4,6,10,12,16,18,22,24-Octa-O-methyl-2,8,14,20-tetra­pentylresorcin[4]arene

Pansuriya, P.B.; Friedrich, H.B.; Maguire, G.E.M.

doi:10.1107/S1600536811034003

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2565

https://doi.org/10.1107/S1600536811034003

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4,6,10,12,16,18,22,24-Octa-O-methyl-2,8,14,20-tetrapentylresorcin[4]arene

Pramod B. Pansuriya,^a Holger B. Friedrich ^a and Glenn E. M. Maguire ^a ^*

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

(Received 16 August 2011; accepted 19 August 2011; online 14 September 2011)

The complete molecule of the title compound, C₅₆H₈₀O₈, is generated by a crystallographic inversion centre. The dihedral angle between the aromatic ring and the unique half of the molecule is 81.52 (16)°. There are no π–π interactions in the crystal structure.

Related literature

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002 ); Kim et al. (2005 ); Liu et al. (2010 ); D'Acquarica et al. (2011 ). For related structures, see: Botta et al. (2007 ); Iwanek (1998 ); Davis et al. (2001 ); Gerkensmeier et al. (2001 ); Moore & Matthews (2009 ).

Experimental

Crystal data

C₅₆H₈₀O₈
M_r = 881.20
Triclinic, $[P \overline 1]$
a = 8.2084 (2) Å
b = 14.1270 (2) Å
c = 23.1489 (4) Å
α = 98.929 (1)°
β = 97.914 (1)°
γ = 103.581 (1)°
V = 2534.93 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.44 × 0.39 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
42741 measured reflections
12226 independent reflections
7816 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.148
S = 0.99
12226 reflections
589 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811034003/hg5082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811034003/hg5082Isup2.hkl

checkCIF report

Comment top

Resorcin[4]arenes are easily prepared macromolecules that are used for a range of applications in supramolecular chemistry such as catalysis (Gibson & Rebek, 2002), self-assembled nanoparticles (Kim et al., 2005), molecular recognition (Liu et al., 2010) and noncompetitive inhibitors for R-chymotrypsin (D'Acquarica et al., 2011).

The different conformers of resorcin[4]arenes that can occur in solution have been extensively reported (Moore & Matthews, 2009). Their topology has been classified into four diffrent structures i.e. rccc (cone/crown), rctt (chair), rctc (diamond), rccc (boat). The most commonly reported single-crystal X-ray structures have been the crown and boat isomers (Davis et al., 2001; Gerkensmeier et al., 2001). In the title compound, a pair of aromatic rings are almost coplanar (C8—C9—C11—C12—C13), whereas the others are orthogonal at an angle of 86.91° from the plane facing the side-chains. This creates an rctt conformation (Fig 1). Botta et al. have described the only other rctt octamethoxy-resorcin[4]arene structure thus far (Botta et al., 2007) which had ethyl ester side chains. Iwanek have reported the only rctc octamethoxy resorcinarene (Iwanek, 1998) with isopropyl side chains. There are no π–π interactions in the crystal matrix (Fig. 2).

Related literature top

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002); Kim et al. (2005); Liu et al. (2010); D'Acquarica et al. (2011). For related structures, see: Botta et al. (2007); Iwanek (1998); Davis et al. (2001); Gerkensmeier et al. (2001); Moore & Matthews (2009).

Experimental top

1,3-Dimethoxybenzene (1.054 g, 7.63 mmol) and hexanal (0.764 g, 7.63 mmol) were added to diethyl ether (20 ml) followed by addition of thionyl chloride (0.907 g, 7.63 mmol). The solution was stirred at room temperature for 24 h. Subsequently, methanol (40 ml) was added, and the mixture was stirred for 1 h. The resulting precipitate was collected by filtration and washed with methanol. The yield was 0.65 g (36%). m.p. = 516–519 K.

Crystals suitable for single-crystal X-ray diffraction were grown in methanol: methylene chloride (1:2) at room temperature.

Structure description top

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002); Kim et al. (2005); Liu et al. (2010); D'Acquarica et al. (2011). For related structures, see: Botta et al. (2007); Iwanek (1998); Davis et al. (2001); Gerkensmeier et al. (2001); Moore & Matthews (2009).

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atomic numbering scheme. The H atoms have been omitted clarity. Displacement ellipsoids are drawn at 40% probability, symmetry code (i): 1 - x, -y, -z.
	Fig. 2. The packing of the title compound along the [110] axis. All H atoms have been omitted for clarity.

4,6,10,12,16,18,22,24-Octa-O-methyl-2,8,14,20- tetrapentylresorcin[4]arene top

Crystal data top

C₅₆H₈₀O₈	Z = 2
M_r = 881.20	F(000) = 960
Triclinic, P1	D_x = 1.154 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2084 (2) Å	Cell parameters from 9018 reflections
b = 14.1270 (2) Å	θ = 2.6–28.0°
c = 23.1489 (4) Å	µ = 0.08 mm⁻¹
α = 98.929 (1)°	T = 173 K
β = 97.914 (1)°	Plate, colourless
γ = 103.581 (1)°	0.44 × 0.39 × 0.13 mm
V = 2534.93 (8) Å³

Data collection top

Bruker APEXII CCD diffractometer	7816 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 28.0°, θ_min = 0.9°
φ and ω scans	h = −10→10
42741 measured reflections	k = −18→18
12226 independent reflections	l = −30→30

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0817P)²] where P = (F_o² + 2F_c²)/3
12226 reflections	(Δ/σ)_max = 0.001
589 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₅₆H₈₀O₈	γ = 103.581 (1)°
M_r = 881.20	V = 2534.93 (8) Å³
Triclinic, P1	Z = 2
a = 8.2084 (2) Å	Mo Kα radiation
b = 14.1270 (2) Å	µ = 0.08 mm⁻¹
c = 23.1489 (4) Å	T = 173 K
α = 98.929 (1)°	0.44 × 0.39 × 0.13 mm
β = 97.914 (1)°

Data collection top

Bruker APEXII CCD diffractometer	7816 reflections with I > 2σ(I)
42741 measured reflections	R_int = 0.046
12226 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 0.99	Δρ_max = 0.39 e Å⁻³
12226 reflections	Δρ_min = −0.26 e Å⁻³
589 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

	x	y	z	U_iso*/U_eq
C1	0.57192 (19)	0.04899 (10)	−0.06674 (6)	0.0238 (3)
H1	0.4525	0.0246	−0.0692	0.029*
C2	0.65461 (18)	0.00564 (10)	−0.10787 (6)	0.0207 (3)
C3	0.82972 (18)	0.04165 (10)	−0.10628 (6)	0.0195 (3)
C4	0.91774 (18)	0.11977 (10)	−0.05978 (6)	0.0208 (3)
H4	1.0373	0.1438	−0.0571	0.025*
C5	0.84136 (19)	0.16501 (10)	−0.01687 (6)	0.0219 (3)
C6	0.66495 (19)	0.12805 (10)	−0.02208 (6)	0.0235 (3)
C7	0.9370 (2)	0.25271 (10)	0.03240 (6)	0.0239 (3)
H7	0.8554	0.2941	0.0391	0.029*
C8	1.03311 (19)	0.26193 (10)	0.19982 (6)	0.0246 (3)
H8	1.0392	0.3073	0.2354	0.029*
C9	0.99799 (19)	0.28811 (10)	0.14464 (6)	0.0244 (3)
C10	0.98417 (18)	0.22153 (10)	0.09158 (6)	0.0221 (3)
C11	1.01599 (18)	0.13015 (10)	0.09603 (6)	0.0209 (3)
H11	1.0101	0.0848	0.0604	0.025*
C12	1.05618 (18)	0.10183 (10)	0.15035 (6)	0.0200 (3)
C13	1.05902 (18)	0.16881 (10)	0.20215 (6)	0.0221 (3)
C14	1.08814 (17)	0.00129 (10)	0.15609 (6)	0.0189 (3)
H14	1.1731	0.0135	0.1936	0.023*
C15	0.3894 (2)	−0.10994 (12)	−0.15630 (7)	0.0338 (4)
H15A	0.3671	−0.1293	−0.1187	0.051*
H15B	0.3444	−0.1677	−0.1888	0.051*
H15C	0.3336	−0.0577	−0.1637	0.051*
C16	0.4127 (2)	0.16205 (13)	0.00749 (8)	0.0373 (4)
H16A	0.3828	0.1829	−0.0301	0.056*
H16B	0.3788	0.2029	0.0396	0.056*
H16C	0.3531	0.0921	0.0043	0.056*
C17	1.0271 (3)	0.45754 (13)	0.18855 (9)	0.0643 (7)
H17A	0.9504	0.4463	0.2172	0.096*
H17B	1.0256	0.5204	0.1758	0.096*
H17C	1.1432	0.4604	0.2073	0.096*
C18	1.0755 (2)	0.19585 (11)	0.30801 (7)	0.0300 (4)
H18A	1.1562	0.2614	0.3144	0.045*
H18B	1.1003	0.1636	0.3415	0.045*
H18C	0.9591	0.2034	0.3049	0.045*
C19	1.0918 (2)	0.32067 (11)	0.01602 (7)	0.0289 (4)
H19A	1.1528	0.3718	0.0515	0.035*
H19B	1.1707	0.2808	0.0045	0.035*
C20	1.0443 (3)	0.37200 (13)	−0.03473 (8)	0.0459 (5)
H20A	0.9915	0.3207	−0.0710	0.055*
H20B	0.9576	0.4069	−0.0245	0.055*
C21	1.1938 (3)	0.44644 (15)	−0.04869 (10)	0.0658 (7)
H21A	1.1493	0.4820	−0.0783	0.079*
H21B	1.2496	0.4961	−0.0120	0.079*
C22	1.3244 (4)	0.40150 (18)	−0.07211 (12)	0.0925 (10)
H22A	1.2664	0.3424	−0.1035	0.111*
H22B	1.3876	0.3791	−0.0396	0.111*
C23	1.4507 (4)	0.4738 (2)	−0.09782 (13)	0.1321 (16)
H23A	1.3920	0.4874	−0.1342	0.198*
H23B	1.5432	0.4444	−0.1071	0.198*
H23C	1.4979	0.5359	−0.0687	0.198*
C24	0.92534 (19)	−0.07005 (10)	0.16585 (7)	0.0255 (3)
H24A	0.8710	−0.0325	0.1937	0.031*
H24B	0.8449	−0.0933	0.1274	0.031*
C25	0.9520 (2)	−0.16053 (11)	0.19023 (8)	0.0348 (4)
H25A	0.8401	−0.2095	0.1847	0.042*
H25B	1.0242	−0.1916	0.1666	0.042*
C26	1.0343 (3)	−0.13830 (14)	0.25552 (9)	0.0462 (5)
H26A	0.9687	−0.1010	0.2787	0.055*
H26B	1.1510	−0.0948	0.2603	0.055*
C27	1.0449 (3)	−0.22990 (16)	0.28167 (10)	0.0611 (6)
H27A	0.9287	−0.2744	0.2760	0.073*
H27B	1.1136	−0.2662	0.2595	0.073*
C28	1.1227 (4)	−0.2061 (2)	0.34712 (12)	0.0945 (10)
H28A	1.2352	−0.1591	0.3535	0.142*
H28B	1.1344	−0.2672	0.3603	0.142*
H28C	1.0488	−0.1766	0.3700	0.142*
C29	0.92260 (19)	0.44372 (10)	0.56863 (6)	0.0225 (3)
H29	1.0429	0.4674	0.5734	0.027*
C30	0.83704 (18)	0.47882 (9)	0.61160 (6)	0.0196 (3)
C31	0.66025 (17)	0.44376 (9)	0.60632 (6)	0.0172 (3)
C32	0.57479 (18)	0.37462 (9)	0.55514 (6)	0.0172 (3)
H32	0.4544	0.3515	0.5501	0.021*
C33	0.65478 (18)	0.33708 (9)	0.51066 (6)	0.0178 (3)
C34	0.83149 (18)	0.37388 (10)	0.51865 (6)	0.0203 (3)
C35	0.56261 (18)	0.25566 (9)	0.45731 (6)	0.0187 (3)
H35	0.6422	0.2131	0.4502	0.022*
C36	0.49061 (18)	0.26418 (10)	0.29213 (6)	0.0210 (3)
H36	0.4891	0.2221	0.2557	0.025*
C37	0.52010 (18)	0.23300 (10)	0.34572 (6)	0.0200 (3)
C38	0.52755 (18)	0.29423 (10)	0.40005 (6)	0.0184 (3)
C39	0.49580 (17)	0.38639 (9)	0.39833 (6)	0.0184 (3)
H39	0.4980	0.4285	0.4348	0.022*
C40	0.46084 (17)	0.41983 (9)	0.34553 (6)	0.0173 (3)
C41	0.46333 (18)	0.35759 (10)	0.29239 (6)	0.0191 (3)
C42	0.42842 (17)	0.52173 (9)	0.34370 (6)	0.0175 (3)
H42	0.3481	0.5141	0.3056	0.021*
C43	1.0998 (2)	0.58625 (13)	0.66741 (8)	0.0365 (4)
H43A	1.1532	0.5312	0.6683	0.055*
H43B	1.1440	0.6354	0.7044	0.055*
H43C	1.1260	0.6174	0.6336	0.055*
C44	1.0860 (2)	0.34697 (12)	0.48723 (7)	0.0324 (4)
H44A	1.1474	0.4175	0.4968	0.049*
H44B	1.1223	0.3140	0.4527	0.049*
H44C	1.1112	0.3161	0.5213	0.049*
C45	0.5143 (3)	0.07023 (12)	0.29651 (8)	0.0532 (6)
H45A	0.4027	0.0656	0.2731	0.080*
H45B	0.5165	0.0054	0.3062	0.080*
H45C	0.6034	0.0905	0.2734	0.080*
C46	0.4490 (2)	0.33674 (11)	0.18674 (6)	0.0304 (4)
H46A	0.5665	0.3314	0.1885	0.046*
H46B	0.4189	0.3690	0.1537	0.046*
H46C	0.3715	0.2702	0.1805	0.046*
C47	0.39980 (19)	0.18682 (10)	0.46791 (6)	0.0225 (3)
H47A	0.3190	0.2268	0.4771	0.027*
H47B	0.3461	0.1378	0.4308	0.027*
C48	0.4288 (2)	0.13113 (10)	0.51825 (7)	0.0256 (3)
H48A	0.5097	0.0912	0.5093	0.031*
H48B	0.4817	0.1799	0.5555	0.031*
C49	0.2662 (2)	0.06318 (13)	0.52775 (8)	0.0374 (4)
H49A	0.1814	0.1019	0.5330	0.045*
H49B	0.2189	0.0106	0.4918	0.045*
C50	0.2925 (2)	0.01513 (13)	0.58115 (8)	0.0406 (4)
H50A	0.3348	0.0677	0.6174	0.049*
H50B	0.3811	−0.0211	0.5767	0.049*
C51	0.1312 (3)	−0.0566 (2)	0.58920 (13)	0.0899 (10)
H51A	0.0454	−0.0204	0.5964	0.135*
H51B	0.1572	−0.0875	0.6232	0.135*
H51C	0.0871	−0.1081	0.5532	0.135*
C52	0.59415 (19)	0.59643 (10)	0.33991 (6)	0.0221 (3)
H52A	0.6719	0.6113	0.3788	0.027*
H52B	0.6497	0.5646	0.3099	0.027*
C53	0.5731 (2)	0.69418 (10)	0.32391 (7)	0.0297 (4)
H53A	0.4973	0.7195	0.3486	0.036*
H53B	0.6857	0.7434	0.3340	0.036*
C54	0.5003 (3)	0.68609 (13)	0.25889 (8)	0.0410 (4)
H54A	0.3838	0.6412	0.2497	0.049*
H54B	0.5708	0.6556	0.2341	0.049*
C55	0.4927 (3)	0.78484 (15)	0.24201 (10)	0.0575 (6)
H55A	0.4229	0.8156	0.2669	0.069*
H55B	0.6093	0.8296	0.2509	0.069*
C56	0.4189 (4)	0.7761 (2)	0.17737 (12)	0.0945 (10)
H56A	0.4914	0.7498	0.1523	0.142*
H56B	0.4135	0.8418	0.1698	0.142*
H56C	0.3039	0.7312	0.1680	0.142*
O1	0.56951 (13)	−0.07364 (7)	−0.15298 (4)	0.0257 (2)
O2	0.59201 (14)	0.17402 (8)	0.02027 (5)	0.0325 (3)
O3	0.97265 (16)	0.37925 (8)	0.13885 (5)	0.0350 (3)
O4	1.09114 (14)	0.13645 (7)	0.25449 (4)	0.0283 (3)
O5	0.91909 (13)	0.54939 (7)	0.66135 (4)	0.0261 (2)
O6	0.90743 (13)	0.33729 (8)	0.47391 (4)	0.0278 (2)
O7	0.54300 (15)	0.14038 (7)	0.34895 (4)	0.0301 (3)
O8	0.43475 (14)	0.39443 (7)	0.24128 (4)	0.0263 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0197 (8)	0.0303 (8)	0.0234 (8)	0.0085 (6)	0.0057 (6)	0.0063 (6)
C2	0.0215 (8)	0.0224 (7)	0.0174 (7)	0.0059 (6)	0.0010 (6)	0.0041 (5)
C3	0.0198 (8)	0.0232 (7)	0.0171 (7)	0.0085 (6)	0.0026 (6)	0.0052 (5)
C4	0.0185 (7)	0.0250 (7)	0.0198 (7)	0.0084 (6)	0.0018 (6)	0.0042 (6)
C5	0.0245 (8)	0.0223 (7)	0.0195 (7)	0.0098 (6)	0.0004 (6)	0.0033 (6)
C6	0.0262 (8)	0.0294 (8)	0.0187 (7)	0.0139 (7)	0.0060 (6)	0.0043 (6)
C7	0.0280 (8)	0.0252 (7)	0.0191 (7)	0.0128 (6)	0.0003 (6)	0.0002 (6)
C8	0.0259 (8)	0.0253 (7)	0.0193 (7)	0.0056 (6)	0.0032 (6)	−0.0029 (6)
C9	0.0249 (8)	0.0238 (7)	0.0234 (8)	0.0076 (6)	0.0032 (6)	0.0007 (6)
C10	0.0197 (8)	0.0258 (7)	0.0199 (7)	0.0066 (6)	0.0024 (6)	0.0021 (6)
C11	0.0183 (7)	0.0239 (7)	0.0185 (7)	0.0052 (6)	0.0032 (6)	−0.0009 (6)
C12	0.0151 (7)	0.0232 (7)	0.0203 (7)	0.0037 (6)	0.0031 (6)	0.0019 (6)
C13	0.0195 (8)	0.0266 (7)	0.0185 (7)	0.0037 (6)	0.0030 (6)	0.0033 (6)
C14	0.0171 (7)	0.0217 (7)	0.0164 (7)	0.0050 (6)	0.0013 (5)	0.0011 (5)
C15	0.0189 (8)	0.0413 (9)	0.0336 (9)	0.0016 (7)	0.0038 (7)	−0.0052 (7)
C16	0.0304 (10)	0.0522 (10)	0.0357 (10)	0.0234 (8)	0.0100 (8)	0.0049 (8)
C17	0.116 (2)	0.0300 (10)	0.0376 (11)	0.0288 (12)	−0.0175 (12)	−0.0077 (8)
C18	0.0345 (9)	0.0345 (8)	0.0193 (8)	0.0061 (7)	0.0075 (7)	0.0019 (6)
C19	0.0347 (9)	0.0233 (7)	0.0249 (8)	0.0056 (7)	0.0008 (7)	0.0010 (6)
C20	0.0613 (13)	0.0311 (9)	0.0397 (11)	0.0055 (9)	−0.0024 (9)	0.0103 (8)
C21	0.0915 (19)	0.0416 (11)	0.0523 (13)	−0.0068 (12)	−0.0001 (13)	0.0225 (10)
C22	0.115 (2)	0.0700 (16)	0.0653 (17)	−0.0333 (16)	0.0468 (17)	−0.0061 (13)
C23	0.139 (3)	0.136 (3)	0.072 (2)	−0.070 (2)	0.023 (2)	0.0325 (19)
C24	0.0224 (8)	0.0280 (8)	0.0258 (8)	0.0058 (6)	0.0074 (6)	0.0027 (6)
C25	0.0353 (10)	0.0287 (8)	0.0433 (10)	0.0063 (7)	0.0173 (8)	0.0094 (7)
C26	0.0498 (12)	0.0475 (11)	0.0482 (12)	0.0150 (9)	0.0130 (10)	0.0223 (9)
C27	0.0573 (14)	0.0705 (14)	0.0784 (17)	0.0280 (12)	0.0308 (13)	0.0490 (13)
C28	0.098 (2)	0.136 (3)	0.084 (2)	0.052 (2)	0.0280 (17)	0.079 (2)
C29	0.0169 (7)	0.0254 (7)	0.0250 (8)	0.0057 (6)	0.0044 (6)	0.0037 (6)
C30	0.0202 (8)	0.0185 (7)	0.0190 (7)	0.0054 (6)	0.0014 (6)	0.0019 (5)
C31	0.0193 (7)	0.0173 (6)	0.0176 (7)	0.0077 (6)	0.0039 (5)	0.0060 (5)
C32	0.0155 (7)	0.0178 (6)	0.0192 (7)	0.0054 (5)	0.0019 (5)	0.0057 (5)
C33	0.0211 (7)	0.0168 (6)	0.0174 (7)	0.0081 (6)	0.0020 (6)	0.0049 (5)
C34	0.0231 (8)	0.0219 (7)	0.0192 (7)	0.0102 (6)	0.0070 (6)	0.0047 (6)
C35	0.0237 (8)	0.0184 (6)	0.0147 (7)	0.0090 (6)	0.0009 (6)	0.0025 (5)
C36	0.0241 (8)	0.0205 (7)	0.0172 (7)	0.0058 (6)	0.0036 (6)	0.0007 (5)
C37	0.0223 (8)	0.0174 (6)	0.0205 (7)	0.0067 (6)	0.0030 (6)	0.0028 (5)
C38	0.0176 (7)	0.0202 (7)	0.0170 (7)	0.0051 (6)	0.0022 (5)	0.0031 (5)
C39	0.0188 (7)	0.0192 (6)	0.0162 (7)	0.0045 (6)	0.0028 (6)	0.0022 (5)
C40	0.0158 (7)	0.0168 (6)	0.0196 (7)	0.0044 (5)	0.0040 (5)	0.0037 (5)
C41	0.0207 (7)	0.0200 (7)	0.0160 (7)	0.0038 (6)	0.0023 (6)	0.0048 (5)
C42	0.0193 (7)	0.0174 (6)	0.0157 (7)	0.0061 (6)	0.0021 (5)	0.0021 (5)
C43	0.0180 (8)	0.0458 (10)	0.0355 (9)	0.0021 (7)	0.0019 (7)	−0.0108 (8)
C44	0.0256 (9)	0.0426 (9)	0.0337 (9)	0.0185 (7)	0.0094 (7)	0.0039 (7)
C45	0.0998 (18)	0.0261 (9)	0.0289 (10)	0.0269 (10)	−0.0118 (10)	−0.0045 (7)
C46	0.0438 (10)	0.0317 (8)	0.0169 (7)	0.0108 (7)	0.0074 (7)	0.0048 (6)
C47	0.0263 (8)	0.0193 (7)	0.0213 (7)	0.0061 (6)	0.0014 (6)	0.0039 (6)
C48	0.0297 (9)	0.0228 (7)	0.0249 (8)	0.0066 (6)	0.0035 (6)	0.0079 (6)
C49	0.0338 (10)	0.0387 (9)	0.0422 (10)	0.0058 (8)	0.0060 (8)	0.0218 (8)
C50	0.0422 (11)	0.0429 (10)	0.0439 (11)	0.0115 (8)	0.0125 (9)	0.0251 (8)
C51	0.0470 (14)	0.123 (2)	0.126 (2)	0.0163 (14)	0.0252 (15)	0.104 (2)
C52	0.0230 (8)	0.0219 (7)	0.0230 (7)	0.0063 (6)	0.0076 (6)	0.0053 (6)
C53	0.0356 (10)	0.0213 (7)	0.0358 (9)	0.0069 (7)	0.0156 (7)	0.0089 (7)
C54	0.0529 (12)	0.0415 (10)	0.0394 (10)	0.0214 (9)	0.0156 (9)	0.0200 (8)
C55	0.0609 (14)	0.0596 (12)	0.0794 (16)	0.0330 (11)	0.0356 (12)	0.0489 (12)
C56	0.110 (2)	0.136 (2)	0.092 (2)	0.079 (2)	0.0461 (18)	0.090 (2)
O1	0.0166 (5)	0.0309 (5)	0.0248 (6)	0.0030 (4)	0.0032 (4)	−0.0031 (4)
O2	0.0275 (6)	0.0447 (7)	0.0265 (6)	0.0164 (5)	0.0079 (5)	−0.0032 (5)
O3	0.0528 (8)	0.0250 (5)	0.0251 (6)	0.0174 (5)	−0.0037 (5)	−0.0030 (4)
O4	0.0382 (7)	0.0284 (5)	0.0171 (5)	0.0084 (5)	0.0040 (5)	0.0025 (4)
O5	0.0169 (5)	0.0300 (5)	0.0247 (6)	0.0017 (4)	0.0022 (4)	−0.0063 (4)
O6	0.0225 (6)	0.0368 (6)	0.0244 (6)	0.0115 (5)	0.0074 (4)	−0.0019 (5)
O7	0.0506 (8)	0.0198 (5)	0.0205 (5)	0.0172 (5)	−0.0007 (5)	−0.0005 (4)
O8	0.0404 (7)	0.0240 (5)	0.0161 (5)	0.0109 (5)	0.0049 (5)	0.0052 (4)

Geometric parameters (Å, º) top

C1—C6	1.387 (2)	C29—C30	1.3896 (19)
C1—C2	1.3908 (19)	C29—C34	1.3900 (19)
C1—H1	0.9500	C29—H29	0.9500
C2—O1	1.3790 (16)	C30—O5	1.3743 (16)
C2—C3	1.4009 (19)	C30—C31	1.4004 (19)
C3—C4	1.3933 (19)	C31—C32	1.3928 (18)
C3—C14ⁱ	1.5299 (18)	C31—C42ⁱⁱ	1.5263 (17)
C4—C5	1.3968 (19)	C32—C33	1.3972 (18)
C4—H4	0.9500	C32—H32	0.9500
C5—C6	1.400 (2)	C33—C34	1.3967 (19)
C5—C7	1.5200 (19)	C33—C35	1.5211 (18)
C6—O2	1.3740 (16)	C34—O6	1.3752 (15)
C7—C10	1.530 (2)	C35—C38	1.5262 (18)
C7—C19	1.534 (2)	C35—C47	1.5317 (19)
C7—H7	1.0000	C35—H35	1.0000
C8—C13	1.389 (2)	C36—C41	1.3886 (18)
C8—C9	1.395 (2)	C36—C37	1.3887 (19)
C8—H8	0.9500	C36—H36	0.9500
C9—O3	1.3750 (17)	C37—O7	1.3765 (15)
C9—C10	1.3996 (19)	C37—C38	1.3965 (18)
C10—C11	1.3919 (19)	C38—C39	1.3919 (18)
C11—C12	1.3980 (19)	C39—C40	1.3947 (19)
C11—H11	0.9500	C39—H39	0.9500
C12—C13	1.4014 (18)	C40—C41	1.4023 (18)
C12—C14	1.5257 (18)	C40—C42	1.5300 (17)
C13—O4	1.3736 (17)	C41—O8	1.3777 (16)
C14—C3ⁱ	1.5299 (18)	C42—C31ⁱⁱ	1.5263 (17)
C14—C24	1.5407 (19)	C42—C52	1.5360 (18)
C14—H14	1.0000	C42—H42	1.0000
C15—O1	1.4335 (17)	C43—O5	1.4314 (18)
C15—H15A	0.9800	C43—H43A	0.9800
C15—H15B	0.9800	C43—H43B	0.9800
C15—H15C	0.9800	C43—H43C	0.9800
C16—O2	1.4249 (19)	C44—O6	1.4252 (18)
C16—H16A	0.9800	C44—H44A	0.9800
C16—H16B	0.9800	C44—H44B	0.9800
C16—H16C	0.9800	C44—H44C	0.9800
C17—O3	1.4064 (19)	C45—O7	1.3961 (18)
C17—H17A	0.9800	C45—H45A	0.9800
C17—H17B	0.9800	C45—H45B	0.9800
C17—H17C	0.9800	C45—H45C	0.9800
C18—O4	1.4241 (17)	C46—O8	1.4277 (16)
C18—H18A	0.9800	C46—H46A	0.9800
C18—H18B	0.9800	C46—H46B	0.9800
C18—H18C	0.9800	C46—H46C	0.9800
C19—C20	1.526 (2)	C47—C48	1.5264 (19)
C19—H19A	0.9900	C47—H47A	0.9900
C19—H19B	0.9900	C47—H47B	0.9900
C20—C21	1.525 (3)	C48—C49	1.516 (2)
C20—H20A	0.9900	C48—H48A	0.9900
C20—H20B	0.9900	C48—H48B	0.9900
C21—C22	1.489 (4)	C49—C50	1.514 (2)
C21—H21A	0.9900	C49—H49A	0.9900
C21—H21B	0.9900	C49—H49B	0.9900
C22—C23	1.528 (3)	C50—C51	1.520 (3)
C22—H22A	0.9900	C50—H50A	0.9900
C22—H22B	0.9900	C50—H50B	0.9900
C23—H23A	0.9800	C51—H51A	0.9800
C23—H23B	0.9800	C51—H51B	0.9800
C23—H23C	0.9800	C51—H51C	0.9800
C24—C25	1.524 (2)	C52—C53	1.5254 (19)
C24—H24A	0.9900	C52—H52A	0.9900
C24—H24B	0.9900	C52—H52B	0.9900
C25—C26	1.520 (2)	C53—C54	1.517 (2)
C25—H25A	0.9900	C53—H53A	0.9900
C25—H25B	0.9900	C53—H53B	0.9900
C26—C27	1.526 (2)	C54—C55	1.519 (2)
C26—H26A	0.9900	C54—H54A	0.9900
C26—H26B	0.9900	C54—H54B	0.9900
C27—C28	1.514 (3)	C55—C56	1.510 (3)
C27—H27A	0.9900	C55—H55A	0.9900
C27—H27B	0.9900	C55—H55B	0.9900
C28—H28A	0.9800	C56—H56A	0.9800
C28—H28B	0.9800	C56—H56B	0.9800
C28—H28C	0.9800	C56—H56C	0.9800

C6—C1—C2	119.56 (14)	O5—C30—C31	116.04 (12)
C6—C1—H1	120.2	C29—C30—C31	121.34 (13)
C2—C1—H1	120.2	C32—C31—C30	116.62 (12)
O1—C2—C1	122.32 (13)	C32—C31—C42ⁱⁱ	123.23 (12)
O1—C2—C3	116.16 (12)	C30—C31—C42ⁱⁱ	120.10 (12)
C1—C2—C3	121.51 (13)	C31—C32—C33	124.22 (13)
C4—C3—C2	116.56 (12)	C31—C32—H32	117.9
C4—C3—C14ⁱ	123.66 (13)	C33—C32—H32	117.9
C2—C3—C14ⁱ	119.69 (12)	C34—C33—C32	116.61 (12)
C3—C4—C5	124.16 (14)	C34—C33—C35	119.34 (12)
C3—C4—H4	117.9	C32—C33—C35	123.95 (13)
C5—C4—H4	117.9	O6—C34—C29	122.85 (13)
C4—C5—C6	116.57 (13)	O6—C34—C33	115.71 (12)
C4—C5—C7	123.90 (13)	C29—C34—C33	121.44 (12)
C6—C5—C7	119.48 (12)	C33—C35—C38	113.56 (11)
O2—C6—C1	122.73 (13)	C33—C35—C47	114.02 (11)
O2—C6—C5	115.69 (13)	C38—C35—C47	110.54 (12)
C1—C6—C5	121.57 (13)	C33—C35—H35	106.0
C5—C7—C10	112.62 (12)	C38—C35—H35	106.0
C5—C7—C19	114.10 (12)	C47—C35—H35	106.0
C10—C7—C19	111.39 (12)	C41—C36—C37	119.24 (12)
C5—C7—H7	106.0	C41—C36—H36	120.4
C10—C7—H7	106.0	C37—C36—H36	120.4
C19—C7—H7	106.0	O7—C37—C36	122.64 (12)
C13—C8—C9	119.31 (13)	O7—C37—C38	115.69 (12)
C13—C8—H8	120.3	C36—C37—C38	121.67 (12)
C9—C8—H8	120.3	C39—C38—C37	117.28 (12)
O3—C9—C8	122.60 (13)	C39—C38—C35	123.77 (12)
O3—C9—C10	116.08 (13)	C37—C38—C35	118.91 (12)
C8—C9—C10	121.32 (13)	C38—C39—C40	123.09 (12)
C11—C10—C9	117.39 (13)	C38—C39—H39	118.5
C11—C10—C7	123.70 (12)	C40—C39—H39	118.5
C9—C10—C7	118.91 (12)	C39—C40—C41	117.36 (12)
C10—C11—C12	123.19 (13)	C39—C40—C42	123.08 (12)
C10—C11—H11	118.4	C41—C40—C42	119.50 (12)
C12—C11—H11	118.4	O8—C41—C36	122.85 (12)
C11—C12—C13	117.26 (13)	O8—C41—C40	115.90 (11)
C11—C12—C14	123.93 (12)	C36—C41—C40	121.24 (12)
C13—C12—C14	118.74 (12)	C31ⁱⁱ—C42—C40	112.82 (10)
O4—C13—C8	123.07 (12)	C31ⁱⁱ—C42—C52	114.20 (11)
O4—C13—C12	115.54 (12)	C40—C42—C52	109.85 (11)
C8—C13—C12	121.38 (13)	C31ⁱⁱ—C42—H42	106.5
C12—C14—C3ⁱ	113.62 (11)	C40—C42—H42	106.5
C12—C14—C24	110.26 (11)	C52—C42—H42	106.5
C3ⁱ—C14—C24	114.38 (11)	O5—C43—H43A	109.5
C12—C14—H14	105.9	O5—C43—H43B	109.5
C3ⁱ—C14—H14	105.9	H43A—C43—H43B	109.5
C24—C14—H14	105.9	O5—C43—H43C	109.5
O1—C15—H15A	109.5	H43A—C43—H43C	109.5
O1—C15—H15B	109.5	H43B—C43—H43C	109.5
H15A—C15—H15B	109.5	O6—C44—H44A	109.5
O1—C15—H15C	109.5	O6—C44—H44B	109.5
H15A—C15—H15C	109.5	H44A—C44—H44B	109.5
H15B—C15—H15C	109.5	O6—C44—H44C	109.5
O2—C16—H16A	109.5	H44A—C44—H44C	109.5
O2—C16—H16B	109.5	H44B—C44—H44C	109.5
H16A—C16—H16B	109.5	O7—C45—H45A	109.5
O2—C16—H16C	109.5	O7—C45—H45B	109.5
H16A—C16—H16C	109.5	H45A—C45—H45B	109.5
H16B—C16—H16C	109.5	O7—C45—H45C	109.5
O3—C17—H17A	109.5	H45A—C45—H45C	109.5
O3—C17—H17B	109.5	H45B—C45—H45C	109.5
H17A—C17—H17B	109.5	O8—C46—H46A	109.5
O3—C17—H17C	109.5	O8—C46—H46B	109.5
H17A—C17—H17C	109.5	H46A—C46—H46B	109.5
H17B—C17—H17C	109.5	O8—C46—H46C	109.5
O4—C18—H18A	109.5	H46A—C46—H46C	109.5
O4—C18—H18B	109.5	H46B—C46—H46C	109.5
H18A—C18—H18B	109.5	C48—C47—C35	114.04 (12)
O4—C18—H18C	109.5	C48—C47—H47A	108.7
H18A—C18—H18C	109.5	C35—C47—H47A	108.7
H18B—C18—H18C	109.5	C48—C47—H47B	108.7
C20—C19—C7	113.16 (14)	C35—C47—H47B	108.7
C20—C19—H19A	108.9	H47A—C47—H47B	107.6
C7—C19—H19A	108.9	C49—C48—C47	113.11 (13)
C20—C19—H19B	108.9	C49—C48—H48A	109.0
C7—C19—H19B	108.9	C47—C48—H48A	109.0
H19A—C19—H19B	107.8	C49—C48—H48B	109.0
C21—C20—C19	114.37 (17)	C47—C48—H48B	109.0
C21—C20—H20A	108.7	H48A—C48—H48B	107.8
C19—C20—H20A	108.7	C50—C49—C48	113.07 (14)
C21—C20—H20B	108.7	C50—C49—H49A	109.0
C19—C20—H20B	108.7	C48—C49—H49A	109.0
H20A—C20—H20B	107.6	C50—C49—H49B	109.0
C22—C21—C20	114.38 (17)	C48—C49—H49B	109.0
C22—C21—H21A	108.7	H49A—C49—H49B	107.8
C20—C21—H21A	108.7	C49—C50—C51	113.19 (17)
C22—C21—H21B	108.7	C49—C50—H50A	108.9
C20—C21—H21B	108.7	C51—C50—H50A	108.9
H21A—C21—H21B	107.6	C49—C50—H50B	108.9
C21—C22—C23	112.6 (3)	C51—C50—H50B	108.9
C21—C22—H22A	109.1	H50A—C50—H50B	107.8
C23—C22—H22A	109.1	C50—C51—H51A	109.5
C21—C22—H22B	109.1	C50—C51—H51B	109.5
C23—C22—H22B	109.1	H51A—C51—H51B	109.5
H22A—C22—H22B	107.8	C50—C51—H51C	109.5
C22—C23—H23A	109.5	H51A—C51—H51C	109.5
C22—C23—H23B	109.5	H51B—C51—H51C	109.5
H23A—C23—H23B	109.5	C53—C52—C42	115.35 (12)
C22—C23—H23C	109.5	C53—C52—H52A	108.4
H23A—C23—H23C	109.5	C42—C52—H52A	108.4
H23B—C23—H23C	109.5	C53—C52—H52B	108.4
C25—C24—C14	115.33 (13)	C42—C52—H52B	108.4
C25—C24—H24A	108.4	H52A—C52—H52B	107.5
C14—C24—H24A	108.4	C54—C53—C52	114.01 (13)
C25—C24—H24B	108.4	C54—C53—H53A	108.7
C14—C24—H24B	108.4	C52—C53—H53A	108.7
H24A—C24—H24B	107.5	C54—C53—H53B	108.7
C26—C25—C24	114.49 (14)	C52—C53—H53B	108.7
C26—C25—H25A	108.6	H53A—C53—H53B	107.6
C24—C25—H25A	108.6	C53—C54—C55	113.92 (16)
C26—C25—H25B	108.6	C53—C54—H54A	108.8
C24—C25—H25B	108.6	C55—C54—H54A	108.8
H25A—C25—H25B	107.6	C53—C54—H54B	108.8
C25—C26—C27	114.59 (17)	C55—C54—H54B	108.8
C25—C26—H26A	108.6	H54A—C54—H54B	107.7
C27—C26—H26A	108.6	C56—C55—C54	113.6 (2)
C25—C26—H26B	108.6	C56—C55—H55A	108.8
C27—C26—H26B	108.6	C54—C55—H55A	108.8
H26A—C26—H26B	107.6	C56—C55—H55B	108.8
C28—C27—C26	113.6 (2)	C54—C55—H55B	108.8
C28—C27—H27A	108.8	H55A—C55—H55B	107.7
C26—C27—H27A	108.8	C55—C56—H56A	109.5
C28—C27—H27B	108.8	C55—C56—H56B	109.5
C26—C27—H27B	108.8	H56A—C56—H56B	109.5
H27A—C27—H27B	107.7	C55—C56—H56C	109.5
C27—C28—H28A	109.5	H56A—C56—H56C	109.5
C27—C28—H28B	109.5	H56B—C56—H56C	109.5
H28A—C28—H28B	109.5	C2—O1—C15	117.02 (11)
C27—C28—H28C	109.5	C6—O2—C16	117.76 (12)
H28A—C28—H28C	109.5	C9—O3—C17	118.75 (13)
H28B—C28—H28C	109.5	C13—O4—C18	118.20 (11)
C30—C29—C34	119.75 (13)	C30—O5—C43	116.80 (11)
C30—C29—H29	120.1	C34—O6—C44	117.70 (12)
C34—C29—H29	120.1	C37—O7—C45	119.00 (12)
O5—C30—C29	122.62 (13)	C41—O8—C46	117.68 (11)

C6—C1—C2—O1	179.45 (13)	C31—C32—C33—C34	−1.21 (19)
C6—C1—C2—C3	−1.7 (2)	C31—C32—C33—C35	174.97 (12)
O1—C2—C3—C4	−178.09 (12)	C30—C29—C34—O6	178.80 (12)
C1—C2—C3—C4	3.0 (2)	C30—C29—C34—C33	−0.6 (2)
O1—C2—C3—C14ⁱ	5.19 (18)	C32—C33—C34—O6	−178.93 (11)
C1—C2—C3—C14ⁱ	−173.70 (13)	C35—C33—C34—O6	4.70 (18)
C2—C3—C4—C5	−2.1 (2)	C32—C33—C34—C29	0.49 (19)
C14ⁱ—C3—C4—C5	174.45 (13)	C35—C33—C34—C29	−175.88 (12)
C3—C4—C5—C6	−0.1 (2)	C34—C33—C35—C38	−81.52 (16)
C3—C4—C5—C7	−177.63 (13)	C32—C33—C35—C38	102.39 (15)
C2—C1—C6—O2	−179.54 (13)	C34—C33—C35—C47	150.64 (12)
C2—C1—C6—C5	−0.7 (2)	C32—C33—C35—C47	−25.45 (18)
C4—C5—C6—O2	−179.51 (12)	C41—C36—C37—O7	177.96 (13)
C7—C5—C6—O2	−1.86 (19)	C41—C36—C37—C38	−1.7 (2)
C4—C5—C6—C1	1.5 (2)	O7—C37—C38—C39	−176.61 (12)
C7—C5—C6—C1	179.19 (13)	C36—C37—C38—C39	3.1 (2)
C4—C5—C7—C10	−98.86 (16)	O7—C37—C38—C35	1.04 (19)
C6—C5—C7—C10	83.67 (16)	C36—C37—C38—C35	−179.26 (13)
C4—C5—C7—C19	29.4 (2)	C33—C35—C38—C39	−32.11 (19)
C6—C5—C7—C19	−148.07 (14)	C47—C35—C38—C39	97.51 (15)
C13—C8—C9—O3	−179.32 (13)	C33—C35—C38—C37	150.41 (13)
C13—C8—C9—C10	1.6 (2)	C47—C35—C38—C37	−79.97 (16)
O3—C9—C10—C11	177.45 (13)	C37—C38—C39—C40	−1.3 (2)
C8—C9—C10—C11	−3.4 (2)	C35—C38—C39—C40	−178.77 (13)
O3—C9—C10—C7	−2.0 (2)	C38—C39—C40—C41	−1.9 (2)
C8—C9—C10—C7	177.10 (14)	C38—C39—C40—C42	−179.11 (12)
C5—C7—C10—C11	29.8 (2)	C37—C36—C41—O8	179.39 (13)
C19—C7—C10—C11	−99.88 (16)	C37—C36—C41—C40	−1.6 (2)
C5—C7—C10—C9	−150.77 (13)	C39—C40—C41—O8	−177.60 (12)
C19—C7—C10—C9	79.56 (16)	C42—C40—C41—O8	−0.27 (19)
C9—C10—C11—C12	1.7 (2)	C39—C40—C41—C36	3.3 (2)
C7—C10—C11—C12	−178.89 (13)	C42—C40—C41—C36	−179.34 (13)
C10—C11—C12—C13	1.9 (2)	C39—C40—C42—C31ⁱⁱ	−32.87 (18)
C10—C11—C12—C14	178.79 (13)	C41—C40—C42—C31ⁱⁱ	149.96 (13)
C9—C8—C13—O4	−178.79 (13)	C39—C40—C42—C52	95.80 (15)
C9—C8—C13—C12	2.1 (2)	C41—C40—C42—C52	−81.38 (15)
C11—C12—C13—O4	177.07 (12)	C33—C35—C47—C48	−60.43 (16)
C14—C12—C13—O4	−0.02 (19)	C38—C35—C47—C48	170.21 (11)
C11—C12—C13—C8	−3.8 (2)	C35—C47—C48—C49	−179.75 (13)
C14—C12—C13—C8	179.12 (13)	C47—C48—C49—C50	−174.79 (14)
C11—C12—C14—C3ⁱ	32.57 (19)	C48—C49—C50—C51	−177.45 (18)
C13—C12—C14—C3ⁱ	−150.54 (13)	C31ⁱⁱ—C42—C52—C53	−65.20 (16)
C11—C12—C14—C24	−97.35 (16)	C40—C42—C52—C53	166.90 (12)
C13—C12—C14—C24	79.54 (16)	C42—C52—C53—C54	−74.83 (17)
C5—C7—C19—C20	63.96 (17)	C52—C53—C54—C55	−175.36 (14)
C10—C7—C19—C20	−167.15 (13)	C53—C54—C55—C56	−179.55 (18)
C7—C19—C20—C21	175.30 (16)	C1—C2—O1—C15	0.5 (2)
C19—C20—C21—C22	65.6 (3)	C3—C2—O1—C15	−178.42 (13)
C20—C21—C22—C23	167.7 (2)	C1—C6—O2—C16	−20.1 (2)
C12—C14—C24—C25	−162.65 (12)	C5—C6—O2—C16	160.93 (13)
C3ⁱ—C14—C24—C25	67.83 (17)	C8—C9—O3—C17	17.2 (2)
C14—C24—C25—C26	73.33 (18)	C10—C9—O3—C17	−163.64 (17)
C24—C25—C26—C27	174.15 (15)	C8—C13—O4—C18	8.3 (2)
C25—C26—C27—C28	−178.36 (18)	C12—C13—O4—C18	−172.56 (13)
C34—C29—C30—O5	−178.55 (13)	C29—C30—O5—C43	0.0 (2)
C34—C29—C30—C31	1.3 (2)	C31—C30—O5—C43	−179.86 (13)
O5—C30—C31—C32	177.96 (11)	C29—C34—O6—C44	19.75 (19)
C29—C30—C31—C32	−1.94 (19)	C33—C34—O6—C44	−160.84 (13)
O5—C30—C31—C42ⁱⁱ	−4.43 (18)	C36—C37—O7—C45	−8.4 (2)
C29—C30—C31—C42ⁱⁱ	175.67 (12)	C38—C37—O7—C45	171.30 (16)
C30—C31—C32—C33	1.92 (19)	C36—C41—O8—C46	−5.6 (2)
C42ⁱⁱ—C31—C32—C33	−175.61 (12)	C40—C41—O8—C46	175.33 (13)

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₅₆H₈₀O₈
M_r	881.20
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.2084 (2), 14.1270 (2), 23.1489 (4)
α, β, γ (°)	98.929 (1), 97.914 (1), 103.581 (1)
V (Å³)	2534.93 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.44 × 0.39 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	42741, 12226, 7816
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.148, 0.99
No. of reflections	12226
No. of parameters	589
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.26

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

Acknowledgements

The authors thank Dr Manuel Fernandes from the University of the Witwatersrand for his assistance with the data collection and refinement.

References

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