Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109007331/fg3073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109007331/fg3073292Ksup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109007331/fg3073393Ksup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109007331/fg3073150Ksup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109007331/fg307390Ksup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270109007331/fg3073fig1Ssup6.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270109007331/fg3073fig2Ssup7.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270109007331/fg3073fig3Ssup8.pdf |
CCDC references: 633197; 633198; 633199; 633200
Racemic 1,1'-bi-2,2'-naphthol (2 g m, 6.9 mmol) was dissolved in dichloromethane (10 ml) under nitrogen atmosphere. Triethylamine (1.947 ml, 13.8 mmol) and ethyl chloroformate (1.334 ml, 13.8 mmol) were added, and the mixture was stirred for 30 min. The reaction mixture was washed with water and the solvent evaporated in vacuo to obtain the racemic 1,1'-binaphthalene-2,2'-diyl diethyl biscarbonate (2.39 g, 6.7 mmol, 99%; Kulkarni, 2003). 1H NMR (300 MHz, CDCl3): δ 1.0 (3H, t), 3.9 (2H, q), 7.1–8.0 (12H, m). HR–MS: 453.1314 (M+Na), 315.1414, 431.1520 448.1765 [C26H22O6 molecular Mass (M) = 430.1415]. The compound was crystallized from ethyl acetate by slow evaporation at room temperature, resulting in two different morphological forms, blocks and plates. The crystallographic data collected on crystals of both morphologies gave the same unit-cell parameters and same results, thus ruling out the possibility of concomitant polymorphs.
All non hydrogen atoms were refined anisotropically and the occupancy refinements with the 90 K data were done using the PART command in SHELXL97. All hydrogen atoms were positioned geometrically with fixed C–H distances in the range 0.93–0.97 Å and refined using the riding model with Uiso(H)= 1.2Ueq(Csp2) and 1.5Ueq(Csp3).
For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Version 6.14; Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), POV-RAY (Persistence of Vision Team, 2004) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).
C26H22O6 | Z = 2 |
Mr = 430.44 | F(000) = 452 |
Triclinic, P1 | Dx = 1.294 Mg m−3 |
Hall symbol: -P 1 | Melting point: 417.67 K |
a = 9.7614 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0379 (14) Å | Cell parameters from 558 reflections |
c = 12.3947 (17) Å | θ = 0.9–28.0° |
α = 89.490 (2)° | µ = 0.09 mm−1 |
β = 84.810 (2)° | T = 292 K |
γ = 65.989 (2)° | Block, colourless |
V = 1104.3 (3) Å3 | 0.50 × 0.31 × 0.25 mm |
Bruker SMART CCD area detector diffractometer | 4176 independent reflections |
Radiation source: fine-focus sealed tube | 2806 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ϕ and ω scans | θmax = 25.7°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.907, Tmax = 0.977 | k = −12→12 |
11287 measured reflections | l = −15→15 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0996P)2 + 0.1958P] where P = (Fo2 + 2Fc2)/3 |
4176 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C26H22O6 | γ = 65.989 (2)° |
Mr = 430.44 | V = 1104.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.7614 (14) Å | Mo Kα radiation |
b = 10.0379 (14) Å | µ = 0.09 mm−1 |
c = 12.3947 (17) Å | T = 292 K |
α = 89.490 (2)° | 0.50 × 0.31 × 0.25 mm |
β = 84.810 (2)° |
Bruker SMART CCD area detector diffractometer | 4176 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2806 reflections with I > 2σ(I) |
Tmin = 0.907, Tmax = 0.977 | Rint = 0.016 |
11287 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.23 e Å−3 |
4176 reflections | Δρmin = −0.20 e Å−3 |
291 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 | ||
C1 | 1.0259 (2) | 0.2977 (2) | 0.38275 (16) | 0.0554 (5) | |
C2 | 1.0067 (3) | 0.2070 (3) | 0.46549 (17) | 0.0684 (6) | |
H2 | 0.9434 | 0.1599 | 0.4576 | 0.082* | |
C3 | 1.0801 (3) | 0.1880 (3) | 0.5566 (2) | 0.0893 (8) | |
H3 | 1.0657 | 0.1286 | 0.6105 | 0.107* | |
C4 | 1.1759 (3) | 0.2560 (4) | 0.5699 (3) | 0.0987 (10) | |
H4 | 1.2257 | 0.2415 | 0.6323 | 0.118* | |
C5 | 1.1975 (3) | 0.3431 (3) | 0.4931 (3) | 0.0897 (9) | |
H5 | 1.2621 | 0.3881 | 0.5032 | 0.108* | |
C6 | 1.1229 (2) | 0.3671 (2) | 0.3970 (2) | 0.0678 (6) | |
C7 | 1.1414 (3) | 0.4590 (3) | 0.3149 (3) | 0.0824 (8) | |
H7 | 1.2064 | 0.5043 | 0.3229 | 0.099* | |
C8 | 1.0667 (3) | 0.4825 (3) | 0.2252 (2) | 0.0781 (7) | |
H8 | 1.0795 | 0.5438 | 0.1724 | 0.094* | |
C9 | 0.9699 (3) | 0.4136 (2) | 0.21267 (17) | 0.0615 (5) | |
C10 | 0.9479 (2) | 0.3220 (2) | 0.28763 (15) | 0.0539 (5) | |
C11 | 0.8536 (3) | 0.2422 (2) | 0.26830 (16) | 0.0627 (6) | |
C12 | 0.9227 (4) | 0.1030 (3) | 0.21078 (19) | 0.0835 (8) | |
C13 | 1.0751 (5) | 0.0434 (3) | 0.1689 (2) | 0.1004 (10) | |
H13 | 1.1350 | 0.0936 | 0.1790 | 0.120* | |
C14 | 1.1354 (6) | −0.0878 (3) | 0.1135 (3) | 0.1424 (17) | |
H14 | 1.2360 | −0.1269 | 0.0858 | 0.171* | |
C15 | 1.0460 (11) | −0.1627 (6) | 0.0987 (5) | 0.192 (4) | |
H15 | 1.0883 | −0.2512 | 0.0599 | 0.230* | |
C16 | 0.9017 (9) | −0.1125 (6) | 0.1381 (4) | 0.167 (3) | |
H16 | 0.8457 | −0.1665 | 0.1277 | 0.200* | |
C17 | 0.8333 (6) | 0.0253 (4) | 0.1966 (3) | 0.1182 (14) | |
C18 | 0.6830 (7) | 0.0816 (6) | 0.2395 (4) | 0.147 (2) | |
H18 | 0.6261 | 0.0280 | 0.2312 | 0.176* | |
C19 | 0.6170 (4) | 0.2147 (5) | 0.2940 (3) | 0.1216 (14) | |
H19 | 0.5166 | 0.2515 | 0.3221 | 0.146* | |
C20 | 0.7060 (3) | 0.2936 (3) | 0.3062 (2) | 0.0788 (7) | |
C21 | 0.5269 (3) | 0.5350 (4) | 0.3290 (2) | 0.0897 (9) | |
C22 | 0.3675 (4) | 0.7853 (6) | 0.3700 (5) | 0.1561 (18) | |
H22A | 0.3376 | 0.7733 | 0.2995 | 0.187* | |
H22B | 0.2816 | 0.8040 | 0.4229 | 0.187* | |
C23 | 0.4017 (6) | 0.9005 (6) | 0.3690 (7) | 0.230 (4) | |
H23A | 0.4183 | 0.9214 | 0.4409 | 0.345* | |
H23B | 0.3201 | 0.9832 | 0.3439 | 0.345* | |
H23C | 0.4915 | 0.8802 | 0.3213 | 0.345* | |
C24 | 0.7757 (3) | 0.5487 (3) | 0.10833 (17) | 0.0656 (6) | |
C25 | 0.5867 (4) | 0.6550 (4) | −0.0087 (3) | 0.1133 (11) | |
H25A | 0.5167 | 0.6803 | 0.0562 | 0.136* | |
H25B | 0.5431 | 0.6212 | −0.0640 | 0.136* | |
C26 | 0.6070 (5) | 0.7833 (4) | −0.0454 (3) | 0.1382 (15) | |
H26A | 0.6442 | 0.8207 | 0.0109 | 0.207* | |
H26B | 0.5123 | 0.8563 | −0.0629 | 0.207* | |
H26C | 0.6781 | 0.7582 | −0.1086 | 0.207* | |
O1 | 0.64499 (18) | 0.4264 (2) | 0.36659 (13) | 0.0844 (5) | |
O2 | 0.4691 (2) | 0.5291 (3) | 0.24982 (19) | 0.1154 (8) | |
O3 | 0.4910 (2) | 0.6486 (3) | 0.39597 (18) | 0.1068 (7) | |
O4 | 0.9022 (2) | 0.42899 (16) | 0.11537 (11) | 0.0759 (5) | |
O5 | 0.71982 (19) | 0.6436 (2) | 0.17533 (14) | 0.0841 (5) | |
O6 | 0.7267 (2) | 0.5393 (2) | 0.01436 (13) | 0.0903 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0463 (10) | 0.0558 (11) | 0.0577 (11) | −0.0136 (9) | −0.0074 (9) | −0.0070 (9) |
C2 | 0.0719 (14) | 0.0765 (14) | 0.0572 (12) | −0.0281 (12) | −0.0191 (10) | 0.0066 (10) |
C3 | 0.0922 (19) | 0.0984 (19) | 0.0635 (15) | −0.0203 (16) | −0.0299 (13) | 0.0056 (13) |
C4 | 0.0806 (19) | 0.110 (2) | 0.0832 (19) | −0.0094 (17) | −0.0398 (15) | −0.0162 (17) |
C5 | 0.0547 (14) | 0.0895 (18) | 0.117 (2) | −0.0165 (13) | −0.0278 (14) | −0.0306 (17) |
C6 | 0.0456 (11) | 0.0625 (13) | 0.0879 (16) | −0.0144 (10) | −0.0051 (10) | −0.0182 (12) |
C7 | 0.0563 (13) | 0.0702 (15) | 0.123 (2) | −0.0301 (12) | 0.0008 (14) | −0.0157 (15) |
C8 | 0.0773 (16) | 0.0609 (14) | 0.0935 (18) | −0.0310 (12) | 0.0195 (14) | −0.0006 (12) |
C9 | 0.0703 (13) | 0.0527 (11) | 0.0558 (12) | −0.0209 (10) | 0.0025 (10) | −0.0019 (9) |
C10 | 0.0597 (12) | 0.0518 (11) | 0.0497 (11) | −0.0224 (9) | −0.0040 (9) | −0.0004 (8) |
C11 | 0.0856 (16) | 0.0722 (14) | 0.0469 (11) | −0.0456 (12) | −0.0251 (10) | 0.0182 (9) |
C12 | 0.153 (3) | 0.0653 (14) | 0.0540 (13) | −0.0594 (17) | −0.0473 (15) | 0.0240 (11) |
C13 | 0.156 (3) | 0.0589 (15) | 0.0689 (16) | −0.0256 (17) | −0.0161 (18) | 0.0030 (12) |
C14 | 0.247 (5) | 0.0606 (18) | 0.086 (2) | −0.026 (2) | −0.025 (2) | −0.0018 (16) |
C15 | 0.404 (11) | 0.074 (3) | 0.101 (3) | −0.087 (5) | −0.097 (5) | 0.018 (2) |
C16 | 0.352 (9) | 0.099 (4) | 0.115 (4) | −0.137 (5) | −0.135 (5) | 0.051 (3) |
C17 | 0.223 (4) | 0.095 (2) | 0.092 (2) | −0.106 (3) | −0.096 (3) | 0.0478 (17) |
C18 | 0.231 (5) | 0.159 (4) | 0.151 (4) | −0.160 (4) | −0.133 (4) | 0.093 (3) |
C19 | 0.132 (3) | 0.172 (4) | 0.125 (3) | −0.115 (3) | −0.075 (2) | 0.078 (3) |
C20 | 0.0931 (18) | 0.108 (2) | 0.0636 (14) | −0.0651 (17) | −0.0355 (13) | 0.0300 (14) |
C21 | 0.0590 (15) | 0.143 (3) | 0.0812 (18) | −0.0543 (17) | −0.0184 (14) | 0.0344 (18) |
C22 | 0.076 (2) | 0.167 (4) | 0.202 (5) | −0.021 (3) | −0.044 (3) | 0.051 (4) |
C23 | 0.125 (4) | 0.120 (4) | 0.415 (11) | −0.007 (3) | −0.081 (5) | −0.015 (5) |
C24 | 0.0774 (15) | 0.0726 (15) | 0.0523 (12) | −0.0371 (13) | −0.0014 (11) | 0.0011 (11) |
C25 | 0.118 (3) | 0.132 (3) | 0.090 (2) | −0.046 (2) | −0.0384 (19) | 0.003 (2) |
C26 | 0.141 (3) | 0.114 (3) | 0.133 (3) | −0.016 (2) | −0.059 (3) | 0.005 (2) |
O1 | 0.0609 (10) | 0.1310 (15) | 0.0651 (10) | −0.0409 (10) | −0.0184 (8) | 0.0198 (10) |
O2 | 0.0984 (14) | 0.161 (2) | 0.1133 (15) | −0.0712 (15) | −0.0594 (13) | 0.0460 (14) |
O3 | 0.0681 (12) | 0.1398 (19) | 0.0970 (14) | −0.0256 (12) | −0.0139 (10) | 0.0168 (14) |
O4 | 0.1117 (13) | 0.0584 (9) | 0.0484 (8) | −0.0259 (9) | −0.0043 (8) | 0.0049 (6) |
O5 | 0.0699 (10) | 0.0953 (12) | 0.0727 (10) | −0.0180 (9) | −0.0106 (8) | −0.0172 (9) |
O6 | 0.1201 (15) | 0.0950 (13) | 0.0563 (10) | −0.0421 (12) | −0.0189 (9) | 0.0033 (8) |
C1—C6 | 1.409 (3) | C16—C17 | 1.437 (7) |
C1—C2 | 1.415 (3) | C16—H16 | 0.9300 |
C1—C10 | 1.427 (3) | C17—C18 | 1.394 (6) |
C2—C3 | 1.363 (3) | C18—C19 | 1.376 (6) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.385 (4) | C19—C20 | 1.411 (4) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.346 (4) | C20—O1 | 1.408 (3) |
C4—H4 | 0.9300 | C21—O2 | 1.189 (3) |
C5—C6 | 1.420 (4) | C21—O3 | 1.323 (4) |
C5—H5 | 0.9300 | C21—O1 | 1.342 (3) |
C6—C7 | 1.416 (4) | C22—C23 | 1.327 (6) |
C7—C8 | 1.351 (4) | C22—O3 | 1.468 (4) |
C7—H7 | 0.9300 | C22—H22A | 0.9700 |
C8—C9 | 1.397 (3) | C22—H22B | 0.9700 |
C8—H8 | 0.9300 | C23—H23A | 0.9600 |
C9—C10 | 1.366 (3) | C23—H23B | 0.9600 |
C9—O4 | 1.405 (3) | C23—H23C | 0.9600 |
C10—C11 | 1.480 (3) | C24—O5 | 1.185 (3) |
C11—C20 | 1.357 (4) | C24—O6 | 1.317 (3) |
C11—C12 | 1.442 (4) | C24—O4 | 1.337 (3) |
C12—C13 | 1.408 (4) | C25—O6 | 1.439 (4) |
C12—C17 | 1.409 (5) | C25—C26 | 1.445 (5) |
C13—C14 | 1.366 (4) | C25—H25A | 0.9700 |
C13—H13 | 0.9300 | C25—H25B | 0.9700 |
C14—C15 | 1.387 (9) | C26—H26A | 0.9600 |
C14—H14 | 0.9300 | C26—H26B | 0.9600 |
C15—C16 | 1.333 (9) | C26—H26C | 0.9600 |
C15—H15 | 0.9300 | ||
C6—C1—C2 | 118.28 (19) | C17—C16—H16 | 120.2 |
C6—C1—C10 | 119.9 (2) | C18—C17—C12 | 120.2 (4) |
C2—C1—C10 | 121.81 (18) | C18—C17—C16 | 121.6 (5) |
C3—C2—C1 | 120.7 (2) | C12—C17—C16 | 118.2 (5) |
C3—C2—H2 | 119.7 | C19—C18—C17 | 121.5 (3) |
C1—C2—H2 | 119.7 | C19—C18—H18 | 119.2 |
C2—C3—C4 | 120.7 (3) | C17—C18—H18 | 119.2 |
C2—C3—H3 | 119.6 | C18—C19—C20 | 118.2 (4) |
C4—C3—H3 | 119.6 | C18—C19—H19 | 120.9 |
C5—C4—C3 | 120.5 (2) | C20—C19—H19 | 120.9 |
C5—C4—H4 | 119.7 | C11—C20—O1 | 117.3 (2) |
C3—C4—H4 | 119.7 | C11—C20—C19 | 122.6 (3) |
C4—C5—C6 | 120.9 (2) | O1—C20—C19 | 119.9 (3) |
C4—C5—H5 | 119.5 | O2—C21—O3 | 127.6 (3) |
C6—C5—H5 | 119.5 | O2—C21—O1 | 126.0 (4) |
C1—C6—C7 | 118.5 (2) | O3—C21—O1 | 106.4 (2) |
C1—C6—C5 | 118.9 (3) | C23—C22—O3 | 114.1 (4) |
C7—C6—C5 | 122.6 (2) | C23—C22—H22A | 108.7 |
C8—C7—C6 | 121.4 (2) | O3—C22—H22A | 108.7 |
C8—C7—H7 | 119.3 | C23—C22—H22B | 108.7 |
C6—C7—H7 | 119.3 | O3—C22—H22B | 108.7 |
C7—C8—C9 | 119.4 (2) | H22A—C22—H22B | 107.6 |
C7—C8—H8 | 120.3 | C22—C23—H23A | 109.5 |
C9—C8—H8 | 120.3 | C22—C23—H23B | 109.5 |
C10—C9—C8 | 122.6 (2) | H23A—C23—H23B | 109.5 |
C10—C9—O4 | 118.20 (19) | C22—C23—H23C | 109.5 |
C8—C9—O4 | 119.0 (2) | H23A—C23—H23C | 109.5 |
C9—C10—C1 | 118.23 (19) | H23B—C23—H23C | 109.5 |
C9—C10—C11 | 121.30 (18) | O5—C24—O6 | 127.5 (2) |
C1—C10—C11 | 120.36 (17) | O5—C24—O4 | 125.5 (2) |
C20—C11—C12 | 119.2 (2) | O6—C24—O4 | 107.0 (2) |
C20—C11—C10 | 122.0 (2) | O6—C25—C26 | 111.9 (3) |
C12—C11—C10 | 118.7 (2) | O6—C25—H25A | 109.2 |
C13—C12—C17 | 119.6 (3) | C26—C25—H25A | 109.2 |
C13—C12—C11 | 122.2 (2) | O6—C25—H25B | 109.2 |
C17—C12—C11 | 118.2 (3) | C26—C25—H25B | 109.2 |
C14—C13—C12 | 120.2 (4) | H25A—C25—H25B | 107.9 |
C14—C13—H13 | 119.9 | C25—C26—H26A | 109.5 |
C12—C13—H13 | 119.9 | C25—C26—H26B | 109.5 |
C13—C14—C15 | 119.8 (5) | H26A—C26—H26B | 109.5 |
C13—C14—H14 | 120.1 | C25—C26—H26C | 109.5 |
C15—C14—H14 | 120.1 | H26A—C26—H26C | 109.5 |
C16—C15—C14 | 122.5 (5) | H26B—C26—H26C | 109.5 |
C16—C15—H15 | 118.8 | C21—O1—C20 | 116.8 (2) |
C14—C15—H15 | 118.8 | C21—O3—C22 | 117.3 (3) |
C15—C16—C17 | 119.7 (6) | C24—O4—C9 | 116.35 (16) |
C15—C16—H16 | 120.2 | C24—O6—C25 | 116.6 (2) |
C6—C1—C2—C3 | 0.2 (3) | C11—C12—C13—C14 | −179.0 (2) |
C10—C1—C2—C3 | −178.6 (2) | C12—C13—C14—C15 | −0.1 (5) |
C1—C2—C3—C4 | −0.5 (4) | C13—C14—C15—C16 | −0.9 (8) |
C2—C3—C4—C5 | 0.4 (4) | C14—C15—C16—C17 | 1.1 (9) |
C3—C4—C5—C6 | 0.0 (4) | C13—C12—C17—C18 | 178.7 (3) |
C2—C1—C6—C7 | −179.42 (19) | C11—C12—C17—C18 | −1.3 (4) |
C10—C1—C6—C7 | −0.6 (3) | C13—C12—C17—C16 | −0.8 (4) |
C2—C1—C6—C5 | 0.2 (3) | C11—C12—C17—C16 | 179.2 (3) |
C10—C1—C6—C5 | 179.01 (19) | C15—C16—C17—C18 | −179.7 (5) |
C4—C5—C6—C1 | −0.3 (3) | C15—C16—C17—C12 | −0.2 (7) |
C4—C5—C6—C7 | 179.3 (2) | C12—C17—C18—C19 | 1.6 (5) |
C1—C6—C7—C8 | 1.0 (3) | C16—C17—C18—C19 | −178.9 (3) |
C5—C6—C7—C8 | −178.6 (2) | C17—C18—C19—C20 | −0.3 (5) |
C6—C7—C8—C9 | −0.5 (4) | C12—C11—C20—O1 | 176.90 (17) |
C7—C8—C9—C10 | −0.4 (3) | C10—C11—C20—O1 | −0.8 (3) |
C7—C8—C9—O4 | −174.9 (2) | C12—C11—C20—C19 | 1.6 (3) |
C8—C9—C10—C1 | 0.7 (3) | C10—C11—C20—C19 | −176.1 (2) |
O4—C9—C10—C1 | 175.26 (17) | C18—C19—C20—C11 | −1.3 (4) |
C8—C9—C10—C11 | −175.4 (2) | C18—C19—C20—O1 | −176.5 (2) |
O4—C9—C10—C11 | −0.9 (3) | O2—C21—O1—C20 | 0.2 (4) |
C6—C1—C10—C9 | −0.2 (3) | O3—C21—O1—C20 | −178.5 (2) |
C2—C1—C10—C9 | 178.54 (18) | C11—C20—O1—C21 | 121.8 (2) |
C6—C1—C10—C11 | 175.95 (19) | C19—C20—O1—C21 | −62.7 (3) |
C2—C1—C10—C11 | −5.3 (3) | O2—C21—O3—C22 | −1.2 (4) |
C9—C10—C11—C20 | −95.4 (2) | O1—C21—O3—C22 | 177.5 (3) |
C1—C10—C11—C20 | 88.6 (2) | C23—C22—O3—C21 | −128.4 (6) |
C9—C10—C11—C12 | 86.9 (2) | O5—C24—O4—C9 | 2.6 (3) |
C1—C10—C11—C12 | −89.1 (2) | O6—C24—O4—C9 | −177.10 (18) |
C20—C11—C12—C13 | 179.7 (2) | C10—C9—O4—C24 | 100.8 (2) |
C10—C11—C12—C13 | −2.5 (3) | C8—C9—O4—C24 | −84.4 (2) |
C20—C11—C12—C17 | −0.2 (3) | O5—C24—O6—C25 | −2.2 (4) |
C10—C11—C12—C17 | 177.52 (19) | O4—C24—O6—C25 | 177.5 (2) |
C17—C12—C13—C14 | 1.0 (4) | C26—C25—O6—C24 | 79.9 (3) |
C26H22O6 | Z = 2 |
Mr = 430.44 | F(000) = 452 |
Triclinic, P1 | Dx = 1.265 Mg m−3 |
Hall symbol: -P 1 | Melting point: 417.67 K |
a = 9.8546 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0864 (19) Å | Cell parameters from 450 reflections |
c = 12.539 (2) Å | θ = 0.9–28.0° |
α = 89.469 (4)° | µ = 0.09 mm−1 |
β = 85.207 (4)° | T = 393 K |
γ = 65.578 (3)° | Block, colourless |
V = 1130.4 (3) Å3 | 0.50 × 0.31 × 0.25 mm |
Bruker SMART CCD area detector diffractometer | 4606 independent reflections |
Radiation source: fine-focus sealed tube | 2113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.909, Tmax = 0.978 | k = −12→12 |
12123 measured reflections | l = −15→15 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1049P)2 + 0.0489P] where P = (Fo2 + 2Fc2)/3 |
4606 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C26H22O6 | γ = 65.578 (3)° |
Mr = 430.44 | V = 1130.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8546 (18) Å | Mo Kα radiation |
b = 10.0864 (19) Å | µ = 0.09 mm−1 |
c = 12.539 (2) Å | T = 393 K |
α = 89.469 (4)° | 0.50 × 0.31 × 0.25 mm |
β = 85.207 (4)° |
Bruker SMART CCD area detector diffractometer | 4606 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2113 reflections with I > 2σ(I) |
Tmin = 0.909, Tmax = 0.978 | Rint = 0.025 |
12123 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.20 e Å−3 |
4606 reflections | Δρmin = −0.14 e Å−3 |
291 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 | ||
C9 | 0.4676 (3) | 0.4121 (3) | 0.2136 (2) | 0.0823 (7) | |
C8 | 0.5634 (4) | 0.4807 (3) | 0.2248 (3) | 0.1059 (9) | |
H8 | 0.5755 | 0.5415 | 0.1722 | 0.127* | |
C7 | 0.6380 (3) | 0.4568 (4) | 0.3137 (3) | 0.1100 (11) | |
H7 | 0.7028 | 0.5012 | 0.3215 | 0.132* | |
C6 | 0.6202 (3) | 0.3660 (3) | 0.3953 (3) | 0.0907 (8) | |
C5 | 0.6952 (3) | 0.3431 (4) | 0.4899 (4) | 0.1178 (12) | |
H5 | 0.7590 | 0.3880 | 0.4995 | 0.141* | |
C4 | 0.6745 (4) | 0.2563 (5) | 0.5660 (3) | 0.1305 (14) | |
H4 | 0.7246 | 0.2414 | 0.6277 | 0.157* | |
C3 | 0.5801 (4) | 0.1899 (4) | 0.5532 (2) | 0.1200 (11) | |
H3 | 0.5658 | 0.1317 | 0.6070 | 0.144* | |
C2 | 0.5071 (3) | 0.2078 (3) | 0.4632 (2) | 0.0939 (8) | |
H2 | 0.4451 | 0.1603 | 0.4555 | 0.113* | |
C1 | 0.5246 (2) | 0.2975 (3) | 0.38136 (19) | 0.0741 (7) | |
C10 | 0.4465 (3) | 0.3221 (2) | 0.28768 (18) | 0.0711 (6) | |
C11 | 0.3517 (3) | 0.2437 (3) | 0.26877 (19) | 0.0819 (7) | |
C12 | 0.4182 (5) | 0.1051 (3) | 0.2127 (2) | 0.1033 (10) | |
C13 | 0.5704 (6) | 0.0449 (4) | 0.1702 (3) | 0.1303 (13) | |
H13 | 0.6302 | 0.0943 | 0.1799 | 0.156* | |
C14 | 0.6292 (8) | −0.0873 (5) | 0.1146 (3) | 0.185 (2) | |
H14 | 0.7284 | −0.1266 | 0.0860 | 0.222* | |
C15 | 0.5395 (13) | −0.1612 (9) | 0.1016 (7) | 0.236 (6) | |
H15 | 0.5804 | −0.2499 | 0.0638 | 0.284* | |
C16 | 0.3984 (12) | −0.1098 (7) | 0.1411 (6) | 0.211 (4) | |
H16 | 0.3421 | −0.1628 | 0.1314 | 0.253* | |
C17 | 0.3314 (8) | 0.0272 (5) | 0.1990 (3) | 0.1428 (17) | |
C18 | 0.1821 (9) | 0.0866 (7) | 0.2427 (5) | 0.173 (3) | |
H18 | 0.1244 | 0.0346 | 0.2346 | 0.208* | |
C19 | 0.1185 (5) | 0.2178 (6) | 0.2967 (3) | 0.1450 (16) | |
H19 | 0.0195 | 0.2547 | 0.3257 | 0.174* | |
C20 | 0.2061 (4) | 0.2951 (4) | 0.3071 (3) | 0.0981 (9) | |
C21 | 0.0277 (4) | 0.5372 (5) | 0.3321 (3) | 0.1146 (11) | |
C22 | −0.1321 (5) | 0.7855 (7) | 0.3744 (5) | 0.193 (2) | |
H22A | −0.1686 | 0.7727 | 0.3075 | 0.231* | |
H22B | −0.2126 | 0.8056 | 0.4304 | 0.231* | |
C23 | −0.0969 (7) | 0.8987 (7) | 0.3675 (8) | 0.271 (4) | |
H23A | −0.0584 | 0.9106 | 0.4328 | 0.406* | |
H23B | −0.1845 | 0.9850 | 0.3558 | 0.406* | |
H23C | −0.0222 | 0.8826 | 0.3088 | 0.406* | |
C24 | 0.2760 (4) | 0.5497 (4) | 0.1086 (2) | 0.0918 (8) | |
C25 | 0.0881 (6) | 0.6574 (6) | −0.0097 (4) | 0.1675 (17) | |
H25A | 0.0460 | 0.6229 | −0.0647 | 0.201* | |
H25B | 0.0179 | 0.6836 | 0.0537 | 0.201* | |
C26 | 0.1087 (7) | 0.7799 (7) | −0.0452 (5) | 0.221 (3) | |
H26A | 0.1338 | 0.8239 | 0.0132 | 0.332* | |
H26B | 0.0182 | 0.8486 | −0.0717 | 0.332* | |
H26C | 0.1884 | 0.7513 | −0.1014 | 0.332* | |
O1 | 0.1472 (2) | 0.4271 (3) | 0.36652 (15) | 0.1072 (7) | |
O2 | −0.0321 (3) | 0.5314 (3) | 0.2544 (2) | 0.1511 (10) | |
O3 | −0.0057 (3) | 0.6493 (4) | 0.3976 (2) | 0.1366 (9) | |
O4 | 0.3986 (3) | 0.4290 (2) | 0.11726 (13) | 0.1001 (6) | |
O5 | 0.2275 (3) | 0.5428 (3) | 0.01496 (16) | 0.1252 (8) | |
O6 | 0.2217 (2) | 0.6446 (3) | 0.17393 (18) | 0.1189 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C9 | 0.0893 (18) | 0.0724 (15) | 0.0784 (17) | −0.0280 (14) | 0.0012 (14) | −0.0010 (13) |
C8 | 0.103 (2) | 0.088 (2) | 0.126 (3) | −0.0442 (19) | 0.018 (2) | −0.0016 (18) |
C7 | 0.0753 (19) | 0.099 (2) | 0.161 (3) | −0.0432 (17) | 0.003 (2) | −0.023 (2) |
C6 | 0.0632 (16) | 0.0860 (18) | 0.113 (2) | −0.0214 (15) | −0.0047 (15) | −0.0203 (17) |
C5 | 0.0738 (19) | 0.120 (3) | 0.146 (3) | −0.0222 (19) | −0.030 (2) | −0.038 (2) |
C4 | 0.106 (3) | 0.147 (3) | 0.113 (3) | −0.019 (3) | −0.050 (2) | −0.021 (3) |
C3 | 0.119 (3) | 0.130 (3) | 0.092 (2) | −0.027 (2) | −0.0423 (19) | 0.0096 (18) |
C2 | 0.0957 (19) | 0.104 (2) | 0.0793 (17) | −0.0360 (16) | −0.0231 (15) | 0.0092 (15) |
C1 | 0.0612 (14) | 0.0752 (15) | 0.0779 (16) | −0.0196 (13) | −0.0097 (12) | −0.0067 (12) |
C10 | 0.0739 (15) | 0.0684 (14) | 0.0703 (14) | −0.0289 (12) | −0.0050 (12) | −0.0003 (12) |
C11 | 0.107 (2) | 0.0892 (19) | 0.0649 (14) | −0.0526 (17) | −0.0276 (14) | 0.0185 (13) |
C12 | 0.174 (3) | 0.086 (2) | 0.0731 (17) | −0.070 (2) | −0.050 (2) | 0.0239 (16) |
C13 | 0.195 (4) | 0.081 (2) | 0.096 (2) | −0.038 (2) | −0.011 (2) | 0.0025 (18) |
C14 | 0.303 (7) | 0.082 (3) | 0.121 (3) | −0.033 (3) | −0.010 (3) | −0.009 (2) |
C15 | 0.474 (16) | 0.104 (5) | 0.133 (5) | −0.110 (8) | −0.097 (7) | 0.016 (4) |
C16 | 0.437 (13) | 0.115 (5) | 0.147 (6) | −0.158 (7) | −0.151 (7) | 0.051 (4) |
C17 | 0.250 (5) | 0.113 (3) | 0.115 (3) | −0.111 (4) | −0.101 (3) | 0.051 (2) |
C18 | 0.255 (7) | 0.182 (5) | 0.181 (5) | −0.170 (6) | −0.137 (5) | 0.095 (4) |
C19 | 0.154 (3) | 0.193 (4) | 0.147 (3) | −0.122 (4) | −0.069 (3) | 0.072 (3) |
C20 | 0.111 (2) | 0.124 (3) | 0.0896 (19) | −0.073 (2) | −0.0412 (18) | 0.0306 (19) |
C21 | 0.077 (2) | 0.169 (4) | 0.113 (3) | −0.065 (2) | −0.023 (2) | 0.040 (3) |
C22 | 0.102 (3) | 0.196 (5) | 0.245 (6) | −0.021 (4) | −0.046 (3) | 0.050 (5) |
C23 | 0.158 (5) | 0.163 (5) | 0.442 (13) | −0.009 (5) | −0.069 (6) | 0.001 (7) |
C24 | 0.102 (2) | 0.097 (2) | 0.0776 (19) | −0.0431 (19) | −0.0020 (17) | 0.0007 (17) |
C25 | 0.200 (5) | 0.152 (4) | 0.139 (3) | −0.053 (4) | −0.056 (3) | 0.016 (3) |
C26 | 0.217 (6) | 0.187 (5) | 0.203 (5) | −0.014 (5) | −0.084 (4) | 0.001 (5) |
O1 | 0.0784 (13) | 0.1540 (19) | 0.0913 (13) | −0.0479 (13) | −0.0214 (10) | 0.0186 (13) |
O2 | 0.1265 (19) | 0.190 (3) | 0.159 (2) | −0.0774 (18) | −0.0736 (17) | 0.0463 (19) |
O3 | 0.0937 (17) | 0.162 (2) | 0.1313 (19) | −0.0298 (17) | −0.0134 (14) | 0.0085 (18) |
O4 | 0.1336 (17) | 0.0802 (12) | 0.0721 (11) | −0.0306 (12) | −0.0065 (11) | 0.0088 (9) |
O5 | 0.153 (2) | 0.1263 (18) | 0.0842 (14) | −0.0423 (16) | −0.0267 (13) | 0.0101 (12) |
O6 | 0.1020 (15) | 0.1224 (16) | 0.1077 (15) | −0.0204 (13) | −0.0145 (12) | −0.0206 (14) |
C9—C10 | 1.355 (3) | C16—C17 | 1.434 (8) |
C9—C8 | 1.398 (4) | C16—H16 | 0.9300 |
C9—O4 | 1.411 (3) | C17—C18 | 1.402 (7) |
C8—C7 | 1.352 (4) | C18—C19 | 1.365 (7) |
C8—H8 | 0.9300 | C18—H18 | 0.9300 |
C7—C6 | 1.415 (4) | C19—C20 | 1.396 (5) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C6—C1 | 1.401 (4) | C20—O1 | 1.404 (4) |
C6—C5 | 1.416 (4) | C21—O2 | 1.194 (4) |
C5—C4 | 1.349 (5) | C21—O3 | 1.313 (4) |
C5—H5 | 0.9300 | C21—O1 | 1.342 (4) |
C4—C3 | 1.372 (5) | C22—C23 | 1.324 (7) |
C4—H4 | 0.9300 | C22—O3 | 1.470 (5) |
C3—C2 | 1.360 (4) | C22—H22A | 0.9700 |
C3—H3 | 0.9300 | C22—H22B | 0.9700 |
C2—C1 | 1.408 (3) | C23—H23A | 0.9600 |
C2—H2 | 0.9300 | C23—H23B | 0.9600 |
C1—C10 | 1.422 (3) | C23—H23C | 0.9600 |
C10—C11 | 1.484 (3) | C24—O6 | 1.179 (3) |
C11—C20 | 1.354 (4) | C24—O5 | 1.317 (3) |
C11—C12 | 1.436 (4) | C24—O4 | 1.326 (3) |
C12—C17 | 1.401 (5) | C25—C26 | 1.396 (7) |
C12—C13 | 1.422 (5) | C25—O5 | 1.439 (5) |
C13—C14 | 1.382 (5) | C25—H25A | 0.9700 |
C13—H13 | 0.9300 | C25—H25B | 0.9700 |
C14—C15 | 1.391 (11) | C26—H26A | 0.9600 |
C14—H14 | 0.9300 | C26—H26B | 0.9600 |
C15—C16 | 1.320 (12) | C26—H26C | 0.9600 |
C15—H15 | 0.9300 | ||
C10—C9—C8 | 123.0 (3) | C17—C16—H16 | 119.8 |
C10—C9—O4 | 118.6 (2) | C12—C17—C18 | 118.5 (5) |
C8—C9—O4 | 118.2 (3) | C12—C17—C16 | 118.8 (6) |
C7—C8—C9 | 118.6 (3) | C18—C17—C16 | 122.7 (6) |
C7—C8—H8 | 120.7 | C19—C18—C17 | 122.4 (5) |
C9—C8—H8 | 120.7 | C19—C18—H18 | 118.8 |
C8—C7—C6 | 121.7 (3) | C17—C18—H18 | 118.8 |
C8—C7—H7 | 119.1 | C18—C19—C20 | 118.1 (5) |
C6—C7—H7 | 119.1 | C18—C19—H19 | 120.9 |
C1—C6—C7 | 118.4 (3) | C20—C19—H19 | 120.9 |
C1—C6—C5 | 119.5 (3) | C11—C20—C19 | 122.9 (4) |
C7—C6—C5 | 122.1 (3) | C11—C20—O1 | 117.0 (3) |
C4—C5—C6 | 120.3 (3) | C19—C20—O1 | 119.8 (4) |
C4—C5—H5 | 119.8 | O2—C21—O3 | 127.9 (4) |
C6—C5—H5 | 119.8 | O2—C21—O1 | 124.8 (5) |
C5—C4—C3 | 120.5 (3) | O3—C21—O1 | 107.2 (3) |
C5—C4—H4 | 119.8 | C23—C22—O3 | 113.2 (5) |
C3—C4—H4 | 119.8 | C23—C22—H22A | 108.9 |
C2—C3—C4 | 121.1 (4) | O3—C22—H22A | 108.9 |
C2—C3—H3 | 119.5 | C23—C22—H22B | 108.9 |
C4—C3—H3 | 119.5 | O3—C22—H22B | 108.9 |
C3—C2—C1 | 120.6 (3) | H22A—C22—H22B | 107.8 |
C3—C2—H2 | 119.7 | C22—C23—H23A | 109.5 |
C1—C2—H2 | 119.7 | C22—C23—H23B | 109.5 |
C6—C1—C2 | 118.0 (2) | H23A—C23—H23B | 109.5 |
C6—C1—C10 | 119.9 (2) | C22—C23—H23C | 109.5 |
C2—C1—C10 | 122.1 (2) | H23A—C23—H23C | 109.5 |
C9—C10—C1 | 118.3 (2) | H23B—C23—H23C | 109.5 |
C9—C10—C11 | 121.0 (2) | O6—C24—O5 | 127.1 (3) |
C1—C10—C11 | 120.5 (2) | O6—C24—O4 | 125.4 (3) |
C20—C11—C12 | 118.6 (3) | O5—C24—O4 | 107.4 (3) |
C20—C11—C10 | 122.2 (3) | C26—C25—O5 | 111.0 (5) |
C12—C11—C10 | 119.1 (3) | C26—C25—H25A | 109.4 |
C17—C12—C13 | 119.0 (4) | O5—C25—H25A | 109.4 |
C17—C12—C11 | 119.5 (4) | C26—C25—H25B | 109.4 |
C13—C12—C11 | 121.5 (3) | O5—C25—H25B | 109.4 |
C14—C13—C12 | 119.7 (5) | H25A—C25—H25B | 108.0 |
C14—C13—H13 | 120.1 | C25—C26—H26A | 109.5 |
C12—C13—H13 | 120.1 | C25—C26—H26B | 109.5 |
C13—C14—C15 | 119.8 (7) | H26A—C26—H26B | 109.5 |
C13—C14—H14 | 120.1 | C25—C26—H26C | 109.5 |
C15—C14—H14 | 120.1 | H26A—C26—H26C | 109.5 |
C16—C15—C14 | 122.2 (9) | H26B—C26—H26C | 109.5 |
C16—C15—H15 | 118.9 | C21—O1—C20 | 117.7 (3) |
C14—C15—H15 | 118.9 | C21—O3—C22 | 117.3 (4) |
C15—C16—C17 | 120.4 (9) | C24—O4—C9 | 116.9 (2) |
C15—C16—H16 | 119.8 | C24—O5—C25 | 117.8 (3) |
C10—C9—C8—C7 | −0.3 (4) | C11—C12—C13—C14 | −178.5 (3) |
O4—C9—C8—C7 | −175.4 (3) | C12—C13—C14—C15 | −0.7 (7) |
C9—C8—C7—C6 | −0.7 (4) | C13—C14—C15—C16 | −0.3 (12) |
C8—C7—C6—C1 | 1.3 (4) | C14—C15—C16—C17 | 0.6 (14) |
C8—C7—C6—C5 | −178.5 (3) | C13—C12—C17—C18 | 179.0 (3) |
C1—C6—C5—C4 | −0.2 (4) | C11—C12—C17—C18 | −1.2 (5) |
C7—C6—C5—C4 | 179.6 (3) | C13—C12—C17—C16 | −0.9 (5) |
C6—C5—C4—C3 | −0.4 (5) | C11—C12—C17—C16 | 178.9 (3) |
C5—C4—C3—C2 | 1.1 (5) | C15—C16—C17—C12 | 0.0 (10) |
C4—C3—C2—C1 | −1.2 (5) | C15—C16—C17—C18 | −179.9 (7) |
C7—C6—C1—C2 | −179.7 (2) | C12—C17—C18—C19 | 0.8 (6) |
C5—C6—C1—C2 | 0.0 (3) | C16—C17—C18—C19 | −179.3 (4) |
C7—C6—C1—C10 | −1.0 (3) | C17—C18—C19—C20 | 0.7 (6) |
C5—C6—C1—C10 | 178.7 (2) | C12—C11—C20—C19 | 1.6 (4) |
C3—C2—C1—C6 | 0.7 (4) | C10—C11—C20—C19 | −175.2 (3) |
C3—C2—C1—C10 | −178.0 (2) | C12—C11—C20—O1 | 176.6 (2) |
C8—C9—C10—C1 | 0.5 (4) | C10—C11—C20—O1 | −0.2 (4) |
O4—C9—C10—C1 | 175.7 (2) | C18—C19—C20—C11 | −2.0 (5) |
C8—C9—C10—C11 | −175.7 (2) | C18—C19—C20—O1 | −176.9 (3) |
O4—C9—C10—C11 | −0.6 (3) | O2—C21—O1—C20 | −0.2 (4) |
C6—C1—C10—C9 | 0.2 (3) | O3—C21—O1—C20 | −178.6 (2) |
C2—C1—C10—C9 | 178.8 (2) | C11—C20—O1—C21 | 122.5 (3) |
C6—C1—C10—C11 | 176.4 (2) | C19—C20—O1—C21 | −62.3 (3) |
C2—C1—C10—C11 | −4.9 (3) | O2—C21—O3—C22 | 0.3 (6) |
C9—C10—C11—C20 | −96.2 (3) | O1—C21—O3—C22 | 178.6 (3) |
C1—C10—C11—C20 | 87.6 (3) | C23—C22—O3—C21 | −125.9 (7) |
C9—C10—C11—C12 | 87.0 (3) | O6—C24—O4—C9 | 1.2 (4) |
C1—C10—C11—C12 | −89.2 (3) | O5—C24—O4—C9 | −178.5 (2) |
C20—C11—C12—C17 | 0.1 (4) | C10—C9—O4—C24 | 102.2 (3) |
C10—C11—C12—C17 | 177.0 (2) | C8—C9—O4—C24 | −82.4 (3) |
C20—C11—C12—C13 | 179.9 (3) | O6—C24—O5—C25 | −4.3 (5) |
C10—C11—C12—C13 | −3.2 (4) | O4—C24—O5—C25 | 175.3 (3) |
C17—C12—C13—C14 | 1.3 (5) | C26—C25—O5—C24 | 81.1 (5) |
C26H22O6 | Z = 4 |
Mr = 430.44 | F(000) = 904 |
Triclinic, P1 | Dx = 1.336 Mg m−3 |
Hall symbol: -P 1 | Melting point: 417.67 K |
a = 10.8028 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.798 (3) Å | Cell parameters from 615 reflections |
c = 15.926 (3) Å | θ = 0.9–28.0° |
α = 63.692 (2)° | µ = 0.10 mm−1 |
β = 72.394 (3)° | T = 150 K |
γ = 73.200 (3)° | Block, colourless |
V = 2139.2 (7) Å3 | 0.50 × 0.31 × 0.25 mm |
Bruker SMART CCD area detector diffractometer | 8704 independent reflections |
Radiation source: fine-focus sealed tube | 6807 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.906, Tmax = 0.977 | k = −18→18 |
22856 measured reflections | l = −19→19 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0697P)2 + 0.7813P] where P = (Fo2 + 2Fc2)/3 |
8704 reflections | (Δ/σ)max < 0.001 |
581 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C26H22O6 | γ = 73.200 (3)° |
Mr = 430.44 | V = 2139.2 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.8028 (18) Å | Mo Kα radiation |
b = 14.798 (3) Å | µ = 0.10 mm−1 |
c = 15.926 (3) Å | T = 150 K |
α = 63.692 (2)° | 0.50 × 0.31 × 0.25 mm |
β = 72.394 (3)° |
Bruker SMART CCD area detector diffractometer | 8704 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6807 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 0.977 | Rint = 0.024 |
22856 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.57 e Å−3 |
8704 reflections | Δρmin = −0.47 e Å−3 |
581 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 | ||
C9 | 0.88531 (17) | 0.66802 (13) | 0.53583 (12) | 0.0301 (4) | |
C8 | 0.86489 (19) | 0.58282 (14) | 0.62148 (14) | 0.0375 (4) | |
H8 | 0.9185 | 0.5176 | 0.6280 | 0.045* | |
C7 | 0.76734 (19) | 0.59438 (15) | 0.69546 (14) | 0.0409 (5) | |
H7 | 0.7536 | 0.5367 | 0.7539 | 0.049* | |
C6 | 0.68609 (18) | 0.69068 (15) | 0.68679 (13) | 0.0359 (4) | |
C5 | 0.5870 (2) | 0.70589 (19) | 0.76367 (14) | 0.0474 (5) | |
H5 | 0.5724 | 0.6494 | 0.8230 | 0.057* | |
C4 | 0.5123 (2) | 0.7999 (2) | 0.75396 (16) | 0.0527 (6) | |
H4 | 0.4477 | 0.8090 | 0.8067 | 0.063* | |
C3 | 0.5304 (2) | 0.88385 (18) | 0.66612 (16) | 0.0487 (5) | |
H3 | 0.4766 | 0.9490 | 0.6595 | 0.058* | |
C2 | 0.62456 (18) | 0.87264 (15) | 0.59011 (14) | 0.0374 (4) | |
H2 | 0.6354 | 0.9301 | 0.5311 | 0.045* | |
C1 | 0.70627 (16) | 0.77624 (14) | 0.59825 (12) | 0.0303 (4) | |
C10 | 0.80967 (16) | 0.76329 (13) | 0.52119 (12) | 0.0270 (4) | |
C11 | 0.83061 (16) | 0.85082 (13) | 0.42699 (12) | 0.0285 (4) | |
C12 | 0.76089 (17) | 0.87052 (15) | 0.35535 (13) | 0.0351 (4) | |
C13 | 0.67404 (19) | 0.80690 (18) | 0.37007 (17) | 0.0473 (5) | |
H13 | 0.6569 | 0.7516 | 0.4299 | 0.057* | |
C14 | 0.6143 (2) | 0.8254 (2) | 0.2973 (2) | 0.0631 (7) | |
H14 | 0.5567 | 0.7821 | 0.3073 | 0.076* | |
C15 | 0.6378 (2) | 0.9072 (2) | 0.20887 (19) | 0.0688 (9) | |
H15 | 0.5982 | 0.9177 | 0.1587 | 0.083* | |
C16 | 0.7167 (2) | 0.9716 (2) | 0.19449 (16) | 0.0607 (7) | |
H16 | 0.7287 | 1.0283 | 0.1350 | 0.073* | |
C17 | 0.78115 (19) | 0.95580 (16) | 0.26613 (13) | 0.0429 (5) | |
C18 | 0.8647 (2) | 1.02079 (16) | 0.25272 (14) | 0.0478 (5) | |
H18 | 0.8751 | 1.0794 | 0.1946 | 0.057* | |
C19 | 0.9305 (2) | 1.00156 (15) | 0.32084 (13) | 0.0417 (5) | |
H19 | 0.9867 | 1.0459 | 0.3107 | 0.050* | |
C20 | 0.91428 (17) | 0.91493 (13) | 0.40667 (12) | 0.0308 (4) | |
C21 | 1.11330 (18) | 0.87624 (13) | 0.45672 (13) | 0.0352 (4) | |
C22 | 1.2960 (2) | 0.8445 (3) | 0.5246 (2) | 0.0839 (10) | |
H22A | 1.3412 | 0.8404 | 0.4619 | 0.101* | |
H22B | 1.3231 | 0.9014 | 0.5275 | 0.101* | |
C23 | 1.3368 (3) | 0.7566 (3) | 0.5942 (3) | 0.1322 (19) | |
H23A | 1.2810 | 0.7543 | 0.6562 | 0.198* | |
H23B | 1.4287 | 0.7528 | 0.5946 | 0.198* | |
H23C | 1.3305 | 0.6984 | 0.5828 | 0.198* | |
C24 | 1.10839 (17) | 0.64031 (13) | 0.46319 (12) | 0.0296 (4) | |
C25 | 1.3244 (2) | 0.61181 (19) | 0.37615 (15) | 0.0492 (5) | |
H25A | 1.3447 | 0.6573 | 0.3988 | 0.059* | |
H25B | 1.3692 | 0.6291 | 0.3082 | 0.059* | |
C26 | 1.3759 (2) | 0.5030 (2) | 0.43362 (16) | 0.0549 (6) | |
H26A | 1.3347 | 0.4866 | 0.5013 | 0.082* | |
H26B | 1.4719 | 0.4930 | 0.4255 | 0.082* | |
H26C | 1.3550 | 0.4577 | 0.4118 | 0.082* | |
C9' | 0.65209 (16) | 0.84072 (12) | −0.05936 (12) | 0.0261 (3) | |
C8' | 0.66681 (18) | 0.91318 (13) | −0.15391 (13) | 0.0326 (4) | |
H8' | 0.6143 | 0.9799 | −0.1693 | 0.039* | |
C7' | 0.75771 (18) | 0.88624 (14) | −0.22322 (12) | 0.0334 (4) | |
H7' | 0.7693 | 0.9352 | −0.2873 | 0.040* | |
C6' | 0.83525 (16) | 0.78688 (13) | −0.20170 (11) | 0.0272 (4) | |
C5' | 0.93010 (17) | 0.75710 (15) | −0.27287 (12) | 0.0350 (4) | |
H5' | 0.9439 | 0.8055 | −0.3371 | 0.042* | |
C4' | 1.00187 (17) | 0.66022 (16) | −0.25068 (13) | 0.0377 (4) | |
H4' | 1.0651 | 0.6417 | −0.2994 | 0.045* | |
C3' | 0.98268 (17) | 0.58778 (15) | −0.15622 (13) | 0.0358 (4) | |
H3' | 1.0319 | 0.5200 | −0.1415 | 0.043* | |
C2' | 0.89383 (16) | 0.61386 (13) | −0.08533 (12) | 0.0285 (4) | |
H2' | 0.8830 | 0.5643 | −0.0215 | 0.034* | |
C1' | 0.81749 (15) | 0.71388 (12) | −0.10563 (11) | 0.0235 (3) | |
C10' | 0.72427 (15) | 0.74340 (12) | −0.03325 (11) | 0.0227 (3) | |
C11' | 0.71286 (15) | 0.67215 (12) | 0.06926 (11) | 0.0239 (3) | |
C12' | 0.79007 (16) | 0.67694 (12) | 0.12552 (11) | 0.0265 (4) | |
C13' | 0.87661 (17) | 0.74736 (14) | 0.08752 (13) | 0.0326 (4) | |
H13' | 0.8834 | 0.7944 | 0.0227 | 0.039* | |
C14' | 0.95090 (19) | 0.74904 (16) | 0.14263 (15) | 0.0415 (5) | |
H14' | 1.0089 | 0.7969 | 0.1156 | 0.050* | |
C15' | 0.9424 (2) | 0.68083 (18) | 0.23856 (15) | 0.0463 (5) | |
H15' | 0.9940 | 0.6828 | 0.2764 | 0.056* | |
C16' | 0.85976 (19) | 0.61167 (16) | 0.27742 (13) | 0.0412 (5) | |
H16' | 0.8545 | 0.5657 | 0.3425 | 0.049* | |
C17' | 0.78184 (17) | 0.60691 (14) | 0.22295 (12) | 0.0313 (4) | |
C18' | 0.69883 (18) | 0.53345 (15) | 0.26066 (12) | 0.0366 (4) | |
H18' | 0.6937 | 0.4860 | 0.3253 | 0.044* | |
C19' | 0.62607 (18) | 0.52923 (14) | 0.20625 (13) | 0.0349 (4) | |
H19' | 0.5709 | 0.4795 | 0.2325 | 0.042* | |
C20' | 0.63401 (16) | 0.59991 (13) | 0.11036 (12) | 0.0273 (4) | |
C21' | 0.43476 (17) | 0.60739 (13) | 0.07454 (12) | 0.0303 (4) | |
C22' | 0.2503 (2) | 0.6301 (2) | 0.01457 (18) | 0.0619 (7) | |
H22C | 0.2153 | 0.5668 | 0.0594 | 0.074* | |
H22D | 0.2098 | 0.6833 | 0.0414 | 0.074* | |
C23' | 0.2168 (2) | 0.6646 (2) | −0.07797 (19) | 0.0620 (6) | |
H23D | 0.2478 | 0.7292 | −0.1211 | 0.093* | |
H23E | 0.1208 | 0.6753 | −0.0701 | 0.093* | |
H23F | 0.2593 | 0.6126 | −0.1051 | 0.093* | |
C24' | 0.44117 (16) | 0.85632 (12) | 0.03596 (12) | 0.0271 (4) | |
C25' | 0.2437 (2) | 0.86349 (16) | 0.14989 (14) | 0.0436 (5) | |
H25C | 0.2178 | 0.8549 | 0.2178 | 0.052* | |
H25D | 0.2331 | 0.8010 | 0.1465 | 0.052* | |
C26' | 0.1550 (2) | 0.95425 (17) | 0.09355 (16) | 0.0487 (5) | |
H26D | 0.1690 | 1.0167 | 0.0937 | 0.073* | |
H26E | 0.0628 | 0.9464 | 0.1225 | 0.073* | |
H26F | 0.1750 | 0.9592 | 0.0276 | 0.073* | |
O1' | 0.56796 (11) | 0.59333 (9) | 0.05038 (8) | 0.0310 (3) | |
O2' | 0.36942 (12) | 0.61512 (11) | 0.14712 (9) | 0.0402 (3) | |
O3' | 0.39300 (12) | 0.61031 (11) | 0.00350 (10) | 0.0394 (3) | |
O4' | 0.56635 (11) | 0.87177 (9) | 0.01344 (9) | 0.0314 (3) | |
O5' | 0.39527 (12) | 0.83001 (10) | −0.00720 (9) | 0.0341 (3) | |
O3 | 1.15425 (13) | 0.86851 (12) | 0.53001 (10) | 0.0479 (4) | |
O1 | 0.97992 (12) | 0.89703 (9) | 0.47804 (8) | 0.0329 (3) | |
O2 | 1.17874 (14) | 0.86644 (11) | 0.38475 (10) | 0.0491 (4) | |
O6' | 0.38202 (12) | 0.87517 (10) | 0.11379 (9) | 0.0371 (3) | |
O4 | 0.98174 (12) | 0.65430 (10) | 0.45787 (9) | 0.0350 (3) | |
O6 | 1.18207 (13) | 0.62973 (10) | 0.38380 (9) | 0.0398 (3) | |
O5 | 1.14496 (12) | 0.63774 (11) | 0.52801 (9) | 0.0373 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C9 | 0.0281 (9) | 0.0341 (9) | 0.0336 (9) | −0.0039 (7) | −0.0095 (7) | −0.0169 (8) |
C8 | 0.0382 (10) | 0.0291 (9) | 0.0468 (11) | −0.0063 (8) | −0.0172 (9) | −0.0104 (8) |
C7 | 0.0416 (11) | 0.0400 (11) | 0.0378 (10) | −0.0204 (9) | −0.0118 (9) | −0.0019 (9) |
C6 | 0.0309 (9) | 0.0461 (11) | 0.0321 (9) | −0.0189 (8) | −0.0036 (7) | −0.0109 (8) |
C5 | 0.0386 (11) | 0.0695 (15) | 0.0338 (10) | −0.0292 (11) | 0.0042 (8) | −0.0154 (10) |
C4 | 0.0364 (11) | 0.0826 (17) | 0.0441 (12) | −0.0239 (11) | 0.0147 (9) | −0.0358 (12) |
C3 | 0.0331 (11) | 0.0619 (14) | 0.0531 (13) | −0.0070 (10) | 0.0044 (9) | −0.0337 (11) |
C2 | 0.0286 (9) | 0.0444 (11) | 0.0386 (10) | −0.0059 (8) | −0.0005 (8) | −0.0200 (9) |
C1 | 0.0236 (8) | 0.0396 (10) | 0.0307 (9) | −0.0102 (7) | −0.0030 (7) | −0.0150 (8) |
C10 | 0.0245 (8) | 0.0313 (9) | 0.0283 (8) | −0.0065 (7) | −0.0063 (7) | −0.0127 (7) |
C11 | 0.0253 (8) | 0.0321 (9) | 0.0258 (8) | 0.0031 (7) | −0.0040 (7) | −0.0150 (7) |
C12 | 0.0288 (9) | 0.0438 (10) | 0.0336 (10) | 0.0109 (8) | −0.0094 (7) | −0.0246 (8) |
C13 | 0.0339 (11) | 0.0639 (14) | 0.0575 (13) | 0.0066 (10) | −0.0162 (9) | −0.0403 (12) |
C14 | 0.0385 (12) | 0.0931 (19) | 0.0873 (19) | 0.0169 (12) | −0.0293 (12) | −0.0680 (17) |
C15 | 0.0503 (14) | 0.109 (2) | 0.0624 (16) | 0.0374 (15) | −0.0358 (13) | −0.0629 (17) |
C16 | 0.0502 (13) | 0.0862 (18) | 0.0399 (12) | 0.0324 (13) | −0.0222 (10) | −0.0383 (12) |
C17 | 0.0372 (10) | 0.0540 (12) | 0.0293 (10) | 0.0202 (9) | −0.0104 (8) | −0.0242 (9) |
C18 | 0.0492 (12) | 0.0449 (12) | 0.0258 (10) | 0.0069 (10) | 0.0008 (9) | −0.0080 (9) |
C19 | 0.0418 (11) | 0.0375 (10) | 0.0321 (10) | −0.0057 (8) | 0.0032 (8) | −0.0095 (8) |
C20 | 0.0301 (9) | 0.0337 (9) | 0.0239 (8) | −0.0040 (7) | −0.0001 (7) | −0.0118 (7) |
C21 | 0.0314 (9) | 0.0280 (9) | 0.0331 (10) | −0.0081 (7) | 0.0005 (8) | −0.0034 (8) |
C22 | 0.0305 (12) | 0.117 (3) | 0.0653 (17) | −0.0192 (14) | −0.0124 (12) | 0.0030 (17) |
C23 | 0.0530 (18) | 0.112 (3) | 0.155 (4) | −0.0312 (18) | −0.051 (2) | 0.043 (3) |
C24 | 0.0346 (9) | 0.0288 (9) | 0.0274 (9) | −0.0051 (7) | −0.0067 (7) | −0.0129 (7) |
C25 | 0.0386 (11) | 0.0784 (16) | 0.0359 (11) | −0.0163 (11) | 0.0065 (9) | −0.0324 (11) |
C26 | 0.0330 (11) | 0.0853 (18) | 0.0487 (13) | −0.0033 (11) | −0.0079 (9) | −0.0330 (13) |
C9' | 0.0245 (8) | 0.0281 (8) | 0.0305 (9) | −0.0030 (7) | −0.0077 (7) | −0.0152 (7) |
C8' | 0.0352 (10) | 0.0246 (8) | 0.0377 (10) | −0.0028 (7) | −0.0162 (8) | −0.0079 (7) |
C7' | 0.0373 (10) | 0.0339 (9) | 0.0255 (9) | −0.0127 (8) | −0.0103 (7) | −0.0021 (7) |
C6' | 0.0249 (8) | 0.0351 (9) | 0.0239 (8) | −0.0123 (7) | −0.0049 (6) | −0.0095 (7) |
C5' | 0.0310 (9) | 0.0543 (12) | 0.0214 (8) | −0.0181 (8) | 0.0009 (7) | −0.0138 (8) |
C4' | 0.0262 (9) | 0.0606 (13) | 0.0323 (10) | −0.0072 (8) | 0.0031 (7) | −0.0294 (9) |
C3' | 0.0283 (9) | 0.0444 (11) | 0.0370 (10) | 0.0012 (8) | −0.0046 (8) | −0.0238 (9) |
C2' | 0.0255 (8) | 0.0338 (9) | 0.0256 (8) | −0.0024 (7) | −0.0044 (7) | −0.0133 (7) |
C1' | 0.0187 (7) | 0.0310 (8) | 0.0231 (8) | −0.0069 (6) | −0.0033 (6) | −0.0119 (7) |
C10' | 0.0209 (8) | 0.0264 (8) | 0.0222 (8) | −0.0066 (6) | −0.0046 (6) | −0.0091 (6) |
C11' | 0.0224 (8) | 0.0254 (8) | 0.0218 (8) | 0.0007 (6) | −0.0013 (6) | −0.0125 (7) |
C12' | 0.0242 (8) | 0.0289 (8) | 0.0255 (8) | 0.0037 (7) | −0.0045 (6) | −0.0154 (7) |
C13' | 0.0327 (9) | 0.0345 (9) | 0.0336 (9) | −0.0002 (7) | −0.0107 (7) | −0.0171 (8) |
C14' | 0.0354 (10) | 0.0494 (12) | 0.0503 (12) | −0.0034 (9) | −0.0156 (9) | −0.0269 (10) |
C15' | 0.0376 (11) | 0.0680 (14) | 0.0448 (12) | 0.0062 (10) | −0.0200 (9) | −0.0342 (11) |
C16' | 0.0349 (10) | 0.0572 (13) | 0.0270 (9) | 0.0104 (9) | −0.0115 (8) | −0.0205 (9) |
C17' | 0.0271 (9) | 0.0375 (10) | 0.0235 (8) | 0.0062 (7) | −0.0036 (7) | −0.0150 (7) |
C18' | 0.0326 (10) | 0.0404 (10) | 0.0222 (8) | 0.0019 (8) | −0.0002 (7) | −0.0080 (8) |
C19' | 0.0319 (9) | 0.0327 (9) | 0.0293 (9) | −0.0069 (7) | 0.0050 (7) | −0.0091 (8) |
C20' | 0.0247 (8) | 0.0308 (9) | 0.0260 (8) | −0.0022 (7) | −0.0009 (7) | −0.0151 (7) |
C21' | 0.0295 (9) | 0.0278 (9) | 0.0333 (9) | −0.0119 (7) | 0.0013 (7) | −0.0125 (7) |
C22' | 0.0299 (11) | 0.108 (2) | 0.0606 (15) | −0.0248 (12) | −0.0003 (10) | −0.0424 (15) |
C23' | 0.0386 (12) | 0.0725 (17) | 0.0722 (17) | −0.0086 (11) | −0.0145 (11) | −0.0247 (14) |
C24' | 0.0315 (9) | 0.0219 (8) | 0.0261 (8) | −0.0020 (7) | −0.0058 (7) | −0.0094 (7) |
C25' | 0.0461 (12) | 0.0475 (12) | 0.0374 (10) | −0.0174 (9) | 0.0107 (9) | −0.0237 (9) |
C26' | 0.0357 (11) | 0.0577 (13) | 0.0566 (13) | −0.0104 (10) | 0.0030 (9) | −0.0324 (11) |
O1' | 0.0274 (6) | 0.0376 (7) | 0.0320 (6) | −0.0099 (5) | 0.0014 (5) | −0.0194 (5) |
O2' | 0.0322 (7) | 0.0503 (8) | 0.0327 (7) | −0.0119 (6) | 0.0049 (6) | −0.0160 (6) |
O3' | 0.0296 (7) | 0.0528 (8) | 0.0457 (8) | −0.0129 (6) | −0.0016 (6) | −0.0283 (7) |
O4' | 0.0271 (6) | 0.0347 (6) | 0.0395 (7) | 0.0027 (5) | −0.0093 (5) | −0.0242 (6) |
O5' | 0.0337 (7) | 0.0420 (7) | 0.0315 (6) | −0.0121 (6) | −0.0006 (5) | −0.0194 (6) |
O3 | 0.0315 (7) | 0.0650 (10) | 0.0416 (8) | −0.0123 (7) | −0.0076 (6) | −0.0136 (7) |
O1 | 0.0302 (6) | 0.0405 (7) | 0.0283 (6) | −0.0114 (5) | −0.0002 (5) | −0.0144 (5) |
O2 | 0.0401 (8) | 0.0514 (9) | 0.0348 (7) | −0.0031 (6) | 0.0063 (6) | −0.0105 (7) |
O6' | 0.0392 (7) | 0.0420 (7) | 0.0334 (7) | −0.0049 (6) | −0.0018 (6) | −0.0228 (6) |
O4 | 0.0341 (7) | 0.0403 (7) | 0.0364 (7) | 0.0046 (5) | −0.0130 (5) | −0.0231 (6) |
O6 | 0.0401 (7) | 0.0519 (8) | 0.0322 (7) | −0.0014 (6) | −0.0066 (6) | −0.0252 (6) |
O5 | 0.0344 (7) | 0.0552 (8) | 0.0297 (7) | −0.0160 (6) | −0.0009 (5) | −0.0217 (6) |
C9—C10 | 1.367 (2) | C9'—C10' | 1.368 (2) |
C9—C8 | 1.398 (3) | C9'—C8' | 1.402 (2) |
C9—O4 | 1.409 (2) | C9'—O4' | 1.4106 (19) |
C8—C7 | 1.361 (3) | C8'—C7' | 1.360 (3) |
C8—H8 | 0.9500 | C8'—H8' | 0.9500 |
C7—C6 | 1.413 (3) | C7'—C6' | 1.413 (2) |
C7—H7 | 0.9500 | C7'—H7' | 0.9500 |
C6—C5 | 1.417 (3) | C6'—C5' | 1.417 (2) |
C6—C1 | 1.425 (3) | C6'—C1' | 1.422 (2) |
C5—C4 | 1.359 (3) | C5'—C4' | 1.362 (3) |
C5—H5 | 0.9500 | C5'—H5' | 0.9500 |
C4—C3 | 1.404 (3) | C4'—C3' | 1.402 (3) |
C4—H4 | 0.9500 | C4'—H4' | 0.9500 |
C3—C2 | 1.365 (3) | C3'—C2' | 1.364 (2) |
C3—H3 | 0.9500 | C3'—H3' | 0.9500 |
C2—C1 | 1.417 (3) | C2'—C1' | 1.417 (2) |
C2—H2 | 0.9500 | C2'—H2' | 0.9500 |
C1—C10 | 1.430 (2) | C1'—C10' | 1.423 (2) |
C10—C11 | 1.490 (2) | C10'—C11' | 1.490 (2) |
C11—C20 | 1.367 (2) | C11'—C20' | 1.366 (2) |
C11—C12 | 1.433 (2) | C11'—C12' | 1.430 (2) |
C12—C13 | 1.415 (3) | C12'—C13' | 1.410 (2) |
C12—C17 | 1.429 (3) | C12'—C17' | 1.426 (2) |
C13—C14 | 1.379 (3) | C13'—C14' | 1.368 (2) |
C13—H13 | 0.9500 | C13'—H13' | 0.9500 |
C14—C15 | 1.401 (4) | C14'—C15' | 1.401 (3) |
C14—H14 | 0.9500 | C14'—H14' | 0.9500 |
C15—C16 | 1.359 (4) | C15'—C16' | 1.364 (3) |
C15—H15 | 0.9500 | C15'—H15' | 0.9500 |
C16—C17 | 1.411 (3) | C16'—C17' | 1.413 (3) |
C16—H16 | 0.9500 | C16'—H16' | 0.9500 |
C17—C18 | 1.410 (3) | C17'—C18' | 1.416 (3) |
C18—C19 | 1.357 (3) | C18'—C19' | 1.364 (3) |
C18—H18 | 0.9500 | C18'—H18' | 0.9500 |
C19—C20 | 1.405 (2) | C19'—C20' | 1.411 (2) |
C19—H19 | 0.9500 | C19'—H19' | 0.9500 |
C20—O1 | 1.406 (2) | C20'—O1' | 1.402 (2) |
C21—O2 | 1.197 (2) | C21'—O2' | 1.194 (2) |
C21—O3 | 1.317 (2) | C21'—O3' | 1.319 (2) |
C21—O1 | 1.352 (2) | C21'—O1' | 1.351 (2) |
C22—C23 | 1.343 (4) | C22'—C23' | 1.454 (3) |
C22—O3 | 1.453 (3) | C22'—O3' | 1.454 (2) |
C22—H22A | 0.9900 | C22'—H22C | 0.9900 |
C22—H22B | 0.9900 | C22'—H22D | 0.9900 |
C23—H23A | 0.9800 | C23'—H23D | 0.9800 |
C23—H23B | 0.9800 | C23'—H23E | 0.9800 |
C23—H23C | 0.9800 | C23'—H23F | 0.9800 |
C24—O5 | 1.194 (2) | C24'—O5' | 1.194 (2) |
C24—O6 | 1.323 (2) | C24'—O6' | 1.322 (2) |
C24—O4 | 1.346 (2) | C24'—O4' | 1.350 (2) |
C25—O6 | 1.459 (2) | C25'—O6' | 1.461 (2) |
C25—C26 | 1.492 (3) | C25'—C26' | 1.495 (3) |
C25—H25A | 0.9900 | C25'—H25C | 0.9900 |
C25—H25B | 0.9900 | C25'—H25D | 0.9900 |
C26—H26A | 0.9800 | C26'—H26D | 0.9800 |
C26—H26B | 0.9800 | C26'—H26E | 0.9800 |
C26—H26C | 0.9800 | C26'—H26F | 0.9800 |
C10—C9—C8 | 123.22 (16) | C7'—C8'—H8' | 120.6 |
C10—C9—O4 | 117.75 (15) | C9'—C8'—H8' | 120.6 |
C8—C9—O4 | 118.85 (15) | C8'—C7'—C6' | 121.28 (16) |
C7—C8—C9 | 119.23 (17) | C8'—C7'—H7' | 119.4 |
C7—C8—H8 | 120.4 | C6'—C7'—H7' | 119.4 |
C9—C8—H8 | 120.4 | C7'—C6'—C5' | 122.19 (16) |
C8—C7—C6 | 121.12 (17) | C7'—C6'—C1' | 119.15 (15) |
C8—C7—H7 | 119.4 | C5'—C6'—C1' | 118.66 (16) |
C6—C7—H7 | 119.4 | C4'—C5'—C6' | 121.11 (16) |
C7—C6—C5 | 122.39 (18) | C4'—C5'—H5' | 119.4 |
C7—C6—C1 | 118.92 (17) | C6'—C5'—H5' | 119.4 |
C5—C6—C1 | 118.68 (18) | C5'—C4'—C3' | 120.18 (16) |
C4—C5—C6 | 121.1 (2) | C5'—C4'—H4' | 119.9 |
C4—C5—H5 | 119.4 | C3'—C4'—H4' | 119.9 |
C6—C5—H5 | 119.4 | C2'—C3'—C4' | 120.52 (17) |
C5—C4—C3 | 120.20 (19) | C2'—C3'—H3' | 119.7 |
C5—C4—H4 | 119.9 | C4'—C3'—H3' | 119.7 |
C3—C4—H4 | 119.9 | C3'—C2'—C1' | 120.90 (16) |
C2—C3—C4 | 120.6 (2) | C3'—C2'—H2' | 119.5 |
C2—C3—H3 | 119.7 | C1'—C2'—H2' | 119.5 |
C4—C3—H3 | 119.7 | C2'—C1'—C6' | 118.61 (14) |
C3—C2—C1 | 120.72 (19) | C2'—C1'—C10' | 122.20 (14) |
C3—C2—H2 | 119.6 | C6'—C1'—C10' | 119.19 (15) |
C1—C2—H2 | 119.6 | C9'—C10'—C1' | 118.46 (14) |
C2—C1—C6 | 118.62 (16) | C9'—C10'—C11' | 120.95 (14) |
C2—C1—C10 | 121.92 (16) | C1'—C10'—C11' | 120.45 (14) |
C6—C1—C10 | 119.45 (16) | C20'—C11'—C12' | 118.91 (15) |
C9—C10—C1 | 118.04 (16) | C20'—C11'—C10' | 121.86 (14) |
C9—C10—C11 | 121.39 (15) | C12'—C11'—C10' | 119.20 (14) |
C1—C10—C11 | 120.54 (15) | C13'—C12'—C17' | 118.49 (15) |
C20—C11—C12 | 118.19 (16) | C13'—C12'—C11' | 122.29 (15) |
C20—C11—C10 | 121.70 (15) | C17'—C12'—C11' | 119.22 (15) |
C12—C11—C10 | 120.11 (16) | C14'—C13'—C12' | 121.00 (17) |
C13—C12—C17 | 119.17 (18) | C14'—C13'—H13' | 119.5 |
C13—C12—C11 | 121.76 (18) | C12'—C13'—H13' | 119.5 |
C17—C12—C11 | 119.06 (18) | C13'—C14'—C15' | 120.66 (19) |
C14—C13—C12 | 119.9 (2) | C13'—C14'—H14' | 119.7 |
C14—C13—H13 | 120.1 | C15'—C14'—H14' | 119.7 |
C12—C13—H13 | 120.1 | C16'—C15'—C14' | 119.78 (18) |
C13—C14—C15 | 120.7 (3) | C16'—C15'—H15' | 120.1 |
C13—C14—H14 | 119.6 | C14'—C15'—H15' | 120.1 |
C15—C14—H14 | 119.6 | C15'—C16'—C17' | 121.42 (18) |
C16—C15—C14 | 120.3 (2) | C15'—C16'—H16' | 119.3 |
C16—C15—H15 | 119.8 | C17'—C16'—H16' | 119.3 |
C14—C15—H15 | 119.8 | C16'—C17'—C18' | 122.49 (17) |
C15—C16—C17 | 121.3 (2) | C16'—C17'—C12' | 118.65 (17) |
C15—C16—H16 | 119.4 | C18'—C17'—C12' | 118.84 (16) |
C17—C16—H16 | 119.4 | C19'—C18'—C17' | 121.47 (16) |
C18—C17—C16 | 122.4 (2) | C19'—C18'—H18' | 119.3 |
C18—C17—C12 | 119.04 (18) | C17'—C18'—H18' | 119.3 |
C16—C17—C12 | 118.5 (2) | C18'—C19'—C20' | 118.98 (17) |
C19—C18—C17 | 121.51 (19) | C18'—C19'—H19' | 120.5 |
C19—C18—H18 | 119.2 | C20'—C19'—H19' | 120.5 |
C17—C18—H18 | 119.2 | C11'—C20'—O1' | 116.69 (14) |
C18—C19—C20 | 118.9 (2) | C11'—C20'—C19' | 122.58 (16) |
C18—C19—H19 | 120.6 | O1'—C20'—C19' | 120.55 (15) |
C20—C19—H19 | 120.6 | O2'—C21'—O3' | 127.56 (17) |
C11—C20—C19 | 123.18 (17) | O2'—C21'—O1' | 125.45 (17) |
C11—C20—O1 | 118.07 (15) | O3'—C21'—O1' | 106.99 (14) |
C19—C20—O1 | 118.60 (16) | C23'—C22'—O3' | 109.51 (18) |
O2—C21—O3 | 128.02 (18) | C23'—C22'—H22C | 109.8 |
O2—C21—O1 | 125.31 (19) | O3'—C22'—H22C | 109.8 |
O3—C21—O1 | 106.67 (15) | C23'—C22'—H22D | 109.8 |
C23—C22—O3 | 114.1 (2) | O3'—C22'—H22D | 109.8 |
C23—C22—H22A | 108.7 | H22C—C22'—H22D | 108.2 |
O3—C22—H22A | 108.7 | C22'—C23'—H23D | 109.5 |
C23—C22—H22B | 108.7 | C22'—C23'—H23E | 109.5 |
O3—C22—H22B | 108.7 | H23D—C23'—H23E | 109.5 |
H22A—C22—H22B | 107.6 | C22'—C23'—H23F | 109.5 |
C22—C23—H23A | 109.5 | H23D—C23'—H23F | 109.5 |
C22—C23—H23B | 109.5 | H23E—C23'—H23F | 109.5 |
H23A—C23—H23B | 109.5 | O5'—C24'—O6' | 127.66 (16) |
C22—C23—H23C | 109.5 | O5'—C24'—O4' | 125.38 (15) |
H23A—C23—H23C | 109.5 | O6'—C24'—O4' | 106.96 (14) |
H23B—C23—H23C | 109.5 | O6'—C25'—C26' | 111.53 (16) |
O5—C24—O6 | 127.59 (17) | O6'—C25'—H25C | 109.3 |
O5—C24—O4 | 125.70 (16) | C26'—C25'—H25C | 109.3 |
O6—C24—O4 | 106.70 (14) | O6'—C25'—H25D | 109.3 |
O6—C25—C26 | 111.50 (18) | C26'—C25'—H25D | 109.3 |
O6—C25—H25A | 109.3 | H25C—C25'—H25D | 108.0 |
C26—C25—H25A | 109.3 | C25'—C26'—H26D | 109.5 |
O6—C25—H25B | 109.3 | C25'—C26'—H26E | 109.5 |
C26—C25—H25B | 109.3 | H26D—C26'—H26E | 109.5 |
H25A—C25—H25B | 108.0 | C25'—C26'—H26F | 109.5 |
C25—C26—H26A | 109.5 | H26D—C26'—H26F | 109.5 |
C25—C26—H26B | 109.5 | H26E—C26'—H26F | 109.5 |
H26A—C26—H26B | 109.5 | C21'—O1'—C20' | 117.15 (12) |
C25—C26—H26C | 109.5 | C21'—O3'—C22' | 115.02 (15) |
H26A—C26—H26C | 109.5 | C24'—O4'—C9' | 115.70 (12) |
H26B—C26—H26C | 109.5 | C21—O3—C22 | 117.08 (19) |
C10'—C9'—C8' | 123.11 (15) | C21—O1—C20 | 116.62 (13) |
C10'—C9'—O4' | 118.17 (14) | C24'—O6'—C25' | 115.63 (14) |
C8'—C9'—O4' | 118.53 (14) | C24—O4—C9 | 116.23 (13) |
C7'—C8'—C9' | 118.78 (16) | C24—O6—C25 | 115.41 (14) |
C10—C9—C8—C7 | −1.6 (3) | C7'—C6'—C1'—C10' | −1.4 (2) |
O4—C9—C8—C7 | −176.59 (16) | C5'—C6'—C1'—C10' | 178.88 (14) |
C9—C8—C7—C6 | 0.4 (3) | C8'—C9'—C10'—C1' | −0.8 (2) |
C8—C7—C6—C5 | −177.62 (18) | O4'—C9'—C10'—C1' | −175.79 (13) |
C8—C7—C6—C1 | 1.0 (3) | C8'—C9'—C10'—C11' | 174.86 (15) |
C7—C6—C5—C4 | 178.45 (19) | O4'—C9'—C10'—C11' | −0.1 (2) |
C1—C6—C5—C4 | −0.2 (3) | C2'—C1'—C10'—C9' | −178.30 (15) |
C6—C5—C4—C3 | 1.4 (3) | C6'—C1'—C10'—C9' | 1.8 (2) |
C5—C4—C3—C2 | −1.3 (3) | C2'—C1'—C10'—C11' | 6.0 (2) |
C4—C3—C2—C1 | −0.2 (3) | C6'—C1'—C10'—C11' | −173.93 (14) |
C3—C2—C1—C6 | 1.4 (3) | C9'—C10'—C11'—C20' | 97.87 (19) |
C3—C2—C1—C10 | −177.09 (17) | C1'—C10'—C11'—C20' | −86.52 (19) |
C7—C6—C1—C2 | −179.90 (17) | C9'—C10'—C11'—C12' | −84.37 (19) |
C5—C6—C1—C2 | −1.2 (3) | C1'—C10'—C11'—C12' | 91.24 (18) |
C7—C6—C1—C10 | −1.4 (2) | C20'—C11'—C12'—C13' | 178.17 (15) |
C5—C6—C1—C10 | 177.30 (16) | C10'—C11'—C12'—C13' | 0.3 (2) |
C8—C9—C10—C1 | 1.2 (3) | C20'—C11'—C12'—C17' | −0.5 (2) |
O4—C9—C10—C1 | 176.23 (14) | C10'—C11'—C12'—C17' | −178.33 (14) |
C8—C9—C10—C11 | −176.84 (16) | C17'—C12'—C13'—C14' | −0.2 (2) |
O4—C9—C10—C11 | −1.8 (2) | C11'—C12'—C13'—C14' | −178.90 (16) |
C2—C1—C10—C9 | 178.80 (16) | C12'—C13'—C14'—C15' | −0.2 (3) |
C6—C1—C10—C9 | 0.3 (2) | C13'—C14'—C15'—C16' | 0.3 (3) |
C2—C1—C10—C11 | −3.2 (2) | C14'—C15'—C16'—C17' | 0.0 (3) |
C6—C1—C10—C11 | 178.35 (15) | C15'—C16'—C17'—C18' | 177.72 (18) |
C9—C10—C11—C20 | −91.0 (2) | C15'—C16'—C17'—C12' | −0.5 (3) |
C1—C10—C11—C20 | 91.0 (2) | C13'—C12'—C17'—C16' | 0.6 (2) |
C9—C10—C11—C12 | 89.9 (2) | C11'—C12'—C17'—C16' | 179.28 (14) |
C1—C10—C11—C12 | −88.1 (2) | C13'—C12'—C17'—C18' | −177.70 (15) |
C20—C11—C12—C13 | 178.97 (16) | C11'—C12'—C17'—C18' | 1.0 (2) |
C10—C11—C12—C13 | −1.9 (2) | C16'—C17'—C18'—C19' | −178.93 (16) |
C20—C11—C12—C17 | −0.1 (2) | C12'—C17'—C18'—C19' | −0.7 (3) |
C10—C11—C12—C17 | 179.08 (15) | C17'—C18'—C19'—C20' | −0.1 (3) |
C17—C12—C13—C14 | 2.5 (3) | C12'—C11'—C20'—O1' | −175.38 (13) |
C11—C12—C13—C14 | −176.53 (17) | C10'—C11'—C20'—O1' | 2.4 (2) |
C12—C13—C14—C15 | −0.5 (3) | C12'—C11'—C20'—C19' | −0.3 (2) |
C13—C14—C15—C16 | −2.1 (3) | C10'—C11'—C20'—C19' | 177.44 (15) |
C14—C15—C16—C17 | 2.6 (3) | C18'—C19'—C20'—C11' | 0.6 (3) |
C15—C16—C17—C18 | 179.31 (19) | C18'—C19'—C20'—O1' | 175.50 (15) |
C15—C16—C17—C12 | −0.5 (3) | O2'—C21'—O1'—C20' | −7.6 (2) |
C13—C12—C17—C18 | 178.15 (17) | O3'—C21'—O1'—C20' | 172.62 (13) |
C11—C12—C17—C18 | −2.8 (2) | C11'—C20'—O1'—C21' | −121.40 (16) |
C13—C12—C17—C16 | −2.0 (2) | C19'—C20'—O1'—C21' | 63.4 (2) |
C11—C12—C17—C16 | 177.07 (16) | O2'—C21'—O3'—C22' | 3.1 (3) |
C16—C17—C18—C19 | −176.88 (18) | O1'—C21'—O3'—C22' | −177.12 (17) |
C12—C17—C18—C19 | 3.0 (3) | C23'—C22'—O3'—C21' | 161.4 (2) |
C17—C18—C19—C20 | −0.2 (3) | O5'—C24'—O4'—C9' | −8.8 (2) |
C12—C11—C20—C19 | 3.0 (3) | O6'—C24'—O4'—C9' | 170.79 (13) |
C10—C11—C20—C19 | −176.19 (16) | C10'—C9'—O4'—C24' | −91.69 (17) |
C12—C11—C20—O1 | 178.35 (14) | C8'—C9'—O4'—C24' | 93.12 (18) |
C10—C11—C20—O1 | −0.8 (2) | O2—C21—O3—C22 | −0.4 (3) |
C18—C19—C20—C11 | −2.9 (3) | O1—C21—O3—C22 | 179.06 (19) |
C18—C19—C20—O1 | −178.24 (16) | C23—C22—O3—C21 | −119.3 (4) |
C10'—C9'—C8'—C7' | −0.5 (3) | O2—C21—O1—C20 | −4.3 (3) |
O4'—C9'—C8'—C7' | 174.40 (15) | O3—C21—O1—C20 | 176.18 (14) |
C9'—C8'—C7'—C6' | 0.9 (3) | C11—C20—O1—C21 | 119.31 (17) |
C8'—C7'—C6'—C5' | 179.74 (16) | C19—C20—O1—C21 | −65.1 (2) |
C8'—C7'—C6'—C1' | 0.1 (2) | O5'—C24'—O6'—C25' | −0.9 (3) |
C7'—C6'—C5'—C4' | −178.69 (17) | O4'—C24'—O6'—C25' | 179.53 (14) |
C1'—C6'—C5'—C4' | 1.0 (2) | C26'—C25'—O6'—C24' | −78.8 (2) |
C6'—C5'—C4'—C3' | 0.1 (3) | O5—C24—O4—C9 | 0.7 (3) |
C5'—C4'—C3'—C2' | −1.1 (3) | O6—C24—O4—C9 | −179.62 (14) |
C4'—C3'—C2'—C1' | 1.1 (3) | C10—C9—O4—C24 | 109.50 (17) |
C3'—C2'—C1'—C6' | 0.0 (2) | C8—C9—O4—C24 | −75.2 (2) |
C3'—C2'—C1'—C10' | −179.89 (15) | O5—C24—O6—C25 | 0.7 (3) |
C7'—C6'—C1'—C2' | 178.66 (15) | O4—C24—O6—C25 | −178.97 (15) |
C5'—C6'—C1'—C2' | −1.0 (2) | C26—C25—O6—C24 | 78.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5′—H5′···O1i | 0.95 | 2.59 | 3.519 (2) | 165 |
C7—H7···O2′ii | 0.95 | 2.57 | 3.405 (3) | 146 |
C16—H16···O5′iii | 0.95 | 2.56 | 3.369 (3) | 143 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z. |
C26H22O6 | Z = 4 |
Mr = 430.44 | F(000) = 904 |
Triclinic, P1 | Dx = 1.350 Mg m−3 |
Hall symbol: -P 1 | Melting point: 417.67 K |
a = 10.7955 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.726 (2) Å | Cell parameters from 667 reflections |
c = 15.887 (3) Å | θ = 0.9–28.0° |
α = 63.491 (2)° | µ = 0.10 mm−1 |
β = 72.400 (2)° | T = 90 K |
γ = 73.011 (2)° | Block, colourless |
V = 2117.4 (6) Å3 | 0.50 × 0.31 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 8616 independent reflections |
Radiation source: fine-focus sealed tube | 7378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.946, Tmax = 0.981 | k = −18→18 |
22555 measured reflections | l = −19→19 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0477P)2 + 0.6139P] where P = (Fo2 + 2Fc2)/3 |
8616 reflections | (Δ/σ)max = 0.001 |
601 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C26H22O6 | γ = 73.011 (2)° |
Mr = 430.44 | V = 2117.4 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.7955 (17) Å | Mo Kα radiation |
b = 14.726 (2) Å | µ = 0.10 mm−1 |
c = 15.887 (3) Å | T = 90 K |
α = 63.491 (2)° | 0.50 × 0.31 × 0.25 mm |
β = 72.400 (2)° |
Bruker SMART CCD area-detector diffractometer | 8616 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7378 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.981 | Rint = 0.027 |
22555 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.26 e Å−3 |
8616 reflections | Δρmin = −0.21 e Å−3 |
601 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | Occ. (<1) | |
C22 | 0.7959 (4) | 0.8568 (4) | 0.5293 (3) | 0.0276 (10) | 0.585 (10) |
H22E | 0.8060 | 0.8981 | 0.5610 | 0.033* | 0.585 (10) |
H22F | 0.8466 | 0.8810 | 0.4624 | 0.033* | 0.585 (10) |
C23 | 0.8452 (4) | 0.7442 (3) | 0.5825 (4) | 0.0345 (13) | 0.585 (10) |
H23G | 0.7923 | 0.7208 | 0.6478 | 0.052* | 0.585 (10) |
H23H | 0.9380 | 0.7336 | 0.5852 | 0.052* | 0.585 (10) |
H23I | 0.8374 | 0.7046 | 0.5491 | 0.052* | 0.585 (10) |
C23A | 0.8293 (5) | 0.7778 (6) | 0.6167 (4) | 0.0398 (18) | 0.415 (10) |
H23D | 0.8013 | 0.8347 | 0.6386 | 0.060* | 0.415 (10) |
H23E | 0.9244 | 0.7519 | 0.6143 | 0.060* | 0.415 (10) |
H23F | 0.7808 | 0.7220 | 0.6614 | 0.060* | 0.415 (10) |
C22A | 0.8012 (5) | 0.8158 (6) | 0.5187 (4) | 0.0306 (15) | 0.415 (10) |
H22C | 0.8150 | 0.7579 | 0.4992 | 0.037* | 0.415 (10) |
H22D | 0.8581 | 0.8657 | 0.4704 | 0.037* | 0.415 (10) |
C1 | 0.20721 (15) | 0.77630 (13) | 0.59744 (12) | 0.0219 (3) | |
C2 | 0.12453 (16) | 0.87333 (14) | 0.58953 (13) | 0.0271 (4) | |
H2 | 0.1346 | 0.9315 | 0.5304 | 0.033* | |
C3 | 0.03050 (17) | 0.88369 (16) | 0.66642 (14) | 0.0351 (4) | |
H3 | −0.0237 | 0.9492 | 0.6603 | 0.042* | |
C4 | 0.01330 (18) | 0.79860 (16) | 0.75426 (14) | 0.0369 (5) | |
H4 | −0.0511 | 0.8072 | 0.8075 | 0.044* | |
C5 | 0.08831 (17) | 0.70397 (15) | 0.76358 (13) | 0.0323 (4) | |
H5 | 0.0741 | 0.6467 | 0.8229 | 0.039* | |
C6 | 0.18762 (16) | 0.68944 (13) | 0.68599 (12) | 0.0246 (4) | |
C7 | 0.26963 (17) | 0.59241 (13) | 0.69448 (12) | 0.0275 (4) | |
H7 | 0.2562 | 0.5340 | 0.7530 | 0.033* | |
C8 | 0.36738 (16) | 0.58159 (13) | 0.62015 (12) | 0.0252 (4) | |
H8 | 0.4215 | 0.5161 | 0.6264 | 0.030* | |
C9 | 0.38743 (15) | 0.66821 (13) | 0.53430 (11) | 0.0210 (3) | |
C10 | 0.31070 (15) | 0.76401 (12) | 0.51998 (11) | 0.0192 (3) | |
C11 | 0.33177 (15) | 0.85305 (12) | 0.42564 (11) | 0.0200 (3) | |
C12 | 0.26192 (16) | 0.87375 (13) | 0.35337 (12) | 0.0243 (4) | |
C13 | 0.17506 (17) | 0.81067 (15) | 0.36689 (14) | 0.0310 (4) | |
H13 | 0.1572 | 0.7549 | 0.4269 | 0.037* | |
C14 | 0.11626 (18) | 0.82964 (18) | 0.29348 (16) | 0.0414 (5) | |
H14 | 0.0590 | 0.7862 | 0.3030 | 0.050* | |
C15 | 0.14006 (19) | 0.91226 (18) | 0.20492 (15) | 0.0436 (6) | |
H15 | 0.1007 | 0.9235 | 0.1543 | 0.052* | |
C16 | 0.21920 (18) | 0.97647 (17) | 0.19113 (13) | 0.0383 (5) | |
H16 | 0.2320 | 1.0337 | 0.1315 | 0.046* | |
C17 | 0.28290 (17) | 0.95962 (14) | 0.26401 (12) | 0.0284 (4) | |
C18 | 0.36674 (17) | 1.02458 (14) | 0.25106 (12) | 0.0315 (4) | |
H18 | 0.3776 | 1.0837 | 0.1928 | 0.038* | |
C19 | 0.43232 (17) | 1.00443 (13) | 0.32016 (12) | 0.0274 (4) | |
H19 | 0.4885 | 1.0487 | 0.3105 | 0.033* | |
C20 | 0.41536 (15) | 0.91693 (12) | 0.40607 (11) | 0.0210 (3) | |
C21 | 0.61483 (16) | 0.87553 (12) | 0.45709 (12) | 0.0255 (4) | |
C24 | 0.61102 (16) | 0.63978 (12) | 0.46244 (11) | 0.0201 (3) | |
C25 | 0.82829 (17) | 0.60976 (15) | 0.37653 (13) | 0.0313 (4) | |
H25A | 0.8490 | 0.6547 | 0.3998 | 0.038* | |
H25B | 0.8743 | 0.6269 | 0.3086 | 0.038* | |
C26 | 0.87755 (17) | 0.49884 (15) | 0.43522 (13) | 0.0341 (4) | |
H26A | 0.8357 | 0.4828 | 0.5030 | 0.051* | |
H26B | 0.9737 | 0.4871 | 0.4278 | 0.051* | |
H26C | 0.8554 | 0.4542 | 0.4132 | 0.051* | |
C20' | 0.13416 (15) | 0.60040 (12) | 0.11077 (11) | 0.0187 (3) | |
C19' | 0.12606 (16) | 0.53001 (12) | 0.20730 (11) | 0.0230 (3) | |
H19' | 0.0710 | 0.4798 | 0.2342 | 0.028* | |
C18' | 0.19902 (16) | 0.53532 (13) | 0.26157 (11) | 0.0240 (4) | |
H18' | 0.1938 | 0.4883 | 0.3268 | 0.029* | |
C17' | 0.28190 (15) | 0.60917 (12) | 0.22280 (11) | 0.0214 (3) | |
C16' | 0.36030 (16) | 0.61415 (14) | 0.27734 (12) | 0.0273 (4) | |
H16' | 0.3549 | 0.5684 | 0.3429 | 0.033* | |
C15' | 0.44313 (17) | 0.68335 (15) | 0.23734 (13) | 0.0305 (4) | |
H15' | 0.4949 | 0.6856 | 0.2750 | 0.037* | |
C14' | 0.45232 (17) | 0.75143 (14) | 0.14049 (13) | 0.0276 (4) | |
H14' | 0.5108 | 0.7992 | 0.1129 | 0.033* | |
C13' | 0.37758 (16) | 0.74953 (12) | 0.08540 (12) | 0.0225 (3) | |
H13' | 0.3843 | 0.7964 | 0.0201 | 0.027* | |
C12' | 0.29059 (15) | 0.67849 (12) | 0.12468 (11) | 0.0184 (3) | |
C11' | 0.21325 (14) | 0.67327 (11) | 0.06863 (10) | 0.0167 (3) | |
C10' | 0.22481 (14) | 0.74405 (11) | −0.03459 (10) | 0.0157 (3) | |
C1' | 0.31780 (14) | 0.71264 (12) | −0.10659 (10) | 0.0160 (3) | |
C2' | 0.39285 (15) | 0.61133 (12) | −0.08485 (11) | 0.0193 (3) | |
H2' | 0.3809 | 0.5618 | −0.0205 | 0.023* | |
C3' | 0.48238 (15) | 0.58382 (13) | −0.15525 (12) | 0.0237 (4) | |
H3' | 0.5311 | 0.5152 | −0.1397 | 0.028* | |
C4' | 0.50275 (16) | 0.65655 (14) | −0.25060 (12) | 0.0252 (4) | |
H4' | 0.5663 | 0.6373 | −0.2989 | 0.030* | |
C5' | 0.43166 (16) | 0.75451 (13) | −0.27398 (11) | 0.0235 (4) | |
H5' | 0.4461 | 0.8028 | −0.3387 | 0.028* | |
C6' | 0.33666 (15) | 0.78551 (12) | −0.20348 (11) | 0.0192 (3) | |
C7' | 0.25975 (16) | 0.88624 (12) | −0.22613 (11) | 0.0229 (3) | |
H7' | 0.2716 | 0.9350 | −0.2908 | 0.028* | |
C8' | 0.16925 (16) | 0.91473 (12) | −0.15734 (12) | 0.0223 (3) | |
H8' | 0.1176 | 0.9824 | −0.1736 | 0.027* | |
C9' | 0.15362 (14) | 0.84257 (12) | −0.06214 (11) | 0.0179 (3) | |
C24' | −0.05559 (15) | 0.85619 (11) | 0.03557 (11) | 0.0185 (3) | |
C22' | −0.25006 (17) | 0.63371 (18) | 0.01373 (14) | 0.0402 (5) | |
H22A | −0.2887 | 0.6914 | 0.0354 | 0.048* | |
H22B | −0.2874 | 0.5722 | 0.0625 | 0.048* | |
C23' | −0.28214 (18) | 0.66189 (15) | −0.08012 (14) | 0.0356 (4) | |
H23A | −0.2451 | 0.7229 | −0.1279 | 0.053* | |
H23B | −0.3784 | 0.6772 | −0.0739 | 0.053* | |
H23C | −0.2442 | 0.6042 | −0.1007 | 0.053* | |
C21' | −0.06467 (15) | 0.60717 (12) | 0.07451 (11) | 0.0208 (3) | |
C25' | −0.25062 (17) | 0.86056 (14) | 0.15249 (12) | 0.0301 (4) | |
H25C | −0.2750 | 0.8515 | 0.2207 | 0.036* | |
H25D | −0.2600 | 0.7972 | 0.1495 | 0.036* | |
C26' | −0.34292 (17) | 0.95149 (14) | 0.09693 (14) | 0.0327 (4) | |
H26D | −0.3307 | 1.0147 | 0.0972 | 0.049* | |
H26E | −0.4345 | 0.9419 | 0.1268 | 0.049* | |
H26F | −0.3238 | 0.9571 | 0.0306 | 0.049* | |
O1 | 0.48113 (10) | 0.89777 (9) | 0.47800 (8) | 0.0231 (3) | |
O2 | 0.68034 (12) | 0.86481 (10) | 0.38532 (9) | 0.0356 (3) | |
O3 | 0.65607 (12) | 0.86795 (11) | 0.53045 (9) | 0.0369 (3) | |
O4 | 0.48449 (11) | 0.65512 (9) | 0.45591 (8) | 0.0235 (3) | |
O5 | 0.64750 (11) | 0.63555 (9) | 0.52858 (8) | 0.0249 (3) | |
O6 | 0.68558 (11) | 0.62979 (9) | 0.38265 (8) | 0.0261 (3) | |
O4' | 0.06850 (10) | 0.87497 (8) | 0.01032 (8) | 0.0210 (2) | |
O5' | −0.10235 (11) | 0.82830 (9) | −0.00620 (8) | 0.0231 (3) | |
O6' | −0.11323 (11) | 0.87465 (9) | 0.11421 (8) | 0.0246 (3) | |
O1' | 0.06884 (10) | 0.59305 (8) | 0.05039 (8) | 0.0206 (2) | |
O2' | −0.13064 (11) | 0.61388 (9) | 0.14806 (8) | 0.0265 (3) | |
O3' | −0.10676 (11) | 0.61154 (9) | 0.00270 (8) | 0.0257 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C22 | 0.0206 (17) | 0.028 (2) | 0.037 (2) | −0.0067 (16) | −0.0080 (14) | −0.0125 (17) |
C23 | 0.0281 (18) | 0.028 (2) | 0.051 (3) | −0.0041 (15) | −0.0182 (18) | −0.0125 (18) |
C23A | 0.026 (3) | 0.060 (4) | 0.042 (3) | −0.006 (2) | −0.008 (2) | −0.029 (3) |
C22A | 0.016 (2) | 0.042 (4) | 0.039 (3) | −0.005 (3) | −0.0024 (19) | −0.022 (3) |
C1 | 0.0164 (8) | 0.0290 (9) | 0.0225 (8) | −0.0069 (7) | −0.0019 (6) | −0.0116 (7) |
C2 | 0.0217 (8) | 0.0315 (9) | 0.0259 (9) | −0.0046 (7) | −0.0002 (7) | −0.0123 (8) |
C3 | 0.0229 (9) | 0.0451 (11) | 0.0364 (11) | −0.0037 (8) | 0.0036 (8) | −0.0230 (9) |
C4 | 0.0237 (9) | 0.0585 (13) | 0.0305 (10) | −0.0139 (9) | 0.0099 (8) | −0.0251 (10) |
C5 | 0.0263 (9) | 0.0469 (11) | 0.0228 (9) | −0.0196 (8) | 0.0029 (7) | −0.0101 (8) |
C6 | 0.0200 (8) | 0.0329 (9) | 0.0235 (9) | −0.0128 (7) | −0.0027 (7) | −0.0094 (7) |
C7 | 0.0297 (9) | 0.0277 (9) | 0.0237 (9) | −0.0156 (7) | −0.0074 (7) | −0.0013 (7) |
C8 | 0.0254 (9) | 0.0209 (8) | 0.0320 (9) | −0.0059 (7) | −0.0110 (7) | −0.0085 (7) |
C9 | 0.0172 (8) | 0.0268 (8) | 0.0240 (8) | −0.0040 (6) | −0.0044 (6) | −0.0142 (7) |
C10 | 0.0167 (7) | 0.0245 (8) | 0.0200 (8) | −0.0053 (6) | −0.0045 (6) | −0.0102 (7) |
C11 | 0.0175 (8) | 0.0223 (8) | 0.0177 (8) | 0.0028 (6) | −0.0016 (6) | −0.0110 (7) |
C12 | 0.0191 (8) | 0.0308 (9) | 0.0243 (9) | 0.0076 (7) | −0.0055 (7) | −0.0187 (7) |
C13 | 0.0226 (9) | 0.0388 (10) | 0.0364 (10) | 0.0039 (8) | −0.0089 (8) | −0.0230 (9) |
C14 | 0.0248 (10) | 0.0602 (14) | 0.0569 (14) | 0.0079 (9) | −0.0162 (9) | −0.0429 (12) |
C15 | 0.0312 (11) | 0.0688 (15) | 0.0392 (12) | 0.0220 (10) | −0.0198 (9) | −0.0394 (12) |
C16 | 0.0315 (10) | 0.0534 (12) | 0.0243 (9) | 0.0189 (9) | −0.0112 (8) | −0.0232 (9) |
C17 | 0.0244 (9) | 0.0353 (10) | 0.0207 (8) | 0.0115 (7) | −0.0057 (7) | −0.0165 (8) |
C18 | 0.0308 (10) | 0.0294 (9) | 0.0188 (8) | 0.0040 (8) | 0.0018 (7) | −0.0063 (7) |
C19 | 0.0269 (9) | 0.0256 (9) | 0.0226 (9) | −0.0031 (7) | 0.0025 (7) | −0.0092 (7) |
C20 | 0.0196 (8) | 0.0247 (8) | 0.0165 (8) | −0.0020 (6) | 0.0016 (6) | −0.0107 (7) |
C21 | 0.0204 (8) | 0.0205 (8) | 0.0233 (9) | −0.0050 (7) | 0.0011 (7) | −0.0009 (7) |
C24 | 0.0240 (8) | 0.0179 (8) | 0.0190 (8) | −0.0042 (6) | −0.0038 (6) | −0.0079 (6) |
C25 | 0.0245 (9) | 0.0477 (11) | 0.0256 (9) | −0.0105 (8) | 0.0040 (7) | −0.0211 (9) |
C26 | 0.0213 (9) | 0.0533 (12) | 0.0319 (10) | −0.0030 (8) | −0.0046 (7) | −0.0232 (9) |
C20' | 0.0170 (7) | 0.0203 (8) | 0.0186 (8) | 0.0006 (6) | −0.0017 (6) | −0.0112 (6) |
C19' | 0.0195 (8) | 0.0212 (8) | 0.0210 (8) | −0.0041 (6) | 0.0036 (6) | −0.0066 (7) |
C18' | 0.0211 (8) | 0.0260 (9) | 0.0152 (8) | 0.0016 (7) | 0.0003 (6) | −0.0059 (7) |
C17' | 0.0178 (8) | 0.0254 (8) | 0.0177 (8) | 0.0054 (6) | −0.0019 (6) | −0.0125 (7) |
C16' | 0.0220 (8) | 0.0381 (10) | 0.0182 (8) | 0.0065 (7) | −0.0066 (7) | −0.0138 (8) |
C15' | 0.0236 (9) | 0.0458 (11) | 0.0295 (9) | 0.0036 (8) | −0.0115 (7) | −0.0234 (9) |
C14' | 0.0232 (9) | 0.0321 (9) | 0.0344 (10) | −0.0016 (7) | −0.0087 (7) | −0.0193 (8) |
C13' | 0.0218 (8) | 0.0242 (8) | 0.0232 (8) | −0.0010 (7) | −0.0051 (7) | −0.0122 (7) |
C12' | 0.0164 (7) | 0.0205 (8) | 0.0181 (8) | 0.0025 (6) | −0.0020 (6) | −0.0118 (7) |
C11' | 0.0142 (7) | 0.0174 (7) | 0.0162 (7) | 0.0014 (6) | 0.0003 (6) | −0.0094 (6) |
C10' | 0.0135 (7) | 0.0189 (7) | 0.0162 (7) | −0.0043 (6) | −0.0029 (6) | −0.0074 (6) |
C1' | 0.0133 (7) | 0.0216 (8) | 0.0158 (7) | −0.0055 (6) | −0.0029 (6) | −0.0082 (6) |
C2' | 0.0184 (8) | 0.0219 (8) | 0.0168 (8) | −0.0024 (6) | −0.0030 (6) | −0.0081 (6) |
C3' | 0.0185 (8) | 0.0296 (9) | 0.0267 (9) | 0.0009 (7) | −0.0047 (7) | −0.0174 (7) |
C4' | 0.0169 (8) | 0.0406 (10) | 0.0223 (8) | −0.0050 (7) | 0.0012 (6) | −0.0194 (8) |
C5' | 0.0208 (8) | 0.0362 (10) | 0.0147 (8) | −0.0114 (7) | 0.0000 (6) | −0.0096 (7) |
C6' | 0.0163 (7) | 0.0251 (8) | 0.0188 (8) | −0.0078 (6) | −0.0032 (6) | −0.0086 (7) |
C7' | 0.0257 (8) | 0.0231 (8) | 0.0172 (8) | −0.0086 (7) | −0.0059 (7) | −0.0020 (7) |
C8' | 0.0230 (8) | 0.0170 (8) | 0.0272 (9) | −0.0014 (6) | −0.0097 (7) | −0.0075 (7) |
C9' | 0.0150 (7) | 0.0214 (8) | 0.0213 (8) | −0.0023 (6) | −0.0038 (6) | −0.0125 (7) |
C24' | 0.0220 (8) | 0.0139 (7) | 0.0169 (8) | −0.0002 (6) | −0.0040 (6) | −0.0055 (6) |
C22' | 0.0192 (9) | 0.0701 (15) | 0.0418 (11) | −0.0152 (9) | 0.0010 (8) | −0.0313 (11) |
C23' | 0.0248 (9) | 0.0378 (11) | 0.0446 (11) | −0.0038 (8) | −0.0094 (8) | −0.0161 (9) |
C21' | 0.0210 (8) | 0.0182 (8) | 0.0232 (8) | −0.0088 (6) | 0.0013 (7) | −0.0087 (7) |
C25' | 0.0308 (10) | 0.0341 (10) | 0.0255 (9) | −0.0129 (8) | 0.0091 (7) | −0.0169 (8) |
C26' | 0.0231 (9) | 0.0394 (11) | 0.0399 (11) | −0.0081 (8) | 0.0036 (8) | −0.0242 (9) |
O1 | 0.0186 (6) | 0.0299 (6) | 0.0206 (6) | −0.0069 (5) | −0.0001 (5) | −0.0107 (5) |
O2 | 0.0280 (7) | 0.0344 (7) | 0.0256 (7) | −0.0002 (5) | 0.0059 (5) | −0.0062 (6) |
O3 | 0.0197 (6) | 0.0534 (9) | 0.0286 (7) | −0.0088 (6) | −0.0056 (5) | −0.0066 (6) |
O4 | 0.0222 (6) | 0.0281 (6) | 0.0235 (6) | 0.0017 (5) | −0.0073 (5) | −0.0152 (5) |
O5 | 0.0225 (6) | 0.0375 (7) | 0.0198 (6) | −0.0105 (5) | −0.0005 (5) | −0.0151 (5) |
O6 | 0.0254 (6) | 0.0348 (7) | 0.0206 (6) | −0.0009 (5) | −0.0030 (5) | −0.0170 (5) |
O4' | 0.0170 (5) | 0.0236 (6) | 0.0265 (6) | 0.0015 (4) | −0.0043 (5) | −0.0167 (5) |
O5' | 0.0225 (6) | 0.0278 (6) | 0.0222 (6) | −0.0083 (5) | 0.0001 (5) | −0.0131 (5) |
O6' | 0.0256 (6) | 0.0284 (6) | 0.0212 (6) | −0.0032 (5) | 0.0000 (5) | −0.0150 (5) |
O1' | 0.0181 (5) | 0.0250 (6) | 0.0212 (6) | −0.0060 (5) | 0.0003 (4) | −0.0127 (5) |
O2' | 0.0223 (6) | 0.0326 (7) | 0.0221 (6) | −0.0083 (5) | 0.0035 (5) | −0.0116 (5) |
O3' | 0.0182 (6) | 0.0356 (7) | 0.0305 (6) | −0.0082 (5) | −0.0003 (5) | −0.0202 (6) |
C22—O3 | 1.466 (4) | C26—H26C | 0.9800 |
C22—C23 | 1.501 (6) | C20'—C11' | 1.370 (2) |
C23A—C22A | 1.496 (9) | C20'—O1' | 1.4056 (18) |
C23A—H23D | 0.9800 | C20'—C19' | 1.410 (2) |
C23A—H23E | 0.9800 | C19'—C18' | 1.370 (2) |
C23A—H23F | 0.9800 | C19'—H19' | 0.9500 |
C22A—O3 | 1.525 (6) | C18'—C17' | 1.414 (2) |
C22A—H22C | 0.9900 | C18'—H18' | 0.9500 |
C22A—H22D | 0.9900 | C17'—C16' | 1.417 (2) |
C1—C2 | 1.420 (2) | C17'—C12' | 1.424 (2) |
C1—C6 | 1.425 (2) | C16'—C15' | 1.361 (3) |
C1—C10 | 1.430 (2) | C16'—H16' | 0.9500 |
C2—C3 | 1.368 (2) | C15'—C14' | 1.404 (3) |
C2—H2 | 0.9500 | C15'—H15' | 0.9500 |
C3—C4 | 1.404 (3) | C14'—C13' | 1.371 (2) |
C3—H3 | 0.9500 | C14'—H14' | 0.9500 |
C4—C5 | 1.360 (3) | C13'—C12' | 1.415 (2) |
C4—H4 | 0.9500 | C13'—H13' | 0.9500 |
C5—C6 | 1.420 (2) | C12'—C11' | 1.430 (2) |
C5—H5 | 0.9500 | C11'—C10' | 1.489 (2) |
C6—C7 | 1.416 (2) | C10'—C9' | 1.368 (2) |
C7—C8 | 1.360 (2) | C10'—C1' | 1.427 (2) |
C7—H7 | 0.9500 | C1'—C2' | 1.416 (2) |
C8—C9 | 1.401 (2) | C1'—C6' | 1.423 (2) |
C8—H8 | 0.9500 | C2'—C3' | 1.368 (2) |
C9—C10 | 1.368 (2) | C2'—H2' | 0.9500 |
C9—O4 | 1.4118 (18) | C3'—C4' | 1.406 (2) |
C10—C11 | 1.494 (2) | C3'—H3' | 0.9500 |
C11—C20 | 1.364 (2) | C4'—C5' | 1.362 (2) |
C11—C12 | 1.434 (2) | C4'—H4' | 0.9500 |
C12—C13 | 1.413 (3) | C5'—C6' | 1.415 (2) |
C12—C17 | 1.427 (2) | C5'—H5' | 0.9500 |
C13—C14 | 1.376 (3) | C6'—C7' | 1.416 (2) |
C13—H13 | 0.9500 | C7'—C8' | 1.360 (2) |
C14—C15 | 1.401 (3) | C7'—H7' | 0.9500 |
C14—H14 | 0.9500 | C8'—C9' | 1.400 (2) |
C15—C16 | 1.359 (3) | C8'—H8' | 0.9500 |
C15—H15 | 0.9500 | C9'—O4' | 1.4113 (18) |
C16—C17 | 1.414 (2) | C24'—O5' | 1.1963 (18) |
C16—H16 | 0.9500 | C24'—O6' | 1.3252 (18) |
C17—C18 | 1.412 (3) | C24'—O4' | 1.3506 (19) |
C18—C19 | 1.361 (2) | C22'—O3' | 1.457 (2) |
C18—H18 | 0.9500 | C22'—C23' | 1.480 (3) |
C19—C20 | 1.405 (2) | C22'—H22A | 0.9900 |
C19—H19 | 0.9500 | C22'—H22B | 0.9900 |
C20—O1 | 1.4056 (19) | C23'—H23A | 0.9800 |
C21—O2 | 1.197 (2) | C23'—H23B | 0.9800 |
C21—O3 | 1.318 (2) | C23'—H23C | 0.9800 |
C21—O1 | 1.3534 (19) | C21'—O2' | 1.2004 (19) |
C24—O5 | 1.2003 (18) | C21'—O3' | 1.3201 (19) |
C24—O6 | 1.3253 (18) | C21'—O1' | 1.3526 (18) |
C24—O4 | 1.3461 (19) | C25'—O6' | 1.461 (2) |
C25—O6 | 1.463 (2) | C25'—C26' | 1.504 (3) |
C25—C26 | 1.501 (3) | C25'—H25C | 0.9900 |
C25—H25A | 0.9900 | C25'—H25D | 0.9900 |
C25—H25B | 0.9900 | C26'—H26D | 0.9800 |
C26—H26A | 0.9800 | C26'—H26E | 0.9800 |
C26—H26B | 0.9800 | C26'—H26F | 0.9800 |
O3—C22—C23 | 106.8 (3) | C18'—C19'—H19' | 120.6 |
C22A—C23A—H23D | 109.5 | C20'—C19'—H19' | 120.6 |
C22A—C23A—H23E | 109.5 | C19'—C18'—C17' | 121.53 (15) |
H23D—C23A—H23E | 109.5 | C19'—C18'—H18' | 119.2 |
C22A—C23A—H23F | 109.5 | C17'—C18'—H18' | 119.2 |
H23D—C23A—H23F | 109.5 | C18'—C17'—C16' | 122.22 (15) |
H23E—C23A—H23F | 109.5 | C18'—C17'—C12' | 118.94 (14) |
C23A—C22A—O3 | 103.3 (5) | C16'—C17'—C12' | 118.81 (15) |
C23A—C22A—H22C | 111.1 | C15'—C16'—C17' | 121.12 (16) |
O3—C22A—H22C | 111.1 | C15'—C16'—H16' | 119.4 |
C23A—C22A—H22D | 111.1 | C17'—C16'—H16' | 119.4 |
O3—C22A—H22D | 111.1 | C16'—C15'—C14' | 120.17 (16) |
H22C—C22A—H22D | 109.1 | C16'—C15'—H15' | 119.9 |
C2—C1—C6 | 118.74 (15) | C14'—C15'—H15' | 119.9 |
C2—C1—C10 | 121.89 (15) | C13'—C14'—C15' | 120.54 (16) |
C6—C1—C10 | 119.37 (15) | C13'—C14'—H14' | 119.7 |
C3—C2—C1 | 120.51 (17) | C15'—C14'—H14' | 119.7 |
C3—C2—H2 | 119.7 | C14'—C13'—C12' | 120.76 (16) |
C1—C2—H2 | 119.7 | C14'—C13'—H13' | 119.6 |
C2—C3—C4 | 120.70 (18) | C12'—C13'—H13' | 119.6 |
C2—C3—H3 | 119.7 | C13'—C12'—C17' | 118.61 (14) |
C4—C3—H3 | 119.7 | C13'—C12'—C11' | 122.09 (14) |
C5—C4—C3 | 120.34 (16) | C17'—C12'—C11' | 119.30 (14) |
C5—C4—H4 | 119.8 | C20'—C11'—C12' | 118.83 (14) |
C3—C4—H4 | 119.8 | C20'—C11'—C10' | 121.84 (13) |
C4—C5—C6 | 121.03 (17) | C12'—C11'—C10' | 119.28 (13) |
C4—C5—H5 | 119.5 | C9'—C10'—C1' | 118.44 (13) |
C6—C5—H5 | 119.5 | C9'—C10'—C11' | 121.08 (13) |
C7—C6—C5 | 122.24 (16) | C1'—C10'—C11' | 120.33 (13) |
C7—C6—C1 | 119.10 (15) | C2'—C1'—C6' | 118.71 (13) |
C5—C6—C1 | 118.64 (16) | C2'—C1'—C10' | 122.18 (13) |
C8—C7—C6 | 120.99 (15) | C6'—C1'—C10' | 119.11 (13) |
C8—C7—H7 | 119.5 | C3'—C2'—C1' | 120.85 (15) |
C6—C7—H7 | 119.5 | C3'—C2'—H2' | 119.6 |
C7—C8—C9 | 119.25 (16) | C1'—C2'—H2' | 119.6 |
C7—C8—H8 | 120.4 | C2'—C3'—C4' | 120.33 (15) |
C9—C8—H8 | 120.4 | C2'—C3'—H3' | 119.8 |
C10—C9—C8 | 123.17 (15) | C4'—C3'—H3' | 119.8 |
C10—C9—O4 | 117.86 (14) | C5'—C4'—C3' | 120.26 (14) |
C8—C9—O4 | 118.78 (14) | C5'—C4'—H4' | 119.9 |
C9—C10—C1 | 118.10 (15) | C3'—C4'—H4' | 119.9 |
C9—C10—C11 | 121.28 (14) | C4'—C5'—C6' | 121.10 (15) |
C1—C10—C11 | 120.60 (14) | C4'—C5'—H5' | 119.5 |
C20—C11—C12 | 118.39 (15) | C6'—C5'—H5' | 119.5 |
C20—C11—C10 | 121.72 (14) | C5'—C6'—C7' | 122.25 (15) |
C12—C11—C10 | 119.89 (14) | C5'—C6'—C1' | 118.73 (14) |
C13—C12—C17 | 118.84 (16) | C7'—C6'—C1' | 119.02 (14) |
C13—C12—C11 | 122.20 (16) | C8'—C7'—C6' | 121.41 (15) |
C17—C12—C11 | 118.94 (16) | C8'—C7'—H7' | 119.3 |
C14—C13—C12 | 120.28 (19) | C6'—C7'—H7' | 119.3 |
C14—C13—H13 | 119.9 | C7'—C8'—C9' | 118.78 (14) |
C12—C13—H13 | 119.9 | C7'—C8'—H8' | 120.6 |
C13—C14—C15 | 120.7 (2) | C9'—C8'—H8' | 120.6 |
C13—C14—H14 | 119.7 | C10'—C9'—C8' | 123.20 (14) |
C15—C14—H14 | 119.7 | C10'—C9'—O4' | 117.92 (13) |
C16—C15—C14 | 120.28 (18) | C8'—C9'—O4' | 118.67 (13) |
C16—C15—H15 | 119.9 | O5'—C24'—O6' | 127.60 (15) |
C14—C15—H15 | 119.9 | O5'—C24'—O4' | 125.62 (14) |
C15—C16—C17 | 121.14 (19) | O6'—C24'—O4' | 106.77 (13) |
C15—C16—H16 | 119.4 | O3'—C22'—C23' | 108.48 (15) |
C17—C16—H16 | 119.4 | O3'—C22'—H22A | 110.0 |
C18—C17—C16 | 122.21 (18) | C23'—C22'—H22A | 110.0 |
C18—C17—C12 | 119.09 (15) | O3'—C22'—H22B | 110.0 |
C16—C17—C12 | 118.70 (18) | C23'—C22'—H22B | 110.0 |
C19—C18—C17 | 121.46 (16) | H22A—C22'—H22B | 108.4 |
C19—C18—H18 | 119.3 | C22'—C23'—H23A | 109.5 |
C17—C18—H18 | 119.3 | C22'—C23'—H23B | 109.5 |
C18—C19—C20 | 118.77 (17) | H23A—C23'—H23B | 109.5 |
C18—C19—H19 | 120.6 | C22'—C23'—H23C | 109.5 |
C20—C19—H19 | 120.6 | H23A—C23'—H23C | 109.5 |
C11—C20—O1 | 118.16 (14) | H23B—C23'—H23C | 109.5 |
C11—C20—C19 | 123.23 (15) | O2'—C21'—O3' | 127.34 (15) |
O1—C20—C19 | 118.48 (14) | O2'—C21'—O1' | 125.53 (15) |
O2—C21—O3 | 127.91 (16) | O3'—C21'—O1' | 107.13 (12) |
O2—C21—O1 | 125.41 (17) | O6'—C25'—C26' | 111.38 (14) |
O3—C21—O1 | 106.69 (14) | O6'—C25'—H25C | 109.4 |
O5—C24—O6 | 127.41 (15) | C26'—C25'—H25C | 109.4 |
O5—C24—O4 | 125.91 (14) | O6'—C25'—H25D | 109.4 |
O6—C24—O4 | 106.68 (13) | C26'—C25'—H25D | 109.4 |
O6—C25—C26 | 111.27 (14) | H25C—C25'—H25D | 108.0 |
O6—C25—H25A | 109.4 | C25'—C26'—H26D | 109.5 |
C26—C25—H25A | 109.4 | C25'—C26'—H26E | 109.5 |
O6—C25—H25B | 109.4 | H26D—C26'—H26E | 109.5 |
C26—C25—H25B | 109.4 | C25'—C26'—H26F | 109.5 |
H25A—C25—H25B | 108.0 | H26D—C26'—H26F | 109.5 |
C25—C26—H26A | 109.5 | H26E—C26'—H26F | 109.5 |
C25—C26—H26B | 109.5 | C21—O1—C20 | 116.63 (12) |
H26A—C26—H26B | 109.5 | C21—O3—C22 | 122.7 (2) |
C25—C26—H26C | 109.5 | C21—O3—C22A | 105.9 (3) |
H26A—C26—H26C | 109.5 | C24—O4—C9 | 116.05 (12) |
H26B—C26—H26C | 109.5 | C24—O6—C25 | 115.36 (12) |
C11'—C20'—O1' | 116.40 (13) | C24'—O4'—C9' | 115.28 (11) |
C11'—C20'—C19' | 122.64 (14) | C24'—O6'—C25' | 115.38 (12) |
O1'—C20'—C19' | 120.75 (14) | C21'—O1'—C20' | 116.82 (11) |
C18'—C19'—C20' | 118.76 (15) | C21'—O3'—C22' | 114.58 (13) |
C6—C1—C2—C3 | 1.9 (2) | C19'—C20'—C11'—C12' | −0.1 (2) |
C10—C1—C2—C3 | −176.85 (16) | O1'—C20'—C11'—C10' | 2.6 (2) |
C1—C2—C3—C4 | −0.5 (3) | C19'—C20'—C11'—C10' | 177.38 (14) |
C2—C3—C4—C5 | −1.3 (3) | C13'—C12'—C11'—C20' | 178.05 (14) |
C3—C4—C5—C6 | 1.6 (3) | C17'—C12'—C11'—C20' | −0.9 (2) |
C4—C5—C6—C7 | 178.21 (16) | C13'—C12'—C11'—C10' | 0.5 (2) |
C4—C5—C6—C1 | −0.2 (3) | C17'—C12'—C11'—C10' | −178.53 (13) |
C2—C1—C6—C7 | 179.99 (15) | C20'—C11'—C10'—C9' | 98.58 (18) |
C10—C1—C6—C7 | −1.2 (2) | C12'—C11'—C10'—C9' | −83.91 (18) |
C2—C1—C6—C5 | −1.6 (2) | C20'—C11'—C10'—C1' | −85.88 (18) |
C10—C1—C6—C5 | 177.21 (14) | C12'—C11'—C10'—C1' | 91.64 (17) |
C5—C6—C7—C8 | −177.41 (16) | C9'—C10'—C1'—C2' | −178.18 (14) |
C1—C6—C7—C8 | 1.0 (2) | C11'—C10'—C1'—C2' | 6.2 (2) |
C6—C7—C8—C9 | 0.5 (2) | C9'—C10'—C1'—C6' | 2.2 (2) |
C7—C8—C9—C10 | −1.8 (2) | C11'—C10'—C1'—C6' | −173.44 (13) |
C7—C8—C9—O4 | −176.70 (14) | C6'—C1'—C2'—C3' | 0.4 (2) |
C8—C9—C10—C1 | 1.5 (2) | C10'—C1'—C2'—C3' | −179.24 (14) |
O4—C9—C10—C1 | 176.45 (13) | C1'—C2'—C3'—C4' | 0.9 (2) |
C8—C9—C10—C11 | −177.10 (14) | C2'—C3'—C4'—C5' | −1.2 (2) |
O4—C9—C10—C11 | −2.2 (2) | C3'—C4'—C5'—C6' | 0.3 (2) |
C2—C1—C10—C9 | 178.75 (15) | C4'—C5'—C6'—C7' | −178.82 (15) |
C6—C1—C10—C9 | 0.0 (2) | C4'—C5'—C6'—C1' | 1.0 (2) |
C2—C1—C10—C11 | −2.6 (2) | C2'—C1'—C6'—C5' | −1.3 (2) |
C6—C1—C10—C11 | 178.66 (14) | C10'—C1'—C6'—C5' | 178.30 (13) |
C9—C10—C11—C20 | −90.40 (19) | C2'—C1'—C6'—C7' | 178.53 (14) |
C1—C10—C11—C20 | 91.01 (19) | C10'—C1'—C6'—C7' | −1.9 (2) |
C9—C10—C11—C12 | 90.36 (18) | C5'—C6'—C7'—C8' | −179.76 (15) |
C1—C10—C11—C12 | −88.23 (18) | C1'—C6'—C7'—C8' | 0.4 (2) |
C20—C11—C12—C13 | 178.96 (15) | C6'—C7'—C8'—C9' | 0.7 (2) |
C10—C11—C12—C13 | −1.8 (2) | C1'—C10'—C9'—C8' | −1.2 (2) |
C20—C11—C12—C17 | 0.3 (2) | C11'—C10'—C9'—C8' | 174.44 (14) |
C10—C11—C12—C17 | 179.59 (14) | C1'—C10'—C9'—O4' | −175.83 (12) |
C17—C12—C13—C14 | 2.6 (2) | C11'—C10'—C9'—O4' | −0.2 (2) |
C11—C12—C13—C14 | −176.01 (15) | C7'—C8'—C9'—C10' | −0.3 (2) |
C12—C13—C14—C15 | −0.8 (3) | C7'—C8'—C9'—O4' | 174.33 (13) |
C13—C14—C15—C16 | −1.6 (3) | O2—C21—O1—C20 | −4.8 (2) |
C14—C15—C16—C17 | 2.3 (3) | O3—C21—O1—C20 | 175.49 (13) |
C15—C16—C17—C18 | 179.30 (16) | C11—C20—O1—C21 | 118.62 (15) |
C15—C16—C17—C12 | −0.4 (2) | C19—C20—O1—C21 | −65.38 (19) |
C13—C12—C17—C18 | 178.27 (15) | O2—C21—O3—C22 | 7.9 (4) |
C11—C12—C17—C18 | −3.1 (2) | O1—C21—O3—C22 | −172.4 (3) |
C13—C12—C17—C16 | −2.0 (2) | O2—C21—O3—C22A | −14.2 (4) |
C11—C12—C17—C16 | 176.69 (14) | O1—C21—O3—C22A | 165.5 (3) |
C16—C17—C18—C19 | −176.76 (16) | C23—C22—O3—C21 | −99.4 (4) |
C12—C17—C18—C19 | 3.0 (2) | C23—C22—O3—C22A | −44.0 (7) |
C17—C18—C19—C20 | −0.1 (2) | C23A—C22A—O3—C21 | −161.8 (6) |
C12—C11—C20—O1 | 178.49 (13) | C23A—C22A—O3—C22 | 64.3 (8) |
C10—C11—C20—O1 | −0.8 (2) | O5—C24—O4—C9 | 0.6 (2) |
C12—C11—C20—C19 | 2.7 (2) | O6—C24—O4—C9 | −179.78 (12) |
C10—C11—C20—C19 | −176.57 (14) | C10—C9—O4—C24 | 110.39 (16) |
C18—C19—C20—C11 | −2.9 (2) | C8—C9—O4—C24 | −74.46 (18) |
C18—C19—C20—O1 | −178.64 (14) | O5—C24—O6—C25 | 1.0 (2) |
C11'—C20'—C19'—C18' | 0.7 (2) | O4—C24—O6—C25 | −178.53 (13) |
O1'—C20'—C19'—C18' | 175.27 (13) | C26—C25—O6—C24 | 78.16 (17) |
C20'—C19'—C18'—C17' | −0.2 (2) | O5'—C24'—O4'—C9' | −10.6 (2) |
C19'—C18'—C17'—C16' | −178.53 (14) | O6'—C24'—O4'—C9' | 169.40 (12) |
C19'—C18'—C17'—C12' | −0.8 (2) | C10'—C9'—O4'—C24' | −89.04 (16) |
C18'—C17'—C16'—C15' | 177.45 (15) | C8'—C9'—O4'—C24' | 96.07 (16) |
C12'—C17'—C16'—C15' | −0.3 (2) | O5'—C24'—O6'—C25' | −1.1 (2) |
C17'—C16'—C15'—C14' | 0.0 (3) | O4'—C24'—O6'—C25' | 178.88 (12) |
C16'—C15'—C14'—C13' | 0.4 (3) | C26'—C25'—O6'—C24' | −78.88 (17) |
C15'—C14'—C13'—C12' | −0.5 (2) | O2'—C21'—O1'—C20' | −8.8 (2) |
C14'—C13'—C12'—C17' | 0.2 (2) | O3'—C21'—O1'—C20' | 171.44 (12) |
C14'—C13'—C12'—C11' | −178.78 (14) | C11'—C20'—O1'—C21' | −121.79 (14) |
C18'—C17'—C12'—C13' | −177.61 (14) | C19'—C20'—O1'—C21' | 63.36 (18) |
C16'—C17'—C12'—C13' | 0.2 (2) | O2'—C21'—O3'—C22' | 4.3 (2) |
C18'—C17'—C12'—C11' | 1.4 (2) | O1'—C21'—O3'—C22' | −176.00 (14) |
C16'—C17'—C12'—C11' | 179.19 (13) | C23'—C22'—O3'—C21' | 166.07 (15) |
O1'—C20'—C11'—C12' | −174.90 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5′—H5′···O1i | 0.95 | 2.57 | 3.497 (2) | 166 |
C7—H7···O2′ii | 0.95 | 2.54 | 3.369 (3) | 146 |
C16—H16···O5′iii | 0.95 | 2.54 | 3.327 (3) | 140 |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z. |
Experimental details
(292K) | (393K) | (150K) | (90K) | |
Crystal data | ||||
Chemical formula | C26H22O6 | C26H22O6 | C26H22O6 | C26H22O6 |
Mr | 430.44 | 430.44 | 430.44 | 430.44 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 292 | 393 | 150 | 90 |
a, b, c (Å) | 9.7614 (14), 10.0379 (14), 12.3947 (17) | 9.8546 (18), 10.0864 (19), 12.539 (2) | 10.8028 (18), 14.798 (3), 15.926 (3) | 10.7955 (17), 14.726 (2), 15.887 (3) |
α, β, γ (°) | 89.490 (2), 84.810 (2), 65.989 (2) | 89.469 (4), 85.207 (4), 65.578 (3) | 63.692 (2), 72.394 (3), 73.200 (3) | 63.491 (2), 72.400 (2), 73.011 (2) |
V (Å3) | 1104.3 (3) | 1130.4 (3) | 2139.2 (7) | 2117.4 (6) |
Z | 2 | 2 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.10 | 0.10 |
Crystal size (mm) | 0.50 × 0.31 × 0.25 | 0.50 × 0.31 × 0.25 | 0.50 × 0.31 × 0.25 | 0.50 × 0.31 × 0.25 |
Data collection | ||||
Diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.907, 0.977 | 0.909, 0.978 | 0.906, 0.977 | 0.946, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11287, 4176, 2806 | 12123, 4606, 2113 | 22856, 8704, 6807 | 22555, 8616, 7378 |
Rint | 0.016 | 0.025 | 0.024 | 0.027 |
(sin θ/λ)max (Å−1) | 0.610 | 0.625 | 0.625 | 0.625 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.191, 1.05 | 0.059, 0.220, 1.03 | 0.049, 0.139, 1.04 | 0.048, 0.114, 1.09 |
No. of reflections | 4176 | 4606 | 8704 | 8616 |
No. of parameters | 291 | 291 | 581 | 601 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.20 | 0.20, −0.14 | 0.57, −0.47 | 0.26, −0.21 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Version 6.14; Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), POV-RAY (Persistence of Vision Team, 2004) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C5'—H5'···O1i | 0.9500 | 2.5900 | 3.519 (2) | 165.00 |
C7—H7···O2'ii | 0.9500 | 2.5700 | 3.405 (3) | 146.00 |
C16—H16···O5'iii | 0.9500 | 2.5600 | 3.369 (3) | 143.00 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5'—H5'···O1i | 0.95 | 2.57 | 3.497 (2) | 166 |
C7—H7···O2'ii | 0.95 | 2.54 | 3.369 (3) | 146 |
C16—H16···O5'iii | 0.95 | 2.54 | 3.327 (3) | 140 |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z. |
The appearance of a short carbon–carbon bond is often encountered in crystal structure determinations and is explained either as a consequence of thermal effects or as a structural disorder of some kind; theoretical calculations support both these observations. In crystal structures, long and short bonds have been treated as a consequence of rotational oscillations of molecules in crystals, as proposed by Cruickshank (1956). Dunitz (1999) has observed that 'the discrepancy between the 'curiously short' carbon–carbon double bond distance in 3-ethynylcyclopropene, as measured experimentally by X-ray analysis [1.255 (2) Å], compared with the value derived from high level ab initio calculations (ca 1.28 Å), is largely due to neglect of corrections for molecular motion in the crystal'. It was suggested that THMA (thermal motion analysis) clearly brings out the importance of thermal corrections between the X-ray distances and theoretically computed values (Dunitz, Maverick & Trueblood, 1988 and/or Dunitz, Shomaker & Trueblood, 1988; Dunitz, 1995). On the other hand, the shortening of the bond is explained as either due to ring strain (Xie & Schaffer, 1981 or????1989; Ermer & Lex, 1987) or owing to special electronic effects (Ermer et al., 1989; Allen, 1980,1981; Hagen et al., 1972; Traetteberg et al., 1984; Irngartinger et al., 1984). It has been argued that hybridization alone is not the cause for short C—C bonds, indeed symmetry and geometrical constraints play a significant role (Huntley et al., 2005). We have determined the crystal structure of racemic 1,1'-binaphthalene-2,2'-diyl diethyl biscarbonate, (I), at room temperature and have observed a very short Csp3—Csp3 bond length of 1.327 (6) Å in one of the terminal ethyl groups.
In this structure, there are no strains involved and no significant electronic effects in the molecule. One would expect that analysis of the structure determined at different temperatures (in this case at 393, 150 and 90 K) for the same crystal should reveal whether the shortening is due either entirely to thermal effects or to positional disorder. The bond length corrections due to thermal effects are applied based on the THMA (Dunitz, Maverick & Trueblood, 1988 and/or Dunitz, Shomaker & Trueblood, 1988; Dunitz, 1995) analysis before comparisons of variations in bond lengths. It is of interest to note that the unit cell at 150 K is a supercell of that observed at 292 K, and this feature, as shown in Fig. 1, explains the near doubling of the unit-cell volume observed at lower temperatures (150 and 90 K). The transformation matrix is (110, 101, 011).
At 292 K, the compound crystallizes in space group P1 with Z = 2. Fig. 2 shows the molecular structure with the atom numbering. All displacement ellipsoids are large and, in particular, those associated with the short-bond atoms C22 and C23 are very large. Thermal motion analysis using the program THMA (Dunitz, Maverick & Trueblood, 1988 and/or Dunitz, Shomaker & Trueblood, 1988; Dunitz, 1995) was used to obtain corrected bond lengths for all bonds; however, the C22—C23 bond continues to be exceptionally short [1.327 (6) Å]. From a search of the Cambridge Structural Database (Version 5.29 of 2008; Allen, 2002), this is one of a number of short single C—C bonds found in the literature for a molecule of this type, i.e. in which there is either no highly strained ring or no well known electronic effect due to conjugation. Fig. 3 is a packing diagram, with the orientation of the unit cell and hence its contents similar to that of the resulting supercell at low temperatures to ensure easy comparison. The packing in the lattice is mainly through weak interactions involving an intermolecular π–π [3.880 (2) Å] stacking interaction between the centroids of the C12–C17 rings at (x, y, z) and (-x + 2, -y, -z).
At 393 K, the cell parameters and the packing of the molecules in the unit cell are similar to those at room temperature. However, the displacement parameters of all atoms show the expected increase, and in particular those of both C22 and C23 are remarkably enhanced (Fig. 1S, supplementary material). It is noteworthy that the THMA analysis results in a C22–C23 bond length of 1.335 Å, suggesting that the bond shortening is certainly not only due to thermal effects.
The same crystal when cooled to 150 K indexes uniquely with Z = 4 and a cell volume almost double that of the 292K structure. It is noteworthy that the short C—C bond is now associated with only one molecule [THMA-corrected C22—C23=1.343 (4) Å], and the second molecule shows a closer to normal bond length [THMA-corrected C22'—C23' = 1.454 (3) Å]. Thus it appears that resolution of the overlap of molecules is beginning to take place at this temperature. The molecule is shown in Fig. 2S (supplmentary material), and details of the C—H···O hydorgen bonding are given in Table 1.
At 90 K, the cell volume contracts slightly compared with that at 150 K; however, the disorder at the C22—C23 site is now resolved. Fig. 5 shows the molecular structure of the compound, and the features of the positionally disordered C22 and C23 atoms now correspond to normal bond lengths [1.502 (5) Å none of the values in the CIF correspond to this]. The refinements suggest an occupancy ratio of 58:42 for the disordered atoms C22 and C22A, respectively. The refinements were carried out keeping the constraint on occupancy for C22 and C23 as one block and that for C22A and C23A as another block. The packing in the lattice (Fig. 4) is mainly through weak interactions involving intermolecular C—H···O contacts (Table 2) and π–π stacking interactions [with centroid–centroid distances of 3.849 (2) and 3.960 (1) Å, {for which rings?} with symmetry codes (-x + 1, -y +1, -z + 1) and (-x +1, -y +1, -z) ]. There are two types of C—H···π interactions [C3—H3···π and C3'—H3'···π, with H···π distances of 2.86 and 2.88 Å, {for which rings?} with symmetry operations (-x + 2, -y, -z + 1) and (-x + 1, -y +1, -z), respectively].
The formation of a terminal short bond withou the influence of strain or hybridization is of fundamental importance. The results clearly indicate that positional disorder could be the cause, and the structural analysis at different temperatures clearly brings out the salient features of such an effect. It is to be noted that thermal effects alone cannot resolve such unusual observed bond lengths. The unit cell at 150 K and below shows a supercell formation.