Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012669/hk2027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012669/hk2027Isup2.hkl |
CCDC reference: 608354
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PLATON (Spek, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
C26H38O6 | F(000) = 484 |
Mr = 446.56 | Dx = 1.207 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 10.8379 (11) Å | θ = 17.6–28.5° |
b = 8.3682 (11) Å | µ = 0.68 mm−1 |
c = 13.621 (8) Å | T = 298 K |
β = 95.92 (3)° | Prism, colourless |
V = 1228.7 (8) Å3 | 0.24 × 0.20 × 0.20 mm |
Z = 2 |
Enraf–Nonius MACH-3 diffractometer | 1905 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
Graphite monochromator | θmax = 72.5°, θmin = 3.3° |
profile data from ω/2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.774, Tmax = 0.873 | l = −16→16 |
5138 measured reflections | 3 standard reflections every 300 min |
2614 independent reflections | intensity decay: 9.6% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.1662P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.13 e Å−3 |
2614 reflections | Δρmin = −0.11 e Å−3 |
312 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0046 (7) |
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: 0.3 (3) |
Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 8.18 (1H, s), 8.10 (1H, s), 8.03 (1H, s), 5.67–5.56 (1H, m), 5.27 (1H, br t), 5.07 (1H, d, J = 2.5 Hz), 4.90 (1H, dd, J = 17.1 and 1.4 Hz), 4.83 (1H, dd, J = 10.1 and 1.8 Hz), 4.77–4.67 (1H, m), 0.96 (3H, s), 0.94 (3H, d, J = 64.5 Hz), 0.78 (3H, s); 13C NMR (75.25 MHz, CDCl3, δ, p.p.m.): 160.6 (two C atoms), 160.5, 144.2, 112.3, 75.1, 73.7, 70.7, 46.8, 44.9, 43.0, 40.8, 40.5, 37.7, 34.5, 34.4, 34.2, 31.3, 28.6, 27.3, 26.5, 25.6, 22.7, 22.4, 19.5, 12.3. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O3 | −0.0882 (3) | 0.4552 (4) | 0.0473 (2) | 0.0912 (9) | |
O7 | 0.15510 (18) | 0.1524 (3) | 0.31694 (15) | 0.0595 (6) | |
O12 | 0.45942 (18) | 0.1791 (3) | 0.11610 (14) | 0.0554 (5) | |
O31A | −0.1810 (6) | 0.6756 (8) | −0.0013 (6) | 0.149 (4) | 0.613 (8) |
O31B | −0.2425 (6) | 0.5447 (14) | 0.1049 (6) | 0.114 (4) | 0.387 (8) |
O71 | 0.0698 (4) | 0.0430 (6) | 0.4426 (3) | 0.1544 (18) | |
O121 | 0.5430 (3) | 0.2983 (4) | −0.00949 (19) | 0.0915 (9) | |
C1 | 0.2083 (3) | 0.6525 (4) | 0.1506 (2) | 0.0658 (9) | |
H1A | 0.1751 | 0.7568 | 0.1646 | 0.079* | |
H1B | 0.2854 | 0.6694 | 0.1216 | 0.079* | |
C2 | 0.1172 (3) | 0.5694 (5) | 0.0748 (2) | 0.0718 (10) | |
H2A | 0.1011 | 0.6363 | 0.0167 | 0.086* | |
H2B | 0.1521 | 0.4692 | 0.0550 | 0.086* | |
C3 | −0.0013 (3) | 0.5387 (4) | 0.1194 (2) | 0.0663 (9) | |
H3 | −0.0376 | 0.6409 | 0.1367 | 0.080* | |
C4 | 0.0213 (3) | 0.4364 (4) | 0.2110 (2) | 0.0600 (8) | |
H4A | 0.0543 | 0.3336 | 0.1938 | 0.072* | |
H4B | −0.0566 | 0.4182 | 0.2385 | 0.072* | |
C5 | 0.1126 (3) | 0.5179 (4) | 0.2879 (2) | 0.0546 (7) | |
H5 | 0.0738 | 0.6187 | 0.3047 | 0.066* | |
C6 | 0.1328 (3) | 0.4208 (4) | 0.3845 (2) | 0.0595 (8) | |
H6A | 0.1676 | 0.4910 | 0.4369 | 0.071* | |
H6B | 0.0528 | 0.3844 | 0.4017 | 0.071* | |
C7 | 0.2171 (3) | 0.2776 (4) | 0.3801 (2) | 0.0532 (7) | |
H7 | 0.2367 | 0.2350 | 0.4469 | 0.064* | |
C8 | 0.3375 (3) | 0.3173 (4) | 0.3368 (2) | 0.0462 (6) | |
H8 | 0.3851 | 0.3885 | 0.3836 | 0.055* | |
C9 | 0.3146 (3) | 0.4084 (4) | 0.2382 (2) | 0.0470 (6) | |
H9 | 0.2646 | 0.3382 | 0.1922 | 0.056* | |
C10 | 0.2375 (3) | 0.5628 (4) | 0.2487 (2) | 0.0519 (7) | |
C11 | 0.4368 (3) | 0.4395 (4) | 0.1935 (2) | 0.0535 (7) | |
H11A | 0.4176 | 0.4827 | 0.1276 | 0.064* | |
H11B | 0.4833 | 0.5200 | 0.2329 | 0.064* | |
C12 | 0.5192 (2) | 0.2917 (4) | 0.1871 (2) | 0.0485 (7) | |
H12 | 0.5987 | 0.3247 | 0.1652 | 0.058* | |
C13 | 0.5434 (2) | 0.2052 (3) | 0.28595 (19) | 0.0459 (6) | |
C14 | 0.4175 (2) | 0.1701 (4) | 0.32502 (19) | 0.0451 (6) | |
H14 | 0.3711 | 0.1030 | 0.2751 | 0.054* | |
C15 | 0.4499 (3) | 0.0638 (4) | 0.4141 (2) | 0.0547 (7) | |
H15A | 0.3816 | −0.0068 | 0.4247 | 0.066* | |
H15B | 0.4709 | 0.1270 | 0.4732 | 0.066* | |
C16 | 0.5637 (3) | −0.0323 (4) | 0.3868 (2) | 0.0551 (7) | |
H16A | 0.6333 | −0.0180 | 0.4368 | 0.066* | |
H16B | 0.5440 | −0.1453 | 0.3818 | 0.066* | |
C17 | 0.5958 (2) | 0.0323 (4) | 0.2866 (2) | 0.0496 (7) | |
H17 | 0.5454 | −0.0274 | 0.2351 | 0.060* | |
C18 | 0.6273 (3) | 0.3131 (4) | 0.3556 (2) | 0.0588 (8) | |
H18A | 0.7041 | 0.3313 | 0.3281 | 0.088* | |
H18B | 0.6436 | 0.2620 | 0.4187 | 0.088* | |
H18C | 0.5865 | 0.4134 | 0.3636 | 0.088* | |
C19 | 0.3085 (3) | 0.6827 (4) | 0.3197 (3) | 0.0696 (9) | |
H19A | 0.3377 | 0.6293 | 0.3801 | 0.104* | |
H19B | 0.2542 | 0.7685 | 0.3336 | 0.104* | |
H19C | 0.3779 | 0.7248 | 0.2896 | 0.104* | |
C20 | 0.7330 (3) | 0.0013 (4) | 0.2718 (2) | 0.0594 (8) | |
H20 | 0.7851 | 0.0549 | 0.3249 | 0.071* | |
C21 | 0.7693 (4) | 0.0617 (6) | 0.1733 (3) | 0.0883 (13) | |
H21A | 0.8522 | 0.0275 | 0.1651 | 0.132* | |
H21B | 0.7657 | 0.1763 | 0.1720 | 0.132* | |
H21C | 0.7130 | 0.0195 | 0.1206 | 0.132* | |
C22 | 0.7566 (3) | −0.1761 (5) | 0.2797 (3) | 0.0731 (10) | |
H22 | 0.7138 | −0.2404 | 0.2320 | 0.088* | |
C23 | 0.8307 (4) | −0.2474 (6) | 0.3462 (3) | 0.0881 (12) | |
H23A | 0.8756 | −0.1881 | 0.3954 | 0.106* | |
H23B | 0.8390 | −0.3579 | 0.3448 | 0.106* | |
C31A | −0.1746 (10) | 0.5396 (14) | −0.0041 (8) | 0.092 (3) | 0.613 (8) |
H31A | −0.2342 | 0.4850 | −0.0453 | 0.111* | 0.613 (8) |
C31B | −0.1953 (12) | 0.477 (2) | 0.0427 (13) | 0.080 (4) | 0.387 (8) |
H31B | −0.2450 | 0.4396 | −0.0122 | 0.096* | 0.387 (8) |
C71 | 0.0867 (4) | 0.0472 (5) | 0.3579 (3) | 0.0829 (11) | |
H71 | 0.0480 | −0.0309 | 0.3170 | 0.100* | |
C121 | 0.4798 (3) | 0.1984 (5) | 0.0229 (2) | 0.0660 (9) | |
H121 | 0.4408 | 0.1266 | −0.0222 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.092 (2) | 0.0736 (18) | 0.1001 (19) | 0.0190 (16) | −0.0270 (16) | −0.0263 (16) |
O7 | 0.0540 (11) | 0.0581 (13) | 0.0685 (13) | −0.0075 (10) | 0.0167 (10) | 0.0003 (11) |
O12 | 0.0587 (11) | 0.0600 (13) | 0.0488 (10) | −0.0012 (11) | 0.0122 (9) | −0.0012 (10) |
O31A | 0.134 (5) | 0.077 (4) | 0.213 (8) | 0.000 (4) | −0.088 (5) | 0.015 (5) |
O31B | 0.057 (4) | 0.164 (10) | 0.116 (7) | 0.009 (5) | −0.007 (4) | −0.063 (7) |
O71 | 0.195 (4) | 0.162 (4) | 0.117 (3) | −0.095 (4) | 0.070 (3) | 0.009 (3) |
O121 | 0.118 (2) | 0.102 (2) | 0.0607 (14) | −0.010 (2) | 0.0373 (14) | 0.0042 (16) |
C1 | 0.068 (2) | 0.0506 (18) | 0.081 (2) | 0.0085 (17) | 0.0206 (17) | 0.0097 (18) |
C2 | 0.092 (2) | 0.066 (2) | 0.0578 (18) | 0.018 (2) | 0.0079 (17) | 0.0069 (17) |
C3 | 0.0678 (19) | 0.059 (2) | 0.070 (2) | 0.0127 (18) | −0.0048 (16) | −0.0132 (17) |
C4 | 0.0536 (16) | 0.059 (2) | 0.0680 (18) | 0.0016 (16) | 0.0075 (14) | −0.0034 (17) |
C5 | 0.0555 (15) | 0.0504 (17) | 0.0596 (16) | 0.0079 (14) | 0.0137 (13) | −0.0031 (15) |
C6 | 0.0580 (17) | 0.068 (2) | 0.0548 (16) | 0.0047 (17) | 0.0170 (13) | −0.0083 (17) |
C7 | 0.0495 (14) | 0.0614 (19) | 0.0507 (15) | 0.0025 (15) | 0.0146 (12) | 0.0003 (15) |
C8 | 0.0464 (14) | 0.0489 (16) | 0.0453 (14) | −0.0018 (13) | 0.0142 (11) | −0.0007 (13) |
C9 | 0.0477 (14) | 0.0458 (14) | 0.0488 (14) | −0.0003 (12) | 0.0106 (11) | −0.0007 (13) |
C10 | 0.0543 (15) | 0.0433 (15) | 0.0593 (16) | 0.0047 (14) | 0.0121 (13) | −0.0013 (14) |
C11 | 0.0559 (15) | 0.0489 (17) | 0.0584 (17) | 0.0003 (14) | 0.0198 (13) | 0.0063 (14) |
C12 | 0.0465 (14) | 0.0511 (17) | 0.0499 (15) | −0.0064 (13) | 0.0142 (12) | −0.0043 (14) |
C13 | 0.0449 (13) | 0.0480 (16) | 0.0460 (14) | −0.0039 (13) | 0.0112 (11) | −0.0039 (13) |
C14 | 0.0467 (13) | 0.0478 (15) | 0.0420 (13) | −0.0009 (13) | 0.0097 (11) | 0.0018 (13) |
C15 | 0.0541 (15) | 0.0590 (18) | 0.0524 (15) | 0.0007 (15) | 0.0125 (12) | 0.0060 (15) |
C16 | 0.0520 (15) | 0.0548 (18) | 0.0588 (17) | 0.0011 (14) | 0.0074 (13) | 0.0061 (15) |
C17 | 0.0459 (14) | 0.0537 (17) | 0.0495 (15) | 0.0002 (14) | 0.0068 (11) | −0.0021 (13) |
C18 | 0.0541 (16) | 0.0616 (19) | 0.0613 (17) | −0.0080 (15) | 0.0085 (14) | −0.0124 (16) |
C19 | 0.0665 (19) | 0.0507 (19) | 0.092 (2) | −0.0001 (17) | 0.0109 (17) | −0.0145 (19) |
C20 | 0.0501 (16) | 0.064 (2) | 0.0651 (18) | 0.0098 (15) | 0.0119 (13) | 0.0001 (16) |
C21 | 0.072 (2) | 0.114 (4) | 0.084 (2) | 0.025 (3) | 0.0336 (19) | 0.020 (3) |
C22 | 0.064 (2) | 0.070 (2) | 0.085 (2) | 0.0177 (19) | 0.0108 (19) | −0.008 (2) |
C23 | 0.078 (2) | 0.076 (3) | 0.115 (3) | 0.017 (2) | 0.034 (2) | 0.008 (3) |
C31A | 0.083 (6) | 0.089 (7) | 0.099 (7) | 0.006 (5) | −0.023 (5) | −0.001 (5) |
C31B | 0.062 (6) | 0.089 (10) | 0.086 (9) | 0.005 (7) | −0.005 (6) | −0.038 (8) |
C71 | 0.076 (2) | 0.074 (3) | 0.104 (3) | −0.015 (2) | 0.031 (2) | 0.010 (2) |
C121 | 0.073 (2) | 0.075 (2) | 0.0507 (18) | 0.007 (2) | 0.0121 (15) | −0.0050 (18) |
O3—C31B | 1.170 (13) | C11—H11B | 0.9700 |
O3—C31A | 1.316 (10) | C12—C13 | 1.527 (4) |
O3—C3 | 1.466 (4) | C12—H12 | 0.9800 |
O7—C71 | 1.313 (4) | C13—C18 | 1.538 (4) |
O7—C7 | 1.473 (4) | C13—C14 | 1.543 (3) |
O71—C71 | 1.187 (5) | C13—C17 | 1.554 (4) |
O12—C121 | 1.320 (4) | C14—C15 | 1.517 (4) |
O12—C12 | 1.454 (3) | C14—H14 | 0.9800 |
O121—C121 | 1.193 (4) | C15—C16 | 1.549 (4) |
C1—C2 | 1.521 (5) | C15—H15A | 0.9700 |
C1—C10 | 1.536 (4) | C15—H15B | 0.9700 |
C1—H1A | 0.9700 | C16—C17 | 1.541 (4) |
C1—H1B | 0.9700 | C16—H16A | 0.9700 |
C2—C3 | 1.498 (5) | C16—H16B | 0.9700 |
C2—H2A | 0.9700 | C17—C20 | 1.543 (4) |
C2—H2B | 0.9700 | C17—H17 | 0.9800 |
C3—C4 | 1.513 (5) | C18—H18A | 0.9600 |
C3—H3 | 0.9800 | C18—H18B | 0.9600 |
C4—C5 | 1.525 (4) | C18—H18C | 0.9600 |
C4—H4A | 0.9700 | C19—H19A | 0.9600 |
C4—H4B | 0.9700 | C19—H19B | 0.9600 |
C5—C6 | 1.542 (4) | C19—H19C | 0.9600 |
C5—C10 | 1.552 (4) | C20—C22 | 1.508 (5) |
C5—H5 | 0.9800 | C20—C21 | 1.524 (5) |
C6—C7 | 1.512 (4) | C20—H20 | 0.9800 |
C6—H6A | 0.9700 | C21—H21A | 0.9600 |
C6—H6B | 0.9700 | C21—H21B | 0.9600 |
C7—C8 | 1.524 (4) | C21—H21C | 0.9600 |
C7—H7 | 0.9800 | C22—C23 | 1.292 (5) |
C8—C14 | 1.524 (4) | C22—H22 | 0.9300 |
C8—C9 | 1.541 (4) | C23—H23A | 0.9300 |
C8—H8 | 0.9800 | C23—H23B | 0.9300 |
C9—C11 | 1.536 (4) | C71—H71 | 0.9300 |
C9—C10 | 1.554 (4) | C121—H121 | 0.9300 |
C9—H9 | 0.9800 | C31A—O31A | 1.141 (11) |
C10—C19 | 1.543 (5) | C31A—H31A | 0.9300 |
C11—C12 | 1.533 (4) | C31B—O31B | 1.179 (14) |
C11—H11A | 0.9700 | C31B—H31B | 0.9300 |
C31B—O3—C3 | 121.8 (7) | C13—C12—H12 | 109.0 |
C31A—O3—C3 | 118.3 (5) | C11—C12—H12 | 109.0 |
C71—O7—C7 | 118.2 (3) | C12—C13—C18 | 107.6 (2) |
C121—O12—C12 | 116.9 (3) | C12—C13—C14 | 108.4 (2) |
C2—C1—C10 | 115.3 (3) | C18—C13—C14 | 112.7 (2) |
C2—C1—H1A | 108.4 | C12—C13—C17 | 118.4 (2) |
C10—C1—H1A | 108.4 | C18—C13—C17 | 110.5 (2) |
C2—C1—H1B | 108.4 | C14—C13—C17 | 99.0 (2) |
C10—C1—H1B | 108.4 | C15—C14—C8 | 118.5 (2) |
H1A—C1—H1B | 107.5 | C15—C14—C13 | 104.3 (2) |
C3—C2—C1 | 109.1 (3) | C8—C14—C13 | 114.5 (2) |
C3—C2—H2A | 109.9 | C15—C14—H14 | 106.2 |
C1—C2—H2A | 109.9 | C8—C14—H14 | 106.2 |
C3—C2—H2B | 109.9 | C13—C14—H14 | 106.2 |
C1—C2—H2B | 109.9 | C14—C15—C16 | 103.7 (2) |
H2A—C2—H2B | 108.3 | C14—C15—H15A | 111.0 |
O3—C3—C2 | 109.2 (3) | C16—C15—H15A | 111.0 |
O3—C3—C4 | 108.7 (3) | C14—C15—H15B | 111.0 |
C2—C3—C4 | 111.0 (3) | C16—C15—H15B | 111.0 |
O3—C3—H3 | 109.3 | H15A—C15—H15B | 109.0 |
C2—C3—H3 | 109.3 | C17—C16—C15 | 106.8 (2) |
C4—C3—H3 | 109.3 | C17—C16—H16A | 110.4 |
C3—C4—C5 | 110.6 (3) | C15—C16—H16A | 110.4 |
C3—C4—H4A | 109.5 | C17—C16—H16B | 110.4 |
C5—C4—H4A | 109.5 | C15—C16—H16B | 110.4 |
C3—C4—H4B | 109.5 | H16A—C16—H16B | 108.6 |
C5—C4—H4B | 109.5 | C16—C17—C20 | 111.4 (2) |
H4A—C4—H4B | 108.1 | C16—C17—C13 | 102.5 (2) |
C4—C5—C6 | 112.1 (3) | C20—C17—C13 | 120.8 (2) |
C4—C5—C10 | 113.5 (2) | C16—C17—H17 | 107.1 |
C6—C5—C10 | 111.7 (2) | C20—C17—H17 | 107.1 |
C4—C5—H5 | 106.3 | C13—C17—H17 | 107.1 |
C6—C5—H5 | 106.3 | C13—C18—H18A | 109.5 |
C10—C5—H5 | 106.3 | C13—C18—H18B | 109.5 |
C7—C6—C5 | 114.7 (2) | H18A—C18—H18B | 109.5 |
C7—C6—H6A | 108.6 | C13—C18—H18C | 109.5 |
C5—C6—H6A | 108.6 | H18A—C18—H18C | 109.5 |
C7—C6—H6B | 108.6 | H18B—C18—H18C | 109.5 |
C5—C6—H6B | 108.6 | C10—C19—H19A | 109.5 |
H6A—C6—H6B | 107.6 | C10—C19—H19B | 109.5 |
O7—C7—C6 | 110.2 (2) | H19A—C19—H19B | 109.5 |
O7—C7—C8 | 106.6 (2) | C10—C19—H19C | 109.5 |
C6—C7—C8 | 112.8 (3) | H19A—C19—H19C | 109.5 |
O7—C7—H7 | 109.0 | H19B—C19—H19C | 109.5 |
C6—C7—H7 | 109.0 | C22—C20—C21 | 109.4 (3) |
C8—C7—H7 | 109.0 | C22—C20—C17 | 108.4 (3) |
C14—C8—C7 | 112.5 (2) | C21—C20—C17 | 113.5 (3) |
C14—C8—C9 | 110.5 (2) | C22—C20—H20 | 108.5 |
C7—C8—C9 | 112.2 (2) | C21—C20—H20 | 108.5 |
C14—C8—H8 | 107.1 | C17—C20—H20 | 108.5 |
C7—C8—H8 | 107.1 | C20—C21—H21A | 109.5 |
C9—C8—H8 | 107.1 | C20—C21—H21B | 109.5 |
C11—C9—C8 | 111.1 (2) | H21A—C21—H21B | 109.5 |
C11—C9—C10 | 112.9 (2) | C20—C21—H21C | 109.5 |
C8—C9—C10 | 111.8 (2) | H21A—C21—H21C | 109.5 |
C11—C9—H9 | 106.9 | H21B—C21—H21C | 109.5 |
C8—C9—H9 | 106.9 | C23—C22—C20 | 126.4 (4) |
C10—C9—H9 | 106.9 | C23—C22—H22 | 116.8 |
C1—C10—C19 | 105.8 (3) | C20—C22—H22 | 116.8 |
C1—C10—C5 | 108.0 (2) | C22—C23—H23A | 120.0 |
C19—C10—C5 | 109.8 (2) | C22—C23—H23B | 120.0 |
C1—C10—C9 | 113.0 (2) | H23A—C23—H23B | 120.0 |
C19—C10—C9 | 111.1 (2) | O71—C71—O7 | 125.7 (4) |
C5—C10—C9 | 109.0 (2) | O71—C71—H71 | 117.1 |
C12—C11—C9 | 114.6 (2) | O7—C71—H71 | 117.1 |
C12—C11—H11A | 108.6 | O121—C121—O12 | 126.9 (4) |
C9—C11—H11A | 108.6 | O121—C121—H121 | 116.5 |
C12—C11—H11B | 108.6 | O12—C121—H121 | 116.5 |
C9—C11—H11B | 108.6 | O31A—C31A—O3 | 124.0 (9) |
H11A—C11—H11B | 107.6 | O31A—C31A—H31A | 118.0 |
O12—C12—C13 | 107.7 (2) | O3—C31A—H31A | 118.0 |
O12—C12—C11 | 109.8 (2) | O3—C31B—O31B | 122.6 (12) |
C13—C12—C11 | 112.4 (2) | O3—C31B—H31B | 118.7 |
O12—C12—H12 | 109.0 | O31B—C31B—H31B | 118.7 |
C10—C1—C2—C3 | 56.8 (4) | C9—C11—C12—O12 | 67.3 (3) |
C31B—O3—C3—C2 | −145.9 (13) | C9—C11—C12—C13 | −52.5 (3) |
C31A—O3—C3—C2 | −98.9 (8) | O12—C12—C13—C18 | 169.8 (2) |
C31B—O3—C3—C4 | 92.8 (13) | C11—C12—C13—C18 | −69.2 (3) |
C31A—O3—C3—C4 | 139.8 (7) | O12—C12—C13—C14 | −68.0 (3) |
C1—C2—C3—O3 | −178.6 (3) | C11—C12—C13—C14 | 53.0 (3) |
C1—C2—C3—C4 | −58.8 (4) | O12—C12—C13—C17 | 43.6 (3) |
O3—C3—C4—C5 | 179.4 (3) | C11—C12—C13—C17 | 164.6 (2) |
C2—C3—C4—C5 | 59.2 (4) | C7—C8—C14—C15 | −53.4 (3) |
C3—C4—C5—C6 | 177.1 (2) | C9—C8—C14—C15 | −179.7 (2) |
C3—C4—C5—C10 | −55.3 (3) | C7—C8—C14—C13 | −177.2 (2) |
C4—C5—C6—C7 | 77.2 (3) | C9—C8—C14—C13 | 56.5 (3) |
C10—C5—C6—C7 | −51.4 (4) | C12—C13—C14—C15 | 171.8 (2) |
C71—O7—C7—C6 | −88.7 (3) | C18—C13—C14—C15 | −69.1 (3) |
C71—O7—C7—C8 | 148.5 (3) | C17—C13—C14—C15 | 47.7 (3) |
C5—C6—C7—O7 | −70.5 (3) | C12—C13—C14—C8 | −57.0 (3) |
C5—C6—C7—C8 | 48.5 (4) | C18—C13—C14—C8 | 62.1 (3) |
O7—C7—C8—C14 | −54.4 (3) | C17—C13—C14—C8 | 178.9 (2) |
C6—C7—C8—C14 | −175.5 (2) | C8—C14—C15—C16 | −161.0 (2) |
O7—C7—C8—C9 | 71.0 (3) | C13—C14—C15—C16 | −32.2 (3) |
C6—C7—C8—C9 | −50.1 (3) | C14—C15—C16—C17 | 3.8 (3) |
C14—C8—C9—C11 | −50.6 (3) | C15—C16—C17—C20 | 156.1 (3) |
C7—C8—C9—C11 | −177.1 (3) | C15—C16—C17—C13 | 25.5 (3) |
C14—C8—C9—C10 | −177.8 (2) | C12—C13—C17—C16 | −160.7 (2) |
C7—C8—C9—C10 | 55.7 (3) | C18—C13—C17—C16 | 74.6 (3) |
C2—C1—C10—C19 | −168.8 (3) | C14—C13—C17—C16 | −43.9 (3) |
C2—C1—C10—C5 | −51.3 (4) | C12—C13—C17—C20 | 74.8 (3) |
C2—C1—C10—C9 | 69.4 (3) | C18—C13—C17—C20 | −50.0 (3) |
C4—C5—C10—C1 | 49.8 (4) | C14—C13—C17—C20 | −168.5 (3) |
C6—C5—C10—C1 | 177.6 (3) | C16—C17—C20—C22 | 57.7 (4) |
C4—C5—C10—C19 | 164.7 (3) | C13—C17—C20—C22 | 178.0 (3) |
C6—C5—C10—C19 | −67.5 (3) | C16—C17—C20—C21 | 179.5 (3) |
C4—C5—C10—C9 | −73.4 (3) | C13—C17—C20—C21 | −60.2 (4) |
C6—C5—C10—C9 | 54.5 (3) | C21—C20—C22—C23 | 119.6 (5) |
C11—C9—C10—C1 | 56.3 (3) | C17—C20—C22—C23 | −116.1 (4) |
C8—C9—C10—C1 | −177.6 (2) | C7—O7—C71—O71 | −0.1 (6) |
C11—C9—C10—C19 | −62.5 (3) | C12—O12—C121—O121 | 0.5 (5) |
C8—C9—C10—C19 | 63.7 (3) | C31B—O3—C31A—O31A | 113 (2) |
C11—C9—C10—C5 | 176.4 (2) | C3—O3—C31A—O31A | 5.8 (18) |
C8—C9—C10—C5 | −57.4 (3) | C31A—O3—C31B—O31B | −111 (3) |
C8—C9—C11—C12 | 50.2 (3) | C3—O3—C31B—O31B | −13 (3) |
C10—C9—C11—C12 | 176.8 (3) | C17—C20—C22—C23 | −116.1 (4) |
C121—O12—C12—C13 | −150.2 (3) | C21—C20—C22—C23 | 119.6 (5) |
C121—O12—C12—C11 | 87.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O31Ai | 0.97 | 2.59 | 3.5331 | 164 |
C4—H4A···O7 | 0.97 | 2.43 | 3.0662 | 122 |
C14—H14···O12 | 0.98 | 2.54 | 2.9286 | 104 |
C17—H17···O12 | 0.98 | 2.48 | 2.8947 | 105 |
C22—H22···O31Bii | 0.93 | 2.57 | 3.3366 | 140 |
C31A—H31B···O121iii | 1.13 | 2.59 | 3.6611 | 158 |
C121—H121···O31Bi | 0.93 | 2.42 | 3.2211 | 144 |
Symmetry codes: (i) −x, y−1/2, −z; (ii) x+1, y−1, z; (iii) x−1, y, z. |