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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2790.
Published online 2010 October 9. doi:  10.1107/S1600536810039929
PMCID: PMC3009164

Oleanolic acid ethanol monosolvate

Abstract

Crystals of the title compound (systematic name: 3β-hy­droxy­olean-12-en-28-oic acid ethanol monosolvate), C30H48O3·C2H5OH, were obtained from unsuccessful co-crystallization trials. The asymmetric unit contains two symmetry-independent oleanolic acid mol­ecules, as well as two ethanol solvent mol­ecules. Inter­molecular O—H(...)O hydrogen bonds stabilize the crystal packing. In the oleanolic acid mol­ecules, ring C has a slightly distorted envelope conformation, while rings A, B, D and E adopt chair conformations and rings D and E are cis-fused. Both independent ethanol mol­ecules are orientationally disordered [occupancy ratios of 0.742 (8):0.258 (8) and 0.632 (12):0.368 (12).

Related literature

For the biological activity of oleanolic acid and its derivatives, see: Liu (1995 [triangle], 2005 [triangle]). For 1a,3a-dimethylcyclohexane, see: Spirlet et al. (1980 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For ring conformation analysis, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2790-scheme1.jpg

Experimental

Crystal data

  • C30H48O3·C2H6O
  • M r = 502.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2790-efi1.jpg
  • a = 16.3616 (14) Å
  • b = 7.2587 (5) Å
  • c = 25.786 (2) Å
  • β = 107.500 (9)°
  • V = 2920.7 (4) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.57 mm−1
  • T = 130 K
  • 0.34 × 0.11 × 0.08 mm

Data collection

  • Oxford Diffraction SuperNova Atlas diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 [triangle]) T min = 0.901, T max = 1.000
  • 21878 measured reflections
  • 11079 independent reflections
  • 10744 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.114
  • S = 1.09
  • 11079 reflections
  • 732 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.20 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4907 Friedel pairs
  • Flack parameter: 0.01 (13)

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039929/bt5364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039929/bt5364Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support from Poznan University of Medical Sciences (grant No. 501-02-03308417-05160-50437).

supplementary crystallographic information

Comment

Oleanolic acid is a pentacyclic triterpenoid occurring abundantly in plants as a glycoside or a free compound. Oleanolic acid and some of its derivatives, both natural and semi-synthetic, show interesting biological activity which is the reason for the extensive studies on this class of compounds (Liu, 1995; 2005). There are 135 structures deposited in CSD Database, version 5.31 (Allen, 2002). However, the X-ray analysis of the structure of oleanolic acid has not been undertaken because of the difficulties with obtaining a crystal suitable for the investigations.

The structure presented in this paper was solved for the crystal obtained during the unsuccessful co-crystallization attempts. Crystallization process was carried out using ethanol with the addition of 12α-bromo-3a-aza-A-homo-18β-olean-28,13β-olide. The impact of the latter one on the crystals size requires further investigations.

Oleanolic acid crystallizes in form of an ethanol solvate. The asymmetric unit contains two symmetry-independent triterpenoid molecules (host) and two ethanol molecules (guest). Both solvent molecules are orientationally disordered. The figure 1 shows that in ethanol molecule A all atoms whereas in molecule B only methylene and methyl groups are split into two alternative positions. In molecule A the non-H atoms assigned to O1AA, C1AA and C2AA positions have the site occupancy factor of 63% whereas in molecule B the carbon atoms assigned to C1BA and C2BA positions have the factor of 74%.

The conformational differences between the symmetry-independent oleanolic acid molecules A and B are significant only in the angular arrangement of the carboxylic group. In molecule A, the carbonyl group C28═O2 adopts conformation halfway between synperiplanar and synclinal (-sp/-sc) with respect to C17—C18 bond [torsional angle C18A—C17A—C28A—O2A: -27.6 (2)°]. In molecule B, the conformation is halfway between anticlinal and antiperiplanar (+ac/+ap)[torsional angle: C18B—C17B—C28B—O2B: 145.84 (16)°]. The angular orientation of the carboxylic group in both independent molecules A and B is stabilized by the intermolecular hydrogen bonds in which this group acts both as a proton donor and acceptor (Fig. 2, Table 1).

In both independent molecules, rings A, B, D and E have chair conformation distorted to a different degree. Ring C assumes an envelope conformation [Cremer & Pople (1975) parameters molecule A: Q = 0.565 (2) Å, θ = 51.1 (2)°, [var phi] = 1.7 (2)°; molecule B: Q = 0.544 (2) Å, θ = 50.5 (2)°, [var phi] = 4.5 (3)°].

The dihedral angles A/B, B/C, C/D and D/E in molecule A are 17.41 (8), 13.75 (10), 14.13 (10) and 57.92 (6)°, while in molecule B are 14.68 (10), 12.34 (11), 17.47 (10) and 60.26 (6)°. Rings A/B and B/C are trans-, whereas rings D/E are cis-fused. Each of the axial methyl groups C24, C25 and C26 repulses the adjacent methyls. This results in the lengthening of the interatomic distances C24···C25 and C25···C26 [molecule A: 3.2434 (23) and 3.2648 (23) Å; molecule B: 3.2645 (25) and 3.1958 (24) Å] in comparison with the undistorted molecule of 1a,3a-dimethylcyclohexane in which the distance between the methyl carbons is merely 2.52 Å [Spirlet et al., 1980]. An additional consequence of the repulsive interactions between the methyl groups is deformation of the angles C4—C5—C10 and C8—C9—C10 to the values of 117.30 (13) and 117.33 (12)° (molecule A) and 117.90 (13) and 116.98 (13)° (molecule B).

The hydroxyl group at C3 in molecules A and B of oleanolic acid is equatorial with respect to ring A and adopts β orientation.

In the crystal lattice, the symmetry-independent molecules A and B of oleanolic acid are connected with hydrogen bonds O1A-H11···O2B and O1B-H12···O2Ai (Fig. 2, Table 1) into infinite chains extending along the c axis. The hydrogen bonds involve the C3 hydroxyl group and the carbonyl oxygen atom of the C17 carboxylic group. Both of the mentioned functional groups form also hydrogen bonds with the solvent molecules. The ethanol molecules marked A are hydrogen bonded (O1AA-H1AO···O1A and O3B-H32···O1AA) to the triterpenoid molecules A and B belonging to the same chain, whereas the ethanol molecules B are linked through the O3A—H31···O1BAii and O1BA-H1BO···O1B hydrogen bonds with the triterpenoide molecules A and B but from the adjacent chains (Fig. 2, Table 1). Therefore, the ethanol molecules B connect the chains of triterpenoid molecules into two-dimensional layers that extend parallel to the bc plane. The layer thickness is about half of the a parameter length.

Experimental

Oleanolic acid was extracted from mistletoe leaves. Equimolar quantities of oleanolic acid and 12α-bromo-3a-aza-A-homo-18β-olean-28,13β-olide as an additive were dissolved together in hot ethanol and the mixture was set aside to crystallize at room temperature.

Refinement

Except for the triterpenoide hydroxyl and carboxylic groups H atoms which were refined freely the remaining H atoms were positioned into the idealized positions and were refined within the riding model approximation: Cmethyl—H = 0.96 Å, Cmethylene—H = 0.97 Å, Cmethine—H = 0.98 Å, C(sp2)—H = 0.93 Å, O—H = 0.82 Å; Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H. The methyl atoms were refined as a rigid group, which was allowed to rotate. 4907 Friedel pairs were used to determine the absolute configuration which is also known by reference to the chirality of the oleanane derivatives.

Figures

Fig. 1.
The independent molecules of oleanolic acid and ethanol showing the atomic labelling scheme. Non-H atoms are drawn as 30% probability displacement ellipsoids and H atoms are drawn as spheres of an arbitrary size.
Fig. 2.
The hydrogen bonding (dashed and dotted lines) in the title structure. Symmetry codes: (i) x, y, -1 + z; (ii) x, 1 + y, 1 + z. The H atoms not involved in hydrogen bonds have been omitted for clarity.

Crystal data

C30H48O3·C2H6OF(000) = 1112
Mr = 502.75Dx = 1.143 Mg m3
Monoclinic, P21Melting point = 582–583 K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54184 Å
a = 16.3616 (14) ÅCell parameters from 11811 reflections
b = 7.2587 (5) Åθ = 2.8–75.2°
c = 25.786 (2) ŵ = 0.56 mm1
β = 107.500 (9)°T = 130 K
V = 2920.7 (4) Å3Prism, colourless
Z = 40.34 × 0.11 × 0.08 mm

Data collection

Oxford Diffraction SuperNova Atlas diffractometer11079 independent reflections
Radiation source: SuperNova (Cu) X-ray Source10744 reflections with I > 2σ(I)
mirrorRint = 0.025
Detector resolution: 10.5357 pixels mm-1θmax = 72.1°, θmin = 8.9°
ω scansh = −20→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)k = −8→8
Tmin = 0.901, Tmax = 1.000l = −23→31
21878 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114w = 1/[σ2(Fo2) + (0.0678P)2 + 0.6434P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
11079 reflectionsΔρmax = 0.22 e Å3
732 parametersΔρmin = −0.20 e Å3
1 restraintAbsolute structure: Flack (1983), 4907 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (13)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O1A0.90339 (8)0.6221 (2)0.57647 (5)0.0313 (3)
O2A0.77763 (8)0.93170 (18)0.96632 (5)0.0301 (3)
O3A0.70930 (8)1.18974 (18)0.93395 (5)0.0316 (3)
C1A0.86540 (10)0.5160 (2)0.70946 (6)0.0238 (3)
H1A0.89690.43460.73840.029*
H1B0.80740.46880.69560.029*
C2A0.90733 (10)0.5118 (2)0.66370 (7)0.0256 (3)
H2A0.96730.54520.67820.031*
H2B0.90420.38790.64910.031*
C3A0.86311 (10)0.6437 (3)0.61866 (6)0.0249 (3)
H3A0.80320.60490.60390.030*
C4A0.86382 (10)0.8445 (2)0.63751 (6)0.0229 (3)
C5A0.82363 (9)0.8450 (2)0.68520 (6)0.0208 (3)
H5A0.76470.80190.66880.025*
C6A0.81396 (10)1.0361 (2)0.70722 (6)0.0232 (3)
H6A0.79641.12310.67740.028*
H6B0.86861.07640.73150.028*
C7A0.74730 (10)1.0319 (2)0.73782 (6)0.0231 (3)
H7A0.69181.00380.71230.028*
H7B0.74381.15340.75260.028*
C8A0.76693 (10)0.8902 (2)0.78446 (6)0.0201 (3)
C9A0.79544 (10)0.7030 (2)0.76614 (6)0.0202 (3)
H9A0.74330.65170.74070.024*
C10A0.86222 (10)0.7093 (2)0.73320 (6)0.0202 (3)
C11A0.81932 (11)0.5671 (2)0.81433 (7)0.0261 (3)
H11A0.81310.44230.80020.031*
H11B0.87910.58500.83480.031*
C12A0.76539 (10)0.5886 (2)0.85225 (6)0.0231 (3)
H12A0.77520.50530.88090.028*
C13A0.70544 (10)0.7145 (2)0.84866 (6)0.0202 (3)
C14A0.68265 (10)0.8523 (2)0.80123 (6)0.0210 (3)
C15A0.64668 (11)1.0357 (2)0.81549 (6)0.0236 (3)
H15A0.69431.11510.83380.028*
H15B0.61481.09630.78200.028*
C16A0.58848 (10)1.0150 (2)0.85147 (6)0.0229 (3)
H16A0.53700.94910.83160.027*
H16B0.57161.13610.86040.027*
C17A0.63323 (10)0.9107 (2)0.90410 (6)0.0216 (3)
C18A0.65581 (10)0.7139 (2)0.89009 (6)0.0202 (3)
H18A0.69370.66060.92360.024*
C19A0.57587 (10)0.5889 (2)0.87175 (6)0.0231 (3)
H19A0.53960.63180.83680.028*
H19B0.59410.46460.86680.028*
C20A0.52282 (10)0.5835 (2)0.91188 (6)0.0242 (3)
C21A0.49777 (11)0.7811 (2)0.92099 (7)0.0252 (3)
H21A0.46110.83020.88690.030*
H21B0.46520.78020.94680.030*
C22A0.57532 (11)0.9061 (2)0.94220 (7)0.0247 (3)
H22A0.60900.86380.97790.030*
H22B0.55591.03010.94610.030*
C23A0.80474 (11)0.9573 (3)0.59050 (6)0.0292 (4)
H23A0.82180.93980.55830.044*
H23B0.80901.08550.60010.044*
H23C0.74660.91690.58380.044*
C24A0.95432 (11)0.9281 (3)0.65146 (7)0.0281 (4)
H24A0.99480.84530.67480.042*
H24B0.95541.04380.66970.042*
H24C0.96930.94730.61860.042*
C25A0.95356 (10)0.7606 (2)0.76792 (6)0.0241 (3)
H25A0.96620.70120.80270.036*
H25B0.95760.89170.77290.036*
H25C0.99390.72090.74980.036*
C26A0.83793 (10)0.9721 (2)0.83296 (6)0.0243 (3)
H26A0.88641.00520.82130.037*
H26B0.85500.88240.86150.037*
H26C0.81641.07980.84620.037*
C27A0.60956 (10)0.7624 (3)0.75467 (6)0.0243 (3)
H27A0.62280.63510.75110.036*
H27B0.60440.82550.72110.036*
H27C0.55640.77140.76310.036*
C28A0.71465 (10)1.0086 (2)0.93722 (6)0.0226 (3)
C29A0.44085 (12)0.4713 (3)0.88732 (8)0.0340 (4)
H29A0.40830.46650.91270.051*
H29B0.45570.34860.87960.051*
H29C0.40720.52870.85430.051*
C30A0.57331 (12)0.4954 (3)0.96598 (7)0.0299 (4)
H30A0.62750.55660.98000.045*
H30B0.58270.36740.96030.045*
H30C0.54140.50700.99150.045*
O1B0.81330 (9)0.66050 (18)0.04267 (5)0.0304 (3)
O2B0.79977 (8)0.7474 (2)0.47278 (5)0.0320 (3)
O3B0.71731 (10)0.4977 (2)0.45176 (6)0.0428 (3)
C1B0.71248 (10)0.5072 (2)0.14822 (6)0.0238 (3)
H1C0.69860.38380.15730.029*
H1D0.65940.57600.13560.029*
C2B0.75329 (11)0.4953 (2)0.10215 (6)0.0254 (3)
H2C0.80400.41820.11350.031*
H2D0.71320.43850.07060.031*
C3B0.77771 (11)0.6836 (2)0.08688 (6)0.0250 (3)
H3B0.72520.75680.07360.030*
C4B0.84041 (11)0.7895 (2)0.13473 (6)0.0243 (3)
C5B0.80132 (10)0.7879 (2)0.18307 (6)0.0219 (3)
H5B0.74880.86120.17010.026*
C6B0.85528 (11)0.8903 (3)0.23372 (7)0.0264 (3)
H6C0.87761.00290.22290.032*
H6D0.90350.81410.25310.032*
C7B0.80119 (11)0.9368 (2)0.27121 (7)0.0278 (4)
H7C0.75751.02500.25290.033*
H7D0.83770.99570.30370.033*
C8B0.75715 (10)0.7698 (2)0.28832 (6)0.0237 (3)
C9B0.71504 (10)0.6467 (2)0.23786 (6)0.0222 (3)
H9B0.66700.71970.21530.027*
C10B0.77086 (9)0.5999 (2)0.19971 (6)0.0214 (3)
C11B0.67340 (11)0.4763 (3)0.25505 (7)0.0281 (3)
H11C0.62920.43010.22360.034*
H11D0.71650.38080.26670.034*
C12B0.63430 (11)0.5113 (3)0.29992 (7)0.0270 (3)
H12B0.60450.41470.30950.032*
C13B0.63866 (10)0.6688 (3)0.32707 (6)0.0248 (3)
C14B0.68334 (10)0.8376 (2)0.31246 (6)0.0247 (3)
C15B0.72356 (11)0.9623 (3)0.36257 (7)0.0281 (3)
H15C0.78060.91670.38110.034*
H15D0.72971.08560.34970.034*
C16B0.67345 (12)0.9750 (3)0.40403 (7)0.0302 (4)
H16C0.70771.04110.43590.036*
H16D0.62141.04500.38830.036*
C17B0.65013 (11)0.7866 (3)0.42139 (7)0.0276 (4)
C18B0.59397 (10)0.6814 (3)0.37119 (6)0.0269 (3)
H18B0.58780.55530.38300.032*
C19B0.50291 (11)0.7641 (3)0.35052 (7)0.0298 (4)
H19C0.50680.88670.33650.036*
H19D0.46890.68940.32060.036*
C20B0.45584 (11)0.7770 (3)0.39395 (7)0.0339 (4)
C21B0.51280 (12)0.8853 (3)0.44276 (7)0.0373 (4)
H21C0.51741.01170.43180.045*
H21D0.48560.88690.47140.045*
C22B0.60269 (12)0.8040 (3)0.46524 (7)0.0355 (4)
H22C0.59850.68300.48020.043*
H22D0.63620.88150.49460.043*
C23B0.84380 (13)0.9892 (3)0.11599 (7)0.0320 (4)
H23D0.78921.04680.11100.048*
H23E0.85720.99030.08220.048*
H23F0.88711.05540.14300.048*
C24B0.93099 (11)0.7092 (3)0.14856 (7)0.0316 (4)
H24D0.95440.73360.11930.047*
H24E0.92870.57860.15380.047*
H24F0.96660.76520.18130.047*
C25B0.84530 (10)0.4654 (2)0.22509 (7)0.0260 (3)
H25D0.82890.38220.24910.039*
H25E0.89500.53380.24510.039*
H25F0.85830.39660.19680.039*
C26B0.82541 (11)0.6599 (3)0.33183 (7)0.0289 (4)
H26D0.79960.55170.34160.043*
H26E0.84820.73540.36350.043*
H26F0.87090.62440.31750.043*
C27B0.61333 (11)0.9524 (3)0.27131 (7)0.0287 (4)
H27D0.57821.01280.29000.043*
H27E0.57850.87240.24380.043*
H27F0.64001.04300.25460.043*
C28B0.73084 (11)0.6762 (3)0.45021 (6)0.0285 (4)
C29B0.37235 (12)0.8830 (4)0.37015 (8)0.0411 (5)
H29D0.34140.88790.39640.062*
H29E0.33810.82180.33790.062*
H29F0.38501.00590.36120.062*
C30B0.43526 (13)0.5863 (4)0.41156 (8)0.0397 (4)
H30D0.40610.59870.43860.060*
H30E0.48750.51870.42650.060*
H30F0.39920.52150.38070.060*
O1BA0.84055 (9)0.3450 (2)−0.00132 (7)0.0463 (4)
H1BO0.8341 (18)0.446 (5)0.0130 (12)0.057 (8)*
C1BA0.9207 (2)0.3265 (6)−0.0114 (2)0.0467 (10)0.742 (8)
H1BA0.92810.4274−0.03420.056*0.742 (8)
H1BB0.92140.2124−0.03080.056*0.742 (8)
C2BA0.9930 (2)0.3264 (6)0.04001 (16)0.0608 (12)0.742 (8)
H2BA1.04610.31070.03180.091*0.742 (8)
H2BB0.98570.22700.06280.091*0.742 (8)
H2BC0.99400.44130.05860.091*0.742 (8)
C1BB0.9313 (7)0.3021 (18)0.0183 (6)0.050 (3)0.258 (8)
H1BC0.94000.17990.03420.060*0.258 (8)
H1BD0.96110.39050.04570.060*0.258 (8)
C2BB0.9646 (8)0.311 (2)−0.0308 (5)0.073 (4)0.258 (8)
H2BD1.02530.2893−0.01940.109*0.258 (8)
H2BE0.95320.4314−0.04710.109*0.258 (8)
H2BF0.93640.2197−0.05680.109*0.258 (8)
O1AA0.8414 (4)0.3086 (9)0.5142 (3)0.0323 (10)0.632 (12)
H1AO0.86550.39690.53230.048*0.632 (12)
C1AA0.9004 (3)0.2115 (7)0.49363 (15)0.0420 (13)0.632 (12)
H1AA0.88200.08440.48680.050*0.632 (12)
H1AB0.95640.21210.52060.050*0.632 (12)
C2AA0.9069 (3)0.2957 (11)0.4424 (2)0.0619 (17)0.632 (12)
H2AA0.94620.22580.42920.093*0.632 (12)
H2AB0.92710.42010.44940.093*0.632 (12)
H2AC0.85150.29570.41570.093*0.632 (12)
O1AB0.8662 (7)0.3365 (18)0.5130 (5)0.039 (2)0.368 (12)
H2AO0.88590.38970.54220.058*0.368 (12)
C1AB0.9355 (7)0.2945 (18)0.4897 (4)0.068 (3)0.368 (12)
H1AC0.98280.23700.51700.082*0.368 (12)
H1AD0.95620.40730.47790.082*0.368 (12)
C2AB0.9031 (6)0.170 (3)0.4434 (5)0.084 (4)0.368 (12)
H2AD0.94820.14220.42790.125*0.368 (12)
H2AE0.85640.22720.41650.125*0.368 (12)
H2AF0.88350.05750.45550.125*0.368 (12)
H110.8743 (19)0.675 (5)0.5475 (12)0.061 (9)*
H310.759 (2)1.243 (5)0.9581 (12)0.065 (9)*
H120.8009 (16)0.748 (4)0.0208 (10)0.042 (6)*
H320.770 (2)0.444 (6)0.4732 (14)0.089 (11)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0295 (6)0.0428 (8)0.0240 (6)0.0069 (6)0.0118 (5)−0.0030 (5)
O2A0.0295 (6)0.0258 (6)0.0305 (6)−0.0034 (5)0.0021 (5)0.0030 (5)
O3A0.0313 (6)0.0205 (6)0.0394 (7)−0.0025 (5)0.0052 (5)−0.0034 (5)
C1A0.0218 (7)0.0241 (8)0.0277 (7)−0.0007 (6)0.0105 (6)−0.0010 (6)
C2A0.0239 (7)0.0257 (8)0.0292 (8)0.0016 (6)0.0111 (6)−0.0051 (7)
C3A0.0196 (7)0.0328 (9)0.0247 (8)−0.0009 (6)0.0101 (6)−0.0053 (7)
C4A0.0186 (7)0.0296 (8)0.0221 (7)−0.0002 (6)0.0085 (6)−0.0002 (6)
C5A0.0175 (7)0.0239 (8)0.0215 (7)−0.0035 (6)0.0067 (6)−0.0013 (6)
C6A0.0272 (8)0.0208 (8)0.0229 (7)−0.0013 (6)0.0095 (6)0.0022 (6)
C7A0.0273 (8)0.0202 (7)0.0233 (7)0.0028 (6)0.0100 (6)0.0018 (6)
C8A0.0204 (7)0.0210 (7)0.0191 (7)0.0002 (6)0.0061 (6)0.0006 (6)
C9A0.0199 (7)0.0200 (7)0.0218 (7)−0.0009 (6)0.0081 (6)0.0011 (6)
C10A0.0185 (7)0.0198 (7)0.0225 (7)−0.0012 (6)0.0066 (6)−0.0020 (6)
C11A0.0274 (8)0.0240 (8)0.0311 (8)0.0048 (6)0.0152 (6)0.0055 (7)
C12A0.0256 (8)0.0214 (7)0.0238 (7)0.0018 (6)0.0098 (6)0.0055 (6)
C13A0.0209 (7)0.0196 (7)0.0202 (7)−0.0029 (6)0.0063 (5)−0.0007 (6)
C14A0.0214 (7)0.0216 (8)0.0209 (7)0.0007 (6)0.0079 (6)0.0007 (6)
C15A0.0267 (8)0.0230 (8)0.0221 (7)0.0033 (6)0.0088 (6)0.0044 (6)
C16A0.0242 (7)0.0207 (7)0.0243 (7)0.0044 (6)0.0081 (6)0.0011 (6)
C17A0.0225 (7)0.0221 (8)0.0214 (7)−0.0004 (6)0.0082 (6)−0.0003 (6)
C18A0.0210 (7)0.0202 (7)0.0201 (7)0.0012 (6)0.0076 (5)0.0021 (6)
C19A0.0251 (8)0.0229 (7)0.0225 (7)−0.0019 (6)0.0091 (6)−0.0023 (6)
C20A0.0235 (8)0.0266 (8)0.0255 (7)−0.0053 (7)0.0117 (6)−0.0037 (7)
C21A0.0231 (8)0.0281 (8)0.0279 (8)0.0003 (6)0.0128 (6)−0.0020 (6)
C22A0.0286 (8)0.0230 (8)0.0256 (7)−0.0006 (6)0.0129 (6)−0.0030 (6)
C23A0.0297 (8)0.0365 (9)0.0224 (7)0.0047 (7)0.0094 (6)0.0014 (7)
C24A0.0237 (8)0.0358 (10)0.0273 (8)−0.0051 (7)0.0112 (6)0.0003 (7)
C25A0.0207 (7)0.0282 (8)0.0235 (7)−0.0025 (6)0.0070 (6)−0.0006 (6)
C26A0.0251 (8)0.0256 (8)0.0229 (7)−0.0055 (6)0.0081 (6)−0.0028 (6)
C27A0.0195 (7)0.0320 (8)0.0219 (7)−0.0014 (6)0.0072 (6)−0.0001 (6)
C28A0.0273 (8)0.0229 (8)0.0197 (7)−0.0009 (7)0.0104 (6)−0.0003 (6)
C29A0.0283 (8)0.0382 (10)0.0398 (9)−0.0109 (8)0.0167 (7)−0.0104 (8)
C30A0.0353 (9)0.0302 (9)0.0298 (8)0.0012 (7)0.0180 (7)0.0045 (7)
O1B0.0434 (7)0.0258 (6)0.0245 (6)0.0068 (5)0.0143 (5)0.0036 (5)
O2B0.0263 (6)0.0409 (7)0.0272 (6)−0.0008 (5)0.0057 (5)−0.0005 (5)
O3B0.0427 (8)0.0333 (8)0.0437 (8)−0.0025 (6)0.0001 (6)0.0025 (6)
C1B0.0209 (7)0.0242 (8)0.0246 (7)−0.0006 (6)0.0045 (6)−0.0002 (6)
C2B0.0255 (8)0.0257 (9)0.0229 (7)0.0007 (7)0.0039 (6)−0.0040 (6)
C3B0.0266 (8)0.0249 (8)0.0229 (7)0.0048 (6)0.0068 (6)0.0016 (6)
C4B0.0239 (8)0.0239 (8)0.0249 (7)−0.0008 (6)0.0071 (6)0.0001 (6)
C5B0.0176 (7)0.0241 (8)0.0225 (7)0.0022 (6)0.0037 (6)0.0000 (6)
C6B0.0222 (8)0.0299 (9)0.0264 (8)−0.0058 (7)0.0061 (6)−0.0024 (7)
C7B0.0282 (8)0.0266 (9)0.0284 (8)−0.0073 (7)0.0080 (7)−0.0071 (7)
C8B0.0236 (8)0.0243 (8)0.0226 (7)−0.0005 (6)0.0061 (6)−0.0010 (6)
C9B0.0196 (7)0.0215 (8)0.0237 (7)−0.0004 (6)0.0040 (6)0.0004 (6)
C10B0.0184 (7)0.0214 (7)0.0226 (7)0.0025 (6)0.0035 (6)0.0000 (6)
C11B0.0295 (8)0.0260 (8)0.0317 (8)−0.0042 (7)0.0135 (7)−0.0038 (7)
C12B0.0261 (8)0.0285 (9)0.0277 (8)−0.0025 (7)0.0100 (6)0.0016 (7)
C13B0.0225 (7)0.0297 (8)0.0207 (7)0.0008 (6)0.0043 (6)0.0018 (6)
C14B0.0245 (8)0.0250 (8)0.0245 (7)0.0008 (7)0.0073 (6)−0.0009 (6)
C15B0.0304 (8)0.0267 (8)0.0278 (8)−0.0033 (7)0.0097 (7)−0.0035 (7)
C16B0.0290 (8)0.0339 (10)0.0270 (8)0.0023 (7)0.0072 (6)−0.0059 (7)
C17B0.0239 (8)0.0352 (9)0.0230 (7)0.0007 (7)0.0060 (6)−0.0027 (7)
C18B0.0233 (8)0.0348 (9)0.0223 (7)0.0004 (7)0.0062 (6)0.0005 (7)
C19B0.0246 (8)0.0402 (10)0.0232 (7)−0.0005 (7)0.0052 (6)−0.0023 (7)
C20B0.0254 (8)0.0498 (12)0.0268 (8)−0.0006 (8)0.0082 (7)−0.0050 (8)
C21B0.0282 (9)0.0572 (13)0.0275 (8)0.0007 (9)0.0101 (7)−0.0102 (8)
C22B0.0284 (9)0.0540 (13)0.0234 (8)−0.0024 (8)0.0070 (7)−0.0078 (8)
C23B0.0405 (10)0.0260 (9)0.0310 (8)−0.0054 (8)0.0129 (7)0.0006 (7)
C24B0.0237 (8)0.0418 (10)0.0305 (8)0.0013 (7)0.0098 (6)0.0011 (7)
C25B0.0234 (8)0.0275 (8)0.0263 (7)0.0031 (7)0.0061 (6)0.0023 (7)
C26B0.0236 (8)0.0362 (9)0.0252 (8)0.0037 (7)0.0048 (6)−0.0010 (7)
C27B0.0303 (8)0.0285 (8)0.0282 (8)0.0067 (7)0.0101 (7)0.0025 (7)
C28B0.0284 (8)0.0366 (10)0.0205 (7)0.0000 (7)0.0076 (6)−0.0013 (7)
C29B0.0262 (9)0.0610 (14)0.0351 (9)0.0027 (9)0.0076 (7)−0.0065 (9)
C30B0.0321 (9)0.0582 (13)0.0307 (9)−0.0052 (9)0.0122 (7)0.0011 (9)
O1BA0.0316 (7)0.0417 (9)0.0636 (10)−0.0043 (6)0.0111 (7)−0.0254 (8)
C1BA0.0359 (18)0.052 (2)0.052 (2)−0.0029 (14)0.0139 (19)−0.0133 (18)
C2BA0.038 (2)0.065 (2)0.071 (2)0.0032 (16)0.0046 (18)−0.0057 (19)
C1BB0.035 (7)0.067 (7)0.049 (6)0.016 (4)0.012 (6)−0.002 (6)
C2BB0.079 (8)0.079 (8)0.086 (8)−0.001 (7)0.063 (7)−0.005 (7)
O1AA0.032 (3)0.028 (2)0.0386 (14)−0.0019 (17)0.012 (2)−0.0017 (13)
C1AA0.037 (2)0.039 (2)0.049 (2)0.0004 (18)0.0110 (15)−0.0104 (16)
C2AA0.063 (3)0.064 (4)0.075 (3)0.004 (3)0.044 (3)0.001 (3)
O1AB0.037 (5)0.036 (4)0.038 (3)−0.001 (3)0.003 (3)−0.006 (3)
C1AB0.057 (5)0.073 (7)0.080 (6)−0.012 (5)0.027 (4)−0.040 (5)
C2AB0.063 (5)0.101 (11)0.099 (7)−0.021 (6)0.043 (5)−0.040 (7)

Geometric parameters (Å, °)

O1A—C3A1.4401 (19)C4B—C5B1.563 (2)
O1A—H110.85 (3)C5B—C6B1.531 (2)
O2A—C28A1.213 (2)C5B—C10B1.557 (2)
O3A—C28A1.319 (2)C5B—H5B0.9800
O3A—H310.95 (3)C6B—C7B1.532 (2)
C1A—C2A1.533 (2)C6B—H6C0.9700
C1A—C10A1.538 (2)C6B—H6D0.9700
C1A—H1A0.9700C7B—C8B1.541 (2)
C1A—H1B0.9700C7B—H7C0.9700
C2A—C3A1.511 (2)C7B—H7D0.9700
C2A—H2A0.9700C8B—C26B1.546 (2)
C2A—H2B0.9700C8B—C9B1.558 (2)
C3A—C4A1.535 (2)C8B—C14B1.594 (2)
C3A—H3A0.9800C9B—C11B1.540 (2)
C4A—C23A1.539 (2)C9B—C10B1.568 (2)
C4A—C24A1.539 (2)C9B—H9B0.9800
C4A—C5A1.5591 (19)C10B—C25B1.545 (2)
C5A—C6A1.525 (2)C11B—C12B1.503 (2)
C5A—C10A1.559 (2)C11B—H11C0.9700
C5A—H5A0.9800C11B—H11D0.9700
C6A—C7A1.527 (2)C12B—C13B1.331 (3)
C6A—H6A0.9700C12B—H12B0.9300
C6A—H6B0.9700C13B—C18B1.529 (2)
C7A—C8A1.541 (2)C13B—C14B1.531 (2)
C7A—H7A0.9700C14B—C27B1.549 (2)
C7A—H7B0.9700C14B—C15B1.553 (2)
C8A—C26A1.547 (2)C15B—C16B1.533 (2)
C8A—C9A1.555 (2)C15B—H15C0.9700
C8A—C14A1.588 (2)C15B—H15D0.9700
C9A—C11A1.542 (2)C16B—C17B1.523 (3)
C9A—C10A1.573 (2)C16B—H16C0.9700
C9A—H9A0.9800C16B—H16D0.9700
C10A—C25A1.539 (2)C17B—C28B1.532 (2)
C11A—C12A1.509 (2)C17B—C18B1.545 (2)
C11A—H11A0.9700C17B—C22B1.557 (2)
C11A—H11B0.9700C18B—C19B1.545 (2)
C12A—C13A1.324 (2)C18B—H18B0.9800
C12A—H12A0.9300C19B—C20B1.541 (2)
C13A—C18A1.524 (2)C19B—H19C0.9700
C13A—C14A1.537 (2)C19B—H19D0.9700
C14A—C15A1.544 (2)C20B—C30B1.526 (3)
C14A—C27A1.560 (2)C20B—C29B1.527 (3)
C15A—C16A1.524 (2)C20B—C21B1.538 (3)
C15A—H15A0.9700C21B—C22B1.528 (3)
C15A—H15B0.9700C21B—H21C0.9700
C16A—C17A1.534 (2)C21B—H21D0.9700
C16A—H16A0.9700C22B—H22C0.9700
C16A—H16B0.9700C22B—H22D0.9700
C17A—C28A1.525 (2)C23B—H23D0.9600
C17A—C18A1.545 (2)C23B—H23E0.9600
C17A—C22A1.557 (2)C23B—H23F0.9600
C18A—C19A1.545 (2)C24B—H24D0.9600
C18A—H18A0.9800C24B—H24E0.9600
C19A—C20A1.538 (2)C24B—H24F0.9600
C19A—H19A0.9700C25B—H25D0.9600
C19A—H19B0.9700C25B—H25E0.9600
C20A—C21A1.529 (2)C25B—H25F0.9600
C20A—C30A1.531 (2)C26B—H26D0.9600
C20A—C29A1.534 (2)C26B—H26E0.9600
C21A—C22A1.522 (2)C26B—H26F0.9600
C21A—H21A0.9700C27B—H27D0.9600
C21A—H21B0.9700C27B—H27E0.9600
C22A—H22A0.9700C27B—H27F0.9600
C22A—H22B0.9700C29B—H29D0.9600
C23A—H23A0.9600C29B—H29E0.9600
C23A—H23B0.9600C29B—H29F0.9600
C23A—H23C0.9600C30B—H30D0.9600
C24A—H24A0.9600C30B—H30E0.9600
C24A—H24B0.9600C30B—H30F0.9600
C24A—H24C0.9600O1BA—C1BA1.418 (4)
C25A—H25A0.9600O1BA—C1BB1.451 (10)
C25A—H25B0.9600O1BA—H1BO0.84 (3)
C25A—H25C0.9600C1BA—C2BA1.487 (6)
C26A—H26A0.9600C1BA—H1BA0.9700
C26A—H26B0.9600C1BA—H1BB0.9700
C26A—H26C0.9600C2BA—H2BA0.9600
C27A—H27A0.9600C2BA—H2BB0.9600
C27A—H27B0.9600C2BA—H2BC0.9600
C27A—H27C0.9600C1BB—C2BB1.522 (15)
C29A—H29A0.9600C1BB—H1BC0.9700
C29A—H29B0.9600C1BB—H1BD0.9700
C29A—H29C0.9600C2BB—H2BD0.9600
C30A—H30A0.9600C2BB—H2BE0.9600
C30A—H30B0.9600C2BB—H2BF0.9600
C30A—H30C0.9600O1AA—C1AA1.422 (7)
O1B—C3B1.4373 (19)O1AA—H1AO0.8200
O1B—H120.83 (3)C1AA—C2AA1.487 (7)
O2B—C28B1.218 (2)C1AA—H1AA0.9700
O3B—C28B1.317 (3)C1AA—H1AB0.9700
O3B—H320.96 (4)C2AA—H2AA0.9600
C1B—C2B1.530 (2)C2AA—H2AB0.9600
C1B—C10B1.538 (2)C2AA—H2AC0.9600
C1B—H1C0.9700O1AB—C1AB1.466 (13)
C1B—H1D0.9700O1AB—H2AO0.8200
C2B—C3B1.509 (2)C1AB—C2AB1.467 (15)
C2B—H2C0.9700C1AB—H1AC0.9700
C2B—H2D0.9700C1AB—H1AD0.9700
C3B—C4B1.551 (2)C2AB—H2AD0.9600
C3B—H3B0.9800C2AB—H2AE0.9600
C4B—C24B1.531 (2)C2AB—H2AF0.9600
C4B—C23B1.534 (2)
C3A—O1A—H11111 (2)C6B—C5B—C10B109.91 (13)
C28A—O3A—H31110 (2)C6B—C5B—C4B114.05 (13)
C2A—C1A—C10A113.64 (13)C10B—C5B—C4B117.90 (13)
C2A—C1A—H1A108.8C6B—C5B—H5B104.5
C10A—C1A—H1A108.8C10B—C5B—H5B104.5
C2A—C1A—H1B108.8C4B—C5B—H5B104.5
C10A—C1A—H1B108.8C5B—C6B—C7B110.55 (13)
H1A—C1A—H1B107.7C5B—C6B—H6C109.5
C3A—C2A—C1A110.93 (13)C7B—C6B—H6C109.5
C3A—C2A—H2A109.5C5B—C6B—H6D109.5
C1A—C2A—H2A109.5C7B—C6B—H6D109.5
C3A—C2A—H2B109.5H6C—C6B—H6D108.1
C1A—C2A—H2B109.5C6B—C7B—C8B114.57 (14)
H2A—C2A—H2B108.0C6B—C7B—H7C108.6
O1A—C3A—C2A106.81 (13)C8B—C7B—H7C108.6
O1A—C3A—C4A112.41 (14)C6B—C7B—H7D108.6
C2A—C3A—C4A113.71 (13)C8B—C7B—H7D108.6
O1A—C3A—H3A107.9H7C—C7B—H7D107.6
C2A—C3A—H3A107.9C7B—C8B—C26B108.41 (14)
C4A—C3A—H3A107.9C7B—C8B—C9B109.85 (13)
C3A—C4A—C23A108.20 (13)C26B—C8B—C9B110.60 (14)
C3A—C4A—C24A111.30 (14)C7B—C8B—C14B110.08 (14)
C23A—C4A—C24A107.86 (14)C26B—C8B—C14B110.05 (13)
C3A—C4A—C5A106.67 (13)C9B—C8B—C14B107.85 (13)
C23A—C4A—C5A107.83 (13)C11B—C9B—C8B110.07 (13)
C24A—C4A—C5A114.78 (13)C11B—C9B—C10B113.45 (13)
C6A—C5A—C10A109.99 (12)C8B—C9B—C10B116.98 (13)
C6A—C5A—C4A114.28 (13)C11B—C9B—H9B105.0
C10A—C5A—C4A117.30 (13)C8B—C9B—H9B105.0
C6A—C5A—H5A104.6C10B—C9B—H9B105.0
C10A—C5A—H5A104.6C1B—C10B—C25B107.16 (13)
C4A—C5A—H5A104.6C1B—C10B—C5B108.24 (12)
C5A—C6A—C7A110.16 (13)C25B—C10B—C5B113.20 (13)
C5A—C6A—H6A109.6C1B—C10B—C9B107.99 (12)
C7A—C6A—H6A109.6C25B—C10B—C9B113.89 (13)
C5A—C6A—H6B109.6C5B—C10B—C9B106.15 (13)
C7A—C6A—H6B109.6C12B—C11B—C9B114.41 (14)
H6A—C6A—H6B108.1C12B—C11B—H11C108.7
C6A—C7A—C8A113.76 (13)C9B—C11B—H11C108.7
C6A—C7A—H7A108.8C12B—C11B—H11D108.7
C8A—C7A—H7A108.8C9B—C11B—H11D108.7
C6A—C7A—H7B108.8H11C—C11B—H11D107.6
C8A—C7A—H7B108.8C13B—C12B—C11B125.63 (16)
H7A—C7A—H7B107.7C13B—C12B—H12B117.2
C7A—C8A—C26A107.68 (13)C11B—C12B—H12B117.2
C7A—C8A—C9A110.93 (12)C12B—C13B—C18B118.76 (16)
C26A—C8A—C9A111.13 (13)C12B—C13B—C14B120.79 (15)
C7A—C8A—C14A109.49 (12)C18B—C13B—C14B120.37 (15)
C26A—C8A—C14A110.41 (12)C13B—C14B—C27B106.83 (13)
C9A—C8A—C14A107.20 (13)C13B—C14B—C15B112.09 (13)
C11A—C9A—C8A109.91 (12)C27B—C14B—C15B107.32 (14)
C11A—C9A—C10A113.88 (13)C13B—C14B—C8B108.83 (14)
C8A—C9A—C10A117.33 (12)C27B—C14B—C8B112.92 (13)
C11A—C9A—H9A104.8C15B—C14B—C8B108.89 (13)
C8A—C9A—H9A104.8C16B—C15B—C14B115.71 (14)
C10A—C9A—H9A104.8C16B—C15B—H15C108.4
C1A—C10A—C25A108.01 (13)C14B—C15B—H15C108.4
C1A—C10A—C5A108.34 (12)C16B—C15B—H15D108.4
C25A—C10A—C5A113.54 (13)C14B—C15B—H15D108.4
C1A—C10A—C9A107.50 (12)H15C—C15B—H15D107.4
C25A—C10A—C9A113.78 (12)C17B—C16B—C15B112.61 (15)
C5A—C10A—C9A105.41 (12)C17B—C16B—H16C109.1
C12A—C11A—C9A113.60 (13)C15B—C16B—H16C109.1
C12A—C11A—H11A108.8C17B—C16B—H16D109.1
C9A—C11A—H11A108.8C15B—C16B—H16D109.1
C12A—C11A—H11B108.8H16C—C16B—H16D107.8
C9A—C11A—H11B108.8C16B—C17B—C28B110.88 (14)
H11A—C11A—H11B107.7C16B—C17B—C18B109.61 (14)
C13A—C12A—C11A126.24 (15)C28B—C17B—C18B110.91 (15)
C13A—C12A—H12A116.9C16B—C17B—C22B111.36 (15)
C11A—C12A—H12A116.9C28B—C17B—C22B103.61 (13)
C12A—C13A—C18A119.28 (14)C18B—C17B—C22B110.35 (14)
C12A—C13A—C14A120.18 (14)C13B—C18B—C19B113.21 (13)
C18A—C13A—C14A120.44 (13)C13B—C18B—C17B110.87 (14)
C13A—C14A—C15A112.98 (12)C19B—C18B—C17B111.48 (14)
C13A—C14A—C27A106.66 (13)C13B—C18B—H18B107.0
C15A—C14A—C27A106.56 (13)C19B—C18B—H18B107.0
C13A—C14A—C8A107.86 (12)C17B—C18B—H18B107.0
C15A—C14A—C8A109.88 (13)C20B—C19B—C18B114.44 (14)
C27A—C14A—C8A112.96 (12)C20B—C19B—H19C108.7
C16A—C15A—C14A114.39 (13)C18B—C19B—H19C108.7
C16A—C15A—H15A108.7C20B—C19B—H19D108.7
C14A—C15A—H15A108.7C18B—C19B—H19D108.7
C16A—C15A—H15B108.7H19C—C19B—H19D107.6
C14A—C15A—H15B108.7C30B—C20B—C29B109.03 (16)
H15A—C15A—H15B107.6C30B—C20B—C21B110.73 (16)
C15A—C16A—C17A111.58 (13)C29B—C20B—C21B108.66 (17)
C15A—C16A—H16A109.3C30B—C20B—C19B111.38 (17)
C17A—C16A—H16A109.3C29B—C20B—C19B108.71 (15)
C15A—C16A—H16B109.3C21B—C20B—C19B108.27 (15)
C17A—C16A—H16B109.3C22B—C21B—C20B112.96 (17)
H16A—C16A—H16B108.0C22B—C21B—H21C109.0
C28A—C17A—C16A111.69 (13)C20B—C21B—H21C109.0
C28A—C17A—C18A109.38 (13)C22B—C21B—H21D109.0
C16A—C17A—C18A109.48 (12)C20B—C21B—H21D109.0
C28A—C17A—C22A104.57 (12)H21C—C21B—H21D107.8
C16A—C17A—C22A110.46 (13)C21B—C22B—C17B112.89 (15)
C18A—C17A—C22A111.20 (13)C21B—C22B—H22C109.0
C13A—C18A—C19A111.57 (12)C17B—C22B—H22C109.0
C13A—C18A—C17A112.13 (12)C21B—C22B—H22D109.0
C19A—C18A—C17A112.01 (13)C17B—C22B—H22D109.0
C13A—C18A—H18A106.9H22C—C22B—H22D107.8
C19A—C18A—H18A106.9C4B—C23B—H23D109.5
C17A—C18A—H18A106.9C4B—C23B—H23E109.5
C20A—C19A—C18A113.95 (13)H23D—C23B—H23E109.5
C20A—C19A—H19A108.8C4B—C23B—H23F109.5
C18A—C19A—H19A108.8H23D—C23B—H23F109.5
C20A—C19A—H19B108.8H23E—C23B—H23F109.5
C18A—C19A—H19B108.8C4B—C24B—H24D109.5
H19A—C19A—H19B107.7C4B—C24B—H24E109.5
C21A—C20A—C30A110.37 (14)H24D—C24B—H24E109.5
C21A—C20A—C29A108.66 (14)C4B—C24B—H24F109.5
C30A—C20A—C29A108.63 (15)H24D—C24B—H24F109.5
C21A—C20A—C19A108.14 (13)H24E—C24B—H24F109.5
C30A—C20A—C19A111.38 (13)C10B—C25B—H25D109.5
C29A—C20A—C19A109.62 (13)C10B—C25B—H25E109.5
C22A—C21A—C20A112.43 (13)H25D—C25B—H25E109.5
C22A—C21A—H21A109.1C10B—C25B—H25F109.5
C20A—C21A—H21A109.1H25D—C25B—H25F109.5
C22A—C21A—H21B109.1H25E—C25B—H25F109.5
C20A—C21A—H21B109.1C8B—C26B—H26D109.5
H21A—C21A—H21B107.8C8B—C26B—H26E109.5
C21A—C22A—C17A112.69 (13)H26D—C26B—H26E109.5
C21A—C22A—H22A109.1C8B—C26B—H26F109.5
C17A—C22A—H22A109.1H26D—C26B—H26F109.5
C21A—C22A—H22B109.1H26E—C26B—H26F109.5
C17A—C22A—H22B109.1C14B—C27B—H27D109.5
H22A—C22A—H22B107.8C14B—C27B—H27E109.5
C4A—C23A—H23A109.5H27D—C27B—H27E109.5
C4A—C23A—H23B109.5C14B—C27B—H27F109.5
H23A—C23A—H23B109.5H27D—C27B—H27F109.5
C4A—C23A—H23C109.5H27E—C27B—H27F109.5
H23A—C23A—H23C109.5O2B—C28B—O3B122.88 (18)
H23B—C23A—H23C109.5O2B—C28B—C17B123.32 (18)
C4A—C24A—H24A109.5O3B—C28B—C17B113.62 (16)
C4A—C24A—H24B109.5C20B—C29B—H29D109.5
H24A—C24A—H24B109.5C20B—C29B—H29E109.5
C4A—C24A—H24C109.5H29D—C29B—H29E109.5
H24A—C24A—H24C109.5C20B—C29B—H29F109.5
H24B—C24A—H24C109.5H29D—C29B—H29F109.5
C10A—C25A—H25A109.5H29E—C29B—H29F109.5
C10A—C25A—H25B109.5C20B—C30B—H30D109.5
H25A—C25A—H25B109.5C20B—C30B—H30E109.5
C10A—C25A—H25C109.5H30D—C30B—H30E109.5
H25A—C25A—H25C109.5C20B—C30B—H30F109.5
H25B—C25A—H25C109.5H30D—C30B—H30F109.5
C8A—C26A—H26A109.5H30E—C30B—H30F109.5
C8A—C26A—H26B109.5C1BA—O1BA—C1BB30.4 (5)
H26A—C26A—H26B109.5C1BA—O1BA—H1BO114 (2)
C8A—C26A—H26C109.5C1BB—O1BA—H1BO107 (2)
H26A—C26A—H26C109.5O1BA—C1BA—C2BA111.7 (4)
H26B—C26A—H26C109.5O1BA—C1BA—H1BA109.3
C14A—C27A—H27A109.5C2BA—C1BA—H1BA109.3
C14A—C27A—H27B109.5O1BA—C1BA—H1BB109.3
H27A—C27A—H27B109.5C2BA—C1BA—H1BB109.3
C14A—C27A—H27C109.5H1BA—C1BA—H1BB107.9
H27A—C27A—H27C109.5C1BA—C2BA—H2BA109.5
H27B—C27A—H27C109.5C1BA—C2BA—H2BB109.5
O2A—C28A—O3A121.74 (16)H2BA—C2BA—H2BB109.5
O2A—C28A—C17A124.65 (15)C1BA—C2BA—H2BC109.5
O3A—C28A—C17A113.51 (14)H2BA—C2BA—H2BC109.5
C20A—C29A—H29A109.5H2BB—C2BA—H2BC109.5
C20A—C29A—H29B109.5O1BA—C1BB—C2BB106.6 (11)
H29A—C29A—H29B109.5O1BA—C1BB—H1BC110.4
C20A—C29A—H29C109.5C2BB—C1BB—H1BC110.4
H29A—C29A—H29C109.5O1BA—C1BB—H1BD110.4
H29B—C29A—H29C109.5C2BB—C1BB—H1BD110.4
C20A—C30A—H30A109.5H1BC—C1BB—H1BD108.6
C20A—C30A—H30B109.5C1BB—C2BB—H2BD109.5
H30A—C30A—H30B109.5C1BB—C2BB—H2BE109.5
C20A—C30A—H30C109.5H2BD—C2BB—H2BE109.5
H30A—C30A—H30C109.5C1BB—C2BB—H2BF109.5
H30B—C30A—H30C109.5H2BD—C2BB—H2BF109.5
C3B—O1B—H12112.0 (17)H2BE—C2BB—H2BF109.5
C28B—O3B—H32107 (3)O1AA—C1AA—C2AA111.4 (4)
C2B—C1B—C10B113.09 (13)O1AA—C1AA—H1AA109.3
C2B—C1B—H1C109.0C2AA—C1AA—H1AA109.3
C10B—C1B—H1C109.0O1AA—C1AA—H1AB109.3
C2B—C1B—H1D109.0C2AA—C1AA—H1AB109.3
C10B—C1B—H1D109.0H1AA—C1AA—H1AB108.0
H1C—C1B—H1D107.8C1AA—C2AA—H2AA109.5
C3B—C2B—C1B111.29 (13)C1AA—C2AA—H2AB109.5
C3B—C2B—H2C109.4H2AA—C2AA—H2AB109.5
C1B—C2B—H2C109.4C1AA—C2AA—H2AC109.5
C3B—C2B—H2D109.4H2AA—C2AA—H2AC109.5
C1B—C2B—H2D109.4H2AB—C2AA—H2AC109.5
H2C—C2B—H2D108.0C1AB—O1AB—H2AO109.5
O1B—C3B—C2B107.66 (13)O1AB—C1AB—C2AB109.2 (9)
O1B—C3B—C4B111.10 (13)O1AB—C1AB—H1AC109.9
C2B—C3B—C4B113.90 (13)C2AB—C1AB—H1AC109.9
O1B—C3B—H3B108.0O1AB—C1AB—H1AD109.9
C2B—C3B—H3B108.0C2AB—C1AB—H1AD109.9
C4B—C3B—H3B108.0H1AC—C1AB—H1AD108.3
C24B—C4B—C23B107.98 (15)C1AB—C2AB—H2AD109.5
C24B—C4B—C3B111.04 (14)C1AB—C2AB—H2AE109.5
C23B—C4B—C3B107.20 (13)H2AD—C2AB—H2AE109.5
C24B—C4B—C5B114.26 (13)C1AB—C2AB—H2AF109.5
C23B—C4B—C5B108.69 (13)H2AD—C2AB—H2AF109.5
C3B—C4B—C5B107.43 (13)H2AE—C2AB—H2AF109.5
C10A—C1A—C2A—C3A−55.77 (18)C1B—C2B—C3B—O1B−178.54 (12)
C1A—C2A—C3A—O1A−176.66 (13)C1B—C2B—C3B—C4B57.79 (18)
C1A—C2A—C3A—C4A58.75 (18)O1B—C3B—C4B—C24B−47.93 (18)
O1A—C3A—C4A—C23A67.63 (17)C2B—C3B—C4B—C24B73.85 (17)
C2A—C3A—C4A—C23A−170.86 (13)O1B—C3B—C4B—C23B69.80 (17)
O1A—C3A—C4A—C24A−50.70 (17)C2B—C3B—C4B—C23B−168.41 (14)
C2A—C3A—C4A—C24A70.81 (17)O1B—C3B—C4B—C5B−173.53 (13)
O1A—C3A—C4A—C5A−176.59 (12)C2B—C3B—C4B—C5B−51.75 (17)
C2A—C3A—C4A—C5A−55.08 (17)C24B—C4B—C5B—C6B57.20 (19)
C3A—C4A—C5A—C6A−176.53 (13)C23B—C4B—C5B—C6B−63.45 (18)
C23A—C4A—C5A—C6A−60.50 (17)C3B—C4B—C5B—C6B−179.14 (14)
C24A—C4A—C5A—C6A59.71 (19)C24B—C4B—C5B—C10B−73.97 (18)
C3A—C4A—C5A—C10A52.57 (17)C23B—C4B—C5B—C10B165.37 (13)
C23A—C4A—C5A—C10A168.59 (14)C3B—C4B—C5B—C10B49.69 (17)
C24A—C4A—C5A—C10A−71.19 (19)C10B—C5B—C6B—C7B−63.43 (17)
C10A—C5A—C6A—C7A−65.99 (16)C4B—C5B—C6B—C7B161.60 (14)
C4A—C5A—C6A—C7A159.62 (12)C5B—C6B—C7B—C8B55.46 (19)
C5A—C6A—C7A—C8A56.35 (17)C6B—C7B—C8B—C26B75.53 (17)
C6A—C7A—C8A—C26A77.31 (16)C6B—C7B—C8B—C9B−45.43 (18)
C6A—C7A—C8A—C9A−44.50 (18)C6B—C7B—C8B—C14B−164.04 (13)
C6A—C7A—C8A—C14A−162.62 (13)C7B—C8B—C9B—C11B178.20 (14)
C7A—C8A—C9A—C11A176.98 (13)C26B—C8B—C9B—C11B58.57 (17)
C26A—C8A—C9A—C11A57.21 (16)C14B—C8B—C9B—C11B−61.82 (17)
C14A—C8A—C9A—C11A−63.52 (15)C7B—C8B—C9B—C10B46.79 (18)
C7A—C8A—C9A—C10A44.78 (17)C26B—C8B—C9B—C10B−72.84 (17)
C26A—C8A—C9A—C10A−74.99 (16)C14B—C8B—C9B—C10B166.77 (13)
C14A—C8A—C9A—C10A164.28 (12)C2B—C1B—C10B—C25B−70.40 (17)
C2A—C1A—C10A—C25A−73.17 (16)C2B—C1B—C10B—C5B52.00 (17)
C2A—C1A—C10A—C5A50.21 (17)C2B—C1B—C10B—C9B166.52 (13)
C2A—C1A—C10A—C9A163.67 (13)C6B—C5B—C10B—C1B176.57 (13)
C6A—C5A—C10A—C1A176.33 (12)C4B—C5B—C10B—C1B−50.41 (17)
C4A—C5A—C10A—C1A−50.82 (17)C6B—C5B—C10B—C25B−64.80 (17)
C6A—C5A—C10A—C25A−63.69 (16)C4B—C5B—C10B—C25B68.22 (17)
C4A—C5A—C10A—C25A69.16 (17)C6B—C5B—C10B—C9B60.85 (15)
C6A—C5A—C10A—C9A61.51 (15)C4B—C5B—C10B—C9B−166.13 (12)
C4A—C5A—C10A—C9A−165.64 (13)C11B—C9B—C10B—C1B59.73 (17)
C11A—C9A—C10A—C1A61.57 (17)C8B—C9B—C10B—C1B−170.44 (13)
C8A—C9A—C10A—C1A−168.05 (12)C11B—C9B—C10B—C25B−59.15 (18)
C11A—C9A—C10A—C25A−57.98 (18)C8B—C9B—C10B—C25B70.68 (18)
C8A—C9A—C10A—C25A72.40 (17)C11B—C9B—C10B—C5B175.62 (13)
C11A—C9A—C10A—C5A176.98 (13)C8B—C9B—C10B—C5B−54.54 (16)
C8A—C9A—C10A—C5A−52.64 (16)C8B—C9B—C11B—C12B35.28 (19)
C8A—C9A—C11A—C12A34.48 (19)C10B—C9B—C11B—C12B168.52 (13)
C10A—C9A—C11A—C12A168.45 (13)C9B—C11B—C12B—C13B−5.0 (3)
C9A—C11A—C12A—C13A−3.4 (2)C11B—C12B—C13B—C18B179.16 (15)
C11A—C12A—C13A—C18A178.90 (15)C11B—C12B—C13B—C14B2.5 (3)
C11A—C12A—C13A—C14A2.5 (3)C12B—C13B—C14B—C27B92.89 (19)
C12A—C13A—C14A—C15A−153.16 (15)C18B—C13B—C14B—C27B−83.77 (17)
C18A—C13A—C14A—C15A30.47 (19)C12B—C13B—C14B—C15B−149.83 (16)
C12A—C13A—C14A—C27A90.09 (17)C18B—C13B—C14B—C15B33.5 (2)
C18A—C13A—C14A—C27A−86.28 (16)C12B—C13B—C14B—C8B−29.3 (2)
C12A—C13A—C14A—C8A−31.5 (2)C18B—C13B—C14B—C8B154.02 (13)
C18A—C13A—C14A—C8A152.11 (13)C7B—C8B—C14B—C13B177.90 (13)
C7A—C8A—C14A—C13A−178.58 (12)C26B—C8B—C14B—C13B−62.66 (17)
C26A—C8A—C14A—C13A−60.20 (17)C9B—C8B—C14B—C13B58.07 (16)
C9A—C8A—C14A—C13A61.00 (15)C7B—C8B—C14B—C27B59.45 (18)
C7A—C8A—C14A—C15A−55.04 (16)C26B—C8B—C14B—C27B178.88 (15)
C26A—C8A—C14A—C15A63.35 (16)C9B—C8B—C14B—C27B−60.38 (18)
C9A—C8A—C14A—C15A−175.46 (12)C7B—C8B—C14B—C15B−59.64 (17)
C7A—C8A—C14A—C27A63.80 (17)C26B—C8B—C14B—C15B59.79 (18)
C26A—C8A—C14A—C27A−177.82 (14)C9B—C8B—C14B—C15B−179.47 (13)
C9A—C8A—C14A—C27A−56.62 (16)C13B—C14B—C15B—C16B−35.3 (2)
C13A—C14A—C15A—C16A−37.70 (18)C27B—C14B—C15B—C16B81.70 (18)
C27A—C14A—C15A—C16A79.11 (16)C8B—C14B—C15B—C16B−155.77 (14)
C8A—C14A—C15A—C16A−158.19 (12)C14B—C15B—C16B—C17B50.7 (2)
C14A—C15A—C16A—C17A55.35 (18)C15B—C16B—C17B—C28B62.82 (18)
C15A—C16A—C17A—C28A59.27 (18)C15B—C16B—C17B—C18B−59.97 (18)
C15A—C16A—C17A—C18A−62.03 (17)C15B—C16B—C17B—C22B177.62 (13)
C15A—C16A—C17A—C22A175.20 (13)C12B—C13B—C18B—C19B−94.9 (2)
C12A—C13A—C18A—C19A−88.40 (18)C14B—C13B—C18B—C19B81.82 (19)
C14A—C13A—C18A—C19A88.01 (17)C12B—C13B—C18B—C17B138.96 (17)
C12A—C13A—C18A—C17A145.03 (15)C14B—C13B—C18B—C17B−44.3 (2)
C14A—C13A—C18A—C17A−38.57 (19)C16B—C17B—C18B—C13B55.20 (18)
C28A—C17A—C18A—C13A−70.36 (15)C28B—C17B—C18B—C13B−67.57 (19)
C16A—C17A—C18A—C13A52.32 (16)C22B—C17B—C18B—C13B178.20 (15)
C22A—C17A—C18A—C13A174.65 (12)C16B—C17B—C18B—C19B−71.90 (18)
C28A—C17A—C18A—C19A163.31 (12)C28B—C17B—C18B—C19B165.33 (15)
C16A—C17A—C18A—C19A−74.01 (15)C22B—C17B—C18B—C19B51.1 (2)
C22A—C17A—C18A—C19A48.32 (16)C13B—C18B—C19B—C20B179.45 (16)
C13A—C18A—C19A—C20A−179.70 (13)C17B—C18B—C19B—C20B−54.7 (2)
C17A—C18A—C19A—C20A−53.06 (17)C18B—C19B—C20B—C30B−67.1 (2)
C18A—C19A—C20A—C21A56.21 (17)C18B—C19B—C20B—C29B172.74 (17)
C18A—C19A—C20A—C30A−65.23 (19)C18B—C19B—C20B—C21B54.9 (2)
C18A—C19A—C20A—C29A174.52 (15)C30B—C20B—C21B—C22B67.6 (2)
C30A—C20A—C21A—C22A64.42 (17)C29B—C20B—C21B—C22B−172.67 (17)
C29A—C20A—C21A—C22A−176.56 (14)C19B—C20B—C21B—C22B−54.8 (2)
C19A—C20A—C21A—C22A−57.64 (17)C20B—C21B—C22B—C17B55.9 (2)
C20A—C21A—C22A—C17A56.85 (18)C16B—C17B—C22B—C21B69.4 (2)
C28A—C17A—C22A—C21A−168.81 (14)C28B—C17B—C22B—C21B−171.41 (17)
C16A—C17A—C22A—C21A70.90 (17)C18B—C17B—C22B—C21B−52.6 (2)
C18A—C17A—C22A—C21A−50.87 (18)C16B—C17B—C28B—O2B23.8 (2)
C16A—C17A—C28A—O2A−148.96 (15)C18B—C17B—C28B—O2B145.84 (16)
C18A—C17A—C28A—O2A−27.6 (2)C22B—C17B—C28B—O2B−95.76 (19)
C22A—C17A—C28A—O2A91.56 (18)C16B—C17B—C28B—O3B−160.88 (15)
C16A—C17A—C28A—O3A34.65 (19)C18B—C17B—C28B—O3B−38.9 (2)
C18A—C17A—C28A—O3A156.01 (13)C22B—C17B—C28B—O3B79.55 (19)
C22A—C17A—C28A—O3A−84.82 (16)C1BB—O1BA—C1BA—C2BA−17.4 (10)
C10B—C1B—C2B—C3B−57.70 (18)C1BA—O1BA—C1BB—C2BB−4.0 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1BA—H1BO···O1B0.84 (3)1.81 (3)2.652 (2)177 (3)
O1AA—H1AO···O1A0.821.982.794 (7)170
O1A—H11···O2B0.85 (3)2.02 (3)2.8503 (18)168 (3)
O1B—H12···O2Ai0.83 (3)1.89 (3)2.7204 (18)174 (3)
O3A—H31···O1BAii0.95 (3)1.61 (3)2.552 (2)177 (3)
O3B—H32···O1AA0.96 (4)1.64 (4)2.575 (7)163 (4)
C15A—H15A···O3A0.972.583.1222 (19)116
C15B—H15C···O2B0.972.603.152 (2)116
C23A—H23A···O2B0.962.543.375 (2)145

Symmetry codes: (i) x, y, z−1; (ii) x, y+1, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5364).

References

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