Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031223/ci6660sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031223/ci6660Isup2.hkl |
CCDC reference: 290003
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C35H42O4 | Z = 2 |
Mr = 526.69 | F(000) = 568 |
Triclinic, P1 | Dx = 1.175 Mg m−3 |
Hall symbol: -P 1 | Melting point = 395–396 K |
a = 9.4790 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.2440 (5) Å | Cell parameters from 10469 reflections |
c = 13.9979 (6) Å | θ = 1.8–25.0° |
α = 75.869 (1)° | µ = 0.08 mm−1 |
β = 83.737 (1)° | T = 293 K |
γ = 70.930 (1)° | Block, brown |
V = 1488.23 (11) Å3 | 0.48 × 0.37 × 0.13 mm |
Siemens SMART CCD area-detector diffractometer | 5239 independent reflections |
Radiation source: fine-focus sealed tube | 4278 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.3 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→14 |
Tmin = 0.965, Tmax = 0.991 | l = −16→16 |
14446 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0635P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3 |
5239 reflections | (Δ/σ)max = 0.036 |
377 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−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 | ||
O1 | 1.00599 (19) | 0.13978 (16) | −0.15314 (10) | 0.0881 (4) | |
O2 | 0.89413 (14) | 0.31400 (13) | −0.06645 (9) | 0.0726 (4) | |
O3 | 0.80079 (13) | 0.48401 (11) | 0.01304 (8) | 0.0721 (4) | |
O4 | 0.97036 (12) | 0.47280 (10) | 0.31833 (8) | 0.0606 (3) | |
C1 | 0.88455 (17) | 0.42811 (14) | 0.08457 (11) | 0.0535 (4) | |
C2 | 0.88338 (16) | 0.48386 (13) | 0.16387 (11) | 0.0503 (4) | |
C3 | 0.96854 (16) | 0.42331 (13) | 0.24254 (11) | 0.0485 (4) | |
C4 | 1.06953 (16) | 0.29658 (13) | 0.25806 (10) | 0.0466 (3) | |
C5 | 1.30873 (19) | −0.02372 (14) | 0.07418 (12) | 0.0594 (4) | |
C6 | 1.3116 (2) | −0.07398 (16) | −0.00495 (13) | 0.0681 (5) | |
C7 | 1.2066 (2) | −0.01701 (18) | −0.07844 (14) | 0.0732 (5) | |
H7A | 1.2087 | −0.0532 | −0.1300 | 0.088* | |
C8 | 1.1012 (2) | 0.08979 (17) | −0.07736 (12) | 0.0659 (5) | |
C9 | 0.98950 (17) | 0.25682 (15) | 0.00816 (11) | 0.0553 (4) | |
C10 | 1.18358 (17) | 0.13928 (13) | 0.16124 (11) | 0.0511 (4) | |
H10A | 1.2469 | 0.0990 | 0.2135 | 0.061* | |
C11 | 1.22404 (16) | 0.29034 (13) | 0.29012 (11) | 0.0502 (4) | |
H11A | 1.2100 | 0.3182 | 0.3507 | 0.060* | |
H11B | 1.2860 | 0.2080 | 0.3044 | 0.060* | |
C12 | 1.30549 (16) | 0.36021 (14) | 0.21644 (12) | 0.0513 (4) | |
C13 | 1.37576 (18) | 0.42937 (16) | 0.23325 (14) | 0.0630 (4) | |
C14 | 1.4626 (3) | 0.4889 (2) | 0.15338 (19) | 0.0997 (8) | |
H14A | 1.4539 | 0.4697 | 0.0922 | 0.149* | |
H14B | 1.5658 | 0.4618 | 0.1701 | 0.149* | |
H14C | 1.4237 | 0.5732 | 0.1468 | 0.149* | |
C15 | 1.3811 (3) | 0.4514 (3) | 0.3334 (2) | 0.1261 (11) | |
H15A | 1.3121 | 0.4198 | 0.3777 | 0.189* | |
H15B | 1.3543 | 0.5351 | 0.3290 | 0.189* | |
H15C | 1.4803 | 0.4134 | 0.3575 | 0.189* | |
C16 | 1.4272 (3) | −0.19005 (18) | −0.01631 (17) | 0.0941 (7) | |
H16A | 1.4325 | −0.2481 | 0.0444 | 0.141* | |
H16B | 1.5229 | −0.1782 | −0.0326 | 0.141* | |
H16C | 1.3993 | −0.2173 | −0.0680 | 0.141* | |
C17 | 0.79698 (19) | 0.60776 (15) | 0.15827 (14) | 0.0637 (4) | |
H17A | 0.7493 | 0.6538 | 0.1006 | 0.076* | |
C18 | 0.7867 (2) | 0.65433 (16) | 0.23498 (15) | 0.0697 (5) | |
H18A | 0.7377 | 0.7349 | 0.2291 | 0.084* | |
C19 | 0.85137 (19) | 0.58143 (14) | 0.33088 (13) | 0.0628 (4) | |
C20 | 0.7332 (3) | 0.5388 (2) | 0.39783 (17) | 0.0954 (7) | |
H20A | 0.6952 | 0.4936 | 0.3660 | 0.143* | |
H20B | 0.6531 | 0.6059 | 0.4110 | 0.143* | |
H20C | 0.7770 | 0.4900 | 0.4587 | 0.143* | |
C21 | 0.9231 (3) | 0.6456 (2) | 0.3793 (2) | 0.1058 (8) | |
H21A | 1.0063 | 0.6606 | 0.3389 | 0.159* | |
H21B | 0.9575 | 0.5977 | 0.4427 | 0.159* | |
H21C | 0.8516 | 0.7194 | 0.3873 | 0.159* | |
C22 | 0.98484 (16) | 0.30918 (13) | 0.08695 (11) | 0.0491 (4) | |
C23 | 1.08296 (15) | 0.24663 (13) | 0.16638 (10) | 0.0466 (3) | |
C24 | 1.09385 (18) | 0.14490 (15) | 0.00248 (11) | 0.0550 (4) | |
C25 | 1.19672 (17) | 0.08550 (14) | 0.07970 (11) | 0.0523 (4) | |
C26 | 1.00195 (18) | 0.21973 (14) | 0.34523 (11) | 0.0555 (4) | |
H26A | 1.0722 | 0.1403 | 0.3603 | 0.067* | |
H26B | 0.9917 | 0.2527 | 0.4030 | 0.067* | |
C27 | 0.85391 (19) | 0.21107 (16) | 0.32719 (12) | 0.0583 (4) | |
C28 | 0.8149 (2) | 0.11463 (15) | 0.33942 (12) | 0.0611 (4) | |
C29 | 0.6575 (2) | 0.1218 (2) | 0.32390 (16) | 0.0865 (6) | |
H29A | 0.6014 | 0.2024 | 0.2963 | 0.130* | |
H29B | 0.6120 | 0.0946 | 0.3859 | 0.130* | |
H29C | 0.6584 | 0.0728 | 0.2795 | 0.130* | |
C30 | 0.9194 (3) | −0.00843 (19) | 0.36967 (19) | 0.1001 (7) | |
H30A | 1.0190 | −0.0054 | 0.3717 | 0.150* | |
H30B | 0.9172 | −0.0536 | 0.3229 | 0.150* | |
H30C | 0.8892 | −0.0453 | 0.4338 | 0.150* | |
C31 | 1.41925 (19) | −0.08518 (15) | 0.15577 (13) | 0.0645 (4) | |
H31A | 1.5084 | −0.1371 | 0.1301 | 0.077* | |
H31B | 1.4480 | −0.0261 | 0.1773 | 0.077* | |
C32 | 1.3570 (2) | −0.15653 (14) | 0.24264 (13) | 0.0638 (4) | |
H32A | 1.3026 | −0.2007 | 0.2275 | 0.077* | |
C33 | 1.3685 (2) | −0.16519 (15) | 0.33710 (13) | 0.0649 (4) | |
C34 | 1.4521 (3) | −0.1026 (2) | 0.37594 (18) | 0.1056 (8) | |
H34A | 1.4977 | −0.0592 | 0.3220 | 0.158* | |
H34B | 1.5280 | −0.1594 | 0.4185 | 0.158* | |
H34C | 1.3846 | −0.0488 | 0.4124 | 0.158* | |
C35 | 1.2975 (3) | −0.2411 (2) | 0.41490 (15) | 0.0901 (6) | |
H35A | 1.2419 | −0.2752 | 0.3840 | 0.135* | |
H35B | 1.2315 | −0.1933 | 0.4566 | 0.135* | |
H35C | 1.3738 | −0.3032 | 0.4538 | 0.135* | |
H1O2 | 0.842 (3) | 0.392 (2) | −0.0523 (18) | 0.112 (8)* | |
H1O1 | 0.943 (3) | 0.212 (2) | −0.1422 (17) | 0.097 (8)* | |
H12 | 1.3076 (18) | 0.3505 (14) | 0.1517 (13) | 0.060 (5)* | |
H27 | 0.778 (2) | 0.2862 (17) | 0.3090 (13) | 0.074 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1011 (11) | 0.1047 (12) | 0.0647 (8) | −0.0289 (10) | −0.0139 (8) | −0.0299 (8) |
O2 | 0.0687 (8) | 0.0868 (9) | 0.0566 (7) | −0.0120 (7) | −0.0182 (6) | −0.0150 (6) |
O3 | 0.0655 (7) | 0.0760 (8) | 0.0577 (7) | −0.0010 (6) | −0.0191 (6) | −0.0049 (6) |
O4 | 0.0574 (7) | 0.0575 (7) | 0.0621 (7) | −0.0066 (5) | −0.0090 (5) | −0.0172 (5) |
C1 | 0.0446 (8) | 0.0601 (9) | 0.0486 (8) | −0.0150 (7) | −0.0033 (6) | 0.0001 (7) |
C2 | 0.0422 (8) | 0.0504 (8) | 0.0513 (9) | −0.0120 (7) | −0.0021 (6) | −0.0019 (7) |
C3 | 0.0425 (8) | 0.0514 (8) | 0.0516 (8) | −0.0175 (7) | 0.0018 (6) | −0.0091 (7) |
C4 | 0.0432 (8) | 0.0479 (8) | 0.0445 (8) | −0.0127 (6) | −0.0032 (6) | −0.0039 (6) |
C5 | 0.0628 (10) | 0.0534 (9) | 0.0581 (10) | −0.0208 (8) | 0.0114 (8) | −0.0076 (7) |
C6 | 0.0824 (13) | 0.0598 (10) | 0.0611 (11) | −0.0273 (9) | 0.0202 (9) | −0.0145 (8) |
C7 | 0.0968 (14) | 0.0737 (12) | 0.0578 (11) | −0.0368 (11) | 0.0160 (10) | −0.0247 (9) |
C8 | 0.0758 (12) | 0.0775 (12) | 0.0515 (10) | −0.0345 (10) | 0.0043 (8) | −0.0154 (8) |
C9 | 0.0512 (9) | 0.0674 (10) | 0.0466 (8) | −0.0219 (8) | −0.0043 (7) | −0.0055 (7) |
C10 | 0.0488 (8) | 0.0516 (9) | 0.0487 (8) | −0.0143 (7) | −0.0046 (6) | −0.0040 (7) |
C11 | 0.0473 (8) | 0.0519 (8) | 0.0476 (8) | −0.0112 (7) | −0.0078 (6) | −0.0071 (7) |
C12 | 0.0437 (8) | 0.0586 (9) | 0.0486 (9) | −0.0124 (7) | −0.0043 (6) | −0.0100 (7) |
C13 | 0.0490 (9) | 0.0652 (10) | 0.0769 (11) | −0.0196 (8) | −0.0023 (8) | −0.0166 (9) |
C14 | 0.0780 (14) | 0.1100 (18) | 0.1134 (18) | −0.0539 (13) | −0.0084 (12) | 0.0069 (14) |
C15 | 0.133 (2) | 0.182 (3) | 0.125 (2) | −0.101 (2) | 0.0271 (18) | −0.090 (2) |
C16 | 0.1210 (19) | 0.0671 (12) | 0.0837 (14) | −0.0176 (12) | 0.0229 (13) | −0.0249 (11) |
C17 | 0.0549 (10) | 0.0563 (10) | 0.0672 (11) | −0.0065 (8) | −0.0080 (8) | −0.0024 (8) |
C18 | 0.0637 (11) | 0.0528 (10) | 0.0832 (13) | −0.0060 (8) | −0.0071 (9) | −0.0123 (9) |
C19 | 0.0616 (10) | 0.0502 (9) | 0.0733 (11) | −0.0097 (8) | −0.0039 (8) | −0.0176 (8) |
C20 | 0.0815 (14) | 0.0917 (15) | 0.0962 (16) | −0.0141 (12) | 0.0205 (12) | −0.0182 (12) |
C21 | 0.128 (2) | 0.0668 (13) | 0.128 (2) | −0.0209 (13) | −0.0501 (17) | −0.0257 (13) |
C22 | 0.0435 (8) | 0.0553 (9) | 0.0461 (8) | −0.0171 (7) | −0.0021 (6) | −0.0042 (7) |
C23 | 0.0425 (8) | 0.0497 (8) | 0.0465 (8) | −0.0178 (6) | −0.0006 (6) | −0.0042 (6) |
C24 | 0.0578 (9) | 0.0614 (10) | 0.0484 (9) | −0.0257 (8) | 0.0042 (7) | −0.0099 (7) |
C25 | 0.0538 (9) | 0.0533 (9) | 0.0498 (8) | −0.0224 (7) | 0.0063 (7) | −0.0072 (7) |
C26 | 0.0581 (9) | 0.0546 (9) | 0.0491 (9) | −0.0175 (7) | 0.0021 (7) | −0.0044 (7) |
C27 | 0.0531 (9) | 0.0546 (10) | 0.0618 (10) | −0.0168 (8) | 0.0082 (7) | −0.0075 (8) |
C28 | 0.0730 (11) | 0.0639 (10) | 0.0510 (9) | −0.0292 (9) | 0.0070 (8) | −0.0141 (8) |
C29 | 0.0845 (14) | 0.1052 (16) | 0.0866 (14) | −0.0545 (13) | 0.0128 (11) | −0.0245 (12) |
C30 | 0.126 (2) | 0.0623 (12) | 0.1154 (18) | −0.0331 (13) | −0.0193 (15) | −0.0141 (12) |
C31 | 0.0603 (10) | 0.0534 (9) | 0.0690 (11) | −0.0088 (8) | 0.0083 (8) | −0.0107 (8) |
C32 | 0.0714 (11) | 0.0506 (9) | 0.0681 (11) | −0.0203 (8) | −0.0005 (8) | −0.0099 (8) |
C33 | 0.0679 (11) | 0.0544 (10) | 0.0661 (11) | −0.0115 (8) | 0.0012 (8) | −0.0139 (8) |
C34 | 0.142 (2) | 0.1033 (18) | 0.0871 (16) | −0.0539 (17) | −0.0180 (15) | −0.0214 (13) |
C35 | 0.0983 (16) | 0.0875 (14) | 0.0712 (13) | −0.0262 (12) | 0.0080 (11) | −0.0017 (11) |
O1—C8 | 1.359 (2) | C16—H16B | 0.96 |
O1—H1O1 | 0.93 (2) | C16—H16C | 0.96 |
O2—C9 | 1.3541 (19) | C17—C18 | 1.314 (3) |
O2—H1O2 | 0.98 (3) | C17—H17A | 0.93 |
O3—C1 | 1.2591 (18) | C18—C19 | 1.487 (3) |
O4—C3 | 1.3483 (18) | C18—H18A | 0.93 |
O4—C19 | 1.4705 (19) | C19—C21 | 1.500 (3) |
C1—C2 | 1.435 (2) | C19—C20 | 1.523 (3) |
C1—C22 | 1.451 (2) | C20—H20A | 0.96 |
C2—C3 | 1.348 (2) | C20—H20B | 0.96 |
C2—C17 | 1.457 (2) | C20—H20C | 0.96 |
C3—C4 | 1.510 (2) | C21—H21A | 0.96 |
C4—C23 | 1.528 (2) | C21—H21B | 0.96 |
C4—C11 | 1.551 (2) | C21—H21C | 0.96 |
C4—C26 | 1.564 (2) | C22—C23 | 1.426 (2) |
C5—C6 | 1.386 (2) | C24—C25 | 1.425 (2) |
C5—C25 | 1.424 (2) | C26—C27 | 1.494 (2) |
C5—C31 | 1.515 (2) | C26—H26A | 0.97 |
C6—C7 | 1.398 (3) | C26—H26B | 0.97 |
C6—C16 | 1.517 (3) | C27—C28 | 1.316 (2) |
C7—C8 | 1.364 (3) | C27—H27 | 0.961 (19) |
C7—H7A | 0.93 | C28—C30 | 1.495 (3) |
C8—C24 | 1.425 (2) | C28—C29 | 1.503 (3) |
C9—C22 | 1.395 (2) | C29—H29A | 0.96 |
C9—C24 | 1.419 (2) | C29—H29B | 0.96 |
C10—C23 | 1.362 (2) | C29—H29C | 0.96 |
C10—C25 | 1.426 (2) | C30—H30A | 0.96 |
C10—H10A | 0.93 | C30—H30B | 0.96 |
C11—C12 | 1.490 (2) | C30—H30C | 0.96 |
C11—H11A | 0.97 | C31—C32 | 1.501 (2) |
C11—H11B | 0.97 | C31—H31A | 0.97 |
C12—C13 | 1.310 (2) | C31—H31B | 0.97 |
C12—H12 | 0.940 (17) | C32—C33 | 1.314 (2) |
C13—C14 | 1.501 (3) | C32—H32A | 0.93 |
C13—C15 | 1.499 (3) | C33—C34 | 1.484 (3) |
C14—H14A | 0.96 | C33—C35 | 1.502 (3) |
C14—H14B | 0.96 | C34—H34A | 0.96 |
C14—H14C | 0.96 | C34—H34B | 0.96 |
C15—H15A | 0.96 | C34—H34C | 0.96 |
C15—H15B | 0.96 | C35—H35A | 0.96 |
C15—H15C | 0.96 | C35—H35B | 0.96 |
C16—H16A | 0.96 | C35—H35C | 0.96 |
C8—O1—H1O1 | 107.7 (14) | O4—C19—C20 | 105.12 (14) |
C9—O2—H1O2 | 105.0 (14) | C18—C19—C20 | 110.22 (16) |
C3—O4—C19 | 120.20 (12) | C21—C19—C20 | 112.12 (19) |
O3—C1—C2 | 119.55 (15) | C19—C20—H20A | 109.5 |
O3—C1—C22 | 120.96 (15) | C19—C20—H20B | 109.5 |
C2—C1—C22 | 119.47 (13) | H20A—C20—H20B | 109.5 |
C3—C2—C1 | 120.05 (14) | C19—C20—H20C | 109.5 |
C3—C2—C17 | 119.15 (15) | H20A—C20—H20C | 109.5 |
C1—C2—C17 | 120.73 (14) | H20B—C20—H20C | 109.5 |
O4—C3—C2 | 121.69 (14) | C19—C21—H21A | 109.5 |
O4—C3—C4 | 112.25 (12) | C19—C21—H21B | 109.5 |
C2—C3—C4 | 126.06 (14) | H21A—C21—H21B | 109.5 |
C3—C4—C23 | 111.86 (12) | C19—C21—H21C | 109.5 |
C3—C4—C11 | 108.91 (12) | H21A—C21—H21C | 109.5 |
C23—C4—C11 | 111.81 (12) | H21B—C21—H21C | 109.5 |
C3—C4—C26 | 108.31 (12) | C9—C22—C23 | 119.35 (14) |
C23—C4—C26 | 108.65 (12) | C9—C22—C1 | 119.34 (14) |
C11—C4—C26 | 107.14 (11) | C23—C22—C1 | 121.26 (14) |
C6—C5—C25 | 119.00 (16) | C10—C23—C22 | 118.98 (14) |
C6—C5—C31 | 121.02 (16) | C10—C23—C4 | 120.65 (13) |
C25—C5—C31 | 119.95 (15) | C22—C23—C4 | 120.30 (13) |
C5—C6—C7 | 120.13 (17) | C9—C24—C8 | 122.94 (16) |
C5—C6—C16 | 122.27 (19) | C9—C24—C25 | 118.48 (14) |
C7—C6—C16 | 117.60 (18) | C8—C24—C25 | 118.58 (16) |
C8—C7—C6 | 122.42 (17) | C24—C25—C5 | 120.31 (15) |
C8—C7—H7A | 118.8 | C24—C25—C10 | 117.88 (14) |
C6—C7—H7A | 118.8 | C5—C25—C10 | 121.81 (15) |
O1—C8—C7 | 118.29 (17) | C27—C26—C4 | 115.37 (13) |
O1—C8—C24 | 122.23 (18) | C27—C26—H26A | 108.4 |
C7—C8—C24 | 119.48 (17) | C4—C26—H26A | 108.4 |
O2—C9—C22 | 119.89 (15) | C27—C26—H26B | 108.4 |
O2—C9—C24 | 118.22 (15) | C4—C26—H26B | 108.4 |
C22—C9—C24 | 121.88 (14) | H26A—C26—H26B | 107.5 |
C23—C10—C25 | 123.29 (14) | C28—C27—C26 | 127.87 (17) |
C23—C10—H10A | 118.4 | C28—C27—H27 | 117.7 (11) |
C25—C10—H10A | 118.4 | C26—C27—H27 | 114.3 (11) |
C12—C11—C4 | 115.06 (12) | C27—C28—C30 | 124.04 (18) |
C12—C11—H11A | 108.5 | C27—C28—C29 | 121.16 (18) |
C4—C11—H11A | 108.5 | C30—C28—C29 | 114.79 (17) |
C12—C11—H11B | 108.5 | C28—C29—H29A | 109.5 |
C4—C11—H11B | 108.5 | C28—C29—H29B | 109.5 |
H11A—C11—H11B | 107.5 | H29A—C29—H29B | 109.5 |
C13—C12—C11 | 127.09 (16) | C28—C29—H29C | 109.5 |
C13—C12—H12 | 118.2 (10) | H29A—C29—H29C | 109.5 |
C11—C12—H12 | 114.7 (10) | H29B—C29—H29C | 109.5 |
C12—C13—C14 | 121.92 (18) | C28—C30—H30A | 109.5 |
C12—C13—C15 | 123.10 (18) | C28—C30—H30B | 109.5 |
C14—C13—C15 | 114.94 (18) | H30A—C30—H30B | 109.5 |
C13—C14—H14A | 109.5 | C28—C30—H30C | 109.5 |
C13—C14—H14B | 109.5 | H30A—C30—H30C | 109.5 |
H14A—C14—H14B | 109.5 | H30B—C30—H30C | 109.5 |
C13—C14—H14C | 109.5 | C32—C31—C5 | 112.56 (15) |
H14A—C14—H14C | 109.5 | C32—C31—H31A | 109.1 |
H14B—C14—H14C | 109.5 | C5—C31—H31A | 109.1 |
C13—C15—H15A | 109.5 | C32—C31—H31B | 109.1 |
C13—C15—H15B | 109.5 | C5—C31—H31B | 109.1 |
H15A—C15—H15B | 109.5 | H31A—C31—H31B | 107.8 |
C13—C15—H15C | 109.5 | C33—C32—C31 | 128.99 (17) |
H15A—C15—H15C | 109.5 | C33—C32—H32A | 115.5 |
H15B—C15—H15C | 109.5 | C31—C32—H32A | 115.5 |
C6—C16—H16A | 109.5 | C32—C33—C34 | 123.56 (18) |
C6—C16—H16B | 109.5 | C32—C33—C35 | 121.88 (18) |
H16A—C16—H16B | 109.5 | C34—C33—C35 | 114.56 (18) |
C6—C16—H16C | 109.5 | C33—C34—H34A | 109.5 |
H16A—C16—H16C | 109.5 | C33—C34—H34B | 109.5 |
H16B—C16—H16C | 109.5 | H34A—C34—H34B | 109.5 |
C18—C17—C2 | 119.80 (16) | C33—C34—H34C | 109.5 |
C18—C17—H17A | 120.1 | H34A—C34—H34C | 109.5 |
C2—C17—H17A | 120.1 | H34B—C34—H34C | 109.5 |
C17—C18—C19 | 121.66 (16) | C33—C35—H35A | 109.5 |
C17—C18—H18A | 119.2 | C33—C35—H35B | 109.5 |
C19—C18—H18A | 119.2 | H35A—C35—H35B | 109.5 |
O4—C19—C18 | 111.55 (14) | C33—C35—H35C | 109.5 |
O4—C19—C21 | 105.41 (15) | H35A—C35—H35C | 109.5 |
C18—C19—C21 | 112.12 (16) | H35B—C35—H35C | 109.5 |
O3—C1—C2—C3 | 177.57 (14) | C2—C1—C22—C9 | −177.77 (13) |
C22—C1—C2—C3 | −3.9 (2) | O3—C1—C22—C23 | 178.23 (14) |
O3—C1—C2—C17 | −5.7 (2) | C2—C1—C22—C23 | −0.3 (2) |
C22—C1—C2—C17 | 172.84 (13) | C25—C10—C23—C22 | 0.2 (2) |
C19—O4—C3—C2 | 16.6 (2) | C25—C10—C23—C4 | 177.03 (13) |
C19—O4—C3—C4 | −162.97 (12) | C9—C22—C23—C10 | 2.9 (2) |
C1—C2—C3—O4 | 179.95 (13) | C1—C22—C23—C10 | −174.60 (13) |
C17—C2—C3—O4 | 3.2 (2) | C9—C22—C23—C4 | −173.96 (13) |
C1—C2—C3—C4 | −0.5 (2) | C1—C22—C23—C4 | 8.6 (2) |
C17—C2—C3—C4 | −177.29 (14) | C3—C4—C23—C10 | 171.54 (12) |
O4—C3—C4—C23 | −172.39 (11) | C11—C4—C23—C10 | 49.09 (18) |
C2—C3—C4—C23 | 8.0 (2) | C26—C4—C23—C10 | −68.94 (17) |
O4—C3—C4—C11 | −48.30 (15) | C3—C4—C23—C22 | −11.68 (18) |
C2—C3—C4—C11 | 132.13 (15) | C11—C4—C23—C22 | −134.13 (13) |
O4—C3—C4—C26 | 67.90 (15) | C26—C4—C23—C22 | 107.84 (14) |
C2—C3—C4—C26 | −111.67 (16) | O2—C9—C24—C8 | −0.8 (2) |
C25—C5—C6—C7 | 0.7 (2) | C22—C9—C24—C8 | −179.76 (14) |
C31—C5—C6—C7 | 178.67 (16) | O2—C9—C24—C25 | 178.63 (14) |
C25—C5—C6—C16 | 179.97 (16) | C22—C9—C24—C25 | −0.3 (2) |
C31—C5—C6—C16 | −2.1 (3) | O1—C8—C24—C9 | −1.5 (3) |
C5—C6—C7—C8 | 1.7 (3) | C7—C8—C24—C9 | 178.78 (15) |
C16—C6—C7—C8 | −177.57 (18) | O1—C8—C24—C25 | 179.11 (15) |
C6—C7—C8—O1 | 178.49 (17) | C7—C8—C24—C25 | −0.7 (2) |
C6—C7—C8—C24 | −1.7 (3) | C9—C24—C25—C5 | −176.43 (14) |
C3—C4—C11—C12 | −62.23 (16) | C8—C24—C25—C5 | 3.0 (2) |
C23—C4—C11—C12 | 61.89 (17) | C9—C24—C25—C10 | 3.3 (2) |
C26—C4—C11—C12 | −179.17 (13) | C8—C24—C25—C10 | −177.25 (14) |
C4—C11—C12—C13 | 135.35 (17) | C6—C5—C25—C24 | −3.0 (2) |
C11—C12—C13—C14 | 175.82 (17) | C31—C5—C25—C24 | 178.95 (14) |
C11—C12—C13—C15 | −1.7 (3) | C6—C5—C25—C10 | 177.24 (14) |
C3—C2—C17—C18 | −9.2 (2) | C31—C5—C25—C10 | −0.8 (2) |
C1—C2—C17—C18 | 174.02 (16) | C23—C10—C25—C24 | −3.3 (2) |
C2—C17—C18—C19 | −4.8 (3) | C23—C10—C25—C5 | 176.40 (14) |
C3—O4—C19—C18 | −28.1 (2) | C3—C4—C26—C27 | 64.66 (17) |
C3—O4—C19—C21 | −150.03 (17) | C23—C4—C26—C27 | −57.05 (17) |
C3—O4—C19—C20 | 91.34 (18) | C11—C4—C26—C27 | −178.01 (14) |
C17—C18—C19—O4 | 22.2 (2) | C4—C26—C27—C28 | 128.95 (18) |
C17—C18—C19—C21 | 140.2 (2) | C26—C27—C28—C30 | −3.6 (3) |
C17—C18—C19—C20 | −94.1 (2) | C26—C27—C28—C29 | 176.06 (16) |
O2—C9—C22—C23 | 178.24 (13) | C6—C5—C31—C32 | −96.08 (18) |
C24—C9—C22—C23 | −2.8 (2) | C25—C5—C31—C32 | 81.87 (19) |
O2—C9—C22—C1 | −4.2 (2) | C5—C31—C32—C33 | −137.49 (19) |
C24—C9—C22—C1 | 174.71 (13) | C31—C32—C33—C34 | −0.7 (3) |
O3—C1—C22—C9 | 0.8 (2) | C31—C32—C33—C35 | 179.63 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2 | 0.93 (2) | 1.75 (2) | 2.579 (2) | 147 (2) |
O2—H1O2···O3 | 0.98 (2) | 1.55 (2) | 2.463 (2) | 154 (2) |