Packing in three cyclo­octitol acetates

Three cyclo­octitol derivatives, in the form of a tetra­acetate, (1S*,2R*,3S*,4S*)-2,3,4-triacetoxy­cyclo­octan-1-ylmethyl ace­tate, C₁₇H₂₆O₈, and two regioisomeric acetonide triacetates, (3aS*,4R*,8S*,9S*,9aS*)-8,9-diacet­oxy-2,2-dimethyl­cyclo­octano­[d][1,3]dioxan-4-ymethyl acetate and (3aS,4R,7S,9R,9aS)-7,9-diacet­oxy-2,2-dimethyl­cyclo­octano[d][1,3]dioxan-4-ylmethyl acetate, both C₁₈H₂₈O₈, have been studied. The conformation of the cyclo­octane ring in the three compounds is quite close to the boat–chair form of the parent hydro­carbon. Packing is effected through weak C—H...O and van der Waals contacts.

S1. Comment

Details of the synthesis of the three cyclooctitol derivatives (I)–(III) have been reported previously (Mehta & Pallavi, 2002). The synthetic scheme provided, through moderate regio- and stereocontrol, a convenient access to cyclooctitols – an emerging class of medium ring glycomimics which have been projected to provide better adaptability at the active site of a glycosidase enzyme than cyclohexitols and cyclopentitols (Wang et al., 2000; Paquette & Zhang, 2006). Though interesting in their own right, studies into the solid-state supramolecular assemblies of cyclooctitols or their derivatives have been rarely reported in the literature (Salamci et al., 2006; Kawazoe et al., 2001; Andriuzzi et al., 2005; Wang et al., 2001). We report here details of the conformations of the eight-membered carbocyclic rings in the crystal structures of the three cyclooctitol derivatives (I)–(III) and examine how these molecules pack in the solid state. Preliminary details of the structures of (II) and (III) in CIF form were a minor part of the Mehta & Pallavi (2002) publication.

In the monocyclic cyclooctane tetraacetate (I) (Fig. 1), the puckering parameters (Cremer & Pople, 1975) of the cyclooctane ring [q₂ = 1.0294 (18) Å, q₃ = 0.5718 (19) Å, q₄ = -0.3209 (19) Å, ϕ₂ = 5.05 (10)°, ϕ₃ = 180.00 (19)° and Q_T = 1.2206 (19) Å] are in conformity with those of the boat–chair (BC) form (Evans & Boeyens, 1988; Allen et al., 1996), which is the predominant conformer of the cyclooctane molecule as revealed through gas-phase electron diffraction analysis at 300 K and an NMR study in solution at 161.5 K (Rocha et al., 1998). The crystal packing of (I) is realised mainly through van der Waals interactions. The shortest intermolecular contact is between a poorly resolved methyl hydrogen H13A and an adjacent inversion-related carbonyl O atom (O6; Table 1), giving rise to potential dimers [graph-set motif R²₂(8); Bernstein et al., 1995], as shown in Fig. 2(a). As methyl H atoms are not noted for their acidity and the H-atom positions are not well defined in this room- temperature structure determination, this may be an adventitious contact. Such a motif, though very similar to the archetypical carboxylic acid dimer synthon (Fig. 2b), is not commonly encountered. A Cambridge Structural Database search (CSD; Version 5.28 of November 2006; Allen, 2002) for the centrosymmetric R²₂(8) C—H···O motif (as shown in Fig. 2a) in organic molecules, whose crystal structures were refined to R < 0.1, with low-temperature data and correctly oriented methyl H atoms, only generated eight hits.

Owing to its fusion with the 1,3-dioxolane ring, the eight-membered ring in bicyclic cyclooctitol triacetate (II) (Fig. 3) distorts slightly from the expected BC conformation, as revealed by its puckering parameters [q₂ = 0.8958 (17) Å, q₃ = 0.6673 (17) Å, q₄ = -0.3004 (17) Å, ϕ₂ = 258.18 (11)°, ϕ₃ = 123.87 (14)° and Q_T = 1.1567 (17) Å]. The puckering parameters of the five-membered 1,3-dioxolane ring [q₂ = 0.3380 (15) Å and ϕ₂ = 158.2 (3)°] best describe a half-chair (T) conformation, twisted at the C12—O2 bond (Cremer & Pople, 1975). As with (I) the crystal packing of (II) involves mainly van der Waals interactions; the shortest contact is between methylene atom H6B (on C6) and carbonyl atom O8 of an adjacent glide-related molecule (Table 2), and gives rise to chains extending along c as shown in Fig. 4.

In the bicyclic cyclooctitol triacetate (III) (Fig. 5), a regioisomer of (II), the eight-membered ring distorts slightly, as with (II), through its fusion with the 1,3-dioxolane ring, from the expected BC conformation [puckering parameters q₂ = 0.845 (2) Å, q₃ = 0.657 (2) Å, q₄ = -0.321 (2) Å, ϕ₂ = 81.50 (16)°, ϕ₃ = 306.9 (2)° and Q_T = 1.118 (2) Å]. As in (II), the puckering parameters of the five-membered 1,3-dioxolane ring in (III) [q₂ = 0.330 (2) Å and ϕ₂ = 348.8 (4)°] best describe a half-chair (T) conformation, twisted at the C12—O2 bond. As with (I), the packing is realised mainly through van der Waals interactions; the shortest intermolecular contact is between the poorly resolved methyl atom H16A and an adjacent inversion-related carbonyl atom O6 (Table 3) at (1 - x, -y, -z), which would give rise to dimers with graph-set motif R²₂(24) involving the transannular acetate groups at atoms C1 and C4.

To summarize, the present study reports on the conformations and packing of three cyclooctitol acetates. Two types of packing interactions are observed; centrosymmetric dimers and glide-related chains.

Related literature

For related literature, see: Allen (2002); Allen et al. (1996); Andriuzzi et al. (2005); Bernstein et al. (1995); Cremer & Pople (1975); Evans & Boeyens (1988); Kawazoe et al. (2001); Mehta & Pallavi (2002); Paquette & Zhang (2006); Rocha et al. (1998); Salamci et al. (2006); Wang et al. (2000, 2001).

S2. Experimental

####The cyclooctitol derivatives (I)–(III) were prepared as previously reported (Mehta & Pallavi, 2002). Crystals of (I)–(III), suitable for single-crystal X-ray diffraction analysis, were grown from their dilute solutions in a 1:2 dichloromethane–petroleum ether mixture by slow solvent evaporation.

S3. Refinement

All H atoms were initially located in a difference Fourier map. The methine (CH) and methylene (CH₂) H atoms were then placed in geometrically idealized positions and allowed to ride on their parent atoms with C—H distances of 0.97 and 0.98 Å and U_iso(H) values of 1.2U_eq(C). The methyl H atoms were not well defined in difference maps and were constrained to an ideal geometry with a C—H distance of 0.96 Å and U_iso(H) values of 1.5U_eq(C). During refinement, each methyl group was allowed to rotate freely about its C—C bond.

Computing details

For all compounds, data collection: SMART (Bruker, 1998). Cell refinement: SAINT (Bruker, 1998) for (I), (II); SMART (Bruker, 1998) for (III). For all compounds, data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. A view of the tetraacetate (I), with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. (a) The centrosymmetric C—H···O motif employed in the CSD search and seen in (I); (b) its similarity to the carboxylic acid dimer synthon.
	Fig. 3. A view of the triacetate (II), with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 4. The molecular packing of (II). H atoms that are not involved in hydrogen bonding have been omitted for clarity. Dotted lines indicate hydrogen bonds.
	Fig. 5. A view of the triacetate (III), with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

(I) (1S*,2R*,3S*,4S*)-2,3,4-triacetoxycyclooctan-1-ylmethyl acetate

Crystal data

C17H26O8	Z = 2
Mr = 358.38	F(000) = 384
Triclinic, P1	Dx = 1.255 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1632 (9) Å	Cell parameters from 3830 reflections
b = 9.2131 (9) Å	θ = 2.3–27.2°
c = 11.5904 (11) Å	µ = 0.10 mm^−1
α = 94.709 (2)°	T = 291 K
β = 92.486 (2)°	Block, colorless
γ = 102.912 (2)°	0.35 × 0.31 × 0.28 mm
V = 948.60 (16) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	2880 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ϕ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.936, Tmax = 0.973	k = −11→11
9524 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.2015P] where P = (Fo^2 + 2Fc^2)/3
3500 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

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.

Four outlier reflections (3,5,4; 1,5,4; 3,5,1 & 2,4,0) were omitted from the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.08290 (14)	−0.27858 (13)	0.64446 (11)	0.0558 (3)
O2	0.39354 (12)	−0.00780 (12)	0.71670 (9)	0.0431 (3)
O3	0.21602 (13)	0.21760 (13)	0.84362 (10)	0.0525 (3)
O4	0.50109 (13)	0.29004 (13)	0.80950 (11)	0.0549 (3)
O5	0.1437 (2)	−0.49528 (18)	0.59574 (18)	0.0971 (6)
O6	0.32805 (19)	−0.0823 (2)	0.88951 (14)	0.0927 (6)
O7	−0.02687 (16)	0.1234 (2)	0.79527 (15)	0.0824 (5)
O8	0.5895 (2)	0.53633 (18)	0.83651 (18)	0.1099 (7)
C1	0.18533 (18)	−0.04200 (18)	0.57279 (14)	0.0458 (4)
C2	0.24739 (17)	0.02391 (17)	0.69560 (14)	0.0412 (4)
C3	0.25241 (18)	0.19096 (17)	0.72402 (14)	0.0434 (4)
C4	0.39964 (19)	0.30473 (18)	0.71365 (16)	0.0481 (4)
C5	0.47793 (19)	0.2891 (2)	0.60217 (16)	0.0522 (4)
C6	0.3929 (2)	0.3070 (2)	0.49114 (18)	0.0594 (5)
C7	0.2531 (2)	0.1873 (2)	0.45203 (17)	0.0579 (5)
C8	0.2625 (2)	0.0262 (2)	0.46816 (15)	0.0542 (4)
C9	0.1765 (2)	−0.2093 (2)	0.55887 (16)	0.0541 (4)
C10	0.0756 (2)	−0.4235 (2)	0.65305 (18)	0.0623 (5)
C11	−0.0309 (4)	−0.4824 (3)	0.7399 (3)	0.1075 (10)
C12	0.4205 (2)	−0.0590 (2)	0.81891 (16)	0.0554 (5)
C13	0.5756 (2)	−0.0812 (3)	0.83197 (19)	0.0703 (6)
C14	0.0719 (2)	0.1760 (2)	0.86732 (19)	0.0586 (5)
C15	0.0541 (3)	0.2038 (3)	0.9943 (2)	0.0897 (8)
C16	0.5868 (2)	0.4139 (2)	0.86471 (19)	0.0666 (5)
C17	0.6809 (3)	0.3798 (3)	0.9613 (2)	0.0966 (9)
H1	0.0817	−0.0303	0.5659	0.055*
H2	0.1809	−0.0304	0.7495	0.049*
H3	0.1751	0.2168	0.6738	0.052*
H4	0.3802	0.4053	0.7229	0.058*
H5A	0.5725	0.3629	0.6091	0.063*
H5B	0.5011	0.1912	0.5950	0.063*
H6A	0.4614	0.3122	0.4293	0.071*
H6B	0.3645	0.4024	0.5004	0.071*
H7A	0.2296	0.1937	0.3705	0.069*
H7B	0.1703	0.2091	0.4943	0.069*
H8A	0.3676	0.0229	0.4756	0.065*
H8B	0.2185	−0.0366	0.3984	0.065*
H9A	0.1348	−0.2508	0.4817	0.065*
H9B	0.2761	−0.2279	0.5689	0.065*
H11A	−0.0622	−0.5892	0.7254	0.161*
H11B	−0.1169	−0.4394	0.7342	0.161*
H11C	0.0174	−0.4567	0.8163	0.161*
H13A	0.6112	−0.0607	0.9121	0.105*
H13B	0.6398	−0.0146	0.7864	0.105*
H13C	0.5761	−0.1827	0.8059	0.105*
H15A	−0.0504	0.1774	1.0090	0.134*
H15B	0.0940	0.3077	1.0191	0.134*
H15C	0.1072	0.1440	1.0364	0.134*
H17A	0.7285	0.4709	1.0073	0.145*
H17B	0.7561	0.3326	0.9305	0.145*
H17C	0.6191	0.3138	1.0088	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0617 (8)	0.0398 (6)	0.0653 (8)	0.0106 (5)	0.0148 (6)	−0.0012 (5)
O2	0.0450 (6)	0.0440 (6)	0.0430 (6)	0.0137 (5)	0.0056 (5)	0.0081 (5)
O3	0.0532 (7)	0.0500 (7)	0.0520 (7)	0.0093 (5)	0.0105 (5)	−0.0052 (5)
O4	0.0510 (7)	0.0452 (7)	0.0640 (8)	0.0031 (5)	−0.0032 (6)	0.0052 (6)
O5	0.1223 (15)	0.0640 (10)	0.1197 (14)	0.0469 (10)	0.0361 (12)	0.0088 (9)
O6	0.0842 (11)	0.1445 (16)	0.0643 (10)	0.0401 (11)	0.0227 (8)	0.0483 (10)
O7	0.0501 (8)	0.1106 (13)	0.0809 (11)	0.0069 (8)	0.0139 (8)	0.0030 (9)
O8	0.1387 (17)	0.0506 (10)	0.1218 (16)	−0.0079 (10)	−0.0423 (13)	0.0067 (9)
C1	0.0423 (9)	0.0464 (9)	0.0479 (9)	0.0099 (7)	0.0025 (7)	0.0001 (7)
C2	0.0382 (8)	0.0406 (8)	0.0453 (9)	0.0090 (6)	0.0072 (6)	0.0045 (7)
C3	0.0422 (8)	0.0421 (9)	0.0466 (9)	0.0113 (7)	0.0062 (7)	0.0018 (7)
C4	0.0473 (9)	0.0383 (8)	0.0589 (10)	0.0096 (7)	0.0030 (8)	0.0065 (7)
C5	0.0427 (9)	0.0483 (9)	0.0656 (11)	0.0061 (7)	0.0090 (8)	0.0142 (8)
C6	0.0596 (11)	0.0597 (11)	0.0633 (12)	0.0161 (9)	0.0128 (9)	0.0208 (9)
C7	0.0546 (10)	0.0711 (12)	0.0514 (10)	0.0172 (9)	0.0049 (8)	0.0172 (9)
C8	0.0552 (10)	0.0604 (11)	0.0453 (9)	0.0106 (8)	0.0035 (8)	0.0018 (8)
C9	0.0546 (10)	0.0495 (10)	0.0554 (10)	0.0081 (8)	0.0091 (8)	−0.0047 (8)
C10	0.0779 (13)	0.0467 (10)	0.0646 (12)	0.0206 (9)	0.0045 (10)	0.0000 (9)
C11	0.162 (3)	0.0584 (14)	0.104 (2)	0.0189 (16)	0.056 (2)	0.0150 (13)
C12	0.0627 (11)	0.0609 (11)	0.0455 (10)	0.0180 (9)	0.0052 (8)	0.0108 (8)
C13	0.0724 (13)	0.0880 (15)	0.0588 (12)	0.0345 (11)	−0.0029 (10)	0.0144 (11)
C14	0.0568 (11)	0.0492 (10)	0.0701 (12)	0.0110 (8)	0.0210 (10)	0.0021 (9)
C15	0.1029 (19)	0.0821 (16)	0.0773 (16)	0.0059 (14)	0.0417 (14)	−0.0084 (12)
C16	0.0660 (12)	0.0543 (12)	0.0692 (13)	−0.0071 (9)	−0.0009 (10)	0.0050 (10)
C17	0.0948 (19)	0.0936 (19)	0.0832 (17)	−0.0148 (14)	−0.0268 (14)	0.0185 (14)

Geometric parameters (Å, º)

O1—C10	1.334 (2)	C6—H6A	0.9700
O1—C9	1.436 (2)	C6—H6B	0.9700
O2—C12	1.344 (2)	C7—C8	1.532 (3)
O2—C2	1.4480 (18)	C7—H7A	0.9700
O3—C14	1.338 (2)	C7—H7B	0.9700
O3—C3	1.454 (2)	C8—H8A	0.9700
O4—C16	1.328 (2)	C8—H8B	0.9700
O4—C4	1.452 (2)	C9—H9A	0.9700
O5—C10	1.190 (2)	C9—H9B	0.9700
O6—C12	1.201 (2)	C10—C11	1.482 (3)
O7—C14	1.193 (3)	C11—H11A	0.9600
O8—C16	1.195 (3)	C11—H11B	0.9600
C1—C9	1.520 (2)	C11—H11C	0.9600
C1—C2	1.534 (2)	C12—C13	1.483 (3)
C1—C8	1.538 (2)	C13—H13A	0.9600
C1—H1	0.9800	C13—H13B	0.9600
C2—C3	1.537 (2)	C13—H13C	0.9600
C2—H2	0.9800	C14—C15	1.495 (3)
C3—C4	1.528 (2)	C15—H15A	0.9600
C3—H3	0.9800	C15—H15B	0.9600
C4—C5	1.517 (3)	C15—H15C	0.9600
C4—H4	0.9800	C16—C17	1.480 (3)
C5—C6	1.515 (3)	C17—H17A	0.9600
C5—H5A	0.9700	C17—H17B	0.9600
C5—H5B	0.9700	C17—H17C	0.9600
C6—C7	1.517 (3)
O1—C9—C1	108.74 (13)	C6—C5—H5B	108.2
O1—C10—C11	111.12 (18)	C6—C7—H7A	108.3
O1—C9—H9A	109.9	C6—C7—H7B	108.3
O1—C9—H9B	109.9	C7—C8—C1	116.02 (15)
O2—C2—C1	108.94 (12)	C7—C6—H6A	108.0
O2—C2—C3	111.27 (12)	C7—C6—H6B	108.0
O2—C12—C13	111.79 (16)	C7—C8—H8A	108.3
O2—C2—H2	106.8	C7—C8—H8B	108.3
O3—C3—C2	109.65 (12)	C8—C1—H1	106.3
O3—C3—C4	104.46 (13)	C8—C7—H7A	108.3
O3—C14—C15	110.8 (2)	C8—C7—H7B	108.3
O3—C3—H3	107.9	C9—C1—C2	110.27 (14)
O4—C4—C3	106.89 (13)	C9—C1—C8	107.91 (14)
O4—C4—C5	108.02 (13)	C9—C1—H1	106.3
O4—C16—C17	111.48 (19)	C10—O1—C9	116.82 (14)
O4—C4—H4	108.4	C10—C11—H11A	109.5
O5—C10—O1	123.6 (2)	C10—C11—H11B	109.5
O5—C10—C11	125.2 (2)	C10—C11—H11C	109.5
O6—C12—O2	122.65 (18)	C12—O2—C2	116.98 (13)
O6—C12—C13	125.56 (18)	C12—C13—H13A	109.5
O7—C14—O3	123.40 (19)	C12—C13—H13B	109.5
O7—C14—C15	125.8 (2)	C12—C13—H13C	109.5
O8—C16—O4	123.4 (2)	C14—O3—C3	117.32 (14)
O8—C16—C17	125.1 (2)	C14—C15—H15A	109.5
C1—C2—C3	115.66 (13)	C14—C15—H15B	109.5
C1—C2—H2	106.8	C14—C15—H15C	109.5
C1—C8—H8A	108.3	C16—O4—C4	118.24 (15)
C1—C8—H8B	108.3	C16—C17—H17A	109.5
C1—C9—H9A	109.9	C16—C17—H17B	109.5
C1—C9—H9B	109.9	C16—C17—H17C	109.5
C2—C1—C8	119.04 (14)	H5A—C5—H5B	107.3
C2—C1—H1	106.3	H6A—C6—H6B	107.2
C2—C3—H3	107.9	H7A—C7—H7B	107.4
C3—C2—H2	106.8	H8A—C8—H8B	107.4
C3—C4—H4	108.4	H9A—C9—H9B	108.3
C4—C3—C2	118.71 (13)	H11A—C11—H11B	109.5
C4—C3—H3	107.9	H11A—C11—H11C	109.5
C4—C5—H5A	108.2	H11B—C11—H11C	109.5
C4—C5—H5B	108.2	H13A—C13—H13B	109.5
C5—C4—C3	116.57 (15)	H13A—C13—H13C	109.5
C5—C6—C7	117.39 (15)	H13B—C13—H13C	109.5
C5—C4—H4	108.4	H15A—C15—H15B	109.5
C5—C6—H6A	108.0	H15A—C15—H15C	109.5
C5—C6—H6B	108.0	H15B—C15—H15C	109.5
C6—C5—C4	116.57 (15)	H17A—C17—H17B	109.5
C6—C7—C8	115.85 (15)	H17A—C17—H17C	109.5
C6—C5—H5A	108.2	H17B—C17—H17C	109.5
O2—C2—C3—O3	−92.05 (14)	C4—C5—C6—C7	−67.7 (2)
O2—C2—C3—C4	27.8 (2)	C5—C6—C7—C8	−39.7 (2)
O3—C3—C4—O4	50.57 (16)	C6—C7—C8—C1	101.90 (19)
O3—C3—C4—C5	171.46 (13)	C8—C1—C2—O2	−67.74 (18)
O4—C4—C5—C6	−177.73 (14)	C8—C1—C2—C3	58.4 (2)
C1—C2—C3—O3	142.95 (14)	C8—C1—C9—O1	−170.34 (14)
C1—C2—C3—C4	−97.19 (17)	C9—O1—C10—O5	1.4 (3)
C2—O2—C12—O6	2.1 (3)	C9—O1—C10—C11	−176.9 (2)
C2—O2—C12—C13	−177.67 (15)	C9—C1—C2—O2	57.71 (16)
C2—C1—C8—C7	−65.8 (2)	C9—C1—C2—C3	−176.11 (13)
C2—C1—C9—O1	58.12 (18)	C9—C1—C8—C7	167.59 (15)
C2—C3—C4—O4	−71.91 (18)	C10—O1—C9—C1	−173.02 (15)
C2—C3—C4—C5	49.0 (2)	C12—O2—C2—C1	−134.39 (15)
C3—O3—C14—O7	−2.4 (3)	C12—O2—C2—C3	96.94 (16)
C3—O3—C14—C15	177.18 (16)	C14—O3—C3—C4	156.07 (15)
C3—C4—C5—C6	62.0 (2)	C14—O3—C3—C2	−75.70 (17)
C4—O4—C16—O8	−3.3 (3)	C16—O4—C4—C5	94.67 (18)
C4—O4—C16—C17	178.76 (19)	C16—O4—C4—C3	−139.15 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O6^i	0.96	2.53	3.439 (3)	158

Symmetry code: (i) −x+1, −y, −z+2.

(II) (3aS*,4R*,8S*,9S*,9aS*)-8,9-diacetoxy-2,2-dimethylcyclooctano[d][1,3]dioxan- 4-ylmethyl acetate

Crystal data

C18H28O8	F(000) = 1600
Mr = 372.40	Dx = 1.249 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 6079 reflections
a = 19.206 (12) Å	θ = 2.5–23.2°
b = 26.611 (17) Å	µ = 0.10 mm^−1
c = 7.748 (5) Å	T = 291 K
V = 3960 (4) Å^3	Block, colorless
Z = 8	0.49 × 0.40 × 0.39 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	2811 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ϕ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.905, Tmax = 0.963	k = −32→31
24680 measured reflections	l = −9→9

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.5339P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3822 reflections	Δρmax = 0.20 e Å^−3
241 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (7)

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
O1	0.36504 (7)	0.03567 (4)	0.57587 (15)	0.0572 (3)
O2	0.37167 (6)	0.16104 (4)	0.33097 (14)	0.0485 (3)
O3	0.42318 (6)	0.15849 (5)	0.06869 (15)	0.0573 (3)
O4	0.55129 (6)	0.09492 (4)	−0.00990 (14)	0.0545 (3)
O5	0.63693 (6)	0.15585 (5)	0.17851 (18)	0.0599 (4)
O6	0.28183 (10)	0.03769 (6)	0.7786 (3)	0.1044 (6)
O7	0.56806 (11)	0.01831 (6)	0.1032 (2)	0.0927 (5)
O8	0.65717 (8)	0.21449 (7)	−0.0215 (3)	0.1084 (7)
C1	0.44384 (9)	0.10386 (6)	0.5024 (2)	0.0466 (4)
C2	0.40687 (8)	0.11323 (6)	0.32878 (19)	0.0426 (4)
C3	0.44821 (9)	0.11430 (6)	0.15464 (19)	0.0460 (4)
C4	0.52782 (9)	0.11449 (6)	0.1571 (2)	0.0459 (4)
C5	0.56172 (8)	0.16590 (6)	0.1733 (2)	0.0498 (4)
C6	0.54235 (10)	0.19576 (6)	0.3339 (2)	0.0566 (5)
C7	0.54956 (10)	0.16793 (7)	0.5068 (2)	0.0605 (5)
C8	0.48163 (10)	0.14897 (7)	0.5859 (2)	0.0558 (5)
C9	0.39077 (10)	0.08430 (7)	0.6343 (2)	0.0558 (5)
C10	0.31114 (11)	0.01621 (8)	0.6648 (3)	0.0657 (5)
C11	0.29365 (13)	−0.03550 (8)	0.6004 (3)	0.0794 (6)
C12	0.36064 (9)	0.17491 (7)	0.1549 (2)	0.0504 (4)
C13	0.35623 (12)	0.23183 (8)	0.1452 (3)	0.0775 (6)
C14	0.29713 (10)	0.14911 (9)	0.0788 (3)	0.0723 (6)
C15	0.56993 (10)	0.04642 (7)	−0.0192 (3)	0.0579 (5)
C16	0.59024 (13)	0.03250 (9)	−0.2002 (3)	0.0849 (7)
C17	0.67830 (10)	0.18315 (7)	0.0761 (3)	0.0612 (5)
C18	0.75396 (11)	0.16998 (9)	0.0991 (3)	0.0801 (6)
H1	0.4784	0.0773	0.4841	0.056*
H2	0.3709	0.0873	0.3172	0.051*
H3	0.4333	0.0852	0.0866	0.055*
H4	0.5446	0.0926	0.2498	0.055*
H5	0.5509	0.1859	0.0705	0.060*
H6A	0.4945	0.2068	0.3222	0.068*
H6B	0.5714	0.2256	0.3381	0.068*
H7B	0.5803	0.1394	0.4901	0.073*
H7A	0.5718	0.1903	0.5889	0.073*
H8A	0.4492	0.1769	0.5877	0.067*
H8B	0.4912	0.1402	0.7051	0.067*
H9A	0.4126	0.0809	0.7465	0.067*
H9B	0.3524	0.1078	0.6447	0.067*
H11A	0.2635	−0.0519	0.6815	0.119*
H11B	0.3357	−0.0547	0.5877	0.119*
H11C	0.2706	−0.0330	0.4907	0.119*
H13A	0.3149	0.2430	0.2031	0.116*
H13B	0.3547	0.2421	0.0266	0.116*
H13C	0.3963	0.2463	0.2000	0.116*
H14A	0.3030	0.1133	0.0851	0.108*
H14B	0.2918	0.1590	−0.0397	0.108*
H14C	0.2564	0.1587	0.1427	0.108*
H16A	0.6248	0.0065	−0.1970	0.127*
H16B	0.6089	0.0615	−0.2579	0.127*
H16C	0.5500	0.0207	−0.2615	0.127*
H18A	0.7792	0.1786	−0.0037	0.120*
H18B	0.7583	0.1346	0.1203	0.120*
H18C	0.7726	0.1883	0.1952	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0677 (8)	0.0580 (7)	0.0459 (7)	0.0006 (6)	0.0129 (6)	0.0107 (5)
O2	0.0550 (7)	0.0517 (6)	0.0387 (6)	0.0092 (5)	0.0003 (5)	0.0046 (5)
O3	0.0481 (7)	0.0809 (8)	0.0430 (6)	0.0048 (6)	0.0039 (5)	0.0207 (6)
O4	0.0655 (8)	0.0517 (7)	0.0463 (6)	0.0091 (6)	0.0155 (5)	0.0031 (5)
O5	0.0425 (7)	0.0692 (8)	0.0681 (8)	0.0016 (6)	0.0030 (6)	0.0177 (6)
O6	0.1149 (14)	0.0836 (10)	0.1146 (14)	0.0059 (9)	0.0697 (12)	0.0064 (9)
O7	0.1433 (16)	0.0661 (9)	0.0687 (9)	0.0340 (9)	−0.0128 (9)	0.0078 (7)
O8	0.0637 (10)	0.1253 (14)	0.1362 (16)	0.0088 (9)	0.0157 (10)	0.0750 (13)
C1	0.0494 (9)	0.0519 (9)	0.0384 (8)	0.0086 (7)	0.0012 (7)	0.0028 (7)
C2	0.0448 (9)	0.0437 (8)	0.0393 (8)	−0.0005 (7)	0.0019 (7)	0.0031 (6)
C3	0.0512 (10)	0.0517 (9)	0.0353 (8)	−0.0034 (7)	0.0013 (7)	−0.0009 (7)
C4	0.0506 (9)	0.0501 (9)	0.0370 (8)	0.0029 (7)	0.0047 (7)	0.0028 (6)
C5	0.0394 (9)	0.0542 (9)	0.0557 (10)	0.0010 (7)	−0.0008 (7)	0.0070 (7)
C6	0.0520 (11)	0.0512 (9)	0.0667 (11)	−0.0047 (8)	−0.0028 (8)	−0.0044 (8)
C7	0.0563 (11)	0.0693 (11)	0.0560 (11)	−0.0020 (9)	−0.0105 (9)	−0.0134 (9)
C8	0.0610 (11)	0.0661 (11)	0.0404 (9)	0.0068 (9)	−0.0048 (8)	−0.0060 (8)
C9	0.0672 (12)	0.0595 (10)	0.0406 (9)	0.0087 (9)	0.0088 (8)	0.0049 (7)
C10	0.0676 (13)	0.0679 (12)	0.0616 (11)	0.0091 (10)	0.0185 (10)	0.0225 (9)
C11	0.0847 (16)	0.0777 (14)	0.0758 (14)	−0.0104 (12)	0.0116 (12)	0.0168 (11)
C12	0.0472 (10)	0.0636 (10)	0.0404 (9)	0.0021 (8)	−0.0010 (7)	0.0116 (7)
C13	0.0831 (15)	0.0685 (12)	0.0809 (14)	0.0069 (11)	−0.0155 (11)	0.0253 (11)
C14	0.0518 (11)	0.1020 (16)	0.0631 (12)	−0.0047 (11)	−0.0098 (9)	0.0054 (11)
C15	0.0555 (11)	0.0578 (10)	0.0603 (11)	0.0130 (8)	−0.0002 (9)	−0.0037 (9)
C16	0.0927 (17)	0.0835 (14)	0.0786 (15)	0.0155 (13)	0.0258 (13)	−0.0182 (12)
C17	0.0504 (11)	0.0695 (11)	0.0636 (11)	0.0008 (9)	0.0058 (9)	0.0098 (9)
C18	0.0496 (11)	0.1068 (16)	0.0840 (15)	0.0002 (12)	0.0068 (11)	0.0154 (12)

Geometric parameters (Å, º)

O1—C10	1.347 (2)	C7—C8	1.527 (3)
O1—C9	1.457 (2)	C7—H7B	0.9700
O2—C12	1.429 (2)	C7—H7A	0.9700
O2—C2	1.441 (2)	C8—H8A	0.9700
O3—C3	1.434 (2)	C8—H8B	0.9700
O3—C12	1.442 (2)	C9—H9A	0.9700
O4—C15	1.341 (2)	C9—H9B	0.9700
O4—C4	1.466 (2)	C10—C11	1.502 (3)
O5—C17	1.338 (2)	C11—H11A	0.9600
O5—C5	1.470 (2)	C11—H11B	0.9600
O6—C10	1.192 (3)	C11—H11C	0.9600
O7—C15	1.208 (2)	C12—C14	1.519 (3)
O8—C17	1.197 (2)	C12—C13	1.519 (3)
C1—C9	1.534 (2)	C13—H13A	0.9600
C1—C2	1.542 (2)	C13—H13B	0.9600
C1—C8	1.545 (2)	C13—H13C	0.9600
C1—H1	0.9800	C14—H14A	0.9600
C2—C3	1.566 (2)	C14—H14B	0.9600
C2—H2	0.9800	C14—H14C	0.9600
C3—C4	1.529 (3)	C15—C16	1.502 (3)
C3—H3	0.9800	C16—H16A	0.9600
C4—C5	1.520 (2)	C16—H16B	0.9600
C4—H4	0.9800	C16—H16C	0.9600
C5—C6	1.523 (3)	C17—C18	1.505 (3)
C5—H5	0.9800	C18—H18A	0.9600
C6—C7	1.537 (3)	C18—H18B	0.9600
C6—H6A	0.9700	C18—H18C	0.9600
C6—H6B	0.9700
O1—C9—C1	108.65 (13)	C6—C7—H7B	108.4
O1—C10—C11	110.75 (17)	C7—C6—H6A	108.3
O1—C9—H9A	110.0	C7—C6—H6B	108.3
O1—C9—H9B	110.0	C7—C8—C1	119.35 (14)
O2—C12—O3	103.91 (12)	C7—C8—H8A	107.5
O2—C2—C1	110.41 (12)	C7—C8—H8B	107.5
O2—C2—C3	103.42 (12)	C8—C1—H1	107.6
O2—C12—C13	108.23 (15)	C8—C7—C6	115.59 (16)
O2—C12—C14	111.91 (15)	C8—C7—H7A	108.4
O2—C2—H2	106.9	C8—C7—H7B	108.4
O3—C3—C2	104.18 (12)	C9—C1—C2	109.27 (15)
O3—C3—C4	109.76 (13)	C9—C1—C8	107.27 (14)
O3—C12—C14	110.61 (16)	C9—C1—H1	107.6
O3—C12—C13	109.01 (15)	C10—O1—C9	116.31 (15)
O3—C3—H3	107.5	C10—C11—H11A	109.5
O4—C4—C3	107.19 (12)	C10—C11—H11B	109.5
O4—C4—C5	105.14 (12)	C10—C11—H11C	109.5
O4—C4—H4	109.6	C12—O2—C2	106.64 (11)
O4—C15—C16	110.91 (17)	C12—C13—H13A	109.5
O5—C5—C4	105.04 (13)	C12—C13—H13B	109.5
O5—C5—C6	108.21 (14)	C12—C13—H13C	109.5
O5—C5—H5	109.3	C12—C14—H14A	109.5
O5—C17—C18	112.14 (17)	C12—C14—H14B	109.5
O6—C10—O1	123.8 (2)	C12—C14—H14C	109.5
O6—C10—C11	125.41 (19)	C14—C12—C13	112.76 (16)
O7—C15—O4	123.05 (18)	C15—O4—C4	118.14 (13)
O7—C15—C16	126.01 (18)	C15—C16—H16A	109.5
O8—C17—O5	123.50 (18)	C15—C16—H16B	109.5
O8—C17—C18	124.35 (18)	C15—C16—H16C	109.5
C1—C2—C3	121.43 (14)	C17—O5—C5	117.96 (14)
C1—C2—H2	106.9	C17—C18—H18A	109.5
C1—C8—H8A	107.5	C17—C18—H18B	109.5
C1—C8—H8B	107.5	C17—C18—H18C	109.5
C1—C9—H9A	110.0	H6A—C6—H6B	107.4
C1—C9—H9B	110.0	H7B—C7—H7A	107.4
C2—C1—C8	117.15 (14)	H8A—C8—H8B	107.0
C2—C1—H1	107.6	H9A—C9—H9B	108.3
C2—C3—H3	107.5	H11A—C11—H11B	109.5
C3—O3—C12	108.21 (12)	H11A—C11—H11C	109.5
C3—C2—H2	106.9	H11B—C11—H11C	109.5
C3—C4—H4	109.6	H13A—C13—H13B	109.5
C4—C3—C2	119.77 (13)	H13A—C13—H13C	109.5
C4—C5—C6	115.63 (14)	H13B—C13—H13C	109.5
C4—C3—H3	107.5	H14A—C14—H14B	109.5
C4—C5—H5	109.3	H14A—C14—H14C	109.5
C5—C4—C3	115.60 (14)	H14B—C14—H14C	109.5
C5—C6—C7	116.05 (16)	H16A—C16—H16B	109.5
C5—C4—H4	109.6	H16A—C16—H16C	109.5
C5—C6—H6A	108.3	H16B—C16—H16C	109.5
C5—C6—H6B	108.3	H18A—C18—H18B	109.5
C6—C5—H5	109.3	H18A—C18—H18C	109.5
C6—C7—H7A	108.4	H18B—C18—H18C	109.5
O2—C2—C3—O3	−8.55 (15)	C4—C5—C6—C7	50.7 (2)
O2—C2—C3—C4	114.55 (15)	C5—O5—C17—O8	−1.5 (3)
O3—C3—C4—O4	−82.64 (15)	C5—O5—C17—C18	178.17 (16)
O3—C3—C4—C5	34.19 (18)	C5—C6—C7—C8	−102.44 (19)
O4—C4—C5—O5	−63.89 (15)	C6—C7—C8—C1	71.9 (2)
O4—C4—C5—C6	176.93 (13)	C8—C1—C2—O2	−40.97 (19)
O5—C5—C6—C7	−66.71 (19)	C8—C1—C9—O1	−167.84 (14)
C1—C2—C3—O3	−133.02 (14)	C8—C1—C2—C3	80.19 (19)
C1—C2—C3—C4	−9.9 (2)	C9—O1—C10—O6	4.6 (3)
C2—O2—C12—O3	−38.03 (16)	C9—O1—C10—C11	−175.50 (16)
C2—O2—C12—C14	81.35 (18)	C9—C1—C2—O2	81.22 (16)
C2—O2—C12—C13	−153.80 (15)	C9—C1—C2—C3	−157.62 (14)
C2—C1—C8—C7	−72.5 (2)	C9—C1—C8—C7	164.33 (16)
C2—C1—C9—O1	64.22 (17)	C10—O1—C9—C1	−171.44 (15)
C2—C3—C4—O4	157.01 (13)	C12—O2—C2—C1	159.91 (13)
C2—C3—C4—C5	−86.16 (18)	C12—O2—C2—C3	28.56 (15)
C3—O3—C12—O2	32.26 (16)	C12—O3—C3—C2	−14.29 (16)
C3—O3—C12—C14	−87.99 (17)	C12—O3—C3—C4	−143.70 (13)
C3—O3—C12—C13	147.48 (15)	C15—O4—C4—C3	−98.44 (17)
C3—C4—C5—O5	178.14 (12)	C15—O4—C4—C5	138.04 (15)
C3—C4—C5—C6	58.95 (19)	C17—O5—C5—C4	132.15 (16)
C4—O4—C15—O7	0.2 (3)	C17—O5—C5—C6	−103.81 (18)
C4—O4—C15—C16	178.18 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O8^i	0.97	2.54	3.438 (3)	154

Symmetry code: (i) x, −y+1/2, z+1/2.

(III) (3aS,4R,7S,9R,9aS)- 7,9-diacetoxy-2,2-dimethylcyclooctano[d][1,3]dioxan-4-ylmethyl acetate

Crystal data

C18H28O8	Z = 2
Mr = 372.40	F(000) = 400
Triclinic, P1	Dx = 1.270 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7179 (16) Å	Cell parameters from 928 reflections
b = 11.486 (2) Å	θ = 2.7–21.5°
c = 11.720 (2) Å	µ = 0.10 mm^−1
α = 76.515 (4)°	T = 291 K
β = 74.547 (4)°	Block, colorless
γ = 85.394 (4)°	0.33 × 0.27 × 0.26 mm
V = 973.6 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4173 independent reflections
Radiation source: fine-focus sealed tube	2082 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
ϕ and ω scans	θmax = 27.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.925, Tmax = 0.975	k = −14→15
10725 measured reflections	l = −14→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0581P)^2] where P = (Fo^2 + 2Fc^2)/3
4173 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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
O1	0.4724 (2)	0.31733 (17)	−0.14187 (14)	0.0695 (5)
O2	0.4013 (2)	0.21958 (14)	0.25870 (13)	0.0613 (5)
O3	0.55392 (19)	0.07209 (14)	0.35402 (13)	0.0531 (4)
O4	0.88059 (19)	−0.03719 (13)	0.24337 (13)	0.0488 (4)
O5	0.9688 (2)	0.37502 (14)	0.20690 (15)	0.0571 (5)
O6	0.2064 (3)	0.3310 (2)	−0.17762 (19)	0.1138 (9)
O7	1.1420 (2)	−0.01806 (15)	0.10044 (15)	0.0642 (5)
O8	0.8464 (3)	0.3479 (2)	0.40654 (18)	0.0887 (7)
C1	0.5517 (3)	0.2329 (2)	0.04448 (18)	0.0450 (6)
C2	0.4817 (3)	0.1515 (2)	0.16985 (19)	0.0468 (6)
C3	0.6105 (3)	0.06371 (19)	0.23100 (18)	0.0419 (5)
C4	0.8123 (3)	0.07878 (18)	0.18684 (19)	0.0421 (5)
C5	0.8945 (3)	0.17267 (19)	0.2264 (2)	0.0467 (6)
C6	0.8333 (3)	0.30177 (19)	0.19161 (19)	0.0453 (6)
C7	0.8233 (3)	0.3468 (2)	0.0612 (2)	0.0545 (6)
C8	0.6351 (3)	0.3499 (2)	0.0414 (2)	0.0543 (6)
C9	0.3969 (3)	0.2592 (2)	−0.01649 (19)	0.0606 (7)
C10	0.3641 (4)	0.3475 (2)	−0.2136 (2)	0.0593 (7)
C11	0.4569 (4)	0.4076 (3)	−0.3385 (2)	0.0753 (8)
C12	0.3919 (3)	0.1414 (2)	0.3741 (2)	0.0511 (6)
C13	0.3972 (4)	0.2129 (3)	0.4646 (2)	0.0834 (10)
C14	0.2323 (3)	0.0614 (3)	0.4150 (2)	0.0817 (9)
C15	1.0460 (3)	−0.0740 (2)	0.1920 (2)	0.0495 (6)
C16	1.0927 (3)	−0.1914 (2)	0.2647 (2)	0.0700 (8)
C17	0.9597 (4)	0.3909 (2)	0.3175 (3)	0.0608 (7)
C18	1.1072 (4)	0.4684 (2)	0.3136 (3)	0.0817 (9)
H1	0.6440	0.1875	−0.0035	0.054*
H2	0.3866	0.1034	0.1638	0.056*
H3	0.5848	−0.0173	0.2274	0.050*
H4	0.8500	0.0905	0.0983	0.051*
H5A	1.0238	0.1688	0.1937	0.056*
H5B	0.8714	0.1508	0.3141	0.056*
H6	0.7166	0.3148	0.2465	0.054*
H7A	0.9004	0.2961	0.0122	0.065*
H7B	0.8708	0.4270	0.0321	0.065*
H8A	0.5544	0.3867	0.1025	0.065*
H8B	0.6377	0.4027	−0.0368	0.065*
H9A	0.3398	0.1855	−0.0117	0.073*
H9B	0.3076	0.3112	0.0233	0.073*
H11A	0.3753	0.4181	−0.3894	0.113*
H11B	0.5583	0.3594	−0.3691	0.113*
H11C	0.4973	0.4843	−0.3381	0.113*
H13A	0.5046	0.2591	0.4367	0.125*
H13B	0.3963	0.1598	0.5413	0.125*
H13C	0.2939	0.2658	0.4739	0.125*
H14A	0.1238	0.1092	0.4269	0.123*
H14B	0.2360	0.0066	0.4900	0.123*
H14C	0.2349	0.0173	0.3544	0.123*
H16A	1.0095	−0.2506	0.2678	0.105*
H16B	1.0862	−0.1838	0.3456	0.105*
H16C	1.2125	−0.2156	0.2276	0.105*
H18A	1.0983	0.4792	0.3938	0.123*
H18B	1.0976	0.5449	0.2607	0.123*
H18C	1.2211	0.4312	0.2838	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0469 (10)	0.1120 (15)	0.0398 (10)	−0.0031 (9)	−0.0184 (8)	0.0114 (9)
O2	0.0586 (10)	0.0676 (11)	0.0379 (9)	0.0225 (9)	−0.0012 (8)	0.0066 (8)
O3	0.0411 (9)	0.0721 (11)	0.0360 (9)	0.0117 (8)	−0.0082 (7)	0.0021 (8)
O4	0.0436 (9)	0.0452 (9)	0.0490 (9)	0.0105 (7)	−0.0067 (7)	−0.0030 (7)
O5	0.0568 (11)	0.0540 (11)	0.0604 (11)	−0.0121 (8)	−0.0172 (8)	−0.0061 (8)
O6	0.0609 (14)	0.199 (3)	0.0696 (14)	−0.0107 (15)	−0.0287 (11)	0.0102 (15)
O7	0.0506 (10)	0.0702 (12)	0.0619 (12)	0.0076 (9)	−0.0004 (9)	−0.0142 (10)
O8	0.0923 (15)	0.1126 (17)	0.0636 (13)	−0.0180 (13)	−0.0116 (12)	−0.0284 (12)
C1	0.0360 (12)	0.0598 (16)	0.0331 (12)	0.0024 (11)	−0.0090 (10)	0.0007 (11)
C2	0.0390 (13)	0.0578 (15)	0.0404 (13)	−0.0020 (11)	−0.0144 (10)	0.0005 (11)
C3	0.0417 (13)	0.0410 (13)	0.0398 (13)	−0.0021 (10)	−0.0114 (10)	−0.0008 (10)
C4	0.0420 (13)	0.0408 (13)	0.0373 (12)	0.0060 (10)	−0.0103 (10)	0.0014 (10)
C5	0.0389 (13)	0.0467 (14)	0.0517 (14)	−0.0011 (11)	−0.0138 (11)	−0.0026 (11)
C6	0.0406 (13)	0.0448 (14)	0.0468 (14)	−0.0066 (10)	−0.0097 (10)	−0.0027 (11)
C7	0.0533 (15)	0.0504 (15)	0.0514 (15)	−0.0097 (12)	−0.0115 (12)	0.0062 (12)
C8	0.0549 (15)	0.0545 (16)	0.0443 (14)	0.0039 (12)	−0.0143 (11)	0.0074 (11)
C9	0.0452 (14)	0.086 (2)	0.0405 (14)	−0.0034 (13)	−0.0134 (11)	0.0091 (13)
C10	0.0522 (16)	0.0786 (19)	0.0463 (15)	0.0064 (14)	−0.0201 (13)	−0.0059 (13)
C11	0.080 (2)	0.100 (2)	0.0435 (16)	0.0007 (17)	−0.0249 (14)	−0.0008 (15)
C12	0.0409 (13)	0.0624 (16)	0.0378 (13)	0.0068 (12)	−0.0071 (10)	0.0071 (12)
C13	0.113 (3)	0.079 (2)	0.0426 (16)	0.0028 (18)	−0.0004 (16)	−0.0080 (15)
C14	0.0495 (16)	0.126 (3)	0.0546 (17)	−0.0235 (17)	−0.0115 (13)	0.0154 (16)
C15	0.0440 (14)	0.0527 (15)	0.0540 (16)	0.0089 (12)	−0.0144 (12)	−0.0173 (13)
C16	0.0662 (18)	0.0572 (17)	0.080 (2)	0.0199 (14)	−0.0181 (15)	−0.0113 (15)
C17	0.0662 (19)	0.0533 (17)	0.067 (2)	0.0050 (14)	−0.0250 (15)	−0.0139 (15)
C18	0.092 (2)	0.0627 (19)	0.108 (2)	−0.0067 (16)	−0.0510 (19)	−0.0221 (17)

Geometric parameters (Å, º)

O1—C10	1.310 (3)	C7—C8	1.528 (3)
O1—C9	1.447 (2)	C7—H7A	0.9700
O2—C12	1.426 (2)	C7—H7B	0.9700
O2—C2	1.428 (3)	C8—H8A	0.9700
O3—C3	1.415 (2)	C8—H8B	0.9700
O3—C12	1.422 (3)	C9—H9A	0.9700
O4—C15	1.339 (3)	C9—H9B	0.9700
O4—C4	1.467 (2)	C10—C11	1.477 (3)
O5—C17	1.333 (3)	C11—H11A	0.9600
O5—C6	1.465 (3)	C11—H11B	0.9600
O6—C10	1.193 (3)	C11—H11C	0.9600
O7—C15	1.202 (3)	C12—C13	1.496 (3)
O8—C17	1.200 (3)	C12—C14	1.501 (3)
C1—C8	1.524 (3)	C13—H13A	0.9600
C1—C9	1.525 (3)	C13—H13B	0.9600
C1—C2	1.531 (3)	C13—H13C	0.9600
C1—H1	0.9800	C14—H14A	0.9600
C2—C3	1.549 (3)	C14—H14B	0.9600
C2—H2	0.9800	C14—H14C	0.9600
C3—C4	1.515 (3)	C15—C16	1.492 (3)
C3—H3	0.9800	C16—H16A	0.9600
C4—C5	1.510 (3)	C16—H16B	0.9600
C4—H4	0.9800	C16—H16C	0.9600
C5—C6	1.516 (3)	C17—C18	1.486 (4)
C5—H5A	0.9700	C18—H18A	0.9600
C5—H5B	0.9700	C18—H18B	0.9600
C6—C7	1.516 (3)	C18—H18C	0.9600
C6—H6	0.9800
O1—C9—C1	107.10 (17)	C6—C7—C8	115.03 (18)
O1—C10—C11	113.0 (2)	C6—C7—H7A	108.5
O1—C9—H9A	110.3	C6—C7—H7B	108.5
O1—C9—H9B	110.3	C7—C6—H6	109.5
O2—C2—C1	111.31 (18)	C7—C8—H8A	107.5
O2—C2—C3	103.14 (16)	C7—C8—H8B	107.5
O2—C2—H2	107.0	C8—C1—C2	116.44 (19)
O2—C12—C13	109.7 (2)	C8—C1—C9	109.8 (2)
O2—C12—C14	112.3 (2)	C8—C1—H1	107.5
O3—C3—C2	103.74 (16)	C8—C7—H7A	108.5
O3—C3—C4	109.03 (17)	C8—C7—H7B	108.5
O3—C3—H3	107.5	C9—C1—C2	107.85 (17)
O3—C12—O2	103.51 (16)	C9—C1—H1	107.5
O3—C12—C13	108.2 (2)	C10—O1—C9	118.31 (18)
O3—C12—C14	110.2 (2)	C10—C11—H11A	109.5
O4—C4—C3	102.42 (15)	C10—C11—H11B	109.5
O4—C4—C5	106.16 (17)	C10—C11—H11C	109.5
O4—C4—H4	109.9	C12—O2—C2	106.45 (16)
O4—C15—C16	110.6 (2)	C12—C13—H13A	109.5
O5—C6—C5	106.17 (17)	C12—C13—H13B	109.5
O5—C6—C7	105.38 (16)	C12—C13—H13C	109.5
O5—C6—H6	109.5	C12—C14—H14A	109.5
O5—C17—C18	110.6 (3)	C12—C14—H14B	109.5
O6—C10—O1	121.9 (2)	C12—C14—H14C	109.5
O6—C10—C11	125.0 (2)	C13—C12—C14	112.5 (2)
O7—C15—O4	123.7 (2)	C15—O4—C4	118.76 (17)
O7—C15—C16	125.7 (2)	C15—C16—H16A	109.5
O8—C17—O5	123.7 (3)	C15—C16—H16B	109.5
O8—C17—C18	125.7 (3)	C15—C16—H16C	109.5
C1—C2—C3	120.74 (17)	C17—O5—C6	118.87 (19)
C1—C8—C7	119.1 (2)	C17—C18—H18A	109.5
C1—C2—H2	107.0	C17—C18—H18B	109.5
C1—C8—H8A	107.5	C17—C18—H18C	109.5
C1—C9—H9A	110.3	H5A—C5—H5B	107.1
C1—C9—H9B	110.3	H7A—C7—H7B	107.5
C1—C8—H8B	107.5	H8A—C8—H8B	107.0
C2—C1—H1	107.5	H9A—C9—H9B	108.6
C2—C3—H3	107.5	H11A—C11—H11B	109.5
C3—O3—C12	110.06 (15)	H11A—C11—H11C	109.5
C3—C2—H2	107.0	H11B—C11—H11C	109.5
C3—C4—H4	109.9	H13A—C13—H13B	109.5
C4—C3—C2	120.79 (17)	H13A—C13—H13C	109.5
C4—C3—H3	107.5	H13B—C13—H13C	109.5
C4—C5—C6	118.00 (18)	H14A—C14—H14B	109.5
C4—C5—H5A	107.8	H14A—C14—H14C	109.5
C4—C5—H5B	107.8	H14B—C14—H14C	109.5
C5—C4—C3	117.95 (18)	H16A—C16—H16B	109.5
C5—C4—H4	109.9	H16A—C16—H16C	109.5
C5—C6—C7	116.38 (19)	H16B—C16—H16C	109.5
C5—C6—H6	109.5	H18A—C18—H18B	109.5
C6—C5—H5A	107.8	H18A—C18—H18C	109.5
C6—C5—H5B	107.8	H18B—C18—H18C	109.5
O2—C2—C3—O3	14.3 (2)	C4—C5—C6—C7	−46.1 (3)
O2—C2—C3—C4	−108.1 (2)	C5—C6—C7—C8	100.1 (2)
O3—C3—C4—O4	75.32 (19)	C6—O5—C17—O8	0.3 (4)
O3—C3—C4—C5	−40.7 (2)	C6—O5—C17—C18	−179.44 (19)
O4—C4—C5—C6	−174.07 (17)	C6—C7—C8—C1	−75.8 (3)
O5—C6—C7—C8	−142.6 (2)	C8—C1—C2—O2	37.3 (3)
C1—C2—C3—O3	139.3 (2)	C8—C1—C9—O1	62.4 (2)
C1—C2—C3—C4	16.8 (3)	C8—C1—C2—C3	−83.7 (3)
C2—O2—C12—O3	37.1 (2)	C9—O1—C10—O6	1.9 (4)
C2—O2—C12—C13	152.4 (2)	C9—O1—C10—C11	179.1 (2)
C2—O2—C12—C14	−81.7 (2)	C9—C1—C2—O2	−86.6 (2)
C2—C1—C8—C7	75.4 (3)	C9—C1—C2—C3	152.4 (2)
C2—C1—C9—O1	−169.73 (19)	C9—C1—C8—C7	−161.68 (18)
C2—C3—C4—O4	−164.81 (18)	C10—O1—C9—C1	179.1 (2)
C2—C3—C4—C5	79.1 (3)	C12—O3—C3—C4	138.10 (18)
C3—O3—C12—O2	−27.7 (2)	C12—O3—C3—C2	8.2 (2)
C3—O3—C12—C13	−144.03 (19)	C12—O2—C2—C1	−162.57 (17)
C3—O3—C12—C14	92.6 (2)	C12—O2—C2—C3	−31.7 (2)
C3—C4—C5—C6	−60.0 (3)	C15—O4—C4—C3	155.64 (18)
C4—O4—C15—O7	−1.1 (3)	C15—O4—C4—C5	−80.1 (2)
C4—O4—C15—C16	178.2 (2)	C17—O5—C6—C5	−82.0 (2)
C4—C5—C6—O5	−163.02 (17)	C17—O5—C6—C7	154.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O6^i	0.96	2.53	3.399 (3)	151

Symmetry code: (i) −x+1, −y, −z.