The title compound, alisol B monoacetate or 11-hydroxy-24,25-epoxy-3-oxoprotost-13(17)-en-23-yl acetate, C32H50O5, is a protostane-type triterpenoid which was isolated from the Chinese herbal medicine Alismatis Rhizoma (the rhizome of Alisma orientalis Juzep.). The molecule contains three six-membered rings, two of which adopt slightly distorted half-chair conformations while the third exhibits a chair conformation, and one five-membered ring, which adopts an envelope conformation. There is an intermolecular hydrogen bond between the hydroxy and epoxy groups, forming zigzag molecular chains along the b axis.
Supporting information
CCDC reference: 227038
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.086
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C25 - C26 = 7.16 su
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C2
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O5
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C4
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C25
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C31
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 27.50
From the CIF: _reflns_number_total 3990
Count of symmetry unique reflns 3990
Completeness (_total/calc) 100.00%
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
2 ALERT level B = Potentially serious problem
8 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
8 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: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Siemens, 1991); software used to prepare material for publication: SHELXTL/PC.
11-hydroxy-24,25-epoxy-3-oxoprotost-13 (17)-en-23-yl acetate
top
Crystal data top
C32H50O5 | Dx = 1.111 Mg m−3 |
Mr = 514.72 | Melting point: 444(1) K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.716 (1) Å | Cell parameters from 35 reflections |
b = 14.495 (2) Å | θ = 3.1–14.9° |
c = 27.526 (5) Å | µ = 0.07 mm−1 |
V = 3078.6 (8) Å3 | T = 296 K |
Z = 4 | Prisms, colorless |
F(000) = 1128 | 0.56 × 0.56 × 0.46 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.010 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.5° |
Graphite monochromator | h = 0→10 |
ω scans | k = 0→18 |
4120 measured reflections | l = −1→35 |
3990 independent reflections | 3 standard reflections every 97 reflections |
1961 reflections with I > 2σ(I) | intensity decay: 2.3% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.045P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.086 | (Δ/σ)max < 0.001 |
S = 0.80 | Δρmax = 0.11 e Å−3 |
3990 reflections | Δρmin = −0.10 e Å−3 |
346 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0071 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: see text |
Secondary atom site location: difference Fourier map | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.1410 (3) | 1.23849 (15) | 0.07938 (8) | 0.0993 (7) | |
O2 | 0.1038 (2) | 0.86385 (12) | 0.17467 (7) | 0.0665 (5) | |
H2O | 0.1547 | 0.8688 | 0.2007 | 0.143 (17)* | |
O3 | 0.3269 (2) | 0.46639 (12) | 0.21618 (6) | 0.0652 (5) | |
O4 | 0.4181 (3) | 0.59758 (15) | 0.25097 (7) | 0.0846 (6) | |
O5 | 0.7135 (3) | 0.40579 (15) | 0.23722 (6) | 0.0902 (6) | |
C1 | 0.1127 (3) | 0.99191 (18) | 0.08611 (10) | 0.0648 (7) | |
H1A | 0.1048 | 0.9430 | 0.0622 | 0.078* | |
H1B | 0.0281 | 0.9794 | 0.1113 | 0.078* | |
C2 | 0.0690 (4) | 1.0846 (2) | 0.06167 (14) | 0.1076 (12) | |
H2A | 0.0597 | 1.0741 | 0.0270 | 0.129* | |
H2B | −0.0443 | 1.1040 | 0.0730 | 0.129* | |
C3 | 0.1921 (4) | 1.1619 (2) | 0.06958 (10) | 0.0722 (8) | |
C4 | 0.3816 (4) | 1.13999 (18) | 0.06097 (11) | 0.0707 (8) | |
C5 | 0.4169 (3) | 1.03574 (16) | 0.07055 (9) | 0.0551 (6) | |
H5 | 0.3911 | 1.0042 | 0.0399 | 0.066* | |
C6 | 0.6055 (3) | 1.01342 (17) | 0.08183 (12) | 0.0742 (8) | |
H6A | 0.6803 | 1.0490 | 0.0606 | 0.089* | |
H6B | 0.6312 | 1.0308 | 0.1151 | 0.089* | |
C7 | 0.6425 (3) | 0.91142 (17) | 0.07502 (10) | 0.0695 (8) | |
H7A | 0.7430 | 0.8955 | 0.0945 | 0.083* | |
H7B | 0.6729 | 0.9012 | 0.0413 | 0.083* | |
C8 | 0.4934 (3) | 0.84476 (15) | 0.08847 (8) | 0.0496 (6) | |
C9 | 0.3640 (3) | 0.89269 (15) | 0.12418 (7) | 0.0449 (6) | |
H9 | 0.4310 | 0.9032 | 0.1539 | 0.054* | |
C10 | 0.2966 (3) | 0.99142 (15) | 0.10877 (8) | 0.0493 (6) | |
C11 | 0.2182 (3) | 0.82553 (17) | 0.13929 (8) | 0.0529 (6) | |
H11 | 0.1495 | 0.8120 | 0.1102 | 0.063* | |
C12 | 0.2871 (3) | 0.73318 (16) | 0.15891 (8) | 0.0548 (7) | |
H12A | 0.3353 | 0.7427 | 0.1911 | 0.066* | |
H12B | 0.1918 | 0.6899 | 0.1618 | 0.066* | |
C13 | 0.4232 (3) | 0.69298 (16) | 0.12660 (8) | 0.0503 (6) | |
C14 | 0.5714 (3) | 0.75707 (16) | 0.11416 (9) | 0.0547 (6) | |
C15 | 0.6832 (4) | 0.69566 (17) | 0.07991 (10) | 0.0782 (8) | |
H15A | 0.7040 | 0.7273 | 0.0494 | 0.094* | |
H15B | 0.7941 | 0.6823 | 0.0949 | 0.094* | |
C16 | 0.5837 (4) | 0.60685 (18) | 0.07102 (10) | 0.0780 (8) | |
H16A | 0.5446 | 0.6034 | 0.0376 | 0.094* | |
H16B | 0.6556 | 0.5536 | 0.0780 | 0.094* | |
C17 | 0.4319 (3) | 0.61110 (16) | 0.10529 (8) | 0.0535 (6) | |
C18 | 0.3993 (4) | 0.81542 (17) | 0.04167 (8) | 0.0667 (8) | |
H18A | 0.3165 | 0.7681 | 0.0491 | 0.080* | |
H18B | 0.4822 | 0.7922 | 0.0187 | 0.080* | |
H18C | 0.3406 | 0.8677 | 0.0280 | 0.080* | |
C19 | 0.2898 (4) | 1.05037 (17) | 0.15521 (8) | 0.0680 (8) | |
H19A | 0.4050 | 1.0585 | 0.1677 | 0.082* | |
H19B | 0.2197 | 1.0199 | 0.1791 | 0.082* | |
H19C | 0.2406 | 1.1095 | 0.1478 | 0.082* | |
C20 | 0.3108 (4) | 0.53144 (16) | 0.11117 (8) | 0.0605 (7) | |
H20 | 0.2198 | 0.5502 | 0.1339 | 0.073* | |
C21 | 0.2224 (5) | 0.5046 (2) | 0.06310 (9) | 0.0975 (11) | |
H21A | 0.1597 | 0.5566 | 0.0506 | 0.117* | |
H21B | 0.1437 | 0.4544 | 0.0687 | 0.117* | |
H21C | 0.3088 | 0.4859 | 0.0400 | 0.117* | |
C22 | 0.4037 (4) | 0.44743 (16) | 0.13312 (8) | 0.0619 (7) | |
H22A | 0.3231 | 0.3961 | 0.1340 | 0.074* | |
H22B | 0.4985 | 0.4302 | 0.1118 | 0.074* | |
C23 | 0.4752 (3) | 0.46240 (18) | 0.18381 (8) | 0.0561 (6) | |
H23 | 0.5391 | 0.5208 | 0.1851 | 0.067* | |
C24 | 0.5881 (4) | 0.3857 (2) | 0.20006 (9) | 0.0682 (8) | |
H24 | 0.5284 | 0.3265 | 0.2040 | 0.082* | |
C25 | 0.7731 (4) | 0.3780 (2) | 0.18956 (10) | 0.0792 (9) | |
C26 | 0.8660 (4) | 0.4522 (3) | 0.16269 (11) | 0.1160 (13) | |
H26A | 0.8183 | 0.5111 | 0.1714 | 0.139* | |
H26B | 0.8527 | 0.4426 | 0.1284 | 0.139* | |
H26C | 0.9868 | 0.4507 | 0.1710 | 0.139* | |
C27 | 0.8574 (5) | 0.2855 (2) | 0.18818 (13) | 0.1227 (13) | |
H27A | 0.9742 | 0.2905 | 0.1999 | 0.147* | |
H27B | 0.8586 | 0.2630 | 0.1554 | 0.147* | |
H27C | 0.7938 | 0.2434 | 0.2084 | 0.147* | |
C28 | 0.4936 (4) | 1.20606 (19) | 0.09086 (15) | 0.1138 (13) | |
H28A | 0.4580 | 1.2684 | 0.0847 | 0.137* | |
H28B | 0.6130 | 1.1987 | 0.0818 | 0.137* | |
H28C | 0.4801 | 1.1925 | 0.1248 | 0.137* | |
C29 | 0.4127 (6) | 1.1604 (2) | 0.00692 (12) | 0.1233 (15) | |
H29A | 0.3375 | 1.1226 | −0.0124 | 0.148* | |
H29B | 0.5312 | 1.1471 | −0.0011 | 0.148* | |
H29C | 0.3890 | 1.2243 | 0.0005 | 0.148* | |
C30 | 0.6744 (4) | 0.77881 (19) | 0.16060 (10) | 0.0763 (8) | |
H30A | 0.6044 | 0.8154 | 0.1820 | 0.092* | |
H30B | 0.7775 | 0.8124 | 0.1523 | 0.092* | |
H30C | 0.7057 | 0.7222 | 0.1765 | 0.092* | |
C31 | 0.3155 (4) | 0.5357 (2) | 0.24799 (9) | 0.0641 (7) | |
C32 | 0.1559 (4) | 0.5270 (2) | 0.27812 (10) | 0.0958 (10) | |
H32A | 0.1688 | 0.5629 | 0.3072 | 0.115* | |
H32B | 0.1380 | 0.4635 | 0.2865 | 0.115* | |
H32C | 0.0580 | 0.5492 | 0.2600 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1017 (17) | 0.0812 (14) | 0.1151 (17) | 0.0312 (14) | 0.0119 (15) | 0.0120 (13) |
O2 | 0.0557 (11) | 0.0767 (12) | 0.0673 (12) | −0.0033 (10) | 0.0226 (11) | −0.0059 (10) |
O3 | 0.0677 (12) | 0.0661 (11) | 0.0617 (10) | −0.0121 (11) | 0.0147 (10) | −0.0034 (10) |
O4 | 0.0896 (15) | 0.0840 (14) | 0.0803 (13) | −0.0118 (15) | 0.0070 (13) | −0.0177 (11) |
O5 | 0.0965 (15) | 0.1173 (16) | 0.0570 (11) | 0.0167 (15) | 0.0002 (12) | 0.0066 (11) |
C1 | 0.0511 (16) | 0.0728 (18) | 0.0705 (17) | −0.0066 (15) | −0.0042 (15) | 0.0021 (15) |
C2 | 0.082 (2) | 0.098 (2) | 0.143 (3) | −0.010 (2) | −0.034 (2) | 0.034 (2) |
C3 | 0.074 (2) | 0.074 (2) | 0.0690 (18) | 0.0044 (19) | 0.0039 (17) | 0.0169 (16) |
C4 | 0.070 (2) | 0.0563 (16) | 0.085 (2) | −0.0049 (16) | 0.0216 (17) | 0.0006 (15) |
C5 | 0.0549 (16) | 0.0488 (14) | 0.0615 (15) | −0.0069 (14) | 0.0072 (14) | −0.0025 (12) |
C6 | 0.0499 (16) | 0.0565 (16) | 0.116 (2) | −0.0131 (15) | 0.0175 (17) | 0.0029 (17) |
C7 | 0.0526 (16) | 0.0653 (17) | 0.0906 (19) | −0.0048 (15) | 0.0215 (16) | 0.0072 (15) |
C8 | 0.0437 (14) | 0.0533 (14) | 0.0517 (14) | −0.0102 (12) | 0.0115 (13) | −0.0017 (12) |
C9 | 0.0390 (13) | 0.0563 (13) | 0.0394 (12) | −0.0094 (12) | 0.0005 (11) | −0.0050 (11) |
C10 | 0.0401 (13) | 0.0580 (15) | 0.0498 (13) | −0.0048 (13) | 0.0023 (12) | −0.0053 (12) |
C11 | 0.0481 (15) | 0.0657 (16) | 0.0448 (13) | −0.0094 (14) | 0.0085 (13) | −0.0077 (12) |
C12 | 0.0559 (16) | 0.0585 (16) | 0.0500 (13) | −0.0124 (14) | 0.0131 (14) | −0.0032 (12) |
C13 | 0.0511 (15) | 0.0536 (14) | 0.0462 (13) | −0.0071 (14) | 0.0077 (13) | 0.0006 (12) |
C14 | 0.0471 (14) | 0.0548 (14) | 0.0622 (15) | −0.0061 (13) | 0.0130 (14) | −0.0007 (13) |
C15 | 0.0739 (19) | 0.0634 (17) | 0.097 (2) | 0.0023 (17) | 0.0344 (18) | 0.0068 (16) |
C16 | 0.096 (2) | 0.0621 (17) | 0.0761 (17) | 0.006 (2) | 0.0283 (18) | 0.0026 (15) |
C17 | 0.0630 (16) | 0.0527 (15) | 0.0449 (13) | −0.0059 (15) | 0.0067 (13) | 0.0015 (12) |
C18 | 0.087 (2) | 0.0700 (16) | 0.0434 (13) | −0.0041 (18) | 0.0134 (15) | −0.0032 (12) |
C19 | 0.0803 (19) | 0.0703 (18) | 0.0535 (14) | 0.0027 (17) | 0.0010 (16) | −0.0100 (13) |
C20 | 0.0730 (17) | 0.0552 (15) | 0.0533 (14) | −0.0133 (16) | −0.0002 (15) | −0.0023 (13) |
C21 | 0.123 (3) | 0.098 (2) | 0.0710 (18) | −0.031 (2) | −0.023 (2) | −0.0037 (16) |
C22 | 0.0752 (18) | 0.0509 (14) | 0.0594 (16) | −0.0113 (15) | 0.0122 (16) | −0.0053 (12) |
C23 | 0.0595 (16) | 0.0567 (15) | 0.0520 (14) | −0.0106 (15) | 0.0103 (14) | 0.0030 (13) |
C24 | 0.0724 (19) | 0.0651 (18) | 0.0670 (17) | −0.0020 (18) | 0.0073 (17) | 0.0083 (15) |
C25 | 0.075 (2) | 0.098 (2) | 0.0646 (18) | 0.004 (2) | 0.0093 (16) | 0.0103 (17) |
C26 | 0.074 (2) | 0.173 (4) | 0.102 (2) | −0.019 (3) | 0.005 (2) | 0.025 (3) |
C27 | 0.116 (3) | 0.140 (3) | 0.113 (3) | 0.049 (3) | 0.009 (3) | −0.001 (2) |
C28 | 0.090 (2) | 0.0566 (18) | 0.194 (4) | −0.0108 (19) | 0.011 (3) | −0.021 (2) |
C29 | 0.173 (4) | 0.0740 (19) | 0.123 (3) | 0.030 (3) | 0.075 (3) | 0.038 (2) |
C30 | 0.0580 (17) | 0.0731 (18) | 0.098 (2) | −0.0027 (16) | −0.0125 (17) | 0.0076 (16) |
C31 | 0.073 (2) | 0.0685 (18) | 0.0508 (15) | 0.0062 (19) | 0.0050 (17) | 0.0064 (16) |
C32 | 0.101 (2) | 0.105 (2) | 0.082 (2) | 0.001 (2) | 0.030 (2) | −0.0023 (19) |
Geometric parameters (Å, º) top
O1—C3 | 1.208 (3) | C15—H15B | 0.9700 |
O2—C11 | 1.427 (3) | C16—C17 | 1.506 (3) |
O2—H2O | 0.8200 | C16—H16A | 0.9700 |
O3—C31 | 1.335 (3) | C16—H16B | 0.9700 |
O3—C23 | 1.451 (3) | C17—C20 | 1.494 (3) |
O4—C31 | 1.200 (3) | C18—H18A | 0.9600 |
O5—C24 | 1.438 (3) | C18—H18B | 0.9600 |
O5—C25 | 1.447 (3) | C18—H18C | 0.9600 |
C1—C2 | 1.540 (4) | C19—H19A | 0.9600 |
C1—C10 | 1.550 (3) | C19—H19B | 0.9600 |
C1—H1A | 0.9700 | C19—H19C | 0.9600 |
C1—H1B | 0.9700 | C20—C22 | 1.537 (3) |
C2—C3 | 1.486 (4) | C20—C21 | 1.539 (3) |
C2—H2A | 0.9700 | C20—H20 | 0.9800 |
C2—H2B | 0.9700 | C21—H21A | 0.9600 |
C3—C4 | 1.515 (4) | C21—H21B | 0.9600 |
C4—C28 | 1.530 (4) | C21—H21C | 0.9600 |
C4—C29 | 1.536 (4) | C22—C23 | 1.516 (3) |
C4—C5 | 1.558 (3) | C22—H22A | 0.9700 |
C5—C6 | 1.523 (4) | C22—H22B | 0.9700 |
C5—C10 | 1.543 (3) | C23—C24 | 1.481 (4) |
C5—H5 | 0.9800 | C23—H23 | 0.9800 |
C6—C7 | 1.517 (3) | C24—C25 | 1.461 (4) |
C6—H6A | 0.9700 | C24—H24 | 0.9800 |
C6—H6B | 0.9700 | C25—C26 | 1.489 (4) |
C7—C8 | 1.547 (3) | C25—C27 | 1.492 (4) |
C7—H7A | 0.9700 | C26—H26A | 0.9600 |
C7—H7B | 0.9700 | C26—H26B | 0.9600 |
C8—C18 | 1.539 (3) | C26—H26C | 0.9600 |
C8—C9 | 1.564 (3) | C27—H27A | 0.9600 |
C8—C14 | 1.574 (3) | C27—H27B | 0.9600 |
C9—C11 | 1.545 (3) | C27—H27C | 0.9600 |
C9—C10 | 1.581 (3) | C28—H28A | 0.9600 |
C9—H9 | 0.9800 | C28—H28B | 0.9600 |
C10—C19 | 1.539 (3) | C28—H28C | 0.9600 |
C11—C12 | 1.538 (3) | C29—H29A | 0.9600 |
C11—H11 | 0.9800 | C29—H29B | 0.9600 |
C12—C13 | 1.494 (3) | C29—H29C | 0.9600 |
C12—H12A | 0.9700 | C30—H30A | 0.9600 |
C12—H12B | 0.9700 | C30—H30B | 0.9600 |
C13—C17 | 1.325 (3) | C30—H30C | 0.9600 |
C13—C14 | 1.513 (3) | C31—C32 | 1.490 (4) |
C14—C30 | 1.538 (3) | C32—H32A | 0.9600 |
C14—C15 | 1.557 (3) | C32—H32B | 0.9600 |
C15—C16 | 1.518 (3) | C32—H32C | 0.9600 |
C15—H15A | 0.9700 | | |
| | | |
C11—O2—H2O | 109.5 | H16A—C16—H16B | 108.8 |
C31—O3—C23 | 119.0 (2) | C13—C17—C20 | 127.8 (2) |
C24—O5—C25 | 60.83 (17) | C13—C17—C16 | 110.7 (2) |
C2—C1—C10 | 112.4 (2) | C20—C17—C16 | 121.5 (2) |
C2—C1—H1A | 109.1 | C8—C18—H18A | 109.5 |
C10—C1—H1A | 109.1 | C8—C18—H18B | 109.5 |
C2—C1—H1B | 109.1 | H18A—C18—H18B | 109.5 |
C10—C1—H1B | 109.1 | C8—C18—H18C | 109.5 |
H1A—C1—H1B | 107.9 | H18A—C18—H18C | 109.5 |
C3—C2—C1 | 117.0 (3) | H18B—C18—H18C | 109.5 |
C3—C2—H2A | 108.0 | C10—C19—H19A | 109.5 |
C1—C2—H2A | 108.0 | C10—C19—H19B | 109.5 |
C3—C2—H2B | 108.0 | H19A—C19—H19B | 109.5 |
C1—C2—H2B | 108.0 | C10—C19—H19C | 109.5 |
H2A—C2—H2B | 107.3 | H19A—C19—H19C | 109.5 |
O1—C3—C2 | 121.2 (3) | H19B—C19—H19C | 109.5 |
O1—C3—C4 | 122.9 (3) | C17—C20—C22 | 111.3 (2) |
C2—C3—C4 | 115.8 (3) | C17—C20—C21 | 112.3 (2) |
C3—C4—C28 | 109.3 (3) | C22—C20—C21 | 110.1 (2) |
C3—C4—C29 | 105.2 (3) | C17—C20—H20 | 107.6 |
C28—C4—C29 | 108.2 (3) | C22—C20—H20 | 107.6 |
C3—C4—C5 | 110.2 (2) | C21—C20—H20 | 107.6 |
C28—C4—C5 | 114.7 (2) | C20—C21—H21A | 109.5 |
C29—C4—C5 | 108.9 (2) | C20—C21—H21B | 109.5 |
C6—C5—C10 | 110.3 (2) | H21A—C21—H21B | 109.5 |
C6—C5—C4 | 114.1 (2) | C20—C21—H21C | 109.5 |
C10—C5—C4 | 114.4 (2) | H21A—C21—H21C | 109.5 |
C6—C5—H5 | 105.7 | H21B—C21—H21C | 109.5 |
C10—C5—H5 | 105.7 | C23—C22—C20 | 114.7 (2) |
C4—C5—H5 | 105.7 | C23—C22—H22A | 108.6 |
C7—C6—C5 | 111.2 (2) | C20—C22—H22A | 108.6 |
C7—C6—H6A | 109.4 | C23—C22—H22B | 108.6 |
C5—C6—H6A | 109.4 | C20—C22—H22B | 108.6 |
C7—C6—H6B | 109.4 | H22A—C22—H22B | 107.6 |
C5—C6—H6B | 109.4 | O3—C23—C24 | 107.95 (19) |
H6A—C6—H6B | 108.0 | O3—C23—C22 | 106.53 (19) |
C6—C7—C8 | 116.1 (2) | C24—C23—C22 | 112.6 (2) |
C6—C7—H7A | 108.3 | O3—C23—H23 | 109.9 |
C8—C7—H7A | 108.3 | C24—C23—H23 | 109.9 |
C6—C7—H7B | 108.3 | C22—C23—H23 | 109.9 |
C8—C7—H7B | 108.3 | O5—C24—C25 | 59.90 (17) |
H7A—C7—H7B | 107.4 | O5—C24—C23 | 117.3 (2) |
C18—C8—C7 | 108.85 (19) | C25—C24—C23 | 124.9 (3) |
C18—C8—C9 | 110.35 (19) | O5—C24—H24 | 114.5 |
C7—C8—C9 | 110.34 (18) | C25—C24—H24 | 114.5 |
C18—C8—C14 | 109.48 (19) | C23—C24—H24 | 114.5 |
C7—C8—C14 | 109.13 (19) | O5—C25—C24 | 59.28 (18) |
C9—C8—C14 | 108.68 (17) | O5—C25—C26 | 113.7 (3) |
C11—C9—C8 | 110.75 (17) | C24—C25—C26 | 120.9 (3) |
C11—C9—C10 | 113.76 (18) | O5—C25—C27 | 114.3 (3) |
C8—C9—C10 | 116.34 (17) | C24—C25—C27 | 120.0 (3) |
C11—C9—H9 | 104.9 | C26—C25—C27 | 115.3 (3) |
C8—C9—H9 | 104.9 | C25—C26—H26A | 109.5 |
C10—C9—H9 | 104.9 | C25—C26—H26B | 109.5 |
C19—C10—C5 | 110.83 (19) | H26A—C26—H26B | 109.5 |
C19—C10—C1 | 107.5 (2) | C25—C26—H26C | 109.5 |
C5—C10—C1 | 105.94 (18) | H26A—C26—H26C | 109.5 |
C19—C10—C9 | 106.91 (18) | H26B—C26—H26C | 109.5 |
C5—C10—C9 | 111.20 (18) | C25—C27—H27A | 109.5 |
C1—C10—C9 | 114.43 (19) | C25—C27—H27B | 109.5 |
O2—C11—C12 | 108.24 (18) | H27A—C27—H27B | 109.5 |
O2—C11—C9 | 112.89 (18) | C25—C27—H27C | 109.5 |
C12—C11—C9 | 113.0 (2) | H27A—C27—H27C | 109.5 |
O2—C11—H11 | 107.5 | H27B—C27—H27C | 109.5 |
C12—C11—H11 | 107.5 | C4—C28—H28A | 109.5 |
C9—C11—H11 | 107.5 | C4—C28—H28B | 109.5 |
C13—C12—C11 | 111.91 (19) | H28A—C28—H28B | 109.5 |
C13—C12—H12A | 109.2 | C4—C28—H28C | 109.5 |
C11—C12—H12A | 109.2 | H28A—C28—H28C | 109.5 |
C13—C12—H12B | 109.2 | H28B—C28—H28C | 109.5 |
C11—C12—H12B | 109.2 | C4—C29—H29A | 109.5 |
H12A—C12—H12B | 107.9 | C4—C29—H29B | 109.5 |
C17—C13—C12 | 130.4 (2) | H29A—C29—H29B | 109.5 |
C17—C13—C14 | 114.3 (2) | C4—C29—H29C | 109.5 |
C12—C13—C14 | 115.24 (19) | H29A—C29—H29C | 109.5 |
C13—C14—C30 | 109.18 (19) | H29B—C29—H29C | 109.5 |
C13—C14—C15 | 101.81 (19) | C14—C30—H30A | 109.5 |
C30—C14—C15 | 109.5 (2) | C14—C30—H30B | 109.5 |
C13—C14—C8 | 107.96 (19) | H30A—C30—H30B | 109.5 |
C30—C14—C8 | 113.93 (19) | C14—C30—H30C | 109.5 |
C15—C14—C8 | 113.66 (19) | H30A—C30—H30C | 109.5 |
C16—C15—C14 | 107.6 (2) | H30B—C30—H30C | 109.5 |
C16—C15—H15A | 110.2 | O4—C31—O3 | 124.4 (3) |
C14—C15—H15A | 110.2 | O4—C31—C32 | 124.7 (3) |
C16—C15—H15B | 110.2 | O3—C31—C32 | 110.9 (3) |
C14—C15—H15B | 110.2 | C31—C32—H32A | 109.5 |
H15A—C15—H15B | 108.5 | C31—C32—H32B | 109.5 |
C17—C16—C15 | 104.9 (2) | H32A—C32—H32B | 109.5 |
C17—C16—H16A | 110.8 | C31—C32—H32C | 109.5 |
C15—C16—H16A | 110.8 | H32A—C32—H32C | 109.5 |
C17—C16—H16B | 110.8 | H32B—C32—H32C | 109.5 |
C15—C16—H16B | 110.8 | | |
| | | |
C10—C1—C2—C3 | −9.0 (4) | C17—C13—C14—C30 | −116.9 (2) |
C1—C2—C3—O1 | −135.1 (3) | C12—C13—C14—C30 | 65.7 (3) |
C1—C2—C3—C4 | 49.2 (4) | C17—C13—C14—C15 | −1.2 (3) |
O1—C3—C4—C28 | 29.6 (4) | C12—C13—C14—C15 | −178.58 (19) |
C2—C3—C4—C28 | −154.8 (3) | C17—C13—C14—C8 | 118.7 (2) |
O1—C3—C4—C29 | −86.3 (4) | C12—C13—C14—C8 | −58.7 (3) |
C2—C3—C4—C29 | 89.3 (3) | C18—C8—C14—C13 | −60.6 (2) |
O1—C3—C4—C5 | 156.5 (3) | C7—C8—C14—C13 | −179.66 (19) |
C2—C3—C4—C5 | −27.9 (4) | C9—C8—C14—C13 | 60.0 (2) |
C3—C4—C5—C6 | −157.9 (3) | C18—C8—C14—C30 | 177.9 (2) |
C28—C4—C5—C6 | −34.1 (4) | C7—C8—C14—C30 | 58.9 (3) |
C29—C4—C5—C6 | 87.1 (3) | C9—C8—C14—C30 | −61.5 (2) |
C3—C4—C5—C10 | −29.5 (3) | C18—C8—C14—C15 | 51.5 (3) |
C28—C4—C5—C10 | 94.3 (3) | C7—C8—C14—C15 | −67.5 (3) |
C29—C4—C5—C10 | −144.5 (3) | C9—C8—C14—C15 | 172.11 (19) |
C10—C5—C6—C7 | 67.6 (3) | C13—C14—C15—C16 | 5.9 (3) |
C4—C5—C6—C7 | −162.0 (2) | C30—C14—C15—C16 | 121.4 (2) |
C5—C6—C7—C8 | −34.8 (4) | C8—C14—C15—C16 | −109.9 (2) |
C6—C7—C8—C18 | 99.6 (3) | C14—C15—C16—C17 | −8.2 (3) |
C6—C7—C8—C9 | −21.6 (3) | C12—C13—C17—C20 | −5.5 (4) |
C6—C7—C8—C14 | −140.9 (2) | C14—C13—C17—C20 | 177.6 (2) |
C18—C8—C9—C11 | 61.7 (2) | C12—C13—C17—C16 | 172.8 (2) |
C7—C8—C9—C11 | −177.98 (19) | C14—C13—C17—C16 | −4.1 (3) |
C14—C8—C9—C11 | −58.4 (2) | C15—C16—C17—C13 | 7.7 (3) |
C18—C8—C9—C10 | −70.2 (2) | C15—C16—C17—C20 | −173.9 (2) |
C7—C8—C9—C10 | 50.1 (2) | C13—C17—C20—C22 | −117.2 (3) |
C14—C8—C9—C10 | 169.71 (18) | C16—C17—C20—C22 | 64.7 (3) |
C6—C5—C10—C19 | 80.6 (3) | C13—C17—C20—C21 | 118.8 (3) |
C4—C5—C10—C19 | −49.6 (3) | C16—C17—C20—C21 | −59.3 (3) |
C6—C5—C10—C1 | −163.1 (2) | C17—C20—C22—C23 | 62.6 (3) |
C4—C5—C10—C1 | 66.7 (3) | C21—C20—C22—C23 | −172.2 (2) |
C6—C5—C10—C9 | −38.2 (3) | C31—O3—C23—C24 | 107.9 (3) |
C4—C5—C10—C9 | −168.4 (2) | C31—O3—C23—C22 | −130.9 (2) |
C2—C1—C10—C19 | 74.0 (3) | C20—C22—C23—O3 | 71.5 (3) |
C2—C1—C10—C5 | −44.6 (3) | C20—C22—C23—C24 | −170.4 (2) |
C2—C1—C10—C9 | −167.4 (2) | C25—O5—C24—C23 | −116.4 (3) |
C11—C9—C10—C19 | 89.0 (2) | O3—C23—C24—O5 | −86.2 (3) |
C8—C9—C10—C19 | −140.5 (2) | C22—C23—C24—O5 | 156.5 (2) |
C11—C9—C10—C5 | −149.91 (18) | O3—C23—C24—C25 | −157.1 (3) |
C8—C9—C10—C5 | −19.4 (2) | C22—C23—C24—C25 | 85.6 (3) |
C11—C9—C10—C1 | −29.9 (3) | C24—O5—C25—C26 | 113.0 (3) |
C8—C9—C10—C1 | 100.6 (2) | C24—O5—C25—C27 | −111.7 (3) |
C8—C9—C11—O2 | 175.68 (19) | C23—C24—C25—O5 | 104.0 (3) |
C10—C9—C11—O2 | −51.1 (2) | O5—C24—C25—C26 | −100.9 (3) |
C8—C9—C11—C12 | 52.4 (2) | C23—C24—C25—C26 | 3.1 (4) |
C10—C9—C11—C12 | −174.35 (17) | O5—C24—C25—C27 | 102.1 (3) |
O2—C11—C12—C13 | −173.75 (19) | C23—C24—C25—C27 | −153.9 (3) |
C9—C11—C12—C13 | −47.9 (2) | C23—O3—C31—O4 | 2.3 (4) |
C11—C12—C13—C17 | −124.4 (3) | C23—O3—C31—C32 | −179.4 (2) |
C11—C12—C13—C14 | 52.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O5i | 0.82 | 2.06 | 2.870 (3) | 170 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |