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

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ISSN: 2056-9890

7-De­acetyl­gedunin

aResearch Centre of Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand, and bResearch Centre of Bioorganic Chemistry and Center for Petroleum, Petrochemicals and Advanced Materials, Chulalongkorn University, Bangkok 10330, Thailand
*Correspondence e-mail: nongnuj.j@chula.ac.th

(Received 5 December 2010; accepted 11 December 2010; online 18 December 2010)

The title compound [systematic name: (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(furan-3-yl)-5-hy­droxy-4b,7,7,10a,12a-penta­methyl-4b,5,6,6a,7,10a,10b,11,12,12a-deca­hydro­naphtho­[2,1-f]oxireno[2,3-d]isochromene-3,8(1H,3aH)-dione], C26H32O6, which is a limonoid-type triterpene isolated from the seeds of X. moluccensis, crystallizes with three independent mol­ecules with very similar geometries in the asymmetric unit. In each mol­ecule, the four fused six-membered rings of the genudin core adopt distorted half-chair, chair, twist-boat and twisted half-chair conformations. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into helical chains propagated in [100]. Weak non-classical C—H⋯O contacts further consolidate the crystal packing.

Related literature

For general background to limonoid and its potential bio­activity, see: Koul et al. (2004[Koul, O., Sing, G., Singh, R., Daniewski, W. M. & Berlozecki, S. (2004). J. Biosci. 29, 409-416.]); Endo et al. (2002[Endo, T., Kita, M., Shimada, T., Moriguchi, T., Hidaki, T., Matsumoto, R., Hasegawa, S. & Omura, M. (2002). Plant Biotechnol. 19, 397-403.]); Nakagawa et al. (2001[Nakagawa, H., Duan, H. & Takaishi, Y. (2001). Chem. Pharm. Bull. 49, 649-651.]); Pudhom et al. (2009[Pudhom, K., Sommit, D., Nuclear, P., Ngamrojanavanich, N. & Petsom, A. (2009). J. Nat. Prod. 72, 2188-2191.]). For related structures, see: Waratchareeyakul et al. (2004[Waratchareeyakul, W., Chantrapromma, S., Fun, H.-K., Razak, I. A., Karalai, C. & Ponglimanont, C. (2004). Acta Cryst. E60, o1964-o1966.]); Hofer et al. (2009[Hofer, M., Greger, H. & Mereiter, K. (2009). Acta Cryst. E65, o1942-o1943.]). For limonoids with novel skeletons extracted from Xylocarpus granatum Koenig, see: Wu et al. (2004[Wu, J., Xiao, Q., Huang, J., Xiao, Z., Qi, S., Li, Q. & Zhang, S. (2004). Org. Lett. 6, 1841-1844.]); Cui et al. (2005[Cui, J., Deng, Z., Li, J., Fu, H., Proksch, P. & Lin, W. (2005). Phytochemistry, 66, 2334-2339.], 2007[Cui, J., Wu, J., Deng, Z., Proksch, P. & Lin, W. (2007). J. Nat. Prod. 70, 772-778.]); Zhou et al. (2006[Zhou, Y., Cheng, F., Wu, J. & Zou, K. (2006). J. Nat. Prod. 69, 1083-1085.]); Li et al. (2009[Li, M.-Y., Yang, X.-B., Pan, J.-P., Feng, G., Xiao, Q., Sinkkonen, J., Satyanandamurty, T. & Wu, J. (2009). J. Nat. Prod. 72, 2110-2114.]). The absolute configuration was assigned on the basis of literature data, see: Pudhom et al. (2009[Pudhom, K., Sommit, D., Nuclear, P., Ngamrojanavanich, N. & Petsom, A. (2009). J. Nat. Prod. 72, 2188-2191.]); Mitsui et al. (2006);[Mitsui, K., Saito, H., Yamamura, R., Fukaya, H., Hitotsuyanagi, Y. & Takeya, K. (2006). J. Nat. Prod. 69, 1310-1314.] Waratchareeyakul et al. (2004[Waratchareeyakul, W., Chantrapromma, S., Fun, H.-K., Razak, I. A., Karalai, C. & Ponglimanont, C. (2004). Acta Cryst. E60, o1964-o1966.]); Hofer et al. (2009[Hofer, M., Greger, H. & Mereiter, K. (2009). Acta Cryst. E65, o1942-o1943.]).

[Scheme 1]

Experimental

Crystal data
  • C26H32O6

  • Mr = 440.52

  • Orthorhombic, P 21 21 21

  • a = 12.3642 (4) Å

  • b = 12.8445 (5) Å

  • c = 43.5584 (15) Å

  • V = 6917.6 (4) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.48 × 0.40 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • 38709 measured reflections

  • 9382 independent reflections

  • 6530 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.212

  • S = 0.99

  • 9382 reflections

  • 891 parameters

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

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4A—H4OA⋯O1 1.01 (6) 1.83 (6) 2.818 (5) 169 (5)
O4—H4O⋯O1B 0.81 (5) 2.14 (5) 2.952 (5) 177 (4)
O4B—H4OB⋯O5Ai 0.88 (7) 2.06 (7) 2.849 (5) 149 (6)
C7—H7⋯O1A 0.98 2.55 3.525 (6) 172
C11—H11A⋯O3ii 0.97 2.45 3.278 (6) 143
C21B—H21B⋯O5Biii 0.93 2.52 3.369 (9) 151
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Limonoid research from the Meliaceae family is of growing interest due to a range of biological activities, such as insect antifeedants and growth regulators, antibacterial, antifungal, antimalarial, anticancer and antiviral activities on humans (Koul et al., 2004; Endo et al., 2002; Nakagawa et al., 2001). Such a focused interest upon limonoids from the family Meliaceae has already resulted in the discovery of several limonoids with novel skeletons, mostly, but not exclusively, from within the genus Xylocarpus, and, in particular, the cannonball mangrove, Xylocarpus granatum Koenig (Wu et al., 2004; Cui et al., 2005; Zhou et al., 2006; Cui et al., 2007; Li et al., 2009; Pudhom et al., 2009). Limonoid derivatives have been found in all Xylocarpus plants studied, but their distribution and content may vary both between different plant species, and between parts or geocultivars of the same species. This, combined with their wide ranging structural diversity and potential biological significance across this plant family, prompted us to investigate another plant in this genus, Xylocarpus moluccensis. Herein, the complete assignments of NMR data and the crystal and molecular structure of 7-deacetylgedunin obtained from the seeds of X. moluccensis, were reported for the first time.

The asymmetric unit of the title compound contains three crystallographically independent molecules. There is very little difference between the bond lengths and angles of these molecules. The molecule consists of four fused six membered rings (A, B, C and D) of genudin core. All the rings are all trans fused and adopt distorted half-chair, chair, twist-boat, and twisted half-chair conformation, respectively. The furan ring is planar and nearly perpendicular orientation to the main plane of the molecule.

In the crystal structure, molecules related by translation along the a axis are linked into chains through O—H···O hydrogen bonds. Weak non-classical C—H···O contacts are also observed in the structure.

The absolute configuration was assigned on the basis of literature data (Pudhom et al., 2009; Mitsui et al., 2006; Waratchareeyakul et al., 2004; Hofer et al., 2009).

Related literature top

For general background to limonoid and its potential bioctivity, see: Koul et al. (2004); Endo et al. (2002); Nakagawa et al. (2001); Pudhom et al. (2009). For related structures, see: Waratchareeyakul et al. (2004); Hofer et al. (2009). For limonoids with novel skeletons extracted from Xylocarpus granatum Koenig, see: Wu et al. (2004); Cui et al. (2005, 2007); Zhou et al. (2006); Li et al. (2009). The absolute configuration was assigned on the basis of literature data (Pudhom et al., 2009; Mitsui et al., 2006; Waratchareeyakul et al., 2004; Hofer et al., 2009).

Experimental top

General Experimental Procedures. Melting point was measured using a Fisher-Johns melting point apparatus. HRESIMS spectrum was obtained using a Bruker micrOTOF mass spectrometer. The NMR spectra were recorded on a Varian YH400 spectrometer at 400 MHz for 1H NMR and at 100 MHz for 13C NMR using TMS (tetramethylsilane) as internal standard.

Plant Material. Fruits of X. moluccensis were collected from Phuket Province, Thailand, in December 2009. Plants materials were identified by Royal Forest Department, Bangkok, Thailand.

Extraction and Isolation of 7-Deacetylgedunin (1). Air-dried powdered seeds of X. moluccensis (3 kg) were extracted with MeOH (5L x 2, each for three days). The extract was concentrated under reduced pressure, followed by suspension in water and extraction with EtOAc. The resulting EtOAc crude extract (35 g) was chromatographed on a silica gel column eluted with a gradient of acetone–n-hexane (from 1:9 to 1:0) to yield 12 fractions. Fraction 7 (2.80 g) was then applied to a silica gel column and eluted with a 1:2 mixture of acetone–n-hexane to afford 12 subfractions. Subfraction 4 was further purified by silica gel column chromatography (acetone–n-hexane; 1:4) and recrystallized from EtOAc–n-hexane (1:1) to afford 7-deacetylgedunin (1, 15.0 mg).

7-Deacetylgedunin (1): colorless crystals; mp 246–247 oC; 1H NMR (400 MHz, CDCl3) d 7.41 (1H, s, H-21), 7.40 (1H, s, H-23), 7.10 (1H, d, J = 10.4 Hz, H-1), 6.35 (1H, s, H-22), 5.84 (1H, d, J = 10.4 Hz, H-2), 5.60 (1H, s, H-17), 3.90 (1H, s, H-15), 3.57 (1H, br s, H-7), 2.52 (1H, m, H-9), 2.49 (1H, m, H-5), 1.95 (1H, m, H-11b), 1.89 (1H, m, H-6a), 1.80 (1H, m, H-11b), 1.71 (1H, m, H-12a), 1.69 (1H, m, H-6 b), 1.54 (1H, m, H-12b), 1.23 (3H, s, CH3-18), 1.19 (3H, s, CH3-19), 1.14 (3H, s, CH3-28), 1.09 (3H, s, CH3-29), 1.00 (3H, s, CH3-30); 13C NMR (100 MHz, CDCl3) d 204.6 (C, C-3), 168.3 (C, C-16), 157.8 (CH, C-1), 143.0 (CH, C-23), 141.2 (CH, C-21), 125.7 (CH, C-2), 120.6 (C, C-20), 110.0 (CH, C-22), 78.5 (CH, C-17), 70.0 (C, C-14), 69.7 (CH, C-7), 57.8 (CH, C-15), 44.6 (CH, C-5), 44.2 (C, C-4), 43.7 (C, C-8), 40.7 (C, C-10), 38.3 (C, C-13), 38.0 (CH, C-9), 27.3 (CH2, C-6), 27.2 (CH3, C-28), 26.4 (CH2, C-12), 21.5 (CH3, C-29), 19.9 (CH3, C-19), 18.7 (CH3, C-30), 17.8 (CH3, C-18), 15.0 (CH2, C-11); HRESIMS m/z 463.2101 [M+Na]+ (calcd for C26H32O6Na, 463.2097).

Refinement top

C-bound H atoms were geometrically positioned and treated as riding atoms with distances C—H = 0.96 Å (CH3), 0.97 Å (CH2), 0.93 Å (CH), and Uiso(H) = 1.20 Ueq(C) for methylene and aromatic, 1.50 Ueq(C) for methyl. O-bound H atoms were located on a difference map and refined isotropically. The absolute structure could not be determined from the X-ray analysis, but it was known from earlier work on related compounds (e.g. Pudhom et al., 2009; Mitsui et al., 2006; Waratchareeyakul et al., 2004). 6,498 Friedel pairs were therefore merged before the final refinement.

Structure description top

Limonoid research from the Meliaceae family is of growing interest due to a range of biological activities, such as insect antifeedants and growth regulators, antibacterial, antifungal, antimalarial, anticancer and antiviral activities on humans (Koul et al., 2004; Endo et al., 2002; Nakagawa et al., 2001). Such a focused interest upon limonoids from the family Meliaceae has already resulted in the discovery of several limonoids with novel skeletons, mostly, but not exclusively, from within the genus Xylocarpus, and, in particular, the cannonball mangrove, Xylocarpus granatum Koenig (Wu et al., 2004; Cui et al., 2005; Zhou et al., 2006; Cui et al., 2007; Li et al., 2009; Pudhom et al., 2009). Limonoid derivatives have been found in all Xylocarpus plants studied, but their distribution and content may vary both between different plant species, and between parts or geocultivars of the same species. This, combined with their wide ranging structural diversity and potential biological significance across this plant family, prompted us to investigate another plant in this genus, Xylocarpus moluccensis. Herein, the complete assignments of NMR data and the crystal and molecular structure of 7-deacetylgedunin obtained from the seeds of X. moluccensis, were reported for the first time.

The asymmetric unit of the title compound contains three crystallographically independent molecules. There is very little difference between the bond lengths and angles of these molecules. The molecule consists of four fused six membered rings (A, B, C and D) of genudin core. All the rings are all trans fused and adopt distorted half-chair, chair, twist-boat, and twisted half-chair conformation, respectively. The furan ring is planar and nearly perpendicular orientation to the main plane of the molecule.

In the crystal structure, molecules related by translation along the a axis are linked into chains through O—H···O hydrogen bonds. Weak non-classical C—H···O contacts are also observed in the structure.

The absolute configuration was assigned on the basis of literature data (Pudhom et al., 2009; Mitsui et al., 2006; Waratchareeyakul et al., 2004; Hofer et al., 2009).

For general background to limonoid and its potential bioctivity, see: Koul et al. (2004); Endo et al. (2002); Nakagawa et al. (2001); Pudhom et al. (2009). For related structures, see: Waratchareeyakul et al. (2004); Hofer et al. (2009). For limonoids with novel skeletons extracted from Xylocarpus granatum Koenig, see: Wu et al. (2004); Cui et al. (2005, 2007); Zhou et al. (2006); Li et al. (2009). The absolute configuration was assigned on the basis of literature data (Pudhom et al., 2009; Mitsui et al., 2006; Waratchareeyakul et al., 2004; Hofer et al., 2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme in one independent molecule.
(1S,3aS,4aR,4bS,5R,6aR,10aR, 10bR,12aS)-1-(furan-3-yl)-5-hydroxy-4b,7,7,10a,12a-pentamethyl- 4b,5,6,6a,7,10a,10b,11,12,12a-decahydronaphtho[2,1-f]oxireno[2,3- d]isochromene-3,8(1H,3aH)-dione top
Crystal data top
C26H32O6Z = 12
Mr = 440.52F(000) = 2832
Orthorhombic, P212121Dx = 1.269 Mg m3
Hall symbol: P 2ac 2abMo Kα radiation, λ = 0.71073 Å
a = 12.3642 (4) ŵ = 0.09 mm1
b = 12.8445 (5) ÅT = 296 K
c = 43.5584 (15) ÅPrism, colourless
V = 6917.6 (4) Å30.48 × 0.40 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
6530 reflections with I > 2σ(I)
Radiation source: Mo KαRint = 0.059
Graphite monochromatorθmax = 28.3°, θmin = 1.7°
φ and ω scansh = 816
38709 measured reflectionsk = 1717
9382 independent reflectionsl = 2858
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.1415P)2 + 0.6215P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.068(Δ/σ)max = 0.011
wR(F2) = 0.212Δρmax = 0.41 e Å3
S = 0.99Δρmin = 0.40 e Å3
9382 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
891 parametersExtinction coefficient: 0.0120 (11)
0 restraints
Crystal data top
C26H32O6V = 6917.6 (4) Å3
Mr = 440.52Z = 12
Orthorhombic, P212121Mo Kα radiation
a = 12.3642 (4) ŵ = 0.09 mm1
b = 12.8445 (5) ÅT = 296 K
c = 43.5584 (15) Å0.48 × 0.40 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
6530 reflections with I > 2σ(I)
38709 measured reflectionsRint = 0.059
9382 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.212H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.41 e Å3
9382 reflectionsΔρmin = 0.40 e Å3
891 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
C10.2329 (5)0.3351 (4)0.79409 (14)0.0681 (15)
H10.27830.28870.7840.082*
C20.1516 (6)0.2994 (4)0.81028 (17)0.0771 (17)
H20.14170.22770.81140.092*
C30.0755 (5)0.3666 (4)0.82667 (12)0.0584 (12)
C40.1132 (4)0.4728 (4)0.83638 (10)0.0506 (11)
C50.2300 (4)0.4960 (3)0.82397 (9)0.0428 (9)
H50.2790.45920.8380.051*
C60.2623 (4)0.6099 (3)0.82612 (10)0.0452 (9)
H6A0.24410.63630.84630.054*
H6B0.22190.64980.81110.054*
C70.3837 (4)0.6246 (3)0.82045 (9)0.0442 (9)
H70.40110.69890.82170.053*
C80.4174 (4)0.5835 (3)0.78881 (9)0.0399 (9)
C90.3780 (4)0.4687 (3)0.78542 (9)0.0406 (9)
H90.41560.43040.80170.049*
C100.2539 (4)0.4503 (3)0.79171 (10)0.0447 (10)
C110.4186 (5)0.4204 (4)0.75536 (10)0.0572 (12)
H11A0.41680.34520.75740.069*
H11B0.36870.43910.73910.069*
C120.5328 (4)0.4528 (4)0.74565 (9)0.0493 (11)
H12A0.52750.50780.73050.059*
H12B0.56830.39390.73610.059*
C130.6023 (4)0.4911 (3)0.77253 (9)0.0418 (9)
C140.5430 (4)0.5869 (3)0.78525 (9)0.0416 (9)
C150.6123 (4)0.6585 (4)0.80297 (12)0.0543 (11)
H150.57810.69840.81950.065*
C160.7301 (4)0.6339 (4)0.80624 (12)0.0576 (12)
C170.7122 (4)0.5284 (4)0.76025 (10)0.0522 (11)
H170.69940.58090.74430.063*
C180.6207 (4)0.4083 (4)0.79754 (10)0.0511 (11)
H18A0.69390.41280.80480.077*
H18B0.60810.34030.78910.077*
H18C0.57170.42030.81430.077*
C190.1780 (5)0.4887 (5)0.76595 (11)0.0638 (14)
H19A0.20110.46020.74670.096*
H19B0.18040.56340.7650.096*
H19C0.10540.46660.77020.096*
C200.7835 (4)0.4456 (5)0.74728 (12)0.0619 (14)
C210.7901 (5)0.4192 (6)0.71699 (13)0.0825 (19)
H210.75090.45070.70130.099*
C220.8579 (5)0.3800 (5)0.76247 (14)0.0716 (16)
H220.87240.37930.78340.086*
C230.9039 (5)0.3185 (6)0.7410 (2)0.089 (2)
H230.95660.26860.7450.107*
C280.1188 (5)0.4697 (6)0.87202 (12)0.0689 (15)
H28A0.14190.53620.87960.103*
H28B0.16940.41720.87830.103*
H28C0.04860.45360.88010.103*
C290.0279 (4)0.5528 (4)0.82682 (13)0.0620 (13)
H29A0.05090.62110.8330.093*
H29B0.03970.53650.83650.093*
H29C0.01920.55120.80490.093*
C300.3711 (5)0.6552 (4)0.76355 (11)0.0583 (12)
H30A0.39210.62930.74380.087*
H30B0.39880.72440.76620.087*
H30C0.29360.65640.7650.087*
O10.7827 (3)0.6660 (3)0.82751 (10)0.0790 (12)
O20.7768 (3)0.5761 (3)0.78487 (8)0.0626 (9)
O30.5820 (3)0.6830 (3)0.77226 (9)0.0639 (9)
O40.4456 (3)0.5692 (3)0.84286 (7)0.0515 (8)
H4O0.417 (4)0.585 (4)0.8589 (11)0.036 (11)*
O50.0150 (3)0.3360 (4)0.83266 (11)0.0803 (12)
O60.8623 (4)0.3401 (5)0.71286 (12)0.0992 (16)
C1A0.9781 (4)1.0580 (5)0.92122 (11)0.0641 (15)
H1A0.93791.11070.93040.077*
C2A1.0459 (5)1.0028 (5)0.93859 (11)0.0684 (16)
H2A1.04961.0170.95950.082*
C3A1.1140 (4)0.9214 (4)0.92606 (10)0.0503 (10)
C4A1.0875 (4)0.8730 (4)0.89477 (10)0.0484 (10)
C5A0.9809 (4)0.9208 (3)0.88216 (8)0.0419 (9)
H5A0.92390.88780.89440.05*
C6A0.9539 (4)0.8910 (4)0.84898 (9)0.0518 (11)
H6A10.99970.93010.83510.062*
H6A20.96840.81750.84590.062*
C7A0.8359 (4)0.9135 (3)0.84180 (8)0.0436 (10)
H7A0.82170.8940.82040.052*
C8A0.8068 (4)1.0282 (3)0.84607 (8)0.0404 (9)
C9A0.8434 (4)1.0640 (3)0.87876 (9)0.0400 (9)
H9A0.794 (2)1.017 (2)0.8948 (7)0.048*
C10A0.9641 (4)1.0386 (3)0.88735 (9)0.0437 (9)
C11A0.8101 (4)1.1775 (4)0.88503 (13)0.0551 (12)
H11C0.86211.22340.87530.066*
H11D0.81341.190.9070.066*
C12A0.6951 (4)1.2064 (4)0.87344 (13)0.0535 (12)
H12C0.65991.250.88860.064*
H12D0.70141.24640.85460.064*
C13A0.6247 (4)1.1109 (3)0.86738 (9)0.0439 (9)
C14A0.6823 (4)1.0445 (3)0.84370 (8)0.0432 (9)
C15A0.6110 (4)0.9696 (4)0.82740 (10)0.0546 (12)
H15A0.64350.90430.82030.066*
C16A0.4943 (4)0.9683 (4)0.83523 (10)0.0568 (12)
C17A0.5149 (4)1.1464 (4)0.85369 (12)0.0580 (12)
H17A0.52921.18680.8350.07*
C18A0.5998 (4)1.0475 (4)0.89699 (9)0.0497 (10)
H18D0.52331.0360.89850.075*
H18E0.62441.08560.91460.075*
H18F0.63650.98160.89610.075*
C19A1.0486 (4)1.1073 (4)0.87135 (16)0.0673 (14)
H19D1.02361.1780.87090.101*
H19E1.05951.0830.85070.101*
H19F1.11571.10380.88240.101*
C20A0.4448 (4)1.2091 (4)0.87418 (14)0.0638 (14)
C21A0.4463 (6)1.3170 (5)0.87942 (19)0.087 (2)
H21A0.49321.36370.870.105*
C23A0.3716 (5)1.3422 (5)0.8996 (2)0.084 (2)
H23A0.35821.40890.9070.101*
C22A0.3633 (6)1.1741 (6)0.8930 (2)0.098 (2)
H22A0.34251.10490.89520.118*
C28A1.1867 (5)0.8851 (6)0.87352 (14)0.0790 (18)
H28D1.19880.95750.86940.118*
H28E1.17360.8490.85460.118*
H28F1.24930.85610.88340.118*
C29A1.0675 (5)0.7570 (4)0.90139 (12)0.0665 (14)
H29D1.13190.72650.90980.1*
H29E1.04880.72190.88270.1*
H29F1.00930.750.91580.1*
C30A0.8591 (5)1.0937 (4)0.82029 (11)0.0625 (13)
H30D0.93631.08580.8210.094*
H30E0.84071.16570.82310.094*
H30F0.83291.07040.80070.094*
O1A0.4394 (4)0.8906 (3)0.83252 (10)0.0811 (12)
O2A0.4484 (3)1.0553 (3)0.84539 (9)0.0640 (9)
O3A0.6444 (3)1.0643 (3)0.81249 (7)0.0626 (10)
O4A0.7686 (3)0.8530 (3)0.86112 (7)0.0523 (8)
H4OA0.777 (5)0.782 (5)0.8515 (13)0.065 (16)*
O5A1.1935 (3)0.8921 (4)0.94055 (9)0.0722 (11)
O6A0.3180 (4)1.2554 (5)0.90785 (18)0.120 (2)
C1B0.7433 (4)1.0404 (5)0.97920 (15)0.0711 (17)
H1B0.79810.99990.97080.085*
C2B0.7529 (4)1.1433 (5)0.97816 (15)0.0710 (16)
H2B0.81311.17210.96850.085*
C3B0.6718 (5)1.2134 (4)0.99168 (12)0.0594 (13)
C4B0.5592 (4)1.1725 (4)0.99750 (11)0.0520 (11)
C5B0.5477 (3)1.0577 (3)0.98712 (9)0.0402 (9)
H5B0.54341.06150.96470.048*
C6B0.4429 (3)1.0062 (4)0.99666 (9)0.0442 (9)
H6B10.38291.0530.99270.053*
H6B20.44470.99141.01850.053*
C7B0.4263 (3)0.9037 (3)0.97855 (8)0.0365 (8)
H7B0.35840.87120.9850.044*
C8B0.5194 (3)0.8268 (3)0.98340 (8)0.0347 (8)
C9B0.6275 (3)0.8821 (3)0.97583 (9)0.0392 (9)
H9B0.62160.9020.95420.047*
C10B0.6472 (3)0.9864 (4)0.99346 (10)0.0468 (10)
C11B0.7244 (3)0.8066 (4)0.97729 (12)0.0528 (12)
H11E0.78140.83360.96420.063*
H11F0.75190.80610.99820.063*
C12B0.7007 (4)0.6938 (4)0.96770 (11)0.0480 (10)
H12E0.76480.6640.95830.058*
H12F0.68350.6530.98580.058*
C13B0.6063 (3)0.6881 (3)0.94497 (8)0.0350 (8)
C14B0.5059 (3)0.7298 (3)0.96164 (8)0.0333 (8)
C15B0.4036 (3)0.7000 (4)0.94751 (9)0.0411 (9)
H15B0.34320.74920.94910.049*
C16B0.4068 (3)0.6311 (4)0.91999 (9)0.0454 (10)
C17B0.5830 (3)0.5723 (3)0.93720 (9)0.0386 (8)
H17B0.56620.53540.95630.046*
C18B0.6283 (4)0.7494 (4)0.91519 (9)0.0459 (10)
H18G0.6220.82260.91920.069*
H18H0.57660.72950.89980.069*
H18I0.70.73410.9080.069*
C19B0.6749 (5)0.9765 (5)1.02792 (12)0.0696 (16)
H19G0.72610.92111.03080.104*
H19H0.61030.96151.03930.104*
H19I0.70561.04071.03510.104*
C20B0.6723 (4)0.5152 (4)0.92109 (10)0.0460 (10)
C21B0.7413 (5)0.4496 (4)0.93466 (14)0.0652 (14)
H21B0.73930.43090.95530.078*
C22B0.7025 (5)0.5200 (4)0.88938 (13)0.0629 (13)
H22B0.6690.55840.8740.076*
C23B0.7888 (5)0.4578 (5)0.88646 (18)0.0765 (18)
H23B0.82560.44650.86810.092*
C28B0.4850 (5)1.2395 (5)0.97733 (15)0.0708 (15)
H28G0.49471.31160.98250.106*
H28H0.41111.220.98080.106*
H28I0.50291.22880.95610.106*
C29B0.5307 (5)1.1919 (5)1.03137 (13)0.0689 (15)
H29G0.58121.15561.04430.103*
H29H0.45891.16711.03540.103*
H29I0.53431.26521.03560.103*
C30B0.5157 (4)0.7846 (4)1.01660 (9)0.0479 (10)
H30G0.51320.84191.03070.072*
H30H0.57910.74361.02050.072*
H30I0.45240.74221.01920.072*
O1B0.3378 (3)0.6324 (3)0.90038 (8)0.0638 (10)
O2B0.4888 (2)0.5657 (3)0.91689 (6)0.0472 (7)
O3B0.4382 (2)0.6494 (3)0.97506 (6)0.0473 (7)
O4B0.4197 (3)0.9291 (3)0.94662 (6)0.0457 (7)
H4OB0.356 (6)0.926 (5)0.9378 (14)0.077 (19)*
O5B0.6974 (4)1.3024 (3)0.99746 (13)0.0910 (15)
O6B0.8156 (4)0.4137 (4)0.91363 (13)0.0871 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.074 (4)0.042 (3)0.088 (4)0.019 (3)0.016 (3)0.017 (3)
C20.079 (4)0.042 (3)0.110 (5)0.013 (3)0.013 (4)0.008 (3)
C30.060 (3)0.050 (3)0.065 (3)0.008 (2)0.000 (2)0.010 (2)
C40.041 (2)0.060 (3)0.050 (2)0.000 (2)0.0023 (18)0.004 (2)
C50.043 (2)0.042 (2)0.0444 (19)0.0048 (19)0.0045 (17)0.0015 (17)
C60.046 (2)0.039 (2)0.050 (2)0.0038 (19)0.0041 (18)0.0074 (18)
C70.047 (2)0.036 (2)0.050 (2)0.0022 (19)0.0042 (18)0.0123 (18)
C80.053 (2)0.0269 (18)0.0400 (18)0.0009 (18)0.0020 (17)0.0012 (15)
C90.052 (2)0.0325 (19)0.0377 (17)0.0053 (19)0.0003 (17)0.0038 (16)
C100.047 (2)0.037 (2)0.050 (2)0.0079 (19)0.0040 (19)0.0059 (18)
C110.078 (3)0.048 (3)0.045 (2)0.010 (3)0.005 (2)0.017 (2)
C120.068 (3)0.044 (2)0.0367 (18)0.001 (2)0.0045 (19)0.0073 (18)
C130.050 (2)0.035 (2)0.0405 (18)0.0029 (18)0.0060 (17)0.0026 (16)
C140.055 (2)0.0248 (18)0.0446 (19)0.0062 (18)0.0041 (18)0.0028 (16)
C150.056 (3)0.038 (2)0.069 (3)0.008 (2)0.011 (2)0.011 (2)
C160.057 (3)0.044 (3)0.072 (3)0.012 (2)0.007 (2)0.019 (2)
C170.058 (3)0.052 (3)0.047 (2)0.007 (2)0.010 (2)0.003 (2)
C180.060 (3)0.043 (2)0.050 (2)0.004 (2)0.006 (2)0.0024 (19)
C190.058 (3)0.077 (4)0.056 (3)0.004 (3)0.017 (2)0.006 (3)
C200.053 (3)0.068 (3)0.065 (3)0.008 (3)0.015 (2)0.021 (3)
C210.072 (4)0.113 (5)0.062 (3)0.006 (4)0.021 (3)0.015 (3)
C220.051 (3)0.088 (4)0.075 (3)0.002 (3)0.002 (3)0.031 (3)
C230.060 (4)0.079 (4)0.128 (6)0.006 (3)0.011 (4)0.041 (4)
C280.053 (3)0.096 (4)0.058 (3)0.002 (3)0.005 (2)0.004 (3)
C290.051 (3)0.060 (3)0.076 (3)0.006 (2)0.006 (2)0.002 (3)
C300.073 (3)0.045 (3)0.056 (2)0.001 (2)0.008 (2)0.017 (2)
O10.069 (2)0.071 (3)0.097 (3)0.009 (2)0.004 (2)0.045 (2)
O20.059 (2)0.057 (2)0.072 (2)0.0079 (18)0.0111 (17)0.0232 (18)
O30.072 (2)0.0352 (16)0.085 (2)0.0049 (17)0.014 (2)0.0123 (17)
O40.0522 (18)0.064 (2)0.0378 (14)0.0053 (17)0.0031 (14)0.0063 (14)
O50.054 (2)0.076 (3)0.111 (3)0.017 (2)0.005 (2)0.015 (2)
O60.076 (3)0.116 (4)0.105 (3)0.001 (3)0.030 (3)0.053 (3)
C1A0.061 (3)0.071 (3)0.060 (3)0.027 (3)0.024 (2)0.035 (3)
C2A0.061 (3)0.093 (4)0.051 (2)0.018 (3)0.019 (2)0.024 (3)
C3A0.038 (2)0.058 (3)0.055 (2)0.004 (2)0.0024 (19)0.003 (2)
C4A0.044 (2)0.055 (3)0.046 (2)0.008 (2)0.0047 (18)0.0039 (19)
C5A0.047 (2)0.042 (2)0.0365 (17)0.0058 (19)0.0088 (16)0.0001 (17)
C6A0.064 (3)0.051 (3)0.0400 (19)0.002 (2)0.010 (2)0.0117 (19)
C7A0.059 (3)0.041 (2)0.0299 (16)0.010 (2)0.0030 (17)0.0076 (16)
C8A0.051 (2)0.036 (2)0.0345 (17)0.0064 (19)0.0046 (16)0.0021 (16)
C9A0.046 (2)0.035 (2)0.0393 (17)0.0017 (18)0.0075 (16)0.0063 (16)
C10A0.044 (2)0.039 (2)0.048 (2)0.0009 (19)0.0101 (18)0.0073 (18)
C11A0.049 (3)0.036 (2)0.080 (3)0.002 (2)0.021 (2)0.016 (2)
C12A0.046 (2)0.034 (2)0.081 (3)0.0051 (19)0.022 (2)0.001 (2)
C13A0.050 (2)0.035 (2)0.046 (2)0.0054 (19)0.0137 (18)0.0014 (17)
C14A0.054 (2)0.042 (2)0.0339 (16)0.011 (2)0.0125 (17)0.0047 (17)
C15A0.064 (3)0.059 (3)0.0413 (19)0.008 (3)0.013 (2)0.009 (2)
C16A0.062 (3)0.058 (3)0.050 (2)0.015 (3)0.016 (2)0.005 (2)
C17A0.051 (3)0.057 (3)0.066 (3)0.011 (2)0.024 (2)0.009 (2)
C18A0.052 (3)0.052 (3)0.045 (2)0.002 (2)0.0010 (18)0.0026 (19)
C19A0.043 (3)0.054 (3)0.105 (4)0.007 (2)0.004 (3)0.014 (3)
C20A0.048 (3)0.052 (3)0.092 (4)0.002 (2)0.023 (3)0.004 (3)
C21A0.087 (5)0.052 (3)0.123 (5)0.009 (3)0.018 (4)0.003 (4)
C23A0.052 (3)0.052 (3)0.148 (6)0.011 (3)0.009 (4)0.025 (4)
C22A0.065 (4)0.071 (4)0.158 (7)0.001 (4)0.002 (4)0.023 (5)
C28A0.062 (3)0.102 (5)0.073 (3)0.018 (3)0.029 (3)0.001 (3)
C29A0.085 (4)0.057 (3)0.058 (3)0.022 (3)0.007 (3)0.001 (2)
C30A0.069 (3)0.064 (3)0.055 (2)0.015 (3)0.004 (2)0.022 (2)
O1A0.081 (3)0.069 (2)0.093 (3)0.033 (2)0.008 (2)0.018 (2)
O2A0.054 (2)0.061 (2)0.077 (2)0.0121 (18)0.0223 (17)0.0044 (19)
O3A0.069 (2)0.081 (2)0.0379 (14)0.018 (2)0.0184 (15)0.0142 (16)
O4A0.070 (2)0.0401 (17)0.0472 (15)0.0099 (16)0.0113 (15)0.0050 (13)
O5A0.0462 (19)0.086 (3)0.085 (2)0.016 (2)0.0177 (17)0.009 (2)
O6A0.063 (3)0.117 (5)0.181 (6)0.025 (3)0.001 (3)0.018 (4)
C1B0.035 (2)0.073 (4)0.105 (4)0.011 (2)0.007 (3)0.051 (3)
C2B0.050 (3)0.063 (3)0.100 (4)0.022 (3)0.020 (3)0.031 (3)
C3B0.062 (3)0.048 (3)0.068 (3)0.012 (2)0.003 (2)0.014 (2)
C4B0.053 (3)0.044 (2)0.058 (2)0.000 (2)0.003 (2)0.015 (2)
C5B0.0341 (19)0.044 (2)0.0422 (18)0.0002 (18)0.0031 (15)0.0108 (17)
C6B0.035 (2)0.051 (2)0.046 (2)0.0056 (19)0.0036 (17)0.0070 (18)
C7B0.0296 (18)0.046 (2)0.0343 (16)0.0013 (17)0.0038 (15)0.0006 (16)
C8B0.0290 (17)0.046 (2)0.0292 (15)0.0020 (16)0.0021 (14)0.0074 (15)
C9B0.0282 (17)0.045 (2)0.0444 (18)0.0021 (17)0.0055 (15)0.0149 (18)
C10B0.033 (2)0.050 (3)0.057 (2)0.0032 (19)0.0057 (17)0.023 (2)
C11B0.0281 (19)0.056 (3)0.075 (3)0.010 (2)0.011 (2)0.024 (2)
C12B0.039 (2)0.051 (3)0.054 (2)0.007 (2)0.0103 (18)0.013 (2)
C13B0.0284 (17)0.038 (2)0.0386 (17)0.0045 (16)0.0020 (14)0.0044 (16)
C14B0.0284 (17)0.038 (2)0.0334 (16)0.0021 (16)0.0004 (14)0.0020 (15)
C15B0.0327 (19)0.051 (2)0.0394 (18)0.0051 (18)0.0015 (15)0.0071 (17)
C16B0.037 (2)0.053 (3)0.046 (2)0.008 (2)0.0029 (17)0.0072 (19)
C17B0.0346 (19)0.039 (2)0.0421 (18)0.0014 (18)0.0008 (15)0.0022 (16)
C18B0.049 (2)0.045 (2)0.0429 (19)0.005 (2)0.0096 (18)0.0012 (18)
C19B0.057 (3)0.077 (4)0.075 (3)0.016 (3)0.030 (3)0.032 (3)
C20B0.043 (2)0.039 (2)0.057 (2)0.0009 (19)0.0005 (19)0.0065 (19)
C21B0.065 (3)0.054 (3)0.077 (3)0.022 (3)0.009 (3)0.017 (3)
C22B0.065 (3)0.049 (3)0.074 (3)0.009 (3)0.019 (3)0.007 (2)
C23B0.063 (4)0.057 (3)0.109 (5)0.002 (3)0.029 (3)0.022 (3)
C28B0.073 (4)0.051 (3)0.089 (4)0.013 (3)0.005 (3)0.002 (3)
C29B0.079 (4)0.057 (3)0.071 (3)0.004 (3)0.017 (3)0.028 (3)
C30B0.054 (3)0.057 (3)0.0322 (17)0.004 (2)0.0059 (18)0.0030 (17)
O1B0.0500 (19)0.083 (3)0.0583 (18)0.0103 (19)0.0159 (16)0.0279 (18)
O2B0.0402 (15)0.0530 (18)0.0485 (14)0.0010 (14)0.0024 (12)0.0141 (13)
O3B0.0439 (16)0.0572 (18)0.0407 (13)0.0134 (15)0.0060 (12)0.0001 (13)
O4B0.0355 (15)0.0604 (19)0.0412 (13)0.0014 (15)0.0048 (12)0.0041 (13)
O5B0.076 (3)0.055 (2)0.141 (4)0.016 (2)0.018 (3)0.026 (3)
O6B0.063 (2)0.066 (3)0.133 (4)0.020 (2)0.000 (3)0.032 (3)
Geometric parameters (Å, º) top
C1—C21.312 (9)C14A—O3A1.460 (4)
C1—C101.505 (7)C14A—C15A1.486 (6)
C1—H10.93C15A—O3A1.440 (6)
C2—C31.462 (9)C15A—C16A1.482 (8)
C2—H20.93C15A—H15A0.98
C3—O51.215 (7)C16A—O1A1.213 (6)
C3—C41.503 (7)C16A—O2A1.330 (7)
C4—C291.530 (7)C17A—O2A1.475 (6)
C4—C281.555 (7)C17A—C20A1.482 (8)
C4—C51.570 (6)C17A—H17A0.98
C5—C61.520 (6)C18A—H18D0.96
C5—C101.552 (6)C18A—H18E0.96
C5—H50.98C18A—H18F0.96
C6—C71.532 (7)C19A—H19D0.96
C6—H6A0.97C19A—H19E0.96
C6—H6B0.97C19A—H19F0.96
C7—O41.431 (5)C20A—C22A1.375 (10)
C7—C81.534 (6)C20A—C21A1.404 (9)
C7—H70.98C21A—C23A1.316 (11)
C8—C301.545 (6)C21A—H21A0.93
C8—C91.559 (6)C23A—O6A1.345 (9)
C8—C141.562 (7)C23A—H23A0.93
C9—C111.533 (6)C22A—O6A1.350 (9)
C9—C101.577 (7)C22A—H22A0.93
C9—H90.98C28A—H28D0.96
C10—C191.544 (7)C28A—H28E0.96
C11—C121.532 (7)C28A—H28F0.96
C11—H11A0.97C29A—H29D0.96
C11—H11B0.97C29A—H29E0.96
C12—C131.533 (6)C29A—H29F0.96
C12—H12A0.97C30A—H30D0.96
C12—H12B0.97C30A—H30E0.96
C13—C141.537 (6)C30A—H30F0.96
C13—C171.538 (6)O4A—H4OA1.01 (6)
C13—C181.539 (6)C1B—C2B1.328 (9)
C14—O31.441 (5)C1B—C10B1.510 (7)
C14—C151.474 (7)C1B—H1B0.93
C15—O31.424 (7)C2B—C3B1.471 (8)
C15—C161.497 (8)C2B—H2B0.93
C15—H150.98C3B—O5B1.213 (6)
C16—O11.204 (6)C3B—C4B1.509 (8)
C16—O21.323 (6)C4B—C28B1.534 (8)
C17—O21.471 (6)C4B—C29B1.537 (7)
C17—C201.493 (7)C4B—C5B1.549 (6)
C17—H170.98C5B—C6B1.513 (6)
C18—H18A0.96C5B—C10B1.558 (6)
C18—H18B0.96C5B—H5B0.98
C18—H18C0.96C6B—C7B1.549 (6)
C19—H19A0.96C6B—H6B10.97
C19—H19B0.96C6B—H6B20.97
C19—H19C0.96C7B—O4B1.431 (4)
C20—C211.365 (7)C7B—C8B1.532 (6)
C20—C221.412 (9)C7B—H7B0.98
C21—O61.363 (9)C8B—C30B1.545 (5)
C21—H210.93C8B—C9B1.549 (6)
C22—C231.349 (9)C8B—C14B1.573 (5)
C22—H220.93C9B—C11B1.543 (6)
C23—O61.359 (10)C9B—C10B1.564 (6)
C23—H230.93C9B—H9B0.98
C28—H28A0.96C10B—C19B1.545 (7)
C28—H28B0.96C11B—C12B1.536 (7)
C28—H28C0.96C11B—H11E0.97
C29—H29A0.96C11B—H11F0.97
C29—H29B0.96C12B—C13B1.533 (6)
C29—H29C0.96C12B—H12E0.97
C30—H30A0.96C12B—H12F0.97
C30—H30B0.96C13B—C14B1.535 (5)
C30—H30C0.96C13B—C18B1.542 (6)
O4—H4O0.81 (5)C13B—C17B1.553 (6)
C1A—C2A1.333 (7)C14B—O3B1.453 (5)
C1A—C10A1.506 (6)C14B—C15B1.458 (5)
C1A—H1A0.93C15B—O3B1.431 (5)
C2A—C3A1.449 (7)C15B—C16B1.491 (6)
C2A—H2A0.93C15B—H15B0.98
C3A—O5A1.227 (6)C16B—O1B1.208 (5)
C3A—C4A1.533 (6)C16B—O2B1.324 (6)
C4A—C29A1.539 (8)C17B—O2B1.465 (5)
C4A—C28A1.544 (7)C17B—C20B1.499 (6)
C4A—C5A1.554 (6)C17B—H17B0.98
C5A—C6A1.532 (6)C18B—H18G0.96
C5A—C10A1.543 (6)C18B—H18H0.96
C5A—H5A0.98C18B—H18I0.96
C6A—C7A1.520 (7)C19B—H19G0.96
C6A—H6A10.97C19B—H19H0.96
C6A—H6A20.97C19B—H19I0.96
C7A—O4A1.416 (5)C20B—C21B1.337 (7)
C7A—C8A1.528 (6)C20B—C22B1.432 (7)
C7A—H7A0.98C21B—O6B1.377 (7)
C8A—C30A1.545 (6)C21B—H21B0.93
C8A—C14A1.557 (7)C22B—C23B1.339 (8)
C8A—C9A1.563 (5)C22B—H22B0.93
C9A—C11A1.539 (6)C23B—O6B1.354 (9)
C9A—C10A1.573 (6)C23B—H23B0.93
C9A—H9A1.1028C28B—H28G0.96
C10A—C19A1.536 (7)C28B—H28H0.96
C11A—C12A1.554 (6)C28B—H28I0.96
C11A—H11C0.97C29B—H29G0.96
C11A—H11D0.97C29B—H29H0.96
C12A—C13A1.527 (6)C29B—H29I0.96
C12A—H12C0.97C30B—H30G0.96
C12A—H12D0.97C30B—H30H0.96
C13A—C14A1.516 (6)C30B—H30I0.96
C13A—C17A1.552 (7)O4B—H4OB0.88 (7)
C13A—C18A1.556 (6)
C2—C1—C10120.9 (5)C17A—C13A—C18A107.4 (4)
C2—C1—H1119.5O3A—C14A—C15A58.5 (3)
C10—C1—H1119.5O3A—C14A—C13A112.7 (4)
C1—C2—C3123.3 (5)C15A—C14A—C13A114.2 (4)
C1—C2—H2118.4O3A—C14A—C8A113.7 (4)
C3—C2—H2118.4C15A—C14A—C8A122.1 (4)
O5—C3—C2120.4 (5)C13A—C14A—C8A119.7 (3)
O5—C3—C4121.2 (5)O3A—C15A—C16A113.1 (5)
C2—C3—C4118.3 (5)O3A—C15A—C14A59.9 (3)
C3—C4—C29108.7 (4)C16A—C15A—C14A118.4 (4)
C3—C4—C28105.7 (4)O3A—C15A—H15A117.5
C29—C4—C28108.7 (4)C16A—C15A—H15A117.5
C3—C4—C5111.1 (4)C14A—C15A—H15A117.5
C29—C4—C5114.4 (4)O1A—C16A—O2A119.0 (5)
C28—C4—C5107.9 (4)O1A—C16A—C15A122.1 (6)
C6—C5—C10111.7 (4)O2A—C16A—C15A118.9 (5)
C6—C5—C4113.7 (4)O2A—C17A—C20A104.6 (4)
C10—C5—C4114.5 (4)O2A—C17A—C13A110.4 (4)
C6—C5—H5105.3C20A—C17A—C13A116.1 (4)
C10—C5—H5105.3O2A—C17A—H17A108.5
C4—C5—H5105.3C20A—C17A—H17A108.5
C5—C6—C7111.5 (4)C13A—C17A—H17A108.5
C5—C6—H6A109.3C13A—C18A—H18D109.5
C7—C6—H6A109.3C13A—C18A—H18E109.5
C5—C6—H6B109.3H18D—C18A—H18E109.5
C7—C6—H6B109.3C13A—C18A—H18F109.5
H6A—C6—H6B108H18D—C18A—H18F109.5
O4—C7—C6110.7 (4)H18E—C18A—H18F109.5
O4—C7—C8107.2 (3)C10A—C19A—H19D109.5
C6—C7—C8111.6 (3)C10A—C19A—H19E109.5
O4—C7—H7109.1H19D—C19A—H19E109.5
C6—C7—H7109.1C10A—C19A—H19F109.5
C8—C7—H7109.1H19D—C19A—H19F109.5
C7—C8—C30109.5 (4)H19E—C19A—H19F109.5
C7—C8—C9109.0 (3)C22A—C20A—C21A103.6 (7)
C30—C8—C9112.4 (4)C22A—C20A—C17A127.6 (6)
C7—C8—C14110.5 (3)C21A—C20A—C17A128.8 (6)
C30—C8—C14106.3 (4)C23A—C21A—C20A110.0 (7)
C9—C8—C14109.1 (3)C23A—C21A—H21A125
C11—C9—C8111.2 (3)C20A—C21A—H21A125
C11—C9—C10113.9 (4)C21A—C23A—O6A108.6 (6)
C8—C9—C10115.4 (4)C21A—C23A—H23A125.7
C11—C9—H9105O6A—C23A—H23A125.7
C8—C9—H9105O6A—C22A—C20A109.7 (7)
C10—C9—H9105O6A—C22A—H22A125.2
C1—C10—C19105.1 (4)C20A—C22A—H22A125.2
C1—C10—C5106.0 (4)C4A—C28A—H28D109.5
C19—C10—C5114.9 (4)C4A—C28A—H28E109.5
C1—C10—C9109.1 (4)H28D—C28A—H28E109.5
C19—C10—C9114.7 (4)C4A—C28A—H28F109.5
C5—C10—C9106.6 (3)H28D—C28A—H28F109.5
C12—C11—C9115.3 (4)H28E—C28A—H28F109.5
C12—C11—H11A108.5C4A—C29A—H29D109.5
C9—C11—H11A108.5C4A—C29A—H29E109.5
C12—C11—H11B108.5H29D—C29A—H29E109.5
C9—C11—H11B108.5C4A—C29A—H29F109.5
H11A—C11—H11B107.5H29D—C29A—H29F109.5
C11—C12—C13113.1 (3)H29E—C29A—H29F109.5
C11—C12—H12A109C8A—C30A—H30D109.5
C13—C12—H12A109C8A—C30A—H30E109.5
C11—C12—H12B109H30D—C30A—H30E109.5
C13—C12—H12B109C8A—C30A—H30F109.5
H12A—C12—H12B107.8H30D—C30A—H30F109.5
C12—C13—C14105.4 (4)H30E—C30A—H30F109.5
C12—C13—C17109.3 (3)C16A—O2A—C17A120.7 (4)
C14—C13—C17107.3 (4)C15A—O3A—C14A61.6 (3)
C12—C13—C18113.7 (4)C7A—O4A—H4OA101 (3)
C14—C13—C18111.6 (3)C23A—O6A—C22A108.0 (6)
C17—C13—C18109.3 (4)C2B—C1B—C10B122.9 (5)
O3—C14—C1558.5 (3)C2B—C1B—H1B118.6
O3—C14—C13112.7 (3)C10B—C1B—H1B118.6
C15—C14—C13114.3 (4)C1B—C2B—C3B122.3 (5)
O3—C14—C8113.4 (4)C1B—C2B—H2B118.9
C15—C14—C8123.0 (4)C3B—C2B—H2B118.9
C13—C14—C8119.2 (3)O5B—C3B—C2B118.8 (5)
O3—C15—C1459.6 (3)O5B—C3B—C4B122.3 (5)
O3—C15—C16113.1 (4)C2B—C3B—C4B118.9 (4)
C14—C15—C16119.0 (4)C3B—C4B—C28B105.1 (5)
O3—C15—H15117.4C3B—C4B—C29B108.4 (4)
C14—C15—H15117.4C28B—C4B—C29B108.8 (5)
C16—C15—H15117.4C3B—C4B—C5B111.5 (4)
O1—C16—O2119.8 (5)C28B—C4B—C5B108.2 (4)
O1—C16—C15121.8 (5)C29B—C4B—C5B114.4 (4)
O2—C16—C15118.4 (5)C6B—C5B—C4B114.5 (4)
O2—C17—C20104.6 (4)C6B—C5B—C10B111.7 (4)
O2—C17—C13110.9 (3)C4B—C5B—C10B115.8 (4)
C20—C17—C13115.5 (4)C6B—C5B—H5B104.4
O2—C17—H17108.5C4B—C5B—H5B104.4
C20—C17—H17108.5C10B—C5B—H5B104.4
C13—C17—H17108.5C5B—C6B—C7B110.2 (3)
C13—C18—H18A109.5C5B—C6B—H6B1109.6
C13—C18—H18B109.5C7B—C6B—H6B1109.6
H18A—C18—H18B109.5C5B—C6B—H6B2109.6
C13—C18—H18C109.5C7B—C6B—H6B2109.6
H18A—C18—H18C109.5H6B1—C6B—H6B2108.1
H18B—C18—H18C109.5O4B—C7B—C8B108.9 (3)
C10—C19—H19A109.5O4B—C7B—C6B108.0 (3)
C10—C19—H19B109.5C8B—C7B—C6B112.3 (3)
H19A—C19—H19B109.5O4B—C7B—H7B109.2
C10—C19—H19C109.5C8B—C7B—H7B109.2
H19A—C19—H19C109.5C6B—C7B—H7B109.2
H19B—C19—H19C109.5C7B—C8B—C30B109.4 (3)
C21—C20—C22105.4 (5)C7B—C8B—C9B108.8 (3)
C21—C20—C17125.4 (6)C30B—C8B—C9B112.7 (3)
C22—C20—C17129.2 (5)C7B—C8B—C14B110.3 (3)
O6—C21—C20110.6 (6)C30B—C8B—C14B106.5 (3)
O6—C21—H21124.7C9B—C8B—C14B109.1 (3)
C20—C21—H21124.7C11B—C9B—C8B111.9 (4)
C23—C22—C20107.4 (6)C11B—C9B—C10B113.4 (3)
C23—C22—H22126.3C8B—C9B—C10B115.0 (3)
C20—C22—H22126.3C11B—C9B—H9B105.1
C22—C23—O6110.2 (6)C8B—C9B—H9B105.1
C22—C23—H23124.9C10B—C9B—H9B105.1
O6—C23—H23124.9C1B—C10B—C19B105.2 (4)
C4—C28—H28A109.5C1B—C10B—C5B106.1 (4)
C4—C28—H28B109.5C19B—C10B—C5B113.3 (3)
H28A—C28—H28B109.5C1B—C10B—C9B108.3 (4)
C4—C28—H28C109.5C19B—C10B—C9B116.2 (4)
H28A—C28—H28C109.5C5B—C10B—C9B107.1 (3)
H28B—C28—H28C109.5C12B—C11B—C9B115.6 (3)
C4—C29—H29A109.5C12B—C11B—H11E108.4
C4—C29—H29B109.5C9B—C11B—H11E108.4
H29A—C29—H29B109.5C12B—C11B—H11F108.4
C4—C29—H29C109.5C9B—C11B—H11F108.4
H29A—C29—H29C109.5H11E—C11B—H11F107.4
H29B—C29—H29C109.5C13B—C12B—C11B111.5 (4)
C8—C30—H30A109.5C13B—C12B—H12E109.3
C8—C30—H30B109.5C11B—C12B—H12E109.3
H30A—C30—H30B109.5C13B—C12B—H12F109.3
C8—C30—H30C109.5C11B—C12B—H12F109.3
H30A—C30—H30C109.5H12E—C12B—H12F108
H30B—C30—H30C109.5C12B—C13B—C14B107.1 (3)
C16—O2—C17120.7 (4)C12B—C13B—C18B112.6 (4)
C15—O3—C1461.9 (3)C14B—C13B—C18B111.3 (3)
C7—O4—H4O103 (3)C12B—C13B—C17B109.2 (3)
C23—O6—C21106.3 (5)C14B—C13B—C17B106.8 (3)
C2A—C1A—C10A122.7 (4)C18B—C13B—C17B109.8 (3)
C2A—C1A—H1A118.7O3B—C14B—C15B58.9 (3)
C10A—C1A—H1A118.7O3B—C14B—C13B114.1 (3)
C1A—C2A—C3A122.3 (4)C15B—C14B—C13B114.2 (3)
C1A—C2A—H2A118.8O3B—C14B—C8B112.5 (3)
C3A—C2A—H2A118.8C15B—C14B—C8B123.7 (3)
O5A—C3A—C2A119.5 (4)C13B—C14B—C8B118.4 (3)
O5A—C3A—C4A120.2 (4)O3B—C15B—C14B60.4 (2)
C2A—C3A—C4A120.2 (4)O3B—C15B—C16B113.3 (4)
C3A—C4A—C29A105.1 (4)C14B—C15B—C16B118.2 (4)
C3A—C4A—C28A108.8 (4)O3B—C15B—H15B117.5
C29A—C4A—C28A109.7 (5)C14B—C15B—H15B117.5
C3A—C4A—C5A109.6 (4)C16B—C15B—H15B117.4
C29A—C4A—C5A108.2 (4)O1B—C16B—O2B118.5 (4)
C28A—C4A—C5A114.9 (4)O1B—C16B—C15B122.8 (4)
C6A—C5A—C10A110.7 (4)O2B—C16B—C15B118.7 (4)
C6A—C5A—C4A114.8 (4)O2B—C17B—C20B105.9 (3)
C10A—C5A—C4A116.7 (4)O2B—C17B—C13B109.5 (3)
C6A—C5A—H5A104.3C20B—C17B—C13B115.7 (3)
C10A—C5A—H5A104.3O2B—C17B—H17B108.5
C4A—C5A—H5A104.3C20B—C17B—H17B108.5
C7A—C6A—C5A110.9 (3)C13B—C17B—H17B108.5
C7A—C6A—H6A1109.5C13B—C18B—H18G109.5
C5A—C6A—H6A1109.5C13B—C18B—H18H109.5
C7A—C6A—H6A2109.5H18G—C18B—H18H109.5
C5A—C6A—H6A2109.5C13B—C18B—H18I109.5
H6A1—C6A—H6A2108.1H18G—C18B—H18I109.5
O4A—C7A—C6A109.7 (4)H18H—C18B—H18I109.5
O4A—C7A—C8A108.6 (3)C10B—C19B—H19G109.5
C6A—C7A—C8A112.6 (4)C10B—C19B—H19H109.5
O4A—C7A—H7A108.6H19G—C19B—H19H109.5
C6A—C7A—H7A108.6C10B—C19B—H19I109.5
C8A—C7A—H7A108.6H19G—C19B—H19I109.5
C7A—C8A—C30A109.8 (4)H19H—C19B—H19I109.5
C7A—C8A—C14A110.7 (4)C21B—C20B—C22B106.7 (5)
C30A—C8A—C14A107.0 (4)C21B—C20B—C17B124.8 (4)
C7A—C8A—C9A109.1 (3)C22B—C20B—C17B128.5 (4)
C30A—C8A—C9A112.4 (4)C20B—C21B—O6B110.0 (5)
C14A—C8A—C9A107.9 (3)C20B—C21B—H21B125
C11A—C9A—C8A111.3 (4)O6B—C21B—H21B125
C11A—C9A—C10A114.1 (4)C23B—C22B—C20B105.9 (6)
C8A—C9A—C10A115.5 (3)C23B—C22B—H22B127.1
C11A—C9A—H9A104.9C20B—C22B—H22B127.1
C8A—C9A—H9A104.9C22B—C23B—O6B111.2 (5)
C10A—C9A—H9A104.9C22B—C23B—H23B124.4
C1A—C10A—C19A105.7 (4)O6B—C23B—H23B124.4
C1A—C10A—C5A106.9 (4)C4B—C28B—H28G109.5
C19A—C10A—C5A113.9 (4)C4B—C28B—H28H109.5
C1A—C10A—C9A107.9 (4)H28G—C28B—H28H109.5
C19A—C10A—C9A114.7 (4)C4B—C28B—H28I109.5
C5A—C10A—C9A107.3 (3)H28G—C28B—H28I109.5
C9A—C11A—C12A114.4 (4)H28H—C28B—H28I109.5
C9A—C11A—H11C108.7C4B—C29B—H29G109.5
C12A—C11A—H11C108.7C4B—C29B—H29H109.5
C9A—C11A—H11D108.7H29G—C29B—H29H109.5
C12A—C11A—H11D108.7C4B—C29B—H29I109.5
H11C—C11A—H11D107.6H29G—C29B—H29I109.5
C13A—C12A—C11A112.7 (4)H29H—C29B—H29I109.5
C13A—C12A—H12C109.1C8B—C30B—H30G109.5
C11A—C12A—H12C109.1C8B—C30B—H30H109.5
C13A—C12A—H12D109.1H30G—C30B—H30H109.5
C11A—C12A—H12D109.1C8B—C30B—H30I109.5
H12C—C12A—H12D107.8H30G—C30B—H30I109.5
C14A—C13A—C12A107.6 (4)H30H—C30B—H30I109.5
C14A—C13A—C17A108.3 (3)C16B—O2B—C17B120.7 (3)
C12A—C13A—C17A109.2 (4)C15B—O3B—C14B60.8 (2)
C14A—C13A—C18A111.3 (4)C7B—O4B—H4OB118 (4)
C12A—C13A—C18A113.0 (4)C23B—O6B—C21B106.2 (4)
C10—C1—C2—C30.7 (10)C12A—C13A—C14A—O3A95.7 (4)
C1—C2—C3—O5155.8 (7)C17A—C13A—C14A—O3A22.2 (5)
C1—C2—C3—C425.4 (9)C18A—C13A—C14A—O3A140.1 (4)
O5—C3—C4—C2949.6 (6)C12A—C13A—C14A—C15A160.0 (4)
C2—C3—C4—C29131.7 (5)C17A—C13A—C14A—C15A42.2 (5)
O5—C3—C4—C2867.0 (6)C18A—C13A—C14A—C15A75.7 (5)
C2—C3—C4—C28111.8 (6)C12A—C13A—C14A—C8A42.0 (5)
O5—C3—C4—C5176.2 (5)C17A—C13A—C14A—C8A159.9 (4)
C2—C3—C4—C55.0 (6)C18A—C13A—C14A—C8A82.2 (5)
C3—C4—C5—C6165.9 (4)C7A—C8A—C14A—O3A89.1 (4)
C29—C4—C5—C642.4 (5)C30A—C8A—C14A—O3A30.5 (5)
C28—C4—C5—C678.6 (5)C9A—C8A—C14A—O3A151.6 (3)
C3—C4—C5—C1035.7 (5)C7A—C8A—C14A—C15A22.6 (5)
C29—C4—C5—C1087.7 (5)C30A—C8A—C14A—C15A97.0 (5)
C28—C4—C5—C10151.2 (4)C9A—C8A—C14A—C15A141.9 (4)
C10—C5—C6—C760.8 (5)C7A—C8A—C14A—C13A133.6 (4)
C4—C5—C6—C7167.6 (3)C30A—C8A—C14A—C13A106.8 (4)
C5—C6—C7—O460.8 (5)C9A—C8A—C14A—C13A14.3 (5)
C5—C6—C7—C858.6 (5)C13A—C14A—C15A—O3A102.7 (4)
O4—C7—C8—C30168.4 (4)C8A—C14A—C15A—O3A100.0 (4)
C6—C7—C8—C3070.1 (5)O3A—C14A—C15A—C16A101.7 (5)
O4—C7—C8—C968.2 (4)C13A—C14A—C15A—C16A1.0 (6)
C6—C7—C8—C953.2 (5)C8A—C14A—C15A—C16A158.3 (4)
O4—C7—C8—C1451.7 (4)O3A—C15A—C16A—O1A140.7 (5)
C6—C7—C8—C14173.1 (3)C14A—C15A—C16A—O1A152.2 (5)
C7—C8—C9—C11174.8 (4)O3A—C15A—C16A—O2A38.9 (5)
C30—C8—C9—C1163.6 (5)C14A—C15A—C16A—O2A28.2 (7)
C14—C8—C9—C1154.1 (5)C14A—C13A—C17A—O2A58.8 (5)
C7—C8—C9—C1053.4 (4)C12A—C13A—C17A—O2A175.7 (4)
C30—C8—C9—C1068.2 (5)C18A—C13A—C17A—O2A61.5 (5)
C14—C8—C9—C10174.2 (3)C14A—C13A—C17A—C20A177.7 (4)
C2—C1—C10—C1983.3 (7)C12A—C13A—C17A—C20A65.5 (6)
C2—C1—C10—C538.8 (7)C18A—C13A—C17A—C20A57.3 (5)
C2—C1—C10—C9153.3 (6)O2A—C17A—C20A—C22A28.2 (8)
C6—C5—C10—C1172.4 (4)C13A—C17A—C20A—C22A93.8 (7)
C4—C5—C10—C156.5 (5)O2A—C17A—C20A—C21A152.9 (6)
C6—C5—C10—C1972.0 (5)C13A—C17A—C20A—C21A85.1 (7)
C4—C5—C10—C1959.1 (5)C22A—C20A—C21A—C23A0.0 (8)
C6—C5—C10—C956.2 (5)C17A—C20A—C21A—C23A179.2 (6)
C4—C5—C10—C9172.7 (4)C20A—C21A—C23A—O6A1.2 (9)
C11—C9—C10—C161.3 (5)C21A—C20A—C22A—O6A1.3 (8)
C8—C9—C10—C1168.3 (4)C17A—C20A—C22A—O6A179.6 (6)
C11—C9—C10—C1956.3 (5)O1A—C16A—O2A—C17A170.3 (4)
C8—C9—C10—C1974.2 (5)C15A—C16A—O2A—C17A10.1 (6)
C11—C9—C10—C5175.4 (4)C20A—C17A—O2A—C16A159.3 (4)
C8—C9—C10—C554.2 (4)C13A—C17A—O2A—C16A33.7 (6)
C8—C9—C11—C1237.1 (6)C16A—C15A—O3A—C14A110.4 (4)
C10—C9—C11—C12169.6 (4)C13A—C14A—O3A—C15A105.4 (4)
C9—C11—C12—C1322.8 (6)C8A—C14A—O3A—C15A114.3 (5)
C11—C12—C13—C1461.3 (5)C21A—C23A—O6A—C22A2.0 (9)
C11—C12—C13—C17176.3 (4)C20A—C22A—O6A—C23A2.0 (9)
C11—C12—C13—C1861.3 (5)C10B—C1B—C2B—C3B1.8 (10)
C12—C13—C14—O393.9 (4)C1B—C2B—C3B—O5B160.3 (7)
C17—C13—C14—O322.5 (5)C1B—C2B—C3B—C4B20.5 (9)
C18—C13—C14—O3142.2 (4)O5B—C3B—C4B—C28B61.3 (7)
C12—C13—C14—C15158.2 (4)C2B—C3B—C4B—C28B117.9 (6)
C17—C13—C14—C1541.9 (5)O5B—C3B—C4B—C29B54.9 (8)
C18—C13—C14—C1577.9 (5)C2B—C3B—C4B—C29B125.9 (6)
C12—C13—C14—C842.6 (5)O5B—C3B—C4B—C5B178.2 (5)
C17—C13—C14—C8158.9 (4)C2B—C3B—C4B—C5B1.0 (7)
C18—C13—C14—C881.3 (5)C3B—C4B—C5B—C6B171.0 (4)
C7—C8—C14—O390.7 (4)C28B—C4B—C5B—C6B73.9 (5)
C30—C8—C14—O328.0 (5)C29B—C4B—C5B—C6B47.4 (6)
C9—C8—C14—O3149.5 (3)C3B—C4B—C5B—C10B38.7 (5)
C7—C8—C14—C1524.2 (5)C28B—C4B—C5B—C10B153.8 (4)
C30—C8—C14—C1594.6 (5)C29B—C4B—C5B—C10B84.8 (5)
C9—C8—C14—C15144.0 (4)C4B—C5B—C6B—C7B165.6 (4)
C7—C8—C14—C13133.1 (4)C10B—C5B—C6B—C7B60.2 (4)
C30—C8—C14—C13108.1 (4)C5B—C6B—C7B—O4B61.6 (4)
C9—C8—C14—C1313.3 (5)C5B—C6B—C7B—C8B58.4 (4)
C13—C14—C15—O3102.7 (4)O4B—C7B—C8B—C30B170.6 (3)
C8—C14—C15—O399.0 (4)C6B—C7B—C8B—C30B69.8 (4)
O3—C14—C15—C16101.2 (5)O4B—C7B—C8B—C9B65.8 (4)
C13—C14—C15—C161.4 (6)C6B—C7B—C8B—C9B53.7 (4)
C8—C14—C15—C16159.8 (4)O4B—C7B—C8B—C14B53.8 (4)
O3—C15—C16—O1138.1 (5)C6B—C7B—C8B—C14B173.4 (3)
C14—C15—C16—O1155.1 (5)C7B—C8B—C9B—C11B174.8 (3)
O3—C15—C16—O241.3 (6)C30B—C8B—C9B—C11B63.7 (4)
C14—C15—C16—O225.6 (7)C14B—C8B—C9B—C11B54.3 (4)
C12—C13—C17—O2173.9 (4)C7B—C8B—C9B—C10B53.9 (4)
C14—C13—C17—O260.2 (5)C30B—C8B—C9B—C10B67.6 (5)
C18—C13—C17—O261.0 (5)C14B—C8B—C9B—C10B174.4 (3)
C12—C13—C17—C2067.3 (5)C2B—C1B—C10B—C19B86.7 (7)
C14—C13—C17—C20179.0 (4)C2B—C1B—C10B—C5B33.7 (7)
C18—C13—C17—C2057.8 (5)C2B—C1B—C10B—C9B148.5 (6)
O2—C17—C20—C21142.9 (6)C6B—C5B—C10B—C1B172.7 (4)
C13—C17—C20—C2194.9 (7)C4B—C5B—C10B—C1B53.8 (5)
O2—C17—C20—C2236.0 (7)C6B—C5B—C10B—C19B72.3 (5)
C13—C17—C20—C2286.2 (7)C4B—C5B—C10B—C19B61.2 (5)
C22—C20—C21—O61.2 (7)C6B—C5B—C10B—C9B57.1 (4)
C17—C20—C21—O6179.6 (5)C4B—C5B—C10B—C9B169.3 (4)
C21—C20—C22—C230.3 (7)C11B—C9B—C10B—C1B60.4 (5)
C17—C20—C22—C23179.4 (6)C8B—C9B—C10B—C1B169.0 (4)
C20—C22—C23—O60.7 (8)C11B—C9B—C10B—C19B57.7 (5)
O1—C16—O2—C17174.5 (5)C8B—C9B—C10B—C19B72.9 (5)
C15—C16—O2—C176.1 (7)C11B—C9B—C10B—C5B174.5 (4)
C20—C17—O2—C16162.8 (5)C8B—C9B—C10B—C5B54.9 (5)
C13—C17—O2—C1637.6 (6)C8B—C9B—C11B—C12B33.0 (5)
C16—C15—O3—C14111.1 (5)C10B—C9B—C11B—C12B165.2 (4)
C13—C14—O3—C15105.5 (4)C9B—C11B—C12B—C13B27.0 (6)
C8—C14—O3—C15115.5 (4)C11B—C12B—C13B—C14B62.4 (5)
C22—C23—O6—C211.5 (8)C11B—C12B—C13B—C18B60.2 (5)
C20—C21—O6—C231.7 (8)C11B—C12B—C13B—C17B177.6 (4)
C10A—C1A—C2A—C3A1.9 (10)C12B—C13B—C14B—O3B96.2 (4)
C1A—C2A—C3A—O5A160.9 (6)C18B—C13B—C14B—O3B140.4 (3)
C1A—C2A—C3A—C4A18.5 (9)C17B—C13B—C14B—O3B20.6 (4)
O5A—C3A—C4A—C29A61.6 (6)C12B—C13B—C14B—C15B161.3 (4)
C2A—C3A—C4A—C29A118.9 (6)C18B—C13B—C14B—C15B75.2 (4)
O5A—C3A—C4A—C28A55.8 (7)C17B—C13B—C14B—C15B44.5 (4)
C2A—C3A—C4A—C28A123.6 (6)C12B—C13B—C14B—C8B39.6 (5)
O5A—C3A—C4A—C5A177.7 (5)C18B—C13B—C14B—C8B83.8 (4)
C2A—C3A—C4A—C5A2.8 (6)C17B—C13B—C14B—C8B156.4 (3)
C3A—C4A—C5A—C6A171.5 (4)C7B—C8B—C14B—O3B86.6 (4)
C29A—C4A—C5A—C6A74.4 (5)C30B—C8B—C14B—O3B32.0 (4)
C28A—C4A—C5A—C6A48.6 (6)C9B—C8B—C14B—O3B153.9 (3)
C3A—C4A—C5A—C10A39.5 (5)C7B—C8B—C14B—C15B20.0 (5)
C29A—C4A—C5A—C10A153.6 (4)C30B—C8B—C14B—C15B98.7 (4)
C28A—C4A—C5A—C10A83.4 (5)C9B—C8B—C14B—C15B139.5 (4)
C10A—C5A—C6A—C7A61.9 (5)C7B—C8B—C14B—C13B136.9 (3)
C4A—C5A—C6A—C7A163.3 (4)C30B—C8B—C14B—C13B104.4 (4)
C5A—C6A—C7A—O4A61.8 (5)C9B—C8B—C14B—C13B17.5 (4)
C5A—C6A—C7A—C8A59.2 (5)C13B—C14B—C15B—O3B104.5 (4)
O4A—C7A—C8A—C30A167.0 (4)C8B—C14B—C15B—O3B97.7 (4)
C6A—C7A—C8A—C30A71.3 (4)O3B—C14B—C15B—C16B102.3 (4)
O4A—C7A—C8A—C14A49.1 (4)C13B—C14B—C15B—C16B2.2 (5)
C6A—C7A—C8A—C14A170.8 (3)C8B—C14B—C15B—C16B160.0 (4)
O4A—C7A—C8A—C9A69.5 (4)O3B—C15B—C16B—O1B140.6 (5)
C6A—C7A—C8A—C9A52.2 (4)C14B—C15B—C16B—O1B151.7 (5)
C7A—C8A—C9A—C11A176.7 (4)O3B—C15B—C16B—O2B39.4 (5)
C30A—C8A—C9A—C11A61.3 (5)C14B—C15B—C16B—O2B28.3 (6)
C14A—C8A—C9A—C11A56.3 (5)C12B—C13B—C17B—O2B176.7 (3)
C7A—C8A—C9A—C10A51.2 (5)C14B—C13B—C17B—O2B61.3 (4)
C30A—C8A—C9A—C10A70.8 (5)C18B—C13B—C17B—O2B59.4 (4)
C14A—C8A—C9A—C10A171.5 (3)C12B—C13B—C17B—C20B63.7 (4)
C2A—C1A—C10A—C19A89.2 (7)C14B—C13B—C17B—C20B179.1 (3)
C2A—C1A—C10A—C5A32.4 (8)C18B—C13B—C17B—C20B60.2 (4)
C2A—C1A—C10A—C9A147.6 (6)O2B—C17B—C20B—C21B137.4 (5)
C6A—C5A—C10A—C1A172.7 (4)C13B—C17B—C20B—C21B101.0 (6)
C4A—C5A—C10A—C1A53.4 (5)O2B—C17B—C20B—C22B43.8 (6)
C6A—C5A—C10A—C19A71.0 (5)C13B—C17B—C20B—C22B77.7 (6)
C4A—C5A—C10A—C19A62.9 (5)C22B—C20B—C21B—O6B1.3 (6)
C6A—C5A—C10A—C9A57.1 (4)C17B—C20B—C21B—O6B177.7 (4)
C4A—C5A—C10A—C9A169.0 (3)C21B—C20B—C22B—C23B1.0 (6)
C11A—C9A—C10A—C1A60.6 (5)C17B—C20B—C22B—C23B178.0 (5)
C8A—C9A—C10A—C1A168.6 (4)C20B—C22B—C23B—O6B0.3 (7)
C11A—C9A—C10A—C19A56.9 (5)O1B—C16B—O2B—C17B170.2 (4)
C8A—C9A—C10A—C19A73.9 (5)C15B—C16B—O2B—C17B9.8 (6)
C11A—C9A—C10A—C5A175.5 (4)C20B—C17B—O2B—C16B161.0 (4)
C8A—C9A—C10A—C5A53.7 (4)C13B—C17B—O2B—C16B35.5 (5)
C8A—C9A—C11A—C12A41.0 (6)C16B—C15B—O3B—C14B110.2 (4)
C10A—C9A—C11A—C12A173.8 (4)C13B—C14B—O3B—C15B104.8 (3)
C9A—C11A—C12A—C13A18.1 (7)C8B—C14B—O3B—C15B116.8 (4)
C11A—C12A—C13A—C14A58.5 (5)C22B—C23B—O6B—C21B0.5 (7)
C11A—C12A—C13A—C17A175.9 (4)C20B—C21B—O6B—C23B1.1 (6)
C11A—C12A—C13A—C18A64.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4A—H4OA···O11.01 (6)1.83 (6)2.818 (5)169 (5)
O4—H4O···O1B0.81 (5)2.14 (5)2.952 (5)177 (4)
O4B—H4OB···O5Ai0.88 (7)2.06 (7)2.849 (5)149 (6)
C7—H7···O1A0.982.553.525 (6)172
C11—H11A···O3ii0.972.453.278 (6)143
C21B—H21B···O5Biii0.932.523.369 (9)151
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+3/2; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC26H32O6
Mr440.52
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)12.3642 (4), 12.8445 (5), 43.5584 (15)
V3)6917.6 (4)
Z12
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.48 × 0.40 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
38709, 9382, 6530
Rint0.059
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.212, 0.99
No. of reflections9382
No. of parameters891
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.40

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4A—H4OA···O11.01 (6)1.83 (6)2.818 (5)169 (5)
O4—H4O···O1B0.81 (5)2.14 (5)2.952 (5)177 (4)
O4B—H4OB···O5Ai0.88 (7)2.06 (7)2.849 (5)149 (6)
C7—H7···O1A0.982.553.525 (6)172.4
C11—H11A···O3ii0.972.453.278 (6)142.8
C21B—H21B···O5Biii0.932.523.369 (9)151.3
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+3/2; (iii) x, y1, z.
 

Acknowledgements

Financial support from a Chulalongkorn University Graduate School Thesis Grant is gratefully acknowledged. The authors also thank the Center for Petroleum, Petrochemicals and Advanced Materials, Chulalongkorn University, for partial support. Finally, the authors are grateful for research funds from the Faculty of Science (A1B1), the Thai Government Stimulus Package 2 (TKK2555), under the Project for the Establishment of a Comprehensive Center for Innovative Food, Health Products and Agriculture, for support of the X-ray Crystallographic analysis.

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