Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010601136X/sk3014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010601136X/sk3014Isup2.hkl |
CCDC reference: 616138
3α-Hydroxy-7-oxo-5β-cholanic acid (7-ketolithocholic acid, isolatable from the bile of guinea pig and nutria), purchased from TCI America, Portland, Oregon, USA (Quantity?), was dissolved in acetone (Volume?) and subjected to Jones oxidation (Is a reference needed here?), yielding 92% of (I). Refrigerating an acetonitrile solution produced the crystal used (m.p. 433 K). Compound (I) may also be obtained by oxidation of either `ursodeoxycholic' or `chenodeoxycholic' acids, the latter being one of the two principal steroidal acids in human bile. The sign of rotation for (I) is well established (Kagan & Jacques, 1957) and the absolute stereochemistry of (I), consistent with our experimental Flack parameter (Flack, 1983), corresponds to that of other steroids and bile acids (Fieser & Fieser, 1959; Klyne & Buckingham, 1978).
All H atoms of (I) were found in electron-density difference maps but were placed in calculated positions and allowed to refine as riding on their respective C or O atoms. The O—H distances were fixed at 0.84 Å. For methyl, methylene and methine H atoms, C—H distances were fixed at 0.98, 0.99 and 1.00 Å, respectively. Uiso(H) = 1.5Ueq(parent) for H atoms on O and methyl C atoms, and 1.2Ueq(parent) for all others. [Please check added text and correct as necessary]
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C24H36O4 | Dx = 1.226 Mg m−3 |
Mr = 388.53 | Melting point: 433 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab' | Cell parameters from 27061 reflections |
a = 7.6177 (1) Å | θ = 2.2–69.6° |
b = 27.6911 (4) Å | µ = 0.65 mm−1 |
c = 29.9256 (4) Å | T = 100 K |
V = 6312.58 (15) Å3 | Block, colourless |
Z = 12 | 0.22 × 0.13 × 0.12 mm |
F(000) = 2544 |
Bruker SMART CCD APEX II area-detector diffractometer | 10459 independent reflections |
Radiation source: fine-focus sealed tube | 9648 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 69.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −7→9 |
Tmin = 0.871, Tmax = 0.927 | k = −27→33 |
27061 measured reflections | l = −35→23 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0471P)2 + 1.0308P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.091 | (Δ/σ)max = 0.01 |
S = 1.07 | Δρmax = 0.21 e Å−3 |
10459 reflections | Δρmin = −0.16 e Å−3 |
758 parameters | Extinction correction: SHELXL97 (Sheldrick,1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00006 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.14 (13) |
C24H36O4 | V = 6312.58 (15) Å3 |
Mr = 388.53 | Z = 12 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.6177 (1) Å | µ = 0.65 mm−1 |
b = 27.6911 (4) Å | T = 100 K |
c = 29.9256 (4) Å | 0.22 × 0.13 × 0.12 mm |
Bruker SMART CCD APEX II area-detector diffractometer | 10459 independent reflections |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | 9648 reflections with I > 2σ(I) |
Tmin = 0.871, Tmax = 0.927 | Rint = 0.022 |
27061 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.091 | Δρmax = 0.21 e Å−3 |
S = 1.07 | Δρmin = −0.16 e Å−3 |
10459 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
758 parameters | Absolute structure parameter: 0.14 (13) |
0 restraints |
Experimental. crystal mounted on cryoloop using Paratone-N |
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 | ||
C1B | 0.0703 (3) | 0.08970 (7) | 0.10454 (7) | 0.0242 (4) | |
H1BA | −0.0392 | 0.1074 | 0.0975 | 0.029* | |
H1BB | 0.0424 | 0.0656 | 0.1279 | 0.029* | |
O1C | 0.2229 (3) | 1.05006 (6) | 0.23980 (6) | 0.0541 (5) | |
C1C | 0.3510 (3) | 0.95205 (7) | 0.30150 (6) | 0.0221 (4) | |
H1CA | 0.3438 | 0.9772 | 0.3250 | 0.026* | |
H1CB | 0.4562 | 0.9322 | 0.3077 | 0.026* | |
O1B | 0.3251 (2) | −0.00527 (5) | 0.06408 (5) | 0.0315 (3) | |
O2C | −0.20804 (18) | 0.87207 (5) | 0.22685 (4) | 0.0261 (3) | |
O2B | 0.67573 (17) | 0.17489 (5) | 0.08846 (5) | 0.0303 (3) | |
C2B | 0.1317 (3) | 0.06287 (7) | 0.06220 (7) | 0.0256 (4) | |
H2BA | 0.0416 | 0.0391 | 0.0530 | 0.031* | |
H2BB | 0.1478 | 0.0862 | 0.0375 | 0.031* | |
C2C | 0.3751 (3) | 0.97685 (7) | 0.25622 (7) | 0.0279 (4) | |
H2CA | 0.4811 | 0.9975 | 0.2567 | 0.033* | |
H2CB | 0.3895 | 0.9524 | 0.2324 | 0.033* | |
O3B | 0.26444 (19) | 0.46326 (5) | 0.09675 (4) | 0.0270 (3) | |
O3C | 0.1446 (2) | 0.56650 (5) | 0.14071 (5) | 0.0334 (4) | |
C3B | 0.3013 (3) | 0.03752 (7) | 0.07151 (6) | 0.0234 (4) | |
C3C | 0.2153 (3) | 1.00698 (7) | 0.24737 (7) | 0.0328 (5) | |
O4C | 0.33746 (18) | 0.51493 (5) | 0.16933 (4) | 0.0253 (3) | |
H4CC | 0.3125 | 0.4993 | 0.1462 | 0.038* | |
O4B | 0.1241 (2) | 0.52327 (5) | 0.06194 (5) | 0.0348 (4) | |
H4BC | 0.1319 | 0.5364 | 0.0872 | 0.052* | |
C4C | 0.0440 (3) | 0.98022 (8) | 0.25057 (7) | 0.0301 (5) | |
H4CA | 0.0337 | 0.9581 | 0.2247 | 0.036* | |
H4CB | −0.0536 | 1.0038 | 0.2487 | 0.036* | |
C4B | 0.4423 (2) | 0.06828 (7) | 0.09164 (6) | 0.0218 (4) | |
H4BA | 0.4874 | 0.0907 | 0.0686 | 0.026* | |
H4BB | 0.5408 | 0.0473 | 0.1011 | 0.026* | |
C5B | 0.3792 (3) | 0.09785 (7) | 0.13217 (6) | 0.0208 (4) | |
H5BA | 0.3569 | 0.0747 | 0.1572 | 0.025* | |
C5C | 0.0247 (3) | 0.95082 (7) | 0.29388 (6) | 0.0232 (4) | |
H5CA | 0.0096 | 0.9744 | 0.3189 | 0.028* | |
C6B | 0.5301 (3) | 0.13179 (7) | 0.14703 (6) | 0.0245 (4) | |
H6BA | 0.5032 | 0.1458 | 0.1767 | 0.029* | |
H6BB | 0.6411 | 0.1134 | 0.1494 | 0.029* | |
C6C | −0.1459 (3) | 0.92032 (7) | 0.29117 (7) | 0.0258 (4) | |
H6CA | −0.1781 | 0.9088 | 0.3214 | 0.031* | |
H6CB | −0.2431 | 0.9407 | 0.2798 | 0.031* | |
C7C | −0.1204 (2) | 0.87750 (7) | 0.26052 (6) | 0.0215 (4) | |
C7B | 0.5491 (3) | 0.17147 (7) | 0.11283 (6) | 0.0218 (4) | |
C8C | 0.0299 (2) | 0.84461 (6) | 0.27338 (6) | 0.0176 (4) | |
H8CA | 0.0118 | 0.8339 | 0.3050 | 0.021* | |
C8B | 0.3872 (2) | 0.20283 (6) | 0.10814 (6) | 0.0178 (4) | |
H8BA | 0.3528 | 0.2146 | 0.1385 | 0.021* | |
C9C | 0.1994 (2) | 0.87638 (6) | 0.27151 (6) | 0.0182 (4) | |
H9CA | 0.2027 | 0.8908 | 0.2409 | 0.022* | |
C9B | 0.2394 (2) | 0.16826 (6) | 0.09051 (6) | 0.0171 (4) | |
H9BA | 0.2854 | 0.1536 | 0.0623 | 0.021* | |
C10B | 0.2056 (3) | 0.12557 (6) | 0.12331 (6) | 0.0201 (4) | |
C10C | 0.1875 (2) | 0.91968 (6) | 0.30481 (6) | 0.0193 (4) | |
C11C | 0.3682 (2) | 0.84661 (6) | 0.27623 (7) | 0.0214 (4) | |
H11A | 0.3833 | 0.8377 | 0.3080 | 0.026* | |
H11B | 0.4692 | 0.8671 | 0.2676 | 0.026* | |
C11B | 0.0724 (2) | 0.19599 (6) | 0.07756 (6) | 0.0198 (4) | |
H11C | 0.0090 | 0.2050 | 0.1052 | 0.024* | |
H11D | −0.0048 | 0.1741 | 0.0603 | 0.024* | |
C12B | 0.1042 (2) | 0.24190 (6) | 0.04995 (6) | 0.0196 (4) | |
H12A | 0.1481 | 0.2328 | 0.0200 | 0.024* | |
H12B | −0.0083 | 0.2593 | 0.0460 | 0.024* | |
C12C | 0.3715 (2) | 0.80036 (7) | 0.24790 (6) | 0.0219 (4) | |
H12C | 0.3755 | 0.8091 | 0.2158 | 0.026* | |
H12D | 0.4788 | 0.7817 | 0.2549 | 0.026* | |
C13C | 0.2096 (2) | 0.76890 (6) | 0.25675 (6) | 0.0181 (4) | |
C13B | 0.2372 (2) | 0.27552 (6) | 0.07246 (6) | 0.0169 (4) | |
C14C | 0.0479 (2) | 0.79995 (6) | 0.24422 (6) | 0.0171 (4) | |
H14A | 0.0660 | 0.8114 | 0.2129 | 0.021* | |
C14B | 0.4087 (2) | 0.24625 (6) | 0.07752 (6) | 0.0177 (4) | |
H14B | 0.4396 | 0.2336 | 0.0472 | 0.021* | |
C15B | 0.5460 (3) | 0.28426 (7) | 0.08952 (7) | 0.0247 (4) | |
H15A | 0.6647 | 0.2737 | 0.0802 | 0.030* | |
H15B | 0.5466 | 0.2906 | 0.1221 | 0.030* | |
C15C | −0.1060 (2) | 0.76445 (6) | 0.24341 (6) | 0.0202 (4) | |
H15C | −0.1987 | 0.7755 | 0.2226 | 0.024* | |
H15D | −0.1573 | 0.7605 | 0.2736 | 0.024* | |
C16C | −0.0219 (2) | 0.71675 (6) | 0.22697 (6) | 0.0187 (4) | |
H16A | −0.0667 | 0.7083 | 0.1969 | 0.022* | |
H16B | −0.0506 | 0.6900 | 0.2477 | 0.022* | |
C16B | 0.4886 (2) | 0.32975 (7) | 0.06333 (6) | 0.0227 (4) | |
H16C | 0.5712 | 0.3362 | 0.0385 | 0.027* | |
H16D | 0.4869 | 0.3582 | 0.0833 | 0.027* | |
C17B | 0.3007 (2) | 0.31960 (6) | 0.04470 (6) | 0.0184 (4) | |
H17A | 0.3136 | 0.3088 | 0.0130 | 0.022* | |
C17C | 0.1806 (2) | 0.72495 (6) | 0.22534 (6) | 0.0175 (4) | |
H17B | 0.2108 | 0.7356 | 0.1943 | 0.021* | |
C18B | 0.1676 (3) | 0.29308 (7) | 0.11795 (6) | 0.0212 (4) | |
H18A | 0.1275 | 0.2653 | 0.1355 | 0.032* | |
H18B | 0.0693 | 0.3153 | 0.1132 | 0.032* | |
H18C | 0.2615 | 0.3098 | 0.1341 | 0.032* | |
C18C | 0.2049 (3) | 0.75198 (6) | 0.30556 (6) | 0.0201 (4) | |
H18D | 0.2232 | 0.7797 | 0.3254 | 0.030* | |
H18E | 0.2980 | 0.7281 | 0.3105 | 0.030* | |
H18F | 0.0906 | 0.7373 | 0.3120 | 0.030* | |
C19C | 0.1761 (3) | 0.90257 (7) | 0.35363 (6) | 0.0239 (4) | |
H19A | 0.1687 | 0.9307 | 0.3734 | 0.036* | |
H19B | 0.2810 | 0.8837 | 0.3611 | 0.036* | |
H19C | 0.0714 | 0.8824 | 0.3575 | 0.036* | |
C19B | 0.1309 (3) | 0.14349 (7) | 0.16807 (6) | 0.0275 (4) | |
H19D | 0.1112 | 0.1159 | 0.1879 | 0.041* | |
H19E | 0.0194 | 0.1602 | 0.1628 | 0.041* | |
H19F | 0.2145 | 0.1658 | 0.1820 | 0.041* | |
C20B | 0.1860 (3) | 0.36548 (6) | 0.04463 (6) | 0.0190 (4) | |
H20A | 0.1765 | 0.3772 | 0.0761 | 0.023* | |
C20C | 0.2825 (2) | 0.67792 (6) | 0.23457 (6) | 0.0188 (4) | |
H20B | 0.2514 | 0.6664 | 0.2652 | 0.023* | |
C21C | 0.4830 (3) | 0.68510 (7) | 0.23239 (6) | 0.0236 (4) | |
H21A | 0.5419 | 0.6543 | 0.2384 | 0.035* | |
H21B | 0.5188 | 0.7090 | 0.2548 | 0.035* | |
H21C | 0.5159 | 0.6966 | 0.2026 | 0.035* | |
C21B | −0.0008 (3) | 0.35638 (7) | 0.02719 (7) | 0.0257 (4) | |
H21D | −0.0676 | 0.3866 | 0.0279 | 0.039* | |
H21E | −0.0589 | 0.3323 | 0.0461 | 0.039* | |
H21F | 0.0050 | 0.3444 | −0.0036 | 0.039* | |
C22C | 0.2232 (3) | 0.63960 (6) | 0.20082 (6) | 0.0204 (4) | |
H22A | 0.0941 | 0.6363 | 0.2030 | 0.024* | |
H22B | 0.2506 | 0.6515 | 0.1704 | 0.024* | |
C22B | 0.2757 (3) | 0.40527 (6) | 0.01701 (6) | 0.0221 (4) | |
H22C | 0.3983 | 0.4086 | 0.0275 | 0.027* | |
H22D | 0.2800 | 0.3947 | −0.0146 | 0.027* | |
C23C | 0.3050 (3) | 0.58969 (7) | 0.20637 (6) | 0.0248 (4) | |
H23A | 0.4344 | 0.5928 | 0.2069 | 0.030* | |
H23B | 0.2672 | 0.5757 | 0.2353 | 0.030* | |
C23B | 0.1885 (3) | 0.45498 (6) | 0.01880 (6) | 0.0242 (4) | |
H23C | 0.2453 | 0.4760 | −0.0037 | 0.029* | |
H23D | 0.0638 | 0.4514 | 0.0101 | 0.029* | |
C24C | 0.2525 (2) | 0.55633 (6) | 0.16906 (6) | 0.0209 (4) | |
C24B | 0.1960 (3) | 0.47999 (6) | 0.06339 (6) | 0.0219 (4) | |
O1A | 0.2803 (2) | −0.49928 (6) | −0.16173 (5) | 0.0421 (4) | |
C1A | 0.1323 (3) | −0.42128 (7) | −0.08165 (7) | 0.0253 (4) | |
H1AA | 0.1422 | −0.4517 | −0.0645 | 0.030* | |
H1AB | 0.0240 | −0.4047 | −0.0717 | 0.030* | |
O2A | 0.68691 (18) | −0.31652 (5) | −0.13052 (4) | 0.0274 (3) | |
C2A | 0.1143 (3) | −0.43359 (7) | −0.13136 (7) | 0.0280 (4) | |
H2AA | 0.0114 | −0.4548 | −0.1362 | 0.034* | |
H2AB | 0.0976 | −0.4037 | −0.1490 | 0.034* | |
O3A | 0.2354 (3) | 0.02130 (5) | −0.03940 (5) | 0.0450 (4) | |
C3A | 0.2787 (3) | −0.45881 (7) | −0.14572 (6) | 0.0302 (5) | |
O4A | 0.2099 (2) | −0.05186 (5) | −0.00978 (4) | 0.0386 (4) | |
H4AC | 0.2457 | −0.0373 | 0.0131 | 0.058* | |
C4A | 0.4453 (3) | −0.43121 (8) | −0.13653 (7) | 0.0275 (4) | |
H4AA | 0.4499 | −0.4026 | −0.1563 | 0.033* | |
H4AB | 0.5473 | −0.4519 | −0.1437 | 0.033* | |
C5A | 0.4590 (3) | −0.41457 (7) | −0.08738 (6) | 0.0252 (4) | |
H5AA | 0.4760 | −0.4441 | −0.0687 | 0.030* | |
C6A | 0.6249 (3) | −0.38302 (7) | −0.08185 (7) | 0.0250 (4) | |
H6AA | 0.6551 | −0.3806 | −0.0497 | 0.030* | |
H6AB | 0.7247 | −0.3985 | −0.0975 | 0.030* | |
C7A | 0.5960 (3) | −0.33292 (7) | −0.10072 (6) | 0.0226 (4) | |
C8A | 0.4400 (2) | −0.30677 (7) | −0.08124 (6) | 0.0211 (4) | |
H8AA | 0.4545 | −0.3059 | −0.0480 | 0.025* | |
C9A | 0.2756 (2) | −0.33799 (7) | −0.09198 (6) | 0.0218 (4) | |
H9AA | 0.2760 | −0.3431 | −0.1251 | 0.026* | |
C10A | 0.2911 (3) | −0.38904 (7) | −0.07038 (6) | 0.0227 (4) | |
C11A | 0.1020 (3) | −0.31243 (7) | −0.08093 (7) | 0.0276 (4) | |
H11E | 0.0832 | −0.3137 | −0.0482 | 0.033* | |
H11F | 0.0046 | −0.3303 | −0.0953 | 0.033* | |
C12A | 0.0946 (2) | −0.25925 (7) | −0.09619 (7) | 0.0253 (4) | |
H12E | 0.0929 | −0.2580 | −0.1293 | 0.030* | |
H12F | −0.0153 | −0.2444 | −0.0852 | 0.030* | |
C13A | 0.2506 (2) | −0.23040 (7) | −0.07902 (6) | 0.0210 (4) | |
C14A | 0.4173 (2) | −0.25511 (7) | −0.09763 (6) | 0.0201 (4) | |
H14C | 0.4030 | −0.2568 | −0.1308 | 0.024* | |
C15A | 0.5659 (3) | −0.21942 (7) | −0.08849 (6) | 0.0239 (4) | |
H15E | 0.6591 | −0.2222 | −0.1114 | 0.029* | |
H15F | 0.6180 | −0.2251 | −0.0586 | 0.029* | |
C16A | 0.4765 (2) | −0.16919 (7) | −0.09070 (7) | 0.0241 (4) | |
H16E | 0.5246 | −0.1502 | −0.1159 | 0.029* | |
H16F | 0.4970 | −0.1511 | −0.0626 | 0.029* | |
C17A | 0.2769 (2) | −0.17831 (7) | −0.09754 (6) | 0.0207 (4) | |
H17C | 0.2561 | −0.1798 | −0.1305 | 0.025* | |
C18A | 0.2509 (3) | −0.22842 (7) | −0.02745 (6) | 0.0260 (4) | |
H18G | 0.2344 | −0.2610 | −0.0155 | 0.039* | |
H18H | 0.1552 | −0.2076 | −0.0172 | 0.039* | |
H18I | 0.3633 | −0.2154 | −0.0170 | 0.039* | |
C19A | 0.2986 (3) | −0.38614 (7) | −0.01886 (6) | 0.0286 (4) | |
H19G | 0.3082 | −0.4188 | −0.0064 | 0.043* | |
H19H | 0.1915 | −0.3708 | −0.0077 | 0.043* | |
H19I | 0.4009 | −0.3671 | −0.0098 | 0.043* | |
C20A | 0.1627 (3) | −0.13683 (7) | −0.07929 (6) | 0.0226 (4) | |
H20C | 0.1861 | −0.1336 | −0.0465 | 0.027* | |
C21A | −0.0329 (3) | −0.14693 (8) | −0.08574 (7) | 0.0295 (4) | |
H21G | −0.1014 | −0.1199 | −0.0738 | 0.044* | |
H21H | −0.0647 | −0.1766 | −0.0699 | 0.044* | |
H21I | −0.0580 | −0.1507 | −0.1177 | 0.044* | |
C22A | 0.2149 (3) | −0.08917 (7) | −0.10212 (6) | 0.0278 (4) | |
H22E | 0.3433 | −0.0850 | −0.0987 | 0.033* | |
H22F | 0.1908 | −0.0924 | −0.1345 | 0.033* | |
C23A | 0.1247 (3) | −0.04276 (7) | −0.08543 (7) | 0.0303 (5) | |
H23E | 0.1320 | −0.0182 | −0.1094 | 0.036* | |
H23F | −0.0012 | −0.0500 | −0.0806 | 0.036* | |
C24A | 0.1961 (3) | −0.02083 (7) | −0.04335 (7) | 0.0262 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1B | 0.0199 (9) | 0.0179 (9) | 0.0349 (10) | 0.0017 (8) | 0.0034 (8) | 0.0045 (8) |
O1C | 0.0667 (12) | 0.0287 (8) | 0.0670 (11) | −0.0068 (9) | −0.0081 (10) | 0.0215 (8) |
C1C | 0.0235 (10) | 0.0184 (9) | 0.0244 (9) | −0.0038 (8) | −0.0004 (8) | −0.0016 (8) |
O1B | 0.0382 (8) | 0.0198 (7) | 0.0367 (7) | 0.0064 (6) | −0.0096 (7) | −0.0073 (6) |
O2C | 0.0215 (7) | 0.0257 (7) | 0.0311 (7) | 0.0006 (6) | −0.0046 (6) | −0.0006 (6) |
O2B | 0.0161 (7) | 0.0273 (7) | 0.0474 (8) | 0.0000 (6) | 0.0003 (7) | 0.0038 (7) |
C2B | 0.0221 (10) | 0.0203 (9) | 0.0344 (10) | −0.0013 (8) | −0.0070 (9) | −0.0023 (9) |
C2C | 0.0309 (11) | 0.0241 (10) | 0.0285 (10) | −0.0092 (9) | 0.0028 (9) | 0.0003 (9) |
O3B | 0.0353 (8) | 0.0194 (6) | 0.0263 (7) | 0.0012 (6) | −0.0041 (6) | −0.0023 (6) |
O3C | 0.0380 (9) | 0.0246 (7) | 0.0377 (8) | 0.0120 (7) | −0.0165 (7) | −0.0090 (6) |
C3B | 0.0284 (10) | 0.0199 (9) | 0.0218 (9) | 0.0010 (8) | −0.0007 (8) | −0.0002 (7) |
C3C | 0.0468 (13) | 0.0258 (10) | 0.0258 (9) | −0.0050 (10) | −0.0051 (10) | 0.0064 (9) |
O4C | 0.0318 (8) | 0.0192 (6) | 0.0249 (6) | 0.0061 (6) | −0.0038 (6) | −0.0018 (5) |
O4B | 0.0476 (9) | 0.0215 (7) | 0.0353 (8) | 0.0088 (7) | −0.0133 (7) | −0.0082 (6) |
C4C | 0.0354 (12) | 0.0249 (10) | 0.0300 (10) | 0.0052 (9) | −0.0092 (10) | 0.0022 (9) |
C4B | 0.0206 (9) | 0.0191 (9) | 0.0258 (9) | 0.0037 (7) | −0.0002 (8) | −0.0022 (8) |
C5B | 0.0253 (10) | 0.0175 (9) | 0.0197 (8) | 0.0026 (8) | −0.0005 (8) | 0.0009 (7) |
C5C | 0.0237 (10) | 0.0196 (9) | 0.0264 (9) | 0.0021 (8) | −0.0008 (8) | −0.0038 (8) |
C6B | 0.0258 (10) | 0.0223 (10) | 0.0256 (9) | 0.0041 (8) | −0.0077 (8) | −0.0018 (8) |
C6C | 0.0199 (10) | 0.0236 (10) | 0.0340 (10) | 0.0033 (8) | 0.0001 (8) | −0.0052 (8) |
C7C | 0.0150 (9) | 0.0221 (9) | 0.0274 (10) | −0.0027 (8) | 0.0025 (8) | 0.0006 (8) |
C7B | 0.0192 (9) | 0.0200 (9) | 0.0262 (9) | −0.0016 (8) | −0.0072 (8) | −0.0040 (8) |
C8C | 0.0164 (8) | 0.0186 (9) | 0.0177 (8) | −0.0019 (7) | 0.0011 (7) | 0.0011 (7) |
C8B | 0.0189 (9) | 0.0170 (9) | 0.0176 (8) | −0.0013 (8) | −0.0021 (7) | −0.0024 (7) |
C9C | 0.0187 (9) | 0.0166 (8) | 0.0195 (8) | −0.0017 (8) | 0.0002 (8) | 0.0004 (7) |
C9B | 0.0176 (9) | 0.0159 (8) | 0.0179 (8) | 0.0015 (7) | 0.0023 (7) | −0.0016 (7) |
C10B | 0.0215 (9) | 0.0174 (8) | 0.0215 (9) | 0.0016 (8) | 0.0045 (8) | 0.0009 (7) |
C10C | 0.0200 (9) | 0.0176 (8) | 0.0202 (9) | −0.0030 (8) | 0.0011 (8) | −0.0007 (7) |
C11C | 0.0155 (9) | 0.0185 (9) | 0.0302 (10) | −0.0025 (7) | −0.0010 (8) | −0.0018 (8) |
C11B | 0.0160 (9) | 0.0162 (8) | 0.0270 (9) | −0.0013 (7) | −0.0009 (8) | 0.0013 (8) |
C12B | 0.0184 (9) | 0.0177 (9) | 0.0227 (9) | 0.0016 (7) | −0.0013 (8) | −0.0005 (7) |
C12C | 0.0168 (9) | 0.0216 (9) | 0.0273 (9) | 0.0005 (8) | 0.0027 (8) | −0.0025 (8) |
C13C | 0.0183 (9) | 0.0171 (8) | 0.0189 (8) | 0.0003 (8) | 0.0005 (7) | −0.0007 (7) |
C13B | 0.0170 (9) | 0.0165 (8) | 0.0172 (8) | −0.0005 (7) | 0.0004 (7) | −0.0019 (7) |
C14C | 0.0153 (9) | 0.0177 (9) | 0.0184 (8) | −0.0023 (7) | −0.0010 (7) | −0.0004 (7) |
C14B | 0.0156 (8) | 0.0188 (9) | 0.0187 (8) | 0.0000 (7) | 0.0001 (7) | −0.0022 (7) |
C15B | 0.0200 (9) | 0.0230 (9) | 0.0312 (10) | −0.0009 (8) | −0.0057 (8) | 0.0007 (9) |
C15C | 0.0181 (9) | 0.0200 (9) | 0.0224 (9) | −0.0011 (8) | −0.0009 (8) | −0.0023 (8) |
C16C | 0.0203 (9) | 0.0176 (9) | 0.0183 (8) | −0.0023 (7) | −0.0009 (8) | −0.0007 (7) |
C16B | 0.0195 (9) | 0.0197 (9) | 0.0290 (9) | −0.0035 (8) | −0.0024 (8) | −0.0006 (8) |
C17B | 0.0199 (9) | 0.0181 (8) | 0.0171 (8) | −0.0016 (8) | 0.0015 (8) | −0.0031 (7) |
C17C | 0.0199 (9) | 0.0183 (9) | 0.0144 (8) | −0.0020 (8) | 0.0016 (7) | 0.0007 (7) |
C18B | 0.0240 (10) | 0.0198 (9) | 0.0199 (9) | 0.0011 (8) | 0.0029 (8) | −0.0004 (7) |
C18C | 0.0212 (9) | 0.0197 (8) | 0.0194 (8) | 0.0002 (8) | −0.0016 (8) | −0.0021 (7) |
C19C | 0.0285 (10) | 0.0226 (9) | 0.0206 (9) | −0.0036 (8) | −0.0015 (8) | 0.0001 (8) |
C19B | 0.0334 (11) | 0.0242 (10) | 0.0250 (9) | 0.0048 (9) | 0.0107 (9) | 0.0031 (8) |
C20B | 0.0226 (9) | 0.0165 (8) | 0.0179 (8) | −0.0001 (8) | 0.0005 (8) | −0.0013 (7) |
C20C | 0.0203 (9) | 0.0192 (9) | 0.0169 (8) | 0.0001 (8) | 0.0011 (7) | 0.0002 (7) |
C21C | 0.0230 (10) | 0.0200 (9) | 0.0277 (9) | 0.0002 (8) | −0.0007 (8) | −0.0017 (8) |
C21B | 0.0260 (10) | 0.0193 (9) | 0.0318 (10) | 0.0005 (8) | −0.0037 (9) | 0.0031 (8) |
C22C | 0.0221 (9) | 0.0196 (9) | 0.0194 (8) | 0.0021 (8) | −0.0003 (8) | −0.0019 (7) |
C22B | 0.0279 (10) | 0.0184 (9) | 0.0200 (8) | −0.0017 (8) | 0.0009 (8) | 0.0005 (7) |
C23C | 0.0291 (10) | 0.0199 (9) | 0.0254 (9) | 0.0021 (9) | −0.0033 (9) | −0.0012 (8) |
C23B | 0.0322 (10) | 0.0174 (9) | 0.0230 (9) | −0.0032 (8) | −0.0016 (9) | 0.0015 (7) |
C24C | 0.0198 (9) | 0.0175 (9) | 0.0255 (9) | −0.0005 (7) | 0.0024 (8) | 0.0031 (8) |
C24B | 0.0205 (9) | 0.0165 (8) | 0.0287 (10) | −0.0042 (8) | −0.0005 (8) | 0.0014 (8) |
O1A | 0.0505 (10) | 0.0324 (8) | 0.0435 (8) | −0.0075 (8) | 0.0081 (8) | −0.0085 (7) |
C1A | 0.0223 (10) | 0.0242 (10) | 0.0295 (10) | −0.0021 (8) | 0.0018 (8) | 0.0025 (8) |
O2A | 0.0206 (7) | 0.0343 (8) | 0.0274 (7) | −0.0006 (6) | 0.0040 (6) | 0.0056 (6) |
C2A | 0.0253 (10) | 0.0257 (10) | 0.0331 (10) | −0.0075 (9) | −0.0044 (9) | 0.0013 (9) |
O3A | 0.0637 (12) | 0.0236 (8) | 0.0477 (9) | −0.0042 (8) | −0.0092 (9) | 0.0024 (7) |
C3A | 0.0399 (12) | 0.0268 (11) | 0.0237 (9) | −0.0033 (10) | −0.0001 (9) | 0.0032 (8) |
O4A | 0.0666 (11) | 0.0245 (7) | 0.0246 (7) | −0.0136 (8) | −0.0056 (8) | 0.0006 (6) |
C4A | 0.0255 (10) | 0.0301 (11) | 0.0270 (10) | 0.0029 (9) | 0.0016 (8) | −0.0020 (9) |
C5A | 0.0256 (10) | 0.0250 (10) | 0.0251 (9) | 0.0002 (8) | −0.0021 (8) | 0.0046 (9) |
C6A | 0.0191 (9) | 0.0289 (10) | 0.0271 (10) | 0.0015 (8) | −0.0014 (8) | 0.0051 (8) |
C7A | 0.0180 (9) | 0.0290 (10) | 0.0208 (9) | −0.0039 (8) | −0.0051 (8) | 0.0010 (8) |
C8A | 0.0185 (9) | 0.0263 (10) | 0.0183 (8) | −0.0038 (8) | −0.0017 (7) | 0.0023 (8) |
C9A | 0.0194 (9) | 0.0242 (9) | 0.0219 (8) | −0.0037 (8) | −0.0010 (8) | 0.0005 (8) |
C10A | 0.0222 (9) | 0.0239 (9) | 0.0220 (9) | −0.0035 (8) | 0.0013 (8) | 0.0032 (8) |
C11A | 0.0178 (9) | 0.0262 (10) | 0.0388 (11) | −0.0048 (8) | 0.0000 (9) | 0.0006 (9) |
C12A | 0.0157 (9) | 0.0241 (10) | 0.0361 (11) | −0.0003 (8) | −0.0011 (8) | −0.0029 (9) |
C13A | 0.0175 (9) | 0.0258 (9) | 0.0197 (9) | −0.0023 (8) | 0.0008 (7) | 0.0005 (8) |
C14A | 0.0178 (9) | 0.0252 (10) | 0.0172 (8) | −0.0009 (8) | 0.0003 (7) | 0.0026 (8) |
C15A | 0.0206 (9) | 0.0272 (10) | 0.0238 (9) | −0.0038 (8) | 0.0011 (8) | 0.0039 (8) |
C16A | 0.0207 (9) | 0.0265 (10) | 0.0250 (9) | −0.0033 (8) | 0.0023 (8) | 0.0023 (9) |
C17A | 0.0215 (9) | 0.0251 (9) | 0.0156 (8) | −0.0032 (8) | 0.0005 (7) | −0.0008 (7) |
C18A | 0.0272 (10) | 0.0285 (10) | 0.0222 (9) | −0.0005 (8) | 0.0060 (8) | 0.0019 (8) |
C19A | 0.0304 (11) | 0.0327 (11) | 0.0226 (9) | −0.0024 (9) | 0.0035 (9) | 0.0035 (8) |
C20A | 0.0247 (10) | 0.0246 (9) | 0.0186 (8) | −0.0023 (8) | 0.0005 (8) | −0.0026 (8) |
C21A | 0.0265 (10) | 0.0309 (11) | 0.0312 (10) | 0.0024 (9) | 0.0005 (9) | −0.0051 (9) |
C22A | 0.0332 (11) | 0.0288 (10) | 0.0215 (9) | −0.0001 (9) | 0.0025 (9) | −0.0008 (8) |
C23A | 0.0360 (11) | 0.0249 (10) | 0.0300 (10) | 0.0024 (9) | −0.0001 (10) | 0.0038 (9) |
C24A | 0.0254 (10) | 0.0216 (9) | 0.0318 (10) | 0.0017 (9) | 0.0031 (9) | 0.0014 (8) |
C1B—C10B | 1.538 (3) | C18C—H18D | 0.9800 |
C1B—C2B | 1.542 (3) | C18C—H18E | 0.9800 |
C1B—H1BA | 0.9900 | C18C—H18F | 0.9800 |
C1B—H1BB | 0.9900 | C19C—H19A | 0.9800 |
O1C—C3C | 1.216 (2) | C19C—H19B | 0.9800 |
C1C—C2C | 1.530 (3) | C19C—H19C | 0.9800 |
C1C—C10C | 1.537 (2) | C19B—H19D | 0.9800 |
C1C—H1CA | 0.9900 | C19B—H19E | 0.9800 |
C1C—H1CB | 0.9900 | C19B—H19F | 0.9800 |
O1B—C3B | 1.219 (2) | C20B—C21B | 1.536 (3) |
O2C—C7C | 1.218 (2) | C20B—C22B | 1.538 (2) |
O2B—C7B | 1.213 (2) | C20B—H20A | 1.0000 |
C2B—C3B | 1.496 (3) | C20C—C22C | 1.533 (2) |
C2B—H2BA | 0.9900 | C20C—C21C | 1.542 (3) |
C2B—H2BB | 0.9900 | C20C—H20B | 1.0000 |
C2C—C3C | 1.499 (3) | C21C—H21A | 0.9800 |
C2C—H2CA | 0.9900 | C21C—H21B | 0.9800 |
C2C—H2CB | 0.9900 | C21C—H21C | 0.9800 |
O3B—C24B | 1.218 (2) | C21B—H21D | 0.9800 |
O3C—C24C | 1.214 (2) | C21B—H21E | 0.9800 |
C3B—C4B | 1.498 (3) | C21B—H21F | 0.9800 |
C3C—C4C | 1.504 (3) | C22C—C23C | 1.525 (2) |
O4C—C24C | 1.317 (2) | C22C—H22A | 0.9900 |
O4C—H4CC | 0.8400 | C22C—H22B | 0.9900 |
O4B—C24B | 1.318 (2) | C22B—C23B | 1.529 (2) |
O4B—H4BC | 0.8400 | C22B—H22C | 0.9900 |
C4C—C5C | 1.537 (3) | C22B—H22D | 0.9900 |
C4C—H4CA | 0.9900 | C23C—C24C | 1.503 (3) |
C4C—H4CB | 0.9900 | C23C—H23A | 0.9900 |
C4B—C5B | 1.540 (3) | C23C—H23B | 0.9900 |
C4B—H4BA | 0.9900 | C23B—C24B | 1.504 (3) |
C4B—H4BB | 0.9900 | C23B—H23C | 0.9900 |
C5B—C6B | 1.550 (3) | C23B—H23D | 0.9900 |
C5B—C10B | 1.552 (2) | O1A—C3A | 1.219 (2) |
C5B—H5BA | 1.0000 | C1A—C2A | 1.532 (3) |
C5C—C10C | 1.546 (3) | C1A—C10A | 1.541 (3) |
C5C—C6C | 1.552 (3) | C1A—H1AA | 0.9900 |
C5C—H5CA | 1.0000 | C1A—H1AB | 0.9900 |
C6B—C7B | 1.508 (3) | O2A—C7A | 1.217 (2) |
C6B—H6BA | 0.9900 | C2A—C3A | 1.497 (3) |
C6B—H6BB | 0.9900 | C2A—H2AA | 0.9900 |
C6C—C7C | 1.512 (3) | C2A—H2AB | 0.9900 |
C6C—H6CA | 0.9900 | O3A—C24A | 1.210 (2) |
C6C—H6CB | 0.9900 | C3A—C4A | 1.507 (3) |
C7C—C8C | 1.513 (2) | O4A—C24A | 1.326 (2) |
C7B—C8B | 1.515 (2) | O4A—H4AC | 0.8400 |
C8C—C14C | 1.520 (2) | C4A—C5A | 1.545 (3) |
C8C—C9C | 1.563 (2) | C4A—H4AA | 0.9900 |
C8C—H8CA | 1.0000 | C4A—H4AB | 0.9900 |
C8B—C14B | 1.520 (2) | C5A—C6A | 1.545 (3) |
C8B—C9B | 1.569 (2) | C5A—C10A | 1.547 (3) |
C8B—H8BA | 1.0000 | C5A—H5AA | 1.0000 |
C9C—C11C | 1.534 (2) | C6A—C7A | 1.514 (3) |
C9C—C10C | 1.562 (2) | C6A—H6AA | 0.9900 |
C9C—H9CA | 1.0000 | C6A—H6AB | 0.9900 |
C9B—C11B | 1.536 (2) | C7A—C8A | 1.509 (3) |
C9B—C10B | 1.558 (2) | C8A—C14A | 1.522 (3) |
C9B—H9BA | 1.0000 | C8A—C9A | 1.555 (2) |
C10B—C19B | 1.538 (2) | C8A—H8AA | 1.0000 |
C10C—C19C | 1.538 (2) | C9A—C11A | 1.535 (3) |
C11C—C12C | 1.536 (2) | C9A—C10A | 1.559 (2) |
C11C—H11A | 0.9900 | C9A—H9AA | 1.0000 |
C11C—H11B | 0.9900 | C10A—C19A | 1.545 (2) |
C11B—C12B | 1.536 (2) | C11A—C12A | 1.543 (3) |
C11B—H11C | 0.9900 | C11A—H11E | 0.9900 |
C11B—H11D | 0.9900 | C11A—H11F | 0.9900 |
C12B—C13B | 1.532 (2) | C12A—C13A | 1.522 (3) |
C12B—H12A | 0.9900 | C12A—H12E | 0.9900 |
C12B—H12B | 0.9900 | C12A—H12F | 0.9900 |
C12C—C13C | 1.533 (2) | C13A—C18A | 1.544 (2) |
C12C—H12C | 0.9900 | C13A—C14A | 1.546 (2) |
C12C—H12D | 0.9900 | C13A—C17A | 1.558 (2) |
C13C—C18C | 1.534 (2) | C14A—C15A | 1.527 (2) |
C13C—C14C | 1.548 (2) | C14A—H14C | 1.0000 |
C13C—C17C | 1.553 (2) | C15A—C16A | 1.550 (3) |
C13B—C18B | 1.540 (2) | C15A—H15E | 0.9900 |
C13B—C14B | 1.545 (2) | C15A—H15F | 0.9900 |
C13B—C17B | 1.553 (2) | C16A—C17A | 1.555 (3) |
C14C—C15C | 1.530 (2) | C16A—H16E | 0.9900 |
C14C—H14A | 1.0000 | C16A—H16F | 0.9900 |
C14B—C15B | 1.527 (2) | C17A—C20A | 1.541 (3) |
C14B—H14B | 1.0000 | C17A—H17C | 1.0000 |
C15B—C16B | 1.547 (3) | C18A—H18G | 0.9800 |
C15B—H15A | 0.9900 | C18A—H18H | 0.9800 |
C15B—H15B | 0.9900 | C18A—H18I | 0.9800 |
C15C—C16C | 1.548 (2) | C19A—H19G | 0.9800 |
C15C—H15C | 0.9900 | C19A—H19H | 0.9800 |
C15C—H15D | 0.9900 | C19A—H19I | 0.9800 |
C16C—C17C | 1.560 (2) | C20A—C21A | 1.528 (3) |
C16C—H16A | 0.9900 | C20A—C22A | 1.538 (3) |
C16C—H16B | 0.9900 | C20A—H20C | 1.0000 |
C16B—C17B | 1.562 (2) | C21A—H21G | 0.9800 |
C16B—H16C | 0.9900 | C21A—H21H | 0.9800 |
C16B—H16D | 0.9900 | C21A—H21I | 0.9800 |
C17B—C20B | 1.542 (2) | C22A—C23A | 1.541 (3) |
C17B—H17A | 1.0000 | C22A—H22E | 0.9900 |
C17C—C20C | 1.541 (2) | C22A—H22F | 0.9900 |
C17C—H17B | 1.0000 | C23A—C24A | 1.500 (3) |
C18B—H18A | 0.9800 | C23A—H23E | 0.9900 |
C18B—H18B | 0.9800 | C23A—H23F | 0.9900 |
C18B—H18C | 0.9800 | ||
C10B—C1B—C2B | 114.08 (16) | H18D—C18C—H18F | 109.5 |
C10B—C1B—H1BA | 108.7 | H18E—C18C—H18F | 109.5 |
C2B—C1B—H1BA | 108.7 | C10C—C19C—H19A | 109.5 |
C10B—C1B—H1BB | 108.7 | C10C—C19C—H19B | 109.5 |
C2B—C1B—H1BB | 108.7 | H19A—C19C—H19B | 109.5 |
H1BA—C1B—H1BB | 107.6 | C10C—C19C—H19C | 109.5 |
C2C—C1C—C10C | 114.59 (16) | H19A—C19C—H19C | 109.5 |
C2C—C1C—H1CA | 108.6 | H19B—C19C—H19C | 109.5 |
C10C—C1C—H1CA | 108.6 | C10B—C19B—H19D | 109.5 |
C2C—C1C—H1CB | 108.6 | C10B—C19B—H19E | 109.5 |
C10C—C1C—H1CB | 108.6 | H19D—C19B—H19E | 109.5 |
H1CA—C1C—H1CB | 107.6 | C10B—C19B—H19F | 109.5 |
C3B—C2B—C1B | 109.58 (16) | H19D—C19B—H19F | 109.5 |
C3B—C2B—H2BA | 109.8 | H19E—C19B—H19F | 109.5 |
C1B—C2B—H2BA | 109.8 | C21B—C20B—C22B | 110.29 (15) |
C3B—C2B—H2BB | 109.8 | C21B—C20B—C17B | 112.96 (15) |
C1B—C2B—H2BB | 109.8 | C22B—C20B—C17B | 109.82 (15) |
H2BA—C2B—H2BB | 108.2 | C21B—C20B—H20A | 107.9 |
C3C—C2C—C1C | 107.99 (17) | C22B—C20B—H20A | 107.9 |
C3C—C2C—H2CA | 110.1 | C17B—C20B—H20A | 107.9 |
C1C—C2C—H2CA | 110.1 | C22C—C20C—C17C | 108.57 (14) |
C3C—C2C—H2CB | 110.1 | C22C—C20C—C21C | 110.68 (15) |
C1C—C2C—H2CB | 110.1 | C17C—C20C—C21C | 112.47 (15) |
H2CA—C2C—H2CB | 108.4 | C22C—C20C—H20B | 108.3 |
O1B—C3B—C2B | 123.42 (19) | C17C—C20C—H20B | 108.3 |
O1B—C3B—C4B | 121.26 (19) | C21C—C20C—H20B | 108.3 |
C2B—C3B—C4B | 115.32 (16) | C20C—C21C—H21A | 109.5 |
O1C—C3C—C2C | 122.7 (2) | C20C—C21C—H21B | 109.5 |
O1C—C3C—C4C | 122.5 (2) | H21A—C21C—H21B | 109.5 |
C2C—C3C—C4C | 114.78 (16) | C20C—C21C—H21C | 109.5 |
C24C—O4C—H4CC | 109.5 | H21A—C21C—H21C | 109.5 |
C24B—O4B—H4BC | 109.5 | H21B—C21C—H21C | 109.5 |
C3C—C4C—C5C | 113.44 (17) | C20B—C21B—H21D | 109.5 |
C3C—C4C—H4CA | 108.9 | C20B—C21B—H21E | 109.5 |
C5C—C4C—H4CA | 108.9 | H21D—C21B—H21E | 109.5 |
C3C—C4C—H4CB | 108.9 | C20B—C21B—H21F | 109.5 |
C5C—C4C—H4CB | 108.9 | H21D—C21B—H21F | 109.5 |
H4CA—C4C—H4CB | 107.7 | H21E—C21B—H21F | 109.5 |
C3B—C4B—C5B | 113.26 (16) | C23C—C22C—C20C | 115.80 (15) |
C3B—C4B—H4BA | 108.9 | C23C—C22C—H22A | 108.3 |
C5B—C4B—H4BA | 108.9 | C20C—C22C—H22A | 108.3 |
C3B—C4B—H4BB | 108.9 | C23C—C22C—H22B | 108.3 |
C5B—C4B—H4BB | 108.9 | C20C—C22C—H22B | 108.3 |
H4BA—C4B—H4BB | 107.7 | H22A—C22C—H22B | 107.4 |
C4B—C5B—C6B | 108.46 (15) | C23B—C22B—C20B | 115.66 (16) |
C4B—C5B—C10B | 113.23 (15) | C23B—C22B—H22C | 108.4 |
C6B—C5B—C10B | 112.40 (15) | C20B—C22B—H22C | 108.4 |
C4B—C5B—H5BA | 107.5 | C23B—C22B—H22D | 108.4 |
C6B—C5B—H5BA | 107.5 | C20B—C22B—H22D | 108.4 |
C10B—C5B—H5BA | 107.5 | H22C—C22B—H22D | 107.4 |
C4C—C5C—C10C | 113.39 (16) | C24C—C23C—C22C | 111.56 (15) |
C4C—C5C—C6C | 108.93 (16) | C24C—C23C—H23A | 109.3 |
C10C—C5C—C6C | 112.31 (15) | C22C—C23C—H23A | 109.3 |
C4C—C5C—H5CA | 107.3 | C24C—C23C—H23B | 109.3 |
C10C—C5C—H5CA | 107.3 | C22C—C23C—H23B | 109.3 |
C6C—C5C—H5CA | 107.3 | H23A—C23C—H23B | 108.0 |
C7B—C6B—C5B | 108.55 (15) | C24B—C23B—C22B | 115.41 (16) |
C7B—C6B—H6BA | 110.0 | C24B—C23B—H23C | 108.4 |
C5B—C6B—H6BA | 110.0 | C22B—C23B—H23C | 108.4 |
C7B—C6B—H6BB | 110.0 | C24B—C23B—H23D | 108.4 |
C5B—C6B—H6BB | 110.0 | C22B—C23B—H23D | 108.4 |
H6BA—C6B—H6BB | 108.4 | H23C—C23B—H23D | 107.5 |
C7C—C6C—C5C | 110.51 (15) | O3C—C24C—O4C | 122.61 (17) |
C7C—C6C—H6CA | 109.5 | O3C—C24C—C23C | 123.81 (17) |
C5C—C6C—H6CA | 109.5 | O4C—C24C—C23C | 113.56 (16) |
C7C—C6C—H6CB | 109.5 | O3B—C24B—O4B | 123.41 (17) |
C5C—C6C—H6CB | 109.5 | O3B—C24B—C23B | 124.62 (17) |
H6CA—C6C—H6CB | 108.1 | O4B—C24B—C23B | 111.93 (16) |
O2C—C7C—C8C | 123.44 (17) | C2A—C1A—C10A | 114.32 (16) |
O2C—C7C—C6C | 121.87 (17) | C2A—C1A—H1AA | 108.7 |
C8C—C7C—C6C | 114.55 (16) | C10A—C1A—H1AA | 108.7 |
O2B—C7B—C6B | 122.75 (18) | C2A—C1A—H1AB | 108.7 |
O2B—C7B—C8B | 123.16 (17) | C10A—C1A—H1AB | 108.7 |
C6B—C7B—C8B | 113.73 (16) | H1AA—C1A—H1AB | 107.6 |
C7C—C8C—C14C | 114.34 (15) | C3A—C2A—C1A | 107.91 (17) |
C7C—C8C—C9C | 106.09 (14) | C3A—C2A—H2AA | 110.1 |
C14C—C8C—C9C | 111.29 (14) | C1A—C2A—H2AA | 110.1 |
C7C—C8C—H8CA | 108.3 | C3A—C2A—H2AB | 110.1 |
C14C—C8C—H8CA | 108.3 | C1A—C2A—H2AB | 110.1 |
C9C—C8C—H8CA | 108.3 | H2AA—C2A—H2AB | 108.4 |
C7B—C8B—C14B | 114.92 (15) | O1A—C3A—C2A | 123.4 (2) |
C7B—C8B—C9B | 105.39 (14) | O1A—C3A—C4A | 122.0 (2) |
C14B—C8B—C9B | 110.93 (14) | C2A—C3A—C4A | 114.55 (16) |
C7B—C8B—H8BA | 108.5 | C24A—O4A—H4AC | 109.5 |
C14B—C8B—H8BA | 108.5 | C3A—C4A—C5A | 112.47 (17) |
C9B—C8B—H8BA | 108.5 | C3A—C4A—H4AA | 109.1 |
C11C—C9C—C10C | 113.73 (15) | C5A—C4A—H4AA | 109.1 |
C11C—C9C—C8C | 112.73 (13) | C3A—C4A—H4AB | 109.1 |
C10C—C9C—C8C | 111.19 (14) | C5A—C4A—H4AB | 109.1 |
C11C—C9C—H9CA | 106.2 | H4AA—C4A—H4AB | 107.8 |
C10C—C9C—H9CA | 106.2 | C6A—C5A—C4A | 109.03 (16) |
C8C—C9C—H9CA | 106.2 | C6A—C5A—C10A | 112.50 (16) |
C11B—C9B—C10B | 113.68 (15) | C4A—C5A—C10A | 113.16 (16) |
C11B—C9B—C8B | 111.97 (14) | C6A—C5A—H5AA | 107.3 |
C10B—C9B—C8B | 111.69 (14) | C4A—C5A—H5AA | 107.3 |
C11B—C9B—H9BA | 106.3 | C10A—C5A—H5AA | 107.3 |
C10B—C9B—H9BA | 106.3 | C7A—C6A—C5A | 111.04 (15) |
C8B—C9B—H9BA | 106.3 | C7A—C6A—H6AA | 109.4 |
C1B—C10B—C19B | 106.17 (16) | C5A—C6A—H6AA | 109.4 |
C1B—C10B—C5B | 108.32 (15) | C7A—C6A—H6AB | 109.4 |
C19B—C10B—C5B | 109.03 (15) | C5A—C6A—H6AB | 109.4 |
C1B—C10B—C9B | 111.76 (15) | H6AA—C6A—H6AB | 108.0 |
C19B—C10B—C9B | 111.42 (15) | O2A—C7A—C8A | 123.52 (18) |
C5B—C10B—C9B | 110.01 (15) | O2A—C7A—C6A | 122.16 (18) |
C1C—C10C—C19C | 106.67 (15) | C8A—C7A—C6A | 114.23 (16) |
C1C—C10C—C5C | 108.12 (14) | C7A—C8A—C14A | 114.57 (15) |
C19C—C10C—C5C | 109.11 (15) | C7A—C8A—C9A | 106.72 (15) |
C1C—C10C—C9C | 111.08 (15) | C14A—C8A—C9A | 111.38 (15) |
C19C—C10C—C9C | 111.88 (14) | C7A—C8A—H8AA | 108.0 |
C5C—C10C—C9C | 109.85 (14) | C14A—C8A—H8AA | 108.0 |
C9C—C11C—C12C | 114.28 (15) | C9A—C8A—H8AA | 108.0 |
C9C—C11C—H11A | 108.7 | C11A—C9A—C8A | 113.11 (15) |
C12C—C11C—H11A | 108.7 | C11A—C9A—C10A | 113.21 (16) |
C9C—C11C—H11B | 108.7 | C8A—C9A—C10A | 110.92 (15) |
C12C—C11C—H11B | 108.7 | C11A—C9A—H9AA | 106.3 |
H11A—C11C—H11B | 107.6 | C8A—C9A—H9AA | 106.3 |
C9B—C11B—C12B | 114.77 (15) | C10A—C9A—H9AA | 106.3 |
C9B—C11B—H11C | 108.6 | C1A—C10A—C19A | 106.12 (16) |
C12B—C11B—H11C | 108.6 | C1A—C10A—C5A | 108.21 (15) |
C9B—C11B—H11D | 108.6 | C19A—C10A—C5A | 108.75 (16) |
C12B—C11B—H11D | 108.6 | C1A—C10A—C9A | 112.01 (15) |
H11C—C11B—H11D | 107.5 | C19A—C10A—C9A | 111.68 (15) |
C13B—C12B—C11B | 111.78 (15) | C5A—C10A—C9A | 109.92 (15) |
C13B—C12B—H12A | 109.3 | C9A—C11A—C12A | 114.06 (16) |
C11B—C12B—H12A | 109.3 | C9A—C11A—H11E | 108.7 |
C13B—C12B—H12B | 109.3 | C12A—C11A—H11E | 108.7 |
C11B—C12B—H12B | 109.3 | C9A—C11A—H11F | 108.7 |
H12A—C12B—H12B | 107.9 | C12A—C11A—H11F | 108.7 |
C13C—C12C—C11C | 111.42 (15) | H11E—C11A—H11F | 107.6 |
C13C—C12C—H12C | 109.3 | C13A—C12A—C11A | 111.88 (16) |
C11C—C12C—H12C | 109.3 | C13A—C12A—H12E | 109.2 |
C13C—C12C—H12D | 109.3 | C11A—C12A—H12E | 109.2 |
C11C—C12C—H12D | 109.3 | C13A—C12A—H12F | 109.2 |
H12C—C12C—H12D | 108.0 | C11A—C12A—H12F | 109.2 |
C18C—C13C—C12C | 110.89 (15) | H12E—C12A—H12F | 107.9 |
C18C—C13C—C14C | 112.43 (15) | C12A—C13A—C18A | 110.93 (16) |
C12C—C13C—C14C | 106.41 (14) | C12A—C13A—C14A | 106.70 (15) |
C18C—C13C—C17C | 109.50 (14) | C18A—C13A—C14A | 111.99 (15) |
C12C—C13C—C17C | 117.06 (15) | C12A—C13A—C17A | 117.80 (16) |
C14C—C13C—C17C | 100.12 (14) | C18A—C13A—C17A | 108.82 (15) |
C12B—C13B—C18B | 110.64 (15) | C14A—C13A—C17A | 100.13 (14) |
C12B—C13B—C14B | 106.47 (14) | C8A—C14A—C15A | 117.81 (15) |
C18B—C13B—C14B | 111.74 (14) | C8A—C14A—C13A | 113.13 (15) |
C12B—C13B—C17B | 116.62 (14) | C15A—C14A—C13A | 104.93 (15) |
C18B—C13B—C17B | 109.38 (14) | C8A—C14A—H14C | 106.8 |
C14B—C13B—C17B | 101.64 (14) | C15A—C14A—H14C | 106.8 |
C8C—C14C—C15C | 117.57 (15) | C13A—C14A—H14C | 106.8 |
C8C—C14C—C13C | 112.62 (14) | C14A—C15A—C16A | 104.34 (15) |
C15C—C14C—C13C | 104.87 (14) | C14A—C15A—H15E | 110.9 |
C8C—C14C—H14A | 107.1 | C16A—C15A—H15E | 110.9 |
C15C—C14C—H14A | 107.1 | C14A—C15A—H15F | 110.9 |
C13C—C14C—H14A | 107.1 | C16A—C15A—H15F | 110.9 |
C8B—C14B—C15B | 118.51 (15) | H15E—C15A—H15F | 108.9 |
C8B—C14B—C13B | 112.51 (14) | C15A—C16A—C17A | 106.82 (15) |
C15B—C14B—C13B | 103.92 (14) | C15A—C16A—H16E | 110.4 |
C8B—C14B—H14B | 107.1 | C17A—C16A—H16E | 110.4 |
C15B—C14B—H14B | 107.1 | C15A—C16A—H16F | 110.4 |
C13B—C14B—H14B | 107.1 | C17A—C16A—H16F | 110.4 |
C14B—C15B—C16B | 104.39 (14) | H16E—C16A—H16F | 108.6 |
C14B—C15B—H15A | 110.9 | C20A—C17A—C16A | 112.60 (15) |
C16B—C15B—H15A | 110.9 | C20A—C17A—C13A | 119.43 (15) |
C14B—C15B—H15B | 110.9 | C16A—C17A—C13A | 103.25 (15) |
C16B—C15B—H15B | 110.9 | C20A—C17A—H17C | 107.0 |
H15A—C15B—H15B | 108.9 | C16A—C17A—H17C | 107.0 |
C14C—C15C—C16C | 103.66 (14) | C13A—C17A—H17C | 107.0 |
C14C—C15C—H15C | 111.0 | C13A—C18A—H18G | 109.5 |
C16C—C15C—H15C | 111.0 | C13A—C18A—H18H | 109.5 |
C14C—C15C—H15D | 111.0 | H18G—C18A—H18H | 109.5 |
C16C—C15C—H15D | 111.0 | C13A—C18A—H18I | 109.5 |
H15C—C15C—H15D | 109.0 | H18G—C18A—H18I | 109.5 |
C15C—C16C—C17C | 107.15 (14) | H18H—C18A—H18I | 109.5 |
C15C—C16C—H16A | 110.3 | C10A—C19A—H19G | 109.5 |
C17C—C16C—H16A | 110.3 | C10A—C19A—H19H | 109.5 |
C15C—C16C—H16B | 110.3 | H19G—C19A—H19H | 109.5 |
C17C—C16C—H16B | 110.3 | C10A—C19A—H19I | 109.5 |
H16A—C16C—H16B | 108.5 | H19G—C19A—H19I | 109.5 |
C15B—C16B—C17B | 107.07 (15) | H19H—C19A—H19I | 109.5 |
C15B—C16B—H16C | 110.3 | C21A—C20A—C22A | 110.66 (17) |
C17B—C16B—H16C | 110.3 | C21A—C20A—C17A | 111.67 (16) |
C15B—C16B—H16D | 110.3 | C22A—C20A—C17A | 109.64 (15) |
C17B—C16B—H16D | 110.3 | C21A—C20A—H20C | 108.3 |
H16C—C16B—H16D | 108.6 | C22A—C20A—H20C | 108.3 |
C20B—C17B—C13B | 118.16 (15) | C17A—C20A—H20C | 108.3 |
C20B—C17B—C16B | 111.81 (14) | C20A—C21A—H21G | 109.5 |
C13B—C17B—C16B | 103.63 (14) | C20A—C21A—H21H | 109.5 |
C20B—C17B—H17A | 107.6 | H21G—C21A—H21H | 109.5 |
C13B—C17B—H17A | 107.6 | C20A—C21A—H21I | 109.5 |
C16B—C17B—H17A | 107.6 | H21G—C21A—H21I | 109.5 |
C20C—C17C—C13C | 118.82 (14) | H21H—C21A—H21I | 109.5 |
C20C—C17C—C16C | 111.66 (14) | C23A—C22A—C20A | 117.15 (16) |
C13C—C17C—C16C | 103.62 (14) | C23A—C22A—H22E | 108.0 |
C20C—C17C—H17B | 107.4 | C20A—C22A—H22E | 108.0 |
C13C—C17C—H17B | 107.4 | C23A—C22A—H22F | 108.0 |
C16C—C17C—H17B | 107.4 | C20A—C22A—H22F | 108.0 |
C13B—C18B—H18A | 109.5 | H22E—C22A—H22F | 107.3 |
C13B—C18B—H18B | 109.5 | C24A—C23A—C22A | 116.59 (18) |
H18A—C18B—H18B | 109.5 | C24A—C23A—H23E | 108.1 |
C13B—C18B—H18C | 109.5 | C22A—C23A—H23E | 108.1 |
H18A—C18B—H18C | 109.5 | C24A—C23A—H23F | 108.1 |
H18B—C18B—H18C | 109.5 | C22A—C23A—H23F | 108.1 |
C13C—C18C—H18D | 109.5 | H23E—C23A—H23F | 107.3 |
C13C—C18C—H18E | 109.5 | O3A—C24A—O4A | 122.06 (19) |
H18D—C18C—H18E | 109.5 | O3A—C24A—C23A | 124.19 (19) |
C13C—C18C—H18F | 109.5 | O4A—C24A—C23A | 113.73 (17) |
C10B—C1B—C2B—C3B | 56.0 (2) | C14B—C15B—C16B—C17B | 10.99 (19) |
C10C—C1C—C2C—C3C | 58.6 (2) | C12B—C13B—C17B—C20B | 83.72 (19) |
C1B—C2B—C3B—O1B | 127.5 (2) | C18B—C13B—C17B—C20B | −42.7 (2) |
C1B—C2B—C3B—C4B | −51.5 (2) | C14B—C13B—C17B—C20B | −160.99 (14) |
C1C—C2C—C3C—O1C | 123.7 (2) | C12B—C13B—C17B—C16B | −151.99 (15) |
C1C—C2C—C3C—C4C | −53.7 (2) | C18B—C13B—C17B—C16B | 81.55 (17) |
O1C—C3C—C4C—C5C | −127.2 (2) | C14B—C13B—C17B—C16B | −36.70 (16) |
C2C—C3C—C4C—C5C | 50.3 (2) | C15B—C16B—C17B—C20B | 144.54 (15) |
O1B—C3B—C4B—C5B | −129.71 (19) | C15B—C16B—C17B—C13B | 16.23 (18) |
C2B—C3B—C4B—C5B | 49.3 (2) | C18C—C13C—C17C—C20C | −45.6 (2) |
C3B—C4B—C5B—C6B | −174.40 (15) | C12C—C13C—C17C—C20C | 81.7 (2) |
C3B—C4B—C5B—C10B | −48.9 (2) | C14C—C13C—C17C—C20C | −163.91 (15) |
C3C—C4C—C5C—C10C | −47.8 (2) | C18C—C13C—C17C—C16C | 78.94 (17) |
C3C—C4C—C5C—C6C | −173.61 (17) | C12C—C13C—C17C—C16C | −153.80 (15) |
C4B—C5B—C6B—C7B | 72.01 (19) | C14C—C13C—C17C—C16C | −39.38 (16) |
C10B—C5B—C6B—C7B | −54.0 (2) | C15C—C16C—C17C—C20C | 149.29 (14) |
C4C—C5C—C6C—C7C | 75.5 (2) | C15C—C16C—C17C—C13C | 20.25 (18) |
C10C—C5C—C6C—C7C | −51.0 (2) | C13B—C17B—C20B—C21B | −58.9 (2) |
C5C—C6C—C7C—O2C | −118.9 (2) | C16B—C17B—C20B—C21B | −179.04 (15) |
C5C—C6C—C7C—C8C | 56.9 (2) | C13B—C17B—C20B—C22B | 177.52 (15) |
C5B—C6B—C7B—O2B | −111.5 (2) | C16B—C17B—C20B—C22B | 57.39 (19) |
C5B—C6B—C7B—C8B | 61.76 (19) | C13C—C17C—C20C—C22C | 176.80 (15) |
O2C—C7C—C8C—C14C | −7.9 (3) | C16C—C17C—C20C—C22C | 56.29 (19) |
C6C—C7C—C8C—C14C | 176.32 (15) | C13C—C17C—C20C—C21C | −60.4 (2) |
O2C—C7C—C8C—C9C | 115.09 (19) | C16C—C17C—C20C—C21C | 179.12 (14) |
C6C—C7C—C8C—C9C | −60.65 (19) | C17C—C20C—C22C—C23C | −177.34 (15) |
O2B—C7B—C8B—C14B | −12.8 (3) | C21C—C20C—C22C—C23C | 58.8 (2) |
C6B—C7B—C8B—C14B | 173.92 (15) | C21B—C20B—C22B—C23B | 62.3 (2) |
O2B—C7B—C8B—C9B | 109.62 (19) | C17B—C20B—C22B—C23B | −172.55 (15) |
C6B—C7B—C8B—C9B | −63.64 (18) | C20C—C22C—C23C—C24C | −174.27 (16) |
C7C—C8C—C9C—C11C | −170.62 (15) | C20B—C22B—C23B—C24B | 67.2 (2) |
C14C—C8C—C9C—C11C | −45.69 (19) | C22C—C23C—C24C—O3C | −6.9 (3) |
C7C—C8C—C9C—C10C | 60.30 (18) | C22C—C23C—C24C—O4C | 171.78 (16) |
C14C—C8C—C9C—C10C | −174.77 (14) | C22B—C23B—C24B—O3B | −0.3 (3) |
C7B—C8B—C9B—C11B | −171.88 (14) | C22B—C23B—C24B—O4B | 177.66 (17) |
C14B—C8B—C9B—C11B | −46.91 (19) | C10A—C1A—C2A—C3A | 58.7 (2) |
C7B—C8B—C9B—C10B | 59.32 (18) | C1A—C2A—C3A—O1A | 121.6 (2) |
C14B—C8B—C9B—C10B | −175.71 (14) | C1A—C2A—C3A—C4A | −55.3 (2) |
C2B—C1B—C10B—C19B | −172.97 (16) | O1A—C3A—C4A—C5A | −124.6 (2) |
C2B—C1B—C10B—C5B | −56.0 (2) | C2A—C3A—C4A—C5A | 52.2 (2) |
C2B—C1B—C10B—C9B | 65.4 (2) | C3A—C4A—C5A—C6A | −175.23 (16) |
C4B—C5B—C10B—C1B | 51.3 (2) | C3A—C4A—C5A—C10A | −49.2 (2) |
C6B—C5B—C10B—C1B | 174.63 (15) | C4A—C5A—C6A—C7A | 76.3 (2) |
C4B—C5B—C10B—C19B | 166.41 (16) | C10A—C5A—C6A—C7A | −50.1 (2) |
C6B—C5B—C10B—C19B | −70.25 (19) | C5A—C6A—C7A—O2A | −121.0 (2) |
C4B—C5B—C10B—C9B | −71.13 (19) | C5A—C6A—C7A—C8A | 55.8 (2) |
C6B—C5B—C10B—C9B | 52.21 (19) | O2A—C7A—C8A—C14A | −7.3 (3) |
C11B—C9B—C10B—C1B | 56.18 (19) | C6A—C7A—C8A—C14A | 175.96 (15) |
C8B—C9B—C10B—C1B | −175.94 (14) | O2A—C7A—C8A—C9A | 116.4 (2) |
C11B—C9B—C10B—C19B | −62.4 (2) | C6A—C7A—C8A—C9A | −60.27 (19) |
C8B—C9B—C10B—C19B | 65.5 (2) | C7A—C8A—C9A—C11A | −170.83 (16) |
C11B—C9B—C10B—C5B | 176.54 (14) | C14A—C8A—C9A—C11A | −45.1 (2) |
C8B—C9B—C10B—C5B | −55.58 (18) | C7A—C8A—C9A—C10A | 60.71 (18) |
C2C—C1C—C10C—C19C | −174.22 (16) | C14A—C8A—C9A—C10A | −173.57 (15) |
C2C—C1C—C10C—C5C | −57.0 (2) | C2A—C1A—C10A—C19A | −173.26 (17) |
C2C—C1C—C10C—C9C | 63.6 (2) | C2A—C1A—C10A—C5A | −56.7 (2) |
C4C—C5C—C10C—C1C | 49.7 (2) | C2A—C1A—C10A—C9A | 64.6 (2) |
C6C—C5C—C10C—C1C | 173.72 (15) | C6A—C5A—C10A—C1A | 174.47 (16) |
C4C—C5C—C10C—C19C | 165.35 (16) | C4A—C5A—C10A—C1A | 50.3 (2) |
C6C—C5C—C10C—C19C | −70.63 (19) | C6A—C5A—C10A—C19A | −70.7 (2) |
C4C—C5C—C10C—C9C | −71.66 (19) | C4A—C5A—C10A—C19A | 165.20 (17) |
C6C—C5C—C10C—C9C | 52.36 (19) | C6A—C5A—C10A—C9A | 51.9 (2) |
C11C—C9C—C10C—C1C | 53.83 (19) | C4A—C5A—C10A—C9A | −72.3 (2) |
C8C—C9C—C10C—C1C | −177.62 (14) | C11A—C9A—C10A—C1A | 53.3 (2) |
C11C—C9C—C10C—C19C | −65.3 (2) | C8A—C9A—C10A—C1A | −178.32 (15) |
C8C—C9C—C10C—C19C | 63.3 (2) | C11A—C9A—C10A—C19A | −65.6 (2) |
C11C—C9C—C10C—C5C | 173.40 (15) | C8A—C9A—C10A—C19A | 62.8 (2) |
C8C—C9C—C10C—C5C | −58.05 (18) | C11A—C9A—C10A—C5A | 173.61 (16) |
C10C—C9C—C11C—C12C | 172.74 (15) | C8A—C9A—C10A—C5A | −57.99 (19) |
C8C—C9C—C11C—C12C | 45.0 (2) | C8A—C9A—C11A—C12A | 44.4 (2) |
C10B—C9B—C11B—C12B | 172.84 (15) | C10A—C9A—C11A—C12A | 171.68 (16) |
C8B—C9B—C11B—C12B | 45.1 (2) | C9A—C11A—C12A—C13A | −53.0 (2) |
C9B—C11B—C12B—C13B | −52.7 (2) | C11A—C12A—C13A—C18A | −62.9 (2) |
C9C—C11C—C12C—C13C | −53.6 (2) | C11A—C12A—C13A—C14A | 59.4 (2) |
C11C—C12C—C13C—C18C | −62.5 (2) | C11A—C12A—C13A—C17A | 170.83 (16) |
C11C—C12C—C13C—C14C | 60.06 (18) | C7A—C8A—C14A—C15A | −60.4 (2) |
C11C—C12C—C13C—C17C | 170.91 (15) | C9A—C8A—C14A—C15A | 178.40 (15) |
C11B—C12B—C13B—C18B | −62.64 (19) | C7A—C8A—C14A—C13A | 176.82 (15) |
C11B—C12B—C13B—C14B | 58.97 (18) | C9A—C8A—C14A—C13A | 55.58 (19) |
C11B—C12B—C13B—C17B | 171.53 (15) | C12A—C13A—C14A—C8A | −62.32 (19) |
C7C—C8C—C14C—C15C | −61.3 (2) | C18A—C13A—C14A—C8A | 59.2 (2) |
C9C—C8C—C14C—C15C | 178.53 (15) | C17A—C13A—C14A—C8A | 174.43 (14) |
C7C—C8C—C14C—C13C | 176.62 (15) | C12A—C13A—C14A—C15A | 167.96 (15) |
C9C—C8C—C14C—C13C | 56.45 (18) | C18A—C13A—C14A—C15A | −70.48 (19) |
C18C—C13C—C14C—C8C | 58.39 (19) | C17A—C13A—C14A—C15A | 44.71 (16) |
C12C—C13C—C14C—C8C | −63.19 (18) | C8A—C14A—C15A—C16A | −157.44 (16) |
C17C—C13C—C14C—C8C | 174.52 (14) | C13A—C14A—C15A—C16A | −30.55 (18) |
C18C—C13C—C14C—C15C | −70.61 (18) | C14A—C15A—C16A—C17A | 4.13 (19) |
C12C—C13C—C14C—C15C | 167.81 (14) | C15A—C16A—C17A—C20A | 153.45 (15) |
C17C—C13C—C14C—C15C | 45.52 (16) | C15A—C16A—C17A—C13A | 23.30 (18) |
C7B—C8B—C14B—C15B | −61.1 (2) | C12A—C13A—C17A—C20A | 78.1 (2) |
C9B—C8B—C14B—C15B | 179.51 (15) | C18A—C13A—C17A—C20A | −49.2 (2) |
C7B—C8B—C14B—C13B | 177.49 (14) | C14A—C13A—C17A—C20A | −166.79 (15) |
C9B—C8B—C14B—C13B | 58.08 (18) | C12A—C13A—C17A—C16A | −156.02 (16) |
C12B—C13B—C14B—C8B | −63.49 (18) | C18A—C13A—C17A—C16A | 76.66 (18) |
C18B—C13B—C14B—C8B | 57.42 (19) | C14A—C13A—C17A—C16A | −40.91 (16) |
C17B—C13B—C14B—C8B | 173.96 (14) | C16A—C17A—C20A—C21A | −179.13 (16) |
C12B—C13B—C14B—C15B | 167.10 (14) | C13A—C17A—C20A—C21A | −57.8 (2) |
C18B—C13B—C14B—C15B | −72.00 (17) | C16A—C17A—C20A—C22A | 57.8 (2) |
C17B—C13B—C14B—C15B | 44.55 (16) | C13A—C17A—C20A—C22A | 179.17 (16) |
C8B—C14B—C15B—C16B | −160.06 (16) | C21A—C20A—C22A—C23A | 61.1 (2) |
C13B—C14B—C15B—C16B | −34.37 (18) | C17A—C20A—C22A—C23A | −175.30 (17) |
C8C—C14C—C15C—C16C | −159.10 (15) | C20A—C22A—C23A—C24A | 80.2 (2) |
C13C—C14C—C15C—C16C | −33.11 (17) | C22A—C23A—C24A—O3A | 129.8 (2) |
C14C—C15C—C16C—C17C | 7.62 (18) | C22A—C23A—C24A—O4A | −51.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H1AA···O1Bi | 0.99 | 2.69 | 3.145 (2) | 108 |
C4A—H4AA···O2Cii | 0.99 | 2.57 | 3.369 (2) | 137 |
C6A—H6AA···O4Aiii | 0.99 | 2.62 | 3.345 (2) | 130 |
C11A—H11F···O2Aiv | 0.99 | 2.67 | 3.495 (2) | 141 |
C16A—H16E···O3Cii | 0.99 | 2.60 | 3.459 (2) | 145 |
C22A—H22E···O3Cii | 0.99 | 2.67 | 3.527 (3) | 145 |
C1C—H1CA···O4Cv | 0.99 | 2.65 | 3.070 (2) | 106 |
C2C—H2CA···O4Cv | 0.99 | 2.65 | 3.297 (2) | 123 |
C11B—H11D···O2Biv | 0.99 | 2.58 | 3.095 (2) | 113 |
C19B—H19D···O1Cvi | 0.98 | 2.54 | 3.434 (2) | 152 |
C6C—H6CB···O4Cvii | 0.99 | 2.66 | 3.223 (2) | 117 |
C14C—H14A···O2Aviii | 1.00 | 2.64 | 3.593 (2) | 161 |
O4A—H4AC···O1B | 0.84 | 1.87 | 2.7055 (19) | 180 |
O4B—H4BC···O3C | 0.84 | 1.81 | 2.6485 (19) | 178 |
O4C—H4CC···O3B | 0.84 | 1.82 | 2.6598 (18) | 178 |
Symmetry codes: (i) x−1/2, −y−1/2, −z; (ii) x+1/2, −y+1/2, −z; (iii) x+1/2, −y−1/2, −z; (iv) x−1, y, z; (v) −x+1, y+1/2, −z+1/2; (vi) x, y−1, z; (vii) −x, y+1/2, −z+1/2; (viii) x−1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C24H36O4 |
Mr | 388.53 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 100 |
a, b, c (Å) | 7.6177 (1), 27.6911 (4), 29.9256 (4) |
V (Å3) | 6312.58 (15) |
Z | 12 |
Radiation type | Cu Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.22 × 0.13 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD APEX II area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.871, 0.927 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27061, 10459, 9648 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.608 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.091, 1.07 |
No. of reflections | 10459 |
No. of parameters | 758 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.16 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.14 (13) |
Computer programs: SMART (Bruker, 2000), SMART, SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
O3B—C24B | 1.218 (2) | O4B—C24B | 1.318 (2) |
O3C—C24C | 1.214 (2) | O3A—C24A | 1.210 (2) |
O4C—C24C | 1.317 (2) | O4A—C24A | 1.326 (2) |
O3C—C24C—C23C | 123.81 (17) | O4B—C24B—C23B | 111.93 (16) |
O4C—C24C—C23C | 113.56 (16) | O3A—C24A—C23A | 124.19 (19) |
O3B—C24B—C23B | 124.62 (17) | O4A—C24A—C23A | 113.73 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H1AA···O1Bi | 0.99 | 2.69 | 3.145 (2) | 108 |
C4A—H4AA···O2Cii | 0.99 | 2.57 | 3.369 (2) | 137 |
C6A—H6AA···O4Aiii | 0.99 | 2.62 | 3.345 (2) | 130 |
C11A—H11F···O2Aiv | 0.99 | 2.67 | 3.495 (2) | 141 |
C16A—H16E···O3Cii | 0.99 | 2.60 | 3.459 (2) | 145 |
C22A—H22E···O3Cii | 0.99 | 2.67 | 3.527 (3) | 145 |
C1C—H1CA···O4Cv | 0.99 | 2.65 | 3.070 (2) | 106 |
C2C—H2CA···O4Cv | 0.99 | 2.65 | 3.297 (2) | 123 |
C11B—H11D···O2Biv | 0.99 | 2.58 | 3.095 (2) | 113 |
C19B—H19D···O1Cvi | 0.98 | 2.54 | 3.434 (2) | 152 |
C6C—H6CB···O4Cvii | 0.99 | 2.66 | 3.223 (2) | 117 |
C14C—H14A···O2Aviii | 1.00 | 2.64 | 3.593 (2) | 161 |
O4A—H4AC···O1B | 0.84 | 1.87 | 2.7055 (19) | 180 |
O4B—H4BC···O3C | 0.84 | 1.81 | 2.6485 (19) | 178 |
O4C—H4CC···O3B | 0.84 | 1.82 | 2.6598 (18) | 178 |
Symmetry codes: (i) x−1/2, −y−1/2, −z; (ii) x+1/2, −y+1/2, −z; (iii) x+1/2, −y−1/2, −z; (iv) x−1, y, z; (v) −x+1, y+1/2, −z+1/2; (vi) x, y−1, z; (vii) −x, y+1/2, −z+1/2; (viii) x−1/2, −y+1/2, −z. |
For our study of H-bonding modes in crystalline keto acids, steroid examples are of special value as molecularly rigid single enantiomers with the potential for multiple ketone receptors. The title compound (I) supplements our previous reports on steroidal diketo acids related to the bile acids (Thompson et al., 2001; Newman et al., 2002; Lalancette & Thompson, 2003). The natural bile acids all have cis AB ring junctures, a carboxyl in the C17 side-chain and oxygenation at the 3-position; most are oxygenated at the 6-, 7- and/or 12-positions as well. Various combinations of these acids are present in substantial quantities in vertebrate bile, where they function as surfactants, and are isolatable directly from gall bladders. Although the ring-oxygenation typically involves hydroxyl groups, a few natural bile acids contain ketone functions as well (Fieser & Fieser, 1959). Compound (I) is not known to occur naturally, but was produced by oxidation of a known natural source (Experimental).
Fig. 1 shows the asymmetric unit for (I), consisting of three molecules, designated (IA), (IB) & (IC), which have significant conformational differences only at the extremity of the 5-carbon acid-chain attached at C17. Superimposition of truncated molecules lacking the carboxyl (C24) and stripped of all H atoms shows negligible differences, with r.m.s. deviations averaging less than 0.1 Å.
All three molecules have an anti conformational arrangement about the C20—C22 bond, but only (IC) also has an anti conformation about C22—C23, whose torsion angle (C20—C22—C23—C24) is −174.27 (16)°. The two remaining molecules have similar gauche arrangements about C22—C23, with the above torsion angle being 80.2 (2)° for (IA) and 67.2 (2)° for (IB). However, these two molecules differ in the conformation of their carboxyl groups; the torsion angle O3—C24—C23—C22 is 129.8 (2)° for (IA) and −0.3 (3)° for (IB).
Values typical of C—O bond lengths and C—C—O angles in highly ordered dimeric carboxyls are 1.21 & 1.31 Å and 123 & 112°, respectively (Borthwick, 1980). Full or partial averaging of these lengths and angles by disorder is common in dimeric acids, but is invariably absent in other H-bonding modes, which cannot support the underlying averaging mechanisms. All the carboxyl groups in (I) show negligible disordering (see Table 1).
Fig. 1 also illustrates the entire H-bonding scheme, which consists of (IA), (IB) & (IC), with no H bonding beyond the three molecules shown. This leaves the two C3 ketone functions at the remote ends of this block without H-bonding partners, as is the case for all the B-ring ketones at C7.
Fig. 2 shows the packing of the cell with the chosen asymmetric unit and includes extra molecules to illustrate its isolation from other H bonding. Within the 2.7 Å range we standardly survey for non-bonded H···O packing interactions (Steiner, 1997), a dozen intermolecular C—H···O close contacts exist (see Table 2).
We characterize the geometry of H bonding to carbonyls using a combination of H···O=C angle and H···O=C—C torsion angle. These describe the approach of the acid H atom to the receptor O in terms of its deviation from, respectively, C=O axiality (ideal = 120°) and planarity with the carbonyl (ideal = 0°). In the acid-to-ketone connection in (I), these two angles are 124.3° and 40.2°.
The solid-state (KBr) infrared spectrum of (I) has broad C=O absorption centered at 1703 cm−1, which is shifted to 1711 cm−1 in CHCl3 solution. In addition, the KBr spectrum contains a much smaller peak at 1653 cm−1, absent in CHCl3 and probably due to the single ketone (of the six in the asymmetric unit) whose position is shifted by H bonding.