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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o879-o880

3β,6β-Diacet­­oxy-5,9α-dihy­dr­oxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate

aDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy
*Correspondence e-mail: vinpicci@unina.it, roberto.centore@unina.it

(Received 3 May 2013; accepted 8 May 2013; online 11 May 2013)

The title compound, C31H48O7·0.04CH3COOH, is a polyoxy­genated steroid obtained by selective chemical oxidation of 7-de­hydro­cholesteryl acetate. The asymmetric unit comprises three mol­ecules of the steroid (Z′ = 3) and a mol­ecule of acetic acid which has occupancy factor 0.131 (5). The geometric parameters of the independent mol­ecules do not reveal significant differences. In one mol­ecule, the terminal isopropyl group is disordered over two sets of sites with occupancy ratio 0.869 (5):0.131 (5). The three mol­ecules reveal different hydrogen-bonding patterns. Each of them is involved in an intra­molecular S(6) hydrogen-bonding motif, involving hy­droxy groups as donor and acceptor. In the crystal, two independent mol­ecules form dimers through hydrogen bonding between an OH donor and an acetate carbonyl acceptor, giving rise to R22(16) ring patterns. A single hydrogen bond between the OH group and a ketone carbonyl group is observed between two symmetry-independent mol­ecules.

Related literature

For general information on the isolation of polyoxygenated steroids from marine source, see: Piccialli & Sica (1986[Piccialli, V. & Sica, D. (1986). J. Nat. Prod. 49, 779-783.], 1987[Piccialli, V. & Sica, D. (1987). J. Nat. Prod. 50, 915-920.]); Migliuolo et al. (1990[Migliuolo, A., Notaro, G., Piccialli, V. & Sica, D. (1990). J. Nat. Prod. 53, 1414-1424.]); Notaro et al. (1991[Notaro, G., Piccialli, V., Sica, D. & Corriero, G. (1991). J. Nat. Prod. 54, 1570-1575.], 1992[Notaro, G., Piccialli, V., Sica, D. & Pronzato, R. (1992). J. Nat. Prod. 55, 773-779.]). For the synthesis of polyoxygenated steroids, see: Madaio et al. (1988[Madaio, A., Piccialli, V. & Sica, D. (1988). Tetrahedron Lett. 29, 5999-6000.]); Migliuolo et al. (1992[Migliuolo, A., Piccialli, V. & Sica, D. (1992). Steroids, 57, 344-347.]). For new selective oxidation protocols, see: Piccialli et al. (1993[Piccialli, V., Smaldone, D. M. A. & Sica, D. (1993). Tetrahedron, 49, 4211-4228.], 2013[Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. pp. 1781-1789.]); Notaro et al. (1994[Notaro, G., Piccialli, V., Sica, D. & Smaldone, D. M. A. (1994). Tetrahedron, 50, 4835-4852.]); Bifulco et al. (2003[Bifulco, G., Caserta, T., Gomez-Paloma, L. & Piccialli, V. (2003). Tetrahedron Lett. 44, 5499-5503.]); Caserta et al. (2005[Caserta, T., Piccialli, V., Gomez-Paloma, L. & Bifulco, G. (2005). Tetrahedron, 61, 927-939.]). For the cytotoxic activity of polyoxygenated steroids, see: Chen et al. (2011[Chen, B.-W., Chang, S.-M., Huang, C.-Y., Su, J.-H., Wen, Z.-H., Wu, Y.-C. & Sheu, J.-H. (2011). Org. Biomol. Chem. 9, 3272-3278.]). For a general survey of hydrogen bonding and hydrogen-bonding synthons in crystals, see: Allen et al. (1999[Allen, F. H., Motherwell, W. D. S., Raithby, P. R., Shields, G. P. & Taylor, R. (1999). New J. Chem. pp. 25-34.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For recent examples of hydrogen bonding in crystals, see: Centore, Fusco, Jazbinsek et al. (2013[Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.]); Centore et al. (2013a[Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.],b[Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.]); Centore, Fusco, Capobianco et al. (2013[Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. doi:10.1002/ejoc.201201653.]). For the presence of multiple mol­ecules in the asymmetric unit, see: Desiraju (2007[Desiraju, G. R. (2007). CrystEngComm, 9, 91-92.]).

[Scheme 1]

Experimental

Crystal data
  • C31H48O7·0.04C2H4O2

  • Mr = 535.45

  • Orthorhombic, P 21 21 21

  • a = 10.242 (2) Å

  • b = 28.556 (5) Å

  • c = 30.214 (6) Å

  • V = 8837 (3) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.45 × 0.30 × 0.17 mm

Data collection
  • Bruker–Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.986

  • 82574 measured reflections

  • 11048 independent reflections

  • 6969 reflections with I > 2σ(I)

  • Rint = 0.097

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.185

  • S = 1.00

  • 11048 reflections

  • 1072 parameters

  • 13 restraints

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1AO⋯O3Ci 0.95 1.79 2.745 (4) 177
O1B—H1BO⋯O5C 0.80 2.02 2.819 (4) 175
O1C—H1CO⋯O5B 0.89 1.81 2.699 (4) 178
O2A—H2AO⋯O1A 0.93 1.88 2.691 (4) 145
O2B—H2BO⋯O1B 0.90 1.80 2.628 (4) 153
O2C—H2CO⋯O1C 1.05 1.77 2.614 (4) 134
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1999[Nonius, B. V. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

Polyoxygenated steroids possessing a wide range of oxygenation and nuclear substitution patterns have been isolated from a variety of marine organisms. Some of them show antitumour and antinflammatory activities as well as other biological effects. Thus, the research in this field is still very active. Previous studies in our group focused on the isolation of polyoxygenated steroids from marine sources (Piccialli & Sica, 1986, 1987; Notaro et al., 1991) as well as on the synthesis (Madaio, Piccialli & Sica, 1988; Migliuolo et al., 1992) of some of them exploiting new ruthenium tetroxide oxygenation protocols developed in our laboratories (Piccialli et al., 2013; Notaro et al., 1994). As a continuation of our interest in this field, we have now undertaken a study aimed at preparing a new collection of polyoxygenated steroids for structure-activity relationship studies and in particular at the synthesis of new 9,11-secosteroids. Many representatives of this sub-class of steroids have been shown to possess in vitro cytotoxic activity against various human cancer cell lines (Chen et al., 2011). Due to its functionalization pattern, the title compound, shown in the Scheme, is a good starting product to further oxygenate the steroid nucleus at C and D rings, as well as to obtain the 9,11-secosteroid motif. For now, the title compound has been synthesized starting from commercially available 7-dehydrocholesteryl acetate (Fig. 1).

The X-ray analysis of the title compound confirms the structure and stereochemistry of the synthesized compound. The asymmetric unit contains three independent molecules that have similar geometric parameters (Fig. 2). Rings A and C of the steroid skeleton adopt a chair conformation. Ring B, which contains a double bond at C7=C8, adopts a half- chair conformation with twist at C5—C10 bond. The five-membered D ring is in envelope conformation, with C13 at the flap. In the steroid core trans junctions at A/B and C/D rings are observed. The acetyl group at C3 (ring A) is equatorial while acetyl group at C6 (ring B) is axial. The lateral alkyl chain is fully extended. In one molecule, two different positions were found for the isopropyl group of the lateral alkylic chain (occupancy factor refined to 0.869 (5) for C25B/C26B/C27B; 0.131 (5) for C25Z/C26Z/C27Z). In the crystal, acetic acid solvent of crystallization was found with occupancy factor refined to 0.131 (5).

The molecule of the title compound contains several H–bonding donor and acceptor groups (Allen et al., 1999; Steiner, 2002) that are responsible for the formation of H bonds (Centore et al., 2013a, 2013b; Centore, Fusco, Jazbinsek et al. 2013; Centore, Fusco, Capobianco et al. 2013). The three independent molecules A, B and C are involved in intra and intermolecular H bonding patterns (Fig. 3). In each of the three independent molecules there is an intramolecular H bonding motif S(6) between hydroxy O2 donor and hydroxy O1 acceptor of the same molecule. Molecules B and C create dimers through intermolecular H bonding between OH donors (O1B and O1C) and acetate carbonyl acceptors (O5C and O5B), giving rise to ring patterns R22(16). Molecules C and A are involved in a single intermolecular H bond between OH donor (O1A) and ketone carbonyl acceptor (O3C).

Related literature top

For general information on the isolation of polyoxygenated steroids from marine source, see: Piccialli & Sica (1986, 1987); Migliuolo et al. (1990); Notaro et al. (1992). For the synthesis of polyoxygenated steroids, see: Madaio et al. (1988); Notaro et al. (1991), Migliuolo et al. (1992). For new selective oxidation protocols, see: Piccialli et al. (1993, 2013); Notaro et al. (1994); Bifulco et al. (2003); Caserta et al. (2005). For the cytotoxic activity of polyoxygenated steroids, see: Chen et al. (2011). For a general survey of hydrogen bonding and hydrogen-bonding synthons in crystals, see: Allen et al. (1999); Steiner (2002). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). For recent examples of hydrogen bonding in crystals, see: Centore, Fusco, Jazbinsek et al. (2013); Centore et al. (2013a,b); Centore, Fusco, Capobianco et al. (2013). For the presence of multiple molecules in the asymmetric unit, see: Desiraju (2007).

Experimental top

The title compound was synthesized starting from commercially available 7-dehydrocholesteryl acetate according to a procedure already described (Notaro et al., 1994). Crystals suitable for X-ray analysis were obtained from acetic acid solution by slow evaporation of the solvent.

Refinement top

The H atom of the hydroxy groups were located in difference map with exception of carboxy H atom of the acetic acid solvent molecule that was not assigned. Other H atoms were generated stereochemically. All H atoms were refined by the riding model with Uiso=1.2×Ueq of the carrier atom (1.5 for H atoms of the methyl groups). Some reflections with theta below 3° were removed from the final refinement (OMIT instruction) because their intensities were strongly affected by the beamstop. Some constraints were introduced in the refinement to handle the disorder of the terminal isopropyl group of molecule B. In the absence of strong anomalous scatterer the Flack parameter is not meaningful. Data were merged using MERG 3 instruction and the absolute configuration was assigned on the basis of the known chirality of the precursor used in the synthesis.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003) and SADABS (Bruker, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. Synthesis of the title compound by ruthenium catalyzed selective oxidation of 7-dehydrocholesteryl acetate.
[Figure 2] Fig. 2. ORTEP views of the three independent molecules, thermal ellipsoids are drawn at 30% probability level. In the B molecule, the terminal isopropyl group refined with the minor occupancy factor and the solvent molecule are drawn in open line.
[Figure 3] Fig. 3. H-bonding pattern joining the three independent molecules. The H-bonds are shown as dashed lines.
3β,6β-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate top
Crystal data top
C31H48O7·0.04C2H4O2F(000) = 3498
Mr = 535.45Dx = 1.207 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 454 reflections
a = 10.242 (2) Åθ = 4.9–20.8°
b = 28.556 (5) ŵ = 0.08 mm1
c = 30.214 (6) ÅT = 173 K
V = 8837 (3) Å3Block, colorless
Z = 120.45 × 0.30 × 0.17 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
11048 independent reflections
Radiation source: normal-focus sealed tube6969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.1°
CCD rotation images, thick slices scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 3537
Tmin = 0.963, Tmax = 0.986l = 3938
82574 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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1168P)2]
where P = (Fo2 + 2Fc2)/3
11048 reflections(Δ/σ)max = 0.004
1072 parametersΔρmax = 0.29 e Å3
13 restraintsΔρmin = 0.31 e Å3
Crystal data top
C31H48O7·0.04C2H4O2V = 8837 (3) Å3
Mr = 535.45Z = 12
Orthorhombic, P212121Mo Kα radiation
a = 10.242 (2) ŵ = 0.08 mm1
b = 28.556 (5) ÅT = 173 K
c = 30.214 (6) Å0.45 × 0.30 × 0.17 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
11048 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
6969 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.986Rint = 0.097
82574 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06313 restraints
wR(F2) = 0.185H-atom parameters constrained
S = 1.00Δρmax = 0.29 e Å3
11048 reflectionsΔρmin = 0.31 e Å3
1072 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*/UeqOcc. (<1)
C1A0.9865 (4)0.37429 (15)0.18977 (14)0.0322 (10)
H1A11.03720.34640.19880.039*
H1A21.03780.39130.16710.039*
C1B0.2980 (5)0.42430 (15)0.42610 (15)0.0399 (11)
H1B10.25780.45070.44230.048*
H1B20.22670.40510.41340.048*
C1C0.2794 (4)0.11749 (15)0.36525 (15)0.0387 (11)
H1C10.23280.09000.35310.046*
H1C20.21440.13730.38070.046*
C2A0.9669 (4)0.40597 (15)0.22994 (14)0.0350 (10)
H2A10.92090.38840.25350.042*
H2A21.05300.41580.24160.042*
C2B0.3766 (5)0.39443 (16)0.45845 (17)0.0464 (12)
H2B10.44400.41400.47290.056*
H2B20.31800.38210.48180.056*
C2C0.3383 (5)0.14542 (15)0.32700 (16)0.0412 (11)
H2C10.39950.12540.31010.049*
H2C20.26820.15580.30670.049*
C3A0.8882 (5)0.44887 (14)0.21755 (14)0.0339 (10)
H3A0.93840.46850.19610.041*
C3B0.4408 (4)0.35442 (15)0.43489 (16)0.0381 (11)
H3B0.37280.33230.42360.046*
C3C0.4097 (5)0.18743 (15)0.34513 (15)0.0378 (11)
H3C0.34630.20970.35890.045*
C4A0.7591 (4)0.43526 (14)0.19780 (14)0.0313 (9)
H4A10.71220.46380.18820.038*
H4A20.70540.41960.22060.038*
C4B0.5264 (4)0.37100 (14)0.39673 (14)0.0331 (10)
H4B10.56170.34340.38090.040*
H4B20.60110.38900.40870.040*
C4C0.5132 (4)0.17375 (14)0.37843 (14)0.0347 (10)
H4C10.55320.20240.39090.042*
H4C20.58270.15580.36320.042*
C5A0.7760 (4)0.40225 (14)0.15796 (13)0.0304 (9)
C5B0.4507 (4)0.40168 (14)0.36422 (14)0.0306 (9)
C5C0.4572 (4)0.14427 (14)0.41599 (15)0.0332 (10)
C6A0.6421 (4)0.39143 (14)0.13707 (14)0.0333 (10)
H6A0.60970.42040.12210.040*
C6B0.5359 (4)0.41803 (15)0.32564 (14)0.0313 (10)
H6B0.54440.39120.30450.038*
C6C0.5675 (5)0.13146 (16)0.44961 (15)0.0414 (12)
H6C0.58610.16000.46780.050*
C7A0.6504 (4)0.35362 (14)0.10349 (14)0.0325 (10)
H7A0.57590.34800.08560.039*
C7B0.4826 (4)0.45851 (15)0.30054 (14)0.0349 (10)
H7B0.52920.46850.27500.042*
C7C0.5268 (5)0.09265 (16)0.48091 (15)0.0400 (11)
H7C0.58360.08510.50470.048*
C8A0.7566 (4)0.32687 (13)0.09680 (13)0.0292 (9)
C8B0.3742 (4)0.48185 (14)0.31118 (14)0.0308 (9)
C8C0.4142 (4)0.06810 (14)0.47696 (13)0.0313 (10)
C9A0.8781 (4)0.32994 (13)0.12531 (13)0.0279 (9)
C9B0.2987 (4)0.47081 (14)0.35379 (14)0.0318 (10)
C9C0.3169 (4)0.07645 (13)0.43965 (14)0.0313 (10)
C10A0.8560 (4)0.35833 (13)0.16923 (13)0.0271 (9)
C10B0.3832 (4)0.44372 (14)0.38819 (14)0.0321 (10)
C10C0.3815 (4)0.10057 (13)0.39901 (14)0.0291 (9)
C11A0.9371 (4)0.28079 (14)0.13319 (14)0.0302 (9)
C11B0.2357 (4)0.51585 (14)0.37272 (15)0.0372 (11)
C11C0.2459 (4)0.02994 (14)0.42841 (14)0.0335 (10)
C12A0.9345 (5)0.24626 (14)0.09543 (14)0.0337 (10)
H12A0.95780.21480.10680.040*
H12B1.00120.25540.07330.040*
C12B0.1645 (5)0.54625 (15)0.33994 (15)0.0398 (11)
H12C0.12810.57410.35510.048*
H12D0.09130.52850.32660.048*
C12C0.1979 (5)0.00168 (15)0.46683 (15)0.0377 (11)
H12E0.15410.02700.45610.045*
H12F0.13390.02010.48410.045*
C13A0.8006 (4)0.24362 (13)0.07263 (13)0.0301 (9)
C13B0.2604 (4)0.56181 (14)0.30351 (14)0.0316 (9)
C13C0.3142 (4)0.01141 (14)0.49610 (14)0.0312 (10)
C14A0.7657 (4)0.29391 (13)0.05852 (13)0.0303 (9)
H14A0.83970.30520.03980.036*
C14B0.3091 (4)0.51648 (15)0.28100 (13)0.0337 (10)
H14B0.22920.50040.26950.040*
C14C0.3758 (5)0.03435 (14)0.51265 (14)0.0346 (10)
H14C0.30490.05050.52950.041*
C15A0.6501 (5)0.28780 (15)0.02776 (15)0.0413 (11)
H15A0.64340.31440.00680.050*
H15B0.56760.28540.04470.050*
C15B0.3821 (5)0.53441 (16)0.24014 (15)0.0462 (12)
H15E0.38420.51040.21650.055*
H15F0.47270.54340.24770.055*
C15C0.4737 (5)0.01892 (15)0.54743 (14)0.0379 (10)
H15C0.49110.04430.56890.046*
H15D0.55710.00910.53370.046*
C16A0.6796 (5)0.24186 (15)0.00312 (15)0.0400 (11)
H16A0.70320.24840.02800.048*
H16B0.60200.22120.00340.048*
C16B0.3010 (5)0.57762 (17)0.22566 (15)0.0456 (12)
H16C0.35870.60510.22140.055*
H16D0.25530.57110.19750.055*
C16C0.4055 (5)0.02247 (16)0.56966 (15)0.0399 (11)
H16E0.37820.01390.60000.048*
H16F0.46540.04960.57140.048*
C17A0.7960 (4)0.21796 (14)0.02762 (13)0.0316 (10)
H17A0.87740.22640.01120.038*
C17B0.2012 (5)0.58737 (15)0.26287 (14)0.0365 (10)
H17B0.11930.57030.25480.044*
C17C0.2833 (4)0.03506 (14)0.54091 (13)0.0322 (10)
H17C0.20750.01780.55390.039*
C18A0.7001 (5)0.22420 (14)0.10532 (14)0.0358 (10)
H18A0.72480.19230.11390.054*
H18B0.61380.22370.09130.054*
H18C0.69720.24420.13170.054*
C18B0.3712 (5)0.58937 (16)0.32442 (16)0.0415 (11)
H18D0.42920.60120.30120.062*
H18E0.42060.56890.34440.062*
H18F0.33530.61580.34120.062*
C18C0.4115 (5)0.04103 (15)0.47005 (15)0.0371 (11)
H18G0.45050.02200.44650.056*
H18H0.36610.06790.45690.056*
H18I0.48020.05220.49000.056*
C19A0.7801 (4)0.32707 (14)0.20199 (13)0.0320 (10)
H19G0.83970.30410.21510.048*
H19H0.71000.31070.18620.048*
H19I0.74240.34660.22540.048*
C19B0.4890 (4)0.47704 (15)0.40673 (15)0.0362 (10)
H19A0.52680.49530.38250.054*
H19B0.55780.45860.42110.054*
H19C0.44950.49830.42840.054*
C19C0.4764 (4)0.06638 (14)0.37703 (14)0.0330 (10)
H19D0.52220.04840.39990.050*
H19E0.54010.08390.35940.050*
H19F0.42780.04500.35780.050*
C20A0.7851 (5)0.16422 (14)0.02699 (14)0.0345 (10)
H20A0.69880.15570.04020.041*
C20B0.1652 (5)0.63964 (15)0.26693 (15)0.0405 (11)
H20B0.24760.65750.27250.049*
C20C0.2483 (5)0.08717 (14)0.54216 (13)0.0338 (10)
H20C0.32330.10490.52930.041*
C21A0.8898 (5)0.14014 (15)0.05398 (16)0.0425 (12)
H21D0.88520.10630.04910.064*
H21E0.87620.14680.08550.064*
H21F0.97580.15170.04490.064*
C21B0.0726 (6)0.64996 (17)0.30456 (17)0.0556 (14)
H21G0.00580.63050.30150.083*
H21H0.04790.68310.30380.083*
H21I0.11550.64290.33280.083*
C21C0.1283 (5)0.09820 (17)0.51466 (17)0.0514 (13)
H21A0.05650.07760.52350.077*
H21B0.10280.13090.51940.077*
H21C0.14800.09330.48330.077*
C22A0.7871 (5)0.14571 (15)0.02089 (14)0.0398 (11)
H22A0.73860.16780.04010.048*
H22B0.87850.14460.03150.048*
C22B0.1075 (5)0.65710 (16)0.22319 (15)0.0452 (12)
H22C0.17100.65040.19930.054*
H22D0.02770.63880.21680.054*
C22C0.2307 (5)0.10359 (16)0.59008 (15)0.0448 (12)
H22E0.31140.09600.60660.054*
H22F0.15890.08520.60350.054*
C23A0.7274 (5)0.09747 (15)0.02517 (15)0.0400 (11)
H23A0.63390.09950.01710.048*
H23B0.77020.07640.00350.048*
C23B0.0727 (6)0.70907 (17)0.22135 (18)0.0574 (14)
H23C0.00470.71550.24380.069*
H23D0.15100.72760.22940.069*
C23C0.2013 (6)0.15500 (17)0.59671 (15)0.0489 (13)
H23E0.11170.16130.58590.059*
H23F0.26210.17340.57810.059*
C24A0.7379 (5)0.07539 (15)0.07094 (15)0.0390 (11)
H24A0.82980.06610.07610.047*
H24B0.71490.09920.09340.047*
C24C0.2115 (6)0.17211 (19)0.64309 (16)0.0576 (14)
H24C0.30480.17000.65140.069*
H24D0.16440.14920.66180.069*
C25A0.6507 (5)0.03259 (15)0.07753 (16)0.0434 (12)
H25A0.55810.04300.07390.052*
C25C0.1671 (10)0.2182 (2)0.65672 (18)0.089 (2)
H25C0.07080.21280.65890.107*
C26A0.6777 (6)0.00509 (17)0.04207 (17)0.0555 (15)
H26A0.62030.03200.04700.083*
H26B0.66110.00800.01260.083*
H26C0.76900.01510.04410.083*
C26C0.1710 (7)0.25678 (18)0.6255 (2)0.0674 (17)
H26D0.13820.24620.59670.101*
H26E0.11640.28250.63640.101*
H26F0.26120.26770.62230.101*
C27A0.6643 (5)0.01231 (17)0.12347 (16)0.0507 (13)
H27A0.64420.03650.14550.076*
H27B0.60360.01400.12690.076*
H27C0.75400.00120.12780.076*
C27C0.1988 (7)0.2302 (2)0.70375 (18)0.0783 (19)
H27G0.14870.25780.71280.117*
H27H0.17620.20370.72290.117*
H27I0.29240.23680.70640.117*
C28A0.8326 (5)0.52074 (17)0.25385 (17)0.0476 (13)
C28B0.5104 (5)0.28518 (15)0.47368 (15)0.0376 (11)
C28C0.4840 (5)0.25682 (15)0.30774 (16)0.0382 (11)
C29A0.7923 (6)0.54130 (17)0.29682 (17)0.0516 (13)
H29A0.76620.57400.29240.077*
H29B0.86560.54000.31760.077*
H29C0.71850.52350.30880.077*
C29B0.5981 (6)0.26760 (17)0.50848 (18)0.0584 (15)
H29D0.65060.29350.52010.088*
H29E0.65600.24370.49600.088*
H29F0.54630.25390.53250.088*
C29C0.5692 (6)0.27443 (18)0.27093 (18)0.0546 (14)
H29G0.52570.30060.25600.082*
H29H0.58460.24910.24970.082*
H29I0.65270.28510.28310.082*
C30A0.4499 (5)0.40755 (19)0.17975 (17)0.0444 (12)
C30B0.7633 (4)0.39888 (16)0.33229 (15)0.0356 (10)
C30C0.7866 (5)0.14783 (18)0.43033 (16)0.0459 (13)
C31A0.3517 (5)0.3866 (2)0.20930 (19)0.0591 (15)
H31G0.31200.41110.22750.089*
H31H0.39370.36340.22850.089*
H31I0.28390.37130.19150.089*
C31B0.8882 (5)0.41365 (19)0.35334 (18)0.0481 (13)
H31A0.87610.44400.36790.072*
H31B0.95620.41630.33070.072*
H31C0.91450.39030.37540.072*
C31C0.9060 (5)0.12716 (19)0.40886 (19)0.0561 (14)
H31D0.97780.14980.41020.084*
H31E0.88670.11970.37790.084*
H31F0.93120.09850.42450.084*
O1A0.8478 (3)0.42643 (9)0.12391 (9)0.0362 (7)
H1AO0.82320.45820.11870.043*
O1B0.3478 (3)0.37467 (10)0.34475 (11)0.0405 (8)
H1BO0.36670.34760.34130.049*
O1C0.3636 (3)0.17171 (10)0.43997 (11)0.0485 (9)
H1CO0.38920.20130.44380.058*
O2A0.9809 (3)0.34985 (10)0.09829 (9)0.0361 (7)
H2AO0.95550.38100.09770.043*
O2B0.1830 (3)0.44513 (11)0.34136 (12)0.0452 (8)
H2BO0.21680.41620.34030.054*
O2C0.2089 (3)0.10155 (11)0.45839 (11)0.0462 (8)
H2CO0.23340.13720.46080.055*
O3A0.9891 (3)0.27009 (10)0.16771 (11)0.0440 (8)
O3B0.2412 (4)0.52654 (11)0.41166 (11)0.0510 (9)
O3C0.2310 (3)0.01689 (11)0.39123 (10)0.0456 (8)
O4A0.8634 (3)0.47536 (10)0.25800 (9)0.0385 (7)
O4B0.5250 (3)0.33030 (10)0.46650 (10)0.0407 (8)
O4C0.4774 (3)0.21033 (10)0.30791 (10)0.0427 (8)
O5A0.8372 (6)0.54073 (13)0.21993 (13)0.0853 (16)
O5B0.4347 (4)0.26170 (11)0.45286 (13)0.0602 (10)
O5C0.4292 (4)0.28112 (11)0.33343 (13)0.0537 (9)
O6A0.5444 (3)0.37677 (11)0.16954 (10)0.0388 (7)
O6B0.6680 (3)0.43061 (10)0.34042 (10)0.0352 (7)
O6C0.6855 (3)0.11783 (10)0.42892 (10)0.0400 (8)
O7A0.4481 (4)0.44727 (14)0.16561 (14)0.0640 (11)
O7B0.7464 (3)0.36348 (11)0.31171 (11)0.0467 (8)
O7C0.7797 (4)0.18617 (13)0.44649 (14)0.0630 (11)
C24B0.0242 (7)0.72549 (18)0.17701 (16)0.0579 (15)0.869 (5)
H24E0.05790.70850.17050.069*0.869 (5)
H24F0.08890.71590.15440.069*0.869 (5)
C25B0.0018 (7)0.77782 (19)0.17113 (19)0.0556 (17)0.869 (5)
H25B0.08250.79490.17520.067*0.869 (5)
C26B0.0958 (7)0.7950 (2)0.2048 (2)0.079 (2)0.869 (5)
H26G0.17910.77850.20140.118*0.869 (5)
H26H0.10970.82870.20080.118*0.869 (5)
H26I0.06070.78920.23450.118*0.869 (5)
C27B0.0514 (10)0.7879 (2)0.1256 (2)0.085 (3)0.869 (5)
H27D0.11860.76500.11770.128*0.869 (5)
H27E0.02090.78600.10440.128*0.869 (5)
H27F0.08900.81950.12480.128*0.869 (5)
C24Z0.0242 (7)0.72549 (18)0.17701 (16)0.0579 (15)0.131 (5)
H24G0.01390.69770.15780.069*0.131 (5)
H24H0.09280.74540.16360.069*0.131 (5)
C25Z0.1036 (17)0.7528 (6)0.1760 (6)0.049 (10)*0.131 (5)
H25Z0.17560.73220.18690.059*0.131 (5)
C26Z0.132 (3)0.7669 (11)0.1295 (6)0.047 (10)*0.131 (5)
H26J0.22620.77250.12630.070*0.131 (5)
H26K0.10540.74180.10940.070*0.131 (5)
H26L0.08430.79560.12240.070*0.131 (5)
C27Z0.0958 (7)0.7950 (2)0.2048 (2)0.079 (2)0.131 (5)
H27J0.02450.81530.19470.118*0.131 (5)
H27K0.07940.78530.23540.118*0.131 (5)
H27L0.17850.81230.20340.118*0.131 (5)
O10.060 (3)0.8409 (9)0.0564 (9)0.049 (7)*0.131 (5)
O20.116 (2)0.8592 (7)0.0144 (7)0.036 (6)*0.131 (5)
C30.161 (3)0.8090 (12)0.0734 (11)0.038 (8)*0.131 (5)
H3D0.20120.78460.05500.057*0.131 (5)
H3E0.11390.79430.09790.057*0.131 (5)
H3F0.22990.82940.08530.057*0.131 (5)
C40.071 (4)0.8368 (14)0.0467 (14)0.053 (11)*0.131 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.032 (2)0.031 (2)0.034 (2)0.0028 (18)0.002 (2)0.0026 (19)
C1B0.038 (3)0.034 (2)0.048 (3)0.003 (2)0.018 (2)0.006 (2)
C1C0.031 (3)0.032 (2)0.053 (3)0.002 (2)0.004 (2)0.006 (2)
C2A0.030 (2)0.036 (2)0.039 (2)0.0011 (19)0.006 (2)0.002 (2)
C2B0.047 (3)0.040 (3)0.052 (3)0.003 (2)0.016 (3)0.010 (2)
C2C0.041 (3)0.030 (2)0.053 (3)0.002 (2)0.011 (2)0.008 (2)
C3A0.040 (3)0.031 (2)0.031 (2)0.003 (2)0.005 (2)0.0055 (18)
C3B0.033 (3)0.030 (2)0.052 (3)0.002 (2)0.003 (2)0.004 (2)
C3C0.038 (3)0.031 (2)0.045 (3)0.002 (2)0.004 (2)0.005 (2)
C4A0.032 (2)0.028 (2)0.034 (2)0.0011 (18)0.002 (2)0.0032 (17)
C4B0.030 (2)0.028 (2)0.042 (2)0.0012 (18)0.002 (2)0.0017 (19)
C4C0.036 (3)0.031 (2)0.037 (2)0.008 (2)0.003 (2)0.0032 (19)
C5A0.035 (2)0.027 (2)0.030 (2)0.0014 (18)0.0055 (19)0.0003 (17)
C5B0.026 (2)0.027 (2)0.038 (2)0.0020 (18)0.0056 (19)0.0039 (18)
C5C0.035 (3)0.026 (2)0.039 (2)0.0036 (19)0.005 (2)0.0041 (19)
C6A0.034 (2)0.032 (2)0.034 (2)0.0065 (19)0.001 (2)0.0017 (18)
C6B0.021 (2)0.037 (2)0.036 (2)0.0015 (18)0.0035 (19)0.0116 (19)
C6C0.045 (3)0.037 (2)0.042 (3)0.019 (2)0.005 (2)0.002 (2)
C7A0.036 (3)0.031 (2)0.031 (2)0.005 (2)0.006 (2)0.0008 (18)
C7B0.036 (3)0.036 (2)0.033 (2)0.001 (2)0.004 (2)0.0061 (18)
C7C0.041 (3)0.044 (3)0.035 (2)0.011 (2)0.003 (2)0.003 (2)
C8A0.037 (3)0.0239 (19)0.027 (2)0.0020 (19)0.0007 (19)0.0034 (16)
C8B0.027 (2)0.031 (2)0.035 (2)0.0024 (18)0.0023 (19)0.0058 (19)
C8C0.037 (3)0.029 (2)0.028 (2)0.0016 (19)0.0096 (19)0.0067 (17)
C9A0.031 (2)0.0242 (19)0.029 (2)0.0007 (18)0.0031 (19)0.0021 (17)
C9B0.023 (2)0.028 (2)0.044 (2)0.0002 (18)0.0035 (19)0.0003 (19)
C9C0.031 (2)0.0213 (19)0.041 (2)0.0002 (18)0.010 (2)0.0071 (18)
C10A0.028 (2)0.028 (2)0.026 (2)0.0004 (18)0.0012 (18)0.0025 (16)
C10B0.028 (2)0.027 (2)0.041 (2)0.0004 (18)0.006 (2)0.0014 (18)
C10C0.029 (2)0.0231 (19)0.036 (2)0.0022 (18)0.0007 (19)0.0012 (17)
C11A0.029 (2)0.030 (2)0.032 (2)0.0006 (18)0.003 (2)0.0013 (18)
C11B0.033 (3)0.032 (2)0.046 (3)0.001 (2)0.018 (2)0.004 (2)
C11C0.032 (2)0.030 (2)0.039 (2)0.0027 (19)0.002 (2)0.0033 (19)
C12A0.037 (3)0.027 (2)0.037 (2)0.0064 (19)0.002 (2)0.0011 (18)
C12B0.036 (3)0.035 (2)0.048 (3)0.008 (2)0.012 (2)0.003 (2)
C12C0.036 (3)0.028 (2)0.049 (3)0.0061 (19)0.001 (2)0.004 (2)
C13A0.033 (2)0.027 (2)0.030 (2)0.0062 (18)0.0003 (19)0.0000 (17)
C13B0.031 (2)0.030 (2)0.034 (2)0.0049 (18)0.004 (2)0.0036 (18)
C13C0.025 (2)0.027 (2)0.041 (2)0.0017 (18)0.000 (2)0.0052 (18)
C14A0.036 (2)0.026 (2)0.028 (2)0.0029 (19)0.0025 (19)0.0014 (17)
C14B0.033 (2)0.036 (2)0.032 (2)0.001 (2)0.002 (2)0.0091 (19)
C14C0.032 (2)0.029 (2)0.043 (2)0.0027 (19)0.004 (2)0.0051 (19)
C15A0.049 (3)0.033 (2)0.042 (3)0.011 (2)0.006 (2)0.003 (2)
C15B0.056 (3)0.046 (3)0.036 (3)0.017 (2)0.009 (2)0.002 (2)
C15C0.035 (3)0.040 (2)0.039 (2)0.005 (2)0.001 (2)0.007 (2)
C16A0.052 (3)0.033 (2)0.035 (2)0.010 (2)0.008 (2)0.0027 (19)
C16B0.054 (3)0.046 (3)0.037 (2)0.015 (2)0.008 (2)0.000 (2)
C16C0.036 (3)0.039 (2)0.044 (3)0.005 (2)0.007 (2)0.001 (2)
C17A0.032 (2)0.030 (2)0.033 (2)0.0022 (18)0.000 (2)0.0002 (18)
C17B0.037 (3)0.034 (2)0.038 (2)0.002 (2)0.002 (2)0.0025 (19)
C17C0.031 (3)0.032 (2)0.033 (2)0.0010 (19)0.0000 (19)0.0054 (18)
C18A0.042 (3)0.029 (2)0.037 (2)0.004 (2)0.007 (2)0.0021 (18)
C18B0.045 (3)0.036 (2)0.044 (3)0.002 (2)0.001 (2)0.002 (2)
C18C0.043 (3)0.032 (2)0.036 (2)0.006 (2)0.008 (2)0.0039 (19)
C19A0.035 (3)0.030 (2)0.031 (2)0.0005 (19)0.0009 (19)0.0042 (17)
C19B0.036 (3)0.033 (2)0.040 (2)0.006 (2)0.000 (2)0.0066 (19)
C19C0.039 (3)0.030 (2)0.030 (2)0.0003 (19)0.000 (2)0.0009 (18)
C20A0.034 (3)0.028 (2)0.041 (2)0.0010 (19)0.006 (2)0.0014 (18)
C20B0.048 (3)0.032 (2)0.041 (3)0.001 (2)0.001 (2)0.003 (2)
C20C0.036 (3)0.035 (2)0.030 (2)0.003 (2)0.002 (2)0.0067 (18)
C21A0.051 (3)0.027 (2)0.049 (3)0.011 (2)0.002 (2)0.004 (2)
C21B0.079 (4)0.038 (3)0.050 (3)0.019 (3)0.009 (3)0.001 (2)
C21C0.056 (3)0.044 (3)0.054 (3)0.015 (3)0.012 (3)0.004 (2)
C22A0.048 (3)0.035 (2)0.037 (2)0.005 (2)0.007 (2)0.0001 (19)
C22B0.055 (3)0.038 (2)0.042 (3)0.009 (2)0.002 (2)0.003 (2)
C22C0.055 (3)0.041 (3)0.038 (2)0.011 (2)0.005 (2)0.008 (2)
C23A0.040 (3)0.036 (2)0.044 (3)0.002 (2)0.010 (2)0.004 (2)
C23B0.071 (4)0.045 (3)0.056 (3)0.013 (3)0.010 (3)0.004 (3)
C23C0.060 (3)0.047 (3)0.040 (3)0.011 (3)0.002 (3)0.003 (2)
C24A0.036 (3)0.036 (2)0.044 (2)0.004 (2)0.001 (2)0.005 (2)
C24C0.064 (4)0.064 (3)0.045 (3)0.020 (3)0.001 (3)0.002 (3)
C25A0.038 (3)0.037 (2)0.055 (3)0.003 (2)0.002 (2)0.006 (2)
C25C0.159 (8)0.061 (4)0.048 (3)0.010 (4)0.010 (4)0.012 (3)
C26A0.077 (4)0.038 (3)0.052 (3)0.004 (3)0.005 (3)0.001 (2)
C26C0.076 (4)0.047 (3)0.080 (4)0.008 (3)0.011 (4)0.012 (3)
C27A0.054 (3)0.045 (3)0.053 (3)0.002 (3)0.008 (3)0.004 (2)
C27C0.090 (5)0.094 (5)0.052 (3)0.004 (4)0.006 (4)0.020 (3)
C28A0.060 (3)0.033 (3)0.050 (3)0.001 (2)0.006 (3)0.011 (2)
C28B0.044 (3)0.028 (2)0.041 (2)0.002 (2)0.005 (2)0.007 (2)
C28C0.034 (3)0.033 (2)0.047 (3)0.004 (2)0.017 (2)0.003 (2)
C29A0.059 (3)0.041 (3)0.055 (3)0.008 (2)0.010 (3)0.013 (2)
C29B0.081 (4)0.039 (3)0.056 (3)0.000 (3)0.018 (3)0.005 (2)
C29C0.062 (4)0.046 (3)0.056 (3)0.019 (3)0.003 (3)0.008 (2)
C30A0.029 (3)0.055 (3)0.049 (3)0.010 (2)0.004 (2)0.020 (3)
C30B0.029 (2)0.039 (2)0.039 (2)0.002 (2)0.003 (2)0.001 (2)
C30C0.051 (3)0.046 (3)0.041 (3)0.019 (3)0.010 (2)0.018 (2)
C31A0.033 (3)0.085 (4)0.059 (3)0.003 (3)0.007 (3)0.019 (3)
C31B0.032 (3)0.059 (3)0.054 (3)0.001 (2)0.006 (2)0.005 (3)
C31C0.044 (3)0.059 (3)0.065 (3)0.003 (3)0.001 (3)0.019 (3)
O1A0.0453 (19)0.0248 (14)0.0386 (16)0.0054 (13)0.0084 (15)0.0098 (13)
O1B0.0315 (17)0.0238 (14)0.066 (2)0.0037 (13)0.0086 (16)0.0078 (14)
O1C0.054 (2)0.0249 (15)0.067 (2)0.0057 (15)0.0196 (19)0.0116 (15)
O2A0.0394 (18)0.0319 (15)0.0370 (16)0.0021 (14)0.0106 (15)0.0021 (13)
O2B0.0251 (17)0.0385 (17)0.072 (2)0.0044 (14)0.0050 (17)0.0068 (16)
O2C0.0397 (19)0.0372 (17)0.062 (2)0.0032 (15)0.0069 (17)0.0024 (16)
O3A0.052 (2)0.0349 (16)0.0454 (19)0.0099 (15)0.0109 (17)0.0005 (14)
O3B0.069 (2)0.0398 (17)0.0440 (19)0.0176 (18)0.0202 (18)0.0037 (15)
O3C0.057 (2)0.0400 (17)0.0402 (18)0.0097 (17)0.0074 (17)0.0001 (14)
O4A0.0439 (19)0.0333 (16)0.0382 (16)0.0012 (14)0.0020 (15)0.0079 (13)
O4B0.0453 (19)0.0274 (15)0.0492 (18)0.0055 (14)0.0103 (16)0.0027 (14)
O4C0.052 (2)0.0314 (16)0.0444 (17)0.0047 (15)0.0062 (17)0.0057 (14)
O5A0.165 (5)0.042 (2)0.050 (2)0.010 (3)0.002 (3)0.0033 (19)
O5B0.070 (3)0.0261 (17)0.085 (3)0.0068 (17)0.022 (2)0.0035 (18)
O5C0.063 (2)0.0297 (17)0.069 (2)0.0055 (17)0.004 (2)0.0033 (18)
O6A0.0289 (17)0.0438 (17)0.0437 (18)0.0053 (14)0.0039 (15)0.0016 (15)
O6B0.0241 (16)0.0368 (16)0.0449 (17)0.0014 (13)0.0037 (14)0.0060 (14)
O6C0.0361 (18)0.0408 (17)0.0430 (17)0.0118 (15)0.0061 (15)0.0055 (14)
O7A0.057 (2)0.058 (2)0.077 (3)0.025 (2)0.003 (2)0.014 (2)
O7B0.0333 (18)0.0415 (18)0.066 (2)0.0061 (15)0.0030 (17)0.0136 (17)
O7C0.055 (2)0.048 (2)0.086 (3)0.0241 (19)0.008 (2)0.003 (2)
C24B0.080 (4)0.050 (3)0.044 (3)0.006 (3)0.011 (3)0.007 (2)
C25B0.074 (5)0.042 (3)0.051 (4)0.000 (3)0.015 (3)0.007 (3)
C26B0.104 (6)0.058 (4)0.076 (4)0.023 (4)0.026 (4)0.005 (3)
C27B0.132 (8)0.060 (4)0.063 (4)0.007 (5)0.026 (5)0.014 (4)
C24Z0.080 (4)0.050 (3)0.044 (3)0.006 (3)0.011 (3)0.007 (2)
C27Z0.104 (6)0.058 (4)0.076 (4)0.023 (4)0.026 (4)0.005 (3)
Geometric parameters (Å, º) top
C1A—C2A1.527 (6)C18B—H18E0.9800
C1A—C10A1.543 (6)C18B—H18F0.9800
C1A—H1A10.9900C18C—H18G0.9800
C1A—H1A20.9900C18C—H18H0.9800
C1B—C2B1.527 (7)C18C—H18I0.9800
C1B—C10B1.544 (6)C19A—H19G0.9800
C1B—H1B10.9900C19A—H19H0.9800
C1B—H1B20.9900C19A—H19I0.9800
C1C—C2C1.528 (6)C19B—H19A0.9800
C1C—C10C1.539 (6)C19B—H19B0.9800
C1C—H1C10.9900C19B—H19C0.9800
C1C—H1C20.9900C19C—H19D0.9800
C2A—C3A1.514 (6)C19C—H19E0.9800
C2A—H2A10.9900C19C—H19F0.9800
C2A—H2A20.9900C20A—C21A1.512 (6)
C2B—C3B1.499 (6)C20A—C22A1.540 (6)
C2B—H2B10.9900C20A—H20A1.0000
C2B—H2B20.9900C20B—C21B1.510 (7)
C2C—C3C1.508 (6)C20B—C22B1.531 (6)
C2C—H2C10.9900C20B—H20B1.0000
C2C—H2C20.9900C20C—C21C1.517 (7)
C3A—O4A1.460 (5)C20C—C22C1.532 (6)
C3A—C4A1.501 (6)C20C—H20C1.0000
C3A—H3A1.0000C21A—H21D0.9800
C3B—O4B1.460 (5)C21A—H21E0.9800
C3B—C4B1.524 (6)C21A—H21F0.9800
C3B—H3B1.0000C21B—H21G0.9800
C3C—O4C1.474 (5)C21B—H21H0.9800
C3C—C4C1.513 (6)C21B—H21I0.9800
C3C—H3C1.0000C21C—H21A0.9800
C4A—C5A1.539 (6)C21C—H21B0.9800
C4A—H4A10.9900C21C—H21C0.9800
C4A—H4A20.9900C22A—C23A1.513 (6)
C4B—C5B1.528 (6)C22A—H22A0.9900
C4B—H4B10.9900C22A—H22B0.9900
C4B—H4B20.9900C22B—C23B1.527 (6)
C4C—C5C1.525 (6)C22B—H22C0.9900
C4C—H4C10.9900C22B—H22D0.9900
C4C—H4C20.9900C22C—C23C1.512 (6)
C5A—O1A1.441 (5)C22C—H22E0.9900
C5A—C10A1.536 (6)C22C—H22F0.9900
C5A—C6A1.541 (6)C23A—C24A1.524 (6)
C5B—O1B1.432 (5)C23A—H23A0.9900
C5B—C6B1.530 (6)C23A—H23B0.9900
C5B—C10B1.563 (6)C23B—C24B1.504 (7)
C5C—O1C1.435 (5)C23B—H23C0.9900
C5C—C10C1.556 (6)C23B—H23D0.9900
C5C—C6C1.562 (6)C23C—C24C1.488 (7)
C6A—O6A1.462 (5)C23C—H23E0.9900
C6A—C7A1.484 (6)C23C—H23F0.9900
C6A—H6A1.0000C24A—C25A1.527 (6)
C6B—O6B1.469 (5)C24A—H24A0.9900
C6B—C7B1.486 (6)C24A—H24B0.9900
C6B—H6B1.0000C24C—C25C1.453 (7)
C6C—O6C1.415 (6)C24C—H24C0.9900
C6C—C7C1.516 (6)C24C—H24D0.9900
C6C—H6C1.0000C25A—C27A1.511 (7)
C7A—C8A1.344 (6)C25A—C26A1.544 (7)
C7A—H7A0.9500C25A—H25A1.0000
C7B—C8B1.334 (6)C25C—C26C1.450 (7)
C7B—H7B0.9500C25C—C27C1.497 (8)
C7C—C8C1.355 (6)C25C—H25C1.0000
C7C—H7C0.9500C26A—H26A0.9800
C8A—C14A1.494 (5)C26A—H26B0.9800
C8A—C9A1.516 (6)C26A—H26C0.9800
C8B—C14B1.501 (6)C26C—H26D0.9800
C8B—C9B1.535 (6)C26C—H26E0.9800
C8C—C14C1.499 (6)C26C—H26F0.9800
C8C—C9C1.523 (6)C27A—H27A0.9800
C9A—O2A1.449 (5)C27A—H27B0.9800
C9A—C11A1.546 (6)C27A—H27C0.9800
C9A—C10A1.572 (6)C27C—H27G0.9800
C9B—O2B1.443 (5)C27C—H27H0.9800
C9B—C11B1.548 (6)C27C—H27I0.9800
C9B—C10B1.558 (6)C28A—O5A1.174 (6)
C9C—O2C1.434 (5)C28A—O4A1.340 (6)
C9C—C11C1.552 (6)C28A—C29A1.483 (7)
C9C—C10C1.556 (6)C28B—O5B1.203 (5)
C10A—C19A1.543 (6)C28B—O4B1.315 (5)
C10B—C19B1.547 (6)C28B—C29B1.471 (7)
C10C—C19C1.530 (6)C28C—O5C1.183 (6)
C11A—O3A1.210 (5)C28C—O4C1.329 (5)
C11A—C12A1.508 (6)C28C—C29C1.500 (7)
C11B—O3B1.217 (5)C29A—H29A0.9800
C11B—C12B1.506 (6)C29A—H29B0.9800
C11C—O3C1.193 (5)C29A—H29C0.9800
C11C—C12C1.497 (6)C29B—H29D0.9800
C12A—C13A1.536 (6)C29B—H29E0.9800
C12A—H12A0.9900C29B—H29F0.9800
C12A—H12B0.9900C29C—H29G0.9800
C12B—C13B1.541 (6)C29C—H29H0.9800
C12B—H12C0.9900C29C—H29I0.9800
C12B—H12D0.9900C30A—O7A1.212 (6)
C12C—C13C1.530 (6)C30A—O6A1.343 (5)
C12C—H12E0.9900C30A—C31A1.472 (7)
C12C—H12F0.9900C30B—O7B1.199 (5)
C13A—C18A1.531 (6)C30B—O6B1.355 (5)
C13A—C14A1.540 (5)C30B—C31B1.489 (7)
C13A—C17A1.545 (6)C30C—O7C1.201 (6)
C13B—C18B1.518 (6)C30C—O6C1.345 (5)
C13B—C14B1.545 (6)C30C—C31C1.505 (7)
C13B—C17B1.552 (6)C31A—H31G0.9800
C13C—C18C1.526 (6)C31A—H31H0.9800
C13C—C14C1.535 (6)C31A—H31I0.9800
C13C—C17C1.546 (6)C31B—H31A0.9800
C14A—C15A1.515 (6)C31B—H31B0.9800
C14A—H14A1.0000C31B—H31C0.9800
C14B—C15B1.532 (6)C31C—H31D0.9800
C14B—H14B1.0000C31C—H31E0.9800
C14C—C15C1.518 (6)C31C—H31F0.9800
C14C—H14C1.0000O1A—H1AO0.9542
C15A—C16A1.538 (6)O1B—H1BO0.8049
C15A—H15A0.9900O1C—H1CO0.8929
C15A—H15B0.9900O2A—H2AO0.9280
C15B—C16B1.550 (6)O2B—H2BO0.8964
C15B—H15E0.9900O2C—H2CO1.0507
C15B—H15F0.9900C24B—C25B1.528 (7)
C15C—C16C1.528 (6)C24B—H24E0.9900
C15C—H15C0.9900C24B—H24F0.9900
C15C—H15D0.9900C25B—C26B1.485 (8)
C16A—C17A1.561 (6)C25B—C27B1.495 (8)
C16A—H16A0.9900C25B—H25B1.0000
C16A—H16B0.9900C26B—H26G0.9800
C16B—C17B1.545 (6)C26B—H26H0.9800
C16B—H16C0.9900C26B—H26I0.9800
C16B—H16D0.9900C27B—H27D0.9800
C16C—C17C1.565 (6)C27B—H27E0.9800
C16C—H16E0.9900C27B—H27F0.9800
C16C—H16F0.9900C25Z—C26Z1.488 (13)
C17A—C20A1.539 (5)C25Z—H25Z1.0000
C17A—H17A1.0000C26Z—H26J0.9800
C17B—C20B1.542 (6)C26Z—H26K0.9800
C17B—H17B1.0000C26Z—H26L0.9800
C17C—C20C1.531 (6)O1—C41.38 (5)
C17C—H17C1.0000O2—C41.25 (4)
C18A—H18A0.9800C3—C41.47 (5)
C18A—H18B0.9800C3—H3D0.9800
C18A—H18C0.9800C3—H3E0.9800
C18B—H18D0.9800C3—H3F0.9800
C2A—C1A—C10A112.4 (3)C13A—C17A—H17A107.2
C2A—C1A—H1A1109.1C16A—C17A—H17A107.2
C10A—C1A—H1A1109.1C20B—C17B—C16B113.0 (4)
C2A—C1A—H1A2109.1C20B—C17B—C13B119.1 (4)
C10A—C1A—H1A2109.1C16B—C17B—C13B103.4 (3)
H1A1—C1A—H1A2107.9C20B—C17B—H17B106.9
C2B—C1B—C10B112.2 (4)C16B—C17B—H17B106.9
C2B—C1B—H1B1109.2C13B—C17B—H17B106.9
C10B—C1B—H1B1109.2C20C—C17C—C13C119.6 (3)
C2B—C1B—H1B2109.2C20C—C17C—C16C113.4 (4)
C10B—C1B—H1B2109.2C13C—C17C—C16C102.8 (3)
H1B1—C1B—H1B2107.9C20C—C17C—H17C106.8
C2C—C1C—C10C113.4 (4)C13C—C17C—H17C106.8
C2C—C1C—H1C1108.9C16C—C17C—H17C106.8
C10C—C1C—H1C1108.9C13A—C18A—H18A109.5
C2C—C1C—H1C2108.9C13A—C18A—H18B109.5
C10C—C1C—H1C2108.9H18A—C18A—H18B109.5
H1C1—C1C—H1C2107.7C13A—C18A—H18C109.5
C3A—C2A—C1A110.7 (3)H18A—C18A—H18C109.5
C3A—C2A—H2A1109.5H18B—C18A—H18C109.5
C1A—C2A—H2A1109.5C13B—C18B—H18D109.5
C3A—C2A—H2A2109.5C13B—C18B—H18E109.5
C1A—C2A—H2A2109.5H18D—C18B—H18E109.5
H2A1—C2A—H2A2108.1C13B—C18B—H18F109.5
C3B—C2B—C1B110.7 (4)H18D—C18B—H18F109.5
C3B—C2B—H2B1109.5H18E—C18B—H18F109.5
C1B—C2B—H2B1109.5C13C—C18C—H18G109.5
C3B—C2B—H2B2109.5C13C—C18C—H18H109.5
C1B—C2B—H2B2109.5H18G—C18C—H18H109.5
H2B1—C2B—H2B2108.1C13C—C18C—H18I109.5
C3C—C2C—C1C109.4 (4)H18G—C18C—H18I109.5
C3C—C2C—H2C1109.8H18H—C18C—H18I109.5
C1C—C2C—H2C1109.8C10A—C19A—H19G109.5
C3C—C2C—H2C2109.8C10A—C19A—H19H109.5
C1C—C2C—H2C2109.8H19G—C19A—H19H109.5
H2C1—C2C—H2C2108.2C10A—C19A—H19I109.5
O4A—C3A—C4A108.3 (3)H19G—C19A—H19I109.5
O4A—C3A—C2A107.8 (3)H19H—C19A—H19I109.5
C4A—C3A—C2A111.0 (3)C10B—C19B—H19A109.5
O4A—C3A—H3A109.9C10B—C19B—H19B109.5
C4A—C3A—H3A109.9H19A—C19B—H19B109.5
C2A—C3A—H3A109.9C10B—C19B—H19C109.5
O4B—C3B—C2B108.0 (4)H19A—C19B—H19C109.5
O4B—C3B—C4B107.6 (3)H19B—C19B—H19C109.5
C2B—C3B—C4B112.0 (4)C10C—C19C—H19D109.5
O4B—C3B—H3B109.7C10C—C19C—H19E109.5
C2B—C3B—H3B109.7H19D—C19C—H19E109.5
C4B—C3B—H3B109.7C10C—C19C—H19F109.5
O4C—C3C—C2C107.7 (4)H19D—C19C—H19F109.5
O4C—C3C—C4C107.0 (3)H19E—C19C—H19F109.5
C2C—C3C—C4C112.1 (4)C21A—C20A—C17A113.3 (4)
O4C—C3C—H3C110.0C21A—C20A—C22A109.9 (4)
C2C—C3C—H3C110.0C17A—C20A—C22A110.7 (3)
C4C—C3C—H3C110.0C21A—C20A—H20A107.6
C3A—C4A—C5A111.7 (3)C17A—C20A—H20A107.6
C3A—C4A—H4A1109.3C22A—C20A—H20A107.6
C5A—C4A—H4A1109.3C21B—C20B—C22B110.1 (4)
C3A—C4A—H4A2109.3C21B—C20B—C17B113.5 (4)
C5A—C4A—H4A2109.3C22B—C20B—C17B109.8 (4)
H4A1—C4A—H4A2107.9C21B—C20B—H20B107.7
C3B—C4B—C5B111.9 (4)C22B—C20B—H20B107.7
C3B—C4B—H4B1109.2C17B—C20B—H20B107.7
C5B—C4B—H4B1109.2C21C—C20C—C17C112.2 (4)
C3B—C4B—H4B2109.2C21C—C20C—C22C111.0 (4)
C5B—C4B—H4B2109.2C17C—C20C—C22C110.4 (3)
H4B1—C4B—H4B2107.9C21C—C20C—H20C107.7
C3C—C4C—C5C112.0 (4)C17C—C20C—H20C107.7
C3C—C4C—H4C1109.2C22C—C20C—H20C107.7
C5C—C4C—H4C1109.2C20A—C21A—H21D109.5
C3C—C4C—H4C2109.2C20A—C21A—H21E109.5
C5C—C4C—H4C2109.2H21D—C21A—H21E109.5
H4C1—C4C—H4C2107.9C20A—C21A—H21F109.5
O1A—C5A—C10A106.1 (3)H21D—C21A—H21F109.5
O1A—C5A—C4A108.8 (3)H21E—C21A—H21F109.5
C10A—C5A—C4A112.7 (3)C20B—C21B—H21G109.5
O1A—C5A—C6A105.0 (3)C20B—C21B—H21H109.5
C10A—C5A—C6A113.7 (3)H21G—C21B—H21H109.5
C4A—C5A—C6A110.0 (3)C20B—C21B—H21I109.5
O1B—C5B—C4B109.2 (3)H21G—C21B—H21I109.5
O1B—C5B—C6B105.7 (3)H21H—C21B—H21I109.5
C4B—C5B—C6B112.0 (3)C20C—C21C—H21A109.5
O1B—C5B—C10B106.2 (3)C20C—C21C—H21B109.5
C4B—C5B—C10B111.5 (3)H21A—C21C—H21B109.5
C6B—C5B—C10B111.8 (3)C20C—C21C—H21C109.5
O1C—C5C—C4C109.0 (3)H21A—C21C—H21C109.5
O1C—C5C—C10C105.7 (3)H21B—C21C—H21C109.5
C4C—C5C—C10C112.6 (3)C23A—C22A—C20A112.8 (4)
O1C—C5C—C6C106.4 (3)C23A—C22A—H22A109.0
C4C—C5C—C6C110.0 (4)C20A—C22A—H22A109.0
C10C—C5C—C6C112.8 (3)C23A—C22A—H22B109.0
O6A—C6A—C7A106.8 (3)C20A—C22A—H22B109.0
O6A—C6A—C5A113.0 (3)H22A—C22A—H22B107.8
C7A—C6A—C5A112.0 (4)C23B—C22B—C20B116.0 (4)
O6A—C6A—H6A108.3C23B—C22B—H22C108.3
C7A—C6A—H6A108.3C20B—C22B—H22C108.3
C5A—C6A—H6A108.3C23B—C22B—H22D108.3
O6B—C6B—C7B107.6 (3)C20B—C22B—H22D108.3
O6B—C6B—C5B111.6 (3)H22C—C22B—H22D107.4
C7B—C6B—C5B114.6 (3)C23C—C22C—C20C116.5 (4)
O6B—C6B—H6B107.6C23C—C22C—H22E108.2
C7B—C6B—H6B107.6C20C—C22C—H22E108.2
C5B—C6B—H6B107.6C23C—C22C—H22F108.2
O6C—C6C—C7C108.0 (4)C20C—C22C—H22F108.2
O6C—C6C—C5C113.2 (4)H22E—C22C—H22F107.3
C7C—C6C—C5C112.2 (4)C22A—C23A—C24A115.2 (4)
O6C—C6C—H6C107.7C22A—C23A—H23A108.5
C7C—C6C—H6C107.7C24A—C23A—H23A108.5
C5C—C6C—H6C107.7C22A—C23A—H23B108.5
C8A—C7A—C6A124.3 (4)C24A—C23A—H23B108.5
C8A—C7A—H7A117.9H23A—C23A—H23B107.5
C6A—C7A—H7A117.9C24B—C23B—C22B114.4 (4)
C8B—C7B—C6B124.8 (4)C24B—C23B—H23C108.7
C8B—C7B—H7B117.6C22B—C23B—H23C108.7
C6B—C7B—H7B117.6C24B—C23B—H23D108.7
C8C—C7C—C6C123.9 (4)C22B—C23B—H23D108.7
C8C—C7C—H7C118.0H23C—C23B—H23D107.6
C6C—C7C—H7C118.0C24C—C23C—C22C115.4 (4)
C7A—C8A—C14A121.7 (4)C24C—C23C—H23E108.4
C7A—C8A—C9A123.1 (4)C22C—C23C—H23E108.4
C14A—C8A—C9A115.2 (4)C24C—C23C—H23F108.4
C7B—C8B—C14B123.6 (4)C22C—C23C—H23F108.4
C7B—C8B—C9B121.3 (4)H23E—C23C—H23F107.5
C14B—C8B—C9B114.9 (3)C23A—C24A—C25A114.1 (4)
C7C—C8C—C14C119.5 (4)C23A—C24A—H24A108.7
C7C—C8C—C9C122.8 (4)C25A—C24A—H24A108.7
C14C—C8C—C9C117.5 (4)C23A—C24A—H24B108.7
O2A—C9A—C8A107.4 (3)C25A—C24A—H24B108.7
O2A—C9A—C11A99.2 (3)H24A—C24A—H24B107.6
C8A—C9A—C11A110.8 (3)C25C—C24C—C23C122.9 (5)
O2A—C9A—C10A112.2 (3)C25C—C24C—H24C106.6
C8A—C9A—C10A113.0 (3)C23C—C24C—H24C106.6
C11A—C9A—C10A113.2 (3)C25C—C24C—H24D106.6
O2B—C9B—C8B107.4 (3)C23C—C24C—H24D106.6
O2B—C9B—C11B100.2 (3)H24C—C24C—H24D106.6
C8B—C9B—C11B110.4 (3)C27A—C25A—C24A111.9 (4)
O2B—C9B—C10B112.2 (3)C27A—C25A—C26A110.7 (4)
C8B—C9B—C10B112.4 (3)C24A—C25A—C26A111.2 (4)
C11B—C9B—C10B113.4 (4)C27A—C25A—H25A107.6
O2C—C9C—C8C106.9 (3)C24A—C25A—H25A107.6
O2C—C9C—C11C98.8 (3)C26A—C25A—H25A107.6
C8C—C9C—C11C109.6 (3)C26C—C25C—C24C119.7 (5)
O2C—C9C—C10C114.7 (3)C26C—C25C—C27C116.0 (5)
C8C—C9C—C10C112.0 (3)C24C—C25C—C27C114.0 (6)
C11C—C9C—C10C113.9 (3)C26C—C25C—H25C100.8
C5A—C10A—C1A108.0 (3)C24C—C25C—H25C100.8
C5A—C10A—C19A110.3 (3)C27C—C25C—H25C100.8
C1A—C10A—C19A110.4 (3)C25A—C26A—H26A109.5
C5A—C10A—C9A108.1 (3)C25A—C26A—H26B109.5
C1A—C10A—C9A111.5 (3)H26A—C26A—H26B109.5
C19A—C10A—C9A108.4 (3)C25A—C26A—H26C109.5
C1B—C10B—C19B110.4 (4)H26A—C26A—H26C109.5
C1B—C10B—C9B111.0 (3)H26B—C26A—H26C109.5
C19B—C10B—C9B109.0 (3)C25C—C26C—H26D109.5
C1B—C10B—C5B108.5 (3)C25C—C26C—H26E109.5
C19B—C10B—C5B109.3 (3)H26D—C26C—H26E109.5
C9B—C10B—C5B108.6 (3)C25C—C26C—H26F109.5
C19C—C10C—C1C110.2 (3)H26D—C26C—H26F109.5
C19C—C10C—C9C109.3 (3)H26E—C26C—H26F109.5
C1C—C10C—C9C111.9 (3)C25A—C27A—H27A109.5
C19C—C10C—C5C109.7 (3)C25A—C27A—H27B109.5
C1C—C10C—C5C107.8 (3)H27A—C27A—H27B109.5
C9C—C10C—C5C107.9 (3)C25A—C27A—H27C109.5
O3A—C11A—C12A119.6 (4)H27A—C27A—H27C109.5
O3A—C11A—C9A122.3 (4)H27B—C27A—H27C109.5
C12A—C11A—C9A118.0 (3)C25C—C27C—H27G109.5
O3B—C11B—C12B120.9 (4)C25C—C27C—H27H109.5
O3B—C11B—C9B123.1 (4)H27G—C27C—H27H109.5
C12B—C11B—C9B116.0 (4)C25C—C27C—H27I109.5
O3C—C11C—C12C121.3 (4)H27G—C27C—H27I109.5
O3C—C11C—C9C122.2 (4)H27H—C27C—H27I109.5
C12C—C11C—C9C116.4 (4)O5A—C28A—O4A122.8 (5)
C11A—C12A—C13A112.8 (3)O5A—C28A—C29A125.6 (5)
C11A—C12A—H12A109.0O4A—C28A—C29A111.5 (4)
C13A—C12A—H12A109.0O5B—C28B—O4B122.2 (4)
C11A—C12A—H12B109.0O5B—C28B—C29B125.3 (4)
C13A—C12A—H12B109.0O4B—C28B—C29B112.5 (4)
H12A—C12A—H12B107.8O5C—C28C—O4C124.0 (5)
C11B—C12B—C13B109.1 (4)O5C—C28C—C29C124.5 (4)
C11B—C12B—H12C109.9O4C—C28C—C29C111.6 (4)
C13B—C12B—H12C109.9C28A—C29A—H29A109.5
C11B—C12B—H12D109.9C28A—C29A—H29B109.5
C13B—C12B—H12D109.9H29A—C29A—H29B109.5
H12C—C12B—H12D108.3C28A—C29A—H29C109.5
C11C—C12C—C13C108.9 (4)H29A—C29A—H29C109.5
C11C—C12C—H12E109.9H29B—C29A—H29C109.5
C13C—C12C—H12E109.9C28B—C29B—H29D109.5
C11C—C12C—H12F109.9C28B—C29B—H29E109.5
C13C—C12C—H12F109.9H29D—C29B—H29E109.5
H12E—C12C—H12F108.3C28B—C29B—H29F109.5
C18A—C13A—C12A109.2 (3)H29D—C29B—H29F109.5
C18A—C13A—C14A111.1 (3)H29E—C29B—H29F109.5
C12A—C13A—C14A106.6 (3)C28C—C29C—H29G109.5
C18A—C13A—C17A112.0 (3)C28C—C29C—H29H109.5
C12A—C13A—C17A116.4 (3)H29G—C29C—H29H109.5
C14A—C13A—C17A101.0 (3)C28C—C29C—H29I109.5
C18B—C13B—C12B109.2 (4)H29G—C29C—H29I109.5
C18B—C13B—C14B112.1 (4)H29H—C29C—H29I109.5
C12B—C13B—C14B106.2 (3)O7A—C30A—O6A122.9 (5)
C18B—C13B—C17B112.2 (4)O7A—C30A—C31A125.7 (5)
C12B—C13B—C17B116.8 (4)O6A—C30A—C31A111.4 (5)
C14B—C13B—C17B99.9 (3)O7B—C30B—O6B123.6 (4)
C18C—C13C—C12C110.2 (4)O7B—C30B—C31B125.7 (4)
C18C—C13C—C14C111.8 (4)O6B—C30B—C31B110.6 (4)
C12C—C13C—C14C107.5 (3)O7C—C30C—O6C123.2 (5)
C18C—C13C—C17C110.1 (3)O7C—C30C—C31C125.5 (5)
C12C—C13C—C17C116.9 (3)O6C—C30C—C31C111.2 (4)
C14C—C13C—C17C99.8 (3)C30A—C31A—H31G109.5
C8A—C14A—C15A119.9 (4)C30A—C31A—H31H109.5
C8A—C14A—C13A112.8 (3)H31G—C31A—H31H109.5
C15A—C14A—C13A104.1 (3)C30A—C31A—H31I109.5
C8A—C14A—H14A106.4H31G—C31A—H31I109.5
C15A—C14A—H14A106.4H31H—C31A—H31I109.5
C13A—C14A—H14A106.4C30B—C31B—H31A109.5
C8B—C14B—C15B119.5 (4)C30B—C31B—H31B109.5
C8B—C14B—C13B115.3 (3)H31A—C31B—H31B109.5
C15B—C14B—C13B103.4 (3)C30B—C31B—H31C109.5
C8B—C14B—H14B105.8H31A—C31B—H31C109.5
C15B—C14B—H14B105.8H31B—C31B—H31C109.5
C13B—C14B—H14B105.8C30C—C31C—H31D109.5
C8C—C14C—C15C120.7 (4)C30C—C31C—H31E109.5
C8C—C14C—C13C114.9 (3)H31D—C31C—H31E109.5
C15C—C14C—C13C104.5 (3)C30C—C31C—H31F109.5
C8C—C14C—H14C105.1H31D—C31C—H31F109.5
C15C—C14C—H14C105.1H31E—C31C—H31F109.5
C13C—C14C—H14C105.1C5A—O1A—H1AO116.0
C14A—C15A—C16A104.0 (4)C5B—O1B—H1BO113.3
C14A—C15A—H15A111.0C5C—O1C—H1CO112.8
C16A—C15A—H15A111.0C9A—O2A—H2AO100.6
C14A—C15A—H15B111.0C9B—O2B—H2BO99.3
C16A—C15A—H15B111.0C9C—O2C—H2CO109.1
H15A—C15A—H15B109.0C28A—O4A—C3A117.7 (3)
C14B—C15B—C16B103.4 (4)C28B—O4B—C3B120.2 (4)
C14B—C15B—H15E111.1C28C—O4C—C3C118.0 (4)
C16B—C15B—H15E111.1C30A—O6A—C6A117.4 (4)
C14B—C15B—H15F111.1C30B—O6B—C6B116.4 (3)
C16B—C15B—H15F111.1C30C—O6C—C6C117.9 (4)
H15E—C15B—H15F109.0C23B—C24B—C25B117.8 (4)
C14C—C15C—C16C103.1 (3)C23B—C24B—H24E107.9
C14C—C15C—H15C111.1C25B—C24B—H24E107.9
C16C—C15C—H15C111.1C23B—C24B—H24F107.9
C14C—C15C—H15D111.1C25B—C24B—H24F107.9
C16C—C15C—H15D111.1H24E—C24B—H24F107.2
H15C—C15C—H15D109.1C26B—C25B—C27B110.3 (6)
C15A—C16A—C17A107.0 (4)C26B—C25B—C24B110.9 (5)
C15A—C16A—H16A110.3C27B—C25B—C24B110.8 (5)
C17A—C16A—H16A110.3C26B—C25B—H25B108.2
C15A—C16A—H16B110.3C27B—C25B—H25B108.2
C17A—C16A—H16B110.3C24B—C25B—H25B108.2
H16A—C16A—H16B108.6C26Z—C25Z—H25Z108.9
C17B—C16B—C15B107.0 (4)C25Z—C26Z—H26J109.5
C17B—C16B—H16C110.3C25Z—C26Z—H26K109.5
C15B—C16B—H16C110.3H26J—C26Z—H26K109.5
C17B—C16B—H16D110.3C25Z—C26Z—H26L109.5
C15B—C16B—H16D110.3H26J—C26Z—H26L109.5
H16C—C16B—H16D108.6H26K—C26Z—H26L109.5
C15C—C16C—C17C107.4 (3)C4—C3—H3D109.5
C15C—C16C—H16E110.2C4—C3—H3E109.5
C17C—C16C—H16E110.2H3D—C3—H3E109.5
C15C—C16C—H16F110.2C4—C3—H3F109.5
C17C—C16C—H16F110.2H3D—C3—H3F109.5
H16E—C16C—H16F108.5H3E—C3—H3F109.5
C20A—C17A—C13A119.1 (3)O2—C4—O1119 (4)
C20A—C17A—C16A112.0 (4)O2—C4—C3118 (4)
C13A—C17A—C16A103.5 (3)O1—C4—C3123 (3)
C20A—C17A—H17A107.2
C10A—C1A—C2A—C3A58.2 (5)C10B—C9B—C11B—O3B6.8 (6)
C10B—C1B—C2B—C3B57.9 (5)O2B—C9B—C11B—C12B66.5 (4)
C10C—C1C—C2C—C3C58.5 (5)C8B—C9B—C11B—C12B46.6 (5)
C1A—C2A—C3A—O4A175.1 (3)C10B—C9B—C11B—C12B173.8 (4)
C1A—C2A—C3A—C4A56.7 (5)O2C—C9C—C11C—O3C114.6 (5)
C1B—C2B—C3B—O4B174.1 (4)C8C—C9C—C11C—O3C133.9 (4)
C1B—C2B—C3B—C4B55.8 (5)C10C—C9C—C11C—O3C7.5 (6)
C1C—C2C—C3C—O4C173.7 (3)O2C—C9C—C11C—C12C66.1 (4)
C1C—C2C—C3C—C4C56.2 (5)C8C—C9C—C11C—C12C45.4 (5)
O4A—C3A—C4A—C5A173.3 (3)C10C—C9C—C11C—C12C171.8 (4)
C2A—C3A—C4A—C5A55.2 (5)O3A—C11A—C12A—C13A135.9 (4)
O4B—C3B—C4B—C5B173.4 (3)C9A—C11A—C12A—C13A47.0 (5)
C2B—C3B—C4B—C5B54.9 (5)O3B—C11B—C12B—C13B121.3 (5)
O4C—C3C—C4C—C5C172.9 (3)C9B—C11B—C12B—C13B59.4 (5)
C2C—C3C—C4C—C5C55.1 (5)O3C—C11C—C12C—C13C119.5 (5)
C3A—C4A—C5A—O1A62.3 (4)C9C—C11C—C12C—C13C59.7 (5)
C3A—C4A—C5A—C10A55.2 (5)C11A—C12A—C13A—C18A65.1 (4)
C3A—C4A—C5A—C6A176.8 (3)C11A—C12A—C13A—C14A55.0 (4)
C3B—C4B—C5B—O1B62.7 (4)C11A—C12A—C13A—C17A166.8 (3)
C3B—C4B—C5B—C6B179.5 (3)C11B—C12B—C13B—C18B60.1 (5)
C3B—C4B—C5B—C10B54.4 (5)C11B—C12B—C13B—C14B60.9 (4)
C3C—C4C—C5C—O1C63.2 (4)C11B—C12B—C13B—C17B171.3 (4)
C3C—C4C—C5C—C10C53.8 (5)C11C—C12C—C13C—C18C61.2 (4)
C3C—C4C—C5C—C6C179.5 (3)C11C—C12C—C13C—C14C60.9 (4)
O1A—C5A—C6A—O6A166.5 (3)C11C—C12C—C13C—C17C172.1 (3)
C10A—C5A—C6A—O6A78.0 (4)C7A—C8A—C14A—C15A3.9 (6)
C4A—C5A—C6A—O6A49.6 (4)C9A—C8A—C14A—C15A179.8 (3)
O1A—C5A—C6A—C7A72.8 (4)C7A—C8A—C14A—C13A127.1 (4)
C10A—C5A—C6A—C7A42.8 (5)C9A—C8A—C14A—C13A56.6 (5)
C4A—C5A—C6A—C7A170.3 (3)C18A—C13A—C14A—C8A58.2 (5)
O1B—C5B—C6B—O6B158.8 (3)C12A—C13A—C14A—C8A60.6 (5)
C4B—C5B—C6B—O6B39.9 (4)C17A—C13A—C14A—C8A177.3 (4)
C10B—C5B—C6B—O6B86.1 (4)C18A—C13A—C14A—C15A73.3 (4)
O1B—C5B—C6B—C7B78.5 (4)C12A—C13A—C14A—C15A167.8 (3)
C4B—C5B—C6B—C7B162.6 (3)C17A—C13A—C14A—C15A45.7 (4)
C10B—C5B—C6B—C7B36.6 (5)C7B—C8B—C14B—C15B13.4 (6)
O1C—C5C—C6C—O6C160.8 (3)C9B—C8B—C14B—C15B173.1 (4)
C4C—C5C—C6C—O6C42.9 (5)C7B—C8B—C14B—C13B137.6 (4)
C10C—C5C—C6C—O6C83.7 (4)C9B—C8B—C14B—C13B48.9 (5)
O1C—C5C—C6C—C7C76.5 (4)C18B—C13B—C14B—C8B61.1 (5)
C4C—C5C—C6C—C7C165.5 (4)C12B—C13B—C14B—C8B58.1 (5)
C10C—C5C—C6C—C7C38.9 (5)C17B—C13B—C14B—C8B179.9 (4)
O6A—C6A—C7A—C8A114.5 (4)C18B—C13B—C14B—C15B71.2 (4)
C5A—C6A—C7A—C8A9.8 (6)C12B—C13B—C14B—C15B169.6 (4)
O6B—C6B—C7B—C8B120.5 (4)C17B—C13B—C14B—C15B47.8 (4)
C5B—C6B—C7B—C8B4.3 (6)C7C—C8C—C14C—C15C14.2 (6)
O6C—C6C—C7C—C8C118.2 (5)C9C—C8C—C14C—C15C171.5 (4)
C5C—C6C—C7C—C8C7.3 (6)C7C—C8C—C14C—C13C140.8 (4)
C6A—C7A—C8A—C14A171.5 (4)C9C—C8C—C14C—C13C44.8 (5)
C6A—C7A—C8A—C9A4.6 (6)C18C—C13C—C14C—C8C66.0 (5)
C6B—C7B—C8B—C14B168.2 (4)C12C—C13C—C14C—C8C55.1 (5)
C6B—C7B—C8B—C9B5.0 (6)C17C—C13C—C14C—C8C177.6 (4)
C6C—C7C—C8C—C14C172.9 (4)C18C—C13C—C14C—C15C68.6 (4)
C6C—C7C—C8C—C9C1.2 (7)C12C—C13C—C14C—C15C170.3 (3)
C7A—C8A—C9A—O2A111.0 (4)C17C—C13C—C14C—C15C47.8 (4)
C14A—C8A—C9A—O2A65.3 (4)C8A—C14A—C15A—C16A162.8 (4)
C7A—C8A—C9A—C11A141.7 (4)C13A—C14A—C15A—C16A35.5 (4)
C14A—C8A—C9A—C11A42.0 (4)C8B—C14B—C15B—C16B165.4 (4)
C7A—C8A—C9A—C10A13.3 (5)C13B—C14B—C15B—C16B35.6 (5)
C14A—C8A—C9A—C10A170.4 (3)C8C—C14C—C15C—C16C167.6 (4)
C7B—C8B—C9B—O2B105.0 (4)C13C—C14C—C15C—C16C36.3 (4)
C14B—C8B—C9B—O2B68.7 (4)C14A—C15A—C16A—C17A11.7 (5)
C7B—C8B—C9B—C11B146.7 (4)C14B—C15B—C16B—C17B9.5 (5)
C14B—C8B—C9B—C11B39.6 (5)C14C—C15C—C16C—C17C10.6 (5)
C7B—C8B—C9B—C10B18.9 (5)C18A—C13A—C17A—C20A43.8 (5)
C14B—C8B—C9B—C10B167.4 (3)C12A—C13A—C17A—C20A82.9 (5)
C7C—C8C—C9C—O2C104.8 (4)C14A—C13A—C17A—C20A162.2 (4)
C14C—C8C—C9C—O2C69.4 (4)C18A—C13A—C17A—C16A81.2 (4)
C7C—C8C—C9C—C11C149.1 (4)C12A—C13A—C17A—C16A152.1 (4)
C14C—C8C—C9C—C11C36.7 (5)C14A—C13A—C17A—C16A37.1 (4)
C7C—C8C—C9C—C10C21.7 (5)C15A—C16A—C17A—C20A145.7 (4)
C14C—C8C—C9C—C10C164.2 (3)C15A—C16A—C17A—C13A16.2 (5)
O1A—C5A—C10A—C1A65.2 (4)C15B—C16B—C17B—C20B149.9 (4)
C4A—C5A—C10A—C1A53.8 (4)C15B—C16B—C17B—C13B19.8 (5)
C6A—C5A—C10A—C1A179.9 (3)C18B—C13B—C17B—C20B48.2 (5)
O1A—C5A—C10A—C19A174.0 (3)C12B—C13B—C17B—C20B78.9 (5)
C4A—C5A—C10A—C19A67.0 (4)C14B—C13B—C17B—C20B167.2 (4)
C6A—C5A—C10A—C19A59.1 (4)C18B—C13B—C17B—C16B78.1 (4)
O1A—C5A—C10A—C9A55.6 (4)C12B—C13B—C17B—C16B154.8 (4)
C4A—C5A—C10A—C9A174.6 (3)C14B—C13B—C17B—C16B40.9 (4)
C6A—C5A—C10A—C9A59.2 (4)C18C—C13C—C17C—C20C48.3 (5)
C2A—C1A—C10A—C5A55.7 (4)C12C—C13C—C17C—C20C78.5 (5)
C2A—C1A—C10A—C19A65.0 (4)C14C—C13C—C17C—C20C166.0 (4)
C2A—C1A—C10A—C9A174.4 (3)C18C—C13C—C17C—C16C78.4 (4)
O2A—C9A—C10A—C5A78.5 (4)C12C—C13C—C17C—C16C154.8 (4)
C8A—C9A—C10A—C5A43.2 (4)C14C—C13C—C17C—C16C39.4 (4)
C11A—C9A—C10A—C5A170.3 (3)C15C—C16C—C17C—C20C149.0 (4)
O2A—C9A—C10A—C1A40.2 (4)C15C—C16C—C17C—C13C18.4 (4)
C8A—C9A—C10A—C1A161.8 (3)C13A—C17A—C20A—C21A53.9 (5)
C11A—C9A—C10A—C1A71.1 (4)C16A—C17A—C20A—C21A174.8 (4)
O2A—C9A—C10A—C19A162.0 (3)C13A—C17A—C20A—C22A177.9 (4)
C8A—C9A—C10A—C19A76.4 (4)C16A—C17A—C20A—C22A61.2 (5)
C11A—C9A—C10A—C19A50.7 (4)C16B—C17B—C20B—C21B177.3 (4)
C2B—C1B—C10B—C19B63.4 (5)C13B—C17B—C20B—C21B55.6 (6)
C2B—C1B—C10B—C9B175.7 (4)C16B—C17B—C20B—C22B59.0 (5)
C2B—C1B—C10B—C5B56.4 (5)C13B—C17B—C20B—C22B179.4 (4)
O2B—C9B—C10B—C1B47.0 (5)C13C—C17C—C20C—C21C59.4 (5)
C8B—C9B—C10B—C1B168.2 (3)C16C—C17C—C20C—C21C179.0 (4)
C11B—C9B—C10B—C1B65.6 (4)C13C—C17C—C20C—C22C176.2 (4)
O2B—C9B—C10B—C19B168.8 (3)C16C—C17C—C20C—C22C54.6 (5)
C8B—C9B—C10B—C19B70.0 (4)C21A—C20A—C22A—C23A75.7 (5)
C11B—C9B—C10B—C19B56.2 (4)C17A—C20A—C22A—C23A158.4 (4)
O2B—C9B—C10B—C5B72.2 (4)C21B—C20B—C22B—C23B57.0 (6)
C8B—C9B—C10B—C5B49.0 (4)C17B—C20B—C22B—C23B177.3 (4)
C11B—C9B—C10B—C5B175.2 (3)C21C—C20C—C22C—C23C57.4 (6)
O1B—C5B—C10B—C1B64.4 (4)C17C—C20C—C22C—C23C177.5 (4)
C4B—C5B—C10B—C1B54.5 (5)C20A—C22A—C23A—C24A174.5 (4)
C6B—C5B—C10B—C1B179.2 (3)C20B—C22B—C23B—C24B176.4 (5)
O1B—C5B—C10B—C19B175.1 (3)C20C—C22C—C23C—C24C168.0 (5)
C4B—C5B—C10B—C19B66.0 (4)C22A—C23A—C24A—C25A166.4 (4)
C6B—C5B—C10B—C19B60.3 (4)C22C—C23C—C24C—C25C170.0 (6)
O1B—C5B—C10B—C9B56.4 (4)C23A—C24A—C25A—C27A179.6 (4)
C4B—C5B—C10B—C9B175.2 (3)C23A—C24A—C25A—C26A56.0 (5)
C6B—C5B—C10B—C9B58.5 (4)C23C—C24C—C25C—C26C30.3 (12)
C2C—C1C—C10C—C19C63.6 (5)C23C—C24C—C25C—C27C174.1 (6)
C2C—C1C—C10C—C9C174.6 (3)O5A—C28A—O4A—C3A7.6 (8)
C2C—C1C—C10C—C5C56.1 (5)C29A—C28A—O4A—C3A172.0 (4)
O2C—C9C—C10C—C19C169.3 (3)C4A—C3A—O4A—C28A80.4 (5)
C8C—C9C—C10C—C19C68.7 (4)C2A—C3A—O4A—C28A159.5 (4)
C11C—C9C—C10C—C19C56.4 (5)O5B—C28B—O4B—C3B5.0 (7)
O2C—C9C—C10C—C1C46.9 (5)C29B—C28B—O4B—C3B176.5 (4)
C8C—C9C—C10C—C1C169.0 (3)C2B—C3B—O4B—C28B124.3 (4)
C11C—C9C—C10C—C1C65.9 (4)C4B—C3B—O4B—C28B114.6 (4)
O2C—C9C—C10C—C5C71.5 (4)O5C—C28C—O4C—C3C7.0 (7)
C8C—C9C—C10C—C5C50.6 (4)C29C—C28C—O4C—C3C173.2 (4)
C11C—C9C—C10C—C5C175.7 (3)C2C—C3C—O4C—C28C143.4 (4)
O1C—C5C—C10C—C19C174.1 (3)C4C—C3C—O4C—C28C95.9 (4)
C4C—C5C—C10C—C19C67.0 (5)O7A—C30A—O6A—C6A5.2 (6)
C6C—C5C—C10C—C19C58.2 (5)C31A—C30A—O6A—C6A174.4 (4)
O1C—C5C—C10C—C1C65.9 (4)C7A—C6A—O6A—C30A129.6 (4)
C4C—C5C—C10C—C1C53.0 (5)C5A—C6A—O6A—C30A106.8 (4)
C6C—C5C—C10C—C1C178.2 (3)O7B—C30B—O6B—C6B4.8 (6)
O1C—C5C—C10C—C9C55.1 (4)C31B—C30B—O6B—C6B173.7 (4)
C4C—C5C—C10C—C9C174.0 (3)C7B—C6B—O6B—C30B130.8 (4)
C6C—C5C—C10C—C9C60.8 (4)C5B—C6B—O6B—C30B102.6 (4)
O2A—C9A—C11A—O3A102.4 (5)O7C—C30C—O6C—C6C3.4 (7)
C8A—C9A—C11A—O3A144.9 (4)C31C—C30C—O6C—C6C177.2 (4)
C10A—C9A—C11A—O3A16.6 (6)C7C—C6C—O6C—C30C127.6 (4)
O2A—C9A—C11A—C12A74.6 (4)C5C—C6C—O6C—C30C107.5 (4)
C8A—C9A—C11A—C12A38.1 (5)C22B—C23B—C24B—C25B174.9 (6)
C10A—C9A—C11A—C12A166.3 (4)C23B—C24B—C25B—C26B56.2 (8)
O2B—C9B—C11B—O3B112.9 (5)C23B—C24B—C25B—C27B179.1 (7)
C8B—C9B—C11B—O3B134.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1AO···O3Ci0.951.792.745 (4)177
O1B—H1BO···O5C0.802.022.819 (4)175
O1C—H1CO···O5B0.891.812.699 (4)178
O2A—H2AO···O1A0.931.882.691 (4)145
O2B—H2BO···O1B0.901.802.628 (4)153
O2C—H2CO···O1C1.051.772.614 (4)134
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC31H48O7·0.04C2H4O2
Mr535.45
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)10.242 (2), 28.556 (5), 30.214 (6)
V3)8837 (3)
Z12
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.45 × 0.30 × 0.17
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.963, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
82574, 11048, 6969
Rint0.097
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.185, 1.00
No. of reflections11048
No. of parameters1072
No. of restraints13
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.31

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003) and SADABS (Bruker, 2001), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1AO···O3Ci0.951.792.745 (4)177.2
O1B—H1BO···O5C0.802.022.819 (4)175.3
O1C—H1CO···O5B0.891.812.699 (4)177.6
O2A—H2AO···O1A0.931.882.691 (4)145.0
O2B—H2BO···O1B0.901.802.628 (4)153.4
O2C—H2CO···O1C1.051.772.614 (4)133.9
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

Acknowledgements

The authors thank the Centro Inter­dipartimentale di Metodologie Chimico–Fisiche, Università degli Studi di Napoli "Federico II" for the X-ray facilities.

References

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Volume 69| Part 6| June 2013| Pages o879-o880
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