The conformation of (-)-membrenone-C, (2S,2'R,3S,3'S)-(1S)-2,2'-ethane-1,1-diylbis(6-ethyl-3,5-dimethyl-2,3-dihydro-4H-pyran-4-one), C20H30O4, in the solid state is found to be the same as that predicted in solution by 1H NMR spectroscopy and nOe (nuclear Overhauser effect) correlations.
Supporting information
CCDC reference: 227782
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.079
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C4 = 5.08 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11
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 27.70
From the CIF: _reflns_number_total 2294
Count of symmetry unique reflns 2463
Completeness (_total/calc) 93.14%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999) and Xtal3.7 ADDREF SORTRF (Hall et al., 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: Xtal3.7 CRYLSQ; molecular graphics: Xtal3.7; software used to prepare material for publication: Xtal3.7 BONDLA CIFIO.
(2
S,2'
R,3
S,3'
S)-(1
S)-2,2'-ethane-1,1-diylbis(6-ethyl-3,5-dimethyl-2,3-dihydro- 4
H-pyran-4-one)
top
Crystal data top
C20H30O4 | F(000) = 728 |
Mr = 334.46 | Dx = 1.201 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: p_2ac_2ab | Cell parameters from 3123 reflections |
a = 9.836 (3) Å | θ = 2.6–25.1° |
b = 13.065 (4) Å | µ = 0.08 mm−1 |
c = 14.391 (4) Å | T = 123 K |
V = 1849.3 (10) Å3 | Needle, colourless |
Z = 4 | 0.75 × 0.12 × 0.11 mm |
Data collection top
Bruker P4 CCD area-detector diffractometer | 1648 reflections with F2 > 2σ(F2) |
Radiation source: sealed tube | Rint = 0.07 |
Graphite monochromator | θmax = 27.7° |
ω scans | h = −12→12 |
12757 measured reflections | k = −16→17 |
2294 independent reflections | l = −18→6 |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.02Fo2)2]1/2 |
wR(F2) = 0.079 | (Δ/σ)max = 0.0003 |
S = 1.20 | Δρmax = 0.26 e Å−3 |
2177 reflections | Δρmin = −0.33 e Å−3 |
217 parameters | |
Special details top
Experimental. A 1 mm diameter collimator was used. |
Refinement. Refinement of F2 against reflections with F2>0. 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 > 2σ(F2) is used only for calculating
R-factors(gt) etc. and is not relevant to the choice of
reflections for refinement Friedel related data were averaged because an
attempt to refine a Flack parameter was unsuccessful. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7737 (3) | 0.97960 (17) | 0.70830 (14) | 0.0241 (13) | |
C2 | 0.7805 (3) | 1.08753 (18) | 0.66693 (14) | 0.0229 (13) | |
C2' | 0.7483 (3) | 0.89901 (17) | 0.63256 (14) | 0.0226 (13) | |
C3 | 0.7927 (2) | 1.17478 (18) | 0.73629 (14) | 0.0248 (14) | |
C3' | 0.6243 (3) | 0.91530 (17) | 0.57182 (13) | 0.0221 (13) | |
C4 | 0.8026 (3) | 1.2748 (2) | 0.68225 (15) | 0.0255 (14) | |
C4' | 0.6040 (3) | 0.82316 (19) | 0.50883 (14) | 0.0260 (14) | |
C5 | 0.8773 (3) | 1.26960 (18) | 0.59387 (14) | 0.0239 (14) | |
C5' | 0.6524 (3) | 0.72541 (19) | 0.54290 (14) | 0.0252 (14) | |
C6 | 0.9264 (2) | 1.17911 (19) | 0.56446 (13) | 0.0244 (14) | |
C6' | 0.7073 (3) | 0.71902 (19) | 0.62872 (15) | 0.0247 (14) | |
C7 | 0.6755 (3) | 1.1768 (2) | 0.80563 (15) | 0.0348 (16) | |
C7' | 0.4931 (3) | 0.93527 (19) | 0.62545 (15) | 0.0306 (15) | |
C8 | 0.9024 (3) | 1.36845 (18) | 0.54250 (16) | 0.0349 (16) | |
C8' | 0.6251 (3) | 0.63131 (19) | 0.48516 (16) | 0.0360 (16) | |
C9 | 1.0178 (3) | 1.16186 (19) | 0.48291 (15) | 0.0300 (15) | |
C9' | 0.7450 (3) | 0.62110 (17) | 0.67683 (15) | 0.0305 (15) | |
C10 | 0.9428 (3) | 1.1174 (2) | 0.39987 (16) | 0.0407 (17) | |
C10' | 0.7649 (3) | 0.62845 (18) | 0.78042 (17) | 0.0388 (16) | |
C11 | 0.8992 (3) | 0.95350 (18) | 0.76603 (15) | 0.0315 (15) | |
O1 | 0.89603 (17) | 1.08727 (12) | 0.60472 (9) | 0.0239 (9) | |
O1' | 0.73589 (17) | 0.80256 (11) | 0.68176 (9) | 0.0246 (9) | |
O4 | 0.7559 (2) | 1.35533 (12) | 0.71207 (11) | 0.0355 (11) | |
O4' | 0.54170 (18) | 0.83307 (14) | 0.43506 (10) | 0.0369 (11) | |
H2 | 0.69634 | 1.10126 | 0.63704 | 0.02900* | |
H2' | 0.82189 | 0.90175 | 0.58980 | 0.02900* | |
H3 | 0.87252 | 1.16517 | 0.77258 | 0.03200* | |
H3' | 0.64284 | 0.97538 | 0.53690 | 0.02800* | |
H7a | 0.68755 | 1.23257 | 0.84726 | 0.05200* | |
H7b | 0.67375 | 1.11461 | 0.83928 | 0.05200* | |
H7c | 0.59224 | 1.18522 | 0.77289 | 0.05200* | |
H7'a | 0.42032 | 0.94509 | 0.58291 | 0.04600* | |
H7'b | 0.50349 | 0.99545 | 0.66228 | 0.04600* | |
H7'c | 0.47368 | 0.87888 | 0.66462 | 0.04600* | |
H9a | 1.08761 | 1.11532 | 0.50063 | 0.03700* | |
H9b | 1.05719 | 1.22521 | 0.46548 | 0.03700* | |
H9'a | 0.82733 | 0.59700 | 0.65037 | 0.03800* | |
H9'b | 0.67459 | 0.57270 | 0.66575 | 0.03800* | |
H10a | 1.00447 | 1.10793 | 0.34993 | 0.06200* | |
H10b | 0.87291 | 1.16360 | 0.38124 | 0.06200* | |
H10c | 0.90333 | 1.05371 | 0.41639 | 0.06200* | |
H10'a | 0.78858 | 0.56316 | 0.80435 | 0.05900* | |
H10'b | 0.68328 | 0.65144 | 0.80868 | 0.05900* | |
H10'c | 0.83602 | 0.67575 | 0.79330 | 0.05900* | |
H1 | 0.69787 | 0.97880 | 0.74954 | 0.03000* | |
H11a | 0.89020 | 0.88609 | 0.79014 | 0.04800* | |
H11b | 0.90722 | 1.00071 | 0.81578 | 0.04800* | |
H11c | 0.97757 | 0.95717 | 0.72777 | 0.04800* | |
H8a | 0.86329 | 1.36752 | 0.48239 | 0.05300* | |
H8b | 0.99815 | 1.38100 | 0.53693 | 0.05300* | |
H8c | 0.86381 | 1.42533 | 0.57655 | 0.05300* | |
H8'a | 0.69304 | 0.57924 | 0.49619 | 0.05200* | |
H8'b | 0.62681 | 0.64629 | 0.41960 | 0.05200* | |
H8'c | 0.53836 | 0.60220 | 0.49937 | 0.05200* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0325 (16) | 0.0227 (13) | 0.0170 (11) | −0.0013 (12) | −0.0022 (11) | 0.0019 (10) |
C2 | 0.0226 (15) | 0.0225 (13) | 0.0234 (12) | 0.0007 (12) | 0.0019 (11) | 0.0026 (10) |
C2' | 0.0284 (15) | 0.0186 (13) | 0.0209 (11) | −0.0030 (12) | 0.0020 (11) | 0.0036 (10) |
C3 | 0.0300 (15) | 0.0244 (14) | 0.0200 (11) | −0.0009 (12) | −0.0008 (10) | −0.0015 (11) |
C3' | 0.0281 (15) | 0.0175 (13) | 0.0207 (11) | −0.0034 (12) | −0.0005 (11) | 0.0070 (10) |
C4 | 0.0250 (16) | 0.0250 (15) | 0.0265 (12) | −0.0020 (12) | −0.0063 (11) | 0.0001 (11) |
C4' | 0.0250 (15) | 0.0309 (15) | 0.0222 (12) | −0.0059 (13) | 0.0023 (11) | −0.0000 (11) |
C5 | 0.0296 (15) | 0.0209 (14) | 0.0213 (11) | −0.0014 (12) | −0.0069 (11) | 0.0020 (10) |
C5' | 0.0274 (16) | 0.0235 (15) | 0.0247 (12) | −0.0045 (12) | 0.0006 (11) | −0.0042 (11) |
C6 | 0.0240 (14) | 0.0284 (15) | 0.0208 (12) | −0.0048 (13) | −0.0037 (10) | 0.0024 (11) |
C6' | 0.0234 (15) | 0.0225 (14) | 0.0282 (13) | −0.0031 (12) | 0.0045 (10) | 0.0005 (11) |
C7 | 0.0431 (18) | 0.0277 (15) | 0.0335 (14) | 0.0001 (13) | 0.0107 (12) | −0.0012 (13) |
C7' | 0.0302 (16) | 0.0316 (16) | 0.0300 (13) | 0.0005 (13) | −0.0028 (12) | 0.0034 (12) |
C8 | 0.0457 (19) | 0.0313 (17) | 0.0276 (13) | −0.0063 (14) | −0.0015 (13) | 0.0007 (11) |
C8' | 0.0419 (19) | 0.0326 (17) | 0.0335 (14) | −0.0065 (14) | −0.0008 (13) | −0.0094 (11) |
C9 | 0.0360 (17) | 0.0291 (15) | 0.0250 (12) | −0.0074 (13) | 0.0046 (11) | −0.0016 (11) |
C9' | 0.0342 (17) | 0.0225 (14) | 0.0347 (13) | −0.0014 (13) | 0.0035 (13) | 0.0025 (11) |
C10 | 0.055 (2) | 0.0424 (18) | 0.0251 (12) | −0.0006 (15) | 0.0001 (13) | −0.0043 (12) |
C10' | 0.055 (2) | 0.0273 (15) | 0.0340 (13) | 0.0028 (15) | −0.0055 (14) | 0.0092 (11) |
C11 | 0.0410 (18) | 0.0259 (15) | 0.0277 (13) | −0.0002 (13) | −0.0092 (13) | 0.0021 (11) |
O1 | 0.0302 (11) | 0.0203 (9) | 0.0213 (8) | 0.0006 (8) | 0.0043 (7) | 0.0018 (7) |
O1' | 0.0355 (11) | 0.0177 (9) | 0.0207 (8) | −0.0001 (8) | −0.0021 (7) | 0.0022 (6) |
O4 | 0.0465 (12) | 0.0196 (10) | 0.0402 (10) | 0.0049 (10) | 0.0059 (10) | −0.0036 (8) |
O4' | 0.0452 (12) | 0.0415 (11) | 0.0239 (9) | −0.0006 (10) | −0.0091 (8) | −0.0004 (8) |
Geometric parameters (Å, º) top
C2—C3 | 1.520 (3) | C7—H7c | 0.951 |
C2—C1 | 1.532 (3) | C7'—H7'a | 0.951 |
C2—O1 | 1.447 (3) | C7'—H7'b | 0.954 |
C2—H2 | 0.950 | C7'—H7'c | 0.947 |
C2'—C3' | 1.516 (3) | C8—H8a | 0.947 |
C2'—C1 | 1.536 (3) | C8—H8b | 0.959 |
C2'—O1' | 1.451 (3) | C8—H8c | 0.968 |
C2'—H2' | 0.950 | C8'—H8'a | 0.967 |
C3—C4 | 1.524 (3) | C8'—H8'b | 0.964 |
C3—C7 | 1.525 (3) | C8'—H8'c | 0.956 |
C3—H3 | 0.952 | C9—C10 | 1.520 (3) |
C3'—C4' | 1.520 (3) | C9—H9a | 0.952 |
C3'—C7' | 1.527 (4) | C9—H9b | 0.948 |
C3'—H3' | 0.950 | C9'—C10' | 1.507 (3) |
C4—C5 | 1.470 (3) | C9'—H9'a | 0.948 |
C4—O4 | 1.226 (3) | C9'—H9'b | 0.952 |
C4'—C5' | 1.448 (3) | C10—H10a | 0.948 |
C4'—O4' | 1.233 (3) | C10—H10b | 0.954 |
C5—C6 | 1.346 (3) | C10—H10c | 0.948 |
C5—C8 | 1.508 (3) | C10'—H10'a | 0.949 |
C5'—C6' | 1.351 (3) | C10'—H10'b | 0.949 |
C5'—C8' | 1.508 (3) | C10'—H10'c | 0.952 |
C6—C9 | 1.495 (3) | C1—C11 | 1.527 (4) |
C6—O1 | 1.366 (3) | C1—H1 | 0.953 |
C6'—C9' | 1.501 (3) | C11—H11a | 0.951 |
C6'—O1' | 1.361 (3) | C11—H11b | 0.948 |
C7—H7a | 0.951 | C11—H11c | 0.948 |
C7—H7b | 0.946 | | |
| | | |
C3—C2—C1 | 116.01 (17) | H7'a—C7'—H7'c | 109.7 |
C3—C2—O1 | 110.25 (19) | H7'b—C7'—H7'c | 109.4 |
C3—C2—H2 | 103.0 | C5—C8—H8a | 111.7 |
C1—C2—O1 | 105.81 (18) | C5—C8—H8b | 110.4 |
C1—C2—H2 | 108.2 | C5—C8—H8c | 110.2 |
O1—C2—H2 | 113.87 | H8a—C8—H8b | 109.0 |
C3'—C2'—C1 | 116.3 (2) | H8a—C8—H8c | 108.2 |
C3'—C2'—O1' | 109.6 (2) | H8b—C8—H8c | 107.2 |
C3'—C2'—H2' | 103.53 | C5'—C8'—H8'a | 111.1 |
C1—C2'—O1' | 105.24 (16) | C5'—C8'—H8'b | 111.8 |
C1—C2'—H2' | 108.1 | C5'—C8'—H8'c | 111.4 |
O1'—C2'—H2' | 114.4 | H8'a—C8'—H8'b | 107.0 |
C2—C3—C4 | 108.24 (17) | H8'a—C8'—H8'c | 107.6 |
C2—C3—C7 | 112.5 (2) | H8'b—C8'—H8'c | 107.8 |
C2—C3—H3 | 109.1 | C6—C9—C10 | 112.5 (2) |
C4—C3—C7 | 111.6 (2) | C6—C9—H9a | 108.6 |
C4—C3—H3 | 109.9 | C6—C9—H9b | 108.8 |
C7—C3—H3 | 105.49 | C10—C9—H9a | 108.4 |
C2'—C3'—C4' | 109.8 (2) | C10—C9—H9b | 108.9 |
C2'—C3'—C7' | 114.40 (17) | H9a—C9—H9b | 109.5 |
C2'—C3'—H3' | 105.5 | C6'—C9'—C10' | 115.7 (2) |
C4'—C3'—C7' | 109.0 (2) | C6'—C9'—H9'a | 108.0 |
C4'—C3'—H3' | 111.36 | C6'—C9'—H9'b | 108.0 |
C7'—C3'—H3' | 106.8 | C10'—C9'—H9'a | 107.9 |
C3—C4—C5 | 115.7 (2) | C10'—C9'—H9'b | 107.6 |
C3—C4—O4 | 122.2 (2) | H9'a—C9'—H9'b | 109.5 |
C5—C4—O4 | 122.0 (2) | C9—C10—H10a | 109.6 |
C3'—C4'—C5' | 116.95 (18) | C9—C10—H10b | 109.2 |
C3'—C4'—O4' | 119.7 (2) | C9—C10—H10c | 109.7 |
C5'—C4'—O4' | 123.2 (2) | H10a—C10—H10b | 109.3 |
C4—C5—C6 | 119.5 (2) | H10a—C10—H10c | 109.8 |
C4—C5—C8 | 117.8 (2) | H10b—C10—H10c | 109.3 |
C6—C5—C8 | 122.6 (2) | C9'—C10'—H10'a | 109.5 |
C4'—C5'—C6' | 119.7 (2) | C9'—C10'—H10'b | 109.5 |
C4'—C5'—C8' | 118.3 (2) | C9'—C10'—H10'c | 109.2 |
C6'—C5'—C8' | 121.6 (2) | H10'a—C10'—H10'b | 109.7 |
C5—C6—C9 | 126.5 (2) | H10'a—C10'—H10'c | 109.4 |
C5—C6—O1 | 124.0 (2) | H10'b—C10'—H10'c | 109.4 |
C9—C6—O1 | 109.4 (2) | C2—C1—C2' | 111.24 (17) |
C5'—C6'—C9' | 125.0 (2) | C2—C1—C11 | 112.4 (2) |
C5'—C6'—O1' | 123.1 (2) | C2—C1—H1 | 106.6 |
C9'—C6'—O1' | 111.95 (18) | C2'—C1—C11 | 111.4 (2) |
C3—C7—H7a | 109.3 | C2'—C1—H1 | 107.9 |
C3—C7—H7b | 109.5 | C11—C1—H1 | 106.95 |
C3—C7—H7c | 109.2 | C1—C11—H11a | 109.3 |
H7a—C7—H7b | 109.8 | C1—C11—H11b | 109.4 |
H7a—C7—H7c | 109.3 | C1—C11—H11c | 109.3 |
H7b—C7—H7c | 109.7 | H11a—C11—H11b | 109.6 |
C3'—C7'—H7'a | 109.5 | H11a—C11—H11c | 109.6 |
C3'—C7'—H7'b | 109.3 | H11b—C11—H11c | 109.8 |
C3'—C7'—H7'c | 109.8 | C2—O1—C6 | 115.63 (17) |
H7'a—C7'—H7'b | 109.1 | C2'—O1'—C6' | 116.12 (16) |
| | | |
C1—C2—C3—C4 | 178.2 (2) | C3—C4—C5—C6 | 2.6 (3) |
C1—C2—C3—C7 | −58.0 (3) | C3—C4—C5—C8 | −173.9 (2) |
C1—C2—C3—H3 | 58.6 | O4—C4—C5—C6 | 180.0 (2) |
O1—C2—C3—C4 | 58.0 (2) | O4—C4—C5—C8 | 3.5 (4) |
O1—C2—C3—C7 | −178.26 (18) | C3'—C4'—C5'—C6' | 2.6 (3) |
O1—C2—C3—H3 | −61.6 | C3'—C4'—C5'—C8' | 175.8 (2) |
H2—C2—C3—C4 | −63.9 | O4'—C4'—C5'—C6' | −173.1 (2) |
H2—C2—C3—C7 | 59.9 | O4'—C4'—C5'—C8' | 0.0 (4) |
H2—C2—C3—H3 | 176.6 | C4—C5—C6—C9 | −172.3 (2) |
C3—C2—C1—C2' | 174.8 (2) | C4—C5—C6—O1 | 9.5 (4) |
C3—C2—C1—C11 | −59.5 (3) | C8—C5—C6—C9 | 4.0 (4) |
C3—C2—C1—H1 | 57.4 | C8—C5—C6—O1 | −174.2 (2) |
O1—C2—C1—C2' | −62.7 (2) | C4—C5—C8—H8a | −120.4 |
O1—C2—C1—C11 | 63.0 (2) | C4—C5—C8—H8b | 118.2 |
O1—C2—C1—H1 | 179.94 | C4—C5—C8—H8c | −0.0 |
H2—C2—C1—C2' | 59.7 | C6—C5—C8—H8a | 63.3 |
H2—C2—C1—C11 | −174.58 | C6—C5—C8—H8b | −58.1 |
H2—C2—C1—H1 | −57.7 | C6—C5—C8—H8c | −176.4 |
C3—C2—O1—C6 | −49.7 (2) | C4'—C5'—C6'—C9' | 171.9 (2) |
C1—C2—O1—C6 | −175.86 (17) | C4'—C5'—C6'—O1' | −8.6 (4) |
H2—C2—O1—C6 | 65.5 | C8'—C5'—C6'—C9' | −1.0 (4) |
C1—C2'—C3'—C4' | −173.15 (19) | C8'—C5'—C6'—O1' | 178.6 (2) |
C1—C2'—C3'—C7' | −50.2 (3) | C4'—C5'—C8'—H8'a | 153.1 |
C1—C2'—C3'—H3' | 66.8 | C4'—C5'—C8'—H8'b | 33.7 |
O1'—C2'—C3'—C4' | −54.0 (2) | C4'—C5'—C8'—H8'c | −87.0 |
O1'—C2'—C3'—C7' | 68.9 (2) | C6'—C5'—C8'—H8'a | −33.9 |
O1'—C2'—C3'—H3' | −174.05 | C6'—C5'—C8'—H8'b | −153.3 |
H2'—C2'—C3'—C4' | 68.5 | C6'—C5'—C8'—H8'c | 86.0 |
H2'—C2'—C3'—C7' | −168.6 | C5—C6—C9—C10 | −104.1 (3) |
H2'—C2'—C3'—H3' | −51.6 | C5—C6—C9—H9a | 135.8 |
C3'—C2'—C1—C2 | −55.0 (3) | C5—C6—C9—H9b | 16.7 |
C3'—C2'—C1—C11 | 178.7 (2) | O1—C6—C9—C10 | 74.3 (2) |
C3'—C2'—C1—H1 | 61.6 | O1—C6—C9—H9a | −45.8 |
O1'—C2'—C1—C2 | −176.5 (2) | O1—C6—C9—H9b | −164.9 |
O1'—C2'—C1—C11 | 57.2 (2) | C5—C6—O1—C2 | 15.2 (3) |
O1'—C2'—C1—H1 | −59.9 | C9—C6—O1—C2 | −163.29 (18) |
H2'—C2'—C1—C2 | 60.8 | C5'—C6'—C9'—C10' | −162.5 (3) |
H2'—C2'—C1—C11 | −65.4 | C5'—C6'—C9'—H9'a | 76.5 |
H2'—C2'—C1—H1 | 177.5 | C5'—C6'—C9'—H9'b | −41.8 |
C3'—C2'—O1'—C6' | 51.7 (2) | O1'—C6'—C9'—C10' | 18.0 (3) |
C1—C2'—O1'—C6' | 177.5 (2) | O1'—C6'—C9'—H9'a | −103.1 |
H2'—C2'—O1'—C6' | −64.1 | O1'—C6'—C9'—H9'b | 138.6 |
C2—C3—C4—C5 | −35.2 (3) | C5'—C6'—O1'—C2' | −20.1 (3) |
C2—C3—C4—O4 | 147.5 (2) | C9'—C6'—O1'—C2' | 159.5 (2) |
C7—C3—C4—C5 | −159.5 (2) | C6—C9—C10—H10a | 179.8 |
C7—C3—C4—O4 | 23.1 (3) | C6—C9—C10—H10b | 60.2 |
H3—C3—C4—C5 | 83.8 | C6—C9—C10—H10c | −59.6 |
H3—C3—C4—O4 | −93.5 | H9a—C9—C10—H10a | −60.0 |
C2—C3—C7—H7a | −179.9 | H9a—C9—C10—H10b | −179.7 |
C2—C3—C7—H7b | 59.9 | H9a—C9—C10—H10c | 60.6 |
C2—C3—C7—H7c | −60.3 | H9b—C9—C10—H10a | 59.1 |
C4—C3—C7—H7a | −58.0 | H9b—C9—C10—H10b | −60.6 |
C4—C3—C7—H7b | −178.2 | H9b—C9—C10—H10c | 179.7 |
C4—C3—C7—H7c | 61.6 | C6'—C9'—C10'—H10'a | −179.8 |
H3—C3—C7—H7a | 61.3 | C6'—C9'—C10'—H10'b | 59.8 |
H3—C3—C7—H7b | −58.9 | C6'—C9'—C10'—H10'c | −60.0 |
H3—C3—C7—H7c | −179.1 | H9'a—C9'—C10'—H10'a | −58.8 |
C2'—C3'—C4'—C5' | 28.5 (3) | H9'a—C9'—C10'—H10'b | −179.1 |
C2'—C3'—C4'—O4' | −155.5 (2) | H9'a—C9'—C10'—H10'c | 61.0 |
C7'—C3'—C4'—C5' | −97.5 (2) | H9'b—C9'—C10'—H10'a | 59.3 |
C7'—C3'—C4'—O4' | 78.4 (3) | H9'b—C9'—C10'—H10'b | −61.0 |
H3'—C3'—C4'—C5' | 145.0 | H9'b—C9'—C10'—H10'c | 179.1 |
H3'—C3'—C4'—O4' | −39.1 | C2—C1—C11—H11a | 179.9 |
C2'—C3'—C7'—H7'a | 179.7 | C2—C1—C11—H11b | 60.0 |
C2'—C3'—C7'—H7'b | 60.1 | C2—C1—C11—H11c | −60.2 |
C2'—C3'—C7'—H7'c | −59.9 | C2'—C1—C11—H11a | −54.4 |
C4'—C3'—C7'—H7'a | −57.0 | C2'—C1—C11—H11b | −174.4 |
C4'—C3'—C7'—H7'b | −176.5 | C2'—C1—C11—H11c | 65.4 |
C4'—C3'—C7'—H7'c | 63.4 | H1—C1—C11—H11a | 63.2 |
H3'—C3'—C7'—H7'a | 63.4 | H1—C1—C11—H11b | −56.7 |
H3'—C3'—C7'—H7'b | −56.1 | H1—C1—C11—H11c | −176.9 |
H3'—C3'—C7'—H7'c | −176.2 | | |