Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013487/bt2304sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013487/bt2304Isup2.hkl |
CCDC reference: 646747
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.006 Å
- R factor = 0.053
- wR factor = 0.121
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 28.44 From the CIF: _reflns_number_total 2212 Count of symmetry unique reflns 2427 Completeness (_total/calc) 91.14% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2007).
C20H20O6 | F(000) = 376 |
Mr = 356.36 | Dx = 1.358 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 741 reflections |
a = 11.631 (2) Å | θ = 1.5–28.4° |
b = 5.5969 (10) Å | µ = 0.10 mm−1 |
c = 13.577 (2) Å | T = 291 K |
β = 99.548 (3)° | Elongated plate, colourless |
V = 871.6 (3) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 2212 independent reflections |
Radiation source: fine-focus sealed tube | 962 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 0.70 pixels mm-1 | θmax = 28.4°, θmin = 1.5° |
φ and ω scans | h = −15→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→7 |
Tmin = 0.944, Tmax = 0.989 | l = −17→16 |
5459 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full with fixed elements per cycle | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0445P)2] where P = (Fo2 + 2Fc2)/3 |
2212 reflections | (Δ/σ)max = 0.002 |
235 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
Experimental. Siemens SMART CCD diffractometer equipped with a normal focus, 2.4 kW sealed tube X-ray source (Mo Kα radiation, λ = 0.71073 Å) operating at 40 kV and 35 mA. The data collection covered about 1.3 hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 90, 180 °) for the crystal and each exposure of 30 s covered 0.3° in ω to give a total of 1315 frames. The crystal-to-detector distance was 5.029 cm and the detector swing angle was -30°. Coverage of the unique set was over 99% complete. Crystal decay was monitored by repeating fifty frames from the initial set at the end of the data collection. The analysis of the duplicate reflections indicated that crystal decay was negligible. Unit-cell parameters were determined by a least-squares fit of 721 reflections in the range 1.52–28.44. Absorption and other corrections were made using a multi-scan technique (SADABS; Sheldrick, 1996) |
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 > σ(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 | 0.5123 (2) | 0.6948 (6) | 0.92797 (19) | 0.0669 (13) | |
O2 | 0.4101 (3) | 1.0461 (6) | 0.8799 (2) | 0.0670 (14) | |
O3 | 0.7643 (2) | 0.6936 (6) | 0.47714 (19) | 0.0684 (14) | |
O4 | 0.8821 (2) | 0.3713 (7) | 0.5262 (2) | 0.0748 (14) | |
O5 | −0.0201 (3) | 1.1777 (7) | 0.9281 (2) | 0.0863 (16) | |
O6 | −0.1625 (2) | 0.8933 (8) | 0.8829 (2) | 0.0886 (18) | |
C1 | 0.4003 (3) | 0.7965 (8) | 0.8966 (3) | 0.0525 (19) | |
C2 | 0.3541 (3) | 0.6753 (9) | 0.7977 (2) | 0.0457 (14) | |
C3 | 0.4657 (3) | 0.6445 (8) | 0.7521 (3) | 0.0446 (14) | |
C4 | 0.5586 (3) | 0.6050 (9) | 0.8449 (3) | 0.0624 (19) | |
C5 | 0.4613 (3) | 0.4444 (9) | 0.6750 (3) | 0.0591 (19) | |
C6 | 0.5749 (3) | 0.4140 (8) | 0.6361 (3) | 0.0469 (17) | |
C7 | 0.6097 (3) | 0.5858 (8) | 0.5727 (3) | 0.0503 (17) | |
C8 | 0.7130 (3) | 0.5523 (8) | 0.5405 (3) | 0.0450 (17) | |
C9 | 0.8791 (4) | 0.6053 (10) | 0.4868 (3) | 0.072 (2) | |
C10 | 0.7832 (3) | 0.3608 (9) | 0.5701 (3) | 0.0526 (19) | |
C11 | 0.7536 (3) | 0.1887 (9) | 0.6323 (3) | 0.0650 (19) | |
C12 | 0.6474 (4) | 0.2211 (9) | 0.6660 (3) | 0.0618 (19) | |
C13 | 0.2558 (3) | 0.8025 (9) | 0.7291 (3) | 0.0562 (18) | |
C14 | 0.1426 (3) | 0.8190 (8) | 0.7698 (3) | 0.0488 (17) | |
C15 | 0.1216 (3) | 1.0075 (8) | 0.8323 (3) | 0.0568 (17) | |
C16 | 0.0171 (4) | 1.0093 (9) | 0.8653 (3) | 0.0588 (19) | |
C17 | −0.1322 (4) | 1.1016 (11) | 0.9413 (4) | 0.094 (3) | |
C18 | −0.0655 (3) | 0.8429 (10) | 0.8399 (3) | 0.0586 (19) | |
C19 | −0.0499 (3) | 0.6557 (10) | 0.7793 (3) | 0.0687 (19) | |
C20 | 0.0569 (3) | 0.6473 (9) | 0.7447 (3) | 0.0593 (19) | |
H1 | 0.34900 | 0.76550 | 0.94560 | 0.0630* | |
H2 | 0.32630 | 0.51590 | 0.81220 | 0.0550* | |
H2A | 0.42720 | 1.11590 | 0.93340 | 0.0810* | |
H3 | 0.48230 | 0.79540 | 0.72070 | 0.0540* | |
H4A | 0.57620 | 0.43610 | 0.85370 | 0.0750* | |
H4B | 0.62980 | 0.68900 | 0.83800 | 0.0750* | |
H5A | 0.44210 | 0.29550 | 0.70500 | 0.0710* | |
H5B | 0.39970 | 0.47870 | 0.61940 | 0.0710* | |
H7 | 0.56370 | 0.71890 | 0.55300 | 0.0600* | |
H9A | 0.93170 | 0.70770 | 0.53100 | 0.0870* | |
H9B | 0.90400 | 0.60330 | 0.42210 | 0.0870* | |
H11 | 0.80120 | 0.05740 | 0.65120 | 0.0780* | |
H12 | 0.62460 | 0.10990 | 0.70980 | 0.0740* | |
H13A | 0.28140 | 0.96290 | 0.71630 | 0.0680* | |
H13B | 0.24120 | 0.71890 | 0.66560 | 0.0680* | |
H15 | 0.17670 | 1.12670 | 0.85050 | 0.0680* | |
H17A | −0.18860 | 1.22710 | 0.92070 | 0.1130* | |
H17B | −0.13260 | 1.06670 | 1.01120 | 0.1130* | |
H19 | −0.10700 | 0.54010 | 0.76180 | 0.0820* | |
H20 | 0.07090 | 0.52180 | 0.70340 | 0.0710* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0573 (19) | 0.097 (3) | 0.0429 (16) | 0.018 (2) | −0.0023 (15) | 0.006 (2) |
O2 | 0.084 (2) | 0.060 (3) | 0.054 (2) | −0.005 (2) | 0.0029 (17) | −0.0026 (18) |
O3 | 0.060 (2) | 0.087 (3) | 0.0634 (19) | 0.004 (2) | 0.0254 (17) | 0.014 (2) |
O4 | 0.055 (2) | 0.100 (3) | 0.072 (2) | 0.013 (2) | 0.0181 (18) | −0.007 (2) |
O5 | 0.075 (2) | 0.081 (3) | 0.111 (3) | −0.005 (2) | 0.039 (2) | −0.029 (3) |
O6 | 0.052 (2) | 0.123 (4) | 0.093 (3) | −0.008 (2) | 0.0186 (19) | −0.011 (3) |
C1 | 0.047 (3) | 0.071 (4) | 0.039 (3) | 0.006 (3) | 0.006 (2) | 0.003 (3) |
C2 | 0.040 (2) | 0.054 (3) | 0.043 (2) | −0.006 (2) | 0.0066 (19) | 0.010 (3) |
C3 | 0.033 (2) | 0.057 (3) | 0.045 (2) | −0.007 (2) | 0.0096 (19) | 0.002 (3) |
C4 | 0.048 (3) | 0.086 (4) | 0.054 (3) | −0.002 (3) | 0.011 (2) | −0.010 (3) |
C5 | 0.056 (3) | 0.054 (4) | 0.069 (3) | −0.012 (3) | 0.015 (2) | −0.010 (3) |
C6 | 0.041 (3) | 0.051 (3) | 0.049 (3) | −0.013 (3) | 0.008 (2) | −0.013 (3) |
C7 | 0.051 (3) | 0.049 (3) | 0.051 (3) | 0.000 (2) | 0.009 (2) | −0.004 (3) |
C8 | 0.047 (3) | 0.051 (3) | 0.039 (3) | 0.000 (3) | 0.013 (2) | −0.001 (2) |
C9 | 0.055 (3) | 0.101 (5) | 0.064 (3) | −0.005 (3) | 0.021 (2) | −0.005 (4) |
C10 | 0.044 (3) | 0.057 (4) | 0.056 (3) | 0.002 (3) | 0.006 (2) | −0.009 (3) |
C11 | 0.063 (3) | 0.051 (4) | 0.078 (3) | 0.005 (3) | 0.003 (3) | −0.009 (3) |
C12 | 0.073 (3) | 0.043 (4) | 0.070 (3) | −0.004 (3) | 0.014 (3) | 0.001 (3) |
C13 | 0.048 (3) | 0.078 (4) | 0.041 (2) | −0.003 (3) | 0.003 (2) | 0.003 (3) |
C14 | 0.046 (3) | 0.053 (3) | 0.046 (3) | −0.002 (3) | 0.004 (2) | 0.003 (3) |
C15 | 0.053 (3) | 0.048 (3) | 0.070 (3) | −0.005 (3) | 0.012 (3) | −0.001 (3) |
C16 | 0.057 (3) | 0.057 (4) | 0.063 (3) | 0.001 (3) | 0.012 (3) | −0.005 (3) |
C17 | 0.072 (4) | 0.109 (6) | 0.107 (5) | 0.010 (4) | 0.029 (3) | −0.005 (5) |
C18 | 0.037 (3) | 0.082 (4) | 0.055 (3) | −0.002 (3) | 0.002 (2) | 0.002 (3) |
C19 | 0.052 (3) | 0.082 (4) | 0.068 (3) | −0.023 (3) | −0.002 (3) | −0.010 (4) |
C20 | 0.058 (3) | 0.069 (4) | 0.048 (3) | −0.012 (3) | 0.000 (2) | −0.008 (3) |
O1—C1 | 1.421 (5) | C14—C20 | 1.386 (6) |
O1—C4 | 1.420 (5) | C14—C15 | 1.401 (6) |
O2—C1 | 1.423 (6) | C15—C16 | 1.363 (6) |
O3—C8 | 1.375 (5) | C16—C18 | 1.341 (7) |
O3—C9 | 1.409 (5) | C18—C19 | 1.363 (7) |
O4—C9 | 1.413 (7) | C19—C20 | 1.400 (5) |
O4—C10 | 1.382 (4) | C1—H1 | 0.9800 |
O5—C16 | 1.387 (6) | C2—H2 | 0.9800 |
O5—C17 | 1.411 (6) | C3—H3 | 0.9800 |
O6—C17 | 1.421 (7) | C4—H4A | 0.9700 |
O6—C18 | 1.383 (5) | C4—H4B | 0.9700 |
O2—H2A | 0.8200 | C5—H5A | 0.9700 |
C1—C2 | 1.521 (5) | C5—H5B | 0.9700 |
C2—C13 | 1.526 (5) | C7—H7 | 0.9300 |
C2—C3 | 1.538 (5) | C9—H9A | 0.9700 |
C3—C4 | 1.534 (6) | C9—H9B | 0.9700 |
C3—C5 | 1.528 (6) | C11—H11 | 0.9300 |
C5—C6 | 1.512 (5) | C12—H12 | 0.9300 |
C6—C12 | 1.389 (6) | C13—H13A | 0.9700 |
C6—C7 | 1.395 (6) | C13—H13B | 0.9700 |
C7—C8 | 1.358 (5) | C15—H15 | 0.9300 |
C8—C10 | 1.367 (6) | C17—H17A | 0.9700 |
C10—C11 | 1.362 (6) | C17—H17B | 0.9700 |
C11—C12 | 1.398 (6) | C19—H19 | 0.9300 |
C13—C14 | 1.513 (5) | C20—H20 | 0.9300 |
O1···O2i | 2.744 (4) | C11···H19x | 2.9400 |
O1···C1i | 3.297 (5) | C12···H4A | 3.0500 |
O2···O1ii | 2.744 (4) | C13···H9Biii | 3.0400 |
O2···C15 | 3.317 (5) | C13···H5B | 3.0200 |
O3···C5iii | 3.365 (5) | C14···H9Biii | 3.0200 |
O3···O4 | 2.296 (5) | C18···H11xiii | 3.0200 |
O4···C9iv | 3.182 (6) | C20···H9Aviii | 3.0400 |
O5···C16v | 3.359 (5) | H2···O2xii | 2.9000 |
O5···C17v | 3.297 (7) | H2···H5A | 2.4700 |
O5···C19vi | 3.336 (6) | H2A···O1ii | 1.9500 |
O5···O6 | 2.306 (5) | H2A···C1ii | 2.9700 |
O5···C18v | 3.275 (5) | H2A···C4ii | 2.9900 |
O1···H2Ai | 1.9500 | H3···O2 | 2.8200 |
O2···H3 | 2.8200 | H3···C7 | 2.9300 |
O2···H15 | 2.7200 | H3···H12vi | 2.4400 |
O2···H2vi | 2.9000 | H3···H13A | 2.5100 |
O2···H13A | 2.5100 | H4A···C6 | 2.9500 |
O2···H5Avi | 2.8300 | H4A···C12 | 3.0500 |
O3···H5Biii | 2.6600 | H4A···H5A | 2.4700 |
O3···H13Avii | 2.9000 | H4B···O6x | 2.6500 |
O4···H9Biv | 2.8900 | H5A···O2xii | 2.8300 |
O4···H13Bvii | 2.8900 | H5A···H2 | 2.4700 |
O4···H9Aiv | 2.5900 | H5A···H4A | 2.4700 |
O5···H17Bv | 2.8400 | H5A···H12 | 2.3500 |
O6···H4Bviii | 2.6500 | H5B···C13 | 3.0200 |
C1···C15 | 3.424 (5) | H5B···H13B | 2.4500 |
C1···O1ii | 3.297 (5) | H5B···O3vii | 2.6600 |
C4···C12 | 3.524 (6) | H7···C6iii | 3.0000 |
C5···O3vii | 3.365 (5) | H9A···C20x | 3.0400 |
C9···C13vii | 3.521 (6) | H9A···O4ix | 2.5900 |
C9···O4ix | 3.182 (6) | H9B···O4ix | 2.8900 |
C10···C19x | 3.568 (6) | H9B···C13vii | 3.0400 |
C12···C4 | 3.524 (6) | H9B···C14vii | 3.0200 |
C13···C9iii | 3.521 (6) | H11···C18xiv | 3.0200 |
C15···C1 | 3.424 (5) | H12···H3xii | 2.4400 |
C15···O2 | 3.317 (5) | H12···H5A | 2.3500 |
C16···O5xi | 3.359 (5) | H13A···O2 | 2.5100 |
C16···C17xi | 3.568 (7) | H13A···H3 | 2.5100 |
C17···C16v | 3.568 (7) | H13A···H15 | 2.5300 |
C17···O5xi | 3.297 (7) | H13A···O3iii | 2.9000 |
C18···O5xi | 3.275 (5) | H13B···C5 | 2.9700 |
C19···C10viii | 3.568 (6) | H13B···H5B | 2.4500 |
C19···O5xii | 3.336 (6) | H13B···H20 | 2.4000 |
C1···H2Ai | 2.9700 | H13B···O4iii | 2.8900 |
C4···H2Ai | 2.9900 | H15···O2 | 2.7200 |
C5···H13B | 2.9700 | H15···H13A | 2.5300 |
C6···H7vii | 3.0000 | H17B···O5xi | 2.8400 |
C6···H4A | 2.9500 | H19···C10viii | 2.8800 |
C7···H3 | 2.9300 | H19···C11viii | 2.9400 |
C10···H19x | 2.8800 | H20···H13B | 2.4000 |
C1—O1—C4 | 110.7 (3) | O2—C1—H1 | 111.00 |
C8—O3—C9 | 104.1 (3) | C2—C1—H1 | 111.00 |
C9—O4—C10 | 103.5 (3) | C1—C2—H2 | 108.00 |
C16—O5—C17 | 105.2 (4) | C3—C2—H2 | 108.00 |
C17—O6—C18 | 105.0 (3) | C13—C2—H2 | 108.00 |
C1—O2—H2A | 110.00 | C2—C3—H3 | 109.00 |
O1—C1—C2 | 105.0 (3) | C4—C3—H3 | 109.00 |
O2—C1—C2 | 108.9 (3) | C5—C3—H3 | 109.00 |
O1—C1—O2 | 110.3 (3) | O1—C4—H4A | 110.00 |
C1—C2—C3 | 102.0 (3) | O1—C4—H4B | 110.00 |
C3—C2—C13 | 113.8 (3) | C3—C4—H4A | 110.00 |
C1—C2—C13 | 116.8 (4) | C3—C4—H4B | 110.00 |
C2—C3—C4 | 102.3 (3) | H4A—C4—H4B | 109.00 |
C4—C3—C5 | 113.3 (4) | C3—C5—H5A | 109.00 |
C2—C3—C5 | 115.1 (3) | C3—C5—H5B | 109.00 |
O1—C4—C3 | 107.1 (3) | C6—C5—H5A | 109.00 |
C3—C5—C6 | 113.0 (3) | C6—C5—H5B | 109.00 |
C5—C6—C7 | 119.9 (4) | H5A—C5—H5B | 108.00 |
C5—C6—C12 | 120.6 (4) | C6—C7—H7 | 121.00 |
C7—C6—C12 | 119.5 (4) | C8—C7—H7 | 121.00 |
C6—C7—C8 | 117.8 (4) | O3—C9—H9A | 110.00 |
O3—C8—C7 | 128.4 (4) | O3—C9—H9B | 110.00 |
C7—C8—C10 | 122.1 (4) | O4—C9—H9A | 110.00 |
O3—C8—C10 | 109.6 (3) | O4—C9—H9B | 110.00 |
O3—C9—O4 | 108.9 (4) | H9A—C9—H9B | 108.00 |
O4—C10—C8 | 109.8 (4) | C10—C11—H11 | 122.00 |
C8—C10—C11 | 122.5 (4) | C12—C11—H11 | 122.00 |
O4—C10—C11 | 127.7 (4) | C6—C12—H12 | 119.00 |
C10—C11—C12 | 116.0 (4) | C11—C12—H12 | 119.00 |
C6—C12—C11 | 122.1 (4) | C2—C13—H13A | 109.00 |
C2—C13—C14 | 114.5 (3) | C2—C13—H13B | 109.00 |
C13—C14—C20 | 120.1 (4) | C14—C13—H13A | 109.00 |
C15—C14—C20 | 118.7 (3) | C14—C13—H13B | 109.00 |
C13—C14—C15 | 121.1 (4) | H13A—C13—H13B | 107.00 |
C14—C15—C16 | 117.3 (4) | C14—C15—H15 | 121.00 |
O5—C16—C15 | 126.4 (4) | C16—C15—H15 | 121.00 |
O5—C16—C18 | 110.3 (4) | O5—C17—H17A | 110.00 |
C15—C16—C18 | 123.4 (4) | O5—C17—H17B | 110.00 |
O5—C17—O6 | 109.0 (4) | O6—C17—H17A | 110.00 |
O6—C18—C16 | 110.5 (4) | O6—C17—H17B | 110.00 |
O6—C18—C19 | 127.7 (4) | H17A—C17—H17B | 108.00 |
C16—C18—C19 | 121.8 (4) | C18—C19—H19 | 122.00 |
C18—C19—C20 | 116.3 (4) | C20—C19—H19 | 122.00 |
C14—C20—C19 | 122.4 (4) | C14—C20—H20 | 119.00 |
O1—C1—H1 | 111.00 | C19—C20—H20 | 119.00 |
C4—O1—C1—O2 | −93.1 (4) | C3—C5—C6—C12 | 106.2 (5) |
C4—O1—C1—C2 | 24.0 (4) | C5—C6—C7—C8 | 179.3 (4) |
C1—O1—C4—C3 | −2.3 (5) | C12—C6—C7—C8 | 1.8 (6) |
C9—O3—C8—C7 | 167.6 (4) | C5—C6—C12—C11 | −179.4 (4) |
C9—O3—C8—C10 | −12.0 (4) | C7—C6—C12—C11 | −1.9 (6) |
C8—O3—C9—O4 | 20.0 (4) | C6—C7—C8—O3 | 178.9 (4) |
C10—O4—C9—O3 | −20.1 (4) | C6—C7—C8—C10 | −1.5 (6) |
C9—O4—C10—C8 | 12.5 (4) | O3—C8—C10—O4 | −0.4 (5) |
C9—O4—C10—C11 | −168.8 (4) | O3—C8—C10—C11 | −179.2 (4) |
C17—O5—C16—C15 | −179.4 (5) | C7—C8—C10—O4 | 180.0 (4) |
C17—O5—C16—C18 | 0.8 (5) | C7—C8—C10—C11 | 1.2 (7) |
C16—O5—C17—O6 | −2.3 (5) | O4—C10—C11—C12 | −179.7 (4) |
C18—O6—C17—O5 | 2.8 (5) | C8—C10—C11—C12 | −1.1 (6) |
C17—O6—C18—C16 | −2.3 (5) | C10—C11—C12—C6 | 1.5 (6) |
C17—O6—C18—C19 | 178.0 (5) | C2—C13—C14—C15 | 86.7 (5) |
O1—C1—C2—C3 | −35.3 (4) | C2—C13—C14—C20 | −93.9 (5) |
O1—C1—C2—C13 | −160.0 (3) | C13—C14—C15—C16 | 179.7 (4) |
O2—C1—C2—C3 | 82.8 (4) | C20—C14—C15—C16 | 0.4 (6) |
O2—C1—C2—C13 | −41.9 (4) | C13—C14—C20—C19 | −179.2 (4) |
C1—C2—C3—C4 | 32.9 (4) | C15—C14—C20—C19 | 0.2 (6) |
C1—C2—C3—C5 | 156.2 (4) | C14—C15—C16—O5 | 179.4 (4) |
C13—C2—C3—C4 | 159.5 (4) | C14—C15—C16—C18 | −0.9 (7) |
C13—C2—C3—C5 | −77.2 (5) | O5—C16—C18—O6 | 1.0 (5) |
C1—C2—C13—C14 | −65.7 (5) | O5—C16—C18—C19 | −179.4 (4) |
C3—C2—C13—C14 | 175.9 (4) | C15—C16—C18—O6 | −178.9 (4) |
C2—C3—C4—O1 | −19.9 (5) | C15—C16—C18—C19 | 0.8 (7) |
C5—C3—C4—O1 | −144.4 (3) | O6—C18—C19—C20 | 179.4 (4) |
C2—C3—C5—C6 | −177.3 (3) | C16—C18—C19—C20 | −0.3 (7) |
C4—C3—C5—C6 | −60.1 (5) | C18—C19—C20—C14 | −0.2 (7) |
C3—C5—C6—C7 | −71.2 (5) |
Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+2; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y−1/2, −z+1; (v) −x, y+1/2, −z+2; (vi) x, y+1, z; (vii) −x+1, y−1/2, −z+1; (viii) x−1, y, z; (ix) −x+2, y+1/2, −z+1; (x) x+1, y, z; (xi) −x, y−1/2, −z+2; (xii) x, y−1, z; (xiii) x−1, y+1, z; (xiv) x+1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1ii | 0.82 | 1.95 | 2.744 (4) | 164 |
C9—H9A···O4ix | 0.97 | 2.59 | 3.182 (6) | 120 |
C13—H13A···O2 | 0.97 | 2.51 | 2.838 (5) | 100 |
Symmetry codes: (ii) −x+1, y+1/2, −z+2; (ix) −x+2, y+1/2, −z+1. |