The absolute configuration of the title compound, C
38H
44O
8, and in particular of its chiral cyclophane moiety, was determined by reference to the internal standard, (1
S)-camphanoate. Molecules are associated into columns parallel to the
b axis by a series of C—H
O interactions.
Supporting information
CCDC reference: 202987
Key indicators
- Single-crystal X-ray study
- T = 178 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.095
- Data-to-parameter ratio = 9.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
DIFF_012 Alert A _diffrn_reflns_av_R_equivalents is missing
R factor for symmetry-equivalent intensities.
The following tests will not be performed
RINTA
PLAT_728 Alert A D-H..A Calc 166.66, Rep 1667.00, Dev. 1500.34 Deg.
C9 -H9A -O30 1.555 1.555 1.455
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _reflns_number_total 4034
Count of symmetry unique reflns 3728
Completeness (_total/calc) 108.21%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 306
Fraction of Friedel pairs measured 0.082
Are heavy atom types Z>Si present no
ALERT: MoKa measured Friedel data cannot be used to
determine absolute structure in a light-atom
study EXCEPT under VERY special conditions.
It is preferred that Friedel data is merged in such cases.
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
(
S)-4,16-Dihydroxymethyl-[2.2]paracyclophane bis-(1
S)-camphanoate
top
Crystal data top
C38H44O8 | Z = 1 |
Mr = 628.73 | F(000) = 336 |
Triclinic, P1 | Dx = 1.292 Mg m−3 |
a = 6.740 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.295 (3) Å | Cell parameters from 49 reflections |
c = 11.647 (3) Å | θ = 10–11.5° |
α = 67.18 (2)° | µ = 0.09 mm−1 |
β = 81.59 (2)° | T = 178 K |
γ = 85.49 (2)° | Prism, colourless |
V = 808.2 (4) Å3 | 0.70 × 0.35 × 0.20 mm |
Data collection top
Nicolet R3 diffractometer | θmax = 27.5°, θmin = 3.1° |
Radiation source: fine-focus sealed tube | h = −8→0 |
Graphite monochromator | k = −14→14 |
ωn scans | l = −15→14 |
4034 measured reflections | 3 standard reflections every 147 reflections |
4034 independent reflections | intensity decay: none |
3519 reflections with I > 2σ(I) | |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.1873P] where P = (Fo2 + 2Fc2)/3 |
4034 reflections | (Δ/σ)max < 0.001 |
421 parameters | Δρmax = 0.19 e Å−3 |
453 restraints | Δρmin = −0.22 e Å−3 |
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 | |
C1 | 0.5265 (5) | 0.9990 (3) | 0.3334 (3) | 0.0424 (7) | |
H1A | 0.6293 | 0.9729 | 0.2772 | 0.051* | |
H1B | 0.5610 | 1.0851 | 0.3270 | 0.051* | |
C2 | 0.3163 (4) | 1.0089 (2) | 0.2861 (2) | 0.0360 (6) | |
H2A | 0.2761 | 1.1006 | 0.2469 | 0.043* | |
H2B | 0.3286 | 0.9719 | 0.2208 | 0.043* | |
C3 | 0.1544 (4) | 0.9398 (2) | 0.3904 (2) | 0.0258 (5) | |
C4 | 0.0925 (3) | 0.8158 (2) | 0.4130 (2) | 0.0242 (4) | |
C5 | 0.0213 (3) | 0.7341 (2) | 0.5351 (2) | 0.0241 (4) | |
H5 | −0.0170 | 0.6497 | 0.5502 | 0.029* | |
C6 | 0.0056 (3) | 0.7745 (2) | 0.6352 (2) | 0.0287 (5) | |
C7 | 0.0185 (4) | 0.9056 (2) | 0.6046 (2) | 0.0302 (5) | |
H7 | −0.0244 | 0.9401 | 0.6669 | 0.036* | |
C8 | 0.0926 (4) | 0.9865 (2) | 0.4851 (2) | 0.0305 (5) | |
H8 | 0.1019 | 1.0756 | 0.4669 | 0.037* | |
C9 | 0.0097 (4) | 0.6810 (3) | 0.7692 (2) | 0.0367 (6) | |
H9A | −0.0346 | 0.5963 | 0.7771 | 0.044* | |
H9B | −0.0871 | 0.7113 | 0.8250 | 0.044* | |
C10 | 0.2261 (5) | 0.6637 (3) | 0.8150 (2) | 0.0388 (6) | |
H10A | 0.2206 | 0.6975 | 0.8821 | 0.047* | |
H10B | 0.2619 | 0.5710 | 0.8511 | 0.047* | |
C11 | 0.3881 (4) | 0.7324 (2) | 0.7091 (2) | 0.0298 (5) | |
C12 | 0.4381 (4) | 0.8573 (2) | 0.6881 (2) | 0.0339 (5) | |
H12 | 0.4224 | 0.8846 | 0.7565 | 0.041* | |
C13 | 0.5105 (4) | 0.9426 (2) | 0.5687 (3) | 0.0355 (6) | |
H13 | 0.5432 | 1.0273 | 0.5563 | 0.043* | |
C14 | 0.5352 (4) | 0.9045 (2) | 0.4677 (2) | 0.0318 (5) | |
C15 | 0.5296 (3) | 0.7732 (2) | 0.4950 (2) | 0.0280 (5) | |
H15 | 0.5765 | 0.7418 | 0.4309 | 0.034* | |
C16 | 0.4573 (3) | 0.6874 (2) | 0.6137 (2) | 0.0260 (5) | |
C17 | 0.1057 (4) | 0.7661 (2) | 0.3094 (2) | 0.0287 (5) | |
H17A | −0.0041 | 0.7057 | 0.3272 | 0.034* | |
H17B | 0.0906 | 0.8385 | 0.2288 | 0.034* | |
O17 | 0.3001 (3) | 0.70012 (15) | 0.29985 (15) | 0.0292 (4) | |
C18 | 0.4348 (4) | 0.5498 (2) | 0.6300 (2) | 0.0312 (5) | |
H18A | 0.3100 | 0.5145 | 0.6857 | 0.037* | |
H18B | 0.4292 | 0.5442 | 0.5477 | 0.037* | |
O18 | 0.6117 (3) | 0.47748 (15) | 0.68636 (15) | 0.0308 (4) | |
C19 | 0.3429 (4) | 0.6714 (2) | 0.1981 (2) | 0.0280 (5) | |
O19 | 0.2371 (3) | 0.69805 (19) | 0.11642 (17) | 0.0426 (5) | |
C20 | 0.5391 (4) | 0.5977 (2) | 0.1960 (2) | 0.0251 (4) | |
O20 | 0.6523 (3) | 0.59661 (15) | 0.29415 (15) | 0.0295 (4) | |
C21 | 0.6824 (4) | 0.6478 (2) | 0.0727 (2) | 0.0324 (5) | |
H21A | 0.7473 | 0.7276 | 0.0623 | 0.039* | |
H21B | 0.6119 | 0.6638 | −0.0009 | 0.039* | |
C22 | 0.8361 (4) | 0.5346 (2) | 0.0924 (2) | 0.0326 (5) | |
H22A | 0.9722 | 0.5616 | 0.0928 | 0.039* | |
H22B | 0.8405 | 0.5001 | 0.0258 | 0.039* | |
C23 | 0.7561 (3) | 0.4330 (2) | 0.2231 (2) | 0.0255 (4) | |
C24 | 0.7848 (4) | 0.4952 (2) | 0.3137 (2) | 0.0281 (5) | |
O24 | 0.9019 (3) | 0.47038 (18) | 0.38927 (17) | 0.0361 (4) | |
C25 | 0.5244 (3) | 0.4519 (2) | 0.2238 (2) | 0.0244 (4) | |
C26 | 0.4405 (4) | 0.4232 (2) | 0.1227 (2) | 0.0331 (5) | |
H26A | 0.4442 | 0.3302 | 0.1443 | 0.040* | |
H26B | 0.5218 | 0.4654 | 0.0416 | 0.040* | |
H26C | 0.3016 | 0.4557 | 0.1174 | 0.040* | |
C27 | 0.4054 (4) | 0.3782 (2) | 0.3523 (2) | 0.0310 (5) | |
H27A | 0.2655 | 0.4092 | 0.3524 | 0.037* | |
H27B | 0.4642 | 0.3921 | 0.4180 | 0.037* | |
H27C | 0.4107 | 0.2862 | 0.3684 | 0.037* | |
C28 | 0.8493 (4) | 0.2998 (2) | 0.2557 (2) | 0.0334 (5) | |
H28A | 0.9943 | 0.3039 | 0.2544 | 0.040* | |
H28B | 0.8236 | 0.2652 | 0.1942 | 0.040* | |
H28C | 0.7904 | 0.2438 | 0.3397 | 0.040* | |
C29 | 0.6389 (4) | 0.3607 (2) | 0.6834 (2) | 0.0265 (5) | |
O29 | 0.5302 (3) | 0.31145 (16) | 0.64158 (16) | 0.0348 (4) | |
C30 | 0.8202 (4) | 0.2893 (2) | 0.7412 (2) | 0.0253 (4) | |
O30 | 0.9363 (3) | 0.36855 (15) | 0.77927 (17) | 0.0353 (4) | |
C31 | 0.9723 (4) | 0.2382 (3) | 0.6579 (2) | 0.0354 (6) | |
H31A | 1.0531 | 0.3082 | 0.5927 | 0.042* | |
H31B | 0.9047 | 0.1930 | 0.6172 | 0.042* | |
C32 | 1.1021 (4) | 0.1445 (2) | 0.7552 (2) | 0.0333 (5) | |
H32A | 1.2431 | 0.1721 | 0.7358 | 0.040* | |
H32B | 1.0987 | 0.0562 | 0.7573 | 0.040* | |
C33 | 1.0038 (4) | 0.1513 (2) | 0.8822 (2) | 0.0272 (5) | |
C34 | 1.0475 (4) | 0.2860 (2) | 0.8676 (2) | 0.0321 (5) | |
O34 | 1.1590 (3) | 0.32332 (19) | 0.9172 (2) | 0.0485 (5) | |
C35 | 0.7768 (3) | 0.1699 (2) | 0.8656 (2) | 0.0254 (4) | |
C36 | 0.6482 (4) | 0.2045 (3) | 0.9675 (2) | 0.0419 (6) | |
H36A | 0.5130 | 0.2302 | 0.9438 | 0.050* | |
H36B | 0.7083 | 0.2759 | 0.9771 | 0.050* | |
H36C | 0.6404 | 0.1298 | 1.0471 | 0.050* | |
C37 | 0.6854 (4) | 0.0579 (2) | 0.8514 (3) | 0.0382 (6) | |
H37A | 0.6858 | −0.0180 | 0.9297 | 0.046* | |
H37B | 0.7644 | 0.0390 | 0.7827 | 0.046* | |
H37C | 0.5471 | 0.0807 | 0.8327 | 0.046* | |
C38 | 1.0673 (4) | 0.0461 (3) | 0.9999 (3) | 0.0400 (6) | |
H38A | 1.2120 | 0.0498 | 0.9999 | 0.048* | |
H38B | 1.0353 | −0.0378 | 1.0017 | 0.048* | |
H38C | 0.9954 | 0.0583 | 1.0741 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0368 (14) | 0.0362 (14) | 0.0410 (14) | −0.0119 (12) | −0.0027 (12) | 0.0008 (11) |
C2 | 0.0408 (15) | 0.0293 (12) | 0.0300 (12) | −0.0043 (11) | −0.0053 (11) | −0.0017 (10) |
C3 | 0.0263 (11) | 0.0230 (10) | 0.0267 (11) | 0.0040 (9) | −0.0076 (9) | −0.0072 (8) |
C4 | 0.0209 (10) | 0.0267 (10) | 0.0264 (11) | 0.0050 (9) | −0.0047 (9) | −0.0120 (9) |
C5 | 0.0225 (11) | 0.0218 (10) | 0.0285 (11) | 0.0006 (8) | −0.0034 (9) | −0.0102 (9) |
C6 | 0.0203 (11) | 0.0370 (12) | 0.0299 (11) | −0.0003 (9) | 0.0019 (9) | −0.0157 (10) |
C7 | 0.0284 (12) | 0.0357 (12) | 0.0332 (12) | 0.0061 (10) | −0.0033 (10) | −0.0218 (10) |
C8 | 0.0318 (13) | 0.0232 (10) | 0.0393 (13) | 0.0039 (10) | −0.0097 (11) | −0.0140 (9) |
C9 | 0.0394 (14) | 0.0421 (14) | 0.0264 (12) | −0.0051 (12) | 0.0052 (11) | −0.0133 (10) |
C10 | 0.0498 (16) | 0.0412 (14) | 0.0228 (11) | −0.0002 (12) | −0.0049 (11) | −0.0095 (10) |
C11 | 0.0341 (13) | 0.0313 (12) | 0.0248 (11) | 0.0061 (10) | −0.0103 (10) | −0.0105 (9) |
C12 | 0.0371 (14) | 0.0355 (13) | 0.0363 (13) | 0.0070 (11) | −0.0111 (11) | −0.0207 (11) |
C13 | 0.0322 (13) | 0.0280 (12) | 0.0499 (15) | −0.0009 (10) | −0.0113 (12) | −0.0167 (11) |
C14 | 0.0235 (12) | 0.0325 (12) | 0.0338 (12) | −0.0051 (10) | −0.0023 (10) | −0.0064 (10) |
C15 | 0.0235 (11) | 0.0335 (12) | 0.0308 (12) | 0.0026 (9) | −0.0044 (9) | −0.0166 (10) |
C16 | 0.0256 (11) | 0.0235 (10) | 0.0310 (11) | 0.0057 (9) | −0.0109 (9) | −0.0112 (9) |
C17 | 0.0297 (12) | 0.0311 (11) | 0.0288 (11) | 0.0061 (10) | −0.0073 (10) | −0.0152 (9) |
O17 | 0.0314 (9) | 0.0337 (9) | 0.0254 (8) | 0.0098 (7) | −0.0074 (7) | −0.0152 (7) |
C18 | 0.0325 (13) | 0.0247 (11) | 0.0390 (13) | 0.0067 (10) | −0.0148 (11) | −0.0127 (10) |
O18 | 0.0337 (9) | 0.0242 (8) | 0.0361 (9) | 0.0076 (7) | −0.0142 (8) | −0.0114 (7) |
C19 | 0.0327 (12) | 0.0283 (11) | 0.0242 (10) | 0.0048 (9) | −0.0062 (9) | −0.0115 (9) |
O19 | 0.0480 (11) | 0.0551 (12) | 0.0352 (9) | 0.0209 (10) | −0.0187 (9) | −0.0280 (9) |
C20 | 0.0302 (12) | 0.0246 (10) | 0.0224 (10) | 0.0011 (9) | −0.0057 (9) | −0.0105 (8) |
O20 | 0.0298 (9) | 0.0314 (8) | 0.0320 (8) | 0.0038 (7) | −0.0092 (7) | −0.0162 (7) |
C21 | 0.0351 (13) | 0.0289 (11) | 0.0282 (11) | 0.0008 (10) | −0.0002 (10) | −0.0070 (9) |
C22 | 0.0312 (12) | 0.0328 (12) | 0.0296 (12) | −0.0011 (10) | 0.0058 (10) | −0.0106 (10) |
C23 | 0.0244 (11) | 0.0246 (10) | 0.0272 (11) | 0.0020 (9) | −0.0012 (9) | −0.0107 (9) |
C24 | 0.0255 (11) | 0.0280 (11) | 0.0296 (11) | −0.0011 (9) | −0.0016 (9) | −0.0102 (9) |
O24 | 0.0336 (9) | 0.0415 (10) | 0.0354 (9) | 0.0025 (8) | −0.0111 (8) | −0.0154 (8) |
C25 | 0.0247 (11) | 0.0244 (10) | 0.0252 (11) | 0.0016 (9) | −0.0023 (9) | −0.0112 (8) |
C26 | 0.0337 (13) | 0.0369 (13) | 0.0358 (12) | 0.0026 (11) | −0.0063 (11) | −0.0215 (11) |
C27 | 0.0283 (12) | 0.0316 (12) | 0.0301 (11) | −0.0035 (10) | 0.0017 (10) | −0.0099 (9) |
C28 | 0.0307 (13) | 0.0277 (11) | 0.0426 (14) | 0.0034 (10) | −0.0041 (11) | −0.0153 (10) |
C29 | 0.0316 (12) | 0.0211 (10) | 0.0252 (10) | 0.0014 (9) | −0.0054 (9) | −0.0070 (8) |
O29 | 0.0377 (10) | 0.0285 (8) | 0.0413 (10) | 0.0036 (7) | −0.0158 (8) | −0.0136 (8) |
C30 | 0.0282 (11) | 0.0210 (10) | 0.0267 (11) | 0.0014 (9) | −0.0068 (9) | −0.0085 (8) |
O30 | 0.0375 (10) | 0.0231 (8) | 0.0475 (10) | 0.0002 (7) | −0.0170 (8) | −0.0120 (7) |
C31 | 0.0299 (13) | 0.0453 (14) | 0.0283 (12) | 0.0051 (11) | −0.0011 (10) | −0.0132 (11) |
C32 | 0.0296 (12) | 0.0346 (12) | 0.0376 (13) | 0.0069 (10) | −0.0029 (10) | −0.0177 (10) |
C33 | 0.0283 (12) | 0.0224 (10) | 0.0298 (11) | 0.0033 (9) | −0.0078 (9) | −0.0079 (9) |
C34 | 0.0294 (12) | 0.0294 (12) | 0.0405 (13) | 0.0039 (10) | −0.0117 (11) | −0.0150 (10) |
O34 | 0.0480 (12) | 0.0417 (11) | 0.0691 (14) | 0.0060 (9) | −0.0308 (11) | −0.0288 (10) |
C35 | 0.0272 (11) | 0.0236 (10) | 0.0238 (10) | 0.0019 (9) | −0.0050 (9) | −0.0070 (8) |
C36 | 0.0374 (14) | 0.0552 (17) | 0.0305 (13) | 0.0071 (13) | −0.0028 (11) | −0.0155 (12) |
C37 | 0.0363 (14) | 0.0258 (12) | 0.0495 (15) | −0.0032 (11) | −0.0103 (12) | −0.0089 (11) |
C38 | 0.0417 (15) | 0.0345 (13) | 0.0378 (14) | 0.0070 (12) | −0.0164 (12) | −0.0049 (11) |
Geometric parameters (Å, º) top
C1—C14 | 1.520 (3) | C21—C22 | 1.548 (4) |
C1—C2 | 1.575 (4) | C21—H21A | 0.9900 |
C1—H1A | 0.9900 | C21—H21B | 0.9900 |
C1—H1B | 0.9900 | C22—C23 | 1.558 (3) |
C2—C3 | 1.512 (3) | C22—H22A | 0.9900 |
C2—H2A | 0.9900 | C22—H22B | 0.9900 |
C2—H2B | 0.9900 | C23—C28 | 1.510 (3) |
C3—C8 | 1.397 (3) | C23—C24 | 1.518 (3) |
C3—C4 | 1.407 (3) | C23—C25 | 1.559 (3) |
C4—C5 | 1.399 (3) | C24—O24 | 1.205 (3) |
C4—C17 | 1.505 (3) | C25—C26 | 1.526 (3) |
C5—C6 | 1.395 (3) | C25—C27 | 1.538 (3) |
C5—H5 | 0.9500 | C26—H26A | 0.9800 |
C6—C7 | 1.388 (3) | C26—H26B | 0.9800 |
C6—C9 | 1.511 (3) | C26—H26C | 0.9800 |
C7—C8 | 1.380 (4) | C27—H27A | 0.9800 |
C7—H7 | 0.9500 | C27—H27B | 0.9800 |
C8—H8 | 0.9500 | C27—H27C | 0.9800 |
C9—C10 | 1.598 (4) | C28—H28A | 0.9800 |
C9—H9A | 0.9900 | C28—H28B | 0.9800 |
C9—H9B | 0.9900 | C28—H28C | 0.9800 |
C10—C11 | 1.521 (4) | C29—O29 | 1.210 (3) |
C10—H10A | 0.9900 | C29—C30 | 1.504 (3) |
C10—H10B | 0.9900 | C30—O30 | 1.459 (3) |
C11—C12 | 1.394 (3) | C30—C31 | 1.541 (3) |
C11—C16 | 1.401 (3) | C30—C35 | 1.557 (3) |
C12—C13 | 1.392 (4) | O30—C34 | 1.364 (3) |
C12—H12 | 0.9500 | C31—C32 | 1.544 (3) |
C13—C14 | 1.386 (4) | C31—H31A | 0.9900 |
C13—H13 | 0.9500 | C31—H31B | 0.9900 |
C14—C15 | 1.392 (3) | C32—C33 | 1.558 (3) |
C15—C16 | 1.388 (3) | C32—H32A | 0.9900 |
C15—H15 | 0.9500 | C32—H32B | 0.9900 |
C16—C18 | 1.508 (3) | C33—C34 | 1.511 (3) |
C17—O17 | 1.467 (3) | C33—C38 | 1.517 (3) |
C17—H17A | 0.9900 | C33—C35 | 1.558 (3) |
C17—H17B | 0.9900 | C34—O34 | 1.201 (3) |
O17—C19 | 1.333 (3) | C35—C36 | 1.522 (3) |
C18—O18 | 1.477 (3) | C35—C37 | 1.524 (3) |
C18—H18A | 0.9900 | C36—H36A | 0.9800 |
C18—H18B | 0.9900 | C36—H36B | 0.9800 |
O18—C29 | 1.330 (3) | C36—H36C | 0.9800 |
C19—O19 | 1.202 (3) | C37—H37A | 0.9800 |
C19—C20 | 1.509 (3) | C37—H37B | 0.9800 |
C20—O20 | 1.460 (3) | C37—H37C | 0.9800 |
C20—C21 | 1.538 (3) | C38—H38A | 0.9800 |
C20—C25 | 1.559 (3) | C38—H38B | 0.9800 |
O20—C24 | 1.363 (3) | C38—H38C | 0.9800 |
| | | |
C14—C1—C2 | 114.1 (2) | C23—C22—H22A | 111.0 |
C14—C1—H1A | 108.7 | C21—C22—H22B | 111.0 |
C2—C1—H1A | 108.7 | C23—C22—H22B | 111.0 |
C14—C1—H1B | 108.7 | H22A—C22—H22B | 109.0 |
C2—C1—H1B | 108.7 | C28—C23—C24 | 113.9 (2) |
H1A—C1—H1B | 107.6 | C28—C23—C22 | 115.87 (19) |
C3—C2—C1 | 112.8 (2) | C24—C23—C22 | 103.53 (19) |
C3—C2—H2A | 109.0 | C28—C23—C25 | 119.6 (2) |
C1—C2—H2A | 109.0 | C24—C23—C25 | 99.17 (18) |
C3—C2—H2B | 109.0 | C22—C23—C25 | 102.27 (19) |
C1—C2—H2B | 109.0 | O24—C24—O20 | 121.6 (2) |
H2A—C2—H2B | 107.8 | O24—C24—C23 | 130.8 (2) |
C8—C3—C4 | 116.4 (2) | O20—C24—C23 | 107.52 (19) |
C8—C3—C2 | 119.1 (2) | C26—C25—C27 | 109.3 (2) |
C4—C3—C2 | 123.0 (2) | C26—C25—C23 | 114.97 (19) |
C5—C4—C3 | 119.8 (2) | C27—C25—C23 | 113.48 (19) |
C5—C4—C17 | 118.4 (2) | C26—C25—C20 | 114.46 (18) |
C3—C4—C17 | 121.8 (2) | C27—C25—C20 | 112.70 (18) |
C6—C5—C4 | 121.1 (2) | C23—C25—C20 | 91.09 (17) |
C6—C5—H5 | 119.4 | C25—C26—H26A | 109.5 |
C4—C5—H5 | 119.4 | C25—C26—H26B | 109.5 |
C7—C6—C5 | 116.6 (2) | H26A—C26—H26B | 109.5 |
C7—C6—C9 | 120.4 (2) | C25—C26—H26C | 109.5 |
C5—C6—C9 | 122.2 (2) | H26A—C26—H26C | 109.5 |
C8—C7—C6 | 121.0 (2) | H26B—C26—H26C | 109.5 |
C8—C7—H7 | 119.5 | C25—C27—H27A | 109.5 |
C6—C7—H7 | 119.5 | C25—C27—H27B | 109.5 |
C7—C8—C3 | 121.2 (2) | H27A—C27—H27B | 109.5 |
C7—C8—H8 | 119.4 | C25—C27—H27C | 109.5 |
C3—C8—H8 | 119.4 | H27A—C27—H27C | 109.5 |
C6—C9—C10 | 113.3 (2) | H27B—C27—H27C | 109.5 |
C6—C9—H9A | 108.9 | C23—C28—H28A | 109.5 |
C10—C9—H9A | 108.9 | C23—C28—H28B | 109.5 |
C6—C9—H9B | 108.9 | H28A—C28—H28B | 109.5 |
C10—C9—H9B | 108.9 | C23—C28—H28C | 109.5 |
H9A—C9—H9B | 107.7 | H28A—C28—H28C | 109.5 |
C11—C10—C9 | 112.5 (2) | H28B—C28—H28C | 109.5 |
C11—C10—H10A | 109.1 | O29—C29—O18 | 125.3 (2) |
C9—C10—H10A | 109.1 | O29—C29—C30 | 120.9 (2) |
C11—C10—H10B | 109.1 | O18—C29—C30 | 113.7 (2) |
C9—C10—H10B | 109.1 | O30—C30—C29 | 111.95 (18) |
H10A—C10—H10B | 107.8 | O30—C30—C31 | 105.2 (2) |
C12—C11—C16 | 116.8 (2) | C29—C30—C31 | 116.25 (19) |
C12—C11—C10 | 120.0 (2) | O30—C30—C35 | 102.18 (17) |
C16—C11—C10 | 121.6 (2) | C29—C30—C35 | 115.79 (19) |
C13—C12—C11 | 121.2 (2) | C31—C30—C35 | 104.00 (18) |
C13—C12—H12 | 119.4 | C34—O30—C30 | 106.50 (17) |
C11—C12—H12 | 119.4 | C30—C31—C32 | 101.49 (18) |
C14—C13—C12 | 120.3 (2) | C30—C31—H31A | 111.5 |
C14—C13—H13 | 119.8 | C32—C31—H31A | 111.5 |
C12—C13—H13 | 119.8 | C30—C31—H31B | 111.5 |
C13—C14—C15 | 117.0 (2) | C32—C31—H31B | 111.5 |
C13—C14—C1 | 122.5 (2) | H31A—C31—H31B | 109.3 |
C15—C14—C1 | 119.3 (2) | C31—C32—C33 | 104.00 (19) |
C16—C15—C14 | 121.5 (2) | C31—C32—H32A | 111.0 |
C16—C15—H15 | 119.2 | C33—C32—H32A | 111.0 |
C14—C15—H15 | 119.2 | C31—C32—H32B | 111.0 |
C15—C16—C11 | 119.9 (2) | C33—C32—H32B | 111.0 |
C15—C16—C18 | 117.5 (2) | H32A—C32—H32B | 109.0 |
C11—C16—C18 | 122.3 (2) | C34—C33—C38 | 114.7 (2) |
O17—C17—C4 | 109.78 (18) | C34—C33—C32 | 103.25 (19) |
O17—C17—H17A | 109.7 | C38—C33—C32 | 116.0 (2) |
C4—C17—H17A | 109.7 | C34—C33—C35 | 99.14 (18) |
O17—C17—H17B | 109.7 | C38—C33—C35 | 118.8 (2) |
C4—C17—H17B | 109.7 | C32—C33—C35 | 102.52 (19) |
H17A—C17—H17B | 108.2 | O34—C34—O30 | 122.0 (2) |
C19—O17—C17 | 115.01 (18) | O34—C34—C33 | 130.7 (2) |
O18—C18—C16 | 106.69 (19) | O30—C34—C33 | 107.3 (2) |
O18—C18—H18A | 110.4 | C36—C35—C37 | 109.7 (2) |
C16—C18—H18A | 110.4 | C36—C35—C30 | 112.1 (2) |
O18—C18—H18B | 110.4 | C37—C35—C30 | 114.73 (19) |
C16—C18—H18B | 110.4 | C36—C35—C33 | 113.5 (2) |
H18A—C18—H18B | 108.6 | C37—C35—C33 | 114.6 (2) |
C29—O18—C18 | 114.83 (18) | C30—C35—C33 | 91.31 (17) |
O19—C19—O17 | 124.7 (2) | C35—C36—H36A | 109.5 |
O19—C19—C20 | 122.3 (2) | C35—C36—H36B | 109.5 |
O17—C19—C20 | 112.93 (19) | H36A—C36—H36B | 109.5 |
O20—C20—C19 | 111.00 (18) | C35—C36—H36C | 109.5 |
O20—C20—C21 | 106.02 (19) | H36A—C36—H36C | 109.5 |
C19—C20—C21 | 115.87 (19) | H36B—C36—H36C | 109.5 |
O20—C20—C25 | 102.61 (16) | C35—C37—H37A | 109.5 |
C19—C20—C25 | 116.3 (2) | C35—C37—H37B | 109.5 |
C21—C20—C25 | 103.71 (18) | H37A—C37—H37B | 109.5 |
C24—O20—C20 | 106.11 (17) | C35—C37—H37C | 109.5 |
C20—C21—C22 | 101.45 (18) | H37A—C37—H37C | 109.5 |
C20—C21—H21A | 111.5 | H37B—C37—H37C | 109.5 |
C22—C21—H21A | 111.5 | C33—C38—H38A | 109.5 |
C20—C21—H21B | 111.5 | C33—C38—H38B | 109.5 |
C22—C21—H21B | 111.5 | H38A—C38—H38B | 109.5 |
H21A—C21—H21B | 109.3 | C33—C38—H38C | 109.5 |
C21—C22—C23 | 103.79 (18) | H38A—C38—H38C | 109.5 |
C21—C22—H22A | 111.0 | H38B—C38—H38C | 109.5 |
| | | |
C14—C1—C2—C3 | 9.9 (3) | C28—C23—C24—O20 | −164.18 (19) |
C1—C2—C3—C8 | 66.9 (3) | C22—C23—C24—O20 | 69.1 (2) |
C1—C2—C3—C4 | −98.9 (3) | C25—C23—C24—O20 | −36.0 (2) |
C8—C3—C4—C5 | −16.3 (3) | C28—C23—C25—C26 | −66.8 (3) |
C2—C3—C4—C5 | 149.8 (2) | C24—C23—C25—C26 | 168.89 (19) |
C8—C3—C4—C17 | 165.4 (2) | C22—C23—C25—C26 | 62.8 (2) |
C2—C3—C4—C17 | −28.5 (3) | C28—C23—C25—C27 | 60.0 (3) |
C3—C4—C5—C6 | 1.7 (3) | C24—C23—C25—C27 | −64.3 (2) |
C17—C4—C5—C6 | 180.0 (2) | C22—C23—C25—C27 | −170.39 (19) |
C4—C5—C6—C7 | 14.4 (3) | C28—C23—C25—C20 | 175.4 (2) |
C4—C5—C6—C9 | −155.5 (2) | C24—C23—C25—C20 | 51.13 (18) |
C5—C6—C7—C8 | −15.8 (4) | C22—C23—C25—C20 | −54.98 (19) |
C9—C6—C7—C8 | 154.3 (2) | O20—C20—C25—C26 | −170.92 (19) |
C6—C7—C8—C3 | 1.0 (4) | C19—C20—C25—C26 | 67.7 (3) |
C4—C3—C8—C7 | 15.2 (4) | C21—C20—C25—C26 | −60.7 (2) |
C2—C3—C8—C7 | −151.5 (2) | O20—C20—C25—C27 | 63.4 (2) |
C7—C6—C9—C10 | −72.6 (3) | C19—C20—C25—C27 | −58.0 (3) |
C5—C6—C9—C10 | 96.9 (3) | C21—C20—C25—C27 | 173.6 (2) |
C6—C9—C10—C11 | −7.1 (3) | O20—C20—C25—C23 | −52.72 (18) |
C9—C10—C11—C12 | 93.2 (3) | C19—C20—C25—C23 | −174.06 (19) |
C9—C10—C11—C16 | −71.8 (3) | C21—C20—C25—C23 | 57.5 (2) |
C16—C11—C12—C13 | 14.7 (4) | C18—O18—C29—O29 | −1.5 (3) |
C10—C11—C12—C13 | −151.0 (3) | C18—O18—C29—C30 | 179.89 (19) |
C11—C12—C13—C14 | −0.3 (4) | O29—C29—C30—O30 | 176.8 (2) |
C12—C13—C14—C15 | −14.3 (4) | O18—C29—C30—O30 | −4.5 (3) |
C12—C13—C14—C1 | 153.5 (3) | O29—C29—C30—C31 | 55.9 (3) |
C2—C1—C14—C13 | −97.1 (3) | O18—C29—C30—C31 | −125.4 (2) |
C2—C1—C14—C15 | 70.5 (3) | O29—C29—C30—C35 | −66.6 (3) |
C13—C14—C15—C16 | 14.6 (4) | O18—C29—C30—C35 | 112.0 (2) |
C1—C14—C15—C16 | −153.6 (2) | C29—C30—O30—C34 | 158.5 (2) |
C14—C15—C16—C11 | −0.1 (4) | C31—C30—O30—C34 | −74.4 (2) |
C14—C15—C16—C18 | 173.0 (2) | C35—C30—O30—C34 | 34.0 (2) |
C12—C11—C16—C15 | −14.4 (3) | O30—C30—C31—C32 | 69.3 (2) |
C10—C11—C16—C15 | 151.0 (2) | C29—C30—C31—C32 | −166.2 (2) |
C12—C11—C16—C18 | 172.8 (2) | C35—C30—C31—C32 | −37.7 (2) |
C10—C11—C16—C18 | −21.8 (4) | C30—C31—C32—C33 | 1.5 (2) |
C5—C4—C17—O17 | −87.5 (3) | C31—C32—C33—C34 | −67.9 (2) |
C3—C4—C17—O17 | 90.7 (3) | C31—C32—C33—C38 | 165.8 (2) |
C4—C17—O17—C19 | −169.00 (19) | C31—C32—C33—C35 | 34.8 (2) |
C15—C16—C18—O18 | 99.8 (2) | C30—O30—C34—O34 | −179.8 (3) |
C11—C16—C18—O18 | −87.3 (3) | C30—O30—C34—C33 | 1.7 (3) |
C16—C18—O18—C29 | −166.57 (19) | C38—C33—C34—O34 | 17.8 (4) |
C17—O17—C19—O19 | 1.6 (3) | C32—C33—C34—O34 | −109.4 (3) |
C17—O17—C19—C20 | −177.01 (19) | C35—C33—C34—O34 | 145.3 (3) |
O19—C19—C20—O20 | 170.7 (2) | C38—C33—C34—O30 | −163.9 (2) |
O17—C19—C20—O20 | −10.7 (3) | C32—C33—C34—O30 | 69.0 (2) |
O19—C19—C20—C21 | 49.7 (3) | C35—C33—C34—O30 | −36.3 (2) |
O17—C19—C20—C21 | −131.7 (2) | O30—C30—C35—C36 | 63.6 (2) |
O19—C19—C20—C25 | −72.5 (3) | C29—C30—C35—C36 | −58.4 (3) |
O17—C19—C20—C25 | 106.1 (2) | C31—C30—C35—C36 | 172.8 (2) |
C19—C20—O20—C24 | 159.30 (18) | O30—C30—C35—C37 | −170.41 (19) |
C21—C20—O20—C24 | −74.1 (2) | C29—C30—C35—C37 | 67.7 (3) |
C25—C20—O20—C24 | 34.4 (2) | C31—C30—C35—C37 | −61.1 (3) |
O20—C20—C21—C22 | 69.5 (2) | O30—C30—C35—C33 | −52.50 (19) |
C19—C20—C21—C22 | −166.9 (2) | C29—C30—C35—C33 | −174.43 (19) |
C25—C20—C21—C22 | −38.2 (2) | C31—C30—C35—C33 | 56.8 (2) |
C20—C21—C22—C23 | 1.6 (2) | C34—C33—C35—C36 | −63.3 (2) |
C21—C22—C23—C28 | 167.0 (2) | C38—C33—C35—C36 | 61.4 (3) |
C21—C22—C23—C24 | −67.6 (2) | C32—C33—C35—C36 | −169.2 (2) |
C21—C22—C23—C25 | 35.1 (2) | C34—C33—C35—C37 | 169.6 (2) |
C20—O20—C24—O24 | 179.1 (2) | C38—C33—C35—C37 | −65.6 (3) |
C20—O20—C24—C23 | 1.2 (2) | C32—C33—C35—C37 | 63.7 (2) |
C28—C23—C24—O24 | 18.2 (4) | C34—C33—C35—C30 | 51.53 (19) |
C22—C23—C24—O24 | −108.5 (3) | C38—C33—C35—C30 | 176.3 (2) |
C25—C23—C24—O24 | 146.5 (3) | C32—C33—C35—C30 | −54.34 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22A···O19i | 0.99 | 2.56 | 3.493 (4) | 157 |
C32—H32A···O29i | 0.99 | 2.44 | 3.381 (3) | 159 |
C17—H17A···O24ii | 0.99 | 2.58 | 3.442 (3) | 146 |
C27—H27A···O24ii | 0.98 | 2.51 | 3.486 (3) | 171 |
C9—H9A···O30ii | 0.99 | 2.59 | 3.556 (3) | 167 |
C36—H36A···O34ii | 0.98 | 2.54 | 3.503 (4) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |