Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104015951/fr1490sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104015951/fr1490IIIsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104015951/fr1490IVsup3.hkl |
CCDC references: 251319; 251320
To a solution (1.0 M) of (I) in benzene was added one equivalent of diphenylisobenzofuran, (II). The reaction mixture was shielded from laboratory light and heated at the reflux temperature. When the reaction was complete (8.5 h for n=1 and 6 h for n=2), the volatile constituents were removed under reduced pressure, and the residue was purified by column chromatography on silica gel. The reaction with n=1 resulted in the isolation of two adducts in a 78:22 ratio, with (III) as the minor component. When the co-reactant was (I) with n=2, compound (IV) was formed exclusively. Compounds (III) and (IV) were crystallized by dissolving each in a minimal amount of ethyl acetate, and then adding hexane until the solution turned slightly cloudy. The melting points of (III) and (IV) are 406–408 K and 411–413 K, respectively.
The H atoms for both structures were placed at calculated positions and treated using using a riding model, with Uiso(H) values of 1.2Ueq(C). The C—H distances ranged from 0.95 to 1.00 Å, depending on the type of C atom. PLATON (Spek, 2003) was used to calculated some geometric parameters.
For both compounds, data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: reference?.
Fig. 1. The structure of (III), drawn with 50% probability displacement ellipsoids. | |
Fig. 2. The structure of (IV), drawn with 50% probability displacement ellipsoids. |
C27H20O3 | F(000) = 824 |
Mr = 392.43 | Dx = 1.337 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4662 reflections |
a = 10.322 (1) Å | θ = 2.0–27.5° |
b = 14.239 (1) Å | µ = 0.09 mm−1 |
c = 14.138 (1) Å | T = 200 K |
β = 110.254 (4)° | Chunk, pale yellow |
V = 1949.3 (3) Å3 | 0.35 × 0.31 × 0.19 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3424 reflections with I > 2σ(I) |
Radiation source: fine–focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
ϕ and ω scans | h = −13→13 |
41110 measured reflections | k = −18→18 |
4474 independent reflections | l = −18→18 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.4364P] where P = (Fo2 + 2Fc2)/3 |
4474 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C27H20O3 | V = 1949.3 (3) Å3 |
Mr = 392.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.322 (1) Å | µ = 0.09 mm−1 |
b = 14.239 (1) Å | T = 200 K |
c = 14.138 (1) Å | 0.35 × 0.31 × 0.19 mm |
β = 110.254 (4)° |
Nonius KappaCCD diffractometer | 3424 reflections with I > 2σ(I) |
41110 measured reflections | Rint = 0.036 |
4474 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
4474 reflections | Δρmin = −0.23 e Å−3 |
271 parameters |
Experimental. All work was done at 200 K using an Oxford Cryosystems Cryostream Cooler. A quadrant of reciprocal space was measured with a redundancy factor of 4.2, which means that 90% of the data was measured at least 4.2 times. A combination of phi and omega scans with a frame width of 1.0° was used for data collection. Data integration was done with DENZO (Otwinowski & Minor, 1997). Scaling and merging of the data was done with SCALEPACK (Otwinowski & Minor, 1997). |
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 | 0.78521 (9) | 0.91350 (6) | 0.79337 (6) | 0.0249 (2) | |
O2 | 0.92312 (12) | 0.92687 (9) | 0.53963 (9) | 0.0499 (3) | |
O3 | 0.38837 (11) | 0.86833 (8) | 0.51460 (9) | 0.0464 (3) | |
C1 | 0.87191 (13) | 0.91525 (9) | 0.73112 (9) | 0.0245 (3) | |
C2 | 0.88851 (13) | 0.81059 (9) | 0.71718 (9) | 0.0244 (3) | |
C3 | 0.99011 (14) | 0.75818 (10) | 0.69891 (10) | 0.0293 (3) | |
H3 | 1.0731 | 0.7865 | 0.6983 | 0.035* | |
C4 | 0.96651 (15) | 0.66200 (10) | 0.68136 (10) | 0.0328 (3) | |
H4 | 1.0353 | 0.6240 | 0.6698 | 0.039* | |
C5 | 0.84444 (15) | 0.62133 (10) | 0.68061 (10) | 0.0328 (3) | |
H5 | 0.8310 | 0.5558 | 0.6690 | 0.039* | |
C6 | 0.74068 (14) | 0.67491 (10) | 0.69667 (10) | 0.0292 (3) | |
H6 | 0.6561 | 0.6470 | 0.6945 | 0.035* | |
C7 | 0.76466 (13) | 0.76999 (9) | 0.71587 (9) | 0.0251 (3) | |
C8 | 0.67729 (13) | 0.85079 (9) | 0.73182 (9) | 0.0254 (3) | |
C9 | 0.62651 (14) | 0.90870 (9) | 0.63186 (10) | 0.0285 (3) | |
H9 | 0.5710 | 0.9626 | 0.6426 | 0.034* | |
C10 | 0.53647 (14) | 0.85611 (10) | 0.53852 (11) | 0.0346 (3) | |
C11 | 0.57426 (18) | 0.85937 (12) | 0.44781 (12) | 0.0457 (4) | |
H11 | 0.5085 | 0.8379 | 0.3863 | 0.055* | |
C12 | 0.69449 (18) | 0.89046 (12) | 0.44641 (12) | 0.0459 (4) | |
H12 | 0.7102 | 0.8917 | 0.3841 | 0.055* | |
C13 | 0.80386 (16) | 0.92290 (10) | 0.53727 (11) | 0.0349 (3) | |
C14 | 0.76543 (14) | 0.94965 (10) | 0.62811 (10) | 0.0283 (3) | |
H14 | 0.7602 | 1.0197 | 0.6304 | 0.034* | |
C15 | 0.44699 (16) | 0.77763 (12) | 0.54481 (13) | 0.0456 (4) | |
H15A | 0.4275 | 0.7281 | 0.4926 | 0.055* | |
H15B | 0.4543 | 0.7551 | 0.6127 | 0.055* | |
C16 | 0.99695 (13) | 0.97469 (9) | 0.78415 (10) | 0.0258 (3) | |
C17 | 1.06064 (15) | 0.96424 (11) | 0.88772 (11) | 0.0363 (3) | |
H17 | 1.0288 | 0.9173 | 0.9222 | 0.044* | |
C18 | 1.16971 (16) | 1.02129 (12) | 0.94119 (11) | 0.0432 (4) | |
H18 | 1.2114 | 1.0140 | 1.0121 | 0.052* | |
C19 | 1.21823 (15) | 1.08892 (11) | 0.89182 (12) | 0.0399 (4) | |
H19 | 1.2936 | 1.1279 | 0.9285 | 0.048* | |
C20 | 1.15666 (15) | 1.09941 (11) | 0.78916 (12) | 0.0381 (4) | |
H20 | 1.1898 | 1.1458 | 0.7550 | 0.046* | |
C21 | 1.04651 (14) | 1.04270 (10) | 0.73515 (11) | 0.0332 (3) | |
H21 | 1.0049 | 1.0505 | 0.6643 | 0.040* | |
C22 | 0.57793 (13) | 0.83223 (10) | 0.78705 (10) | 0.0290 (3) | |
C23 | 0.61108 (15) | 0.76515 (11) | 0.86332 (10) | 0.0339 (3) | |
H23 | 0.6920 | 0.7282 | 0.8762 | 0.041* | |
C24 | 0.52772 (17) | 0.75131 (13) | 0.92095 (11) | 0.0435 (4) | |
H24 | 0.5519 | 0.7054 | 0.9729 | 0.052* | |
C25 | 0.40968 (18) | 0.80445 (13) | 0.90257 (13) | 0.0493 (4) | |
H25 | 0.3531 | 0.7957 | 0.9424 | 0.059* | |
C26 | 0.37405 (18) | 0.87026 (13) | 0.82627 (15) | 0.0510 (5) | |
H26 | 0.2922 | 0.9062 | 0.8132 | 0.061* | |
C27 | 0.45736 (16) | 0.88431 (11) | 0.76832 (13) | 0.0418 (4) | |
H27 | 0.4319 | 0.9296 | 0.7158 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0243 (4) | 0.0265 (5) | 0.0248 (5) | −0.0026 (4) | 0.0095 (4) | −0.0024 (4) |
O2 | 0.0553 (7) | 0.0586 (8) | 0.0441 (7) | −0.0114 (6) | 0.0276 (6) | −0.0065 (6) |
O3 | 0.0313 (5) | 0.0467 (7) | 0.0494 (7) | 0.0033 (5) | −0.0009 (5) | −0.0034 (5) |
C1 | 0.0262 (6) | 0.0251 (7) | 0.0233 (6) | −0.0005 (5) | 0.0102 (5) | 0.0009 (5) |
C2 | 0.0276 (6) | 0.0238 (7) | 0.0208 (6) | 0.0000 (5) | 0.0072 (5) | 0.0011 (5) |
C3 | 0.0289 (7) | 0.0316 (7) | 0.0287 (7) | 0.0011 (6) | 0.0117 (6) | 0.0014 (6) |
C4 | 0.0369 (8) | 0.0309 (8) | 0.0319 (7) | 0.0071 (6) | 0.0136 (6) | −0.0008 (6) |
C5 | 0.0431 (8) | 0.0235 (7) | 0.0297 (7) | 0.0012 (6) | 0.0100 (6) | −0.0017 (6) |
C6 | 0.0308 (7) | 0.0275 (7) | 0.0278 (7) | −0.0038 (6) | 0.0082 (6) | 0.0003 (5) |
C7 | 0.0270 (6) | 0.0258 (7) | 0.0218 (6) | 0.0008 (5) | 0.0074 (5) | 0.0018 (5) |
C8 | 0.0233 (6) | 0.0257 (7) | 0.0251 (6) | −0.0009 (5) | 0.0057 (5) | −0.0023 (5) |
C9 | 0.0281 (7) | 0.0274 (7) | 0.0273 (7) | 0.0026 (5) | 0.0062 (5) | −0.0008 (5) |
C10 | 0.0306 (7) | 0.0347 (8) | 0.0307 (7) | 0.0041 (6) | 0.0006 (6) | −0.0008 (6) |
C11 | 0.0502 (10) | 0.0496 (10) | 0.0283 (8) | 0.0003 (8) | 0.0020 (7) | −0.0069 (7) |
C12 | 0.0580 (10) | 0.0519 (10) | 0.0266 (8) | 0.0001 (8) | 0.0132 (7) | −0.0030 (7) |
C13 | 0.0435 (8) | 0.0335 (8) | 0.0291 (7) | −0.0015 (6) | 0.0143 (6) | 0.0039 (6) |
C14 | 0.0330 (7) | 0.0244 (7) | 0.0256 (6) | 0.0011 (5) | 0.0076 (5) | 0.0013 (5) |
C15 | 0.0411 (9) | 0.0411 (9) | 0.0425 (9) | −0.0051 (7) | −0.0008 (7) | −0.0014 (7) |
C16 | 0.0262 (6) | 0.0243 (7) | 0.0281 (7) | 0.0008 (5) | 0.0110 (5) | −0.0017 (5) |
C17 | 0.0360 (8) | 0.0417 (9) | 0.0300 (7) | −0.0073 (7) | 0.0099 (6) | 0.0033 (6) |
C18 | 0.0395 (8) | 0.0567 (10) | 0.0294 (8) | −0.0092 (7) | 0.0068 (6) | −0.0041 (7) |
C19 | 0.0330 (8) | 0.0415 (9) | 0.0453 (9) | −0.0097 (7) | 0.0135 (7) | −0.0118 (7) |
C20 | 0.0362 (8) | 0.0350 (8) | 0.0446 (9) | −0.0091 (6) | 0.0159 (7) | 0.0001 (7) |
C21 | 0.0340 (7) | 0.0332 (8) | 0.0318 (7) | −0.0042 (6) | 0.0107 (6) | 0.0022 (6) |
C22 | 0.0247 (6) | 0.0309 (7) | 0.0314 (7) | −0.0045 (6) | 0.0097 (5) | −0.0074 (6) |
C23 | 0.0299 (7) | 0.0435 (9) | 0.0279 (7) | −0.0048 (6) | 0.0095 (6) | −0.0034 (6) |
C24 | 0.0466 (9) | 0.0551 (10) | 0.0315 (8) | −0.0152 (8) | 0.0169 (7) | −0.0059 (7) |
C25 | 0.0475 (10) | 0.0606 (11) | 0.0515 (10) | −0.0181 (8) | 0.0322 (8) | −0.0192 (9) |
C26 | 0.0381 (9) | 0.0518 (11) | 0.0732 (12) | −0.0016 (8) | 0.0322 (9) | −0.0139 (9) |
C27 | 0.0356 (8) | 0.0381 (9) | 0.0560 (10) | 0.0013 (7) | 0.0215 (7) | −0.0018 (7) |
O1—C1 | 1.4565 (15) | C12—C13 | 1.461 (2) |
O1—C8 | 1.4575 (15) | C12—H12 | 0.9500 |
O2—C13 | 1.2211 (18) | C13—C14 | 1.5180 (19) |
O3—C15 | 1.427 (2) | C14—H14 | 1.0000 |
O3—C10 | 1.4572 (17) | C15—H15A | 0.9900 |
C1—C16 | 1.5080 (18) | C15—H15B | 0.9900 |
C1—C2 | 1.5206 (18) | C16—C21 | 1.3874 (19) |
C1—C14 | 1.5686 (18) | C16—C17 | 1.3899 (19) |
C2—C3 | 1.3824 (19) | C17—C18 | 1.382 (2) |
C2—C7 | 1.3972 (18) | C17—H17 | 0.9500 |
C3—C4 | 1.398 (2) | C18—C19 | 1.381 (2) |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C4—C5 | 1.383 (2) | C19—C20 | 1.376 (2) |
C4—H4 | 0.9500 | C19—H19 | 0.9500 |
C5—C6 | 1.396 (2) | C20—C21 | 1.388 (2) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C6—C7 | 1.3860 (19) | C21—H21 | 0.9500 |
C6—H6 | 0.9500 | C22—C23 | 1.392 (2) |
C7—C8 | 1.5260 (18) | C22—C27 | 1.393 (2) |
C8—C22 | 1.5118 (18) | C23—C24 | 1.389 (2) |
C8—C9 | 1.5617 (18) | C23—H23 | 0.9500 |
C9—C10 | 1.5221 (19) | C24—C25 | 1.380 (3) |
C9—C14 | 1.5657 (19) | C24—H24 | 0.9500 |
C9—H9 | 1.0000 | C25—C26 | 1.379 (3) |
C10—C11 | 1.465 (2) | C25—H25 | 0.9500 |
C10—C15 | 1.472 (2) | C26—C27 | 1.392 (2) |
C11—C12 | 1.324 (2) | C26—H26 | 0.9500 |
C11—H11 | 0.9500 | C27—H27 | 0.9500 |
C1—O1—C8 | 98.75 (9) | O2—C13—C14 | 121.43 (13) |
C15—O3—C10 | 61.35 (10) | C12—C13—C14 | 118.33 (13) |
O1—C1—C16 | 107.95 (10) | C13—C14—C9 | 116.47 (12) |
O1—C1—C2 | 100.48 (9) | C13—C14—C1 | 113.76 (11) |
C16—C1—C2 | 119.93 (11) | C9—C14—C1 | 101.99 (10) |
O1—C1—C14 | 100.76 (10) | C13—C14—H14 | 108.1 |
C16—C1—C14 | 119.36 (11) | C9—C14—H14 | 108.1 |
C2—C1—C14 | 105.06 (10) | C1—C14—H14 | 108.1 |
C3—C2—C7 | 121.59 (12) | O3—C15—C10 | 60.32 (10) |
C3—C2—C1 | 132.85 (12) | O3—C15—H15A | 117.7 |
C7—C2—C1 | 105.29 (11) | C10—C15—H15A | 117.7 |
C2—C3—C4 | 117.72 (13) | O3—C15—H15B | 117.7 |
C2—C3—H3 | 121.1 | C10—C15—H15B | 117.7 |
C4—C3—H3 | 121.1 | H15A—C15—H15B | 114.9 |
C5—C4—C3 | 120.91 (13) | C21—C16—C17 | 118.63 (13) |
C5—C4—H4 | 119.5 | C21—C16—C1 | 122.92 (12) |
C3—C4—H4 | 119.5 | C17—C16—C1 | 118.36 (12) |
C4—C5—C6 | 121.19 (13) | C18—C17—C16 | 120.80 (14) |
C4—C5—H5 | 119.4 | C18—C17—H17 | 119.6 |
C6—C5—H5 | 119.4 | C16—C17—H17 | 119.6 |
C7—C6—C5 | 118.08 (13) | C19—C18—C17 | 120.18 (14) |
C7—C6—H6 | 121.0 | C19—C18—H18 | 119.9 |
C5—C6—H6 | 121.0 | C17—C18—H18 | 119.9 |
C6—C7—C2 | 120.48 (12) | C20—C19—C18 | 119.53 (14) |
C6—C7—C8 | 133.69 (12) | C20—C19—H19 | 120.2 |
C2—C7—C8 | 105.71 (11) | C18—C19—H19 | 120.2 |
O1—C8—C22 | 108.28 (10) | C19—C20—C21 | 120.55 (14) |
O1—C8—C7 | 100.46 (9) | C19—C20—H20 | 119.7 |
C22—C8—C7 | 119.06 (11) | C21—C20—H20 | 119.7 |
O1—C8—C9 | 99.47 (10) | C16—C21—C20 | 120.31 (13) |
C22—C8—C9 | 118.98 (11) | C16—C21—H21 | 119.8 |
C7—C8—C9 | 107.14 (10) | C20—C21—H21 | 119.8 |
C10—C9—C8 | 115.96 (11) | C23—C22—C27 | 118.45 (13) |
C10—C9—C14 | 116.44 (12) | C23—C22—C8 | 119.43 (12) |
C8—C9—C14 | 101.71 (10) | C27—C22—C8 | 122.00 (13) |
C10—C9—H9 | 107.4 | C24—C23—C22 | 121.06 (15) |
C8—C9—H9 | 107.4 | C24—C23—H23 | 119.5 |
C14—C9—H9 | 107.4 | C22—C23—H23 | 119.5 |
O3—C10—C11 | 111.66 (12) | C25—C24—C23 | 119.84 (16) |
O3—C10—C15 | 58.33 (9) | C25—C24—H24 | 120.1 |
C11—C10—C15 | 116.09 (14) | C23—C24—H24 | 120.1 |
O3—C10—C9 | 114.77 (12) | C26—C25—C24 | 119.92 (15) |
C11—C10—C9 | 118.41 (13) | C26—C25—H25 | 120.0 |
C15—C10—C9 | 121.91 (13) | C24—C25—H25 | 120.0 |
C12—C11—C10 | 123.96 (14) | C25—C26—C27 | 120.40 (16) |
C12—C11—H11 | 118.0 | C25—C26—H26 | 119.8 |
C10—C11—H11 | 118.0 | C27—C26—H26 | 119.8 |
C11—C12—C13 | 122.39 (15) | C26—C27—C22 | 120.32 (16) |
C11—C12—H12 | 118.8 | C26—C27—H27 | 119.8 |
C13—C12—H12 | 118.8 | C22—C27—H27 | 119.8 |
O2—C13—C12 | 120.23 (14) | ||
C8—O1—C1—C16 | −177.64 (10) | C11—C12—C13—O2 | 160.20 (17) |
C8—O1—C1—C2 | −51.25 (11) | C11—C12—C13—C14 | −18.8 (2) |
C8—O1—C1—C14 | 56.46 (11) | O2—C13—C14—C9 | −158.41 (14) |
O1—C1—C2—C3 | −153.39 (14) | C12—C13—C14—C9 | 20.60 (19) |
C16—C1—C2—C3 | −35.5 (2) | O2—C13—C14—C1 | −40.20 (19) |
C14—C1—C2—C3 | 102.34 (16) | C12—C13—C14—C1 | 138.81 (14) |
O1—C1—C2—C7 | 32.76 (12) | C10—C9—C14—C13 | −7.02 (17) |
C16—C1—C2—C7 | 150.68 (11) | C8—C9—C14—C13 | 120.02 (12) |
C14—C1—C2—C7 | −71.51 (12) | C10—C9—C14—C1 | −131.48 (12) |
C7—C2—C3—C4 | −1.56 (19) | C8—C9—C14—C1 | −4.44 (12) |
C1—C2—C3—C4 | −174.59 (13) | O1—C1—C14—C13 | −156.86 (11) |
C2—C3—C4—C5 | 1.1 (2) | C16—C1—C14—C13 | 85.30 (15) |
C3—C4—C5—C6 | 0.4 (2) | C2—C1—C14—C13 | −52.80 (14) |
C4—C5—C6—C7 | −1.5 (2) | O1—C1—C14—C9 | −30.60 (12) |
C5—C6—C7—C2 | 1.10 (19) | C16—C1—C14—C9 | −148.44 (11) |
C5—C6—C7—C8 | 176.58 (13) | C2—C1—C14—C9 | 73.45 (12) |
C3—C2—C7—C6 | 0.45 (19) | C11—C10—C15—O3 | −100.41 (14) |
C1—C2—C7—C6 | 175.16 (12) | C9—C10—C15—O3 | 101.29 (14) |
C3—C2—C7—C8 | −176.15 (12) | O1—C1—C16—C21 | −134.13 (13) |
C1—C2—C7—C8 | −1.44 (13) | C2—C1—C16—C21 | 111.84 (15) |
C1—O1—C8—C22 | 175.73 (10) | C14—C1—C16—C21 | −20.08 (19) |
C1—O1—C8—C7 | 50.19 (10) | O1—C1—C16—C17 | 42.28 (16) |
C1—O1—C8—C9 | −59.35 (10) | C2—C1—C16—C17 | −71.75 (16) |
C6—C7—C8—O1 | 153.74 (14) | C14—C1—C16—C17 | 156.33 (12) |
C2—C7—C8—O1 | −30.31 (12) | C21—C16—C17—C18 | 1.0 (2) |
C6—C7—C8—C22 | 35.9 (2) | C1—C16—C17—C18 | −175.58 (14) |
C2—C7—C8—C22 | −148.18 (11) | C16—C17—C18—C19 | −0.9 (2) |
C6—C7—C8—C9 | −102.85 (16) | C17—C18—C19—C20 | 0.4 (2) |
C2—C7—C8—C9 | 73.10 (12) | C18—C19—C20—C21 | 0.0 (2) |
O1—C8—C9—C10 | 165.37 (11) | C17—C16—C21—C20 | −0.6 (2) |
C22—C8—C9—C10 | −77.51 (15) | C1—C16—C21—C20 | 175.82 (13) |
C7—C8—C9—C10 | 61.24 (14) | C19—C20—C21—C16 | 0.1 (2) |
O1—C8—C9—C14 | 38.02 (11) | O1—C8—C22—C23 | −81.07 (15) |
C22—C8—C9—C14 | 155.14 (11) | C7—C8—C22—C23 | 32.65 (18) |
C7—C8—C9—C14 | −66.10 (12) | C9—C8—C22—C23 | 166.53 (12) |
C15—O3—C10—C11 | 108.12 (15) | O1—C8—C22—C27 | 94.92 (15) |
C15—O3—C10—C9 | −113.54 (15) | C7—C8—C22—C27 | −151.36 (13) |
C8—C9—C10—O3 | 96.05 (14) | C9—C8—C22—C27 | −17.48 (19) |
C14—C9—C10—O3 | −144.34 (12) | C27—C22—C23—C24 | −1.2 (2) |
C8—C9—C10—C11 | −128.57 (14) | C8—C22—C23—C24 | 174.95 (13) |
C14—C9—C10—C11 | −8.96 (18) | C22—C23—C24—C25 | 0.2 (2) |
C8—C9—C10—C15 | 29.24 (18) | C23—C24—C25—C26 | 0.8 (2) |
C14—C9—C10—C15 | 148.86 (13) | C24—C25—C26—C27 | −0.8 (3) |
O3—C10—C11—C12 | 149.43 (17) | C25—C26—C27—C22 | −0.2 (3) |
C15—C10—C11—C12 | −146.33 (17) | C23—C22—C27—C26 | 1.2 (2) |
C9—C10—C11—C12 | 12.8 (2) | C8—C22—C27—C26 | −174.83 (14) |
C10—C11—C12—C13 | 1.5 (3) |
C28H22O3 | F(000) = 856 |
Mr = 406.46 | Dx = 1.339 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4806 reflections |
a = 8.434 (1) Å | θ = 2.0–27.5° |
b = 13.586 (1) Å | µ = 0.09 mm−1 |
c = 17.597 (2) Å | T = 200 K |
β = 90.646 (4)° | Rectangular chunk, pale yellow |
V = 2016.3 (4) Å3 | 0.35 × 0.27 × 0.23 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3513 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
ϕ and ω scans | h = −10→10 |
38808 measured reflections | k = −17→17 |
4609 independent reflections | l = −22→22 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0627P)2 + 0.2487P] where P = (Fo2 + 2Fc2)/3 |
4609 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C28H22O3 | V = 2016.3 (4) Å3 |
Mr = 406.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.434 (1) Å | µ = 0.09 mm−1 |
b = 13.586 (1) Å | T = 200 K |
c = 17.597 (2) Å | 0.35 × 0.27 × 0.23 mm |
β = 90.646 (4)° |
Nonius KappaCCD diffractometer | 3513 reflections with I > 2σ(I) |
38808 measured reflections | Rint = 0.035 |
4609 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.19 e Å−3 |
4609 reflections | Δρmin = −0.24 e Å−3 |
280 parameters |
Experimental. All work was done at 200 K using an Oxford Cryosystems Cryostream Cooler. A quadrant of reciprocal space was measured with a redundancy factor of 4.1, which means that 90% of the data was measured at least 4.1 times. A combination of phi and omega scans with a frame width of 1.0° was used for data collection. Data integration was done with DENZO (Otwinowski & Minor, 1997). Scaling and merging of the data was done with SCALEPACK (Otwinowski & Minor, 1997). |
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 | 0.17223 (9) | 0.11593 (6) | 0.37571 (5) | 0.0274 (2) | |
O2 | 0.55310 (11) | −0.11098 (7) | 0.39718 (5) | 0.0379 (2) | |
O3 | 0.59848 (11) | 0.28872 (6) | 0.36886 (5) | 0.0392 (2) | |
C1 | 0.25689 (14) | 0.02912 (8) | 0.35240 (7) | 0.0258 (3) | |
C2 | 0.31367 (14) | 0.05935 (9) | 0.27394 (7) | 0.0266 (3) | |
C3 | 0.35910 (15) | 0.00763 (10) | 0.20995 (7) | 0.0323 (3) | |
H3 | 0.3456 | −0.0617 | 0.2067 | 0.039* | |
C4 | 0.42534 (17) | 0.06086 (10) | 0.15041 (7) | 0.0389 (3) | |
H4 | 0.4566 | 0.0272 | 0.1057 | 0.047* | |
C5 | 0.44655 (17) | 0.16172 (10) | 0.15505 (7) | 0.0372 (3) | |
H5 | 0.4908 | 0.1962 | 0.1134 | 0.045* | |
C6 | 0.40365 (15) | 0.21327 (9) | 0.22019 (7) | 0.0308 (3) | |
H6 | 0.4197 | 0.2823 | 0.2240 | 0.037* | |
C7 | 0.33717 (14) | 0.16081 (9) | 0.27897 (6) | 0.0266 (3) | |
C8 | 0.29413 (14) | 0.18929 (9) | 0.35950 (7) | 0.0265 (3) | |
C9 | 0.43228 (14) | 0.15023 (9) | 0.41230 (6) | 0.0267 (3) | |
H9 | 0.4103 | 0.1719 | 0.4654 | 0.032* | |
C10 | 0.59935 (15) | 0.18506 (9) | 0.39192 (7) | 0.0309 (3) | |
C11 | 0.68060 (15) | 0.12162 (10) | 0.33536 (8) | 0.0366 (3) | |
H11 | 0.7503 | 0.1517 | 0.3002 | 0.044* | |
C12 | 0.65986 (15) | 0.02474 (10) | 0.33186 (7) | 0.0361 (3) | |
H12 | 0.7207 | −0.0134 | 0.2975 | 0.043* | |
C13 | 0.54382 (14) | −0.02355 (9) | 0.38060 (7) | 0.0294 (3) | |
C14 | 0.40708 (14) | 0.03738 (9) | 0.40820 (6) | 0.0259 (3) | |
H14 | 0.3762 | 0.0132 | 0.4596 | 0.031* | |
C15 | 0.16015 (14) | −0.06286 (9) | 0.36315 (7) | 0.0274 (3) | |
C16 | 0.02298 (15) | −0.05935 (10) | 0.40624 (8) | 0.0341 (3) | |
H16 | −0.0122 | 0.0017 | 0.4263 | 0.041* | |
C17 | −0.06263 (16) | −0.14436 (11) | 0.42007 (9) | 0.0427 (4) | |
H17 | −0.1558 | −0.1412 | 0.4498 | 0.051* | |
C18 | −0.01417 (16) | −0.23345 (10) | 0.39119 (8) | 0.0404 (3) | |
H18 | −0.0742 | −0.2913 | 0.4004 | 0.049* | |
C19 | 0.12263 (17) | −0.23803 (10) | 0.34863 (8) | 0.0381 (3) | |
H19 | 0.1573 | −0.2994 | 0.3290 | 0.046* | |
C20 | 0.20920 (16) | −0.15349 (9) | 0.33446 (7) | 0.0330 (3) | |
H20 | 0.3027 | −0.1573 | 0.3050 | 0.040* | |
C21 | 0.22890 (14) | 0.29088 (9) | 0.37393 (7) | 0.0290 (3) | |
C22 | 0.13493 (17) | 0.33565 (11) | 0.31866 (8) | 0.0409 (3) | |
H22 | 0.1146 | 0.3024 | 0.2721 | 0.049* | |
C23 | 0.07030 (19) | 0.42824 (12) | 0.33038 (9) | 0.0504 (4) | |
H23 | 0.0068 | 0.4581 | 0.2919 | 0.060* | |
C24 | 0.09832 (18) | 0.47701 (11) | 0.39802 (9) | 0.0487 (4) | |
H24 | 0.0553 | 0.5407 | 0.4060 | 0.058* | |
C25 | 0.18906 (19) | 0.43274 (11) | 0.45392 (9) | 0.0482 (4) | |
H25 | 0.2071 | 0.4657 | 0.5009 | 0.058* | |
C26 | 0.25408 (17) | 0.34055 (10) | 0.44207 (8) | 0.0388 (3) | |
H26 | 0.3167 | 0.3109 | 0.4810 | 0.047* | |
C27 | 0.6901 (2) | 0.31675 (12) | 0.43573 (9) | 0.0510 (4) | |
H27A | 0.6295 | 0.3573 | 0.4720 | 0.061* | |
H27B | 0.7921 | 0.3488 | 0.4235 | 0.061* | |
C28 | 0.70866 (17) | 0.21050 (10) | 0.46077 (8) | 0.0413 (3) | |
H28A | 0.6622 | 0.1956 | 0.5109 | 0.050* | |
H28B | 0.8179 | 0.1845 | 0.4569 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0286 (4) | 0.0241 (4) | 0.0294 (4) | 0.0007 (3) | 0.0030 (3) | −0.0005 (3) |
O2 | 0.0408 (5) | 0.0288 (5) | 0.0441 (5) | 0.0043 (4) | −0.0041 (4) | −0.0011 (4) |
O3 | 0.0438 (5) | 0.0300 (5) | 0.0438 (5) | −0.0067 (4) | −0.0058 (4) | 0.0094 (4) |
C1 | 0.0271 (6) | 0.0244 (6) | 0.0258 (6) | 0.0016 (5) | 0.0008 (5) | −0.0002 (5) |
C2 | 0.0264 (6) | 0.0280 (6) | 0.0252 (6) | −0.0008 (5) | −0.0024 (5) | 0.0012 (5) |
C3 | 0.0377 (7) | 0.0299 (7) | 0.0293 (6) | −0.0019 (5) | 0.0009 (5) | −0.0041 (5) |
C4 | 0.0492 (8) | 0.0412 (8) | 0.0265 (6) | −0.0029 (6) | 0.0057 (6) | −0.0055 (6) |
C5 | 0.0464 (8) | 0.0388 (8) | 0.0265 (6) | −0.0051 (6) | 0.0049 (6) | 0.0042 (6) |
C6 | 0.0357 (7) | 0.0292 (7) | 0.0275 (6) | −0.0011 (5) | −0.0014 (5) | 0.0023 (5) |
C7 | 0.0275 (6) | 0.0280 (6) | 0.0242 (6) | 0.0020 (5) | −0.0031 (5) | 0.0001 (5) |
C8 | 0.0297 (6) | 0.0256 (6) | 0.0243 (6) | −0.0015 (5) | 0.0004 (5) | 0.0016 (5) |
C9 | 0.0320 (6) | 0.0261 (6) | 0.0219 (6) | 0.0002 (5) | −0.0010 (5) | 0.0000 (5) |
C10 | 0.0339 (7) | 0.0283 (7) | 0.0304 (6) | −0.0036 (5) | −0.0044 (5) | 0.0053 (5) |
C11 | 0.0299 (7) | 0.0439 (8) | 0.0360 (7) | −0.0014 (6) | 0.0035 (5) | 0.0066 (6) |
C12 | 0.0316 (7) | 0.0411 (8) | 0.0355 (7) | 0.0043 (6) | 0.0034 (5) | −0.0025 (6) |
C13 | 0.0316 (6) | 0.0301 (7) | 0.0264 (6) | 0.0016 (5) | −0.0064 (5) | −0.0028 (5) |
C14 | 0.0300 (6) | 0.0258 (6) | 0.0220 (6) | −0.0007 (5) | 0.0005 (5) | 0.0016 (5) |
C15 | 0.0271 (6) | 0.0281 (6) | 0.0270 (6) | −0.0005 (5) | −0.0023 (5) | 0.0030 (5) |
C16 | 0.0277 (6) | 0.0321 (7) | 0.0427 (7) | 0.0036 (5) | 0.0018 (5) | 0.0042 (6) |
C17 | 0.0274 (7) | 0.0433 (9) | 0.0575 (9) | 0.0007 (6) | 0.0058 (6) | 0.0135 (7) |
C18 | 0.0355 (7) | 0.0347 (8) | 0.0510 (8) | −0.0098 (6) | −0.0034 (6) | 0.0088 (6) |
C19 | 0.0468 (8) | 0.0290 (7) | 0.0385 (7) | −0.0050 (6) | −0.0013 (6) | −0.0006 (6) |
C20 | 0.0365 (7) | 0.0297 (7) | 0.0330 (7) | −0.0025 (5) | 0.0040 (5) | −0.0009 (5) |
C21 | 0.0313 (6) | 0.0259 (6) | 0.0299 (6) | 0.0008 (5) | 0.0045 (5) | 0.0008 (5) |
C22 | 0.0455 (8) | 0.0412 (8) | 0.0361 (7) | 0.0119 (6) | 0.0001 (6) | −0.0006 (6) |
C23 | 0.0514 (9) | 0.0491 (9) | 0.0509 (9) | 0.0213 (7) | 0.0080 (7) | 0.0122 (7) |
C24 | 0.0530 (9) | 0.0284 (8) | 0.0650 (10) | 0.0102 (7) | 0.0207 (8) | 0.0033 (7) |
C25 | 0.0579 (10) | 0.0351 (8) | 0.0516 (9) | 0.0017 (7) | 0.0057 (7) | −0.0130 (7) |
C26 | 0.0471 (8) | 0.0326 (7) | 0.0368 (7) | 0.0047 (6) | −0.0005 (6) | −0.0038 (6) |
C27 | 0.0604 (10) | 0.0428 (9) | 0.0498 (9) | −0.0202 (7) | −0.0077 (8) | 0.0010 (7) |
C28 | 0.0406 (8) | 0.0418 (8) | 0.0413 (8) | −0.0091 (6) | −0.0115 (6) | 0.0045 (6) |
O1—C1 | 1.4408 (14) | C13—C14 | 1.5046 (17) |
O1—C8 | 1.4623 (14) | C14—H14 | 1.0000 |
O2—C13 | 1.2255 (15) | C15—C16 | 1.3913 (18) |
O3—C27 | 1.4514 (17) | C15—C20 | 1.3954 (18) |
O3—C10 | 1.4656 (15) | C16—C17 | 1.3852 (19) |
C1—C15 | 1.5054 (16) | C16—H16 | 0.9500 |
C1—C2 | 1.5228 (16) | C17—C18 | 1.376 (2) |
C1—C14 | 1.5979 (16) | C17—H17 | 0.9500 |
C2—C3 | 1.3851 (17) | C18—C19 | 1.384 (2) |
C2—C7 | 1.3953 (17) | C18—H18 | 0.9500 |
C3—C4 | 1.3950 (18) | C19—C20 | 1.3851 (18) |
C3—H3 | 0.9500 | C19—H19 | 0.9500 |
C4—C5 | 1.3842 (19) | C20—H20 | 0.9500 |
C4—H4 | 0.9500 | C21—C22 | 1.3882 (18) |
C5—C6 | 1.3945 (18) | C21—C26 | 1.3901 (18) |
C5—H5 | 0.9500 | C22—C23 | 1.387 (2) |
C6—C7 | 1.3802 (17) | C22—H22 | 0.9500 |
C6—H6 | 0.9500 | C23—C24 | 1.380 (2) |
C7—C8 | 1.5169 (16) | C23—H23 | 0.9500 |
C8—C21 | 1.5084 (16) | C24—C25 | 1.378 (2) |
C8—C9 | 1.5742 (16) | C24—H24 | 0.9500 |
C9—C10 | 1.5328 (17) | C25—C26 | 1.384 (2) |
C9—C14 | 1.5494 (16) | C25—H25 | 0.9500 |
C9—H9 | 1.0000 | C26—H26 | 0.9500 |
C10—C11 | 1.4896 (19) | C27—C28 | 1.517 (2) |
C10—C28 | 1.5531 (17) | C27—H27A | 0.9900 |
C11—C12 | 1.3291 (19) | C27—H27B | 0.9900 |
C11—H11 | 0.9500 | C28—H28A | 0.9900 |
C12—C13 | 1.4638 (18) | C28—H28B | 0.9900 |
C12—H12 | 0.9500 | ||
C1—O1—C8 | 98.66 (8) | C13—C14—C1 | 111.61 (9) |
C27—O3—C10 | 91.53 (9) | C9—C14—C1 | 101.86 (9) |
O1—C1—C15 | 111.88 (9) | C13—C14—H14 | 108.7 |
O1—C1—C2 | 101.49 (9) | C9—C14—H14 | 108.7 |
C15—C1—C2 | 120.95 (10) | C1—C14—H14 | 108.7 |
O1—C1—C14 | 99.18 (8) | C16—C15—C20 | 118.63 (11) |
C15—C1—C14 | 114.09 (9) | C16—C15—C1 | 119.69 (11) |
C2—C1—C14 | 106.44 (9) | C20—C15—C1 | 121.58 (11) |
C3—C2—C7 | 120.82 (11) | C17—C16—C15 | 120.37 (13) |
C3—C2—C1 | 133.86 (11) | C17—C16—H16 | 119.8 |
C7—C2—C1 | 104.77 (10) | C15—C16—H16 | 119.8 |
C2—C3—C4 | 117.67 (12) | C18—C17—C16 | 120.72 (13) |
C2—C3—H3 | 121.2 | C18—C17—H17 | 119.6 |
C4—C3—H3 | 121.2 | C16—C17—H17 | 119.6 |
C5—C4—C3 | 121.43 (12) | C17—C18—C19 | 119.48 (13) |
C5—C4—H4 | 119.3 | C17—C18—H18 | 120.3 |
C3—C4—H4 | 119.3 | C19—C18—H18 | 120.3 |
C4—C5—C6 | 120.74 (12) | C18—C19—C20 | 120.30 (13) |
C4—C5—H5 | 119.6 | C18—C19—H19 | 119.9 |
C6—C5—H5 | 119.6 | C20—C19—H19 | 119.9 |
C7—C6—C5 | 117.91 (12) | C19—C20—C15 | 120.50 (12) |
C7—C6—H6 | 121.0 | C19—C20—H20 | 119.7 |
C5—C6—H6 | 121.0 | C15—C20—H20 | 119.7 |
C6—C7—C2 | 121.41 (11) | C22—C21—C26 | 118.17 (12) |
C6—C7—C8 | 132.21 (11) | C22—C21—C8 | 119.30 (11) |
C2—C7—C8 | 106.01 (10) | C26—C21—C8 | 122.48 (11) |
O1—C8—C21 | 109.41 (9) | C23—C22—C21 | 121.02 (13) |
O1—C8—C7 | 100.64 (9) | C23—C22—H22 | 119.5 |
C21—C8—C7 | 118.83 (10) | C21—C22—H22 | 119.5 |
O1—C8—C9 | 99.93 (9) | C24—C23—C22 | 119.98 (14) |
C21—C8—C9 | 118.55 (10) | C24—C23—H23 | 120.0 |
C7—C8—C9 | 106.38 (9) | C22—C23—H23 | 120.0 |
C10—C9—C14 | 114.88 (10) | C25—C24—C23 | 119.64 (14) |
C10—C9—C8 | 115.73 (9) | C25—C24—H24 | 120.2 |
C14—C9—C8 | 101.88 (9) | C23—C24—H24 | 120.2 |
C10—C9—H9 | 108.0 | C24—C25—C26 | 120.35 (14) |
C14—C9—H9 | 108.0 | C24—C25—H25 | 119.8 |
C8—C9—H9 | 108.0 | C26—C25—H25 | 119.8 |
O3—C10—C11 | 111.83 (11) | C25—C26—C21 | 120.82 (13) |
O3—C10—C9 | 111.08 (10) | C25—C26—H26 | 119.6 |
C11—C10—C9 | 114.12 (10) | C21—C26—H26 | 119.6 |
O3—C10—C28 | 90.19 (9) | O3—C27—C28 | 92.18 (10) |
C11—C10—C28 | 112.11 (11) | O3—C27—H27A | 113.3 |
C9—C10—C28 | 115.18 (11) | C28—C27—H27A | 113.3 |
C12—C11—C10 | 122.86 (12) | O3—C27—H27B | 113.3 |
C12—C11—H11 | 118.6 | C28—C27—H27B | 113.3 |
C10—C11—H11 | 118.6 | H27A—C27—H27B | 110.6 |
C11—C12—C13 | 120.35 (12) | C27—C28—C10 | 85.80 (10) |
C11—C12—H12 | 119.8 | C27—C28—H28A | 114.4 |
C13—C12—H12 | 119.8 | C10—C28—H28A | 114.4 |
O2—C13—C12 | 122.18 (12) | C27—C28—H28B | 114.4 |
O2—C13—C14 | 120.24 (12) | C10—C28—H28B | 114.4 |
C12—C13—C14 | 117.55 (11) | H28A—C28—H28B | 111.5 |
C13—C14—C9 | 117.01 (10) | ||
C8—O1—C1—C15 | 179.44 (9) | C11—C12—C13—C14 | 25.18 (17) |
C8—O1—C1—C2 | −50.23 (10) | O2—C13—C14—C9 | 157.48 (10) |
C8—O1—C1—C14 | 58.76 (9) | C12—C13—C14—C9 | −24.54 (14) |
O1—C1—C2—C3 | −157.19 (13) | O2—C13—C14—C1 | −85.78 (13) |
C15—C1—C2—C3 | −32.77 (19) | C12—C13—C14—C1 | 92.21 (12) |
C14—C1—C2—C3 | 99.54 (15) | C10—C9—C14—C13 | −3.57 (14) |
O1—C1—C2—C7 | 31.60 (11) | C8—C9—C14—C13 | 122.35 (10) |
C15—C1—C2—C7 | 156.02 (10) | C10—C9—C14—C1 | −125.53 (10) |
C14—C1—C2—C7 | −71.68 (11) | C8—C9—C14—C1 | 0.38 (11) |
C7—C2—C3—C4 | −1.47 (18) | O1—C1—C14—C13 | −160.98 (9) |
C1—C2—C3—C4 | −171.57 (12) | C15—C1—C14—C13 | 79.97 (13) |
C2—C3—C4—C5 | 0.6 (2) | C2—C1—C14—C13 | −56.02 (12) |
C3—C4—C5—C6 | 0.7 (2) | O1—C1—C14—C9 | −35.36 (10) |
C4—C5—C6—C7 | −1.10 (19) | C15—C1—C14—C9 | −154.42 (10) |
C5—C6—C7—C2 | 0.19 (18) | C2—C1—C14—C9 | 69.60 (11) |
C5—C6—C7—C8 | 172.23 (12) | O1—C1—C15—C16 | −12.96 (15) |
C3—C2—C7—C6 | 1.12 (18) | C2—C1—C15—C16 | −132.37 (12) |
C1—C2—C7—C6 | 173.75 (11) | C14—C1—C15—C16 | 98.62 (13) |
C3—C2—C7—C8 | −172.75 (11) | O1—C1—C15—C20 | 170.72 (10) |
C1—C2—C7—C8 | −0.12 (12) | C2—C1—C15—C20 | 51.30 (16) |
C1—O1—C8—C21 | 175.70 (9) | C14—C1—C15—C20 | −77.71 (14) |
C1—O1—C8—C7 | 49.80 (10) | C20—C15—C16—C17 | −0.07 (18) |
C1—O1—C8—C9 | −59.12 (9) | C1—C15—C16—C17 | −176.51 (12) |
C6—C7—C8—O1 | 156.29 (12) | C15—C16—C17—C18 | −0.3 (2) |
C2—C7—C8—O1 | −30.78 (11) | C16—C17—C18—C19 | 0.7 (2) |
C6—C7—C8—C21 | 36.99 (19) | C17—C18—C19—C20 | −0.7 (2) |
C2—C7—C8—C21 | −150.08 (10) | C18—C19—C20—C15 | 0.3 (2) |
C6—C7—C8—C9 | −99.94 (15) | C16—C15—C20—C19 | 0.09 (18) |
C2—C7—C8—C9 | 72.99 (11) | C1—C15—C20—C19 | 176.46 (11) |
O1—C8—C9—C10 | 159.55 (10) | O1—C8—C21—C22 | −81.31 (14) |
C21—C8—C9—C10 | −81.81 (13) | C7—C8—C21—C22 | 33.36 (17) |
C7—C8—C9—C10 | 55.26 (13) | C9—C8—C21—C22 | 165.13 (11) |
O1—C8—C9—C14 | 34.20 (10) | O1—C8—C21—C26 | 96.14 (14) |
C21—C8—C9—C14 | 152.84 (10) | C7—C8—C21—C26 | −149.19 (12) |
C7—C8—C9—C14 | −70.09 (11) | C9—C8—C21—C26 | −17.43 (17) |
C27—O3—C10—C11 | −118.22 (12) | C26—C21—C22—C23 | 1.2 (2) |
C27—O3—C10—C9 | 113.00 (11) | C8—C21—C22—C23 | 178.78 (13) |
C27—O3—C10—C28 | −4.21 (11) | C21—C22—C23—C24 | −0.4 (2) |
C14—C9—C10—O3 | 158.28 (9) | C22—C23—C24—C25 | −0.8 (2) |
C8—C9—C10—O3 | 39.89 (14) | C23—C24—C25—C26 | 1.0 (2) |
C14—C9—C10—C11 | 30.73 (14) | C24—C25—C26—C21 | −0.2 (2) |
C8—C9—C10—C11 | −87.65 (13) | C22—C21—C26—C25 | −0.9 (2) |
C14—C9—C10—C28 | −101.05 (12) | C8—C21—C26—C25 | −178.41 (13) |
C8—C9—C10—C28 | 140.56 (11) | C10—O3—C27—C28 | 4.32 (12) |
O3—C10—C11—C12 | −160.88 (12) | O3—C27—C28—C10 | −4.08 (11) |
C9—C10—C11—C12 | −33.72 (17) | O3—C10—C28—C27 | 4.04 (11) |
C28—C10—C11—C12 | 99.53 (15) | C11—C10—C28—C27 | 117.80 (13) |
C10—C11—C12—C13 | 5.06 (19) | C9—C10—C28—C27 | −109.48 (13) |
C11—C12—C13—O2 | −156.88 (13) |
Experimental details
(III) | (IV) | |
Crystal data | ||
Chemical formula | C27H20O3 | C28H22O3 |
Mr | 392.43 | 406.46 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 200 | 200 |
a, b, c (Å) | 10.322 (1), 14.239 (1), 14.138 (1) | 8.434 (1), 13.586 (1), 17.597 (2) |
β (°) | 110.254 (4) | 90.646 (4) |
V (Å3) | 1949.3 (3) | 2016.3 (4) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 |
Crystal size (mm) | 0.35 × 0.31 × 0.19 | 0.35 × 0.27 × 0.23 |
Data collection | ||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41110, 4474, 3424 | 38808, 4609, 3513 |
Rint | 0.036 | 0.035 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.118, 1.05 | 0.041, 0.112, 1.04 |
No. of reflections | 4474 | 4609 |
No. of parameters | 271 | 280 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.23 | 0.19, −0.24 |
Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), reference?.
O3—C15 | 1.427 (2) | C10—C15 | 1.472 (2) |
O3—C10 | 1.4572 (17) | C11—C12 | 1.324 (2) |
C9—C10 | 1.5221 (19) | C12—C13 | 1.461 (2) |
C9—C14 | 1.5657 (19) | C13—C14 | 1.5180 (19) |
C10—C11 | 1.465 (2) | ||
C1—O1—C8 | 98.75 (9) | O3—C10—C9 | 114.77 (12) |
C15—O3—C10 | 61.35 (10) | C11—C10—C9 | 118.41 (13) |
O3—C10—C11 | 111.66 (12) | C15—C10—C9 | 121.91 (13) |
O3—C10—C15 | 58.33 (9) | O3—C15—C10 | 60.32 (10) |
C11—C10—C15 | 116.09 (14) |
O3—C27 | 1.4514 (17) | C10—C28 | 1.5531 (17) |
O3—C10 | 1.4656 (15) | C11—C12 | 1.3291 (19) |
C9—C10 | 1.5328 (17) | C12—C13 | 1.4638 (18) |
C9—C14 | 1.5494 (16) | C13—C14 | 1.5046 (17) |
C10—C11 | 1.4896 (19) | C27—C28 | 1.517 (2) |
C1—O1—C8 | 98.66 (8) | O3—C10—C28 | 90.19 (9) |
C27—O3—C10 | 91.53 (9) | C11—C10—C28 | 112.11 (11) |
O3—C10—C11 | 111.83 (11) | C9—C10—C28 | 115.18 (11) |
O3—C10—C9 | 111.08 (10) | O3—C27—C28 | 92.18 (10) |
C11—C10—C9 | 114.12 (10) | C27—C28—C10 | 85.80 (10) |
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Cross-conjugated cyclohexadienones carrying an oxaspiro ring, as in (I), hold interest as Diels–Alder dienophiles in that control of π-facial diastereoselectivity by the heteroatom is operative (Wipf & Kim, 1994; Tran-Hu—Dâu et al., 2001; Silvero et al., 1998; Takagi et al., 2003; Paquette et al., 2003). Irrespective of the size of the spiro ring and the resultant changes in basicity at the O center and overall steric contributions, diene approach from the direction syn to the O atom is heavily preferred (Ohkata et al., 2004). Diphenylisobenzofuran, (II) (Newman, 1961), one of the notably reactive dienes, is used in the present study because this compound often leads to crystalline products. We compare here the structural features of (III), the minor Diels–Alder adduct from the reaction of diphenylisobenzofuran with (I) (n=1), with those of (IV), the sole [4 + 2] product formed upon reaction of diphenylisobenzofuran with (I) (n = 2).
The size of the oxaspiro ring and the relative configuration of the spirocyclic atom C10 are the main features that differentiate these two structures. For both structures, the six-membered ring containing the spiro C atom (C9–C14) is in a boat conformation. In (III), atoms C10 and C13 lie 0.112 (1) and 0.236 (1) Å, respectively, from the least-squares plane defined by atoms C9, C11, C12 and C14. In (IV), atoms C10 and C13 lie 0.382 (1) and 0.284 (1) Å, respectively, from the analogous plane. The two boat conformations are bent in opposite directions, as seen in Figs. 1 and 2.
Another conformational difference between the two structures is seen in the orientation of the phenyl rings. This can be described by the dihedral angle between a phenyl ring and the plane defined by atoms C1, O1 and C8. In (III), the dihedral angle between the C22–C27 phenyl ring and the C1/O1/C8 plane is 84.0 (1)°. The analogous angle in (IV) is 83.9 (1)°, where the phenyl ring consists of atoms C21–C26. Note that both phenyl rings are located on the same end of the molecule as the spiro ring. For the other two phenyl rings, the dihedral angles are significantly different; in (III), this dihedral angle is 44.5 (1)°, while for (IV) it is 11.9 (1)°.
The oxetane ring in (IV) can be compared with the structure of oxetane (C3H6O), which was determined at two temperatures, viz. 90 and 140 K (Luger & Buschmann, 1984). Oxetane was found to have several interesting features, including ring puckering, as described by the dihedral angle between the C/O/C and C/C/C planes, of 10.7 (1)° at 90 K and 8.7 (2)° at 140 K, long C—O bond lengths of 1.460 (1) Å at 90 K and 1.443 (2) Å at 140 K, and an acute C—C—C angle of 84.79 (9)° at 90 K and 85.0 (1)° at 140 K. These same features are observed in (IV), with a ring-puckering angle of 5.8 (1)°, long O3—C27 O3—C10 bond lengths of 1.4514 (17) and 1.4656 (15) Å, and an acute C27—C28—C10 angle of 85.8 (1)°. There is only one other structure in the Cambridge Structural Database (Allen, 2002, Version 5.25 of November 2003) that contains an analogous spiro oxetane ring, where the spiro C atom is located adjacent to the O atom, namely 6,8,9-tris(ethyleneoxy)-2,4,10- trioxatricyclo(3.3.1.1)decane (Paquette et al., 2001). This compound contains three spiro oxetane rings and exhibits the above-mentioned features of (IV) and oxetane.