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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages o3305-o3306
https://doi.org/10.1107/S1600536811047180

4,5,6,10,11,12,16,17,18,22,23,24-Dodeca­kis­[(meth­­oxy­carbon­yl)meth­­oxy]-2,8,14,20-tetra­pentyl­resorcin[4]arene

Pramod B. Pansuriya,a Holger B. Friedricha and Glenn E. M. Maguirea*

aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 4 November 2011; accepted 8 November 2011; online 16 November 2011)

The title compound, C84H112O36, has a macrocyclic structure. It has 12 (meth­oxy­carbon­yl)meth­oxy `head groups' in the upper rim and exhibits a flattened boat geometry. Intra­molecular C—H⋯O hydrogen bonds occur. In the crystal, inter­molecular C—H⋯O contacts occur. The `head groups' and the pentyl `feet' contain disordered (0.5:0.5 occupancy ratio) atoms.

Related literature

For applications of resorcin[4]arenes, see: Gerkensmeier et al. (1999[Gerkensmeier, T., Iwanek, W., Agena, C., Fröhlich, R., Kotila, S., Näther, C. & Mattay, J. (1999). Eur. J. Org. Chem. pp. 2257-2262.]); Palmer & Rebek (2005[Palmer, L. C. & Rebek, J. Jr (2005). Org. Lett. 7, 787-789.]); Demura et al. (2005[Demura, M., Yoshida, T., Hirokawa, T., Kumaki, Y., Aizawa, T., Nitta, K., Bitterc, I. & Tóthd, K. (2005). Bioorg. Med. Chem. Lett. 15, 1367-1370.]); Kulikov et al. (2009[Kulikov, O. V., Li, R. & Gokel, G. W. (2009). Angew. Chem. Int. Ed. 48, 375-377.]); Jin et al. (2009[Jin, P., Dalgarno, S. J., Warren, J. E., Teat, S. J. & Atwood, J. L. (2009). Chem. Commun. pp. 3348-3350.]). For structural information, see: McKay et al. (2007[McKay, M. G., Friedrich, H. B. & Maguire, G. E. M. (2007). Acta Cryst. E63, o4345.]); Pansuriya et al. (2011[Pansuriya, P. B., Friedrich, H. B. & Maguire, G. E. M. (2011). Acta Cryst. E67, o2907.]). For the synthesis of tetra­meth­oxy resorcin[4]arenes, see: Gerkensmeier et al. (1999[Gerkensmeier, T., Iwanek, W., Agena, C., Fröhlich, R., Kotila, S., Näther, C. & Mattay, J. (1999). Eur. J. Org. Chem. pp. 2257-2262.]).

[Scheme 1]

Experimental

Crystal data

  • C84H112O36

  • Mr = 1697.74

  • Triclinic, [P \overline 1]

  • a = 13.8526 (7) Å

  • b = 13.9033 (7) Å

  • c = 23.7333 (11) Å

  • α = 102.231 (1)°

  • β = 90.865 (1)°

  • γ = 94.900 (1)°

  • V = 4448.3 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 173 K

  • 0.49 × 0.32 × 0.28 mm
Data collection

  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.973

  • 48747 measured reflections

  • 21987 independent reflections

  • 14127 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.251

  • S = 1.05

  • 21987 reflections

  • 1084 parameters

  • 19 restraints

  • H-atom parameters constrained

  • Δρmax = 0.93 e Å−3

  • Δρmin = −0.99 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C32—H32B⋯O18i 0.99 2.55 3.304 (4) 133
C34A—H34A⋯O12i 1.16 2.29 3.085 (9) 124
C45—H45A⋯O29ii 0.98 2.33 3.304 (5) 175
C45—H45B⋯O35iii 0.98 2.52 3.471 (6) 163
C48B—H48F⋯O5Aiv 0.98 2.53 3.406 (13) 149
C59A—H59A⋯O17v 0.98 2.37 3.093 (10) 130
C59A—H59D⋯O17v 0.93 2.35 3.093 (10) 137
C62—H62B⋯O23vi 0.98 2.51 3.415 (6) 153
C73—H73A⋯O1iv 0.98 2.55 3.491 (4) 160
C79—H79B⋯O11iii 0.98 2.54 3.443 (5) 153
C84A—H84D⋯O27i 0.98 2.39 3.242 (10) 145
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z; (iv) x+1, y, z; (v) -x+2, -y+1, -z+1; (vi) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047180/hg5135sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047180/hg5135Isup2.hkl

checkCIF report


Comment top

In recent years, resorcin[4]arene derivatives with wide ranging features such as constellation isomerism, molecular interaction, synthetic ion channel, and multidented ligand effects (Gerkensmeier et al., 1999; Palmer & Rebek, 2005; Demura et al., 2005; Kulikov et al., 2009; Jin et al., 2009 Have been investigated. Herein, we report the crystal structure of a resorcin[4]arene containing twelve (methoxycarbonyl)methoxy head groups on the upper rim. The title compound is a more flexible analogue compared to resorcin[4]arene structures that we have recently reported (McKay et al., 2007, Pansuriya et al., 2011).

The title compound has an rccc (partial boat) configuration (Fig. 1) and is similar to our previously reported tetramethoxy resorcin[4]arene structure which had a boat configuration (Pansuriya et al., 2011). The rings containing C1—C6 and the opposite ring C15—C20, are almost co-planar (dihedral angle 8.36°) whilst the other pair of aromatic rings C8—C13 and C22—C27 are almost parallel (dihedral angle 8.59°). Several non-classical inter and intramolecular hydrogen bonds (C—H···O) are present in the structure. In the packing structure the (methoxycarbonyl)methoxy groups as well as the feet interlock with each other in the [010] plane (Fig. 2).

Related literature top

For applications of resorcin[4]arenes, see: Gerkensmeier et al. (1999); Palmer & Rebek (2005); Demura et al. (2005); Kulikov et al. (2009); Jin et al. (2009). For structural information, see: McKay et al. (2007); Pansuriya et al. (2011). For the synthesis of tetramethoxy resorcin[4]arenes, see: Gerkensmeier et al. (1999).

Experimental top

In dry degased acetonitrile (100 ml) 2,8,14,20-tetrapentyl-5,11,17,23-tetrahydroxyresorc[4]-arene (Gerkensmeier et al., 1999) (0.499 g, 0.6 mmol) and anhydrous potassium carbonate (2.355 g, 17.1 mmol) were added. The reaction was stirred at 70 °C for ten minutes and then methyl acetyl bromide (1275 µl, 13.8 mmol) was added dropwise. This was allowed to reflux for 24 h and cooled to room temperature. The solvent was reduced in vacuum and the resulting residue extracted with DCM (100 ml). After being washed with 1M HCl (50 ml), water (50 ml) and brine (50 ml), the organic layer was dried over anhydrous magnesium sulfate. The solvent was reduced to complete dryness to afford pure product as a white solid (Yield: 0.8 g, 80%).

Crystal suitable for X-ray diffraction analysis were grown at room temperature from a solution of DCM:methanol (2:1).

Refinement top

Several parts of the molecule were disordered and modelled as two positions for each atom with site occupancy factor of 0.50. The disordered moieties are: C48A versus. C48B; C59A versus. C59B; C82A, C83A and C84A versus. C82B, C83B and C84B; C33A, C34A, O5A and O6A versus. C33B, C34B, O5B and O6B. The anisotropic displacement parameters of these disordered atoms and the bond distances of the disordered moieties were restrained during refinements. All hydrogen atoms were placed at calculated positions with attach distances ranging from 0.95 Å to 1.00 Å and refined as riding on their parent atoms with Uiso (H) = 1.2 or 1.5 Ueq (C).

Structure description top

In recent years, resorcin[4]arene derivatives with wide ranging features such as constellation isomerism, molecular interaction, synthetic ion channel, and multidented ligand effects (Gerkensmeier et al., 1999; Palmer & Rebek, 2005; Demura et al., 2005; Kulikov et al., 2009; Jin et al., 2009 Have been investigated. Herein, we report the crystal structure of a resorcin[4]arene containing twelve (methoxycarbonyl)methoxy head groups on the upper rim. The title compound is a more flexible analogue compared to resorcin[4]arene structures that we have recently reported (McKay et al., 2007, Pansuriya et al., 2011).

The title compound has an rccc (partial boat) configuration (Fig. 1) and is similar to our previously reported tetramethoxy resorcin[4]arene structure which had a boat configuration (Pansuriya et al., 2011). The rings containing C1—C6 and the opposite ring C15—C20, are almost co-planar (dihedral angle 8.36°) whilst the other pair of aromatic rings C8—C13 and C22—C27 are almost parallel (dihedral angle 8.59°). Several non-classical inter and intramolecular hydrogen bonds (C—H···O) are present in the structure. In the packing structure the (methoxycarbonyl)methoxy groups as well as the feet interlock with each other in the [010] plane (Fig. 2).

For applications of resorcin[4]arenes, see: Gerkensmeier et al. (1999); Palmer & Rebek (2005); Demura et al. (2005); Kulikov et al. (2009); Jin et al. (2009). For structural information, see: McKay et al. (2007); Pansuriya et al. (2011). For the synthesis of tetramethoxy resorcin[4]arenes, see: Gerkensmeier et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atomic numbering; the hydrogen atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing of the title compound in the [010] plane. All hydrogen atoms have been omitted for clarity.
4,5,6,10,11,12,16,17,18,22,23,24-Dodecakis[(methoxycarbonyl)methoxy]- 2,8,14,20-tetrapentylresorcin[4]arene top
Crystal data top
C84H112O36Z = 2
Mr = 1697.74F(000) = 1808
Triclinic, P1Dx = 1.268 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.8526 (7) ÅCell parameters from 48747 reflections
b = 13.9033 (7) Åθ = 1.5–28.4°
c = 23.7333 (11) ŵ = 0.10 mm−1
α = 102.231 (1)°T = 173 K
β = 90.865 (1)°Block, colourless
γ = 94.900 (1)°0.49 × 0.32 × 0.28 mm
V = 4448.3 (4) Å3
Data collection top
Bruker Kappa DUO APEXII
diffractometer		21987 independent reflections
Radiation source: fine-focus sealed tube14127 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
0.5° φ scans and ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		h = −18→18
Tmin = 0.953, Tmax = 0.973k = −18→18
48747 measured reflectionsl = −31→31
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.251H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1324P)2 + 2.1604P]
where P = (Fo2 + 2Fc2)/3
21987 reflections(Δ/σ)max < 0.001
1084 parametersΔρmax = 0.93 e Å−3
19 restraintsΔρmin = −0.99 e Å−3
Crystal data top
C84H112O36γ = 94.900 (1)°
Mr = 1697.74V = 4448.3 (4) Å3
Triclinic, P1Z = 2
a = 13.8526 (7) ÅMo Kα radiation
b = 13.9033 (7) ŵ = 0.10 mm−1
c = 23.7333 (11) ÅT = 173 K
α = 102.231 (1)°0.49 × 0.32 × 0.28 mm
β = 90.865 (1)°
Data collection top
Bruker Kappa DUO APEXII
diffractometer		21987 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		14127 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.973Rint = 0.027
48747 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07319 restraints
wR(F2) = 0.251H-atom parameters constrained
S = 1.05Δρmax = 0.93 e Å−3
21987 reflectionsΔρmin = −0.99 e Å−3
1084 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)
O10.13264 (12)0.31173 (13)0.14032 (7)0.0429 (4)
O20.10243 (17)0.13560 (17)0.06370 (10)0.0651 (6)
O30.0785 (2)0.2129 (2)−0.00817 (9)0.0840 (8)
O40.16273 (13)0.51494 (14)0.14819 (7)0.0464 (4)
O6B−0.0588 (11)0.6228 (14)0.1755 (8)0.155 (5)0.50
O70.31777 (14)0.62305 (13)0.21628 (7)0.0467 (4)
O80.4637 (2)0.7610 (2)0.20494 (13)0.0881 (8)
O90.3824 (2)0.79052 (18)0.12883 (11)0.0858 (8)
O100.58545 (13)0.52770 (12)0.18926 (7)0.0424 (4)
O110.6304 (3)0.5992 (2)0.09343 (11)0.1022 (11)
O120.6798 (2)0.74647 (17)0.14643 (11)0.0775 (7)
O130.75594 (12)0.43942 (15)0.19019 (7)0.0467 (4)
O140.89365 (17)0.3820 (3)0.11323 (10)0.0892 (9)
O150.78558 (19)0.3844 (3)0.04323 (10)0.0923 (9)
O160.79734 (11)0.34439 (14)0.28147 (7)0.0451 (4)
O170.92758 (17)0.47149 (18)0.35766 (10)0.0703 (6)
O181.04481 (14)0.43717 (19)0.29349 (9)0.0634 (6)
O190.81969 (12)0.24638 (13)0.42267 (7)0.0437 (4)
O201.06736 (17)0.3149 (2)0.40676 (13)0.0815 (8)
O210.9688 (2)0.3370 (3)0.48027 (13)0.1046 (11)
O220.80037 (13)0.04236 (14)0.40250 (8)0.0475 (4)
O230.92065 (18)−0.0667 (2)0.44649 (12)0.0789 (7)
O240.83115 (18)−0.05890 (19)0.52536 (10)0.0731 (7)
O250.63472 (15)−0.06190 (13)0.34663 (9)0.0549 (5)
O260.72536 (18)−0.19955 (18)0.38958 (13)0.0739 (7)
O270.7890 (2)−0.25356 (19)0.30427 (12)0.0887 (9)
O280.61969 (12)0.05048 (12)0.20480 (7)0.0413 (4)
O290.76894 (14)0.02241 (16)0.12940 (9)0.0601 (5)
O300.84630 (14)0.16619 (17)0.17455 (9)0.0614 (6)
O310.57879 (13)0.15382 (12)0.12059 (7)0.0420 (4)
O320.71822 (16)0.16864 (18)0.04556 (9)0.0675 (6)
O330.65902 (15)0.02776 (16)−0.01339 (9)0.0618 (5)
O340.39248 (13)0.21417 (13)0.11147 (7)0.0449 (4)
O350.48113 (19)0.22384 (16)0.00985 (9)0.0676 (6)
O360.52875 (17)0.38380 (16)0.04393 (9)0.0615 (5)
C10.27237 (16)0.31799 (17)0.20164 (10)0.0360 (5)
C20.21143 (16)0.36646 (18)0.17209 (10)0.0371 (5)
C30.22623 (17)0.46773 (18)0.17690 (10)0.0386 (5)
C40.30425 (18)0.52186 (17)0.21001 (10)0.0377 (5)
C50.36682 (16)0.47595 (17)0.24047 (9)0.0340 (4)
C60.34837 (16)0.37460 (17)0.23617 (10)0.0354 (5)
H60.38900.34260.25750.042*
C70.44980 (17)0.53857 (16)0.27734 (9)0.0346 (5)
H70.46810.59440.25800.042*
C80.54085 (16)0.48511 (15)0.27913 (9)0.0318 (4)
C90.60583 (16)0.48333 (16)0.23463 (9)0.0341 (5)
C100.69133 (16)0.43676 (17)0.23376 (9)0.0356 (5)
C110.71685 (15)0.39636 (17)0.28034 (9)0.0343 (5)
C120.65470 (15)0.39848 (16)0.32667 (9)0.0309 (4)
C130.56720 (15)0.44136 (15)0.32418 (9)0.0308 (4)
H130.52370.44060.35470.037*
C140.68698 (16)0.35817 (16)0.37786 (9)0.0324 (4)
H140.75850.37600.38280.039*
C150.67284 (16)0.24601 (16)0.36732 (9)0.0328 (4)
C160.74106 (17)0.19455 (18)0.38985 (10)0.0372 (5)
C170.72957 (18)0.09213 (18)0.38165 (10)0.0405 (5)
C180.64867 (18)0.03932 (17)0.35140 (11)0.0407 (5)
C190.57916 (17)0.08802 (17)0.32812 (9)0.0350 (5)
C200.59211 (16)0.19039 (16)0.33727 (9)0.0324 (4)
H200.54400.22400.32250.039*
C210.49368 (17)0.02652 (16)0.29302 (10)0.0359 (5)
H210.5174−0.03790.27390.043*
C220.46404 (16)0.07671 (16)0.24526 (9)0.0345 (5)
C230.53180 (16)0.09029 (16)0.20368 (10)0.0350 (5)
C240.50914 (17)0.13776 (16)0.15997 (9)0.0362 (5)
C250.41828 (17)0.17231 (17)0.15692 (9)0.0364 (5)
C260.34932 (16)0.16143 (16)0.19821 (10)0.0353 (5)
C270.37446 (16)0.11397 (16)0.24166 (10)0.0341 (4)
H270.32850.10670.27010.041*
C280.25388 (17)0.20660 (18)0.19525 (11)0.0398 (5)
H280.22460.17940.15570.048*
C290.1248 (2)0.3151 (2)0.08097 (11)0.0519 (6)
H29A0.18640.34460.06860.062*
H29B0.07230.35600.07450.062*
C300.1024 (2)0.2094 (3)0.04659 (12)0.0537 (7)
C310.0546 (4)0.1173 (4)−0.04665 (17)0.1165 (19)
H31A0.03840.1267−0.08530.175*
H31B−0.00100.0826−0.03210.175*
H31C0.11040.0780−0.04850.175*
C320.0816 (2)0.5415 (3)0.18191 (14)0.0644 (8)
H32A0.10310.59330.21630.077*
H32B0.05230.48320.19530.077*
C33B0.0316 (6)0.6084 (8)0.1556 (4)0.060 (2)0.50
C34B−0.1142 (10)0.6568 (10)0.1266 (7)0.155 (5)0.50
H34A−0.18030.66900.13830.233*0.50
H34B−0.11660.60500.09130.233*0.50
H34C−0.08050.71770.11940.233*0.50
C350.3204 (4)0.6603 (3)0.16515 (16)0.0885 (14)
H35A0.25710.68480.15830.106*
H35B0.33170.60650.13190.106*
C360.3975 (3)0.7411 (2)0.16959 (14)0.0651 (8)
C370.4514 (4)0.8719 (3)0.12526 (17)0.0892 (13)
H37A0.43170.90210.09370.134*
H37B0.51560.84810.11800.134*
H37C0.45400.92110.16170.134*
C380.41432 (18)0.58630 (17)0.33713 (10)0.0385 (5)
H38A0.34910.60830.33250.046*
H38B0.40850.53610.36120.046*
C390.48218 (19)0.67438 (18)0.36810 (10)0.0430 (5)
H39A0.54750.65230.37220.052*
H39B0.48750.72460.34410.052*
C400.4492 (2)0.7219 (2)0.42729 (11)0.0499 (6)
H40A0.45240.67450.45290.060*
H40B0.38070.73580.42400.060*
C410.5095 (3)0.8174 (2)0.45475 (12)0.0563 (7)
H41A0.57820.80380.45740.068*
H41B0.50540.86530.42950.068*
C420.4774 (4)0.8637 (3)0.51429 (15)0.0848 (12)
H42A0.51890.92460.52970.127*
H42B0.48270.81730.53980.127*
H42C0.41000.87910.51190.127*
C430.6397 (3)0.6229 (2)0.19571 (13)0.0613 (8)
H43A0.70570.61990.21150.074*
H43B0.60750.67290.22320.074*
C440.6463 (3)0.6519 (2)0.13949 (14)0.0647 (8)
C450.6989 (4)0.7835 (3)0.0947 (2)0.0969 (14)
H45A0.72340.85340.10540.145*
H45B0.63880.77660.07130.145*
H45C0.74730.74570.07240.145*
C460.72502 (19)0.3873 (2)0.13404 (11)0.0485 (6)
H46A0.67380.42090.11850.058*
H46B0.69880.31910.13490.058*
C470.8126 (2)0.3856 (3)0.09716 (12)0.0596 (8)
C490.88925 (19)0.3759 (3)0.26271 (12)0.0618 (8)
H49A0.87980.41710.23420.074*
H49B0.92090.31720.24320.074*
C500.95370 (19)0.4331 (2)0.31051 (12)0.0469 (6)
C511.1197 (3)0.4892 (4)0.33409 (18)0.0851 (12)
H51A1.18240.48710.31550.128*
H51B1.12210.45780.36730.128*
H51C1.10560.55810.34710.128*
C520.64378 (17)0.40365 (17)0.43593 (9)0.0349 (5)
H52A0.57220.39200.43220.042*
H52B0.66580.36940.46570.042*
C530.6716 (2)0.51402 (18)0.45618 (10)0.0440 (6)
H53A0.74140.52800.44970.053*
H53B0.63460.54990.43250.053*
C540.6527 (2)0.5531 (2)0.51943 (11)0.0471 (6)
H54A0.58300.53850.52590.056*
H54B0.68990.51720.54300.056*
C550.6792 (3)0.6621 (2)0.54015 (13)0.0608 (8)
H55A0.63860.69810.51850.073*
H55B0.74760.67740.53110.073*
C560.6672 (3)0.7004 (3)0.60402 (14)0.0701 (9)
H56A0.68560.77170.61400.105*
H56B0.70870.66690.62600.105*
H56C0.59930.68730.61340.105*
C570.90769 (18)0.2393 (2)0.39250 (12)0.0471 (6)
H57A0.89910.25980.35540.057*
H57B0.92340.16960.38380.057*
C580.9896 (2)0.3023 (2)0.42670 (15)0.0582 (7)
C600.7784 (2)0.0235 (2)0.45776 (12)0.0521 (7)
H60A0.7130−0.01170.45650.063*
H60B0.77960.08650.48660.063*
C610.8536 (2)−0.0389 (2)0.47394 (14)0.0549 (7)
C620.8964 (4)−0.1161 (4)0.5486 (2)0.0988 (14)
H62A0.8737−0.12660.58590.148*
H62B0.9613−0.08080.55380.148*
H62C0.8989−0.18020.52200.148*
C630.6997 (3)−0.1183 (2)0.31008 (15)0.0736 (10)
H63A0.7548−0.07430.30120.088*
H63B0.6658−0.15250.27340.088*
C640.7369 (2)−0.1944 (2)0.34179 (17)0.0613 (8)
C650.8307 (4)−0.3291 (3)0.3290 (2)0.1020 (15)
H65A0.8673−0.37030.29970.153*
H65B0.7786−0.37050.34210.153*
H65C0.8742−0.29720.36180.153*
C660.41294 (18)0.00307 (18)0.33315 (11)0.0416 (5)
H66A0.4433−0.01180.36800.050*
H66B0.37810.06280.34570.050*
C670.3390 (2)−0.08324 (19)0.30649 (13)0.0494 (6)
H67A0.3056−0.06760.27280.059*
H67B0.3732−0.14300.29270.059*
C680.2637 (3)−0.1046 (2)0.34966 (17)0.0691 (9)
H68A0.2979−0.11360.38490.083*
H68B0.2260−0.04660.36080.083*
C690.1947 (3)−0.1945 (3)0.3272 (3)0.1151 (14)
H69A0.2319−0.25270.31550.138*
H69B0.1589−0.18520.29260.138*
C710.70280 (17)0.1200 (2)0.21429 (11)0.0440 (6)
H71A0.73440.11990.25200.053*
H71B0.68270.18700.21560.053*
C720.77419 (18)0.0953 (2)0.16712 (11)0.0460 (6)
C730.9223 (2)0.1517 (3)0.13299 (15)0.0713 (10)
H73A0.97200.20770.14210.107*
H73B0.89470.14690.09410.107*
H73C0.95160.09060.13460.107*
C740.57699 (19)0.07468 (19)0.07079 (10)0.0426 (5)
H74A0.51470.06880.04880.051*
H74B0.58410.01140.08250.051*
C750.6599 (2)0.0980 (2)0.03421 (11)0.0466 (6)
C760.7376 (3)0.0367 (3)−0.05216 (16)0.0840 (12)
H76A0.7301−0.0189−0.08550.126*
H76B0.79970.0362−0.03190.126*
H76C0.73620.0989−0.06520.126*
C770.4464 (2)0.30404 (19)0.10712 (11)0.0454 (6)
H77A0.50040.31910.13630.054*
H77B0.40390.35880.11510.054*
C780.4864 (2)0.2963 (2)0.04783 (11)0.0487 (6)
C790.5725 (3)0.3904 (3)−0.01014 (14)0.0715 (9)
H79A0.60120.4580−0.00800.107*
H79B0.52290.3729−0.04140.107*
H79C0.62320.3447−0.01770.107*
C800.17789 (19)0.1841 (2)0.23849 (14)0.0523 (7)
H80A0.20910.19920.27750.063*
H80B0.12600.22900.23890.063*
C48A0.8589 (6)0.3402 (9)0.0006 (3)0.0923 (9)0.50
H48A0.83700.3417−0.03860.138*0.50
H48B0.86490.27160.00350.138*0.50
H48C0.92190.37860.00950.138*0.50
C59A1.0468 (7)0.3747 (9)0.5269 (4)0.1046 (11)0.50
H59A1.01650.39900.56360.157*0.50
H59B1.08820.42870.51660.157*0.50
H59C1.08610.32090.53060.157*0.50
C48B0.8624 (6)0.4000 (9)0.0032 (3)0.0923 (9)0.50
H48D0.83320.3995−0.03470.138*0.50
H48E0.90560.3469−0.00030.138*0.50
H48F0.89960.46380.01800.138*0.50
C59B1.0539 (7)0.4097 (9)0.5074 (4)0.1046 (11)0.50
H59D1.04040.43830.54760.157*0.50
H59E1.06330.46260.48600.157*0.50
H59F1.11280.37510.50620.157*0.50
C700.1219 (3)−0.2139 (3)0.3726 (3)0.1151 (14)
H70A0.0780−0.27270.35630.173*
H70B0.0842−0.15680.38390.173*
H70C0.1569−0.22480.40660.173*
C82A0.0532 (9)0.0504 (7)0.2614 (6)0.0989 (10)0.50
H82A0.00300.09720.26250.119*0.50
H82B0.07900.05750.30140.119*0.50
C83B0.0037 (7)−0.0223 (7)0.2817 (5)0.0989 (10)0.50
H83A−0.0426−0.01280.31340.119*0.50
H83B0.0552−0.06140.29180.119*0.50
C83A0.0065 (7)−0.0521 (7)0.2412 (5)0.0989 (10)0.50
H83C0.0549−0.10090.23980.119*0.50
H83D−0.0238−0.06030.20230.119*0.50
C84B−0.0498 (6)−0.0769 (7)0.2240 (4)0.0989 (10)0.50
H84A−0.0870−0.13700.22990.148*0.50
H84B−0.0021−0.09470.19440.148*0.50
H84C−0.0939−0.03340.21150.148*0.50
C84A−0.0696 (6)−0.0663 (7)0.2845 (5)0.0989 (10)0.50
H84D−0.1002−0.13420.27440.148*0.50
H84E−0.1188−0.01990.28400.148*0.50
H84F−0.0390−0.05410.32320.148*0.50
C82B0.0481 (9)0.0789 (7)0.2726 (6)0.0989 (10)0.50
H82C0.07530.11750.31030.119*0.50
H82D−0.00500.11460.26090.119*0.50
C810.1314 (3)0.0780 (3)0.2262 (2)0.0989 (10)
H81A0.10670.06180.18560.119*
H81B0.18360.03460.22880.119*
O5A0.0172 (6)0.5699 (6)0.0932 (4)0.106 (3)0.50
O5B0.0472 (7)0.6391 (9)0.1141 (5)0.142 (5)0.50
C33A0.0037 (8)0.5812 (9)0.1459 (6)0.105 (6)0.50
O6A−0.0469 (7)0.6352 (10)0.1866 (5)0.0859 (19)0.50
C34A−0.1111 (6)0.6977 (7)0.1668 (4)0.0859 (19)0.50
H34D−0.14490.73350.19960.129*0.50
H34E−0.15870.65710.13870.129*0.50
H34F−0.07370.74500.14850.129*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0356 (9)0.0551 (10)0.0370 (8)−0.0006 (7)−0.0095 (7)0.0098 (7)
O20.0721 (15)0.0595 (13)0.0586 (13)0.0093 (11)0.0098 (11)−0.0008 (10)
O30.106 (2)0.0953 (19)0.0388 (11)−0.0154 (15)−0.0057 (12)−0.0014 (11)
O40.0482 (10)0.0555 (11)0.0404 (9)0.0099 (8)−0.0066 (8)0.0196 (8)
O6B0.125 (7)0.112 (6)0.231 (11)0.071 (6)−0.026 (6)0.022 (7)
O70.0620 (11)0.0381 (9)0.0422 (9)0.0031 (8)−0.0084 (8)0.0145 (7)
O80.100 (2)0.0786 (17)0.0863 (18)−0.0127 (15)−0.0174 (16)0.0284 (15)
O90.133 (2)0.0634 (14)0.0619 (14)−0.0249 (15)−0.0115 (14)0.0291 (12)
O100.0578 (11)0.0359 (8)0.0332 (8)−0.0006 (7)0.0016 (7)0.0088 (7)
O110.177 (3)0.0711 (17)0.0541 (14)−0.0273 (18)−0.0237 (17)0.0209 (13)
O120.1058 (19)0.0533 (13)0.0777 (16)−0.0071 (12)0.0090 (14)0.0294 (12)
O130.0377 (9)0.0685 (12)0.0285 (8)−0.0081 (8)0.0049 (7)0.0034 (8)
O140.0456 (13)0.167 (3)0.0556 (13)0.0179 (15)0.0090 (10)0.0216 (16)
O150.0693 (14)0.170 (3)0.0415 (10)0.0178 (16)0.0131 (9)0.0290 (15)
O160.0279 (8)0.0666 (12)0.0386 (9)0.0077 (7)0.0033 (7)0.0047 (8)
O170.0631 (14)0.0711 (14)0.0623 (13)−0.0039 (11)−0.0017 (11)−0.0137 (11)
O180.0353 (10)0.0942 (16)0.0617 (13)−0.0055 (10)−0.0047 (9)0.0241 (12)
O190.0376 (9)0.0507 (10)0.0384 (9)0.0070 (7)−0.0098 (7)−0.0006 (7)
O200.0443 (13)0.0868 (18)0.119 (2)−0.0046 (11)−0.0089 (13)0.0388 (16)
O210.0631 (14)0.139 (3)0.0811 (18)−0.0007 (15)−0.0243 (13)−0.0405 (16)
O220.0459 (10)0.0533 (11)0.0466 (10)0.0184 (8)−0.0058 (8)0.0127 (8)
O230.0677 (15)0.0925 (18)0.0885 (18)0.0362 (14)0.0008 (13)0.0352 (15)
O240.0823 (16)0.0794 (16)0.0677 (14)0.0196 (13)−0.0118 (12)0.0344 (13)
O250.0630 (12)0.0341 (9)0.0673 (12)0.0115 (8)−0.0115 (10)0.0087 (8)
O260.0749 (16)0.0640 (14)0.0901 (19)0.0155 (12)−0.0053 (13)0.0297 (13)
O270.123 (2)0.0605 (14)0.0801 (17)0.0475 (15)−0.0207 (16)−0.0041 (12)
O280.0348 (8)0.0406 (9)0.0451 (9)0.0050 (7)0.0010 (7)0.0008 (7)
O290.0497 (11)0.0590 (12)0.0600 (12)0.0065 (9)0.0083 (9)−0.0143 (10)
O300.0403 (10)0.0736 (14)0.0565 (12)−0.0069 (9)0.0134 (9)−0.0134 (10)
O310.0464 (9)0.0415 (9)0.0328 (8)−0.0035 (7)0.0043 (7)−0.0014 (7)
O320.0633 (13)0.0753 (15)0.0506 (12)−0.0166 (11)0.0139 (10)−0.0084 (10)
O330.0573 (12)0.0663 (13)0.0495 (11)0.0030 (10)0.0080 (9)−0.0146 (9)
O340.0531 (10)0.0437 (9)0.0367 (9)−0.0041 (8)−0.0109 (8)0.0099 (7)
O350.1036 (18)0.0573 (13)0.0397 (10)0.0062 (12)0.0008 (11)0.0056 (9)
O360.0785 (15)0.0582 (12)0.0456 (11)−0.0073 (10)0.0035 (10)0.0117 (9)
C10.0340 (11)0.0359 (11)0.0359 (11)0.0014 (9)−0.0039 (9)0.0039 (9)
C20.0330 (11)0.0443 (12)0.0332 (11)0.0034 (9)−0.0024 (9)0.0070 (9)
C30.0390 (12)0.0478 (13)0.0312 (11)0.0079 (10)−0.0016 (9)0.0120 (10)
C40.0448 (13)0.0373 (12)0.0316 (11)0.0044 (10)0.0027 (9)0.0089 (9)
C50.0361 (11)0.0355 (11)0.0291 (10)0.0026 (9)−0.0006 (8)0.0041 (8)
C60.0335 (11)0.0370 (11)0.0346 (11)0.0041 (9)−0.0049 (9)0.0052 (9)
C70.0388 (12)0.0314 (10)0.0318 (10)0.0008 (9)−0.0019 (9)0.0037 (8)
C80.0330 (11)0.0282 (10)0.0306 (10)−0.0022 (8)−0.0026 (8)0.0004 (8)
C90.0390 (12)0.0325 (11)0.0277 (10)−0.0043 (9)−0.0016 (8)0.0031 (8)
C100.0327 (11)0.0401 (12)0.0297 (10)−0.0060 (9)0.0038 (8)0.0011 (9)
C110.0270 (10)0.0401 (12)0.0311 (10)−0.0013 (8)−0.0010 (8)−0.0012 (9)
C120.0287 (10)0.0329 (10)0.0277 (10)−0.0013 (8)−0.0017 (8)0.0003 (8)
C130.0290 (10)0.0319 (10)0.0282 (10)−0.0015 (8)0.0012 (8)0.0009 (8)
C140.0297 (10)0.0354 (11)0.0294 (10)0.0019 (8)−0.0011 (8)0.0011 (8)
C150.0338 (11)0.0353 (11)0.0272 (10)0.0079 (8)0.0003 (8)0.0004 (8)
C160.0348 (11)0.0442 (12)0.0308 (10)0.0074 (9)−0.0044 (9)0.0028 (9)
C170.0435 (13)0.0435 (13)0.0357 (11)0.0154 (10)−0.0031 (10)0.0068 (10)
C180.0462 (13)0.0337 (11)0.0411 (12)0.0090 (10)−0.0031 (10)0.0040 (9)
C190.0371 (11)0.0357 (11)0.0308 (10)0.0046 (9)−0.0035 (9)0.0037 (9)
C200.0317 (10)0.0354 (11)0.0289 (10)0.0069 (8)−0.0020 (8)0.0031 (8)
C210.0389 (12)0.0307 (11)0.0367 (11)0.0030 (9)−0.0011 (9)0.0044 (9)
C220.0368 (11)0.0304 (10)0.0324 (10)−0.0004 (8)−0.0037 (9)−0.0003 (8)
C230.0332 (11)0.0318 (11)0.0351 (11)0.0013 (8)−0.0032 (9)−0.0029 (8)
C240.0405 (12)0.0330 (11)0.0307 (10)−0.0035 (9)0.0007 (9)−0.0002 (8)
C250.0408 (12)0.0341 (11)0.0313 (10)−0.0027 (9)−0.0067 (9)0.0029 (9)
C260.0353 (11)0.0306 (10)0.0363 (11)−0.0017 (8)−0.0068 (9)0.0013 (9)
C270.0333 (11)0.0320 (11)0.0344 (11)−0.0010 (8)−0.0024 (9)0.0028 (8)
C280.0344 (12)0.0387 (12)0.0434 (12)−0.0013 (9)−0.0095 (10)0.0051 (10)
C290.0517 (15)0.0635 (17)0.0391 (13)0.0016 (13)−0.0092 (11)0.0101 (12)
C300.0435 (15)0.072 (2)0.0391 (13)0.0032 (13)0.0040 (11)−0.0015 (13)
C310.151 (5)0.121 (4)0.052 (2)−0.033 (3)−0.005 (2)−0.022 (2)
C320.0660 (19)0.076 (2)0.0591 (18)0.0308 (16)0.0038 (15)0.0217 (16)
C33B0.031 (4)0.085 (7)0.075 (5)0.012 (4)0.007 (4)0.040 (5)
C34B0.125 (7)0.112 (6)0.231 (11)0.071 (6)−0.026 (6)0.022 (7)
C350.128 (3)0.076 (2)0.066 (2)−0.036 (2)−0.030 (2)0.0446 (19)
C360.098 (3)0.0474 (16)0.0461 (16)0.0030 (16)−0.0016 (17)0.0039 (13)
C370.139 (4)0.0513 (19)0.071 (2)−0.021 (2)0.012 (2)0.0100 (17)
C380.0410 (12)0.0374 (12)0.0347 (11)0.0073 (9)−0.0010 (9)0.0012 (9)
C390.0493 (14)0.0378 (12)0.0377 (12)0.0049 (10)−0.0013 (10)−0.0013 (10)
C400.0567 (16)0.0461 (14)0.0414 (13)0.0085 (12)0.0046 (12)−0.0048 (11)
C410.078 (2)0.0455 (15)0.0406 (14)0.0053 (14)0.0006 (13)−0.0015 (11)
C420.121 (3)0.064 (2)0.0566 (19)0.010 (2)0.017 (2)−0.0172 (16)
C430.087 (2)0.0431 (15)0.0505 (16)−0.0134 (14)0.0028 (15)0.0111 (12)
C440.087 (2)0.0494 (16)0.0578 (18)−0.0105 (15)−0.0114 (16)0.0181 (14)
C450.126 (4)0.078 (3)0.098 (3)−0.011 (2)−0.003 (3)0.052 (2)
C460.0421 (14)0.0633 (17)0.0336 (12)−0.0011 (12)0.0051 (10)−0.0019 (11)
C470.0452 (16)0.094 (2)0.0373 (13)0.0063 (15)0.0070 (12)0.0085 (14)
C490.0312 (13)0.105 (3)0.0439 (15)0.0020 (14)0.0041 (11)0.0059 (15)
C500.0412 (13)0.0519 (15)0.0478 (14)0.0013 (11)−0.0024 (11)0.0124 (12)
C510.054 (2)0.113 (3)0.086 (3)−0.030 (2)−0.0198 (18)0.035 (2)
C520.0380 (12)0.0375 (11)0.0262 (10)0.0037 (9)−0.0014 (8)0.0002 (8)
C530.0537 (15)0.0384 (12)0.0347 (12)0.0003 (11)0.0001 (10)−0.0025 (9)
C540.0508 (15)0.0464 (14)0.0371 (12)0.0049 (11)0.0022 (11)−0.0068 (10)
C550.076 (2)0.0436 (15)0.0527 (16)0.0025 (14)0.0028 (15)−0.0108 (12)
C560.073 (2)0.0630 (19)0.0570 (18)0.0024 (16)0.0021 (16)−0.0254 (15)
C570.0383 (13)0.0549 (15)0.0479 (14)0.0084 (11)−0.0042 (11)0.0094 (12)
C580.0447 (16)0.0565 (17)0.072 (2)0.0068 (13)−0.0126 (14)0.0106 (15)
C600.0568 (16)0.0580 (16)0.0442 (14)0.0186 (13)−0.0061 (12)0.0122 (12)
C610.0550 (17)0.0511 (16)0.0612 (17)0.0082 (13)−0.0139 (14)0.0177 (13)
C620.111 (3)0.098 (3)0.108 (3)0.024 (3)−0.015 (3)0.065 (3)
C630.108 (3)0.0476 (17)0.0611 (19)0.0343 (18)−0.0197 (19)−0.0059 (14)
C640.0600 (18)0.0381 (14)0.079 (2)0.0095 (12)−0.0238 (16)−0.0015 (14)
C650.117 (4)0.071 (3)0.122 (4)0.047 (3)−0.019 (3)0.017 (2)
C660.0452 (13)0.0385 (12)0.0407 (12)0.0013 (10)0.0003 (10)0.0083 (10)
C670.0494 (15)0.0386 (13)0.0584 (16)−0.0021 (11)−0.0012 (12)0.0090 (12)
C680.0627 (19)0.0501 (17)0.093 (3)0.0002 (14)0.0207 (18)0.0137 (16)
C690.0762 (19)0.0654 (17)0.197 (4)−0.0128 (14)0.046 (2)0.017 (2)
C710.0348 (12)0.0506 (14)0.0408 (13)0.0022 (10)−0.0006 (10)−0.0027 (10)
C720.0365 (13)0.0538 (15)0.0438 (13)0.0066 (11)−0.0002 (10)0.0005 (11)
C730.0426 (16)0.091 (2)0.067 (2)−0.0053 (15)0.0179 (14)−0.0103 (17)
C740.0451 (13)0.0406 (12)0.0365 (12)0.0009 (10)−0.0017 (10)−0.0032 (10)
C750.0485 (14)0.0508 (15)0.0368 (12)0.0083 (12)−0.0003 (11)−0.0007 (11)
C760.077 (2)0.099 (3)0.061 (2)0.005 (2)0.0257 (18)−0.0157 (19)
C770.0550 (15)0.0402 (13)0.0393 (12)0.0015 (11)−0.0015 (11)0.0062 (10)
C780.0585 (16)0.0483 (15)0.0396 (13)0.0061 (12)−0.0070 (12)0.0100 (11)
C790.082 (2)0.086 (2)0.0485 (17)−0.0080 (19)0.0041 (16)0.0244 (16)
C800.0321 (12)0.0546 (16)0.0726 (19)−0.0001 (11)−0.0024 (12)0.0212 (14)
C48A0.0693 (14)0.170 (3)0.0415 (10)0.0178 (16)0.0131 (9)0.0290 (15)
C59A0.0631 (14)0.139 (3)0.0811 (18)−0.0007 (15)−0.0243 (13)−0.0405 (16)
C48B0.0693 (14)0.170 (3)0.0415 (10)0.0178 (16)0.0131 (9)0.0290 (15)
C59B0.0631 (14)0.139 (3)0.0811 (18)−0.0007 (15)−0.0243 (13)−0.0405 (16)
C700.0762 (19)0.0654 (17)0.197 (4)−0.0128 (14)0.046 (2)0.017 (2)
C82A0.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
C83B0.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
C83A0.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
C84B0.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
C84A0.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
C82B0.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
C810.0645 (14)0.092 (2)0.143 (3)−0.0269 (14)−0.0132 (17)0.045 (2)
O5A0.100 (5)0.121 (6)0.117 (6)0.031 (5)−0.037 (5)0.066 (5)
O5B0.134 (8)0.219 (11)0.140 (8)0.123 (8)0.081 (6)0.140 (8)
C33A0.082 (9)0.060 (6)0.174 (13)−0.002 (5)−0.075 (9)0.036 (7)
O6A0.065 (3)0.102 (4)0.109 (4)0.049 (3)0.026 (3)0.045 (4)
C34A0.065 (3)0.102 (4)0.109 (4)0.049 (3)0.026 (3)0.045 (4)
Geometric parameters (Å, º) top
O1—C21.389 (3)C40—C411.521 (4)
O1—C291.422 (3)C40—H40A0.9900
O2—C301.181 (4)C40—H40B0.9900
O3—C301.348 (4)C41—C421.513 (4)
O3—C311.453 (5)C41—H41A0.9900
O4—C31.392 (3)C41—H41B0.9900
O4—C321.419 (4)C42—H42A0.9800
O6B—C33B1.361 (14)C42—H42B0.9800
O6B—C34B1.558 (15)C42—H42C0.9800
O7—C41.379 (3)C43—C441.476 (4)
O7—C351.417 (3)C43—H43A0.9900
O8—C361.207 (4)C43—H43B0.9900
O9—C361.324 (4)C45—H45A0.9800
O9—C371.435 (4)C45—H45B0.9800
O10—C91.386 (3)C45—H45C0.9800
O10—C431.442 (3)C46—C471.506 (4)
O11—C441.186 (4)C46—H46A0.9900
O12—C441.331 (4)C46—H46B0.9900
O12—C451.448 (4)C49—C501.477 (4)
O13—C101.382 (3)C49—H49A0.9900
O13—C461.416 (3)C49—H49B0.9900
O14—C471.188 (4)C51—H51A0.9800
O15—C471.325 (4)C51—H51B0.9800
O15—C48B1.469 (8)C51—H51C0.9800
O15—C48A1.519 (9)C52—C531.522 (3)
O16—C111.382 (3)C52—H52A0.9900
O16—C491.420 (3)C52—H52B0.9900
O17—C501.208 (3)C53—C541.519 (3)
O18—C501.331 (3)C53—H53A0.9900
O18—C511.440 (4)C53—H53B0.9900
O19—C161.384 (3)C54—C551.503 (4)
O19—C571.423 (3)C54—H54A0.9900
O20—C581.197 (4)C54—H54B0.9900
O21—C581.306 (4)C55—C561.513 (4)
O21—C59A1.512 (9)C55—H55A0.9900
O21—C59B1.525 (10)C55—H55B0.9900
O22—C171.390 (3)C56—H56A0.9800
O22—C601.423 (3)C56—H56B0.9800
O23—C611.187 (4)C56—H56C0.9800
O24—C611.343 (4)C57—C581.489 (4)
O24—C621.431 (4)C57—H57A0.9900
O25—C181.384 (3)C57—H57B0.9900
O25—C631.426 (4)C60—C611.506 (4)
O26—C641.164 (4)C60—H60A0.9900
O27—C641.342 (4)C60—H60B0.9900
O27—C651.462 (4)C62—H62A0.9800
O28—C231.382 (3)C62—H62B0.9800
O28—C711.421 (3)C62—H62C0.9800
O29—C721.198 (3)C63—C641.540 (4)
O30—C721.324 (3)C63—H63A0.9900
O30—C731.451 (3)C63—H63B0.9900
O31—C241.390 (3)C65—H65A0.9800
O31—C741.432 (3)C65—H65B0.9800
O32—C751.199 (3)C65—H65C0.9800
O33—C751.326 (3)C66—C671.529 (3)
O33—C761.450 (4)C66—H66A0.9900
O34—C251.385 (3)C66—H66B0.9900
O34—C771.424 (3)C67—C681.527 (4)
O35—C781.197 (3)C67—H67A0.9900
O36—C781.327 (3)C67—H67B0.9900
O36—C791.445 (4)C68—C691.503 (5)
C1—C21.392 (3)C68—H68A0.9900
C1—C61.400 (3)C68—H68B0.9900
C1—C281.523 (3)C69—C701.537 (6)
C2—C31.385 (3)C69—H69A0.9900
C3—C41.392 (3)C69—H69B0.9900
C4—C51.397 (3)C71—C721.509 (4)
C5—C61.392 (3)C71—H71A0.9900
C5—C71.524 (3)C71—H71B0.9900
C6—H60.9500C73—H73A0.9800
C7—C81.522 (3)C73—H73B0.9800
C7—C381.540 (3)C73—H73C0.9800
C7—H71.0000C74—C751.504 (4)
C8—C91.396 (3)C74—H74A0.9900
C8—C131.396 (3)C74—H74B0.9900
C9—C101.396 (3)C76—H76A0.9800
C10—C111.396 (3)C76—H76B0.9800
C11—C121.404 (3)C76—H76C0.9800
C12—C131.402 (3)C77—C781.506 (4)
C12—C141.518 (3)C77—H77A0.9900
C13—H130.9500C77—H77B0.9900
C14—C151.521 (3)C79—H79A0.9800
C14—C521.542 (3)C79—H79B0.9800
C14—H141.0000C79—H79C0.9800
C15—C201.397 (3)C80—C811.525 (5)
C15—C161.398 (3)C80—H80A0.9900
C16—C171.391 (3)C80—H80B0.9900
C17—C181.386 (4)C48A—H48A0.9800
C18—C191.395 (3)C48A—H48B0.9800
C19—C201.389 (3)C48A—H48C0.9800
C19—C211.524 (3)C59A—H59A0.9800
C20—H200.9500C59A—H59B0.9800
C21—C221.520 (3)C59A—H59C0.9800
C21—C661.538 (3)C48B—H48D0.9800
C21—H211.0000C48B—H48E0.9800
C22—C271.393 (3)C48B—H48F0.9800
C22—C231.403 (3)C59B—H59D0.9800
C23—C241.388 (3)C59B—H59E0.9800
C24—C251.391 (3)C59B—H59F0.9800
C25—C261.401 (3)C70—H70A0.9800
C26—C271.392 (3)C70—H70B0.9800
C26—C281.518 (3)C70—H70C0.9800
C27—H270.9500C82A—C811.453 (11)
C28—C801.540 (4)C82A—C83A1.491 (11)
C28—H281.0000C82A—H82A0.9900
C29—C301.526 (4)C82A—H82B0.9900
C29—H29A0.9900C83B—C82B1.545 (11)
C29—H29B0.9900C83B—C84B1.560 (12)
C31—H31A0.9800C83B—H83A0.9900
C31—H31B0.9800C83B—H83B0.9900
C31—H31C0.9800C83A—C84A1.512 (11)
C32—C33B1.442 (11)C83A—H83C0.9900
C32—C33A1.571 (13)C83A—H83D0.9900
C32—H32A0.9900C84B—H84A0.9800
C32—H32B0.9900C84B—H84B0.9800
C33B—O5B1.169 (10)C84B—H84C0.9800
C34B—H34A0.9800C84A—H84D0.9800
C34B—H34B0.9800C84A—H84E0.9800
C34B—H34C0.9800C84A—H84F0.9800
C35—C361.468 (5)C82B—C811.606 (12)
C35—H35A0.9900C82B—H82C0.9900
C35—H35B0.9900C82B—H82D0.9900
C37—H37A0.9800C81—H81A0.9900
C37—H37B0.9800C81—H81B0.9900
C37—H37C0.9800O5A—C33A1.246 (14)
C38—C391.525 (3)C33A—O6A1.338 (14)
C38—H38A0.9900O6A—C34A1.435 (10)
C38—H38B0.9900C34A—H34D0.9800
C39—C401.515 (3)C34A—H34E0.9800
C39—H39A0.9900C34A—H34F0.9800
C39—H39B0.9900
C2—O1—C29117.03 (19)O18—C51—H51A109.5
C30—O3—C31115.0 (3)O18—C51—H51B109.5
C3—O4—C32111.32 (19)H51A—C51—H51B109.5
C33B—O6B—C34B105.2 (12)O18—C51—H51C109.5
C4—O7—C35117.1 (2)H51A—C51—H51C109.5
C36—O9—C37117.7 (3)H51B—C51—H51C109.5
C9—O10—C43111.29 (19)C53—C52—C14113.71 (19)
C44—O12—C45117.1 (3)C53—C52—H52A108.8
C10—O13—C46116.97 (18)C14—C52—H52A108.8
C47—O15—C48B117.3 (4)C53—C52—H52B108.8
C47—O15—C48A111.8 (4)C14—C52—H52B108.8
C48B—O15—C48A31.7 (5)H52A—C52—H52B107.7
C11—O16—C49122.9 (2)C54—C53—C52113.5 (2)
C50—O18—C51118.5 (3)C54—C53—H53A108.9
C16—O19—C57112.58 (18)C52—C53—H53A108.9
C58—O21—C59A122.0 (5)C54—C53—H53B108.9
C58—O21—C59B107.1 (5)C52—C53—H53B108.9
C59A—O21—C59B28.2 (6)H53A—C53—H53B107.7
C17—O22—C60111.9 (2)C55—C54—C53114.2 (2)
C61—O24—C62115.8 (3)C55—C54—H54A108.7
C18—O25—C63115.3 (2)C53—C54—H54A108.7
C64—O27—C65113.1 (3)C55—C54—H54B108.7
C23—O28—C71115.44 (18)C53—C54—H54B108.7
C72—O30—C73115.7 (2)H54A—C54—H54B107.6
C24—O31—C74113.09 (18)C54—C55—C56114.6 (3)
C75—O33—C76116.3 (3)C54—C55—H55A108.6
C25—O34—C77116.58 (18)C56—C55—H55A108.6
C78—O36—C79116.8 (2)C54—C55—H55B108.6
C2—C1—C6118.0 (2)C56—C55—H55B108.6
C2—C1—C28119.1 (2)H55A—C55—H55B107.6
C6—C1—C28122.9 (2)C55—C56—H56A109.5
C3—C2—O1120.9 (2)C55—C56—H56B109.5
C3—C2—C1120.6 (2)H56A—C56—H56B109.5
O1—C2—C1118.4 (2)C55—C56—H56C109.5
C2—C3—C4120.2 (2)H56A—C56—H56C109.5
C2—C3—O4119.6 (2)H56B—C56—H56C109.5
C4—C3—O4120.2 (2)O19—C57—C58111.6 (2)
O7—C4—C3120.5 (2)O19—C57—H57A109.3
O7—C4—C5118.6 (2)C58—C57—H57A109.3
C3—C4—C5120.8 (2)O19—C57—H57B109.3
C6—C5—C4117.6 (2)C58—C57—H57B109.3
C6—C5—C7123.4 (2)H57A—C57—H57B108.0
C4—C5—C7119.0 (2)O20—C58—O21124.7 (3)
C5—C6—C1122.6 (2)O20—C58—C57122.1 (3)
C5—C6—H6118.7O21—C58—C57113.2 (3)
C1—C6—H6118.7O22—C60—C61107.9 (2)
C8—C7—C5113.69 (18)O22—C60—H60A110.1
C8—C7—C38114.30 (18)C61—C60—H60A110.1
C5—C7—C38110.53 (19)O22—C60—H60B110.1
C8—C7—H7105.8C61—C60—H60B110.1
C5—C7—H7105.8H60A—C60—H60B108.4
C38—C7—H7105.8O23—C61—O24125.4 (3)
C9—C8—C13116.8 (2)O23—C61—C60126.9 (3)
C9—C8—C7118.77 (19)O24—C61—C60107.8 (3)
C13—C8—C7124.38 (19)O24—C62—H62A109.5
O10—C9—C8119.8 (2)O24—C62—H62B109.5
O10—C9—C10118.2 (2)H62A—C62—H62B109.5
C8—C9—C10121.9 (2)O24—C62—H62C109.5
O13—C10—C11119.4 (2)H62A—C62—H62C109.5
O13—C10—C9120.5 (2)H62B—C62—H62C109.5
C11—C10—C9119.7 (2)O25—C63—C64108.1 (3)
O16—C11—C10123.28 (19)O25—C63—H63A110.1
O16—C11—C12116.2 (2)C64—C63—H63A110.1
C10—C11—C12120.2 (2)O25—C63—H63B110.1
C13—C12—C11118.01 (19)C64—C63—H63B110.1
C13—C12—C14123.25 (19)H63A—C63—H63B108.4
C11—C12—C14118.70 (19)O26—C64—O27125.4 (3)
C8—C13—C12123.25 (19)O26—C64—C63127.6 (3)
C8—C13—H13118.4O27—C64—C63107.0 (3)
C12—C13—H13118.4O27—C65—H65A109.5
C12—C14—C15113.19 (17)O27—C65—H65B109.5
C12—C14—C52115.35 (18)H65A—C65—H65B109.5
C15—C14—C52109.74 (18)O27—C65—H65C109.5
C12—C14—H14105.9H65A—C65—H65C109.5
C15—C14—H14105.9H65B—C65—H65C109.5
C52—C14—H14105.9C67—C66—C21115.0 (2)
C20—C15—C16117.2 (2)C67—C66—H66A108.5
C20—C15—C14123.04 (19)C21—C66—H66A108.5
C16—C15—C14119.74 (19)C67—C66—H66B108.5
O19—C16—C17119.2 (2)C21—C66—H66B108.5
O19—C16—C15119.6 (2)H66A—C66—H66B107.5
C17—C16—C15121.2 (2)C68—C67—C66111.9 (2)
C18—C17—O22119.9 (2)C68—C67—H67A109.2
C18—C17—C16120.1 (2)C66—C67—H67A109.2
O22—C17—C16120.0 (2)C68—C67—H67B109.2
O25—C18—C17119.6 (2)C66—C67—H67B109.2
O25—C18—C19119.8 (2)H67A—C67—H67B107.9
C17—C18—C19120.5 (2)C69—C68—C67113.9 (3)
C20—C19—C18118.3 (2)C69—C68—H68A108.8
C20—C19—C21123.12 (19)C67—C68—H68A108.8
C18—C19—C21118.6 (2)C69—C68—H68B108.8
C19—C20—C15122.8 (2)C67—C68—H68B108.8
C19—C20—H20118.6H68A—C68—H68B107.7
C15—C20—H20118.6C68—C69—C70111.9 (4)
C22—C21—C19109.33 (18)C68—C69—H69A109.2
C22—C21—C66116.00 (19)C70—C69—H69A109.2
C19—C21—C66110.29 (19)C68—C69—H69B109.2
C22—C21—H21106.9C70—C69—H69B109.2
C19—C21—H21106.9H69A—C69—H69B107.9
C66—C21—H21106.9O28—C71—C72111.0 (2)
C27—C22—C23117.7 (2)O28—C71—H71A109.4
C27—C22—C21123.7 (2)C72—C71—H71A109.4
C23—C22—C21118.5 (2)O28—C71—H71B109.4
O28—C23—C24120.2 (2)C72—C71—H71B109.4
O28—C23—C22118.9 (2)H71A—C71—H71B108.0
C24—C23—C22120.8 (2)O29—C72—O30124.5 (2)
C23—C24—O31119.7 (2)O29—C72—C71126.2 (2)
C23—C24—C25120.0 (2)O30—C72—C71109.3 (2)
O31—C24—C25120.2 (2)O30—C73—H73A109.5
O34—C25—C24120.6 (2)O30—C73—H73B109.5
O34—C25—C26118.5 (2)H73A—C73—H73B109.5
C24—C25—C26120.8 (2)O30—C73—H73C109.5
C27—C26—C25117.8 (2)H73A—C73—H73C109.5
C27—C26—C28123.5 (2)H73B—C73—H73C109.5
C25—C26—C28118.6 (2)O31—C74—C75107.5 (2)
C26—C27—C22122.9 (2)O31—C74—H74A110.2
C26—C27—H27118.6C75—C74—H74A110.2
C22—C27—H27118.6O31—C74—H74B110.2
C26—C28—C1110.00 (18)C75—C74—H74B110.2
C26—C28—C80115.9 (2)H74A—C74—H74B108.5
C1—C28—C80109.4 (2)O32—C75—O33124.5 (3)
C26—C28—H28107.0O32—C75—C74126.1 (2)
C1—C28—H28107.0O33—C75—C74109.4 (2)
C80—C28—H28107.0O33—C76—H76A109.5
O1—C29—C30107.8 (2)O33—C76—H76B109.5
O1—C29—H29A110.1H76A—C76—H76B109.5
C30—C29—H29A110.1O33—C76—H76C109.5
O1—C29—H29B110.1H76A—C76—H76C109.5
C30—C29—H29B110.1H76B—C76—H76C109.5
H29A—C29—H29B108.5O34—C77—C78110.7 (2)
O2—C30—O3124.0 (3)O34—C77—H77A109.5
O2—C30—C29127.6 (3)C78—C77—H77A109.5
O3—C30—C29108.3 (3)O34—C77—H77B109.5
O3—C31—H31A109.5C78—C77—H77B109.5
O3—C31—H31B109.5H77A—C77—H77B108.1
H31A—C31—H31B109.5O35—C78—O36124.8 (3)
O3—C31—H31C109.5O35—C78—C77126.3 (3)
H31A—C31—H31C109.5O36—C78—C77108.9 (2)
H31B—C31—H31C109.5O36—C79—H79A109.5
O4—C32—C33B107.7 (4)O36—C79—H79B109.5
O4—C32—C33A110.8 (6)H79A—C79—H79B109.5
C33B—C32—C33A19.7 (6)O36—C79—H79C109.5
O4—C32—H32A109.5H79A—C79—H79C109.5
C33B—C32—H32A93.4H79B—C79—H79C109.5
C33A—C32—H32A109.5C81—C80—C28115.1 (3)
O4—C32—H32B109.5C81—C80—H80A108.5
C33B—C32—H32B126.9C28—C80—H80A108.5
C33A—C32—H32B109.5C81—C80—H80B108.5
H32A—C32—H32B108.1C28—C80—H80B108.5
O5B—C33B—O6B113.3 (11)H80A—C80—H80B107.5
O5B—C33B—C32131.3 (8)O15—C48A—H48A109.5
O6B—C33B—C32113.9 (9)O15—C48A—H48B109.5
O6B—C34B—H34A109.5H48A—C48A—H48B109.5
O6B—C34B—H34B109.5O15—C48A—H48C109.5
H34A—C34B—H34B109.5H48A—C48A—H48C109.5
O6B—C34B—H34C109.5H48B—C48A—H48C109.5
H34A—C34B—H34C109.5O21—C59A—H59A109.5
H34B—C34B—H34C109.5O21—C59A—H59B109.5
O7—C35—C36110.8 (3)H59A—C59A—H59B109.5
O7—C35—H35A109.5O21—C59A—H59C109.5
C36—C35—H35A109.5H59A—C59A—H59C109.5
O7—C35—H35B109.5H59B—C59A—H59C109.5
C36—C35—H35B109.5O15—C48B—H48D109.5
H35A—C35—H35B108.1O15—C48B—H48E109.5
O8—C36—O9124.8 (3)H48D—C48B—H48E109.5
O8—C36—C35126.1 (3)O15—C48B—H48F109.5
O9—C36—C35109.1 (3)H48D—C48B—H48F109.5
O9—C37—H37A109.5H48E—C48B—H48F109.5
O9—C37—H37B109.5O21—C59B—H59D109.5
H37A—C37—H37B109.5O21—C59B—H59E109.5
O9—C37—H37C109.5H59D—C59B—H59E109.5
H37A—C37—H37C109.5O21—C59B—H59F109.5
H37B—C37—H37C109.5H59D—C59B—H59F109.5
C39—C38—C7112.7 (2)H59E—C59B—H59F109.5
C39—C38—H38A109.1C69—C70—H70A109.5
C7—C38—H38A109.1C69—C70—H70B109.5
C39—C38—H38B109.1H70A—C70—H70B109.5
C7—C38—H38B109.1C69—C70—H70C109.5
H38A—C38—H38B107.8H70A—C70—H70C109.5
C40—C39—C38113.6 (2)H70B—C70—H70C109.5
C40—C39—H39A108.8C81—C82A—C83A114.8 (9)
C38—C39—H39A108.8C81—C82A—H82A108.6
C40—C39—H39B108.8C83A—C82A—H82A108.6
C38—C39—H39B108.8C81—C82A—H82B108.6
H39A—C39—H39B107.7C83A—C82A—H82B108.6
C39—C40—C41113.4 (2)H82A—C82A—H82B107.5
C39—C40—H40A108.9C82B—C83B—C84B107.3 (9)
C41—C40—H40A108.9C82B—C83B—H83A110.2
C39—C40—H40B108.9C84B—C83B—H83A110.2
C41—C40—H40B108.9C82B—C83B—H83B110.2
H40A—C40—H40B107.7C84B—C83B—H83B110.2
C42—C41—C40113.2 (3)H83A—C83B—H83B108.5
C42—C41—H41A108.9C82A—C83A—C84A106.1 (9)
C40—C41—H41A108.9C82A—C83A—H83C110.5
C42—C41—H41B108.9C84A—C83A—H83C110.5
C40—C41—H41B108.9C82A—C83A—H83D110.5
H41A—C41—H41B107.7C84A—C83A—H83D110.5
C41—C42—H42A109.5H83C—C83A—H83D108.7
C41—C42—H42B109.5C83B—C84B—H84A109.5
H42A—C42—H42B109.5C83B—C84B—H84B109.5
C41—C42—H42C109.5H84A—C84B—H84B109.5
H42A—C42—H42C109.5C83B—C84B—H84C109.5
H42B—C42—H42C109.5H84A—C84B—H84C109.5
O10—C43—C44110.3 (2)H84B—C84B—H84C109.5
O10—C43—H43A109.6C83A—C84A—H84D109.5
C44—C43—H43A109.6C83A—C84A—H84E109.5
O10—C43—H43B109.6H84D—C84A—H84E109.5
C44—C43—H43B109.6C83A—C84A—H84F109.5
H43A—C43—H43B108.1H84D—C84A—H84F109.5
O11—C44—O12122.7 (3)H84E—C84A—H84F109.5
O11—C44—C43126.4 (3)C83B—C82B—C81117.2 (8)
O12—C44—C43110.7 (3)C83B—C82B—H82C108.0
O12—C45—H45A109.5C81—C82B—H82C108.0
O12—C45—H45B109.5C83B—C82B—H82D108.0
H45A—C45—H45B109.5C81—C82B—H82D108.0
O12—C45—H45C109.5H82C—C82B—H82D107.2
H45A—C45—H45C109.5C82A—C81—C80119.8 (6)
H45B—C45—H45C109.5C82A—C81—C82B15.5 (6)
O13—C46—C47106.8 (2)C80—C81—C82B104.4 (5)
O13—C46—H46A110.4C82A—C81—H81A107.4
C47—C46—H46A110.4C80—C81—H81A107.4
O13—C46—H46B110.4C82B—C81—H81A114.0
C47—C46—H46B110.4C82A—C81—H81B107.4
H46A—C46—H46B108.6C80—C81—H81B107.4
O14—C47—O15124.7 (3)C82B—C81—H81B116.3
O14—C47—C46125.4 (3)H81A—C81—H81B106.9
O15—C47—C46109.8 (3)O5A—C33A—O6A139.2 (12)
O16—C49—C50112.8 (2)O5A—C33A—C32116.0 (10)
O16—C49—H49A109.0O6A—C33A—C32103.2 (10)
C50—C49—H49A109.0C33A—O6A—C34A115.9 (10)
O16—C49—H49B109.0O6A—C34A—H34D109.5
C50—C49—H49B109.0O6A—C34A—H34E109.5
H49A—C49—H49B107.8H34D—C34A—H34E109.5
O17—C50—O18125.1 (3)O6A—C34A—H34F109.5
O17—C50—C49125.2 (3)H34D—C34A—H34F109.5
O18—C50—C49109.7 (2)H34E—C34A—H34F109.5
C29—O1—C2—C358.8 (3)O31—C24—C25—O346.5 (3)
C29—O1—C2—C1−124.6 (2)C23—C24—C25—C261.2 (3)
C6—C1—C2—C30.1 (3)O31—C24—C25—C26−176.5 (2)
C28—C1—C2—C3−180.0 (2)O34—C25—C26—C27176.28 (19)
C6—C1—C2—O1−176.4 (2)C24—C25—C26—C27−0.8 (3)
C28—C1—C2—O13.5 (3)O34—C25—C26—C28−7.0 (3)
O1—C2—C3—C4178.5 (2)C24—C25—C26—C28175.9 (2)
C1—C2—C3—C42.0 (4)C25—C26—C27—C22−0.6 (3)
O1—C2—C3—O4−1.8 (3)C28—C26—C27—C22−177.1 (2)
C1—C2—C3—O4−178.2 (2)C23—C22—C27—C261.5 (3)
C32—O4—C3—C286.8 (3)C21—C22—C27—C26178.7 (2)
C32—O4—C3—C4−93.5 (3)C27—C26—C28—C1116.1 (2)
C35—O7—C4—C3−53.3 (4)C25—C26—C28—C1−60.4 (3)
C35—O7—C4—C5130.7 (3)C27—C26—C28—C80−8.7 (3)
C2—C3—C4—O7−178.2 (2)C25—C26—C28—C80174.8 (2)
O4—C3—C4—O72.1 (3)C2—C1—C28—C26146.5 (2)
C2—C3—C4—C5−2.2 (3)C6—C1—C28—C26−33.6 (3)
O4—C3—C4—C5178.0 (2)C2—C1—C28—C80−85.1 (3)
O7—C4—C5—C6176.3 (2)C6—C1—C28—C8094.9 (3)
C3—C4—C5—C60.3 (3)C2—O1—C29—C30133.5 (2)
O7—C4—C5—C7−2.5 (3)C31—O3—C30—O2−1.8 (5)
C3—C4—C5—C7−178.5 (2)C31—O3—C30—C29−179.8 (3)
C4—C5—C6—C11.9 (3)O1—C29—C30—O2−8.3 (4)
C7—C5—C6—C1−179.3 (2)O1—C29—C30—O3169.6 (2)
C2—C1—C6—C5−2.1 (3)C3—O4—C32—C33B167.3 (5)
C28—C1—C6—C5177.9 (2)C3—O4—C32—C33A−172.1 (5)
C6—C5—C7—C835.2 (3)C34B—O6B—C33B—O5B11.2 (19)
C4—C5—C7—C8−146.0 (2)C34B—O6B—C33B—C32−156.6 (10)
C6—C5—C7—C38−94.9 (3)O4—C32—C33B—O5B1.1 (17)
C4—C5—C7—C3883.9 (2)C33A—C32—C33B—O5B−101 (3)
C5—C7—C8—C983.9 (2)O4—C32—C33B—O6B166.1 (11)
C38—C7—C8—C9−147.9 (2)C33A—C32—C33B—O6B64 (2)
C5—C7—C8—C13−99.6 (2)C4—O7—C35—C36−138.0 (3)
C38—C7—C8—C1328.6 (3)C37—O9—C36—O82.0 (6)
C43—O10—C9—C8101.5 (3)C37—O9—C36—C35−178.9 (4)
C43—O10—C9—C10−79.2 (3)O7—C35—C36—O815.1 (6)
C13—C8—C9—O10−178.33 (18)O7—C35—C36—O9−163.9 (3)
C7—C8—C9—O10−1.6 (3)C8—C7—C38—C3969.2 (3)
C13—C8—C9—C102.5 (3)C5—C7—C38—C39−161.0 (2)
C7—C8—C9—C10179.23 (19)C7—C38—C39—C40−179.4 (2)
C46—O13—C10—C11119.3 (3)C38—C39—C40—C41−172.4 (2)
C46—O13—C10—C9−67.6 (3)C39—C40—C41—C42−179.0 (3)
O10—C9—C10—O133.2 (3)C9—O10—C43—C44159.1 (3)
C8—C9—C10—O13−177.6 (2)C45—O12—C44—O11−1.4 (6)
O10—C9—C10—C11176.31 (19)C45—O12—C44—C43174.4 (4)
C8—C9—C10—C11−4.5 (3)O10—C43—C44—O11−16.1 (6)
C49—O16—C11—C1043.8 (3)O10—C43—C44—O12168.3 (3)
C49—O16—C11—C12−142.5 (2)C10—O13—C46—C47−169.9 (2)
O13—C10—C11—O16−10.5 (3)C48B—O15—C47—O14−12.9 (8)
C9—C10—C11—O16176.3 (2)C48A—O15—C47—O1421.6 (7)
O13—C10—C11—C12176.11 (19)C48B—O15—C47—C46169.7 (6)
C9—C10—C11—C122.9 (3)C48A—O15—C47—C46−155.8 (5)
O16—C11—C12—C13−173.41 (19)O13—C46—C47—O1433.3 (5)
C10—C11—C12—C130.5 (3)O13—C46—C47—O15−149.3 (3)
O16—C11—C12—C149.0 (3)C11—O16—C49—C5095.5 (3)
C10—C11—C12—C14−177.2 (2)C51—O18—C50—O171.5 (5)
C9—C8—C13—C121.1 (3)C51—O18—C50—C49−179.5 (3)
C7—C8—C13—C12−175.48 (19)O16—C49—C50—O17−17.7 (5)
C11—C12—C13—C8−2.5 (3)O16—C49—C50—O18163.2 (3)
C14—C12—C13—C8175.00 (19)C12—C14—C52—C53−62.3 (3)
C13—C12—C14—C15102.7 (2)C15—C14—C52—C53168.46 (19)
C11—C12—C14—C15−79.8 (2)C14—C52—C53—C54−164.5 (2)
C13—C12—C14—C52−24.8 (3)C52—C53—C54—C55−179.7 (2)
C11—C12—C14—C52152.7 (2)C53—C54—C55—C56−176.0 (3)
C12—C14—C15—C20−38.9 (3)C16—O19—C57—C58175.2 (2)
C52—C14—C15—C2091.6 (2)C59A—O21—C58—O20−16.0 (8)
C12—C14—C15—C16143.3 (2)C59B—O21—C58—O2010.5 (7)
C52—C14—C15—C16−86.3 (2)C59A—O21—C58—C57160.5 (6)
C57—O19—C16—C1776.0 (3)C59B—O21—C58—C57−173.0 (6)
C57—O19—C16—C15−106.3 (2)O19—C57—C58—O20−172.1 (3)
C20—C15—C16—O19−176.48 (19)O19—C57—C58—O2111.3 (4)
C14—C15—C16—O191.5 (3)C17—O22—C60—C61174.5 (2)
C20—C15—C16—C171.2 (3)C62—O24—C61—O232.0 (5)
C14—C15—C16—C17179.1 (2)C62—O24—C61—C60−178.6 (3)
C60—O22—C17—C18−86.5 (3)O22—C60—C61—O231.2 (5)
C60—O22—C17—C1695.1 (3)O22—C60—C61—O24−178.3 (2)
O19—C16—C17—C18176.7 (2)C18—O25—C63—C64133.8 (3)
C15—C16—C17—C18−1.0 (4)C65—O27—C64—O261.0 (5)
O19—C16—C17—O22−4.9 (3)C65—O27—C64—C63178.9 (3)
C15—C16—C17—O22177.4 (2)O25—C63—C64—O26−8.9 (5)
C63—O25—C18—C17−71.0 (3)O25—C63—C64—O27173.3 (3)
C63—O25—C18—C19112.0 (3)C22—C21—C66—C6773.6 (3)
O22—C17—C18—O255.8 (4)C19—C21—C66—C67−161.4 (2)
C16—C17—C18—O25−175.9 (2)C21—C66—C67—C68177.6 (2)
O22—C17—C18—C19−177.2 (2)C66—C67—C68—C69−174.8 (3)
C16—C17—C18—C191.1 (4)C67—C68—C69—C70178.9 (4)
O25—C18—C19—C20175.5 (2)C23—O28—C71—C72−125.3 (2)
C17—C18—C19—C20−1.5 (4)C73—O30—C72—O290.3 (4)
O25—C18—C19—C21−5.6 (3)C73—O30—C72—C71178.6 (3)
C17—C18—C19—C21177.4 (2)O28—C71—C72—O29−7.2 (4)
C18—C19—C20—C151.8 (3)O28—C71—C72—O30174.4 (2)
C21—C19—C20—C15−177.1 (2)C24—O31—C74—C75−175.9 (2)
C16—C15—C20—C19−1.6 (3)C76—O33—C75—O323.1 (5)
C14—C15—C20—C19−179.5 (2)C76—O33—C75—C74−177.0 (3)
C20—C19—C21—C2232.4 (3)O31—C74—C75—O321.8 (4)
C18—C19—C21—C22−146.5 (2)O31—C74—C75—O33−178.1 (2)
C20—C19—C21—C66−96.3 (3)C25—O34—C77—C78126.8 (2)
C18—C19—C21—C6684.8 (3)C79—O36—C78—O35−0.9 (4)
C19—C21—C22—C27−115.9 (2)C79—O36—C78—C77179.4 (3)
C66—C21—C22—C279.5 (3)O34—C77—C78—O35−5.0 (4)
C19—C21—C22—C2361.3 (3)O34—C77—C78—O36174.6 (2)
C66—C21—C22—C23−173.3 (2)C26—C28—C80—C81−71.2 (3)
C71—O28—C23—C2465.9 (3)C1—C28—C80—C81163.7 (3)
C71—O28—C23—C22−117.9 (2)C81—C82A—C83A—C84A178.2 (10)
C27—C22—C23—O28−177.33 (18)C84B—C83B—C82B—C81−64.7 (12)
C21—C22—C23—O285.3 (3)C83A—C82A—C81—C80173.5 (8)
C27—C22—C23—C24−1.1 (3)C83A—C82A—C81—C82B169 (5)
C21—C22—C23—C24−178.5 (2)C28—C80—C81—C82A−175.0 (8)
O28—C23—C24—O31−6.4 (3)C28—C80—C81—C82B−173.7 (6)
C22—C23—C24—O31177.47 (19)C83B—C82B—C81—C82A10 (3)
O28—C23—C24—C25175.99 (19)C83B—C82B—C81—C80−165.5 (9)
C22—C23—C24—C25−0.2 (3)O4—C32—C33A—O5A10.1 (12)
C74—O31—C24—C2390.4 (2)C33B—C32—C33A—O5A95 (2)
C74—O31—C24—C25−92.0 (3)O4—C32—C33A—O6A−157.9 (8)
C77—O34—C25—C24−64.7 (3)C33B—C32—C33A—O6A−73.3 (19)
C77—O34—C25—C26118.2 (2)O5A—C33A—O6A—C34A4 (2)
C23—C24—C25—O34−175.9 (2)C32—C33A—O6A—C34A167.7 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32B···O18i0.992.553.304 (4)133
C34A—H34A···O12i1.162.293.085 (9)124
C45—H45A···O29ii0.982.333.304 (5)175
C45—H45B···O35iii0.982.523.471 (6)163
C48B—H48F···O5Aiv0.982.533.406 (13)149
C59A—H59A···O17v0.982.373.093 (10)130
C59A—H59D···O17v0.932.353.093 (10)137
C62—H62B···O23vi0.982.513.415 (6)153
C73—H73A···O1iv0.982.553.491 (4)160
C79—H79B···O11iii0.982.543.443 (5)153
C84A—H84D···O27i0.982.393.242 (10)145
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+1; (vi) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC84H112O36
Mr1697.74
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)13.8526 (7), 13.9033 (7), 23.7333 (11)
α, β, γ (°)102.231 (1), 90.865 (1), 94.900 (1)
V (Å3)4448.3 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.49 × 0.32 × 0.28
Data collection
DiffractometerBruker Kappa DUO APEXII
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.953, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections		48747, 21987, 14127
Rint0.027
(sin θ/λ)max (Å−1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.251, 1.05
No. of reflections21987
No. of parameters1084
No. of restraints19
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.93, −0.99

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32B···O18i0.992.553.304 (4)133
C34A—H34A···O12i1.162.293.085 (9)124
C45—H45A···O29ii0.982.333.304 (5)175
C45—H45B···O35iii0.982.523.471 (6)163
C48B—H48F···O5Aiv0.982.533.406 (13)149
C59A—H59A···O17v0.982.373.093 (10)130
C59A—H59D···O17v0.932.353.093 (10)137
C62—H62B···O23vi0.982.513.415 (6)153
C73—H73A···O1iv0.982.553.491 (4)160
C79—H79B···O11iii0.982.543.443 (5)153
C84A—H84D···O27i0.982.393.242 (10)145
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+1; (vi) −x+2, −y, −z+1.
 

Acknowledgements

The authors wish to thank Dr Hong Su from the Chemistry Department of the University of Cape Town for her assistance with the data collection and refinement and the DST – National Research Foundation Centre of Excellence in Catalysis, C*Change for financial support.

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages o3305-o3306
https://doi.org/10.1107/S1600536811047180
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