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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o221.
Published online 2009 January 8. doi:  10.1107/S1600536808043481
PMCID: PMC2968271

Preaustinoid A: a meroterpene produced by Penicillium sp.

Abstract

The title meroterpene preaustinoid A (systematic name: methyl 15-hydr­oxy-2,6,6,10,13,15-hexa­methyl-17-methyl­ene-7,14,16-trioxotetra­cyclo­[11.3.1.02,11.05,10]hepta­decane-1-car­box­yl­ate), C26H36O6, features a fused four-ring arrangement. Three rings are in different distorted chair conformations and the other is in a distorted boat conformation. The absolute configuration was established based on [αD] = −4.97° (c = 1.10 g l−1, CH2Cl2). In the crystal, the mol­ecules are connected into supra­molecular chains via O—H(...)O hydrogen bonds.

Related literature

For related literature, see: dos Santos & Rodrigues-Fo (2002 [triangle]). For structure analysis, see: Cremer and Pople (1975 [triangle]); Iulek and Zukerman-Schpector (1997 [triangle])).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o221-scheme1.jpg

Experimental

Crystal data

  • C26H36O6
  • M r = 444.55
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o221-efi1.jpg
  • a = 8.5023 (2) Å
  • b = 13.5405 (2) Å
  • c = 19.7127 (4) Å
  • V = 2269.43 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 290 (2) K
  • 0.37 × 0.28 × 0.11 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 27134 measured reflections
  • 2938 independent reflections
  • 2677 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.093
  • S = 1.03
  • 2938 reflections
  • 297 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: APEX2, COSMO and BIS (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043481/tk2346sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043481/tk2346Isup2.hkl

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

Acknowledgments

We thank FAPESP, CNPq and CAPES for financial support. Professor R. A. Burrow of the Federal University of Santa Maria is gratefully acknowledged for helping with the collection of the intensity data.

supplementary crystallographic information

Comment

Endophytic fungi have been a rich source of important biologically active secondary metabolites, in particular meroterpenoids, a class of complex metabolites derived from a mixed terpenoid-polyketide biosynthetic pathway. During an on-going study of substances produced by endophytic fungi, the title compound (I) was isolated and its structure postulated based on APCIMS (Atmospheric Pressure Chemical Ionization Mass Spectrometry), HREIMS (High Resolution Electrospray Mass Spectrometry) and a variety of NMR studies (dos Santos and Rodrigues-Fo, 2002). As suitable crystals were subsequently obtained, a crystal structure determination was undertaken. The four fused rings are in different distorted conformations. Rings A and C are distorted towards a half-chair conformation, ring B is distorted towards a half-boat conformation, and ring D is a boat conformation that is highly distorted towards a half-boat. The ring-puckering parameters (Cremer & Pople, 1975, Iulek & Zukerman-Shpector, 1997) for rings A,B,C, D are: q2 = 0.062 (2), 0.093 (2), 0.059 (2), 0.582 (2) Å, q3 = -0.524 (2), 0.577 (2), -0.624 (2), -0.139 (2) Å, Q = 0.528 (2), 0.584 (2), 0.627 (2), 0.599 (2)°, [var phi]2 = 90 (2), 172 (1), -149 (2), -122.4 (2)°, and θ2 = 173.3 (2), 9.1 (2), 174.6 (2), 103.4 (2)°, respectively. The absolute configuration was established based on the [αD] = -4.97° (c 1.10 g/L, CH2Cl2) and the results reported in dos Santos & Rodrigues-Fo (2002). The molecules are linked into a supramolecular chain via intermolecular O-H···O hydrogen bonds, Table 1.

Experimental

Compound (I), Preaustinoid A, was produced during cultivation of Penicillum sp over sterilized rice, and isolated from the methanol extract of the culture. Suitable crystals were obtained, by slow evaporation, from a mixture of dichloromethane, methanol and water.

Refinement

In the absence of significant anomalous scattering effects, Friedel pairs were averaged in the final refinement. The H atoms were refined in the riding-model approximation with C—H = 0.93 - 0.98 Å and (0.82 for O—H), and with Uiso(H) = 1.5Ueq(methyl-C) or 1.2Ueq(remaining-C and –O).

Figures

Fig. 1.
The molecular structure of (I) showing atom labelling scheme and displacement ellipsoids at the 30% probability level (arbitrary spheres for the H atoms).

Crystal data

C26H36O6F(000) = 960
Mr = 444.55Dx = 1.301 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 22936 reflections
a = 8.5023 (2) Åθ = 1.0–27.5°
b = 13.5405 (2) ŵ = 0.09 mm1
c = 19.7127 (4) ÅT = 290 K
V = 2269.43 (8) Å3Prism, colorless
Z = 40.37 × 0.28 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer2677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 27.5°, θmin = 1.8°
[var phi] and ω scansh = −11→9
27134 measured reflectionsk = −17→17
2938 independent reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.093w = 1/[σ2(Fo2) + (0.0531P)2 + 0.3814P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2938 reflectionsΔρmax = 0.22 e Å3
297 parametersΔρmin = −0.13 e Å3
0 restraintsAbsolute structure: [αD] = -4.97° and results in dos Santos & Rodrigues-Fo (2002)
Primary atom site location: structure-invariant direct methods

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
C10.6598 (2)1.07289 (12)1.05643 (9)0.0288 (4)
C20.6226 (2)1.08110 (12)0.97653 (9)0.0285 (4)
C30.4489 (2)1.10698 (14)0.96387 (10)0.0339 (4)
H3A0.38351.06660.99310.041*
H3B0.43141.17560.97600.041*
C40.3986 (2)1.09105 (13)0.89014 (10)0.0335 (4)
H4A0.45881.13430.86070.040*
H4B0.28821.10760.88510.040*
C50.4252 (2)0.98347 (13)0.86909 (9)0.0281 (4)
H50.37890.94440.90590.034*
C60.3310 (2)0.95241 (13)0.80444 (10)0.0333 (4)
C70.3688 (3)0.84397 (14)0.78946 (10)0.0375 (4)
C80.5381 (3)0.81430 (17)0.79148 (13)0.0480 (5)
H8A0.59250.84370.75320.058*
H8B0.54560.74310.78710.058*
C90.6192 (3)0.84641 (14)0.85749 (10)0.0379 (4)
H9A0.72990.82940.85510.045*
H9B0.57360.81030.89520.045*
C100.6034 (2)0.95805 (13)0.87113 (9)0.0289 (4)
C110.6583 (2)0.97663 (12)0.94619 (8)0.0266 (3)
H110.59670.93040.97370.032*
C120.8309 (2)0.94807 (15)0.95867 (10)0.0346 (4)
H12A0.89860.99480.93550.041*
H12B0.85030.88330.93940.041*
C130.8741 (2)0.94642 (14)1.03528 (10)0.0338 (4)
C140.7714 (3)0.86428 (14)1.06479 (10)0.0372 (4)
C150.6277 (3)0.89190 (13)1.10736 (9)0.0346 (4)
C160.5554 (2)0.99228 (14)1.08868 (9)0.0322 (4)
C170.8335 (2)1.04648 (13)1.06521 (9)0.0317 (4)
C180.6196 (2)1.16872 (13)1.09524 (10)0.0341 (4)
C190.5811 (3)1.23338 (17)1.20486 (12)0.0498 (6)
H19A0.47801.25641.19280.075*
H19B0.65581.28581.19890.075*
H19C0.58111.21261.25140.075*
C200.7279 (3)1.16296 (14)0.94607 (10)0.0392 (5)
H20A0.70831.22410.96920.059*
H20B0.70431.17060.89870.059*
H20C0.83641.14500.95130.059*
C210.1540 (3)0.96145 (17)0.81845 (13)0.0475 (5)
H21A0.12810.92530.85880.071*
H21B0.09610.93490.78080.071*
H21C0.12701.02970.82450.071*
C220.3678 (3)1.01321 (16)0.74011 (10)0.0448 (5)
H22A0.35521.08220.74980.067*
H22B0.29690.99440.70440.067*
H22C0.47411.00080.72610.067*
C230.7051 (2)1.01368 (17)0.81888 (10)0.0409 (5)
H23A0.70110.97980.77610.061*
H23B0.81191.01630.83460.061*
H23C0.66561.07960.81340.061*
C241.0483 (3)0.91813 (19)1.04234 (13)0.0496 (6)
H24A1.07570.91491.08950.074*
H24B1.11220.96691.02030.074*
H24C1.06580.85491.02160.074*
C250.5021 (3)0.81210 (15)1.10693 (14)0.0515 (6)
H25A0.41820.83061.13690.077*
H25B0.54710.75081.12180.077*
H25C0.46160.80451.06180.077*
C260.9386 (3)1.10751 (16)1.09100 (11)0.0429 (5)
H26A1.04431.09011.09150.051*
H26B0.90691.16801.10870.051*
O10.5918 (2)1.24745 (10)1.07174 (8)0.0472 (4)
O20.6234 (2)1.15134 (10)1.16213 (7)0.0466 (4)
O30.2674 (2)0.78454 (11)0.77637 (9)0.0544 (4)
O40.8037 (2)0.77818 (11)1.05593 (10)0.0617 (5)
O50.6898 (2)0.90860 (11)1.17396 (7)0.0485 (4)
H1O50.71630.85581.19070.058*
O60.41897 (17)1.00801 (12)1.10126 (8)0.0465 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0316 (9)0.0236 (7)0.0311 (8)−0.0013 (7)−0.0004 (7)−0.0008 (6)
C20.0322 (9)0.0238 (7)0.0295 (8)0.0008 (7)−0.0008 (7)0.0006 (6)
C30.0352 (10)0.0299 (8)0.0365 (9)0.0057 (8)−0.0024 (8)−0.0049 (7)
C40.0348 (9)0.0282 (8)0.0375 (9)0.0073 (8)−0.0057 (8)−0.0025 (7)
C50.0288 (9)0.0265 (8)0.0291 (8)0.0009 (7)0.0010 (7)0.0010 (6)
C60.0334 (9)0.0303 (8)0.0362 (9)0.0002 (8)−0.0034 (8)−0.0013 (7)
C70.0468 (12)0.0338 (9)0.0319 (9)−0.0007 (9)−0.0064 (9)−0.0024 (7)
C80.0513 (13)0.0410 (11)0.0516 (13)0.0118 (10)−0.0063 (11)−0.0160 (10)
C90.0407 (11)0.0352 (9)0.0378 (10)0.0111 (9)−0.0046 (9)−0.0064 (8)
C100.0282 (9)0.0300 (8)0.0285 (8)0.0025 (7)0.0025 (7)0.0004 (7)
C110.0268 (8)0.0265 (8)0.0265 (8)0.0016 (7)0.0018 (7)0.0012 (6)
C120.0299 (9)0.0406 (10)0.0331 (9)0.0070 (8)0.0009 (8)−0.0012 (8)
C130.0309 (9)0.0345 (9)0.0360 (9)0.0056 (8)−0.0044 (8)−0.0009 (8)
C140.0451 (11)0.0336 (9)0.0329 (9)0.0053 (9)−0.0056 (9)0.0001 (7)
C150.0445 (11)0.0279 (8)0.0313 (9)−0.0043 (8)−0.0031 (8)0.0014 (7)
C160.0373 (10)0.0308 (9)0.0284 (8)−0.0032 (8)0.0007 (8)−0.0023 (7)
C170.0331 (9)0.0318 (8)0.0302 (8)0.0006 (8)−0.0011 (8)0.0027 (7)
C180.0344 (10)0.0303 (8)0.0376 (10)−0.0015 (8)−0.0026 (8)−0.0041 (7)
C190.0606 (15)0.0438 (11)0.0450 (11)−0.0037 (11)0.0107 (11)−0.0153 (10)
C200.0450 (12)0.0331 (9)0.0396 (10)−0.0096 (9)−0.0007 (9)0.0069 (8)
C210.0339 (11)0.0461 (11)0.0624 (14)−0.0015 (9)−0.0053 (10)−0.0104 (10)
C220.0533 (13)0.0453 (11)0.0358 (10)0.0002 (10)−0.0068 (10)0.0038 (9)
C230.0356 (10)0.0544 (12)0.0328 (9)−0.0030 (9)0.0050 (8)0.0065 (9)
C240.0362 (11)0.0583 (13)0.0543 (13)0.0131 (11)−0.0111 (10)−0.0098 (11)
C250.0584 (14)0.0319 (10)0.0642 (14)−0.0127 (10)−0.0048 (12)0.0048 (10)
C260.0375 (11)0.0417 (11)0.0496 (12)−0.0050 (9)−0.0073 (9)−0.0005 (9)
O10.0638 (10)0.0288 (6)0.0490 (8)0.0075 (7)−0.0084 (8)−0.0050 (6)
O20.0698 (11)0.0342 (7)0.0359 (7)0.0028 (7)0.0037 (8)−0.0064 (6)
O30.0614 (11)0.0355 (8)0.0664 (10)−0.0091 (8)−0.0145 (9)−0.0019 (7)
O40.0825 (13)0.0312 (7)0.0716 (11)0.0123 (8)0.0137 (10)−0.0002 (7)
O50.0746 (12)0.0382 (7)0.0327 (7)0.0031 (8)−0.0117 (7)−0.0005 (6)
O60.0388 (8)0.0467 (8)0.0539 (9)−0.0008 (7)0.0106 (7)0.0049 (7)

Geometric parameters (Å, °)

C1—C171.529 (3)C13—C241.536 (3)
C1—C161.544 (3)C14—O41.210 (2)
C1—C181.545 (2)C14—C151.529 (3)
C1—C21.610 (2)C15—O51.433 (2)
C2—C31.538 (3)C15—C251.519 (3)
C2—C201.546 (3)C15—C161.536 (3)
C2—C111.566 (2)C16—O61.205 (2)
C3—C41.530 (3)C17—C261.319 (3)
C3—H3A0.9700C18—O11.186 (2)
C3—H3B0.9700C18—O21.340 (2)
C4—C51.531 (2)C19—O21.440 (2)
C4—H4A0.9700C19—H19A0.9600
C4—H4B0.9700C19—H19B0.9600
C5—C101.554 (2)C19—H19C0.9600
C5—C61.563 (3)C20—H20A0.9600
C5—H50.9800C20—H20B0.9600
C6—C71.532 (3)C20—H20C0.9600
C6—C211.535 (3)C21—H21A0.9600
C6—C221.544 (3)C21—H21B0.9600
C7—O31.207 (3)C21—H21C0.9600
C7—C81.495 (3)C22—H22A0.9600
C8—C91.536 (3)C22—H22B0.9600
C8—H8A0.9700C22—H22C0.9600
C8—H8B0.9700C23—H23A0.9600
C9—C101.541 (2)C23—H23B0.9600
C9—H9A0.9700C23—H23C0.9600
C9—H9B0.9700C24—H24A0.9600
C10—C231.541 (3)C24—H24B0.9600
C10—C111.572 (2)C24—H24C0.9600
C11—C121.538 (3)C25—H25A0.9600
C11—H110.9800C25—H25B0.9600
C12—C131.554 (3)C25—H25C0.9600
C12—H12A0.9700C26—H26A0.9300
C12—H12B0.9700C26—H26B0.9300
C13—C171.518 (3)O5—H1O50.8200
C13—C141.529 (3)
C17—C1—C16110.07 (14)C17—C13—C24114.00 (17)
C17—C1—C18110.75 (15)C14—C13—C24109.54 (17)
C16—C1—C18105.22 (15)C17—C13—C12108.14 (15)
C17—C1—C2108.47 (15)C14—C13—C12104.21 (16)
C16—C1—C2109.79 (14)C24—C13—C12108.61 (17)
C18—C1—C2112.51 (14)O4—C14—C13121.1 (2)
C3—C2—C20109.24 (15)O4—C14—C15119.7 (2)
C3—C2—C11109.27 (15)C13—C14—C15119.16 (16)
C20—C2—C11112.77 (15)O5—C15—C25112.11 (17)
C3—C2—C1111.30 (15)O5—C15—C14104.29 (17)
C20—C2—C1108.39 (14)C25—C15—C14112.63 (17)
C11—C2—C1105.86 (13)O5—C15—C16103.14 (14)
C4—C3—C2112.98 (16)C25—C15—C16110.30 (17)
C4—C3—H3A109.0C14—C15—C16113.86 (16)
C2—C3—H3A109.0O6—C16—C15119.46 (18)
C4—C3—H3B109.0O6—C16—C1120.88 (18)
C2—C3—H3B109.0C15—C16—C1119.63 (17)
H3A—C3—H3B107.8C26—C17—C13123.72 (19)
C3—C4—C5110.50 (15)C26—C17—C1123.45 (18)
C3—C4—H4A109.6C13—C17—C1112.61 (16)
C5—C4—H4A109.6O1—C18—O2123.17 (17)
C3—C4—H4B109.6O1—C18—C1127.27 (18)
C5—C4—H4B109.6O2—C18—C1109.54 (15)
H4A—C4—H4B108.1O2—C19—H19A109.5
C4—C5—C10110.34 (15)O2—C19—H19B109.5
C4—C5—C6113.65 (15)H19A—C19—H19B109.5
C10—C5—C6117.46 (15)O2—C19—H19C109.5
C4—C5—H5104.6H19A—C19—H19C109.5
C10—C5—H5104.6H19B—C19—H19C109.5
C6—C5—H5104.6C2—C20—H20A109.5
C7—C6—C21108.47 (17)C2—C20—H20B109.5
C7—C6—C22108.08 (17)H20A—C20—H20B109.5
C21—C6—C22107.68 (18)C2—C20—H20C109.5
C7—C6—C5107.91 (15)H20A—C20—H20C109.5
C21—C6—C5109.53 (17)H20B—C20—H20C109.5
C22—C6—C5114.99 (16)C6—C21—H21A109.5
O3—C7—C8120.95 (19)C6—C21—H21B109.5
O3—C7—C6122.0 (2)H21A—C21—H21B109.5
C8—C7—C6117.03 (18)C6—C21—H21C109.5
C7—C8—C9112.26 (18)H21A—C21—H21C109.5
C7—C8—H8A109.2H21B—C21—H21C109.5
C9—C8—H8A109.2C6—C22—H22A109.5
C7—C8—H8B109.2C6—C22—H22B109.5
C9—C8—H8B109.2H22A—C22—H22B109.5
H8A—C8—H8B107.9C6—C22—H22C109.5
C8—C9—C10112.73 (17)H22A—C22—H22C109.5
C8—C9—H9A109.0H22B—C22—H22C109.5
C10—C9—H9A109.0C10—C23—H23A109.5
C8—C9—H9B109.0C10—C23—H23B109.5
C10—C9—H9B109.0H23A—C23—H23B109.5
H9A—C9—H9B107.8C10—C23—H23C109.5
C23—C10—C9108.29 (16)H23A—C23—H23C109.5
C23—C10—C5114.92 (15)H23B—C23—H23C109.5
C9—C10—C5107.32 (16)C13—C24—H24A109.5
C23—C10—C11112.61 (16)C13—C24—H24B109.5
C9—C10—C11107.17 (14)H24A—C24—H24B109.5
C5—C10—C11106.16 (14)C13—C24—H24C109.5
C12—C11—C2110.55 (15)H24A—C24—H24C109.5
C12—C11—C10113.19 (15)H24B—C24—H24C109.5
C2—C11—C10116.54 (14)C15—C25—H25A109.5
C12—C11—H11105.1C15—C25—H25B109.5
C2—C11—H11105.1H25A—C25—H25B109.5
C10—C11—H11105.1C15—C25—H25C109.5
C11—C12—C13112.61 (15)H25A—C25—H25C109.5
C11—C12—H12A109.1H25B—C25—H25C109.5
C13—C12—H12A109.1C17—C26—H26A120.0
C11—C12—H12B109.1C17—C26—H26B120.0
C13—C12—H12B109.1H26A—C26—H26B120.0
H12A—C12—H12B107.8C18—O2—C19115.72 (16)
C17—C13—C14111.82 (16)C15—O5—H1O5109.5
C17—C1—C2—C3179.65 (14)C5—C10—C11—C2−54.13 (19)
C16—C1—C2—C359.35 (19)C2—C11—C12—C1358.8 (2)
C18—C1—C2—C3−57.47 (19)C10—C11—C12—C13−168.36 (15)
C17—C1—C2—C20−60.19 (18)C11—C12—C13—C17−55.3 (2)
C16—C1—C2—C20179.50 (15)C11—C12—C13—C1463.8 (2)
C18—C1—C2—C2062.69 (19)C11—C12—C13—C24−179.52 (17)
C17—C1—C2—C1161.04 (17)C17—C13—C14—O4−167.3 (2)
C16—C1—C2—C11−59.27 (18)C24—C13—C14—O4−40.0 (3)
C18—C1—C2—C11−176.09 (15)C12—C13—C14—O476.1 (2)
C20—C2—C3—C474.34 (19)C17—C13—C14—C1511.4 (2)
C11—C2—C3—C4−49.46 (19)C24—C13—C14—C15138.78 (18)
C1—C2—C3—C4−166.01 (14)C12—C13—C14—C15−105.16 (19)
C2—C3—C4—C558.4 (2)O4—C14—C15—O595.3 (2)
C3—C4—C5—C10−63.8 (2)C13—C14—C15—O5−83.44 (19)
C3—C4—C5—C6161.82 (16)O4—C14—C15—C25−26.5 (3)
C4—C5—C6—C7179.97 (16)C13—C14—C15—C25154.76 (18)
C10—C5—C6—C749.0 (2)O4—C14—C15—C16−153.0 (2)
C4—C5—C6—C21−62.1 (2)C13—C14—C15—C1628.2 (2)
C10—C5—C6—C21166.93 (17)O5—C15—C16—O6−91.8 (2)
C4—C5—C6—C2259.3 (2)C25—C15—C16—O628.1 (3)
C10—C5—C6—C22−71.7 (2)C14—C15—C16—O6155.85 (18)
C21—C6—C7—O315.0 (3)O5—C15—C16—C186.0 (2)
C22—C6—C7—O3−101.4 (2)C25—C15—C16—C1−154.06 (18)
C5—C6—C7—O3133.6 (2)C14—C15—C16—C1−26.3 (2)
C21—C6—C7—C8−165.2 (2)C17—C1—C16—O6163.11 (18)
C22—C6—C7—C878.4 (2)C18—C1—C16—O643.8 (2)
C5—C6—C7—C8−46.6 (2)C2—C1—C16—O6−77.6 (2)
O3—C7—C8—C9−128.7 (2)C17—C1—C16—C15−14.7 (2)
C6—C7—C8—C951.5 (3)C18—C1—C16—C15−134.06 (16)
C7—C8—C9—C10−55.0 (3)C2—C1—C16—C15104.64 (18)
C8—C9—C10—C23−70.2 (2)C14—C13—C17—C26129.3 (2)
C8—C9—C10—C554.4 (2)C24—C13—C17—C264.4 (3)
C8—C9—C10—C11168.11 (17)C12—C13—C17—C26−116.5 (2)
C4—C5—C10—C23−65.9 (2)C14—C13—C17—C1−55.9 (2)
C6—C5—C10—C2366.6 (2)C24—C13—C17—C1179.19 (18)
C4—C5—C10—C9173.62 (15)C12—C13—C17—C158.3 (2)
C6—C5—C10—C9−53.9 (2)C16—C1—C17—C26−128.2 (2)
C4—C5—C10—C1159.28 (18)C18—C1—C17—C26−12.3 (3)
C6—C5—C10—C11−168.29 (14)C2—C1—C17—C26111.7 (2)
C3—C2—C11—C12−179.43 (15)C16—C1—C17—C1357.01 (19)
C20—C2—C11—C1258.88 (19)C18—C1—C17—C13172.94 (15)
C1—C2—C11—C12−59.47 (17)C2—C1—C17—C13−63.13 (18)
C3—C2—C11—C1049.48 (19)C17—C1—C18—O1108.2 (2)
C20—C2—C11—C10−72.2 (2)C16—C1—C18—O1−132.9 (2)
C1—C2—C11—C10169.43 (14)C2—C1—C18—O1−13.4 (3)
C23—C10—C11—C12−57.4 (2)C17—C1—C18—O2−70.5 (2)
C9—C10—C11—C1261.6 (2)C16—C1—C18—O248.4 (2)
C5—C10—C11—C12176.01 (14)C2—C1—C18—O2167.95 (16)
C23—C10—C11—C272.4 (2)O1—C18—O2—C194.0 (3)
C9—C10—C11—C2−168.58 (16)C1—C18—O2—C19−177.29 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H1O5···O3i0.822.052.870 (2)173
C23—H23A···O5ii0.962.683.173 (2)112

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2346).

References

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