organic compounds
(10R,13R)-17-(6-Hydroxy-5-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol hemihydrate: a bioactive steroid isolated from the Indian herb Artemisia reticulata
aBio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085, India, bInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, and cAccident and Emergency Department, Franco Vietnamese Hospital, 7 Nguyen Luong Bang Street, Ho Chi Minh City, Vietnam
*Correspondence e-mail: nguyendonhuquynh@yahoo.com
The title tetracyclic steroidal compound, C27H46O2·0.5H2O, crystallized as a monohydrate with two independent molecules (1 and 2) in the In both molecules, the conformations of the three cyclohexane rings (A, B and C) are chair, half-chair and chair, respectively. The fourth ring, D, has a twisted conformation on the bond linking the D and C rings. The is stabilized by hydrogen bonding with the two independent molecules being linked through the solvent water molecule via various O—H⋯O hydrogen bonds, forming layers parallel to (-101).
CCDC reference: 1564133
Structure description
The title compound was isolated from a methanol extract of the herb A. reticulata (in local dialect Kirmani aajowan) by (CC) over SiO2 gel by gradient solvent elution. This herb has been credited with different kinds of pharmacological activities, and has been used as a folklore medicine for conventional therapy against various ailments: malaria (Klayman et al., 1984; Malagon et al., 1997; Newton & White, 1999), cancer (Efferth et al., 2001; Lai & Singh, 1995), cardiovascular (Guantai & Addae-Mensah, 1999), vasodilatory (Walker, 1996), hepatitis (Aniya et al., 2000) and diabetes (Iriadam et al., 2006). It is found as a major constituent in many ayurvedic and herbal drug preparations, such as forkolin, Afsanteen and others, in Indian traditional medicinal systems (Nadkarni, 1954; Satyavati et al., 1987; Subramoniam et al., 1996; Drury, 1978). The Artemisia species are a rich source of bioactive sesquiterpenenoids (Klayman et al., 1984), such as artemisin and artemisinin, and isolated from A. annua (Klayman, 1985) exhibit antiplasmodial activity (Li et al., 1982). It is also under clinical trials to eradicate malaria.
We are looking for alternative abundant sources of artemisin and artemisinin from other varieties of Artemisia species. Unfortunately, phytochemical investigations revealed that the species of A. reticulata used by us did not possess the aforesaid Instead of that, a colourless solid substance was isolated as a minor constituent by column chromatographic separation. Herein, we report on the extraction and of this minor colourless solid constituent assigned as a tetracyclic steroid based on chemical evidence. This solid substantiated the LB test (Liebermann Burchard Test), and a colour reaction on spraying with 10% aqueous H2SO4 onto a micro TLC plate followed by heating at 393 K for 5 min developed a pink-coloured spot on the TLC. These chemical tests revealed that the compound is a steroid. It shows a very close structural resemblance to the cyclopenteno perhydrophenanthreen skeleton viz. cholesterol (Craven, 1976; Marc, 1979; Naora et al., 1986), but with different substituents.
The molecular structure of the title compound is illustrated in Fig. 1. It crystallizes as a monohydrate with two independent molecules (1 and 2) in the The two molecules are almost identical (Fig. 2) and here the geometry will be described for molecule 1 only. It has an alkyl (1-hydroxy-2-isopropylhexyl) side chain located at atom C17 of the cyclopentane D ring. This side chain undergoes considerable thermal liberation and bond strain. The molecule is composed of a series of fused rings (A, B, C and D). Rings A and C have chair conformations while ring B has a half-chair conformation, and the five-membered ring D is twisted on bond C13—C14. In addition to the tetracyclic moiety, two –CH3 groups are present at positions C5 and C13, at ring junctures A/B and C/D, respectively. At atom C2 in ring A there is an –OH group and in ring D the alkyl side chain, (1-hydroxy-2-isopropylhexyl), at atom C17.
There is total of eleven asymmetric centres in the title molecule at various positions, such as C2, C5, C9, C10, C13, C14, C17, C20, C24 and C25. Among them, five asymmetric centres located at carbon atoms C2, C9, C10, C14, C25, and the remaining six chiral centres located at atoms C5, C13, C17, C20, C24, have relative S and R configurations, respectively; see Fig. 3.
In the crystal, molecules are linked via O—H⋯Owater, Owater—H⋯O and other O—H⋯O hydrogen bonds, forming layers lying parallel to (01); see Table 1 and Figs. 4 and 5.
Synthesis and crystallization
The title steroid was isolated as a colourless solid from a methanol extract of A. reticulata by means of CC/SiO2 gel by with a mixture of a binary solvent system, hexane and ethyl acetate. The desired compound was purified by reverse-phase high-pressure Suitable crystals for X-ray diffraction were obtained after being recrystallized three times from ethyl acetate:hexane (1:4) at room temperature by slow evaporation of the solvents.
Refinement
Crystal data, data collection and structure . In both molecules the alkyl (1-hydroxy-2-isopropylhexyl) side chain located at atom C17 of the cyclopentane D ring undergoes considerable thermal liberation and bond strain, and it was necessary to use a number of ISOR, DELU and DFIX restraints during the process. Nevertheless, the final R factors are still relatively high: R[F2 > 2σ(F2)] = 0.11 and wR(F2) = 0.32.
details are summarized in Table 2Structural data
CCDC reference: 1564133
https://doi.org/10.1107/S2414314617010860/su4157sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010860/su4157Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617010860/su4157Isup3.cml
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C27H46O2·0.5H2O | F(000) = 916 |
Mr = 411.64 | Dx = 1.047 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4107 (8) Å | Cell parameters from 2353 reflections |
b = 7.5175 (6) Å | θ = 2.5–28.0° |
c = 36.979 (3) Å | µ = 0.06 mm−1 |
β = 93.375 (8)° | T = 150 K |
V = 2611.5 (4) Å3 | Prism, colourless |
Z = 4 | 0.32 × 0.28 × 0.12 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 4382 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.048 |
Rotation method data acquisition using ω scans | θmax = 25.4°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −11→10 |
Tmin = 0.980, Tmax = 0.992 | k = −6→9 |
10852 measured reflections | l = −44→43 |
6720 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.319 | w = 1/[σ2(Fo2) + (0.1665P)2 + 5.0834P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
6720 reflections | Δρmax = 0.86 e Å−3 |
538 parameters | Δρmin = −0.40 e Å−3 |
70 restraints | Absolute structure: Flack x determined using 911 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.1 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.2212 (7) | 0.5959 (10) | 0.51417 (15) | 0.0389 (17) | |
H1O | 1.2907 | 0.5340 | 0.5220 | 0.047* | |
O2 | 0.823 (2) | 0.891 (3) | 0.1325 (4) | 0.199 (8) | |
H2O | 0.7706 | 0.9808 | 0.1287 | 0.239* | |
C1 | 1.0884 (10) | 0.6980 (13) | 0.4597 (2) | 0.033 (2) | |
H1A | 1.1043 | 0.8239 | 0.4667 | 0.039* | |
H1B | 0.9996 | 0.6579 | 0.4703 | 0.039* | |
C2 | 1.2097 (9) | 0.5885 (13) | 0.4751 (2) | 0.030 (2) | |
H2 | 1.2999 | 0.6356 | 0.4658 | 0.036* | |
C3 | 1.1923 (10) | 0.3970 (14) | 0.4635 (2) | 0.034 (2) | |
H3A | 1.1050 | 0.3469 | 0.4732 | 0.041* | |
H3B | 1.2747 | 0.3264 | 0.4733 | 0.041* | |
C4 | 1.1819 (8) | 0.3852 (12) | 0.4217 (2) | 0.022 (2) | |
H4A | 1.1650 | 0.2597 | 0.4146 | 0.027* | |
H4B | 1.2744 | 0.4214 | 0.4126 | 0.027* | |
C5 | 1.0630 (8) | 0.5016 (11) | 0.4032 (2) | 0.0200 (18) | |
C6 | 1.0707 (9) | 0.6856 (13) | 0.4193 (2) | 0.028 (2) | |
C7 | 1.0664 (8) | 0.8326 (12) | 0.3990 (2) | 0.027 (2) | |
H7 | 1.0720 | 0.9437 | 0.4112 | 0.032* | |
C8 | 1.0535 (9) | 0.8360 (12) | 0.3582 (2) | 0.0228 (19) | |
H8A | 1.1473 | 0.8651 | 0.3489 | 0.027* | |
H8B | 0.9857 | 0.9305 | 0.3501 | 0.027* | |
C9 | 1.0025 (8) | 0.6589 (12) | 0.3425 (2) | 0.0208 (18) | |
H9 | 0.8990 | 0.6451 | 0.3466 | 0.025* | |
C10 | 1.0854 (8) | 0.5048 (11) | 0.3617 (2) | 0.0180 (18) | |
H10 | 1.1885 | 0.5311 | 0.3594 | 0.022* | |
C11 | 1.0569 (9) | 0.3277 (12) | 0.3426 (2) | 0.027 (2) | |
H11A | 0.9593 | 0.2885 | 0.3473 | 0.033* | |
H11B | 1.1238 | 0.2380 | 0.3534 | 0.033* | |
C12 | 1.0716 (8) | 0.3307 (12) | 0.3014 (2) | 0.0228 (19) | |
H12A | 1.0440 | 0.2135 | 0.2910 | 0.027* | |
H12B | 1.1722 | 0.3533 | 0.2963 | 0.027* | |
C13 | 0.9762 (8) | 0.4771 (13) | 0.2835 (2) | 0.026 (2) | |
C14 | 1.0230 (8) | 0.6501 (12) | 0.3018 (2) | 0.0221 (19) | |
H14 | 1.1279 | 0.6585 | 0.2992 | 0.027* | |
C15 | 0.9558 (10) | 0.7972 (12) | 0.2775 (2) | 0.030 (2) | |
H15A | 1.0122 | 0.9083 | 0.2797 | 0.036* | |
H15B | 0.8570 | 0.8223 | 0.2838 | 0.036* | |
C16 | 0.9591 (11) | 0.7173 (14) | 0.2386 (3) | 0.037 (2) | |
H16A | 0.8641 | 0.7280 | 0.2258 | 0.044* | |
H16B | 1.0288 | 0.7823 | 0.2245 | 0.044* | |
C17 | 1.0020 (9) | 0.5190 (12) | 0.2424 (2) | 0.025 (2) | |
H17 | 1.1066 | 0.5105 | 0.2393 | 0.030* | |
C18 | 0.9162 (8) | 0.4185 (14) | 0.4110 (2) | 0.031 (2) | |
H18A | 0.9097 | 0.2984 | 0.4007 | 0.038* | |
H18B | 0.9070 | 0.4123 | 0.4373 | 0.038* | |
H18C | 0.8397 | 0.4925 | 0.4000 | 0.038* | |
C19 | 0.8177 (8) | 0.4387 (13) | 0.2871 (2) | 0.028 (2) | |
H19A | 0.7925 | 0.3263 | 0.2749 | 0.033* | |
H19B | 0.7984 | 0.4300 | 0.3127 | 0.033* | |
H19C | 0.7609 | 0.5353 | 0.2758 | 0.033* | |
C20 | 0.9263 (10) | 0.4050 (14) | 0.2131 (2) | 0.033 (2) | |
H20 | 0.8222 | 0.4114 | 0.2169 | 0.039* | |
C21 | 0.9678 (11) | 0.2102 (14) | 0.2151 (2) | 0.041 (3) | |
H21A | 0.9157 | 0.1447 | 0.1956 | 0.049* | |
H21B | 1.0704 | 0.1986 | 0.2123 | 0.049* | |
H21C | 0.9442 | 0.1614 | 0.2385 | 0.049* | |
C22 | 0.9471 (12) | 0.4818 (16) | 0.1754 (2) | 0.045 (3) | |
H22A | 0.9936 | 0.5989 | 0.1792 | 0.054* | |
H22B | 1.0169 | 0.4042 | 0.1641 | 0.054* | |
C23 | 0.8380 (15) | 0.507 (2) | 0.1502 (3) | 0.080 (4) | |
H23A | 0.7725 | 0.5923 | 0.1610 | 0.095* | |
H23B | 0.7864 | 0.3920 | 0.1483 | 0.095* | |
C24 | 0.8551 (17) | 0.569 (2) | 0.1118 (3) | 0.082 (4) | |
H24 | 0.9587 | 0.5873 | 0.1084 | 0.099* | |
C25 | 0.778 (2) | 0.748 (3) | 0.1070 (4) | 0.107 (6) | |
H25 | 0.6757 | 0.7237 | 0.1112 | 0.129* | |
C26 | 0.780 (2) | 0.818 (3) | 0.0665 (5) | 0.146 (8) | |
H26A | 0.7502 | 0.7218 | 0.0497 | 0.175* | |
H26B | 0.7149 | 0.9186 | 0.0630 | 0.175* | |
H26C | 0.8769 | 0.8555 | 0.0616 | 0.175* | |
C27 | 0.798 (3) | 0.423 (3) | 0.0849 (5) | 0.195 (11) | |
H27A | 0.8086 | 0.4623 | 0.0600 | 0.234* | |
H27B | 0.8514 | 0.3123 | 0.0893 | 0.234* | |
H27C | 0.6967 | 0.4010 | 0.0885 | 0.234* | |
O3 | 0.5647 (7) | 0.8560 (10) | 0.46662 (15) | 0.0392 (17) | |
H3O | 0.5645 | 0.7492 | 0.4733 | 0.047* | |
O4 | 0.297 (4) | 0.608 (6) | 0.0743 (10) | 0.45 (2) | |
H4O | 0.3496 | 0.6316 | 0.0928 | 0.535* | |
C28 | 0.5988 (11) | 0.7558 (14) | 0.4054 (2) | 0.039 (3) | |
H28A | 0.5939 | 0.6299 | 0.4131 | 0.047* | |
H28B | 0.6994 | 0.7940 | 0.4083 | 0.047* | |
C29 | 0.5111 (10) | 0.8677 (13) | 0.4296 (2) | 0.030 (2) | |
H29 | 0.4115 | 0.8209 | 0.4279 | 0.036* | |
C30 | 0.5077 (10) | 1.0581 (13) | 0.4164 (2) | 0.028 (2) | |
H30A | 0.6050 | 1.1085 | 0.4186 | 0.033* | |
H30B | 0.4466 | 1.1299 | 0.4317 | 0.033* | |
C31 | 0.4496 (8) | 1.0675 (12) | 0.3768 (2) | 0.0229 (19) | |
H31A | 0.4499 | 1.1932 | 0.3688 | 0.027* | |
H31B | 0.3495 | 1.0261 | 0.3754 | 0.027* | |
C32 | 0.5349 (8) | 0.9554 (12) | 0.3506 (2) | 0.0191 (19) | |
C33 | 0.5488 (10) | 0.7694 (12) | 0.3656 (2) | 0.028 (2) | |
C34 | 0.5214 (9) | 0.6197 (12) | 0.3461 (2) | 0.027 (2) | |
H34 | 0.5325 | 0.5078 | 0.3579 | 0.032* | |
C35 | 0.4745 (8) | 0.6239 (11) | 0.3068 (2) | 0.0215 (19) | |
H35A | 0.5243 | 0.5283 | 0.2942 | 0.026* | |
H35B | 0.3712 | 0.5982 | 0.3043 | 0.026* | |
C36 | 0.5019 (9) | 0.7967 (12) | 0.2887 (2) | 0.0225 (19) | |
H36 | 0.6066 | 0.8082 | 0.2861 | 0.027* | |
C37 | 0.4521 (8) | 0.9557 (12) | 0.3122 (2) | 0.0194 (18) | |
H37 | 0.3496 | 0.9340 | 0.3165 | 0.023* | |
C38 | 0.4590 (9) | 1.1335 (12) | 0.2924 (2) | 0.0233 (19) | |
H38A | 0.4130 | 1.2260 | 0.3068 | 0.028* | |
H38B | 0.5600 | 1.1676 | 0.2907 | 0.028* | |
C39 | 0.3867 (10) | 1.1291 (13) | 0.2544 (2) | 0.030 (2) | |
H39A | 0.3986 | 1.2461 | 0.2427 | 0.036* | |
H39B | 0.2835 | 1.1081 | 0.2561 | 0.036* | |
C40 | 0.4477 (8) | 0.9850 (13) | 0.2310 (2) | 0.026 (2) | |
C41 | 0.4258 (9) | 0.8085 (13) | 0.2510 (2) | 0.027 (2) | |
H41 | 0.3216 | 0.8007 | 0.2548 | 0.033* | |
C42 | 0.4571 (11) | 0.6626 (16) | 0.2235 (2) | 0.042 (3) | |
H42A | 0.4069 | 0.5506 | 0.2288 | 0.050* | |
H42B | 0.5605 | 0.6388 | 0.2232 | 0.050* | |
C43 | 0.3979 (12) | 0.7470 (14) | 0.1874 (3) | 0.046 (3) | |
H43A | 0.3107 | 0.6834 | 0.1784 | 0.056* | |
H43B | 0.4693 | 0.7369 | 0.1689 | 0.056* | |
C44 | 0.3630 (10) | 0.9462 (15) | 0.1939 (2) | 0.038 (2) | |
H44 | 0.2592 | 0.9550 | 0.1980 | 0.046* | |
C45 | 0.6833 (8) | 1.0364 (15) | 0.3488 (2) | 0.032 (2) | |
H45A | 0.6750 | 1.1574 | 0.3391 | 0.038* | |
H45B | 0.7300 | 1.0402 | 0.3732 | 0.038* | |
H45C | 0.7399 | 0.9636 | 0.3330 | 0.038* | |
C46 | 0.6025 (9) | 1.0197 (14) | 0.2246 (2) | 0.034 (2) | |
H46A | 0.6386 | 0.9246 | 0.2095 | 0.041* | |
H46B | 0.6113 | 1.1341 | 0.2122 | 0.041* | |
H46C | 0.6580 | 1.0228 | 0.2478 | 0.041* | |
C47 | 0.3906 (10) | 1.0561 (15) | 0.1608 (2) | 0.036 (2) | |
H47 | 0.4924 | 1.0380 | 0.1553 | 0.044* | |
C48 | 0.3685 (15) | 1.2558 (16) | 0.1667 (3) | 0.061 (4) | |
H48A | 0.3877 | 1.3205 | 0.1445 | 0.073* | |
H48B | 0.2700 | 1.2774 | 0.1727 | 0.073* | |
H48C | 0.4336 | 1.2971 | 0.1866 | 0.073* | |
C49 | 0.2989 (12) | 0.9932 (19) | 0.1280 (2) | 0.056 (3) | |
H49A | 0.2739 | 0.8679 | 0.1329 | 0.068* | |
H49B | 0.2092 | 1.0618 | 0.1281 | 0.068* | |
C50 | 0.3399 (17) | 0.998 (3) | 0.0938 (3) | 0.122 (8) | |
H50A | 0.4325 | 0.9351 | 0.0940 | 0.146* | |
H50B | 0.3598 | 1.1242 | 0.0884 | 0.146* | |
C51 | 0.252 (2) | 0.927 (3) | 0.0612 (4) | 0.110 (6) | |
H51 | 0.1506 | 0.9138 | 0.0676 | 0.132* | |
C52 | 0.306 (4) | 0.749 (4) | 0.0484 (9) | 0.210 (14) | |
H52 | 0.4063 | 0.7621 | 0.0414 | 0.253* | |
C53 | 0.215 (4) | 0.667 (6) | 0.0166 (9) | 0.30 (2) | |
H53A | 0.2098 | 0.7493 | −0.0039 | 0.359* | |
H53B | 0.2578 | 0.5546 | 0.0094 | 0.359* | |
H53C | 0.1183 | 0.6438 | 0.0243 | 0.359* | |
C54 | 0.259 (3) | 1.059 (4) | 0.0312 (7) | 0.241 (14) | |
H54A | 0.2246 | 1.1749 | 0.0392 | 0.290* | |
H54B | 0.3582 | 1.0714 | 0.0246 | 0.290* | |
H54C | 0.2001 | 1.0189 | 0.0101 | 0.290* | |
O1W | 0.6405 (9) | 0.4363 (12) | 0.4827 (2) | 0.055 (2) | |
H11W | 0.618 (11) | 0.552 (11) | 0.487 (3) | 0.066* | |
H12W | 0.566 (10) | 0.385 (14) | 0.491 (3) | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.054 (4) | 0.043 (5) | 0.019 (3) | 0.005 (4) | −0.003 (3) | 0.000 (3) |
O2 | 0.225 (14) | 0.192 (16) | 0.179 (13) | 0.031 (13) | −0.006 (11) | −0.043 (12) |
C1 | 0.048 (6) | 0.030 (6) | 0.020 (4) | 0.005 (5) | 0.003 (4) | −0.006 (4) |
C2 | 0.032 (5) | 0.030 (6) | 0.028 (5) | −0.001 (4) | 0.002 (4) | −0.003 (4) |
C3 | 0.041 (5) | 0.034 (6) | 0.025 (5) | 0.002 (5) | 0.001 (4) | 0.002 (4) |
C4 | 0.029 (5) | 0.019 (5) | 0.019 (4) | 0.003 (4) | 0.004 (3) | 0.001 (4) |
C5 | 0.018 (4) | 0.010 (4) | 0.032 (4) | 0.005 (3) | 0.001 (3) | −0.001 (4) |
C6 | 0.025 (5) | 0.023 (5) | 0.035 (5) | 0.001 (4) | 0.004 (4) | 0.000 (4) |
C7 | 0.027 (5) | 0.016 (5) | 0.039 (5) | 0.002 (4) | 0.003 (4) | −0.010 (4) |
C8 | 0.020 (4) | 0.018 (5) | 0.030 (4) | 0.002 (4) | −0.001 (3) | −0.004 (4) |
C9 | 0.015 (4) | 0.013 (5) | 0.035 (5) | 0.003 (4) | 0.004 (3) | −0.002 (4) |
C10 | 0.014 (4) | 0.011 (4) | 0.029 (4) | 0.001 (3) | −0.001 (3) | −0.001 (4) |
C11 | 0.029 (5) | 0.013 (5) | 0.039 (5) | 0.003 (4) | −0.003 (4) | 0.002 (4) |
C12 | 0.020 (4) | 0.018 (5) | 0.030 (4) | 0.006 (4) | 0.000 (3) | −0.001 (4) |
C13 | 0.018 (4) | 0.030 (6) | 0.030 (5) | −0.003 (4) | 0.000 (3) | −0.001 (4) |
C14 | 0.014 (4) | 0.025 (5) | 0.027 (4) | −0.003 (4) | −0.001 (3) | 0.007 (4) |
C15 | 0.040 (5) | 0.014 (5) | 0.035 (5) | 0.009 (4) | 0.001 (4) | 0.004 (4) |
C16 | 0.040 (6) | 0.034 (6) | 0.037 (5) | 0.002 (5) | −0.001 (4) | 0.008 (5) |
C17 | 0.022 (4) | 0.029 (6) | 0.025 (4) | 0.000 (4) | 0.009 (3) | 0.004 (4) |
C18 | 0.026 (5) | 0.044 (6) | 0.025 (4) | −0.002 (5) | 0.009 (3) | 0.004 (5) |
C19 | 0.026 (5) | 0.029 (5) | 0.029 (4) | −0.005 (4) | 0.008 (4) | −0.004 (4) |
C20 | 0.036 (5) | 0.040 (6) | 0.023 (4) | −0.004 (5) | 0.000 (4) | −0.003 (4) |
C21 | 0.058 (7) | 0.040 (7) | 0.023 (5) | 0.008 (5) | −0.010 (4) | 0.000 (5) |
C22 | 0.074 (7) | 0.037 (7) | 0.025 (5) | 0.012 (6) | 0.002 (5) | −0.006 (5) |
C23 | 0.103 (11) | 0.090 (12) | 0.044 (7) | 0.002 (9) | −0.004 (7) | −0.010 (8) |
C24 | 0.096 (8) | 0.101 (9) | 0.049 (6) | 0.007 (8) | −0.011 (6) | 0.004 (7) |
C25 | 0.136 (10) | 0.112 (11) | 0.073 (8) | −0.008 (9) | −0.003 (8) | −0.013 (8) |
C26 | 0.208 (17) | 0.143 (17) | 0.085 (11) | 0.000 (15) | 0.002 (11) | 0.011 (12) |
C27 | 0.32 (2) | 0.19 (2) | 0.080 (11) | 0.030 (18) | 0.003 (14) | −0.006 (14) |
O3 | 0.057 (4) | 0.038 (4) | 0.022 (3) | 0.005 (4) | 0.001 (3) | 0.010 (3) |
O4 | 0.45 (3) | 0.45 (3) | 0.43 (3) | −0.03 (2) | 0.00 (2) | −0.03 (2) |
C28 | 0.065 (7) | 0.021 (6) | 0.028 (5) | 0.002 (5) | −0.011 (5) | 0.009 (4) |
C29 | 0.036 (5) | 0.032 (6) | 0.023 (4) | −0.009 (4) | 0.004 (4) | 0.000 (4) |
C30 | 0.035 (5) | 0.023 (5) | 0.026 (4) | 0.003 (4) | 0.005 (4) | −0.003 (4) |
C31 | 0.027 (4) | 0.014 (5) | 0.028 (4) | 0.008 (4) | 0.009 (3) | −0.004 (4) |
C32 | 0.015 (4) | 0.022 (5) | 0.020 (4) | 0.007 (4) | −0.003 (3) | −0.001 (4) |
C33 | 0.046 (5) | 0.017 (5) | 0.019 (4) | 0.001 (4) | −0.003 (4) | 0.007 (4) |
C34 | 0.031 (5) | 0.006 (5) | 0.042 (5) | 0.007 (4) | 0.001 (4) | 0.004 (4) |
C35 | 0.021 (4) | 0.014 (5) | 0.030 (4) | 0.006 (4) | 0.002 (3) | 0.000 (4) |
C36 | 0.032 (5) | 0.013 (5) | 0.023 (4) | 0.002 (4) | 0.002 (4) | −0.010 (4) |
C37 | 0.017 (4) | 0.020 (5) | 0.022 (4) | −0.001 (4) | 0.008 (3) | 0.006 (4) |
C38 | 0.036 (5) | 0.013 (5) | 0.021 (4) | 0.011 (4) | 0.005 (3) | 0.001 (4) |
C39 | 0.044 (5) | 0.022 (5) | 0.024 (4) | 0.008 (5) | 0.004 (4) | 0.007 (4) |
C40 | 0.021 (4) | 0.032 (6) | 0.025 (4) | 0.008 (4) | 0.001 (3) | −0.002 (4) |
C41 | 0.026 (5) | 0.024 (5) | 0.031 (5) | −0.001 (4) | 0.006 (4) | −0.007 (4) |
C42 | 0.055 (6) | 0.040 (7) | 0.030 (5) | 0.004 (6) | 0.001 (4) | −0.012 (5) |
C43 | 0.067 (7) | 0.034 (7) | 0.036 (5) | 0.000 (6) | −0.012 (5) | −0.009 (5) |
C44 | 0.041 (6) | 0.039 (6) | 0.033 (5) | 0.003 (5) | −0.008 (4) | 0.004 (5) |
C45 | 0.020 (4) | 0.053 (7) | 0.023 (4) | −0.001 (5) | 0.003 (3) | −0.004 (5) |
C46 | 0.037 (5) | 0.034 (6) | 0.030 (5) | −0.003 (5) | 0.003 (4) | 0.000 (4) |
C47 | 0.040 (6) | 0.041 (7) | 0.029 (5) | 0.006 (5) | 0.006 (4) | 0.002 (5) |
C48 | 0.098 (10) | 0.045 (8) | 0.039 (6) | 0.020 (7) | 0.004 (6) | 0.007 (6) |
C49 | 0.076 (8) | 0.064 (9) | 0.027 (5) | 0.018 (7) | −0.013 (5) | 0.000 (6) |
C50 | 0.109 (12) | 0.22 (3) | 0.039 (7) | −0.054 (15) | 0.007 (7) | −0.017 (11) |
C51 | 0.133 (10) | 0.127 (11) | 0.068 (8) | 0.000 (9) | −0.016 (7) | −0.005 (8) |
C52 | 0.217 (16) | 0.211 (17) | 0.200 (16) | −0.007 (11) | −0.012 (11) | −0.008 (11) |
C53 | 0.32 (3) | 0.30 (3) | 0.27 (3) | −0.03 (2) | −0.02 (2) | 0.00 (2) |
C54 | 0.33 (2) | 0.23 (2) | 0.164 (18) | −0.06 (2) | −0.052 (17) | 0.005 (18) |
O1W | 0.069 (5) | 0.046 (5) | 0.052 (4) | 0.006 (5) | 0.021 (4) | 0.014 (4) |
O1—C2 | 1.442 (9) | O3—H3O | 0.8400 |
O1—H1O | 0.8400 | O4—C52 | 1.43 (2) |
O2—C25 | 1.479 (17) | O4—H4O | 0.8400 |
O2—H2O | 0.8400 | C28—C29 | 1.508 (13) |
C1—C2 | 1.493 (12) | C28—C33 | 1.520 (11) |
C1—C6 | 1.500 (11) | C28—H28A | 0.9900 |
C1—H1A | 0.9900 | C28—H28B | 0.9900 |
C1—H1B | 0.9900 | C29—C30 | 1.511 (13) |
C2—C3 | 1.510 (13) | C29—H29 | 1.0000 |
C2—H2 | 1.0000 | C30—C31 | 1.534 (11) |
C3—C4 | 1.543 (10) | C30—H30A | 0.9900 |
C3—H3A | 0.9900 | C30—H30B | 0.9900 |
C3—H3B | 0.9900 | C31—C32 | 1.545 (11) |
C4—C5 | 1.548 (11) | C31—H31A | 0.9900 |
C4—H4A | 0.9900 | C31—H31B | 0.9900 |
C4—H4B | 0.9900 | C32—C33 | 1.508 (12) |
C5—C6 | 1.504 (12) | C32—C45 | 1.528 (11) |
C5—C18 | 1.559 (11) | C32—C37 | 1.579 (10) |
C5—C10 | 1.561 (11) | C33—C34 | 1.353 (12) |
C6—C7 | 1.335 (12) | C34—C35 | 1.495 (11) |
C7—C8 | 1.504 (11) | C34—H34 | 0.9500 |
C7—H7 | 0.9500 | C35—C36 | 1.491 (12) |
C8—C9 | 1.518 (12) | C35—H35A | 0.9900 |
C8—H8A | 0.9900 | C35—H35B | 0.9900 |
C8—H8B | 0.9900 | C36—C41 | 1.531 (11) |
C9—C14 | 1.532 (11) | C36—C37 | 1.566 (11) |
C9—C10 | 1.546 (11) | C36—H36 | 1.0000 |
C9—H9 | 1.0000 | C37—C38 | 1.528 (11) |
C10—C11 | 1.524 (12) | C37—H37 | 1.0000 |
C10—H10 | 1.0000 | C38—C39 | 1.526 (11) |
C11—C12 | 1.537 (11) | C38—H38A | 0.9900 |
C11—H11A | 0.9900 | C38—H38B | 0.9900 |
C11—H11B | 0.9900 | C39—C40 | 1.519 (12) |
C12—C13 | 1.545 (12) | C39—H39A | 0.9900 |
C12—H12A | 0.9900 | C39—H39B | 0.9900 |
C12—H12B | 0.9900 | C40—C46 | 1.513 (12) |
C13—C14 | 1.519 (13) | C40—C41 | 1.538 (13) |
C13—C19 | 1.532 (11) | C40—C44 | 1.574 (11) |
C13—C17 | 1.585 (11) | C41—C42 | 1.536 (13) |
C14—C15 | 1.537 (11) | C41—H41 | 1.0000 |
C14—H14 | 1.0000 | C42—C43 | 1.553 (13) |
C15—C16 | 1.560 (13) | C42—H42A | 0.9900 |
C15—H15A | 0.9900 | C42—H42B | 0.9900 |
C15—H15B | 0.9900 | C43—C44 | 1.555 (15) |
C16—C17 | 1.549 (13) | C43—H43A | 0.9900 |
C16—H16A | 0.9900 | C43—H43B | 0.9900 |
C16—H16B | 0.9900 | C44—C47 | 1.513 (13) |
C17—C20 | 1.525 (12) | C44—H44 | 1.0000 |
C17—H17 | 1.0000 | C45—H45A | 0.9800 |
C18—H18A | 0.9800 | C45—H45B | 0.9800 |
C18—H18B | 0.9800 | C45—H45C | 0.9800 |
C18—H18C | 0.9800 | C46—H46A | 0.9800 |
C19—H19A | 0.9800 | C46—H46B | 0.9800 |
C19—H19B | 0.9800 | C46—H46C | 0.9800 |
C19—H19C | 0.9800 | C47—C49 | 1.520 (13) |
C20—C21 | 1.516 (14) | C47—C48 | 1.533 (15) |
C20—C22 | 1.530 (13) | C47—H47 | 1.0000 |
C20—H20 | 1.0000 | C48—H48A | 0.9800 |
C21—H21A | 0.9800 | C48—H48B | 0.9800 |
C21—H21B | 0.9800 | C48—H48C | 0.9800 |
C21—H21C | 0.9800 | C49—C50 | 1.346 (15) |
C22—C23 | 1.358 (15) | C49—H49A | 0.9900 |
C22—H22A | 0.9900 | C49—H49B | 0.9900 |
C22—H22B | 0.9900 | C50—C51 | 1.52 (2) |
C23—C24 | 1.514 (17) | C50—H50A | 0.9900 |
C23—H23A | 0.9900 | C50—H50B | 0.9900 |
C23—H23B | 0.9900 | C51—C54 | 1.496 (19) |
C24—C27 | 1.559 (18) | C51—C52 | 1.51 (2) |
C24—C25 | 1.54 (2) | C51—H51 | 1.0000 |
C24—H24 | 1.0000 | C52—C53 | 1.54 (2) |
C25—C26 | 1.59 (2) | C52—H52 | 1.0000 |
C25—H25 | 1.0000 | C53—H53A | 0.9800 |
C26—H26A | 0.9800 | C53—H53B | 0.9800 |
C26—H26B | 0.9800 | C53—H53C | 0.9800 |
C26—H26C | 0.9800 | C54—H54A | 0.9800 |
C27—H27A | 0.9800 | C54—H54B | 0.9800 |
C27—H27B | 0.9800 | C54—H54C | 0.9800 |
C27—H27C | 0.9800 | O1W—H11W | 0.91 (8) |
O3—C29 | 1.435 (10) | O1W—H12W | 0.87 (7) |
C2—O1—H1O | 109.5 | C52—O4—H4O | 109.5 |
C25—O2—H2O | 109.5 | C29—C28—C33 | 112.7 (8) |
C2—C1—C6 | 112.6 (7) | C29—C28—H28A | 109.0 |
C2—C1—H1A | 109.1 | C33—C28—H28A | 109.0 |
C6—C1—H1A | 109.1 | C29—C28—H28B | 109.0 |
C2—C1—H1B | 109.1 | C33—C28—H28B | 109.0 |
C6—C1—H1B | 109.1 | H28A—C28—H28B | 107.8 |
H1A—C1—H1B | 107.8 | O3—C29—C28 | 111.0 (7) |
O1—C2—C1 | 111.8 (7) | O3—C29—C30 | 111.4 (7) |
O1—C2—C3 | 108.9 (8) | C28—C29—C30 | 109.9 (7) |
C1—C2—C3 | 110.4 (8) | O3—C29—H29 | 108.2 |
O1—C2—H2 | 108.6 | C28—C29—H29 | 108.2 |
C1—C2—H2 | 108.6 | C30—C29—H29 | 108.2 |
C3—C2—H2 | 108.6 | C29—C30—C31 | 110.5 (7) |
C2—C3—C4 | 109.9 (8) | C29—C30—H30A | 109.6 |
C2—C3—H3A | 109.7 | C31—C30—H30A | 109.6 |
C4—C3—H3A | 109.7 | C29—C30—H30B | 109.6 |
C2—C3—H3B | 109.7 | C31—C30—H30B | 109.6 |
C4—C3—H3B | 109.7 | H30A—C30—H30B | 108.1 |
H3A—C3—H3B | 108.2 | C30—C31—C32 | 113.9 (7) |
C3—C4—C5 | 114.3 (7) | C30—C31—H31A | 108.8 |
C3—C4—H4A | 108.7 | C32—C31—H31A | 108.8 |
C5—C4—H4A | 108.7 | C30—C31—H31B | 108.8 |
C3—C4—H4B | 108.7 | C32—C31—H31B | 108.8 |
C5—C4—H4B | 108.7 | H31A—C31—H31B | 107.7 |
H4A—C4—H4B | 107.6 | C33—C32—C45 | 109.0 (7) |
C6—C5—C18 | 108.6 (7) | C33—C32—C31 | 108.1 (7) |
C6—C5—C4 | 109.2 (7) | C45—C32—C31 | 108.7 (7) |
C18—C5—C4 | 108.5 (7) | C33—C32—C37 | 111.1 (7) |
C6—C5—C10 | 111.5 (7) | C45—C32—C37 | 111.4 (6) |
C18—C5—C10 | 111.1 (6) | C31—C32—C37 | 108.5 (6) |
C4—C5—C10 | 107.9 (6) | C34—C33—C28 | 119.8 (8) |
C7—C6—C1 | 120.5 (9) | C34—C33—C32 | 124.4 (7) |
C7—C6—C5 | 122.7 (8) | C28—C33—C32 | 115.7 (8) |
C1—C6—C5 | 116.8 (8) | C33—C34—C35 | 122.5 (8) |
C6—C7—C8 | 125.1 (8) | C33—C34—H34 | 118.8 |
C6—C7—H7 | 117.5 | C35—C34—H34 | 118.8 |
C8—C7—H7 | 117.5 | C36—C35—C34 | 114.0 (7) |
C7—C8—C9 | 111.9 (7) | C36—C35—H35A | 108.8 |
C7—C8—H8A | 109.2 | C34—C35—H35A | 108.8 |
C9—C8—H8A | 109.2 | C36—C35—H35B | 108.8 |
C7—C8—H8B | 109.2 | C34—C35—H35B | 108.8 |
C9—C8—H8B | 109.2 | H35A—C35—H35B | 107.7 |
H8A—C8—H8B | 107.9 | C35—C36—C41 | 112.1 (7) |
C8—C9—C14 | 111.1 (7) | C35—C36—C37 | 110.5 (6) |
C8—C9—C10 | 110.0 (6) | C41—C36—C37 | 108.8 (7) |
C14—C9—C10 | 109.3 (6) | C35—C36—H36 | 108.5 |
C8—C9—H9 | 108.8 | C41—C36—H36 | 108.5 |
C14—C9—H9 | 108.8 | C37—C36—H36 | 108.5 |
C10—C9—H9 | 108.8 | C38—C37—C36 | 112.3 (6) |
C11—C10—C9 | 111.8 (6) | C38—C37—C32 | 113.5 (7) |
C11—C10—C5 | 114.4 (7) | C36—C37—C32 | 110.5 (6) |
C9—C10—C5 | 111.7 (6) | C38—C37—H37 | 106.7 |
C11—C10—H10 | 106.1 | C36—C37—H37 | 106.7 |
C9—C10—H10 | 106.1 | C32—C37—H37 | 106.7 |
C5—C10—H10 | 106.1 | C39—C38—C37 | 113.2 (7) |
C10—C11—C12 | 115.0 (7) | C39—C38—H38A | 108.9 |
C10—C11—H11A | 108.5 | C37—C38—H38A | 108.9 |
C12—C11—H11A | 108.5 | C39—C38—H38B | 108.9 |
C10—C11—H11B | 108.5 | C37—C38—H38B | 108.9 |
C12—C11—H11B | 108.5 | H38A—C38—H38B | 107.8 |
H11A—C11—H11B | 107.5 | C38—C39—C40 | 112.1 (7) |
C11—C12—C13 | 110.7 (7) | C38—C39—H39A | 109.2 |
C11—C12—H12A | 109.5 | C40—C39—H39A | 109.2 |
C13—C12—H12A | 109.5 | C38—C39—H39B | 109.2 |
C11—C12—H12B | 109.5 | C40—C39—H39B | 109.2 |
C13—C12—H12B | 109.5 | H39A—C39—H39B | 107.9 |
H12A—C12—H12B | 108.1 | C46—C40—C39 | 111.5 (8) |
C14—C13—C19 | 112.4 (7) | C46—C40—C41 | 112.5 (7) |
C14—C13—C12 | 105.8 (6) | C39—C40—C41 | 106.0 (7) |
C19—C13—C12 | 111.9 (8) | C46—C40—C44 | 109.7 (7) |
C14—C13—C17 | 101.5 (7) | C39—C40—C44 | 116.0 (7) |
C19—C13—C17 | 109.0 (6) | C41—C40—C44 | 100.6 (7) |
C12—C13—C17 | 115.8 (7) | C42—C41—C36 | 117.6 (8) |
C13—C14—C9 | 115.2 (7) | C42—C41—C40 | 105.2 (7) |
C13—C14—C15 | 104.9 (6) | C36—C41—C40 | 114.7 (7) |
C9—C14—C15 | 118.2 (7) | C42—C41—H41 | 106.2 |
C13—C14—H14 | 105.9 | C36—C41—H41 | 106.2 |
C9—C14—H14 | 105.9 | C40—C41—H41 | 106.2 |
C15—C14—H14 | 105.9 | C41—C42—C43 | 101.8 (8) |
C14—C15—C16 | 103.4 (7) | C41—C42—H42A | 111.4 |
C14—C15—H15A | 111.1 | C43—C42—H42A | 111.4 |
C16—C15—H15A | 111.1 | C41—C42—H42B | 111.4 |
C14—C15—H15B | 111.1 | C43—C42—H42B | 111.4 |
C16—C15—H15B | 111.1 | H42A—C42—H42B | 109.3 |
H15A—C15—H15B | 109.1 | C42—C43—C44 | 109.2 (8) |
C17—C16—C15 | 107.9 (7) | C42—C43—H43A | 109.8 |
C17—C16—H16A | 110.1 | C44—C43—H43A | 109.8 |
C15—C16—H16A | 110.1 | C42—C43—H43B | 109.8 |
C17—C16—H16B | 110.1 | C44—C43—H43B | 109.8 |
C15—C16—H16B | 110.1 | H43A—C43—H43B | 108.3 |
H16A—C16—H16B | 108.4 | C47—C44—C43 | 110.6 (8) |
C20—C17—C16 | 111.7 (7) | C47—C44—C40 | 120.2 (9) |
C20—C17—C13 | 118.6 (7) | C43—C44—C40 | 102.3 (8) |
C16—C17—C13 | 102.9 (7) | C47—C44—H44 | 107.7 |
C20—C17—H17 | 107.7 | C43—C44—H44 | 107.7 |
C16—C17—H17 | 107.7 | C40—C44—H44 | 107.7 |
C13—C17—H17 | 107.7 | C32—C45—H45A | 109.5 |
C5—C18—H18A | 109.5 | C32—C45—H45B | 109.5 |
C5—C18—H18B | 109.5 | H45A—C45—H45B | 109.5 |
H18A—C18—H18B | 109.5 | C32—C45—H45C | 109.5 |
C5—C18—H18C | 109.5 | H45A—C45—H45C | 109.5 |
H18A—C18—H18C | 109.5 | H45B—C45—H45C | 109.5 |
H18B—C18—H18C | 109.5 | C40—C46—H46A | 109.5 |
C13—C19—H19A | 109.5 | C40—C46—H46B | 109.5 |
C13—C19—H19B | 109.5 | H46A—C46—H46B | 109.5 |
H19A—C19—H19B | 109.5 | C40—C46—H46C | 109.5 |
C13—C19—H19C | 109.5 | H46A—C46—H46C | 109.5 |
H19A—C19—H19C | 109.5 | H46B—C46—H46C | 109.5 |
H19B—C19—H19C | 109.5 | C44—C47—C49 | 111.0 (9) |
C21—C20—C17 | 113.6 (7) | C44—C47—C48 | 112.8 (9) |
C21—C20—C22 | 111.3 (8) | C49—C47—C48 | 110.0 (10) |
C17—C20—C22 | 110.8 (8) | C44—C47—H47 | 107.6 |
C21—C20—H20 | 106.9 | C49—C47—H47 | 107.6 |
C17—C20—H20 | 106.9 | C48—C47—H47 | 107.6 |
C22—C20—H20 | 106.9 | C47—C48—H48A | 109.5 |
C20—C21—H21A | 109.5 | C47—C48—H48B | 109.5 |
C20—C21—H21B | 109.5 | H48A—C48—H48B | 109.5 |
H21A—C21—H21B | 109.5 | C47—C48—H48C | 109.5 |
C20—C21—H21C | 109.5 | H48A—C48—H48C | 109.5 |
H21A—C21—H21C | 109.5 | H48B—C48—H48C | 109.5 |
H21B—C21—H21C | 109.5 | C50—C49—C47 | 124.1 (12) |
C23—C22—C20 | 123.0 (11) | C50—C49—H49A | 106.3 |
C23—C22—H22A | 106.6 | C47—C49—H49A | 106.3 |
C20—C22—H22A | 106.6 | C50—C49—H49B | 106.3 |
C23—C22—H22B | 106.6 | C47—C49—H49B | 106.3 |
C20—C22—H22B | 106.6 | H49A—C49—H49B | 106.4 |
H22A—C22—H22B | 106.5 | C49—C50—C51 | 124.3 (14) |
C22—C23—C24 | 124.6 (13) | C49—C50—H50A | 106.2 |
C22—C23—H23A | 106.2 | C51—C50—H50A | 106.2 |
C24—C23—H23A | 106.2 | C49—C50—H50B | 106.2 |
C22—C23—H23B | 106.2 | C51—C50—H50B | 106.2 |
C24—C23—H23B | 106.2 | H50A—C50—H50B | 106.4 |
H23A—C23—H23B | 106.4 | C54—C51—C52 | 109 (2) |
C27—C24—C23 | 109.2 (14) | C54—C51—C50 | 107.9 (18) |
C27—C24—C25 | 113.6 (14) | C52—C51—C50 | 112 (2) |
C23—C24—C25 | 107.7 (13) | C54—C51—H51 | 109.2 |
C27—C24—H24 | 108.7 | C52—C51—H51 | 109.2 |
C23—C24—H24 | 108.7 | C50—C51—H51 | 109.2 |
C25—C24—H24 | 108.7 | O4—C52—C51 | 114 (3) |
O2—C25—C26 | 110.1 (17) | O4—C52—C53 | 99 (3) |
O2—C25—C24 | 116.7 (14) | C51—C52—C53 | 114 (3) |
C26—C25—C24 | 111.5 (15) | O4—C52—H52 | 109.6 |
O2—C25—H25 | 106.0 | C51—C52—H52 | 109.6 |
C26—C25—H25 | 106.0 | C53—C52—H52 | 109.6 |
C24—C25—H25 | 106.0 | C52—C53—H53A | 109.5 |
C25—C26—H26A | 109.5 | C52—C53—H53B | 109.5 |
C25—C26—H26B | 109.5 | H53A—C53—H53B | 109.5 |
H26A—C26—H26B | 109.5 | C52—C53—H53C | 109.5 |
C25—C26—H26C | 109.5 | H53A—C53—H53C | 109.5 |
H26A—C26—H26C | 109.5 | H53B—C53—H53C | 109.5 |
H26B—C26—H26C | 109.5 | C51—C54—H54A | 109.5 |
C24—C27—H27A | 109.5 | C51—C54—H54B | 109.5 |
C24—C27—H27B | 109.5 | H54A—C54—H54B | 109.5 |
H27A—C27—H27B | 109.5 | C51—C54—H54C | 109.5 |
C24—C27—H27C | 109.5 | H54A—C54—H54C | 109.5 |
H27A—C27—H27C | 109.5 | H54B—C54—H54C | 109.5 |
H27B—C27—H27C | 109.5 | H11W—O1W—H12W | 99 (8) |
C29—O3—H3O | 109.5 | ||
C6—C1—C2—O1 | −177.4 (8) | C33—C28—C29—O3 | −178.0 (8) |
C6—C1—C2—C3 | −56.1 (11) | C33—C28—C29—C30 | −54.3 (11) |
O1—C2—C3—C4 | −179.2 (6) | O3—C29—C30—C31 | −179.8 (6) |
C1—C2—C3—C4 | 57.7 (10) | C28—C29—C30—C31 | 56.8 (10) |
C2—C3—C4—C5 | −55.2 (10) | C29—C30—C31—C32 | −57.6 (10) |
C3—C4—C5—C6 | 47.6 (10) | C30—C31—C32—C33 | 51.7 (9) |
C3—C4—C5—C18 | −70.6 (9) | C30—C31—C32—C45 | −66.6 (9) |
C3—C4—C5—C10 | 169.0 (7) | C30—C31—C32—C37 | 172.2 (7) |
C2—C1—C6—C7 | −126.5 (10) | C29—C28—C33—C34 | −128.1 (10) |
C2—C1—C6—C5 | 51.6 (11) | C29—C28—C33—C32 | 52.5 (11) |
C18—C5—C6—C7 | −109.5 (9) | C45—C32—C33—C34 | −110.2 (10) |
C4—C5—C6—C7 | 132.4 (8) | C31—C32—C33—C34 | 131.8 (9) |
C10—C5—C6—C7 | 13.2 (11) | C37—C32—C33—C34 | 12.9 (12) |
C18—C5—C6—C1 | 72.4 (9) | C45—C32—C33—C28 | 69.1 (10) |
C4—C5—C6—C1 | −45.7 (10) | C31—C32—C33—C28 | −48.9 (10) |
C10—C5—C6—C1 | −164.9 (7) | C37—C32—C33—C28 | −167.8 (7) |
C1—C6—C7—C8 | 178.1 (7) | C28—C33—C34—C35 | −178.9 (8) |
C5—C6—C7—C8 | 0.1 (13) | C32—C33—C34—C35 | 0.3 (14) |
C6—C7—C8—C9 | 16.8 (11) | C33—C34—C35—C36 | 17.4 (12) |
C7—C8—C9—C14 | −166.8 (6) | C34—C35—C36—C41 | −168.3 (7) |
C7—C8—C9—C10 | −45.6 (9) | C34—C35—C36—C37 | −46.9 (9) |
C8—C9—C10—C11 | −170.0 (7) | C35—C36—C37—C38 | −172.1 (7) |
C14—C9—C10—C11 | −47.8 (9) | C41—C36—C37—C38 | −48.7 (9) |
C8—C9—C10—C5 | 60.4 (8) | C35—C36—C37—C32 | 60.0 (9) |
C14—C9—C10—C5 | −177.4 (6) | C41—C36—C37—C32 | −176.6 (7) |
C6—C5—C10—C11 | −171.2 (7) | C33—C32—C37—C38 | −169.0 (7) |
C18—C5—C10—C11 | −50.0 (9) | C45—C32—C37—C38 | −47.2 (9) |
C4—C5—C10—C11 | 68.8 (9) | C31—C32—C37—C38 | 72.3 (8) |
C6—C5—C10—C9 | −43.0 (9) | C33—C32—C37—C36 | −41.8 (9) |
C18—C5—C10—C9 | 78.3 (9) | C45—C32—C37—C36 | 80.0 (9) |
C4—C5—C10—C9 | −162.9 (6) | C31—C32—C37—C36 | −160.5 (7) |
C9—C10—C11—C12 | 49.0 (9) | C36—C37—C38—C39 | 50.1 (9) |
C5—C10—C11—C12 | 177.3 (6) | C32—C37—C38—C39 | 176.4 (6) |
C10—C11—C12—C13 | −54.7 (9) | C37—C38—C39—C40 | −56.3 (10) |
C11—C12—C13—C14 | 57.5 (8) | C38—C39—C40—C46 | −64.1 (10) |
C11—C12—C13—C19 | −65.1 (9) | C38—C39—C40—C41 | 58.7 (9) |
C11—C12—C13—C17 | 169.1 (7) | C38—C39—C40—C44 | 169.4 (8) |
C19—C13—C14—C9 | 60.0 (9) | C35—C36—C41—C42 | −56.5 (11) |
C12—C13—C14—C9 | −62.3 (8) | C37—C36—C41—C42 | −178.9 (8) |
C17—C13—C14—C9 | 176.3 (6) | C35—C36—C41—C40 | 179.1 (7) |
C19—C13—C14—C15 | −71.7 (8) | C37—C36—C41—C40 | 56.7 (9) |
C12—C13—C14—C15 | 166.0 (7) | C46—C40—C41—C42 | −69.9 (9) |
C17—C13—C14—C15 | 44.6 (8) | C39—C40—C41—C42 | 167.9 (7) |
C8—C9—C14—C13 | 179.5 (6) | C44—C40—C41—C42 | 46.7 (8) |
C10—C9—C14—C13 | 58.0 (8) | C46—C40—C41—C36 | 60.8 (9) |
C8—C9—C14—C15 | −55.4 (9) | C39—C40—C41—C36 | −61.3 (9) |
C10—C9—C14—C15 | −176.9 (7) | C44—C40—C41—C36 | 177.5 (7) |
C13—C14—C15—C16 | −34.1 (8) | C36—C41—C42—C43 | −164.7 (8) |
C9—C14—C15—C16 | −164.0 (7) | C40—C41—C42—C43 | −35.7 (9) |
C14—C15—C16—C17 | 9.8 (9) | C41—C42—C43—C44 | 10.8 (11) |
C15—C16—C17—C20 | 145.0 (7) | C42—C43—C44—C47 | 146.2 (9) |
C15—C16—C17—C13 | 16.7 (9) | C42—C43—C44—C40 | 17.0 (11) |
C14—C13—C17—C20 | −160.9 (7) | C46—C40—C44—C47 | −42.0 (12) |
C19—C13—C17—C20 | −42.1 (11) | C39—C40—C44—C47 | 85.5 (11) |
C12—C13—C17—C20 | 85.1 (9) | C41—C40—C44—C47 | −160.7 (9) |
C14—C13—C17—C16 | −37.1 (8) | C46—C40—C44—C43 | 81.0 (10) |
C19—C13—C17—C16 | 81.6 (9) | C39—C40—C44—C43 | −151.6 (9) |
C12—C13—C17—C16 | −151.1 (8) | C41—C40—C44—C43 | −37.7 (9) |
C16—C17—C20—C21 | 178.6 (8) | C43—C44—C47—C49 | 60.2 (11) |
C13—C17—C20—C21 | −62.1 (11) | C40—C44—C47—C49 | 179.0 (9) |
C16—C17—C20—C22 | 52.5 (10) | C43—C44—C47—C48 | −175.8 (9) |
C13—C17—C20—C22 | 171.8 (8) | C40—C44—C47—C48 | −56.9 (13) |
C21—C20—C22—C23 | 101.2 (14) | C44—C47—C49—C50 | −146.9 (16) |
C17—C20—C22—C23 | −131.5 (13) | C48—C47—C49—C50 | 87.5 (18) |
C20—C22—C23—C24 | −175.1 (13) | C47—C49—C50—C51 | 176.9 (17) |
C22—C23—C24—C27 | 118.7 (18) | C49—C50—C51—C54 | 137 (2) |
C22—C23—C24—C25 | −117.5 (17) | C49—C50—C51—C52 | −103 (3) |
C27—C24—C25—O2 | 177.7 (17) | C54—C51—C52—O4 | −177 (3) |
C23—C24—C25—O2 | 57 (2) | C50—C51—C52—O4 | 64 (4) |
C27—C24—C25—C26 | −55 (2) | C54—C51—C52—C53 | −64 (3) |
C23—C24—C25—C26 | −175.8 (14) | C50—C51—C52—C53 | 177 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O1W | 0.84 | 2.48 | 3.282 (11) | 161 |
O1W—H11W···O3 | 0.91 (8) | 2.45 (9) | 3.282 (11) | 151 (10) |
O1W—H12W···O3i | 0.87 (7) | 2.07 (9) | 2.834 (9) | 147 (10) |
O1—H1O···O3ii | 0.84 | 1.94 | 2.766 (9) | 169 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y−1/2, −z+1. |
Acknowledgements
The authors thank Professor Dr Hartmut, FG Strukturforschung, Material-und Geowissenschaften, Technische Universit at Darmstadt, and Professor Kingston, Department of Chemistry, Virginia Polytechnic Institute and State University, USA, for their kind co-operation to record XRD of the crystal, for providing diffractometer time and for carrying out the antiproliferative bioassay against the cancer cell line.
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