6,6′-Dimeth­oxy­gossypolone

6,6′-Dimeth­oxy­gossypolone (systematic name: 7,7′-dihy­droxy-5,5′-diisopropyl-6,6′-dimeth­oxy-3,3′-dimethyl-1,1′,4,4′-tetraoxo-2,2′-binaphthalene-8,8′-dicarbaldehyde), C₃₂H₃₀O₁₀, is a dimeric mol­ecule formed by oxidation of 6,6′-dimeth­oxy­gossypol. When crystallized from acetone, 6,6′-dimeth­oxy­gossypolone has monoclinic (P2₁/c) symmetry, and there are two mol­ecules within the asymmetric unit. Of the four independent quinoid rings, three display flattened boat conformations and one displays a flattened chair/half-chair conformation. The angles between the planes of the two bridged naphtho­quinone structures are fairly acute, with values of about 68 and 69°. The structure has several intra­molecular O—H...O and C—H...O hydrogen bonds and several weak inter­molecular C—H...O hydrogen bonds, but no inter­molecular O—H...O hydrogen bonds.

S1. Comment

Gossypol is a disesquiterpene of the cotton plant that is of research interest because of its wide sphere of bioactivity (Wang et al., 2009). Gossypolone is prepared from gossypol by mild oxidation with ferric chloride (Haas & Shirley, 1965). Like its parent compound, gossypolone exhibits anticancer and antifungal effects (Paizieva et al., 1977; Dao et al., 2000). As part of an effort to generate related compounds of this family, 6,6'-dimethoxygossypol was isolated from cotton roots (Dowd & Pelitire, 2006) and oxidized to prepare 6,6'-dimethoxygossypolone, (I), which was then crystallized and studied by X-ray diffraction (Fig. 1).

Like gossypol and gossypolone, (I) exists in the aldehyde tautomeric form. The aldehyde groups are oriented coplanar with the extended naphthyl ring planes, which allows for the formation of O—H···O hydrogen bonds between the O3 and O8 hydroxyl H atoms and the carbonyl O atoms (Table 1), and the formation of C—H···O hydrogen bonds between the formyl H atoms and quinoid ring atoms O1 and O6. This tautomerization, orientation and basic pattern of hydrogen bonding are also observed in related gossypol and gossypolone crystal structures (Talipov et al., 1995; Gdaniec et al., 1996). The isopropyl groups of (I) are oriented with the single H atoms of the ternary C atoms lying close to the extended naphthyl ring planes, and such that the methyl groups are directed outward and away from the center of the molecule. This orientation gives torsion angles involving the H atoms of the ternary C atoms close to either 0 or 180°, depending on the naphthalene ring atom used to define the angle (Table 1). This orientation is supported by intramolecular C—H···O hydrogen bonds formed between the H atoms of the ternary C atoms and quinoid ring atoms O5 and O10, as well as by several C—H···O interactions formed between the H atoms of the isopropyl methyl groups and the methoxy O atoms at the 6 and 6' positions. A similar orientation of the isopropyl groups is observed in the crystal structures of hemigossypolone and gossypolone. It is also observed in most, but not all, gossypol crystal forms (Talipov et al., 1995; Gdaniec et al., 1996).

Compound (I) also exhibits structural differences with gossypol, gossypolone and other substituted 1,4-naphthoquinones. All gossypol and most 1,4-naphthoquinone structures, including the bridged 2,2'-binaphtho-1,4-quinone (Ammon et al., 1969), have their naphthalene or naphthoquinone rings in close to planar conformations. In contrast, the quinoid rings in gossypolone-type structures exhibit a modest degree of puckering. In hemigossypolone, the quinoid ring has a flattened boat conformation, with a Cremer–Pople (Cremer & Pople, 1975) puckering amplitude (Q) of 0.222 (6) Å and orientation θ and ψ angles of 109 (1) and 15 (2)°, respectively. In gossypolone, the quinoid rings also have flattened boat conformations, with Q = 0.213 (4) Å and θ and ψ angles of 104 (1) and 356 (1)°, respectively. In the Cremer–Pople system for describing six-atom ring puckering, Q is a measure of the average displacement of the ring atoms away from a best-fit plane, ψ describes where the puckering occurs around the ring and θ is an inversion angle that accounts for the possibility of inverted ring forms. In this system, boat conformers have θ angles near 90°, with ψ angles near 0, 60, 120, 180, 240 or 300°. In (I), three of the four quinoid rings are found in a flattened boat conformation (Fig. 2), with Q values between 0.25 and 0.31 Å, θ angles between 83 and 92°, and ϕ angles near either 0 or 180° (Table 3). The fourth ring, however, has a different conformation. This ring has an angle of 35.0 (6)°, which is between that of an ideal chair form with θ = 0° and an ideal half-chair form with θ = 40.8° (Cremer & Szabo, 1995). The observed ring puckering appears to occur because of 1,3-steric interactions between the O atoms of the quinoid rings and the formyl and isopropyl groups at the naphthyl 5- and 8-positions.

In related 1,4-naphthoquinone structures, specific substitutions at both the 5- and 8-positions appear to be necessary to observe puckering within the quinoid ring. A single C-, N- or Cl-atom substituent at either of these positions, e.g. as found in 5-chloro-1,4-naphthoquinone (Scheringer, 1973), 5-acetamide-2,3-dimethyl-1,4-naphthoquinone (Feldman et al., 2007) or dimethyl-7-hydroxy-1,4,-naphthoquinone-6,8-dicarboxylate (Furuichi et al., 1992), results in little quinoid ring puckering. O-atom substituents at both the 5- and 8-positions result in variable puckering. If one or both O-atom substituents are part of hydroxy groups, intramolecular hydrogen bonds form with the quinoid O atoms at the 1- or 4-positions. This added stabilization appears to negate the steric effects and minimal ring puckering is observed, e.g. as found in 2,5-dihydroxy-3,8-dimethoxy-7-methyl-1,4-naphthoquinone (Cannon et al., 1980). Derivatized hydroxyl groups, however, lose this additional stabilization and some puckering is observed, as in 2,5,8-triacetoxy-3-methoxy-6-methyl-1,4-naphthoquinone (Cannon et al., 1987), which has a flattened-boat conformation with a puckering amplitude of 0.113 (3) Å. Structures with two C- or larger atom substituents at the 5- and 8-positions generally exhibit puckering of the quinoid rings. Examples include 5,8-bi(2-thienyl)-1,4-naphthoquinone (Jones, 2004), with a puckering amplitude of 0.309 (3) Å, and 5-(p-methoxyphenyl)-8-(p-cyanophenyl)-1,4-naphthoquinone (Jones & Dix, 2004), with a puckering amplitude of 0.104 (3) Å. When puckering occurs, a flattened-boat conformation is usually observed. The exception to this appears to be the chair/half-chair ring form found in (I).

Additionally, the naphthoquinoid rings of (I) are oriented less close to perpendicular than they are in gossypolone and most related structures. From the best-fit planes of the ten atoms of each naphthoquinoid ring, the dihedral angles for the two bridged ring systems in the asymmetric unit are 67.69 (4) and 68.87 (4)° (Fig. 3). The same angle is 84.6° (Fig. 3) in the gossypolone structure (Talipov et al., 1995), and the range reported for gossypol structures is 70–110° (Gdaniec et al., 1996). Because of the shorter C═O bonds of gossypolone compared with the longer C—OH bonds of gossypol, rotation about the inter-naphthyl bridge bond should be less restricted in 2,2'-binaphthoquinone-based structures than for comparable 2,2'-binaphthalene-based structures. Hence, these compounds should be more likely to exhibit smaller angles between the bridged rings. The effect has, in essence, been observed both experimentally, in that gossypolone Schiff bases are more prone to isomerization at room temperature than are gossypol Schiff bases (Dao et al., 2004), and computationally from MM3 modeling studies, which indicate that the binapthyl rotational barrier is lower for gossypolone than it is for gossypol (Beisel et al., 2005).

In gossypol and gossypolone crystal structures, the 6-position hydroxyl groups donate to the O atoms of the hydroxyl groups at the 5-position. However, these intramolecular interactions are weak, and these hydroxyl groups often also donate into intermolecular hydrogen bonds (Gdaniec et al., 1996). For both hemigossypolone and gossypolone, these intermolecular interactions result in column-like assemblies (Talipov et al., 1995). Because methylation of the 6-position hydroxyl groups in (I) eliminates these donating groups, no intermolecular O—H···O hydrogen bonding is possible. However, several weak intermolecular C—H···O interactions are present.

An intramolecular C—H···O hydrogen bond exists between the aldehyde H27_1 atom and the carbonyl O6_2 atom of a neighbouring molecule at (x+1, -y+1, -z+1) (supplementary Fig. S1A). This interaction ties together pairs of molecules of (I) into dimeric units that are also supported by hydrophobic stacking interactions between both pairs of naphthoquinone rings. This dimer is tied to an adjacent dimer (formed from a pair of molecules of the opposite chirality) through an additional pair of C—H···O interactions between atom H32A_1 and the carbonyl O6_1 atom of the molecule at (-x+2, -y+1 -z+1) (supplementary Fig. S1B). These four-molecule assemblies then pack into layers that are supported by three additional weak C—H···O interactions. The alignment of these groups is slightly offset, such that the layers formed are skewed relative to the long axis of the individual molecules and the assemblies (supplementary Fig. S2). Adjacent layers are held together only by hydrophobic interactions between molecules from opposing layers.

S2. Experimental

A mixture of gossypol, 6-methoxygossypol and 6,6'-dimethoxygossypol was isolated from the root bark of Gossypium barbadense St. Vincent Sea Island cotton, as described previously by Dowd & Pelitire (2006). The mixture was oxidized to form the equivalent gossypolone compounds by the method of Haas & Shirley (1965). Compound (I) was separated by preparative reverse-phase high-performance liquid chromatography, with a mobile phase of acetonitrile and aqueous phosphate buffer. A single crystal was prepared by dissolving a few milligrams of (I) in acetone and allowing petroleum ether to diffuse into the solution over a period of several weeks.

S3. Refinement

Hydroxyl H-atom positions were refined, but their isotropic displacement parameters were constrained to 1.5U_eq(O). The remaining H atoms were placed in idealized positions, with C—H = 0.98 Å [Please check added text], and allowed to ride on their parent C atoms, with U_iso(H) = 1.5U_eq(C) for methyl H atoms or 1.2U_eq(C) for H atoms on ternary C and carbonyl atoms.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure and atom numbering of the two independent molecules of (I). Displacement ellipsoids are drawn at the 50% probability level. Intramolecular O—H···O hydrogen bonds are shown as dashed lines.
	Fig. 2. The puckering of the four independent quinoid rings in the crystal structure of (I).
	Fig. 3. Views along the bridge bond, showing the relative orientations of the naphthoquinoid rings of (I) and gossypolone (Talipov et al., 1995).

7,7'-dihydroxy-5,5'-diisopropyl-6,6'-dimethoxy-3,3'-dimethyl- 1,1',4,4'-tetraoxo-2,2'-binaphthalene-8,8'-dicarbaldehyde

Crystal data

C32H30O10	F(000) = 2416
Mr = 574.56	Dx = 1.407 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9418 reflections
a = 17.8278 (10) Å	θ = 2.4–28.4°
b = 26.2103 (16) Å	µ = 0.11 mm^−1
c = 12.2116 (7) Å	T = 100 K
β = 108.069 (1)°	Plate, orange
V = 5424.7 (5) Å^3	0.60 × 0.40 × 0.10 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer	13486 independent reflections
Radiation source: fine-focus sealed tube	11234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ϕ and ω scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2005)	h = −23→23
Tmin = 0.940, Tmax = 0.990	k = −35→35
88778 measured reflections	l = −16→9

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0633P)^2 + 2.866P] where P = (Fo^2 + 2Fc^2)/3
13486 reflections	(Δ/σ)max = 0.001
785 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.22 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
C1_1	0.81494 (7)	0.52986 (5)	0.79170 (11)	0.0159 (2)
O1_1	0.84972 (6)	0.56914 (4)	0.78312 (9)	0.0206 (2)
C2_1	0.85000 (7)	0.48002 (5)	0.77695 (11)	0.0160 (2)
O2_1	0.74032 (6)	0.66087 (4)	0.92291 (10)	0.0253 (2)
C3_1	0.80623 (8)	0.43732 (5)	0.76033 (11)	0.0181 (2)
O3_1	0.60663 (6)	0.61884 (4)	0.90052 (10)	0.0233 (2)
H3_1	0.6435 (12)	0.6424 (8)	0.9180 (19)	0.035*
C4_1	0.71979 (8)	0.44161 (5)	0.74642 (12)	0.0187 (2)
O4_1	0.51307 (5)	0.53704 (4)	0.84777 (9)	0.0216 (2)
C5_1	0.61423 (7)	0.48770 (5)	0.80909 (11)	0.0167 (2)
O5_1	0.67622 (6)	0.40844 (4)	0.69051 (10)	0.0284 (2)
C6_1	0.58676 (7)	0.53426 (5)	0.83582 (11)	0.0171 (2)
O6_1	0.88604 (5)	0.51753 (4)	0.58820 (8)	0.01958 (19)
C7_1	0.63560 (7)	0.57775 (5)	0.86249 (11)	0.0169 (2)
O7_1	0.98587 (6)	0.62288 (4)	0.45321 (10)	0.0281 (2)
C8_1	0.71244 (7)	0.57610 (5)	0.85479 (11)	0.0152 (2)
O8_1	1.13021 (6)	0.60246 (4)	0.52150 (9)	0.0207 (2)
H8_1	1.0852 (12)	0.6165 (8)	0.4849 (18)	0.031*
C9_1	0.73808 (7)	0.53054 (5)	0.81551 (11)	0.0154 (2)
O9_1	1.25211 (5)	0.54482 (4)	0.65614 (8)	0.01910 (19)
C10_1	0.69042 (7)	0.48701 (5)	0.79385 (11)	0.0160 (2)
O10_1	1.13135 (6)	0.45897 (5)	0.93276 (9)	0.0284 (2)
C11_1	0.94345 (7)	0.50993 (5)	0.67270 (11)	0.0157 (2)
C12_1	0.93272 (7)	0.48290 (5)	0.77380 (11)	0.0164 (2)
C13_1	0.99468 (8)	0.46204 (5)	0.85369 (11)	0.0177 (2)
C14_1	1.07642 (8)	0.47055 (5)	0.84809 (11)	0.0179 (2)
C15_1	1.16519 (7)	0.50027 (5)	0.73316 (11)	0.0155 (2)
C16_1	1.17717 (7)	0.53678 (5)	0.65690 (11)	0.0153 (2)
C17_1	1.11394 (7)	0.56654 (5)	0.58860 (11)	0.0155 (2)
C18_1	1.03654 (7)	0.55850 (5)	0.59214 (11)	0.0152 (2)
C19_1	1.02462 (7)	0.52309 (5)	0.67259 (11)	0.0147 (2)
C20_1	1.08882 (7)	0.49714 (5)	0.74712 (11)	0.0151 (2)
C21_1	0.83444 (9)	0.38541 (5)	0.74122 (13)	0.0236 (3)
H21A_1	0.8873	0.3880	0.7332	0.035*
H21B_1	0.7982	0.3707	0.6709	0.035*
H21C_1	0.8363	0.3635	0.8070	0.035*
C22_1	0.76461 (8)	0.61976 (5)	0.89941 (12)	0.0186 (2)
H22_1	0.8195	0.6160	0.9106	0.022*
C23_1	0.56466 (8)	0.43987 (5)	0.80409 (13)	0.0212 (3)
H23_1	0.5978	0.4102	0.7961	0.025*
C24_1	0.49117 (10)	0.43977 (7)	0.69774 (15)	0.0335 (4)
H24A_1	0.4556	0.4673	0.7044	0.050*
H24B_1	0.4640	0.4069	0.6923	0.050*
H24C_1	0.5069	0.4450	0.6285	0.050*
C25_1	0.54454 (10)	0.43196 (6)	0.91637 (14)	0.0279 (3)
H25A_1	0.5933	0.4315	0.9816	0.042*
H25B_1	0.5168	0.3994	0.9129	0.042*
H25C_1	0.5107	0.4599	0.9264	0.042*
C26_1	0.98874 (8)	0.43185 (6)	0.95492 (13)	0.0235 (3)
H26A_1	0.9362	0.4364	0.9630	0.035*
H26B_1	1.0288	0.4438	1.0250	0.035*
H26C_1	0.9974	0.3956	0.9429	0.035*
C27_1	0.97411 (8)	0.59187 (5)	0.52199 (12)	0.0202 (3)
H27_1	0.9228	0.5895	0.5298	0.024*
C28_1	1.23144 (7)	0.46335 (5)	0.79168 (11)	0.0178 (2)
H28_1	1.2085	0.4371	0.8315	0.021*
C29_1	1.26143 (9)	0.43494 (6)	0.70359 (13)	0.0251 (3)
H29A_1	1.2167	0.4198	0.6444	0.038*
H29B_1	1.2980	0.4080	0.7426	0.038*
H29C_1	1.2887	0.4589	0.6675	0.038*
C30_1	1.29848 (8)	0.48951 (6)	0.88448 (12)	0.0242 (3)
H30A_1	1.3198	0.5175	0.8498	0.036*
H30B_1	1.3403	0.4647	0.9184	0.036*
H30C_1	1.2782	0.5031	0.9446	0.036*
C31_1	0.45975 (9)	0.57186 (7)	0.77045 (18)	0.0349 (4)
H31A_1	0.4797	0.6068	0.7870	0.052*
H31B_1	0.4076	0.5694	0.7809	0.052*
H31C_1	0.4557	0.5631	0.6908	0.052*
C32_1	1.26957 (8)	0.55469 (5)	0.55027 (12)	0.0202 (3)
H32A_1	1.2286	0.5393	0.4857	0.030*
H32B_1	1.3209	0.5398	0.5549	0.030*
H32C_1	1.2711	0.5916	0.5383	0.030*
C1_2	0.00138 (7)	0.31135 (5)	0.30576 (11)	0.0172 (2)
O1_2	0.03129 (6)	0.34501 (4)	0.26395 (9)	0.0221 (2)
C2_2	0.05224 (7)	0.27071 (5)	0.37578 (12)	0.0173 (2)
O2_2	−0.16125 (6)	0.39876 (4)	0.05202 (10)	0.0288 (2)
C3_2	0.02896 (8)	0.24518 (5)	0.45454 (12)	0.0184 (2)
O3_2	−0.26968 (6)	0.37473 (4)	0.13699 (9)	0.0231 (2)
H3_2	−0.2451 (12)	0.3903 (8)	0.0972 (19)	0.035*
C4_2	−0.05019 (8)	0.25623 (5)	0.46709 (12)	0.0195 (3)
O4_2	−0.32048 (5)	0.31660 (4)	0.28147 (9)	0.0215 (2)
C5_2	−0.19283 (8)	0.28029 (5)	0.36143 (12)	0.0176 (2)
O5_2	−0.06106 (6)	0.24532 (4)	0.55807 (10)	0.0280 (2)
C6_2	−0.24377 (7)	0.31246 (5)	0.28205 (12)	0.0179 (2)
O6_2	0.17518 (6)	0.33520 (4)	0.49354 (9)	0.0217 (2)
C7_2	−0.21703 (8)	0.34394 (5)	0.20832 (11)	0.0177 (2)
O7_2	0.31180 (6)	0.44714 (4)	0.45276 (9)	0.0244 (2)
C8_2	−0.13795 (7)	0.34131 (5)	0.20897 (11)	0.0170 (2)
O8_2	0.42407 (6)	0.40243 (4)	0.40817 (9)	0.0210 (2)
H8_2	0.3962 (12)	0.4273 (8)	0.4304 (18)	0.031*
C9_2	−0.08483 (7)	0.31075 (5)	0.29347 (11)	0.0164 (2)
O9_2	0.48367 (6)	0.31890 (4)	0.34043 (9)	0.0231 (2)
C10_2	−0.11112 (8)	0.28186 (5)	0.37037 (12)	0.0171 (2)
O10_2	0.27576 (6)	0.17962 (4)	0.34149 (10)	0.0282 (2)
C11_2	0.18893 (7)	0.30788 (5)	0.42112 (11)	0.0159 (2)
C12_2	0.13326 (7)	0.26633 (5)	0.36663 (11)	0.0170 (2)
C13_2	0.16006 (8)	0.22497 (5)	0.32538 (12)	0.0194 (3)
C14_2	0.24586 (8)	0.22173 (5)	0.33635 (12)	0.0194 (3)
C15_2	0.36570 (8)	0.27191 (5)	0.32462 (12)	0.0187 (3)
C16_2	0.41035 (7)	0.31599 (5)	0.35520 (11)	0.0182 (2)
C17_2	0.38033 (7)	0.36009 (5)	0.39309 (11)	0.0166 (2)
C18_2	0.30569 (7)	0.35908 (5)	0.40976 (11)	0.0156 (2)
C19_2	0.26317 (7)	0.31281 (5)	0.38960 (11)	0.0151 (2)
C20_2	0.29194 (7)	0.27027 (5)	0.34691 (11)	0.0168 (2)
C21_2	0.08031 (8)	0.20962 (6)	0.54191 (13)	0.0248 (3)
H21A_2	0.1319	0.2068	0.5296	0.037*
H21B_2	0.0555	0.1759	0.5339	0.037*
H21C_2	0.0872	0.2229	0.6194	0.037*
C22_2	−0.11690 (8)	0.36826 (5)	0.11726 (12)	0.0222 (3)
H22_2	−0.0668	0.3618	0.1080	0.027*
C23_2	−0.22403 (8)	0.24510 (5)	0.43677 (13)	0.0219 (3)
H23_2	−0.1814	0.2197	0.4712	0.026*
C24_2	−0.29757 (9)	0.21436 (6)	0.37215 (17)	0.0323 (3)
H24A_2	−0.3046	0.1862	0.4208	0.048*
H24B_2	−0.2912	0.2006	0.3009	0.048*
H24C_2	−0.3440	0.2366	0.3534	0.048*
C25_2	−0.23586 (9)	0.27546 (6)	0.53752 (14)	0.0276 (3)
H25A_2	−0.2737	0.3031	0.5075	0.041*
H25B_2	−0.1853	0.2899	0.5839	0.041*
H25C_2	−0.2562	0.2528	0.5855	0.041*
C26_2	0.11245 (9)	0.17853 (6)	0.27785 (15)	0.0295 (3)
H26A_2	0.1297	0.1502	0.3322	0.044*
H26B_2	0.1199	0.1694	0.2041	0.044*
H26C_2	0.0565	0.1856	0.2661	0.044*
C27_2	0.27335 (8)	0.40738 (5)	0.43612 (11)	0.0187 (2)
H27_2	0.2211	0.4079	0.4405	0.022*
C28_2	0.39484 (9)	0.22823 (6)	0.26552 (14)	0.0271 (3)
H28_2	0.3519	0.2021	0.2452	0.033*
C29_2	0.46744 (12)	0.20222 (7)	0.34682 (18)	0.0403 (4)
H29A_2	0.4833	0.1738	0.3068	0.060*
H29B_2	0.4549	0.1893	0.4144	0.060*
H29C_2	0.5107	0.2269	0.3715	0.060*
C30_2	0.40659 (10)	0.24520 (6)	0.15215 (15)	0.0312 (3)
H30A_2	0.4477	0.2714	0.1677	0.047*
H30B_2	0.3570	0.2592	0.1013	0.047*
H30C_2	0.4225	0.2158	0.1149	0.047*
C31_2	−0.38104 (8)	0.30437 (7)	0.17555 (15)	0.0305 (3)
H31A_2	−0.3803	0.3295	0.1165	0.046*
H31B_2	−0.4327	0.3050	0.1883	0.046*
H31C_2	−0.3713	0.2703	0.1498	0.046*
C32_2	0.54795 (9)	0.32766 (7)	0.44458 (15)	0.0318 (3)
H32A_2	0.5398	0.3601	0.4790	0.048*
H32B_2	0.5977	0.3290	0.4264	0.048*
H32C_2	0.5501	0.2999	0.4991	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1_1	0.0141 (5)	0.0191 (6)	0.0142 (5)	−0.0012 (4)	0.0039 (4)	0.0007 (4)
O1_1	0.0183 (4)	0.0201 (5)	0.0246 (5)	−0.0038 (4)	0.0083 (4)	0.0001 (4)
C2_1	0.0144 (5)	0.0196 (6)	0.0145 (5)	0.0001 (4)	0.0050 (4)	0.0010 (4)
O2_1	0.0228 (5)	0.0197 (5)	0.0342 (6)	−0.0026 (4)	0.0102 (4)	−0.0055 (4)
C3_1	0.0179 (6)	0.0202 (6)	0.0172 (6)	−0.0003 (5)	0.0069 (5)	−0.0005 (5)
O3_1	0.0189 (5)	0.0207 (5)	0.0327 (6)	−0.0008 (4)	0.0117 (4)	−0.0043 (4)
C4_1	0.0179 (6)	0.0194 (6)	0.0200 (6)	−0.0023 (5)	0.0076 (5)	−0.0010 (5)
O4_1	0.0148 (4)	0.0262 (5)	0.0263 (5)	−0.0003 (4)	0.0101 (4)	0.0031 (4)
C5_1	0.0147 (6)	0.0209 (6)	0.0141 (6)	−0.0038 (5)	0.0037 (4)	0.0000 (4)
O5_1	0.0231 (5)	0.0277 (5)	0.0356 (6)	−0.0084 (4)	0.0109 (4)	−0.0131 (4)
C6_1	0.0126 (5)	0.0238 (6)	0.0157 (6)	−0.0021 (5)	0.0056 (4)	0.0029 (5)
O6_1	0.0158 (4)	0.0236 (5)	0.0174 (4)	−0.0008 (4)	0.0024 (3)	0.0001 (4)
C7_1	0.0162 (6)	0.0182 (6)	0.0164 (6)	0.0007 (5)	0.0053 (5)	0.0018 (5)
O7_1	0.0251 (5)	0.0304 (5)	0.0293 (6)	0.0070 (4)	0.0092 (4)	0.0136 (4)
C8_1	0.0135 (5)	0.0171 (6)	0.0142 (5)	−0.0007 (4)	0.0031 (4)	0.0018 (4)
O8_1	0.0210 (5)	0.0201 (5)	0.0235 (5)	0.0026 (4)	0.0104 (4)	0.0070 (4)
C9_1	0.0134 (5)	0.0180 (6)	0.0141 (5)	−0.0006 (4)	0.0034 (4)	0.0015 (4)
O9_1	0.0142 (4)	0.0268 (5)	0.0171 (4)	−0.0017 (4)	0.0059 (3)	0.0029 (4)
C10_1	0.0149 (6)	0.0185 (6)	0.0145 (6)	−0.0019 (4)	0.0043 (4)	0.0002 (4)
O10_1	0.0173 (5)	0.0475 (7)	0.0203 (5)	0.0045 (4)	0.0057 (4)	0.0121 (5)
C11_1	0.0153 (6)	0.0162 (6)	0.0160 (6)	0.0013 (4)	0.0053 (4)	−0.0006 (4)
C12_1	0.0152 (6)	0.0182 (6)	0.0167 (6)	−0.0009 (4)	0.0063 (5)	−0.0012 (4)
C13_1	0.0165 (6)	0.0211 (6)	0.0167 (6)	0.0003 (5)	0.0069 (5)	0.0017 (5)
C14_1	0.0156 (6)	0.0220 (6)	0.0167 (6)	0.0016 (5)	0.0061 (5)	0.0022 (5)
C15_1	0.0142 (5)	0.0179 (6)	0.0139 (5)	0.0001 (4)	0.0035 (4)	−0.0010 (4)
C16_1	0.0142 (5)	0.0175 (6)	0.0146 (6)	−0.0010 (4)	0.0052 (4)	−0.0027 (4)
C17_1	0.0187 (6)	0.0140 (5)	0.0146 (5)	−0.0002 (4)	0.0062 (5)	−0.0004 (4)
C18_1	0.0161 (6)	0.0152 (5)	0.0140 (5)	0.0005 (4)	0.0043 (4)	−0.0007 (4)
C19_1	0.0151 (5)	0.0157 (5)	0.0138 (5)	0.0000 (4)	0.0050 (4)	−0.0018 (4)
C20_1	0.0151 (6)	0.0164 (5)	0.0140 (5)	−0.0004 (4)	0.0046 (4)	−0.0003 (4)
C21_1	0.0237 (7)	0.0196 (6)	0.0291 (7)	−0.0005 (5)	0.0106 (6)	−0.0026 (5)
C22_1	0.0170 (6)	0.0197 (6)	0.0190 (6)	−0.0017 (5)	0.0053 (5)	−0.0001 (5)
C23_1	0.0190 (6)	0.0212 (6)	0.0249 (7)	−0.0068 (5)	0.0088 (5)	−0.0030 (5)
C24_1	0.0287 (8)	0.0399 (9)	0.0283 (8)	−0.0149 (7)	0.0039 (6)	−0.0058 (7)
C25_1	0.0351 (8)	0.0248 (7)	0.0271 (7)	−0.0109 (6)	0.0146 (6)	−0.0001 (6)
C26_1	0.0197 (6)	0.0303 (7)	0.0218 (7)	0.0013 (5)	0.0082 (5)	0.0095 (5)
C27_1	0.0191 (6)	0.0195 (6)	0.0207 (6)	0.0028 (5)	0.0044 (5)	0.0018 (5)
C28_1	0.0140 (5)	0.0211 (6)	0.0185 (6)	0.0025 (5)	0.0051 (5)	0.0043 (5)
C29_1	0.0267 (7)	0.0243 (7)	0.0269 (7)	0.0068 (5)	0.0122 (6)	0.0033 (5)
C30_1	0.0170 (6)	0.0358 (8)	0.0180 (6)	−0.0008 (5)	0.0025 (5)	0.0046 (5)
C31_1	0.0164 (6)	0.0351 (8)	0.0532 (11)	0.0039 (6)	0.0107 (7)	0.0137 (7)
C32_1	0.0199 (6)	0.0247 (6)	0.0180 (6)	−0.0016 (5)	0.0090 (5)	0.0013 (5)
C1_2	0.0161 (6)	0.0186 (6)	0.0186 (6)	−0.0021 (5)	0.0078 (5)	−0.0034 (5)
O1_2	0.0198 (5)	0.0229 (5)	0.0265 (5)	−0.0032 (4)	0.0115 (4)	0.0014 (4)
C2_2	0.0137 (5)	0.0189 (6)	0.0202 (6)	−0.0019 (4)	0.0064 (5)	−0.0054 (5)
O2_2	0.0265 (5)	0.0318 (6)	0.0309 (6)	0.0045 (4)	0.0130 (4)	0.0112 (4)
C3_2	0.0161 (6)	0.0184 (6)	0.0203 (6)	−0.0012 (5)	0.0052 (5)	−0.0027 (5)
O3_2	0.0186 (5)	0.0264 (5)	0.0254 (5)	0.0037 (4)	0.0083 (4)	0.0046 (4)
C4_2	0.0179 (6)	0.0189 (6)	0.0234 (7)	−0.0007 (5)	0.0087 (5)	−0.0003 (5)
O4_2	0.0136 (4)	0.0272 (5)	0.0256 (5)	−0.0002 (4)	0.0091 (4)	−0.0027 (4)
C5_2	0.0176 (6)	0.0158 (6)	0.0219 (6)	−0.0020 (5)	0.0099 (5)	−0.0034 (5)
O5_2	0.0259 (5)	0.0354 (6)	0.0260 (5)	0.0043 (4)	0.0127 (4)	0.0084 (4)
C6_2	0.0143 (6)	0.0194 (6)	0.0220 (6)	−0.0020 (5)	0.0086 (5)	−0.0048 (5)
O6_2	0.0208 (5)	0.0240 (5)	0.0236 (5)	−0.0025 (4)	0.0117 (4)	−0.0070 (4)
C7_2	0.0164 (6)	0.0183 (6)	0.0185 (6)	−0.0004 (5)	0.0054 (5)	−0.0033 (5)
O7_2	0.0288 (5)	0.0189 (5)	0.0279 (5)	−0.0016 (4)	0.0123 (4)	−0.0025 (4)
C8_2	0.0173 (6)	0.0167 (6)	0.0191 (6)	−0.0014 (4)	0.0085 (5)	−0.0018 (5)
O8_2	0.0178 (4)	0.0226 (5)	0.0239 (5)	−0.0034 (4)	0.0084 (4)	−0.0007 (4)
C9_2	0.0153 (6)	0.0162 (6)	0.0196 (6)	−0.0016 (4)	0.0080 (5)	−0.0031 (5)
O9_2	0.0150 (4)	0.0318 (5)	0.0254 (5)	0.0021 (4)	0.0105 (4)	0.0023 (4)
C10_2	0.0170 (6)	0.0156 (6)	0.0201 (6)	−0.0009 (4)	0.0079 (5)	−0.0018 (5)
O10_2	0.0297 (5)	0.0198 (5)	0.0389 (6)	0.0031 (4)	0.0162 (5)	−0.0013 (4)
C11_2	0.0133 (5)	0.0174 (6)	0.0174 (6)	0.0014 (4)	0.0055 (4)	−0.0008 (4)
C12_2	0.0140 (5)	0.0198 (6)	0.0176 (6)	0.0003 (4)	0.0055 (4)	−0.0005 (5)
C13_2	0.0183 (6)	0.0208 (6)	0.0196 (6)	−0.0019 (5)	0.0068 (5)	−0.0025 (5)
C14_2	0.0213 (6)	0.0193 (6)	0.0196 (6)	0.0007 (5)	0.0091 (5)	−0.0019 (5)
C15_2	0.0188 (6)	0.0205 (6)	0.0188 (6)	0.0059 (5)	0.0088 (5)	0.0026 (5)
C16_2	0.0138 (6)	0.0244 (6)	0.0182 (6)	0.0042 (5)	0.0075 (5)	0.0046 (5)
C17_2	0.0151 (6)	0.0205 (6)	0.0138 (5)	0.0002 (5)	0.0039 (4)	0.0018 (4)
C18_2	0.0151 (5)	0.0177 (6)	0.0145 (6)	0.0017 (4)	0.0053 (4)	0.0011 (4)
C19_2	0.0133 (5)	0.0183 (6)	0.0143 (5)	0.0021 (4)	0.0050 (4)	0.0005 (4)
C20_2	0.0164 (6)	0.0174 (6)	0.0172 (6)	0.0016 (4)	0.0060 (5)	−0.0009 (4)
C21_2	0.0209 (6)	0.0277 (7)	0.0250 (7)	0.0029 (5)	0.0062 (5)	0.0044 (6)
C22_2	0.0207 (6)	0.0245 (7)	0.0236 (7)	−0.0015 (5)	0.0102 (5)	0.0020 (5)
C23_2	0.0204 (6)	0.0189 (6)	0.0313 (7)	0.0001 (5)	0.0151 (6)	0.0036 (5)
C24_2	0.0262 (7)	0.0242 (7)	0.0496 (10)	−0.0065 (6)	0.0164 (7)	0.0008 (7)
C25_2	0.0307 (7)	0.0290 (7)	0.0295 (8)	0.0048 (6)	0.0187 (6)	0.0057 (6)
C26_2	0.0254 (7)	0.0256 (7)	0.0382 (9)	−0.0060 (6)	0.0109 (6)	−0.0125 (6)
C27_2	0.0202 (6)	0.0196 (6)	0.0178 (6)	0.0017 (5)	0.0080 (5)	0.0004 (5)
C28_2	0.0296 (7)	0.0239 (7)	0.0342 (8)	0.0065 (6)	0.0190 (6)	−0.0012 (6)
C29_2	0.0443 (10)	0.0330 (9)	0.0489 (11)	0.0224 (8)	0.0221 (8)	0.0074 (8)
C30_2	0.0336 (8)	0.0334 (8)	0.0323 (8)	−0.0028 (6)	0.0187 (7)	−0.0084 (6)
C31_2	0.0148 (6)	0.0437 (9)	0.0323 (8)	−0.0039 (6)	0.0063 (6)	−0.0067 (7)
C32_2	0.0156 (6)	0.0461 (9)	0.0331 (8)	0.0046 (6)	0.0065 (6)	0.0048 (7)

Geometric parameters (Å, º)

C1_1—O1_1	1.2228 (16)	C1_2—O1_2	1.2216 (16)
C1_1—C2_1	1.4832 (18)	C1_2—C2_2	1.4856 (19)
C1_1—C9_1	1.4865 (17)	C1_2—C9_2	1.4972 (17)
C2_1—C3_1	1.3432 (18)	C2_2—C3_2	1.3389 (19)
C2_1—C12_1	1.4890 (17)	C2_2—C12_2	1.4873 (17)
O2_1—C22_1	1.2281 (17)	O2_2—C22_2	1.2281 (18)
C3_1—C21_1	1.4939 (19)	C3_2—C4_2	1.4942 (18)
C3_1—C4_1	1.5014 (18)	C3_2—C21_2	1.4964 (19)
O3_1—C7_1	1.3384 (16)	O3_2—C7_2	1.3357 (16)
O3_1—H3_1	0.88 (2)	O3_2—H3_2	0.85 (2)
C4_1—O5_1	1.2232 (17)	C4_2—O5_2	1.2195 (18)
C4_1—C10_1	1.4878 (18)	C4_2—C10_2	1.4935 (19)
O4_1—C6_1	1.3681 (15)	O4_2—C6_2	1.3696 (15)
O4_1—C31_1	1.4392 (19)	O4_2—C31_2	1.4406 (18)
C5_1—C6_1	1.3908 (19)	C5_2—C6_2	1.3890 (19)
C5_1—C10_1	1.4271 (17)	C5_2—C10_2	1.4271 (17)
C5_1—C23_1	1.5242 (18)	C5_2—C23_2	1.5246 (18)
C6_1—C7_1	1.4099 (18)	C6_2—C7_2	1.4089 (19)
O6_1—C11_1	1.2235 (16)	O6_2—C11_2	1.2204 (16)
C7_1—C8_1	1.4026 (17)	C7_2—C8_2	1.4091 (17)
O7_1—C27_1	1.2326 (17)	O7_2—C27_2	1.2292 (17)
C8_1—C9_1	1.4145 (18)	C8_2—C9_2	1.4131 (18)
C8_1—C22_1	1.4686 (17)	C8_2—C22_2	1.4679 (18)
O8_1—C17_1	1.3377 (15)	O8_2—C17_2	1.3360 (16)
O8_1—H8_1	0.87 (2)	O8_2—H8_2	0.91 (2)
C9_1—C10_1	1.3980 (17)	C9_2—C10_2	1.3958 (18)
O9_1—C16_1	1.3554 (15)	O9_2—C16_2	1.3759 (15)
O9_1—C32_1	1.4439 (16)	O9_2—C32_2	1.4421 (19)
O10_1—C14_1	1.2216 (16)	O10_2—C14_2	1.2187 (17)
C11_1—C12_1	1.4865 (18)	C11_2—C12_2	1.4846 (17)
C11_1—C19_1	1.4881 (17)	C11_2—C19_2	1.4943 (17)
C12_1—C13_1	1.3425 (18)	C12_2—C13_2	1.3440 (18)
C13_1—C14_1	1.4966 (17)	C13_2—C26_2	1.4946 (19)
C13_1—C26_1	1.4988 (18)	C13_2—C14_2	1.4959 (18)
C14_1—C20_1	1.4913 (18)	C14_2—C20_2	1.4982 (18)
C15_1—C16_1	1.3973 (18)	C15_2—C16_2	1.3869 (19)
C15_1—C20_1	1.4260 (17)	C15_2—C20_2	1.4238 (18)
C15_1—C28_1	1.5226 (17)	C15_2—C28_2	1.5278 (19)
C16_1—C17_1	1.4112 (17)	C16_2—C17_2	1.4108 (18)
C17_1—C18_1	1.4097 (17)	C17_2—C18_2	1.4074 (17)
C18_1—C19_1	1.4145 (17)	C18_2—C19_2	1.4107 (17)
C18_1—C27_1	1.4650 (17)	C18_2—C27_2	1.4675 (18)
C19_1—C20_1	1.3982 (17)	C19_2—C20_2	1.3942 (17)
C21_1—H21A_1	0.9800	C21_2—H21A_2	0.9800
C21_1—H21B_1	0.9800	C21_2—H21B_2	0.9800
C21_1—H21C_1	0.9800	C21_2—H21C_2	0.9800
C22_1—H22_1	0.9500	C22_2—H22_2	0.9500
C23_1—C24_1	1.532 (2)	C23_2—C24_2	1.533 (2)
C23_1—C25_1	1.535 (2)	C23_2—C25_2	1.534 (2)
C23_1—H23_1	1.0000	C23_2—H23_2	1.0000
C24_1—H24A_1	0.9800	C24_2—H24A_2	0.9800
C24_1—H24B_1	0.9800	C24_2—H24B_2	0.9800
C24_1—H24C_1	0.9800	C24_2—H24C_2	0.9800
C25_1—H25A_1	0.9800	C25_2—H25A_2	0.9800
C25_1—H25B_1	0.9800	C25_2—H25B_2	0.9800
C25_1—H25C_1	0.9800	C25_2—H25C_2	0.9800
C26_1—H26A_1	0.9800	C26_2—H26A_2	0.9800
C26_1—H26B_1	0.9800	C26_2—H26B_2	0.9800
C26_1—H26C_1	0.9800	C26_2—H26C_2	0.9800
C27_1—H27_1	0.9500	C27_2—H27_2	0.9500
C28_1—C30_1	1.5305 (19)	C28_2—C29_2	1.526 (2)
C28_1—C29_1	1.5344 (19)	C28_2—C30_2	1.529 (2)
C28_1—H28_1	1.0000	C28_2—H28_2	1.0000
C29_1—H29A_1	0.9800	C29_2—H29A_2	0.9800
C29_1—H29B_1	0.9800	C29_2—H29B_2	0.9800
C29_1—H29C_1	0.9800	C29_2—H29C_2	0.9800
C30_1—H30A_1	0.9800	C30_2—H30A_2	0.9800
C30_1—H30B_1	0.9800	C30_2—H30B_2	0.9800
C30_1—H30C_1	0.9800	C30_2—H30C_2	0.9800
C31_1—H31A_1	0.9800	C31_2—H31A_2	0.9800
C31_1—H31B_1	0.9800	C31_2—H31B_2	0.9800
C31_1—H31C_1	0.9800	C31_2—H31C_2	0.9800
C32_1—H32A_1	0.9800	C32_2—H32A_2	0.9800
C32_1—H32B_1	0.9800	C32_2—H32B_2	0.9800
C32_1—H32C_1	0.9800	C32_2—H32C_2	0.9800
O1_1—C1_1—C2_1	119.16 (11)	O1_2—C1_2—C2_2	119.39 (12)
O1_1—C1_1—C9_1	121.96 (12)	O1_2—C1_2—C9_2	122.22 (12)
C2_1—C1_1—C9_1	118.89 (11)	C2_2—C1_2—C9_2	118.33 (11)
C3_1—C2_1—C1_1	120.35 (11)	C3_2—C2_2—C1_2	120.12 (11)
C3_1—C2_1—C12_1	124.89 (12)	C3_2—C2_2—C12_2	122.69 (12)
C1_1—C2_1—C12_1	114.62 (11)	C1_2—C2_2—C12_2	116.47 (11)
C2_1—C3_1—C21_1	125.06 (12)	C2_2—C3_2—C4_2	119.33 (12)
C2_1—C3_1—C4_1	118.86 (12)	C2_2—C3_2—C21_2	124.47 (12)
C21_1—C3_1—C4_1	115.72 (11)	C4_2—C3_2—C21_2	115.85 (12)
C7_1—O3_1—H3_1	108.0 (14)	C7_2—O3_2—H3_2	106.2 (14)
O5_1—C4_1—C10_1	123.14 (12)	O5_2—C4_2—C10_2	122.94 (12)
O5_1—C4_1—C3_1	117.49 (12)	O5_2—C4_2—C3_2	118.03 (12)
C10_1—C4_1—C3_1	119.25 (11)	C10_2—C4_2—C3_2	118.98 (12)
C6_1—O4_1—C31_1	115.12 (11)	C6_2—O4_2—C31_2	117.13 (11)
C6_1—C5_1—C10_1	117.41 (11)	C6_2—C5_2—C10_2	117.83 (12)
C6_1—C5_1—C23_1	119.28 (11)	C6_2—C5_2—C23_2	120.42 (11)
C10_1—C5_1—C23_1	123.22 (12)	C10_2—C5_2—C23_2	121.75 (12)
O4_1—C6_1—C5_1	119.44 (11)	O4_2—C6_2—C5_2	119.17 (12)
O4_1—C6_1—C7_1	118.48 (12)	O4_2—C6_2—C7_2	119.05 (12)
C5_1—C6_1—C7_1	121.77 (11)	C5_2—C6_2—C7_2	121.59 (12)
O3_1—C7_1—C8_1	122.56 (12)	O3_2—C7_2—C6_2	117.51 (12)
O3_1—C7_1—C6_1	116.98 (11)	O3_2—C7_2—C8_2	122.19 (12)
C8_1—C7_1—C6_1	120.37 (12)	C6_2—C7_2—C8_2	120.27 (12)
C7_1—C8_1—C9_1	118.28 (11)	C7_2—C8_2—C9_2	118.33 (12)
C7_1—C8_1—C22_1	118.06 (11)	C7_2—C8_2—C22_2	117.66 (12)
C9_1—C8_1—C22_1	123.33 (11)	C9_2—C8_2—C22_2	123.91 (12)
C17_1—O8_1—H8_1	105.7 (13)	C17_2—O8_2—H8_2	106.7 (12)
C10_1—C9_1—C8_1	120.78 (11)	C10_2—C9_2—C8_2	120.66 (12)
C10_1—C9_1—C1_1	119.75 (11)	C10_2—C9_2—C1_2	119.13 (12)
C8_1—C9_1—C1_1	119.40 (11)	C8_2—C9_2—C1_2	120.13 (11)
C16_1—O9_1—C32_1	121.37 (10)	C16_2—O9_2—C32_2	114.88 (11)
C9_1—C10_1—C5_1	120.81 (12)	C9_2—C10_2—C5_2	120.80 (12)
C9_1—C10_1—C4_1	117.37 (11)	C9_2—C10_2—C4_2	117.54 (11)
C5_1—C10_1—C4_1	121.67 (11)	C5_2—C10_2—C4_2	121.49 (12)
O6_1—C11_1—C12_1	119.25 (11)	O6_2—C11_2—C12_2	119.91 (11)
O6_1—C11_1—C19_1	121.39 (12)	O6_2—C11_2—C19_2	121.94 (11)
C12_1—C11_1—C19_1	119.14 (11)	C12_2—C11_2—C19_2	118.06 (11)
C13_1—C12_1—C11_1	120.59 (11)	C13_2—C12_2—C11_2	119.59 (11)
C13_1—C12_1—C2_1	123.98 (12)	C13_2—C12_2—C2_2	123.83 (12)
C11_1—C12_1—C2_1	115.42 (11)	C11_2—C12_2—C2_2	116.07 (11)
C12_1—C13_1—C14_1	119.96 (12)	C12_2—C13_2—C26_2	125.27 (12)
C12_1—C13_1—C26_1	124.17 (12)	C12_2—C13_2—C14_2	119.00 (12)
C14_1—C13_1—C26_1	115.80 (11)	C26_2—C13_2—C14_2	115.48 (12)
O10_1—C14_1—C20_1	122.04 (12)	O10_2—C14_2—C13_2	118.35 (12)
O10_1—C14_1—C13_1	117.42 (12)	O10_2—C14_2—C20_2	123.04 (12)
C20_1—C14_1—C13_1	120.24 (11)	C13_2—C14_2—C20_2	118.52 (11)
C16_1—C15_1—C20_1	117.91 (11)	C16_2—C15_2—C20_2	117.43 (12)
C16_1—C15_1—C28_1	119.43 (11)	C16_2—C15_2—C28_2	120.04 (12)
C20_1—C15_1—C28_1	122.53 (11)	C20_2—C15_2—C28_2	122.49 (12)
O9_1—C16_1—C15_1	117.77 (11)	O9_2—C16_2—C15_2	120.00 (12)
O9_1—C16_1—C17_1	121.23 (11)	O9_2—C16_2—C17_2	118.05 (12)
C15_1—C16_1—C17_1	120.87 (11)	C15_2—C16_2—C17_2	121.76 (12)
O8_1—C17_1—C18_1	121.62 (11)	O8_2—C17_2—C18_2	122.24 (12)
O8_1—C17_1—C16_1	117.76 (11)	O8_2—C17_2—C16_2	117.46 (11)
C18_1—C17_1—C16_1	120.62 (11)	C18_2—C17_2—C16_2	120.26 (12)
C17_1—C18_1—C19_1	118.60 (11)	C17_2—C18_2—C19_2	118.15 (11)
C17_1—C18_1—C27_1	117.78 (11)	C17_2—C18_2—C27_2	117.96 (11)
C19_1—C18_1—C27_1	123.19 (11)	C19_2—C18_2—C27_2	123.61 (11)
C20_1—C19_1—C18_1	120.15 (11)	C20_2—C19_2—C18_2	120.84 (11)
C20_1—C19_1—C11_1	119.12 (11)	C20_2—C19_2—C11_2	119.02 (11)
C18_1—C19_1—C11_1	120.55 (11)	C18_2—C19_2—C11_2	120.02 (11)
C19_1—C20_1—C15_1	120.89 (11)	C19_2—C20_2—C15_2	121.07 (12)
C19_1—C20_1—C14_1	117.66 (11)	C19_2—C20_2—C14_2	117.12 (11)
C15_1—C20_1—C14_1	121.17 (11)	C15_2—C20_2—C14_2	121.56 (11)
C3_1—C21_1—H21A_1	109.5	C3_2—C21_2—H21A_2	109.5
C3_1—C21_1—H21B_1	109.5	C3_2—C21_2—H21B_2	109.5
H21A_1—C21_1—H21B_1	109.5	H21A_2—C21_2—H21B_2	109.5
C3_1—C21_1—H21C_1	109.5	C3_2—C21_2—H21C_2	109.5
H21A_1—C21_1—H21C_1	109.5	H21A_2—C21_2—H21C_2	109.5
H21B_1—C21_1—H21C_1	109.5	H21B_2—C21_2—H21C_2	109.5
O2_1—C22_1—C8_1	122.80 (12)	O2_2—C22_2—C8_2	122.87 (13)
O2_1—C22_1—H22_1	118.6	O2_2—C22_2—H22_2	118.6
C8_1—C22_1—H22_1	118.6	C8_2—C22_2—H22_2	118.6
C5_1—C23_1—C24_1	111.60 (12)	C5_2—C23_2—C24_2	114.92 (13)
C5_1—C23_1—C25_1	111.63 (11)	C5_2—C23_2—C25_2	109.68 (11)
C24_1—C23_1—C25_1	112.44 (12)	C24_2—C23_2—C25_2	112.17 (12)
C5_1—C23_1—H23_1	106.9	C5_2—C23_2—H23_2	106.5
C24_1—C23_1—H23_1	106.9	C24_2—C23_2—H23_2	106.5
C25_1—C23_1—H23_1	106.9	C25_2—C23_2—H23_2	106.5
C23_1—C24_1—H24A_1	109.5	C23_2—C24_2—H24A_2	109.5
C23_1—C24_1—H24B_1	109.5	C23_2—C24_2—H24B_2	109.5
H24A_1—C24_1—H24B_1	109.5	H24A_2—C24_2—H24B_2	109.5
C23_1—C24_1—H24C_1	109.5	C23_2—C24_2—H24C_2	109.5
H24A_1—C24_1—H24C_1	109.5	H24A_2—C24_2—H24C_2	109.5
H24B_1—C24_1—H24C_1	109.5	H24B_2—C24_2—H24C_2	109.5
C23_1—C25_1—H25A_1	109.5	C23_2—C25_2—H25A_2	109.5
C23_1—C25_1—H25B_1	109.5	C23_2—C25_2—H25B_2	109.5
H25A_1—C25_1—H25B_1	109.5	H25A_2—C25_2—H25B_2	109.5
C23_1—C25_1—H25C_1	109.5	C23_2—C25_2—H25C_2	109.5
H25A_1—C25_1—H25C_1	109.5	H25A_2—C25_2—H25C_2	109.5
H25B_1—C25_1—H25C_1	109.5	H25B_2—C25_2—H25C_2	109.5
C13_1—C26_1—H26A_1	109.5	C13_2—C26_2—H26A_2	109.5
C13_1—C26_1—H26B_1	109.5	C13_2—C26_2—H26B_2	109.5
H26A_1—C26_1—H26B_1	109.5	H26A_2—C26_2—H26B_2	109.5
C13_1—C26_1—H26C_1	109.5	C13_2—C26_2—H26C_2	109.5
H26A_1—C26_1—H26C_1	109.5	H26A_2—C26_2—H26C_2	109.5
H26B_1—C26_1—H26C_1	109.5	H26B_2—C26_2—H26C_2	109.5
O7_1—C27_1—C18_1	122.23 (13)	O7_2—C27_2—C18_2	122.06 (12)
O7_1—C27_1—H27_1	118.9	O7_2—C27_2—H27_2	119.0
C18_1—C27_1—H27_1	118.9	C18_2—C27_2—H27_2	119.0
C15_1—C28_1—C30_1	112.13 (11)	C29_2—C28_2—C15_2	111.81 (14)
C15_1—C28_1—C29_1	111.57 (11)	C29_2—C28_2—C30_2	113.10 (13)
C30_1—C28_1—C29_1	112.01 (11)	C15_2—C28_2—C30_2	111.83 (12)
C15_1—C28_1—H28_1	106.9	C29_2—C28_2—H28_2	106.5
C30_1—C28_1—H28_1	106.9	C15_2—C28_2—H28_2	106.5
C29_1—C28_1—H28_1	106.9	C30_2—C28_2—H28_2	106.5
C28_1—C29_1—H29A_1	109.5	C28_2—C29_2—H29A_2	109.5
C28_1—C29_1—H29B_1	109.5	C28_2—C29_2—H29B_2	109.5
H29A_1—C29_1—H29B_1	109.5	H29A_2—C29_2—H29B_2	109.5
C28_1—C29_1—H29C_1	109.5	C28_2—C29_2—H29C_2	109.5
H29A_1—C29_1—H29C_1	109.5	H29A_2—C29_2—H29C_2	109.5
H29B_1—C29_1—H29C_1	109.5	H29B_2—C29_2—H29C_2	109.5
C28_1—C30_1—H30A_1	109.5	C28_2—C30_2—H30A_2	109.5
C28_1—C30_1—H30B_1	109.5	C28_2—C30_2—H30B_2	109.5
H30A_1—C30_1—H30B_1	109.5	H30A_2—C30_2—H30B_2	109.5
C28_1—C30_1—H30C_1	109.5	C28_2—C30_2—H30C_2	109.5
H30A_1—C30_1—H30C_1	109.5	H30A_2—C30_2—H30C_2	109.5
H30B_1—C30_1—H30C_1	109.5	H30B_2—C30_2—H30C_2	109.5
O4_1—C31_1—H31A_1	109.5	O4_2—C31_2—H31A_2	109.5
O4_1—C31_1—H31B_1	109.5	O4_2—C31_2—H31B_2	109.5
H31A_1—C31_1—H31B_1	109.5	H31A_2—C31_2—H31B_2	109.5
O4_1—C31_1—H31C_1	109.5	O4_2—C31_2—H31C_2	109.5
H31A_1—C31_1—H31C_1	109.5	H31A_2—C31_2—H31C_2	109.5
H31B_1—C31_1—H31C_1	109.5	H31B_2—C31_2—H31C_2	109.5
O9_1—C32_1—H32A_1	109.5	O9_2—C32_2—H32A_2	109.5
O9_1—C32_1—H32B_1	109.5	O9_2—C32_2—H32B_2	109.5
H32A_1—C32_1—H32B_1	109.5	H32A_2—C32_2—H32B_2	109.5
O9_1—C32_1—H32C_1	109.5	O9_2—C32_2—H32C_2	109.5
H32A_1—C32_1—H32C_1	109.5	H32A_2—C32_2—H32C_2	109.5
H32B_1—C32_1—H32C_1	109.5	H32B_2—C32_2—H32C_2	109.5
O1_1—C1_1—C2_1—C3_1	−165.15 (13)	O1_2—C1_2—C2_2—C3_2	155.85 (13)
C9_1—C1_1—C2_1—C3_1	14.32 (18)	C9_2—C1_2—C2_2—C3_2	−21.44 (18)
O1_1—C1_1—C2_1—C12_1	10.63 (17)	O1_2—C1_2—C2_2—C12_2	−14.71 (18)
C9_1—C1_1—C2_1—C12_1	−169.90 (11)	C9_2—C1_2—C2_2—C12_2	168.01 (11)
C1_1—C2_1—C3_1—C21_1	178.21 (13)	C1_2—C2_2—C3_2—C4_2	2.97 (19)
C12_1—C2_1—C3_1—C21_1	2.9 (2)	C12_2—C2_2—C3_2—C4_2	172.92 (12)
C1_1—C2_1—C3_1—C4_1	5.40 (19)	C1_2—C2_2—C3_2—C21_2	−169.95 (13)
C12_1—C2_1—C3_1—C4_1	−169.92 (12)	C12_2—C2_2—C3_2—C21_2	0.0 (2)
C2_1—C3_1—C4_1—O5_1	153.00 (14)	C2_2—C3_2—C4_2—O5_2	−158.03 (13)
C21_1—C3_1—C4_1—O5_1	−20.47 (19)	C21_2—C3_2—C4_2—O5_2	15.49 (19)
C2_1—C3_1—C4_1—C10_1	−23.11 (18)	C2_2—C3_2—C4_2—C10_2	19.55 (18)
C21_1—C3_1—C4_1—C10_1	163.43 (12)	C21_2—C3_2—C4_2—C10_2	−166.94 (12)
C31_1—O4_1—C6_1—C5_1	−120.71 (15)	C31_2—O4_2—C6_2—C5_2	−122.28 (14)
C31_1—O4_1—C6_1—C7_1	65.59 (17)	C31_2—O4_2—C6_2—C7_2	62.68 (17)
C10_1—C5_1—C6_1—O4_1	178.04 (11)	C10_2—C5_2—C6_2—O4_2	−171.82 (11)
C23_1—C5_1—C6_1—O4_1	−5.35 (18)	C23_2—C5_2—C6_2—O4_2	7.55 (19)
C10_1—C5_1—C6_1—C7_1	−8.48 (19)	C10_2—C5_2—C6_2—C7_2	3.09 (19)
C23_1—C5_1—C6_1—C7_1	168.13 (12)	C23_2—C5_2—C6_2—C7_2	−177.54 (12)
O4_1—C6_1—C7_1—O3_1	1.45 (18)	O4_2—C6_2—C7_2—O3_2	−3.20 (18)
C5_1—C6_1—C7_1—O3_1	−172.09 (12)	C5_2—C6_2—C7_2—O3_2	−178.12 (12)
O4_1—C6_1—C7_1—C8_1	178.07 (11)	O4_2—C6_2—C7_2—C8_2	178.57 (11)
C5_1—C6_1—C7_1—C8_1	4.53 (19)	C5_2—C6_2—C7_2—C8_2	3.66 (19)
O3_1—C7_1—C8_1—C9_1	178.84 (12)	O3_2—C7_2—C8_2—C9_2	175.02 (12)
C6_1—C7_1—C8_1—C9_1	2.41 (18)	C6_2—C7_2—C8_2—C9_2	−6.84 (19)
O3_1—C7_1—C8_1—C22_1	5.18 (19)	O3_2—C7_2—C8_2—C22_2	−8.43 (19)
C6_1—C7_1—C8_1—C22_1	−171.25 (12)	C6_2—C7_2—C8_2—C22_2	169.70 (12)
C7_1—C8_1—C9_1—C10_1	−5.08 (18)	C7_2—C8_2—C9_2—C10_2	3.30 (19)
C22_1—C8_1—C9_1—C10_1	168.22 (12)	C22_2—C8_2—C9_2—C10_2	−173.01 (12)
C7_1—C8_1—C9_1—C1_1	171.95 (11)	C7_2—C8_2—C9_2—C1_2	−173.22 (11)
C22_1—C8_1—C9_1—C1_1	−14.75 (19)	C22_2—C8_2—C9_2—C1_2	10.47 (19)
O1_1—C1_1—C9_1—C10_1	162.56 (12)	O1_2—C1_2—C9_2—C10_2	−160.07 (13)
C2_1—C1_1—C9_1—C10_1	−16.90 (17)	C2_2—C1_2—C9_2—C10_2	17.13 (17)
O1_1—C1_1—C9_1—C8_1	−14.50 (19)	O1_2—C1_2—C9_2—C8_2	16.51 (19)
C2_1—C1_1—C9_1—C8_1	166.05 (11)	C2_2—C1_2—C9_2—C8_2	−166.29 (12)
C8_1—C9_1—C10_1—C5_1	1.00 (19)	C8_2—C9_2—C10_2—C5_2	3.48 (19)
C1_1—C9_1—C10_1—C5_1	−176.02 (11)	C1_2—C9_2—C10_2—C5_2	−179.96 (11)
C8_1—C9_1—C10_1—C4_1	176.61 (12)	C8_2—C9_2—C10_2—C4_2	−171.83 (12)
C1_1—C9_1—C10_1—C4_1	−0.41 (17)	C1_2—C9_2—C10_2—C4_2	4.73 (18)
C6_1—C5_1—C10_1—C9_1	5.72 (18)	C6_2—C5_2—C10_2—C9_2	−6.65 (19)
C23_1—C5_1—C10_1—C9_1	−170.74 (12)	C23_2—C5_2—C10_2—C9_2	173.99 (12)
C6_1—C5_1—C10_1—C4_1	−169.70 (12)	C6_2—C5_2—C10_2—C4_2	168.48 (12)
C23_1—C5_1—C10_1—C4_1	13.84 (19)	C23_2—C5_2—C10_2—C4_2	−10.89 (19)
O5_1—C4_1—C10_1—C9_1	−155.70 (14)	O5_2—C4_2—C10_2—C9_2	154.23 (14)
C3_1—C4_1—C10_1—C9_1	20.17 (18)	C3_2—C4_2—C10_2—C9_2	−23.22 (18)
O5_1—C4_1—C10_1—C5_1	19.9 (2)	O5_2—C4_2—C10_2—C5_2	−21.0 (2)
C3_1—C4_1—C10_1—C5_1	−164.27 (12)	C3_2—C4_2—C10_2—C5_2	161.50 (12)
O6_1—C11_1—C12_1—C13_1	162.19 (13)	O6_2—C11_2—C12_2—C13_2	−153.28 (14)
C19_1—C11_1—C12_1—C13_1	−12.53 (18)	C19_2—C11_2—C12_2—C13_2	23.21 (18)
O6_1—C11_1—C12_1—C2_1	−16.43 (17)	O6_2—C11_2—C12_2—C2_2	18.86 (18)
C19_1—C11_1—C12_1—C2_1	168.85 (11)	C19_2—C11_2—C12_2—C2_2	−164.66 (11)
C3_1—C2_1—C12_1—C13_1	−69.29 (19)	C3_2—C2_2—C12_2—C13_2	72.60 (19)
C1_1—C2_1—C12_1—C13_1	115.15 (14)	C1_2—C2_2—C12_2—C13_2	−117.11 (15)
C3_1—C2_1—C12_1—C11_1	109.27 (15)	C3_2—C2_2—C12_2—C11_2	−99.16 (15)
C1_1—C2_1—C12_1—C11_1	−66.28 (15)	C1_2—C2_2—C12_2—C11_2	71.13 (15)
C11_1—C12_1—C13_1—C14_1	6.40 (19)	C11_2—C12_2—C13_2—C26_2	174.44 (14)
C2_1—C12_1—C13_1—C14_1	−175.10 (12)	C2_2—C12_2—C13_2—C26_2	3.0 (2)
C11_1—C12_1—C13_1—C26_1	−176.73 (13)	C11_2—C12_2—C13_2—C14_2	0.5 (2)
C2_1—C12_1—C13_1—C26_1	1.8 (2)	C2_2—C12_2—C13_2—C14_2	−171.02 (12)
C12_1—C13_1—C14_1—O10_1	166.98 (14)	C12_2—C13_2—C14_2—O10_2	152.30 (14)
C26_1—C13_1—C14_1—O10_1	−10.15 (19)	C26_2—C13_2—C14_2—O10_2	−22.25 (19)
C12_1—C13_1—C14_1—C20_1	−6.88 (19)	C12_2—C13_2—C14_2—C20_2	−24.45 (19)
C26_1—C13_1—C14_1—C20_1	175.99 (12)	C26_2—C13_2—C14_2—C20_2	161.00 (13)
C32_1—O9_1—C16_1—C15_1	142.20 (12)	C32_2—O9_2—C16_2—C15_2	−119.98 (15)
C32_1—O9_1—C16_1—C17_1	−41.88 (17)	C32_2—O9_2—C16_2—C17_2	64.96 (16)
C20_1—C15_1—C16_1—O9_1	170.58 (11)	C20_2—C15_2—C16_2—O9_2	177.12 (12)
C28_1—C15_1—C16_1—O9_1	−13.40 (17)	C28_2—C15_2—C16_2—O9_2	−4.98 (19)
C20_1—C15_1—C16_1—C17_1	−5.35 (18)	C20_2—C15_2—C16_2—C17_2	−8.00 (19)
C28_1—C15_1—C16_1—C17_1	170.66 (12)	C28_2—C15_2—C16_2—C17_2	169.89 (13)
O9_1—C16_1—C17_1—O8_1	1.08 (18)	O9_2—C16_2—C17_2—O8_2	2.37 (18)
C15_1—C16_1—C17_1—O8_1	176.88 (11)	C15_2—C16_2—C17_2—O8_2	−172.60 (12)
O9_1—C16_1—C17_1—C18_1	−178.60 (11)	O9_2—C16_2—C17_2—C18_2	−179.87 (11)
C15_1—C16_1—C17_1—C18_1	−2.81 (19)	C15_2—C16_2—C17_2—C18_2	5.2 (2)
O8_1—C17_1—C18_1—C19_1	−174.34 (11)	O8_2—C17_2—C18_2—C19_2	178.79 (11)
C16_1—C17_1—C18_1—C19_1	5.33 (18)	C16_2—C17_2—C18_2—C19_2	1.14 (18)
O8_1—C17_1—C18_1—C27_1	−1.69 (18)	O8_2—C17_2—C18_2—C27_2	4.64 (18)
C16_1—C17_1—C18_1—C27_1	177.98 (12)	C16_2—C17_2—C18_2—C27_2	−173.01 (12)
C17_1—C18_1—C19_1—C20_1	0.45 (18)	C17_2—C18_2—C19_2—C20_2	−4.25 (18)
C27_1—C18_1—C19_1—C20_1	−171.78 (12)	C27_2—C18_2—C19_2—C20_2	169.54 (12)
C17_1—C18_1—C19_1—C11_1	−174.63 (11)	C17_2—C18_2—C19_2—C11_2	171.79 (11)
C27_1—C18_1—C19_1—C11_1	13.14 (19)	C27_2—C18_2—C19_2—C11_2	−14.42 (19)
O6_1—C11_1—C19_1—C20_1	−155.12 (12)	O6_2—C11_2—C19_2—C20_2	153.37 (13)
C12_1—C11_1—C19_1—C20_1	19.48 (17)	C12_2—C11_2—C19_2—C20_2	−23.04 (17)
O6_1—C11_1—C19_1—C18_1	20.02 (19)	O6_2—C11_2—C19_2—C18_2	−22.74 (19)
C12_1—C11_1—C19_1—C18_1	−165.38 (11)	C12_2—C11_2—C19_2—C18_2	160.85 (12)
C18_1—C19_1—C20_1—C15_1	−8.82 (18)	C18_2—C19_2—C20_2—C15_2	1.28 (19)
C11_1—C19_1—C20_1—C15_1	166.33 (11)	C11_2—C19_2—C20_2—C15_2	−174.79 (12)
C18_1—C19_1—C20_1—C14_1	165.16 (11)	C18_2—C19_2—C20_2—C14_2	175.63 (11)
C11_1—C19_1—C20_1—C14_1	−19.69 (17)	C11_2—C19_2—C20_2—C14_2	−0.45 (18)
C16_1—C15_1—C20_1—C19_1	11.19 (18)	C16_2—C15_2—C20_2—C19_2	4.81 (19)
C28_1—C15_1—C20_1—C19_1	−164.69 (12)	C28_2—C15_2—C20_2—C19_2	−173.03 (13)
C16_1—C15_1—C20_1—C14_1	−162.57 (12)	C16_2—C15_2—C20_2—C14_2	−169.29 (12)
C28_1—C15_1—C20_1—C14_1	21.54 (18)	C28_2—C15_2—C20_2—C14_2	12.9 (2)
O10_1—C14_1—C20_1—C19_1	−159.91 (13)	O10_2—C14_2—C20_2—C19_2	−152.55 (14)
C13_1—C14_1—C20_1—C19_1	13.66 (18)	C13_2—C14_2—C20_2—C19_2	24.04 (18)
O10_1—C14_1—C20_1—C15_1	14.0 (2)	O10_2—C14_2—C20_2—C15_2	21.8 (2)
C13_1—C14_1—C20_1—C15_1	−172.38 (12)	C13_2—C14_2—C20_2—C15_2	−161.65 (12)
C7_1—C8_1—C22_1—O2_1	−13.9 (2)	C7_2—C8_2—C22_2—O2_2	11.4 (2)
C9_1—C8_1—C22_1—O2_1	172.80 (13)	C9_2—C8_2—C22_2—O2_2	−172.24 (14)
C6_1—C5_1—C23_1—C24_1	72.03 (16)	C6_2—C5_2—C23_2—C24_2	47.99 (17)
C10_1—C5_1—C23_1—C24_1	−111.57 (15)	C10_2—C5_2—C23_2—C24_2	−132.66 (14)
C6_1—C5_1—C23_1—C25_1	−54.74 (17)	C6_2—C5_2—C23_2—C25_2	−79.46 (16)
C10_1—C5_1—C23_1—C25_1	121.67 (14)	C10_2—C5_2—C23_2—C25_2	99.89 (15)
C17_1—C18_1—C27_1—O7_1	6.9 (2)	C17_2—C18_2—C27_2—O7_2	−5.85 (19)
C19_1—C18_1—C27_1—O7_1	179.20 (13)	C19_2—C18_2—C27_2—O7_2	−179.65 (13)
C16_1—C15_1—C28_1—C30_1	72.39 (15)	C16_2—C15_2—C28_2—C29_2	68.91 (18)
C20_1—C15_1—C28_1—C30_1	−111.79 (14)	C20_2—C15_2—C28_2—C29_2	−113.31 (16)
C16_1—C15_1—C28_1—C29_1	−54.18 (16)	C16_2—C15_2—C28_2—C30_2	−59.07 (18)
C20_1—C15_1—C28_1—C29_1	121.64 (13)	C20_2—C15_2—C28_2—C30_2	118.71 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3_1—H3_1···O2_1	0.88 (2)	1.78 (2)	2.5622 (14)	148 (2)
O8_1—H8_1···O7_1	0.87 (2)	1.70 (2)	2.5044 (15)	153 (2)
O3_2—H3_2···O2_2	0.85 (2)	1.76 (2)	2.5405 (15)	151 (2)
O8_2—H8_2···O7_2	0.91 (2)	1.69 (2)	2.5203 (14)	149.6 (18)
C22_1—H22_1···O1_1	0.95	2.18	2.7232 (18)	115
C23_1—H23_1···O5_1	1.00	2.18	2.8756 (19)	126
C24_1—H24A_1···O4_1	0.98	2.52	3.093 (2)	117
C25_1—H25C_1···O4_1	0.98	2.24	2.8828 (19)	122
C26_1—H26A_1···O2_2^i	0.98	2.52	3.3579 (19)	144
C27_1—H27_1···O6_1	0.95	2.19	2.7754 (17)	119
C27_1—H27_1···O6_2^ii	0.95	2.59	3.2343 (18)	125
C28_1—H28_1···O10_1	1.00	2.19	2.8412 (17)	121
C29_1—H29C_1···O9_1	0.98	2.34	2.9322 (19)	118
C30_1—H30A_1···O9_1	0.98	2.41	3.0216 (17)	120
C31_1—H31A_1···O3_1	0.98	2.28	2.884 (2)	119
C32_1—H32A_1···O6_1^iii	0.98	2.46	3.3509 (17)	150
C21_2—H21A_2···O2_1^iv	0.98	2.48	3.3453 (19)	147
C22_2—H22_2···O1_2	0.95	2.19	2.7612 (18)	117
C23_2—H23_2···O5_2	1.00	2.18	2.8224 (19)	120
C24_2—H24C_2···O4_2	0.98	2.36	2.8798 (19)	112
C26_2—H26B_2···O7_1^v	0.98	2.55	3.177 (2)	122
C27_2—H27_2···O6_2	0.95	2.25	2.8098 (18)	117
C28_2—H28_2···O10_2	1.00	2.14	2.866 (2)	128
C29_2—H29C_2···O9_2	0.98	2.47	3.075 (2)	120
C30_2—H30A_2···O9_2	0.98	2.36	2.991 (2)	122
C31_2—H31A_2···O3_2	0.98	2.25	2.854 (2)	119
C32_2—H32A_2···O8_2	0.98	2.26	2.882 (2)	120

Symmetry codes: (i) x+1, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1, y−1/2, −z+1/2.