Different inter­action motifs of dipolar S=O...C=O contacts that associate diastereomers of 2,4(6)-di-O-benzoyl-6(4)-O-{[(1S)-7,7-dimethyl-2-oxo­bicyclo­[2.2.1]heptan-1-ylmethyl]­sulfon­yl}-myo-inositol 1,3,5-orthoacetate

Diastereomeric mixtures of 2,4(6)-di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol 1,3,5-orthoesters associate in their crystal structures via different geometries of S=O...C=O short contacts, depending upon the substitution. A comparison of the dimeric association in the orthoacetate and orthoformate (solvated) derivatives shows a sheared parallel motif of dipolar S=O...C=O contacts bridging the former, whereas perpendicular S=O...C=O contacts occur in the latter. The title compound, C₃₂H₃₄O₁₁S, is chiral, owing to the presence of the camphor moiety.

S1. Comment

The importance of non-covalent intermolecular interactions is being increasingly recognized because of their role in crystal engineering, host–guest complexes, enzyme–substrate binding and drug design (Desiraju & Steiner, 1999). The understanding of weak interactions in molecular crystals can be utilized for the design and synthesis of functional supramolecular assemblies (Desiraju, 1989). Amongst these, dipolar contacts are of considerable interest because of their involvement in the conformational stabilization of proteins (Maccallum et al., 1995) and the structure-based design of drugs (Hof & Diedrich, 2004). The geometrical preferences of S═O···C═O contacts and their role in the formation of inclusion crystals of 2,4(6)-di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol 1,3,5-orthoformate were first recognized by us (Manoj et al., 2005, 2006). In order to explore the dipolar association of this framework, a diastereomeric mixture, (I) and (II), of the orthoacetate derivative was prepared. Suitable single crystals containing a 1:1 mixture of (I) and (II) were obtained from a dichloromethane–methanol mixture. We did not observe any (pseudo)polymorphic modifications under different crystallization methods or solvents. Synthetically protected myo-inositol 1,3,5-orthoester derivatives also serve as key intermediates (Sureshan et al., 2003) for the preparation of biologically relevant myo-inositol phosphates, which play a significant role in cellular signal transduction (Potter & Lampe, 1995).

The crystal structure of the title compound shows short intramolecular C—H···O interactions (Fig. 1) between atom H23A (H23D) of the camphorsulfonyl methylene group and atom O7 (O7') of the equatorial benzoyl group in both diastereomers (Table 1). Compared with the conformation of the orthoformate derivative (Manoj et al., 2005, 2006), the orthoacetate shows a significant orientational change in the camphorsulfonate group (see supplementary figures for molecular overlapping), which could be due to this intramolecular C—H···O interaction.

In the absence of conventional hydrogen bonding, diastereomers (I) and (II) are associated via dipolar S═O···C═O short contacts and weak hydrogen bonds. The crystal structure shows dimeric bridging (Fig. 1) and the contacts between the diastereomers are asymmetric. The (S═)O···C(═O) distances are 3.144 (5) and 3.556 (5) Å [O9···C16' = 3.144 (5) Å, O9···C16'═O8' = 92.2 (1)° and S1═O9···C16' = 123.6 (1)°; O9'···C16 = 3.556 (5) Å, O9'···C16═O8 = 94.7 (1)° and S1'═ O9'···C16 = 103.6 (1)°], with complementary C—H···O contacts of 2.63 and 2.41 Å, respectively (Table 1). These complementary interactions (the shorter of the S═O···C═O contacts is accompanied by a longer C—H···O interaction and vice versa) between diastereomers were also seen in the solvates of the orthoformate derivative (Manoj et al., 2005, 2006).

The basic difference in the association of the diastereomers in the title compound and its orthoformate analogue (Manoj et al., 2005, 2006) is in the geometry of the dipolar S═O···C═O contacts. We have classified the S═O···C═O interaction motifs as Types I, II and III (Fig. 2a), similar to carbonyl–carbonyl interactions (Allen et al., 1998). In all the crystalline solvates of orthoformate (Manoj et al., 2005, 2006), the contacts were of Type I (Fig. 2b), whereas in the orthoacetate crystals they are of Type III (Fig. 2c). In the case of C═O···C═ O contacts, the frequency of occurrence of the various motifs is of the order Type II > Type III > Type I (Allen et al., 1998). A survey of the Cambridge Structural Database (CSD, Version 5.28; Allen, 2002) was carried out to see how S═ O···C═O contacts are distributed amongst these three types. The CSD was used for the geometric analysis of non-covalent intermolecular interactions with a distance (D) cut-off of 3.6 Å (twice the van der Waals radius of carbon, with a tolerance of 0.2 Å). The angle criteria for Type I were A1 = 90±10° and A2 = 160±20°, for Type II they were A1 = 90±10° and A2 = 90±20°, and for Type III they were A1 = 90±10° and A2 = 120±20°. All searches were carried out with error-free coordinates and restricted entries of disordered, ionic, polymeric and powdered structures. Interestingly, the maximum number of hits (235) was found for Type III, followed by Type I (111 hits) and Type II contacts (21 hits). The preferred Type III motif (and also the less preferred Type II) in S═O···C═ O contacts may be due to the heterodipoles having different van der Waals radii for S and C atoms. The Type III dipolar S═O···C═O interaction motif is indeed observed in the binding of N-tosyl-D-proline (ligand) to thymidylate synthase (from Escherichia coli), an essential enzyme in pyrimidine metabolism with therapeutic applications in cancer and infectious diseases (Erlanson et al., 2000).

Diastereomers (I) and (II), associated via S═O···C═O (and C—H···O) interactions, are packed in the crystal structure only via weak intermolecular interactions such as C—H···π and C—H···O by translation. These dimeric units, translated along the diagonal to the a and c axes, form somewhat off-centred C—H···π interactions between the methyl H atoms (H31E and H31C) of the camphor moiety and the phenyl ring of the axial benzoyl groups, as shown in Fig. 3; details are given in Table 1. [Please check additions to Table 1]. These molecular rows are linked to unit-translated ones along the b axis by very weak head-to-head C—H···O contacts, forming layers as shown in Fig. 3; details are given in Table 1. [Please check additions to Table 1]. These layers are linked along the third dimension via symmetric C—H···O contacts (Table 1) between the axial benzoyl atoms O8 and O8' and inositol ring atoms H3' and H1, respectively (see supplementary figures). Additionally, they are also linked via C18'—H18'···O1 and C12—H12···O10 contacts (Table 1) along the b axis.

The rectangular net of each of the diastereomers interlocks into the other via the equatorial benzoyl groups (Fig. 4), leaving no possibility of any guest inclusion, whereas the orthoformate derivative (Manoj et al., 2005, 2006) had the diastereomers organized in such a way that they created voids for the guests (see supplementary figures).

In conclusion, different motifs of association of S═O and C═O were observed in the crystals of 2,4(6)-di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol 1,3,5-orthoformate and its orthoacetate analogue. The experimentally observed motifs of these S═O···C═O contacts are expected to be of considerable interest in the context of improved binding of drug molecules containing S═O groups to their receptors (Erlanson et al., 2000).

Related literature

For related literature, see: Allen (2002); Allen et al. (1998); Desiraju (1989); Desiraju & Steiner (1999); Erlanson et al. (2000); Hof & Diedrich (2004); Maccallum et al. (1995); Manoj et al. (2005, 2006); Potter & Lampe (1995); Sureshan et al. (2003).

S2. Experimental

The preparation of 2,4(6)-di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol 1,3,5-orthoacetate, a mixture of diastereomers (I) and (II), was carried out as follows. A mixture of pyridine (10 ml), racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoacetate (0.412 g, 1 mmol) and (1S)-10-camphorsulfonyl chloride (0.751 g, 3 mmol) was stirred at room temperature for 24 h. Pyridine was evaporated under reduced pressure and the residue obtained was worked up with chloroform. The crude product was purified (0.451 g, 72%) by flash column chromatography over silica (eluent: ethyl acetate–petroleum ether 1:9 v/v). The mixture of diastereomers (I) and (II) was crystallized from a mixture of dichloromethane and methanol (4:1 v/v) in a closed container at room temperature (m.p. 426–427 K). Spectroscopic analysis: IR (CHCl₃, ν, cm^-1): 1718, 1733; ¹H NMR (CDCl₃, 200 MHz, δ, p.p.m.): 0.71–0.77 (2s, 3H), 0.92–1.02 (2s, 3H), 1.43 (s, 1H), 1.62 (s, 3H), 1.64–1.73 (m, 1H), 1.88–2.10 (m, 3H), 2.26–2.42 (m, 2H), 2.81–2.98 (m, 1H), 3.46–3.59 (2d, 1H), 4.61–4.76 (m, 2H), 4.76–4.83 (m, 1H), 5.47–5.59 (m, 2H), 5.78–5.86 (m, 1H), 7.43–7.63 (m, 6H), 8.10–8.18 (m, 4H); ¹³C NMR (CDCl₃, 50 MHz, δ, p.p.m.): 19.4, 19.5, 23.9, 24.7, 26.7, 26.8, 42.2, 42.6, 47.9, 48.0, 48.1, 57.7, 57.8, 62.3, 67.3, 67.4, 67.5, 69.8, 70.0, 70.3, 72.4, 72.6, 109.2, 128.4, 128.6, 128.8, 129.3, 129.9, 130.0, 133.5, 133.6, 165.1, 165.9, 213.9. Analysis, calculated for C₃₂H₃₄O₁₁S: C 61.33, H 5.47%; found: C 61.49, H 5.42%.

S3. Refinement

All H atoms were placed in idealized positions, with C—H = 0.98 Å for atoms H27 and H27' and inositol ring H atoms, 0.93 Å for phenyl H atoms, 0.97 Å for methylene H atoms and 0.96 Å for methyl H atoms, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Version 1.5; Macrae et al., 2006); software used to prepare material for publication: SHELXTL97 (Sheldrick, 1997), PLATON (Spek, 2003) and publCIF (Westrip, 2007).

Figures

	Fig. 1. A view of the associated diastereomers of the title compound, with the atom-labelleing scheme; (I) is unprimed and (II) is primed. Displacement ellipsoids are drawn at the 30% probability level. Intermolecular S═ O···C═O and C—H···O contacts and intramolecular C—H···O interactions are shown as dashed lines. Only H atoms involved in these interactions are shown. [Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z].
	Fig. 2. (a) Three possible interaction motifs of S═O···C═O dipolar contacts. (b) Type I contacts in orthoformate crystals (Manoj et al., 2005, 2006). (c) Type III contacts in orthoacetate crystals.
	Fig. 3. A layer of dimers linked via C—H···π (along the diagonal) and C—H···O interactions (along the b axis), both shown as dashed lines. [Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z; (iv) x, y, z + 1; (v) x, y, z - 1; (vi) x - 1, y + 1, z; (vii) x + 1, y + 1, z].
	Fig. 4. Interlocked grids of diastereomers (I) (dark grey) and (II) (light grey), viewed down the a axis.

2,4(6)-di-O-benzoyl-6(4)-O-{[(1S)-7,7-dimethyl-2- oxobicyclo[2.2.1]heptan-1-ylmethyl]sulfonyl}-myo-inositol 1,3,5-orthoacetate

Crystal data

C32H34O11S	Z = 2
Mr = 626.65	F(000) = 660
Triclinic, P1	Dx = 1.444 Mg m^−3
a = 11.5241 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6958 (16) Å	Cell parameters from 5336 reflections
c = 12.453 (2) Å	θ = 2.4–28.1°
α = 80.499 (3)°	µ = 0.18 mm^−1
β = 62.449 (2)°	T = 298 K
γ = 75.937 (2)°	Irregular, colourless
V = 1440.8 (4) Å^3	0.68 × 0.25 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	7596 independent reflections
Radiation source: fine-focus sealed tube	7284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω and ϕ scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.889, Tmax = 0.976	k = −13→13
9388 measured reflections	l = −14→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0711P)^2 + 0.3482P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
7596 reflections	Δρmax = 0.54 e Å^−3
799 parameters	Δρmin = −0.29 e Å^−3
3 restraints	Absolute structure: Flack H D (1983),2944 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.91377 (9)	0.76272 (8)	0.14984 (9)	0.0187 (2)
O1	1.1465 (3)	0.8970 (2)	0.4284 (3)	0.0218 (7)
O2	1.2987 (3)	0.8939 (2)	0.1723 (3)	0.0212 (7)
O3	1.0279 (3)	1.0056 (2)	0.3264 (3)	0.0232 (7)
O4	0.9564 (3)	0.7425 (2)	0.2576 (3)	0.0206 (7)
O5	0.9213 (3)	0.8977 (2)	0.5043 (3)	0.0187 (6)
O6	1.1021 (3)	0.6146 (2)	0.3732 (3)	0.0177 (6)
O7	1.3022 (3)	0.8645 (3)	−0.0028 (3)	0.0322 (8)
O8	1.2234 (3)	0.5181 (2)	0.4719 (3)	0.0280 (7)
O9	0.8311 (3)	0.6800 (3)	0.1748 (3)	0.0313 (7)
O10	0.8645 (3)	0.8859 (2)	0.1355 (3)	0.0308 (8)
O11	1.0921 (4)	0.4874 (3)	−0.0338 (3)	0.0497 (9)
C1	1.1835 (4)	0.7927 (3)	0.3621 (4)	0.0192 (9)
H1	1.2699	0.7471	0.3549	0.023*
C2	1.1899 (4)	0.8301 (3)	0.2382 (4)	0.0196 (9)
H2	1.2065	0.7604	0.1954	0.024*
C3	1.0576 (4)	0.9099 (3)	0.2517 (4)	0.0190 (9)
H3	1.0619	0.9407	0.1720	0.023*
C4	0.9437 (4)	0.8420 (3)	0.3213 (4)	0.0176 (9)
H4	0.8589	0.8959	0.3355	0.021*
C5	0.9430 (4)	0.7942 (3)	0.4431 (4)	0.0160 (8)
H5	0.8707	0.7501	0.4899	0.019*
C6	1.0754 (4)	0.7193 (3)	0.4329 (4)	0.0199 (9)
H6	1.0698	0.6973	0.5143	0.024*
C7	1.0234 (4)	0.9648 (3)	0.4408 (4)	0.0162 (8)
C8	0.9899 (5)	1.0694 (3)	0.5118 (5)	0.0268 (10)
H8A	1.0549	1.1188	0.4677	0.040*
H8B	0.9902	1.0430	0.5889	0.040*
H8C	0.9031	1.1135	0.5243	0.040*
C9	1.3508 (4)	0.8991 (3)	0.0496 (4)	0.0220 (9)
C10	1.4749 (4)	0.9513 (3)	−0.0109 (4)	0.0225 (9)
C11	1.5425 (4)	0.9631 (3)	0.0534 (4)	0.0239 (9)
H11	1.5095	0.9424	0.1361	0.029*
C12	1.6594 (5)	1.0060 (4)	−0.0079 (5)	0.0352 (12)
H12	1.7062	1.0141	0.0335	0.042*
C13	1.7070 (5)	1.0368 (4)	−0.1300 (5)	0.0371 (12)
H13	1.7850	1.0671	−0.1704	0.044*
C14	1.6399 (5)	1.0233 (4)	−0.1934 (5)	0.0353 (11)
H14	1.6736	1.0433	−0.2763	0.042*
C15	1.5228 (5)	0.9802 (4)	−0.1333 (5)	0.0327 (11)
H15	1.4770	0.9709	−0.1753	0.039*
C16	1.1759 (4)	0.5173 (3)	0.4041 (4)	0.0190 (9)
C17	1.1870 (4)	0.4132 (3)	0.3434 (4)	0.0196 (9)
C18	1.2755 (5)	0.3100 (4)	0.3499 (5)	0.0284 (11)
H18	1.3237	0.3062	0.3935	0.034*
C19	1.2905 (5)	0.2130 (4)	0.2902 (5)	0.0314 (11)
H19	1.3496	0.1441	0.2937	0.038*
C20	1.2194 (5)	0.2179 (4)	0.2265 (5)	0.0310 (11)
H20	1.2305	0.1521	0.1873	0.037*
C21	1.1308 (5)	0.3199 (4)	0.2196 (5)	0.0295 (11)
H21	1.0820	0.3225	0.1768	0.035*
C22	1.1160 (4)	0.4176 (4)	0.2771 (4)	0.0244 (10)
H22	1.0583	0.4868	0.2716	0.029*
C23	1.0712 (4)	0.7183 (4)	0.0281 (4)	0.0248 (9)
H23A	1.1243	0.7778	0.0108	0.030*
H23B	1.1156	0.6455	0.0541	0.030*
C24	1.0697 (4)	0.6985 (3)	−0.0893 (4)	0.0195 (9)
C25	0.9431 (5)	0.7463 (4)	−0.1082 (5)	0.0341 (11)
H25A	0.9038	0.8260	−0.0818	0.041*
H25B	0.8775	0.6963	−0.0637	0.041*
C26	0.9919 (5)	0.7444 (4)	−0.2460 (5)	0.0338 (11)
H26A	0.9459	0.6962	−0.2637	0.041*
H26B	0.9795	0.8235	−0.2826	0.041*
C27	1.1405 (4)	0.6895 (4)	−0.2906 (4)	0.0245 (10)
H27	1.1950	0.7029	−0.3779	0.029*
C28	1.1464 (5)	0.5605 (4)	−0.2457 (5)	0.0359 (12)
H28A	1.2363	0.5154	−0.2840	0.043*
H28B	1.0871	0.5257	−0.2605	0.043*
C29	1.1001 (5)	0.5668 (4)	−0.1109 (5)	0.0280 (10)
C30	1.1810 (5)	0.7413 (4)	−0.2087 (4)	0.0267 (10)
C31	1.1679 (7)	0.8752 (4)	−0.2262 (5)	0.0506 (16)
H31A	1.1836	0.9031	−0.1667	0.076*
H31B	1.0797	0.9108	−0.2170	0.076*
H31C	1.2321	0.8960	−0.3060	0.076*
C32	1.3205 (5)	0.6866 (5)	−0.2222 (5)	0.0423 (13)
H32A	1.3839	0.6969	−0.3053	0.064*
H32B	1.3254	0.6039	−0.1984	0.064*
H32C	1.3402	0.7245	−0.1714	0.064*
S1'	0.81494 (9)	0.46341 (8)	0.63126 (9)	0.0208 (2)
O1'	0.7006 (3)	0.2121 (2)	0.4593 (3)	0.0199 (6)
O2'	0.4280 (3)	0.3135 (2)	0.6174 (3)	0.0238 (7)
O3'	0.5755 (3)	0.3181 (2)	0.3608 (3)	0.0222 (7)
O4'	0.6051 (3)	0.6030 (2)	0.4216 (3)	0.0214 (7)
O5'	0.8007 (3)	0.3266 (2)	0.2820 (3)	0.0214 (7)
O6'	0.7551 (3)	0.4798 (2)	0.5350 (3)	0.0198 (6)
O7'	0.4382 (3)	0.3268 (3)	0.7903 (3)	0.0328 (8)
O8'	0.4940 (3)	0.7009 (2)	0.3161 (3)	0.0281 (7)
O9'	0.8589 (3)	0.5701 (3)	0.6179 (3)	0.0352 (8)
O10'	0.9053 (4)	0.3527 (3)	0.6134 (3)	0.0405 (9)
O11'	0.8954 (3)	0.4269 (3)	0.8309 (3)	0.0387 (8)
C1'	0.6679 (4)	0.3069 (3)	0.5344 (4)	0.0199 (9)
H1'	0.6672	0.2750	0.6126	0.024*
C2'	0.5324 (4)	0.3805 (3)	0.5546 (4)	0.0201 (9)
H2'	0.5133	0.4496	0.5993	0.024*
C3'	0.5346 (4)	0.4192 (3)	0.4316 (4)	0.0211 (9)
H3'	0.4458	0.4615	0.4419	0.025*
C4'	0.6375 (4)	0.4988 (3)	0.3580 (4)	0.0190 (9)
H4'	0.6406	0.5206	0.2774	0.023*
C5'	0.7727 (4)	0.4288 (3)	0.3469 (4)	0.0201 (9)
H5'	0.8414	0.4767	0.3009	0.024*
C6'	0.7773 (4)	0.3804 (3)	0.4664 (4)	0.0197 (9)
H6'	0.8646	0.3304	0.4506	0.024*
C7'	0.7036 (4)	0.2547 (3)	0.3456 (5)	0.0240 (10)
C8'	0.7406 (5)	0.1515 (3)	0.2699 (4)	0.0273 (11)
H8D	0.6760	0.1013	0.3109	0.041*
H8E	0.8272	0.1075	0.2582	0.041*
H8F	0.7422	0.1802	0.1925	0.041*
C9'	0.3850 (5)	0.2968 (3)	0.7391 (4)	0.0255 (10)
C10'	0.2662 (4)	0.2417 (3)	0.7985 (4)	0.0255 (10)
C11'	0.1943 (5)	0.2289 (4)	0.7383 (5)	0.0335 (12)
H11'	0.2241	0.2507	0.6559	0.040*
C12'	0.0775 (5)	0.1834 (4)	0.8019 (6)	0.0385 (13)
H12'	0.0285	0.1767	0.7622	0.046*
C13'	0.0344 (5)	0.1485 (4)	0.9228 (6)	0.0473 (16)
H13'	−0.0423	0.1164	0.9643	0.057*
C14'	0.1069 (6)	0.1616 (4)	0.9835 (5)	0.0417 (13)
H14'	0.0782	0.1391	1.0656	0.050*
C15'	0.2194 (5)	0.2076 (4)	0.9207 (5)	0.0324 (11)
H15'	0.2667	0.2165	0.9614	0.039*
C16'	0.5395 (4)	0.7011 (3)	0.3851 (4)	0.0196 (9)
C17'	0.5288 (4)	0.8061 (3)	0.4450 (4)	0.0200 (9)
C18'	0.4413 (5)	0.9095 (4)	0.4368 (4)	0.0278 (10)
H18'	0.3918	0.9122	0.3946	0.033*
C19'	0.4291 (5)	1.0080 (4)	0.4923 (5)	0.0329 (12)
H19'	0.3702	1.0770	0.4887	0.039*
C20'	0.5052 (5)	1.0034 (4)	0.5534 (5)	0.0322 (11)
H20'	0.4977	1.0700	0.5897	0.039*
C21'	0.5923 (5)	0.9007 (4)	0.5607 (5)	0.0318 (11)
H21'	0.6428	0.8982	0.6019	0.038*
C22'	0.6035 (4)	0.8020 (4)	0.5065 (4)	0.0247 (10)
H22'	0.6615	0.7327	0.5113	0.030*
C23'	0.6658 (5)	0.4595 (4)	0.7695 (4)	0.0328 (11)
H23C	0.5927	0.5094	0.7558	0.039*
H23D	0.6497	0.3794	0.7855	0.039*
C24'	0.6589 (5)	0.4964 (4)	0.8832 (5)	0.0287 (10)
C25'	0.6281 (5)	0.6323 (4)	0.8969 (5)	0.0329 (11)
H25C	0.7083	0.6654	0.8523	0.039*
H25D	0.5625	0.6727	0.8684	0.039*
C26'	0.5727 (6)	0.6411 (4)	1.0353 (5)	0.0405 (13)
H26C	0.6244	0.6829	1.0531	0.049*
H26D	0.4800	0.6808	1.0704	0.049*
C27'	0.5878 (5)	0.5104 (4)	1.0825 (5)	0.0297 (11)
H27'	0.5336	0.4968	1.1698	0.036*
C28'	0.7357 (5)	0.4632 (4)	1.0393 (5)	0.0327 (11)
H28C	0.7779	0.5165	1.0551	0.039*
H28D	0.7521	0.3859	1.0779	0.039*
C29'	0.7847 (5)	0.4562 (3)	0.9047 (5)	0.0267 (10)
C30'	0.5541 (5)	0.4511 (4)	1.0013 (5)	0.0320 (11)
C31'	0.4102 (5)	0.4943 (5)	1.0185 (5)	0.0441 (13)
H31D	0.3947	0.5782	1.0013	0.066*
H31E	0.3497	0.4757	1.1007	0.066*
H31F	0.3960	0.4560	0.9642	0.066*
C32'	0.5785 (6)	0.3155 (4)	1.0181 (5)	0.0418 (13)
H32D	0.5489	0.2846	0.9703	0.063*
H32E	0.5298	0.2920	1.1022	0.063*
H32F	0.6720	0.2852	0.9925	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O9	0.0272 (16)	0.0479 (18)	0.0230 (18)	−0.0136 (14)	−0.0115 (14)	−0.0020 (14)
S1	0.0194 (5)	0.0210 (4)	0.0156 (6)	−0.0023 (4)	−0.0083 (4)	−0.0014 (4)
O1	0.0216 (15)	0.0209 (13)	0.0243 (18)	−0.0006 (11)	−0.0114 (14)	−0.0066 (13)
O2	0.0182 (15)	0.0223 (13)	0.0193 (18)	−0.0049 (11)	−0.0040 (13)	−0.0029 (12)
O3	0.0285 (17)	0.0172 (13)	0.0229 (18)	−0.0032 (12)	−0.0116 (15)	0.0002 (12)
O4	0.0259 (16)	0.0187 (13)	0.0217 (17)	−0.0021 (11)	−0.0137 (14)	−0.0061 (12)
O5	0.0217 (15)	0.0207 (13)	0.0126 (16)	−0.0014 (11)	−0.0068 (13)	−0.0051 (12)
O6	0.0222 (15)	0.0163 (12)	0.0146 (15)	−0.0012 (11)	−0.0101 (12)	0.0011 (11)
O7	0.0292 (17)	0.0442 (18)	0.0229 (19)	−0.0162 (14)	−0.0057 (15)	−0.0055 (14)
O8	0.0282 (17)	0.0256 (15)	0.033 (2)	0.0065 (13)	−0.0198 (16)	−0.0070 (14)
O10	0.0459 (19)	0.0250 (14)	0.0236 (18)	0.0078 (13)	−0.0230 (15)	−0.0046 (13)
O11	0.082 (3)	0.0256 (15)	0.044 (2)	−0.0147 (16)	−0.032 (2)	0.0098 (16)
C1	0.020 (2)	0.0182 (18)	0.021 (2)	0.0029 (16)	−0.0123 (19)	−0.0055 (17)
C2	0.015 (2)	0.0174 (17)	0.025 (3)	−0.0048 (15)	−0.0071 (19)	−0.0010 (17)
C3	0.021 (2)	0.0150 (17)	0.017 (2)	−0.0010 (16)	−0.0066 (19)	−0.0015 (17)
C4	0.018 (2)	0.0162 (17)	0.015 (2)	−0.0030 (15)	−0.0048 (18)	−0.0015 (16)
C5	0.0168 (19)	0.0171 (17)	0.014 (2)	−0.0035 (15)	−0.0073 (17)	0.0004 (16)
C6	0.025 (2)	0.0187 (18)	0.019 (2)	−0.0038 (16)	−0.0119 (19)	−0.0026 (17)
C7	0.0143 (19)	0.0223 (18)	0.008 (2)	−0.0024 (15)	−0.0028 (17)	0.0013 (16)
C8	0.029 (2)	0.021 (2)	0.030 (3)	−0.0038 (18)	−0.012 (2)	−0.005 (2)
C9	0.020 (2)	0.0209 (18)	0.023 (2)	−0.0007 (16)	−0.0084 (19)	−0.0051 (17)
C10	0.018 (2)	0.0190 (18)	0.024 (2)	−0.0012 (15)	−0.0039 (18)	−0.0066 (17)
C11	0.019 (2)	0.0240 (19)	0.023 (2)	−0.0027 (16)	−0.0059 (19)	−0.0001 (18)
C12	0.031 (3)	0.031 (2)	0.050 (4)	−0.0077 (19)	−0.021 (2)	−0.007 (2)
C13	0.027 (3)	0.038 (2)	0.039 (3)	−0.012 (2)	−0.004 (2)	−0.008 (2)
C14	0.031 (2)	0.043 (2)	0.020 (3)	−0.020 (2)	0.003 (2)	0.004 (2)
C15	0.037 (3)	0.033 (2)	0.030 (3)	−0.013 (2)	−0.013 (2)	−0.005 (2)
C16	0.0115 (19)	0.0174 (18)	0.020 (3)	−0.0020 (15)	−0.0019 (18)	0.0023 (17)
C17	0.015 (2)	0.0180 (18)	0.018 (2)	−0.0064 (15)	−0.0007 (18)	0.0033 (17)
C18	0.034 (3)	0.0199 (19)	0.031 (3)	−0.0024 (18)	−0.016 (2)	0.000 (2)
C19	0.037 (3)	0.0168 (19)	0.030 (3)	0.0040 (18)	−0.011 (2)	−0.0008 (19)
C20	0.038 (3)	0.019 (2)	0.033 (3)	−0.0085 (19)	−0.010 (2)	−0.005 (2)
C21	0.028 (2)	0.033 (2)	0.029 (3)	−0.0096 (19)	−0.010 (2)	−0.009 (2)
C22	0.024 (2)	0.0242 (19)	0.025 (3)	−0.0027 (17)	−0.012 (2)	−0.0018 (19)
C23	0.019 (2)	0.033 (2)	0.022 (2)	−0.0069 (16)	−0.0077 (18)	−0.0032 (18)
C24	0.022 (2)	0.027 (2)	0.012 (2)	−0.0121 (16)	−0.0074 (18)	0.0035 (17)
C25	0.027 (2)	0.046 (3)	0.025 (3)	0.006 (2)	−0.014 (2)	−0.005 (2)
C26	0.036 (3)	0.039 (2)	0.027 (3)	0.005 (2)	−0.019 (2)	−0.006 (2)
C27	0.025 (2)	0.032 (2)	0.016 (2)	−0.0045 (17)	−0.0087 (19)	−0.0037 (18)
C28	0.043 (3)	0.031 (2)	0.037 (3)	−0.007 (2)	−0.018 (2)	−0.010 (2)
C29	0.036 (3)	0.024 (2)	0.026 (3)	−0.0111 (18)	−0.013 (2)	0.0010 (19)
C30	0.029 (2)	0.030 (2)	0.025 (3)	−0.0086 (17)	−0.012 (2)	−0.0055 (19)
C31	0.091 (5)	0.039 (3)	0.028 (3)	−0.029 (3)	−0.026 (3)	0.004 (2)
C32	0.028 (3)	0.078 (4)	0.026 (3)	−0.018 (2)	−0.009 (2)	−0.013 (3)
S1'	0.0224 (6)	0.0225 (5)	0.0182 (6)	−0.0034 (4)	−0.0103 (5)	0.0002 (4)
O1'	0.0207 (15)	0.0175 (12)	0.0202 (17)	−0.0026 (11)	−0.0077 (13)	−0.0040 (12)
O2'	0.0208 (16)	0.0220 (13)	0.0259 (19)	−0.0057 (12)	−0.0062 (14)	−0.0048 (13)
O3'	0.0238 (15)	0.0156 (12)	0.0283 (19)	−0.0016 (11)	−0.0122 (14)	−0.0049 (12)
O4'	0.0262 (15)	0.0150 (12)	0.0248 (18)	0.0006 (11)	−0.0139 (14)	−0.0048 (12)
O5'	0.0202 (15)	0.0167 (13)	0.0222 (18)	−0.0018 (11)	−0.0057 (13)	−0.0021 (12)
O6'	0.0239 (15)	0.0171 (12)	0.0169 (16)	−0.0014 (11)	−0.0094 (13)	0.0004 (12)
O7'	0.0352 (18)	0.0401 (17)	0.0267 (19)	−0.0166 (14)	−0.0131 (16)	0.0011 (15)
O8'	0.0284 (17)	0.0241 (14)	0.036 (2)	0.0027 (12)	−0.0199 (16)	−0.0065 (14)
O9'	0.048 (2)	0.0446 (18)	0.0256 (18)	−0.0307 (16)	−0.0201 (16)	0.0095 (15)
O10'	0.047 (2)	0.0403 (18)	0.038 (2)	0.0131 (15)	−0.0290 (18)	−0.0121 (16)
O11'	0.0302 (17)	0.0480 (18)	0.0333 (19)	0.0003 (14)	−0.0124 (15)	−0.0075 (15)
C1'	0.022 (2)	0.0211 (19)	0.017 (2)	−0.0023 (16)	−0.0098 (19)	0.0000 (17)
C2'	0.020 (2)	0.0189 (18)	0.017 (2)	−0.0033 (16)	−0.0047 (19)	−0.0025 (16)
C3'	0.019 (2)	0.0146 (17)	0.029 (3)	0.0024 (15)	−0.0116 (19)	−0.0067 (18)
C4'	0.021 (2)	0.0151 (17)	0.022 (2)	−0.0002 (16)	−0.0118 (19)	−0.0025 (17)
C5'	0.020 (2)	0.0172 (18)	0.020 (2)	−0.0054 (15)	−0.0055 (18)	−0.0031 (17)
C6'	0.021 (2)	0.0188 (18)	0.020 (2)	−0.0020 (16)	−0.0106 (19)	−0.0018 (17)
C7'	0.024 (2)	0.0150 (18)	0.035 (3)	0.0007 (16)	−0.016 (2)	−0.0051 (19)
C8'	0.035 (3)	0.0194 (19)	0.026 (3)	0.0001 (18)	−0.014 (2)	−0.0059 (19)
C9'	0.029 (2)	0.0160 (18)	0.023 (3)	−0.0001 (16)	−0.005 (2)	−0.0055 (17)
C10'	0.021 (2)	0.0185 (18)	0.031 (3)	0.0022 (15)	−0.008 (2)	−0.0064 (18)
C11'	0.035 (3)	0.0196 (19)	0.039 (3)	−0.0031 (17)	−0.010 (2)	−0.0062 (19)
C12'	0.026 (2)	0.033 (2)	0.049 (3)	−0.0093 (19)	−0.004 (2)	−0.013 (2)
C13'	0.029 (3)	0.028 (2)	0.061 (4)	−0.014 (2)	0.008 (3)	−0.012 (2)
C14'	0.049 (3)	0.025 (2)	0.038 (3)	−0.009 (2)	−0.008 (3)	0.001 (2)
C15'	0.033 (3)	0.022 (2)	0.033 (3)	−0.0039 (18)	−0.007 (2)	−0.0027 (19)
C16'	0.023 (2)	0.0203 (19)	0.018 (2)	−0.0019 (16)	−0.0128 (19)	−0.0017 (17)
C17'	0.019 (2)	0.0178 (18)	0.017 (2)	−0.0023 (16)	−0.0038 (18)	−0.0007 (17)
C18'	0.031 (2)	0.023 (2)	0.025 (3)	−0.0009 (18)	−0.011 (2)	−0.0018 (19)
C19'	0.043 (3)	0.0184 (19)	0.033 (3)	0.0019 (19)	−0.016 (2)	−0.001 (2)
C20'	0.037 (3)	0.023 (2)	0.027 (3)	−0.0081 (19)	−0.002 (2)	−0.008 (2)
C21'	0.025 (2)	0.035 (2)	0.039 (3)	−0.0104 (19)	−0.012 (2)	−0.009 (2)
C22'	0.014 (2)	0.024 (2)	0.030 (3)	−0.0044 (16)	−0.005 (2)	−0.0013 (19)
C23'	0.026 (2)	0.052 (3)	0.021 (2)	−0.016 (2)	−0.0054 (19)	−0.008 (2)
C24'	0.029 (2)	0.029 (2)	0.027 (3)	−0.0077 (18)	−0.010 (2)	−0.0051 (19)
C25'	0.038 (3)	0.024 (2)	0.036 (3)	0.0009 (19)	−0.019 (2)	−0.002 (2)
C26'	0.040 (3)	0.036 (3)	0.045 (4)	0.003 (2)	−0.019 (3)	−0.016 (2)
C27'	0.036 (3)	0.035 (2)	0.016 (2)	−0.014 (2)	−0.007 (2)	0.0001 (19)
C28'	0.037 (3)	0.036 (2)	0.029 (3)	−0.012 (2)	−0.018 (2)	0.004 (2)
C29'	0.029 (2)	0.023 (2)	0.029 (3)	−0.0025 (17)	−0.014 (2)	−0.0024 (19)
C30'	0.038 (3)	0.038 (2)	0.019 (3)	−0.015 (2)	−0.010 (2)	0.002 (2)
C31'	0.032 (3)	0.069 (3)	0.024 (3)	−0.020 (2)	−0.002 (2)	−0.001 (3)
C32'	0.054 (3)	0.035 (2)	0.036 (3)	−0.028 (2)	−0.012 (3)	0.002 (2)

Geometric parameters (Å, º)

O9—S1	1.419 (3)	S1'—O9'	1.415 (3)
S1—O10	1.428 (3)	S1'—O10'	1.427 (3)
S1—O4	1.596 (3)	S1'—O6'	1.605 (3)
S1—C23	1.766 (4)	S1'—C23'	1.787 (5)
O1—C7	1.399 (5)	O1'—C7'	1.409 (6)
O1—C1	1.451 (4)	O1'—C1'	1.436 (5)
O2—C9	1.355 (6)	O2'—C9'	1.355 (6)
O2—C2	1.450 (5)	O2'—C2'	1.435 (5)
O3—C7	1.407 (5)	O3'—C7'	1.422 (5)
O3—C3	1.449 (5)	O3'—C3'	1.446 (5)
O4—C4	1.455 (4)	O4'—C16'	1.349 (5)
O5—C7	1.417 (5)	O4'—C4'	1.441 (4)
O5—C5	1.445 (4)	O5'—C7'	1.415 (5)
O6—C16	1.361 (5)	O5'—C5'	1.441 (5)
O6—C6	1.433 (4)	O6'—C6'	1.458 (5)
O7—C9	1.200 (5)	O7'—C9'	1.203 (6)
O8—C16	1.203 (5)	O8'—C16'	1.196 (5)
O11—C29	1.207 (6)	O11'—C29'	1.181 (6)
C1—C2	1.505 (6)	C1'—C2'	1.515 (6)
C1—C6	1.523 (6)	C1'—C6'	1.531 (6)
C1—H1	0.9800	C1'—H1'	0.9800
C2—C3	1.533 (5)	C2'—C3'	1.514 (6)
C2—H2	0.9800	C2'—H2'	0.9800
C3—C4	1.528 (6)	C3'—C4'	1.537 (6)
C3—H3	0.9800	C3'—H3'	0.9800
C4—C5	1.525 (6)	C4'—C5'	1.528 (6)
C4—H4	0.9800	C4'—H4'	0.9800
C5—C6	1.523 (5)	C5'—C6'	1.522 (6)
C5—H5	0.9800	C5'—H5'	0.9800
C6—H6	0.9800	C6'—H6'	0.9800
C7—C8	1.496 (5)	C7'—C8'	1.510 (5)
C8—H8A	0.9600	C8'—H8D	0.9600
C8—H8B	0.9600	C8'—H8E	0.9600
C8—H8C	0.9600	C8'—H8F	0.9600
C9—C10	1.504 (6)	C9'—C10'	1.473 (6)
C10—C15	1.373 (7)	C10'—C15'	1.382 (7)
C10—C11	1.390 (6)	C10'—C11'	1.395 (7)
C11—C12	1.379 (7)	C11'—C12'	1.394 (7)
C11—H11	0.9300	C11'—H11'	0.9300
C12—C13	1.373 (8)	C12'—C13'	1.372 (8)
C12—H12	0.9300	C12'—H12'	0.9300
C13—C14	1.382 (8)	C13'—C14'	1.406 (8)
C13—H13	0.9300	C13'—H13'	0.9300
C14—C15	1.382 (7)	C14'—C15'	1.358 (7)
C14—H14	0.9300	C14'—H14'	0.9300
C15—H15	0.9300	C15'—H15'	0.9300
C16—C17	1.486 (5)	C16'—C17'	1.490 (5)
C17—C22	1.394 (6)	C17'—C22'	1.381 (6)
C17—C18	1.396 (6)	C17'—C18'	1.397 (6)
C18—C19	1.390 (6)	C18'—C19'	1.385 (6)
C18—H18	0.9300	C18'—H18'	0.9300
C19—C20	1.367 (7)	C19'—C20'	1.390 (7)
C19—H19	0.9300	C19'—H19'	0.9300
C20—C21	1.389 (7)	C20'—C21'	1.386 (7)
C20—H20	0.9300	C20'—H20'	0.9300
C21—C22	1.382 (6)	C21'—C22'	1.382 (6)
C21—H21	0.9300	C21'—H21'	0.9300
C22—H22	0.9300	C22'—H22'	0.9300
C23—C24	1.527 (6)	C23'—C24'	1.510 (7)
C23—H23A	0.9700	C23'—H23C	0.9700
C23—H23B	0.9700	C23'—H23D	0.9700
C24—C29	1.534 (5)	C24'—C30'	1.520 (7)
C24—C25	1.541 (6)	C24'—C29'	1.543 (6)
C24—C30	1.552 (6)	C24'—C25'	1.562 (6)
C25—C26	1.541 (7)	C25'—C26'	1.549 (8)
C25—H25A	0.9700	C25'—H25C	0.9700
C25—H25B	0.9700	C25'—H25D	0.9700
C26—C27	1.535 (7)	C26'—C27'	1.543 (7)
C26—H26A	0.9700	C26'—H26C	0.9700
C26—H26B	0.9700	C26'—H26D	0.9700
C27—C28	1.516 (6)	C27'—C28'	1.514 (7)
C27—C30	1.552 (6)	C27'—C30'	1.542 (6)
C27—H27	0.9800	C27'—H27'	0.9800
C28—C29	1.517 (7)	C28'—C29'	1.510 (7)
C28—H28A	0.9700	C28'—H28C	0.9700
C28—H28B	0.9700	C28'—H28D	0.9700
C30—C32	1.518 (7)	C30'—C31'	1.534 (8)
C30—C31	1.525 (6)	C30'—C32'	1.539 (7)
C31—H31A	0.9600	C31'—H31D	0.9600
C31—H31B	0.9600	C31'—H31E	0.9600
C31—H31C	0.9600	C31'—H31F	0.9600
C32—H32A	0.9600	C32'—H32D	0.9600
C32—H32B	0.9600	C32'—H32E	0.9600
C32—H32C	0.9600	C32'—H32F	0.9600
O9—S1—O10	119.8 (2)	O9'—S1'—O10'	121.0 (2)
O9—S1—O4	106.13 (18)	O9'—S1'—O6'	104.70 (18)
O10—S1—O4	108.44 (16)	O10'—S1'—O6'	107.53 (17)
O9—S1—C23	110.07 (19)	O9'—S1'—C23'	109.6 (2)
O10—S1—C23	110.9 (2)	O10'—S1'—C23'	111.7 (2)
O4—S1—C23	99.38 (18)	O6'—S1'—C23'	99.89 (19)
C7—O1—C1	112.1 (3)	C7'—O1'—C1'	111.5 (3)
C9—O2—C2	116.3 (3)	C9'—O2'—C2'	115.6 (3)
C7—O3—C3	112.4 (3)	C7'—O3'—C3'	110.8 (3)
C4—O4—S1	120.5 (2)	C16'—O4'—C4'	116.0 (3)
C7—O5—C5	113.0 (3)	C7'—O5'—C5'	111.7 (3)
C16—O6—C6	116.0 (3)	C6'—O6'—S1'	119.8 (2)
O1—C1—C2	109.0 (3)	O1'—C1'—C2'	109.8 (3)
O1—C1—C6	107.4 (3)	O1'—C1'—C6'	106.3 (3)
C2—C1—C6	109.7 (3)	C2'—C1'—C6'	111.0 (3)
O1—C1—H1	110.2	O1'—C1'—H1'	109.9
C2—C1—H1	110.2	C2'—C1'—H1'	109.9
C6—C1—H1	110.2	C6'—C1'—H1'	109.9
O2—C2—C1	107.6 (3)	O2'—C2'—C3'	106.0 (3)
O2—C2—C3	110.4 (3)	O2'—C2'—C1'	112.2 (3)
C1—C2—C3	109.3 (4)	C3'—C2'—C1'	108.0 (4)
O2—C2—H2	109.8	O2'—C2'—H2'	110.2
C1—C2—H2	109.8	C3'—C2'—H2'	110.2
C3—C2—H2	109.8	C1'—C2'—H2'	110.2
O3—C3—C4	105.4 (3)	O3'—C3'—C2'	110.3 (3)
O3—C3—C2	109.0 (3)	O3'—C3'—C4'	105.9 (3)
C4—C3—C2	110.0 (3)	C2'—C3'—C4'	111.1 (3)
O3—C3—H3	110.8	O3'—C3'—H3'	109.8
C4—C3—H3	110.8	C2'—C3'—H3'	109.8
C2—C3—H3	110.8	C4'—C3'—H3'	109.8
O4—C4—C5	107.9 (3)	O4'—C4'—C5'	108.4 (3)
O4—C4—C3	112.9 (3)	O4'—C4'—C3'	110.1 (3)
C5—C4—C3	108.7 (3)	C5'—C4'—C3'	107.2 (3)
O4—C4—H4	109.1	O4'—C4'—H4'	110.4
C5—C4—H4	109.1	C5'—C4'—H4'	110.4
C3—C4—H4	109.1	C3'—C4'—H4'	110.4
O5—C5—C6	106.4 (3)	O5'—C5'—C6'	105.5 (3)
O5—C5—C4	104.9 (3)	O5'—C5'—C4'	106.0 (3)
C6—C5—C4	113.9 (3)	C6'—C5'—C4'	115.4 (4)
O5—C5—H5	110.5	O5'—C5'—H5'	109.9
C6—C5—H5	110.5	C6'—C5'—H5'	109.9
C4—C5—H5	110.5	C4'—C5'—H5'	109.9
O6—C6—C1	111.5 (3)	O6'—C6'—C5'	108.4 (3)
O6—C6—C5	109.0 (3)	O6'—C6'—C1'	111.3 (3)
C1—C6—C5	108.3 (3)	C5'—C6'—C1'	107.6 (3)
O6—C6—H6	109.3	O6'—C6'—H6'	109.8
C1—C6—H6	109.3	C5'—C6'—H6'	109.8
C5—C6—H6	109.3	C1'—C6'—H6'	109.8
O1—C7—O3	110.7 (3)	O1'—C7'—O5'	111.1 (3)
O1—C7—O5	110.5 (3)	O1'—C7'—O3'	110.1 (4)
O3—C7—O5	109.6 (3)	O5'—C7'—O3'	110.7 (3)
O1—C7—C8	109.5 (3)	O1'—C7'—C8'	109.2 (3)
O3—C7—C8	108.5 (3)	O5'—C7'—C8'	107.7 (4)
O5—C7—C8	108.1 (3)	O3'—C7'—C8'	108.0 (3)
C7—C8—H8A	109.5	C7'—C8'—H8D	109.5
C7—C8—H8B	109.5	C7'—C8'—H8E	109.5
H8A—C8—H8B	109.5	H8D—C8'—H8E	109.5
C7—C8—H8C	109.5	C7'—C8'—H8F	109.5
H8A—C8—H8C	109.5	H8D—C8'—H8F	109.5
H8B—C8—H8C	109.5	H8E—C8'—H8F	109.5
O7—C9—O2	122.7 (4)	O7'—C9'—O2'	122.4 (4)
O7—C9—C10	124.9 (4)	O7'—C9'—C10'	125.3 (5)
O2—C9—C10	112.4 (4)	O2'—C9'—C10'	112.2 (4)
C15—C10—C11	121.5 (4)	C15'—C10'—C11'	118.5 (4)
C15—C10—C9	117.3 (4)	C15'—C10'—C9'	118.8 (4)
C11—C10—C9	121.1 (4)	C11'—C10'—C9'	122.6 (5)
C12—C11—C10	118.7 (5)	C12'—C11'—C10'	119.8 (5)
C12—C11—H11	120.7	C12'—C11'—H11'	120.1
C10—C11—H11	120.7	C10'—C11'—H11'	120.1
C13—C12—C11	120.2 (5)	C13'—C12'—C11'	120.5 (5)
C13—C12—H12	119.9	C13'—C12'—H12'	119.7
C11—C12—H12	119.9	C11'—C12'—H12'	119.7
C12—C13—C14	120.6 (5)	C12'—C13'—C14'	119.6 (5)
C12—C13—H13	119.7	C12'—C13'—H13'	120.2
C14—C13—H13	119.7	C14'—C13'—H13'	120.2
C13—C14—C15	119.9 (5)	C15'—C14'—C13'	119.1 (5)
C13—C14—H14	120.1	C15'—C14'—H14'	120.4
C15—C14—H14	120.1	C13'—C14'—H14'	120.4
C10—C15—C14	119.1 (5)	C14'—C15'—C10'	122.4 (5)
C10—C15—H15	120.5	C14'—C15'—H15'	118.8
C14—C15—H15	120.5	C10'—C15'—H15'	118.8
O8—C16—O6	123.4 (4)	O8'—C16'—O4'	123.3 (3)
O8—C16—C17	126.1 (4)	O8'—C16'—C17'	125.8 (4)
O6—C16—C17	110.5 (4)	O4'—C16'—C17'	110.9 (3)
C22—C17—C18	119.7 (4)	C22'—C17'—C18'	120.6 (4)
C22—C17—C16	121.9 (4)	C22'—C17'—C16'	121.2 (3)
C18—C17—C16	118.3 (4)	C18'—C17'—C16'	118.1 (4)
C19—C18—C17	119.1 (4)	C19'—C18'—C17'	119.1 (4)
C19—C18—H18	120.5	C19'—C18'—H18'	120.4
C17—C18—H18	120.5	C17'—C18'—H18'	120.4
C20—C19—C18	120.8 (4)	C18'—C19'—C20'	119.9 (4)
C20—C19—H19	119.6	C18'—C19'—H19'	120.1
C18—C19—H19	119.6	C20'—C19'—H19'	120.1
C19—C20—C21	120.8 (4)	C21'—C20'—C19'	120.7 (4)
C19—C20—H20	119.6	C21'—C20'—H20'	119.7
C21—C20—H20	119.6	C19'—C20'—H20'	119.7
C22—C21—C20	119.2 (5)	C22'—C21'—C20'	119.5 (5)
C22—C21—H21	120.4	C22'—C21'—H21'	120.2
C20—C21—H21	120.4	C20'—C21'—H21'	120.2
C21—C22—C17	120.5 (4)	C17'—C22'—C21'	120.1 (4)
C21—C22—H22	119.8	C17'—C22'—H22'	119.9
C17—C22—H22	119.8	C21'—C22'—H22'	119.9
C24—C23—S1	115.8 (3)	C24'—C23'—S1'	118.8 (3)
C24—C23—H23A	108.3	C24'—C23'—H23C	107.6
S1—C23—H23A	108.3	S1'—C23'—H23C	107.6
C24—C23—H23B	108.3	C24'—C23'—H23D	107.6
S1—C23—H23B	108.3	S1'—C23'—H23D	107.6
H23A—C23—H23B	107.4	H23C—C23'—H23D	107.1
C23—C24—C29	112.0 (4)	C23'—C24'—C30'	115.0 (4)
C23—C24—C25	120.2 (4)	C23'—C24'—C29'	117.4 (4)
C29—C24—C25	103.1 (3)	C30'—C24'—C29'	101.3 (4)
C23—C24—C30	116.1 (3)	C23'—C24'—C25'	115.9 (4)
C29—C24—C30	99.8 (3)	C30'—C24'—C25'	103.4 (4)
C25—C24—C30	103.0 (4)	C29'—C24'—C25'	101.7 (3)
C24—C25—C26	104.5 (4)	C26'—C25'—C24'	103.1 (4)
C24—C25—H25A	110.9	C26'—C25'—H25C	111.1
C26—C25—H25A	110.9	C24'—C25'—H25C	111.1
C24—C25—H25B	110.9	C26'—C25'—H25D	111.1
C26—C25—H25B	110.9	C24'—C25'—H25D	111.1
H25A—C25—H25B	108.9	H25C—C25'—H25D	109.1
C27—C26—C25	102.6 (4)	C27'—C26'—C25'	102.7 (4)
C27—C26—H26A	111.3	C27'—C26'—H26C	111.2
C25—C26—H26A	111.3	C25'—C26'—H26C	111.2
C27—C26—H26B	111.3	C27'—C26'—H26D	111.2
C25—C26—H26B	111.3	C25'—C26'—H26D	111.2
H26A—C26—H26B	109.2	H26C—C26'—H26D	109.1
C28—C27—C26	105.9 (4)	C28'—C27'—C30'	102.8 (4)
C28—C27—C30	102.8 (4)	C28'—C27'—C26'	106.7 (4)
C26—C27—C30	103.3 (4)	C30'—C27'—C26'	102.5 (4)
C28—C27—H27	114.5	C28'—C27'—H27'	114.5
C26—C27—H27	114.5	C30'—C27'—H27'	114.5
C30—C27—H27	114.5	C26'—C27'—H27'	114.5
C27—C28—C29	102.3 (3)	C29'—C28'—C27'	102.6 (4)
C27—C28—H28A	111.3	C29'—C28'—H28C	111.2
C29—C28—H28A	111.3	C27'—C28'—H28C	111.2
C27—C28—H28B	111.3	C29'—C28'—H28D	111.2
C29—C28—H28B	111.3	C27'—C28'—H28D	111.2
H28A—C28—H28B	109.2	H28C—C28'—H28D	109.2
O11—C29—C28	129.2 (4)	O11'—C29'—C28'	127.9 (4)
O11—C29—C24	124.9 (4)	O11'—C29'—C24'	126.9 (4)
C28—C29—C24	105.9 (4)	C28'—C29'—C24'	105.2 (4)
C32—C30—C31	108.8 (4)	C24'—C30'—C31'	114.7 (4)
C32—C30—C24	113.1 (4)	C24'—C30'—C32'	112.9 (4)
C31—C30—C24	113.8 (4)	C31'—C30'—C32'	107.7 (4)
C32—C30—C27	113.8 (4)	C24'—C30'—C27'	94.3 (4)
C31—C30—C27	113.2 (4)	C31'—C30'—C27'	113.3 (4)
C24—C30—C27	93.5 (3)	C32'—C30'—C27'	113.7 (4)
C30—C31—H31A	109.5	C30'—C31'—H31D	109.5
C30—C31—H31B	109.5	C30'—C31'—H31E	109.5
H31A—C31—H31B	109.5	H31D—C31'—H31E	109.5
C30—C31—H31C	109.5	C30'—C31'—H31F	109.5
H31A—C31—H31C	109.5	H31D—C31'—H31F	109.5
H31B—C31—H31C	109.5	H31E—C31'—H31F	109.5
C30—C32—H32A	109.5	C30'—C32'—H32D	109.5
C30—C32—H32B	109.5	C30'—C32'—H32E	109.5
H32A—C32—H32B	109.5	H32D—C32'—H32E	109.5
C30—C32—H32C	109.5	C30'—C32'—H32F	109.5
H32A—C32—H32C	109.5	H32D—C32'—H32F	109.5
H32B—C32—H32C	109.5	H32E—C32'—H32F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O9′	0.98	2.41	3.153 (5)	132
C23—H23A···O7	0.97	2.43	3.347 (5)	158
C5′—H5′···O9	0.98	2.63	3.351 (5)	130
C23′—H23D···O7′	0.97	2.63	3.252 (5)	122
C8′—H8E···O3^i	0.96	2.76	3.658 (6)	155
C8—H8C···O1′^ii	0.96	2.75	3.644 (5)	155
C12—H12···O10^iii	0.93	2.72	3.495 (6)	142
C1—H1···O8′^iii	0.98	2.33	3.275 (5)	161
C28—H28B···O11′^iv	0.97	2.45	3.297 (6)	146
C18′—H18′···O1^v	0.93	2.71	3.485 (6)	142
C3′—H3′···O8^v	0.98	2.35	3.310 (5)	167
C31′—H31E···Cg1^vi	0.96	2.86	3.724	151
C31—H31C···Cg2^vii	0.96	3.06	3.943	153

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x, y, z−1; (v) x−1, y, z; (vi) x−1, y, z+1; (vii) x+1, y, z−1.