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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Pages o795-o796
https://doi.org/10.1107/S1600536813011008

Lup-20(29)-en-28-ol-3-one (betulone)

Stanisław Boryczka,a* Ewa Michalik,b Joachim Kusz,c Maria Nowakd and Elwira Chrobaka

aDepartment of Organic Chemistry, Medical University of Silesia, Sosnowiec 41-200, Poland, bDepartment of Organic Chemistry, Wrocław Medical University, Wrocław 50-556, Poland, cDepartment of Physics of Crystals, Institute of Physics, University of Silesia, Katowice 40-007, Poland, and dDepartment of Solid State Physics, Institute of Physics, University of Silesia, Katowice 40-007, Poland
*Correspondence e-mail: boryczka@sum.edu.pl

(Received 28 March 2013; accepted 23 April 2013; online 27 April 2013)

The asymmetric unit of the title compound, C30H48O2, contains two independent mol­ecules, the main difference between them being that the isopropenyl group is rotated by approximately 180°. In each mol­ecule, the fused six-membered rings have chair–chair–chair–chair conformations and the cyclo­pentane ring adopts an envelope conformation with the C atom bearing the hy­droxy­methyl group as the flap. All ring junctions are trans-fused. With the exception of one of the methyl groups adjacent to the C=O group, all the methyl groups are in axial positions. The isopropenyl group is equatorial and the hy­droxy­methyl group is in an axial orientation. In the crystal, weak C—H⋯O inter­actions link the mol­ecules into chains along [010]. Weak intra­molecular C—H⋯O hydrogen bonds are also observed but the hy­droxy groups are not involved in hydrogen bonds.

Related literature

For the synthesis of betulone, see: Hase et al. (1981[Hase, T. A., Suokas, E. & Weckman, A. (1981). Synth. Commun. 11, 489-492.]). For the isolation of betulone from plants, see: Cole et al. (1991[Cole, B. J. W., Bentley, M. D. & Hua, Y. (1991). Hölzforschung, 45, 265-268.]); Reyes et al. (2006[Reyes, C. P., Núnez, M. J., Jiménez, I. A., Busserolles, J., Alcaraz, M. J. & Bazzocchi, I. L. (2006). Bioorg. Med. Chem. 14, 1573-1579.]); Diouf et al. (2009[Diouf, P. N., Stevanovic, T. & Boutin, Y. (2009). Ind. Crops Prod. 30, 297-303.]); Liu et al. (2010[Liu, Z., Jiang, W., Deng, Z.-W. & Lin, W.-H. (2010). J. Chin. Pharm. Sci. 19, 387-392.]); Kim et al. (2002[Kim, D. K., Nam, I. Y., Kim, J. W., Shin, T. Y. & Lim, J. P. (2002). Arch. Pharm. Res. 25, 617-620.]); Garcez et al. (2003[Garcez, F. R., Garcez, W. S., Miguel, D. L. S., Serea, A. A. T. & Prado, F. C. (2003). J. Braz. Chem. Soc. 14, 461-465.]); Fuchino et al. (1996[Fuchino, H., Konishi, S., Satoh, T., Yagi, A., Saitsu, K., Tatsumi, T. & Tanaka, N. (1996). Chem. Pharm. Bull. 44, 1033-1038.]). For the biological activity of betulone, see: Alakurtti et al. (2010[Alakurtti, S., Bergstrom, P., Sacerdoti-Sierra, N., Jaffe, C. L. & Yli-Kauhaluoma, J. (2010). J. Antibiot. 63, 123-126.]); Hata et al. (2002[Hata, K., Hori, K. & Takahashi, S. (2002). J. Nat. Prod. 65, 645-648.]); Reyes et al. (2006[Reyes, C. P., Núnez, M. J., Jiménez, I. A., Busserolles, J., Alcaraz, M. J. & Bazzocchi, I. L. (2006). Bioorg. Med. Chem. 14, 1573-1579.]). For related structures, see: Mohamed et al. (2006[Mohamed, I. E., Choudhary, M. I., Ali, S., Anjum, S. & Atta-ur-Rahman, (2006). Acta Cryst. E62, o1352-o1354.]); Ding et al. (2009[Ding, W.-M., Jing, L.-J., Yu, T., Wang, Y. & Yan, X.-F. (2009). Acta Cryst. E65, o1982.]); Drebushchak et al. (2010[Drebushchak, T. N., Mikhailenko, M. A., Brezgunova, M. E., Shakhtshneider, T. P. & Kuznetsova, S. A. (2010). J. Struct. Chem. 51, 798-801.]); Boryczka et al. (2011[Boryczka, S., Michalik, E., Jastrzębska, M., Kusz, J., Zubko, M. & Bębenek, E. (2011). J. Chem. Crystallogr. 42, 345-351.], 2012a[Boryczka, S., Bębenek, E., Jastrzębska, M., Kusz, J. & Zubko, M. (2012a). Z. Kristallogr. 227, 379-384.],b[Boryczka, S., Jastrzębska, M., Bębenek, E., Kusz, J., Zubko, M., Kadela, M. & Michalik, E. (2012b). J. Pharm. Sci. 101, 4458-4471.]).

[Scheme 1]

Experimental

Crystal data

  • C30H48O2

  • Mr = 440.71

  • Orthorhombic, P 21 21 21

  • a = 9.4447 (3) Å

  • b = 19.1818 (6) Å

  • c = 28.1141 (7) Å

  • V = 5093.3 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.60 × 0.56 × 0.20 mm
Data collection

  • Oxford Diffraction diffractometer with a Sapphire3 detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]) Tmin = 0.960, Tmax = 0.986

  • 61473 measured reflections

  • 5036 independent reflections

  • 4401 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.141

  • S = 1.03

  • 5036 reflections

  • 609 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.50 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13A—H13A⋯O2A 1.04 (4) 2.52 (3) 3.186 (4) 122 (2)
C13B—H13B⋯O2B 1.02 (3) 2.47 (3) 3.165 (4) 125 (2)
C19A—H19A⋯O2A 0.95 (4) 2.45 (4) 3.006 (5) 118 (3)
C22B—H22C⋯O1Bi 1.05 (4) 2.56 (4) 3.567 (4) 160 (3)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813011008/lh5603sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813011008/lh5603Isup2.hkl

checkCIF report


Comment top

Betulone (lup-20 (29)-en-28-ol-3-one) also known as betulonic alcohol, is a pentacyclic triterpene of the lupane type which was first isolated as a natural product from Betula lenta in 1991 (Cole et al., 1991). Betulone can be also isolated from various plants for example Maytenus cuzcoina and Maytenus chiapensis (Reyes et al., 2006), Betula alleghaniens (Diouf et al., 2009), Excoecaria agallocha (Liu et al., 2010), Ilex macropoda (Kim et al., 2002) and Terminalia glabrescens (Garcez et al., 2003). The continually growing interest in betulone and its derivatives results from their wide spectrum of biological activities such as anti-inflammatory (Reyes et al., 2006), anti-leishmanial (Alakurtti et al., 2010) and anticancer (Hata et al., 2002).

The structure of betulone is based on the 30-carbon skeleton comprising of four 6-membered rings and one cyclopentane ring. It has three available sites for simple chemical modification, namely: keto group at C3, primary hydroxy group at C28 and isopropenyl side chain at C19. These groups and their positions, mutual distances and orientation with respect to the rings can influence hydrogen bonding and the interactions of betulone with other active sites of surrounding species.

Betulone is also known as a derivative of betulin, which is one of the most plentiful triterpenes comprising up to 30% dry weight of the outer bark of the white birch. In comparison to betulin, the content of betulone in the outer bark of different tree species is very low, e.g. about of 0.03% in Betula platyphylla (Fuchino et al., 1996) and for this reason the isolation from raw plant material is poorly profitable. A more effective method to obtain betulone with high yield is to carry out synthesis from betulin (Hase et al., 1981). The crystal structure of betulone has not been reported until now. However, the crystal structures of betulonic acid-DMSO and betulonic acid-DMF solvates (Boryczka et al., 2012b) were earlier described. In addition, the structure of betulinic acid-DMSO solvate (Boryczka et al., 2012a) has also been reported. In the present work, we describe the crystal structure of betulone in order to gain a better understanding of the structure-activity relationships of this important molecule. Betulonic alcohol was obtained by oxidation of naturally occurring betulin in a one-step reaction utilizing Jones-oxidation (CrO3/H2SO4 in acetone-water solution) as the side product.

The asymmetric unit contains two independent molecules (IA and IB). A schematic drawing of the ring and atom labeling is shown in Fig. 1 and the asymmetric unit is shown in Fig. 2. All bond lengths and the angles show normal values. The cyclopentane ring adopts an envelope conformation and the cyclohexane rings are all in chair conformations. All the ring junctions in the lupane nucleus are trans-fused. A similar ring conformation is also observed in 20 (29)-lupene-3β,28β-diacetate (Mohamed et al., 2006), 3,28-diacetoxy-29-bromo-betulin (Ding et al., 2009) and also in betulin-ethanol (Drebushchak et al., 2010), betulin-DMSO (Boryczka et al., 2011), betulinic acid-DMSO (Boryczka et al., 2012a) solvates. However, the conformation of ring A in betulone differs significantly from that observed earlier for betulonic acid-DMSO and DMF solvate, where ring A adopts a boat conformation. The molecules are packed along the a axis, in a zigzag fashion, parallel to the bc plane (Fig. 3). The cyclopentane ring is in an envelope conformation with the C17 atom being displaced from C18/C19/C21/C22 plane by 0.656 (4) Å (IA) and 0.674 (4) Å (IB). The C17—C18—C19—C21 and C19—C21—C22—C17 torsion angles are 27.0 (4)°, -25.4 (4)° (for IA) and 27.5 (3)°, -26.1 (3)° (for IB) respectively. The methyl groups C24, C25, C26, C27 occupy axial positions, but the methyl group C23 and isopropenyl group at C19 are equatorial. Fig. 4 shows the different orientations of the isopropenyl groups in the two independent molecules, (IA and IB). The value of the C21—C19—C20—C29 torsion angle describes the orientation of the isopropenyl group is equal to 92.3 (4)° (IA) and -98.8 (4)° (IB). The value of the C21—C19—C20—C29 torsion angle for betulin-DMSO and betulin-ethanol solvates are -96.8 (5)° and 88.6 (5)°, respectively. The hydroxymethyl group is attached to atom C17 of ring D in an axial orientation. No classical hydrogen bonding involving the hydroxy groups is observed. In the crystal, weak intermolecular C—H···O interactions link molecules into chains along [010]. Weak intramolecular C—H···O hydrogen bonds are also observed.

Related literature top

For the synthesis of betulone, see: Hase et al. (1981). For the isolation of betulone from plants, see: Cole et al. (1991); Reyes et al. (2006); Diouf et al. (2009); Liu et al. (2010); Kim et al. (2002); Garcez et al. (2003); Fuchino et al. (1996). For the biological activity of betulone, see: Alakurtti et al. (2010); Hata et al. (2002); Reyes et al. (2006). For related structures, see: Mohamed et al. (2006); Ding et al. (2009); Drebushchak et al. (2010); Boryczka et al. (2011, 2012a,b).

Experimental top

Betulonic alcohol was obtained by oxidation of naturally occurring betulin in one-step reaction utilizing Jones-oxidation (CrO3/H2SO4 in acetone-water solution) as the side product. The crude material was subjected to column chromatography on silica gel and eluted with CH2Cl2/C2H5OH (40:1, v/v). Betulonic alcohol [m.p. 367-369K, lit. m.p. 367-369K, Hata et al., 2002), Rf=0.68 (silica gel, CH2Cl2/C2H5OH, 40:1, v/v)] was crystallized from methanol, yielding colorless single crystals suitable for the X-ray analysis. 1H NMR (500 MHz, CDCl3) and EI MS data were identical with reported data (Hata et al., 2002).

Refinement top

The aromatic hydrogen atoms were treated as riding on their parent carbon atoms with d(C—H) = 0.95 Å and assigned isotropic atomic displacement parameters equal to 1.2 times the value of the equivalent atomic displacement parameters of the parent carbon atom [Uiso(H)= 1.2Ueq(C)]. The methylene H atoms were constrained to an ideal geometry with d(C—H) = 0.99 A° or d(C—H) = 0.95 Å (for terminal methylene group) and Uiso(H) = 1.2Ueq(C). Methyl H atoms were constrained as riding atoms, fixed to the parent atoms with distance of 0.98 A° and Uiso(H) = 1.5Ueq(C). hydroxy H atoms were constrained as riding atoms with d(O—H) = 0.84 Å and Uiso(H) = 1.5Ueq(O). Hydrogen atoms involved in weak hydrogen bonds were refined freely with Uiso(H) equal to 1.2Ueq of the parent atom. In the absence of significant anomalous dispersion effects the Friedel pairs were merged.

Structure description top

Betulone (lup-20 (29)-en-28-ol-3-one) also known as betulonic alcohol, is a pentacyclic triterpene of the lupane type which was first isolated as a natural product from Betula lenta in 1991 (Cole et al., 1991). Betulone can be also isolated from various plants for example Maytenus cuzcoina and Maytenus chiapensis (Reyes et al., 2006), Betula alleghaniens (Diouf et al., 2009), Excoecaria agallocha (Liu et al., 2010), Ilex macropoda (Kim et al., 2002) and Terminalia glabrescens (Garcez et al., 2003). The continually growing interest in betulone and its derivatives results from their wide spectrum of biological activities such as anti-inflammatory (Reyes et al., 2006), anti-leishmanial (Alakurtti et al., 2010) and anticancer (Hata et al., 2002).

The structure of betulone is based on the 30-carbon skeleton comprising of four 6-membered rings and one cyclopentane ring. It has three available sites for simple chemical modification, namely: keto group at C3, primary hydroxy group at C28 and isopropenyl side chain at C19. These groups and their positions, mutual distances and orientation with respect to the rings can influence hydrogen bonding and the interactions of betulone with other active sites of surrounding species.

Betulone is also known as a derivative of betulin, which is one of the most plentiful triterpenes comprising up to 30% dry weight of the outer bark of the white birch. In comparison to betulin, the content of betulone in the outer bark of different tree species is very low, e.g. about of 0.03% in Betula platyphylla (Fuchino et al., 1996) and for this reason the isolation from raw plant material is poorly profitable. A more effective method to obtain betulone with high yield is to carry out synthesis from betulin (Hase et al., 1981). The crystal structure of betulone has not been reported until now. However, the crystal structures of betulonic acid-DMSO and betulonic acid-DMF solvates (Boryczka et al., 2012b) were earlier described. In addition, the structure of betulinic acid-DMSO solvate (Boryczka et al., 2012a) has also been reported. In the present work, we describe the crystal structure of betulone in order to gain a better understanding of the structure-activity relationships of this important molecule. Betulonic alcohol was obtained by oxidation of naturally occurring betulin in a one-step reaction utilizing Jones-oxidation (CrO3/H2SO4 in acetone-water solution) as the side product.

The asymmetric unit contains two independent molecules (IA and IB). A schematic drawing of the ring and atom labeling is shown in Fig. 1 and the asymmetric unit is shown in Fig. 2. All bond lengths and the angles show normal values. The cyclopentane ring adopts an envelope conformation and the cyclohexane rings are all in chair conformations. All the ring junctions in the lupane nucleus are trans-fused. A similar ring conformation is also observed in 20 (29)-lupene-3β,28β-diacetate (Mohamed et al., 2006), 3,28-diacetoxy-29-bromo-betulin (Ding et al., 2009) and also in betulin-ethanol (Drebushchak et al., 2010), betulin-DMSO (Boryczka et al., 2011), betulinic acid-DMSO (Boryczka et al., 2012a) solvates. However, the conformation of ring A in betulone differs significantly from that observed earlier for betulonic acid-DMSO and DMF solvate, where ring A adopts a boat conformation. The molecules are packed along the a axis, in a zigzag fashion, parallel to the bc plane (Fig. 3). The cyclopentane ring is in an envelope conformation with the C17 atom being displaced from C18/C19/C21/C22 plane by 0.656 (4) Å (IA) and 0.674 (4) Å (IB). The C17—C18—C19—C21 and C19—C21—C22—C17 torsion angles are 27.0 (4)°, -25.4 (4)° (for IA) and 27.5 (3)°, -26.1 (3)° (for IB) respectively. The methyl groups C24, C25, C26, C27 occupy axial positions, but the methyl group C23 and isopropenyl group at C19 are equatorial. Fig. 4 shows the different orientations of the isopropenyl groups in the two independent molecules, (IA and IB). The value of the C21—C19—C20—C29 torsion angle describes the orientation of the isopropenyl group is equal to 92.3 (4)° (IA) and -98.8 (4)° (IB). The value of the C21—C19—C20—C29 torsion angle for betulin-DMSO and betulin-ethanol solvates are -96.8 (5)° and 88.6 (5)°, respectively. The hydroxymethyl group is attached to atom C17 of ring D in an axial orientation. No classical hydrogen bonding involving the hydroxy groups is observed. In the crystal, weak intermolecular C—H···O interactions link molecules into chains along [010]. Weak intramolecular C—H···O hydrogen bonds are also observed.

For the synthesis of betulone, see: Hase et al. (1981). For the isolation of betulone from plants, see: Cole et al. (1991); Reyes et al. (2006); Diouf et al. (2009); Liu et al. (2010); Kim et al. (2002); Garcez et al. (2003); Fuchino et al. (1996). For the biological activity of betulone, see: Alakurtti et al. (2010); Hata et al. (2002); Reyes et al. (2006). For related structures, see: Mohamed et al. (2006); Ding et al. (2009); Drebushchak et al. (2010); Boryczka et al. (2011, 2012a,b).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Atom and ring numbering scheme for the title compound.
[Figure 2] Fig. 2. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% level.
[Figure 3] Fig. 3. View of the unit cell along the crystallographic a axis.
[Figure 4] Fig. 4. Different orientation of isopropenyl group virewd towards the C19/C20/C29/C30 plane in IA and IB.
Lup-20(29)-en-28-ol-3-one top
Crystal data top
C30H48O2F(000) = 1952
Mr = 440.71Dx = 1.149 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 24992 reflections
a = 9.4447 (3) Åθ = 2.5–34.6°
b = 19.1818 (6) ŵ = 0.07 mm−1
c = 28.1141 (7) ÅT = 100 K
V = 5093.3 (3) Å3Plate, colourless
Z = 80.60 × 0.56 × 0.20 mm
Data collection top
Oxford Diffraction
diffractometer with a Sapphire3 detector		5036 independent reflections
Radiation source: fine-focus sealed tube4401 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 16.0328 pixels mm-1θmax = 25.1°, θmin = 2.5°
ω scanh = −8→11
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		k = −22→22
Tmin = 0.960, Tmax = 0.986l = −33→33
61473 measured 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1099P)2]
where P = (Fo2 + 2Fc2)/3
5036 reflections(Δ/σ)max < 0.001
609 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.50 e Å−3
Crystal data top
C30H48O2V = 5093.3 (3) Å3
Mr = 440.71Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 9.4447 (3) ŵ = 0.07 mm−1
b = 19.1818 (6) ÅT = 100 K
c = 28.1141 (7) Å0.60 × 0.56 × 0.20 mm
Data collection top
Oxford Diffraction
diffractometer with a Sapphire3 detector		5036 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		4401 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.986Rint = 0.055
61473 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.55 e Å−3
5036 reflectionsΔρmin = −0.50 e Å−3
609 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A1.1431 (3)0.77637 (14)−0.03486 (10)0.0509 (8)
O2A0.6372 (4)0.28035 (18)0.08472 (12)0.0727 (11)
H2A0.71900.29450.09140.109*
C1A1.0227 (4)0.60249 (18)−0.04338 (11)0.0299 (8)
H1AA0.93110.6232−0.05310.036*
H1AB1.04040.5616−0.06400.036*
C2A1.1415 (4)0.6566 (2)−0.05138 (13)0.0385 (9)
H2AA1.23430.6339−0.04610.046*
H2AB1.13830.6727−0.08480.046*
C3A1.1299 (4)0.71811 (19)−0.01944 (13)0.0320 (8)
C4A1.1037 (4)0.70497 (18)0.03356 (12)0.0309 (8)
C5A0.9920 (3)0.64490 (17)0.03958 (11)0.0255 (7)
H5A0.90100.66560.02820.031*
C6A0.9629 (4)0.62503 (19)0.09145 (11)0.0329 (8)
H6AA1.04050.59510.10350.039*
H6AB0.95940.66770.11130.039*
C7A0.8220 (4)0.58598 (19)0.09519 (11)0.0332 (8)
H7AA0.74470.61750.08500.040*
H7AB0.80500.57370.12890.040*
C8A0.8157 (4)0.51877 (18)0.06497 (10)0.0267 (7)
C9A0.8698 (3)0.53544 (17)0.01340 (10)0.0218 (7)
H9A0.79550.5666−0.00050.026*
C10A1.0118 (3)0.57800 (17)0.00863 (11)0.0251 (7)
C11A0.8664 (4)0.46982 (17)−0.01759 (11)0.0264 (7)
H11A0.93180.4347−0.00410.032*
H11B0.89980.4816−0.05000.032*
C12A0.7174 (3)0.43854 (17)−0.02076 (10)0.0249 (7)
H12A0.72140.3943−0.03880.030*
H12B0.65480.4710−0.03820.030*
C13A0.6552 (3)0.42468 (17)0.02894 (10)0.0240 (7)
H13A0.723 (4)0.3924 (18)0.0478 (12)0.029*
C14A0.6565 (3)0.49143 (17)0.06015 (10)0.0244 (7)
C15A0.5923 (4)0.4738 (2)0.10962 (11)0.0359 (9)
H15A0.66010.44390.12700.043*
H15B0.58230.51770.12780.043*
C16A0.4469 (4)0.4367 (2)0.10862 (12)0.0374 (9)
H16A0.41860.42380.14140.045*
H16B0.37420.46860.09550.045*
C17A0.4564 (4)0.37156 (19)0.07795 (12)0.0341 (8)
C18A0.5063 (4)0.39119 (18)0.02774 (11)0.0268 (7)
H18A0.43990.42800.01600.032*
C19A0.4791 (4)0.32596 (18)−0.00271 (13)0.0341 (8)
H19A0.558 (4)0.296 (2)0.0026 (13)0.041*
C20A0.4436 (4)0.33884 (19)−0.05530 (13)0.0352 (8)
C21A0.3519 (5)0.2879 (2)0.02319 (15)0.0510 (11)
H21A0.26890.28460.00180.061*
H21B0.37990.24030.03310.061*
C22A0.3172 (5)0.3332 (2)0.06692 (15)0.0489 (11)
H22A0.24060.36670.05960.059*
H22B0.28780.30390.09410.059*
C23A1.0466 (4)0.77220 (19)0.05630 (14)0.0409 (9)
H23A1.10710.81150.04730.061*
H23B1.04650.76730.09100.061*
H23C0.94980.78070.04510.061*
C24A1.2508 (4)0.6891 (2)0.05663 (15)0.0453 (10)
H24A1.29780.65180.03880.068*
H24B1.23720.67450.08970.068*
H24C1.30950.73120.05580.068*
C25A1.1442 (4)0.5352 (2)0.02094 (14)0.0364 (8)
H25A1.13410.48790.00830.055*
H25B1.15540.53310.05560.055*
H25C1.22780.55740.00680.055*
C26A0.9099 (4)0.46436 (19)0.09009 (12)0.0342 (8)
H26A1.00510.48360.09460.051*
H26B0.91550.42210.07050.051*
H26C0.86900.45280.12110.051*
C27A0.5578 (4)0.54781 (17)0.03828 (12)0.0291 (8)
H27A0.45910.53250.04080.044*
H27B0.58230.55470.00470.044*
H27C0.56990.59180.05560.044*
C28A0.5492 (5)0.3188 (2)0.10332 (14)0.0447 (10)
H28A0.60130.34540.12790.054*
H28B0.48350.28770.12070.054*
C29A0.3848 (4)0.3965 (2)−0.07222 (14)0.0407 (9)
H29A0.36180.3998−0.10500.049*
H29B0.36560.4345−0.05150.049*
C30A0.4735 (6)0.2800 (3)−0.08691 (16)0.0631 (13)
H30A0.43040.2886−0.11810.095*
H30B0.43410.2373−0.07320.095*
H30C0.57620.2749−0.09060.095*
O1B−0.3496 (3)0.80561 (15)0.28884 (10)0.0480 (7)
O2B0.6246 (3)1.01860 (12)0.13685 (8)0.0344 (6)
H2B0.60401.00230.16370.052*
C1B0.0161 (4)0.84111 (17)0.28726 (11)0.0261 (7)
H1BA0.10420.82360.30220.031*
H1BB−0.01230.88400.30440.031*
C2B−0.1003 (4)0.78616 (18)0.29336 (12)0.0323 (8)
H2BA−0.06570.74100.28090.039*
H2BB−0.12030.78020.32770.039*
C3B−0.2362 (4)0.80529 (17)0.26795 (12)0.0286 (7)
C4B−0.2235 (3)0.82674 (16)0.21577 (11)0.0222 (7)
C5B−0.0983 (3)0.88076 (15)0.21148 (11)0.0185 (6)
H5B−0.13080.92210.23020.022*
C6B−0.0769 (3)0.90864 (16)0.16122 (10)0.0205 (6)
H6BA−0.17000.91960.14690.025*
H6BB−0.03070.87250.14140.025*
C7B0.0147 (3)0.97415 (15)0.16204 (10)0.0197 (6)
H7BA−0.03611.01110.17980.024*
H7BB0.02780.99080.12900.024*
C8B0.1626 (3)0.96323 (15)0.18508 (10)0.0164 (6)
C9B0.1422 (3)0.92689 (14)0.23454 (10)0.0175 (6)
H9BA0.08940.96160.25430.021*
C10B0.0471 (3)0.85976 (15)0.23497 (10)0.0191 (6)
C11B0.2853 (3)0.91725 (16)0.26026 (10)0.0211 (6)
H11C0.26750.89860.29250.025*
H11D0.34230.88240.24270.025*
C12B0.3709 (3)0.98473 (15)0.26455 (10)0.0214 (6)
H12C0.32261.01670.28690.026*
H12D0.46560.97390.27770.026*
C13B0.3881 (3)1.02087 (15)0.21660 (10)0.0173 (6)
H13B0.435 (3)0.9873 (17)0.1934 (11)0.021*
C14B0.2394 (3)1.03694 (15)0.19426 (10)0.0177 (6)
C15B0.2574 (3)1.07779 (16)0.14691 (10)0.0212 (6)
H15C0.29561.04560.12260.025*
H15D0.16271.09320.13600.025*
C16B0.3544 (3)1.14170 (16)0.14973 (11)0.0242 (7)
H16C0.31161.17720.17080.029*
H16D0.36561.16240.11770.029*
C17B0.4999 (3)1.11996 (15)0.16926 (10)0.0212 (7)
C18B0.4813 (3)1.08681 (15)0.21843 (10)0.0200 (6)
H18B0.43041.12160.23870.024*
C19B0.6342 (3)1.08099 (16)0.23816 (11)0.0218 (6)
H19B0.677 (4)1.0405 (19)0.2266 (12)0.026*
C20B0.6521 (4)1.08491 (17)0.29161 (12)0.0287 (7)
C21B0.7161 (4)1.14185 (17)0.21277 (12)0.0276 (7)
H21C0.75371.17510.23650.033*
H21D0.79621.12320.19400.033*
C22B0.6084 (4)1.17815 (17)0.18003 (12)0.0262 (7)
H22C0.551 (4)1.2189 (18)0.1957 (12)0.031*
H22D0.662 (4)1.1975 (18)0.1499 (13)0.031*
C23B−0.3632 (3)0.86105 (17)0.20088 (13)0.0296 (7)
H23D−0.44160.82860.20660.044*
H23E−0.35940.87290.16700.044*
H23F−0.37790.90360.21950.044*
C24B−0.2054 (4)0.76017 (17)0.18541 (13)0.0297 (8)
H24D−0.12750.73220.19820.045*
H24E−0.18420.77320.15250.045*
H24F−0.29310.73290.18630.045*
C25B0.1199 (3)0.79668 (15)0.21113 (12)0.0237 (7)
H25D0.22160.79790.21780.035*
H25E0.10470.79870.17670.035*
H25F0.07940.75340.22370.035*
C26B0.2521 (3)0.91803 (16)0.15102 (10)0.0218 (6)
H26D0.19260.88130.13740.033*
H26E0.33060.89680.16870.033*
H26F0.28990.94730.12540.033*
C27B0.1513 (3)1.08464 (15)0.22700 (11)0.0237 (7)
H27D0.20411.12760.23340.036*
H27E0.13221.06050.25700.036*
H27F0.06151.09610.21140.036*
C28B0.5697 (3)1.07459 (16)0.13205 (11)0.0231 (7)
H28C0.49671.06770.10720.028*
H28D0.64331.10440.11740.028*
C29B0.7480 (5)1.0447 (2)0.31341 (14)0.0483 (11)
H29C0.76361.04950.34660.058*
H29D0.80041.01140.29570.058*
C30B0.5679 (5)1.1375 (2)0.31777 (13)0.0491 (11)
H30D0.60301.14120.35050.074*
H30E0.46821.12330.31820.074*
H30F0.57681.18280.30200.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0601 (19)0.0390 (16)0.0537 (18)−0.0081 (14)0.0087 (15)−0.0007 (13)
O2A0.082 (2)0.081 (2)0.055 (2)0.034 (2)0.027 (2)0.0391 (18)
C1A0.0320 (18)0.0340 (18)0.0237 (16)−0.0067 (16)0.0070 (14)−0.0063 (14)
C2A0.042 (2)0.044 (2)0.0295 (18)−0.0090 (19)0.0083 (17)−0.0069 (16)
C3A0.0208 (17)0.034 (2)0.041 (2)−0.0040 (15)−0.0020 (15)−0.0043 (16)
C4A0.0280 (17)0.0333 (19)0.0314 (18)0.0025 (15)−0.0057 (15)−0.0109 (15)
C5A0.0208 (16)0.0335 (17)0.0223 (16)0.0038 (14)−0.0046 (13)−0.0046 (13)
C6A0.0369 (19)0.042 (2)0.0191 (16)0.0074 (16)−0.0075 (14)−0.0092 (15)
C7A0.0346 (18)0.049 (2)0.0157 (15)0.0052 (17)0.0010 (14)−0.0076 (15)
C8A0.0298 (17)0.0379 (19)0.0125 (14)0.0085 (15)0.0004 (13)0.0003 (13)
C9A0.0215 (15)0.0292 (17)0.0145 (14)0.0062 (14)−0.0005 (12)−0.0001 (12)
C10A0.0228 (16)0.0330 (18)0.0195 (15)0.0030 (14)−0.0002 (13)−0.0038 (13)
C11A0.0289 (17)0.0330 (18)0.0173 (14)0.0018 (15)0.0046 (13)−0.0011 (13)
C12A0.0299 (17)0.0297 (17)0.0152 (15)0.0001 (14)0.0053 (13)0.0011 (13)
C13A0.0254 (16)0.0304 (17)0.0163 (14)0.0050 (15)0.0035 (13)0.0064 (13)
C14A0.0249 (16)0.0348 (18)0.0135 (14)0.0058 (15)0.0039 (12)0.0038 (13)
C15A0.040 (2)0.053 (2)0.0140 (15)0.0062 (18)0.0062 (14)0.0019 (15)
C16A0.0355 (19)0.053 (2)0.0235 (17)0.0058 (18)0.0145 (15)0.0084 (16)
C17A0.0359 (19)0.041 (2)0.0254 (17)0.0050 (17)0.0120 (15)0.0129 (15)
C18A0.0303 (18)0.0296 (17)0.0205 (16)0.0043 (14)0.0067 (14)0.0097 (13)
C19A0.037 (2)0.0275 (18)0.038 (2)−0.0004 (16)0.0083 (16)0.0074 (15)
C20A0.0259 (17)0.041 (2)0.038 (2)−0.0069 (16)0.0049 (15)−0.0043 (16)
C21A0.059 (3)0.048 (2)0.046 (2)−0.016 (2)0.015 (2)0.0079 (19)
C22A0.046 (2)0.052 (2)0.049 (2)−0.007 (2)0.022 (2)0.016 (2)
C23A0.040 (2)0.037 (2)0.046 (2)0.0024 (18)−0.0033 (18)−0.0132 (17)
C24A0.028 (2)0.051 (2)0.057 (3)0.0003 (18)−0.0116 (18)−0.011 (2)
C25A0.0232 (17)0.038 (2)0.048 (2)0.0055 (16)0.0005 (16)−0.0091 (17)
C26A0.0326 (19)0.045 (2)0.0247 (17)0.0053 (17)−0.0061 (14)0.0085 (15)
C27A0.0260 (17)0.0286 (17)0.0327 (18)0.0050 (14)−0.0003 (15)0.0025 (14)
C28A0.051 (2)0.048 (2)0.035 (2)0.005 (2)0.0139 (19)0.0185 (18)
C29A0.041 (2)0.044 (2)0.037 (2)−0.0020 (18)−0.0088 (17)0.0047 (17)
C30A0.074 (3)0.071 (3)0.044 (3)0.019 (3)0.008 (2)−0.008 (2)
O1B0.0398 (15)0.0614 (18)0.0428 (16)−0.0095 (14)0.0111 (13)0.0146 (13)
O2B0.0411 (14)0.0317 (13)0.0302 (12)−0.0012 (12)0.0049 (11)0.0028 (10)
C1B0.0302 (17)0.0276 (16)0.0206 (16)−0.0045 (14)0.0005 (13)0.0040 (13)
C2B0.040 (2)0.0317 (18)0.0254 (17)−0.0080 (16)−0.0008 (15)0.0100 (14)
C3B0.0295 (18)0.0253 (17)0.0310 (18)−0.0106 (15)0.0048 (15)0.0057 (14)
C4B0.0228 (16)0.0197 (15)0.0242 (16)−0.0009 (13)0.0003 (13)0.0021 (13)
C5B0.0184 (15)0.0148 (14)0.0222 (15)−0.0008 (12)0.0001 (12)0.0008 (12)
C6B0.0181 (15)0.0229 (15)0.0206 (15)0.0020 (13)−0.0040 (12)0.0019 (12)
C7B0.0232 (16)0.0181 (14)0.0177 (14)0.0000 (13)−0.0025 (12)0.0055 (12)
C8B0.0175 (14)0.0178 (15)0.0138 (13)−0.0010 (12)−0.0003 (11)0.0023 (11)
C9B0.0228 (15)0.0154 (14)0.0143 (13)−0.0011 (13)0.0006 (12)0.0022 (11)
C10B0.0226 (15)0.0164 (14)0.0185 (15)−0.0007 (13)−0.0016 (12)0.0051 (11)
C11B0.0272 (16)0.0199 (15)0.0162 (14)−0.0015 (13)−0.0017 (12)0.0053 (12)
C12B0.0257 (16)0.0220 (15)0.0165 (14)−0.0007 (14)−0.0022 (13)0.0019 (12)
C13B0.0201 (15)0.0178 (14)0.0139 (13)−0.0010 (13)−0.0006 (12)−0.0019 (12)
C14B0.0193 (15)0.0156 (14)0.0180 (14)−0.0005 (13)0.0001 (12)0.0028 (12)
C15B0.0224 (15)0.0207 (15)0.0206 (15)−0.0008 (13)−0.0015 (12)0.0083 (13)
C16B0.0285 (17)0.0216 (15)0.0225 (15)−0.0010 (14)−0.0019 (14)0.0072 (12)
C17B0.0248 (17)0.0176 (15)0.0211 (15)−0.0007 (13)−0.0009 (13)0.0029 (12)
C18B0.0257 (16)0.0164 (14)0.0180 (14)−0.0009 (13)−0.0019 (12)0.0009 (12)
C19B0.0228 (16)0.0175 (15)0.0250 (15)−0.0039 (13)−0.0040 (13)−0.0005 (13)
C20B0.0319 (18)0.0265 (16)0.0277 (17)−0.0101 (15)−0.0076 (14)0.0008 (14)
C21B0.0304 (17)0.0230 (16)0.0295 (17)−0.0081 (14)−0.0042 (14)0.0010 (14)
C22B0.0292 (17)0.0193 (16)0.0300 (17)−0.0044 (14)0.0006 (14)0.0037 (13)
C23B0.0208 (16)0.0268 (17)0.041 (2)−0.0004 (14)0.0019 (15)0.0018 (14)
C24B0.0271 (17)0.0227 (17)0.039 (2)−0.0002 (14)0.0004 (15)−0.0040 (14)
C25B0.0241 (16)0.0159 (14)0.0309 (17)0.0001 (13)−0.0053 (14)0.0021 (13)
C26B0.0270 (16)0.0217 (15)0.0166 (14)−0.0026 (14)0.0027 (13)−0.0002 (12)
C27B0.0268 (16)0.0161 (14)0.0282 (16)0.0013 (13)−0.0004 (13)0.0017 (13)
C28B0.0204 (15)0.0269 (17)0.0219 (16)−0.0097 (15)−0.0022 (13)0.0015 (13)
C29B0.065 (3)0.047 (2)0.033 (2)−0.011 (2)−0.022 (2)0.0082 (17)
C30B0.053 (3)0.068 (3)0.0266 (19)−0.005 (2)−0.0048 (18)−0.0162 (19)
Geometric parameters (Å, º) top
O1A—C3A1.205 (4)O1B—C3B1.221 (4)
O2A—C28A1.228 (5)O2B—C28B1.200 (4)
O2A—H2A0.8400O2B—H2B0.8400
C1A—C10A1.539 (4)C1B—C2B1.533 (5)
C1A—C2A1.546 (5)C1B—C10B1.541 (4)
C1A—H1AA0.9900C1B—H1BA0.9900
C1A—H1AB0.9900C1B—H1BB0.9900
C2A—C3A1.486 (5)C2B—C3B1.514 (5)
C2A—H2AA0.9900C2B—H2BA0.9900
C2A—H2AB0.9900C2B—H2BB0.9900
C3A—C4A1.531 (5)C3B—C4B1.528 (4)
C4A—C23A1.537 (5)C4B—C23B1.533 (5)
C4A—C24A1.562 (5)C4B—C24B1.546 (4)
C4A—C5A1.572 (5)C4B—C5B1.577 (4)
C5A—C6A1.532 (5)C5B—C6B1.524 (4)
C5A—C10A1.562 (4)C5B—C10B1.576 (4)
C5A—H5A1.0000C5B—H5B1.0000
C6A—C7A1.531 (5)C6B—C7B1.526 (4)
C6A—H6AA0.9900C6B—H6BA0.9900
C6A—H6AB0.9900C6B—H6BB0.9900
C7A—C8A1.545 (5)C7B—C8B1.554 (4)
C7A—H7AA0.9900C7B—H7BA0.9900
C7A—H7AB0.9900C7B—H7BB0.9900
C8A—C26A1.543 (5)C8B—C26B1.543 (4)
C8A—C9A1.570 (4)C8B—C9B1.567 (4)
C8A—C14A1.598 (5)C8B—C14B1.610 (4)
C9A—C11A1.531 (4)C9B—C11B1.544 (4)
C9A—C10A1.576 (4)C9B—C10B1.570 (4)
C9A—H9A1.0000C9B—H9BA1.0000
C10A—C25A1.536 (5)C10B—C25B1.545 (4)
C11A—C12A1.532 (5)C11B—C12B1.531 (4)
C11A—H11A0.9900C11B—H11C0.9900
C11A—H11B0.9900C11B—H11D0.9900
C12A—C13A1.539 (4)C12B—C13B1.525 (4)
C12A—H12A0.9900C12B—H12C0.9900
C12A—H12B0.9900C12B—H12D0.9900
C13A—C18A1.546 (5)C13B—C18B1.542 (4)
C13A—C14A1.552 (4)C13B—C14B1.569 (4)
C13A—H13A1.04 (4)C13B—H13B1.02 (3)
C14A—C27A1.554 (4)C14B—C27B1.542 (4)
C14A—C15A1.554 (4)C14B—C15B1.554 (4)
C15A—C16A1.547 (5)C15B—C16B1.532 (4)
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
C16A—C17A1.521 (5)C16B—C17B1.538 (4)
C16A—H16A0.9900C16B—H16C0.9900
C16A—H16B0.9900C16B—H16D0.9900
C17A—C28A1.517 (5)C17B—C28B1.512 (4)
C17A—C18A1.535 (4)C17B—C18B1.532 (4)
C17A—C22A1.538 (6)C17B—C22B1.546 (4)
C18A—C19A1.538 (5)C18B—C19B1.551 (4)
C18A—H18A1.0000C18B—H18B1.0000
C19A—C20A1.536 (5)C19B—C20B1.514 (4)
C19A—C21A1.582 (5)C19B—C21B1.572 (4)
C19A—H19A0.95 (4)C19B—H19B0.93 (4)
C20A—C29A1.326 (5)C20B—C29B1.338 (5)
C20A—C30A1.463 (6)C20B—C30B1.480 (5)
C21A—C22A1.541 (6)C21B—C22B1.538 (5)
C21A—H21A0.9900C21B—H21C0.9900
C21A—H21B0.9900C21B—H21D0.9900
C22A—H22A0.9900C22B—H22C1.05 (4)
C22A—H22B0.9900C22B—H22D1.05 (4)
C23A—H23A0.9800C23B—H23D0.9800
C23A—H23B0.9800C23B—H23E0.9800
C23A—H23C0.9800C23B—H23F0.9800
C24A—H24A0.9800C24B—H24D0.9800
C24A—H24B0.9800C24B—H24E0.9800
C24A—H24C0.9800C24B—H24F0.9800
C25A—H25A0.9800C25B—H25D0.9800
C25A—H25B0.9800C25B—H25E0.9800
C25A—H25C0.9800C25B—H25F0.9800
C26A—H26A0.9800C26B—H26D0.9800
C26A—H26B0.9800C26B—H26E0.9800
C26A—H26C0.9800C26B—H26F0.9800
C27A—H27A0.9800C27B—H27D0.9800
C27A—H27B0.9800C27B—H27E0.9800
C27A—H27C0.9800C27B—H27F0.9800
C28A—H28A0.9900C28B—H28C0.9900
C28A—H28B0.9900C28B—H28D0.9900
C29A—H29A0.9500C29B—H29C0.9500
C29A—H29B0.9500C29B—H29D0.9500
C30A—H30A0.9800C30B—H30D0.9800
C30A—H30B0.9800C30B—H30E0.9800
C30A—H30C0.9800C30B—H30F0.9800
C28A—O2A—H2A109.5C28B—O2B—H2B109.5
C10A—C1A—C2A113.1 (3)C2B—C1B—C10B113.7 (3)
C10A—C1A—H1AA109.0C2B—C1B—H1BA108.8
C2A—C1A—H1AA109.0C10B—C1B—H1BA108.8
C10A—C1A—H1AB109.0C2B—C1B—H1BB108.8
C2A—C1A—H1AB109.0C10B—C1B—H1BB108.8
H1AA—C1A—H1AB107.8H1BA—C1B—H1BB107.7
C3A—C2A—C1A113.1 (3)C3B—C2B—C1B112.9 (3)
C3A—C2A—H2AA109.0C3B—C2B—H2BA109.0
C1A—C2A—H2AA109.0C1B—C2B—H2BA109.0
C3A—C2A—H2AB109.0C3B—C2B—H2BB109.0
C1A—C2A—H2AB109.0C1B—C2B—H2BB109.0
H2AA—C2A—H2AB107.8H2BA—C2B—H2BB107.8
O1A—C3A—C2A120.7 (3)O1B—C3B—C2B121.2 (3)
O1A—C3A—C4A121.3 (3)O1B—C3B—C4B121.9 (3)
C2A—C3A—C4A118.0 (3)C2B—C3B—C4B116.8 (3)
C3A—C4A—C23A108.9 (3)C3B—C4B—C23B108.1 (3)
C3A—C4A—C24A107.0 (3)C3B—C4B—C24B108.4 (3)
C23A—C4A—C24A107.6 (3)C23B—C4B—C24B107.4 (3)
C3A—C4A—C5A109.5 (3)C3B—C4B—C5B108.0 (2)
C23A—C4A—C5A109.5 (3)C23B—C4B—C5B110.0 (2)
C24A—C4A—C5A114.2 (3)C24B—C4B—C5B114.7 (3)
C6A—C5A—C10A110.3 (3)C6B—C5B—C10B111.3 (2)
C6A—C5A—C4A113.9 (3)C6B—C5B—C4B113.6 (2)
C10A—C5A—C4A117.5 (3)C10B—C5B—C4B117.0 (2)
C6A—C5A—H5A104.5C6B—C5B—H5B104.5
C10A—C5A—H5A104.5C10B—C5B—H5B104.5
C4A—C5A—H5A104.5C4B—C5B—H5B104.5
C7A—C6A—C5A110.0 (3)C5B—C6B—C7B110.5 (2)
C7A—C6A—H6AA109.7C5B—C6B—H6BA109.6
C5A—C6A—H6AA109.7C7B—C6B—H6BA109.6
C7A—C6A—H6AB109.7C5B—C6B—H6BB109.6
C5A—C6A—H6AB109.7C7B—C6B—H6BB109.6
H6AA—C6A—H6AB108.2H6BA—C6B—H6BB108.1
C6A—C7A—C8A113.8 (3)C6B—C7B—C8B113.9 (2)
C6A—C7A—H7AA108.8C6B—C7B—H7BA108.8
C8A—C7A—H7AA108.8C8B—C7B—H7BA108.8
C6A—C7A—H7AB108.8C6B—C7B—H7BB108.8
C8A—C7A—H7AB108.8C8B—C7B—H7BB108.8
H7AA—C7A—H7AB107.7H7BA—C7B—H7BB107.7
C26A—C8A—C7A106.9 (3)C26B—C8B—C7B108.0 (2)
C26A—C8A—C9A111.9 (3)C26B—C8B—C9B111.6 (2)
C7A—C8A—C9A109.0 (3)C7B—C8B—C9B108.6 (2)
C26A—C8A—C14A111.1 (3)C26B—C8B—C14B110.3 (2)
C7A—C8A—C14A110.9 (3)C7B—C8B—C14B110.7 (2)
C9A—C8A—C14A107.1 (2)C9B—C8B—C14B107.7 (2)
C11A—C9A—C8A110.6 (3)C11B—C9B—C8B111.2 (2)
C11A—C9A—C10A113.3 (2)C11B—C9B—C10B113.5 (2)
C8A—C9A—C10A117.4 (2)C8B—C9B—C10B116.2 (2)
C11A—C9A—H9A104.7C11B—C9B—H9BA104.9
C8A—C9A—H9A104.7C8B—C9B—H9BA104.9
C10A—C9A—H9A104.7C10B—C9B—H9BA104.9
C25A—C10A—C1A108.8 (3)C1B—C10B—C25B108.5 (2)
C25A—C10A—C5A114.3 (3)C1B—C10B—C9B107.8 (2)
C1A—C10A—C5A106.6 (3)C25B—C10B—C9B112.6 (2)
C25A—C10A—C9A113.4 (3)C1B—C10B—C5B107.1 (2)
C1A—C10A—C9A107.2 (2)C25B—C10B—C5B113.9 (2)
C5A—C10A—C9A106.0 (2)C9B—C10B—C5B106.6 (2)
C9A—C11A—C12A112.0 (3)C12B—C11B—C9B113.5 (2)
C9A—C11A—H11A109.2C12B—C11B—H11C108.9
C12A—C11A—H11A109.2C9B—C11B—H11C108.9
C9A—C11A—H11B109.2C12B—C11B—H11D108.9
C12A—C11A—H11B109.2C9B—C11B—H11D108.9
H11A—C11A—H11B107.9H11C—C11B—H11D107.7
C11A—C12A—C13A111.4 (3)C13B—C12B—C11B111.8 (2)
C11A—C12A—H12A109.3C13B—C12B—H12C109.3
C13A—C12A—H12A109.3C11B—C12B—H12C109.3
C11A—C12A—H12B109.3C13B—C12B—H12D109.3
C13A—C12A—H12B109.3C11B—C12B—H12D109.3
H12A—C12A—H12B108.0H12C—C12B—H12D107.9
C12A—C13A—C18A113.5 (3)C12B—C13B—C18B113.9 (2)
C12A—C13A—C14A111.6 (3)C12B—C13B—C14B110.3 (2)
C18A—C13A—C14A111.2 (3)C18B—C13B—C14B111.3 (2)
C12A—C13A—H13A109.4 (19)C12B—C13B—H13B109.1 (17)
C18A—C13A—H13A108.9 (19)C18B—C13B—H13B106.8 (18)
C14A—C13A—H13A101.5 (19)C14B—C13B—H13B105.0 (18)
C13A—C14A—C27A110.2 (3)C27B—C14B—C15B105.7 (2)
C13A—C14A—C15A108.9 (3)C27B—C14B—C13B111.2 (2)
C27A—C14A—C15A105.7 (3)C15B—C14B—C13B110.1 (2)
C13A—C14A—C8A109.0 (2)C27B—C14B—C8B112.0 (2)
C27A—C14A—C8A111.7 (3)C15B—C14B—C8B110.8 (2)
C15A—C14A—C8A111.2 (3)C13B—C14B—C8B107.1 (2)
C16A—C15A—C14A115.5 (3)C16B—C15B—C14B115.1 (2)
C16A—C15A—H15A108.4C16B—C15B—H15C108.5
C14A—C15A—H15A108.4C14B—C15B—H15C108.5
C16A—C15A—H15B108.4C16B—C15B—H15D108.5
C14A—C15A—H15B108.4C14B—C15B—H15D108.5
H15A—C15A—H15B107.5H15C—C15B—H15D107.5
C17A—C16A—C15A109.6 (3)C15B—C16B—C17B109.6 (2)
C17A—C16A—H16A109.7C15B—C16B—H16C109.7
C15A—C16A—H16A109.7C17B—C16B—H16C109.7
C17A—C16A—H16B109.7C15B—C16B—H16D109.7
C15A—C16A—H16B109.7C17B—C16B—H16D109.7
H16A—C16A—H16B108.2H16C—C16B—H16D108.2
C28A—C17A—C16A108.4 (3)C28B—C17B—C18B115.8 (2)
C28A—C17A—C18A114.7 (3)C28B—C17B—C16B107.4 (3)
C16A—C17A—C18A109.7 (3)C18B—C17B—C16B109.4 (2)
C28A—C17A—C22A105.6 (3)C28B—C17B—C22B105.2 (3)
C16A—C17A—C22A117.2 (3)C18B—C17B—C22B101.5 (2)
C18A—C17A—C22A101.2 (3)C16B—C17B—C22B117.8 (2)
C17A—C18A—C19A105.1 (3)C17B—C18B—C13B112.1 (2)
C17A—C18A—C13A111.2 (3)C17B—C18B—C19B104.2 (2)
C19A—C18A—C13A120.2 (3)C13B—C18B—C19B119.0 (2)
C17A—C18A—H18A106.5C17B—C18B—H18B107.0
C19A—C18A—H18A106.5C13B—C18B—H18B107.0
C13A—C18A—H18A106.5C19B—C18B—H18B107.0
C20A—C19A—C18A116.2 (3)C20B—C19B—C18B117.1 (3)
C20A—C19A—C21A110.6 (3)C20B—C19B—C21B111.0 (3)
C18A—C19A—C21A104.2 (3)C18B—C19B—C21B104.0 (2)
C20A—C19A—H19A115 (2)C20B—C19B—H19B110 (2)
C18A—C19A—H19A105 (2)C18B—C19B—H19B110 (2)
C21A—C19A—H19A104 (2)C21B—C19B—H19B104 (2)
C29A—C20A—C30A120.4 (4)C29B—C20B—C30B121.9 (3)
C29A—C20A—C19A124.8 (3)C29B—C20B—C19B120.1 (3)
C30A—C20A—C19A114.7 (3)C30B—C20B—C19B117.8 (3)
C22A—C21A—C19A105.6 (3)C22B—C21B—C19B106.4 (3)
C22A—C21A—H21A110.6C22B—C21B—H21C110.4
C19A—C21A—H21A110.6C19B—C21B—H21C110.4
C22A—C21A—H21B110.6C22B—C21B—H21D110.4
C19A—C21A—H21B110.6C19B—C21B—H21D110.4
H21A—C21A—H21B108.8H21C—C21B—H21D108.6
C17A—C22A—C21A104.4 (3)C21B—C22B—C17B103.2 (2)
C17A—C22A—H22A110.9C21B—C22B—H22C115.4 (19)
C21A—C22A—H22A110.9C17B—C22B—H22C106 (2)
C17A—C22A—H22B110.9C21B—C22B—H22D109 (2)
C21A—C22A—H22B110.9C17B—C22B—H22D114.5 (19)
H22A—C22A—H22B108.9H22C—C22B—H22D109 (3)
C4A—C23A—H23A109.5C4B—C23B—H23D109.5
C4A—C23A—H23B109.5C4B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
C4A—C23A—H23C109.5C4B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C4A—C24A—H24A109.5C4B—C24B—H24D109.5
C4A—C24A—H24B109.5C4B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C4A—C24A—H24C109.5C4B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C10A—C25A—H25A109.5C10B—C25B—H25D109.5
C10A—C25A—H25B109.5C10B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C10A—C25A—H25C109.5C10B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
C8A—C26A—H26A109.5C8B—C26B—H26D109.5
C8A—C26A—H26B109.5C8B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C8A—C26A—H26C109.5C8B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5
C14A—C27A—H27A109.5C14B—C27B—H27D109.5
C14A—C27A—H27B109.5C14B—C27B—H27E109.5
H27A—C27A—H27B109.5H27D—C27B—H27E109.5
C14A—C27A—H27C109.5C14B—C27B—H27F109.5
H27A—C27A—H27C109.5H27D—C27B—H27F109.5
H27B—C27A—H27C109.5H27E—C27B—H27F109.5
O2A—C28A—C17A126.3 (4)O2B—C28B—C17B128.7 (3)
O2A—C28A—H28A105.8O2B—C28B—H28C105.1
C17A—C28A—H28A105.8C17B—C28B—H28C105.1
O2A—C28A—H28B105.8O2B—C28B—H28D105.1
C17A—C28A—H28B105.8C17B—C28B—H28D105.1
H28A—C28A—H28B106.2H28C—C28B—H28D105.9
C20A—C29A—H29A120.0C20B—C29B—H29C120.0
C20A—C29A—H29B120.0C20B—C29B—H29D120.0
H29A—C29A—H29B120.0H29C—C29B—H29D120.0
C20A—C30A—H30A109.5C20B—C30B—H30D109.5
C20A—C30A—H30B109.5C20B—C30B—H30E109.5
H30A—C30A—H30B109.5H30D—C30B—H30E109.5
C20A—C30A—H30C109.5C20B—C30B—H30F109.5
H30A—C30A—H30C109.5H30D—C30B—H30F109.5
H30B—C30A—H30C109.5H30E—C30B—H30F109.5
C10A—C1A—C2A—C3A−54.6 (4)C10B—C1B—C2B—C3B−53.5 (4)
C1A—C2A—C3A—O1A−134.1 (4)C1B—C2B—C3B—O1B−127.3 (4)
C1A—C2A—C3A—C4A47.1 (4)C1B—C2B—C3B—C4B50.4 (4)
O1A—C3A—C4A—C23A20.0 (5)O1B—C3B—C4B—C23B11.8 (4)
C2A—C3A—C4A—C23A−161.2 (3)C2B—C3B—C4B—C23B−165.9 (3)
O1A—C3A—C4A—C24A−96.0 (4)O1B—C3B—C4B—C24B−104.3 (4)
C2A—C3A—C4A—C24A82.8 (4)C2B—C3B—C4B—C24B78.0 (3)
O1A—C3A—C4A—C5A139.8 (3)O1B—C3B—C4B—C5B130.8 (3)
C2A—C3A—C4A—C5A−41.5 (4)C2B—C3B—C4B—C5B−46.9 (4)
C3A—C4A—C5A—C6A177.3 (3)C3B—C4B—C5B—C6B−178.0 (3)
C23A—C4A—C5A—C6A−63.4 (4)C23B—C4B—C5B—C6B−60.2 (3)
C24A—C4A—C5A—C6A57.3 (4)C24B—C4B—C5B—C6B61.0 (3)
C3A—C4A—C5A—C10A46.0 (4)C3B—C4B—C5B—C10B50.2 (3)
C23A—C4A—C5A—C10A165.3 (3)C23B—C4B—C5B—C10B167.9 (3)
C24A—C4A—C5A—C10A−73.9 (4)C24B—C4B—C5B—C10B−70.9 (3)
C10A—C5A—C6A—C7A−64.5 (3)C10B—C5B—C6B—C7B−61.5 (3)
C4A—C5A—C6A—C7A160.8 (3)C4B—C5B—C6B—C7B164.0 (2)
C5A—C6A—C7A—C8A58.6 (4)C5B—C6B—C7B—C8B57.8 (3)
C6A—C7A—C8A—C26A72.9 (4)C6B—C7B—C8B—C26B70.7 (3)
C6A—C7A—C8A—C9A−48.2 (4)C6B—C7B—C8B—C9B−50.5 (3)
C6A—C7A—C8A—C14A−165.8 (3)C6B—C7B—C8B—C14B−168.5 (2)
C26A—C8A—C9A—C11A61.5 (4)C26B—C8B—C9B—C11B63.4 (3)
C7A—C8A—C9A—C11A179.5 (3)C7B—C8B—C9B—C11B−177.7 (2)
C14A—C8A—C9A—C11A−60.5 (3)C14B—C8B—C9B—C11B−57.8 (3)
C26A—C8A—C9A—C10A−70.6 (4)C26B—C8B—C9B—C10B−68.5 (3)
C7A—C8A—C9A—C10A47.4 (4)C7B—C8B—C9B—C10B50.4 (3)
C14A—C8A—C9A—C10A167.4 (2)C14B—C8B—C9B—C10B170.3 (2)
C2A—C1A—C10A—C25A−68.0 (4)C2B—C1B—C10B—C25B−69.9 (3)
C2A—C1A—C10A—C5A55.7 (4)C2B—C1B—C10B—C9B167.9 (3)
C2A—C1A—C10A—C9A169.0 (3)C2B—C1B—C10B—C5B53.5 (3)
C6A—C5A—C10A—C25A−66.3 (4)C11B—C9B—C10B—C1B60.4 (3)
C4A—C5A—C10A—C25A66.6 (4)C8B—C9B—C10B—C1B−168.8 (2)
C6A—C5A—C10A—C1A173.5 (3)C11B—C9B—C10B—C25B−59.2 (3)
C4A—C5A—C10A—C1A−53.7 (3)C8B—C9B—C10B—C25B71.6 (3)
C6A—C5A—C10A—C9A59.4 (3)C11B—C9B—C10B—C5B175.1 (2)
C4A—C5A—C10A—C9A−167.7 (3)C8B—C9B—C10B—C5B−54.1 (3)
C11A—C9A—C10A—C25A−57.7 (3)C6B—C5B—C10B—C1B173.1 (2)
C8A—C9A—C10A—C25A73.2 (3)C4B—C5B—C10B—C1B−54.0 (3)
C11A—C9A—C10A—C1A62.5 (3)C6B—C5B—C10B—C25B−66.9 (3)
C8A—C9A—C10A—C1A−166.6 (3)C4B—C5B—C10B—C25B66.0 (3)
C11A—C9A—C10A—C5A176.1 (2)C6B—C5B—C10B—C9B57.9 (3)
C8A—C9A—C10A—C5A−53.0 (3)C4B—C5B—C10B—C9B−169.2 (2)
C8A—C9A—C11A—C12A58.3 (3)C8B—C9B—C11B—C12B53.0 (3)
C10A—C9A—C11A—C12A−167.5 (3)C10B—C9B—C11B—C12B−173.7 (2)
C9A—C11A—C12A—C13A−54.3 (4)C9B—C11B—C12B—C13B−52.1 (3)
C11A—C12A—C13A—C18A−178.4 (3)C11B—C12B—C13B—C18B−176.5 (2)
C11A—C12A—C13A—C14A54.9 (4)C11B—C12B—C13B—C14B57.5 (3)
C12A—C13A—C14A—C27A64.4 (3)C12B—C13B—C14B—C27B59.7 (3)
C18A—C13A—C14A—C27A−63.5 (3)C18B—C13B—C14B—C27B−67.7 (3)
C12A—C13A—C14A—C15A179.9 (3)C12B—C13B—C14B—C15B176.5 (2)
C18A—C13A—C14A—C15A52.0 (3)C18B—C13B—C14B—C15B49.1 (3)
C12A—C13A—C14A—C8A−58.5 (3)C12B—C13B—C14B—C8B−62.9 (3)
C18A—C13A—C14A—C8A173.6 (2)C18B—C13B—C14B—C8B169.7 (2)
C26A—C8A—C14A—C13A−62.2 (3)C26B—C8B—C14B—C27B178.3 (2)
C7A—C8A—C14A—C13A179.1 (2)C7B—C8B—C14B—C27B58.9 (3)
C9A—C8A—C14A—C13A60.3 (3)C9B—C8B—C14B—C27B−59.7 (3)
C26A—C8A—C14A—C27A175.8 (3)C26B—C8B—C14B—C15B60.6 (3)
C7A—C8A—C14A—C27A57.1 (3)C7B—C8B—C14B—C15B−58.9 (3)
C9A—C8A—C14A—C27A−61.7 (3)C9B—C8B—C14B—C15B−177.5 (2)
C26A—C8A—C14A—C15A57.9 (3)C26B—C8B—C14B—C13B−59.6 (3)
C7A—C8A—C14A—C15A−60.8 (3)C7B—C8B—C14B—C13B−179.0 (2)
C9A—C8A—C14A—C15A−179.6 (3)C9B—C8B—C14B—C13B62.4 (3)
C13A—C14A—C15A—C16A−51.1 (4)C27B—C14B—C15B—C16B70.0 (3)
C27A—C14A—C15A—C16A67.3 (4)C13B—C14B—C15B—C16B−50.2 (3)
C8A—C14A—C15A—C16A−171.3 (3)C8B—C14B—C15B—C16B−168.5 (2)
C14A—C15A—C16A—C17A54.3 (4)C14B—C15B—C16B—C17B55.1 (3)
C15A—C16A—C17A—C28A69.0 (3)C15B—C16B—C17B—C28B68.1 (3)
C15A—C16A—C17A—C18A−57.0 (4)C15B—C16B—C17B—C18B−58.4 (3)
C15A—C16A—C17A—C22A−171.7 (3)C15B—C16B—C17B—C22B−173.5 (3)
C28A—C17A—C18A—C19A70.4 (4)C28B—C17B—C18B—C13B−60.6 (3)
C16A—C17A—C18A—C19A−167.2 (3)C16B—C17B—C18B—C13B60.9 (3)
C22A—C17A—C18A—C19A−42.8 (3)C22B—C17B—C18B—C13B−173.8 (2)
C28A—C17A—C18A—C13A−61.1 (4)C28B—C17B—C18B—C19B69.4 (3)
C16A—C17A—C18A—C13A61.3 (4)C16B—C17B—C18B—C19B−169.1 (2)
C22A—C17A—C18A—C13A−174.3 (3)C22B—C17B—C18B—C19B−43.9 (3)
C12A—C13A—C18A—C17A174.0 (3)C12B—C13B—C18B—C17B178.0 (3)
C14A—C13A—C18A—C17A−59.1 (3)C14B—C13B—C18B—C17B−56.5 (3)
C12A—C13A—C18A—C19A50.7 (4)C12B—C13B—C18B—C19B56.2 (4)
C14A—C13A—C18A—C19A177.6 (3)C14B—C13B—C18B—C19B−178.4 (2)
C17A—C18A—C19A—C20A149.0 (3)C17B—C18B—C19B—C20B150.4 (3)
C13A—C18A—C19A—C20A−84.9 (4)C13B—C18B—C19B—C20B−83.9 (3)
C17A—C18A—C19A—C21A27.0 (4)C17B—C18B—C19B—C21B27.5 (3)
C13A—C18A—C19A—C21A153.2 (3)C13B—C18B—C19B—C21B153.2 (3)
C18A—C19A—C20A—C29A−26.2 (5)C18B—C19B—C20B—C29B142.0 (3)
C21A—C19A—C20A—C29A92.3 (4)C21B—C19B—C20B—C29B−98.8 (4)
C18A—C19A—C20A—C30A156.6 (4)C18B—C19B—C20B—C30B−42.1 (4)
C21A—C19A—C20A—C30A−84.8 (4)C21B—C19B—C20B—C30B77.1 (4)
C20A—C19A—C21A—C22A−126.5 (4)C20B—C19B—C21B—C22B−127.4 (3)
C18A—C19A—C21A—C22A−0.9 (4)C18B—C19B—C21B—C22B−0.6 (3)
C28A—C17A—C22A—C21A−78.2 (4)C19B—C21B—C22B—C17B−26.1 (3)
C16A—C17A—C22A—C21A161.0 (3)C28B—C17B—C22B—C21B−78.0 (3)
C18A—C17A—C22A—C21A41.7 (4)C18B—C17B—C22B—C21B43.0 (3)
C19A—C21A—C22A—C17A−25.4 (4)C16B—C17B—C22B—C21B162.4 (3)
C16A—C17A—C28A—O2A−140.3 (5)C16B—C17B—C28B—O2B−130.4 (3)
C18A—C17A—C28A—O2A−17.2 (6)C18B—C17B—C28B—O2B−7.8 (5)
C22A—C17A—C28A—O2A93.3 (5)C22B—C17B—C28B—O2B103.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13A—H13A···O2A1.04 (4)2.52 (3)3.186 (4)122 (2)
C13B—H13B···O2B1.02 (3)2.47 (3)3.165 (4)125 (2)
C19A—H19A···O2A0.95 (4)2.45 (4)3.006 (5)118 (3)
C22B—H22C···O1Bi1.05 (4)2.56 (4)3.567 (4)160 (3)
Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC30H48O2
Mr440.71
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)9.4447 (3), 19.1818 (6), 28.1141 (7)
V (Å3)5093.3 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.60 × 0.56 × 0.20
Data collection
DiffractometerOxford Diffraction
diffractometer with a Sapphire3 detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2008)
Tmin, Tmax0.960, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections		61473, 5036, 4401
Rint0.055
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.141, 1.03
No. of reflections5036
No. of parameters609
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.55, −0.50

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13A—H13A···O2A1.04 (4)2.52 (3)3.186 (4)122 (2)
C13B—H13B···O2B1.02 (3)2.47 (3)3.165 (4)125 (2)
C19A—H19A···O2A0.95 (4)2.45 (4)3.006 (5)118 (3)
C22B—H22C···O1Bi1.05 (4)2.56 (4)3.567 (4)160 (3)
Symmetry code: (i) −x, y+1/2, −z+1/2.
 

Acknowledgements

This work was supported by the Medical University of Silesia in Katowice, Poland (grant No. KNW-1–006/P/2/0).

References

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ISSN: 2056-9890
Volume 69| Part 5| May 2013| Pages o795-o796
https://doi.org/10.1107/S1600536813011008
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