The title compound, C
27H
40O
6, contains two fused cyclohexane rings with chair conformations, fused to a norbornene ring system. The ester groups that are attached to the norbornene unit are in a
cis configuration. There are two molecules in the asymmetric unit. The structure is stabilized by C—H
O intermolecular hydrogen bonds and van der Waals forces.
Supporting information
CCDC reference: 630538
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.086
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.52 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.36 Ratio
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.804 0.990
Tmin(prime) and Tmax expected: 0.933 0.990
RR(prime) = 0.862
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.79 mm
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.57
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.56
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio
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 25.30
From the CIF: _reflns_number_total 4615
Count of symmetry unique reflns 4599
Completeness (_total/calc) 100.35%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 16
Fraction of Friedel pairs measured 0.003
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 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C29 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C30 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C39 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40 = . R
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
17 ALERT level G = General alerts; check
16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000) and PLATON (Spek, 2003).
Maleopimaric acid trimethyl ester
top
Crystal data top
C27H40O6 | F(000) = 1000 |
Mr = 460.59 | Dx = 1.240 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2yb | Cell parameters from 10117 reflections |
a = 8.9848 (15) Å | θ = 3.0–25.3° |
b = 23.456 (4) Å | µ = 0.09 mm−1 |
c = 12.364 (2) Å | T = 193 K |
β = 108.804 (3)° | Block, colorless |
V = 2466.6 (7) Å3 | 0.79 × 0.60 × 0.12 mm |
Z = 4 | |
Data collection top
Rigaku Mercury diffractometer | 4615 independent reflections |
Radiation source: fine-focus sealed tube | 4475 reflections with I > 2/s(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.3°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −28→28 |
Tmin = 0.804, Tmax = 0.990 | l = −14→14 |
24150 measured reflections | |
Refinement top
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0442P)2 + 0.5815P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4615 reflections | Δρmax = 0.41 e Å−3 |
610 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 4148 Friedel pairs |
Primary atom site location: structure-invariant direct methods | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.2386 (2) | 0.15996 (8) | 0.57030 (17) | 0.0363 (5) | |
O2 | 0.4564 (2) | 0.19978 (8) | 0.69011 (17) | 0.0353 (4) | |
O3 | −0.0806 (2) | 0.15003 (9) | 0.65911 (19) | 0.0442 (5) | |
O4 | 0.1616 (2) | 0.15020 (9) | 0.78748 (16) | 0.0367 (5) | |
O5 | 0.5653 (2) | 0.43451 (9) | 0.52519 (17) | 0.0378 (5) | |
O6 | 0.5084 (2) | 0.51223 (9) | 0.4168 (2) | 0.0421 (5) | |
O7 | 0.8790 (2) | 0.55025 (9) | 0.93004 (17) | 0.0363 (4) | |
O8 | 1.0045 (2) | 0.51658 (8) | 0.81400 (18) | 0.0364 (5) | |
O9 | 0.4793 (2) | 0.55359 (9) | 0.81206 (18) | 0.0407 (5) | |
O10 | 0.6372 (2) | 0.55072 (8) | 0.70350 (16) | 0.0341 (4) | |
O11 | 1.2849 (2) | 0.27422 (8) | 0.96366 (17) | 0.0353 (5) | |
O12 | 1.3183 (2) | 0.19470 (8) | 1.06778 (17) | 0.0343 (4) | |
C1 | 0.2207 (3) | 0.25040 (11) | 0.6600 (2) | 0.0251 (5) | |
H1 | 0.2982 | 0.2713 | 0.7243 | 0.030* | |
C2 | 0.0728 (3) | 0.23726 (11) | 0.6960 (2) | 0.0266 (5) | |
H2 | 0.0928 | 0.2546 | 0.7733 | 0.032* | |
C3 | −0.0708 (3) | 0.26870 (11) | 0.6145 (2) | 0.0260 (5) | |
H3 | −0.1678 | 0.2597 | 0.6342 | 0.031* | |
C4 | −0.0346 (3) | 0.33305 (11) | 0.6281 (2) | 0.0281 (6) | |
H4A | −0.0169 | 0.3446 | 0.7083 | 0.034* | |
H4B | −0.1254 | 0.3549 | 0.5786 | 0.034* | |
C5 | 0.1138 (3) | 0.34682 (11) | 0.5946 (2) | 0.0238 (5) | |
H5 | 0.1975 | 0.3573 | 0.6674 | 0.029* | |
C6 | 0.1714 (3) | 0.29075 (10) | 0.5527 (2) | 0.0231 (5) | |
C7 | −0.0898 (3) | 0.25040 (11) | 0.4937 (2) | 0.0256 (5) | |
C8 | 0.0363 (3) | 0.26224 (11) | 0.4639 (2) | 0.0248 (5) | |
H8 | 0.0410 | 0.2532 | 0.3901 | 0.030* | |
C9 | 0.3130 (3) | 0.30108 (11) | 0.5120 (2) | 0.0268 (5) | |
H9A | 0.4078 | 0.3068 | 0.5794 | 0.032* | |
H9B | 0.3306 | 0.2667 | 0.4711 | 0.032* | |
C10 | 0.2921 (3) | 0.35260 (11) | 0.4332 (2) | 0.0271 (5) | |
H10A | 0.2040 | 0.3457 | 0.3619 | 0.033* | |
H10B | 0.3889 | 0.3587 | 0.4129 | 0.033* | |
C11 | 0.2579 (3) | 0.40550 (11) | 0.4937 (2) | 0.0241 (5) | |
H11 | 0.3374 | 0.4042 | 0.5718 | 0.029* | |
C12 | 0.0963 (3) | 0.39947 (11) | 0.5140 (2) | 0.0239 (5) | |
C13 | 0.2897 (3) | 0.46294 (11) | 0.4422 (2) | 0.0268 (5) | |
C14 | 0.2474 (3) | 0.51355 (11) | 0.5071 (2) | 0.0299 (6) | |
H14A | 0.3266 | 0.5161 | 0.5841 | 0.036* | |
H14B | 0.2524 | 0.5493 | 0.4659 | 0.036* | |
C15 | 0.0851 (3) | 0.50816 (12) | 0.5191 (2) | 0.0312 (6) | |
H15A | 0.0045 | 0.5095 | 0.4425 | 0.037* | |
H15B | 0.0665 | 0.5407 | 0.5641 | 0.037* | |
C16 | 0.0695 (3) | 0.45243 (12) | 0.5783 (2) | 0.0297 (6) | |
H16A | −0.0370 | 0.4504 | 0.5855 | 0.036* | |
H16B | 0.1466 | 0.4523 | 0.6563 | 0.036* | |
C17 | 0.3004 (3) | 0.19803 (11) | 0.6345 (2) | 0.0266 (5) | |
C18 | 0.5476 (4) | 0.15331 (15) | 0.6674 (3) | 0.0484 (8) | |
H18A | 0.5199 | 0.1478 | 0.5847 | 0.073* | |
H18B | 0.5249 | 0.1183 | 0.7026 | 0.073* | |
H18C | 0.6598 | 0.1623 | 0.6996 | 0.073* | |
C19 | 0.0399 (3) | 0.17470 (12) | 0.7074 (2) | 0.0310 (6) | |
C20 | 0.1389 (5) | 0.09133 (14) | 0.8119 (3) | 0.0534 (9) | |
H20A | 0.1365 | 0.0677 | 0.7460 | 0.080* | |
H20B | 0.0391 | 0.0873 | 0.8275 | 0.080* | |
H20C | 0.2255 | 0.0790 | 0.8789 | 0.080* | |
C21 | −0.2381 (3) | 0.22056 (13) | 0.4223 (2) | 0.0335 (6) | |
H21 | −0.2756 | 0.1963 | 0.4749 | 0.040* | |
C22 | −0.2088 (4) | 0.18136 (15) | 0.3330 (3) | 0.0447 (8) | |
H22A | −0.1242 | 0.1546 | 0.3704 | 0.067* | |
H22B | −0.1784 | 0.2042 | 0.2771 | 0.067* | |
H22C | −0.3051 | 0.1601 | 0.2940 | 0.067* | |
C23 | −0.3668 (4) | 0.26340 (19) | 0.3670 (4) | 0.0621 (10) | |
H23A | −0.3351 | 0.2869 | 0.3126 | 0.093* | |
H23B | −0.3841 | 0.2879 | 0.4261 | 0.093* | |
H23C | −0.4642 | 0.2431 | 0.3268 | 0.093* | |
C24 | −0.0441 (3) | 0.39261 (12) | 0.4031 (2) | 0.0297 (6) | |
H24A | −0.0575 | 0.4277 | 0.3580 | 0.045* | |
H24B | −0.1399 | 0.3851 | 0.4224 | 0.045* | |
H24C | −0.0242 | 0.3607 | 0.3586 | 0.045* | |
C25 | 0.4683 (3) | 0.46645 (11) | 0.4664 (2) | 0.0283 (6) | |
C26 | 0.6763 (4) | 0.51972 (14) | 0.4401 (3) | 0.0489 (8) | |
H26A | 0.7174 | 0.4880 | 0.4066 | 0.073* | |
H26B | 0.7293 | 0.5205 | 0.5229 | 0.073* | |
H26C | 0.6955 | 0.5557 | 0.4066 | 0.073* | |
C27 | 0.2068 (3) | 0.46948 (13) | 0.3125 (2) | 0.0336 (6) | |
H27A | 0.2286 | 0.4359 | 0.2728 | 0.050* | |
H27B | 0.2459 | 0.5037 | 0.2851 | 0.050* | |
H27C | 0.0931 | 0.4729 | 0.2972 | 0.050* | |
C28 | 0.8053 (3) | 0.45849 (11) | 0.8394 (2) | 0.0245 (5) | |
H28 | 0.8310 | 0.4398 | 0.7749 | 0.029* | |
C29 | 0.6238 (3) | 0.46717 (12) | 0.8026 (2) | 0.0281 (6) | |
H29 | 0.5802 | 0.4467 | 0.7281 | 0.034* | |
C30 | 0.5562 (3) | 0.43618 (12) | 0.8861 (2) | 0.0306 (6) | |
H30 | 0.4415 | 0.4444 | 0.8675 | 0.037* | |
C31 | 0.5842 (3) | 0.37198 (11) | 0.8706 (2) | 0.0316 (6) | |
H31A | 0.5291 | 0.3606 | 0.7906 | 0.038* | |
H31B | 0.5412 | 0.3491 | 0.9210 | 0.038* | |
C32 | 0.7628 (3) | 0.36035 (11) | 0.9007 (2) | 0.0236 (5) | |
H32 | 0.7804 | 0.3513 | 0.8267 | 0.028* | |
C33 | 0.8553 (3) | 0.41708 (11) | 0.9446 (2) | 0.0242 (5) | |
C34 | 0.6449 (3) | 0.45180 (12) | 1.0085 (2) | 0.0318 (6) | |
C35 | 0.7984 (3) | 0.44219 (11) | 1.0361 (2) | 0.0283 (6) | |
H35 | 0.8687 | 0.4508 | 1.1100 | 0.034* | |
C36 | 1.0337 (3) | 0.40819 (11) | 0.9835 (2) | 0.0276 (6) | |
H36A | 1.0676 | 0.4044 | 0.9152 | 0.033* | |
H36B | 1.0857 | 0.4424 | 1.0261 | 0.033* | |
C37 | 1.0879 (3) | 0.35578 (11) | 1.0590 (2) | 0.0278 (6) | |
H37A | 1.0660 | 0.3611 | 1.1318 | 0.033* | |
H37B | 1.2027 | 0.3507 | 1.0767 | 0.033* | |
C38 | 1.0018 (3) | 0.30295 (11) | 0.9976 (2) | 0.0233 (5) | |
H38 | 1.0102 | 0.3052 | 0.9190 | 0.028* | |
C39 | 0.8234 (3) | 0.30730 (11) | 0.9795 (2) | 0.0243 (5) | |
C40 | 1.0829 (3) | 0.24561 (11) | 1.0470 (2) | 0.0239 (5) | |
C41 | 0.9838 (3) | 0.19471 (11) | 0.9836 (2) | 0.0279 (6) | |
H41A | 0.9929 | 0.1922 | 0.9060 | 0.034* | |
H41B | 1.0274 | 0.1591 | 1.0246 | 0.034* | |
C42 | 0.8109 (3) | 0.19892 (11) | 0.9732 (2) | 0.0289 (6) | |
H42A | 0.7998 | 0.1973 | 1.0502 | 0.035* | |
H42B | 0.7532 | 0.1662 | 0.9285 | 0.035* | |
C43 | 0.7400 (3) | 0.25438 (11) | 0.9147 (2) | 0.0287 (6) | |
H43A | 0.6274 | 0.2558 | 0.9084 | 0.034* | |
H43B | 0.7468 | 0.2549 | 0.8363 | 0.034* | |
C44 | 0.8966 (3) | 0.51369 (11) | 0.8679 (2) | 0.0253 (5) | |
C45 | 1.0938 (4) | 0.56897 (14) | 0.8317 (3) | 0.0493 (8) | |
H45A | 1.1377 | 0.5768 | 0.9138 | 0.074* | |
H45B | 1.0248 | 0.6005 | 0.7940 | 0.074* | |
H45C | 1.1796 | 0.5652 | 0.7993 | 0.074* | |
C46 | 0.5727 (3) | 0.52839 (12) | 0.7782 (2) | 0.0304 (6) | |
C47 | 0.6014 (4) | 0.60966 (13) | 0.6735 (3) | 0.0417 (7) | |
H47A | 0.6264 | 0.6327 | 0.7433 | 0.062* | |
H47B | 0.4894 | 0.6135 | 0.6303 | 0.062* | |
H47C | 0.6642 | 0.6229 | 0.6267 | 0.062* | |
C48 | 0.5676 (4) | 0.46984 (15) | 1.0961 (3) | 0.0477 (8) | |
H48 | 0.6534 | 0.4850 | 1.1634 | 0.057* | |
C49 | 0.4480 (5) | 0.51755 (19) | 1.0559 (3) | 0.0653 (11) | |
H49A | 0.4038 | 0.5269 | 1.1166 | 0.098* | |
H49B | 0.3635 | 0.5052 | 0.9876 | 0.098* | |
H49C | 0.4996 | 0.5513 | 1.0376 | 0.098* | |
C50 | 0.5004 (6) | 0.4198 (2) | 1.1378 (5) | 0.0815 (15) | |
H50A | 0.5854 | 0.3939 | 1.1787 | 0.122* | |
H50B | 0.4270 | 0.3999 | 1.0726 | 0.122* | |
H50C | 0.4444 | 0.4327 | 1.1895 | 0.122* | |
C51 | 0.7839 (3) | 0.31216 (12) | 1.0913 (2) | 0.0300 (6) | |
H51A | 0.8411 | 0.3444 | 1.1361 | 0.045* | |
H51B | 0.8148 | 0.2770 | 1.1356 | 0.045* | |
H51C | 0.6706 | 0.3182 | 1.0736 | 0.045* | |
C52 | 1.2383 (3) | 0.24157 (11) | 1.0212 (2) | 0.0269 (5) | |
C53 | 1.4600 (3) | 0.18372 (14) | 1.0395 (3) | 0.0386 (7) | |
H53A | 1.5363 | 0.2142 | 1.0707 | 0.058* | |
H53B | 1.4345 | 0.1824 | 0.9563 | 0.058* | |
H53C | 1.5050 | 0.1471 | 1.0724 | 0.058* | |
C54 | 1.1203 (3) | 0.23944 (13) | 1.1774 (2) | 0.0337 (6) | |
H54A | 1.1871 | 0.2712 | 1.2162 | 0.051* | |
H54B | 1.1755 | 0.2034 | 1.2028 | 0.051* | |
H54C | 1.0222 | 0.2398 | 1.1958 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0317 (10) | 0.0304 (11) | 0.0426 (11) | 0.0004 (8) | 0.0061 (8) | −0.0100 (9) |
O2 | 0.0246 (10) | 0.0334 (11) | 0.0435 (11) | 0.0028 (8) | 0.0050 (8) | −0.0082 (9) |
O3 | 0.0398 (12) | 0.0365 (12) | 0.0567 (13) | −0.0063 (10) | 0.0162 (10) | 0.0040 (10) |
O4 | 0.0454 (12) | 0.0304 (10) | 0.0335 (10) | 0.0051 (9) | 0.0116 (9) | 0.0053 (9) |
O5 | 0.0285 (10) | 0.0346 (11) | 0.0475 (12) | −0.0006 (9) | 0.0084 (9) | 0.0071 (10) |
O6 | 0.0289 (11) | 0.0324 (11) | 0.0686 (14) | 0.0010 (8) | 0.0209 (10) | 0.0149 (10) |
O7 | 0.0450 (11) | 0.0292 (10) | 0.0387 (11) | −0.0052 (9) | 0.0190 (9) | −0.0093 (9) |
O8 | 0.0381 (11) | 0.0277 (10) | 0.0521 (12) | −0.0023 (8) | 0.0265 (10) | −0.0003 (9) |
O9 | 0.0396 (11) | 0.0330 (11) | 0.0530 (12) | 0.0076 (9) | 0.0196 (10) | 0.0039 (10) |
O10 | 0.0399 (11) | 0.0286 (10) | 0.0337 (10) | 0.0062 (9) | 0.0117 (9) | 0.0062 (8) |
O11 | 0.0358 (11) | 0.0344 (11) | 0.0403 (11) | 0.0005 (8) | 0.0185 (9) | 0.0082 (9) |
O12 | 0.0290 (10) | 0.0350 (11) | 0.0418 (11) | 0.0074 (8) | 0.0156 (9) | 0.0108 (9) |
C1 | 0.0259 (13) | 0.0261 (14) | 0.0231 (12) | −0.0012 (10) | 0.0078 (10) | −0.0027 (10) |
C2 | 0.0311 (14) | 0.0301 (14) | 0.0219 (12) | 0.0006 (11) | 0.0130 (10) | −0.0005 (10) |
C3 | 0.0259 (13) | 0.0297 (14) | 0.0256 (13) | 0.0001 (10) | 0.0128 (11) | 0.0006 (11) |
C4 | 0.0317 (14) | 0.0290 (14) | 0.0275 (13) | 0.0032 (11) | 0.0149 (11) | −0.0002 (11) |
C5 | 0.0253 (13) | 0.0268 (13) | 0.0204 (12) | −0.0004 (10) | 0.0089 (10) | −0.0033 (10) |
C6 | 0.0231 (12) | 0.0233 (13) | 0.0244 (12) | 0.0004 (10) | 0.0098 (10) | −0.0010 (10) |
C7 | 0.0255 (13) | 0.0286 (14) | 0.0231 (12) | −0.0008 (10) | 0.0082 (10) | 0.0010 (11) |
C8 | 0.0289 (13) | 0.0247 (13) | 0.0218 (12) | −0.0006 (10) | 0.0095 (10) | −0.0014 (10) |
C9 | 0.0253 (13) | 0.0259 (13) | 0.0326 (13) | −0.0014 (10) | 0.0141 (11) | −0.0058 (11) |
C10 | 0.0286 (14) | 0.0255 (13) | 0.0313 (13) | −0.0021 (11) | 0.0152 (11) | −0.0027 (11) |
C11 | 0.0228 (13) | 0.0250 (13) | 0.0242 (12) | −0.0004 (10) | 0.0071 (10) | −0.0031 (10) |
C12 | 0.0238 (13) | 0.0251 (13) | 0.0228 (12) | −0.0015 (10) | 0.0077 (10) | −0.0027 (10) |
C13 | 0.0260 (13) | 0.0249 (13) | 0.0289 (13) | −0.0016 (10) | 0.0081 (10) | 0.0011 (11) |
C14 | 0.0328 (15) | 0.0222 (13) | 0.0338 (14) | −0.0006 (11) | 0.0094 (12) | 0.0003 (11) |
C15 | 0.0314 (14) | 0.0273 (14) | 0.0361 (15) | 0.0038 (11) | 0.0127 (12) | −0.0027 (12) |
C16 | 0.0297 (14) | 0.0302 (14) | 0.0309 (14) | 0.0028 (11) | 0.0124 (11) | −0.0014 (11) |
C17 | 0.0267 (13) | 0.0261 (13) | 0.0254 (12) | −0.0014 (11) | 0.0064 (11) | 0.0030 (11) |
C18 | 0.0316 (16) | 0.0491 (19) | 0.062 (2) | 0.0079 (14) | 0.0122 (15) | −0.0132 (17) |
C19 | 0.0376 (16) | 0.0352 (15) | 0.0250 (13) | 0.0025 (12) | 0.0167 (12) | 0.0005 (11) |
C20 | 0.073 (2) | 0.0307 (17) | 0.057 (2) | 0.0076 (16) | 0.0217 (18) | 0.0093 (15) |
C21 | 0.0296 (15) | 0.0436 (17) | 0.0284 (13) | −0.0103 (12) | 0.0109 (12) | 0.0009 (12) |
C22 | 0.0419 (18) | 0.0479 (19) | 0.0400 (17) | −0.0153 (14) | 0.0074 (14) | −0.0120 (14) |
C23 | 0.0308 (17) | 0.076 (3) | 0.070 (2) | 0.0030 (17) | 0.0025 (16) | −0.009 (2) |
C24 | 0.0277 (14) | 0.0320 (15) | 0.0282 (13) | −0.0013 (11) | 0.0074 (11) | 0.0018 (11) |
C25 | 0.0315 (14) | 0.0209 (13) | 0.0336 (14) | −0.0021 (11) | 0.0120 (12) | −0.0022 (11) |
C26 | 0.0320 (16) | 0.0363 (17) | 0.086 (3) | 0.0001 (13) | 0.0293 (17) | 0.0104 (17) |
C27 | 0.0317 (15) | 0.0366 (16) | 0.0323 (14) | −0.0011 (12) | 0.0101 (11) | 0.0030 (12) |
C28 | 0.0277 (13) | 0.0230 (13) | 0.0246 (12) | −0.0002 (10) | 0.0108 (10) | −0.0016 (10) |
C29 | 0.0274 (13) | 0.0260 (14) | 0.0281 (13) | 0.0003 (11) | 0.0052 (10) | 0.0002 (11) |
C30 | 0.0229 (13) | 0.0285 (14) | 0.0417 (15) | 0.0022 (11) | 0.0120 (11) | 0.0050 (12) |
C31 | 0.0243 (14) | 0.0305 (15) | 0.0378 (15) | −0.0025 (11) | 0.0069 (11) | 0.0025 (12) |
C32 | 0.0230 (13) | 0.0232 (13) | 0.0244 (12) | −0.0013 (10) | 0.0074 (10) | −0.0011 (10) |
C33 | 0.0260 (13) | 0.0234 (13) | 0.0233 (12) | −0.0005 (10) | 0.0081 (10) | −0.0010 (10) |
C34 | 0.0388 (16) | 0.0254 (14) | 0.0365 (15) | 0.0021 (11) | 0.0196 (12) | 0.0026 (11) |
C35 | 0.0369 (15) | 0.0248 (13) | 0.0244 (13) | 0.0020 (11) | 0.0116 (11) | −0.0007 (10) |
C36 | 0.0267 (14) | 0.0234 (13) | 0.0311 (13) | −0.0014 (10) | 0.0071 (11) | −0.0011 (11) |
C37 | 0.0258 (14) | 0.0266 (13) | 0.0276 (13) | 0.0014 (11) | 0.0040 (11) | −0.0007 (11) |
C38 | 0.0266 (12) | 0.0241 (12) | 0.0197 (11) | −0.0013 (10) | 0.0082 (9) | 0.0005 (10) |
C39 | 0.0268 (13) | 0.0220 (13) | 0.0236 (12) | −0.0002 (10) | 0.0073 (10) | 0.0001 (10) |
C40 | 0.0270 (13) | 0.0233 (13) | 0.0229 (12) | 0.0009 (10) | 0.0099 (10) | 0.0029 (10) |
C41 | 0.0352 (15) | 0.0220 (13) | 0.0315 (14) | 0.0007 (11) | 0.0175 (12) | 0.0006 (11) |
C42 | 0.0322 (14) | 0.0214 (13) | 0.0356 (14) | −0.0049 (11) | 0.0146 (12) | −0.0027 (11) |
C43 | 0.0291 (14) | 0.0266 (14) | 0.0292 (13) | −0.0038 (11) | 0.0077 (11) | −0.0018 (11) |
C44 | 0.0273 (13) | 0.0224 (13) | 0.0264 (13) | 0.0012 (10) | 0.0091 (11) | 0.0043 (11) |
C45 | 0.0448 (19) | 0.0350 (17) | 0.076 (2) | −0.0101 (14) | 0.0304 (17) | −0.0003 (17) |
C46 | 0.0270 (14) | 0.0278 (14) | 0.0312 (14) | 0.0003 (11) | 0.0021 (11) | 0.0004 (11) |
C47 | 0.0505 (18) | 0.0291 (16) | 0.0444 (17) | 0.0009 (13) | 0.0138 (15) | 0.0058 (13) |
C48 | 0.058 (2) | 0.0430 (18) | 0.0540 (19) | 0.0066 (15) | 0.0342 (17) | 0.0039 (15) |
C49 | 0.074 (3) | 0.074 (3) | 0.061 (2) | 0.031 (2) | 0.040 (2) | 0.004 (2) |
C50 | 0.105 (4) | 0.067 (3) | 0.109 (4) | 0.002 (2) | 0.085 (3) | 0.001 (3) |
C51 | 0.0358 (15) | 0.0291 (14) | 0.0280 (13) | 0.0005 (11) | 0.0146 (12) | 0.0022 (11) |
C52 | 0.0288 (14) | 0.0263 (13) | 0.0244 (12) | 0.0014 (11) | 0.0067 (11) | 0.0014 (11) |
C53 | 0.0260 (14) | 0.0435 (18) | 0.0485 (17) | 0.0043 (12) | 0.0152 (13) | 0.0054 (14) |
C54 | 0.0415 (16) | 0.0345 (15) | 0.0256 (13) | 0.0070 (12) | 0.0117 (12) | 0.0049 (12) |
Geometric parameters (Å, º) top
O1—C17 | 1.205 (3) | C24—H24A | 0.9800 |
O2—C17 | 1.348 (3) | C24—H24B | 0.9800 |
O2—C18 | 1.444 (4) | C24—H24C | 0.9800 |
O3—C19 | 1.203 (4) | C26—H26A | 0.9800 |
O4—C19 | 1.344 (3) | C26—H26B | 0.9800 |
O4—C20 | 1.442 (4) | C26—H26C | 0.9800 |
O5—C25 | 1.201 (3) | C27—H27A | 0.9800 |
O6—C25 | 1.342 (3) | C27—H27B | 0.9800 |
O6—C26 | 1.452 (4) | C27—H27C | 0.9800 |
O7—C44 | 1.195 (3) | C28—C44 | 1.512 (4) |
O8—C44 | 1.344 (3) | C28—C29 | 1.559 (3) |
O8—C45 | 1.445 (4) | C28—C33 | 1.569 (3) |
O9—C46 | 1.206 (3) | C28—H28 | 1.0000 |
O10—C46 | 1.345 (3) | C29—C46 | 1.508 (4) |
O10—C47 | 1.440 (4) | C29—C30 | 1.539 (4) |
O11—C52 | 1.208 (3) | C29—H29 | 1.0000 |
O12—C52 | 1.338 (3) | C30—C34 | 1.511 (4) |
O12—C53 | 1.448 (3) | C30—C31 | 1.549 (4) |
C1—C17 | 1.506 (4) | C30—H30 | 1.0000 |
C1—C2 | 1.562 (3) | C31—C32 | 1.551 (4) |
C1—C6 | 1.573 (3) | C31—H31A | 0.9900 |
C1—H1 | 1.0000 | C31—H31B | 0.9900 |
C2—C19 | 1.512 (4) | C32—C39 | 1.566 (3) |
C2—C3 | 1.544 (4) | C32—C33 | 1.570 (3) |
C2—H2 | 1.0000 | C32—H32 | 1.0000 |
C3—C7 | 1.510 (3) | C33—C35 | 1.504 (4) |
C3—C4 | 1.542 (4) | C33—C36 | 1.532 (4) |
C3—H3 | 1.0000 | C34—C35 | 1.328 (4) |
C4—C5 | 1.552 (3) | C34—C48 | 1.524 (4) |
C4—H4A | 0.9900 | C35—H35 | 0.9500 |
C4—H4B | 0.9900 | C36—C37 | 1.525 (4) |
C5—C6 | 1.562 (3) | C36—H36A | 0.9900 |
C5—C12 | 1.563 (4) | C36—H36B | 0.9900 |
C5—H5 | 1.0000 | C37—C38 | 1.527 (4) |
C6—C8 | 1.506 (3) | C37—H37A | 0.9900 |
C6—C9 | 1.531 (3) | C37—H37B | 0.9900 |
C7—C8 | 1.330 (3) | C38—C39 | 1.548 (4) |
C7—C21 | 1.512 (4) | C38—C40 | 1.558 (4) |
C8—H8 | 0.9500 | C38—H38 | 1.0000 |
C9—C10 | 1.525 (4) | C39—C43 | 1.535 (4) |
C9—H9A | 0.9900 | C39—C51 | 1.539 (3) |
C9—H9B | 0.9900 | C40—C52 | 1.532 (3) |
C10—C11 | 1.530 (3) | C40—C54 | 1.543 (3) |
C10—H10A | 0.9900 | C40—C41 | 1.544 (4) |
C10—H10B | 0.9900 | C41—C42 | 1.520 (4) |
C11—C13 | 1.556 (4) | C41—H41A | 0.9900 |
C11—C12 | 1.557 (3) | C41—H41B | 0.9900 |
C11—H11 | 1.0000 | C42—C43 | 1.524 (4) |
C12—C16 | 1.536 (4) | C42—H42A | 0.9900 |
C12—C24 | 1.543 (4) | C42—H42B | 0.9900 |
C13—C25 | 1.536 (4) | C43—H43A | 0.9900 |
C13—C27 | 1.543 (4) | C43—H43B | 0.9900 |
C13—C14 | 1.547 (4) | C45—H45A | 0.9800 |
C14—C15 | 1.519 (4) | C45—H45B | 0.9800 |
C14—H14A | 0.9900 | C45—H45C | 0.9800 |
C14—H14B | 0.9900 | C47—H47A | 0.9800 |
C15—C16 | 1.526 (4) | C47—H47B | 0.9800 |
C15—H15A | 0.9900 | C47—H47C | 0.9800 |
C15—H15B | 0.9900 | C48—C50 | 1.485 (5) |
C16—H16A | 0.9900 | C48—C49 | 1.520 (5) |
C16—H16B | 0.9900 | C48—H48 | 1.0000 |
C18—H18A | 0.9800 | C49—H49A | 0.9800 |
C18—H18B | 0.9800 | C49—H49B | 0.9800 |
C18—H18C | 0.9800 | C49—H49C | 0.9800 |
C20—H20A | 0.9800 | C50—H50A | 0.9800 |
C20—H20B | 0.9800 | C50—H50B | 0.9800 |
C20—H20C | 0.9800 | C50—H50C | 0.9800 |
C21—C23 | 1.518 (5) | C51—H51A | 0.9800 |
C21—C22 | 1.524 (4) | C51—H51B | 0.9800 |
C21—H21 | 1.0000 | C51—H51C | 0.9800 |
C22—H22A | 0.9800 | C53—H53A | 0.9800 |
C22—H22B | 0.9800 | C53—H53B | 0.9800 |
C22—H22C | 0.9800 | C53—H53C | 0.9800 |
C23—H23A | 0.9800 | C54—H54A | 0.9800 |
C23—H23B | 0.9800 | C54—H54B | 0.9800 |
C23—H23C | 0.9800 | C54—H54C | 0.9800 |
| | | |
C17—O2—C18 | 116.1 (2) | C13—C27—H27C | 109.5 |
C19—O4—C20 | 115.3 (2) | H27A—C27—H27C | 109.5 |
C25—O6—C26 | 114.9 (2) | H27B—C27—H27C | 109.5 |
C44—O8—C45 | 115.0 (2) | C44—C28—C29 | 113.2 (2) |
C46—O10—C47 | 116.1 (2) | C44—C28—C33 | 110.4 (2) |
C52—O12—C53 | 115.7 (2) | C29—C28—C33 | 108.41 (19) |
C17—C1—C2 | 113.9 (2) | C44—C28—H28 | 108.2 |
C17—C1—C6 | 109.72 (19) | C29—C28—H28 | 108.2 |
C2—C1—C6 | 108.96 (19) | C33—C28—H28 | 108.2 |
C17—C1—H1 | 108.0 | C46—C29—C30 | 115.0 (2) |
C2—C1—H1 | 108.0 | C46—C29—C28 | 113.9 (2) |
C6—C1—H1 | 108.0 | C30—C29—C28 | 110.1 (2) |
C19—C2—C3 | 112.1 (2) | C46—C29—H29 | 105.6 |
C19—C2—C1 | 115.3 (2) | C30—C29—H29 | 105.6 |
C3—C2—C1 | 109.2 (2) | C28—C29—H29 | 105.6 |
C19—C2—H2 | 106.5 | C34—C30—C29 | 111.3 (2) |
C3—C2—H2 | 106.5 | C34—C30—C31 | 107.8 (2) |
C1—C2—H2 | 106.5 | C29—C30—C31 | 105.2 (2) |
C7—C3—C4 | 109.8 (2) | C34—C30—H30 | 110.8 |
C7—C3—C2 | 108.3 (2) | C29—C30—H30 | 110.8 |
C4—C3—C2 | 107.1 (2) | C31—C30—H30 | 110.8 |
C7—C3—H3 | 110.5 | C30—C31—C32 | 109.7 (2) |
C4—C3—H3 | 110.5 | C30—C31—H31A | 109.7 |
C2—C3—H3 | 110.5 | C32—C31—H31A | 109.7 |
C3—C4—C5 | 110.1 (2) | C30—C31—H31B | 109.7 |
C3—C4—H4A | 109.6 | C32—C31—H31B | 109.7 |
C5—C4—H4A | 109.6 | H31A—C31—H31B | 108.2 |
C3—C4—H4B | 109.6 | C31—C32—C39 | 114.5 (2) |
C5—C4—H4B | 109.6 | C31—C32—C33 | 109.0 (2) |
H4A—C4—H4B | 108.1 | C39—C32—C33 | 114.8 (2) |
C4—C5—C6 | 108.6 (2) | C31—C32—H32 | 106.0 |
C4—C5—C12 | 114.6 (2) | C39—C32—H32 | 106.0 |
C6—C5—C12 | 115.46 (19) | C33—C32—H32 | 106.0 |
C4—C5—H5 | 105.8 | C35—C33—C36 | 113.1 (2) |
C6—C5—H5 | 105.8 | C35—C33—C28 | 107.8 (2) |
C12—C5—H5 | 105.8 | C36—C33—C28 | 109.6 (2) |
C8—C6—C9 | 113.0 (2) | C35—C33—C32 | 108.8 (2) |
C8—C6—C5 | 109.9 (2) | C36—C33—C32 | 112.1 (2) |
C9—C6—C5 | 112.0 (2) | C28—C33—C32 | 105.05 (19) |
C8—C6—C1 | 106.8 (2) | C35—C34—C30 | 112.6 (2) |
C9—C6—C1 | 109.6 (2) | C35—C34—C48 | 122.5 (3) |
C5—C6—C1 | 105.09 (19) | C30—C34—C48 | 124.4 (3) |
C8—C7—C3 | 112.4 (2) | C34—C35—C33 | 116.7 (2) |
C8—C7—C21 | 127.2 (2) | C34—C35—H35 | 121.6 |
C3—C7—C21 | 120.4 (2) | C33—C35—H35 | 121.6 |
C7—C8—C6 | 116.7 (2) | C37—C36—C33 | 113.4 (2) |
C7—C8—H8 | 121.7 | C37—C36—H36A | 108.9 |
C6—C8—H8 | 121.7 | C33—C36—H36A | 108.9 |
C10—C9—C6 | 113.0 (2) | C37—C36—H36B | 108.9 |
C10—C9—H9A | 109.0 | C33—C36—H36B | 108.9 |
C6—C9—H9A | 109.0 | H36A—C36—H36B | 107.7 |
C10—C9—H9B | 109.0 | C36—C37—C38 | 109.8 (2) |
C6—C9—H9B | 109.0 | C36—C37—H37A | 109.7 |
H9A—C9—H9B | 107.8 | C38—C37—H37A | 109.7 |
C9—C10—C11 | 109.5 (2) | C36—C37—H37B | 109.7 |
C9—C10—H10A | 109.8 | C38—C37—H37B | 109.7 |
C11—C10—H10A | 109.8 | H37A—C37—H37B | 108.2 |
C9—C10—H10B | 109.8 | C37—C38—C39 | 110.7 (2) |
C11—C10—H10B | 109.8 | C37—C38—C40 | 114.0 (2) |
H10A—C10—H10B | 108.2 | C39—C38—C40 | 116.4 (2) |
C10—C11—C13 | 114.2 (2) | C37—C38—H38 | 104.8 |
C10—C11—C12 | 110.5 (2) | C39—C38—H38 | 104.8 |
C13—C11—C12 | 116.7 (2) | C40—C38—H38 | 104.8 |
C10—C11—H11 | 104.7 | C43—C39—C51 | 108.3 (2) |
C13—C11—H11 | 104.7 | C43—C39—C38 | 109.3 (2) |
C12—C11—H11 | 104.7 | C51—C39—C38 | 113.8 (2) |
C16—C12—C24 | 108.9 (2) | C43—C39—C32 | 107.73 (19) |
C16—C12—C11 | 108.7 (2) | C51—C39—C32 | 111.5 (2) |
C24—C12—C11 | 113.9 (2) | C38—C39—C32 | 106.1 (2) |
C16—C12—C5 | 108.01 (19) | C52—C40—C54 | 107.8 (2) |
C24—C12—C5 | 111.7 (2) | C52—C40—C41 | 105.1 (2) |
C11—C12—C5 | 105.5 (2) | C54—C40—C41 | 110.7 (2) |
C25—C13—C27 | 108.8 (2) | C52—C40—C38 | 108.3 (2) |
C25—C13—C14 | 105.9 (2) | C54—C40—C38 | 114.1 (2) |
C27—C13—C14 | 110.2 (2) | C41—C40—C38 | 110.3 (2) |
C25—C13—C11 | 106.5 (2) | C42—C41—C40 | 113.5 (2) |
C27—C13—C11 | 114.9 (2) | C42—C41—H41A | 108.9 |
C14—C13—C11 | 110.1 (2) | C40—C41—H41A | 108.9 |
C15—C14—C13 | 113.0 (2) | C42—C41—H41B | 108.9 |
C15—C14—H14A | 109.0 | C40—C41—H41B | 108.9 |
C13—C14—H14A | 109.0 | H41A—C41—H41B | 107.7 |
C15—C14—H14B | 109.0 | C41—C42—C43 | 110.8 (2) |
C13—C14—H14B | 109.0 | C41—C42—H42A | 109.5 |
H14A—C14—H14B | 107.8 | C43—C42—H42A | 109.5 |
C14—C15—C16 | 111.0 (2) | C41—C42—H42B | 109.5 |
C14—C15—H15A | 109.4 | C43—C42—H42B | 109.5 |
C16—C15—H15A | 109.4 | H42A—C42—H42B | 108.1 |
C14—C15—H15B | 109.4 | C42—C43—C39 | 112.5 (2) |
C16—C15—H15B | 109.4 | C42—C43—H43A | 109.1 |
H15A—C15—H15B | 108.0 | C39—C43—H43A | 109.1 |
C15—C16—C12 | 113.0 (2) | C42—C43—H43B | 109.1 |
C15—C16—H16A | 109.0 | C39—C43—H43B | 109.1 |
C12—C16—H16A | 109.0 | H43A—C43—H43B | 107.8 |
C15—C16—H16B | 109.0 | O7—C44—O8 | 123.3 (2) |
C12—C16—H16B | 109.0 | O7—C44—C28 | 126.2 (2) |
H16A—C16—H16B | 107.8 | O8—C44—C28 | 110.6 (2) |
O1—C17—O2 | 122.8 (2) | O8—C45—H45A | 109.5 |
O1—C17—C1 | 126.4 (2) | O8—C45—H45B | 109.5 |
O2—C17—C1 | 110.8 (2) | H45A—C45—H45B | 109.5 |
O2—C18—H18A | 109.5 | O8—C45—H45C | 109.5 |
O2—C18—H18B | 109.5 | H45A—C45—H45C | 109.5 |
H18A—C18—H18B | 109.5 | H45B—C45—H45C | 109.5 |
O2—C18—H18C | 109.5 | O9—C46—O10 | 123.3 (3) |
H18A—C18—H18C | 109.5 | O9—C46—C29 | 126.8 (3) |
H18B—C18—H18C | 109.5 | O10—C46—C29 | 109.7 (2) |
O3—C19—O4 | 123.2 (3) | O10—C47—H47A | 109.5 |
O3—C19—C2 | 126.3 (3) | O10—C47—H47B | 109.5 |
O4—C19—C2 | 110.3 (2) | H47A—C47—H47B | 109.5 |
O4—C20—H20A | 109.5 | O10—C47—H47C | 109.5 |
O4—C20—H20B | 109.5 | H47A—C47—H47C | 109.5 |
H20A—C20—H20B | 109.5 | H47B—C47—H47C | 109.5 |
O4—C20—H20C | 109.5 | C50—C48—C49 | 111.8 (3) |
H20A—C20—H20C | 109.5 | C50—C48—C34 | 110.9 (3) |
H20B—C20—H20C | 109.5 | C49—C48—C34 | 114.1 (3) |
C7—C21—C23 | 110.9 (3) | C50—C48—H48 | 106.5 |
C7—C21—C22 | 112.2 (2) | C49—C48—H48 | 106.5 |
C23—C21—C22 | 110.9 (3) | C34—C48—H48 | 106.5 |
C7—C21—H21 | 107.5 | C48—C49—H49A | 109.5 |
C23—C21—H21 | 107.5 | C48—C49—H49B | 109.5 |
C22—C21—H21 | 107.5 | H49A—C49—H49B | 109.5 |
C21—C22—H22A | 109.5 | C48—C49—H49C | 109.5 |
C21—C22—H22B | 109.5 | H49A—C49—H49C | 109.5 |
H22A—C22—H22B | 109.5 | H49B—C49—H49C | 109.5 |
C21—C22—H22C | 109.5 | C48—C50—H50A | 109.5 |
H22A—C22—H22C | 109.5 | C48—C50—H50B | 109.5 |
H22B—C22—H22C | 109.5 | H50A—C50—H50B | 109.5 |
C21—C23—H23A | 109.5 | C48—C50—H50C | 109.5 |
C21—C23—H23B | 109.5 | H50A—C50—H50C | 109.5 |
H23A—C23—H23B | 109.5 | H50B—C50—H50C | 109.5 |
C21—C23—H23C | 109.5 | C39—C51—H51A | 109.5 |
H23A—C23—H23C | 109.5 | C39—C51—H51B | 109.5 |
H23B—C23—H23C | 109.5 | H51A—C51—H51B | 109.5 |
C12—C24—H24A | 109.5 | C39—C51—H51C | 109.5 |
C12—C24—H24B | 109.5 | H51A—C51—H51C | 109.5 |
H24A—C24—H24B | 109.5 | H51B—C51—H51C | 109.5 |
C12—C24—H24C | 109.5 | O11—C52—O12 | 122.3 (2) |
H24A—C24—H24C | 109.5 | O11—C52—C40 | 126.6 (2) |
H24B—C24—H24C | 109.5 | O12—C52—C40 | 111.1 (2) |
O5—C25—O6 | 121.8 (2) | O12—C53—H53A | 109.5 |
O5—C25—C13 | 126.4 (2) | O12—C53—H53B | 109.5 |
O6—C25—C13 | 111.8 (2) | H53A—C53—H53B | 109.5 |
O6—C26—H26A | 109.5 | O12—C53—H53C | 109.5 |
O6—C26—H26B | 109.5 | H53A—C53—H53C | 109.5 |
H26A—C26—H26B | 109.5 | H53B—C53—H53C | 109.5 |
O6—C26—H26C | 109.5 | C40—C54—H54A | 109.5 |
H26A—C26—H26C | 109.5 | C40—C54—H54B | 109.5 |
H26B—C26—H26C | 109.5 | H54A—C54—H54B | 109.5 |
C13—C27—H27A | 109.5 | C40—C54—H54C | 109.5 |
C13—C27—H27B | 109.5 | H54A—C54—H54C | 109.5 |
H27A—C27—H27B | 109.5 | H54B—C54—H54C | 109.5 |
| | | |
C17—C1—C2—C19 | 4.1 (3) | C44—C28—C29—C46 | 12.3 (3) |
C6—C1—C2—C19 | 126.9 (2) | C33—C28—C29—C46 | 135.1 (2) |
C17—C1—C2—C3 | −123.2 (2) | C44—C28—C29—C30 | −118.7 (2) |
C6—C1—C2—C3 | −0.4 (3) | C33—C28—C29—C30 | 4.1 (3) |
C19—C2—C3—C7 | −72.5 (3) | C46—C29—C30—C34 | −79.4 (3) |
C1—C2—C3—C7 | 56.6 (3) | C28—C29—C30—C34 | 51.0 (3) |
C19—C2—C3—C4 | 169.2 (2) | C46—C29—C30—C31 | 164.2 (2) |
C1—C2—C3—C4 | −61.7 (3) | C28—C29—C30—C31 | −65.4 (3) |
C7—C3—C4—C5 | −56.5 (3) | C34—C30—C31—C32 | −58.2 (3) |
C2—C3—C4—C5 | 60.8 (3) | C29—C30—C31—C32 | 60.5 (3) |
C3—C4—C5—C6 | 2.7 (3) | C30—C31—C32—C39 | 133.9 (2) |
C3—C4—C5—C12 | 133.4 (2) | C30—C31—C32—C33 | 3.8 (3) |
C4—C5—C6—C8 | 50.6 (3) | C44—C28—C33—C35 | 68.5 (3) |
C12—C5—C6—C8 | −79.6 (2) | C29—C28—C33—C35 | −56.0 (3) |
C4—C5—C6—C9 | 177.0 (2) | C44—C28—C33—C36 | −55.0 (3) |
C12—C5—C6—C9 | 46.8 (3) | C29—C28—C33—C36 | −179.5 (2) |
C4—C5—C6—C1 | −64.0 (2) | C44—C28—C33—C32 | −175.57 (19) |
C12—C5—C6—C1 | 165.7 (2) | C29—C28—C33—C32 | 59.9 (2) |
C17—C1—C6—C8 | 71.4 (2) | C31—C32—C33—C35 | 50.4 (3) |
C2—C1—C6—C8 | −53.9 (2) | C39—C32—C33—C35 | −79.4 (3) |
C17—C1—C6—C9 | −51.3 (3) | C31—C32—C33—C36 | 176.3 (2) |
C2—C1—C6—C9 | −176.6 (2) | C39—C32—C33—C36 | 46.5 (3) |
C17—C1—C6—C5 | −171.8 (2) | C31—C32—C33—C28 | −64.8 (2) |
C2—C1—C6—C5 | 62.9 (2) | C39—C32—C33—C28 | 165.38 (19) |
C4—C3—C7—C8 | 57.1 (3) | C29—C30—C34—C35 | −55.4 (3) |
C2—C3—C7—C8 | −59.4 (3) | C31—C30—C34—C35 | 59.4 (3) |
C4—C3—C7—C21 | −124.6 (3) | C29—C30—C34—C48 | 131.6 (3) |
C2—C3—C7—C21 | 118.8 (3) | C31—C30—C34—C48 | −113.6 (3) |
C3—C7—C8—C6 | 0.1 (3) | C30—C34—C35—C33 | −1.2 (3) |
C21—C7—C8—C6 | −178.0 (2) | C48—C34—C35—C33 | 172.0 (3) |
C9—C6—C8—C7 | 178.3 (2) | C36—C33—C35—C34 | 179.2 (2) |
C5—C6—C8—C7 | −55.8 (3) | C28—C33—C35—C34 | 58.0 (3) |
C1—C6—C8—C7 | 57.7 (3) | C32—C33—C35—C34 | −55.5 (3) |
C8—C6—C9—C10 | 78.3 (3) | C35—C33—C36—C37 | 77.6 (3) |
C5—C6—C9—C10 | −46.4 (3) | C28—C33—C36—C37 | −162.1 (2) |
C1—C6—C9—C10 | −162.7 (2) | C32—C33—C36—C37 | −45.9 (3) |
C6—C9—C10—C11 | 56.3 (3) | C33—C36—C37—C38 | 55.3 (3) |
C9—C10—C11—C13 | 160.4 (2) | C36—C37—C38—C39 | −64.9 (3) |
C9—C10—C11—C12 | −65.8 (3) | C36—C37—C38—C40 | 161.5 (2) |
C10—C11—C12—C16 | 178.1 (2) | C37—C38—C39—C43 | 178.4 (2) |
C13—C11—C12—C16 | −49.3 (3) | C40—C38—C39—C43 | −49.2 (3) |
C10—C11—C12—C24 | −60.3 (3) | C37—C38—C39—C51 | −60.4 (3) |
C13—C11—C12—C24 | 72.3 (3) | C40—C38—C39—C51 | 71.9 (3) |
C10—C11—C12—C5 | 62.5 (2) | C37—C38—C39—C32 | 62.5 (2) |
C13—C11—C12—C5 | −164.9 (2) | C40—C38—C39—C32 | −165.1 (2) |
C4—C5—C12—C16 | 63.2 (3) | C31—C32—C39—C43 | 62.4 (3) |
C6—C5—C12—C16 | −169.6 (2) | C33—C32—C39—C43 | −170.5 (2) |
C4—C5—C12—C24 | −56.6 (3) | C31—C32—C39—C51 | −56.3 (3) |
C6—C5—C12—C24 | 70.7 (3) | C33—C32—C39—C51 | 70.8 (3) |
C4—C5—C12—C11 | 179.3 (2) | C31—C32—C39—C38 | 179.3 (2) |
C6—C5—C12—C11 | −53.5 (3) | C33—C32—C39—C38 | −53.6 (3) |
C10—C11—C13—C25 | −67.1 (3) | C37—C38—C40—C52 | −68.1 (3) |
C12—C11—C13—C25 | 162.0 (2) | C39—C38—C40—C52 | 161.1 (2) |
C10—C11—C13—C27 | 53.4 (3) | C37—C38—C40—C54 | 52.0 (3) |
C12—C11—C13—C27 | −77.5 (3) | C39—C38—C40—C54 | −78.9 (3) |
C10—C11—C13—C14 | 178.5 (2) | C37—C38—C40—C41 | 177.3 (2) |
C12—C11—C13—C14 | 47.6 (3) | C39—C38—C40—C41 | 46.5 (3) |
C25—C13—C14—C15 | −164.7 (2) | C52—C40—C41—C42 | −165.6 (2) |
C27—C13—C14—C15 | 77.8 (3) | C54—C40—C41—C42 | 78.3 (3) |
C11—C13—C14—C15 | −49.9 (3) | C38—C40—C41—C42 | −49.0 (3) |
C13—C14—C15—C16 | 56.6 (3) | C40—C41—C42—C43 | 56.3 (3) |
C14—C15—C16—C12 | −59.2 (3) | C41—C42—C43—C39 | −59.3 (3) |
C24—C12—C16—C15 | −70.7 (3) | C51—C39—C43—C42 | −69.9 (3) |
C11—C12—C16—C15 | 53.8 (3) | C38—C39—C43—C42 | 54.5 (3) |
C5—C12—C16—C15 | 167.8 (2) | C32—C39—C43—C42 | 169.4 (2) |
C18—O2—C17—O1 | 0.8 (4) | C45—O8—C44—O7 | −3.1 (4) |
C18—O2—C17—C1 | −176.6 (2) | C45—O8—C44—C28 | 177.5 (2) |
C2—C1—C17—O1 | 52.0 (3) | C29—C28—C44—O7 | 49.6 (3) |
C6—C1—C17—O1 | −70.4 (3) | C33—C28—C44—O7 | −72.1 (3) |
C2—C1—C17—O2 | −130.7 (2) | C29—C28—C44—O8 | −131.0 (2) |
C6—C1—C17—O2 | 106.9 (2) | C33—C28—C44—O8 | 107.3 (2) |
C20—O4—C19—O3 | 0.4 (4) | C47—O10—C46—O9 | 6.2 (4) |
C20—O4—C19—C2 | 175.7 (2) | C47—O10—C46—C29 | −178.8 (2) |
C3—C2—C19—O3 | 1.4 (4) | C30—C29—C46—O9 | −4.5 (4) |
C1—C2—C19—O3 | −124.5 (3) | C28—C29—C46—O9 | −133.0 (3) |
C3—C2—C19—O4 | −173.8 (2) | C30—C29—C46—O10 | −179.2 (2) |
C1—C2—C19—O4 | 60.4 (3) | C28—C29—C46—O10 | 52.2 (3) |
C8—C7—C21—C23 | −98.9 (3) | C35—C34—C48—C50 | −96.5 (4) |
C3—C7—C21—C23 | 83.1 (3) | C30—C34—C48—C50 | 75.9 (4) |
C8—C7—C21—C22 | 25.8 (4) | C35—C34—C48—C49 | 136.2 (3) |
C3—C7—C21—C22 | −152.2 (3) | C30—C34—C48—C49 | −51.5 (4) |
C26—O6—C25—O5 | −0.1 (4) | C53—O12—C52—O11 | −3.5 (4) |
C26—O6—C25—C13 | 177.5 (3) | C53—O12—C52—C40 | 174.3 (2) |
C27—C13—C25—O5 | −132.4 (3) | C54—C40—C52—O11 | −130.0 (3) |
C14—C13—C25—O5 | 109.2 (3) | C41—C40—C52—O11 | 111.8 (3) |
C11—C13—C25—O5 | −8.0 (4) | C38—C40—C52—O11 | −6.2 (4) |
C27—C13—C25—O6 | 50.2 (3) | C54—C40—C52—O12 | 52.3 (3) |
C14—C13—C25—O6 | −68.2 (3) | C41—C40—C52—O12 | −65.8 (3) |
C11—C13—C25—O6 | 174.5 (2) | C38—C40—C52—O12 | 176.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O11i | 1.00 | 2.47 | 3.357 (3) | 147 |
C18—H18C···O3ii | 0.98 | 2.56 | 3.377 (4) | 141 |
C26—H26C···O1iii | 0.98 | 2.51 | 3.389 (4) | 149 |
C29—H29···O5 | 1.00 | 2.49 | 3.386 (3) | 150 |
C53—H53C···O9iv | 0.98 | 2.60 | 3.513 (4) | 156 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y−1/2, −z+2. |