18—H18A | 119.7 |
| C14—C4—C6 | 120.91 (18) | C29—C21—C31 | 120.75 (19) |
| C14—C4—C2 | 119.94 (18) | C29—C21—H21A | 119.6 |
| C6—C4—C2 | 119.08 (16) | C31—C21—H21A | 119.6 |
| C4—C6—C1 | 118.03 (16) | O4—C23—H23A | 109.5 |
| C4—C6—C13 | 120.09 (15) | O4—C23—H23B | 109.5 |
| C1—C6—C13 | 121.84 (15) | H23A—C23—H23B | 109.5 |
| C1—C7—C18 | 120.22 (19) | O4—C23—H23C | 109.5 |
| C1—C7—H7A | 119.9 | H23A—C23—H23C | 109.5 |
| C18—C7—H7A | 119.9 | H23B—C23—H23C | 109.5 |
| C10—C8—C17 | 118.72 (16) | C21—C29—C17 | 119.9 (2) |
| C10—C8—C13 | 121.95 (15) | C21—C29—H29A | 120.0 |
| C17—C8—C13 | 119.33 (15) | C17—C29—H29A | 120.0 |
| O3—C10—C31 | 123.91 (19) | C21—C31—C10 | 120.0 (2) |
| O3—C10—C8 | 115.76 (16) | C21—C31—H31A | 120.0 |
| C31—C10—C8 | 120.29 (19) | C10—C31—H31A | 120.0 |
| C6—C13—C8 | 110.88 (13) |
| Symmetry code: (i) −x, −y, −z+2. |
