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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1271–o1272.
Published online 2009 May 14. doi:  10.1107/S1600536809016997
PMCID: PMC2969566

16α,17α-Ep­oxy-5α-hydr­oxy-6β-nitrooxy-20-oxopregnan-3β-yl acetate

Abstract

The title steroid, C23H33NO8, is a pregnane derivative obtained regio-, stereo- and chemoselectively from the ring opening of the corresponding 5α,6α;16α,17α-diepoxide with bis­muth(III) nitrate. There are two symmetry-independent mol­ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. All rings are trans-fused. The conformations of the six-membered rings are close to chair forms, while the five-membered ring adopts an envelope conformation. The mol­ecules are held together by an extensive O—H(...)O hydrogen-bonding network of chains runnning along the a axis.

Related literature

For epoxy­steroid chemistry, see: Salvador et al. (2006 [triangle], 2008 [triangle]); Pinto et al. (2008a [triangle]). For the synthesis of β-hydr­oxy nitrates, see: Pinto et al. (2007a [triangle]). For the structures of 5α-hydr­oxy-6β-substituted steroids, see: Pinto et al. (2007b [triangle], 2008b [triangle],c [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1271-scheme1.jpg

Experimental

Crystal data

  • C23H33NO8
  • M r = 451.50
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1271-efi1.jpg
  • a = 10.9740 (3) Å
  • b = 11.0721 (3) Å
  • c = 11.1686 (3) Å
  • α = 77.2135 (15)°
  • β = 73.2087 (14)°
  • γ = 64.3465 (14)°
  • V = 1163.81 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 223 K
  • 0.32 × 0.17 × 0.06 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.947, T max = 0.994
  • 24934 measured reflections
  • 5770 independent reflections
  • 4806 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.118
  • S = 1.04
  • 5770 reflections
  • 587 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016997/bt2943sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016997/bt2943Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Fundação para a Ciência e Tecnologia. RMAP thanks the FCT for a grant (No. SFRH/BD/18013/2004).

supplementary crystallographic information

Comment

Epoxysteroids are amongst the most versatile intermediates in the synthesis of biologically important active molecules (Salvador et al., 2006, 2008; Pinto et al., 2008a). Recently, we have reported a new process for the preparation of β-hydroxy nitrates by the use of stoichiometric amounts of bismuth(III) nitrate, in the ring opening reaction of epoxides (Pinto et al., 2007a). Interestingly, the bismuth(III) salt showed a dual action, both as nucleophile donor and reaction promoter. Using this procedure, the ring opening of 5α,6α;16α,17α-diepoxy-20-oxopregnan-3β-yl acetate afforded regio-, stereo- and chemoselectively the title compound (I), bearing an intact 16α,17α-epoxide function (Pinto et al., 2007a).

In order to unequivocally demonstrate the trans-diaxial nature of the ring opening of the 5α,6α;16α,17α-diepoxysteroid and the chemoselectivity for the epoxide fused to ring B, X-ray crystallography study was carried out on suitable single crystals of (I). Related X-ray diffraction studies on 5α-hydroxy-6β-substituted steroids have been recently published by our group (Pinto et al., 2007b, 2008b, 2008c).

There are two symmetry independent molecules in the asymmetric unit (labeled A and B). No significant differences concerning bond lengths and angles were found between molecules A and B. All rings in both molecules are trans-fused. Ring A of molecules A and B adopts a chair conformation, although ring A of molecule B is more distorted, as shown by the Cremer and Pople (1975) puckering parameters [A: Q = 0.582 (3) Å, θ = 2.4 (4)°, [var phi] = 233 (5)° B: Q = 0.583 (4) Å, θ = 6.1 (4)°, [var phi] = 278 (4)°].

Rings B and C have a conformation close to chair. A C14-envelope conformation was found for the five-membered ring D of both molecules, with the following puckering parameters [A: q2 = 0.384 (3) Å and [var phi]2 = 211.6 (5)°; B: q2 = 0.392 (3) Å and [var phi]2 = 211.6 (5)°]. The acetoxy group at C3 and the methyl ketone side chain at C17 are both equatorial to ring A and D, respectively. The substituents at ring B are in axial positions. The hydroxyl at C5 is α-oriented while the bulky nitrate group show β-configuration. The epoxide group fused to the five-membered ring is below the plane of ring D, thus presenting a 16α,17α-configuration. The molecules are hydrogen-bonded via the 5α-hydroxyl and the C20 carbonyl groups acting as donor and acceptor, respectively.

Experimental

The synthesis of 16α,17α-epoxy-5α-hydroxy-6β-nitrate-20-oxopregnan-3β-yl acetate (I) was efficiently accomplished by nucleophilic ring-opening of the corresponding 5α,6α;16α,17α-diepoxysteroid with bismuth(III) nitrate, in 1,4-dioxane (Pinto et al., 2007a). The product of this reaction was isolated in 91% yield and identified as the title compound (I) from IR, 1H and 13C NMR spectroscopy data (Pinto et al., 2007a). Recrystallization from methanol at room temperature gave colourless single crystals suitable for X-ray diffraction analysis.

Refinement

All H atoms were refined as riding on their parent atoms using SHELXL97 defaults, C—H ranging from 0.96 Å to 0.98 Å, O—H = 0.82 Å and Uiso(H) set to 1.2Ueq(C) or 1.5Ueq(Cmethyl, O). In the absence of anomalous scatterers, Friedel pairs had been merged prior to refinement. The absolute configuration was not determined from the X-ray data but was known from the synthetic route.

Figures

Fig. 1.
ORTEPII plot of the title compound. Displacement ellipsoids are drawn at the 50% level.

Crystal data

C23H33NO8Z = 2
Mr = 451.50F(000) = 484
Triclinic, P1Dx = 1.288 Mg m3
Hall symbol: P 1Melting point: 455 K
a = 10.9740 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.0721 (3) ÅCell parameters from 9093 reflections
c = 11.1686 (3) Åθ = 2.3–28.3°
α = 77.2135 (15)°µ = 0.10 mm1
β = 73.2087 (14)°T = 223 K
γ = 64.3465 (14)°Truncated pyramid, clear colourless
V = 1163.81 (6) Å30.32 × 0.17 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer5770 independent reflections
Radiation source: fine-focus sealed tube4806 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] and ω scansθmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)h = −14→14
Tmin = 0.947, Tmax = 0.994k = −14→14
24934 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0639P)2 + 0.1756P] where P = (Fo2 + 2Fc2)/3
5770 reflections(Δ/σ)max = 0.001
587 parametersΔρmax = 0.37 e Å3
3 restraintsΔρmin = −0.27 e Å3

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 (Å2)

xyzUiso*/Ueq
O3A0.06020 (16)0.62076 (15)0.97526 (17)0.0507 (4)
O5A0.25633 (16)0.83696 (15)0.69606 (17)0.0485 (4)
H5A0.19100.84720.66760.073*
O6A0.48378 (19)0.5008 (2)0.6049 (2)0.0654 (5)
O7A0.3044 (3)0.4890 (4)0.5533 (3)0.1164 (12)
O8A0.4744 (3)0.3104 (4)0.6076 (4)0.1458 (16)
O16A0.81145 (17)0.95570 (17)0.41953 (15)0.0499 (4)
O20A1.02169 (17)0.84865 (19)0.62988 (16)0.0544 (4)
O22A−0.1011 (2)0.80189 (19)1.0641 (2)0.0823 (7)
N6A0.4134 (4)0.4278 (4)0.5858 (3)0.0930 (11)
C1A0.3439 (2)0.7488 (2)0.9258 (2)0.0432 (5)
H1A10.40330.73840.98020.052*
H1A20.29460.84460.90430.052*
C2A0.2381 (3)0.6876 (3)0.9985 (2)0.0489 (5)
H2A10.28660.59461.03010.059*
H2A20.17970.73701.07000.059*
C3A0.1494 (2)0.6932 (2)0.9148 (2)0.0425 (5)
H3A0.09190.78760.89180.051*
C4A0.2359 (2)0.6276 (2)0.7965 (2)0.0420 (5)
H4A10.17580.63520.74390.050*
H4A20.28830.53260.81840.050*
C5A0.3353 (2)0.6952 (2)0.7239 (2)0.0362 (4)
C6A0.4110 (2)0.6457 (3)0.5945 (2)0.0489 (6)
H6A0.34190.67070.54440.059*
C7A0.5159 (3)0.7067 (3)0.5227 (2)0.0492 (6)
H7A10.46640.80020.49310.059*
H7A20.57150.65930.44950.059*
C8A0.6127 (2)0.7006 (2)0.60137 (19)0.0355 (4)
H8A0.67440.60660.61980.043*
C9A0.5271 (2)0.7617 (2)0.72606 (18)0.0324 (4)
H9A0.46330.85320.70260.039*
C10A0.4350 (2)0.6846 (2)0.80441 (19)0.0332 (4)
C11A0.6170 (2)0.7770 (3)0.8001 (2)0.0428 (5)
H11A0.67310.68820.83480.051*
H11B0.55660.82810.87000.051*
C12A0.7133 (2)0.8475 (2)0.7209 (2)0.0408 (5)
H12A0.65830.94120.69700.049*
H12B0.77390.84490.77070.049*
C13A0.8004 (2)0.7773 (2)0.60263 (18)0.0335 (4)
C14A0.6984 (2)0.7818 (2)0.53019 (18)0.0365 (4)
H14A0.63250.87590.52280.044*
C15A0.7847 (3)0.7533 (3)0.3968 (2)0.0499 (6)
H15A0.83640.65740.39140.060*
H15B0.72690.79060.33550.060*
C16A0.8799 (3)0.8247 (3)0.3783 (2)0.0504 (6)
H16A0.96280.80470.30970.060*
C17A0.8868 (2)0.8440 (2)0.5022 (2)0.0385 (5)
C18A0.9024 (2)0.6327 (2)0.6365 (2)0.0490 (5)
H18A0.95260.58970.56110.074*
H18B0.85170.58220.69180.074*
H18C0.96620.63620.67760.074*
C19A0.5259 (2)0.5372 (2)0.8420 (2)0.0470 (5)
H19A0.57550.53410.90150.071*
H19B0.59060.49770.76860.071*
H19C0.46820.48770.87950.071*
C20A1.0047 (2)0.8640 (2)0.5232 (2)0.0439 (5)
C21A1.0994 (3)0.9042 (3)0.4129 (3)0.0666 (8)
H21A1.15120.93920.44120.100*
H21B1.04600.97240.35710.100*
H21C1.16200.82710.36930.100*
C22A−0.0654 (2)0.6892 (2)1.0404 (2)0.0445 (5)
C23A−0.1511 (3)0.6078 (3)1.0851 (3)0.0584 (7)
H23A−0.10860.53161.14160.088*
H23B−0.15800.57701.01440.088*
H23C−0.24200.66231.12820.088*
O3B0.03807 (17)0.2481 (2)0.42055 (18)0.0665 (6)
O5B0.30588 (15)0.31642 (16)0.07748 (15)0.0455 (4)
H5B0.24680.31320.04860.068*
O6B0.49821 (17)−0.04860 (16)0.14594 (16)0.0485 (4)
O7B0.3139 (2)−0.0808 (2)0.13150 (19)0.0636 (5)
O8B0.4702 (3)−0.2329 (2)0.2290 (2)0.0815 (7)
O16B0.91153 (17)0.29534 (16)−0.21292 (14)0.0464 (4)
O20B1.10024 (18)0.26700 (19)0.00177 (17)0.0578 (5)
O22B−0.1340 (2)0.4244 (3)0.3654 (4)0.1382 (16)
N6B0.4192 (3)−0.1261 (2)0.1694 (2)0.0557 (6)
C1B0.3450 (2)0.3480 (3)0.3030 (2)0.0499 (6)
H1B10.39500.36740.35010.060*
H1B20.31380.42520.24160.060*
C2B0.2177 (3)0.3285 (3)0.3940 (3)0.0607 (7)
H2B10.24760.25800.46120.073*
H2B20.15630.41120.43140.073*
C3B0.1406 (2)0.2911 (3)0.3268 (2)0.0526 (6)
H3B0.09410.36880.27070.063*
C4B0.2338 (2)0.1719 (3)0.2531 (2)0.0437 (5)
H4B10.18080.15620.20650.052*
H4B20.26760.09190.31100.052*
C5B0.3569 (2)0.1962 (2)0.16149 (19)0.0356 (4)
C6B0.4437 (2)0.0847 (2)0.0747 (2)0.0403 (5)
H6B0.38540.08280.02380.048*
C7B0.5691 (2)0.1061 (2)−0.0130 (2)0.0382 (5)
H7B10.53770.1808−0.07650.046*
H7B20.62740.0261−0.05570.046*
C8B0.6561 (2)0.1351 (2)0.05285 (19)0.0319 (4)
H8B0.70230.05410.10610.038*
C9B0.5642 (2)0.2522 (2)0.13436 (18)0.0324 (4)
H9B0.52050.33050.07720.039*
C10B0.4443 (2)0.2234 (2)0.23346 (19)0.0361 (4)
C11B0.6523 (2)0.2916 (2)0.1920 (2)0.0425 (5)
H11C0.59230.37100.23500.051*
H11D0.69140.21890.25430.051*
C12B0.7707 (2)0.3208 (2)0.0949 (2)0.0398 (5)
H12C0.73220.40250.04040.048*
H12D0.82750.33510.13810.048*
C13B0.8598 (2)0.2044 (2)0.01604 (19)0.0328 (4)
C14B0.7641 (2)0.17770 (19)−0.04354 (18)0.0309 (4)
H14B0.71180.2649−0.08590.037*
C15B0.8623 (2)0.0906 (2)−0.1492 (2)0.0410 (5)
H15C0.9032−0.0036−0.11690.049*
H15D0.81520.0990−0.21380.049*
C16B0.9698 (2)0.1512 (2)−0.1981 (2)0.0446 (5)
H16B1.05860.1020−0.25260.054*
C17B0.9659 (2)0.2245 (2)−0.1007 (2)0.0391 (5)
C18B0.9412 (2)0.0794 (2)0.0968 (2)0.0439 (5)
H18D0.99800.10120.13240.066*
H18E0.99890.00760.04510.066*
H18F0.87750.05140.16320.066*
C19B0.5032 (2)0.1046 (3)0.3303 (2)0.0445 (5)
H19D0.53920.13210.38350.067*
H19E0.57620.03100.28730.067*
H19F0.43100.07630.38070.067*
C20B1.0865 (2)0.2525 (3)−0.0962 (2)0.0491 (6)
C21B1.1848 (4)0.2674 (5)−0.2163 (3)0.1020 (14)
H21D1.24570.3015−0.20190.153*
H21E1.13390.3292−0.27700.153*
H21F1.23830.1812−0.24770.153*
C22B−0.0931 (2)0.3207 (3)0.4269 (2)0.0508 (6)
C23B−0.1833 (3)0.2606 (3)0.5197 (3)0.0667 (8)
H23D−0.23770.31830.58510.100*
H23E−0.12740.17390.55570.100*
H23F−0.24370.25040.47890.100*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O3A0.0356 (8)0.0377 (8)0.0753 (11)−0.0206 (7)0.0026 (8)−0.0061 (7)
O5A0.0339 (8)0.0463 (8)0.0693 (11)−0.0195 (7)−0.0230 (8)0.0087 (8)
O6A0.0541 (10)0.0717 (12)0.0871 (13)−0.0415 (10)0.0103 (9)−0.0404 (10)
O7A0.0903 (19)0.188 (3)0.126 (2)−0.098 (2)0.0199 (17)−0.091 (2)
O8A0.106 (2)0.107 (2)0.229 (4)−0.0783 (19)0.076 (2)−0.101 (2)
O16A0.0482 (9)0.0594 (10)0.0492 (9)−0.0293 (8)−0.0246 (8)0.0158 (7)
O20A0.0399 (9)0.0807 (12)0.0554 (10)−0.0372 (9)−0.0184 (8)0.0065 (9)
O22A0.0664 (12)0.0499 (11)0.1097 (17)−0.0310 (10)0.0361 (12)−0.0248 (11)
N6A0.080 (2)0.112 (3)0.108 (2)−0.071 (2)0.0487 (18)−0.075 (2)
C1A0.0394 (11)0.0564 (13)0.0418 (11)−0.0281 (10)−0.0023 (9)−0.0106 (10)
C2A0.0452 (13)0.0540 (13)0.0465 (13)−0.0262 (11)0.0040 (10)−0.0083 (10)
C3A0.0316 (10)0.0338 (10)0.0613 (14)−0.0193 (9)−0.0007 (10)−0.0028 (10)
C4A0.0317 (10)0.0434 (11)0.0574 (13)−0.0194 (9)−0.0130 (10)−0.0042 (10)
C5A0.0274 (9)0.0408 (10)0.0442 (11)−0.0163 (8)−0.0100 (8)−0.0032 (9)
C6A0.0429 (12)0.0731 (16)0.0485 (13)−0.0348 (12)−0.0119 (10)−0.0133 (12)
C7A0.0485 (13)0.0788 (17)0.0392 (12)−0.0413 (13)−0.0105 (10)−0.0074 (11)
C8A0.0317 (10)0.0466 (11)0.0345 (10)−0.0202 (9)−0.0083 (8)−0.0048 (8)
C9A0.0281 (9)0.0409 (10)0.0332 (9)−0.0165 (8)−0.0096 (8)−0.0039 (8)
C10A0.0279 (9)0.0377 (10)0.0375 (10)−0.0161 (8)−0.0086 (8)−0.0027 (8)
C11A0.0383 (11)0.0677 (15)0.0344 (11)−0.0320 (11)−0.0069 (9)−0.0072 (10)
C12A0.0357 (10)0.0579 (13)0.0419 (11)−0.0284 (10)−0.0110 (9)−0.0063 (10)
C13A0.0280 (9)0.0407 (10)0.0352 (10)−0.0174 (8)−0.0106 (8)0.0020 (8)
C14A0.0346 (10)0.0501 (12)0.0329 (10)−0.0234 (9)−0.0086 (8)−0.0042 (9)
C15A0.0549 (14)0.0716 (16)0.0355 (11)−0.0386 (13)−0.0080 (10)−0.0032 (10)
C16A0.0502 (13)0.0709 (16)0.0370 (11)−0.0363 (13)−0.0061 (10)0.0023 (11)
C17A0.0320 (10)0.0434 (11)0.0389 (11)−0.0170 (9)−0.0111 (8)0.0066 (9)
C18A0.0360 (11)0.0484 (12)0.0602 (14)−0.0190 (10)−0.0143 (11)0.0086 (11)
C19A0.0355 (11)0.0468 (12)0.0591 (14)−0.0190 (10)−0.0165 (10)0.0070 (10)
C20A0.0312 (10)0.0485 (12)0.0527 (13)−0.0197 (9)−0.0129 (10)0.0061 (10)
C21A0.0521 (15)0.096 (2)0.0631 (16)−0.0508 (15)−0.0147 (13)0.0184 (15)
C22A0.0390 (11)0.0392 (11)0.0514 (13)−0.0207 (9)0.0016 (10)−0.0021 (9)
C23A0.0462 (14)0.0622 (15)0.0719 (17)−0.0346 (12)0.0039 (12)−0.0118 (13)
O3B0.0297 (8)0.0783 (12)0.0635 (11)−0.0161 (8)0.0037 (8)0.0164 (10)
O5B0.0340 (8)0.0600 (10)0.0486 (9)−0.0258 (7)−0.0174 (7)0.0090 (7)
O6B0.0491 (9)0.0516 (9)0.0585 (10)−0.0330 (8)−0.0122 (8)−0.0038 (7)
O7B0.0630 (12)0.0880 (14)0.0672 (11)−0.0559 (11)−0.0044 (10)−0.0193 (10)
O8B0.1071 (19)0.0662 (13)0.0834 (15)−0.0555 (13)−0.0197 (13)0.0114 (11)
O16B0.0472 (9)0.0549 (9)0.0446 (8)−0.0313 (8)−0.0177 (7)0.0133 (7)
O20B0.0483 (10)0.0788 (12)0.0646 (11)−0.0426 (9)−0.0236 (9)0.0085 (9)
O22B0.0451 (13)0.116 (2)0.178 (3)−0.0182 (13)−0.0023 (16)0.071 (2)
N6B0.0648 (14)0.0665 (14)0.0500 (12)−0.0458 (12)0.0055 (11)−0.0158 (11)
C1B0.0364 (11)0.0636 (15)0.0512 (13)−0.0185 (11)−0.0018 (10)−0.0224 (11)
C2B0.0428 (13)0.0787 (18)0.0522 (14)−0.0218 (13)0.0102 (11)−0.0233 (13)
C3B0.0330 (11)0.0666 (15)0.0473 (13)−0.0206 (11)−0.0007 (10)0.0059 (11)
C4B0.0314 (10)0.0632 (14)0.0422 (11)−0.0271 (10)−0.0082 (9)0.0007 (10)
C5B0.0273 (9)0.0504 (12)0.0347 (10)−0.0212 (9)−0.0092 (8)0.0000 (9)
C6B0.0398 (11)0.0520 (12)0.0413 (11)−0.0288 (10)−0.0105 (9)−0.0043 (9)
C7B0.0360 (10)0.0527 (12)0.0370 (10)−0.0283 (10)−0.0019 (8)−0.0117 (9)
C8B0.0271 (9)0.0371 (10)0.0368 (10)−0.0173 (8)−0.0082 (8)−0.0031 (8)
C9B0.0263 (9)0.0390 (10)0.0361 (10)−0.0152 (8)−0.0087 (8)−0.0050 (8)
C10B0.0282 (9)0.0486 (11)0.0356 (10)−0.0174 (9)−0.0081 (8)−0.0061 (9)
C11B0.0372 (11)0.0568 (13)0.0448 (12)−0.0242 (10)−0.0086 (9)−0.0159 (10)
C12B0.0374 (11)0.0429 (11)0.0514 (12)−0.0227 (9)−0.0163 (10)−0.0057 (9)
C13B0.0277 (9)0.0378 (10)0.0383 (10)−0.0179 (8)−0.0126 (8)0.0031 (8)
C14B0.0268 (9)0.0327 (9)0.0362 (10)−0.0151 (8)−0.0083 (8)−0.0010 (8)
C15B0.0386 (11)0.0469 (12)0.0400 (11)−0.0238 (10)0.0000 (9)−0.0066 (9)
C16B0.0365 (11)0.0535 (13)0.0441 (12)−0.0238 (10)−0.0027 (9)−0.0014 (10)
C17B0.0314 (10)0.0418 (11)0.0447 (12)−0.0192 (9)−0.0128 (9)0.0101 (9)
C18B0.0362 (11)0.0503 (12)0.0474 (12)−0.0231 (10)−0.0168 (9)0.0133 (10)
C19B0.0372 (11)0.0645 (14)0.0362 (11)−0.0248 (10)−0.0110 (9)−0.0004 (10)
C20B0.0351 (11)0.0604 (14)0.0588 (14)−0.0306 (11)−0.0161 (11)0.0121 (11)
C21B0.081 (2)0.190 (4)0.073 (2)−0.105 (3)0.0000 (18)−0.002 (2)
C22B0.0357 (12)0.0502 (13)0.0587 (14)−0.0153 (10)−0.0060 (11)−0.0006 (11)
C23B0.0380 (13)0.0806 (19)0.0684 (18)−0.0246 (13)0.0039 (12)−0.0014 (15)

Geometric parameters (Å, °)

O3A—C22A1.328 (3)O3B—C22B1.299 (3)
O3A—C3A1.454 (2)O3B—C3B1.467 (3)
O5A—C5A1.440 (3)O5B—C5B1.439 (3)
O5A—H5A0.8200O5B—H5B0.8200
O6A—N6A1.417 (3)O6B—N6B1.403 (2)
O6A—C6A1.445 (3)O6B—C6B1.470 (3)
O7A—N6A1.209 (5)O7B—N6B1.206 (3)
O8A—N6A1.182 (5)O8B—N6B1.204 (3)
O16A—C16A1.426 (3)O16B—C16B1.430 (3)
O16A—C17A1.455 (2)O16B—C17B1.461 (2)
O20A—C20A1.222 (3)O20B—C20B1.200 (3)
O22A—C22A1.201 (3)O22B—C22B1.172 (3)
C1A—C2A1.535 (3)C1B—C2B1.541 (3)
C1A—C10A1.539 (3)C1B—C10B1.542 (3)
C1A—H1A10.9700C1B—H1B10.9700
C1A—H1A20.9700C1B—H1B20.9700
C2A—C3A1.508 (3)C2B—C3B1.502 (4)
C2A—H2A10.9700C2B—H2B10.9700
C2A—H2A20.9700C2B—H2B20.9700
C3A—C4A1.509 (3)C3B—C4B1.513 (4)
C3A—H3A0.9800C3B—H3B0.9800
C4A—C5A1.528 (3)C4B—C5B1.529 (3)
C4A—H4A10.9700C4B—H4B10.9700
C4A—H4A20.9700C4B—H4B20.9700
C5A—C6A1.530 (3)C5B—C6B1.533 (3)
C5A—C10A1.559 (3)C5B—C10B1.568 (3)
C6A—C7A1.525 (3)C6B—C7B1.519 (3)
C6A—H6A0.9800C6B—H6B0.9800
C7A—C8A1.534 (3)C7B—C8B1.527 (3)
C7A—H7A10.9700C7B—H7B10.9700
C7A—H7A20.9700C7B—H7B20.9700
C8A—C14A1.519 (3)C8B—C14B1.519 (3)
C8A—C9A1.546 (3)C8B—C9B1.545 (3)
C8A—H8A0.9800C8B—H8B0.9800
C9A—C11A1.537 (3)C9B—C11B1.545 (3)
C9A—C10A1.556 (3)C9B—C10B1.557 (3)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C19A1.538 (3)C10B—C19B1.535 (3)
C11A—C12A1.542 (3)C11B—C12B1.536 (3)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C13A1.531 (3)C12B—C13B1.519 (3)
C12A—H12A0.9700C12B—H12C0.9700
C12A—H12B0.9700C12B—H12D0.9700
C13A—C17A1.525 (3)C13B—C17B1.525 (3)
C13A—C14A1.539 (3)C13B—C18B1.540 (3)
C13A—C18A1.544 (3)C13B—C14B1.547 (3)
C14A—C15A1.533 (3)C14B—C15B1.534 (3)
C14A—H14A0.9800C14B—H14B0.9800
C15A—C16A1.509 (3)C15B—C16B1.514 (3)
C15A—H15A0.9700C15B—H15C0.9700
C15A—H15B0.9700C15B—H15D0.9700
C16A—C17A1.474 (3)C16B—C17B1.476 (3)
C16A—H16A0.9800C16B—H16B0.9800
C17A—C20A1.491 (3)C17B—C20B1.501 (3)
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C20A—C21A1.488 (3)C20B—C21B1.487 (4)
C21A—H21A0.9600C21B—H21D0.9600
C21A—H21B0.9600C21B—H21E0.9600
C21A—H21C0.9600C21B—H21F0.9600
C22A—C23A1.486 (3)C22B—C23B1.473 (4)
C23A—H23A0.9600C23B—H23D0.9600
C23A—H23B0.9600C23B—H23E0.9600
C23A—H23C0.9600C23B—H23F0.9600
C22A—O3A—C3A117.75 (16)C22B—O3B—C3B119.48 (19)
C5A—O5A—H5A109.5C5B—O5B—H5B109.5
N6A—O6A—C6A115.8 (2)N6B—O6B—C6B115.81 (17)
C16A—O16A—C17A61.54 (15)C16B—O16B—C17B61.39 (14)
O8A—N6A—O7A129.8 (3)O8B—N6B—O7B129.0 (2)
O8A—N6A—O6A111.1 (4)O8B—N6B—O6B111.6 (2)
O7A—N6A—O6A119.1 (3)O7B—N6B—O6B119.4 (2)
C2A—C1A—C10A113.77 (18)C2B—C1B—C10B112.8 (2)
C2A—C1A—H1A1108.8C2B—C1B—H1B1109.0
C10A—C1A—H1A1108.8C10B—C1B—H1B1109.0
C2A—C1A—H1A2108.8C2B—C1B—H1B2109.0
C10A—C1A—H1A2108.8C10B—C1B—H1B2109.0
H1A1—C1A—H1A2107.7H1B1—C1B—H1B2107.8
C3A—C2A—C1A110.73 (19)C3B—C2B—C1B111.1 (2)
C3A—C2A—H2A1109.5C3B—C2B—H2B1109.4
C1A—C2A—H2A1109.5C1B—C2B—H2B1109.4
C3A—C2A—H2A2109.5C3B—C2B—H2B2109.4
C1A—C2A—H2A2109.5C1B—C2B—H2B2109.4
H2A1—C2A—H2A2108.1H2B1—C2B—H2B2108.0
O3A—C3A—C2A112.36 (19)O3B—C3B—C2B108.8 (2)
O3A—C3A—C4A105.21 (17)O3B—C3B—C4B105.5 (2)
C2A—C3A—C4A111.78 (18)C2B—C3B—C4B112.6 (2)
O3A—C3A—H3A109.1O3B—C3B—H3B109.9
C2A—C3A—H3A109.1C2B—C3B—H3B109.9
C4A—C3A—H3A109.1C4B—C3B—H3B109.9
C3A—C4A—C5A110.32 (17)C3B—C4B—C5B111.33 (19)
C3A—C4A—H4A1109.6C3B—C4B—H4B1109.4
C5A—C4A—H4A1109.6C5B—C4B—H4B1109.4
C3A—C4A—H4A2109.6C3B—C4B—H4B2109.4
C5A—C4A—H4A2109.6C5B—C4B—H4B2109.4
H4A1—C4A—H4A2108.1H4B1—C4B—H4B2108.0
O5A—C5A—C4A108.95 (16)O5B—C5B—C4B109.03 (16)
O5A—C5A—C6A104.13 (18)O5B—C5B—C6B104.41 (16)
C4A—C5A—C6A112.31 (18)C4B—C5B—C6B112.52 (17)
O5A—C5A—C10A106.21 (16)O5B—C5B—C10B106.11 (16)
C4A—C5A—C10A111.51 (17)C4B—C5B—C10B110.82 (16)
C6A—C5A—C10A113.19 (16)C6B—C5B—C10B113.46 (16)
O6A—C6A—C7A107.7 (2)O6B—C6B—C7B105.97 (18)
O6A—C6A—C5A111.27 (19)O6B—C6B—C5B111.95 (17)
C7A—C6A—C5A113.30 (18)C7B—C6B—C5B112.54 (17)
O6A—C6A—H6A108.1O6B—C6B—H6B108.8
C7A—C6A—H6A108.1C7B—C6B—H6B108.8
C5A—C6A—H6A108.1C5B—C6B—H6B108.8
C6A—C7A—C8A113.66 (18)C6B—C7B—C8B114.21 (17)
C6A—C7A—H7A1108.8C6B—C7B—H7B1108.7
C8A—C7A—H7A1108.8C8B—C7B—H7B1108.7
C6A—C7A—H7A2108.8C6B—C7B—H7B2108.7
C8A—C7A—H7A2108.8C8B—C7B—H7B2108.7
H7A1—C7A—H7A2107.7H7B1—C7B—H7B2107.6
C14A—C8A—C7A110.26 (17)C14B—C8B—C7B110.35 (16)
C14A—C8A—C9A107.88 (17)C14B—C8B—C9B107.18 (15)
C7A—C8A—C9A110.20 (17)C7B—C8B—C9B110.61 (15)
C14A—C8A—H8A109.5C14B—C8B—H8B109.6
C7A—C8A—H8A109.5C7B—C8B—H8B109.6
C9A—C8A—H8A109.5C9B—C8B—H8B109.6
C11A—C9A—C8A112.49 (16)C8B—C9B—C11B111.29 (16)
C11A—C9A—C10A113.98 (16)C8B—C9B—C10B112.15 (16)
C8A—C9A—C10A111.10 (16)C11B—C9B—C10B113.40 (16)
C11A—C9A—H9A106.2C8B—C9B—H9B106.5
C8A—C9A—H9A106.2C11B—C9B—H9B106.5
C10A—C9A—H9A106.2C10B—C9B—H9B106.5
C19A—C10A—C1A107.93 (18)C19B—C10B—C1B108.82 (19)
C19A—C10A—C9A110.37 (16)C19B—C10B—C9B110.16 (16)
C1A—C10A—C9A111.64 (16)C1B—C10B—C9B110.93 (17)
C19A—C10A—C5A111.83 (17)C19B—C10B—C5B112.43 (18)
C1A—C10A—C5A107.02 (16)C1B—C10B—C5B106.45 (16)
C9A—C10A—C5A108.04 (15)C9B—C10B—C5B108.00 (15)
C9A—C11A—C12A114.04 (17)C12B—C11B—C9B113.84 (17)
C9A—C11A—H11A108.7C12B—C11B—H11C108.8
C12A—C11A—H11A108.7C9B—C11B—H11C108.8
C9A—C11A—H11B108.7C12B—C11B—H11D108.8
C12A—C11A—H11B108.7C9B—C11B—H11D108.8
H11A—C11A—H11B107.6H11C—C11B—H11D107.7
C13A—C12A—C11A110.20 (17)C13B—C12B—C11B110.84 (16)
C13A—C12A—H12A109.6C13B—C12B—H12C109.5
C11A—C12A—H12A109.6C11B—C12B—H12C109.5
C13A—C12A—H12B109.6C13B—C12B—H12D109.5
C11A—C12A—H12B109.6C11B—C12B—H12D109.5
H12A—C12A—H12B108.1H12C—C12B—H12D108.1
C17A—C13A—C12A118.28 (17)C12B—C13B—C17B118.65 (17)
C17A—C13A—C14A101.29 (15)C12B—C13B—C18B110.49 (18)
C12A—C13A—C14A106.94 (16)C17B—C13B—C18B105.91 (16)
C17A—C13A—C18A105.86 (16)C12B—C13B—C14B108.06 (16)
C12A—C13A—C18A111.21 (17)C17B—C13B—C14B100.91 (16)
C14A—C13A—C18A113.05 (18)C18B—C13B—C14B112.58 (16)
C8A—C14A—C15A120.13 (18)C8B—C14B—C15B120.56 (16)
C8A—C14A—C13A113.00 (16)C8B—C14B—C13B113.40 (16)
C15A—C14A—C13A104.83 (17)C15B—C14B—C13B104.89 (16)
C8A—C14A—H14A106.0C8B—C14B—H14B105.6
C15A—C14A—H14A106.0C15B—C14B—H14B105.6
C13A—C14A—H14A106.0C13B—C14B—H14B105.6
C16A—C15A—C14A101.89 (18)C16B—C15B—C14B101.39 (17)
C16A—C15A—H15A111.4C16B—C15B—H15C111.5
C14A—C15A—H15A111.4C14B—C15B—H15C111.5
C16A—C15A—H15B111.4C16B—C15B—H15D111.5
C14A—C15A—H15B111.4C14B—C15B—H15D111.5
H15A—C15A—H15B109.3H15C—C15B—H15D109.3
O16A—C16A—C17A60.22 (14)O16B—C16B—C17B60.32 (14)
O16A—C16A—C15A113.6 (2)O16B—C16B—C15B113.52 (18)
C17A—C16A—C15A109.16 (19)C17B—C16B—C15B109.40 (18)
O16A—C16A—H16A119.8O16B—C16B—H16B119.8
C17A—C16A—H16A119.8C17B—C16B—H16B119.8
C15A—C16A—H16A119.8C15B—C16B—H16B119.8
O16A—C17A—C16A58.24 (15)O16B—C17B—C16B58.29 (14)
O16A—C17A—C20A111.10 (17)O16B—C17B—C20B111.54 (17)
C16A—C17A—C20A123.0 (2)C16B—C17B—C20B123.1 (2)
O16A—C17A—C13A115.75 (16)O16B—C17B—C13B115.73 (16)
C16A—C17A—C13A107.69 (18)C16B—C17B—C13B107.64 (17)
C20A—C17A—C13A123.65 (17)C20B—C17B—C13B123.40 (19)
C13A—C18A—H18A109.5C13B—C18B—H18D109.5
C13A—C18A—H18B109.5C13B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C13A—C18A—H18C109.5C13B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C10A—C19A—H19A109.5C10B—C19B—H19D109.5
C10A—C19A—H19B109.5C10B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C10A—C19A—H19C109.5C10B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
O20A—C20A—C21A120.9 (2)O20B—C20B—C21B121.0 (2)
O20A—C20A—C17A120.1 (2)O20B—C20B—C17B120.5 (2)
C21A—C20A—C17A119.0 (2)C21B—C20B—C17B118.4 (2)
C20A—C21A—H21A109.5C20B—C21B—H21D109.5
C20A—C21A—H21B109.5C20B—C21B—H21E109.5
H21A—C21A—H21B109.5H21D—C21B—H21E109.5
C20A—C21A—H21C109.5C20B—C21B—H21F109.5
H21A—C21A—H21C109.5H21D—C21B—H21F109.5
H21B—C21A—H21C109.5H21E—C21B—H21F109.5
O22A—C22A—O3A122.7 (2)O22B—C22B—O3B122.6 (2)
O22A—C22A—C23A124.9 (2)O22B—C22B—C23B124.0 (2)
O3A—C22A—C23A112.3 (2)O3B—C22B—C23B113.3 (2)
C22A—C23A—H23A109.5C22B—C23B—H23D109.5
C22A—C23A—H23B109.5C22B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
C22A—C23A—H23C109.5C22B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C6A—O6A—N6A—O8A−173.4 (3)C6B—O6B—N6B—O8B−179.4 (2)
C6A—O6A—N6A—O7A5.4 (4)C6B—O6B—N6B—O7B−0.2 (3)
C10A—C1A—C2A—C3A−54.8 (3)C10B—C1B—C2B—C3B−55.8 (3)
C22A—O3A—C3A—C2A90.6 (2)C22B—O3B—C3B—C2B113.4 (3)
C22A—O3A—C3A—C4A−147.5 (2)C22B—O3B—C3B—C4B−125.5 (3)
C1A—C2A—C3A—O3A172.55 (18)C1B—C2B—C3B—O3B169.0 (2)
C1A—C2A—C3A—C4A54.5 (2)C1B—C2B—C3B—C4B52.4 (3)
O3A—C3A—C4A—C5A−179.87 (17)O3B—C3B—C4B—C5B−173.26 (17)
C2A—C3A—C4A—C5A−57.7 (2)C2B—C3B—C4B—C5B−54.7 (3)
C3A—C4A—C5A—O5A−57.2 (2)C3B—C4B—C5B—O5B−58.0 (2)
C3A—C4A—C5A—C6A−172.08 (18)C3B—C4B—C5B—C6B−173.30 (18)
C3A—C4A—C5A—C10A59.7 (2)C3B—C4B—C5B—C10B58.5 (2)
N6A—O6A—C6A—C7A−138.5 (2)N6B—O6B—C6B—C7B−141.69 (18)
N6A—O6A—C6A—C5A96.8 (2)N6B—O6B—C6B—C5B95.3 (2)
O5A—C5A—C6A—O6A−173.49 (17)O5B—C5B—C6B—O6B−176.68 (15)
C4A—C5A—C6A—O6A−55.8 (2)C4B—C5B—C6B—O6B−58.6 (2)
C10A—C5A—C6A—O6A71.6 (2)C10B—C5B—C6B—O6B68.2 (2)
O5A—C5A—C6A—C7A65.0 (2)O5B—C5B—C6B—C7B64.1 (2)
C4A—C5A—C6A—C7A−177.25 (19)C4B—C5B—C6B—C7B−177.82 (18)
C10A—C5A—C6A—C7A−49.9 (3)C10B—C5B—C6B—C7B−51.0 (2)
O6A—C6A—C7A—C8A−75.3 (2)O6B—C6B—C7B—C8B−73.1 (2)
C5A—C6A—C7A—C8A48.2 (3)C5B—C6B—C7B—C8B49.5 (2)
C6A—C7A—C8A—C14A−171.4 (2)C6B—C7B—C8B—C14B−170.62 (17)
C6A—C7A—C8A—C9A−52.4 (3)C6B—C7B—C8B—C9B−52.2 (2)
C14A—C8A—C9A—C11A−51.3 (2)C14B—C8B—C9B—C11B−54.5 (2)
C7A—C8A—C9A—C11A−171.77 (19)C7B—C8B—C9B—C11B−174.82 (17)
C14A—C8A—C9A—C10A179.52 (16)C14B—C8B—C9B—C10B177.30 (15)
C7A—C8A—C9A—C10A59.1 (2)C7B—C8B—C9B—C10B57.0 (2)
C2A—C1A—C10A—C19A−65.6 (2)C2B—C1B—C10B—C19B−63.6 (3)
C2A—C1A—C10A—C9A172.89 (18)C2B—C1B—C10B—C9B175.0 (2)
C2A—C1A—C10A—C5A54.9 (2)C2B—C1B—C10B—C5B57.8 (3)
C11A—C9A—C10A—C19A−65.5 (2)C8B—C9B—C10B—C19B65.8 (2)
C8A—C9A—C10A—C19A62.8 (2)C11B—C9B—C10B—C19B−61.3 (2)
C11A—C9A—C10A—C1A54.5 (2)C8B—C9B—C10B—C1B−173.61 (17)
C8A—C9A—C10A—C1A−177.16 (16)C11B—C9B—C10B—C1B59.3 (2)
C11A—C9A—C10A—C5A171.91 (17)C8B—C9B—C10B—C5B−57.3 (2)
C8A—C9A—C10A—C5A−59.7 (2)C11B—C9B—C10B—C5B175.60 (17)
O5A—C5A—C10A—C19A179.61 (18)O5B—C5B—C10B—C19B178.45 (17)
C4A—C5A—C10A—C19A61.0 (2)C4B—C5B—C10B—C19B60.2 (2)
C6A—C5A—C10A—C19A−66.7 (2)C6B—C5B—C10B—C19B−67.5 (2)
O5A—C5A—C10A—C1A61.6 (2)O5B—C5B—C10B—C1B59.4 (2)
C4A—C5A—C10A—C1A−56.9 (2)C4B—C5B—C10B—C1B−58.8 (2)
C6A—C5A—C10A—C1A175.27 (19)C6B—C5B—C10B—C1B173.45 (18)
O5A—C5A—C10A—C9A−58.7 (2)O5B—C5B—C10B—C9B−59.8 (2)
C4A—C5A—C10A—C9A−177.30 (16)C4B—C5B—C10B—C9B−178.03 (17)
C6A—C5A—C10A—C9A54.9 (2)C6B—C5B—C10B—C9B54.3 (2)
C8A—C9A—C11A—C12A49.7 (3)C8B—C9B—C11B—C12B52.7 (2)
C10A—C9A—C11A—C12A177.32 (18)C10B—C9B—C11B—C12B−179.77 (17)
C9A—C11A—C12A—C13A−53.0 (2)C9B—C11B—C12B—C13B−53.0 (2)
C11A—C12A—C13A—C17A171.14 (17)C11B—C12B—C13B—C17B168.92 (17)
C11A—C12A—C13A—C14A57.8 (2)C11B—C12B—C13B—C18B−68.6 (2)
C11A—C12A—C13A—C18A−66.1 (2)C11B—C12B—C13B—C14B55.0 (2)
C7A—C8A—C14A—C15A−54.1 (3)C7B—C8B—C14B—C15B−52.6 (2)
C9A—C8A—C14A—C15A−174.47 (19)C9B—C8B—C14B—C15B−173.11 (17)
C7A—C8A—C14A—C13A−178.69 (19)C7B—C8B—C14B—C13B−178.11 (17)
C9A—C8A—C14A—C13A60.9 (2)C9B—C8B—C14B—C13B61.38 (19)
C17A—C13A—C14A—C8A170.59 (17)C12B—C13B—C14B—C8B−62.4 (2)
C12A—C13A—C14A—C8A−65.0 (2)C17B—C13B—C14B—C8B172.37 (16)
C18A—C13A—C14A—C8A57.8 (2)C18B—C13B—C14B—C8B59.9 (2)
C17A—C13A—C14A—C15A38.0 (2)C12B—C13B—C14B—C15B164.07 (16)
C12A—C13A—C14A—C15A162.47 (18)C17B—C13B—C14B—C15B38.87 (19)
C18A—C13A—C14A—C15A−74.8 (2)C18B—C13B—C14B—C15B−73.6 (2)
C8A—C14A—C15A—C16A−164.78 (19)C8B—C14B—C15B—C16B−166.35 (17)
C13A—C14A—C15A—C16A−36.4 (2)C13B—C14B—C15B—C16B−37.0 (2)
C17A—O16A—C16A—C15A99.3 (2)C17B—O16B—C16B—C15B99.7 (2)
C14A—C15A—C16A—O16A−44.4 (2)C14B—C15B—C16B—O16B−44.3 (2)
C14A—C15A—C16A—C17A20.6 (3)C14B—C15B—C16B—C17B20.9 (2)
C16A—O16A—C17A—C20A116.6 (2)C16B—O16B—C17B—C20B116.5 (2)
C16A—O16A—C17A—C13A−95.6 (2)C16B—O16B—C17B—C13B−95.6 (2)
C15A—C16A—C17A—O16A−106.9 (2)C15B—C16B—C17B—O16B−106.63 (19)
O16A—C16A—C17A—C20A−95.9 (2)O16B—C16B—C17B—C20B−96.5 (2)
C15A—C16A—C17A—C20A157.2 (2)C15B—C16B—C17B—C20B156.9 (2)
O16A—C16A—C17A—C13A109.81 (17)O16B—C16B—C17B—C13B109.81 (17)
C15A—C16A—C17A—C13A2.9 (3)C15B—C16B—C17B—C13B3.2 (2)
C12A—C13A—C17A—O16A−78.8 (2)C12B—C13B—C17B—O16B−80.6 (2)
C14A—C13A—C17A—O16A37.6 (2)C18B—C13B—C17B—O16B154.57 (18)
C18A—C13A—C17A—O16A155.71 (19)C14B—C13B—C17B—O16B37.1 (2)
C12A—C13A—C17A—C16A−141.5 (2)C12B—C13B—C17B—C16B−143.32 (19)
C14A—C13A—C17A—C16A−25.1 (2)C18B—C13B—C17B—C16B91.89 (19)
C18A—C13A—C17A—C16A93.1 (2)C14B—C13B—C17B—C16B−25.6 (2)
C12A—C13A—C17A—C20A64.4 (3)C12B—C13B—C17B—C20B63.1 (3)
C14A—C13A—C17A—C20A−179.2 (2)C18B—C13B—C17B—C20B−61.7 (3)
C18A—C13A—C17A—C20A−61.0 (3)C14B—C13B—C17B—C20B−179.23 (19)
O16A—C17A—C20A—O20A131.8 (2)O16B—C17B—C20B—O20B141.3 (2)
C16A—C17A—C20A—O20A−163.2 (2)C16B—C17B—C20B—O20B−153.3 (2)
C13A—C17A—C20A—O20A−12.9 (3)C13B—C17B—C20B—O20B−3.7 (4)
O16A—C17A—C20A—C21A−47.5 (3)O16B—C17B—C20B—C21B−36.2 (4)
C16A—C17A—C20A—C21A17.5 (3)C16B—C17B—C20B—C21B29.1 (4)
C13A—C17A—C20A—C21A167.8 (2)C13B—C17B—C20B—C21B178.8 (3)
C3A—O3A—C22A—O22A−9.5 (4)C3B—O3B—C22B—O22B−4.5 (5)
C3A—O3A—C22A—C23A173.6 (2)C3B—O3B—C22B—C23B176.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5A—H5A···O20Ai0.822.012.822 (2)168
O5B—H5B···O20Bi0.822.112.913 (2)168

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2943).

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