Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029519/lh6154sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029519/lh6154Isup2.hkl |
CCDC reference: 234846
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.101
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: TEXSAN–TEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXSAN–TEXRAY; data reduction: TEXSAN–TEXRAY; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.
C18H18O6 | F(000) = 696 |
Mr = 330.32 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.920 (7) Å | θ = 18.6–23.1° |
b = 12.053 (6) Å | µ = 0.10 mm−1 |
c = 15.658 (6) Å | T = 296 K |
β = 101.70 (4)° | Prism, light yellow |
V = 1648.4 (16) Å3 | 0.60 × 0.50 × 0.30 mm |
Z = 4 |
Rigaku AFC-6 diffractometer | Rint = 0.016 |
Radiation source: normal-focus rotating anode | θmax = 25.0°, θmin = 2.2° |
Graphite monochromator | h = 0→10 |
2θ–ω scans | k = 0→14 |
3100 measured reflections | l = −18→18 |
2901 independent reflections | 3 standard reflections every 150 reflections |
1919 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0335P)2 + 0.3604P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2901 reflections | Δρmax = 0.21 e Å−3 |
240 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0178 (15) |
Experimental. Data were collected at room temperature using a Rigaku AFC6R diffractometer. The data were collected using 2θ-ω-scan. Scans of (1.37 + 0.30tanθ) were made at a speed of 8.0ο/min in ω. The weak reflections (I<10.0σI) were rescanned (maximum 3 rescans) and the counts were accumulated to assure good counting statistics. Stationary bacground counts were recored on each side of the reflection·The ratio of peak counting time to backgroud counting time was 2:1. The crystal–to–detector distance was 400 mm. |
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 | 0.09822 (19) | −0.06378 (14) | 0.15409 (11) | 0.0434 (4) | |
C2 | 0.19625 (19) | 0.01258 (15) | 0.12446 (12) | 0.0450 (4) | |
H2 | 0.2357 | 0.0722 | 0.1597 | 0.044 (5)* | |
C3 | 0.2341 (2) | −0.00002 (15) | 0.04427 (12) | 0.0465 (4) | |
C4 | 0.1760 (2) | −0.09056 (15) | −0.00920 (12) | 0.0472 (4) | |
C5 | 0.0789 (2) | −0.16437 (15) | 0.01894 (12) | 0.0492 (5) | |
H5 | 0.0387 | −0.2235 | −0.0166 | 0.044 (5)* | |
C6 | 0.0405 (2) | −0.15131 (15) | 0.09991 (12) | 0.0481 (5) | |
H6 | −0.0250 | −0.2021 | 0.1181 | 0.056 (6)* | |
C7 | 0.05540 (19) | −0.05622 (15) | 0.23897 (12) | 0.0441 (4) | |
H7 | −0.0102 | −0.1118 | 0.2504 | 0.050 (5)* | |
C8 | 0.09545 (19) | 0.01783 (14) | 0.30291 (11) | 0.0430 (4) | |
C9 | 0.3805 (3) | 0.1671 (2) | 0.05904 (17) | 0.0795 (8) | |
H9A | 0.2949 | 0.2105 | 0.0684 | 0.105 (10)* | |
H9B | 0.4415 | 0.2105 | 0.0275 | 0.100 (8)* | |
H9C | 0.4415 | 0.1456 | 0.1143 | 0.109 (10)* | |
C10 | 0.1711 (3) | −0.18840 (19) | −0.14195 (15) | 0.0713 (6) | |
H10A | 0.0612 | −0.1886 | −0.1565 | 0.079 (7)* | |
H10B | 0.2066 | −0.2560 | −0.1122 | 0.077 (7)* | |
H10C | 0.2108 | −0.1827 | −0.1944 | 0.105 (9)* | |
C11 | 0.33326 (19) | 0.11361 (15) | 0.33168 (11) | 0.0433 (4) | |
C12 | 0.4065 (2) | 0.21467 (16) | 0.32813 (12) | 0.0514 (5) | |
C13 | 0.5622 (2) | 0.22145 (19) | 0.36244 (15) | 0.0658 (6) | |
H13 | 0.6134 | 0.2883 | 0.3604 | 0.088 (8)* | |
C14 | 0.6415 (2) | 0.1291 (2) | 0.39975 (16) | 0.0707 (6) | |
H14 | 0.7461 | 0.1343 | 0.4223 | 0.095 (8)* | |
C15 | 0.5684 (2) | 0.0303 (2) | 0.40394 (15) | 0.0671 (6) | |
H15 | 0.6223 | −0.0310 | 0.4301 | 0.092 (8)* | |
C16 | 0.4125 (2) | 0.02229 (17) | 0.36861 (13) | 0.0560 (5) | |
H16 | 0.3621 | −0.0450 | 0.3701 | 0.075 (7)* | |
C17 | 0.3793 (3) | 0.40837 (19) | 0.2980 (2) | 0.0796 (7) | |
H17A | 0.4137 | 0.4260 | 0.3586 | 0.129 (12)* | |
H17B | 0.3027 | 0.4608 | 0.2718 | 0.120 (11)* | |
H17C | 0.4643 | 0.4116 | 0.2690 | 0.113 (10)* | |
C18 | 0.0490 (2) | 0.01075 (15) | 0.38762 (12) | 0.0444 (4) | |
O1 | 0.32630 (16) | 0.07083 (12) | 0.01010 (9) | 0.0636 (4) | |
O2 | 0.22250 (16) | −0.09634 (12) | −0.08689 (9) | 0.0610 (4) | |
O3 | 0.17836 (13) | 0.11280 (10) | 0.29338 (8) | 0.0459 (3) | |
O4 | 0.31587 (16) | 0.29951 (11) | 0.28993 (10) | 0.0716 (4) | |
O5 | 0.09173 (15) | 0.08234 (11) | 0.44459 (8) | 0.0556 (4) | |
O6 | −0.03502 (17) | −0.07398 (11) | 0.39865 (10) | 0.0603 (4) | |
H6A | −0.0556 | −0.0710 | 0.4473 | 0.129 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0377 (9) | 0.0434 (10) | 0.0473 (10) | 0.0015 (8) | 0.0045 (8) | 0.0046 (8) |
C2 | 0.0407 (10) | 0.0458 (10) | 0.0473 (10) | −0.0012 (8) | 0.0066 (8) | −0.0003 (8) |
C3 | 0.0405 (9) | 0.0493 (11) | 0.0497 (10) | 0.0008 (8) | 0.0095 (8) | 0.0044 (8) |
C4 | 0.0459 (10) | 0.0489 (11) | 0.0456 (10) | 0.0095 (9) | 0.0061 (8) | 0.0017 (8) |
C5 | 0.0488 (11) | 0.0441 (10) | 0.0520 (11) | 0.0006 (9) | 0.0040 (9) | −0.0035 (9) |
C6 | 0.0449 (10) | 0.0441 (10) | 0.0537 (11) | −0.0003 (9) | 0.0062 (9) | 0.0028 (8) |
C7 | 0.0373 (9) | 0.0447 (10) | 0.0503 (10) | −0.0002 (8) | 0.0084 (8) | 0.0061 (8) |
C8 | 0.0375 (9) | 0.0437 (10) | 0.0477 (10) | −0.0019 (8) | 0.0086 (8) | 0.0053 (8) |
C9 | 0.0874 (18) | 0.0756 (16) | 0.0825 (18) | −0.0362 (15) | 0.0336 (16) | −0.0110 (14) |
C10 | 0.0863 (19) | 0.0669 (15) | 0.0627 (14) | 0.0026 (13) | 0.0201 (13) | −0.0165 (12) |
C11 | 0.0385 (9) | 0.0526 (11) | 0.0391 (9) | −0.0030 (8) | 0.0088 (7) | −0.0042 (8) |
C12 | 0.0478 (11) | 0.0528 (12) | 0.0535 (11) | −0.0056 (9) | 0.0100 (9) | −0.0021 (9) |
C13 | 0.0487 (12) | 0.0647 (14) | 0.0818 (15) | −0.0143 (11) | 0.0080 (11) | −0.0081 (12) |
C14 | 0.0440 (12) | 0.0793 (16) | 0.0842 (16) | −0.0040 (12) | 0.0024 (11) | −0.0125 (13) |
C15 | 0.0496 (12) | 0.0698 (15) | 0.0777 (15) | 0.0077 (11) | 0.0028 (11) | −0.0002 (12) |
C16 | 0.0452 (11) | 0.0564 (12) | 0.0654 (13) | −0.0010 (10) | 0.0087 (9) | 0.0026 (10) |
C17 | 0.0782 (17) | 0.0530 (14) | 0.109 (2) | −0.0128 (13) | 0.0231 (16) | 0.0118 (14) |
C18 | 0.0383 (9) | 0.0438 (10) | 0.0517 (11) | 0.0015 (8) | 0.0099 (8) | 0.0031 (9) |
O1 | 0.0675 (9) | 0.0671 (9) | 0.0620 (9) | −0.0190 (8) | 0.0272 (7) | −0.0070 (7) |
O2 | 0.0701 (9) | 0.0637 (9) | 0.0533 (8) | −0.0008 (7) | 0.0220 (7) | −0.0089 (7) |
O3 | 0.0393 (6) | 0.0470 (7) | 0.0501 (7) | −0.0046 (6) | 0.0060 (5) | 0.0052 (6) |
O4 | 0.0592 (9) | 0.0513 (9) | 0.0983 (12) | −0.0099 (7) | 0.0016 (8) | 0.0104 (8) |
O5 | 0.0628 (8) | 0.0533 (8) | 0.0546 (8) | −0.0068 (7) | 0.0207 (7) | −0.0058 (6) |
O6 | 0.0694 (9) | 0.0572 (8) | 0.0606 (9) | −0.0157 (7) | 0.0282 (7) | −0.0023 (7) |
C1—C6 | 1.386 (2) | C10—H10B | 0.9600 |
C1—C2 | 1.411 (2) | C10—H10C | 0.9600 |
C1—C7 | 1.458 (3) | C11—C16 | 1.371 (3) |
C2—C3 | 1.373 (3) | C11—C12 | 1.389 (3) |
C2—H2 | 0.9300 | C11—O3 | 1.390 (2) |
C3—O1 | 1.368 (2) | C12—O4 | 1.364 (2) |
C3—C4 | 1.409 (3) | C12—C13 | 1.386 (3) |
C4—O2 | 1.364 (2) | C13—C14 | 1.384 (3) |
C4—C5 | 1.375 (3) | C13—H13 | 0.9300 |
C5—C6 | 1.388 (3) | C14—C15 | 1.365 (3) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C15—C16 | 1.392 (3) |
C7—C8 | 1.335 (2) | C15—H15 | 0.9300 |
C7—H7 | 0.9300 | C16—H16 | 0.9300 |
C8—O3 | 1.387 (2) | C17—O4 | 1.424 (3) |
C8—C18 | 1.470 (3) | C17—H17A | 0.9600 |
C9—O1 | 1.421 (3) | C17—H17B | 0.9600 |
C9—H9A | 0.9600 | C17—H17C | 0.9600 |
C9—H9B | 0.9600 | C18—O5 | 1.244 (2) |
C9—H9C | 0.9600 | C18—O6 | 1.299 (2) |
C10—O2 | 1.423 (2) | O6—H6A | 0.8200 |
C10—H10A | 0.9600 | ||
C6—C1—C2 | 118.25 (17) | H10A—C10—H10C | 109.5 |
C6—C1—C7 | 118.17 (16) | H10B—C10—H10C | 109.5 |
C2—C1—C7 | 123.58 (17) | C16—C11—C12 | 120.96 (17) |
C3—C2—C1 | 120.80 (18) | C16—C11—O3 | 123.96 (16) |
C3—C2—H2 | 119.6 | C12—C11—O3 | 115.05 (16) |
C1—C2—H2 | 119.6 | O4—C12—C13 | 125.72 (18) |
O1—C3—C2 | 124.58 (17) | O4—C12—C11 | 115.67 (17) |
O1—C3—C4 | 115.41 (16) | C13—C12—C11 | 118.61 (19) |
C2—C3—C4 | 120.01 (17) | C12—C13—C14 | 120.2 (2) |
O2—C4—C5 | 125.29 (17) | C12—C13—H13 | 119.9 |
O2—C4—C3 | 115.34 (16) | C14—C13—H13 | 119.9 |
C5—C4—C3 | 119.37 (17) | C15—C14—C13 | 120.9 (2) |
C4—C5—C6 | 120.50 (18) | C15—C14—H14 | 119.6 |
C4—C5—H5 | 119.7 | C13—C14—H14 | 119.6 |
C6—C5—H5 | 119.7 | C14—C15—C16 | 119.3 (2) |
C5—C6—C1 | 121.05 (18) | C14—C15—H15 | 120.3 |
C5—C6—H6 | 119.5 | C16—C15—H15 | 120.3 |
C1—C6—H6 | 119.5 | C11—C16—C15 | 120.0 (2) |
C8—C7—C1 | 130.22 (17) | C11—C16—H16 | 120.0 |
C8—C7—H7 | 114.9 | C15—C16—H16 | 120.0 |
C1—C7—H7 | 114.9 | O4—C17—H17A | 109.5 |
C7—C8—O3 | 122.59 (16) | O4—C17—H17B | 109.5 |
C7—C8—C18 | 123.81 (16) | H17A—C17—H17B | 109.5 |
O3—C8—C18 | 113.51 (15) | O4—C17—H17C | 109.5 |
O1—C9—H9A | 109.5 | H17A—C17—H17C | 109.5 |
O1—C9—H9B | 109.5 | H17B—C17—H17C | 109.5 |
H9A—C9—H9B | 109.5 | O5—C18—O6 | 123.46 (17) |
O1—C9—H9C | 109.5 | O5—C18—C8 | 120.34 (16) |
H9A—C9—H9C | 109.5 | O6—C18—C8 | 116.19 (16) |
H9B—C9—H9C | 109.5 | C3—O1—C9 | 117.71 (16) |
O2—C10—H10A | 109.5 | C4—O2—C10 | 117.47 (16) |
O2—C10—H10B | 109.5 | C8—O3—C11 | 117.66 (13) |
H10A—C10—H10B | 109.5 | C12—O4—C17 | 117.54 (18) |
O2—C10—H10C | 109.5 | C18—O6—H6A | 109.5 |
C6—C1—C2—C3 | −0.4 (3) | O4—C12—C13—C14 | 179.9 (2) |
C7—C1—C2—C3 | 179.01 (17) | C11—C12—C13—C14 | −0.4 (3) |
C1—C2—C3—O1 | 179.02 (17) | C12—C13—C14—C15 | −0.4 (4) |
C1—C2—C3—C4 | −0.6 (3) | C13—C14—C15—C16 | 1.2 (4) |
O1—C3—C4—O2 | 1.4 (2) | C12—C11—C16—C15 | 0.6 (3) |
C2—C3—C4—O2 | −179.01 (16) | O3—C11—C16—C15 | 178.69 (18) |
O1—C3—C4—C5 | −178.24 (16) | C14—C15—C16—C11 | −1.3 (3) |
C2—C3—C4—C5 | 1.4 (3) | C7—C8—C18—O5 | 179.37 (17) |
O2—C4—C5—C6 | 179.21 (17) | O3—C8—C18—O5 | −4.1 (2) |
C3—C4—C5—C6 | −1.2 (3) | C7—C8—C18—O6 | 0.4 (3) |
C4—C5—C6—C1 | 0.3 (3) | O3—C8—C18—O6 | 176.94 (15) |
C2—C1—C6—C5 | 0.6 (3) | C2—C3—O1—C9 | −3.3 (3) |
C7—C1—C6—C5 | −178.89 (16) | C4—C3—O1—C9 | 176.27 (19) |
C6—C1—C7—C8 | 179.26 (18) | C5—C4—O2—C10 | −2.5 (3) |
C2—C1—C7—C8 | −0.2 (3) | C3—C4—O2—C10 | 177.91 (17) |
C1—C7—C8—O3 | 7.4 (3) | C7—C8—O3—C11 | −103.1 (2) |
C1—C7—C8—C18 | −176.45 (17) | C18—C8—O3—C11 | 80.32 (18) |
C16—C11—C12—O4 | −179.95 (17) | C16—C11—O3—C8 | 8.4 (2) |
O3—C11—C12—O4 | 1.8 (2) | C12—C11—O3—C8 | −173.35 (15) |
C16—C11—C12—C13 | 0.3 (3) | C13—C12—O4—C17 | −10.7 (3) |
O3—C11—C12—C13 | −178.00 (17) | C11—C12—O4—C17 | 169.55 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O5i | 0.82 | 1.79 | 2.607 (2) | 173 |
C2—H2···O3 | 0.93 | 2.31 | 2.941 (2) | 125 |
C7—H7···O6 | 0.93 | 2.42 | 2.787 (2) | 103 |
Symmetry code: (i) −x, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register