organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1271-o1272

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

aLaboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, P-3000-295 Coimbra, Portugal, and bCEMDRX, Departamento de Física, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, P-3004-516 Coimbra, Portugal
*Correspondence e-mail: jap@pollux.fis.uc.pt

(Received 30 April 2009; accepted 5 May 2009; online 14 May 2009)

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[Salvador, J. A. R., Silvestre, S. M. & Moreira, V. M. (2006). Curr. Org. Chem. 10, 2227-2257.], 2008[Salvador, J. A. R., Silvestre, S. M. & Moreira, V. M. (2008). Curr. Org. Chem. 12, 492-522.]); Pinto et al. (2008a[Pinto, R. M. A., Salvador, J. A. R. & Paixão, J. A. (2008a). Acta Cryst. C64, o279-o282.]). For the synthesis of β-hydr­oxy nitrates, see: Pinto et al. (2007a[Pinto, R. M. A., Salvador, J. A. R. & Le Roux, C. (2007a). Tetrahedron, 63, 9221-9228.]). For the structures of 5α-hydr­oxy-6β-substituted steroids, see: Pinto et al. (2007b[Pinto, R. M. A., Ramos Silva, M., Matos Beja, A. & Salvador, J. A. R. (2007b). Acta Cryst. E63, o2138-o2139.], 2008b[Pinto, R. M. A., Salvador, J. A. R., Paixão, J. A., Matos Beja, A. & Ramos Silva, M. (2008b). Acta Cryst. E64, o1420.],c[Pinto, R. M. A., Ramos Silva, M., Matos Beja, A., Salvador, J. A. R. & Paixão, J. A. (2008c). Acta Cryst. E64, o2303.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H33NO8

  • Mr = 451.50

  • Triclinic, P 1

  • 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[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.947, Tmax = 0.994

  • 24934 measured reflections

  • 5770 independent reflections

  • 4806 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5A—H5A⋯O20Ai 0.82 2.01 2.822 (2) 168
O5B—H5B⋯O20Bi 0.82 2.11 2.913 (2) 168
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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)°, ϕ = 233 (5)° B: Q = 0.583 (4) Å, θ = 6.1 (4)°, ϕ = 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 ϕ2 = 211.6 (5)°; B: q2 = 0.392 (3) Å and ϕ2 = 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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEPII plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
16α,17α-Epoxy-5α-hydroxy-6β-nitrooxy-20-oxopregnan-3β-yl acetate top
Crystal data top
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 top
Bruker APEXII CCD area-detector
diffractometer
5770 independent reflections
Radiation source: fine-focus sealed tube4806 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1414
Tmin = 0.947, Tmax = 0.994k = 1414
24934 measured reflectionsl = 1414
Refinement top
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 = 1.04 w = 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
Crystal data top
C23H33NO8γ = 64.3465 (14)°
Mr = 451.50V = 1163.81 (6) Å3
Triclinic, P1Z = 2
a = 10.9740 (3) ÅMo Kα radiation
b = 11.0721 (3) ŵ = 0.10 mm1
c = 11.1686 (3) ÅT = 223 K
α = 77.2135 (15)°0.32 × 0.17 × 0.06 mm
β = 73.2087 (14)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5770 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
4806 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.994Rint = 0.025
24934 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0433 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å3
5770 reflectionsΔρmin = 0.27 e Å3
587 parameters
Special details top

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) top
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)
O22A0.1011 (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*
C22A0.0654 (2)0.6892 (2)1.0404 (2)0.0445 (5)
C23A0.1511 (3)0.6078 (3)1.0851 (3)0.0584 (7)
H23A0.10860.53161.14160.088*
H23B0.15800.57701.01440.088*
H23C0.24200.66231.12820.088*
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)
O22B0.1340 (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)
H7B10.53770.18080.07650.046*
H7B20.62740.02610.05570.046*
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)
H14B0.71180.26490.08590.037*
C15B0.8623 (2)0.0906 (2)0.1492 (2)0.0410 (5)
H15C0.90320.00360.11690.049*
H15D0.81520.09900.21380.049*
C16B0.9698 (2)0.1512 (2)0.1981 (2)0.0446 (5)
H16B1.05860.10200.25260.054*
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)
H21D1.24570.30150.20190.153*
H21E1.13390.32920.27700.153*
H21F1.23830.18120.24770.153*
C22B0.0931 (2)0.3207 (3)0.4269 (2)0.0508 (6)
C23B0.1833 (3)0.2606 (3)0.5197 (3)0.0667 (8)
H23D0.23770.31830.58510.100*
H23E0.12740.17390.55570.100*
H23F0.24370.25040.47890.100*
Atomic displacement parameters (Å2) top
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, º) top
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—O8A173.4 (3)C6B—O6B—N6B—O8B179.4 (2)
C6A—O6A—N6A—O7A5.4 (4)C6B—O6B—N6B—O7B0.2 (3)
C10A—C1A—C2A—C3A54.8 (3)C10B—C1B—C2B—C3B55.8 (3)
C22A—O3A—C3A—C2A90.6 (2)C22B—O3B—C3B—C2B113.4 (3)
C22A—O3A—C3A—C4A147.5 (2)C22B—O3B—C3B—C4B125.5 (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—C5A179.87 (17)O3B—C3B—C4B—C5B173.26 (17)
C2A—C3A—C4A—C5A57.7 (2)C2B—C3B—C4B—C5B54.7 (3)
C3A—C4A—C5A—O5A57.2 (2)C3B—C4B—C5B—O5B58.0 (2)
C3A—C4A—C5A—C6A172.08 (18)C3B—C4B—C5B—C6B173.30 (18)
C3A—C4A—C5A—C10A59.7 (2)C3B—C4B—C5B—C10B58.5 (2)
N6A—O6A—C6A—C7A138.5 (2)N6B—O6B—C6B—C7B141.69 (18)
N6A—O6A—C6A—C5A96.8 (2)N6B—O6B—C6B—C5B95.3 (2)
O5A—C5A—C6A—O6A173.49 (17)O5B—C5B—C6B—O6B176.68 (15)
C4A—C5A—C6A—O6A55.8 (2)C4B—C5B—C6B—O6B58.6 (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—C7A177.25 (19)C4B—C5B—C6B—C7B177.82 (18)
C10A—C5A—C6A—C7A49.9 (3)C10B—C5B—C6B—C7B51.0 (2)
O6A—C6A—C7A—C8A75.3 (2)O6B—C6B—C7B—C8B73.1 (2)
C5A—C6A—C7A—C8A48.2 (3)C5B—C6B—C7B—C8B49.5 (2)
C6A—C7A—C8A—C14A171.4 (2)C6B—C7B—C8B—C14B170.62 (17)
C6A—C7A—C8A—C9A52.4 (3)C6B—C7B—C8B—C9B52.2 (2)
C14A—C8A—C9A—C11A51.3 (2)C14B—C8B—C9B—C11B54.5 (2)
C7A—C8A—C9A—C11A171.77 (19)C7B—C8B—C9B—C11B174.82 (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—C19A65.6 (2)C2B—C1B—C10B—C19B63.6 (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—C19A65.5 (2)C8B—C9B—C10B—C19B65.8 (2)
C8A—C9A—C10A—C19A62.8 (2)C11B—C9B—C10B—C19B61.3 (2)
C11A—C9A—C10A—C1A54.5 (2)C8B—C9B—C10B—C1B173.61 (17)
C8A—C9A—C10A—C1A177.16 (16)C11B—C9B—C10B—C1B59.3 (2)
C11A—C9A—C10A—C5A171.91 (17)C8B—C9B—C10B—C5B57.3 (2)
C8A—C9A—C10A—C5A59.7 (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—C19A66.7 (2)C6B—C5B—C10B—C19B67.5 (2)
O5A—C5A—C10A—C1A61.6 (2)O5B—C5B—C10B—C1B59.4 (2)
C4A—C5A—C10A—C1A56.9 (2)C4B—C5B—C10B—C1B58.8 (2)
C6A—C5A—C10A—C1A175.27 (19)C6B—C5B—C10B—C1B173.45 (18)
O5A—C5A—C10A—C9A58.7 (2)O5B—C5B—C10B—C9B59.8 (2)
C4A—C5A—C10A—C9A177.30 (16)C4B—C5B—C10B—C9B178.03 (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—C12B179.77 (17)
C9A—C11A—C12A—C13A53.0 (2)C9B—C11B—C12B—C13B53.0 (2)
C11A—C12A—C13A—C17A171.14 (17)C11B—C12B—C13B—C17B168.92 (17)
C11A—C12A—C13A—C14A57.8 (2)C11B—C12B—C13B—C18B68.6 (2)
C11A—C12A—C13A—C18A66.1 (2)C11B—C12B—C13B—C14B55.0 (2)
C7A—C8A—C14A—C15A54.1 (3)C7B—C8B—C14B—C15B52.6 (2)
C9A—C8A—C14A—C15A174.47 (19)C9B—C8B—C14B—C15B173.11 (17)
C7A—C8A—C14A—C13A178.69 (19)C7B—C8B—C14B—C13B178.11 (17)
C9A—C8A—C14A—C13A60.9 (2)C9B—C8B—C14B—C13B61.38 (19)
C17A—C13A—C14A—C8A170.59 (17)C12B—C13B—C14B—C8B62.4 (2)
C12A—C13A—C14A—C8A65.0 (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—C15A74.8 (2)C18B—C13B—C14B—C15B73.6 (2)
C8A—C14A—C15A—C16A164.78 (19)C8B—C14B—C15B—C16B166.35 (17)
C13A—C14A—C15A—C16A36.4 (2)C13B—C14B—C15B—C16B37.0 (2)
C17A—O16A—C16A—C15A99.3 (2)C17B—O16B—C16B—C15B99.7 (2)
C14A—C15A—C16A—O16A44.4 (2)C14B—C15B—C16B—O16B44.3 (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—C13A95.6 (2)C16B—O16B—C17B—C13B95.6 (2)
C15A—C16A—C17A—O16A106.9 (2)C15B—C16B—C17B—O16B106.63 (19)
O16A—C16A—C17A—C20A95.9 (2)O16B—C16B—C17B—C20B96.5 (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—O16A78.8 (2)C12B—C13B—C17B—O16B80.6 (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—C16A141.5 (2)C12B—C13B—C17B—C16B143.32 (19)
C14A—C13A—C17A—C16A25.1 (2)C18B—C13B—C17B—C16B91.89 (19)
C18A—C13A—C17A—C16A93.1 (2)C14B—C13B—C17B—C16B25.6 (2)
C12A—C13A—C17A—C20A64.4 (3)C12B—C13B—C17B—C20B63.1 (3)
C14A—C13A—C17A—C20A179.2 (2)C18B—C13B—C17B—C20B61.7 (3)
C18A—C13A—C17A—C20A61.0 (3)C14B—C13B—C17B—C20B179.23 (19)
O16A—C17A—C20A—O20A131.8 (2)O16B—C17B—C20B—O20B141.3 (2)
C16A—C17A—C20A—O20A163.2 (2)C16B—C17B—C20B—O20B153.3 (2)
C13A—C17A—C20A—O20A12.9 (3)C13B—C17B—C20B—O20B3.7 (4)
O16A—C17A—C20A—C21A47.5 (3)O16B—C17B—C20B—C21B36.2 (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—O22A9.5 (4)C3B—O3B—C22B—O22B4.5 (5)
C3A—O3A—C22A—C23A173.6 (2)C3B—O3B—C22B—C23B176.3 (2)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC23H33NO8
Mr451.50
Crystal system, space groupTriclinic, P1
Temperature (K)223
a, b, c (Å)10.9740 (3), 11.0721 (3), 11.1686 (3)
α, β, γ (°)77.2135 (15), 73.2087 (14), 64.3465 (14)
V3)1163.81 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.32 × 0.17 × 0.06
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.947, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
24934, 5770, 4806
Rint0.025
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 1.04
No. of reflections5770
No. of parameters587
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.27

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5A—H5A···O20Ai0.822.012.822 (2)168.4
O5B—H5B···O20Bi0.822.112.913 (2)167.7
Symmetry code: (i) x1, y, z.
 

Acknowledgements

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

References

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First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationPinto, R. M. A., Ramos Silva, M., Matos Beja, A. & Salvador, J. A. R. (2007b). Acta Cryst. E63, o2138–o2139.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationSalvador, J. A. R., Silvestre, S. M. & Moreira, V. M. (2006). Curr. Org. Chem. 10, 2227–2257.  Web of Science CrossRef CAS Google Scholar
First citationSalvador, J. A. R., Silvestre, S. M. & Moreira, V. M. (2008). Curr. Org. Chem. 12, 492–522.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Pages o1271-o1272
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