Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019209/rz2030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019209/rz20303sup2.hkl |
CCDC reference: 610878
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
C24H34O8 | F(000) = 484 |
Mr = 450.51 | Dx = 1.240 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2420 reflections |
a = 10.288 (4) Å | θ = 2.7–23.4° |
b = 9.992 (3) Å | µ = 0.09 mm−1 |
c = 11.983 (4) Å | T = 294 K |
β = 101.552 (6)° | Block, colourless |
V = 1206.9 (7) Å3 | 0.26 × 0.22 × 0.16 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 2644 independent reflections |
Radiation source: fine-focus sealed tube | 1831 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 26.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.976, Tmax = 0.985 | k = −12→5 |
6896 measured reflections | l = −15→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.1782P] where P = (Fo2 + 2Fc2)/3 |
2644 reflections | (Δ/σ)max = 0.001 |
300 parameters | Δρmax = 0.31 e Å−3 |
14 restraints | Δρmin = −0.26 e Å−3 |
Experimental. 1H NMR (CDCl3): δ 1.38 (s, 9H), 1.42 (s, 12H), 4.01–4.68 (m, 8H), 5.90 (d, J = 3.9 Hz, 1H), 7.41 (d, J = 2.4 Hz, 1H), 7.48 (d, J = 1.8 Hz, 1H), 9.87 (s, 1H), 1.80 (s, 1H). 13C NMR (CDCl3): δ 197.0, 161.0, 138.6, 133.9, 131.0, 128.3, 120.3, 111.9, 109.1, 105.3, 82.6, 81.6, 81.3, 77.7, 76.7, 72.4, 71.8, 67.5, 34.9, 29.1, 26.9, 26.8, 26.7, 26.2. IR (KBr): ν (cm-1) 3423, 2992, 2969, 2936, 2862, 1655, 1617, 1456, 1440, 1384, 1374, 1321, 1265, 1226, 1212, 1167, 1152, 1081, 1024, 847, 771, 759. |
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 | 0.1023 (3) | 0.2965 (3) | 0.9930 (2) | 0.0679 (8) | |
H1 | 0.015 (4) | 0.301 (6) | 1.000 (5) | 0.099 (17)* | |
O2 | −0.1408 (3) | 0.3831 (4) | 0.9716 (3) | 0.0789 (9) | |
O3 | 0.0917 (2) | 0.7819 (2) | 0.64049 (18) | 0.0503 (6) | |
O4 | −0.0362 (2) | 0.8290 (3) | 0.4037 (2) | 0.0589 (7) | |
O5 | −0.2263 (2) | 0.6466 (3) | 0.5789 (2) | 0.0601 (7) | |
O6 | −0.4041 (3) | 0.7580 (4) | 0.4823 (4) | 0.1014 (13) | |
O7 | 0.1763 (3) | 0.5978 (2) | 0.4034 (2) | 0.0568 (7) | |
O8 | 0.0926 (3) | 0.7598 (3) | 0.2764 (2) | 0.0854 (10) | |
C1 | 0.1675 (3) | 0.6256 (4) | 0.7983 (3) | 0.0467 (8) | |
C2 | 0.2667 (3) | 0.5314 (4) | 0.8375 (3) | 0.0490 (9) | |
H2 | 0.3492 | 0.5445 | 0.8186 | 0.059* | |
C3 | 0.2510 (4) | 0.4192 (4) | 0.9029 (3) | 0.0497 (9) | |
C4 | 0.1250 (4) | 0.4025 (4) | 0.9288 (3) | 0.0491 (8) | |
C5 | 0.0224 (3) | 0.4933 (4) | 0.8886 (3) | 0.0474 (8) | |
C6 | 0.0441 (3) | 0.6033 (4) | 0.8241 (3) | 0.0476 (8) | |
H6 | −0.0250 | 0.6627 | 0.7980 | 0.057* | |
C7 | 0.3643 (4) | 0.3190 (5) | 0.9411 (3) | 0.0656 (11) | |
C8 | 0.3204 (6) | 0.1791 (5) | 0.8930 (5) | 0.0896 (16) | |
H8A | 0.3945 | 0.1189 | 0.9085 | 0.134* | |
H8B | 0.2886 | 0.1853 | 0.8122 | 0.134* | |
H8C | 0.2508 | 0.1462 | 0.9283 | 0.134* | |
C9 | 0.3988 (5) | 0.3144 (7) | 1.0736 (4) | 0.0962 (18) | |
H9A | 0.4318 | 0.4001 | 1.1025 | 0.144* | |
H9B | 0.4653 | 0.2474 | 1.0980 | 0.144* | |
H9C | 0.3205 | 0.2929 | 1.1021 | 0.144* | |
C10 | 0.4904 (4) | 0.3583 (6) | 0.9000 (4) | 0.0853 (15) | |
H10A | 0.5214 | 0.4432 | 0.9322 | 0.128* | |
H10B | 0.4715 | 0.3647 | 0.8184 | 0.128* | |
H10C | 0.5574 | 0.2916 | 0.9236 | 0.128* | |
C11 | −0.1106 (4) | 0.4735 (5) | 0.9127 (3) | 0.0639 (11) | |
H11 | −0.1765 | 0.5338 | 0.8810 | 0.077* | |
C12 | 0.1971 (3) | 0.7468 (4) | 0.7339 (3) | 0.0532 (9) | |
H12A | 0.2142 | 0.8220 | 0.7859 | 0.064* | |
H12B | 0.2771 | 0.7304 | 0.7047 | 0.064* | |
C13 | 0.0707 (3) | 0.6870 (3) | 0.5496 (3) | 0.0413 (8) | |
H13 | 0.0759 | 0.5944 | 0.5772 | 0.050* | |
C14 | −0.0630 (4) | 0.7183 (4) | 0.4720 (3) | 0.0466 (8) | |
H14 | −0.0912 | 0.6412 | 0.4225 | 0.056* | |
C15 | 0.0930 (4) | 0.8160 (4) | 0.3844 (3) | 0.0526 (9) | |
H15 | 0.1391 | 0.9024 | 0.3928 | 0.063* | |
C16 | 0.1659 (4) | 0.7137 (3) | 0.4695 (3) | 0.0458 (8) | |
H16 | 0.2525 | 0.7462 | 0.5098 | 0.055* | |
C17 | −0.1761 (3) | 0.7605 (4) | 0.5285 (3) | 0.0505 (9) | |
H17 | −0.1448 | 0.8279 | 0.5871 | 0.061* | |
C18 | −0.2963 (4) | 0.8138 (5) | 0.4449 (4) | 0.0714 (12) | |
H18A | −0.2994 | 0.9108 | 0.4472 | 0.086* | |
H18B | −0.2946 | 0.7855 | 0.3678 | 0.086* | |
C19 | −0.3644 (4) | 0.6392 (5) | 0.5401 (4) | 0.0697 (12) | |
C20 | −0.3981 (6) | 0.5218 (7) | 0.4613 (7) | 0.134 (3) | |
H20A | −0.3777 | 0.4403 | 0.5035 | 0.201* | |
H20B | −0.3472 | 0.5264 | 0.4025 | 0.201* | |
H20C | −0.4910 | 0.5238 | 0.4277 | 0.201* | |
C21 | −0.4299 (6) | 0.6271 (11) | 0.6403 (6) | 0.156 (3) | |
H21A | −0.4154 | 0.7076 | 0.6847 | 0.234* | |
H21B | −0.3928 | 0.5524 | 0.6863 | 0.234* | |
H21C | −0.5234 | 0.6135 | 0.6142 | 0.234* | |
C22 | 0.1578 (4) | 0.6354 (4) | 0.2863 (3) | 0.0549 (9) | |
C23 | 0.0694 (6) | 0.5346 (6) | 0.2161 (4) | 0.1034 (19) | |
H23A | 0.0504 | 0.5628 | 0.1379 | 0.155* | |
H23B | −0.0119 | 0.5272 | 0.2433 | 0.155* | |
H23C | 0.1131 | 0.4493 | 0.2219 | 0.155* | |
C24 | 0.2892 (5) | 0.6497 (8) | 0.2513 (4) | 0.103 (2) | |
H24A | 0.3421 | 0.7148 | 0.2990 | 0.155* | |
H24B | 0.2753 | 0.6782 | 0.1733 | 0.155* | |
H24C | 0.3343 | 0.5650 | 0.2592 | 0.155* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.078 (2) | 0.0662 (19) | 0.0634 (16) | 0.0010 (17) | 0.0235 (15) | 0.0105 (15) |
O2 | 0.0735 (19) | 0.097 (2) | 0.0728 (19) | −0.0167 (18) | 0.0300 (15) | −0.0030 (19) |
O3 | 0.0585 (14) | 0.0433 (13) | 0.0455 (12) | 0.0015 (12) | 0.0018 (11) | −0.0030 (11) |
O4 | 0.0596 (15) | 0.0560 (17) | 0.0617 (15) | 0.0130 (13) | 0.0134 (12) | 0.0235 (14) |
O5 | 0.0444 (13) | 0.0616 (17) | 0.0737 (17) | 0.0050 (13) | 0.0103 (11) | 0.0162 (15) |
O6 | 0.0512 (17) | 0.068 (2) | 0.170 (4) | 0.0052 (16) | −0.014 (2) | 0.028 (2) |
O7 | 0.0780 (17) | 0.0480 (15) | 0.0460 (13) | 0.0135 (13) | 0.0162 (12) | 0.0070 (12) |
O8 | 0.136 (3) | 0.074 (2) | 0.0483 (15) | 0.043 (2) | 0.0234 (17) | 0.0148 (15) |
C1 | 0.0479 (18) | 0.052 (2) | 0.0378 (16) | −0.0008 (17) | 0.0031 (14) | −0.0031 (17) |
C2 | 0.0438 (18) | 0.057 (2) | 0.0450 (19) | −0.0009 (17) | 0.0066 (15) | −0.0060 (17) |
C3 | 0.055 (2) | 0.054 (2) | 0.0405 (17) | 0.0039 (18) | 0.0100 (15) | −0.0040 (16) |
C4 | 0.061 (2) | 0.050 (2) | 0.0368 (17) | 0.0006 (18) | 0.0111 (15) | −0.0017 (16) |
C5 | 0.0485 (19) | 0.057 (2) | 0.0364 (17) | −0.0034 (17) | 0.0076 (14) | −0.0099 (17) |
C6 | 0.0446 (18) | 0.057 (2) | 0.0380 (17) | 0.0052 (17) | 0.0010 (13) | −0.0059 (17) |
C7 | 0.068 (2) | 0.069 (3) | 0.059 (2) | 0.022 (2) | 0.0109 (19) | 0.007 (2) |
C8 | 0.118 (4) | 0.063 (3) | 0.094 (4) | 0.030 (3) | 0.036 (3) | 0.009 (3) |
C9 | 0.096 (3) | 0.119 (5) | 0.066 (3) | 0.042 (4) | 0.000 (2) | 0.016 (3) |
C10 | 0.060 (3) | 0.105 (4) | 0.092 (3) | 0.031 (3) | 0.018 (2) | 0.006 (3) |
C11 | 0.058 (2) | 0.083 (3) | 0.051 (2) | −0.004 (2) | 0.0141 (18) | −0.013 (2) |
C12 | 0.055 (2) | 0.055 (2) | 0.0462 (18) | −0.0019 (18) | 0.0004 (16) | 0.0002 (18) |
C13 | 0.0504 (19) | 0.0310 (16) | 0.0420 (17) | 0.0006 (14) | 0.0084 (14) | −0.0006 (14) |
C14 | 0.054 (2) | 0.0389 (19) | 0.0446 (17) | −0.0008 (15) | 0.0037 (15) | 0.0028 (16) |
C15 | 0.063 (2) | 0.044 (2) | 0.0521 (19) | −0.0033 (18) | 0.0136 (16) | 0.0091 (18) |
C16 | 0.0496 (19) | 0.0393 (19) | 0.0472 (18) | −0.0046 (15) | 0.0065 (15) | 0.0029 (16) |
C17 | 0.0485 (19) | 0.045 (2) | 0.057 (2) | 0.0029 (17) | 0.0081 (16) | −0.0038 (18) |
C18 | 0.057 (2) | 0.065 (3) | 0.090 (3) | 0.011 (2) | 0.009 (2) | 0.013 (3) |
C19 | 0.043 (2) | 0.069 (3) | 0.094 (3) | 0.004 (2) | 0.006 (2) | 0.012 (3) |
C20 | 0.113 (4) | 0.077 (4) | 0.186 (6) | −0.008 (3) | −0.033 (4) | −0.010 (4) |
C21 | 0.100 (4) | 0.232 (8) | 0.153 (5) | 0.019 (5) | 0.066 (4) | 0.026 (6) |
C22 | 0.066 (2) | 0.053 (2) | 0.0466 (19) | 0.006 (2) | 0.0151 (17) | 0.0085 (19) |
C23 | 0.143 (5) | 0.102 (4) | 0.059 (3) | −0.027 (4) | 0.006 (3) | −0.004 (3) |
C24 | 0.084 (3) | 0.146 (6) | 0.090 (3) | 0.015 (4) | 0.044 (3) | 0.036 (4) |
O1—C4 | 1.357 (4) | C10—H10A | 0.9600 |
O1—H1 | 0.92 (4) | C10—H10B | 0.9600 |
O2—C11 | 1.224 (5) | C10—H10C | 0.9600 |
O3—C13 | 1.428 (4) | C11—H11 | 0.9300 |
O3—C12 | 1.437 (4) | C12—H12A | 0.9700 |
O4—C15 | 1.401 (4) | C12—H12B | 0.9700 |
O4—C14 | 1.435 (4) | C13—C16 | 1.525 (5) |
O5—C19 | 1.406 (4) | C13—C14 | 1.530 (4) |
O5—C17 | 1.432 (4) | C13—H13 | 0.9800 |
O6—C19 | 1.393 (6) | C14—C17 | 1.519 (5) |
O6—C18 | 1.394 (5) | C14—H14 | 0.9800 |
O7—C16 | 1.420 (4) | C15—C16 | 1.530 (5) |
O7—C22 | 1.428 (4) | C15—H15 | 0.9800 |
O8—C22 | 1.407 (5) | C16—H16 | 0.9800 |
O8—C15 | 1.410 (5) | C17—C18 | 1.523 (5) |
C1—C6 | 1.384 (5) | C17—H17 | 0.9800 |
C1—C2 | 1.399 (5) | C18—H18A | 0.9700 |
C1—C12 | 1.499 (5) | C18—H18B | 0.9700 |
C2—C3 | 1.396 (5) | C19—C21 | 1.495 (7) |
C2—H2 | 0.9300 | C19—C20 | 1.502 (8) |
C3—C4 | 1.402 (5) | C20—H20A | 0.9600 |
C3—C7 | 1.535 (5) | C20—H20B | 0.9600 |
C4—C5 | 1.402 (5) | C20—H20C | 0.9600 |
C5—C6 | 1.388 (5) | C21—H21A | 0.9600 |
C5—C11 | 1.467 (5) | C21—H21B | 0.9600 |
C6—H6 | 0.9300 | C21—H21C | 0.9600 |
C7—C10 | 1.527 (6) | C22—C23 | 1.498 (7) |
C7—C8 | 1.544 (7) | C22—C24 | 1.500 (6) |
C7—C9 | 1.557 (6) | C23—H23A | 0.9600 |
C8—H8A | 0.9600 | C23—H23B | 0.9600 |
C8—H8B | 0.9600 | C23—H23C | 0.9600 |
C8—H8C | 0.9600 | C24—H24A | 0.9600 |
C9—H9A | 0.9600 | C24—H24B | 0.9600 |
C9—H9B | 0.9600 | C24—H24C | 0.9600 |
C9—H9C | 0.9600 | ||
C4—O1—H1 | 107 (4) | O4—C14—C13 | 104.6 (3) |
C13—O3—C12 | 114.0 (3) | C17—C14—C13 | 117.5 (3) |
C15—O4—C14 | 108.7 (3) | O4—C14—H14 | 109.1 |
C19—O5—C17 | 109.1 (3) | C17—C14—H14 | 109.1 |
C19—O6—C18 | 109.1 (3) | C13—C14—H14 | 109.1 |
C16—O7—C22 | 108.9 (3) | O4—C15—O8 | 111.1 (3) |
C22—O8—C15 | 111.1 (3) | O4—C15—C16 | 107.8 (3) |
C6—C1—C2 | 117.2 (3) | O8—C15—C16 | 104.9 (3) |
C6—C1—C12 | 122.3 (3) | O4—C15—H15 | 111.0 |
C2—C1—C12 | 120.4 (3) | O8—C15—H15 | 111.0 |
C3—C2—C1 | 124.8 (3) | C16—C15—H15 | 111.0 |
C3—C2—H2 | 117.6 | O7—C16—C13 | 109.8 (3) |
C1—C2—H2 | 117.6 | O7—C16—C15 | 104.8 (3) |
C2—C3—C4 | 115.8 (3) | C13—C16—C15 | 104.3 (3) |
C2—C3—C7 | 121.7 (3) | O7—C16—H16 | 112.5 |
C4—C3—C7 | 122.5 (3) | C13—C16—H16 | 112.5 |
O1—C4—C3 | 119.4 (3) | C15—C16—H16 | 112.5 |
O1—C4—C5 | 119.7 (3) | O5—C17—C14 | 109.9 (3) |
C3—C4—C5 | 120.9 (3) | O5—C17—C18 | 104.0 (3) |
C6—C5—C4 | 120.6 (3) | C14—C17—C18 | 113.5 (3) |
C6—C5—C11 | 118.5 (3) | O5—C17—H17 | 109.8 |
C4—C5—C11 | 120.9 (4) | C14—C17—H17 | 109.8 |
C1—C6—C5 | 120.6 (3) | C18—C17—H17 | 109.8 |
C1—C6—H6 | 119.7 | O6—C18—C17 | 104.0 (3) |
C5—C6—H6 | 119.7 | O6—C18—H18A | 111.0 |
C10—C7—C3 | 112.3 (4) | C17—C18—H18A | 111.0 |
C10—C7—C8 | 108.4 (4) | O6—C18—H18B | 111.0 |
C3—C7—C8 | 109.3 (4) | C17—C18—H18B | 111.0 |
C10—C7—C9 | 107.6 (4) | H18A—C18—H18B | 109.0 |
C3—C7—C9 | 109.1 (3) | O6—C19—O5 | 107.2 (3) |
C8—C7—C9 | 110.1 (4) | O6—C19—C21 | 109.5 (5) |
C7—C8—H8A | 109.5 | O5—C19—C21 | 109.1 (4) |
C7—C8—H8B | 109.5 | O6—C19—C20 | 110.2 (4) |
H8A—C8—H8B | 109.5 | O5—C19—C20 | 109.9 (4) |
C7—C8—H8C | 109.5 | C21—C19—C20 | 110.9 (6) |
H8A—C8—H8C | 109.5 | C19—C20—H20A | 109.5 |
H8B—C8—H8C | 109.5 | C19—C20—H20B | 109.5 |
C7—C9—H9A | 109.5 | H20A—C20—H20B | 109.5 |
C7—C9—H9B | 109.5 | C19—C20—H20C | 109.5 |
H9A—C9—H9B | 109.5 | H20A—C20—H20C | 109.5 |
C7—C9—H9C | 109.5 | H20B—C20—H20C | 109.5 |
H9A—C9—H9C | 109.5 | C19—C21—H21A | 109.5 |
H9B—C9—H9C | 109.5 | C19—C21—H21B | 109.5 |
C7—C10—H10A | 109.5 | H21A—C21—H21B | 109.5 |
C7—C10—H10B | 109.5 | C19—C21—H21C | 109.5 |
H10A—C10—H10B | 109.5 | H21A—C21—H21C | 109.5 |
C7—C10—H10C | 109.5 | H21B—C21—H21C | 109.5 |
H10A—C10—H10C | 109.5 | O8—C22—O7 | 106.5 (3) |
H10B—C10—H10C | 109.5 | O8—C22—C23 | 108.7 (4) |
O2—C11—C5 | 124.6 (4) | O7—C22—C23 | 108.8 (3) |
O2—C11—H11 | 117.7 | O8—C22—C24 | 109.5 (4) |
C5—C11—H11 | 117.7 | O7—C22—C24 | 110.4 (3) |
O3—C12—C1 | 113.5 (3) | C23—C22—C24 | 112.7 (4) |
O3—C12—H12A | 108.9 | C22—C23—H23A | 109.5 |
C1—C12—H12A | 108.9 | C22—C23—H23B | 109.5 |
O3—C12—H12B | 108.9 | H23A—C23—H23B | 109.5 |
C1—C12—H12B | 108.9 | C22—C23—H23C | 109.5 |
H12A—C12—H12B | 107.7 | H23A—C23—H23C | 109.5 |
O3—C13—C16 | 110.2 (3) | H23B—C23—H23C | 109.5 |
O3—C13—C14 | 107.9 (3) | C22—C24—H24A | 109.5 |
C16—C13—C14 | 101.2 (3) | C22—C24—H24B | 109.5 |
O3—C13—H13 | 112.3 | H24A—C24—H24B | 109.5 |
C16—C13—H13 | 112.3 | C22—C24—H24C | 109.5 |
C14—C13—H13 | 112.3 | H24A—C24—H24C | 109.5 |
O4—C14—C17 | 107.0 (3) | H24B—C24—H24C | 109.5 |
C6—C1—C2—C3 | −1.8 (5) | C14—O4—C15—O8 | 98.8 (3) |
C12—C1—C2—C3 | 176.6 (3) | C14—O4—C15—C16 | −15.6 (4) |
C1—C2—C3—C4 | 0.5 (5) | C22—O8—C15—O4 | −116.7 (3) |
C1—C2—C3—C7 | 179.0 (3) | C22—O8—C15—C16 | −0.5 (4) |
C2—C3—C4—O1 | −179.3 (3) | C22—O7—C16—C13 | 130.5 (3) |
C7—C3—C4—O1 | 2.1 (5) | C22—O7—C16—C15 | 19.1 (4) |
C2—C3—C4—C5 | 1.1 (5) | O3—C13—C16—O7 | 160.8 (3) |
C7—C3—C4—C5 | −177.4 (3) | C14—C13—C16—O7 | −85.1 (3) |
O1—C4—C5—C6 | 179.1 (3) | O3—C13—C16—C15 | −87.4 (3) |
C3—C4—C5—C6 | −1.3 (5) | C14—C13—C16—C15 | 26.6 (3) |
O1—C4—C5—C11 | −1.5 (5) | O4—C15—C16—O7 | 107.1 (3) |
C3—C4—C5—C11 | 178.1 (3) | O8—C15—C16—O7 | −11.4 (4) |
C2—C1—C6—C5 | 1.5 (5) | O4—C15—C16—C13 | −8.3 (4) |
C12—C1—C6—C5 | −176.9 (3) | O8—C15—C16—C13 | −126.7 (3) |
C4—C5—C6—C1 | 0.0 (5) | C19—O5—C17—C14 | −127.5 (3) |
C11—C5—C6—C1 | −179.4 (3) | C19—O5—C17—C18 | −5.7 (4) |
C2—C3—C7—C10 | 0.4 (5) | O4—C14—C17—O5 | 168.1 (3) |
C4—C3—C7—C10 | 178.8 (4) | C13—C14—C17—O5 | −74.7 (4) |
C2—C3—C7—C8 | −120.0 (4) | O4—C14—C17—C18 | 52.2 (4) |
C4—C3—C7—C8 | 58.4 (5) | C13—C14—C17—C18 | 169.3 (3) |
C2—C3—C7—C9 | 119.5 (4) | C19—O6—C18—C17 | −26.2 (5) |
C4—C3—C7—C9 | −62.0 (5) | O5—C17—C18—O6 | 19.1 (4) |
C6—C5—C11—O2 | −177.4 (4) | C14—C17—C18—O6 | 138.5 (4) |
C4—C5—C11—O2 | 3.2 (6) | C18—O6—C19—O5 | 23.4 (5) |
C13—O3—C12—C1 | −67.5 (4) | C18—O6—C19—C21 | 141.6 (5) |
C6—C1—C12—O3 | −41.2 (5) | C18—O6—C19—C20 | −96.2 (5) |
C2—C1—C12—O3 | 140.5 (3) | C17—O5—C19—O6 | −9.9 (5) |
C12—O3—C13—C16 | −84.1 (3) | C17—O5—C19—C21 | −128.4 (5) |
C12—O3—C13—C14 | 166.2 (3) | C17—O5—C19—C20 | 109.8 (5) |
C15—O4—C14—C17 | 158.6 (3) | C15—O8—C22—O7 | 12.1 (4) |
C15—O4—C14—C13 | 33.2 (3) | C15—O8—C22—C23 | 129.2 (4) |
O3—C13—C14—O4 | 79.3 (3) | C15—O8—C22—C24 | −107.3 (4) |
C16—C13—C14—O4 | −36.5 (3) | C16—O7—C22—O8 | −19.8 (4) |
O3—C13—C14—C17 | −39.1 (4) | C16—O7—C22—C23 | −136.8 (4) |
C16—C13—C14—C17 | −154.9 (3) | C16—O7—C22—C24 | 99.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.92 (4) | 1.77 (5) | 2.609 (4) | 150 (6) |