Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007419/na6159sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007419/na6159Isup2.hkl |
CCDC reference: 189374
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.109
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 72.57 From the CIF: _reflns_number_total 3063 Count of symmetry unique reflns 1836 Completeness (_total/calc) 166.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1227 Fraction of Friedel pairs measured 0.668 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989b)'; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1996).
C18H20O5 | F(000) = 672 |
Mr = 316.34 | Dx = 1.318 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 20 reflections |
a = 11.920 (1) Å | θ = 9.5–12.3° |
b = 18.114 (2) Å | µ = 0.79 mm−1 |
c = 7.383 (1) Å | T = 293 K |
V = 1594.2 (3) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.28 × 0.18 mm |
Rigaku AFC-5S diffractometer | 2599 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 72.6°, θmin = 4.4° |
ω scans | h = −14→14 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = −22→22 |
Tmin = 0.778, Tmax = 0.879 | l = −8→8 |
6547 measured reflections | 3 standard reflections every 150 reflections |
3063 independent reflections | intensity decay: <2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.17 e Å−3 |
3063 reflections | Δρmin = −0.15 e Å−3 |
217 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0125 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1281 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.1 (2) |
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 | ||
O2 | 1.1501 (1) | 0.01833 (7) | 0.0334 (2) | 0.0657 (4) | |
O80 | 0.9614 (2) | −0.12493 (9) | −0.2710 (2) | 0.0781 (5) | |
O45 | 0.8356 (2) | 0.22429 (8) | −0.0959 (2) | 0.0714 (4) | |
C42 | 0.9993 (2) | 0.15836 (9) | 0.3733 (3) | 0.0526 (5) | |
C8 | 0.9112 (2) | −0.09971 (9) | −0.1162 (3) | 0.0504 (4) | |
C44 | 0.9112 (2) | 0.25600 (9) | 0.2037 (3) | 0.0588 (5) | |
H44 | 0.8888 | 0.3050 | 0.1946 | 0.071* | |
O3 | 1.1653 (2) | −0.05244 (7) | 0.2958 (3) | 0.0793 (6) | |
C9 | 0.9786 (2) | −0.05428 (9) | −0.0090 (3) | 0.0506 (4) | |
C7 | 0.8033 (2) | −0.1174 (1) | −0.0656 (3) | 0.0527 (4) | |
H7 | 0.7596 | −0.1484 | −0.1370 | 0.063* | |
C46 | 0.9208 (2) | 0.13320 (9) | 0.0824 (3) | 0.0501 (4) | |
H46 | 0.9058 | 0.1005 | −0.0118 | 0.060* | |
C10 | 0.9351 (2) | −0.02468 (8) | 0.1487 (3) | 0.0448 (4) | |
C41 | 0.9737 (2) | 0.10775 (8) | 0.2357 (3) | 0.0460 (4) | |
C5 | 0.8247 (2) | −0.04151 (9) | 0.1991 (3) | 0.0503 (4) | |
H5 | 0.7945 | −0.0211 | 0.3040 | 0.060* | |
C6 | 0.7607 (2) | −0.0880 (1) | 0.0943 (3) | 0.0546 (5) | |
H6 | 0.6882 | −0.0999 | 0.1306 | 0.066* | |
O42 | 1.0541 (2) | 0.12912 (7) | 0.5193 (2) | 0.0711 (4) | |
C3 | 1.1301 (2) | 0.01558 (9) | 0.2237 (4) | 0.0581 (5) | |
H3 | 1.1779 (14) | 0.0590 (9) | 0.274 (3) | 0.042 (5)* | |
C45 | 0.8890 (2) | 0.2074 (1) | 0.0652 (3) | 0.0543 (5) | |
C1 | 1.0973 (2) | −0.0404 (2) | −0.0658 (4) | 0.0708 (6) | |
H11 | 1.1405 | −0.0853 | −0.0491 | 0.085* | |
H12 | 1.0985 | −0.0283 | −0.1938 | 0.085* | |
C43 | 0.9670 (2) | 0.2316 (1) | 0.3569 (3) | 0.0608 (5) | |
H43 | 0.9831 | 0.2647 | 0.4497 | 0.073* | |
C4 | 1.0053 (2) | 0.02722 (8) | 0.2617 (3) | 0.0491 (4) | |
H4 | 0.9921 | 0.0149 | 0.3892 | 0.059* | |
C80 | 0.8911 (2) | −0.14799 (15) | −0.4157 (3) | 0.0745 (6) | |
H801 | 0.8306 | −0.1135 | −0.4298 | 0.112* | |
H802 | 0.8613 | −0.1960 | −0.3894 | 0.112* | |
H803 | 0.9340 | −0.1500 | −0.5256 | 0.112* | |
C420 | 1.0894 (2) | 0.1770 (2) | 0.6598 (4) | 0.0860 (8) | |
H421 | 1.0254 | 0.2020 | 0.7095 | 0.129* | |
H422 | 1.1411 | 0.2127 | 0.6119 | 0.129* | |
H423 | 1.1256 | 0.1488 | 0.7531 | 0.129* | |
C450 | 0.7891 (2) | 0.2957 (2) | −0.1159 (4) | 0.0775 (7) | |
H451 | 0.8469 | 0.3321 | −0.1000 | 0.116* | |
H452 | 0.7317 | 0.3031 | −0.0265 | 0.116* | |
H453 | 0.7572 | 0.3006 | −0.2347 | 0.116* | |
H30 | 1.233 (3) | −0.0449 (16) | 0.370 (4) | 0.129 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0424 (6) | 0.0627 (8) | 0.0921 (12) | −0.0108 (5) | 0.0082 (7) | −0.0173 (8) |
O80 | 0.0534 (7) | 0.1005 (11) | 0.0805 (11) | 0.0015 (7) | 0.0040 (8) | −0.0433 (10) |
O45 | 0.0870 (10) | 0.0607 (8) | 0.0666 (10) | 0.0143 (7) | −0.0033 (8) | 0.0149 (7) |
C42 | 0.0513 (9) | 0.0455 (8) | 0.0609 (13) | −0.0025 (7) | −0.0049 (9) | −0.0046 (9) |
C8 | 0.0452 (8) | 0.0471 (8) | 0.0591 (12) | 0.0050 (7) | −0.0014 (8) | −0.0101 (8) |
C44 | 0.0601 (10) | 0.0384 (8) | 0.0780 (15) | 0.0010 (8) | 0.0097 (10) | 0.0005 (9) |
O3 | 0.0660 (8) | 0.0465 (7) | 0.1254 (16) | 0.0066 (6) | −0.0321 (10) | −0.0052 (8) |
C9 | 0.0396 (8) | 0.0468 (8) | 0.0655 (12) | −0.0008 (6) | 0.0022 (8) | −0.0090 (8) |
C7 | 0.0447 (8) | 0.0488 (8) | 0.0645 (12) | −0.0032 (7) | −0.0073 (8) | −0.0042 (9) |
C46 | 0.0499 (8) | 0.0455 (9) | 0.0548 (11) | 0.0002 (6) | 0.0037 (8) | −0.0014 (8) |
C10 | 0.0404 (7) | 0.0377 (7) | 0.0562 (10) | 0.0002 (6) | −0.0046 (7) | −0.0011 (7) |
C41 | 0.0413 (7) | 0.0385 (7) | 0.0581 (11) | −0.0027 (6) | 0.0002 (8) | −0.0031 (8) |
C5 | 0.0474 (9) | 0.0500 (9) | 0.0534 (12) | −0.0056 (7) | 0.0045 (8) | 0.0009 (8) |
C6 | 0.0429 (8) | 0.0595 (10) | 0.0615 (12) | −0.0093 (7) | 0.0000 (9) | 0.0027 (9) |
O42 | 0.0864 (10) | 0.0568 (8) | 0.0701 (10) | 0.0028 (7) | −0.0267 (8) | −0.0144 (7) |
C3 | 0.0456 (8) | 0.0445 (9) | 0.0841 (16) | −0.0004 (7) | −0.0088 (9) | −0.0070 (9) |
C45 | 0.0529 (9) | 0.0468 (9) | 0.0632 (13) | 0.0011 (7) | 0.0040 (9) | 0.0092 (9) |
C1 | 0.0457 (9) | 0.0755 (13) | 0.0912 (17) | −0.0088 (9) | 0.0072 (11) | −0.0274 (13) |
C43 | 0.0657 (11) | 0.0441 (8) | 0.0726 (14) | −0.0041 (8) | 0.0027 (11) | −0.0125 (9) |
C4 | 0.0480 (8) | 0.0392 (7) | 0.0600 (11) | −0.0029 (6) | −0.0046 (8) | −0.0020 (8) |
C80 | 0.0745 (13) | 0.0913 (15) | 0.0575 (14) | 0.0126 (12) | −0.0053 (11) | −0.0119 (13) |
C420 | 0.1020 (18) | 0.0801 (15) | 0.0758 (17) | −0.0053 (13) | −0.0226 (15) | −0.0271 (14) |
C450 | 0.0741 (12) | 0.0619 (12) | 0.0966 (19) | 0.0093 (10) | −0.0005 (14) | 0.0286 (13) |
O2—C3 | 1.426 (3) | C10—C5 | 1.401 (2) |
O2—C1 | 1.436 (2) | C10—C4 | 1.510 (2) |
O80—C8 | 1.369 (2) | C41—C4 | 1.519 (2) |
O80—C80 | 1.420 (3) | C5—C6 | 1.375 (2) |
O45—C45 | 1.383 (3) | C5—H5 | 0.9300 |
O45—C450 | 1.416 (2) | C6—H6 | 0.9300 |
C42—O42 | 1.367 (2) | O42—C420 | 1.416 (3) |
C42—C43 | 1.387 (2) | C3—C4 | 1.529 (2) |
C42—C41 | 1.402 (3) | C3—H3 | 1.04 (2) |
C8—C7 | 1.377 (3) | C1—H11 | 0.9700 |
C8—C9 | 1.396 (2) | C1—H12 | 0.9700 |
C44—C45 | 1.375 (3) | C43—H43 | 0.9300 |
C44—C43 | 1.385 (3) | C4—H4 | 0.9800 |
C44—H44 | 0.9300 | C80—H801 | 0.9600 |
O3—C3 | 1.406 (2) | C80—H802 | 0.9600 |
O3—H30 | 0.99 (3) | C80—H803 | 0.9600 |
C9—C10 | 1.383 (3) | C420—H421 | 0.9600 |
C9—C1 | 1.497 (2) | C420—H422 | 0.9600 |
C7—C6 | 1.390 (3) | C420—H423 | 0.9600 |
C7—H7 | 0.9300 | C450—H451 | 0.9600 |
C46—C41 | 1.375 (3) | C450—H452 | 0.9600 |
C46—C45 | 1.403 (2) | C450—H453 | 0.9600 |
C46—H46 | 0.9300 | ||
C3—O2—C1 | 113.8 (2) | O2—C3—H3 | 104 (1) |
C8—O80—C80 | 117.9 (2) | C4—C3—H3 | 111.3 (9) |
C45—O45—C450 | 118.2 (2) | C44—C45—O45 | 125.9 (2) |
O42—C42—C43 | 124.9 (2) | C44—C45—C46 | 119.6 (2) |
O42—C42—C41 | 115.0 (2) | O45—C45—C46 | 114.5 (2) |
C43—C42—C41 | 120.1 (2) | O2—C1—C9 | 113.3 (2) |
O80—C8—C7 | 123.9 (2) | O2—C1—H11 | 108.9 |
O80—C8—C9 | 114.7 (2) | C9—C1—H11 | 108.9 |
C7—C8—C9 | 121.4 (2) | O2—C1—H12 | 108.9 |
C45—C44—C43 | 119.7 (2) | C9—C1—H12 | 108.9 |
C45—C44—H44 | 120.1 | H11—C1—H12 | 107.7 |
C43—C44—H44 | 120.1 | C44—C43—C42 | 120.7 (2) |
C3—O3—H30 | 110 (2) | C44—C43—H43 | 119.7 |
C10—C9—C8 | 119.3 (2) | C42—C43—H43 | 119.7 |
C10—C9—C1 | 121.7 (2) | C10—C4—C41 | 113.0 (2) |
C8—C9—C1 | 119.0 (2) | C10—C4—C3 | 110.6 (2) |
C8—C7—C6 | 118.9 (2) | C41—C4—C3 | 110.5 (2) |
C8—C7—H7 | 120.6 | C10—C4—H4 | 107.5 |
C6—C7—H7 | 120.6 | C41—C4—H4 | 107.5 |
C41—C46—C45 | 121.3 (2) | C3—C4—H4 | 107.5 |
C41—C46—H46 | 119.3 | O80—C80—H801 | 109.5 |
C45—C46—H46 | 119.3 | O80—C80—H802 | 109.5 |
C9—C10—C5 | 119.4 (2) | H801—C80—H802 | 109.5 |
C9—C10—C4 | 119.9 (2) | O80—C80—H803 | 109.5 |
C5—C10—C4 | 120.6 (2) | H801—C80—H803 | 109.5 |
C46—C41—C42 | 118.5 (2) | H802—C80—H803 | 109.5 |
C46—C41—C4 | 122.7 (2) | O42—C420—H421 | 109.5 |
C42—C41—C4 | 118.8 (2) | O42—C420—H422 | 109.5 |
C6—C5—C10 | 120.3 (2) | H421—C420—H422 | 109.5 |
C6—C5—H5 | 119.8 | O42—C420—H423 | 109.5 |
C10—C5—H5 | 119.8 | H421—C420—H423 | 109.5 |
C5—C6—C7 | 120.6 (2) | H422—C420—H423 | 109.5 |
C5—C6—H6 | 119.7 | O45—C450—H451 | 109.5 |
C7—C6—H6 | 119.7 | O45—C450—H452 | 109.5 |
C42—O42—C420 | 118.8 (2) | H451—C450—H452 | 109.5 |
O3—C3—O2 | 110.7 (2) | O45—C450—H453 | 109.5 |
O3—C3—C4 | 110.0 (2) | H451—C450—H453 | 109.5 |
O2—C3—C4 | 109.8 (2) | H452—C450—H453 | 109.5 |
O3—C3—H3 | 111.3 (9) | ||
C80—O80—C8—C7 | 22.8 (3) | C1—O2—C3—C4 | −64.8 (2) |
C80—O80—C8—C9 | −157.8 (2) | C43—C44—C45—O45 | −179.0 (2) |
O80—C8—C9—C10 | 178.7 (2) | C43—C44—C45—C46 | 1.5 (3) |
C7—C8—C9—C10 | −1.9 (3) | C450—O45—C45—C44 | −6.6 (3) |
O80—C8—C9—C1 | −2.7 (3) | C450—O45—C45—C46 | 172.8 (2) |
C7—C8—C9—C1 | 176.6 (2) | C41—C46—C45—C44 | 0.2 (3) |
O80—C8—C7—C6 | −179.5 (2) | C41—C46—C45—O45 | −179.3 (2) |
C9—C8—C7—C6 | 1.2 (3) | C3—O2—C1—C9 | 44.5 (3) |
C8—C9—C10—C5 | 0.8 (3) | C10—C9—C1—O2 | −13.5 (3) |
C1—C9—C10—C5 | −177.7 (2) | C8—C9—C1—O2 | 168.0 (2) |
C8—C9—C10—C4 | −177.3 (2) | C45—C44—C43—C42 | −1.0 (3) |
C1—C9—C10—C4 | 4.2 (3) | O42—C42—C43—C44 | −179.6 (2) |
C45—C46—C41—C42 | −2.3 (3) | C41—C42—C43—C44 | −1.2 (3) |
C45—C46—C41—C4 | 177.6 (2) | C9—C10—C4—C41 | 101.8 (2) |
O42—C42—C41—C46 | −178.6 (2) | C5—C10—C4—C41 | −76.2 (2) |
C43—C42—C41—C46 | 2.8 (3) | C9—C10—C4—C3 | −22.6 (2) |
O42—C42—C41—C4 | 1.5 (2) | C5—C10—C4—C3 | 159.3 (2) |
C43—C42—C41—C4 | −177.1 (2) | C46—C41—C4—C10 | −23.4 (2) |
C9—C10—C5—C6 | 1.0 (3) | C42—C41—C4—C10 | 156.5 (2) |
C4—C10—C5—C6 | 179.1 (2) | C46—C41—C4—C3 | 101.2 (2) |
C10—C5—C6—C7 | −1.8 (3) | C42—C41—C4—C3 | −79.0 (2) |
C8—C7—C6—C5 | 0.7 (3) | O3—C3—C4—C10 | −70.7 (2) |
C43—C42—O42—C420 | −5.3 (3) | O2—C3—C4—C10 | 51.4 (2) |
C41—C42—O42—C420 | 176.1 (2) | O3—C3—C4—C41 | 163.4 (2) |
C1—O2—C3—O3 | 56.9 (2) | O2—C3—C4—C41 | −74.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H30···O2i | 0.98 (4) | 1.90 (4) | 2.881 (2) | 171 (3) |
Symmetry code: (i) −x+5/2, −y, z+1/2. |
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