17[alpha],21-Di­hydroxy-16[beta]-methylpregna-1,4-diene-3,11,20-trione (meprednisone)

The title compound, C₂₂H₂₈O₅, is a commercial therapeutic agent of the steroid class. Both independent mol­ecules in the asymmetric unit have six-membered A rings that are planar, while the B and C rings adopt normal chair conformations. The five-membered D ring is in a 13[beta],14[alpha]-half-chair con­formation, and the B/C and C/D ring junctions are in trans positions. Cohesion in the crystal is provided by O-H...O hydrogen bonds, which generate chains of mol­ecules that are organized in a plane that lies along the crystallographic b axis.

S1. Comment

Corticosteroids constitute a class of compounds that are able to exert several physiologic and metabolic activities; in particular, the glucocorticoids can affect the lipid, carbohydrate and protein metabolism and, with a lesser potency, the electrolyte balance (Goodman & Gilman, 1993). The title compound, meprednisone, (I), is a steroid anti-inflammatory treatment that is indicated for rheumatic, collagen and skin diseases and possesses an anti-inflammatory potency equivalent to six times that of cortisone. Meprednisone, the 16β-methyl analogue of prednisone (Δ¹ cortisone or 17α,21-dihydroxy-pregna-1,4-diene-3,11,20-trione), has been developed because of the observation that the replacement of the steroid D-ring by a methyl group changes (decreases) the Na⁺ retention characteristics of the compound (Rausser et al., 1966). The structure of prednisone, (II), has been determined by single-crystal X-ray crystallography, and the data have been deposited with the Cambridge Structural Database (CSD, Allen & Kennard, 1993) with refcode PRGDOL (Tseikinsky et al., 1979). The present work, which is part of an ongoing study aimed at the determination of the three-dimensional structures of biologically active compounds (Vega et al., 2001), reports on (I).

Compound (I) crystallized in the space group P2₁, with two independent molecules in the asymmetric unit (see Fig. 1). In the steroid nucleus, the A-ring is planar, whereas the other six-membered rings deviate significantly from planarity and adopt conformations close to chair. The Cremer & Pople (1975) ring puckering parameters are as follows for molecules (I)A and (I)B, respectively: for ring B, Q_T is 0.547 (4) and 0.562 (3) Å, θ₂ is 174.9 (4) and 176.8 (3), and ϕ₂ is 15 (4) and 126 (7)°, and for ring C, Q_T is 0.589 (4) and 0.583 (4) Å, θ₂ is 170.4 (3) and 177.8 (3), and ϕ₂ is 58 (2) and 68 (9)°. In these four rings, the asymmetry parameters indicate the presence of three mirror planes and a twofold axis that is typical of the ideal chair conformation (Duax et al., 1976). The five-membered D-ring is in a 13β, 14α half-chair conformation with ring puckering parameters of q₂ = 0.454 (4) and 0.484 (4) Å and ϕ₂ = 11.9 (4) and 12.8 (4)° [(I)A and (I)B, respectively], while the asymmetry parameters are D_S(C13) = 0.075 (2) and 0.085 (2) and D₂(C13–C14) = 0.026 (2) and 0.024 (2) for (I)A and (I)B, respectively.

A molecular superposition of (I)A on (I)B, using XP (Sheldrick, 1991), gave an r.m.s. deviation of 0.30 Å. As shown in Fig. 2, the molecules differ considerably at the location of atoms O3 (O3A—O3B deviation of 0.791 Å), O11 (0.479 Å) and O21 (0.459 Å). In (I)B, the mean plane of the A-ring is 43.76 (7)° from the least-squares C5···C17 reference plane (Duax et al., 1976); however, in (I)A the dihedral angle is 30.95 (8)°, and consequently O3B lies ca 1 Å further from the C5···C17 reference plane than O3A [2.708 (3) versus 1.743 (2) Å]. This dissimilarity could be an effect of the intermolecular interactions in which the O3 atoms take part. The donor···acceptor distances and the angles of the hydrogen bonds differ by 0.25 Å and 25° (Table 2), thus making the O3B interaction stronger than that of O3A. In (II), atom O3 is contacted weakly to a C atom (D···A = 3.379 Å, H···A = 2.615° and D—H···A 126°). Therefore, the geometry exhibited by molecule (I)A probably arises from the maximization of the O3A hydrogen-bond interaction by a decrease of the donor···acceptor distance, with the concomitant displacement of the A-ring (see also Fig. 3). The deviation of the C11 plane (C9—C11—C12—O11) is 2° greater with respect to the main plane of the chair (C8—C9—C12—C13) in (I)B than in (I)A, the dihedral angles being 52.66 (13)° and 50.61 (16)°, respectively. The weak C1···O11 and C19···O11 hydrogen bonds could exert an effect, but this circumstance seems unlikely because the bonds are comparable in both independent molecules (Table 2). Therefore, a distant effect caused by the corresponding A-ring could be the most plausible explanation. The orientation of the C20 plane (C17—C20—O20—C21) with respect to the C5—C17 reference plane agrees well in both independent molecules, the values of the dihedral angles being 70.9 (1)° and 70.5 (1)° [(I)A and (I)B, resepctively]; thus, O17A and O17B are separated from the C20 plane by 1.593 (2) Å and 1.752 (3) Å, respectively. Concerning the C20 plane, the orientation of O21, as indicated by the torsion angle O20—C20—C21—O21, is plus synperiplanar [6.2 (5)° and 3.8 (5)° for (I)A and (I)B, respectively]. From Table 2, it is evident that O21B, unlike O21A, participates in an intramolecular interaction with O20B, thus forming a five-membered ring.

The comparison of (I) and (II) in XP indicated that the latter is closer to (I)B than to (I)A, the r.m.s. deviations being 0.14 Å and 0.28 Å, respectively. In the superposition between (I)B and (II), the major differences were encountered within the O20—C20—C21—O21 chain, namely for atoms O20 (0.319 Å), C21 (0.255 Å) and O21 (0.248 Å). However, in the superposition with (I)A, the major deviations occurred for atoms O3 (0.824 Å), O20 (0.452 Å) and O11 (0.388 Å). As with (II), O20 is plus synclinal with respect to the C16—C17 bond, the C16—C17—C20—O20 torsion angles being 44.9 (4), 47.9 (2) and 33.2° [(I)A, (I)B and II,respectively]. Note that O20 is further from C16 in (I) than in (II), possibly as a result of the steric hindrance introduced on the O atom by the members of the methyl group. Very weak C—H···O hydrogen bonds can have an effect. The C18···O20 interactions could be regarded as attractive contacts (Table 2), whereas, because of the bent geometry, the C22···O20 interactions (average D···A = 2.872 Å, H···A = 2.609 Å and D—H···A = 96°) could be considered to be repulsive ones, so that the net effect is the enlargement of the O20···C16 distance in (I). In (II), there is a very weak C16···O20 hydrogen bond (D···A = 2.855 Å, H···A = 2.404 Å and D—H···A = 107°), which was not observed in (I).

The longitudinal twist of the steroid nucleus, measured by the value of the pseudo-torsion angle C19—C10···C13—C18 (Duax et al., 1976), is similar in both independent molecules [2.6 (3)° and 2.7 (3)° for (I)A and (I)B, respectively], and this angle is somewhat smaller than that in (II) [4.6°]. In addition, the mutual orientation between O17 and C18 is in good agreement in the three structures, as shown by the value of the torsion angle C18—C13—C17—O17 [164.6 (2), 166.7 (4) and 165.4° for (I)A, (I)B and (II)]. The structural cohesion in the crystal of (I) is achieved through O—H···O -type hydrogen bonds. As shown in Fig. 3, chains are formed by the two independent molecules, which are linked via O21B···O3A hydrogen bonds, and by the two molecules and translated neighbors via O17A···O3B(x − 1, y + 1, z − 1) hydrogen bonds. The chains are propagated by O21A···O17A(-x, y + 1/2, −z) and O17B···O21B(-x + 1, y − 1/2, −z + 1) hydrogen bonds through the crystallographic twofold axis. The propagation direction is nearly perpendicular to the largest dimension of the steroid, and thus the chains are arranged into planes parallel to the b axis.

S2. Experimental

Compound (I) was obtained from LABORATORIOS GADOR SA, Buenos Aires, Argentina. Crystals suitable for X-ray diffraction were obtained via slow evaporation from an aqueous solution.

S3. Refinement

The positional parameters of the hydroxyl atoms H17 and H21 were refined with the distances to their carrier atoms restrained to 0.85 Å and U_iso equal to 1.5U_eq(O). H atoms attached to C atoms were constrained, with C—H distances of 0.98 Å for primary, 0.99 Å for secondary, 1 Å for tertiary and 0.95 Å for aromatic H atoms, and refined in a riding model with their isotropic thermal parameters constrained to 1.2 times larger than those of their hosts. For the final refinement, because the molecule lacks a significant anomalous scatterer at the Mo Kα wavelength, Friedel pairs were merged using the MERG 4 instruction implemented in SHELXL97. The correct enantiomer was chosen to agree with the known chirality of the steroid (Rausser et al., 1966).

Computing details

Data collection: COLLECT (Nonius, 1997–2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1991); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of the structure of (I), showing the numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. An XP (Sheldrick, 1991) plot depicting the superposition of the two independent molecules of (I), viz. (I)A (dashed lines) and (I)B (solid lines).
	Fig. 3. A partial packing diagram showing the O···O hydrogen bonds (dotted lines). Only H atoms attached to O are shown.

(I)

Crystal data

C22H28O5	F(000) = 800
Mr = 372.44	Dx = 1.31 Mg m^−3
Monoclinic, P21	Melting point = 473–478 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.4372 (4) Å	Cell parameters from 3579 reflections
b = 7.8901 (3) Å	θ = 1.0–25.0°
c = 21.1268 (9) Å	µ = 0.09 mm^−1
β = 97.896 (2)°	T = 120 K
V = 1888.42 (13) Å^3	Needle, colorless
Z = 4	0.18 × 0.06 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer	Rint = 0.050
ϕ scans and ω scans with κ offsets	θmax = 25.0°, θmin = 3.2°
6178 measured reflections	h = −13→13
3583 independent reflections	k = −9→7
2757 reflections with I > 2σ(I)	l = −25→24

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2)]
R[F^2 > 2σ(F^2)] = 0.044	(Δ/σ)max = 0.001
wR(F^2) = 0.099	Δρmax = 0.18 e Å^−3
S = 1.05	Δρmin = −0.19 e Å^−3
3583 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
500 parameters	Extinction coefficient: 0.033 (3)
5 restraints

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.

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

	x	y	z	Uiso*/Ueq
C1A	0.1997 (3)	0.3784 (5)	0.33142 (17)	0.0302 (9)
H1A	0.2486	0.3692	0.2987	0.036*
C1B	0.5283 (4)	0.1504 (5)	0.89312 (18)	0.0316 (10)
H1B	0.4925	0.2445	0.87	0.038*
C2A	0.1774 (3)	0.2384 (5)	0.36251 (17)	0.0330 (10)
H2A	0.2109	0.1341	0.3515	0.04*
C2B	0.6238 (3)	0.1805 (5)	0.93548 (17)	0.0325 (10)
H2B	0.6522	0.2932	0.9419	0.039*
C3A	0.1025 (3)	0.2404 (5)	0.41323 (18)	0.0337 (10)
C3B	0.6847 (3)	0.0427 (5)	0.97196 (17)	0.0309 (9)
C4A	0.0422 (3)	0.3984 (5)	0.42203 (18)	0.0334 (10)
H4A	−0.0144	0.4005	0.451	0.04*
C4B	0.6375 (3)	−0.1258 (5)	0.96047 (17)	0.0323 (10)
H4B	0.6764	−0.2178	0.9835	0.039*
C5A	0.0626 (3)	0.5426 (5)	0.39110 (16)	0.0288 (9)
C5B	0.5403 (3)	−0.1582 (5)	0.91834 (17)	0.0292 (9)
C6A	−0.0013 (3)	0.7037 (5)	0.40223 (17)	0.0313 (9)
H6A	0.0546	0.7855	0.4254	0.038*
H6B	−0.0638	0.6796	0.4291	0.038*
C6B	0.4949 (4)	−0.3355 (5)	0.90545 (17)	0.0348 (10)
H6C	0.4138	−0.3446	0.9166	0.042*
H6D	0.5457	−0.4166	0.9324	0.042*
C7A	−0.0568 (3)	0.7816 (5)	0.33896 (17)	0.0327 (10)
H7A	−0.091	0.8932	0.3474	0.039*
H7B	−0.1217	0.7077	0.3193	0.039*
C7B	0.4943 (4)	−0.3799 (5)	0.83468 (17)	0.0337 (10)
H7C	0.5767	−0.389	0.8257	0.04*
H7D	0.4562	−0.4918	0.826	0.04*
C8A	0.0328 (3)	0.8043 (5)	0.29221 (16)	0.0265 (9)
H8A	0.0954	0.8843	0.3117	0.032*
C8B	0.4293 (3)	−0.2484 (5)	0.79002 (16)	0.0258 (9)
H8B	0.3432	−0.2527	0.7941	0.031*
C9A	0.0915 (3)	0.6319 (5)	0.28122 (16)	0.0271 (9)
H9A	0.0254	0.5537	0.2649	0.033*
C9B	0.4766 (3)	−0.0672 (5)	0.80735 (16)	0.0263 (9)
H9B	0.5621	−0.0697	0.802	0.032*
C10A	0.1527 (3)	0.5502 (5)	0.34485 (17)	0.0295 (9)
C10B	0.4732 (3)	−0.0202 (5)	0.87923 (16)	0.0272 (9)
C11A	0.1692 (4)	0.6447 (5)	0.22734 (17)	0.0318 (10)
C11B	0.4197 (3)	0.0604 (5)	0.75856 (17)	0.0292 (9)
C12A	0.1100 (4)	0.7219 (5)	0.16516 (16)	0.0311 (9)
H12A	0.0428	0.6505	0.1465	0.037*
H12B	0.167	0.7297	0.134	0.037*
C12B	0.4358 (3)	0.0220 (5)	0.69022 (16)	0.0297 (9)
H12C	0.5207	0.025	0.6856	0.036*
H12D	0.3945	0.1084	0.6614	0.036*
C13A	0.0663 (3)	0.8994 (5)	0.18027 (16)	0.0260 (9)
C13B	0.3848 (3)	−0.1553 (5)	0.67214 (16)	0.0251 (8)
C14A	−0.0234 (3)	0.8779 (5)	0.22817 (16)	0.0261 (9)
H14A	−0.0852	0.7963	0.209	0.031*
C14B	0.4454 (3)	−0.2849 (5)	0.72050 (16)	0.0287 (9)
H14B	0.532	−0.277	0.7182	0.034*
C15A	−0.0807 (3)	1.0501 (5)	0.22907 (16)	0.0303 (9)
H15A	−0.0324	1.1265	0.2593	0.036*
H15B	−0.1604	1.0405	0.242	0.036*
C15B	0.4042 (3)	−0.4544 (5)	0.69034 (16)	0.0312 (9)
H15C	0.3242	−0.483	0.7	0.037*
H15D	0.4591	−0.5466	0.7063	0.037*
C16A	−0.0884 (3)	1.1184 (5)	0.15971 (17)	0.0289 (9)
H16A	−0.1722	1.1054	0.1395	0.035*
C16B	0.4034 (3)	−0.4271 (5)	0.61704 (16)	0.0298 (9)
H16B	0.4767	−0.4819	0.6058	0.036*
C17A	−0.0124 (3)	0.9921 (5)	0.12496 (16)	0.0255 (9)
C17B	0.4198 (3)	−0.2313 (5)	0.60916 (16)	0.0272 (9)
C18A	0.1736 (3)	1.0074 (6)	0.20684 (17)	0.0343 (10)
H18A	0.1473	1.1213	0.2168	0.051*
H18B	0.228	1.0151	0.1749	0.051*
H18C	0.2141	0.9546	0.2458	0.051*
C18B	0.2505 (3)	−0.1485 (6)	0.67085 (17)	0.0323 (10)
H18D	0.217	−0.0637	0.6396	0.048*
H18E	0.232	−0.1175	0.7133	0.048*
H18F	0.2165	−0.2598	0.6588	0.048*
C19A	0.2594 (3)	0.6596 (6)	0.37593 (18)	0.0357 (10)
H19A	0.3181	0.6682	0.3463	0.054*
H19B	0.2955	0.6059	0.4157	0.054*
H19C	0.2317	0.7733	0.3852	0.054*
C19B	0.3463 (3)	−0.0105 (6)	0.89654 (18)	0.0360 (10)
H19D	0.3021	0.0779	0.8709	0.054*
H19E	0.3494	0.0166	0.942	0.054*
H19F	0.3069	−0.12	0.8877	0.054*
C20A	0.0598 (3)	1.0702 (6)	0.07606 (17)	0.0296 (9)
C20B	0.3531 (3)	−0.1461 (5)	0.55025 (16)	0.0309 (9)
C21A	0.0591 (3)	0.9786 (5)	0.01302 (17)	0.0338 (10)
H21C	0.0794	0.858	0.0213	0.041*
H21D	−0.0213	0.9835	−0.0113	0.041*
C21B	0.4223 (3)	−0.0232 (6)	0.51536 (17)	0.0369 (10)
H21E	0.4602	0.062	0.546	0.044*
H21F	0.4855	−0.0851	0.4974	0.044*
C22A	−0.0596 (4)	1.3063 (5)	0.15932 (18)	0.0344 (10)
H22A	0.0211	1.3247	0.1806	0.052*
H22B	−0.1151	1.3688	0.182	0.052*
H22C	−0.0661	1.3465	0.1151	0.052*
C22B	0.2999 (4)	−0.5138 (5)	0.57646 (18)	0.0371 (10)
H22D	0.3042	−0.4928	0.5311	0.056*
H22E	0.2256	−0.4683	0.5875	0.056*
H22F	0.3032	−0.6361	0.5847	0.056*
O3A	0.0924 (3)	0.1119 (4)	0.44623 (14)	0.0479 (8)
O3B	0.7728 (2)	0.0717 (4)	1.01224 (12)	0.0402 (7)
O11A	0.2722 (2)	0.6003 (4)	0.23357 (12)	0.0389 (7)
O11B	0.3640 (2)	0.1841 (4)	0.77205 (12)	0.0377 (7)
O17A	−0.0898 (2)	0.8660 (4)	0.09262 (12)	0.0310 (7)
H17A	−0.138 (3)	0.926 (5)	0.0647 (17)	0.047*
O17B	0.5435 (2)	−0.1936 (4)	0.61015 (12)	0.0311 (7)
H17B	0.563 (3)	−0.271 (5)	0.5838 (17)	0.047*
O20A	0.1170 (2)	1.1993 (4)	0.08735 (12)	0.0378 (7)
O20B	0.2488 (2)	−0.1672 (4)	0.53174 (12)	0.0368 (7)
O21A	0.1409 (2)	1.0515 (4)	−0.02443 (12)	0.0371 (7)
H21A	0.111 (4)	1.148 (4)	−0.042 (2)	0.056*
O21B	0.3500 (2)	0.0604 (4)	0.46558 (13)	0.0427 (8)
H21B	0.278 (3)	0.040 (7)	0.468 (2)	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.029 (2)	0.036 (3)	0.0241 (19)	0.0033 (19)	−0.0014 (16)	0.0016 (19)
C1B	0.039 (2)	0.028 (2)	0.028 (2)	0.0005 (19)	0.0044 (18)	−0.0028 (18)
C2A	0.034 (2)	0.032 (2)	0.033 (2)	0.0046 (19)	0.0031 (18)	0.002 (2)
C2B	0.034 (2)	0.032 (2)	0.030 (2)	−0.0011 (19)	0.0029 (18)	−0.0020 (19)
C3A	0.037 (2)	0.029 (2)	0.035 (2)	−0.002 (2)	0.0023 (18)	0.006 (2)
C3B	0.032 (2)	0.033 (2)	0.028 (2)	−0.001 (2)	0.0043 (17)	−0.0029 (19)
C4A	0.031 (2)	0.039 (3)	0.031 (2)	0.002 (2)	0.0058 (17)	0.006 (2)
C4B	0.035 (2)	0.036 (3)	0.026 (2)	0.0040 (19)	0.0034 (17)	0.0036 (19)
C5A	0.028 (2)	0.033 (2)	0.0240 (19)	0.0029 (19)	−0.0002 (15)	−0.0006 (19)
C5B	0.031 (2)	0.034 (2)	0.0233 (19)	0.0000 (19)	0.0072 (16)	0.0046 (18)
C6A	0.037 (2)	0.033 (2)	0.025 (2)	0.0055 (19)	0.0095 (17)	0.0037 (19)
C6B	0.041 (2)	0.032 (2)	0.030 (2)	0.000 (2)	0.0001 (18)	0.0040 (19)
C7A	0.034 (2)	0.033 (3)	0.033 (2)	0.0052 (19)	0.0115 (17)	0.0046 (19)
C7B	0.044 (2)	0.029 (2)	0.029 (2)	0.0017 (19)	0.0050 (18)	0.0057 (19)
C8A	0.030 (2)	0.024 (2)	0.0266 (19)	0.0029 (18)	0.0070 (16)	0.0050 (17)
C8B	0.026 (2)	0.028 (2)	0.0242 (19)	0.0020 (17)	0.0068 (15)	0.0076 (17)
C9A	0.030 (2)	0.028 (2)	0.0234 (19)	0.0008 (17)	0.0068 (16)	0.0012 (17)
C9B	0.027 (2)	0.026 (2)	0.0245 (19)	−0.0029 (17)	0.0008 (15)	0.0005 (17)
C10A	0.029 (2)	0.031 (2)	0.028 (2)	0.0015 (18)	0.0031 (15)	0.0025 (19)
C10B	0.026 (2)	0.031 (2)	0.026 (2)	0.0018 (18)	0.0049 (16)	0.0008 (18)
C11A	0.036 (2)	0.030 (2)	0.029 (2)	0.005 (2)	0.0043 (17)	−0.0011 (19)
C11B	0.030 (2)	0.026 (2)	0.030 (2)	−0.0012 (19)	0.0011 (16)	0.0017 (19)
C12A	0.035 (2)	0.034 (2)	0.0244 (19)	0.0048 (19)	0.0055 (17)	−0.0006 (18)
C12B	0.034 (2)	0.028 (2)	0.0275 (19)	−0.0008 (18)	0.0063 (16)	0.0058 (18)
C13A	0.030 (2)	0.026 (2)	0.0230 (19)	0.0015 (17)	0.0053 (16)	0.0013 (17)
C13B	0.027 (2)	0.026 (2)	0.0228 (18)	−0.0001 (17)	0.0052 (15)	0.0018 (17)
C14A	0.025 (2)	0.030 (2)	0.0238 (19)	−0.0010 (17)	0.0068 (15)	0.0017 (18)
C14B	0.030 (2)	0.032 (2)	0.0252 (19)	0.0014 (18)	0.0075 (16)	0.0038 (18)
C15A	0.033 (2)	0.029 (2)	0.031 (2)	0.0074 (19)	0.0106 (16)	0.0045 (19)
C15B	0.038 (2)	0.030 (2)	0.027 (2)	0.004 (2)	0.0076 (17)	0.0007 (19)
C16A	0.030 (2)	0.030 (2)	0.026 (2)	0.0012 (18)	0.0026 (16)	−0.0033 (18)
C16B	0.032 (2)	0.030 (2)	0.0278 (19)	−0.0025 (19)	0.0076 (16)	−0.0017 (18)
C17A	0.031 (2)	0.023 (2)	0.0225 (19)	−0.0003 (17)	0.0031 (16)	0.0001 (17)
C17B	0.023 (2)	0.036 (2)	0.0236 (19)	−0.0027 (17)	0.0051 (16)	0.0013 (18)
C18A	0.034 (2)	0.042 (3)	0.027 (2)	−0.004 (2)	0.0048 (17)	0.001 (2)
C18B	0.029 (2)	0.037 (3)	0.032 (2)	0.0024 (19)	0.0059 (17)	0.003 (2)
C19A	0.031 (2)	0.044 (3)	0.031 (2)	−0.001 (2)	0.0000 (17)	0.000 (2)
C19B	0.033 (2)	0.043 (3)	0.032 (2)	0.005 (2)	0.0063 (17)	−0.005 (2)
C20A	0.028 (2)	0.033 (3)	0.027 (2)	0.002 (2)	0.0034 (16)	0.0035 (19)
C20B	0.033 (2)	0.038 (3)	0.023 (2)	−0.001 (2)	0.0084 (17)	−0.0038 (19)
C21A	0.035 (2)	0.039 (3)	0.030 (2)	−0.004 (2)	0.0121 (18)	0.001 (2)
C21B	0.037 (2)	0.045 (3)	0.028 (2)	0.001 (2)	0.0008 (18)	0.012 (2)
C22A	0.043 (2)	0.032 (2)	0.027 (2)	0.005 (2)	0.0046 (18)	0.0033 (19)
C22B	0.047 (3)	0.029 (2)	0.036 (2)	−0.006 (2)	0.0099 (19)	−0.002 (2)
O3A	0.055 (2)	0.0391 (19)	0.0532 (19)	0.0036 (15)	0.0189 (15)	0.0137 (16)
O3B	0.0390 (16)	0.0412 (19)	0.0375 (15)	0.0000 (14)	−0.0044 (13)	−0.0030 (14)
O11A	0.0340 (17)	0.048 (2)	0.0356 (15)	0.0119 (14)	0.0086 (12)	0.0066 (14)
O11B	0.0446 (18)	0.0316 (17)	0.0356 (16)	0.0075 (14)	0.0011 (13)	−0.0009 (13)
O17A	0.0339 (16)	0.0311 (17)	0.0270 (14)	−0.0012 (13)	0.0002 (11)	0.0001 (13)
O17B	0.0262 (14)	0.0382 (17)	0.0301 (14)	−0.0002 (13)	0.0084 (11)	−0.0013 (13)
O20A	0.0451 (18)	0.0341 (18)	0.0358 (15)	−0.0052 (15)	0.0115 (13)	−0.0004 (14)
O20B	0.0312 (16)	0.0464 (19)	0.0315 (15)	−0.0022 (14)	0.0000 (12)	0.0053 (14)
O21A	0.0419 (17)	0.0396 (19)	0.0320 (15)	0.0014 (15)	0.0134 (12)	0.0057 (14)
O21B	0.0378 (17)	0.052 (2)	0.0385 (15)	0.0005 (16)	0.0061 (13)	0.0203 (15)

Geometric parameters (Å, º)

C1A—C2A	1.328 (5)	C13A—C18A	1.535 (5)
C1A—C10A	1.500 (6)	C13A—C14A	1.547 (5)
C1A—H1A	0.95	C13A—C17A	1.556 (5)
C1B—C2B	1.335 (5)	C13B—C18B	1.534 (5)
C1B—C10B	1.498 (6)	C13B—C14B	1.541 (5)
C1B—H1B	0.95	C13B—C17B	1.561 (5)
C2A—C3A	1.461 (5)	C14A—C15A	1.509 (5)
C2A—H2A	0.95	C14A—H14A	1
C2B—C3B	1.454 (6)	C14B—C15B	1.528 (6)
C2B—H2B	0.95	C14B—H14B	1
C3A—O3A	1.245 (5)	C15A—C16A	1.552 (5)
C3A—C4A	1.449 (6)	C15A—H15A	0.99
C3B—O3B	1.248 (4)	C15A—H15B	0.99
C3B—C4B	1.443 (6)	C15B—C16B	1.562 (5)
C4A—C5A	1.348 (5)	C15B—H15C	0.99
C4A—H4A	0.95	C15B—H15D	0.99
C4B—C5B	1.350 (5)	C16A—C22A	1.518 (6)
C4B—H4B	0.95	C16A—C17A	1.569 (5)
C5A—C6A	1.501 (5)	C16A—H16A	1
C5A—C10A	1.515 (5)	C16B—C22B	1.526 (5)
C5B—C6B	1.504 (6)	C16B—C17B	1.568 (6)
C5B—C10B	1.511 (5)	C16B—H16B	1
C6A—C7A	1.528 (5)	C17A—O17A	1.440 (4)
C6A—H6A	0.99	C17A—C20A	1.537 (5)
C6A—H6B	0.99	C17B—O17B	1.443 (4)
C6B—C7B	1.535 (5)	C17B—C20B	1.524 (5)
C6B—H6C	0.99	C18A—H18A	0.98
C6B—H6D	0.99	C18A—H18B	0.98
C7A—C8A	1.528 (5)	C18A—H18C	0.98
C7A—H7A	0.99	C18B—H18D	0.98
C7A—H7B	0.99	C18B—H18E	0.98
C7B—C8B	1.525 (5)	C18B—H18F	0.98
C7B—H7C	0.99	C19A—H19A	0.98
C7B—H7D	0.99	C19A—H19B	0.98
C8A—C14A	1.530 (5)	C19A—H19C	0.98
C8A—C9A	1.549 (5)	C19B—H19D	0.98
C8A—H8A	1	C19B—H19E	0.98
C8B—C14B	1.532 (5)	C19B—H19F	0.98
C8B—C9B	1.555 (5)	C20A—O20A	1.217 (5)
C8B—H8B	1	C20A—C21A	1.514 (5)
C9A—C11A	1.541 (5)	C20B—O20B	1.214 (4)
C9A—C10A	1.566 (5)	C20B—C21B	1.507 (5)
C9A—H9A	1	C21A—O21A	1.427 (4)
C9B—C11B	1.522 (5)	C21A—H21C	0.99
C9B—C10B	1.569 (5)	C21A—H21D	0.99
C9B—H9B	1	C21B—O21B	1.409 (4)
C10A—C19A	1.565 (5)	C21B—H21E	0.99
C10B—C19B	1.547 (5)	C21B—H21F	0.99
C11A—O11A	1.219 (4)	C22A—H22A	0.98
C11A—C12A	1.520 (5)	C22A—H22B	0.98
C11B—O11B	1.220 (5)	C22A—H22C	0.98
C11B—C12B	1.511 (5)	C22B—H22D	0.98
C12A—C13A	1.535 (5)	C22B—H22E	0.98
C12A—H12A	0.99	C22B—H22F	0.98
C12A—H12B	0.99	O17A—H17A	0.89 (3)
C12B—C13B	1.543 (5)	O17B—H17B	0.88 (3)
C12B—H12C	0.99	O21A—H21A	0.89 (3)
C12B—H12D	0.99	O21B—H21B	0.85 (3)
C2A—C1A—C10A	124.0 (4)	C14A—C13A—C17A	100.1 (3)
C2A—C1A—H1A	118	C18B—C13B—C14B	113.2 (3)
C10A—C1A—H1A	118	C18B—C13B—C12B	108.4 (3)
C2B—C1B—C10B	125.1 (4)	C14B—C13B—C12B	108.5 (3)
C2B—C1B—H1B	117.5	C18B—C13B—C17B	111.8 (3)
C10B—C1B—H1B	117.5	C14B—C13B—C17B	99.5 (3)
C1A—C2A—C3A	121.7 (4)	C12B—C13B—C17B	115.3 (3)
C1A—C2A—H2A	119.1	C15A—C14A—C8A	117.4 (3)
C3A—C2A—H2A	119.1	C15A—C14A—C13A	103.7 (3)
C1B—C2B—C3B	120.7 (4)	C8A—C14A—C13A	112.6 (3)
C1B—C2B—H2B	119.6	C15A—C14A—H14A	107.5
C3B—C2B—H2B	119.6	C8A—C14A—H14A	107.5
O3A—C3A—C4A	123.2 (4)	C13A—C14A—H14A	107.5
O3A—C3A—C2A	120.7 (4)	C15B—C14B—C8B	119.5 (3)
C4A—C3A—C2A	116.1 (4)	C15B—C14B—C13B	102.7 (3)
O3B—C3B—C4B	122.2 (4)	C8B—C14B—C13B	114.1 (3)
O3B—C3B—C2B	120.5 (4)	C15B—C14B—H14B	106.6
C4B—C3B—C2B	117.3 (3)	C8B—C14B—H14B	106.6
C5A—C4A—C3A	123.2 (4)	C13B—C14B—H14B	106.6
C5A—C4A—H4A	118.4	C14A—C15A—C16A	105.6 (3)
C3A—C4A—H4A	118.4	C14A—C15A—H15A	110.6
C5B—C4B—C3B	122.7 (4)	C16A—C15A—H15A	110.6
C5B—C4B—H4B	118.6	C14A—C15A—H15B	110.6
C3B—C4B—H4B	118.6	C16A—C15A—H15B	110.6
C4A—C5A—C6A	121.2 (3)	H15A—C15A—H15B	108.7
C4A—C5A—C10A	121.6 (4)	C14B—C15B—C16B	104.6 (3)
C6A—C5A—C10A	117.2 (3)	C14B—C15B—H15C	110.8
C4B—C5B—C6B	121.9 (4)	C16B—C15B—H15C	110.8
C4B—C5B—C10B	122.3 (4)	C14B—C15B—H15D	110.8
C6B—C5B—C10B	115.7 (3)	C16B—C15B—H15D	110.8
C5A—C6A—C7A	110.9 (3)	H15C—C15B—H15D	108.9
C5A—C6A—H6A	109.5	C22A—C16A—C15A	111.1 (3)
C7A—C6A—H6A	109.5	C22A—C16A—C17A	118.9 (3)
C5A—C6A—H6B	109.5	C15A—C16A—C17A	104.9 (3)
C7A—C6A—H6B	109.5	C22A—C16A—H16A	107.1
H6A—C6A—H6B	108.1	C15A—C16A—H16A	107.1
C5B—C6B—C7B	110.1 (3)	C17A—C16A—H16A	107.1
C5B—C6B—H6C	109.6	C22B—C16B—C15B	113.2 (3)
C7B—C6B—H6C	109.6	C22B—C16B—C17B	118.5 (3)
C5B—C6B—H6D	109.6	C15B—C16B—C17B	104.9 (3)
C7B—C6B—H6D	109.6	C22B—C16B—H16B	106.5
H6C—C6B—H6D	108.2	C15B—C16B—H16B	106.5
C6A—C7A—C8A	112.2 (3)	C17B—C16B—H16B	106.5
C6A—C7A—H7A	109.2	O17A—C17A—C20A	108.0 (3)
C8A—C7A—H7A	109.2	O17A—C17A—C13A	106.6 (3)
C6A—C7A—H7B	109.2	C20A—C17A—C13A	112.6 (3)
C8A—C7A—H7B	109.2	O17A—C17A—C16A	108.5 (3)
H7A—C7A—H7B	107.9	C20A—C17A—C16A	116.3 (3)
C8B—C7B—C6B	112.6 (3)	C13A—C17A—C16A	104.3 (3)
C8B—C7B—H7C	109.1	O17B—C17B—C20B	107.5 (3)
C6B—C7B—H7C	109.1	O17B—C17B—C13B	105.9 (3)
C8B—C7B—H7D	109.1	C20B—C17B—C13B	111.6 (3)
C6B—C7B—H7D	109.1	O17B—C17B—C16B	109.4 (3)
H7C—C7B—H7D	107.8	C20B—C17B—C16B	117.9 (3)
C7A—C8A—C14A	112.3 (3)	C13B—C17B—C16B	103.9 (3)
C7A—C8A—C9A	109.7 (3)	C13A—C18A—H18A	109.5
C14A—C8A—C9A	109.8 (3)	C13A—C18A—H18B	109.5
C7A—C8A—H8A	108.3	H18A—C18A—H18B	109.5
C14A—C8A—H8A	108.3	C13A—C18A—H18C	109.5
C9A—C8A—H8A	108.3	H18A—C18A—H18C	109.5
C7B—C8B—C14B	110.6 (3)	H18B—C18A—H18C	109.5
C7B—C8B—C9B	110.8 (3)	C13B—C18B—H18D	109.5
C14B—C8B—C9B	108.3 (3)	C13B—C18B—H18E	109.5
C7B—C8B—H8B	109	H18D—C18B—H18E	109.5
C14B—C8B—H8B	109	C13B—C18B—H18F	109.5
C9B—C8B—H8B	109	H18D—C18B—H18F	109.5
C11A—C9A—C8A	111.0 (3)	H18E—C18B—H18F	109.5
C11A—C9A—C10A	115.2 (3)	C10A—C19A—H19A	109.5
C8A—C9A—C10A	112.6 (3)	C10A—C19A—H19B	109.5
C11A—C9A—H9A	105.7	H19A—C19A—H19B	109.5
C8A—C9A—H9A	105.7	C10A—C19A—H19C	109.5
C10A—C9A—H9A	105.7	H19A—C19A—H19C	109.5
C11B—C9B—C8B	110.3 (3)	H19B—C19A—H19C	109.5
C11B—C9B—C10B	115.7 (3)	C10B—C19B—H19D	109.5
C8B—C9B—C10B	113.0 (3)	C10B—C19B—H19E	109.5
C11B—C9B—H9B	105.6	H19D—C19B—H19E	109.5
C8B—C9B—H9B	105.6	C10B—C19B—H19F	109.5
C10B—C9B—H9B	105.6	H19D—C19B—H19F	109.5
C1A—C10A—C5A	112.3 (3)	H19E—C19B—H19F	109.5
C1A—C10A—C19A	107.4 (3)	O20A—C20A—C21A	120.6 (3)
C5A—C10A—C19A	108.2 (3)	O20A—C20A—C17A	121.9 (3)
C1A—C10A—C9A	109.8 (3)	C21A—C20A—C17A	117.5 (3)
C5A—C10A—C9A	107.9 (3)	O20B—C20B—C21B	119.3 (3)
C19A—C10A—C9A	111.3 (3)	O20B—C20B—C17B	124.2 (3)
C1B—C10B—C5B	111.8 (3)	C21B—C20B—C17B	116.5 (3)
C1B—C10B—C19B	107.0 (3)	O21A—C21A—C20A	111.8 (3)
C5B—C10B—C19B	109.2 (3)	O21A—C21A—H21C	109.3
C1B—C10B—C9B	109.6 (3)	C20A—C21A—H21C	109.3
C5B—C10B—C9B	106.3 (3)	O21A—C21A—H21D	109.3
C19B—C10B—C9B	112.9 (3)	C20A—C21A—H21D	109.3
O11A—C11A—C12A	121.2 (3)	H21C—C21A—H21D	107.9
O11A—C11A—C9A	123.3 (3)	O21B—C21B—C20B	111.8 (3)
C12A—C11A—C9A	115.6 (3)	O21B—C21B—H21E	109.3
O11B—C11B—C12B	121.3 (3)	C20B—C21B—H21E	109.3
O11B—C11B—C9B	124.0 (3)	O21B—C21B—H21F	109.3
C12B—C11B—C9B	114.7 (3)	C20B—C21B—H21F	109.3
C11A—C12A—C13A	107.8 (3)	H21E—C21B—H21F	107.9
C11A—C12A—H12A	110.2	C16A—C22A—H22A	109.5
C13A—C12A—H12A	110.2	C16A—C22A—H22B	109.5
C11A—C12A—H12B	110.2	H22A—C22A—H22B	109.5
C13A—C12A—H12B	110.2	C16A—C22A—H22C	109.5
H12A—C12A—H12B	108.5	H22A—C22A—H22C	109.5
C11B—C12B—C13B	109.1 (3)	H22B—C22A—H22C	109.5
C11B—C12B—H12C	109.9	C16B—C22B—H22D	109.5
C13B—C12B—H12C	109.9	C16B—C22B—H22E	109.5
C11B—C12B—H12D	109.9	H22D—C22B—H22E	109.5
C13B—C12B—H12D	109.9	C16B—C22B—H22F	109.5
H12C—C12B—H12D	108.3	H22D—C22B—H22F	109.5
C12A—C13A—C18A	108.4 (3)	H22E—C22B—H22F	109.5
C12A—C13A—C14A	107.5 (3)	C17A—O17A—H17A	103 (3)
C18A—C13A—C14A	113.0 (3)	C17B—O17B—H17B	100 (3)
C12A—C13A—C17A	116.3 (3)	C21A—O21A—H21A	109 (3)
C18A—C13A—C17A	111.4 (3)	C21B—O21B—H21B	110 (3)
C10A—C1A—C2A—C3A	0.5 (6)	C11B—C12B—C13B—C18B	67.3 (4)
C10B—C1B—C2B—C3B	1.1 (6)	C11B—C12B—C13B—C14B	−56.0 (4)
C1A—C2A—C3A—O3A	−172.5 (4)	C11B—C12B—C13B—C17B	−166.5 (3)
C1A—C2A—C3A—C4A	7.6 (6)	C7A—C8A—C14A—C15A	60.3 (4)
C1B—C2B—C3B—O3B	−178.9 (3)	C9A—C8A—C14A—C15A	−177.4 (3)
C1B—C2B—C3B—C4B	−0.2 (6)	C7A—C8A—C14A—C13A	−179.3 (3)
O3A—C3A—C4A—C5A	172.7 (4)	C9A—C8A—C14A—C13A	−57.1 (4)
C2A—C3A—C4A—C5A	−7.4 (6)	C12A—C13A—C14A—C15A	−168.1 (3)
O3B—C3B—C4B—C5B	178.1 (3)	C18A—C13A—C14A—C15A	72.4 (4)
C2B—C3B—C4B—C5B	−0.6 (5)	C17A—C13A—C14A—C15A	−46.2 (3)
C3A—C4A—C5A—C6A	−179.5 (3)	C12A—C13A—C14A—C8A	63.9 (4)
C3A—C4A—C5A—C10A	−0.8 (6)	C18A—C13A—C14A—C8A	−55.6 (4)
C3B—C4B—C5B—C6B	177.9 (3)	C17A—C13A—C14A—C8A	−174.1 (3)
C3B—C4B—C5B—C10B	0.4 (6)	C7B—C8B—C14B—C15B	59.4 (5)
C4A—C5A—C6A—C7A	−128.7 (4)	C9B—C8B—C14B—C15B	−178.9 (3)
C10A—C5A—C6A—C7A	52.5 (4)	C7B—C8B—C14B—C13B	−178.7 (3)
C4B—C5B—C6B—C7B	−119.9 (4)	C9B—C8B—C14B—C13B	−57.0 (4)
C10B—C5B—C6B—C7B	57.7 (4)	C18B—C13B—C14B—C15B	69.5 (4)
C5A—C6A—C7A—C8A	−52.9 (5)	C12B—C13B—C14B—C15B	−170.1 (3)
C5B—C6B—C7B—C8B	−52.7 (4)	C17B—C13B—C14B—C15B	−49.3 (3)
C6A—C7A—C8A—C14A	178.5 (3)	C18B—C13B—C14B—C8B	−61.3 (4)
C6A—C7A—C8A—C9A	56.1 (4)	C12B—C13B—C14B—C8B	59.0 (4)
C6B—C7B—C8B—C14B	172.2 (3)	C17B—C13B—C14B—C8B	179.9 (3)
C6B—C7B—C8B—C9B	52.1 (4)	C8A—C14A—C15A—C16A	160.3 (3)
C7A—C8A—C9A—C11A	172.0 (3)	C13A—C14A—C15A—C16A	35.4 (4)
C14A—C8A—C9A—C11A	48.2 (4)	C8B—C14B—C15B—C16B	165.4 (3)
C7A—C8A—C9A—C10A	−57.1 (4)	C13B—C14B—C15B—C16B	38.0 (3)
C14A—C8A—C9A—C10A	179.1 (3)	C14A—C15A—C16A—C22A	−139.8 (3)
C7B—C8B—C9B—C11B	174.4 (3)	C14A—C15A—C16A—C17A	−10.2 (4)
C14B—C8B—C9B—C11B	52.9 (4)	C14B—C15B—C16B—C22B	−141.8 (3)
C7B—C8B—C9B—C10B	−54.3 (4)	C14B—C15B—C16B—C17B	−11.2 (4)
C14B—C8B—C9B—C10B	−175.8 (3)	C12A—C13A—C17A—O17A	39.8 (4)
C2A—C1A—C10A—C5A	−8.3 (5)	C18A—C13A—C17A—O17A	164.7 (3)
C2A—C1A—C10A—C19A	110.5 (4)	C14A—C13A—C17A—O17A	−75.6 (3)
C2A—C1A—C10A—C9A	−128.3 (4)	C12A—C13A—C17A—C20A	−78.5 (4)
C4A—C5A—C10A—C1A	8.3 (5)	C18A—C13A—C17A—C20A	46.4 (4)
C6A—C5A—C10A—C1A	−172.9 (3)	C14A—C13A—C17A—C20A	166.1 (3)
C4A—C5A—C10A—C19A	−110.0 (4)	C12A—C13A—C17A—C16A	154.5 (3)
C6A—C5A—C10A—C19A	68.8 (4)	C18A—C13A—C17A—C16A	−80.6 (3)
C4A—C5A—C10A—C9A	129.5 (4)	C14A—C13A—C17A—C16A	39.2 (3)
C6A—C5A—C10A—C9A	−51.8 (4)	C22A—C16A—C17A—O17A	−140.2 (3)
C11A—C9A—C10A—C1A	−55.4 (4)	C15A—C16A—C17A—O17A	94.9 (3)
C8A—C9A—C10A—C1A	175.8 (3)	C22A—C16A—C17A—C20A	−18.2 (5)
C11A—C9A—C10A—C5A	−178.1 (3)	C15A—C16A—C17A—C20A	−143.2 (3)
C8A—C9A—C10A—C5A	53.1 (4)	C22A—C16A—C17A—C13A	106.4 (4)
C11A—C9A—C10A—C19A	63.4 (4)	C15A—C16A—C17A—C13A	−18.5 (4)
C8A—C9A—C10A—C19A	−65.4 (4)	C18B—C13B—C17B—O17B	166.7 (3)
C2B—C1B—C10B—C5B	−1.1 (5)	C14B—C13B—C17B—O17B	−73.5 (3)
C2B—C1B—C10B—C19B	118.4 (4)	C12B—C13B—C17B—O17B	42.2 (4)
C2B—C1B—C10B—C9B	−118.8 (4)	C18B—C13B—C17B—C20B	50.0 (4)
C4B—C5B—C10B—C1B	0.3 (5)	C14B—C13B—C17B—C20B	169.8 (3)
C6B—C5B—C10B—C1B	−177.3 (3)	C12B—C13B—C17B—C20B	−74.5 (4)
C4B—C5B—C10B—C19B	−117.9 (4)	C18B—C13B—C17B—C16B	−78.1 (4)
C6B—C5B—C10B—C19B	64.5 (4)	C14B—C13B—C17B—C16B	41.7 (3)
C4B—C5B—C10B—C9B	120.0 (4)	C12B—C13B—C17B—C16B	157.5 (3)
C6B—C5B—C10B—C9B	−57.6 (4)	C22B—C16B—C17B—O17B	−139.1 (3)
C11B—C9B—C10B—C1B	−55.6 (4)	C15B—C16B—C17B—O17B	93.6 (3)
C8B—C9B—C10B—C1B	175.8 (3)	C22B—C16B—C17B—C20B	−15.8 (5)
C11B—C9B—C10B—C5B	−176.7 (3)	C15B—C16B—C17B—C20B	−143.2 (3)
C8B—C9B—C10B—C5B	54.8 (4)	C22B—C16B—C17B—C13B	108.2 (3)
C11B—C9B—C10B—C19B	63.6 (4)	C15B—C16B—C17B—C13B	−19.2 (4)
C8B—C9B—C10B—C19B	−65.0 (4)	O17A—C17A—C20A—O20A	167.1 (3)
C8A—C9A—C11A—O11A	127.2 (4)	C13A—C17A—C20A—O20A	−75.4 (5)
C10A—C9A—C11A—O11A	−2.4 (6)	C16A—C17A—C20A—O20A	44.9 (5)
C8A—C9A—C11A—C12A	−51.1 (4)	O17A—C17A—C20A—C21A	−14.0 (4)
C10A—C9A—C11A—C12A	179.3 (3)	C13A—C17A—C20A—C21A	103.5 (4)
C8B—C9B—C11B—O11B	122.7 (4)	C16A—C17A—C20A—C21A	−136.2 (3)
C10B—C9B—C11B—O11B	−7.1 (5)	O17B—C17B—C20B—O20B	172.1 (4)
C8B—C9B—C11B—C12B	−56.5 (4)	C13B—C17B—C20B—O20B	−72.2 (5)
C10B—C9B—C11B—C12B	173.6 (3)	C16B—C17B—C20B—O20B	47.9 (5)
O11A—C11A—C12A—C13A	−121.0 (4)	O17B—C17B—C20B—C21B	−10.5 (4)
C9A—C11A—C12A—C13A	57.4 (4)	C13B—C17B—C20B—C21B	105.2 (4)
O11B—C11B—C12B—C13B	−121.4 (4)	C16B—C17B—C20B—C21B	−134.7 (4)
C9B—C11B—C12B—C13B	57.9 (4)	O20A—C20A—C21A—O21A	6.5 (5)
C11A—C12A—C13A—C18A	61.7 (4)	C17A—C20A—C21A—O21A	−172.5 (3)
C11A—C12A—C13A—C14A	−60.7 (4)	O20B—C20B—C21B—O21B	3.3 (5)
C11A—C12A—C13A—C17A	−171.8 (3)	C17B—C20B—C21B—O21B	−174.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17A—H17A···O3B^i	0.89 (3)	1.81 (3)	2.694 (4)	173 (4)
O17B—H17B···O21B^ii	0.88 (3)	2.03 (3)	2.889 (4)	165 (4)
O21A—H21A···O17A^iii	0.89 (3)	2.03 (3)	2.888 (4)	163 (4)
O21B—H21B···O20B	0.85 (3)	2.17 (5)	2.638 (4)	115 (4)
O21B—H21B···O3A	0.85 (3)	2.19 (4)	2.946 (4)	149 (5)
C1A—H1A···O11A	0.95	2.32	2.915 (5)	120
C1B—H1B···O11B	0.95	2.41	2.970 (5)	117
C18A—H18B···O20A	0.98	2.55	2.937 (4)	104
C18B—H18D···O20B	0.98	2.50	2.942 (4)	107
C19A—H19A···O11A	0.98	2.43	3.067 (4)	122
C19B—H19D···O11B	0.98	2.44	3.076 (5)	122

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