Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002693/gk2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002693/gk2048IIsup2.hkl |
CCDC reference: 636642
Data collection: CRYSOM (Martinez-Ripoll & Cano, 1996); cell refinement: CRYSOM; data reduction: X-RAY80 (Stewart et al., 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C21H32O3 | Dx = 1.191 Mg m−3 |
Mr = 332.47 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 20 reflections |
a = 6.7100 (13) Å | θ = 5.0–10.2° |
b = 9.7380 (19) Å | µ = 0.61 mm−1 |
c = 28.383 (6) Å | T = 293 K |
V = 1854.6 (6) Å3 | Prismatic, colourless |
Z = 4 | 0.2 × 0.2 × 0.2 mm |
F(000) = 728 |
Seifert XRD 3003 SC diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 60.0°, θmin = 3.1° |
Graphite monochromator | h = 0→7 |
ω/2θ scans | k = 0→10 |
1614 measured reflections | l = 0→29 |
1614 independent reflections | 2 standard reflections every 700 reflections |
1274 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0423P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.16 e Å−3 |
1614 reflections | Δρmin = −0.14 e Å−3 |
219 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0065 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs? |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (5) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1829 (4) | 0.4715 (3) | 0.26632 (8) | 0.0672 (8) | |
O2 | 0.2572 (3) | 0.6880 (2) | 0.24895 (7) | 0.0534 (6) | |
O3 | 0.2472 (4) | 1.2470 (2) | 0.47775 (7) | 0.0575 (7) | |
C1 | 0.3118 (6) | 0.5504 (3) | 0.40708 (11) | 0.0533 (10) | |
H1A | 0.4358 | 0.5529 | 0.4246 | 0.064* | |
H1B | 0.2046 | 0.5364 | 0.4295 | 0.064* | |
C2 | 0.3173 (7) | 0.4285 (3) | 0.37330 (13) | 0.0696 (13) | |
H2A | 0.3469 | 0.3454 | 0.3908 | 0.084* | |
H2B | 0.1874 | 0.4174 | 0.3588 | 0.084* | |
C3 | 0.4726 (7) | 0.4482 (3) | 0.33535 (12) | 0.0648 (11) | |
H3A | 0.4633 | 0.3724 | 0.3133 | 0.078* | |
H3B | 0.6035 | 0.4445 | 0.3498 | 0.078* | |
C4 | 0.4546 (5) | 0.5819 (3) | 0.30808 (10) | 0.0441 (8) | |
C5 | 0.4436 (4) | 0.7035 (3) | 0.34378 (10) | 0.0342 (7) | |
H5A | 0.5693 | 0.6969 | 0.3612 | 0.041* | |
C6 | 0.4487 (5) | 0.8469 (3) | 0.32289 (10) | 0.0404 (8) | |
H6A | 0.3190 | 0.8694 | 0.3099 | 0.048* | |
H6B | 0.5456 | 0.8504 | 0.2976 | 0.048* | |
C7 | 0.5039 (5) | 0.9512 (3) | 0.36078 (10) | 0.0423 (8) | |
H7A | 0.6356 | 0.9299 | 0.3728 | 0.051* | |
H7B | 0.5090 | 1.0420 | 0.3468 | 0.051* | |
C8 | 0.3563 (4) | 0.9523 (3) | 0.40153 (9) | 0.0300 (7) | |
C9 | 0.3205 (4) | 0.8048 (3) | 0.42022 (9) | 0.0301 (7) | |
H9A | 0.4478 | 0.7789 | 0.4346 | 0.036* | |
C10 | 0.2816 (5) | 0.6904 (3) | 0.38268 (9) | 0.0332 (7) | |
C11 | 0.1727 (5) | 0.8090 (3) | 0.46211 (10) | 0.0402 (8) | |
H11A | 0.1180 | 0.7176 | 0.4664 | 0.048* | |
H11B | 0.2468 | 0.8316 | 0.4904 | 0.048* | |
C12 | −0.0001 (5) | 0.9099 (3) | 0.45756 (11) | 0.0459 (8) | |
H12A | −0.0996 | 0.8719 | 0.4365 | 0.055* | |
H12B | −0.0616 | 0.9227 | 0.4882 | 0.055* | |
C13 | 0.0686 (5) | 1.0487 (3) | 0.43871 (10) | 0.0427 (8) | |
H13A | −0.0403 | 1.1158 | 0.4379 | 0.051* | |
C14 | 0.1592 (5) | 1.0252 (3) | 0.38958 (10) | 0.0384 (8) | |
H14A | 0.1827 | 1.1114 | 0.3734 | 0.046* | |
H14B | 0.0740 | 0.9676 | 0.3703 | 0.046* | |
C15 | 0.4320 (5) | 1.0451 (3) | 0.44235 (10) | 0.0409 (8) | |
H15A | 0.5109 | 0.9921 | 0.4645 | 0.049* | |
H15B | 0.5133 | 1.1194 | 0.4302 | 0.049* | |
C16 | 0.2456 (5) | 1.1012 (3) | 0.46614 (11) | 0.0407 (8) | |
C17 | 0.2353 (6) | 1.1458 (3) | 0.51503 (11) | 0.0528 (9) | |
H17A | 0.1090 | 1.1357 | 0.5313 | 0.063* | |
H17B | 0.3522 | 1.1322 | 0.5346 | 0.063* | |
C18 | 0.6431 (5) | 0.5976 (4) | 0.27696 (12) | 0.0651 (11) | |
H18A | 0.6352 | 0.6818 | 0.2595 | 0.098* | |
H18B | 0.6515 | 0.5216 | 0.2555 | 0.098* | |
H18C | 0.7595 | 0.5990 | 0.2966 | 0.098* | |
C19 | 0.2806 (5) | 0.5727 (3) | 0.27360 (10) | 0.0420 (8) | |
C20 | 0.0700 (4) | 0.6941 (3) | 0.36222 (10) | 0.0429 (8) | |
H20A | 0.0554 | 0.6222 | 0.3393 | 0.064* | |
H20B | 0.0473 | 0.7814 | 0.3474 | 0.064* | |
H20C | −0.0250 | 0.6811 | 0.3871 | 0.064* | |
C21 | 0.1063 (5) | 0.6890 (4) | 0.21251 (11) | 0.0632 (10) | |
H21A | 0.1038 | 0.7775 | 0.1976 | 0.095* | |
H21B | −0.0216 | 0.6704 | 0.2263 | 0.095* | |
H21C | 0.1365 | 0.6199 | 0.1895 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0743 (18) | 0.0564 (14) | 0.0708 (16) | −0.0180 (15) | −0.0179 (14) | −0.0106 (14) |
O2 | 0.0533 (13) | 0.0564 (14) | 0.0506 (13) | −0.0068 (14) | −0.0154 (13) | −0.0027 (12) |
O3 | 0.0744 (16) | 0.0295 (10) | 0.0687 (14) | −0.0012 (13) | 0.0065 (15) | −0.0100 (12) |
C1 | 0.088 (3) | 0.0263 (16) | 0.0457 (18) | −0.0034 (19) | 0.0003 (19) | 0.0042 (15) |
C2 | 0.122 (4) | 0.0259 (18) | 0.060 (2) | 0.002 (2) | −0.013 (3) | 0.0026 (17) |
C3 | 0.088 (3) | 0.043 (2) | 0.064 (2) | 0.021 (2) | −0.020 (2) | −0.017 (2) |
C4 | 0.0408 (19) | 0.046 (2) | 0.0458 (19) | 0.0085 (18) | −0.0068 (16) | −0.0131 (17) |
C5 | 0.0331 (17) | 0.0349 (17) | 0.0345 (16) | 0.0006 (15) | −0.0073 (15) | −0.0093 (14) |
C6 | 0.0451 (19) | 0.0418 (17) | 0.0341 (16) | −0.0071 (16) | 0.0099 (16) | −0.0027 (15) |
C7 | 0.046 (2) | 0.0375 (17) | 0.0438 (18) | −0.0115 (17) | 0.0083 (16) | 0.0005 (16) |
C8 | 0.0328 (16) | 0.0254 (15) | 0.0319 (16) | −0.0004 (15) | −0.0017 (13) | −0.0024 (13) |
C9 | 0.0330 (16) | 0.0297 (15) | 0.0275 (15) | 0.0001 (14) | −0.0028 (13) | 0.0004 (13) |
C10 | 0.0438 (19) | 0.0266 (15) | 0.0293 (15) | −0.0033 (16) | −0.0043 (15) | 0.0014 (12) |
C11 | 0.0500 (19) | 0.0383 (17) | 0.0323 (16) | −0.0056 (17) | 0.0016 (15) | 0.0007 (15) |
C12 | 0.0374 (18) | 0.056 (2) | 0.0444 (18) | −0.0028 (17) | 0.0051 (15) | −0.0079 (17) |
C13 | 0.0391 (19) | 0.0374 (18) | 0.0516 (19) | 0.0102 (17) | −0.0021 (16) | −0.0078 (17) |
C14 | 0.0444 (18) | 0.0276 (16) | 0.0433 (17) | 0.0011 (16) | −0.0070 (16) | 0.0000 (14) |
C15 | 0.0404 (19) | 0.0360 (17) | 0.0463 (18) | −0.0028 (17) | −0.0007 (16) | −0.0053 (17) |
C16 | 0.0464 (18) | 0.0263 (15) | 0.0495 (18) | 0.0024 (16) | 0.0010 (18) | −0.0105 (14) |
C17 | 0.066 (2) | 0.0417 (18) | 0.051 (2) | −0.001 (2) | 0.000 (2) | −0.0092 (16) |
C18 | 0.039 (2) | 0.089 (3) | 0.067 (2) | 0.009 (2) | −0.0013 (19) | −0.040 (2) |
C19 | 0.042 (2) | 0.045 (2) | 0.0390 (18) | 0.0002 (18) | 0.0024 (16) | −0.0106 (16) |
C20 | 0.0392 (18) | 0.0458 (19) | 0.0437 (18) | −0.0118 (17) | 0.0034 (16) | −0.0090 (16) |
C21 | 0.058 (2) | 0.085 (3) | 0.047 (2) | −0.001 (2) | −0.0171 (19) | −0.003 (2) |
O1—C19 | 1.201 (4) | C9—C11 | 1.549 (4) |
O2—C19 | 1.332 (4) | C9—C10 | 1.564 (4) |
O2—C21 | 1.448 (3) | C9—H9A | 0.9800 |
O3—C17 | 1.448 (3) | C10—C20 | 1.534 (4) |
O3—C16 | 1.458 (3) | C11—C12 | 1.525 (4) |
C1—C2 | 1.527 (4) | C11—H11A | 0.9700 |
C1—C10 | 1.543 (4) | C11—H11B | 0.9700 |
C1—H1A | 0.9700 | C12—C13 | 1.525 (4) |
C1—H1B | 0.9700 | C12—H12A | 0.9700 |
C2—C3 | 1.511 (5) | C12—H12B | 0.9700 |
C2—H2A | 0.9700 | C13—C16 | 1.509 (4) |
C2—H2B | 0.9700 | C13—C14 | 1.538 (4) |
C3—C4 | 1.519 (4) | C13—H13A | 0.9800 |
C3—H3A | 0.9700 | C14—H14A | 0.9700 |
C3—H3B | 0.9700 | C14—H14B | 0.9700 |
C4—C19 | 1.526 (4) | C15—C16 | 1.523 (4) |
C4—C18 | 1.550 (4) | C15—H15A | 0.9700 |
C4—C5 | 1.560 (4) | C15—H15B | 0.9700 |
C5—C6 | 1.518 (4) | C16—C17 | 1.456 (4) |
C5—C10 | 1.555 (4) | C17—H17A | 0.9700 |
C5—H5A | 0.9800 | C17—H17B | 0.9700 |
C6—C7 | 1.525 (4) | C18—H18A | 0.9600 |
C6—H6A | 0.9700 | C18—H18B | 0.9600 |
C6—H6B | 0.9700 | C18—H18C | 0.9600 |
C7—C8 | 1.523 (4) | C20—H20A | 0.9600 |
C7—H7A | 0.9700 | C20—H20B | 0.9600 |
C7—H7B | 0.9700 | C20—H20C | 0.9600 |
C8—C14 | 1.538 (4) | C21—H21A | 0.9600 |
C8—C9 | 1.550 (4) | C21—H21B | 0.9600 |
C8—C15 | 1.555 (4) | C21—H21C | 0.9600 |
C19—O2—C21 | 117.6 (3) | C12—C11—H11A | 108.3 |
C17—O3—C16 | 60.12 (18) | C9—C11—H11A | 108.3 |
C2—C1—C10 | 114.1 (2) | C12—C11—H11B | 108.3 |
C2—C1—H1A | 108.7 | C9—C11—H11B | 108.3 |
C10—C1—H1A | 108.7 | H11A—C11—H11B | 107.4 |
C2—C1—H1B | 108.7 | C13—C12—C11 | 111.8 (3) |
C10—C1—H1B | 108.7 | C13—C12—H12A | 109.3 |
H1A—C1—H1B | 107.6 | C11—C12—H12A | 109.3 |
C3—C2—C1 | 111.4 (3) | C13—C12—H12B | 109.3 |
C3—C2—H2A | 109.3 | C11—C12—H12B | 109.3 |
C1—C2—H2A | 109.3 | H12A—C12—H12B | 107.9 |
C3—C2—H2B | 109.3 | C16—C13—C12 | 110.9 (3) |
C1—C2—H2B | 109.3 | C16—C13—C14 | 102.0 (2) |
H2A—C2—H2B | 108.0 | C12—C13—C14 | 107.8 (3) |
C2—C3—C4 | 114.7 (3) | C16—C13—H13A | 111.9 |
C2—C3—H3A | 108.6 | C12—C13—H13A | 111.9 |
C4—C3—H3A | 108.6 | C14—C13—H13A | 111.9 |
C2—C3—H3B | 108.6 | C13—C14—C8 | 102.0 (2) |
C4—C3—H3B | 108.6 | C13—C14—H14A | 111.4 |
H3A—C3—H3B | 107.6 | C8—C14—H14A | 111.4 |
C3—C4—C19 | 109.7 (3) | C13—C14—H14B | 111.4 |
C3—C4—C18 | 108.1 (3) | C8—C14—H14B | 111.4 |
C19—C4—C18 | 105.3 (2) | H14A—C14—H14B | 109.2 |
C3—C4—C5 | 108.8 (2) | C16—C15—C8 | 105.7 (2) |
C19—C4—C5 | 115.1 (3) | C16—C15—H15A | 110.6 |
C18—C4—C5 | 109.5 (3) | C8—C15—H15A | 110.6 |
C6—C5—C10 | 111.6 (2) | C16—C15—H15B | 110.6 |
C6—C5—C4 | 116.4 (2) | C8—C15—H15B | 110.6 |
C10—C5—C4 | 115.6 (2) | H15A—C15—H15B | 108.7 |
C6—C5—H5A | 103.8 | C17—C16—O3 | 59.63 (17) |
C10—C5—H5A | 103.8 | C17—C16—C13 | 123.7 (3) |
C4—C5—H5A | 103.8 | O3—C16—C13 | 116.9 (3) |
C5—C6—C7 | 110.1 (2) | C17—C16—C15 | 124.7 (3) |
C5—C6—H6A | 109.6 | O3—C16—C15 | 116.4 (3) |
C7—C6—H6A | 109.6 | C13—C16—C15 | 107.2 (2) |
C5—C6—H6B | 109.6 | O3—C17—C16 | 60.26 (18) |
C7—C6—H6B | 109.6 | O3—C17—H17A | 117.7 |
H6A—C6—H6B | 108.2 | C16—C17—H17A | 117.7 |
C8—C7—C6 | 112.5 (2) | O3—C17—H17B | 117.7 |
C8—C7—H7A | 109.1 | C16—C17—H17B | 117.7 |
C6—C7—H7A | 109.1 | H17A—C17—H17B | 114.9 |
C8—C7—H7B | 109.1 | C4—C18—H18A | 109.5 |
C6—C7—H7B | 109.1 | C4—C18—H18B | 109.5 |
H7A—C7—H7B | 107.8 | H18A—C18—H18B | 109.5 |
C7—C8—C14 | 113.3 (2) | C4—C18—H18C | 109.5 |
C7—C8—C9 | 110.7 (2) | H18A—C18—H18C | 109.5 |
C14—C8—C9 | 111.7 (2) | H18B—C18—H18C | 109.5 |
C7—C8—C15 | 110.9 (2) | O1—C19—O2 | 122.4 (3) |
C14—C8—C15 | 100.2 (2) | O1—C19—C4 | 125.2 (3) |
C9—C8—C15 | 109.5 (2) | O2—C19—C4 | 112.2 (3) |
C11—C9—C8 | 109.7 (2) | C10—C20—H20A | 109.5 |
C11—C9—C10 | 115.8 (2) | C10—C20—H20B | 109.5 |
C8—C9—C10 | 116.9 (2) | H20A—C20—H20B | 109.5 |
C11—C9—H9A | 104.2 | C10—C20—H20C | 109.5 |
C8—C9—H9A | 104.2 | H20A—C20—H20C | 109.5 |
C10—C9—H9A | 104.2 | H20B—C20—H20C | 109.5 |
C20—C10—C1 | 108.2 (3) | O2—C21—H21A | 109.5 |
C20—C10—C5 | 112.1 (2) | O2—C21—H21B | 109.5 |
C1—C10—C5 | 107.4 (3) | H21A—C21—H21B | 109.5 |
C20—C10—C9 | 113.3 (2) | O2—C21—H21C | 109.5 |
C1—C10—C9 | 107.6 (2) | H21A—C21—H21C | 109.5 |
C5—C10—C9 | 108.0 (2) | H21B—C21—H21C | 109.5 |
C12—C11—C9 | 116.0 (2) |