Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005234/ww6356sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005234/ww63566sup2.hkl |
CCDC reference: 269889
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H18O5 | F(000) = 568 |
Mr = 266.28 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2988 reflections |
a = 5.8430 (3) Å | θ = 1.6–27.6° |
b = 12.8501 (8) Å | µ = 0.10 mm−1 |
c = 17.5767 (11) Å | T = 150 K |
β = 97.449 (5)° | Prism, colorless |
V = 1308.58 (13) Å3 | 0.57 × 0.40 × 0.27 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 2988 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2624 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.027 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 2.0° |
ω scans | h = −7→7 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −16→16 |
Tmin = 0.944, Tmax = 0.973 | l = −22→22 |
18334 measured reflections |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.2964P] where P = (Fo2 + 2Fc2)/3 |
2988 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.48132 (12) | 0.63003 (6) | 0.45262 (4) | 0.0281 (2) | |
O2 | 0.57775 (12) | 0.58123 (6) | 0.26059 (4) | 0.0260 (2) | |
O3 | 0.82973 (12) | 0.45963 (5) | 0.35702 (4) | 0.0246 (2) | |
O4 | 0.23150 (14) | 0.60181 (7) | 0.19010 (5) | 0.0419 (3) | |
O5 | 0.59197 (13) | 0.34430 (6) | 0.29131 (5) | 0.0358 (3) | |
C1 | 0.47188 (16) | 0.56786 (8) | 0.32919 (6) | 0.0248 (3) | |
C2 | 0.46256 (17) | 0.66961 (8) | 0.37478 (6) | 0.0246 (3) | |
C3 | 0.68437 (16) | 0.73200 (7) | 0.37466 (5) | 0.0231 (2) | |
C4 | 0.6587 (2) | 0.84389 (8) | 0.40308 (7) | 0.0314 (3) | |
C5 | 0.8881 (2) | 0.89057 (9) | 0.43211 (7) | 0.0346 (3) | |
C6 | 1.0378 (2) | 0.83403 (9) | 0.47737 (7) | 0.0358 (3) | |
C7 | 0.9761 (2) | 0.72545 (9) | 0.49856 (6) | 0.0320 (3) | |
C8 | 0.85803 (16) | 0.66476 (8) | 0.42874 (5) | 0.0236 (3) | |
C9 | 0.70085 (17) | 0.57803 (8) | 0.45189 (6) | 0.0258 (3) | |
C10 | 0.63198 (17) | 0.50064 (8) | 0.38717 (6) | 0.0250 (3) | |
C11 | 0.43822 (19) | 0.59999 (8) | 0.19485 (6) | 0.0289 (3) | |
C12 | 0.5770 (2) | 0.61705 (11) | 0.13010 (7) | 0.0381 (3) | |
C13 | 0.78279 (18) | 0.37948 (8) | 0.30738 (6) | 0.0269 (3) | |
C14 | 0.9934 (2) | 0.34322 (10) | 0.27563 (8) | 0.0355 (3) | |
H1 | 0.319 (2) | 0.5365 (10) | 0.3166 (7) | 0.026 (3)* | |
H2 | 0.318 (2) | 0.7090 (9) | 0.3641 (7) | 0.026 (3)* | |
H3 | 0.728 (2) | 0.7353 (9) | 0.3235 (7) | 0.023 (3)* | |
H4A | 0.576 (2) | 0.8847 (11) | 0.3605 (8) | 0.040 (4)* | |
H4B | 0.561 (2) | 0.8441 (11) | 0.4457 (8) | 0.037 (3)* | |
H5 | 0.923 (3) | 0.9619 (12) | 0.4184 (8) | 0.043 (4)* | |
H6 | 1.187 (3) | 0.8609 (12) | 0.4988 (9) | 0.047 (4)* | |
H7A | 1.110 (3) | 0.6863 (12) | 0.5212 (8) | 0.042 (4)* | |
H7B | 0.868 (2) | 0.7301 (10) | 0.5371 (8) | 0.033 (3)* | |
H8 | 0.980 (2) | 0.6348 (10) | 0.3999 (7) | 0.026 (3)* | |
H9 | 0.749 (2) | 0.5464 (10) | 0.5016 (7) | 0.027 (3)* | |
H10 | 0.546 (2) | 0.4437 (10) | 0.4060 (7) | 0.028 (3)* | |
H12A | 0.541 (3) | 0.6835 (17) | 0.1108 (11) | 0.076 (6)* | |
H12B | 0.533 (3) | 0.5668 (15) | 0.0900 (11) | 0.068 (5)* | |
H12C | 0.737 (3) | 0.6092 (14) | 0.1444 (11) | 0.067 (5)* | |
H13A | 1.009 (3) | 0.3832 (15) | 0.2316 (12) | 0.069 (5)* | |
H13B | 0.975 (3) | 0.2718 (15) | 0.2627 (10) | 0.062 (5)* | |
H13C | 1.133 (3) | 0.3556 (12) | 0.3101 (9) | 0.049 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0282 (4) | 0.0288 (4) | 0.0302 (4) | 0.0049 (3) | 0.0148 (3) | 0.0055 (3) |
O2 | 0.0252 (3) | 0.0291 (4) | 0.0240 (3) | −0.0011 (3) | 0.0041 (3) | 0.0023 (3) |
O3 | 0.0241 (3) | 0.0234 (3) | 0.0276 (3) | 0.0022 (3) | 0.0081 (3) | 0.0002 (3) |
O4 | 0.0317 (4) | 0.0475 (5) | 0.0439 (5) | −0.0001 (4) | −0.0047 (4) | 0.0021 (4) |
O5 | 0.0283 (4) | 0.0332 (4) | 0.0461 (5) | −0.0027 (3) | 0.0059 (3) | −0.0059 (3) |
C1 | 0.0210 (4) | 0.0253 (5) | 0.0292 (5) | −0.0021 (4) | 0.0072 (4) | 0.0027 (4) |
C2 | 0.0220 (4) | 0.0248 (5) | 0.0280 (5) | 0.0024 (4) | 0.0067 (4) | 0.0041 (4) |
C3 | 0.0239 (4) | 0.0237 (4) | 0.0220 (4) | −0.0005 (4) | 0.0045 (3) | 0.0024 (4) |
C4 | 0.0339 (5) | 0.0239 (5) | 0.0352 (6) | 0.0023 (4) | 0.0000 (5) | 0.0007 (4) |
C5 | 0.0402 (6) | 0.0279 (5) | 0.0356 (6) | −0.0052 (4) | 0.0048 (5) | −0.0059 (4) |
C6 | 0.0329 (6) | 0.0373 (6) | 0.0363 (6) | −0.0027 (5) | 0.0011 (5) | −0.0118 (5) |
C7 | 0.0324 (5) | 0.0366 (6) | 0.0258 (5) | 0.0073 (4) | −0.0010 (4) | −0.0038 (4) |
C8 | 0.0235 (4) | 0.0259 (5) | 0.0223 (4) | 0.0030 (4) | 0.0060 (4) | 0.0006 (4) |
C9 | 0.0291 (5) | 0.0265 (5) | 0.0236 (5) | 0.0064 (4) | 0.0103 (4) | 0.0056 (4) |
C10 | 0.0250 (5) | 0.0226 (4) | 0.0296 (5) | 0.0020 (4) | 0.0121 (4) | 0.0046 (4) |
C11 | 0.0336 (5) | 0.0218 (5) | 0.0297 (5) | −0.0014 (4) | −0.0017 (4) | −0.0007 (4) |
C12 | 0.0478 (7) | 0.0391 (6) | 0.0266 (5) | −0.0025 (5) | 0.0024 (5) | 0.0027 (5) |
C13 | 0.0283 (5) | 0.0240 (5) | 0.0289 (5) | 0.0013 (4) | 0.0062 (4) | 0.0009 (4) |
C14 | 0.0310 (6) | 0.0361 (6) | 0.0413 (6) | 0.0012 (5) | 0.0121 (5) | −0.0086 (5) |
O1—C2 | 1.450 (1) | C13—C14 | 1.4903 (16) |
O1—C9 | 1.448 (1) | C1—H1 | 0.979 (12) |
O2—C1 | 1.435 (1) | C2—H2 | 0.982 (12) |
O2—C11 | 1.347 (1) | C3—H3 | 0.967 (12) |
O3—C10 | 1.433 (1) | C4—H4A | 0.987 (14) |
O3—C13 | 1.355 (1) | C4—H4B | 0.999 (13) |
O4—C11 | 1.200 (1) | C5—H5 | 0.976 (16) |
O5—C13 | 1.202 (1) | C6—H6 | 0.967 (17) |
C1—C2 | 1.5382 (15) | C7—H7A | 0.971 (17) |
C1—C10 | 1.5533 (14) | C7—H7B | 0.986 (13) |
C2—C3 | 1.5242 (14) | C8—H8 | 1.003 (12) |
C3—C4 | 1.5358 (14) | C9—H9 | 0.972 (12) |
C3—C8 | 1.5587 (13) | C10—H10 | 0.970 (12) |
C4—C5 | 1.4965 (17) | C12—H12A | 0.93 (2) |
C5—C6 | 1.3211 (17) | C12—H12B | 0.966 (19) |
C6—C7 | 1.5001 (16) | C12—H12C | 0.942 (18) |
C7—C8 | 1.5397 (14) | C14—H13A | 0.94 (2) |
C8—C9 | 1.5323 (14) | C14—H13B | 0.948 (19) |
C9—C10 | 1.5252 (15) | C14—H13C | 0.964 (17) |
C11—C12 | 1.4967 (16) | ||
O1···C7i | 3.3894 (14) | C14···H3ix | 2.889 (12) |
O1···C9ii | 3.4002 (13) | H1···O4 | 2.370 (12) |
O1···C10ii | 3.4162 (13) | H1···H13Ci | 2.56 (2) |
O2···C8 | 3.3637 (12) | H2···H4B | 2.561 (18) |
O2···O3 | 2.6144 (10) | H2···H8i | 2.351 (17) |
O2···O5 | 3.0913 (11) | H3···O2 | 2.379 (12) |
O2···C13 | 2.9287 (13) | H3···C14vii | 2.889 (12) |
O3···O2 | 2.6144 (10) | H3···H13Bvii | 2.49 (2) |
O5···C11iii | 3.1555 (13) | H4A···O5v | 2.770 (14) |
O5···C1 | 3.0512 (13) | H4A···C11v | 2.930 (14) |
O5···O2 | 3.0913 (11) | H4B···O1 | 2.795 (14) |
O1···H7Ai | 2.713 (17) | H4B···C7 | 2.913 (13) |
O1···H10ii | 2.684 (12) | H4B···H2 | 2.561 (18) |
O1···H4B | 2.795 (14) | H4B···H6i | 2.49 (2) |
O1···H9ii | 2.807 (13) | H5···O4v | 2.690 (15) |
O1···H7B | 2.845 (13) | H6···H4Bvi | 2.49 (2) |
O2···H3 | 2.379 (12) | H6···C12x | 3.039 (17) |
O3···H7Aiv | 2.833 (15) | H6···H12Bx | 2.59 (2) |
O3···H8 | 2.497 (13) | H7A···O1vi | 2.713 (17) |
O4···H1 | 2.370 (12) | H7A···O3iv | 2.833 (15) |
O4···H13Bv | 2.679 (19) | H7B···O1 | 2.845 (13) |
O4···H5iii | 2.690 (15) | H7B···C4 | 2.904 (14) |
O4···H12Ci | 2.898 (18) | H7B···H9 | 2.517 (18) |
O5···H10 | 2.431 (12) | H8···O3 | 2.497 (13) |
O5···H13Ci | 2.748 (18) | H8···C2vi | 2.944 (12) |
O5···H4Aiii | 2.770 (14) | H8···H2vi | 2.351 (17) |
O5···H12Aiii | 2.86 (2) | H9···H7B | 2.517 (18) |
C1···O5 | 3.0512 (13) | H9···O1ii | 2.807 (13) |
C7···O1vi | 3.3894 (14) | H9···H10ii | 2.520 (17) |
C8···O2 | 3.3637 (12) | H10···O5 | 2.431 (12) |
C9···O1ii | 3.4002 (13) | H10···O1ii | 2.684 (12) |
C10···O1ii | 3.4162 (13) | H10···C9ii | 3.055 (12) |
C11···O5v | 3.1555 (13) | H10···H9ii | 2.520 (17) |
C13···O2 | 2.9287 (13) | H12A···O5v | 2.86 (2) |
C2···H8i | 2.944 (12) | H12B···C4iii | 3.084 (19) |
C4···H12Bv | 3.084 (19) | H12B···H6viii | 2.59 (2) |
C4···H7B | 2.904 (14) | H12C···O4vi | 2.898 (18) |
C5···H13Avii | 3.02 (2) | H13A···C5ix | 3.02 (2) |
C7···H4B | 2.913 (13) | H13B···O4iii | 2.679 (19) |
C9···H10ii | 3.055 (12) | H13B···H3ix | 2.49 (2) |
C11···H4Aiii | 2.930 (14) | H13C···O5vi | 2.748 (18) |
C12···H6viii | 3.039 (17) | H13C···H1vi | 2.56 (2) |
C2—O1—C9 | 96.44 (7) | C4—C3—H3 | 108.1 (7) |
C1—O2—C11 | 117.61 (8) | C8—C3—H3 | 111.2 (7) |
C10—O3—C13 | 114.35 (8) | C3—C4—H4A | 108.0 (8) |
O2—C1—C2 | 112.59 (8) | C3—C4—H4B | 109.6 (8) |
O2—C1—C10 | 109.23 (8) | C5—C4—H4A | 112.0 (8) |
C2—C1—C10 | 100.95 (8) | C5—C4—H4B | 108.5 (8) |
O1—C2—C1 | 100.95 (8) | H4A—C4—H4B | 107.2 (11) |
O1—C2—C3 | 103.03 (8) | C4—C5—H5 | 119.9 (10) |
C1—C2—C3 | 111.03 (8) | C6—C5—H5 | 121.5 (10) |
C2—C3—C4 | 111.90 (8) | C5—C6—H6 | 122.1 (9) |
C2—C3—C8 | 101.19 (7) | C7—C6—H6 | 118.0 (9) |
C4—C3—C8 | 113.82 (8) | C6—C7—H7A | 112.1 (10) |
C3—C4—C5 | 111.42 (9) | C6—C7—H7B | 108.1 (8) |
C4—C5—C6 | 118.60 (10) | C8—C7—H7A | 108.6 (9) |
C5—C6—C7 | 119.96 (11) | C8—C7—H7B | 108.5 (8) |
C6—C7—C8 | 111.75 (9) | H7A—C7—H7B | 107.7 (12) |
C3—C8—C7 | 113.22 (8) | C3—C8—H8 | 110.7 (7) |
C3—C8—C9 | 101.53 (7) | C7—C8—H8 | 108.8 (7) |
C7—C8—C9 | 112.26 (8) | C9—C8—H8 | 110.2 (7) |
O1—C9—C8 | 103.23 (8) | O1—C9—H9 | 109.8 (7) |
O1—C9—C10 | 99.16 (8) | C8—C9—H9 | 115.4 (7) |
C8—C9—C10 | 112.67 (8) | C10—C9—H9 | 114.6 (8) |
O3—C10—C1 | 114.07 (8) | O3—C10—H10 | 109.1 (7) |
O3—C10—C9 | 111.61 (8) | C1—C10—H10 | 110.4 (7) |
C1—C10—C9 | 101.83 (8) | C9—C10—H10 | 109.6 (7) |
O2—C11—O4 | 123.71 (10) | C11—C12—H12A | 107.0 (11) |
O2—C11—C12 | 110.56 (9) | C11—C12—H12B | 109.7 (11) |
O4—C11—C12 | 125.72 (10) | C11—C12—H12C | 113.5 (12) |
O3—C13—O5 | 122.77 (10) | H12A—C12—H12B | 108.7 (17) |
O3—C13—C14 | 111.77 (9) | H12A—C12—H12C | 111.4 (16) |
O5—C13—C14 | 125.46 (10) | H12B—C12—H12C | 106.5 (16) |
O2—C1—H1 | 109.9 (7) | C13—C14—H13A | 108.0 (11) |
C2—C1—H1 | 112.0 (7) | C13—C14—H13B | 108.6 (11) |
C10—C1—H1 | 112.0 (7) | C13—C14—H13C | 112.7 (10) |
O1—C2—H2 | 108.6 (7) | H13A—C14—H13B | 110.5 (16) |
C1—C2—H2 | 115.2 (7) | H13A—C14—H13C | 105.2 (15) |
C3—C2—H2 | 116.1 (7) | H13B—C14—H13C | 111.8 (14) |
C2—C3—H3 | 110.6 (7) | ||
C2—O1—C9—C8 | 54.87 (8) | O1—C2—C3—C8 | 35.61 (9) |
C2—O1—C9—C10 | −61.17 (8) | O1—C2—C3—C4 | −85.94 (9) |
C9—O1—C2—C1 | 58.52 (8) | C4—C3—C8—C7 | −2.12 (12) |
C9—O1—C2—C3 | −56.31 (8) | C8—C3—C4—C5 | 43.60 (12) |
C11—O2—C1—C10 | 154.62 (9) | C2—C3—C8—C7 | −122.32 (9) |
C1—O2—C11—O4 | −3.18 (15) | C4—C3—C8—C9 | 118.42 (9) |
C1—O2—C11—C12 | 177.21 (9) | C2—C3—C8—C9 | −1.78 (9) |
C11—O2—C1—C2 | −94.10 (10) | C2—C3—C4—C5 | 157.56 (9) |
C10—O3—C13—C14 | 177.64 (9) | C3—C4—C5—C6 | −44.92 (15) |
C13—O3—C10—C1 | −74.50 (10) | C4—C5—C6—C7 | 0.03 (17) |
C13—O3—C10—C9 | 170.77 (8) | C5—C6—C7—C8 | 43.92 (15) |
C10—O3—C13—O5 | −1.55 (14) | C6—C7—C8—C3 | −39.92 (12) |
O2—C1—C10—O3 | −6.08 (11) | C6—C7—C8—C9 | −154.16 (9) |
C10—C1—C2—O1 | −32.23 (9) | C3—C8—C9—C10 | 73.39 (9) |
C2—C1—C10—C9 | −4.51 (9) | C7—C8—C9—C10 | −165.39 (9) |
C10—C1—C2—C3 | 76.46 (9) | C7—C8—C9—O1 | 88.63 (9) |
O2—C1—C2—O1 | −148.58 (8) | C3—C8—C9—O1 | −32.59 (9) |
C2—C1—C10—O3 | −124.88 (8) | C8—C9—C10—O3 | 53.31 (11) |
O2—C1—C10—C9 | 114.30 (9) | O1—C9—C10—C1 | 39.80 (9) |
O2—C1—C2—C3 | −39.89 (11) | O1—C9—C10—O3 | 161.89 (8) |
C1—C2—C3—C4 | 166.74 (8) | C8—C9—C10—C1 | −68.77 (10) |
C1—C2—C3—C8 | −71.71 (9) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+2, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2; (vi) x+1, y, z; (vii) −x+2, y+1/2, −z+1/2; (viii) x−1, −y+3/2, z−1/2; (ix) −x+2, y−1/2, −z+1/2; (x) x+1, −y+3/2, z+1/2. |