Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004828/cm6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004828/cm6003Isup2.hkl |
CCDC reference: 183804
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.004 Å
- R factor = 0.065
- wR factor = 0.175
- Data-to-parameter ratio = 13.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.
C18H22O6 | F(000) = 712 |
Mr = 334.36 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.7932 (2) Å | Cell parameters from 6757 reflections |
b = 4.6909 (1) Å | θ = 2.1–26.6° |
c = 25.2138 (3) Å | µ = 0.10 mm−1 |
β = 93.06° | T = 183 K |
V = 1629.06 (5) Å3 | Needle, colourless |
Z = 4 | 0.55 × 0.05 × 0.05 mm |
Siemens SMART CCD diffractometer | 3375 independent reflections |
Radiation source: fine-focus sealed tube | 2422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ω scans | θmax = 26.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −17→17 |
Tmin = 0.946, Tmax = 0.995 | k = −5→5 |
15921 measured reflections | l = −31→31 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0874P)2 + 1.0506P] where P = (Fo2 + 2Fc2)/3 |
3375 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Experimental. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped with a Siemens LT-2 A low temperature device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 30 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 6757 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). |
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. The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2001) based on the method of Blessing (1995). The structure was solved by direct methods and refined by full-matrix least squares on all F2 data using SHELXTL (Bruker, 1997). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.10205 (12) | 0.4087 (4) | 0.58500 (7) | 0.0344 (5) | |
O2 | 0.05841 (12) | 0.0413 (4) | 0.65620 (7) | 0.0329 (5) | |
O3 | 0.45036 (12) | 0.6377 (4) | 0.73276 (7) | 0.0269 (4) | |
H3 | 0.4838 | 0.7863 | 0.7373 | 0.038 (9)* | |
O4 | 0.45032 (14) | 0.6655 (5) | 0.56167 (8) | 0.0392 (5) | |
H4 | 0.4987 | 0.7743 | 0.5641 | 0.082 (15)* | |
O5 | 0.57763 (11) | 0.6548 (4) | 0.65344 (7) | 0.0258 (4) | |
O6 | 0.65691 (13) | 0.8499 (4) | 0.56783 (7) | 0.0339 (5) | |
C1 | 0.32228 (16) | 0.4609 (5) | 0.67451 (9) | 0.0227 (5) | |
C2 | 0.25725 (16) | 0.5123 (6) | 0.63083 (10) | 0.0240 (6) | |
H2 | 0.2736 | 0.6464 | 0.6045 | 0.019 (6)* | |
C3 | 0.17028 (16) | 0.3705 (6) | 0.62583 (10) | 0.0254 (6) | |
C4 | 0.14631 (16) | 0.1734 (5) | 0.66456 (10) | 0.0249 (6) | |
C5 | 0.20889 (17) | 0.1282 (6) | 0.70793 (10) | 0.0276 (6) | |
H5 | 0.1919 | −0.0021 | 0.7347 | 0.023 (7)* | |
C6 | 0.29690 (17) | 0.2718 (6) | 0.71281 (10) | 0.0267 (6) | |
H6 | 0.3398 | 0.2388 | 0.7429 | 0.039 (8)* | |
C7 | 0.1165 (2) | 0.6378 (7) | 0.55016 (11) | 0.0367 (7) | |
H7A | 0.1210 | 0.8161 | 0.5704 | 0.043 (9)* | |
H7B | 0.0618 | 0.6487 | 0.5238 | 0.056 (10)* | |
H7C | 0.1768 | 0.6078 | 0.5321 | 0.064 (11)* | |
C8 | 0.03223 (19) | −0.1590 (6) | 0.69495 (11) | 0.0325 (6) | |
H8A | 0.0831 | −0.3041 | 0.6995 | 0.040 (8)* | |
H8B | −0.0292 | −0.2504 | 0.6834 | 0.035 (8)* | |
H8C | 0.0247 | −0.0612 | 0.7288 | 0.032 (7)* | |
C9 | 0.41805 (16) | 0.6152 (6) | 0.67805 (9) | 0.0227 (5) | |
H9 | 0.4086 | 0.8113 | 0.6631 | 0.015 (6)* | |
C10 | 0.49589 (16) | 0.4630 (6) | 0.64805 (10) | 0.0239 (6) | |
H10 | 0.5128 | 0.2780 | 0.6659 | 0.027 (7)* | |
C11 | 0.47149 (18) | 0.4123 (6) | 0.58993 (10) | 0.0302 (6) | |
H11A | 0.5270 | 0.3159 | 0.5742 | 0.044 (9)* | |
H11B | 0.4148 | 0.2831 | 0.5861 | 0.044 (9)* | |
C12 | 0.66575 (16) | 0.5416 (6) | 0.64104 (10) | 0.0242 (5) | |
C13 | 0.71011 (17) | 0.6559 (6) | 0.59741 (10) | 0.0262 (6) | |
C14 | 0.80334 (18) | 0.5723 (7) | 0.58763 (11) | 0.0333 (7) | |
H14 | 0.8360 | 0.6563 | 0.5593 | 0.030 (7)* | |
C15 | 0.84903 (19) | 0.3667 (7) | 0.61903 (11) | 0.0357 (7) | |
H15 | 0.9131 | 0.3088 | 0.6120 | 0.034 (8)* | |
C16 | 0.80294 (18) | 0.2444 (7) | 0.66039 (11) | 0.0339 (7) | |
H16 | 0.8342 | 0.0990 | 0.6812 | 0.035 (8)* | |
C17 | 0.71054 (18) | 0.3352 (6) | 0.67141 (10) | 0.0287 (6) | |
H17 | 0.6784 | 0.2534 | 0.7001 | 0.026 (7)* | |
C18 | 0.6965 (2) | 0.9488 (8) | 0.52061 (11) | 0.0429 (8) | |
H18A | 0.7581 | 1.0464 | 0.5293 | 0.067 (11)* | |
H18B | 0.6510 | 1.0818 | 0.5026 | 0.042 (9)* | |
H18C | 0.7078 | 0.7867 | 0.4972 | 0.051 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0195 (9) | 0.0442 (13) | 0.0387 (10) | −0.0046 (8) | −0.0067 (7) | 0.0090 (9) |
O2 | 0.0148 (8) | 0.0368 (11) | 0.0468 (11) | −0.0058 (8) | −0.0018 (7) | 0.0067 (9) |
O3 | 0.0184 (9) | 0.0309 (11) | 0.0313 (9) | −0.0048 (8) | −0.0003 (7) | −0.0036 (8) |
O4 | 0.0271 (10) | 0.0531 (14) | 0.0369 (11) | 0.0024 (10) | −0.0039 (8) | 0.0072 (10) |
O5 | 0.0109 (8) | 0.0284 (10) | 0.0384 (10) | −0.0005 (7) | 0.0034 (7) | −0.0037 (8) |
O6 | 0.0246 (9) | 0.0407 (12) | 0.0368 (10) | 0.0034 (8) | 0.0046 (7) | 0.0085 (9) |
C1 | 0.0129 (10) | 0.0231 (13) | 0.0320 (13) | 0.0027 (9) | 0.0014 (9) | −0.0034 (11) |
C2 | 0.0174 (11) | 0.0260 (14) | 0.0287 (13) | 0.0014 (10) | 0.0033 (9) | 0.0012 (11) |
C3 | 0.0153 (11) | 0.0306 (14) | 0.0301 (13) | 0.0031 (10) | −0.0020 (9) | −0.0018 (11) |
C4 | 0.0131 (11) | 0.0240 (13) | 0.0375 (14) | 0.0006 (10) | 0.0010 (9) | −0.0034 (11) |
C5 | 0.0191 (12) | 0.0289 (14) | 0.0350 (14) | 0.0009 (11) | 0.0041 (10) | 0.0061 (12) |
C6 | 0.0159 (11) | 0.0292 (14) | 0.0348 (14) | 0.0038 (10) | −0.0019 (10) | 0.0009 (12) |
C7 | 0.0309 (15) | 0.0460 (19) | 0.0322 (15) | −0.0005 (13) | −0.0064 (11) | 0.0055 (14) |
C8 | 0.0204 (12) | 0.0315 (15) | 0.0463 (16) | −0.0039 (11) | 0.0075 (11) | −0.0011 (13) |
C9 | 0.0156 (11) | 0.0225 (13) | 0.0298 (13) | 0.0023 (10) | 0.0002 (9) | 0.0011 (11) |
C10 | 0.0123 (11) | 0.0260 (13) | 0.0332 (13) | −0.0010 (10) | 0.0006 (9) | 0.0010 (11) |
C11 | 0.0178 (12) | 0.0371 (16) | 0.0357 (14) | 0.0014 (11) | 0.0011 (10) | −0.0059 (13) |
C12 | 0.0130 (11) | 0.0296 (14) | 0.0298 (13) | −0.0001 (10) | −0.0007 (9) | −0.0061 (11) |
C13 | 0.0186 (11) | 0.0293 (14) | 0.0303 (13) | 0.0003 (10) | −0.0017 (9) | −0.0012 (12) |
C14 | 0.0197 (12) | 0.0463 (18) | 0.0342 (14) | −0.0019 (12) | 0.0048 (10) | −0.0054 (13) |
C15 | 0.0179 (12) | 0.0479 (18) | 0.0415 (15) | 0.0040 (12) | 0.0019 (11) | −0.0096 (14) |
C16 | 0.0209 (12) | 0.0396 (17) | 0.0403 (15) | 0.0066 (12) | −0.0074 (11) | −0.0038 (14) |
C17 | 0.0205 (12) | 0.0351 (16) | 0.0302 (13) | −0.0005 (11) | −0.0022 (10) | −0.0019 (12) |
C18 | 0.0400 (17) | 0.052 (2) | 0.0368 (16) | 0.0009 (15) | 0.0030 (12) | 0.0110 (16) |
O1—C3 | 1.369 (3) | C7—H7C | 0.9800 |
O1—C7 | 1.409 (3) | C8—H8A | 0.9800 |
O2—C4 | 1.368 (3) | C8—H8B | 0.9800 |
O2—C8 | 1.416 (3) | C8—H8C | 0.9800 |
O3—C9 | 1.431 (3) | C9—C10 | 1.524 (3) |
O3—H3 | 0.8400 | C9—H9 | 1.0000 |
O4—C11 | 1.408 (3) | C10—C11 | 1.505 (4) |
O4—H4 | 0.8400 | C10—H10 | 1.0000 |
O5—C12 | 1.378 (3) | C11—H11A | 0.9900 |
O5—C10 | 1.443 (3) | C11—H11B | 0.9900 |
O6—C13 | 1.366 (3) | C12—C17 | 1.362 (4) |
O6—C18 | 1.414 (3) | C12—C13 | 1.394 (4) |
C1—C6 | 1.370 (4) | C13—C14 | 1.379 (3) |
C1—C2 | 1.404 (3) | C14—C15 | 1.379 (4) |
C1—C9 | 1.505 (3) | C14—H14 | 0.9500 |
C2—C3 | 1.371 (3) | C15—C16 | 1.375 (4) |
C2—H2 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.397 (4) | C16—C17 | 1.386 (4) |
C4—C5 | 1.373 (4) | C16—H16 | 0.9500 |
C5—C6 | 1.388 (3) | C17—H17 | 0.9500 |
C5—H5 | 0.9500 | C18—H18A | 0.9800 |
C6—H6 | 0.9500 | C18—H18B | 0.9800 |
C7—H7A | 0.9800 | C18—H18C | 0.9800 |
C7—H7B | 0.9800 | ||
C3—O1—C7 | 117.0 (2) | O3—C9—H9 | 108.9 |
C4—O2—C8 | 116.8 (2) | C1—C9—H9 | 108.9 |
C9—O3—H3 | 109.5 | C10—C9—H9 | 108.9 |
C11—O4—H4 | 109.5 | O5—C10—C11 | 108.9 (2) |
C12—O5—C10 | 115.63 (19) | O5—C10—C9 | 103.2 (2) |
C13—O6—C18 | 117.3 (2) | C11—C10—C9 | 115.5 (2) |
C6—C1—C2 | 119.2 (2) | O5—C10—H10 | 109.7 |
C6—C1—C9 | 121.7 (2) | C11—C10—H10 | 109.7 |
C2—C1—C9 | 119.1 (2) | C9—C10—H10 | 109.7 |
C3—C2—C1 | 120.5 (2) | O4—C11—C10 | 112.9 (2) |
C3—C2—H2 | 119.7 | O4—C11—H11A | 109.0 |
C1—C2—H2 | 119.7 | C10—C11—H11A | 109.0 |
O1—C3—C2 | 124.6 (2) | O4—C11—H11B | 109.0 |
O1—C3—C4 | 115.7 (2) | C10—C11—H11B | 109.0 |
C2—C3—C4 | 119.7 (2) | H11A—C11—H11B | 107.8 |
O2—C4—C5 | 124.5 (2) | C17—C12—O5 | 121.7 (2) |
O2—C4—C3 | 115.7 (2) | C17—C12—C13 | 120.8 (2) |
C5—C4—C3 | 119.8 (2) | O5—C12—C13 | 117.4 (2) |
C4—C5—C6 | 120.3 (2) | O6—C13—C14 | 124.8 (2) |
C4—C5—H5 | 119.8 | O6—C13—C12 | 116.2 (2) |
C6—C5—H5 | 119.8 | C14—C13—C12 | 119.0 (2) |
C5—C6—C1 | 120.5 (2) | C13—C14—C15 | 119.9 (3) |
C5—C6—H6 | 119.8 | C13—C14—H14 | 120.1 |
C1—C6—H6 | 119.8 | C15—C14—H14 | 120.1 |
O1—C7—H7A | 109.5 | C16—C15—C14 | 120.8 (2) |
O1—C7—H7B | 109.5 | C16—C15—H15 | 119.6 |
H7A—C7—H7B | 109.5 | C14—C15—H15 | 119.6 |
O1—C7—H7C | 109.5 | C15—C16—C17 | 119.4 (3) |
H7A—C7—H7C | 109.5 | C15—C16—H16 | 120.3 |
H7B—C7—H7C | 109.5 | C17—C16—H16 | 120.3 |
O2—C8—H8A | 109.5 | C12—C17—C16 | 120.0 (3) |
O2—C8—H8B | 109.5 | C12—C17—H17 | 120.0 |
H8A—C8—H8B | 109.5 | C16—C17—H17 | 120.0 |
O2—C8—H8C | 109.5 | O6—C18—H18A | 109.5 |
H8A—C8—H8C | 109.5 | O6—C18—H18B | 109.5 |
H8B—C8—H8C | 109.5 | H18A—C18—H18B | 109.5 |
O3—C9—C1 | 108.66 (19) | O6—C18—H18C | 109.5 |
O3—C9—C10 | 108.77 (18) | H18A—C18—H18C | 109.5 |
C1—C9—C10 | 112.6 (2) | H18B—C18—H18C | 109.5 |
C6—C1—C2—C3 | −1.5 (4) | C12—O5—C10—C9 | 165.07 (19) |
C9—C1—C2—C3 | 178.6 (2) | O3—C9—C10—O5 | −63.5 (2) |
C7—O1—C3—C2 | −9.5 (4) | C1—C9—C10—O5 | 176.02 (19) |
C7—O1—C3—C4 | 169.9 (2) | O3—C9—C10—C11 | 177.8 (2) |
C1—C2—C3—O1 | 179.3 (2) | C1—C9—C10—C11 | 57.3 (3) |
C1—C2—C3—C4 | 0.0 (4) | O5—C10—C11—O4 | −57.8 (3) |
C8—O2—C4—C5 | −1.2 (4) | C9—C10—C11—O4 | 57.7 (3) |
C8—O2—C4—C3 | −179.8 (2) | C10—O5—C12—C17 | −67.8 (3) |
O1—C3—C4—O2 | 0.9 (3) | C10—O5—C12—C13 | 115.1 (3) |
C2—C3—C4—O2 | −179.7 (2) | C18—O6—C13—C14 | 7.1 (4) |
O1—C3—C4—C5 | −177.8 (2) | C18—O6—C13—C12 | −174.2 (2) |
C2—C3—C4—C5 | 1.6 (4) | C17—C12—C13—O6 | 176.4 (2) |
O2—C4—C5—C6 | 179.7 (2) | O5—C12—C13—O6 | −6.5 (3) |
C3—C4—C5—C6 | −1.7 (4) | C17—C12—C13—C14 | −4.8 (4) |
C4—C5—C6—C1 | 0.2 (4) | O5—C12—C13—C14 | 172.3 (2) |
C2—C1—C6—C5 | 1.4 (4) | O6—C13—C14—C15 | −177.7 (3) |
C9—C1—C6—C5 | −178.7 (2) | C12—C13—C14—C15 | 3.6 (4) |
C6—C1—C9—O3 | −26.4 (3) | C13—C14—C15—C16 | −0.4 (4) |
C2—C1—C9—O3 | 153.6 (2) | C14—C15—C16—C17 | −1.8 (4) |
C6—C1—C9—C10 | 94.2 (3) | O5—C12—C17—C16 | −174.3 (2) |
C2—C1—C9—C10 | −85.9 (3) | C13—C12—C17—C16 | 2.6 (4) |
C12—O5—C10—C11 | −71.7 (3) | C15—C16—C17—C12 | 0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O3i | 0.84 | 2.01 | 2.8293 (18) | 165 |
O4—H4···O6 | 0.84 | 2.21 | 2.974 (3) | 152 |
C7—H7A···O2ii | 0.98 | 2.60 | 3.406 (4) | 140 |
C15—H15···O2iii | 0.95 | 2.57 | 3.356 (3) | 140 |
C17—H17···O3iv | 0.95 | 2.58 | 3.492 (3) | 162 |
C18—H18B···O4v | 0.98 | 2.40 | 3.351 (4) | 165 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) x+1, y, z; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1, −y+2, −z+1. |
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