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The crystal structures of five follicular fluid meiosis-activating sterol-related Δ8,14-sterol compounds are presented. These are 4,4-di­methyl-23-phenyl-24-nor-5α-chola-8,14-dien-3β-ol, C31H44O, 4,4-di­methyl-22-phenyl-23,24-dinor-5α-chola-8,14-dien-3β-ol, C30H42O, (20R)-4,4-di­methyl-22-oxa-5α,20-chol­es­ta-8,14,24-trien-3β-ol, C28H44O2, 4,4-di­methyl-23-phenyl-22-oxa-24-nor-5α-chola-8,14-dien-3β-ol–water (4/1), 4C30H42O2·H2O, and 4,4-di­methyl-5α-cholesta-8,14-dien-3-one, C29H46O. Two of the derivatives are inactive and three are active as agonists. Preliminary structure–activity relationship studies showed that the positions of the double bonds in the skeleton and the structures of the side chains are important determinants for activity. The conformations of the skeletons were compared with double-bond isomers retrieved from the Cambridge Structural Database [Allen & Kennard (1993). Chem. Des. Autom. News, 8, 1, 31–37]; no significant differences were found. Thus, conformational changes induced by the double bonds are not discriminative with respect to the activity of the compounds. Comparisons of the side-chain conformations of active and inactive structures revealed that the crystal structures were not conclusive as far as correlation of conformation and activity of the side chains were concerned.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101010010/gg1052sup1.cif
Contains datablocks global, II, III, IV, V, VI

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010010/gg1052IIsup2.hkl
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010010/gg1052IIIsup3.hkl
Contains datablock III

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010010/gg1052IVsup4.hkl
Contains datablock IV

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010010/gg1052Vsup5.hkl
Contains datablock V

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010010/gg1052VIsup6.hkl
Contains datablock VI

CCDC references: 174812; 174813; 174814; 174815; 174816

Comment top

Sterol compounds are intermediates in the biosynthetic pathway of cholesterol. One of these compounds, called follicular fluid-meiosis activating sterol [FF-MAS, (I)], was found to initiate the resumption of prophase I-arrested human oocytes (Byskov et al., 1995). For this reason, FF-MAS may serve as a lead compound in the development of agonists and antagonists to either stimulate or block the production of functional egg cells. A number of FF-MAS-related sterols have been synthesized and tested with a varying number of double bonds at different positions in the steroid skeleton. Very few double-bond configurations were found to yield active compounds. Those that are active have double bonds at positions 8 and 14 or an aromatic C ring (Grønvald et al., 1997). Sterols with Δ5, Δ5,7, Δ7,9(11), Δ8, Δ8(14) etc. double bond(s) gave inactive compounds. Thus, the position and number of double bonds appear to be an important prerequisite for activity, which leads to the question whether there is a correlation between activity and the conformation of the skeleton as induced by the double-bond configuration.

The side-chain structure appears to have an impact on activity as well. FF-MAS-related sterols show a similar structure–activity relationship with respect to the stereochemistry of C-20 as 1α,25-dihydroxy-vitamin D3, 1α,25-(OH)2—D3. It was found that a derivative of 1α,25-(OH)2—D3 with an inverted stereochemistry at C-20 (`unnatural configuration') has a similar affinity for the vitamin D receptor (VDR) as the endogenous ligand 1α,25-(OH)2—D3 with a `natural configuration' at C-20, and even has an increased transcriptional activity (Liu et al., 1997; Väisänen et al., 1999; Boullion et al., 1995). Similarly, analogs of FF-MAS with unnatural C-20 stereochemistry are able to induce meiosis, provided that C-22 is replaced by an O atom. This is exemplified by compound (IV). In contrast, 22-oxa sterols with the C-20 configuration, as in FF-MAS, are in general inactive, as is the case for compound (V). Examination of the crystal structures may provide an understanding of the underlying structure–activity relationships.

In this paper, we present the crystal structures of five FF-MAS derived sterols (II)-(VI). All five compounds have a Δ8,14 double-bond configuration and all but (VI) have a 3β-OH moiety. Compounds (II)-(IV) are active and (V) and (VI) are inactive in in vitro tests. The inactivity of compound (VI) is most likely caused by the absence of the mandatory 3β-OH group. Ellipsoid plots of the major components of one of the molecules in each structure is given in Fig. 1 as representative of that compound.

In the crystal structures of compounds (II)–(V), the hydroxyl groups form hydrogen bonds to other hydroxyl groups present in the structure. Different types of hydrogen-bonding schemes are found. The two independent molecules in the crystal structure of (II) form hydrogen bonds in a pairwise fashion, denoted by a D by the graph-set notation (Etter, 1990; Bernstein et al., 1995). The hydroxyl H atoms are disordered over two positions in which one component donates a hydrogen bond to the other molecule. The second component does not participate in a hydrogen bond, as no hydrogen-bond acceptor was available within 3.6 Å. In the crystal structure of (III), hydrogen bonds are found in a cyclic arrangement of co-operative hydrogen bonds involving the two independent molecules and two of their symmetry-related copies [R44(8) in graph-set notation], with disordered directionality. The hydroxyl H atoms of compound (IV) form spiralling hydrogen-bond chains of which the central axis coincides with the 62 axis [C(2) in graph-set notation], each H atom donates to the molecule on the α-side of the molecule. The O···O distance of the hydrogen bonds is rather long, implying a weaker hydrogen bond. The long donor–acceptor distance is most likely a consequence of packing optimization of the bulky steroid moiety. The water molecule of the monohydrate structure of compound (V) is located at a special position, i.e. on the twofold rotation axis. The structure contains one potential hydrogen-bond donor more than there are potential hydrogen-bond acceptors. The free H atom was placed at electron density found on the twofold axis near the water O atom, taking into account a reasonable geometry. The hydroxyl groups of compound (V) and the other H atom of the water molecule form infinite co-operative hydrogen-bonded chains with disordered directionality. The chains consisted of three different motifs, which can be described by DD33(6)D in unary graph-set notation. The binary notation is C55(10). [unary ?]

To determine whether differences in the conformation of the skeleton can explain differences in activity of double-bond isomers, the skeletal conformations of compounds (II)-(V) and of compound (VI) are compared with those of double-bond sterol isomers in the Cambridge Structural Database (CSD Version of October 2000, 224400 entries; Allen & Kennard, 1993). The CSD was searched for compounds containing the four-ring sterol topology with androstane stereochemistry, containing a varying number of double bonds at different positions. For the Δ8,14 structures presented here and that of an aromatic C ring structure (Ferguson et al., 1982), a type of skeleton that can yield active compounds, it is found that the atomic positions of the superimposed skeletons are very similar. However, differences between the atomic positions of these classes of skeletons with skeleton classes which are known to give inactive compounds (i.e. the Δ5 and fully saturated structures) are of the same magnitude. This finding indicates that, although the positions of the double bonds in the skeletons are important, the skeleton conformation is not the determining factor for the activity of double-bond FF-MAS isomers.

Although the skeletal structure of (V) satisfies the conditions required for activity discussed in the first paragraph, the compound is not active. Its lack of activity is therefore probably related to the structure of the side chain. In order to compare the side-chain conformations of the molecules in all five crystal structures, the skeletons of all independent molecules were superimposed. A stereoview of the superposition of the skeleton atoms of crystal structures (II)-(V) is given in Fig. 2. Rings A, B and C were included in the fit but have been omitted from the figure for clarity. The independent molecules of compound (V) are shown in dark grey, with those of the other compounds in light grey. Table 1 gives successive torsion angles in the side chains of the five structures for each of the independent molecules and for disordered side-chain conformations. The orientations of the side chains correspond to those found for other sterols with both an R and S C-20 stereochemistry (Nes et al., 1984). Compounds (II), (III) and (V), with a natural configuration (see above) at C-20, crystallize with the side chain extended pointing away from ring D (the so-called `north-east' orientation). The orientation of the side chain in the structure of (IV), which has un unnatural C-20 stereochemistry, is called the `north-west' orientation and points upwards in the plane of the paper of the Scheme. It can be seen from Fig. 2 that the phenyl rings of the side chains of compound (II) occupy the same region in space as that of the inactive compound (V). The side chains of the active compounds (II) and (III) occupy different regions in space. The active conformation(s) can therefore not be distilled from the crystal structure conformations. Either the active conformation of compound (II) is a conformation present in solution but not in the crystal structure, or compound (V) is mainly present in another (inactive) conformation in solution.

An interesting aspect of the aromatic C-ring structure mentioned above is the orientation of the side chain with respect to the skeleton. The C17—C20 bond of the aromatic C ring structure points upwards with respect to the plane through the skeleton rings (Fig. 3). This is also found for 1α,25-(OH)2—D3 bound to its receptor (Rochel et al., 2000). By rotation of the C17—C20 torsion angle, the conformation of the side chains of compounds (I)-(VI) can change such that the direction is similar to the side chain of the aromatic C-ring structure. NMR experiments are planned to gain insight into the conformational behavior of the compounds in solution.

Experimental top

Colourless single crystals suitable for X-ray analysis of compounds (II), (III) and (V) were obtained by vapor diffusion of a pyridine solution into CH3CN. Crystals formed after several days. Colourless single crystals of compounds (IV) and (VI) were obtained by slow evaporation of ethanol solutions.

Refinement top

Due to the absence of significant anomalous dispersion, the absolute structure cannot be determined reliably. The configuration was chosen such that for each compound the skeleton stereochemistry corresponds to those of other related androstanes. Friedel pairs were merged for each structure. H atoms were introduced at calculated positions, riding on their carrier atoms. The methyl groups were refined as rigid groups, allowing for rotation around the C—C bonds. The hydroxyl H atoms were also treated as rigid groups. Their initial positions were determined from a circular residual-density map. H atoms were refined with a fixed isotropic displacement parameter related to the value of the equivalent isotropic displacement parameter of the carrier atom by a factor of 1.5 for the methyl and hydroxyl H atoms and 1.2 for all other H atoms. The structure of (III) contains a disordered solvent region (15 e, 170 Å3) that could not be interpreted. A new set of structure factors was calculated using the SQUEEZE algorithm in PLATON (van der Sluis & Spek, 1990). Atoms C25A, C26A and C27A show large anisotropy, (U3/U1)max = 16.7 for C26A. Schomaker & Trueblood (1968) TLS analysis on C22A and the phenyl ring resulted in a maximum libration amplitude <π2> = 152. Since the electron-density map did not show separate peaks, a disorder model was not thought appropriate. The two independent molecules in the crystal structure of (VI) are both disordered, related by intermolecular contacts. A flip of ring A from a chair to a twist-boat conformation of one of the molecules causes a 30° rotation over the C-24 to C-25 dihedral in the other. The occupancy factors of the disorder components in both molecules were linked.

Computing details top

For all compounds, data collection: COLLECT (Nonius, 1998). Cell refinement: DIRAX (Duisenberg, 1992) for (II), (IV), (V); DENZO (Otwinowski & Minor, 1997) for (III); DENZO 1.11.0 (Otwinowski & Minor, 1997) for (VI). Data reduction: EVAL14 (Duisenberg, 1998) for (II), (IV), (V); DENZO (Otwinowski & Minor, 1997) for (III); DENZO 1.11.0 (Otwinowski & Minor, 1997) for (VI). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001). Software used to prepare material for publication: PLATON for (II), (III), (IV), (V); PLATON (Spek, 2001) for (VI).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plots at the 50% probability level for structures (II)-(VI). The disordered systems and the other independent molecules in each of the structures are similar. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Stereoview of the side chains in the crystal structures of compounds (II)-(V) after superposition of the skeletons. Compound (V) is shown in grey, while compounds (II)-(IV) are shown in black. The primes indicate the independent molecules in the structures.
[Figure 3] Fig. 3. Stereoview of the side chains of in the crystal structure of compounds (II)-(IV) (grey) and the structure of the aromatic C ring structure (22α,23α-dibromo-18-nor-12-methyl-5α,17β-ergosta-8,11,13 (14)-triene-3β-t- butyldimethylsylyl ether; Ferguson et al., 1982) (black).
(II) 4,4-dimethyl-23-phenyl-24-nor-5α-cholane-8,14-dien-3β-ol top
Crystal data top
C31H44OF(000) = 952
Mr = 432.66Cell parameters were determined by rotating the crystal simultaneously over phi and chi angles, from which accurate phi angles could be determined (Duisenberg et al. (2000), J. Appl. Cryst., 33, 893-898).
Monoclinic, P21Dx = 1.130 Mg m3
Hall symbol: P 2y1Mo Kα radiation, λ = 0.71073 Å
a = 7.271 (3) ÅCell parameters from 114 reflections
b = 9.733 (5) Åθ = 3.1–16.8°
c = 35.98 (2) ŵ = 0.07 mm1
β = 93.28 (4)°T = 150 K
V = 2542 (2) Å3Block, colourless
Z = 40.3 × 0.3 × 0.3 mm
Data collection top
Enraf-Nonius κ-CCD
diffractometer
4455 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.3°, θmin = 1.1°
Detector resolution: 18.4 pixels mm-1h = 88
ϕ and ω scans with κ offsetsk = 119
15221 measured reflectionsl = 4341
4842 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0516P)2 + 0.49P]
where P = (Fo2 + 2Fc2)/3
4842 reflections(Δ/σ)max = 0.001
590 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.14 e Å3
Crystal data top
C31H44OV = 2542 (2) Å3
Mr = 432.66Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.271 (3) ŵ = 0.07 mm1
b = 9.733 (5) ÅT = 150 K
c = 35.98 (2) Å0.3 × 0.3 × 0.3 mm
β = 93.28 (4)°
Data collection top
Enraf-Nonius κ-CCD
diffractometer
4455 reflections with I > 2σ(I)
15221 measured reflectionsRint = 0.048
4842 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.116H-atom parameters constrained
S = 1.10Δρmax = 0.18 e Å3
4842 reflectionsΔρmin = 0.14 e Å3
590 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/UeqOcc. (<1)
O30.4419 (3)0.1397 (3)0.23703 (5)0.0640 (8)
C10.2140 (4)0.0281 (3)0.14635 (7)0.0487 (9)
C20.2343 (4)0.0734 (4)0.18678 (8)0.0560 (10)
C30.4343 (4)0.0923 (3)0.19911 (7)0.0487 (9)
C40.5510 (4)0.0347 (3)0.19464 (7)0.0448 (8)
C50.5192 (3)0.0820 (3)0.15372 (7)0.0400 (8)
C60.6363 (4)0.2022 (3)0.14302 (8)0.0514 (9)
C70.6471 (4)0.2054 (4)0.10097 (8)0.0544 (10)
C80.4655 (3)0.1839 (3)0.08056 (7)0.0422 (8)
C90.3178 (3)0.1352 (3)0.09692 (7)0.0422 (8)
C100.3181 (3)0.1045 (3)0.13883 (7)0.0410 (8)
C110.1357 (3)0.1184 (4)0.07482 (8)0.0526 (9)
C120.1490 (4)0.1172 (3)0.03286 (8)0.0488 (9)
C130.2719 (3)0.2313 (3)0.01960 (7)0.0431 (8)
C140.4551 (3)0.2179 (3)0.04082 (8)0.0483 (9)
C150.5912 (4)0.2465 (4)0.01906 (9)0.0668 (13)
C160.5235 (4)0.2724 (5)0.02041 (9)0.0705 (13)
C170.3264 (4)0.2176 (3)0.02139 (8)0.0498 (9)
C180.1935 (4)0.3714 (4)0.02795 (9)0.0599 (11)
C190.2190 (4)0.2239 (4)0.15672 (9)0.0603 (10)
C200.2027 (4)0.2782 (3)0.05264 (8)0.0522 (9)
C210.0067 (4)0.2253 (5)0.05316 (9)0.0717 (13)
C220.2811 (5)0.2560 (4)0.09097 (8)0.0608 (11)
C230.3109 (7)0.1080 (4)0.10151 (10)0.0833 (14)
C240.3519 (6)0.0896 (4)0.14184 (10)0.0735 (14)
C250.2123 (8)0.0891 (5)0.16871 (12)0.0998 (19)
C260.2428 (11)0.0731 (6)0.20606 (14)0.124 (3)
C270.4148 (13)0.0544 (5)0.21632 (15)0.123 (3)
C280.5584 (10)0.0551 (5)0.19076 (16)0.109 (2)
C290.5260 (7)0.0723 (4)0.15284 (13)0.0882 (18)
C410.5106 (5)0.1416 (4)0.22411 (9)0.0644 (11)
C420.7521 (4)0.0081 (4)0.20070 (9)0.0638 (10)
O3A0.1669 (3)0.6827 (2)0.26651 (5)0.0616 (7)
C1A0.3386 (4)0.7326 (3)0.36674 (8)0.0482 (9)
C2A0.3449 (4)0.7170 (4)0.32460 (8)0.0526 (9)
C3A0.1562 (4)0.7028 (3)0.30580 (7)0.0491 (9)
C4A0.0278 (4)0.8215 (3)0.31419 (7)0.0452 (8)
C5A0.0316 (3)0.8400 (3)0.35743 (7)0.0401 (8)
C6A0.0964 (3)0.9501 (3)0.37008 (7)0.0499 (9)
C7A0.1294 (3)0.9338 (4)0.41110 (7)0.0510 (9)
C8A0.0435 (3)0.9024 (3)0.43461 (7)0.0384 (7)
C9A0.1981 (3)0.8586 (3)0.42008 (7)0.0391 (7)
C10A0.2238 (3)0.8548 (3)0.37805 (7)0.0396 (8)
C11A0.3655 (3)0.8234 (4)0.44503 (7)0.0504 (9)
C12A0.3338 (3)0.8170 (3)0.48651 (7)0.0431 (8)
C13A0.2109 (3)0.9315 (3)0.49880 (7)0.0374 (7)
C14A0.0347 (3)0.9239 (3)0.47466 (7)0.0387 (7)
C15A0.1096 (3)0.9484 (4)0.49461 (8)0.0528 (9)
C16A0.0561 (4)0.9696 (4)0.53499 (8)0.0583 (10)
C17A0.1403 (3)0.9144 (3)0.53869 (7)0.0419 (8)
C18A0.2982 (4)1.0706 (3)0.49311 (9)0.0551 (10)
C19A0.3262 (4)0.9863 (3)0.36920 (8)0.0548 (10)
C20A0.2570 (4)0.9743 (3)0.57156 (7)0.0502 (9)
C21A0.4473 (4)0.9107 (5)0.57579 (9)0.0712 (13)
C22A0.1607 (4)0.9666 (3)0.60830 (8)0.0574 (10)
C23A0.1224 (6)0.8240 (4)0.62204 (10)0.0733 (14)
C24A0.0272 (5)0.8254 (3)0.65823 (8)0.0565 (10)
C25A0.1577 (5)0.8323 (4)0.65900 (12)0.0784 (14)
C26A0.2409 (7)0.8366 (5)0.6934 (2)0.108 (2)
C27A0.1358 (11)0.8354 (5)0.72547 (16)0.111 (3)
C28A0.0437 (9)0.8281 (5)0.72503 (11)0.101 (2)
C29A0.1270 (6)0.8220 (4)0.69200 (10)0.0751 (12)
C41A0.1667 (4)0.7783 (4)0.30068 (9)0.0640 (13)
C42A0.0758 (4)0.9500 (4)0.29286 (8)0.0577 (10)
H1A0.084400.014800.139400.0580*
H1B0.259300.100600.130800.0580*
H2A0.179800.004900.202300.0670*
H2B0.169000.159200.189700.0670*
H30.484200.165200.183800.0590*
H50.562800.005000.139000.0480*
H6A0.759100.193400.154800.0620*
H6B0.582800.287100.151500.0620*
H7A0.696500.293500.093800.0650*
H7B0.731600.134600.093700.0650*
H11A0.054600.192700.081300.0630*
H11B0.079400.033000.082200.0630*
H12A0.026600.127400.021000.0590*
H12B0.197500.029200.025400.0590*
H150.714600.250000.027400.0800*
H16A0.596800.223000.037700.0850*
H16B0.525600.369600.026300.0850*
H170.334300.118900.026500.0600*
H18A0.268600.441400.017700.0900*
H18B0.192000.383600.054400.0900*
H18C0.070100.378100.017100.0900*
H19A0.102100.238900.143600.0910*
H19B0.292600.305500.155600.0910*
H19C0.200000.202300.182200.0910*
H200.197800.377600.048500.0630*
H21A0.051700.258800.031700.1070*
H21B0.007700.126600.052800.1070*
H21C0.060200.256800.075300.1070*
H22A0.197700.297600.109700.0730*
H22B0.397900.304000.091400.0730*
H23A0.201500.055700.096500.1000*
H23B0.412600.071200.086000.1000*
H250.092000.100000.161700.1200*
H260.144800.075300.223800.1490*
H270.435800.040700.241300.1480*
H280.677900.044300.198200.1310*
H290.624600.071900.135200.1060*
H31A0.390200.070800.252500.0960*0.500
H31C0.372400.223200.238600.0960*0.500
H41A0.562600.112100.247900.0960*
H41B0.379700.152000.225300.0960*
H41C0.563900.228000.217700.0960*
H42A0.783900.069000.181100.0960*
H42B0.769800.054300.224200.0960*
H42C0.829200.071900.200600.0960*
H1C0.287900.649400.376900.0580*
H1D0.463300.743200.377500.0580*
H2C0.405200.796700.314600.0630*
H2D0.417400.636700.319200.0630*
H3A0.101700.619300.315700.0590*
H5A0.018300.753900.366800.0480*
H11C0.460300.891100.441200.0600*
H11D0.412100.735000.437400.0600*
H12C0.278300.729400.492100.0520*
H12D0.451700.822600.500500.0520*
H15A0.230300.952100.484600.0630*
H16C0.136300.918500.550600.0700*
H16D0.060101.066100.541600.0700*
H17A0.130900.815500.543200.0500*
H18D0.314901.084300.467100.0830*
H18E0.415601.074400.506700.0830*
H18F0.219501.141200.501900.0830*
H19D0.362200.983000.344000.0820*
H19E0.433900.994700.385800.0820*
H19F0.247101.063900.372300.0820*
H20A0.274401.072000.566200.0600*
H21D0.514100.931500.554200.1070*
H21E0.436200.812900.578300.1070*
H21F0.512200.947400.597600.1070*
H22C0.236501.014000.627300.0690*
H22D0.044801.015700.605300.0690*
H23C0.237700.774300.625500.0880*
H23D0.045700.775800.603300.0880*
H25A0.230300.834300.636900.0940*
H26A0.368500.840200.693900.1300*
H27A0.191300.839700.748100.1330*
H28A0.115000.827100.747300.1210*
H29A0.254600.815300.692300.0900*
H32A0.239800.754600.256500.0920*0.500
H32C0.223000.595400.262000.0920*0.500
H41D0.164900.743100.275800.0960*
H41E0.247300.856400.301000.0960*
H41F0.210100.708300.316800.0960*
H42D0.009701.027000.302100.0870*
H42E0.042200.937400.266900.0870*
H42F0.205800.966900.296100.0870*
H61A0.212900.944500.355600.0600*
H62A0.043201.039700.365800.0600*
H71A0.183301.017800.420100.0610*
H72A0.217500.860200.414000.0610*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0669 (13)0.0787 (16)0.0469 (11)0.0020 (12)0.0079 (9)0.0171 (11)
C10.0388 (13)0.0593 (18)0.0478 (14)0.0141 (13)0.0008 (11)0.0069 (14)
C20.0470 (14)0.069 (2)0.0523 (15)0.0164 (15)0.0054 (12)0.0103 (15)
C30.0526 (15)0.0521 (17)0.0420 (13)0.0007 (14)0.0068 (11)0.0042 (13)
C40.0384 (13)0.0532 (16)0.0430 (14)0.0009 (12)0.0031 (10)0.0006 (12)
C50.0333 (12)0.0413 (14)0.0455 (13)0.0016 (11)0.0021 (10)0.0020 (11)
C60.0389 (13)0.0533 (17)0.0611 (17)0.0087 (13)0.0054 (12)0.0016 (14)
C70.0343 (13)0.065 (2)0.0634 (18)0.0119 (14)0.0010 (12)0.0146 (15)
C80.0275 (11)0.0451 (14)0.0543 (15)0.0002 (11)0.0047 (10)0.0088 (12)
C90.0304 (12)0.0460 (15)0.0502 (14)0.0005 (11)0.0030 (10)0.0040 (12)
C100.0309 (11)0.0459 (15)0.0466 (14)0.0015 (11)0.0049 (10)0.0015 (12)
C110.0297 (12)0.074 (2)0.0540 (16)0.0091 (13)0.0016 (11)0.0168 (15)
C120.0346 (13)0.0575 (18)0.0537 (16)0.0074 (13)0.0025 (11)0.0124 (14)
C130.0329 (12)0.0480 (15)0.0486 (14)0.0008 (12)0.0048 (10)0.0111 (12)
C140.0308 (12)0.0547 (17)0.0595 (16)0.0027 (12)0.0045 (11)0.0131 (14)
C150.0357 (14)0.102 (3)0.0628 (18)0.0095 (17)0.0043 (12)0.0212 (19)
C160.0448 (15)0.105 (3)0.0624 (19)0.0066 (18)0.0084 (13)0.023 (2)
C170.0432 (14)0.0562 (18)0.0505 (15)0.0030 (13)0.0062 (11)0.0118 (14)
C180.0595 (18)0.0573 (19)0.0629 (18)0.0089 (15)0.0024 (14)0.0066 (15)
C190.0503 (16)0.065 (2)0.0661 (18)0.0127 (15)0.0066 (13)0.0027 (16)
C200.0540 (16)0.0510 (17)0.0516 (15)0.0033 (14)0.0024 (12)0.0137 (13)
C210.0527 (17)0.096 (3)0.0649 (19)0.0032 (19)0.0084 (14)0.025 (2)
C220.074 (2)0.0555 (19)0.0529 (17)0.0030 (16)0.0042 (14)0.0188 (15)
C230.128 (3)0.062 (2)0.061 (2)0.011 (2)0.016 (2)0.0143 (18)
C240.112 (3)0.0483 (19)0.061 (2)0.007 (2)0.012 (2)0.0102 (16)
C250.141 (4)0.081 (3)0.076 (3)0.002 (3)0.007 (3)0.008 (2)
C260.216 (7)0.079 (3)0.074 (3)0.011 (4)0.023 (4)0.001 (3)
C270.241 (8)0.059 (3)0.073 (3)0.013 (4)0.040 (4)0.002 (2)
C280.174 (5)0.055 (3)0.104 (4)0.021 (3)0.053 (4)0.013 (3)
C290.126 (4)0.052 (2)0.088 (3)0.016 (2)0.019 (3)0.0107 (19)
C410.072 (2)0.069 (2)0.0515 (17)0.0028 (18)0.0019 (14)0.0132 (16)
C420.0441 (15)0.085 (2)0.0615 (18)0.0034 (16)0.0050 (13)0.0214 (18)
O3A0.0744 (14)0.0662 (14)0.0445 (10)0.0043 (12)0.0061 (9)0.0050 (10)
C1A0.0396 (13)0.0547 (17)0.0504 (15)0.0098 (13)0.0032 (11)0.0021 (13)
C2A0.0474 (15)0.0603 (19)0.0509 (15)0.0101 (14)0.0102 (12)0.0022 (14)
C3A0.0573 (16)0.0477 (16)0.0425 (14)0.0047 (14)0.0058 (12)0.0030 (12)
C4A0.0429 (13)0.0500 (16)0.0426 (13)0.0028 (12)0.0004 (11)0.0062 (12)
C5A0.0320 (12)0.0437 (14)0.0446 (13)0.0022 (11)0.0013 (10)0.0082 (11)
C6A0.0376 (13)0.0590 (18)0.0524 (15)0.0119 (13)0.0024 (11)0.0078 (14)
C7A0.0340 (12)0.067 (2)0.0518 (15)0.0111 (14)0.0008 (11)0.0039 (15)
C8A0.0299 (11)0.0370 (13)0.0483 (13)0.0037 (10)0.0016 (9)0.0030 (11)
C9A0.0296 (11)0.0400 (14)0.0474 (13)0.0019 (10)0.0006 (10)0.0036 (11)
C10A0.0311 (12)0.0432 (15)0.0444 (13)0.0007 (11)0.0023 (10)0.0049 (11)
C11A0.0351 (13)0.0676 (19)0.0481 (15)0.0145 (13)0.0001 (11)0.0019 (14)
C12A0.0329 (12)0.0476 (15)0.0482 (14)0.0061 (12)0.0034 (10)0.0003 (12)
C13A0.0320 (11)0.0364 (14)0.0440 (13)0.0030 (10)0.0029 (9)0.0008 (11)
C14A0.0329 (11)0.0355 (13)0.0475 (13)0.0022 (10)0.0017 (10)0.0022 (11)
C15A0.0334 (13)0.071 (2)0.0541 (15)0.0076 (14)0.0041 (11)0.0014 (15)
C16A0.0436 (14)0.077 (2)0.0550 (16)0.0110 (15)0.0092 (12)0.0001 (16)
C17A0.0394 (12)0.0388 (14)0.0476 (14)0.0026 (11)0.0044 (10)0.0018 (12)
C18A0.0561 (17)0.0454 (16)0.0639 (18)0.0129 (14)0.0054 (14)0.0015 (14)
C19A0.0491 (15)0.0549 (18)0.0603 (17)0.0112 (14)0.0020 (13)0.0064 (14)
C20A0.0536 (15)0.0465 (16)0.0503 (15)0.0022 (13)0.0014 (12)0.0070 (13)
C21A0.0555 (17)0.098 (3)0.0584 (18)0.001 (2)0.0112 (13)0.015 (2)
C22A0.0734 (19)0.0481 (17)0.0509 (16)0.0046 (16)0.0056 (14)0.0082 (14)
C23A0.110 (3)0.0511 (19)0.061 (2)0.003 (2)0.0236 (19)0.0051 (16)
C24A0.075 (2)0.0412 (16)0.0534 (16)0.0016 (15)0.0052 (14)0.0018 (13)
C25A0.076 (2)0.058 (2)0.100 (3)0.0058 (19)0.005 (2)0.001 (2)
C26A0.085 (3)0.062 (3)0.182 (6)0.008 (2)0.057 (3)0.003 (3)
C27A0.173 (6)0.066 (3)0.099 (4)0.018 (4)0.062 (4)0.006 (3)
C28A0.169 (5)0.078 (3)0.056 (2)0.015 (3)0.000 (3)0.000 (2)
C29A0.085 (2)0.073 (2)0.066 (2)0.008 (2)0.0059 (18)0.0031 (19)
C41A0.0502 (16)0.086 (3)0.0545 (17)0.0070 (17)0.0076 (13)0.0014 (17)
C42A0.0681 (18)0.0582 (19)0.0472 (15)0.0044 (16)0.0058 (13)0.0156 (14)
Geometric parameters (Å, º) top
O3—C31.438 (3)C42—H42A0.9596
O3—H31A0.9617C42—H42B0.9598
O3—H31C0.9604C42—H42C0.9596
O3A—C3A1.434 (3)C1A—C2A1.527 (4)
O3A—H32A0.9604C1A—C10A1.522 (4)
O3A—H32C0.9604C2A—C3A1.501 (4)
C1—C21.519 (4)C3A—C4A1.526 (4)
C1—C101.528 (4)C4A—C42A1.518 (5)
C2—C31.507 (4)C4A—C41A1.528 (4)
C3—C41.513 (4)C4A—C5A1.565 (4)
C4—C421.524 (4)C5A—C10A1.551 (3)
C4—C411.526 (5)C5A—C6A1.507 (4)
C4—C51.547 (4)C6A—C7A1.517 (4)
C5—C101.544 (3)C7A—C8A1.506 (3)
C5—C61.510 (4)C8A—C14A1.461 (4)
C6—C71.520 (4)C8A—C9A1.336 (3)
C7—C81.488 (4)C9A—C11A1.510 (3)
C8—C141.465 (4)C9A—C10A1.535 (4)
C8—C91.340 (3)C10A—C19A1.524 (4)
C9—C111.514 (3)C11A—C12A1.524 (4)
C9—C101.537 (4)C12A—C13A1.510 (4)
C10—C191.529 (4)C13A—C17A1.561 (3)
C11—C121.518 (4)C13A—C14A1.508 (3)
C12—C131.519 (4)C13A—C18A1.514 (4)
C13—C171.555 (4)C14A—C15A1.326 (3)
C13—C141.503 (3)C15A—C16A1.497 (4)
C13—C181.515 (5)C16A—C17A1.524 (4)
C14—C151.326 (4)C17A—C20A1.531 (4)
C15—C161.498 (5)C20A—C21A1.516 (4)
C16—C171.528 (4)C20A—C22A1.533 (4)
C17—C201.518 (4)C22A—C23A1.505 (5)
C20—C221.537 (4)C23A—C24A1.509 (5)
C20—C211.514 (4)C24A—C29A1.379 (5)
C22—C231.508 (5)C24A—C25A1.348 (5)
C23—C241.509 (5)C25A—C26A1.409 (8)
C24—C291.358 (7)C26A—C27A1.347 (9)
C24—C251.361 (6)C27A—C28A1.308 (10)
C25—C261.383 (7)C28A—C29A1.366 (6)
C26—C271.337 (12)C1A—H1C0.9699
C27—C281.351 (10)C1A—H1D0.9708
C28—C291.408 (7)C2A—H2C0.9703
C1—H1A0.9697C2A—H2D0.9686
C1—H1B0.9698C3A—H3A0.9801
C2—H2A0.9689C5A—H5A0.9806
C2—H2B0.9693C6A—H61A0.9703
C3—H30.9805C6A—H62A0.9699
C5—H50.9808C7A—H71A0.9703
C6—H6B0.9700C7A—H72A0.9706
C6—H6A0.9700C11A—H11C0.9691
C7—H7A0.9703C11A—H11D0.9701
C7—H7B0.9691C12A—H12C0.9693
C11—H11B0.9703C12A—H12D0.9705
C11—H11A0.9700C15A—H15A0.9301
C12—H12B0.9700C16A—H16C0.9697
C12—H12A0.9698C16A—H16D0.9698
C15—H150.9303C17A—H17A0.9793
C16—H16A0.9696C18A—H18D0.9598
C16—H16B0.9698C18A—H18E0.9599
C17—H170.9804C18A—H18F0.9594
C18—H18C0.9600C19A—H19D0.9585
C18—H18B0.9597C19A—H19E0.9608
C18—H18A0.9599C19A—H19F0.9597
C19—H19B0.9598C20A—H20A0.9799
C19—H19A0.9595C21A—H21D0.9610
C19—H19C0.9582C21A—H21E0.9600
C20—H200.9799C21A—H21F0.9611
C21—H21A0.9593C22A—H22C0.9700
C21—H21B0.9608C22A—H22D0.9694
C21—H21C0.9596C23A—H23C0.9697
C22—H22B0.9702C23A—H23D0.9709
C22—H22A0.9690C25A—H25A0.9291
C23—H23B0.9692C26A—H26A0.9296
C23—H23A0.9699C27A—H27A0.9301
C25—H250.9302C28A—H28A0.9292
C26—H260.9293C29A—H29A0.9295
C27—H270.9298C41A—H41D0.9593
C28—H280.9297C41A—H41E0.9603
C29—H290.9299C41A—H41F0.9598
C41—H41A0.9597C42A—H42D0.9599
C41—H41B0.9605C42A—H42E0.9597
C41—H41C0.9596C42A—H42F0.9599
O3···O3Ai2.890 (3)H12A···H21A2.3306
O3···C28ii3.405 (6)H12A···H15ix2.5852
O3···C27ii3.255 (6)H12A···H18C2.4656
O3A···C27Aiii3.401 (5)H12B···H16Bii2.5417
O3A···O3iv2.890 (3)H12B···H172.3347
O3···H32Ai1.9561H12B···C83.0920
O3···H42B2.5912H12C···H17A2.3359
O3···H41B2.9021H12C···H16Diii2.5087
O3···H2Ci2.8860H12C···C15Aiii3.0465
O3···H41A2.6250H12D···H18E2.4763
O3A···H42E2.6400H12D···H21D2.2275
O3A···H41D2.5239H12D···C18Ax3.0542
O3A···H26v2.8622H12D···C21A2.8433
O3A···H31Civ2.0619H15···C72.7540
C3···C28ii3.446 (6)H15···H7A2.4372
C9···C183.465 (4)H15···H12Aviii2.5852
C9A···C18A3.387 (4)H15A···H71A2.4499
C12···C213.375 (4)H15A···C7A2.7902
C12A···C21A3.395 (4)H16A···H23B2.5943
C16···C233.598 (5)H16A···C21viii3.0631
C18···C93.465 (4)H16A···C222.9227
C18···C213.454 (5)H16A···H21Aviii2.5762
C18A···C21A3.475 (5)H16A···H22B2.4751
C18A···C9A3.387 (4)H16B···H202.4712
C19···C413.229 (5)H16B···H22B2.5509
C19A···C42A3.227 (4)H16B···H12Bvi2.5417
C21···C123.375 (4)H16B···C223.0534
C21···C183.454 (5)H16C···C22A2.9461
C21A···C12A3.395 (4)H16C···H21Dix2.5558
C21A···C18A3.475 (5)H16C···H22D2.4911
C23···C163.598 (5)H16D···H12Cvii2.5087
C27···O3vi3.255 (6)H16D···H20A2.5408
C27A···O3Avii3.401 (5)H16D···H22D2.4238
C28···O3vi3.405 (6)H16D···C22A2.9721
C28···C3vi3.446 (6)H17···H21B2.5066
C41···C193.229 (5)H17···C232.6965
C42A···C19A3.227 (4)H17···H12B2.3347
C1···H11B2.5259H17···H23B2.2939
C1A···H11D2.5678H17A···C23A2.8420
C2···H19C2.6992H17A···H23D2.3156
C2···H32Ai3.0142H17A···H12C2.3359
C2···H41B2.7720H17A···H21E2.4905
C2A···H42F2.8057H18A···C153.0150
C2A···H19D2.6826H18A···H202.4866
C3···H32Ai2.9696H18A···C203.0031
C3A···H31Civ3.0448H18A···C162.8830
C4···H19C3.0404H18B···C112.7212
C4A···H19D3.0389H18B···C92.9770
C6···H41C2.7788H18B···C82.8991
C6···H19B2.7551H18B···H11A2.3448
C6···H42C2.7450H18C···C202.9065
C6A···H41E2.8109H18C···C212.9464
C6A···H42D2.7117H18C···H21A2.2444
C6A···H19F2.7292H18C···H12A2.4656
C7···H11Aviii3.0879H18C···H202.5853
C7···H152.7540H18D···C8A2.8515
C7A···H15A2.7902H18D···C9A2.8714
C8···H52.7899H18D···C11A2.6922
C8···H12B3.0920H18D···H11C2.3738
C8···H18B2.8991H18E···C12Axi2.9841
C8A···H5A2.8492H18E···H21D2.2865
C8A···H18D2.8515H18E···C21A2.9505
C9···H18B2.9770H18E···H12D2.4763
C9···H6B3.0532H18E···C20A2.8342
C9A···H62A3.0996H18E···H20A2.4267
C9A···H18D2.8714H18F···C16A2.9147
C11···H19A2.7619H18F···C20A2.9861
C11···H1A2.7052H18F···C15A3.0405
C11···H18B2.7212H18F···H20A2.4206
C11···H7Bix3.0574H18F···C15Avii3.0994
C11···H1B3.0333H19A···H6Aix2.5871
C11A···H18D2.6922H19A···C112.7619
C11A···H19E2.7731H19A···H1A2.4769
C11A···H1C3.0062H19A···H11A2.2929
C11A···H1D2.6863H19B···C29vi2.9169
C12···H21A3.0061H19B···H6B2.1311
C12A···H21D2.9200H19B···C28vi2.9188
C12A···H18Ex2.9841H19B···C62.7551
C13···H21A2.9185H19C···C22.6992
C13A···H21D2.8862H19C···C43.0404
C15···H18A3.0150H19C···C412.7080
C15···H7B3.0210H19C···H2A2.1504
C15···H7A2.7912H19C···H41B2.0297
C15A···H71A2.7867H19D···C2A2.6826
C15A···H72A3.0828H19D···C42A2.7178
C15A···H12Cvii3.0465H19D···H2C2.1314
C15A···H18F3.0405H19D···C4A3.0389
C15A···H18Fiii3.0994H19D···H42F2.0158
C16···H22B2.6806H19E···H1D2.4768
C16···H18A2.8830H19E···H11C2.2322
C16A···H22D2.6318H19E···C11A2.7731
C16A···H18F2.9147H19F···H62A2.1235
C17···H23B2.8273H19F···C6A2.7292
C17A···H23D2.8071H19F···C25Avii2.9038
C18···H21A2.9237H20···H18C2.5853
C18···H21Bv3.0429H20···H18A2.4866
C18···H202.7532H20···C182.7532
C18···H11A2.8199H20···H16B2.4712
C18A···H20A2.6453H20A···H16D2.5408
C18A···H21D2.9553H20A···C18A2.6453
C18A···H11C2.8604H20A···H18F2.4206
C18A···H12Dxi3.0542H20A···H18E2.4267
C19···H41B2.7592H21A···C132.9185
C19···H11A2.9177H21A···C123.0061
C19···H6B2.7327H21A···H12A2.3306
C19···H2A2.7899H21A···H16Aix2.5762
C19A···H42F2.7305H21A···H18C2.2444
C19A···H11C2.8690H21A···C182.9237
C19A···H2C2.7792H21B···C232.8994
C19A···H62A2.7316H21B···H172.5066
C20···H18C2.9065H21B···C18xiii3.0429
C20···H18A3.0031H21B···H23A2.2776
C20A···H18E2.8342H21C···H22A2.3391
C20A···H18F2.9861H21D···C12A2.9200
C21···H23A2.7231H21D···C13A2.8862
C21···H18C2.9464H21D···C18A2.9553
C21···H12A2.8291H21D···H12D2.2275
C21···H16Aix3.0631H21D···H16Cviii2.5558
C21A···H18E2.9505H21D···H18E2.2865
C21A···H23C2.7561H21E···H23C2.3213
C21A···H12D2.8433H21E···H17A2.4905
C22···H16B3.0534H21E···C23A2.8469
C22···H16A2.9227H21F···H25Aviii2.5325
C22A···H16D2.9721H21F···H1Cxi2.5821
C22A···H16C2.9461H21F···H22C2.4136
C23···H21B2.8994H22A···C252.9433
C23···H172.6965H22A···H21C2.3391
C23···H7Aii3.0744H22B···H16A2.4751
C23A···H62Aiii2.8652H22B···H16B2.5509
C23A···H17A2.8420H22B···C162.6806
C23A···H21E2.8469H22C···H21F2.4136
C24···H6Bii3.0057H22D···C25A3.0680
C24···H3vi3.0986H22D···C16A2.6318
C24A···H62Aiii2.9164H22D···H5Avii2.5382
C25···H22A2.9433H22D···H16C2.4911
C25A···H3Avii2.9590H22D···H16D2.4238
C25A···H19Fiii2.9038H23A···C212.7231
C25A···H22D3.0680H23A···H252.4716
C26···H28Axii3.0388H23A···H21B2.2776
C26···H41Dxiii3.0318H23B···H292.4129
C26A···H3Avii2.9565H23B···H172.2939
C26A···H32Cvii2.9855H23B···C172.8273
C27···H3vi3.0428H23B···H16A2.5943
C27···H31Cvi2.8044H23C···H21E2.3213
C27A···H32Cvii2.6537H23C···H29A2.4325
C28···H19Bii2.9188H23C···C21A2.7561
C28···H3vi2.7530H23D···H17A2.3156
C28···H31Cvi2.8234H23D···C17A2.8071
C28A···H26xiv3.0926H23D···H25A2.4679
C29···H6Bii2.8876H23D···H62Aiii2.5534
C29···H19Bii2.9169H25···H23A2.4716
C29···H3vi2.7866H25A···H21Fix2.5325
C29A···H42Diii3.0499H25A···H23D2.4679
C41···H6B3.0435H26···C28Axii3.0926
C41···H2A2.8668H26···O3Axiii2.8622
C41···H31A2.4872H26···H41Dxiii2.4941
C41···H19C2.7080H27A···H32Cvii2.5239
C41A···H61A2.5904H27A···H41Bvii2.5060
C42···H6A2.5663H28···H32Cii2.4950
C42A···H32A2.6323H28A···C26xiv3.0388
C42A···H62A2.9424H29···H23B2.4129
C42A···H19D2.7178H29A···H23C2.4325
C42A···H31Aiv2.7848H31A···C412.4872
C42A···H2C2.8914H31A···C42Ai2.7848
H1A···H19A2.4769H31A···H2Ci2.5767
H1A···C112.7052H31A···H32Ai2.0304
H1A···H11B2.1082H31A···H2A2.3870
H1B···C113.0333H31A···H41B2.3786
H1B···H52.4370H31A···H42Fi2.1526
H1B···H11B2.4895H31A···H41A2.1890
H1B···H32.5197H31C···C3Ai3.0448
H1C···C11A3.0062H31C···H2B2.3180
H1C···H3A2.5350H31C···O3Ai2.0619
H1C···H21Fx2.5821H31C···H32Ci2.2607
H1C···H5A2.4558H31C···C27ii2.8044
H1C···H11D2.4542H31C···H32Ai1.2092
H1D···C11A2.6863H31C···C28ii2.8234
H1D···H11D2.2094H32A···C2iv3.0142
H1D···H19E2.4768H32A···C3iv2.9696
H2A···H41B2.2343H32A···H42F2.5301
H2A···C192.7899H32A···H2Biv2.5698
H2A···C412.8668H32A···H2C2.3867
H2A···H19C2.1504H32A···C42A2.6323
H2A···H31A2.3870H32A···O3iv1.9561
H2B···H31C2.3180H32A···H42E2.3306
H2B···H32Ai2.5698H32A···H31Aiv2.0305
H2C···C42A2.8914H32A···H31Civ1.2092
H2C···O3iv2.8860H32C···H31Civ2.2607
H2C···C19A2.7792H32C···H27Aiii2.5239
H2C···H32A2.3867H32C···C26Aiii2.9855
H2C···H42F2.2758H32C···C27Aiii2.6537
H2C···H19D2.1314H32C···H2D2.4621
H2C···H31Aiv2.5767H32C···H28vi2.4950
H2D···H32C2.4621H41A···O32.6250
H3···C27ii3.0428H41A···H31A2.1890
H3···C24ii3.0986H41A···H42B2.4015
H3···H1B2.5197H41B···O32.9021
H3···H52.4030H41B···C22.7720
H3···H42A2.3789H41B···H19C2.0297
H3···C29ii2.7866H41B···H31A2.3786
H3···C28ii2.7530H41B···H27Aiii2.5060
H3A···H5A2.4579H41B···C192.7592
H3A···H1C2.5350H41B···H2A2.2343
H3A···H41F2.4294H41C···C62.7788
H3A···C25Aiii2.9590H41C···H6B2.4618
H3A···C26Aiii2.9565H41C···H42C2.5581
H5···H7B2.4460H41D···O3A2.5239
H5···H42A2.2625H41D···H26v2.4941
H5···H1B2.4370H41D···H42E2.4499
H5···H32.4030H41D···C26v3.0318
H5···C82.7899H41E···H61A2.1449
H5A···H3A2.4579H41E···C6A2.8109
H5A···H41F2.2563H41E···H42D2.4985
H5A···C8A2.8492H41F···H5A2.2563
H5A···H1C2.4558H41F···H3A2.4294
H5A···H22Diii2.5382H42A···H52.2625
H5A···H72A2.5167H42A···H32.3789
H6A···H19Aviii2.5871H42B···H42Exv2.4375
H6A···C422.5663H42B···H41A2.4015
H6A···H42C2.0682H42B···O32.5912
H6B···C192.7327H42C···H6A2.0682
H6B···C413.0435H42C···H41C2.5581
H6B···C93.0532H42C···C62.7450
H6B···H41C2.4618H42D···C6A2.7117
H6B···C24vi3.0057H42D···H41E2.4985
H6B···H19B2.1311H42D···H62A2.3488
H6B···C29vi2.8876H42D···C29Avii3.0499
H7A···C23vi3.0744H42E···O3A2.6400
H7A···H152.4372H42E···H32A2.3306
H7A···C152.7912H42E···H41D2.4499
H7B···C11viii3.0574H42E···H42Bxvi2.4375
H7B···H11Aviii2.4808H42F···C2A2.8057
H7B···C153.0210H42F···C19A2.7305
H7B···H52.4460H42F···H2C2.2758
H11A···H19A2.2929H42F···H19D2.0158
H11A···C192.9177H42F···H31Aiv2.1526
H11A···C7ix3.0879H42F···H32A2.5301
H11A···C182.8199H61A···C41A2.5904
H11A···H7Bix2.4808H61A···H41E2.1449
H11A···H18B2.3448H62A···C9A3.0996
H11B···H1B2.4895H62A···C19A2.7316
H11B···H1A2.1082H62A···C42A2.9424
H11B···C12.5259H62A···H19F2.1235
H11C···H18D2.3738H62A···H42D2.3488
H11C···H19E2.2322H62A···C23Avii2.8652
H11C···C19A2.8690H62A···C24Avii2.9164
H11C···C18A2.8604H62A···H23Dvii2.5534
H11D···H1C2.4542H71A···C15A2.7867
H11D···C1A2.5678H71A···H15A2.4499
H11D···H1D2.2094H72A···C15A3.0828
H12A···C212.8291H72A···H5A2.5167
H31A—O3—H31C109.37C4—C42—H42C109.49
C3—O3—H31A109.28C4—C42—H42A109.47
C3—O3—H31C109.60C4—C42—H42B109.47
H32A—O3A—H32C109.42C2A—C1A—C10A113.0 (2)
C3A—O3A—H32C109.57C1A—C2A—C3A112.2 (2)
C3A—O3A—H32A109.43O3A—C3A—C2A110.9 (2)
C2—C1—C10113.1 (2)O3A—C3A—C4A111.5 (2)
C1—C2—C3110.9 (2)C2A—C3A—C4A113.3 (2)
O3—C3—C4111.8 (2)C3A—C4A—C42A111.3 (2)
O3—C3—C2107.6 (2)C5A—C4A—C42A114.6 (2)
C2—C3—C4114.0 (3)C41A—C4A—C42A107.5 (2)
C5—C4—C42107.9 (2)C5A—C4A—C41A108.1 (2)
C3—C4—C5106.9 (2)C3A—C4A—C5A107.9 (2)
C41—C4—C42108.0 (3)C3A—C4A—C41A107.1 (2)
C5—C4—C41115.7 (2)C6A—C5A—C10A110.2 (2)
C3—C4—C42107.5 (3)C4A—C5A—C6A114.0 (2)
C3—C4—C41110.6 (2)C4A—C5A—C10A116.8 (2)
C4—C5—C6114.7 (2)C5A—C6A—C7A110.8 (2)
C6—C5—C10109.8 (2)C6A—C7A—C8A113.22 (19)
C4—C5—C10117.3 (2)C7A—C8A—C9A122.6 (2)
C5—C6—C7109.4 (2)C7A—C8A—C14A116.3 (2)
C6—C7—C8113.2 (2)C9A—C8A—C14A121.1 (2)
C9—C8—C14120.7 (2)C10A—C9A—C11A116.16 (19)
C7—C8—C14116.4 (2)C8A—C9A—C10A123.1 (2)
C7—C8—C9122.9 (2)C8A—C9A—C11A120.5 (2)
C8—C9—C11120.4 (2)C1A—C10A—C5A107.0 (2)
C8—C9—C10122.9 (2)C1A—C10A—C9A112.4 (2)
C10—C9—C11116.5 (2)C1A—C10A—C19A108.6 (2)
C1—C10—C19108.5 (2)C5A—C10A—C9A108.44 (18)
C5—C10—C9108.43 (19)C9A—C10A—C19A105.9 (2)
C9—C10—C19106.9 (2)C5A—C10A—C19A114.6 (2)
C5—C10—C19114.9 (2)C9A—C11A—C12A115.43 (19)
C1—C10—C9111.4 (2)C11A—C12A—C13A112.4 (2)
C1—C10—C5106.7 (2)C12A—C13A—C17A114.9 (2)
C9—C11—C12114.8 (2)C14A—C13A—C18A108.4 (2)
C11—C12—C13112.3 (2)C12A—C13A—C18A111.1 (2)
C14—C13—C17102.0 (2)C14A—C13A—C17A102.19 (18)
C14—C13—C18108.1 (2)C12A—C13A—C14A107.0 (2)
C12—C13—C18111.2 (2)C17A—C13A—C18A112.5 (2)
C12—C13—C14107.3 (2)C13A—C14A—C15A110.6 (2)
C17—C13—C18112.6 (2)C8A—C14A—C13A119.4 (2)
C12—C13—C17114.9 (2)C8A—C14A—C15A129.8 (2)
C8—C14—C13120.7 (2)C14A—C15A—C16A112.4 (2)
C8—C14—C15128.7 (2)C15A—C16A—C17A103.1 (2)
C13—C14—C15110.6 (3)C13A—C17A—C16A103.8 (2)
C14—C15—C16112.3 (3)C16A—C17A—C20A114.1 (2)
C15—C16—C17102.7 (3)C13A—C17A—C20A118.2 (2)
C13—C17—C16103.8 (2)C21A—C20A—C22A110.7 (2)
C13—C17—C20119.8 (2)C17A—C20A—C22A112.8 (2)
C16—C17—C20113.4 (3)C17A—C20A—C21A112.6 (2)
C17—C20—C22112.0 (3)C20A—C22A—C23A115.5 (3)
C17—C20—C21113.2 (3)C22A—C23A—C24A112.2 (3)
C21—C20—C22109.8 (3)C23A—C24A—C25A121.7 (3)
C20—C22—C23115.2 (3)C23A—C24A—C29A121.0 (3)
C22—C23—C24113.2 (3)C25A—C24A—C29A117.3 (3)
C23—C24—C25120.2 (4)C24A—C25A—C26A119.9 (4)
C25—C24—C29117.5 (4)C25A—C26A—C27A120.1 (5)
C23—C24—C29122.3 (4)C26A—C27A—C28A120.5 (6)
C24—C25—C26122.4 (6)C27A—C28A—C29A120.4 (5)
C25—C26—C27119.2 (6)C24A—C29A—C28A121.9 (4)
C26—C27—C28120.7 (6)C2A—C1A—H1C108.95
C27—C28—C29119.6 (6)C2A—C1A—H1D109.03
C24—C29—C28120.5 (5)C10A—C1A—H1C109.01
C10—C1—H1A108.99C10A—C1A—H1D108.93
C10—C1—H1B108.93H1C—C1A—H1D107.75
C2—C1—H1B108.88C1A—C2A—H2C109.18
C2—C1—H1A108.99C1A—C2A—H2D109.09
H1A—C1—H1B107.79C3A—C2A—H2C109.11
C1—C2—H2A109.37C3A—C2A—H2D109.22
C1—C2—H2B109.42H2C—C2A—H2D107.94
H2A—C2—H2B108.14O3A—C3A—H3A106.92
C3—C2—H2A109.51C2A—C3A—H3A106.90
C3—C2—H2B109.47C4A—C3A—H3A106.93
O3—C3—H3107.78C4A—C5A—H5A104.93
C2—C3—H3107.75C6A—C5A—H5A104.89
C4—C3—H3107.68C10A—C5A—H5A104.83
C4—C5—H5104.54C5A—C6A—H61A109.46
C10—C5—H5104.48C5A—C6A—H62A109.43
C6—C5—H5104.48C7A—C6A—H61A109.55
C7—C6—H6A109.76C7A—C6A—H62A109.58
C5—C6—H6B109.74H61A—C6A—H62A108.01
C5—C6—H6A109.79C6A—C7A—H71A109.02
C7—C6—H6B109.89C6A—C7A—H72A108.90
H6A—C6—H6B108.27C8A—C7A—H71A108.89
C6—C7—H7A108.89C8A—C7A—H72A108.95
H7A—C7—H7B107.86H71A—C7A—H72A107.72
C6—C7—H7B108.89C9A—C11A—H11C108.48
C8—C7—H7A108.94C9A—C11A—H11D108.41
C8—C7—H7B108.97C12A—C11A—H11C108.40
C9—C11—H11A108.58C12A—C11A—H11D108.40
C9—C11—H11B108.59H11C—C11A—H11D107.46
C12—C11—H11A108.60C11A—C12A—H12C109.10
H11A—C11—H11B107.53C11A—C12A—H12D109.08
C12—C11—H11B108.50C13A—C12A—H12C109.15
C13—C12—H12B109.20C13A—C12A—H12D109.06
H12A—C12—H12B107.92H12C—C12A—H12D107.92
C11—C12—H12A109.13C14A—C15A—H15A123.75
C13—C12—H12A109.17C16A—C15A—H15A123.89
C11—C12—H12B109.07C15A—C16A—H16C111.10
C14—C15—H15123.77C15A—C16A—H16D111.21
C16—C15—H15123.94C17A—C16A—H16C111.10
C15—C16—H16A111.22C17A—C16A—H16D111.16
C15—C16—H16B111.28H16C—C16A—H16D109.10
H16A—C16—H16B109.11C13A—C17A—H17A106.68
C17—C16—H16A111.19C16A—C17A—H17A106.68
C17—C16—H16B111.23C20A—C17A—H17A106.69
C13—C17—H17106.43C13A—C18A—H18D109.48
C16—C17—H17106.35C13A—C18A—H18E109.45
C20—C17—H17106.28C13A—C18A—H18F109.47
C13—C18—H18A109.51H18D—C18A—H18E109.44
H18A—C18—H18C109.54H18D—C18A—H18F109.45
H18B—C18—H18C109.36H18E—C18A—H18F109.53
C13—C18—H18B109.50C10A—C19A—H19D109.43
C13—C18—H18C109.52C10A—C19A—H19E109.41
H18A—C18—H18B109.40C10A—C19A—H19F109.49
C10—C19—H19A109.52H19D—C19A—H19E109.50
C10—C19—H19B109.51H19D—C19A—H19F109.52
C10—C19—H19C109.47H19E—C19A—H19F109.47
H19B—C19—H19C109.45C17A—C20A—H20A106.84
H19A—C19—H19B109.50C21A—C20A—H20A106.78
H19A—C19—H19C109.38C22A—C20A—H20A106.72
C17—C20—H20107.23C20A—C21A—H21D109.48
C21—C20—H20107.17C20A—C21A—H21E109.47
C22—C20—H20107.08C20A—C21A—H21F109.45
C20—C21—H21A109.51H21D—C21A—H21E109.51
H21A—C21—H21C109.44H21D—C21A—H21F109.54
H21B—C21—H21C109.50H21E—C21A—H21F109.37
H21A—C21—H21B109.41C20A—C22A—H22C108.38
C20—C21—H21B109.48C20A—C22A—H22D108.48
C20—C21—H21C109.49C23A—C22A—H22C108.40
C20—C22—H22A108.40C23A—C22A—H22D108.38
C20—C22—H22B108.45H22C—C22A—H22D107.41
C23—C22—H22A108.51C22A—C23A—H23C109.11
C23—C22—H22B108.51C22A—C23A—H23D109.11
H22A—C22—H22B107.53C24A—C23A—H23C109.24
C24—C23—H23A109.01C24A—C23A—H23D109.26
H23A—C23—H23B107.81H23C—C23A—H23D107.82
C22—C23—H23B108.91C24A—C25A—H25A120.13
C24—C23—H23B108.89C26A—C25A—H25A119.98
C22—C23—H23A108.87C25A—C26A—H26A119.82
C24—C25—H25118.79C27A—C26A—H26A120.11
C26—C25—H25118.80C26A—C27A—H27A119.75
C27—C26—H26120.42C28A—C27A—H27A119.75
C25—C26—H26120.36C27A—C28A—H28A119.87
C28—C27—H27119.69C29A—C28A—H28A119.78
C26—C27—H27119.64C24A—C29A—H29A119.10
C27—C28—H28120.13C28A—C29A—H29A119.01
C29—C28—H28120.23C4A—C41A—H41D109.47
C24—C29—H29119.78C4A—C41A—H41E109.43
C28—C29—H29119.72C4A—C41A—H41F109.48
C4—C41—H41C109.52H41D—C41A—H41E109.56
H41A—C41—H41C109.43H41D—C41A—H41F109.44
H41B—C41—H41C109.46H41E—C41A—H41F109.43
H41A—C41—H41B109.43C4A—C42A—H42D109.51
C4—C41—H41A109.51C4A—C42A—H42E109.48
C4—C41—H41B109.48C4A—C42A—H42F109.45
H42A—C42—H42B109.40H42D—C42A—H42E109.40
H42A—C42—H42C109.46H42D—C42A—H42F109.46
H42B—C42—H42C109.55H42E—C42A—H42F109.52
C2—C1—C10—C9171.6 (2)C10A—C1A—C2A—C3A57.6 (4)
C2—C1—C10—C1970.9 (3)C2A—C1A—C10A—C19A70.5 (3)
C2—C1—C10—C553.4 (3)C2A—C1A—C10A—C5A53.7 (3)
C10—C1—C2—C357.3 (3)C2A—C1A—C10A—C9A172.7 (2)
C1—C2—C3—O3178.0 (3)C1A—C2A—C3A—O3A177.6 (2)
C1—C2—C3—C457.4 (3)C1A—C2A—C3A—C4A56.1 (4)
O3—C3—C4—C4268.8 (3)C2A—C3A—C4A—C42A75.0 (3)
C2—C3—C4—C42168.8 (2)O3A—C3A—C4A—C41A66.3 (3)
C2—C3—C4—C553.2 (3)O3A—C3A—C4A—C5A177.5 (2)
O3—C3—C4—C4148.8 (3)C2A—C3A—C4A—C41A167.8 (2)
O3—C3—C4—C5175.5 (2)O3A—C3A—C4A—C42A51.0 (3)
C2—C3—C4—C4173.5 (3)C2A—C3A—C4A—C5A51.5 (3)
C42—C4—C5—C660.1 (3)C3A—C4A—C5A—C6A177.3 (2)
C41—C4—C5—C1070.2 (3)C41A—C4A—C5A—C10A168.0 (3)
C41—C4—C5—C660.9 (3)C3A—C4A—C5A—C10A52.4 (3)
C42—C4—C5—C10168.8 (3)C41A—C4A—C5A—C6A61.7 (3)
C3—C4—C5—C6175.5 (2)C42A—C4A—C5A—C6A58.2 (3)
C3—C4—C5—C1053.4 (3)C42A—C4A—C5A—C10A72.1 (3)
C4—C5—C6—C7159.2 (2)C10A—C5A—C6A—C7A63.7 (3)
C4—C5—C10—C9173.8 (2)C4A—C5A—C6A—C7A162.8 (2)
C10—C5—C6—C766.2 (3)C6A—C5A—C10A—C19A65.1 (3)
C4—C5—C10—C153.7 (3)C6A—C5A—C10A—C9A53.0 (3)
C6—C5—C10—C952.9 (3)C4A—C5A—C10A—C9A175.0 (2)
C4—C5—C10—C1966.6 (3)C4A—C5A—C10A—C19A67.0 (3)
C6—C5—C10—C1173.0 (2)C4A—C5A—C10A—C1A53.4 (3)
C6—C5—C10—C1966.7 (3)C6A—C5A—C10A—C1A174.5 (2)
C5—C6—C7—C845.2 (4)C5A—C6A—C7A—C8A43.4 (3)
C6—C7—C8—C14165.8 (3)C6A—C7A—C8A—C9A16.3 (4)
C6—C7—C8—C914.7 (5)C6A—C7A—C8A—C14A163.0 (3)
C7—C8—C14—C13165.9 (3)C7A—C8A—C9A—C10A8.7 (5)
C14—C8—C9—C111.8 (4)C9A—C8A—C14A—C15A169.8 (3)
C9—C8—C14—C15168.7 (3)C7A—C8A—C9A—C11A177.7 (3)
C7—C8—C14—C1510.8 (5)C14A—C8A—C9A—C10A170.6 (3)
C9—C8—C14—C1314.6 (4)C14A—C8A—C9A—C11A3.0 (4)
C7—C8—C9—C103.6 (5)C7A—C8A—C14A—C13A164.0 (3)
C7—C8—C9—C11178.7 (3)C7A—C8A—C14A—C15A10.8 (5)
C14—C8—C9—C10176.9 (3)C9A—C8A—C14A—C13A15.4 (4)
C11—C9—C10—C145.1 (3)C8A—C9A—C11A—C12A10.4 (4)
C8—C9—C10—C19102.0 (3)C10A—C9A—C11A—C12A175.5 (3)
C8—C9—C11—C1218.0 (4)C8A—C9A—C10A—C1A144.7 (3)
C11—C9—C10—C5162.2 (3)C8A—C9A—C10A—C5A26.6 (4)
C11—C9—C10—C1973.3 (3)C8A—C9A—C10A—C19A96.9 (3)
C8—C9—C10—C522.5 (4)C11A—C9A—C10A—C1A41.4 (3)
C10—C9—C11—C12166.6 (3)C11A—C9A—C10A—C5A159.5 (3)
C8—C9—C10—C1139.6 (3)C11A—C9A—C10A—C19A77.1 (3)
C9—C11—C12—C1345.8 (4)C9A—C11A—C12A—C13A41.3 (4)
C11—C12—C13—C1863.4 (3)C11A—C12A—C13A—C17A168.1 (2)
C11—C12—C13—C1454.6 (3)C11A—C12A—C13A—C14A55.4 (3)
C11—C12—C13—C17167.2 (2)C11A—C12A—C13A—C18A62.8 (3)
C12—C13—C14—C15142.2 (3)C17A—C13A—C14A—C8A165.2 (3)
C12—C13—C14—C840.5 (3)C12A—C13A—C14A—C8A44.1 (3)
C18—C13—C14—C1597.8 (3)C12A—C13A—C14A—C15A140.2 (3)
C17—C13—C14—C8161.7 (3)C14A—C13A—C17A—C20A154.7 (2)
C18—C13—C17—C2040.7 (3)C18A—C13A—C17A—C16A88.7 (3)
C14—C13—C17—C1628.6 (3)C18A—C13A—C17A—C20A38.8 (3)
C12—C13—C17—C16144.3 (3)C17A—C13A—C14A—C15A19.1 (3)
C12—C13—C17—C2088.0 (3)C18A—C13A—C14A—C8A75.8 (3)
C18—C13—C14—C879.5 (3)C18A—C13A—C14A—C15A99.9 (3)
C18—C13—C17—C1687.0 (3)C12A—C13A—C17A—C16A142.8 (2)
C14—C13—C17—C20156.3 (3)C12A—C13A—C17A—C20A89.8 (3)
C17—C13—C14—C1521.1 (3)C14A—C13A—C17A—C16A27.3 (3)
C13—C14—C15—C164.5 (4)C8A—C14A—C15A—C16A177.8 (3)
C8—C14—C15—C16178.5 (3)C13A—C14A—C15A—C16A2.6 (4)
C14—C15—C16—C1714.5 (4)C14A—C15A—C16A—C17A15.4 (4)
C15—C16—C17—C1326.3 (4)C15A—C16A—C17A—C13A25.9 (3)
C15—C16—C17—C20157.8 (3)C15A—C16A—C17A—C20A155.9 (3)
C13—C17—C20—C2156.0 (4)C13A—C17A—C20A—C22A172.7 (2)
C16—C17—C20—C2256.1 (4)C13A—C17A—C20A—C21A61.2 (3)
C13—C17—C20—C22179.2 (3)C16A—C17A—C20A—C22A50.3 (3)
C16—C17—C20—C21179.1 (3)C16A—C17A—C20A—C21A176.4 (3)
C21—C20—C22—C2367.7 (4)C17A—C20A—C22A—C23A63.7 (3)
C17—C20—C22—C2359.0 (4)C21A—C20A—C22A—C23A63.5 (4)
C20—C22—C23—C24168.7 (3)C20A—C22A—C23A—C24A179.9 (3)
C22—C23—C24—C2999.7 (5)C22A—C23A—C24A—C25A87.5 (4)
C22—C23—C24—C2580.7 (5)C22A—C23A—C24A—C29A91.4 (4)
C23—C24—C29—C28179.8 (4)C23A—C24A—C25A—C26A178.5 (4)
C25—C24—C29—C280.2 (6)C25A—C24A—C29A—C28A1.3 (6)
C23—C24—C25—C26179.8 (4)C29A—C24A—C25A—C26A0.4 (5)
C29—C24—C25—C260.6 (7)C23A—C24A—C29A—C28A177.6 (4)
C24—C25—C26—C271.5 (8)C24A—C25A—C26A—C27A0.8 (7)
C25—C26—C27—C282.0 (8)C25A—C26A—C27A—C28A1.1 (7)
C26—C27—C28—C291.6 (8)C26A—C27A—C28A—C29A0.2 (8)
C27—C28—C29—C240.7 (7)C27A—C28A—C29A—C24A1.0 (7)
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z; (iii) x, y1/2, z+1; (iv) x, y+1, z; (v) x, y+1/2, z; (vi) x+1, y+1/2, z; (vii) x, y+1/2, z+1; (viii) x+1, y, z; (ix) x1, y, z; (x) x+1, y1/2, z+1; (xi) x+1, y+1/2, z+1; (xii) x, y1, z1; (xiii) x, y1/2, z; (xiv) x, y+1, z+1; (xv) x+1, y1, z; (xvi) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31C···O3Ai0.962.062.890 (3)143
O3A—H32A···O3iv0.961.962.890 (3)164
C41A—H41D···O3A0.962.522.933 (4)106
C42—H42B···O30.962.592.962 (4)103
C42—H42B···O30.962.592.962 (4)103
Symmetry codes: (i) x, y1, z; (iv) x, y+1, z.
(III) 4,4-dimethyl-22-phenyl-23,24-dinor-5α-cholane-8,14-dien-3β-ol top
Crystal data top
C30H42OF(000) = 1840
Mr = 418.64Cell parameters were refined using all reflections, including those with theta greater than 25.25
Monoclinic, C2Dx = 1.061 Mg m3
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 23.785 (9) ÅCell parameters from 32980 reflections
b = 13.610 (3) Åθ = 2.0–28.4°
c = 19.080 (7) ŵ = 0.06 mm1
β = 121.927 (12)°T = 150 K
V = 5242 (3) Å3Block, colourless
Z = 80.2 × 0.2 × 0.1 mm
Data collection top
Enraf-Nonius κ-CCD
diffractometer
4763 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 25.3°, θmin = 2.0°
Detector resolution: 18.4 pixels mm-1h = 2828
ϕ and ω scans with κ offsetsk = 1515
29708 measured reflectionsl = 2222
4917 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0671P)2 + 2.59P]
where P = (Fo2 + 2Fc2)/3
4917 reflections(Δ/σ)max = 0.034
559 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C30H42OV = 5242 (3) Å3
Mr = 418.64Z = 8
Monoclinic, C2Mo Kα radiation
a = 23.785 (9) ŵ = 0.06 mm1
b = 13.610 (3) ÅT = 150 K
c = 19.080 (7) Å0.2 × 0.2 × 0.1 mm
β = 121.927 (12)°
Data collection top
Enraf-Nonius κ-CCD
diffractometer
4763 reflections with I > 2σ(I)
29708 measured reflectionsRint = 0.049
4917 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.119H-atom parameters constrained
S = 1.09Δρmax = 0.27 e Å3
4917 reflectionsΔρmin = 0.29 e Å3
559 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/UeqOcc. (<1)
O30.08993 (10)0.04455 (15)0.06291 (12)0.0359 (6)
C10.16336 (13)0.1789 (2)0.19857 (16)0.0304 (8)
C20.14246 (14)0.0720 (2)0.17404 (17)0.0335 (8)
C30.10875 (13)0.0572 (2)0.08092 (16)0.0296 (8)
C40.15369 (14)0.0875 (2)0.04829 (16)0.0301 (8)
C50.17849 (13)0.1939 (2)0.07838 (15)0.0279 (8)
C60.21886 (17)0.2376 (2)0.04608 (18)0.0409 (10)
C70.22206 (16)0.3491 (2)0.05453 (17)0.0368 (9)
C80.23284 (13)0.3850 (2)0.13453 (16)0.0304 (8)
C90.22266 (14)0.3274 (2)0.18599 (16)0.0330 (8)
C100.21110 (12)0.2162 (2)0.17241 (15)0.0264 (7)
C110.23704 (15)0.3672 (2)0.26750 (17)0.0344 (8)
C120.23541 (14)0.4790 (2)0.27326 (17)0.0328 (8)
C130.27415 (13)0.5293 (2)0.23959 (16)0.0296 (8)
C140.24729 (14)0.4902 (2)0.15252 (16)0.0327 (8)
C150.24786 (16)0.5611 (2)0.10343 (18)0.0405 (9)
C160.26706 (16)0.6586 (2)0.14690 (17)0.0365 (8)
C170.26142 (14)0.6414 (2)0.22320 (16)0.0312 (8)
C180.34844 (14)0.5040 (2)0.29311 (18)0.0385 (9)
C190.27948 (13)0.1668 (2)0.22801 (17)0.0347 (8)
C200.30123 (14)0.7142 (2)0.29405 (16)0.0323 (8)
C210.29462 (18)0.6960 (3)0.36779 (19)0.0450 (10)
C220.27984 (15)0.8202 (2)0.26154 (17)0.0371 (9)
C230.31736 (14)0.8997 (2)0.32460 (16)0.0329 (8)
C240.38048 (14)0.9274 (2)0.34426 (17)0.0366 (8)
C250.41526 (16)1.0001 (2)0.40165 (18)0.0419 (9)
C260.38816 (17)1.0463 (2)0.44186 (18)0.0441 (10)
C270.32556 (18)1.0198 (2)0.42318 (18)0.0458 (10)
C280.29050 (16)0.9475 (2)0.36486 (18)0.0401 (9)
C410.20900 (14)0.0120 (2)0.07354 (18)0.0350 (9)
C420.11015 (16)0.0887 (2)0.04639 (17)0.0385 (9)
O3A0.00040 (10)0.88950 (15)0.10173 (12)0.0365 (6)
C1A0.08220 (13)0.6718 (2)0.24361 (17)0.0330 (8)
C2A0.07077 (13)0.7780 (2)0.21255 (17)0.0346 (8)
C3A0.00763 (13)0.7883 (2)0.12750 (16)0.0301 (8)
C4A0.05429 (13)0.7540 (2)0.12715 (16)0.0311 (8)
C5A0.04046 (12)0.6478 (2)0.16294 (16)0.0285 (8)
C6A0.09909 (14)0.5998 (2)0.1614 (2)0.0385 (9)
C7A0.09049 (14)0.4894 (2)0.16797 (19)0.0372 (8)
C8A0.02110 (13)0.4576 (2)0.23222 (15)0.0294 (8)
C9A0.03143 (13)0.5190 (2)0.26628 (15)0.0293 (8)
C10A0.02396 (13)0.6303 (2)0.24864 (15)0.0279 (8)
C11A0.09998 (13)0.4812 (2)0.32986 (17)0.0325 (8)
C12A0.10804 (13)0.3697 (2)0.32820 (17)0.0321 (8)
C13A0.05136 (13)0.3139 (2)0.32688 (15)0.0274 (7)
C14A0.01292 (13)0.3526 (2)0.25358 (15)0.0297 (8)
C15A0.05732 (14)0.2806 (2)0.21751 (17)0.0366 (8)
C16A0.02954 (15)0.1828 (2)0.25723 (17)0.0379 (8)
C17A0.04616 (14)0.2020 (2)0.30611 (16)0.0313 (8)
C18A0.05176 (14)0.3329 (2)0.40681 (15)0.0326 (8)
C19A0.02426 (16)0.6786 (2)0.32214 (17)0.0383 (9)
C20A0.08561 (14)0.1290 (2)0.37632 (16)0.0329 (8)
C21A0.16049 (15)0.1452 (2)0.42054 (18)0.0379 (9)
C22A0.06730 (18)0.0226 (2)0.34242 (18)0.0445 (10)
C23A0.09743 (14)0.0558 (2)0.40698 (16)0.0350 (8)
C24A0.15314 (19)0.1077 (3)0.4230 (3)0.0683 (14)
C25A0.1788 (3)0.1806 (4)0.4833 (5)0.131 (2)
C26A0.1517 (6)0.2058 (4)0.5238 (3)0.153 (4)
C27A0.0968 (5)0.1565 (4)0.5112 (3)0.112 (3)
C28A0.0682 (2)0.0811 (3)0.4511 (2)0.0615 (14)
C41A0.11193 (14)0.7490 (2)0.03617 (18)0.0390 (9)
C42A0.07358 (15)0.8276 (2)0.1726 (2)0.0396 (10)
H1A0.184800.185100.258000.0360*
H1B0.124100.220000.173200.0360*
H2A0.181200.030000.202400.0400*
H2B0.112200.053000.191200.0400*
H30.068500.097500.053100.0360*
H3B0.070100.048000.004200.0540*0.500
H3C0.056900.057300.076200.0540*0.500
H50.137900.233300.051900.0330*
H6A0.199100.219900.011600.0490*
H6B0.263400.210700.076700.0490*
H7A0.257700.373100.048600.0440*
H7B0.181000.376600.009800.0440*
H11A0.280500.344300.310400.0410*
H11B0.205000.339700.278800.0410*
H12A0.254300.497900.330500.0390*
H12B0.189800.501300.242200.0390*
H150.237700.550900.049800.0490*
H16A0.237100.710100.111900.0440*
H16B0.312000.676300.163400.0440*
H170.214800.651900.204500.0370*
H18A0.371700.535800.270900.0580*
H18B0.354100.434200.293200.0580*
H18C0.365800.526300.348600.0580*
H19A0.297500.186000.284400.0520*
H19B0.309000.187000.210700.0520*
H19C0.274400.096700.223400.0520*
H200.348100.707100.312500.0390*
H21A0.311600.631900.390000.0680*
H21B0.248800.699700.350700.0680*
H21C0.319300.744800.409300.0680*
H22A0.285500.830000.215300.0450*
H22B0.233000.827200.241100.0450*
H240.399500.896300.318300.0440*
H250.457101.018200.413400.0500*
H260.411901.094700.481000.0530*
H270.307001.050500.449800.0550*
H280.248300.930500.352400.0480*
H41A0.242200.039200.065100.0530*
H41B0.190800.046200.040600.0530*
H41C0.228600.004400.130800.0530*
H42A0.137700.095600.069000.0580*
H42B0.079800.142900.063900.0580*
H42C0.085700.028300.065400.0580*
H1C0.122300.668900.298000.0400*
H1D0.088700.630900.206900.0400*
H2C0.067700.820000.251500.0410*
H2D0.108300.799700.209700.0410*
H3A0.012100.747900.088200.0360*
H5A0.034300.608900.124300.0340*
H11C0.110100.500000.384400.0390*
H11D0.132100.513100.320800.0390*
H12C0.149900.350100.376500.0380*
H12D0.109100.352200.279600.0380*
H15A0.100400.289900.173000.0440*
H16C0.041800.131800.216100.0450*
H16D0.044500.164300.293800.0450*
H17A0.060800.193800.267200.0380*
H18D0.016800.295900.405500.0490*
H18E0.045100.401700.411100.0490*
H18F0.093600.312900.453600.0490*
H19D0.062000.655900.373000.0570*
H19E0.015600.661300.320400.0570*
H19F0.026500.748700.318600.0570*
H20A0.072600.137900.416800.0390*
H21D0.171400.208700.446200.0570*
H21E0.173900.141500.381200.0570*
H21F0.183000.095400.461900.0570*
H22C0.019500.015700.312400.0540*
H22D0.081200.012300.303500.0540*
H24A0.173300.093900.393600.0820*
H25A0.217400.212500.495000.1570*
H26A0.169300.257300.561400.1830*
H27A0.078300.172600.542200.1350*
H28A0.030200.048900.441200.0740*
H32A0.036600.894000.045900.0550*0.500
H33A0.040600.902900.103100.0550*0.500
H41D0.104000.696600.008700.0580*
H41E0.115000.810100.009300.0580*
H41F0.152600.737000.033900.0580*
H42D0.105700.797900.182000.0590*
H42E0.092200.885500.139500.0590*
H42F0.034900.845000.224600.0590*
H61A0.102100.624300.207000.0460*
H62A0.139800.616600.110300.0460*
H71A0.121100.461500.181400.0450*
H72A0.101700.463500.114700.0450*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0390 (10)0.0313 (10)0.0384 (10)0.0089 (8)0.0211 (9)0.0049 (8)
C10.0332 (13)0.0332 (15)0.0279 (12)0.0047 (12)0.0183 (11)0.0023 (11)
C20.0397 (15)0.0353 (15)0.0318 (14)0.0092 (12)0.0231 (12)0.0023 (12)
C30.0286 (13)0.0279 (14)0.0298 (13)0.0060 (11)0.0137 (11)0.0027 (10)
C40.0330 (13)0.0302 (14)0.0261 (13)0.0026 (11)0.0150 (11)0.0009 (11)
C50.0295 (13)0.0315 (15)0.0219 (12)0.0002 (11)0.0131 (10)0.0020 (10)
C60.0576 (19)0.0367 (17)0.0300 (14)0.0058 (14)0.0243 (14)0.0009 (12)
C70.0504 (17)0.0333 (15)0.0314 (14)0.0089 (13)0.0249 (13)0.0012 (12)
C80.0329 (14)0.0303 (14)0.0282 (13)0.0019 (11)0.0163 (11)0.0018 (11)
C90.0391 (15)0.0326 (15)0.0252 (13)0.0029 (12)0.0155 (12)0.0018 (11)
C100.0286 (12)0.0293 (13)0.0212 (12)0.0009 (11)0.0131 (10)0.0022 (10)
C110.0444 (16)0.0336 (15)0.0297 (13)0.0085 (12)0.0227 (12)0.0011 (11)
C120.0389 (15)0.0342 (15)0.0280 (13)0.0053 (12)0.0195 (12)0.0029 (11)
C130.0306 (13)0.0276 (14)0.0261 (12)0.0038 (11)0.0119 (11)0.0008 (11)
C140.0395 (15)0.0323 (15)0.0264 (13)0.0060 (12)0.0175 (12)0.0002 (11)
C150.0535 (18)0.0362 (16)0.0304 (14)0.0011 (14)0.0212 (13)0.0010 (12)
C160.0460 (16)0.0323 (15)0.0277 (13)0.0037 (12)0.0171 (12)0.0026 (11)
C170.0316 (14)0.0312 (15)0.0262 (12)0.0018 (11)0.0121 (11)0.0021 (11)
C180.0329 (14)0.0383 (16)0.0385 (15)0.0022 (12)0.0150 (13)0.0057 (13)
C190.0326 (14)0.0380 (16)0.0308 (13)0.0025 (12)0.0149 (12)0.0046 (12)
C200.0359 (14)0.0300 (14)0.0244 (13)0.0038 (11)0.0114 (11)0.0009 (11)
C210.059 (2)0.0405 (18)0.0319 (15)0.0110 (15)0.0216 (15)0.0047 (13)
C220.0404 (16)0.0327 (15)0.0280 (14)0.0012 (12)0.0112 (12)0.0009 (12)
C230.0399 (15)0.0254 (14)0.0274 (13)0.0041 (11)0.0138 (12)0.0040 (11)
C240.0386 (15)0.0378 (16)0.0306 (13)0.0025 (13)0.0164 (12)0.0005 (12)
C250.0407 (16)0.0404 (17)0.0362 (15)0.0030 (13)0.0146 (13)0.0009 (13)
C260.0547 (19)0.0331 (16)0.0280 (14)0.0039 (14)0.0106 (14)0.0004 (12)
C270.066 (2)0.0406 (18)0.0286 (14)0.0182 (16)0.0236 (14)0.0047 (12)
C280.0425 (16)0.0420 (17)0.0371 (15)0.0082 (13)0.0219 (13)0.0074 (13)
C410.0412 (15)0.0320 (15)0.0400 (15)0.0027 (12)0.0270 (13)0.0026 (12)
C420.0470 (17)0.0376 (16)0.0285 (14)0.0110 (13)0.0184 (13)0.0022 (12)
O3A0.0385 (11)0.0320 (11)0.0388 (11)0.0007 (8)0.0204 (9)0.0089 (8)
C1A0.0256 (12)0.0328 (15)0.0322 (13)0.0018 (11)0.0096 (11)0.0050 (12)
C2A0.0278 (13)0.0322 (15)0.0373 (15)0.0054 (11)0.0128 (12)0.0054 (12)
C3A0.0307 (13)0.0290 (14)0.0304 (13)0.0006 (11)0.0160 (11)0.0041 (11)
C4A0.0296 (13)0.0298 (14)0.0305 (13)0.0001 (11)0.0135 (11)0.0047 (11)
C5A0.0259 (12)0.0289 (14)0.0284 (13)0.0006 (10)0.0127 (11)0.0012 (11)
C6A0.0274 (14)0.0392 (17)0.0433 (16)0.0004 (12)0.0149 (13)0.0099 (13)
C7A0.0296 (14)0.0340 (15)0.0391 (15)0.0059 (11)0.0122 (12)0.0082 (12)
C8A0.0299 (13)0.0316 (14)0.0236 (12)0.0007 (11)0.0121 (11)0.0017 (11)
C9A0.0294 (13)0.0290 (14)0.0260 (12)0.0012 (11)0.0122 (11)0.0003 (11)
C10A0.0277 (13)0.0275 (14)0.0250 (12)0.0034 (11)0.0116 (10)0.0003 (10)
C11A0.0272 (13)0.0300 (14)0.0308 (13)0.0039 (11)0.0089 (11)0.0050 (11)
C12A0.0283 (13)0.0321 (15)0.0323 (13)0.0001 (11)0.0136 (11)0.0046 (11)
C13A0.0295 (13)0.0247 (13)0.0232 (12)0.0015 (10)0.0106 (11)0.0000 (10)
C14A0.0321 (13)0.0318 (15)0.0230 (12)0.0038 (11)0.0130 (11)0.0007 (11)
C15A0.0330 (14)0.0372 (16)0.0276 (13)0.0040 (12)0.0079 (12)0.0045 (12)
C16A0.0425 (16)0.0308 (15)0.0242 (12)0.0090 (13)0.0067 (12)0.0006 (11)
C17A0.0392 (15)0.0272 (14)0.0228 (12)0.0028 (11)0.0131 (11)0.0026 (10)
C18A0.0348 (14)0.0341 (15)0.0241 (13)0.0003 (12)0.0123 (11)0.0027 (11)
C19A0.0497 (17)0.0328 (15)0.0307 (14)0.0024 (13)0.0202 (13)0.0027 (12)
C20A0.0402 (15)0.0273 (14)0.0262 (13)0.0020 (12)0.0141 (12)0.0003 (11)
C21A0.0412 (16)0.0347 (16)0.0386 (15)0.0052 (12)0.0217 (13)0.0075 (12)
C22A0.064 (2)0.0301 (16)0.0287 (14)0.0036 (15)0.0172 (14)0.0011 (12)
C23A0.0409 (15)0.0272 (15)0.0288 (13)0.0009 (12)0.0130 (12)0.0014 (11)
C24A0.0431 (19)0.043 (2)0.101 (3)0.0009 (16)0.026 (2)0.008 (2)
C25A0.063 (3)0.038 (3)0.140 (6)0.017 (2)0.050 (3)0.004 (3)
C26A0.251 (11)0.037 (3)0.034 (2)0.031 (5)0.017 (4)0.004 (2)
C27A0.246 (9)0.052 (3)0.064 (3)0.064 (4)0.099 (5)0.026 (3)
C28A0.104 (3)0.0405 (19)0.058 (2)0.017 (2)0.055 (2)0.0121 (17)
C41A0.0338 (15)0.0377 (16)0.0378 (15)0.0020 (12)0.0137 (13)0.0113 (13)
C42A0.0394 (16)0.0365 (17)0.0499 (17)0.0073 (13)0.0283 (14)0.0079 (13)
Geometric parameters (Å, º) top
O3—C31.440 (3)C42—H42C0.9604
O3—H3B0.9595C42—H42A0.9609
O3—H3C0.9604C42—H42B0.9601
O3A—C3A1.442 (3)C1A—C2A1.531 (4)
O3A—H33A0.9601C1A—C10A1.545 (5)
O3A—H32A0.9599C2A—C3A1.527 (4)
C1—C101.548 (5)C3A—C4A1.542 (5)
C1—C21.529 (4)C4A—C42A1.545 (5)
C2—C31.528 (4)C4A—C5A1.558 (4)
C3—C41.550 (5)C4A—C41A1.543 (4)
C4—C411.532 (5)C5A—C10A1.558 (4)
C4—C421.535 (4)C5A—C6A1.526 (5)
C4—C51.554 (4)C6A—C7A1.513 (4)
C5—C101.562 (3)C7A—C8A1.508 (5)
C5—C61.510 (5)C8A—C9A1.350 (4)
C6—C71.524 (4)C8A—C14A1.470 (4)
C7—C81.490 (4)C9A—C11A1.517 (4)
C8—C91.374 (4)C9A—C10A1.541 (4)
C8—C141.470 (4)C10A—C19A1.545 (4)
C9—C111.505 (4)C11A—C12A1.532 (4)
C9—C101.536 (4)C12A—C13A1.536 (5)
C10—C191.548 (4)C13A—C14A1.520 (4)
C11—C121.528 (4)C13A—C18A1.542 (4)
C12—C131.535 (5)C13A—C17A1.562 (4)
C13—C171.555 (4)C14A—C15A1.334 (4)
C13—C141.526 (4)C15A—C16A1.501 (4)
C13—C181.541 (5)C16A—C17A1.550 (5)
C14—C151.350 (4)C17A—C20A1.527 (4)
C15—C161.502 (4)C20A—C22A1.551 (4)
C16—C171.549 (4)C20A—C21A1.531 (5)
C17—C201.534 (4)C22A—C23A1.495 (4)
C20—C211.516 (5)C23A—C28A1.389 (6)
C20—C221.546 (4)C23A—C24A1.386 (6)
C22—C231.510 (4)C24A—C25A1.392 (8)
C23—C281.393 (5)C25A—C26A1.287 (15)
C23—C241.393 (5)C26A—C27A1.372 (17)
C24—C251.380 (4)C27A—C28A1.416 (6)
C25—C261.387 (5)C1A—H1C0.9702
C26—C271.383 (6)C1A—H1D0.9690
C27—C281.386 (4)C2A—H2C0.9704
C1—H1B0.9701C2A—H2D0.9687
C1—H1A0.9702C3A—H3A0.9799
C2—H2A0.9702C5A—H5A0.9796
C2—H2B0.9702C6A—H61A0.9691
C3—H30.9806C6A—H62A0.9705
C5—H50.9793C7A—H71A0.9681
C6—H6B0.9711C7A—H72A0.9704
C6—H6A0.9711C11A—H11C0.9702
C7—H7B0.9699C11A—H11D0.9704
C7—H7A0.9693C12A—H12C0.9702
C11—H11A0.9699C12A—H12D0.9705
C11—H11B0.9701C15A—H15A0.9310
C12—H12B0.9696C16A—H16C0.9698
C12—H12A0.9705C16A—H16D0.9693
C15—H150.9291C17A—H17A0.9789
C16—H16A0.9704C18A—H18D0.9611
C16—H16B0.9715C18A—H18E0.9603
C17—H170.9792C18A—H18F0.9601
C18—H18A0.9596C19A—H19D0.9600
C18—H18C0.9598C19A—H19E0.9602
C18—H18B0.9593C19A—H19F0.9599
C19—H19B0.9607C20A—H20A0.9797
C19—H19A0.9601C21A—H21D0.9589
C19—H19C0.9598C21A—H21E0.9596
C20—H200.9803C21A—H21F0.9602
C21—H21A0.9606C22A—H22C0.9699
C21—H21C0.9598C22A—H22D0.9696
C21—H21B0.9595C24A—H24A0.9297
C22—H22B0.9710C25A—H25A0.9298
C22—H22A0.9695C26A—H26A0.9293
C24—H240.9307C27A—H27A0.9310
C25—H250.9302C28A—H28A0.9295
C26—H260.9297C41A—H41D0.9610
C27—H270.9298C41A—H41E0.9592
C28—H280.9301C41A—H41F0.9591
C41—H41C0.9602C42A—H42D0.9613
C41—H41B0.9602C42A—H42E0.9592
C41—H41A0.9597C42A—H42F0.9599
O3···O3Ai2.749 (4)H11D···C123.0714
O3···O3Aii2.855 (3)H11D···C1A2.5286
O3A···O3iii2.855 (3)H11D···H1C2.1523
O3A···O3iv2.749 (4)H11D···H1D2.4466
O3···H41C2.8872H12A···H18C2.5166
O3···H41B2.6491H12A···C212.8237
O3···H32Aii1.9579H12A···H21A2.1990
O3···H33Ai1.8514H12B···H11D2.5170
O3···H41Eii2.6525H12B···H172.3504
O3···H42C2.5934H12C···C21A2.8848
O3A···H41E2.5869H12C···H18F2.5094
O3A···H42E2.6556H12C···H21D2.2392
O3A···H3Biii2.0089H12D···H17A2.3949
O3A···H42Ciii2.5964H12D···C8A3.0829
O3A···H3Civ1.8055H12D···H11B2.2954
C9···C183.527 (4)H15···C72.7794
C9A···C18A3.531 (4)H15···H7A2.4686
C11···C26Av3.564 (6)H15···H41Axiii2.4836
C12···C213.357 (5)H15A···H16Bviii2.5222
C12A···C21A3.416 (4)H15A···C7A2.7314
C18···C93.527 (4)H15A···H71A2.4095
C18···C213.525 (5)H16A···C222.8915
C18A···C21A3.545 (5)H16A···H41Fxi2.4492
C18A···C9A3.531 (4)H16A···H22A2.3405
C19···C413.273 (4)H16A···C41Axi2.8687
C19A···C42A3.263 (4)H16B···H15Axiv2.5222
C21···C283.424 (5)H16B···C223.0727
C21···C183.525 (5)H16B···H202.5342
C21···C123.357 (5)H16B···H22A2.5325
C21A···C12A3.416 (4)H16B···C15Axiv3.0574
C21A···C18A3.545 (5)H16C···C22A2.8524
C21A···C24A3.448 (5)H16C···H22C2.2727
C24A···C21A3.448 (5)H16C···C42xi2.8114
C26A···C11vi3.564 (6)H16C···H42Axi2.5596
C28···C213.424 (5)H16C···H42Bxi2.5488
C41···C193.273 (4)H16D···C22A3.0069
C42A···C19A3.263 (4)H16D···H18D2.5669
C1···H11B2.5515H16D···H20A2.5457
C1A···H11D2.5286H16D···H22C2.4417
C2···H41C2.7834H16D···H18Aviii2.5102
C2···H19C2.7789H17···H21B2.5441
C2···H33Ai3.0870H17···H22B2.4591
C2A···H19F2.7596H17···H12B2.3504
C2A···H42F2.7951H17A···H22D2.5419
C3···H32Aii3.0564H17A···H12D2.3949
C3···H33Ai2.8182H17A···H21E2.5071
C3A···H3Civ2.8214H18A···C162.8909
C4···H19C3.0456H18A···H16Dxiv2.5102
C6···H19B2.7953H18A···C153.0083
C6···H41A2.7419H18B···C82.9490
C6···H42A2.7927H18B···C93.0507
C6A···H41F2.7838H18B···C112.7166
C6A···H42D2.7411H18B···H11A2.2971
C6A···H19E2.7341H18C···H21A2.3299
C6A···H19Bvii3.0409H18C···H202.5298
C7···H152.7794H18C···H12A2.5166
C7A···H15A2.7314H18C···C202.8794
C8···H52.8429H18C···C212.9984
C8···H18B2.9490H18D···C20A3.0186
C8A···H12D3.0829H18D···C16A2.8791
C8A···H5A2.8098H18D···C15A3.0543
C8A···H18E3.0038H18D···H16D2.5669
C9···H18B3.0507H18D···H20A2.4757
C9A···H18E3.0560H18E···C26vi3.0908
C11···H18B2.7166H18E···C11A2.7234
C11···H1B3.0586H18E···H11C2.2962
C11···H19A2.7862H18E···C8A3.0038
C11···H1A2.7351H18E···C9A3.0560
C11A···H19D2.8166H18F···H21Cvi2.5023
C11A···H1D3.0102H18F···C21A3.0331
C11A···H1C2.7420H18F···H12C2.5094
C11A···H18E2.7234H18F···C20A2.8597
C12···H21A2.8821H18F···H21D2.3941
C12···H11D3.0714H18F···H20A2.4585
C12A···H21D2.9245H19A···H11A2.2942
C12A···H11B2.9449H19A···H1A2.4518
C13···H21A2.8767H19A···C112.7862
C13A···H21D2.9171H19B···H61Axii2.3156
C14A···H24viii2.9897H19B···C62.7953
C15···H7A2.8204H19B···H6B2.2100
C15···H18A3.0083H19B···C6Axii3.0409
C15···H7B3.0034H19C···C22.7789
C15A···H24viii3.0531H19C···C43.0456
C15A···H16Bviii3.0574H19C···C412.6870
C15A···H72A2.9947H19C···H2A2.2269
C15A···H71A2.7807H19C···H41C2.0410
C15A···H18D3.0543H19D···C11A2.8166
C16···H18A2.8909H19D···H1C2.5113
C16···H22A2.5946H19D···H11C2.3653
C16A···H22C2.5183H19E···C6A2.7341
C16A···H18D2.8791H19E···H61A2.1118
C18···H21A2.9881H19F···C42A2.7506
C18···H202.7894H19F···H2C2.2063
C18···H11A2.8298H19F···C2A2.7596
C18A···H11C2.8121H19F···H42F2.0729
C18A···H21D3.0426H20···C182.7894
C18A···H20A2.6880H20···C243.0751
C19···H41C2.8213H20···H18C2.5298
C19···H2A2.8216H20···H16B2.5342
C19···H11A2.8753H20A···C28A3.0652
C19···H6B2.7695H20A···C18A2.6880
C19A···H11C2.9871H20A···H18D2.4757
C19A···H2C2.8391H20A···H18F2.4585
C19A···H61A2.7243H20A···H16D2.5457
C19A···H42F2.7933H21A···C122.8821
C20···H18C2.8794H21A···C132.8767
C20A···H18D3.0186H21A···H18C2.3299
C20A···H18F2.8597H21A···C182.9881
C21···H12A2.8237H21A···H12A2.1990
C21···H18C2.9984H21B···H172.5441
C21A···H12C2.8848H21B···H22B2.5873
C21A···H18F3.0331H21C···C282.8608
C22···H16A2.8915H21C···C232.6418
C22···H16B3.0727H21C···H18Fv2.5023
C22A···H16C2.8524H21D···C12A2.9245
C22A···H16D3.0069H21D···C13A2.9171
C23···H21C2.6418H21D···H12C2.2392
C23A···H21F2.6869H21D···H18F2.3941
C24···H203.0751H21D···C18A3.0426
C24A···H21F2.8528H21D···H25Av2.5032
C24A···H2Ci2.9618H21E···H17A2.5071
C26···H26Aix2.9877H21E···H1A2.5670
C26···H18Ev3.0908H21E···H22D2.5873
C26A···H26x3.0858H21F···C24A2.8528
C26A···H11Avi2.7708H21F···C23A2.6869
C27···H26Aix3.0441H22A···C162.5946
C27A···H11Avi3.0978H22A···H242.5283
C28···H21C2.8608H22A···H16A2.3405
C28···H2Aiv3.0173H22A···H16B2.5325
C28A···H20A3.0652H22B···H282.4086
C41···H6B2.9847H22B···H172.4591
C41···H3B2.9511H22B···H21B2.5873
C41···H19C2.6870H22C···C16A2.5183
C41···H2A2.8743H22C···H28A2.4931
C41A···H32A2.6052H22C···H16C2.2727
C41A···H62A2.5843H22C···H16D2.4417
C41A···H16Axi2.8687H22D···H24A2.4207
C42···H6A2.5729H22D···H17A2.5419
C42···H3B2.5046H22D···H21E2.5873
C42···H16Cxi2.8114H24···H22A2.5283
C42A···H19F2.7506H24···C14Axiv2.9897
C42A···H61A3.0029H24···C15Axiv3.0531
C42A···H2C2.8668H24···H71Axiv2.5488
H1A···C112.7351H24A···H22D2.4207
H1A···H11B2.1480H24A···H28i2.3224
H1A···H19A2.4518H25A···H21Dvi2.5032
H1A···H21E2.5670H26···C26Aix3.0858
H1B···C113.0586H26A···H11Avi2.4963
H1B···H32.5640H26A···C26x2.9877
H1B···H11B2.5131H26A···C27x3.0441
H1B···H52.5100H28···H22B2.4086
H1C···H19D2.5113H28···H24Aiv2.3224
H1C···H11D2.1523H28A···H22C2.4931
H1C···C11A2.7420H32A···H41E1.9727
H1D···C11A3.0102H32A···O3iii1.9579
H1D···H11D2.4466H32A···C41A2.6052
H1D···H3A2.5729H32A···H3Civ2.0879
H1D···H5A2.5011H32A···C3iii3.0564
H2A···C192.8216H32A···H42Ciii2.3028
H2A···C28i3.0173H33A···H3Biv2.4290
H2A···C412.8743H33A···O3iv1.8514
H2A···H19C2.2269H33A···C2iv3.0870
H2A···H41C2.2328H33A···C3iv2.8182
H2B···H3C2.3970H33A···H2D2.2888
H2C···C19A2.8391H33A···H3Civ0.9579
H2C···C24Aiv2.9618H41A···C62.7419
H2C···C42A2.8668H41A···H42A2.5666
H2C···H19F2.2063H41A···H15xv2.4836
H2C···H42F2.2382H41A···H6B2.3734
H2D···H33A2.2888H41B···H3B2.5721
H3···H52.4862H41B···H42C2.4536
H3···H42B2.4641H41B···H41Eii2.4832
H3···H1B2.5640H41B···O32.6491
H3A···H1D2.5729H41C···C22.7834
H3A···H5A2.4648H41C···C192.8213
H3A···H41D2.4461H41C···O32.8872
H3B···C412.9511H41C···H19C2.0410
H3B···H33Ai2.4290H41C···H2A2.2328
H3B···H41B2.5721H41D···H3A2.4461
H3B···C422.5046H41D···H5A2.2738
H3B···H41Eii2.2864H41E···H32A1.9727
H3B···O3Aii2.0089H41E···O3A2.5869
H3B···H42C1.8710H41E···H3Biii2.2864
H3C···H2B2.3970H41E···H42E2.4685
H3C···C3Ai2.8214H41E···O3iii2.6525
H3C···O3Ai1.8055H41E···H41Biii2.4832
H3C···H32Ai2.0879H41F···H42D2.5656
H3C···H33Ai0.9579H41F···H62A2.1055
H5···C82.8429H41F···H6Bvii2.5519
H5···H7B2.5240H41F···H16Axi2.4492
H5···H1B2.5100H41F···C6A2.7838
H5···H32.4862H42A···C62.7927
H5···H42B2.2529H42A···H16Cxi2.5596
H5A···C8A2.8098H42A···H6A2.1219
H5A···H1D2.5011H42A···H41A2.5666
H5A···H3A2.4648H42B···H32.4641
H5A···H41D2.2738H42B···H52.2529
H5A···H72A2.4918H42B···H16Cxi2.5488
H6A···H42A2.1219H42C···H42Eii2.4558
H6A···C422.5729H42C···O32.5934
H6B···C192.7695H42C···H3B1.8710
H6B···H62Axii2.4064H42C···H41B2.4536
H6B···H19B2.2100H42C···O3Aii2.5964
H6B···H41A2.3734H42C···H32Aii2.3028
H6B···C412.9847H42D···C6A2.7411
H6B···H41Fxii2.5519H42D···H41F2.5656
H7A···H152.4686H42D···H61A2.4029
H7A···C152.8204H42E···O3A2.6556
H7B···C153.0034H42E···H41E2.4685
H7B···H52.5240H42E···H42Ciii2.4558
H7B···H72Axi2.4208H42F···C2A2.7951
H11A···C26Av2.7708H42F···C19A2.7933
H11A···H18B2.2971H42F···H2C2.2382
H11A···H19A2.2942H42F···H19F2.0729
H11A···C182.8298H61A···C19A2.7243
H11A···C192.8753H61A···C42A3.0029
H11A···C27Av3.0978H61A···H19E2.1118
H11A···H26Av2.4963H61A···H42D2.4029
H11B···C12.5515H61A···H19Bvii2.3156
H11B···H12D2.2954H62A···C41A2.5843
H11B···H1B2.5131H62A···H41F2.1055
H11B···C12A2.9449H62A···H6Bvii2.4064
H11B···H1A2.1480H71A···C15A2.7807
H11C···H18E2.2962H71A···H15A2.4095
H11C···C19A2.9871H71A···H24viii2.5488
H11C···C18A2.8121H72A···C15A2.9947
H11C···H19D2.3653H72A···H5A2.4918
H11D···H12B2.5170H72A···H7Bxi2.4208
C3—O3—H3B102.97C4—C42—H42C109.40
C3—O3—H3C107.77C4—C42—H42A109.48
H3B—O3—H3C109.49C4—C42—H42B109.44
H32A—O3A—H33A109.48C2A—C1A—C10A112.8 (3)
C3A—O3A—H32A108.26C1A—C2A—C3A111.8 (2)
C3A—O3A—H33A103.57O3A—C3A—C2A108.8 (2)
C2—C1—C10112.9 (3)O3A—C3A—C4A110.3 (3)
C1—C2—C3111.5 (2)C2A—C3A—C4A112.2 (2)
O3—C3—C4110.7 (2)C3A—C4A—C41A107.3 (2)
O3—C3—C2108.1 (2)C5A—C4A—C42A114.3 (2)
C2—C3—C4112.5 (3)C3A—C4A—C42A111.6 (2)
C5—C4—C41114.4 (3)C5A—C4A—C41A108.0 (2)
C5—C4—C42108.2 (2)C3A—C4A—C5A107.4 (2)
C3—C4—C42107.2 (3)C41A—C4A—C42A108.0 (3)
C3—C4—C41110.8 (2)C6A—C5A—C10A109.6 (2)
C41—C4—C42108.0 (2)C4A—C5A—C10A117.7 (2)
C3—C4—C5107.9 (2)C4A—C5A—C6A114.2 (3)
C6—C5—C10110.8 (2)C5A—C6A—C7A110.0 (3)
C4—C5—C10117.8 (2)C6A—C7A—C8A113.2 (3)
C4—C5—C6114.5 (2)C7A—C8A—C9A123.4 (2)
C5—C6—C7110.9 (3)C7A—C8A—C14A115.6 (3)
C6—C7—C8114.0 (2)C9A—C8A—C14A121.0 (3)
C7—C8—C9123.0 (3)C10A—C9A—C11A117.3 (2)
C9—C8—C14119.8 (3)C8A—C9A—C10A122.2 (3)
C7—C8—C14116.8 (2)C8A—C9A—C11A120.3 (2)
C10—C9—C11116.8 (2)C1A—C10A—C5A107.2 (2)
C8—C9—C11120.2 (2)C1A—C10A—C9A111.7 (3)
C8—C9—C10121.7 (3)C1A—C10A—C19A109.1 (2)
C1—C10—C19108.7 (2)C9A—C10A—C19A106.0 (2)
C9—C10—C19106.4 (2)C5A—C10A—C19A114.7 (3)
C1—C10—C9111.4 (2)C5A—C10A—C9A108.4 (2)
C1—C10—C5107.7 (2)C9A—C11A—C12A114.4 (2)
C5—C10—C19114.0 (2)C11A—C12A—C13A111.8 (3)
C5—C10—C9108.7 (2)C12A—C13A—C14A106.9 (2)
C9—C11—C12115.6 (2)C12A—C13A—C17A115.9 (3)
C11—C12—C13111.7 (3)C12A—C13A—C18A110.8 (2)
C12—C13—C18110.8 (2)C14A—C13A—C17A101.4 (2)
C14—C13—C17101.4 (2)C14A—C13A—C18A109.2 (3)
C12—C13—C17115.2 (3)C17A—C13A—C18A111.9 (2)
C17—C13—C18112.7 (2)C8A—C14A—C15A128.2 (3)
C12—C13—C14107.6 (2)C8A—C14A—C13A120.9 (2)
C14—C13—C18108.5 (3)C13A—C14A—C15A110.9 (2)
C13—C14—C15110.7 (2)C14A—C15A—C16A112.0 (3)
C8—C14—C13120.4 (2)C15A—C16A—C17A102.4 (2)
C8—C14—C15128.4 (3)C16A—C17A—C20A113.4 (3)
C14—C15—C16111.1 (3)C13A—C17A—C16A103.2 (2)
C15—C16—C17103.5 (2)C13A—C17A—C20A118.8 (2)
C13—C17—C20119.5 (2)C17A—C20A—C22A109.6 (2)
C16—C17—C20114.3 (3)C17A—C20A—C21A112.7 (3)
C13—C17—C16103.5 (2)C21A—C20A—C22A110.6 (3)
C21—C20—C22110.6 (3)C20A—C22A—C23A114.6 (2)
C17—C20—C22109.3 (2)C22A—C23A—C24A122.1 (4)
C17—C20—C21113.2 (3)C22A—C23A—C28A120.0 (3)
C20—C22—C23114.7 (2)C24A—C23A—C28A117.8 (3)
C22—C23—C24120.5 (3)C23A—C24A—C25A119.7 (5)
C24—C23—C28117.9 (3)C24A—C25A—C26A123.1 (8)
C22—C23—C28121.6 (3)C25A—C26A—C27A119.8 (6)
C23—C24—C25121.1 (3)C26A—C27A—C28A120.1 (8)
C24—C25—C26120.3 (4)C23A—C28A—C27A119.4 (6)
C25—C26—C27119.4 (3)C2A—C1A—H1C108.99
C26—C27—C28120.1 (4)C2A—C1A—H1D109.03
C23—C28—C27121.2 (4)C10A—C1A—H1C108.98
C2—C1—H1A108.99C10A—C1A—H1D109.02
H1A—C1—H1B107.78H1C—C1A—H1D107.90
C2—C1—H1B108.94C1A—C2A—H2C109.24
C10—C1—H1A109.06C1A—C2A—H2D109.23
C10—C1—H1B109.07C3A—C2A—H2C109.26
C1—C2—H2A109.32C3A—C2A—H2D109.27
C1—C2—H2B109.24H2C—C2A—H2D107.95
C3—C2—H2A109.30O3A—C3A—H3A108.46
H2A—C2—H2B108.06C2A—C3A—H3A108.54
C3—C2—H2B109.31C4A—C3A—H3A108.47
C4—C3—H3108.47C4A—C5A—H5A104.63
C2—C3—H3108.51C6A—C5A—H5A104.66
O3—C3—H3108.51C10A—C5A—H5A104.58
C4—C5—H5103.98C5A—C6A—H61A109.63
C6—C5—H5103.88C5A—C6A—H62A109.54
C10—C5—H5103.97C7A—C6A—H61A109.78
C7—C6—H6B109.53C7A—C6A—H62A109.67
H6A—C6—H6B107.97H61A—C6A—H62A108.22
C5—C6—H6B109.43C6A—C7A—H71A108.90
C7—C6—H6A109.52C6A—C7A—H72A108.89
C5—C6—H6A109.49C8A—C7A—H71A108.98
C6—C7—H7A108.73C8A—C7A—H72A108.88
C6—C7—H7B108.69H71A—C7A—H72A107.83
H7A—C7—H7B107.64C9A—C11A—H11C108.68
C8—C7—H7B108.82C9A—C11A—H11D108.67
C8—C7—H7A108.77C12A—C11A—H11C108.70
C12—C11—H11B108.39C12A—C11A—H11D108.70
H11A—C11—H11B107.48H11C—C11A—H11D107.51
C12—C11—H11A108.40C11A—C12A—H12C109.24
C9—C11—H11B108.35C11A—C12A—H12D109.24
C9—C11—H11A108.34C13A—C12A—H12C109.30
C11—C12—H12A109.31C13A—C12A—H12D109.21
C11—C12—H12B109.30H12C—C12A—H12D107.93
C13—C12—H12A109.25C14A—C15A—H15A124.04
C13—C12—H12B109.26C16A—C15A—H15A124.01
H12A—C12—H12B107.90C15A—C16A—H16C111.25
C16—C15—H15124.48C15A—C16A—H16D111.26
C14—C15—H15124.42C17A—C16A—H16C111.34
C15—C16—H16A111.09C17A—C16A—H16D111.25
C15—C16—H16B111.04H16C—C16A—H16D109.20
C17—C16—H16A111.03C13A—C17A—H17A106.94
H16A—C16—H16B109.00C16A—C17A—H17A106.88
C17—C16—H16B111.12C20A—C17A—H17A106.92
C20—C17—H17106.21C13A—C18A—H18D109.49
C16—C17—H17106.25C13A—C18A—H18E109.44
C13—C17—H17106.20C13A—C18A—H18F109.47
C13—C18—H18A109.47H18D—C18A—H18E109.49
C13—C18—H18B109.45H18D—C18A—H18F109.43
C13—C18—H18C109.51H18E—C18A—H18F109.50
H18B—C18—H18C109.45C10A—C19A—H19D109.48
H18A—C18—H18B109.53C10A—C19A—H19E109.49
H18A—C18—H18C109.41C10A—C19A—H19F109.43
C10—C19—H19A109.53H19D—C19A—H19E109.53
C10—C19—H19B109.51H19D—C19A—H19F109.51
C10—C19—H19C109.46H19E—C19A—H19F109.38
H19A—C19—H19B109.45C17A—C20A—H20A107.90
H19B—C19—H19C109.41C21A—C20A—H20A107.95
H19A—C19—H19C109.46C22A—C20A—H20A107.94
C22—C20—H20107.85C20A—C21A—H21D109.45
C17—C20—H20107.92C20A—C21A—H21E109.42
C21—C20—H20107.87C20A—C21A—H21F109.38
C20—C21—H21A109.39H21D—C21A—H21E109.54
C20—C21—H21B109.42H21D—C21A—H21F109.50
C20—C21—H21C109.53H21E—C21A—H21F109.53
H21A—C21—H21B109.55C20A—C22A—H22C108.63
H21A—C21—H21C109.48C20A—C22A—H22D108.66
H21B—C21—H21C109.46C23A—C22A—H22C108.59
C20—C22—H22B108.47C23A—C22A—H22D108.59
H22A—C22—H22B107.64H22C—C22A—H22D107.56
C23—C22—H22A108.58C23A—C24A—H24A120.14
C23—C22—H22B108.60C25A—C24A—H24A120.14
C20—C22—H22A108.59C24A—C25A—H25A118.48
C25—C24—H24119.49C26A—C25A—H25A118.41
C23—C24—H24119.44C25A—C26A—H26A120.02
C24—C25—H25119.81C27A—C26A—H26A120.18
C26—C25—H25119.85C26A—C27A—H27A119.97
C25—C26—H26120.21C28A—C27A—H27A119.93
C27—C26—H26120.37C23A—C28A—H28A120.30
C26—C27—H27119.96C27A—C28A—H28A120.35
C28—C27—H27119.98C4A—C41A—H41D109.42
C23—C28—H28119.37C4A—C41A—H41E109.53
C27—C28—H28119.45C4A—C41A—H41F109.46
C4—C41—H41B109.42H41D—C41A—H41E109.47
H41A—C41—H41C109.46H41D—C41A—H41F109.46
C4—C41—H41C109.46H41E—C41A—H41F109.49
H41A—C41—H41B109.54C4A—C42A—H42D109.47
C4—C41—H41A109.53C4A—C42A—H42E109.50
H41B—C41—H41C109.42C4A—C42A—H42F109.47
H42A—C42—H42B109.54H42D—C42A—H42E109.42
H42A—C42—H42C109.55H42D—C42A—H42F109.44
H42B—C42—H42C109.42H42E—C42A—H42F109.53
C10—C1—C2—C358.2 (3)C2A—C1A—C10A—C19A72.5 (3)
C2—C1—C10—C9171.4 (2)C10A—C1A—C2A—C3A57.9 (3)
C2—C1—C10—C1971.7 (3)C2A—C1A—C10A—C5A52.2 (3)
C2—C1—C10—C552.2 (3)C2A—C1A—C10A—C9A170.7 (2)
C1—C2—C3—O3179.3 (3)C1A—C2A—C3A—C4A58.4 (3)
C1—C2—C3—C458.2 (3)C1A—C2A—C3A—O3A179.3 (3)
C2—C3—C4—C42169.0 (2)C2A—C3A—C4A—C42A72.5 (3)
O3—C3—C4—C4147.7 (3)C2A—C3A—C4A—C41A169.4 (2)
C2—C3—C4—C4173.3 (3)O3A—C3A—C4A—C5A175.0 (2)
O3—C3—C4—C5173.7 (2)O3A—C3A—C4A—C41A69.1 (3)
O3—C3—C4—C4270.0 (3)O3A—C3A—C4A—C42A49.0 (3)
C2—C3—C4—C552.7 (3)C2A—C3A—C4A—C5A53.5 (3)
C3—C4—C5—C6175.5 (2)C41A—C4A—C5A—C6A60.6 (3)
C41—C4—C5—C1072.2 (4)C3A—C4A—C5A—C6A176.0 (2)
C42—C4—C5—C659.8 (4)C3A—C4A—C5A—C10A53.4 (3)
C42—C4—C5—C10167.3 (3)C42A—C4A—C5A—C10A71.0 (4)
C41—C4—C5—C660.8 (3)C41A—C4A—C5A—C10A168.7 (3)
C3—C4—C5—C1051.6 (3)C42A—C4A—C5A—C6A59.6 (3)
C10—C5—C6—C762.1 (3)C4A—C5A—C6A—C7A160.1 (2)
C4—C5—C6—C7161.7 (2)C6A—C5A—C10A—C19A64.0 (3)
C6—C5—C10—C1965.2 (3)C6A—C5A—C10A—C9A54.1 (3)
C6—C5—C10—C953.3 (3)C4A—C5A—C10A—C1A52.5 (3)
C4—C5—C10—C151.3 (3)C4A—C5A—C10A—C9A173.1 (3)
C4—C5—C10—C9172.1 (3)C10A—C5A—C6A—C7A65.4 (3)
C4—C5—C10—C1969.4 (4)C6A—C5A—C10A—C1A174.8 (2)
C6—C5—C10—C1174.1 (2)C4A—C5A—C10A—C19A68.7 (4)
C5—C6—C7—C842.3 (4)C5A—C6A—C7A—C8A43.8 (4)
C6—C7—C8—C14170.3 (3)C6A—C7A—C8A—C14A167.9 (3)
C6—C7—C8—C917.1 (5)C6A—C7A—C8A—C9A14.9 (4)
C7—C8—C9—C1010.9 (5)C9A—C8A—C14A—C13A12.9 (4)
C7—C8—C14—C154.9 (6)C7A—C8A—C9A—C10A6.2 (5)
C9—C8—C14—C1321.0 (5)C7A—C8A—C9A—C11A179.2 (3)
C9—C8—C14—C15168.0 (4)C14A—C8A—C9A—C10A176.7 (3)
C7—C8—C9—C11177.6 (3)C14A—C8A—C9A—C11A2.1 (4)
C14—C8—C9—C10176.7 (3)C7A—C8A—C14A—C13A169.8 (3)
C14—C8—C9—C1110.0 (5)C7A—C8A—C14A—C15A7.6 (5)
C7—C8—C14—C13166.2 (3)C9A—C8A—C14A—C15A169.7 (3)
C11—C9—C10—C1972.2 (4)C11A—C9A—C10A—C19A76.8 (3)
C8—C9—C11—C1223.7 (5)C8A—C9A—C11A—C12A20.4 (4)
C10—C9—C11—C12168.9 (3)C8A—C9A—C10A—C1A143.4 (3)
C8—C9—C10—C1146.7 (3)C8A—C9A—C10A—C5A25.6 (4)
C8—C9—C10—C528.2 (4)C8A—C9A—C10A—C19A97.9 (3)
C8—C9—C10—C1995.0 (3)C11A—C9A—C10A—C1A41.8 (3)
C11—C9—C10—C146.1 (4)C11A—C9A—C10A—C5A159.7 (3)
C11—C9—C10—C5164.6 (3)C10A—C9A—C11A—C12A164.7 (3)
C9—C11—C12—C1346.8 (4)C9A—C11A—C12A—C13A48.4 (3)
C11—C12—C13—C1864.8 (3)C11A—C12A—C13A—C14A55.1 (3)
C11—C12—C13—C1453.6 (3)C11A—C12A—C13A—C17A167.3 (2)
C11—C12—C13—C17165.9 (2)C11A—C12A—C13A—C18A63.8 (3)
C14—C13—C17—C20158.8 (3)C12A—C13A—C14A—C15A143.3 (3)
C18—C13—C17—C1685.4 (3)C12A—C13A—C14A—C8A38.9 (4)
C18—C13—C17—C2043.0 (4)C14A—C13A—C17A—C16A30.4 (3)
C14—C13—C17—C1630.4 (3)C14A—C13A—C17A—C20A156.8 (3)
C12—C13—C14—C842.4 (4)C18A—C13A—C17A—C16A85.9 (3)
C12—C13—C14—C15145.1 (3)C18A—C13A—C17A—C20A40.5 (4)
C17—C13—C14—C8163.7 (3)C17A—C13A—C14A—C15A21.4 (3)
C17—C13—C14—C1523.8 (4)C18A—C13A—C14A—C8A81.0 (3)
C18—C13—C14—C877.4 (4)C18A—C13A—C14A—C15A96.8 (3)
C18—C13—C14—C1595.1 (3)C12A—C13A—C17A—C16A145.7 (2)
C12—C13—C17—C16146.2 (3)C12A—C13A—C17A—C20A87.8 (3)
C12—C13—C17—C2085.4 (4)C17A—C13A—C14A—C8A160.8 (3)
C8—C14—C15—C16178.4 (3)C13A—C14A—C15A—C16A2.8 (4)
C13—C14—C15—C166.7 (4)C8A—C14A—C15A—C16A179.5 (3)
C14—C15—C16—C1713.6 (4)C14A—C15A—C16A—C17A17.2 (4)
C15—C16—C17—C20158.9 (3)C15A—C16A—C17A—C20A159.0 (2)
C15—C16—C17—C1327.3 (3)C15A—C16A—C17A—C13A29.1 (3)
C13—C17—C20—C2156.9 (4)C13A—C17A—C20A—C21A62.0 (4)
C13—C17—C20—C22179.4 (3)C16A—C17A—C20A—C21A176.5 (2)
C16—C17—C20—C21179.8 (3)C16A—C17A—C20A—C22A52.9 (4)
C16—C17—C20—C2256.1 (4)C13A—C17A—C20A—C22A174.3 (3)
C17—C20—C22—C23177.7 (3)C21A—C20A—C22A—C23A61.3 (4)
C21—C20—C22—C2357.1 (4)C17A—C20A—C22A—C23A173.9 (3)
C20—C22—C23—C2479.2 (4)C20A—C22A—C23A—C24A100.3 (4)
C20—C22—C23—C28100.8 (4)C20A—C22A—C23A—C28A82.0 (4)
C28—C23—C24—C250.2 (4)C22A—C23A—C24A—C25A179.4 (4)
C22—C23—C24—C25179.9 (3)C24A—C23A—C28A—C27A1.3 (5)
C22—C23—C28—C27179.4 (3)C28A—C23A—C24A—C25A1.7 (6)
C24—C23—C28—C270.5 (4)C22A—C23A—C28A—C27A179.1 (4)
C23—C24—C25—C260.9 (4)C23A—C24A—C25A—C26A2.8 (9)
C24—C25—C26—C270.8 (4)C24A—C25A—C26A—C27A3.4 (10)
C25—C26—C27—C280.1 (4)C25A—C26A—C27A—C28A2.9 (9)
C26—C27—C28—C230.6 (4)C26A—C27A—C28A—C23A1.9 (7)
Symmetry codes: (i) x, y1, z; (ii) x, y1, z; (iii) x, y+1, z; (iv) x, y+1, z; (v) x+1/2, y+1/2, z+1; (vi) x+1/2, y1/2, z+1; (vii) x1/2, y+1/2, z; (viii) x1/2, y1/2, z; (ix) x+1/2, y+3/2, z+1; (x) x+1/2, y3/2, z+1; (xi) x, y, z; (xii) x+1/2, y1/2, z; (xiii) x+1/2, y+1/2, z; (xiv) x+1/2, y+1/2, z; (xv) x+1/2, y1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···O3Aii0.962.012.855 (3)146
O3—H3C···O3Ai0.961.812.749 (4)167
O3A—H32A···O3iii0.961.962.855 (3)155
O3A—H33A···O3iv0.961.852.749 (4)154
C41A—H41E···O3A0.962.592.971 (4)104
C42—H42C···O30.962.592.988 (4)105
C42—H42C···O3Aii0.962.603.527 (4)163
Symmetry codes: (i) x, y1, z; (ii) x, y1, z; (iii) x, y+1, z; (iv) x, y+1, z.
(IV) 4,4-dimethyl-22-oxa-5α,20β-cholesta-8,14,24-trien-3β-ol top
Crystal data top
C28H44O2Cell parameters were determined by rotating the crystal simultaneously over phi and chi angles, from which accurate phi angles could be determined (Duisenberg et al. (2000), J. Appl. Cryst., 33, 893-898).
Mr = 412.63Dx = 1.079 Mg m3
Hexagonal, P62Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 62Cell parameters from 45 reflections
a = 24.661 (10) Åθ = 3.8–11.5°
c = 7.232 (10) ŵ = 0.07 mm1
V = 3809 (6) Å3T = 150 K
Z = 6Block, colourless
F(000) = 13680.6 × 0.2 × 0.2 mm
Data collection top
Enraf-Nonius κ-CCD
diffractometer
2161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 24.8°, θmin = 1.7°
Detector resolution: 18.4 pixels mm-1h = 2818
ϕ and ω scansk = 2828
13233 measured reflectionsl = 86
2343 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.001P)2 + 8.0P]
where P = (Fo2 + 2Fc2)/3
2343 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.52 e Å3
5 restraintsΔρmin = 0.36 e Å3
Crystal data top
C28H44O2Z = 6
Mr = 412.63Mo Kα radiation
Hexagonal, P62µ = 0.07 mm1
a = 24.661 (10) ÅT = 150 K
c = 7.232 (10) Å0.6 × 0.2 × 0.2 mm
V = 3809 (6) Å3
Data collection top
Enraf-Nonius κ-CCD
diffractometer
2161 reflections with I > 2σ(I)
13233 measured reflectionsRint = 0.045
2343 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0755 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.05Δρmax = 0.52 e Å3
2343 reflectionsΔρmin = 0.36 e Å3
275 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/UeqOcc. (<1)
O30.31323 (17)0.61951 (15)0.2361 (7)0.0297 (11)
O220.3207 (3)0.1657 (3)0.0819 (3)0.042 (2)*0.567 (7)
C10.3016 (2)0.4688 (2)0.0554 (9)0.0266 (17)
C20.3038 (2)0.5330 (2)0.0584 (9)0.0283 (17)
C30.3114 (2)0.5597 (2)0.2543 (8)0.0244 (16)
C40.3703 (2)0.5662 (2)0.3587 (8)0.0267 (17)
C50.3682 (2)0.5010 (2)0.3455 (8)0.0228 (16)
C60.4216 (2)0.4994 (2)0.4494 (9)0.0283 (17)
C70.4047 (2)0.4311 (2)0.4847 (9)0.0276 (16)
C80.3780 (2)0.3895 (2)0.3141 (8)0.0248 (14)
C90.3531 (2)0.4050 (2)0.1686 (9)0.0300 (17)
C100.3604 (2)0.4714 (2)0.1466 (8)0.0240 (14)
C110.3214 (3)0.3593 (2)0.0092 (10)0.051 (2)
C120.3034 (3)0.2898 (2)0.0522 (11)0.051 (2)
C130.3574 (3)0.2863 (2)0.1469 (9)0.0339 (17)
C140.3763 (2)0.3284 (2)0.3195 (9)0.0273 (17)
C150.3929 (3)0.3028 (3)0.4593 (9)0.0351 (17)
C160.3830 (3)0.2387 (3)0.4076 (9)0.0401 (17)
C170.3393 (3)0.2211 (2)0.2373 (10)0.0374 (17)
C180.4144 (3)0.3093 (3)0.0162 (9)0.051 (2)
C190.4186 (3)0.5094 (2)0.0178 (9)0.0339 (17)
C200.3383 (3)0.1706 (3)0.1126 (3)0.058 (3)
C210.3147 (6)0.1054 (7)0.218 (3)0.047 (4)*0.567 (7)
C230.2539 (4)0.1343 (5)0.0719 (14)0.034 (2)*0.567 (7)
C240.2335 (4)0.1398 (4)0.2820 (15)0.083 (3)
C250.1839 (3)0.1008 (3)0.3744 (11)0.054 (2)
C260.1619 (4)0.1202 (5)0.5424 (14)0.100 (4)
C270.1399 (5)0.0327 (4)0.3235 (17)0.129 (5)
C410.4314 (2)0.6230 (2)0.2848 (10)0.0324 (17)
C420.3633 (3)0.5786 (3)0.5664 (9)0.0367 (17)
C23'0.2744 (6)0.1219 (6)0.1623 (17)0.0340*0.433 (7)
C21'0.3308 (10)0.1148 (10)0.215 (3)0.0470*0.433 (7)
O22'0.2816 (3)0.1560 (4)0.0095 (12)0.0420*0.433 (7)
H2A0.338500.562600.017400.0340*
H1B0.264300.438100.120200.0320*
H3O0.311800.632700.339000.0440*
H2B0.265500.528000.004800.0340*
H30.274100.531300.325800.0290*
H6B0.459700.520600.377000.0340*
H7A0.442000.430600.524900.0330*
H7B0.374300.414000.584000.0330*
H11A0.349200.373700.096900.0610*
H11B0.283700.360000.024600.0610*
H50.330100.471600.412300.0270*
H6A0.428800.521200.566300.0340*
H1A0.298400.455000.071800.0320*
H16A0.363200.208900.507400.0480*
H16B0.422300.240900.375800.0480*
H170.296700.204000.285600.0450*
H18A0.446200.303800.075100.0770*
H18B0.430800.352900.011000.0770*
H18C0.401600.285600.096500.0770*
H19A0.456200.519500.084300.0510*
H19B0.420100.547300.021200.0510*
H19C0.415200.484600.088700.0510*
H200.383200.185500.101800.0700*0.567 (7)
H21A0.342300.111500.319200.0710*0.567 (7)
H21B0.314700.075400.133300.0710*0.567 (7)
H21C0.273100.090400.263600.0710*0.567 (7)
H23A0.240100.154900.015200.0410*0.567 (7)
H23B0.236700.090900.035700.0410*0.567 (7)
H240.261400.176000.345200.0990*
H26A0.187300.164700.559300.1500*
H26B0.119000.109300.526000.1500*
H26C0.165400.099100.649300.1500*
H27A0.129400.007300.432600.1940*
H27B0.102500.028600.269600.1940*
H27C0.160100.019300.236100.1940*
H41A0.430900.622600.152100.0480*
H41B0.466800.620600.328400.0480*
H41C0.434100.661100.328200.0480*
H42A0.356100.613400.576100.0550*
H42B0.400900.588100.631800.0550*
H42C0.328500.542100.619100.0550*
H12A0.266900.270800.131900.0620*
H12B0.292700.266100.062200.0620*
H150.408300.322100.572800.0420*
H20'0.375000.188000.031400.0700*0.433 (7)
H21D0.329100.084400.128800.0710*0.433 (7)
H21E0.292800.096700.285900.0710*0.433 (7)
H21F0.365800.127200.297000.0710*0.433 (7)
H23C0.253400.077100.140900.0410*0.433 (7)
H23D0.314600.135300.220200.0410*0.433 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.043 (2)0.0338 (19)0.0196 (17)0.0247 (17)0.0018 (17)0.0008 (16)
C10.033 (3)0.028 (3)0.017 (3)0.014 (2)0.009 (2)0.002 (2)
C20.031 (3)0.032 (3)0.021 (3)0.015 (2)0.007 (2)0.000 (2)
C30.025 (2)0.028 (3)0.020 (3)0.013 (2)0.001 (2)0.001 (2)
C40.030 (3)0.038 (3)0.016 (3)0.020 (2)0.001 (2)0.000 (2)
C50.020 (2)0.029 (3)0.019 (3)0.012 (2)0.001 (2)0.000 (2)
C60.030 (3)0.042 (3)0.017 (3)0.021 (2)0.005 (2)0.004 (2)
C70.026 (3)0.046 (3)0.016 (2)0.022 (2)0.000 (2)0.003 (2)
C80.026 (2)0.030 (3)0.017 (2)0.013 (2)0.001 (2)0.003 (2)
C90.039 (3)0.030 (3)0.022 (3)0.018 (2)0.006 (2)0.001 (2)
C100.030 (3)0.024 (2)0.016 (2)0.012 (2)0.001 (2)0.003 (2)
C110.081 (4)0.030 (3)0.046 (4)0.031 (3)0.036 (4)0.010 (3)
C120.072 (4)0.030 (3)0.052 (4)0.026 (3)0.037 (4)0.006 (3)
C130.046 (3)0.029 (3)0.027 (3)0.019 (3)0.007 (3)0.004 (2)
C140.032 (3)0.037 (3)0.018 (3)0.021 (2)0.001 (2)0.007 (2)
C150.042 (3)0.043 (3)0.024 (3)0.024 (3)0.003 (2)0.004 (3)
C160.048 (3)0.052 (3)0.031 (3)0.033 (3)0.003 (3)0.013 (3)
C170.039 (3)0.037 (3)0.039 (3)0.021 (3)0.001 (3)0.011 (3)
C180.085 (5)0.041 (3)0.021 (3)0.026 (3)0.009 (3)0.006 (3)
C190.046 (3)0.039 (3)0.023 (3)0.026 (3)0.003 (3)0.001 (2)
C200.100 (6)0.047 (4)0.041 (4)0.047 (4)0.020 (4)0.003 (3)
C240.065 (5)0.084 (6)0.083 (6)0.025 (5)0.000 (5)0.011 (5)
C250.055 (4)0.063 (4)0.049 (4)0.034 (4)0.007 (4)0.018 (4)
C260.078 (6)0.162 (9)0.074 (7)0.071 (6)0.011 (5)0.039 (7)
C270.143 (9)0.065 (6)0.111 (9)0.000 (6)0.013 (8)0.036 (6)
C410.028 (3)0.029 (3)0.036 (3)0.011 (2)0.002 (2)0.005 (2)
C420.053 (3)0.049 (3)0.022 (3)0.036 (3)0.008 (3)0.009 (3)
Geometric parameters (Å, º) top
O3—C31.459 (6)C6—H6A0.9694
O22—C201.459 (5)C6—H6B0.9691
O22—C231.429 (14)C7—H7A0.9706
O22'—C201.462 (12)C7—H7B0.9693
O22'—C23'1.461 (15)C11—H11A0.9703
O3—H3O0.8199C11—H11B0.9698
C1—C101.565 (8)C12—H12A0.9697
C1—C21.557 (7)C12—H12B0.9703
C2—C31.534 (9)C15—H150.9294
C3—C41.573 (8)C16—H16A0.9698
C4—C411.552 (7)C16—H16B0.9709
C4—C421.560 (9)C17—H170.9800
C4—C51.586 (7)C18—H18A0.9598
C5—C101.581 (8)C18—H18B0.9610
C5—C61.534 (8)C18—H18C0.9597
C6—C71.541 (7)C19—H19A0.9603
C7—C81.527 (8)C19—H19B0.9591
C8—C91.366 (8)C19—H19C0.9607
C8—C141.487 (7)C20—H200.9800
C9—C111.526 (9)C20—H20'0.9797
C9—C101.563 (7)C21—H21A0.9587
C10—C191.569 (9)C21—H21B0.9605
C11—C121.572 (7)C21—H21C0.9584
C12—C131.538 (11)C21'—H21D0.9597
C13—C181.547 (11)C21'—H21E0.9602
C13—C141.539 (9)C21'—H21F0.9624
C13—C171.579 (7)C23—H23B0.9695
C14—C151.359 (9)C23—H23A0.9714
C15—C161.521 (10)C23'—H23D0.9694
C16—C171.549 (10)C23'—H23C0.9698
C17—C201.528 (9)C24—H240.9301
C20—C21'1.49 (2)C26—H26C0.9596
C20—C211.603 (18)C26—H26B0.9598
C23—C241.627 (15)C26—H26A0.9614
C23'—C241.551 (19)C27—H27B0.9590
C24—C251.301 (13)C27—H27A0.9590
C25—C261.503 (13)C27—H27C0.9599
C25—C271.520 (11)C41—H41A0.9598
C1—H1A0.9703C41—H41B0.9575
C1—H1B0.9708C41—H41C0.9608
C2—H2A0.9700C42—H42B0.9598
C2—H2B0.9701C42—H42C0.9589
C3—H30.9797C42—H42A0.9619
C5—H50.9801
O3···O3i2.979 (8)H12B···O222.8874
O3···O3ii2.979 (8)H15···C72.8068
O22···C183.194 (10)H15···H7A2.3972
O22'···C123.082 (11)H15···H18Cvii2.5315
O3···H42A2.7103H16A···H24vii2.4618
O3···H42Ai2.6474H16A···H21F2.5511
O3···H3Oi2.1807H16A···H23Dvii2.5370
O3···H41C2.7062H16A···C21'2.9396
O3···H2Aii2.9177H16A···C213.0451
O22···H12B2.8874H16A···H21A2.5787
O22···H23C2.0210H16B···H21F2.4943
O22···H18C2.6144H16B···H18A2.5629
O22'···H12B2.6406H16B···H202.3250
O22'···H23B1.4604H16B···C21'3.0162
C9···C183.555 (10)H17···H12A2.3875
C12···C233.510 (13)H17···H21C2.5655
C12···O22'3.082 (11)H17···H23A2.3555
C18···C93.555 (10)H17···C232.9898
C18···O223.194 (10)H17···H21E2.5994
C19···C413.285 (9)H18A···C162.8787
C23···C123.510 (13)H18A···C203.0337
C41···C193.285 (9)H18A···H202.5357
C1···H11B2.5582H18A···H20'2.5147
C2···H41A2.8706H18A···H16B2.5629
C2···H19B2.7695H18A···C153.0686
C6···H19A2.7427H18A···C41iii3.0366
C6···H41B2.7587H18B···H11A2.3939
C6···H7Aiii2.9642H18B···C112.7840
C6···H42B2.8111H18B···C83.0353
C7···H6Biii3.0372H18B···C93.0776
C7···H152.8068H18C···C202.8878
C8···H18B3.0353H18C···H12B2.4927
C8···H52.8967H18C···H15viii2.5315
C8···H21Div3.0454H18C···O222.6144
C9···H18B3.0776H18C···H20'2.3453
C11···H19C2.8727H19A···H6B2.1182
C11···H1A2.7520H19A···C62.7427
C11···H1B3.0233H19B···C22.7695
C11···H18B2.7840H19B···C412.8178
C12···H23A2.8953H19B···H2A2.2253
C12···H23Civ2.9741H19B···H41A2.1437
C15···H7A2.7943H19C···H11A2.3835
C15···H18A3.0686H19C···C112.8727
C16···H21A2.8474H19C···H1A2.5965
C16···H21F2.6859H20···H16B2.3250
C16···H18A2.8787H20···H18A2.5357
C17···H23A2.6900H20···C182.8191
C18···H11A2.8862H20'···H18C2.3453
C18···H202.8191H20'···H23D2.2984
C18···H20'2.6454H20'···C182.6454
C19···H6B2.7517H20'···H18A2.5147
C19···H2A2.8774H20'···H1Bv2.4933
C19···H41A2.8252H21A···C162.8474
C19···H11A3.0148H21A···H16A2.5787
C20···H18A3.0337H21A···H21D1.4937
C20···H18C2.8878H21A···H21E1.1117
C21···H23A3.0449H21B···H21F1.7354
C21···H23B2.5508H21B···C232.9560
C21···H16A3.0451H21B···H23B2.4648
C21···H23C2.9076H21B···C23'2.8306
C21'···H23B2.7662H21B···H21E1.4385
C21'···H23C3.0591H21B···H23C2.5065
C21'···H16B3.0162H21C···H172.5655
C21'···H16A2.9396H21C···C232.7921
C23···H21D3.0565H21C···H21F2.0083
C23···H172.9898H21C···H23B2.3457
C23···H12B2.8940H21C···H21D1.7561
C23···H27C2.8712H21D···C233.0565
C23···H21B2.9560H21D···H21C1.7561
C23···H21E3.0603H21D···C23'2.8904
C23···H21C2.7921H21D···H21A1.4937
C23'···H27C2.7386H21D···C8v3.0454
C23'···H12Av2.8806H21E···H172.5994
C23'···H21D2.8904H21E···H21A1.1117
C23'···H21B2.8306H21E···C233.0603
C24···H27Aiv2.9419H21E···H21B1.4385
C25···H27Aiv2.8025H21F···H21C2.0083
C26···H27Cvi2.9229H21F···H16A2.5511
C27···H27Aiv3.0913H21F···C162.6859
C27···H23C2.7771H21F···H16B2.4943
C27···H23B2.9436H21F···H21B1.7354
C41···H2A2.9718H23A···C172.6900
C41···H6B3.0118H23A···C122.8953
C41···H19B2.8178H23A···H12B2.4411
C41···H18Aiii3.0366H23A···H172.3555
C42···H3O2.7914H23A···C213.0449
C42···H2Avii3.0575H23A···H27Civ2.5844
C42···H6A2.6267H23A···H23C2.3859
H1A···C112.7520H23B···C272.9436
H1A···H11B2.2107H23B···C212.5508
H1A···H19C2.5965H23B···H23D2.1369
H1B···H20'iv2.4933H23B···H27C2.3348
H1B···C113.0233H23B···H21B2.4648
H1B···H52.5372H23B···H21C2.3457
H1B···H11B2.4406H23B···O22'1.4604
H2A···C412.9718H23B···C21'2.7662
H2A···C42viii3.0575H23C···C212.9076
H2A···C192.8774H23C···O222.0210
H2A···O3i2.9177H23C···C21'3.0591
H2A···H3Oi2.5973H23C···C12v2.9741
H2A···H19B2.2253H23C···H12Av2.0998
H2A···H41A2.3479H23C···C272.7771
H3···H52.5494H23C···H21B2.5065
H3···H42C2.4521H23C···H23A2.3859
H3O···C422.7914H23C···H27C2.1261
H3O···H2Aii2.5973H23D···H16Aviii2.5370
H3O···O3ii2.1807H23D···H23B2.1369
H3O···H42A2.2091H23D···H20'2.2984
H3O···H42Ai2.4984H23D···H11Bv2.4478
H5···H1B2.5372H24···H26A2.3033
H5···H32.5494H24···H16Aviii2.4618
H5···H7B2.5092H26A···H242.3033
H5···H42C2.3086H26B···H27B2.5990
H5···C82.8967H26C···H27A2.5218
H6A···C422.6267H27A···C24v2.9419
H6A···H42B2.1342H27A···H26C2.5218
H6B···C413.0118H27A···H27Bv2.5940
H6B···C7iii3.0372H27A···C25v2.8025
H6B···H19A2.1182H27A···C27v3.0913
H6B···H41B2.4092H27B···H27Aiv2.5940
H6B···C192.7517H27B···H26B2.5990
H6B···H7Aiii2.3562H27C···C26ix2.9229
H7A···H6Biii2.3562H27C···H23C2.1261
H7A···C152.7943H27C···C232.8712
H7A···H152.3972H27C···H23Av2.5844
H7A···C6iii2.9642H27C···C23'2.7386
H7B···H11Avii2.4660H27C···H23B2.3348
H7B···H52.5092H41A···C192.8252
H11A···C182.8862H41A···C22.8706
H11A···C193.0148H41A···H2A2.3479
H11A···H7Bviii2.4660H41A···H19B2.1437
H11A···H18B2.3939H41B···C62.7587
H11A···H19C2.3835H41B···H6B2.4092
H11B···C12.5582H41C···H42A2.4567
H11B···H1A2.2107H41C···O32.7062
H11B···H1B2.4406H42A···O32.7103
H11B···H23Div2.4478H42A···H3O2.2091
H12A···C23'iv2.8806H42A···H41C2.4567
H12A···H172.3875H42A···O3ii2.6474
H12A···H23Civ2.0998H42A···H3Oii2.4984
H12B···H23A2.4411H42B···C62.8111
H12B···H18C2.4927H42B···H6A2.1342
H12B···C232.8940H42C···H52.3086
H12B···O22'2.6406H42C···H32.4521
C20—O22—C23102.2 (6)C9—C11—H11B108.60
C20—O22'—C23'113.7 (9)C12—C11—H11A108.55
C3—O3—H3O109.48C12—C11—H11B108.59
C2—C1—C10113.1 (4)H11A—C11—H11B107.60
C1—C2—C3112.6 (5)C11—C12—H12A109.41
C2—C3—C4113.3 (4)C11—C12—H12B109.37
O3—C3—C2106.6 (4)C13—C12—H12A109.20
O3—C3—C4112.3 (4)C13—C12—H12B109.16
C3—C4—C41110.9 (4)H12A—C12—H12B107.98
C5—C4—C41114.8 (4)C14—C15—H15124.06
C5—C4—C42107.8 (4)C16—C15—H15124.17
C3—C4—C42107.2 (5)C15—C16—H16A111.29
C41—C4—C42107.9 (5)C15—C16—H16B111.30
C3—C4—C5107.9 (4)C17—C16—H16A111.30
C6—C5—C10110.0 (4)C17—C16—H16B111.26
C4—C5—C10117.2 (4)H16A—C16—H16B109.20
C4—C5—C6113.8 (4)C13—C17—H17106.39
C5—C6—C7110.1 (4)C16—C17—H17106.45
C6—C7—C8113.0 (5)C20—C17—H17106.42
C7—C8—C9122.5 (4)C13—C18—H18A109.50
C9—C8—C14121.0 (5)C13—C18—H18B109.40
C7—C8—C14116.3 (5)C13—C18—H18C109.49
C10—C9—C11116.4 (5)H18A—C18—H18B109.42
C8—C9—C10122.6 (5)H18A—C18—H18C109.51
C8—C9—C11120.7 (4)H18B—C18—H18C109.50
C1—C10—C9112.4 (4)C10—C19—H19A109.51
C1—C10—C5107.4 (4)C10—C19—H19B109.56
C5—C10—C19113.6 (4)C10—C19—H19C109.46
C1—C10—C19109.1 (5)H19A—C19—H19B109.44
C9—C10—C19106.1 (4)H19A—C19—H19C109.40
C5—C10—C9108.3 (4)H19B—C19—H19C109.46
C9—C11—C12114.6 (6)O22—C20—H20100.82
C11—C12—C13111.7 (5)C17—C20—H20100.76
C12—C13—C18111.2 (6)C17—C20—H20'111.22
C12—C13—C14107.6 (5)C21—C20—H20100.92
C12—C13—C17115.4 (5)O22'—C20—H20'111.26
C17—C13—C18111.6 (6)C21'—C20—H20'111.30
C14—C13—C17100.8 (5)C20—C21—H21A109.42
C14—C13—C18109.6 (5)C20—C21—H21B109.24
C8—C14—C15128.9 (6)C20—C21—H21C109.42
C8—C14—C13120.5 (5)H21A—C21—H21B109.53
C13—C14—C15110.5 (5)H21A—C21—H21C109.68
C14—C15—C16111.8 (5)H21B—C21—H21C109.54
C15—C16—C17102.4 (6)C20—C21'—H21F109.59
C13—C17—C20117.8 (5)C20—C21'—H21D109.59
C16—C17—C20115.0 (6)C20—C21'—H21E109.65
C13—C17—C16103.9 (4)H21E—C21'—H21F109.29
O22—C20—C21115.6 (8)H21D—C21'—H21E109.42
O22'—C20—C1797.2 (6)H21D—C21'—H21F109.29
C17—C20—C21'113.8 (9)O22—C23—H23A111.08
C17—C20—C21112.8 (8)O22—C23—H23B111.18
O22'—C20—C21'111.4 (11)C24—C23—H23A110.98
O22—C20—C17121.3 (6)C24—C23—H23B111.18
O22—C23—C24103.2 (7)H23A—C23—H23B109.14
O22'—C23'—C24102.7 (10)C24—C23'—H23D111.19
C23'—C24—C25125.5 (9)O22'—C23'—H23C111.23
C23—C24—C25129.3 (8)C24—C23'—H23C111.12
C24—C25—C26122.4 (8)O22'—C23'—H23D111.22
C24—C25—C27125.5 (9)H23C—C23'—H23D109.26
C26—C25—C27112.1 (8)C23'—C24—H24105.85
C2—C1—H1A108.98C23—C24—H24115.32
C2—C1—H1B108.90C25—C24—H24115.35
C10—C1—H1A108.98H26A—C26—H26C109.43
C10—C1—H1B109.01H26B—C26—H26C109.46
H1A—C1—H1B107.75C25—C26—H26A109.47
C1—C2—H2A109.05C25—C26—H26B109.50
C1—C2—H2B109.18C25—C26—H26C109.51
C3—C2—H2A109.06H26A—C26—H26B109.47
C3—C2—H2B109.02C25—C27—H27B109.42
H2A—C2—H2B107.84C25—C27—H27C109.46
O3—C3—H3108.28C25—C27—H27A109.44
C2—C3—H3108.13H27B—C27—H27C109.47
C4—C3—H3107.98H27A—C27—H27B109.52
C4—C5—H5104.69H27A—C27—H27C109.51
C6—C5—H5104.91C4—C41—H41A109.48
C10—C5—H5104.87C4—C41—H41B109.55
C5—C6—H6A109.54C4—C41—H41C109.36
C5—C6—H6B109.56H41A—C41—H41B109.64
C7—C6—H6A109.64H41A—C41—H41C109.33
C7—C6—H6B109.79H41B—C41—H41C109.47
H6A—C6—H6B108.22C4—C42—H42C109.49
C6—C7—H7A108.87H42B—C42—H42C109.59
C6—C7—H7B109.03H42A—C42—H42B109.45
C8—C7—H7A109.05H42A—C42—H42C109.31
C8—C7—H7B109.05C4—C42—H42A109.45
H7A—C7—H7B107.72C4—C42—H42B109.53
C9—C11—H11A108.65
C23—O22—C20—C1779.4 (8)C9—C8—C14—C1311.1 (8)
C23—O22—C20—C2163.0 (11)C9—C8—C14—C15172.8 (6)
C20—O22—C23—C24169.8 (6)C11—C9—C10—C5157.9 (5)
C2—C1—C10—C9171.6 (5)C8—C9—C10—C1145.9 (5)
C2—C1—C10—C552.6 (6)C8—C9—C10—C527.4 (7)
C10—C1—C2—C356.5 (6)C8—C9—C10—C1994.9 (6)
C2—C1—C10—C1971.0 (6)C11—C9—C10—C139.4 (7)
C1—C2—C3—C455.5 (5)C11—C9—C10—C1979.7 (6)
C1—C2—C3—O3179.6 (4)C8—C9—C11—C1216.4 (9)
C2—C3—C4—C551.2 (5)C10—C9—C11—C12168.8 (5)
O3—C3—C4—C5172.1 (4)C9—C11—C12—C1346.0 (8)
O3—C3—C4—C4145.6 (6)C11—C12—C13—C17166.3 (6)
O3—C3—C4—C4272.0 (5)C11—C12—C13—C1865.2 (7)
C2—C3—C4—C4175.4 (5)C11—C12—C13—C1454.7 (7)
C2—C3—C4—C42167.1 (4)C12—C13—C14—C15144.0 (5)
C42—C4—C5—C661.9 (6)C12—C13—C14—C839.3 (7)
C3—C4—C5—C6177.4 (5)C14—C13—C17—C1631.5 (7)
C42—C4—C5—C10167.7 (5)C17—C13—C14—C8160.6 (5)
C41—C4—C5—C1072.0 (6)C17—C13—C14—C1522.7 (7)
C3—C4—C5—C1052.3 (6)C18—C13—C14—C881.7 (7)
C41—C4—C5—C658.3 (7)C18—C13—C14—C1595.1 (6)
C10—C5—C6—C764.9 (6)C12—C13—C17—C16147.1 (6)
C4—C5—C6—C7161.3 (5)C12—C13—C17—C2084.3 (8)
C4—C5—C10—C1967.6 (6)C18—C13—C17—C1684.7 (7)
C4—C5—C10—C153.0 (5)C18—C13—C17—C2043.9 (8)
C4—C5—C10—C9174.7 (4)C14—C13—C17—C20160.2 (6)
C6—C5—C10—C1964.4 (5)C13—C14—C15—C164.4 (8)
C6—C5—C10—C1174.9 (4)C8—C14—C15—C16179.3 (6)
C6—C5—C10—C953.3 (5)C14—C15—C16—C1716.4 (8)
C5—C6—C7—C846.1 (6)C15—C16—C17—C20159.8 (5)
C6—C7—C8—C14164.3 (5)C15—C16—C17—C1329.5 (7)
C6—C7—C8—C919.9 (7)C16—C17—C20—O22155.8 (6)
C7—C8—C14—C153.1 (9)C13—C17—C20—O2232.7 (10)
C7—C8—C14—C13173.0 (5)C13—C17—C20—C21176.0 (9)
C7—C8—C9—C1011.3 (8)C16—C17—C20—C2160.8 (10)
C7—C8—C9—C11174.2 (5)O22—C23—C24—C25147.2 (10)
C14—C8—C9—C10173.0 (5)C23—C24—C25—C2715.7 (17)
C14—C8—C9—C111.4 (8)C23—C24—C25—C26161.0 (10)
Symmetry codes: (i) y+1, xy+1, z1/3; (ii) x+y, x+1, z+1/3; (iii) x+1, y+1, z; (iv) xy, x, z+1/3; (v) y, x+y, z1/3; (vi) xy, x, z2/3; (vii) x, y, z+1; (viii) x, y, z1; (ix) y, x+y, z+2/3.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O3ii0.822.182.979 (8)165
Symmetry code: (ii) x+y, x+1, z+1/3.
(V) 4,4-dimethyl-23-phenyl-22-oxa-24-nor-5α-cholane-8,14-dien-3β-ol–water (4/1) top
Crystal data top
4C30H42O2·H2OF(000) = 1924
Mr = 1756.56Cell parameters were determined by rotating the crystal simultaneously over phi and chi angles, from which accurate phi angles could be determined (Duisenberg et al. (2000), J. Appl. Cryst., 33, 893-898).
Monoclinic, C2Dx = 1.112 Mg m3
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 64.902 (4) ÅCell parameters from 47 reflections
b = 7.2926 (14) Åθ = 3.3–12.7°
c = 11.1447 (11) ŵ = 0.07 mm1
β = 96.055 (13)°T = 293 K
V = 5245.4 (12) Å3Block, colourless
Z = 20.2 × 0.2 × 0.15 mm
Data collection top
Enraf-Nonius κ-CCD
diffractometer
3899 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.3°, θmin = 1.3°
Detector resolution: 18.4 pixels mm-1h = 6477
ϕ and ω scansk = 87
17152 measured reflectionsl = 1313
5110 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0324P)2 + 2.9P]
where P = (Fo2 + 2Fc2)/3
5110 reflections(Δ/σ)max = 0.001
596 parametersΔρmax = 0.12 e Å3
4 restraintsΔρmin = 0.12 e Å3
Crystal data top
4C30H42O2·H2OV = 5245.4 (12) Å3
Mr = 1756.56Z = 2
Monoclinic, C2Mo Kα radiation
a = 64.902 (4) ŵ = 0.07 mm1
b = 7.2926 (14) ÅT = 293 K
c = 11.1447 (11) Å0.2 × 0.2 × 0.15 mm
β = 96.055 (13)°
Data collection top
Enraf-Nonius κ-CCD
diffractometer
3899 reflections with I > 2σ(I)
17152 measured reflectionsRint = 0.048
5110 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0454 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.03Δρmax = 0.12 e Å3
5110 reflectionsΔρmin = 0.12 e Å3
596 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/UeqOcc. (<1)
O30.98963 (3)0.0169 (4)0.30176 (19)0.0657 (9)
O220.81057 (3)0.0018 (4)0.1533 (2)0.0663 (9)
C10.93754 (5)0.2162 (5)0.1854 (3)0.0504 (10)
C20.96001 (5)0.2117 (5)0.2418 (3)0.0543 (11)
C30.96793 (5)0.0176 (5)0.2595 (3)0.0505 (10)
C40.95503 (5)0.1007 (4)0.3390 (3)0.0486 (10)
C50.93197 (5)0.0876 (4)0.2840 (2)0.0436 (10)
C60.91688 (5)0.2074 (5)0.3444 (3)0.0574 (11)
C70.89736 (5)0.2372 (5)0.2584 (3)0.0551 (11)
C80.88948 (5)0.0665 (4)0.1923 (3)0.0464 (10)
C90.90101 (5)0.0889 (4)0.1901 (3)0.0459 (10)
C100.92260 (5)0.1074 (4)0.2597 (2)0.0418 (9)
C110.89191 (5)0.2586 (5)0.1244 (3)0.0588 (11)
C120.87355 (5)0.2227 (5)0.0299 (3)0.0545 (11)
C130.85742 (5)0.0933 (5)0.0771 (3)0.0484 (10)
C140.86873 (5)0.0778 (4)0.1257 (3)0.0482 (10)
C150.85702 (5)0.2271 (5)0.1014 (3)0.0587 (11)
C160.83710 (6)0.1815 (5)0.0267 (3)0.0623 (12)
C170.84137 (5)0.0100 (5)0.0213 (3)0.0520 (10)
C180.84692 (6)0.1846 (5)0.1810 (3)0.0649 (12)
C190.91972 (6)0.2185 (5)0.3760 (3)0.0612 (11)
C200.82174 (5)0.1175 (5)0.0642 (3)0.0601 (12)
C210.82544 (6)0.3045 (6)0.1172 (4)0.0873 (17)
C230.78923 (6)0.0393 (6)0.1769 (4)0.0831 (16)
C240.77837 (6)0.1120 (6)0.2510 (3)0.0670 (14)
C250.78816 (6)0.2756 (7)0.2735 (4)0.0785 (16)
C260.77740 (7)0.4140 (7)0.3386 (4)0.0944 (17)
C270.75675 (8)0.3898 (9)0.3804 (4)0.103 (2)
C280.74710 (8)0.2290 (10)0.3586 (5)0.108 (2)
C290.75783 (6)0.0902 (8)0.2943 (4)0.0895 (19)
C410.96254 (6)0.3005 (5)0.3300 (4)0.0759 (16)
C420.95895 (5)0.0438 (6)0.4732 (2)0.0626 (13)
O3A0.99344 (3)0.2002 (4)0.8724 (2)0.0715 (9)
O22A0.81777 (3)0.1715 (4)0.3634 (2)0.0728 (9)
C1A0.93658 (5)0.0714 (5)0.8323 (3)0.0566 (11)
C2A0.95877 (5)0.0824 (5)0.8928 (3)0.0639 (12)
C3A0.97181 (5)0.2082 (5)0.8248 (3)0.0537 (11)
C4A0.96365 (5)0.4055 (5)0.8171 (3)0.0518 (11)
C5A0.94044 (5)0.3956 (4)0.7615 (2)0.0438 (10)
C6A0.92971 (5)0.5792 (5)0.7384 (3)0.0616 (11)
C7A0.91067 (5)0.5582 (5)0.6479 (3)0.0600 (11)
C8A0.89818 (5)0.3876 (5)0.6629 (3)0.0457 (10)
C9A0.90524 (5)0.2475 (4)0.7358 (2)0.0455 (10)
C10A0.92579 (5)0.2606 (4)0.8195 (2)0.0447 (10)
C11A0.89183 (5)0.0796 (5)0.7488 (3)0.0651 (12)
C12A0.87500 (5)0.0493 (5)0.6442 (3)0.0624 (12)
C13A0.86285 (5)0.2238 (5)0.6100 (3)0.0488 (10)
C14A0.87842 (5)0.3740 (4)0.5868 (3)0.0459 (10)
C15A0.87043 (5)0.4839 (5)0.4976 (3)0.0601 (11)
C16A0.84977 (5)0.4169 (6)0.4405 (3)0.0645 (14)
C17A0.84898 (5)0.2192 (5)0.4881 (3)0.0544 (11)
C18A0.85058 (5)0.2892 (6)0.7137 (3)0.0667 (13)
C19A0.91986 (6)0.3209 (6)0.9453 (3)0.0680 (13)
C20A0.82695 (5)0.1433 (5)0.4848 (3)0.0631 (14)
C21A0.82563 (7)0.0575 (7)0.5202 (4)0.0929 (19)
C23A0.79586 (6)0.1640 (8)0.3466 (4)0.0968 (18)
C24A0.78852 (6)0.2706 (7)0.2349 (4)0.0761 (16)
C25A0.77516 (7)0.1930 (8)0.1445 (4)0.0969 (19)
C26A0.76875 (9)0.2920 (14)0.0406 (5)0.131 (3)
C27A0.77567 (10)0.4654 (14)0.0276 (6)0.139 (4)
C28A0.78870 (8)0.5448 (10)0.1186 (6)0.127 (3)
C29A0.79511 (7)0.4458 (8)0.2200 (5)0.099 (2)
C41A0.96695 (6)0.5022 (6)0.9403 (3)0.0658 (12)
C42A0.97621 (6)0.5122 (6)0.7295 (3)0.0799 (14)
O401.000000.7458 (5)0.500000.0872 (16)
H1A0.933000.342800.178300.0600*
H1B0.936800.165200.104700.0600*
H2A0.961000.273700.319200.0650*
H2B0.968600.277300.190100.0650*
H30.966600.039600.179400.0610*
H50.932000.140900.203300.0520*
H6A0.913400.148600.417600.0690*
H6B0.923300.324600.366200.0690*
H7A0.886600.284500.303800.0660*
H7B0.900200.329600.199600.0660*
H11A0.887500.343500.183700.0710*
H11B0.902800.318100.085100.0710*
H12A0.866900.338400.006300.0650*
H12B0.878600.168800.041200.0650*
H150.860800.344600.127600.0710*
H16A0.834200.268400.038800.0750*
H16B0.825600.179700.075500.0750*
H170.848700.008600.092700.0620*
H18A0.836600.103500.206700.0970*
H18B0.857200.209200.247500.0970*
H18C0.840500.297500.152800.0970*
H19A0.911700.326600.354900.0920*
H19B0.912600.144200.429700.0920*
H19C0.933000.253100.415100.0920*
H200.813500.132600.003800.0720*
H21A0.834300.292100.180700.1310*
H21B0.812400.356900.149200.1310*
H21C0.832000.383100.055300.1310*
H23A0.783200.051100.101200.1000*
H23B0.787300.154600.220000.1000*
H250.802000.292700.244700.0940*
H260.784100.523000.354000.1130*
H270.749500.482900.423200.1230*
H280.733200.212300.387100.1290*
H290.751100.019000.280100.1080*
H31O0.993400.132500.339000.0990*0.500
H32O0.997500.002600.234700.0990*0.500
H41A0.959100.344500.249200.1140*
H41B0.977300.305400.350200.1140*
H41C0.955900.376000.385100.1140*
H42A0.948800.100300.517800.0940*
H42B0.972500.083100.505500.0940*
H42C0.958000.087100.479600.0940*
H1C0.928600.008700.879400.0680*
H1D0.936700.017400.752900.0680*
H2C0.958600.126800.974700.0770*
H2D0.964800.039300.896500.0770*
H3B0.971000.161800.741900.0640*
H3C0.994800.239200.955100.1070*0.500
H3D0.998400.076600.867700.1070*0.500
H5A0.941200.345500.680500.0530*
H11C0.885300.090900.822800.0780*
H11D0.900700.027900.756500.0780*
H12C0.881400.005400.574600.0750*
H12D0.865500.044600.666500.0750*
H15A0.876900.589600.473700.0720*
H16C0.849100.419100.353200.0770*
H16D0.838500.490200.465800.0770*
H17A0.856200.142600.433600.0650*
H18D0.843200.399700.689900.1000*
H18E0.860000.312700.784300.1000*
H18F0.840900.196000.731300.1000*
H19D0.910000.236000.972000.1020*
H19E0.913900.441400.939300.1020*
H19F0.932100.322701.002100.1020*
H20A0.819300.216600.539200.0760*
H21D0.834300.129400.473700.1390*
H21E0.811500.098700.504800.1390*
H21F0.830200.071200.604500.1390*
H23C0.790200.216400.416000.1160*
H23D0.791300.037600.337900.1160*
H25A0.770400.073800.153100.1160*
H26A0.759700.239200.019900.1570*
H27A0.771600.530700.042700.1660*
H28A0.793100.665200.111100.1520*
H29A0.804200.499300.280200.1180*
H41D0.981400.526700.960200.0990*
H41E0.962100.424601.000900.0990*
H41F0.959400.615500.936500.0990*
H42D0.973500.462000.649800.1200*
H42E0.990700.501800.755800.1200*
H42F0.972200.639000.728500.1200*
H61A0.925700.627500.813500.0740*
H62A0.939200.665600.707600.0740*
H71A0.901800.663900.654400.0720*
H72A0.915000.558500.567300.0720*
H40A1.000000.6238 (5)0.500000.1310*
H40B0.9991 (15)0.7663 (6)0.5780 (15)0.1310*0.500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0563 (14)0.0739 (17)0.0671 (13)0.0072 (13)0.0074 (11)0.0070 (14)
O220.0544 (14)0.0678 (16)0.0762 (15)0.0016 (13)0.0039 (11)0.0176 (14)
C10.0571 (18)0.0421 (18)0.0525 (17)0.0019 (16)0.0083 (14)0.0058 (15)
C20.059 (2)0.051 (2)0.0535 (18)0.0047 (17)0.0090 (15)0.0113 (16)
C30.0571 (19)0.054 (2)0.0408 (15)0.0044 (17)0.0072 (14)0.0095 (16)
C40.066 (2)0.0347 (18)0.0452 (16)0.0044 (16)0.0067 (15)0.0011 (14)
C50.0639 (19)0.0302 (16)0.0379 (14)0.0000 (15)0.0112 (13)0.0041 (13)
C60.076 (2)0.0385 (18)0.0579 (19)0.0057 (17)0.0081 (17)0.0065 (16)
C70.072 (2)0.0356 (18)0.0597 (18)0.0086 (17)0.0169 (16)0.0035 (16)
C80.0596 (19)0.0340 (17)0.0477 (16)0.0032 (16)0.0153 (14)0.0045 (14)
C90.0554 (18)0.0300 (17)0.0539 (17)0.0014 (15)0.0128 (15)0.0039 (14)
C100.0564 (18)0.0281 (15)0.0432 (15)0.0034 (15)0.0155 (14)0.0057 (14)
C110.062 (2)0.0326 (18)0.081 (2)0.0058 (16)0.0036 (17)0.0024 (17)
C120.0596 (19)0.0380 (18)0.0662 (19)0.0018 (16)0.0085 (16)0.0028 (16)
C130.0550 (18)0.0341 (17)0.0578 (18)0.0032 (15)0.0145 (15)0.0108 (15)
C140.0547 (19)0.0373 (18)0.0550 (17)0.0054 (16)0.0169 (15)0.0028 (15)
C150.067 (2)0.0368 (19)0.072 (2)0.0081 (17)0.0054 (18)0.0018 (17)
C160.072 (2)0.045 (2)0.072 (2)0.0129 (18)0.0175 (18)0.0115 (18)
C170.0576 (19)0.0404 (17)0.0595 (18)0.0031 (16)0.0129 (15)0.0149 (16)
C180.069 (2)0.057 (2)0.070 (2)0.0021 (19)0.0128 (18)0.0200 (18)
C190.073 (2)0.050 (2)0.0630 (19)0.0003 (18)0.0184 (17)0.0178 (17)
C200.058 (2)0.050 (2)0.072 (2)0.0010 (18)0.0060 (17)0.0138 (19)
C210.082 (3)0.057 (3)0.118 (3)0.002 (2)0.012 (2)0.003 (3)
C230.062 (2)0.074 (3)0.111 (3)0.006 (2)0.002 (2)0.011 (3)
C240.058 (2)0.075 (3)0.068 (2)0.009 (2)0.0060 (18)0.002 (2)
C250.064 (2)0.083 (3)0.088 (3)0.013 (2)0.005 (2)0.012 (2)
C260.096 (3)0.087 (3)0.101 (3)0.020 (3)0.014 (3)0.024 (3)
C270.101 (4)0.118 (5)0.087 (3)0.048 (4)0.002 (3)0.017 (3)
C280.073 (3)0.131 (5)0.113 (4)0.018 (4)0.019 (3)0.001 (4)
C290.064 (3)0.099 (4)0.102 (3)0.000 (3)0.007 (2)0.001 (3)
C410.081 (3)0.049 (2)0.095 (3)0.011 (2)0.003 (2)0.001 (2)
C420.076 (2)0.068 (3)0.0433 (16)0.009 (2)0.0042 (15)0.0078 (17)
O3A0.0598 (14)0.0828 (18)0.0708 (14)0.0130 (14)0.0020 (11)0.0133 (15)
O22A0.0555 (14)0.099 (2)0.0633 (14)0.0014 (14)0.0035 (11)0.0062 (15)
C1A0.066 (2)0.0398 (18)0.0630 (19)0.0036 (18)0.0019 (16)0.0115 (16)
C2A0.073 (2)0.047 (2)0.069 (2)0.0123 (19)0.0058 (18)0.0059 (18)
C3A0.0566 (19)0.060 (2)0.0441 (16)0.0101 (17)0.0040 (14)0.0111 (16)
C4A0.061 (2)0.0509 (19)0.0444 (16)0.0039 (17)0.0094 (14)0.0016 (16)
C5A0.0588 (19)0.0363 (16)0.0376 (14)0.0020 (15)0.0106 (13)0.0015 (14)
C6A0.073 (2)0.0383 (19)0.072 (2)0.0033 (19)0.0000 (18)0.0102 (18)
C7A0.071 (2)0.0403 (19)0.067 (2)0.0016 (17)0.0005 (17)0.0150 (17)
C8A0.0548 (18)0.0398 (17)0.0438 (15)0.0054 (15)0.0113 (14)0.0103 (15)
C9A0.0553 (18)0.0383 (18)0.0440 (15)0.0032 (15)0.0099 (13)0.0064 (14)
C10A0.0598 (18)0.0389 (18)0.0366 (14)0.0060 (15)0.0106 (13)0.0070 (14)
C11A0.067 (2)0.047 (2)0.080 (2)0.0040 (19)0.0016 (18)0.0231 (19)
C12A0.061 (2)0.045 (2)0.081 (2)0.0052 (17)0.0060 (18)0.0112 (18)
C13A0.0523 (18)0.0435 (18)0.0519 (17)0.0050 (15)0.0122 (14)0.0094 (15)
C14A0.0584 (19)0.0384 (18)0.0425 (16)0.0062 (15)0.0129 (14)0.0059 (15)
C15A0.062 (2)0.058 (2)0.0605 (19)0.0016 (18)0.0070 (16)0.0159 (19)
C16A0.061 (2)0.074 (3)0.0584 (19)0.005 (2)0.0059 (16)0.0137 (19)
C17A0.0550 (19)0.058 (2)0.0519 (17)0.0048 (17)0.0134 (15)0.0033 (17)
C18A0.064 (2)0.084 (3)0.0545 (18)0.002 (2)0.0170 (16)0.0085 (19)
C19A0.077 (2)0.086 (3)0.0433 (17)0.002 (2)0.0173 (16)0.0016 (18)
C20A0.058 (2)0.071 (3)0.061 (2)0.0030 (18)0.0091 (16)0.0063 (19)
C21A0.083 (3)0.090 (4)0.102 (3)0.024 (3)0.007 (2)0.022 (3)
C23A0.058 (2)0.131 (4)0.099 (3)0.016 (3)0.003 (2)0.026 (3)
C24A0.049 (2)0.106 (4)0.074 (2)0.001 (2)0.0102 (19)0.012 (3)
C25A0.081 (3)0.114 (4)0.095 (3)0.001 (3)0.006 (3)0.005 (3)
C26A0.099 (4)0.214 (8)0.077 (3)0.007 (5)0.004 (3)0.000 (5)
C27A0.089 (4)0.228 (10)0.102 (4)0.029 (5)0.023 (3)0.068 (6)
C28A0.087 (3)0.142 (6)0.155 (5)0.004 (4)0.025 (4)0.069 (5)
C29A0.068 (3)0.121 (5)0.106 (3)0.018 (3)0.006 (2)0.019 (3)
C41A0.073 (2)0.055 (2)0.068 (2)0.0022 (19)0.0015 (18)0.0147 (19)
C42A0.071 (2)0.087 (3)0.083 (2)0.014 (2)0.014 (2)0.018 (2)
O400.101 (3)0.082 (3)0.078 (2)0.00000.007 (2)0.0000
Geometric parameters (Å, º) top
O3—C31.437 (4)C41—H41C0.9601
O22—C201.439 (4)C41—H41A0.9598
O22—C231.409 (4)C41—H41B0.9613
O3—H32O0.9593C42—H42B0.9583
O3—H31O0.9599C42—H42A0.9591
O3A—C3A1.449 (4)C42—H42C0.9597
O22A—C20A1.434 (4)C1A—C10A1.547 (5)
O22A—C23A1.416 (4)C1A—C2A1.527 (5)
O3A—H3D0.9604C2A—C3A1.506 (5)
O3A—H3C0.9597C3A—C4A1.532 (5)
O40—H40B0.89 (2)C4A—C41A1.538 (5)
O40—H40A0.890 (5)C4A—C5A1.569 (4)
C1—C21.526 (5)C4A—C42A1.546 (5)
C1—C101.557 (4)C5A—C10A1.556 (4)
C2—C31.512 (5)C5A—C6A1.519 (5)
C3—C41.545 (5)C6A—C7A1.518 (5)
C4—C421.547 (4)C7A—C8A1.504 (5)
C4—C411.543 (5)C8A—C9A1.355 (4)
C4—C51.559 (4)C8A—C14A1.464 (5)
C5—C61.521 (5)C9A—C11A1.518 (5)
C5—C101.559 (4)C9A—C10A1.548 (4)
C6—C71.521 (5)C10A—C19A1.556 (4)
C7—C81.508 (5)C11A—C12A1.527 (5)
C8—C141.470 (5)C12A—C13A1.524 (5)
C8—C91.360 (4)C13A—C18A1.546 (5)
C9—C111.525 (5)C13A—C17A1.549 (5)
C9—C101.534 (4)C13A—C14A1.531 (5)
C10—C191.556 (4)C14A—C15A1.338 (5)
C11—C121.527 (5)C15A—C16A1.504 (5)
C12—C131.543 (5)C16A—C17A1.539 (6)
C13—C181.554 (5)C17A—C20A1.530 (5)
C13—C171.554 (5)C20A—C21A1.521 (6)
C13—C141.518 (5)C23A—C24A1.502 (7)
C14—C151.339 (5)C24A—C29A1.363 (8)
C15—C161.499 (5)C24A—C25A1.379 (6)
C16—C171.531 (5)C25A—C26A1.391 (9)
C17—C201.529 (5)C26A—C27A1.355 (14)
C20—C211.515 (6)C27A—C28A1.378 (10)
C23—C241.508 (6)C28A—C29A1.368 (9)
C24—C251.387 (6)C1A—H1C0.9707
C24—C291.378 (6)C1A—H1D0.9693
C25—C261.388 (7)C2A—H2C0.9696
C26—C271.383 (7)C2A—H2D0.9691
C27—C281.363 (9)C3A—H3B0.9801
C28—C291.385 (8)C5A—H5A0.9799
C1—H1A0.9698C6A—H61A0.9686
C1—H1B0.9697C6A—H62A0.9689
C2—H2A0.9700C7A—H72A0.9691
C2—H2B0.9692C7A—H71A0.9693
C3—H30.9809C11A—H11D0.9710
C5—H50.9800C11A—H11C0.9697
C6—H6B0.9705C12A—H12C0.9719
C6—H6A0.9692C12A—H12D0.9712
C7—H7B0.9711C15A—H15A0.9301
C7—H7A0.9681C16A—H16C0.9694
C11—H11A0.9705C16A—H16D0.9715
C11—H11B0.9721C17A—H17A0.9801
C12—H12A0.9713C18A—H18D0.9604
C12—H12B0.9719C18A—H18F0.9598
C15—H150.9298C18A—H18E0.9596
C16—H16A0.9700C19A—H19E0.9596
C16—H16B0.9689C19A—H19D0.9600
C17—H170.9787C19A—H19F0.9622
C18—H18B0.9604C20A—H20A0.9815
C18—H18A0.9596C21A—H21D0.9600
C18—H18C0.9605C21A—H21F0.9601
C19—H19C0.9577C21A—H21E0.9631
C19—H19A0.9601C23A—H23D0.9699
C19—H19B0.9611C23A—H23C0.9691
C20—H200.9788C25A—H25A0.9309
C21—H21B0.9622C26A—H26A0.9297
C21—H21C0.9611C27A—H27A0.9310
C21—H21A0.9620C28A—H28A0.9298
C23—H23A0.9706C29A—H29A0.9311
C23—H23B0.9699C41A—H41E0.9593
C25—H250.9298C41A—H41F0.9593
C26—H260.9307C41A—H41D0.9575
C27—H270.9287C42A—H42F0.9604
C28—H280.9323C42A—H42D0.9597
C29—H290.9298C42A—H42E0.9581
O3···O40i2.831 (3)H11B···C12.5206
O3···O40ii2.831 (3)H11B···H1A2.1269
O3···C3Aiii3.419 (4)H11B···H19Exi2.5460
O3···O3Aiii2.816 (3)H11B···H1B2.4614
O3A···O3Aiv2.882 (3)H11C···H19D2.4274
O3A···O3iii2.816 (3)H11C···C18A2.8407
O40···O3v2.831 (3)H11C···H18E2.3126
O40···O3vi2.831 (3)H11C···C19A3.0104
O3···H42B2.7306H11C···H12Bviii2.4924
O3···H40Bii2.15 (3)H11D···H71Ai2.5236
O3···H3Diii2.2237H11D···H1D2.3642
O3···H41B2.5588H11D···C1A2.4992
O3A···H41D2.7201H11D···H1C2.1567
O3A···H32Oiii1.9988H12A···H18C2.5061
O3A···H3Civ2.0124H12A···C212.9008
O3A···H42E2.5513H12A···H21C2.3195
O22···H252.4166H12B···H172.3524
O22···H16A2.7295H12B···H11Cvii2.4924
O22···H18Fvii2.8537H12C···H17A2.3671
O22A···H29A2.6791H12D···H18F2.5283
O22A···H16D2.8619H12D···C21A2.9109
O22A···H16C2.7307H12D···H21F2.3302
O40···H31Ovi2.0071H15···H7A2.4816
O40···H31Ov2.0071H15···C72.7639
C3A···O3iii3.419 (4)H15A···H71A2.5048
C7A···C19v3.543 (5)H15A···C7A2.7798
C9···C183.570 (5)H15A···H72A2.5904
C9A···C18A3.543 (5)H16A···O222.7295
C12···C213.422 (5)H16A···C18Avii3.0627
C12A···C21A3.442 (6)H16A···H21Cv2.5510
C18···C93.570 (5)H16B···H202.5119
C18···C213.574 (6)H16B···H18A2.5870
C18A···C21A3.596 (6)H16C···O22A2.7307
C18A···C9A3.543 (5)H16D···H18D2.5701
C19···C7Ai3.543 (5)H16D···H20A2.5334
C19···C423.276 (5)H16D···O22A2.8619
C19A···C41A3.336 (6)H17···H21A2.5398
C21···C183.574 (6)H17···H12B2.3524
C21···C123.422 (5)H17···C18Avii2.9855
C21A···C18A3.596 (6)H17···H18Fvii2.4004
C21A···C12A3.442 (6)H17A···H21D2.5077
C41A···C19A3.336 (6)H17A···H12C2.3671
C42···C193.276 (5)H18A···C153.0454
C1···H11B2.5206H18A···C203.0727
C1A···H11D2.4992H18A···C162.8911
C2···H19C2.7584H18A···H16B2.5870
C2···H42C2.8177H18A···H202.5867
C2A···H41E2.7696H18B···H11A2.3721
C2A···H19F2.8277H18B···C83.0136
C3···H40Bii3.09 (6)H18B···C112.7819
C3···H3Diii2.8125H18C···H21C2.4089
C3A···H32Oiii2.6332H18C···C213.0646
C6···H42A2.7914H18C···C202.9040
C6···H19B2.7588H18C···H202.5808
C6···H41C2.8087H18C···H12A2.5061
C6A···H41F2.7857H18D···C16A2.8589
C6A···H19E2.7496H18D···C15A2.9820
C6A···H42F2.8056H18D···H20A2.5417
C7···H152.7639H18D···C20A3.0536
C7A···H15A2.7798H18D···H16D2.5701
C8···H18B3.0136H18E···C11A2.7361
C8···H52.8024H18E···H11C2.3126
C8A···H18E2.9961H18E···C9A3.0780
C8A···H5A2.7952H18E···C8A2.9961
C9A···H18E3.0780H18F···O22viii2.8537
C11···H1B3.0225H18F···H20A2.4368
C11···H18B2.7819H18F···H21F2.4636
C11···H19A2.7926H18F···H17viii2.4004
C11···H1A2.7408H18F···C20A2.8266
C11A···H19D2.8741H18F···C21A3.0729
C11A···H1D2.9428H18F···H12D2.5283
C11A···H1C2.7378H19A···C112.7926
C11A···H18E2.7361H19A···H1A2.5244
C12···H21C3.0003H19A···H11A2.3431
C12A···H21F3.0250H19A···H72Ai2.4989
C13···H21C2.9752H19B···H6A2.1405
C13A···H21F3.0158H19B···C62.7588
C15···H7B2.9939H19C···H42C2.0902
C15···H7A2.8347H19C···H72Ai2.5588
C15···H18A3.0454H19C···C22.7584
C15A···H72A2.9653H19C···H2A2.2084
C15A···H71A2.8586H19C···C422.7774
C15A···H7A2.8912H19D···C11A2.8741
C15A···H18D2.9820H19D···H11C2.4274
C16···H18A2.8911H19D···H1C2.4433
C16A···H18D2.8589H19E···C6A2.7496
C18···H202.8009H19E···H11Bxii2.5460
C18···H21C3.0709H19E···H61A2.1495
C18···H11A2.8746H19F···H2C2.2810
C18A···H11C2.8407H19F···C2A2.8277
C18A···H20A2.7113H19F···C41A2.7627
C18A···H16Aviii3.0627H19F···H41E2.0854
C18A···H17viii2.9855H20···H28Ai2.3857
C19···H6A2.7550H20···H18C2.5808
C19···H11A2.9751H20···H23A2.2593
C19···H2A2.8458H20···H18A2.5867
C19···H72Ai2.7243H20···C182.8009
C19···H42C2.7962H20···H16B2.5119
C19A···H41E2.8483H20A···H18F2.4368
C19A···H2C2.8738H20A···C18A2.7113
C19A···H11C3.0104H20A···H23C2.2148
C19A···H61A2.7236H20A···H18D2.5417
C20···H18C2.9040H20A···C25viii3.0850
C20···H18A3.0727H20A···H16D2.5334
C20A···H18F2.8266H21A···H172.5398
C20A···H18D3.0536H21B···C232.7610
C21···H23B2.8349H21B···H23B2.2763
C21···H18C3.0646H21C···C132.9752
C21···H12A2.9008H21C···C183.0709
C21A···H18F3.0729H21C···H12A2.3195
C21A···H12D2.9109H21C···C123.0003
C21A···H23D2.9357H21C···H16Ai2.5510
C23···H21B2.7610H21C···H18C2.4089
C23A···H21E2.7261H21D···H17A2.5077
C24A···H29ix3.0812H21E···H23D2.3774
C25···H20Avii3.0850H21E···C23A2.7261
C27A···H26Aix3.0368H21F···H12D2.3302
C28···H27x3.0490H21F···H18F2.4636
C41···H6B2.6261H21F···C13A3.0158
C41A···H61A3.0334H21F···C12A3.0250
C41A···H2C2.8247H23A···H202.2593
C41A···H3C2.6287H23B···C212.8349
C41A···H19F2.7627H23B···H21B2.2763
C42···H31O3.0975H23B···H292.5719
C42···H2A2.8935H23C···H20A2.2148
C42···H6A3.0531H23D···H25A2.3584
C42···H19C2.7774H23D···C21A2.9357
C42A···H62A2.6376H23D···H21E2.3774
C42A···H40B3.00 (5)H25···O222.4166
H1A···H19A2.5244H25A···H23D2.3584
H1A···C112.7408H26A···C27Axiii3.0368
H1A···H11B2.1269H27···C28xiv3.0490
H1B···H32.5149H28A···H20v2.3857
H1B···H52.5219H29···H23B2.5719
H1B···C113.0225H29···C24Axiii3.0812
H1B···H11B2.4614H29A···O22A2.6791
H1C···C11A2.7378H31O···H2B2.4282
H1C···H19D2.4433H31O···H2A2.3309
H1C···H11D2.1567H31O···O40i2.0071
H1D···H5A2.5517H31O···C423.0975
H1D···H11D2.3642H31O···H40Aii2.5297
H1D···H3B2.4773H31O···H40Ai2.5297
H1D···C11A2.9428H31O···O40ii2.0071
H2A···C192.8458H32O···H3Biii2.3416
H2A···C422.8935H32O···C3Aiii2.6332
H2A···H19C2.2084H32O···O3Aiii1.9988
H2A···H31O2.3309H40A···H31Ovi2.5297
H2A···H42C2.2713H40A···H31Ov2.5297
H2B···H31O2.4282H40B···C42A3.00 (5)
H2C···H19F2.2810H40B···O3vi2.15 (3)
H2C···H41E2.1998H40B···C3vi3.09 (6)
H2C···H3C2.5195H41A···H52.3173
H2C···H3viii2.3724H41A···H32.4220
H2C···C19A2.8738H41B···O32.5588
H2C···C41A2.8247H41B···H42B2.4155
H2D···H41Fi2.5869H41C···H42A2.5663
H2D···H3D2.3918H41C···H6B2.1372
H3···H52.4053H41C···C62.8087
H3···H2Cvii2.3724H41D···H3C2.2728
H3···H41A2.4220H41D···H42E2.4242
H3···H3Diii2.4000H41D···O3A2.7201
H3···H1B2.5149H41D···H41Div2.4828
H3B···H42D2.4306H41E···H2C2.1998
H3B···H1D2.4773H41E···H19F2.0854
H3B···H5A2.3926H41E···C19A2.8483
H3B···H32Oiii2.3416H41E···C2A2.7696
H3C···C41A2.6287H41F···C6A2.7857
H3C···O3Aiv2.0124H41F···H61A2.4572
H3C···H41D2.2728H41F···H42F2.5494
H3C···H2C2.5195H41F···H2Dv2.5869
H3D···O3iii2.2237H42A···H6A2.4715
H3D···H2D2.3918H42A···C62.7914
H3D···H3iii2.4000H42A···H41C2.5663
H3D···C3iii2.8125H42B···O32.7306
H5···H32.4053H42B···H41B2.4155
H5···H1B2.5219H42C···C22.8177
H5···C82.8024H42C···H2A2.2713
H5···H41A2.3173H42C···H19C2.0902
H5···H7B2.4773H42C···C192.7962
H5A···C8A2.7952H42D···H3B2.4306
H5A···H72A2.5384H42D···H5A2.3205
H5A···H42D2.3205H42E···H41D2.4242
H5A···H1D2.5517H42E···O3A2.5513
H5A···H3B2.3926H42F···H62A2.1386
H6A···H19B2.1405H42F···C6A2.8056
H6A···C192.7550H42F···H41F2.5494
H6A···C423.0531H61A···C41A3.0334
H6A···H42A2.4715H61A···H19E2.1495
H6B···C412.6261H61A···H41F2.4572
H6B···H41C2.1372H61A···C19A2.7236
H7A···C152.8347H62A···H42F2.1386
H7A···H152.4816H62A···C42A2.6376
H7A···C15A2.8912H71A···C15A2.8586
H7B···H52.4773H71A···H15A2.5048
H7B···H11Av2.5225H71A···H11Dv2.5236
H7B···C152.9939H72A···C19v2.7243
H11A···C182.8746H72A···H5A2.5384
H11A···C192.9751H72A···H19Av2.4989
H11A···H18B2.3721H72A···H19Cv2.5588
H11A···H7Bi2.5225H72A···H15A2.5904
H11A···H19A2.3431H72A···C15A2.9653
C20—O22—C23115.4 (3)H42B—C42—H42C109.46
C3—O3—H31O109.56H42A—C42—H42B109.28
C3—O3—H32O109.22C4—C42—H42A109.50
H31O—O3—H32O109.55C4—C42—H42B109.50
C20A—O22A—C23A115.5 (3)H42A—C42—H42C109.62
C3A—O3A—H3D109.59C2A—C1A—C10A113.0 (3)
H3C—O3A—H3D109.46C1A—C2A—C3A111.3 (3)
C3A—O3A—H3C109.10O3A—C3A—C2A111.4 (3)
H40A—O40—H40Biii99.7 (4)C2A—C3A—C4A113.0 (3)
H40B—O40—H40Biii160.7 (7)O3A—C3A—C4A112.0 (3)
H40A—O40—H40B99.7 (4)C5A—C4A—C42A108.8 (3)
C2—C1—C10113.1 (3)C5A—C4A—C41A114.3 (3)
C1—C2—C3111.8 (3)C3A—C4A—C5A106.9 (3)
C2—C3—C4113.6 (3)C3A—C4A—C42A107.8 (3)
O3—C3—C4112.4 (3)C41A—C4A—C42A107.4 (3)
O3—C3—C2110.7 (3)C3A—C4A—C41A111.4 (3)
C3—C4—C41107.2 (3)C4A—C5A—C6A115.5 (3)
C5—C4—C42114.6 (3)C6A—C5A—C10A109.8 (3)
C5—C4—C41109.2 (3)C4A—C5A—C10A117.9 (2)
C41—C4—C42107.2 (3)C5A—C6A—C7A110.5 (3)
C3—C4—C5107.2 (2)C6A—C7A—C8A114.8 (3)
C3—C4—C42111.2 (3)C7A—C8A—C14A116.2 (3)
C4—C5—C6115.3 (2)C7A—C8A—C9A122.6 (3)
C4—C5—C10117.7 (2)C9A—C8A—C14A121.1 (3)
C6—C5—C10110.1 (3)C8A—C9A—C10A122.0 (3)
C5—C6—C7109.6 (3)C8A—C9A—C11A120.3 (3)
C6—C7—C8114.0 (3)C10A—C9A—C11A117.3 (2)
C7—C8—C14116.5 (3)C1A—C10A—C19A108.8 (2)
C9—C8—C14121.0 (3)C1A—C10A—C9A110.7 (2)
C7—C8—C9122.5 (3)C5A—C10A—C19A114.6 (3)
C8—C9—C10122.6 (3)C5A—C10A—C9A108.3 (2)
C8—C9—C11119.9 (3)C1A—C10A—C5A108.2 (3)
C10—C9—C11117.3 (3)C9A—C10A—C19A106.3 (3)
C9—C10—C19106.5 (3)C9A—C11A—C12A114.5 (3)
C1—C10—C5107.7 (3)C11A—C12A—C13A112.3 (3)
C5—C10—C9109.0 (2)C12A—C13A—C18A111.4 (3)
C5—C10—C19114.1 (2)C14A—C13A—C17A101.6 (3)
C1—C10—C19108.3 (3)C12A—C13A—C17A116.0 (3)
C1—C10—C9111.3 (2)C12A—C13A—C14A107.8 (3)
C9—C11—C12115.2 (3)C14A—C13A—C18A107.9 (3)
C11—C12—C13112.2 (3)C17A—C13A—C18A111.4 (3)
C12—C13—C17115.3 (3)C8A—C14A—C13A120.3 (3)
C14—C13—C18108.7 (3)C8A—C14A—C15A129.6 (3)
C17—C13—C18112.3 (3)C13A—C14A—C15A110.1 (3)
C12—C13—C18111.0 (3)C14A—C15A—C16A112.2 (3)
C12—C13—C14107.7 (3)C15A—C16A—C17A102.7 (3)
C14—C13—C17101.1 (3)C13A—C17A—C20A119.0 (3)
C8—C14—C15128.2 (3)C16A—C17A—C20A113.3 (3)
C8—C14—C13121.1 (3)C13A—C17A—C16A104.2 (3)
C13—C14—C15110.7 (3)C17A—C20A—C21A114.8 (3)
C14—C15—C16111.7 (3)O22A—C20A—C17A105.4 (3)
C15—C16—C17102.7 (3)O22A—C20A—C21A110.7 (3)
C13—C17—C20119.6 (3)O22A—C23A—C24A108.4 (3)
C13—C17—C16104.0 (3)C23A—C24A—C25A120.9 (5)
C16—C17—C20113.7 (3)C23A—C24A—C29A120.7 (4)
C17—C20—C21115.0 (3)C25A—C24A—C29A118.5 (5)
O22—C20—C21110.3 (3)C24A—C25A—C26A120.3 (6)
O22—C20—C17104.9 (3)C25A—C26A—C27A120.0 (6)
O22—C23—C24110.7 (3)C26A—C27A—C28A119.9 (7)
C25—C24—C29118.7 (4)C27A—C28A—C29A119.7 (7)
C23—C24—C29119.1 (4)C24A—C29A—C28A121.5 (5)
C23—C24—C25122.1 (4)C10A—C1A—H1D108.98
C24—C25—C26120.3 (4)H1C—C1A—H1D107.78
C25—C26—C27120.0 (5)C10A—C1A—H1C108.93
C26—C27—C28119.8 (5)C2A—C1A—H1C108.97
C27—C28—C29120.4 (5)C2A—C1A—H1D109.06
C24—C29—C28120.8 (5)C1A—C2A—H2C109.24
C2—C1—H1B108.99C1A—C2A—H2D109.18
H1A—C1—H1B107.73C3A—C2A—H2C109.46
C10—C1—H1A109.12C3A—C2A—H2D109.48
C10—C1—H1B108.97H2C—C2A—H2D108.08
C2—C1—H1A108.84C4A—C3A—H3B106.71
C3—C2—H2B109.31O3A—C3A—H3B106.55
C1—C2—H2A109.09C2A—C3A—H3B106.68
C3—C2—H2A109.31C4A—C5A—H5A103.97
C1—C2—H2B109.21C6A—C5A—H5A103.85
H2A—C2—H2B108.08C10A—C5A—H5A103.84
O3—C3—H3106.61C7A—C6A—H62A109.48
C2—C3—H3106.46H61A—C6A—H62A107.96
C4—C3—H3106.47C5A—C6A—H61A109.53
C10—C5—H5103.94C5A—C6A—H62A109.64
C4—C5—H5103.99C7A—C6A—H61A109.67
C6—C5—H5104.00C6A—C7A—H71A108.56
C7—C6—H6B109.81C6A—C7A—H72A108.68
C5—C6—H6B109.70C8A—C7A—H71A108.56
C7—C6—H6A109.94C8A—C7A—H72A108.50
H6A—C6—H6B108.12H71A—C7A—H72A107.46
C5—C6—H6A109.66C9A—C11A—H11D108.61
C8—C7—H7A108.86H11C—C11A—H11D107.56
C6—C7—H7B108.63C12A—C11A—H11C108.66
H7A—C7—H7B107.71C12A—C11A—H11D108.68
C6—C7—H7A108.68C9A—C11A—H11C108.61
C8—C7—H7B108.78C13A—C12A—H12D109.09
H11A—C11—H11B107.62H12C—C12A—H12D107.96
C12—C11—H11A108.31C13A—C12A—H12C109.20
C9—C11—H11A108.53C11A—C12A—H12C108.99
C9—C11—H11B108.39C11A—C12A—H12D109.21
C12—C11—H11B108.50C16A—C15A—H15A123.88
C13—C12—H12B109.27C14A—C15A—H15A123.91
C13—C12—H12A109.00C15A—C16A—H16C111.28
C11—C12—H12A109.26C15A—C16A—H16D111.31
C11—C12—H12B109.02C17A—C16A—H16C111.21
H12A—C12—H12B108.00C17A—C16A—H16D111.22
C14—C15—H15124.09H16C—C16A—H16D109.07
C16—C15—H15124.21C16A—C17A—H17A106.55
C17—C16—H16A111.15C13A—C17A—H17A106.52
C15—C16—H16B111.19C20A—C17A—H17A106.59
H16A—C16—H16B109.36C13A—C18A—H18D109.48
C17—C16—H16B111.24C13A—C18A—H18E109.52
C15—C16—H16A111.13H18E—C18A—H18F109.46
C20—C17—H17106.10H18D—C18A—H18F109.42
C13—C17—H17106.31C13A—C18A—H18F109.52
C16—C17—H17106.20H18D—C18A—H18E109.43
H18A—C18—H18B109.56C10A—C19A—H19D109.47
C13—C18—H18B109.36C10A—C19A—H19E109.40
H18B—C18—H18C109.54C10A—C19A—H19F109.34
C13—C18—H18C109.43H19D—C19A—H19E109.59
H18A—C18—H18C109.49H19D—C19A—H19F109.63
C13—C18—H18A109.46H19E—C19A—H19F109.40
H19A—C19—H19B109.36C17A—C20A—H20A108.69
C10—C19—H19A109.46O22A—C20A—H20A108.52
C10—C19—H19C109.55C21A—C20A—H20A108.54
H19A—C19—H19C109.50C20A—C21A—H21D109.48
C10—C19—H19B109.45C20A—C21A—H21E109.43
H19B—C19—H19C109.51H21E—C21A—H21F109.39
C17—C20—H20108.72H21D—C21A—H21F109.46
C21—C20—H20108.82C20A—C21A—H21F109.50
O22—C20—H20108.88H21D—C21A—H21E109.56
H21A—C21—H21C109.28O22A—C23A—H23D109.98
C20—C21—H21B109.42H23C—C23A—H23D108.49
H21A—C21—H21B109.59C24A—C23A—H23C110.10
C20—C21—H21A109.50C24A—C23A—H23D110.02
C20—C21—H21C109.47O22A—C23A—H23C109.83
H21B—C21—H21C109.57C24A—C25A—H25A119.85
H23A—C23—H23B108.11C26A—C25A—H25A119.82
O22—C23—H23B109.50C27A—C26A—H26A120.01
C24—C23—H23A109.45C25A—C26A—H26A119.97
O22—C23—H23A109.48C26A—C27A—H27A119.97
C24—C23—H23B109.55C28A—C27A—H27A120.14
C24—C25—H25119.82C27A—C28A—H28A120.08
C26—C25—H25119.83C29A—C28A—H28A120.20
C27—C26—H26120.13C28A—C29A—H29A119.23
C25—C26—H26119.90C24A—C29A—H29A119.22
C28—C27—H27120.20C4A—C41A—H41E109.44
C26—C27—H27120.01H41D—C41A—H41F109.44
C29—C28—H28119.77C4A—C41A—H41F109.46
C27—C28—H28119.86H41D—C41A—H41E109.46
C24—C29—H29119.58C4A—C41A—H41D109.45
C28—C29—H29119.63H41E—C41A—H41F109.58
H41A—C41—H41C109.43C4A—C42A—H42F109.37
C4—C41—H41B109.49H42D—C42A—H42F109.49
C4—C41—H41C109.50H42E—C42A—H42F109.62
C4—C41—H41A109.44H42D—C42A—H42E109.34
H41A—C41—H41B109.55C4A—C42A—H42D109.58
H41B—C41—H41C109.41C4A—C42A—H42E109.44
C4—C42—H42C109.47
C23—O22—C20—C17159.5 (3)C25—C26—C27—C280.7 (7)
C23—O22—C20—C2176.1 (4)C26—C27—C28—C290.3 (8)
C20—O22—C23—C24168.3 (3)C27—C28—C29—C240.2 (8)
C23A—O22A—C20A—C17A161.7 (4)C2A—C1A—C10A—C9A168.6 (2)
C20A—O22A—C23A—C24A156.2 (4)C2A—C1A—C10A—C19A74.9 (3)
C23A—O22A—C20A—C21A73.6 (4)C10A—C1A—C2A—C3A57.6 (4)
C2—C1—C10—C1972.6 (3)C2A—C1A—C10A—C5A50.1 (3)
C2—C1—C10—C9170.7 (3)C1A—C2A—C3A—O3A172.4 (3)
C10—C1—C2—C356.7 (4)C1A—C2A—C3A—C4A60.5 (4)
C2—C1—C10—C551.3 (3)O3A—C3A—C4A—C42A61.7 (3)
C1—C2—C3—O3174.5 (3)O3A—C3A—C4A—C41A55.9 (4)
C1—C2—C3—C457.9 (4)O3A—C3A—C4A—C5A178.6 (2)
O3—C3—C4—C4163.0 (4)C2A—C3A—C4A—C5A54.6 (3)
C2—C3—C4—C553.0 (3)C2A—C3A—C4A—C41A70.9 (4)
C2—C3—C4—C4273.0 (3)C2A—C3A—C4A—C42A171.4 (3)
C2—C3—C4—C41170.2 (3)C42A—C4A—C5A—C6A60.1 (3)
O3—C3—C4—C5179.8 (3)C3A—C4A—C5A—C10A51.1 (3)
O3—C3—C4—C4253.8 (4)C41A—C4A—C5A—C6A60.0 (4)
C3—C4—C5—C1051.9 (3)C42A—C4A—C5A—C10A167.3 (3)
C3—C4—C5—C6175.5 (3)C3A—C4A—C5A—C6A176.2 (2)
C42—C4—C5—C1072.0 (3)C41A—C4A—C5A—C10A72.7 (4)
C41—C4—C5—C659.7 (4)C4A—C5A—C10A—C19A72.2 (4)
C41—C4—C5—C10167.8 (3)C6A—C5A—C10A—C1A175.6 (2)
C42—C4—C5—C660.6 (4)C4A—C5A—C6A—C7A160.4 (3)
C4—C5—C10—C9172.2 (2)C6A—C5A—C10A—C19A62.9 (3)
C4—C5—C10—C151.4 (3)C10A—C5A—C6A—C7A63.2 (3)
C10—C5—C6—C764.7 (3)C4A—C5A—C10A—C9A169.3 (2)
C6—C5—C10—C1173.8 (2)C4A—C5A—C10A—C1A49.2 (3)
C6—C5—C10—C1965.9 (3)C6A—C5A—C10A—C9A55.6 (3)
C4—C5—C6—C7159.3 (3)C5A—C6A—C7A—C8A39.9 (4)
C6—C5—C10—C952.9 (3)C6A—C7A—C8A—C14A172.8 (3)
C4—C5—C10—C1968.9 (3)C6A—C7A—C8A—C9A11.8 (5)
C5—C6—C7—C843.4 (4)C7A—C8A—C9A—C11A179.2 (3)
C6—C7—C8—C14168.9 (3)C14A—C8A—C9A—C11A5.7 (5)
C6—C7—C8—C913.2 (5)C9A—C8A—C14A—C13A15.2 (5)
C9—C8—C14—C15167.4 (3)C7A—C8A—C9A—C10A6.4 (5)
C9—C8—C14—C1314.5 (5)C7A—C8A—C14A—C15A6.4 (5)
C14—C8—C9—C10179.1 (3)C7A—C8A—C14A—C13A169.3 (3)
C14—C8—C9—C113.9 (5)C9A—C8A—C14A—C15A169.1 (3)
C7—C8—C14—C13167.6 (3)C14A—C8A—C9A—C10A178.4 (3)
C7—C8—C9—C103.1 (5)C8A—C9A—C10A—C5A28.1 (4)
C7—C8—C14—C1510.5 (5)C10A—C9A—C11A—C12A164.8 (3)
C7—C8—C9—C11178.3 (3)C8A—C9A—C10A—C19A95.5 (3)
C8—C9—C11—C1220.5 (4)C8A—C9A—C10A—C1A146.5 (3)
C11—C9—C10—C1974.6 (3)C8A—C9A—C11A—C12A22.2 (4)
C8—C9—C10—C1141.4 (3)C11A—C9A—C10A—C1A40.5 (3)
C11—C9—C10—C143.2 (4)C11A—C9A—C10A—C5A159.0 (2)
C8—C9—C10—C19100.8 (3)C11A—C9A—C10A—C19A77.4 (3)
C11—C9—C10—C5161.8 (3)C9A—C11A—C12A—C13A47.5 (4)
C10—C9—C11—C12164.0 (3)C11A—C12A—C13A—C18A64.6 (4)
C8—C9—C10—C522.8 (4)C11A—C12A—C13A—C14A53.6 (3)
C9—C11—C12—C1346.3 (4)C11A—C12A—C13A—C17A166.6 (3)
C11—C12—C13—C1452.8 (4)C18A—C13A—C14A—C8A81.6 (4)
C11—C12—C13—C1866.0 (4)C18A—C13A—C14A—C15A94.8 (3)
C11—C12—C13—C17164.9 (3)C12A—C13A—C14A—C8A38.8 (4)
C17—C13—C14—C1521.7 (4)C12A—C13A—C14A—C15A144.8 (3)
C18—C13—C14—C881.8 (4)C14A—C13A—C17A—C16A29.8 (3)
C12—C13—C14—C15143.0 (3)C17A—C13A—C14A—C8A161.2 (3)
C17—C13—C14—C8159.8 (3)C17A—C13A—C14A—C15A22.3 (4)
C18—C13—C17—C1685.4 (3)C18A—C13A—C17A—C20A42.5 (4)
C18—C13—C17—C2042.7 (4)C12A—C13A—C17A—C16A146.4 (3)
C12—C13—C14—C838.5 (4)C18A—C13A—C17A—C16A84.8 (3)
C12—C13—C17—C2085.7 (4)C14A—C13A—C17A—C20A157.1 (3)
C14—C13—C17—C1630.2 (3)C12A—C13A—C17A—C20A86.3 (4)
C14—C13—C17—C20158.4 (3)C8A—C14A—C15A—C16A178.6 (3)
C18—C13—C14—C1596.6 (3)C13A—C14A—C15A—C16A5.3 (4)
C12—C13—C17—C16146.1 (3)C14A—C15A—C16A—C17A14.2 (4)
C13—C14—C15—C164.0 (4)C15A—C16A—C17A—C20A157.9 (3)
C8—C14—C15—C16177.7 (3)C15A—C16A—C17A—C13A27.2 (3)
C14—C15—C16—C1715.9 (4)C16A—C17A—C20A—C21A174.6 (3)
C15—C16—C17—C20160.2 (3)C16A—C17A—C20A—O22A52.5 (4)
C15—C16—C17—C1328.4 (3)C13A—C17A—C20A—O22A175.4 (3)
C16—C17—C20—C21177.5 (3)C13A—C17A—C20A—C21A62.5 (4)
C13—C17—C20—O22179.7 (3)O22A—C23A—C24A—C29A51.8 (6)
C13—C17—C20—C2158.9 (4)O22A—C23A—C24A—C25A127.5 (4)
C16—C17—C20—O2256.1 (3)C25A—C24A—C29A—C28A0.3 (7)
O22—C23—C24—C259.4 (5)C23A—C24A—C25A—C26A178.9 (5)
O22—C23—C24—C29173.0 (4)C29A—C24A—C25A—C26A0.4 (7)
C29—C24—C25—C260.1 (6)C23A—C24A—C29A—C28A179.6 (5)
C25—C24—C29—C280.3 (7)C24A—C25A—C26A—C27A0.2 (8)
C23—C24—C25—C26177.7 (4)C25A—C26A—C27A—C28A1.4 (10)
C23—C24—C29—C28177.4 (4)C26A—C27A—C28A—C29A2.1 (10)
C24—C25—C26—C270.6 (7)C27A—C28A—C29A—C24A1.6 (8)
Symmetry codes: (i) x, y1, z; (ii) x+2, y1, z+1; (iii) x+2, y, z+1; (iv) x+2, y, z+2; (v) x, y+1, z; (vi) x+2, y+1, z+1; (vii) x, y, z1; (viii) x, y, z+1; (ix) x+3/2, y+1/2, z; (x) x+3/2, y1/2, z1; (xi) x, y1, z1; (xii) x, y+1, z+1; (xiii) x+3/2, y1/2, z; (xiv) x+3/2, y+1/2, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3C···O3Aiv0.962.012.882 (3)150
O3A—H3D···O3iii0.962.222.816 (3)119
O3—H31O···O40i0.962.012.831 (3)143
O3—H31O···O40ii0.962.012.831 (3)143
O3—H32O···O3Aiii0.962.002.816 (3)142
O40—H40B···O3vi0.892.152.831 (3)133
C25—H25···O220.92982.41662.755 (5)101.38
C41—H41B···O30.96132.55882.944 (5)104.04
C42A—H42E···O3A0.95812.55132.931 (5)103.74
Symmetry codes: (i) x, y1, z; (ii) x+2, y1, z+1; (iii) x+2, y, z+1; (iv) x+2, y, z+2; (vi) x+2, y+1, z+1.
(VI) top
Crystal data top
C29H46OCell parameters were determined using all reflections, including those with theta greater than 25.25
Mr = 410.66Dx = 1.040 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 42635 reflections
a = 10.5743 (7) Åθ = 3.0–26.5°
b = 20.941 (17) ŵ = 0.06 mm1
c = 23.69 (2) ÅT = 293 K
V = 5247 (6) Å3Block, colourless
Z = 80.2 × 0.2 × 0.15 mm
F(000) = 1824
Data collection top
ENRAF-NONIUS κ CCD
diffractometer
3231 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.099
Graphite monochromatorθmax = 25.3°, θmin = 3.0°
Detector resolution: 18.4 pixels mm-1h = 1212
ϕ and ω scans (κ=0)k = 2525
37782 measured reflectionsl = 2828
5260 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.010P)2 + 1.5P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
5260 reflectionsΔρmax = 0.15 e Å3
574 parametersΔρmin = 0.12 e Å3
2 restraintsExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0144 (10)
Crystal data top
C29H46OV = 5247 (6) Å3
Mr = 410.66Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 10.5743 (7) ŵ = 0.06 mm1
b = 20.941 (17) ÅT = 293 K
c = 23.69 (2) Å0.2 × 0.2 × 0.15 mm
Data collection top
ENRAF-NONIUS κ CCD
diffractometer
3231 reflections with I > 2σ(I)
37782 measured reflectionsRint = 0.099
5260 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0512 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.15 e Å3
5260 reflectionsΔρmin = 0.12 e Å3
574 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/UeqOcc. (<1)
O3A1.0172 (5)0.4588 (3)0.5508 (3)0.138 (3)0.761 (6)
C1A0.7534 (6)0.4814 (3)0.4606 (3)0.086 (2)0.761 (6)
C2A0.8345 (6)0.5040 (3)0.5086 (3)0.111 (3)0.761 (6)
C3A0.9054 (5)0.4523 (2)0.5404 (2)0.099 (2)
C4A0.8287 (4)0.3963 (2)0.56080 (17)0.0787 (17)
C5A0.7082 (4)0.38986 (16)0.52378 (14)0.0663 (14)
C6A0.6361 (4)0.32807 (18)0.53176 (17)0.0850 (17)
C7A0.5047 (4)0.33482 (19)0.50785 (15)0.0773 (16)
C8A0.5056 (4)0.36245 (16)0.44906 (14)0.0617 (14)
C9A0.6061 (3)0.39350 (17)0.42801 (14)0.0630 (12)
C10A0.7220 (6)0.4077 (3)0.4621 (3)0.059 (2)0.761 (6)
C11A0.6052 (4)0.4175 (2)0.36760 (15)0.0833 (16)
C12A0.4738 (3)0.42586 (18)0.34231 (15)0.0707 (16)
C13A0.3894 (3)0.36857 (17)0.35261 (13)0.0610 (11)
C14A0.3895 (4)0.35596 (17)0.41635 (14)0.0613 (11)
C15A0.2766 (4)0.3389 (2)0.43424 (17)0.0837 (16)
C16A0.1802 (4)0.3406 (2)0.38780 (17)0.0887 (17)
C17A0.2461 (3)0.37942 (17)0.34144 (14)0.0633 (12)
C18A0.4379 (4)0.30827 (19)0.32266 (17)0.0887 (17)
C19A0.8373 (6)0.3725 (4)0.4337 (3)0.104 (3)0.761 (6)
C20A0.1927 (4)0.36969 (19)0.28222 (15)0.0720 (16)
C21A0.2583 (4)0.4107 (3)0.23856 (18)0.120 (2)
C22A0.0504 (4)0.3812 (2)0.28124 (16)0.0800 (17)
C23A0.0169 (4)0.3732 (2)0.22669 (18)0.0950 (19)
C24A0.1564 (4)0.3839 (2)0.22796 (18)0.0897 (19)
C25A0.2279 (4)0.3865 (3)0.1759 (2)0.125 (2)
C26A0.3654 (4)0.4030 (3)0.1828 (2)0.133 (3)
C27A0.2046 (6)0.3416 (4)0.1313 (3)0.202 (4)
C41A0.7892 (5)0.4121 (3)0.62187 (18)0.126 (2)
C42A0.9128 (5)0.3365 (2)0.5629 (2)0.124 (3)
O3'0.970 (3)0.4793 (12)0.5723 (10)0.1380*0.239 (6)
C1'0.802 (2)0.4505 (10)0.4454 (9)0.0860*0.239 (6)
C2'0.930 (2)0.4579 (11)0.4786 (9)0.1110*0.239 (6)
C10'0.750 (3)0.3901 (12)0.4552 (13)0.0600*0.239 (6)
C19'0.806 (3)0.3317 (11)0.4332 (11)0.1040*0.239 (6)
O30.3761 (3)0.14485 (15)0.09081 (12)0.1007 (12)
C10.0713 (3)0.14639 (19)0.03718 (13)0.0693 (12)
C20.1605 (4)0.1174 (2)0.08126 (16)0.0810 (16)
C30.2948 (4)0.11817 (18)0.06302 (16)0.0727 (14)
C40.3232 (3)0.08178 (18)0.00892 (16)0.0703 (12)
C50.2037 (3)0.08224 (16)0.02902 (14)0.0587 (12)
C60.2302 (4)0.0657 (2)0.09083 (15)0.0807 (17)
C70.1071 (4)0.05070 (18)0.12077 (15)0.0747 (16)
C80.0069 (3)0.09962 (16)0.10938 (13)0.0567 (11)
C90.0132 (3)0.14120 (15)0.06611 (13)0.0566 (11)
C100.1228 (3)0.14330 (15)0.02431 (14)0.0584 (11)
C110.0886 (4)0.19062 (17)0.05780 (16)0.0783 (14)
C120.2142 (4)0.17412 (18)0.08533 (15)0.0720 (14)
C130.1979 (3)0.15346 (16)0.14681 (13)0.0588 (11)
C140.1026 (3)0.09893 (16)0.14751 (13)0.0578 (11)
C150.1349 (4)0.05535 (18)0.18565 (15)0.0703 (14)
C160.2567 (4)0.06990 (17)0.21344 (15)0.0720 (14)
C170.3147 (3)0.12115 (16)0.17462 (13)0.0610 (11)
C180.1448 (4)0.20818 (18)0.18306 (17)0.0843 (16)
C190.1989 (4)0.20501 (17)0.03545 (18)0.0880 (16)
C200.4138 (3)0.16321 (18)0.20336 (15)0.0697 (14)
C210.4663 (4)0.2146 (2)0.16432 (19)0.1027 (19)
C220.5205 (4)0.1217 (2)0.22651 (17)0.0820 (17)
C230.6203 (4)0.1561 (2)0.2608 (2)0.108 (2)
C240.7211 (5)0.1136 (3)0.2831 (2)0.120 (3)
C250.8358 (9)0.1437 (7)0.3085 (4)0.151 (5)0.761 (6)
C260.9290 (7)0.0944 (4)0.3273 (3)0.225 (5)
C270.8107 (13)0.1979 (6)0.3499 (6)0.264 (9)0.761 (6)
C410.4437 (4)0.1080 (2)0.01911 (19)0.104 (2)
C420.3506 (4)0.01217 (19)0.0274 (2)0.1030 (19)
C25'0.806 (4)0.138 (2)0.3357 (19)0.1510*0.239 (6)
C27'0.872 (6)0.193 (3)0.307 (3)0.2650*0.239 (6)
H6C0.680100.293500.512800.1020*
H6D0.631200.317800.571600.1020*
H7C0.455200.362300.532300.0930*
H7D0.464400.293200.507000.0930*
H11C0.652300.387700.344400.1000*
H11D0.648800.458200.366200.1000*
H12C0.434600.463500.358600.0850*
H12D0.481600.432800.302000.0850*
H15A0.258700.327300.471300.1010*
H16C0.103000.361400.400200.1060*
H1C0.796100.491100.425400.1030*0.761 (6)
H1D0.674600.505200.461100.1030*0.761 (6)
H2C0.781200.526700.535200.1330*0.761 (6)
H2D0.895600.534200.494000.1330*0.761 (6)
H5A0.651100.422500.538900.0800*
H19D0.839000.382800.394200.1550*0.761 (6)
H19E0.829900.327100.438300.1550*0.761 (6)
H19F0.914100.387000.451200.1550*0.761 (6)
H20A0.207100.325000.271900.0870*
H21D0.220200.403700.202300.1810*
H21E0.346300.399400.236900.1810*
H21F0.250100.454800.248700.1810*
H22C0.012000.352400.308400.0960*
H22D0.035200.424300.294400.0960*
H23C0.001500.330200.213100.1140*
H23D0.019800.402500.199600.1140*
H24C0.193100.350400.250900.1070*
H24D0.171000.423800.247700.1070*
H25A0.195200.426000.159100.1500*
H26G0.401500.412200.146500.2000*
H26H0.373400.439800.206700.2000*
H26I0.409200.367600.199500.2000*
H27J0.118400.345300.118900.3040*
H27K0.260300.350400.100200.3040*
H27L0.219500.299000.144800.3040*
H41D0.863300.419600.644300.1890*
H41E0.742500.376900.637400.1890*
H41F0.737100.449700.621900.1890*
H42D0.997300.347400.551600.1850*
H42E0.879500.304700.537800.1850*
H42F0.914100.320000.600700.1850*
H16D0.160100.297900.374800.1060*
H17A0.230100.424300.350700.0760*
H18D0.446400.316600.283000.1330*
H18E0.378900.274000.328300.1330*
H18F0.518600.296500.338000.1330*
H1E0.743300.483200.457500.1030*0.239 (6)
H1F0.817500.456000.405400.1030*0.239 (6)
H2E0.988700.425000.466800.1330*0.239 (6)
H2F0.967300.499100.470300.1330*0.239 (6)
H19G0.849500.341400.398800.1550*0.239 (6)
H19H0.743100.299400.426100.1550*0.239 (6)
H19I0.865000.316300.460700.1550*0.239 (6)
H2A0.152500.141200.116200.0970*
H2B0.135100.073700.088600.0970*
H50.150000.047600.014800.0700*
H6A0.271600.101400.109200.0960*
H6B0.286200.029100.092800.0960*
H7A0.122400.048500.161100.0900*
H7B0.077000.009200.108500.0900*
H11A0.059000.231000.073000.0940*
H11B0.102100.196400.017600.0940*
H12A0.269500.211100.083800.0860*
H12B0.254200.139900.064300.0860*
H150.086200.019600.194000.0840*
H16A0.310100.032300.215300.0870*
H1A0.055600.190700.046900.0840*
H1B0.009000.124000.038700.0840*
H18A0.060900.218500.170600.1260*
H18B0.198100.245000.179400.1260*
H18C0.142200.195100.221900.1260*
H19A0.239700.202100.071600.1320*
H19B0.261700.210200.006500.1320*
H19C0.142700.241000.035200.1320*
H200.373200.184600.235400.0840*
H21A0.532000.237700.183400.1540*
H21B0.399700.243500.154000.1540*
H21C0.500200.195000.131000.1540*
H22A0.483600.088600.250000.0990*
H22B0.561900.100700.195000.0990*
H23A0.659100.188700.237300.1300*
H23B0.579500.177600.292200.1300*
H24A0.748900.086200.252500.1440*
H24B0.683200.086300.311500.1440*
H250.877400.164600.276600.1810*0.761 (6)
H26A1.008400.114600.335600.3370*0.761 (6)
H26B0.940700.063500.297800.3370*0.761 (6)
H26C0.897800.073400.360500.3370*0.761 (6)
H27A0.767800.181500.382500.3970*0.761 (6)
H27B0.758900.229700.332100.3970*0.761 (6)
H27C0.889600.216700.361200.3970*0.761 (6)
H41A0.430400.151700.029900.1560*
H41B0.463200.083100.052000.1560*
H41C0.512800.105700.007100.1560*
H42A0.421700.011600.052600.1550*
H42B0.369200.013300.005300.1550*
H42C0.277800.005000.046300.1550*
H16B0.243700.086300.251300.0870*
H170.358700.098100.144400.0730*
H25'0.767800.143100.373100.1810*0.239 (6)
H26D1.003000.120900.328000.3370*0.239 (6)
H26E0.924100.072700.291700.3370*0.239 (6)
H26F0.933900.063600.357200.3370*0.239 (6)
H27D0.851200.231700.326300.3970*0.239 (6)
H27E0.844400.195300.268500.3970*0.239 (6)
H27F0.961400.185900.308300.3970*0.239 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O3A0.084 (4)0.166 (6)0.164 (6)0.044 (4)0.027 (3)0.047 (5)
C1A0.085 (4)0.072 (4)0.101 (4)0.023 (3)0.005 (4)0.020 (3)
C2A0.123 (6)0.085 (4)0.125 (5)0.036 (4)0.035 (5)0.030 (4)
C3A0.090 (4)0.112 (4)0.094 (3)0.033 (3)0.017 (3)0.011 (3)
C4A0.080 (3)0.083 (3)0.073 (3)0.014 (2)0.002 (2)0.004 (2)
C5A0.077 (3)0.061 (2)0.061 (2)0.010 (2)0.002 (2)0.0031 (18)
C6A0.105 (3)0.072 (3)0.078 (3)0.020 (2)0.014 (3)0.018 (2)
C7A0.087 (3)0.079 (3)0.066 (2)0.024 (2)0.007 (2)0.014 (2)
C8A0.073 (3)0.057 (2)0.0551 (19)0.002 (2)0.0063 (19)0.0001 (17)
C9A0.063 (2)0.072 (2)0.054 (2)0.000 (2)0.0100 (19)0.0015 (18)
C10A0.046 (4)0.070 (5)0.062 (3)0.004 (3)0.013 (3)0.004 (3)
C11A0.070 (3)0.117 (3)0.063 (2)0.011 (3)0.006 (2)0.017 (2)
C12A0.070 (3)0.083 (3)0.059 (2)0.005 (2)0.008 (2)0.0082 (19)
C13A0.065 (2)0.062 (2)0.0560 (19)0.007 (2)0.0052 (18)0.0052 (17)
C14A0.066 (2)0.060 (2)0.0578 (19)0.007 (2)0.0071 (19)0.0004 (17)
C15A0.079 (3)0.106 (3)0.066 (2)0.021 (3)0.004 (2)0.011 (2)
C16A0.074 (3)0.111 (3)0.081 (3)0.011 (3)0.003 (2)0.002 (3)
C17A0.064 (2)0.062 (2)0.064 (2)0.0055 (19)0.0063 (19)0.0089 (18)
C18A0.093 (3)0.091 (3)0.082 (3)0.033 (3)0.006 (2)0.019 (2)
C19A0.070 (4)0.160 (7)0.081 (4)0.029 (5)0.018 (3)0.013 (5)
C20A0.070 (3)0.083 (3)0.063 (2)0.015 (2)0.002 (2)0.015 (2)
C21A0.089 (3)0.200 (5)0.072 (3)0.002 (4)0.000 (3)0.025 (3)
C22A0.070 (3)0.095 (3)0.075 (3)0.014 (2)0.001 (2)0.017 (2)
C23A0.072 (3)0.129 (4)0.084 (3)0.018 (3)0.006 (2)0.024 (3)
C24A0.071 (3)0.115 (4)0.083 (3)0.009 (3)0.003 (2)0.019 (3)
C25A0.070 (3)0.208 (6)0.098 (3)0.014 (4)0.013 (3)0.045 (4)
C26A0.076 (3)0.207 (6)0.117 (4)0.019 (4)0.011 (3)0.011 (4)
C27A0.112 (5)0.327 (10)0.168 (6)0.061 (6)0.032 (4)0.147 (7)
C41A0.125 (4)0.176 (5)0.076 (3)0.049 (4)0.008 (3)0.004 (3)
C42A0.114 (4)0.109 (4)0.148 (5)0.000 (4)0.051 (4)0.020 (4)
O30.095 (2)0.110 (2)0.097 (2)0.014 (2)0.0301 (18)0.0116 (18)
C10.068 (2)0.079 (2)0.061 (2)0.004 (2)0.0030 (19)0.015 (2)
C20.082 (3)0.100 (3)0.061 (2)0.009 (2)0.005 (2)0.010 (2)
C30.075 (3)0.073 (2)0.070 (2)0.001 (2)0.013 (2)0.003 (2)
C40.061 (2)0.077 (2)0.073 (2)0.000 (2)0.005 (2)0.004 (2)
C50.053 (2)0.061 (2)0.062 (2)0.0007 (18)0.0014 (18)0.0046 (17)
C60.068 (3)0.096 (3)0.078 (3)0.020 (2)0.005 (2)0.022 (2)
C70.074 (3)0.086 (3)0.064 (2)0.021 (2)0.006 (2)0.023 (2)
C80.059 (2)0.057 (2)0.0541 (19)0.0064 (18)0.0002 (18)0.0058 (17)
C90.061 (2)0.0513 (19)0.0575 (19)0.0049 (18)0.0051 (18)0.0032 (17)
C100.062 (2)0.0523 (19)0.061 (2)0.0037 (18)0.0018 (18)0.0067 (17)
C110.088 (3)0.072 (2)0.075 (2)0.022 (2)0.021 (2)0.023 (2)
C120.077 (3)0.072 (2)0.067 (2)0.023 (2)0.006 (2)0.0136 (19)
C130.067 (2)0.056 (2)0.0535 (19)0.004 (2)0.0051 (17)0.0008 (16)
C140.071 (2)0.054 (2)0.0485 (18)0.0048 (19)0.0024 (18)0.0041 (16)
C150.082 (3)0.067 (2)0.062 (2)0.017 (2)0.008 (2)0.010 (2)
C160.084 (3)0.072 (2)0.060 (2)0.001 (2)0.010 (2)0.0058 (19)
C170.070 (2)0.062 (2)0.0511 (18)0.001 (2)0.0003 (18)0.0041 (17)
C180.095 (3)0.066 (2)0.092 (3)0.011 (2)0.014 (3)0.020 (2)
C190.096 (3)0.068 (2)0.100 (3)0.021 (2)0.016 (3)0.005 (2)
C200.071 (3)0.071 (2)0.067 (2)0.005 (2)0.010 (2)0.009 (2)
C210.102 (4)0.101 (3)0.105 (3)0.033 (3)0.022 (3)0.013 (3)
C220.070 (3)0.092 (3)0.084 (3)0.001 (2)0.011 (2)0.008 (2)
C230.086 (3)0.110 (4)0.128 (4)0.004 (3)0.039 (3)0.009 (3)
C240.093 (4)0.147 (5)0.120 (4)0.021 (4)0.030 (3)0.008 (4)
C250.086 (7)0.212 (10)0.155 (8)0.041 (7)0.062 (6)0.010 (10)
C260.136 (6)0.333 (12)0.206 (8)0.082 (7)0.077 (6)0.058 (8)
C270.251 (16)0.152 (9)0.39 (2)0.055 (10)0.238 (16)0.098 (13)
C410.053 (3)0.158 (5)0.101 (3)0.008 (3)0.003 (2)0.005 (3)
C420.100 (3)0.084 (3)0.125 (4)0.031 (3)0.034 (3)0.014 (3)
Geometric parameters (Å, º) top
O3'—C3A1.17 (3)C42A—H42E0.9597
O3A—C3A1.215 (8)C42A—H42F0.9601
O3—C31.219 (5)C42A—H42D0.9603
C1'—C2'1.57 (3)C1—C21.533 (5)
C1'—C10'1.40 (3)C1—C101.557 (5)
C1A—C10A1.579 (9)C2—C31.485 (6)
C1A—C2A1.501 (10)C3—C41.521 (5)
C2'—C3A1.49 (2)C4—C51.551 (5)
C2A—C3A1.517 (8)C4—C411.538 (5)
C3A—C4A1.506 (6)C4—C421.549 (6)
C4A—C42A1.537 (6)C5—C61.531 (5)
C4A—C5A1.553 (6)C5—C101.542 (5)
C4A—C41A1.542 (6)C6—C71.515 (6)
C5A—C10A1.515 (8)C7—C81.498 (5)
C5A—C10'1.68 (3)C8—C91.347 (4)
C5A—C6A1.514 (5)C8—C141.469 (4)
C6A—C7A1.507 (6)C9—C101.525 (5)
C7A—C8A1.508 (5)C9—C111.506 (5)
C8A—C9A1.342 (5)C10—C191.545 (5)
C8A—C14A1.458 (6)C11—C121.519 (6)
C9A—C10'1.65 (3)C12—C131.529 (5)
C9A—C10A1.498 (7)C13—C141.523 (5)
C9A—C11A1.517 (5)C13—C171.555 (5)
C10'—C19'1.46 (4)C13—C181.538 (5)
C10A—C19A1.576 (10)C14—C151.329 (5)
C11A—C12A1.523 (5)C15—C161.478 (6)
C12A—C13A1.515 (5)C16—C171.541 (5)
C13A—C14A1.533 (5)C17—C201.529 (5)
C13A—C18A1.537 (5)C20—C211.524 (6)
C13A—C17A1.555 (5)C20—C221.526 (5)
C14A—C15A1.316 (6)C22—C231.514 (6)
C15A—C16A1.500 (6)C23—C241.486 (7)
C16A—C17A1.534 (5)C24—C251.494 (12)
C17A—C20A1.526 (5)C24—C25'1.62 (4)
C20A—C22A1.524 (6)C25—C261.495 (15)
C20A—C21A1.513 (6)C25—C271.523 (18)
C22A—C23A1.485 (6)C25'—C261.60 (4)
C23A—C24A1.492 (6)C25'—C27'1.51 (8)
C24A—C25A1.448 (6)C1—H1A0.9703
C25A—C27A1.436 (9)C1—H1B0.9706
C25A—C26A1.503 (6)C2—H2A0.9700
C1'—H1F0.9687C2—H2B0.9694
C1'—H1E0.9677C5—H50.9809
C1A—H1D0.9710C6—H6A0.9695
C1A—H1C0.9699C6—H6B0.9697
C2'—H2F0.9688C7—H7A0.9703
C2'—H2E0.9686C7—H7B0.9701
C2A—H2D0.9680C11—H11A0.9709
C2A—H2C0.9700C11—H11B0.9707
C5A—H5A0.9798C12—H12A0.9710
C6A—H6D0.9695C12—H12B0.9699
C6A—H6C0.9707C15—H150.9299
C7A—H7D0.9704C16—H16A0.9699
C7A—H7C0.9699C16—H16B0.9703
C11A—H11D0.9696C17—H170.9809
C11A—H11C0.9693C18—H18A0.9597
C12A—H12D0.9696C18—H18B0.9590
C12A—H12C0.9706C18—H18C0.9606
C15A—H15A0.9305C19—H19A0.9610
C16A—H16C0.9708C19—H19B0.9609
C16A—H16D0.9693C19—H19C0.9598
C17A—H17A0.9798C20—H200.9804
C18A—H18E0.9603C21—H21A0.9597
C18A—H18D0.9600C21—H21B0.9602
C18A—H18F0.9597C21—H21C0.9593
C19'—H19I0.9580C22—H22A0.9708
C19'—H19H0.9634C22—H22B0.9708
C19'—H19G0.9577C23—H23A0.9718
C19A—H19F0.9611C23—H23B0.9708
C19A—H19D0.9606C24—H24A0.9702
C19A—H19E0.9601C24—H24B0.9697
C20A—H20A0.9792C25—H250.9779
C21A—H21E0.9610C25'—H25'0.9797
C21A—H21F0.9582C26—H26B0.9605
C21A—H21D0.9602C26—H26C0.9597
C22A—H22C0.9709C26—H26D0.9594
C22A—H22D0.9683C26—H26E0.9595
C23A—H23C0.9701C26—H26F0.9595
C23A—H23D0.9690C26—H26A0.9605
C24A—H24C0.9686C27—H27A0.9594
C24A—H24D0.9699C27—H27B0.9599
C25A—H25A0.9809C27—H27C0.9606
C26A—H26G0.9605C27'—H27E0.9590
C26A—H26H0.9600C27'—H27F0.9575
C26A—H26I0.9595C27'—H27D0.9562
C27A—H27J0.9608C41—H41A0.9605
C27A—H27L0.9607C41—H41B0.9601
C27A—H27K0.9612C41—H41C0.9601
C41A—H41E0.9605C42—H42B0.9610
C41A—H41F0.9610C42—H42C0.9604
C41A—H41D0.9597C42—H42A0.9602
O3···H41C2.5876H7D···C15A2.7985
O3···H11Ai2.7217H7D···H15A2.4406
O3···H27Ji2.6552H7D···H42Eviii2.4770
O3'···H2Bii2.6655H11A···H19C2.3227
O3'···H41D2.3971H11A···O3v2.7217
O3'···H41F2.7983H11A···C192.9197
O3'···H42D2.8201H11A···H18A2.3274
O3A···H42D2.3423H11A···C182.8021
O3A···H2Bii2.8541H11B···C12.4786
O3A···H41D2.8688H11B···H1B2.2466
O3A···H42Cii2.8600H11B···H1A2.2651
O3A···H5ii2.8010H11B···H19Bv2.4951
C2'···C7ii3.58 (2)H11C···C19A2.8992
C3···C193.127 (6)H11C···H18F2.3810
C3A···C19A3.115 (9)H11C···C18A2.8586
C7···C2'iii3.58 (2)H11C···C19'2.9058
C9···C183.527 (5)H11C···H19D2.3023
C9A···C18A3.547 (5)H11D···C1A2.5421
C12···C213.366 (6)H11D···C1'2.4843
C12A···C21A3.367 (5)H11D···H1E2.4397
C18···C213.431 (6)H11D···H1F2.0117
C18···C93.527 (5)H11D···H16Aii2.5151
C18A···C9A3.547 (5)H11D···H1D2.4696
C18A···C21A3.490 (7)H11D···H1C2.2064
C19···C413.313 (6)H12A···C212.8242
C19···C33.127 (6)H12A···H21B2.2633
C19'···C42A3.28 (3)H12A···H18B2.4910
C19A···C3A3.115 (9)H12B···H172.3642
C19A···C42A3.252 (9)H12B···C83.0782
C21···C123.366 (6)H12C···H17A2.3206
C21···C183.431 (6)H12C···H6Bix2.3823
C21A···C18A3.490 (7)H12D···H18D2.5024
C21A···C12A3.367 (5)H12D···H21E2.2171
C41···C193.313 (6)H12D···C21A2.8371
C42A···C19'3.28 (3)H15···C72.7591
C42A···C19A3.252 (9)H15···H24Div2.5955
C1···H11B2.4786H15···H22Div2.3887
C1'···H11D2.4843H15···H7A2.4165
C1A···H11D2.5421H15A···C7A2.7462
C2···H19B3.0406H15A···H7D2.4406
C2···H42C2.9655H16A···H22A2.3306
C2···H52.7072H16A···C222.9198
C2'···H5ii2.9941H16A···H11Diii2.5151
C2'···H7Bii2.7981H16B···C41Aviii3.0436
C2'···H42D2.9753H16B···C223.0760
C2'···H19I3.0732H16B···H202.5009
C2A···H41F3.0920H16B···H22A2.5374
C2A···H5A2.6812H16C···H2Ex2.3926
C2A···H1Bii3.0922H16C···C19Ax2.9288
C2A···H19F2.9259H16C···C22A2.9028
C3···H19B2.5592H16C···H19Fx2.3953
C3A···H19F2.5190H16C···H22C2.3859
C4···H19B2.7907H16D···H20A2.5521
C4A···H19F2.7563H16D···C22A3.0500
C4A···H19I2.9290H16D···H22C2.4960
C5···H2Fiii3.0463H17···H12B2.3642
C5···H2B2.8853H17···H21C2.5411
C5A···H2C2.9800H17···H22B2.4612
C6···H19A2.8942H17A···H7Bix2.5916
C6···H42B3.0007H17A···H21F2.5087
C6···H41B2.6551H17A···H22D2.4550
C6A···H41E2.9286H17A···C7ix3.0257
C6A···H19H2.8121H17A···H12C2.3206
C6A···H19I2.9587H18A···C93.0600
C6A···H42E2.6238H18A···H11A2.3274
C6A···H19E3.0172H18A···C82.9691
C7···H17Aiv3.0257H18A···C112.7513
C7···H152.7591H18B···C202.9083
C7···H2Fiii2.8300H18B···C212.9285
C7A···H15A2.7462H18B···H21B2.2153
C8···H18A2.9691H18B···H12A2.4910
C8···H2Diii3.0433H18C···C153.0509
C8···H2Fiii2.8584H18C···C202.9811
C8···H52.9152H18C···H202.4733
C8···H12B3.0782H18C···C162.8948
C8A···H18F2.9750H18D···C20A2.9040
C8A···H19H2.8890H18D···C21A2.9913
C8A···H5A2.9120H18D···H12D2.5024
C9···H6A3.0336H18D···H20A2.5501
C9···H18A3.0600H18D···H21E2.3065
C9···H2Diii2.9318H18E···C15A3.0525
C9A···H18F3.0871H18E···C16A2.8892
C9A···H6C3.0056H18E···H20A2.4953
C10'···H42E2.9839H18E···C20A3.0140
C11···H19C2.7170H18F···C11A2.7840
C11···H19Bv3.0233H18F···H11C2.3810
C11···H18A2.7513H18F···C9A3.0871
C11···H1A2.9119H18F···C8A2.9750
C11···H1B2.8076H19A···H41A2.4812
C11A···H1C2.8855H19A···H6A2.3139
C11A···H1E2.9262H19A···C62.8942
C11A···H1D2.9697H19B···C32.5592
C11A···H19D2.6528H19B···C412.8936
C11A···H18F2.7840H19B···C23.0406
C11A···H1F2.5479H19B···C42.7907
C12···H21B2.9336H19B···H11Bi2.4951
C12A···H21E2.8918H19B···H1A2.5529
C13···H21B2.8526H19B···C11i3.0233
C13A···H21E2.8533H19B···H41A2.2339
C14···H1Ciii3.0382H19C···H11A2.3227
C15···H1Fiii3.0390H19C···C112.7170
C15···H1Ciii3.0440H19C···H1A2.3962
C15···H18C3.0509H19D···C11A2.6528
C15···H7A2.7859H19D···H1C2.4281
C15···H7B3.0490H19D···H11C2.3023
C15A···H7D2.7985H19E···C6A3.0172
C15A···H18E3.0525H19E···C42A3.0860
C15A···H7C3.0340H19E···H6C2.4739
C16···H18C2.8948H19E···H42E2.4603
C16···H22A2.5808H19F···C2A2.9259
C16A···H22C2.6007H19F···C3A2.5190
C16A···H18E2.8892H19F···C4A2.7563
C18···H202.7595H19F···H1C2.5851
C18···H21B2.8786H19F···C42A2.8501
C18···H23C3.0706H19F···H16Cvi2.3953
C18···H11A2.8021H19G···H1F2.4286
C18A···H20A2.7433H19H···C8A2.8890
C18A···H21E2.9511H19H···C6A2.8121
C18A···H11C2.8586H19H···H6C2.1631
C19···H41A2.6937H19I···C6A2.9587
C19···H6A2.8900H19I···C42A2.5096
C19···H11A2.9197H19I···H6C2.3611
C19'···H2E2.8606H19I···H42E1.8493
C19'···H11C2.9058H19I···C2'3.0732
C19'···H6C2.4432H19I···C4A2.9290
C19'···H42E2.6582H20···H23B2.5674
C19A···H16Cvi2.9288H20···H18C2.4733
C19A···H42E2.8808H20···H16B2.5009
C19A···H11C2.8992H20···C182.7595
C19A···H6C3.0021H20A···H18D2.5501
C20···H18B2.9083H20A···H18E2.4953
C20···H18C2.9811H20A···H16D2.5521
C20A···H18E3.0140H20A···C18A2.7433
C20A···H18D2.9040H21A···C232.6749
C21···H12A2.8242H21A···H23A2.1190
C21···H23A2.7278H21B···C122.9336
C21···H18B2.9285H21B···C182.8786
C21A···H23D2.6911H21B···C132.8526
C21A···H12D2.8371H21B···H18B2.2153
C21A···H18D2.9913H21B···H12A2.2633
C22···H16A2.9198H21C···H172.5411
C22···H16B3.0760H21C···H22B2.5738
C22A···H16D3.0500H21D···H23D2.1202
C22A···H16C2.9028H21D···C23A2.6510
C23···H27E2.5145H21E···H18D2.3065
C23···H21A2.6749H21E···C12A2.8918
C23···H27B2.7161H21E···C13A2.8533
C23A···H27J2.8313H21E···C18A2.9511
C23A···H21D2.6510H21E···H12D2.2171
C27···H23B2.8331H21F···H22D2.5970
C27'···H23A2.7935H21F···H17A2.5087
C27A···H23C2.9027H22A···H16A2.3306
C41···H6B2.9244H22A···C162.5808
C41···H6A2.8085H22A···H24B2.5652
C41···H19B2.8936H22A···H16B2.5374
C41A···H16Bvii3.0436H22B···H21C2.5738
C41A···H6D2.8477H22B···H24A2.4204
C42···H6B2.9497H22B···H172.4612
C42···H2B2.9926H22C···H16C2.3859
C42A···H6C2.8766H22C···H16D2.4960
C42A···H19E3.0860H22C···H24C2.5616
C42A···H19F2.8501H22C···C16A2.6007
C42A···H6D3.0104H22D···H24D2.4451
C42A···H2E3.0436H22D···H15ix2.3887
C42A···H19I2.5096H22D···H17A2.4550
H1A···H19B2.5529H22D···H21F2.5970
H1A···H11B2.2651H23A···C212.7278
H1A···C112.9119H23A···C27'2.7935
H1A···H19C2.3962H23A···H27E2.0988
H1B···C112.8076H23A···H21A2.1190
H1B···H11B2.2466H23A···H252.5398
H1B···C2Aiii3.0922H23B···H202.5674
H1B···H2Diii2.3823H23B···C272.8331
H1C···H11D2.2064H23B···H27B2.3839
H1C···C14ii3.0382H23C···C183.0706
H1C···H19D2.4281H23C···H27J2.5709
H1C···H19F2.5851H23C···C27A2.9027
H1C···C11A2.8855H23D···H25A2.5163
H1C···C15ii3.0440H23D···H21D2.1202
H1D···H11D2.4696H23D···C21A2.6911
H1D···H5A2.5414H24A···H26B2.3434
H1D···C11A2.9697H24A···H27E2.5265
H1E···H11D2.4397H24A···H26E2.0916
H1E···H5A2.5072H24A···H22B2.4204
H1E···C11A2.9262H24B···H26C2.5633
H1F···H19G2.4286H24B···H22A2.5652
H1F···C11A2.5479H24C···H22C2.5616
H1F···H11D2.0117H24D···H26H2.3742
H1F···C15ii3.0390H24D···H22D2.4451
H2B···H42C2.4490H24D···H15ix2.5955
H2B···O3Aiii2.8541H25···H23A2.5398
H2B···C422.9926H25A···H23D2.5163
H2B···C52.8853H26A···H41Evii2.5630
H2B···H52.5151H26A···H27C2.5529
H2B···O3'iii2.6655H26B···H24A2.3434
H2C···H5A2.5810H26C···H24B2.5633
H2C···C5A2.9800H26D···H27F1.5047
H2D···C8ii3.0433H26E···H24A2.0916
H2D···C9ii2.9318H26E···H27F2.4350
H2D···H1Bii2.3823H26G···H27K2.2600
H2E···C42A3.0436H26H···H24D2.3742
H2E···C19'2.8606H27B···C232.7161
H2E···H16Cvi2.3926H27B···H23B2.3839
H2E···H42D2.5857H27C···H26A2.5529
H2F···C7ii2.8300H27E···H23A2.0988
H2F···C8ii2.8584H27E···H24A2.5265
H2F···H7Bii2.2082H27E···C232.5145
H2F···H5ii2.2110H27F···H26D1.5047
H2F···C5ii3.0463H27F···H26E2.4350
H5···O3Aiii2.8010H27J···C23A2.8313
H5···C82.9152H27J···H23C2.5709
H5···H2B2.5151H27J···O3v2.6552
H5···H7B2.4842H27K···H26G2.2600
H5···H42C2.2661H41A···H19B2.2339
H5···C2'iii2.9941H41A···H19A2.4812
H5···C22.7072H41A···C192.6937
H5···H2Fiii2.2110H41B···C62.6551
H5A···H41F2.2403H41B···H6B2.3909
H5A···C8A2.9120H41B···H42B2.5075
H5A···H2C2.5810H41B···H6A2.4675
H5A···H7C2.4300H41C···H42A2.4440
H5A···H1E2.5072H41C···O32.5876
H5A···C2A2.6812H41D···O3'2.3971
H5A···H1D2.5414H41D···O3A2.8688
H6A···H19A2.3139H41D···H42F2.3887
H6A···H41B2.4675H41E···H42F2.3385
H6A···C93.0336H41E···H26Aviii2.5630
H6A···C192.8900H41E···C6A2.9286
H6A···C412.8085H41E···H6D2.3125
H6B···C422.9497H41F···C2A3.0920
H6B···H41B2.3909H41F···H5A2.2403
H6B···H42B2.4201H41F···O3'2.7983
H6B···H12Civ2.3823H42A···H41C2.4440
H6B···C412.9244H42B···H41B2.5075
H6C···C9A3.0056H42B···H6B2.4201
H6C···C19A3.0021H42B···C63.0007
H6C···C19'2.4432H42C···H52.2661
H6C···H19H2.1631H42C···O3Aiii2.8600
H6C···H19I2.3611H42C···H2B2.4490
H6C···H42E2.2027H42C···C22.9655
H6C···C42A2.8766H42D···O3A2.3423
H6C···H19E2.4739H42D···H2E2.5857
H6D···C41A2.8477H42D···O3'2.8201
H6D···H41E2.3125H42D···C2'2.9753
H6D···C42A3.0104H42E···H6C2.2027
H7A···H152.4165H42E···C19A2.8808
H7A···C152.7859H42E···C6A2.6238
H7B···H52.4842H42E···H19E2.4603
H7B···H2Fiii2.2082H42E···C10'2.9839
H7B···H17Aiv2.5916H42E···C19'2.6582
H7B···C153.0490H42E···H19I1.8493
H7B···C2'iii2.7981H42E···H7Dvii2.4770
H7C···H5A2.4300H42F···H41D2.3887
H7C···C15A3.0340H42F···H41E2.3385
C2'—C1'—C10'110 (2)C4A—C42A—H42F109.38
C2A—C1A—C10A114.3 (5)C4A—C42A—H42D109.62
C1'—C2'—C3A109.5 (15)H42D—C42A—H42F109.41
C1A—C2A—C3A115.7 (5)H42E—C42A—H42F109.49
O3A—C3A—C4A123.1 (5)H42D—C42A—H42E109.48
O3A—C3A—C2A120.1 (5)C2—C1—C10114.0 (3)
C2'—C3A—C4A118.1 (9)C1—C2—C3112.7 (3)
C2A—C3A—C4A116.7 (4)O3—C3—C2121.5 (4)
O3'—C3A—C4A119.0 (13)O3—C3—C4123.1 (4)
O3'—C3A—C2'119.8 (16)C2—C3—C4115.4 (3)
C3A—C4A—C41A106.3 (4)C3—C4—C5108.9 (3)
C3A—C4A—C42A109.5 (4)C3—C4—C41110.4 (3)
C5A—C4A—C42A115.0 (3)C3—C4—C42105.7 (3)
C41A—C4A—C42A107.5 (4)C5—C4—C41115.0 (3)
C5A—C4A—C41A109.1 (3)C5—C4—C42108.8 (3)
C3A—C4A—C5A109.2 (3)C41—C4—C42107.6 (3)
C4A—C5A—C10'109.2 (11)C4—C5—C6113.8 (3)
C6A—C5A—C10A112.3 (4)C4—C5—C10114.5 (3)
C6A—C5A—C10'104.8 (9)C6—C5—C10111.0 (3)
C4A—C5A—C6A114.6 (3)C5—C6—C7109.7 (3)
C4A—C5A—C10A116.4 (4)C6—C7—C8112.4 (3)
C5A—C6A—C7A109.7 (3)C7—C8—C9123.0 (3)
C6A—C7A—C8A112.2 (3)C7—C8—C14116.1 (3)
C7A—C8A—C9A122.3 (3)C9—C8—C14120.9 (3)
C9A—C8A—C14A121.0 (3)C8—C9—C10123.4 (3)
C7A—C8A—C14A116.7 (3)C8—C9—C11120.6 (3)
C8A—C9A—C11A120.4 (3)C10—C9—C11116.0 (3)
C8A—C9A—C10A122.9 (4)C1—C10—C5107.2 (3)
C10'—C9A—C11A112.8 (11)C1—C10—C9110.1 (3)
C8A—C9A—C10'124.3 (10)C1—C10—C19107.9 (3)
C10A—C9A—C11A116.6 (4)C5—C10—C9110.5 (3)
C5A—C10'—C9A97.7 (16)C5—C10—C19113.1 (3)
C1'—C10'—C5A105.4 (19)C9—C10—C19108.0 (3)
C5A—C10'—C19'117 (2)C9—C11—C12114.4 (3)
C1'—C10'—C9A105.0 (19)C11—C12—C13112.0 (3)
C9A—C10'—C19'106 (2)C12—C13—C14107.3 (3)
C1'—C10'—C19'123 (3)C12—C13—C17115.9 (3)
C1A—C10A—C19A106.6 (5)C12—C13—C18111.2 (3)
C1A—C10A—C5A106.4 (5)C14—C13—C17101.2 (3)
C1A—C10A—C9A110.7 (5)C14—C13—C18108.1 (3)
C9A—C10A—C19A108.1 (5)C17—C13—C18112.2 (3)
C5A—C10A—C9A113.1 (5)C8—C14—C13120.5 (3)
C5A—C10A—C19A111.8 (5)C8—C14—C15128.9 (3)
C9A—C11A—C12A114.5 (3)C13—C14—C15110.6 (3)
C11A—C12A—C13A112.5 (3)C14—C15—C16112.7 (3)
C12A—C13A—C17A115.5 (3)C15—C16—C17103.0 (3)
C12A—C13A—C18A112.3 (3)C13—C17—C16103.9 (3)
C14A—C13A—C17A101.2 (3)C13—C17—C20118.9 (3)
C14A—C13A—C18A108.2 (3)C16—C17—C20114.1 (3)
C17A—C13A—C18A111.5 (3)C17—C20—C21112.7 (3)
C12A—C13A—C14A107.1 (3)C17—C20—C22109.8 (3)
C8A—C14A—C13A120.5 (3)C21—C20—C22110.6 (3)
C8A—C14A—C15A128.2 (3)C20—C22—C23115.9 (3)
C13A—C14A—C15A111.3 (3)C22—C23—C24113.9 (4)
C14A—C15A—C16A111.9 (4)C23—C24—C25118.2 (7)
C15A—C16A—C17A103.2 (3)C23—C24—C25'118.9 (15)
C13A—C17A—C16A104.1 (3)C24—C25—C26111.3 (10)
C13A—C17A—C20A119.8 (3)C24—C25—C27115.6 (9)
C16A—C17A—C20A114.8 (3)C26—C25—C27115.9 (8)
C17A—C20A—C21A112.5 (3)C24—C25'—C26100 (2)
C21A—C20A—C22A110.6 (3)C24—C25'—C27'99 (4)
C17A—C20A—C22A111.0 (3)C26—C25'—C27'90 (3)
C20A—C22A—C23A117.9 (3)C2—C1—H1A108.80
C22A—C23A—C24A116.1 (4)C2—C1—H1B108.77
C23A—C24A—C25A120.3 (4)C10—C1—H1A108.77
C24A—C25A—C27A120.9 (5)C10—C1—H1B108.70
C26A—C25A—C27A113.4 (4)H1A—C1—H1B107.66
C24A—C25A—C26A114.9 (4)C1—C2—H2A108.93
C10'—C1'—H1E109.79C1—C2—H2B109.00
C10'—C1'—H1F109.66C3—C2—H2A109.04
H1E—C1'—H1F108.32C3—C2—H2B109.12
C2'—C1'—H1E109.51H2A—C2—H2B107.92
C2'—C1'—H1F109.39C4—C5—H5105.55
C2A—C1A—H1C108.64C6—C5—H5105.50
C10A—C1A—H1D108.72C10—C5—H5105.49
H1C—C1A—H1D107.61C5—C6—H6A109.74
C2A—C1A—H1D108.62C5—C6—H6B109.67
C10A—C1A—H1C108.78C7—C6—H6A109.73
C1'—C2'—H2E109.69C7—C6—H6B109.77
C3A—C2'—H2E109.83H6A—C6—H6B108.19
C3A—C2'—H2F109.89C6—C7—H7A109.13
C1'—C2'—H2F109.66C6—C7—H7B109.10
H2E—C2'—H2F108.30C8—C7—H7A109.13
C3A—C2A—H2D108.29C8—C7—H7B109.06
H2C—C2A—H2D107.45H7A—C7—H7B107.90
C1A—C2A—H2C108.35C9—C11—H11A108.63
C1A—C2A—H2D108.45C9—C11—H11B108.61
C3A—C2A—H2C108.31C12—C11—H11A108.70
C4A—C5A—H5A103.80C12—C11—H11B108.73
C6A—C5A—H5A103.90H11A—C11—H11B107.63
C10A—C5A—H5A103.88C11—C12—H12A109.21
C10'—C5A—H5A120.83C11—C12—H12B109.19
C5A—C6A—H6D109.76C13—C12—H12A109.21
C7A—C6A—H6C109.75C13—C12—H12B109.24
C5A—C6A—H6C109.77H12A—C12—H12B107.90
H6C—C6A—H6D108.11C14—C15—H15123.72
C7A—C6A—H6D109.73C16—C15—H15123.62
C6A—C7A—H7C109.19C15—C16—H16A111.11
H7C—C7A—H7D107.96C15—C16—H16B111.18
C8A—C7A—H7D109.16C17—C16—H16A111.15
C6A—C7A—H7D109.17C17—C16—H16B111.21
C8A—C7A—H7C109.11H16A—C16—H16B109.13
C9A—C11A—H11D108.69C13—C17—H17106.35
H11C—C11A—H11D107.59C16—C17—H17106.37
C12A—C11A—H11C108.64C20—C17—H17106.47
C12A—C11A—H11D108.62C13—C18—H18A109.48
C9A—C11A—H11C108.58C13—C18—H18B109.51
C13A—C12A—H12C109.11C13—C18—H18C109.45
C13A—C12A—H12D109.12H18A—C18—H18B109.54
H12C—C12A—H12D107.84H18A—C18—H18C109.42
C11A—C12A—H12D109.09H18B—C18—H18C109.43
C11A—C12A—H12C109.05C10—C19—H19A109.45
C16A—C15A—H15A124.06C10—C19—H19B109.43
C14A—C15A—H15A124.00C10—C19—H19C109.46
C17A—C16A—H16D111.16H19A—C19—H19B109.46
H16C—C16A—H16D109.01H19A—C19—H19C109.47
C15A—C16A—H16C111.10H19B—C19—H19C109.55
C15A—C16A—H16D111.11C17—C20—H20107.93
C17A—C16A—H16C111.16C21—C20—H20107.87
C13A—C17A—H17A105.68C22—C20—H20107.80
C16A—C17A—H17A105.64C20—C21—H21A109.50
C20A—C17A—H17A105.67C20—C21—H21B109.42
C13A—C18A—H18D109.51C20—C21—H21C109.49
C13A—C18A—H18E109.45H21A—C21—H21B109.46
C13A—C18A—H18F109.45H21A—C21—H21C109.44
H18D—C18A—H18E109.44H21B—C21—H21C109.52
H18D—C18A—H18F109.52C20—C22—H22A108.39
H18E—C18A—H18F109.45C20—C22—H22B108.36
C10'—C19'—H19I107.71C23—C22—H22A108.19
C10'—C19'—H19G108.79C23—C22—H22B108.29
C10'—C19'—H19H111.81H22A—C22—H22B107.38
H19H—C19'—H19I109.39C22—C23—H23A108.72
H19G—C19'—H19H109.38C22—C23—H23B108.79
H19G—C19'—H19I109.72C24—C23—H23A108.76
C10A—C19A—H19D109.00C24—C23—H23B108.91
H19D—C19A—H19E109.54H23A—C23—H23B107.52
C10A—C19A—H19E110.59C23—C24—H24A107.81
C10A—C19A—H19F108.77C23—C24—H24B107.66
H19D—C19A—H19F109.49C25—C24—H24A107.74
H19E—C19A—H19F109.43C25—C24—H24B107.75
C22A—C20A—H20A107.51H24A—C24—H24B107.17
C17A—C20A—H20A107.44C25'—C24—H24A126.44
C21A—C20A—H20A107.49C25'—C24—H24B83.17
C20A—C21A—H21E109.40C24—C25—H25104.05
C20A—C21A—H21F109.52C26—C25—H25104.05
H21D—C21A—H21E109.40C27—C25—H25104.04
H21D—C21A—H21F109.48C26—C25'—H25'120.62
H21E—C21A—H21F109.59C27'—C25'—H25'121.01
C20A—C21A—H21D109.44C24—C25'—H25'120.14
C20A—C22A—H22C107.73H26A—C26—H26B109.46
C23A—C22A—H22C107.84H26A—C26—H26C109.54
C23A—C22A—H22D107.81C25—C26—H26C109.51
C20A—C22A—H22D107.84C25'—C26—H26D109.30
H22C—C22A—H22D107.22C25'—C26—H26E109.60
C22A—C23A—H23D108.25H26B—C26—H26C109.40
C24A—C23A—H23C108.18H26D—C26—H26E109.46
C22A—C23A—H23C108.25H26D—C26—H26F109.39
H23C—C23A—H23D107.50H26E—C26—H26F109.49
C24A—C23A—H23D108.31C25'—C26—H26F109.59
C23A—C24A—H24C107.37C25—C26—H26A109.46
C23A—C24A—H24D107.24C25—C26—H26B109.47
C25A—C24A—H24C107.22C25—C27—H27A109.52
C25A—C24A—H24D107.18C25—C27—H27B109.47
H24C—C24A—H24D106.83C25—C27—H27C109.48
C24A—C25A—H25A101.15H27B—C27—H27C109.50
C26A—C25A—H25A101.03H27A—C27—H27B109.41
C27A—C25A—H25A101.13H27A—C27—H27C109.45
C25A—C26A—H26G109.46C25'—C27'—H27E109.05
C25A—C26A—H26H109.50H27D—C27'—H27F110.08
C25A—C26A—H26I109.52C25'—C27'—H27F108.89
H26G—C26A—H26H109.40H27D—C27'—H27E110.02
H26G—C26A—H26I109.41C25'—C27'—H27D108.97
H26H—C26A—H26I109.53H27E—C27'—H27F109.81
C25A—C27A—H27J109.58C4—C41—H41A109.49
C25A—C27A—H27K109.48C4—C41—H41C109.46
H27J—C27A—H27K109.36H41A—C41—H41B109.44
H27J—C27A—H27L109.41C4—C41—H41B109.54
H27K—C27A—H27L109.44H41B—C41—H41C109.53
C25A—C27A—H27L109.57H41A—C41—H41C109.35
C4A—C41A—H41D109.49C4—C42—H42B109.43
C4A—C41A—H41E109.52C4—C42—H42C109.52
H41D—C41A—H41E109.46H42A—C42—H42C109.45
H41D—C41A—H41F109.49H42B—C42—H42C109.40
C4A—C41A—H41F109.38H42A—C42—H42B109.53
H41E—C41A—H41F109.50C4—C42—H42A109.50
C4A—C42A—H42E109.45
C10A—C1A—C2A—C3A17.6 (8)C10—C1—C2—C325.1 (5)
C2A—C1A—C10A—C5A35.2 (7)C2—C1—C10—C532.0 (4)
C2A—C1A—C10A—C9A158.5 (5)C2—C1—C10—C9152.2 (3)
C2A—C1A—C10A—C19A84.2 (7)C2—C1—C10—C1990.2 (4)
C1A—C2A—C3A—O3A132.6 (6)C1—C2—C3—O3122.2 (4)
C1A—C2A—C3A—C4A51.2 (7)C1—C2—C3—C459.8 (4)
O3A—C3A—C4A—C5A159.9 (5)O3—C3—C4—C5153.3 (4)
O3A—C3A—C4A—C41A82.6 (6)O3—C3—C4—C4126.2 (5)
O3A—C3A—C4A—C42A33.3 (7)O3—C3—C4—C4290.0 (4)
C2A—C3A—C4A—C5A23.9 (6)C2—C3—C4—C528.7 (4)
C2A—C3A—C4A—C41A93.6 (5)C2—C3—C4—C41155.8 (3)
C2A—C3A—C4A—C42A150.6 (4)C2—C3—C4—C4288.1 (4)
C3A—C4A—C5A—C6A168.2 (3)C3—C4—C5—C6162.4 (3)
C3A—C4A—C5A—C10A34.3 (5)C3—C4—C5—C1033.2 (4)
C41A—C4A—C5A—C6A76.1 (4)C41—C4—C5—C637.9 (4)
C41A—C4A—C5A—C10A150.0 (4)C41—C4—C5—C1091.3 (4)
C42A—C4A—C5A—C6A44.7 (5)C42—C4—C5—C682.9 (4)
C42A—C4A—C5A—C10A89.2 (5)C42—C4—C5—C10147.9 (3)
C4A—C5A—C6A—C7A163.4 (3)C4—C5—C6—C7165.5 (3)
C10A—C5A—C6A—C7A60.8 (5)C10—C5—C6—C763.5 (4)
C4A—C5A—C10A—C1A64.5 (5)C4—C5—C10—C164.1 (3)
C4A—C5A—C10A—C9A173.7 (4)C4—C5—C10—C9176.0 (3)
C4A—C5A—C10A—C19A51.5 (6)C4—C5—C10—C1954.8 (4)
C6A—C5A—C10A—C1A160.6 (4)C6—C5—C10—C1165.3 (3)
C6A—C5A—C10A—C9A38.8 (6)C6—C5—C10—C945.4 (4)
C6A—C5A—C10A—C19A83.5 (6)C6—C5—C10—C1975.8 (4)
C5A—C6A—C7A—C8A48.9 (4)C5—C6—C7—C847.7 (4)
C6A—C7A—C8A—C9A17.6 (5)C6—C7—C8—C917.3 (5)
C6A—C7A—C8A—C14A164.6 (3)C6—C7—C8—C14164.4 (3)
C7A—C8A—C9A—C10A4.6 (6)C7—C8—C9—C100.3 (5)
C7A—C8A—C9A—C11A176.8 (3)C7—C8—C9—C11178.2 (3)
C14A—C8A—C9A—C10A173.1 (4)C14—C8—C9—C10178.6 (3)
C14A—C8A—C9A—C11A5.5 (5)C14—C8—C9—C113.6 (5)
C7A—C8A—C14A—C13A166.2 (3)C7—C8—C14—C13168.9 (3)
C7A—C8A—C14A—C15A12.7 (6)C7—C8—C14—C1510.9 (5)
C9A—C8A—C14A—C13A15.9 (5)C9—C8—C14—C1312.8 (5)
C9A—C8A—C14A—C15A165.1 (4)C9—C8—C14—C15167.4 (4)
C8A—C9A—C10A—C1A125.5 (5)C8—C9—C10—C1132.8 (3)
C8A—C9A—C10A—C5A6.2 (7)C8—C9—C10—C514.6 (4)
C8A—C9A—C10A—C19A118.1 (5)C8—C9—C10—C19109.6 (4)
C11A—C9A—C10A—C1A53.1 (6)C11—C9—C10—C149.2 (4)
C11A—C9A—C10A—C5A172.4 (4)C11—C9—C10—C5167.5 (3)
C11A—C9A—C10A—C19A63.3 (6)C11—C9—C10—C1968.3 (4)
C8A—C9A—C11A—C12A21.4 (5)C8—C9—C11—C1222.1 (5)
C10A—C9A—C11A—C12A157.2 (4)C10—C9—C11—C12159.9 (3)
C9A—C11A—C12A—C13A47.3 (4)C9—C11—C12—C1349.0 (4)
C11A—C12A—C13A—C14A53.8 (4)C11—C12—C13—C1454.5 (4)
C11A—C12A—C13A—C17A165.7 (3)C11—C12—C13—C17166.7 (3)
C11A—C12A—C13A—C18A64.9 (4)C11—C12—C13—C1863.6 (4)
C12A—C13A—C14A—C8A39.6 (4)C12—C13—C14—C837.7 (4)
C12A—C13A—C14A—C15A141.2 (3)C12—C13—C14—C15142.4 (3)
C17A—C13A—C14A—C8A161.0 (3)C17—C13—C14—C8159.7 (3)
C17A—C13A—C14A—C15A19.9 (4)C17—C13—C14—C1520.5 (4)
C18A—C13A—C14A—C8A81.7 (4)C18—C13—C14—C882.3 (4)
C18A—C13A—C14A—C15A97.4 (4)C18—C13—C14—C1597.5 (3)
C12A—C13A—C17A—C16A142.9 (3)C12—C13—C17—C16143.9 (3)
C12A—C13A—C17A—C20A87.2 (4)C12—C13—C17—C2088.0 (4)
C14A—C13A—C17A—C16A27.6 (3)C14—C13—C17—C1628.2 (3)
C14A—C13A—C17A—C20A157.6 (3)C14—C13—C17—C20156.3 (3)
C18A—C13A—C17A—C16A87.3 (3)C18—C13—C17—C1686.8 (3)
C18A—C13A—C17A—C20A42.7 (4)C18—C13—C17—C2041.2 (4)
C8A—C14A—C15A—C16A177.6 (4)C8—C14—C15—C16176.5 (3)
C13A—C14A—C15A—C16A3.3 (5)C13—C14—C15—C163.7 (4)
C14A—C15A—C16A—C17A15.0 (4)C14—C15—C16—C1715.0 (4)
C15A—C16A—C17A—C13A26.3 (4)C15—C16—C17—C1326.7 (3)
C15A—C16A—C17A—C20A159.3 (3)C15—C16—C17—C20157.6 (3)
C13A—C17A—C20A—C21A56.8 (5)C13—C17—C20—C2155.2 (4)
C13A—C17A—C20A—C22A178.5 (3)C13—C17—C20—C22178.9 (3)
C16A—C17A—C20A—C21A178.1 (4)C16—C17—C20—C21178.3 (3)
C16A—C17A—C20A—C22A53.5 (4)C16—C17—C20—C2258.0 (4)
C17A—C20A—C22A—C23A179.5 (3)C17—C20—C22—C23174.8 (3)
C21A—C20A—C22A—C23A54.8 (5)C21—C20—C22—C2360.3 (4)
C20A—C22A—C23A—C24A179.0 (4)C20—C22—C23—C24179.2 (4)
C22A—C23A—C24A—C25A171.0 (4)C22—C23—C24—C25169.2 (5)
C23A—C24A—C25A—C26A175.1 (4)C23—C24—C25—C26178.4 (5)
C23A—C24A—C25A—C27A43.1 (7)C23—C24—C25—C2746.5 (11)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x, y1/2, z+1/2; (v) x+1/2, y+1/2, z; (vi) x+1, y, z; (vii) x+1/2, y+1/2, z+1; (viii) x1/2, y+1/2, z+1; (ix) x, y+1/2, z+1/2; (x) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C42A—H42D···O3A0.962.342.804 (8)109

Experimental details

(II)(III)(IV)(V)
Crystal data
Chemical formulaC31H44OC30H42OC28H44O24C30H42O2·H2O
Mr432.66418.64412.631756.56
Crystal system, space groupMonoclinic, P21Monoclinic, C2Hexagonal, P62Monoclinic, C2
Temperature (K)150150150293
a, b, c (Å)7.271 (3), 9.733 (5), 35.98 (2)23.785 (9), 13.610 (3), 19.080 (7)24.661 (10), 24.661 (10), 7.232 (10)64.902 (4), 7.2926 (14), 11.1447 (11)
α, β, γ (°)90, 93.28 (4), 9090, 121.927 (12), 9090, 90, 12090, 96.055 (13), 90
V3)2542 (2)5242 (3)3809 (6)5245.4 (12)
Z4862
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.070.060.070.07
Crystal size (mm)0.3 × 0.3 × 0.30.2 × 0.2 × 0.10.6 × 0.2 × 0.20.2 × 0.2 × 0.15
Data collection
DiffractometerEnraf-Nonius κ-CCD
diffractometer
Enraf-Nonius κ-CCD
diffractometer
Enraf-Nonius κ-CCD
diffractometer
Enraf-Nonius κ-CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15221, 4842, 4455 29708, 4917, 4763 13233, 2343, 2161 17152, 5110, 3899
Rint0.0480.0490.0450.048
(sin θ/λ)max1)0.6000.6000.5900.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.10 0.046, 0.119, 1.09 0.075, 0.140, 1.05 0.045, 0.106, 1.03
No. of reflections4842491723435110
No. of parameters590559275596
No. of restraints1154
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.140.27, 0.290.52, 0.360.12, 0.12


(VI)
Crystal data
Chemical formulaC29H46O
Mr410.66
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)10.5743 (7), 20.941 (17), 23.69 (2)
α, β, γ (°)90, 90, 90
V3)5247 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.2 × 0.2 × 0.15
Data collection
DiffractometerENRAF-NONIUS κ CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
37782, 5260, 3231
Rint0.099
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.112, 1.01
No. of reflections5260
No. of parameters574
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.12

Computer programs: COLLECT (Nonius, 1998), DIRAX (Duisenberg, 1992), DENZO (Otwinowski & Minor, 1997), DENZO 1.11.0 (Otwinowski & Minor, 1997), EVAL14 (Duisenberg, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), PLATON.

Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O3—H31C···O3Ai0.962.062.890 (3)143
O3A—H32A···O3ii0.961.962.890 (3)164
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···O3Ai0.962.012.855 (3)146
O3—H3C···O3Aii0.961.812.749 (4)167
O3A—H32A···O3iii0.961.962.855 (3)155
O3A—H33A···O3iv0.961.852.749 (4)154
Symmetry codes: (i) x, y1, z; (ii) x, y1, z; (iii) x, y+1, z; (iv) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O3i0.822.182.979 (8)165
Symmetry code: (i) x+y, x+1, z+1/3.
Hydrogen-bond geometry (Å, º) for (V) top
D—H···AD—HH···AD···AD—H···A
O3A—H3C···O3Ai0.962.012.882 (3)150
O3A—H3D···O3ii0.962.222.816 (3)119
O3—H31O···O40iii0.962.012.831 (3)143
O3—H31O···O40iv0.962.012.831 (3)143
O3—H32O···O3Aii0.962.002.816 (3)142
O40—H40B···O3v0.892.152.831 (3)133
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y, z+1; (iii) x, y1, z; (iv) x+2, y1, z+1; (v) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (VI) top
D—H···AD—HH···AD···AD—H···A
C42A—H42D···O3A0.96032.34232.804 (8)108.82
Table 1. Side chain torsion angles of the independent and disordered molecules in the crystal structures of (II)-(VI). Primes indicate a second independent molecule if present, an asterisk indicates the less populated conformation of a disordered side chain. top
MoleculeC17-C20C20-X22X22-C23C23-C24
II179.2 (3)59.0 (4)168.7 (3)-80.7 (5)
II'172.7 (2)63.7 (3)-179.9 (3)87.5 (4)
III179.4 (3)-177.7 (3)79.2 (4)-
III'174.3 (3)-173.9 (3)-100.3 (4)-
IV-32.7 (10)-79.4 (8)169.8 (6)147.2 (10)
IV*-72.1 (7)163.0 (8)-154.2 (8)-132.2 (11)
V175.4 (3)-161.7 (4)156.2 (4)127.5 (4)
V'179.7 (3)-159.5 (3)168.3 (3)-9.4 (5)
VI-178.6 (3)-179.4 (3)179.1 (3)170.9 (4)
VI'-178.9 (3)-174.7 (3)179.1 (4)169.2 (5)
VI'*-178.9 (3)-174.7 (3)179.1 (4)-160.1 (18)
 

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