Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024419/lh6269sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024419/lh6269Isup2.hkl |
CCDC reference: 255870
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Sheldrick, 1997a); software used to prepare material for publication: SHELXTL.
C9H16O4 | Dx = 1.195 Mg m−3 |
Mr = 188.22 | Melting point: 368 K |
Trigonal, P32 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 32 | Cell parameters from 1272 reflections |
a = 13.3072 (14) Å | θ = 3.1–25.8° |
c = 5.1172 (11) Å | µ = 0.09 mm−1 |
V = 784.8 (2) Å3 | T = 193 K |
Z = 3 | Needle, colourless |
F(000) = 306 | 1.25 × 0.06 × 0.06 mm |
Bruker PLATFORM/SMART 1000 CCD area-detector diffractometer | 1068 independent reflections |
Radiation source: fine-focus sealed tube | 797 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
ω scans | h = −16→16 |
Absorption correction: integration (SHELXTL; Sheldrick, 1997a) | k = −14→16 |
Tmin = 0.946, Tmax = 0.996 | l = −5→6 |
4402 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0659P)2 + 0.4028P] where P = (Fo2 + 2Fc2)/3 |
1068 reflections | (Δ/σ)max < 0.001 |
121 parameters | Δρmax = 0.34 e Å−3 |
1 restraint | Δρmin = −0.32 e Å−3 |
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. Hydrogen atoms were refined with fixed C—H and O—H distances and with isotropic displacement parameters 20% greater than those for their attached atoms. The absolute structure could not be determined from the X-ray data (light atoms only), but was assigned on the basis of the established stereochemistry of the precursor compound. Friedel pairs were merged before the final least-squares refinement. |
x | y | z | Uiso*/Ueq | ||
O6 | 0.1319 (4) | 0.1165 (5) | 0.2846 (10) | 0.0576 (13) | |
H6O | 0.1417 | 0.0870 | 0.1487 | 0.069* | |
O7 | 0.1696 (3) | 0.0573 (3) | 0.8012 (8) | 0.0434 (11) | |
H7O | 0.1109 | −0.0008 | 0.7389 | 0.052* | |
O8 | 0.3794 (3) | 0.2766 (3) | 0.8755 (8) | 0.0369 (10) | |
O9 | 0.5754 (3) | 0.2429 (3) | 0.7439 (9) | 0.0394 (10) | |
H9O | 0.6355 | 0.2678 | 0.6520 | 0.047* | |
C1 | 0.5098 (9) | 0.6303 (7) | 1.044 (3) | 0.109 (4) | |
H1A | 0.4771 | 0.6701 | 0.9555 | 0.131* | |
H1B | 0.5788 | 0.6726 | 1.1430 | 0.131* | |
C2 | 0.4589 (7) | 0.5154 (6) | 1.0274 (18) | 0.067 (2) | |
H2 | 0.4942 | 0.4787 | 1.1181 | 0.080* | |
C3 | 0.3529 (6) | 0.4412 (5) | 0.8809 (16) | 0.0544 (18) | |
H3A | 0.3352 | 0.4912 | 0.7696 | 0.065* | |
H3B | 0.2883 | 0.4012 | 1.0067 | 0.065* | |
C4 | 0.3568 (5) | 0.3509 (5) | 0.7097 (13) | 0.0427 (15) | |
H4 | 0.4216 | 0.3905 | 0.5813 | 0.051* | |
C5 | 0.2435 (5) | 0.2817 (6) | 0.5620 (13) | 0.0464 (16) | |
H5A | 0.1778 | 0.2519 | 0.6864 | 0.056* | |
H5B | 0.2345 | 0.3329 | 0.4355 | 0.056* | |
C6 | 0.2407 (4) | 0.1818 (5) | 0.4188 (12) | 0.0391 (14) | |
H6 | 0.3048 | 0.2131 | 0.2873 | 0.047* | |
C7 | 0.2588 (4) | 0.1058 (4) | 0.6078 (12) | 0.0344 (13) | |
H7 | 0.2605 | 0.0417 | 0.5097 | 0.041* | |
C8 | 0.3742 (4) | 0.1783 (4) | 0.7483 (11) | 0.0317 (12) | |
H8 | 0.3758 | 0.1279 | 0.8912 | 0.038* | |
C9 | 0.4781 (4) | 0.2086 (5) | 0.5799 (14) | 0.0412 (14) | |
H9A | 0.4641 | 0.1405 | 0.4743 | 0.049* | |
H9B | 0.4922 | 0.2726 | 0.4594 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O6 | 0.037 (2) | 0.104 (4) | 0.040 (3) | 0.041 (2) | −0.005 (2) | −0.018 (3) |
O7 | 0.0290 (18) | 0.039 (2) | 0.038 (3) | −0.0014 (15) | 0.0032 (17) | −0.0040 (18) |
O8 | 0.0322 (17) | 0.0313 (17) | 0.039 (3) | 0.0095 (15) | 0.0044 (17) | −0.0039 (17) |
O9 | 0.0254 (16) | 0.043 (2) | 0.047 (3) | 0.0146 (15) | −0.0007 (16) | −0.0098 (19) |
C1 | 0.094 (7) | 0.055 (5) | 0.174 (12) | 0.033 (5) | −0.019 (7) | −0.032 (6) |
C2 | 0.065 (4) | 0.055 (4) | 0.085 (7) | 0.033 (3) | 0.009 (4) | −0.004 (4) |
C3 | 0.065 (4) | 0.042 (3) | 0.053 (5) | 0.025 (3) | 0.011 (3) | 0.002 (3) |
C4 | 0.050 (3) | 0.038 (3) | 0.042 (4) | 0.024 (2) | 0.015 (3) | 0.009 (3) |
C5 | 0.051 (3) | 0.059 (3) | 0.042 (4) | 0.037 (3) | 0.005 (3) | 0.007 (3) |
C6 | 0.030 (2) | 0.060 (3) | 0.030 (4) | 0.024 (2) | 0.005 (2) | 0.000 (3) |
C7 | 0.031 (2) | 0.031 (2) | 0.038 (4) | 0.012 (2) | 0.007 (2) | −0.008 (2) |
C8 | 0.028 (2) | 0.027 (2) | 0.034 (4) | 0.0086 (19) | 0.001 (2) | −0.002 (2) |
C9 | 0.030 (2) | 0.041 (3) | 0.050 (4) | 0.016 (2) | −0.003 (3) | −0.008 (3) |
O6—C6 | 1.437 (7) | C3—H3B | 0.9900 |
O6—H6O | 0.8400 | C4—C5 | 1.518 (9) |
O7—C7 | 1.427 (6) | C4—H4 | 1.0000 |
O7—H7O | 0.8400 | C5—C6 | 1.502 (9) |
O8—C8 | 1.431 (6) | C5—H5A | 0.9900 |
O8—C4 | 1.444 (7) | C5—H5B | 0.9900 |
O9—C9 | 1.413 (7) | C6—C7 | 1.503 (8) |
O9—H9O | 0.8400 | C6—H6 | 1.0000 |
C1—C2 | 1.330 (10) | C7—C8 | 1.525 (7) |
C1—H1A | 0.9500 | C7—H7 | 1.0000 |
C1—H1B | 0.9500 | C8—C9 | 1.503 (8) |
C2—C3 | 1.461 (11) | C8—H8 | 1.0000 |
C2—H2 | 0.9500 | C9—H9A | 0.9900 |
C3—C4 | 1.509 (9) | C9—H9B | 0.9900 |
C3—H3A | 0.9900 | ||
C6—O6—H6O | 109.5 | C4—C5—H5B | 109.4 |
C7—O7—H7O | 109.5 | H5A—C5—H5B | 108.0 |
C8—O8—C4 | 115.3 (4) | O6—C6—C5 | 109.9 (4) |
C9—O9—H9O | 109.5 | O6—C6—C7 | 110.6 (5) |
C2—C1—H1A | 120.0 | C5—C6—C7 | 109.9 (5) |
C2—C1—H1B | 120.0 | O6—C6—H6 | 108.8 |
H1A—C1—H1B | 120.0 | C5—C6—H6 | 108.8 |
C1—C2—C3 | 125.0 (9) | C7—C6—H6 | 108.8 |
C1—C2—H2 | 117.5 | O7—C7—C6 | 112.0 (4) |
C3—C2—H2 | 117.5 | O7—C7—C8 | 107.8 (5) |
C2—C3—C4 | 115.5 (6) | C6—C7—C8 | 109.1 (4) |
C2—C3—H3A | 108.4 | O7—C7—H7 | 109.3 |
C4—C3—H3A | 108.4 | C6—C7—H7 | 109.3 |
C2—C3—H3B | 108.4 | C8—C7—H7 | 109.3 |
C4—C3—H3B | 108.4 | O8—C8—C9 | 113.5 (4) |
H3A—C3—H3B | 107.5 | O8—C8—C7 | 111.5 (4) |
O8—C4—C3 | 107.8 (5) | C9—C8—C7 | 113.6 (4) |
O8—C4—C5 | 111.1 (4) | O8—C8—H8 | 105.9 |
C3—C4—C5 | 110.7 (5) | C9—C8—H8 | 105.9 |
O8—C4—H4 | 109.0 | C7—C8—H8 | 105.9 |
C3—C4—H4 | 109.0 | O9—C9—C8 | 108.5 (5) |
C5—C4—H4 | 109.0 | O9—C9—H9A | 110.0 |
C6—C5—C4 | 111.0 (4) | C8—C9—H9A | 110.0 |
C6—C5—H5A | 109.4 | O9—C9—H9B | 110.0 |
C4—C5—H5A | 109.4 | C8—C9—H9B | 110.0 |
C6—C5—H5B | 109.4 | H9A—C9—H9B | 108.4 |
C1—C2—C3—C4 | 133.0 (10) | O6—C6—C7—C8 | −179.4 (4) |
C8—O8—C4—C3 | 173.9 (4) | C5—C6—C7—C8 | −57.9 (5) |
C8—O8—C4—C5 | 52.4 (6) | C4—O8—C8—C9 | 75.2 (6) |
C2—C3—C4—O8 | 59.8 (7) | C4—O8—C8—C7 | −54.5 (5) |
C2—C3—C4—C5 | −178.4 (6) | O7—C7—C8—O8 | −65.7 (5) |
O8—C4—C5—C6 | −52.8 (7) | C6—C7—C8—O8 | 56.1 (5) |
C3—C4—C5—C6 | −172.6 (5) | O7—C7—C8—C9 | 164.6 (4) |
C4—C5—C6—O6 | 179.0 (5) | C6—C7—C8—C9 | −73.6 (5) |
C4—C5—C6—C7 | 57.0 (6) | O8—C8—C9—O9 | 69.1 (6) |
O6—C6—C7—O7 | −60.2 (6) | C7—C8—C9—O9 | −162.2 (4) |
C5—C6—C7—O7 | 61.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6O···O7i | 0.84 | 1.90 | 2.718 (6) | 165 |
O7—H7O···O6ii | 0.84 | 1.82 | 2.661 (5) | 177 |
O9—H9O···O9iii | 0.84 | 1.87 | 2.701 (5) | 170 |
Symmetry codes: (i) x, y, z−1; (ii) −x+y, −x, z+1/3; (iii) −y+1, x−y, z−1/3. |