Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602602X/ci2071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602602X/ci2071Isup2.hkl |
CCDC reference: 618151
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
0.45C23H24O4·0.45C23H24O4·0.05C23H23FO4·0.05C23H23FO4 | F(000) = 779.2 |
Mr = 366.24 | Dx = 1.293 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4330 reflections |
a = 9.6691 (2) Å | θ = 2.2–27.5° |
b = 10.5583 (2) Å | µ = 0.09 mm−1 |
c = 18.9279 (3) Å | T = 100 K |
β = 103.160 (1)° | Needle, yellow |
V = 1881.59 (6) Å3 | 0.42 × 0.13 × 0.11 mm |
Z = 4 |
Bruker SMART APEX2 CCD area-detector diffractometer | 4330 independent reflections |
Radiation source: fine-focus sealed tube | 2691 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −12→13 |
Tmin = 0.986, Tmax = 0.991 | l = −24→24 |
22779 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.5555P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4330 reflections | Δρmax = 0.25 e Å−3 |
317 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0036 (7) |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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) | |
O1 | 0.82345 (14) | 0.38791 (13) | 0.20713 (7) | 0.0463 (4) | |
O2 | 0.7644 (2) | 0.26442 (14) | −0.00561 (8) | 0.0719 (6) | |
O3 | 0.63335 (17) | 0.66797 (16) | −0.09223 (8) | 0.0655 (5) | |
O4 | 0.74149 (13) | 0.60456 (12) | 0.15921 (7) | 0.0396 (4) | |
H1O4 | 0.7721 | 0.5498 | 0.1894 | 0.059* | |
C1 | 0.7768 (2) | 0.20003 (18) | 0.14073 (10) | 0.0366 (5) | |
C2 | 0.6577 (2) | 0.13662 (18) | 0.10279 (11) | 0.0408 (5) | |
H2B | 0.5803 | 0.1822 | 0.0768 | 0.049* | |
C3 | 0.6531 (2) | 0.00565 (19) | 0.10334 (12) | 0.0480 (5) | |
H3A | 0.5722 | −0.0368 | 0.0787 | 0.058* | |
C4 | 0.7701 (3) | −0.0622 (2) | 0.14092 (12) | 0.0528 (6) | |
H4A | 0.7682 | −0.1503 | 0.1405 | 0.063* | |
C5 | 0.8884 (3) | 0.0005 (2) | 0.17863 (12) | 0.0524 (6) | |
H5A | 0.9667 | −0.0454 | 0.2033 | 0.063* | |
C6 | 0.8917 (2) | 0.1308 (2) | 0.18015 (10) | 0.0435 (5) | |
H6A | 0.9706 | 0.1727 | 0.2075 | 0.052* | |
C7 | 0.78273 (19) | 0.34106 (19) | 0.14513 (10) | 0.0367 (5) | |
C8 | 0.73865 (19) | 0.42204 (18) | 0.08205 (9) | 0.0332 (4) | |
C9 | 0.71778 (18) | 0.55371 (18) | 0.09205 (10) | 0.0322 (4) | |
C10 | 0.67817 (19) | 0.6356 (2) | 0.03366 (10) | 0.0371 (5) | |
H10A | 0.6688 | 0.7220 | 0.0410 | 0.16 (3)* | 0.899 (6) |
F1 | 0.6614 (12) | 0.7653 (9) | 0.0377 (6) | 0.054 (6) | 0.101 (6) |
C11 | 0.65296 (19) | 0.5859 (2) | −0.03559 (10) | 0.0393 (5) | |
C12 | 0.65582 (18) | 0.4566 (2) | −0.04853 (10) | 0.0356 (5) | |
C13 | 0.7163 (2) | 0.38013 (18) | 0.00862 (10) | 0.0374 (5) | |
C14 | 0.8071 (2) | 0.24259 (19) | −0.07372 (11) | 0.0412 (5) | |
C15A | 0.7796 (4) | 0.3646 (4) | −0.12604 (19) | 0.0368 (10) | 0.506 (2) |
H15A | 0.7755 | 0.3340 | −0.1754 | 0.044* | 0.506 (2) |
C15B | 0.7294 (4) | 0.4810 (4) | −0.1590 (2) | 0.0361 (10) | 0.494 (2) |
H15B | 0.7229 | 0.4514 | −0.2087 | 0.043* | 0.494 (2) |
C16 | 0.63186 (19) | 0.4082 (2) | −0.12435 (10) | 0.0378 (5) | |
H16A | 0.5651 | 0.3395 | −0.1329 | 0.045* | 0.506 (2) |
H16B | 0.5354 | 0.4247 | −0.1493 | 0.045* | 0.494 (2) |
C17A | 0.5835 (4) | 0.5218 (4) | −0.1802 (2) | 0.0423 (11) | 0.506 (2) |
H17A | 0.5872 | 0.4949 | −0.2287 | 0.051* | 0.506 (2) |
H17B | 0.4865 | 0.5459 | −0.1806 | 0.051* | 0.506 (2) |
C17B | 0.6627 (4) | 0.2590 (4) | −0.1258 (2) | 0.0417 (11) | 0.494 (2) |
H17C | 0.5902 | 0.2110 | −0.1095 | 0.050* | 0.494 (2) |
H17D | 0.6658 | 0.2314 | −0.1743 | 0.050* | 0.494 (2) |
C18 | 0.6761 (2) | 0.6276 (2) | −0.15898 (10) | 0.0444 (5) | |
C19A | 0.8332 (4) | 0.5997 (4) | −0.1486 (2) | 0.0423 (11) | 0.506 (2) |
H19A | 0.8861 | 0.6661 | −0.1188 | 0.051* | 0.506 (2) |
H19D | 0.8572 | 0.6036 | −0.1956 | 0.051* | 0.506 (2) |
C19B | 0.9175 (4) | 0.3162 (4) | −0.0989 (2) | 0.0425 (11) | 0.494 (2) |
H19B | 0.9302 | 0.2792 | −0.1439 | 0.051* | 0.494 (2) |
H19C | 1.0066 | 0.3071 | −0.0634 | 0.051* | 0.494 (2) |
C20 | 0.88502 (19) | 0.4660 (2) | −0.11233 (11) | 0.0415 (5) | |
H20A | 0.9145 | 0.4779 | −0.0608 | 0.050* | 0.506 (2) |
H20B | 0.9668 | 0.4393 | −0.1292 | 0.050* | 0.506 (2) |
H20C | 0.9515 | 0.5028 | −0.1371 | 0.050* | 0.494 (2) |
H20D | 0.8938 | 0.5086 | −0.0667 | 0.050* | 0.494 (2) |
C21A | 0.7419 (5) | 0.1298 (4) | −0.1101 (3) | 0.0524 (12) | 0.506 (2) |
H21A | 0.7470 | 0.0626 | −0.0754 | 0.079* | 0.506 (2) |
H21B | 0.7911 | 0.1050 | −0.1466 | 0.079* | 0.506 (2) |
H21C | 0.6442 | 0.1469 | −0.1325 | 0.079* | 0.506 (2) |
C21B | 0.5507 (5) | 0.6400 (5) | −0.2254 (2) | 0.0560 (13) | 0.494 (2) |
H21D | 0.5052 | 0.7204 | −0.2240 | 0.084* | 0.494 (2) |
H21E | 0.4836 | 0.5733 | −0.2245 | 0.084* | 0.494 (2) |
H21F | 0.5851 | 0.6339 | −0.2690 | 0.084* | 0.494 (2) |
C22A | 0.9639 (4) | 0.2293 (4) | −0.0372 (2) | 0.0473 (11) | 0.506 (2) |
H22A | 0.9771 | 0.1571 | −0.0056 | 0.071* | 0.506 (2) |
H22B | 0.9956 | 0.3043 | −0.0095 | 0.071* | 0.506 (2) |
H22C | 1.0178 | 0.2183 | −0.0735 | 0.071* | 0.506 (2) |
C22B | 0.7894 (5) | 0.7174 (4) | −0.1610 (3) | 0.0534 (12) | 0.494 (2) |
H22D | 0.7523 | 0.8020 | −0.1637 | 0.080* | 0.494 (2) |
H22E | 0.8273 | 0.7008 | −0.2027 | 0.080* | 0.494 (2) |
H22F | 0.8633 | 0.7085 | −0.1178 | 0.080* | 0.494 (2) |
C23A | 0.6375 (5) | 0.7503 (5) | −0.2069 (2) | 0.0577 (13) | 0.506 (2) |
H23A | 0.6987 | 0.8185 | −0.1858 | 0.087* | 0.506 (2) |
H23B | 0.5405 | 0.7732 | −0.2092 | 0.087* | 0.506 (2) |
H23C | 0.6497 | 0.7339 | −0.2550 | 0.087* | 0.506 (2) |
C23B | 0.8483 (6) | 0.0958 (4) | −0.0701 (3) | 0.0609 (14) | 0.494 (2) |
H23D | 0.9396 | 0.0844 | −0.0378 | 0.091* | 0.494 (2) |
H23E | 0.8517 | 0.0665 | −0.1177 | 0.091* | 0.494 (2) |
H23F | 0.7783 | 0.0482 | −0.0526 | 0.091* | 0.494 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0508 (9) | 0.0518 (9) | 0.0347 (8) | 0.0013 (7) | 0.0061 (7) | 0.0039 (7) |
O2 | 0.1473 (17) | 0.0335 (9) | 0.0510 (9) | −0.0005 (10) | 0.0564 (11) | 0.0005 (7) |
O3 | 0.0760 (11) | 0.0814 (12) | 0.0478 (9) | 0.0441 (9) | 0.0325 (8) | 0.0317 (9) |
O4 | 0.0421 (8) | 0.0415 (8) | 0.0355 (7) | −0.0032 (6) | 0.0093 (6) | −0.0026 (6) |
C1 | 0.0396 (11) | 0.0393 (12) | 0.0349 (10) | 0.0044 (9) | 0.0168 (9) | 0.0082 (9) |
C2 | 0.0430 (11) | 0.0389 (12) | 0.0428 (11) | 0.0042 (10) | 0.0145 (9) | 0.0091 (9) |
C3 | 0.0597 (14) | 0.0385 (13) | 0.0486 (13) | −0.0028 (11) | 0.0181 (11) | 0.0066 (10) |
C4 | 0.0769 (17) | 0.0361 (12) | 0.0507 (14) | 0.0117 (12) | 0.0257 (13) | 0.0117 (11) |
C5 | 0.0616 (15) | 0.0518 (15) | 0.0475 (13) | 0.0218 (12) | 0.0202 (12) | 0.0147 (11) |
C6 | 0.0436 (12) | 0.0508 (14) | 0.0390 (11) | 0.0066 (10) | 0.0158 (9) | 0.0108 (10) |
C7 | 0.0333 (10) | 0.0463 (12) | 0.0323 (11) | 0.0012 (9) | 0.0111 (8) | 0.0029 (9) |
C8 | 0.0331 (10) | 0.0372 (11) | 0.0296 (10) | −0.0043 (8) | 0.0078 (8) | 0.0021 (8) |
C9 | 0.0246 (9) | 0.0406 (11) | 0.0326 (10) | −0.0044 (8) | 0.0090 (8) | −0.0008 (9) |
C10 | 0.0313 (10) | 0.0389 (12) | 0.0435 (12) | 0.0029 (9) | 0.0138 (9) | 0.0061 (9) |
F1 | 0.049 (8) | 0.079 (12) | 0.043 (8) | −0.018 (6) | 0.026 (6) | −0.020 (6) |
C11 | 0.0266 (10) | 0.0560 (14) | 0.0377 (11) | 0.0099 (9) | 0.0120 (8) | 0.0148 (10) |
C12 | 0.0238 (9) | 0.0524 (13) | 0.0325 (10) | −0.0073 (9) | 0.0107 (8) | 0.0015 (9) |
C13 | 0.0411 (11) | 0.0353 (11) | 0.0385 (11) | −0.0097 (9) | 0.0148 (9) | 0.0001 (9) |
C14 | 0.0423 (11) | 0.0458 (12) | 0.0396 (11) | 0.0016 (10) | 0.0178 (9) | −0.0018 (9) |
C15A | 0.033 (2) | 0.051 (3) | 0.0285 (19) | −0.0072 (19) | 0.0117 (16) | −0.0040 (18) |
C15B | 0.032 (2) | 0.045 (2) | 0.033 (2) | 0.0001 (18) | 0.0114 (17) | 0.0003 (18) |
C16 | 0.0269 (9) | 0.0560 (13) | 0.0310 (10) | −0.0030 (9) | 0.0078 (8) | 0.0031 (9) |
C17A | 0.030 (2) | 0.066 (3) | 0.031 (2) | −0.002 (2) | 0.0058 (17) | 0.0104 (19) |
C17B | 0.044 (2) | 0.042 (2) | 0.044 (2) | −0.0105 (19) | 0.0174 (19) | −0.0067 (19) |
C18 | 0.0398 (11) | 0.0606 (14) | 0.0351 (11) | 0.0039 (11) | 0.0135 (9) | 0.0153 (10) |
C19A | 0.038 (2) | 0.055 (3) | 0.038 (2) | −0.004 (2) | 0.0180 (18) | 0.008 (2) |
C19B | 0.038 (2) | 0.048 (3) | 0.044 (2) | 0.0083 (19) | 0.0156 (19) | 0.005 (2) |
C20 | 0.0288 (10) | 0.0575 (13) | 0.0417 (11) | −0.0015 (9) | 0.0152 (9) | 0.0112 (10) |
C21A | 0.054 (3) | 0.056 (3) | 0.051 (3) | −0.011 (2) | 0.022 (2) | −0.016 (2) |
C21B | 0.059 (3) | 0.071 (3) | 0.040 (3) | 0.017 (3) | 0.015 (2) | 0.016 (2) |
C22A | 0.041 (2) | 0.045 (3) | 0.057 (3) | 0.0060 (19) | 0.014 (2) | −0.006 (2) |
C22B | 0.067 (3) | 0.043 (3) | 0.055 (3) | −0.001 (2) | 0.024 (2) | 0.008 (2) |
C23A | 0.059 (3) | 0.068 (3) | 0.048 (3) | 0.009 (3) | 0.018 (2) | 0.032 (2) |
C23B | 0.081 (4) | 0.044 (3) | 0.068 (3) | 0.011 (3) | 0.039 (3) | 0.002 (2) |
O1—C7 | 1.252 (2) | C16—C17A | 1.597 (4) |
O2—C13 | 1.356 (2) | C16—C17B | 1.604 (4) |
O2—C14 | 1.459 (2) | C16—H16A | 0.96 |
O3—C11 | 1.358 (2) | C16—H16B | 0.96 |
O3—C18 | 1.479 (2) | C17A—C18 | 1.431 (4) |
O4—C9 | 1.351 (2) | C17A—H17A | 0.97 |
O4—H1O4 | 0.82 | C17A—H17B | 0.97 |
C1—C2 | 1.384 (3) | C17B—H16A | 1.2544 |
C1—C6 | 1.396 (3) | C17B—H17C | 0.97 |
C1—C7 | 1.492 (3) | C17B—H17D | 0.97 |
C2—C3 | 1.384 (3) | C18—C22B | 1.455 (5) |
C2—H2B | 0.93 | C18—C19A | 1.516 (4) |
C3—C4 | 1.390 (3) | C18—C21B | 1.541 (5) |
C3—H3A | 0.93 | C18—C23A | 1.576 (4) |
C4—C5 | 1.372 (3) | C19A—C20 | 1.600 (4) |
C4—H4A | 0.93 | C19A—H19A | 0.97 |
C5—C6 | 1.376 (3) | C19A—H19D | 0.97 |
C5—H5A | 0.93 | C19B—C20 | 1.621 (4) |
C6—H6A | 0.93 | C19B—H19B | 0.97 |
C7—C8 | 1.451 (3) | C19B—H19C | 0.97 |
C8—C9 | 1.424 (3) | C20—H20A | 0.96 |
C8—C13 | 1.427 (3) | C20—H20B | 0.96 |
C9—C10 | 1.387 (3) | C20—H20C | 0.96 |
C10—C11 | 1.381 (3) | C20—H20D | 0.96 |
C10—F1 | 1.383 (10) | C21A—H21A | 0.96 |
C10—H10A | 0.93 | C21A—H21B | 0.96 |
C11—C12 | 1.389 (3) | C21A—H21C | 0.96 |
C12—C13 | 1.370 (3) | C21B—H21D | 0.96 |
C12—C16 | 1.491 (3) | C21B—H21E | 0.96 |
C14—C21A | 1.447 (5) | C21B—H21F | 0.96 |
C14—C19B | 1.484 (4) | C22A—H22A | 0.96 |
C14—C22A | 1.523 (4) | C22A—H22B | 0.96 |
C14—C17B | 1.524 (4) | C22A—H22C | 0.96 |
C14—C23B | 1.598 (5) | C22B—H22D | 0.96 |
C14—C15A | 1.610 (4) | C22B—H22E | 0.96 |
C15A—C20 | 1.460 (4) | C22B—H22F | 0.96 |
C15A—C16 | 1.508 (4) | C23A—H23A | 0.96 |
C15A—H15A | 0.98 | C23A—H23B | 0.96 |
C15B—C16 | 1.481 (4) | C23A—H23C | 0.96 |
C15B—C20 | 1.570 (4) | C23B—H23D | 0.96 |
C15B—C18 | 1.632 (4) | C23B—H23E | 0.96 |
C15B—H15B | 0.98 | C23B—H23F | 0.96 |
C13—O2—C14 | 119.78 (15) | H16B—C17A—H17A | 106.6 |
C11—O3—C18 | 118.35 (16) | C18—C17A—H17B | 109.8 |
C9—O4—H1O4 | 109.5 | C16—C17A—H17B | 109.8 |
C2—C1—C6 | 119.43 (19) | H17A—C17A—H17B | 108.3 |
C2—C1—C7 | 121.92 (17) | C14—C17B—C16 | 104.3 (2) |
C6—C1—C7 | 118.52 (18) | C14—C17B—H16A | 134.6 |
C3—C2—C1 | 120.25 (19) | C14—C17B—H17C | 110.9 |
C3—C2—H2B | 119.9 | C16—C17B—H17C | 110.9 |
C1—C2—H2B | 119.9 | C14—C17B—H17D | 110.9 |
C2—C3—C4 | 119.7 (2) | C16—C17B—H17D | 110.9 |
C2—C3—H3A | 120.1 | H16A—C17B—H17D | 106.7 |
C4—C3—H3A | 120.1 | H17C—C17B—H17D | 108.9 |
C5—C4—C3 | 120.1 (2) | C17A—C18—C22B | 158.1 (3) |
C5—C4—H4A | 119.9 | C17A—C18—O3 | 100.7 (2) |
C3—C4—H4A | 119.9 | C22B—C18—O3 | 101.1 (2) |
C4—C5—C6 | 120.4 (2) | C17A—C18—C19A | 115.4 (3) |
C4—C5—H5A | 119.8 | O3—C18—C19A | 114.4 (2) |
C6—C5—H5A | 119.8 | C22B—C18—C21B | 112.4 (3) |
C5—C6—C1 | 120.0 (2) | O3—C18—C21B | 110.6 (2) |
C5—C6—H6A | 120.0 | C19A—C18—C21B | 134.5 (3) |
C1—C6—H6A | 120.0 | C17A—C18—C23A | 115.4 (3) |
O1—C7—C8 | 120.62 (18) | O3—C18—C23A | 100.3 (2) |
O1—C7—C1 | 116.54 (17) | C19A—C18—C23A | 109.5 (2) |
C8—C7—C1 | 122.80 (17) | C22B—C18—C15B | 112.2 (3) |
C9—C8—C13 | 115.95 (17) | O3—C18—C15B | 115.03 (19) |
C9—C8—C7 | 119.33 (16) | C21B—C18—C15B | 105.7 (3) |
C13—C8—C7 | 124.71 (18) | C23A—C18—C15B | 144.4 (3) |
O4—C9—C10 | 117.34 (17) | C18—C19A—C20 | 115.7 (2) |
O4—C9—C8 | 120.97 (16) | C18—C19A—H19A | 108.4 |
C10—C9—C8 | 121.65 (17) | C20—C19A—H19A | 108.4 |
C11—C10—F1 | 115.5 (5) | C18—C19A—H19D | 108.4 |
C11—C10—C9 | 118.46 (19) | C20—C19A—H19D | 108.4 |
F1—C10—C9 | 126.0 (5) | H19A—C19A—H19D | 107.4 |
C11—C10—H10A | 120.8 | C18—C19A—H20C | 148.5 |
C9—C10—H10A | 120.8 | H19A—C19A—H20C | 97.1 |
O3—C11—C10 | 118.01 (19) | H19D—C19A—H20C | 80.2 |
O3—C11—C12 | 119.54 (18) | C14—C19B—C20 | 115.7 (3) |
C10—C11—C12 | 122.33 (18) | C14—C19B—H19B | 108.4 |
C13—C12—C11 | 117.53 (18) | C20—C19B—H19B | 108.4 |
C13—C12—C16 | 120.21 (18) | C14—C19B—H19C | 108.4 |
C11—C12—C16 | 120.12 (17) | C20—C19B—H19C | 108.4 |
O2—C13—C12 | 118.57 (17) | H19B—C19B—H19C | 107.4 |
O2—C13—C8 | 119.35 (18) | C14—C19B—H20B | 150.3 |
C12—C13—C8 | 121.95 (18) | H19B—C19B—H20B | 84.4 |
C21A—C14—O2 | 111.8 (2) | H19C—C19B—H20B | 92.3 |
C21A—C14—C19B | 123.0 (3) | C15A—C20—C19A | 115.7 (2) |
O2—C14—C19B | 124.8 (2) | C15B—C20—C19B | 108.2 (2) |
C21A—C14—C22A | 114.9 (3) | C15A—C20—H20A | 108.1 |
O2—C14—C22A | 93.8 (2) | C15B—C20—H20A | 125.7 |
O2—C14—C17B | 98.7 (2) | C19A—C20—H20A | 108.2 |
C19B—C14—C17B | 110.6 (3) | C15A—C20—H20B | 108.7 |
C22A—C14—C17B | 167.0 (3) | C15B—C20—H20B | 126.8 |
O2—C14—C23B | 103.5 (2) | C19A—C20—H20B | 108.5 |
C19B—C14—C23B | 109.3 (3) | H20A—C20—H20B | 107.5 |
C17B—C14—C23B | 108.7 (3) | C15B—C20—H20C | 110.3 |
C21A—C14—C15A | 111.9 (3) | C19B—C20—H20C | 110.2 |
O2—C14—C15A | 112.16 (19) | H20A—C20—H20C | 111.5 |
C22A—C14—C15A | 111.1 (2) | C15A—C20—H20D | 114.8 |
C23B—C14—C15A | 143.8 (3) | C15B—C20—H20D | 109.6 |
C20—C15A—C16 | 113.5 (3) | C19B—C20—H20D | 110.0 |
C20—C15A—C14 | 117.8 (3) | H20B—C20—H20D | 121.8 |
C16—C15A—C14 | 104.8 (2) | H20C—C20—H20D | 108.5 |
C20—C15A—H15A | 106.7 | C14—C21A—H21A | 109.5 |
C16—C15A—H15A | 106.7 | C14—C21A—H21B | 109.5 |
C14—C15A—H15A | 106.7 | C14—C21A—H21C | 109.5 |
C16—C15B—C20 | 108.9 (3) | C18—C21B—H21D | 109.5 |
C16—C15B—C18 | 105.0 (2) | C18—C21B—H21E | 109.5 |
C20—C15B—C18 | 111.0 (3) | H21D—C21B—H21E | 109.5 |
C16—C15B—H15B | 110.6 | C18—C21B—H21F | 109.5 |
C20—C15B—H15B | 110.6 | H21D—C21B—H21F | 109.5 |
C18—C15B—H15B | 110.6 | H21E—C21B—H21F | 109.5 |
C15B—C16—C12 | 105.9 (2) | C14—C22A—H22A | 109.5 |
C12—C16—C15A | 100.63 (19) | C14—C22A—H22B | 109.5 |
C12—C16—C17A | 109.7 (2) | C14—C22A—H22C | 109.5 |
C15A—C16—C17A | 110.6 (2) | C18—C22B—H22D | 109.5 |
C15B—C16—C17B | 111.2 (2) | C18—C22B—H22E | 109.5 |
C12—C16—C17B | 111.3 (2) | H22D—C22B—H22E | 109.5 |
C17A—C16—C17B | 138.9 (2) | C18—C22B—H22F | 109.5 |
C15B—C16—H16A | 142.2 | H22D—C22B—H22F | 109.5 |
C12—C16—H16A | 111.8 | H22E—C22B—H22F | 109.5 |
C15A—C16—H16A | 111.7 | C18—C23A—H23A | 109.5 |
C17A—C16—H16A | 111.8 | C18—C23A—H23B | 109.5 |
C15B—C16—H16B | 109.5 | C18—C23A—H23C | 109.5 |
C12—C16—H16B | 109.4 | C14—C23B—H23D | 109.5 |
C15A—C16—H16B | 149.7 | C14—C23B—H23E | 109.5 |
C17B—C16—H16B | 109.5 | H23D—C23B—H23E | 109.5 |
C18—C17A—C16 | 109.3 (2) | C14—C23B—H23F | 109.5 |
C18—C17A—H16B | 138.2 | H23D—C23B—H23F | 109.5 |
C18—C17A—H17A | 109.8 | H23E—C23B—H23F | 109.5 |
C16—C17A—H17A | 109.8 | ||
C6—C1—C2—C3 | −0.7 (3) | C11—C12—C16—C17B | 171.5 (2) |
C7—C1—C2—C3 | −176.32 (17) | C20—C15A—C16—C15B | 41.7 (3) |
C1—C2—C3—C4 | −1.4 (3) | C14—C15A—C16—C15B | 171.6 (3) |
C2—C3—C4—C5 | 1.4 (3) | C20—C15A—C16—C12 | −60.4 (3) |
C3—C4—C5—C6 | 0.6 (3) | C14—C15A—C16—C12 | 69.5 (2) |
C4—C5—C6—C1 | −2.7 (3) | C20—C15A—C16—C17A | 55.5 (3) |
C2—C1—C6—C5 | 2.7 (3) | C14—C15A—C16—C17A | −174.6 (2) |
C7—C1—C6—C5 | 178.51 (17) | C20—C15A—C16—C17B | −169.0 (3) |
C2—C1—C7—O1 | 130.05 (19) | C14—C15A—C16—C17B | −39.1 (2) |
C6—C1—C7—O1 | −45.6 (2) | C15B—C16—C17A—C18 | −48.6 (3) |
C2—C1—C7—C8 | −47.5 (3) | C12—C16—C17A—C18 | 47.5 (3) |
C6—C1—C7—C8 | 136.83 (18) | C15A—C16—C17A—C18 | −62.6 (3) |
O1—C7—C8—C9 | −11.1 (3) | C17B—C16—C17A—C18 | −132.0 (3) |
C1—C7—C8—C9 | 166.34 (16) | C21A—C14—C17B—C16 | −178.2 (3) |
O1—C7—C8—C13 | 167.63 (17) | O2—C14—C17B—C16 | 71.8 (2) |
C1—C7—C8—C13 | −14.9 (3) | C19B—C14—C17B—C16 | −60.6 (3) |
C13—C8—C9—O4 | −177.32 (15) | C22A—C14—C17B—C16 | −93.0 (12) |
C7—C8—C9—O4 | 1.5 (2) | C23B—C14—C17B—C16 | 179.4 (2) |
C13—C8—C9—C10 | 0.0 (2) | C15A—C14—C17B—C16 | −38.7 (2) |
C7—C8—C9—C10 | 178.83 (16) | C15B—C16—C17B—C14 | 68.8 (3) |
O4—C9—C10—C11 | −179.84 (15) | C12—C16—C17B—C14 | −49.0 (3) |
C8—C9—C10—C11 | 2.8 (3) | C15A—C16—C17B—C14 | 41.7 (2) |
O4—C9—C10—F1 | 0.4 (6) | C17A—C16—C17B—C14 | 130.6 (3) |
C8—C9—C10—F1 | −177.0 (6) | C16—C17A—C18—C22B | 104.9 (7) |
C18—O3—C11—C10 | 150.18 (17) | C16—C17A—C18—O3 | −70.2 (3) |
C18—O3—C11—C12 | −25.9 (3) | C16—C17A—C18—C19A | 53.5 (3) |
F1—C10—C11—O3 | 8.6 (5) | C16—C17A—C18—C21B | −177.9 (3) |
C9—C10—C11—O3 | −171.17 (16) | C16—C17A—C18—C23A | −177.2 (2) |
F1—C10—C11—C12 | −175.5 (5) | C16—C17A—C18—C15B | 42.9 (2) |
C9—C10—C11—C12 | 4.8 (3) | C11—O3—C18—C17A | 62.5 (2) |
O3—C11—C12—C13 | 161.02 (16) | C11—O3—C18—C22B | −115.6 (3) |
C10—C11—C12—C13 | −14.9 (3) | C11—O3—C18—C19A | −61.9 (3) |
O3—C11—C12—C16 | −2.4 (3) | C11—O3—C18—C21B | 125.1 (3) |
C10—C11—C12—C16 | −178.27 (16) | C11—O3—C18—C23A | −178.9 (2) |
C14—O2—C13—C12 | 25.8 (3) | C11—O3—C18—C15B | 5.5 (3) |
C14—O2—C13—C8 | −150.07 (18) | C16—C15B—C18—C17A | −45.8 (2) |
C11—C12—C13—O2 | −157.92 (17) | C20—C15B—C18—C17A | −163.4 (3) |
C16—C12—C13—O2 | 5.5 (3) | C16—C15B—C18—C22B | 155.0 (3) |
C11—C12—C13—C8 | 17.8 (3) | C20—C15B—C18—C22B | 37.5 (3) |
C16—C12—C13—C8 | −178.80 (16) | C16—C15B—C18—O3 | 40.1 (3) |
C9—C8—C13—O2 | 165.09 (17) | C20—C15B—C18—O3 | −77.4 (3) |
C7—C8—C13—O2 | −13.7 (3) | C16—C15B—C18—C19A | 145.2 (3) |
C9—C8—C13—C12 | −10.6 (3) | C20—C15B—C18—C19A | 27.6 (2) |
C7—C8—C13—C12 | 170.64 (17) | C16—C15B—C18—C21B | −82.1 (3) |
C13—O2—C14—C21A | −130.2 (3) | C20—C15B—C18—C21B | 160.3 (3) |
C13—O2—C14—C19B | 57.1 (3) | C16—C15B—C18—C23A | −132.3 (4) |
C13—O2—C14—C22A | 111.0 (2) | C20—C15B—C18—C23A | 110.1 (4) |
C13—O2—C14—C17B | −65.6 (3) | C17A—C18—C19A—C20 | −38.2 (4) |
C13—O2—C14—C23B | −177.4 (3) | C22B—C18—C19A—C20 | 163.4 (4) |
C13—O2—C14—C15A | −3.6 (3) | O3—C18—C19A—C20 | 78.0 (3) |
C21A—C14—C15A—C20 | −152.1 (3) | C21B—C18—C19A—C20 | −111.2 (4) |
O2—C14—C15A—C20 | 81.4 (3) | C23A—C18—C19A—C20 | −170.3 (3) |
C19B—C14—C15A—C20 | −36.3 (3) | C15B—C18—C19A—C20 | −28.1 (3) |
C22A—C14—C15A—C20 | −22.1 (4) | C21A—C14—C19B—C20 | 126.1 (4) |
C17B—C14—C15A—C20 | 169.1 (3) | O2—C14—C19B—C20 | −62.1 (4) |
C23B—C14—C15A—C20 | −108.9 (5) | C22A—C14—C19B—C20 | −132.9 (4) |
C21A—C14—C15A—C16 | 80.6 (3) | C17B—C14—C19B—C20 | 55.2 (4) |
O2—C14—C15A—C16 | −45.9 (3) | C23B—C14—C19B—C20 | 174.9 (3) |
C19B—C14—C15A—C16 | −163.6 (3) | C15A—C14—C19B—C20 | 31.6 (2) |
C22A—C14—C15A—C16 | −149.4 (2) | C16—C15A—C20—C15B | −39.4 (2) |
C17B—C14—C15A—C16 | 41.8 (2) | C14—C15A—C20—C15B | −162.3 (4) |
C23B—C14—C15A—C16 | 123.8 (5) | C16—C15A—C20—C19A | −39.4 (3) |
C20—C15B—C16—C12 | 55.6 (3) | C14—C15A—C20—C19A | −162.4 (2) |
C18—C15B—C16—C12 | −63.4 (3) | C16—C15A—C20—C19B | 155.8 (4) |
C20—C15B—C16—C15A | −36.8 (2) | C14—C15A—C20—C19B | 32.8 (3) |
C18—C15B—C16—C15A | −155.8 (3) | C16—C15B—C20—C15A | 38.8 (2) |
C20—C15B—C16—C17A | 158.9 (4) | C18—C15B—C20—C15A | 153.9 (3) |
C18—C15B—C16—C17A | 40.0 (2) | C16—C15B—C20—C19A | −141.3 (3) |
C20—C15B—C16—C17B | −65.5 (3) | C18—C15B—C20—C19A | −26.1 (2) |
C18—C15B—C16—C17B | 175.5 (2) | C16—C15B—C20—C19B | 51.7 (3) |
C13—C12—C16—C15B | −112.5 (2) | C18—C15B—C20—C19B | 166.8 (2) |
C11—C12—C16—C15B | 50.5 (3) | C18—C19A—C20—C15A | 29.5 (4) |
C13—C12—C16—C15A | −54.6 (2) | C18—C19A—C20—C15B | 29.5 (3) |
C11—C12—C16—C15A | 108.4 (2) | C18—C19A—C20—C19B | 78.0 (8) |
C13—C12—C16—C17A | −171.12 (19) | C14—C19B—C20—C15A | −35.2 (3) |
C11—C12—C16—C17A | −8.2 (2) | C14—C19B—C20—C15B | −48.3 (4) |
C13—C12—C16—C17B | 8.6 (3) | C14—C19B—C20—C19A | −91.5 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H1O4···O1 | 0.82 | 1.79 | 2.5211 (19) | 148 |
C5—H5A···O1i | 0.93 | 2.43 | 3.333 (3) | 163 |
Symmetry code: (i) −x+2, y−1/2, −z+1/2. |