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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o331–o332.
Published online 2010 January 9. doi:  10.1107/S1600536810000528
PMCID: PMC2979944

An orthorhombic polymorph of mulinic acid

Abstract

The title compound [systematic name: (3S,3aS,10bR)-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,10,10a,10b-deca­hydro-endo-epidioxy­cyclo­hepta­[e]indene-3a(1H)-carboxylic acid], C20H30O4, is a polymorphic form of a previously reported structure [Loyola et al. (1990 [triangle]). Tetra­hedron, 46, 5413–5420]. The newly found ortho­rhom­bic polymorph crystallizes in P212121 with two mol­ecules in the asymmetric unit. The mol­ecules are linked into discrete D(2) chains by simple O—H(...)O inter­actions. There are only slight variations in the mol­ecular geometry and supra­molecular organization in the crystal structures of the two polymorphs. The densities are 1.145 (monoclinic, P21) and 1.155 Mg m−3 (ortho­rhom­bic, P212121).

Related literature

For background to the structures of mulinic acid, see: Loyola et al. (1990 [triangle], 2004 [triangle]). For their biological activity, see: Munizaga & Gunkel (1958 [triangle]); Araya et al. (2003 [triangle]). For related structures, see: Brito et al. (2008a [triangle],b [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o331-scheme1.jpg

Experimental

Crystal data

  • C20H30O4
  • M r = 334.44
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o331-efi2.jpg
  • a = 7.4160 (15) Å
  • b = 19.374 (4) Å
  • c = 26.767 (5) Å
  • V = 3845.8 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.18 × 0.15 × 0.08 mm

Data collection

  • Nonius KappaCCD area-detector diffractometer
  • 43215 measured reflections
  • 5387 independent reflections
  • 4452 reflections with I > 2σ(I)
  • R int = 0.08

Refinement

  • R[F 2 > 2σ(F 2)] = 0.091
  • wR(F 2) = 0.224
  • S = 1.25
  • 5387 reflections
  • 444 parameters
  • H-atom parameters constrained
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN; 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 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [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/S1600536810000528/om2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000528/om2310Isup2.hkl

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

Acknowledgments

We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system.

supplementary crystallographic information

Comment

Polymorphism in crystalline material may occurs as a result of crystallization from different solvents, crystallizations in the presence of small-molecules or macromolecular additives, or phase transitions etc (Bernstein et al., 1995). We have obtained an orthorhombic modification of (I) by crystallization from a chloroform-acetonitrile (1:1) whereas the monoclinic phase was obtained from ethylacetate-n-hexane solution of (I) (1:1). The title compound was obtained from dried and finely powdered aerial parts of Mulinun crassifolium Phil. (Loyola et al., 1990).This plant, commonly know as chuquican, susurco or espinilla, is used in folk medicine, principally against diabetes, and bronchial (cough) and intestinal disorders (Munizaga & Gunkel, 1958). Mulinane diterpenes exhibit antiplasmodial and anti-tripanosomacruzi (Araya et al., 2003) activity. We report here the crystal structure of a new polymorphic form of a previously reported structure, characterized by different crystal packing according to our X-ray investigation and a lower melting point than the reported for the known monoclinic phase (132–139° vs 185–187°, respectively). We were not able to determine the absolute stereochemistry by X-ray methods, and the configuration shown here was chosen to be in accord with the reported in the previous X-ray diffraction studies (Loyola et al. 2004). The molecule of the title compound is built up from three fused carbocycles, one five-menbered, one six-membered and one seven-membered ring. The five- membered ring has an envelope conformation (ring A) whereas the six-membered ring has a perfect chair conformation (ring B) and the seven-menbered ring has a boat conformation (ring C) respectively. [Q2=0.442 (4) Å, [var phi] =104.8 (6)°; QT=0.556 (4) Å, θ=163.6 (4)°, [var phi] =180.4 (2)°; QT=1.153 (4) Å, [var phi]2 =179.5 (2)°] (Cremer & Pople, 1975). The isopropyl, methyl groups and the carboxylic acid at C3, C8 and C5a are β-oriented respectively, whereas the endo-peroxide group is α-oriented. The molecules are linked into R22 (8) dimers by simple O–H···O interactions (Table 1 and Fig. 2). There are only slight variations in the molecular geometry and supramolecular organization in the crystal structures of the two polymorphs. The densities are 1.145 Mg m-3 (monoclinic, P21) and 1.155 Mg m-3 (orthorhombic, P212121).

Experimental

We have obtained the orthorhombic modification of (I) by recrystallization from chloroform-acetonitrile (1:1) at room temperature. The spectroscopic data are identical to those of monoclinic phase.

Refinement

In the absence of anomalous scatterers, 3871 Friedel pairs were merged. PLATON (Spek, 2009) reports a solvent accessible voids of total area 289.5 Å3 in the structure. However, the low residual electron density does not suggest additional solvent in the structure. This was confirmed using the SQUEEZE procedure (Spek, 2009). All H atoms were refined as riding on their parent atoms, with distances of 0.82 (OH), 0.98 (CH), 0.97 (CH2) and 0.96 (CH3) Å from the parent C and O atoms, with Uiso(H) = 1.2Ueq(C, O) or 1.5Ueq(C).

Figures

Fig. 1.
A view of the molecular structure of the title compound, with the atom numbering scheme. Displacemenent ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
Fig. 2.
Part of the crystal structure, showing the discrete chain D(2) motif. For clarity only the H atoms involved in the hydrogen bonds (dashed lines) are shown.

Crystal data

C20H30O4F(000) = 1456
Mr = 334.44Dx = 1.155 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5298 reflections
a = 7.4160 (15) Åθ = 1.3–28.6°
b = 19.374 (4) ŵ = 0.08 mm1
c = 26.767 (5) ÅT = 293 K
V = 3845.8 (13) Å3Prism, colourless
Z = 80.18 × 0.15 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer4452 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.08
graphiteθmax = 28.6°, θmin = 1.3°
[var phi] scans, and ω scans with κ offsetsh = −9→9
43215 measured reflectionsk = −26→26
5387 independent reflectionsl = −35→35

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.091H-atom parameters constrained
wR(F2) = 0.224w = 1/[σ2(Fo2) + (0.1087P)2 + 1.0561P] where P = (Fo2 + 2Fc2)/3
S = 1.25(Δ/σ)max < 0.001
5387 reflectionsΔρmax = 0.45 e Å3
444 parametersΔρmin = −0.48 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (4)

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O11.0240 (4)0.5230 (2)0.81073 (10)0.0568 (9)
O20.7577 (4)0.5035 (2)0.84418 (9)0.0526 (8)
H20.81480.50860.87010.079*
O31.0415 (5)0.47601 (16)0.62047 (10)0.0487 (7)
O40.9156 (4)0.42951 (17)0.59483 (11)0.0548 (8)
C10.9999 (6)0.5802 (2)0.70754 (15)0.0400 (9)
H1A1.11480.57590.72460.048*
H1B1.02180.59250.67290.048*
C20.8811 (6)0.6343 (2)0.73306 (16)0.0443 (10)
H2A0.85670.67220.71040.053*
H2B0.94110.65250.76240.053*
C30.7038 (5)0.59812 (19)0.74797 (14)0.0353 (8)
H30.62580.59860.71840.042*
C40.6015 (6)0.6359 (2)0.78963 (15)0.0432 (9)
H40.67910.63730.81920.052*
C50.7641 (5)0.52173 (18)0.75618 (12)0.0302 (7)
C60.6212 (5)0.4648 (2)0.75110 (14)0.0384 (9)
H6A0.53560.46790.77840.046*
H6B0.55580.47050.720.046*
C70.7130 (7)0.3948 (2)0.75195 (16)0.0447 (10)
H7A0.6210.360.74670.054*
H7B0.76080.38780.78530.054*
C80.8680 (6)0.38068 (19)0.71418 (15)0.0400 (9)
C90.9969 (5)0.44437 (19)0.70991 (13)0.0347 (8)
H91.07420.44380.73960.042*
C100.8922 (5)0.51262 (18)0.71109 (12)0.0307 (7)
H100.81420.51190.68150.037*
C111.1245 (5)0.4450 (2)0.66369 (14)0.0409 (9)
H111.22740.47420.67260.049*
C121.2001 (7)0.3765 (3)0.64918 (17)0.0552 (12)
H121.31860.36460.65650.066*
C131.0920 (8)0.3340 (2)0.62570 (16)0.0522 (12)
C140.9036 (7)0.3622 (2)0.61696 (16)0.0494 (11)
H140.84560.3320.59230.059*
C150.7823 (6)0.3629 (2)0.66327 (16)0.0469 (10)
H15A0.72720.31770.66620.056*
H15B0.68590.39570.65730.056*
C161.1342 (10)0.2621 (3)0.6100 (2)0.0788 (18)
H16A1.25670.25140.61870.118*
H16B1.11890.25790.57450.118*
H16C1.05440.23070.62670.118*
C170.9659 (9)0.3176 (2)0.7367 (2)0.0638 (14)
H17A1.05230.30030.71320.096*
H17B0.87950.28220.74420.096*
H17C1.02670.33110.76680.096*
C180.5621 (9)0.7103 (3)0.7738 (2)0.0706 (15)
H18A0.49910.73370.80010.106*
H18B0.4890.71020.74420.106*
H18C0.67350.73380.76710.106*
C190.4256 (6)0.6015 (3)0.80408 (19)0.0585 (12)
H19A0.45020.55730.81880.088*
H19B0.35220.59550.77490.088*
H19C0.36290.62990.82780.088*
C200.8616 (5)0.51600 (19)0.80626 (13)0.0331 (8)
O1A0.5588 (4)0.48787 (19)0.43116 (10)0.0542 (8)
O2A0.2933 (4)0.50197 (18)0.39526 (9)0.0485 (8)
H2AA0.35110.49330.36990.073*
O3A0.5334 (5)0.54458 (17)0.62191 (10)0.0529 (8)
O4A0.3982 (5)0.59001 (18)0.64451 (12)0.0583 (9)
C1A0.5303 (6)0.4365 (2)0.53523 (15)0.0413 (9)
H1A10.6460.44310.5190.05*
H1A20.55030.42570.57020.05*
C2A0.4232 (6)0.3791 (2)0.50961 (17)0.0483 (10)
H2A10.40170.34150.53280.058*
H2A20.48990.36130.48120.058*
C3A0.2422 (5)0.41043 (19)0.49212 (13)0.0348 (8)
H3A0.16010.4090.52080.042*
C4A0.1512 (6)0.3704 (2)0.44994 (15)0.0428 (9)
H4A0.22640.37510.420.051*
C5A0.2929 (5)0.48839 (19)0.48342 (12)0.0293 (7)
C6A0.1421 (5)0.5416 (2)0.48575 (14)0.0375 (8)
H6A10.06050.53520.45780.045*
H6A20.07420.5360.51650.045*
C7A0.2246 (6)0.6134 (2)0.48375 (15)0.0441 (10)
H7A10.12750.64670.48680.053*
H7A20.27730.61960.45090.053*
C8A0.3718 (6)0.6322 (2)0.52339 (15)0.0414 (9)
C9A0.5069 (5)0.57135 (19)0.53126 (13)0.0341 (8)
H9A0.59080.57230.5030.041*
C10A0.4126 (5)0.50107 (18)0.52985 (11)0.0305 (7)
H10A0.33060.50060.55860.037*
C11A0.6238 (6)0.5749 (2)0.57973 (15)0.0461 (10)
H11A0.73150.54680.57350.055*
C12A0.6884 (7)0.6452 (3)0.59389 (17)0.0612 (14)
H12A0.80670.65890.5880.073*
C13A0.5714 (9)0.6868 (3)0.61497 (18)0.0599 (14)
C14A0.3857 (7)0.6562 (2)0.62047 (17)0.0519 (11)
H14A0.31920.68640.64330.062*
C15A0.2736 (7)0.6515 (2)0.57253 (17)0.0487 (10)
H15C0.21520.69570.56750.058*
H15D0.17910.61770.5780.058*
C16A0.6059 (11)0.7598 (3)0.6313 (2)0.089 (2)
H16D0.72870.77190.62410.133*
H16E0.58460.76370.66660.133*
H16F0.52630.79040.61370.133*
C17A0.4677 (9)0.6961 (2)0.5010 (2)0.0645 (14)
H17D0.37930.72990.49160.097*
H17E0.53540.68250.47210.097*
H17F0.54770.71550.52540.097*
C18A0.1365 (10)0.2934 (3)0.4622 (3)0.0786 (18)
H18D0.05550.28720.48980.118*
H18E0.25330.27580.47090.118*
H18F0.09130.26910.43360.118*
C19A−0.0363 (7)0.3971 (3)0.4373 (2)0.0663 (14)
H19D−0.0280.44390.42590.099*
H19E−0.1110.39510.46650.099*
H19F−0.08810.36890.41150.099*
C20A0.3954 (5)0.49324 (19)0.43429 (12)0.0337 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0367 (16)0.107 (3)0.0270 (13)−0.0195 (17)−0.0079 (12)0.0018 (15)
O20.0400 (14)0.095 (2)0.0229 (12)−0.0030 (16)0.0021 (11)0.0077 (15)
O30.0585 (18)0.0556 (17)0.0320 (14)−0.0015 (15)0.0073 (14)0.0055 (12)
O40.0499 (18)0.070 (2)0.0448 (17)0.0049 (16)−0.0087 (15)0.0053 (15)
C10.040 (2)0.048 (2)0.0325 (19)−0.0154 (18)0.0021 (17)0.0026 (16)
C20.052 (2)0.042 (2)0.039 (2)−0.010 (2)0.0065 (19)−0.0013 (17)
C30.037 (2)0.0415 (19)0.0277 (17)−0.0020 (16)−0.0024 (16)−0.0018 (15)
C40.042 (2)0.052 (2)0.0352 (19)0.005 (2)−0.0042 (18)−0.0091 (17)
C50.0302 (17)0.0405 (18)0.0200 (14)−0.0088 (15)−0.0019 (13)0.0006 (13)
C60.0318 (19)0.054 (2)0.0297 (17)−0.0150 (17)0.0011 (15)−0.0033 (16)
C70.056 (3)0.039 (2)0.038 (2)−0.0126 (19)0.008 (2)0.0039 (16)
C80.048 (2)0.0360 (18)0.036 (2)−0.0017 (18)0.0025 (18)0.0026 (15)
C90.0317 (18)0.047 (2)0.0253 (16)0.0014 (16)−0.0027 (15)0.0022 (15)
C100.0298 (16)0.0423 (18)0.0200 (14)−0.0042 (15)0.0000 (13)0.0012 (13)
C110.0316 (19)0.059 (2)0.0326 (19)−0.0009 (18)0.0009 (16)−0.0007 (17)
C120.046 (2)0.077 (3)0.043 (2)0.020 (3)0.003 (2)−0.004 (2)
C130.066 (3)0.052 (2)0.038 (2)0.015 (2)0.007 (2)−0.0054 (19)
C140.055 (3)0.055 (2)0.038 (2)0.003 (2)−0.003 (2)−0.0140 (19)
C150.050 (2)0.048 (2)0.043 (2)−0.007 (2)0.0003 (19)−0.0107 (18)
C160.109 (5)0.064 (3)0.064 (3)0.032 (3)0.005 (4)−0.012 (3)
C170.085 (4)0.054 (3)0.053 (3)0.012 (3)0.007 (3)0.014 (2)
C180.077 (4)0.056 (3)0.079 (4)0.015 (3)0.012 (3)−0.009 (3)
C190.039 (2)0.087 (3)0.049 (3)0.000 (2)0.009 (2)−0.009 (2)
C200.0361 (19)0.0412 (19)0.0221 (15)−0.0036 (16)−0.0036 (14)−0.0019 (14)
O1A0.0362 (15)0.101 (2)0.0252 (12)0.0121 (17)0.0038 (11)−0.0004 (15)
O2A0.0437 (15)0.083 (2)0.0188 (11)−0.0009 (17)−0.0032 (11)0.0062 (14)
O3A0.066 (2)0.0612 (18)0.0314 (14)−0.0056 (17)−0.0109 (15)0.0053 (13)
O4A0.062 (2)0.069 (2)0.0445 (17)−0.0099 (18)0.0064 (16)0.0081 (15)
C1A0.039 (2)0.052 (2)0.0333 (19)0.0154 (18)−0.0056 (17)0.0048 (16)
C2A0.055 (3)0.045 (2)0.044 (2)0.014 (2)−0.010 (2)0.0045 (18)
C3A0.040 (2)0.0404 (18)0.0242 (16)0.0053 (17)0.0016 (15)0.0046 (14)
C4A0.050 (2)0.044 (2)0.034 (2)−0.0052 (19)0.0020 (18)−0.0026 (17)
C5A0.0272 (16)0.0405 (17)0.0200 (14)0.0035 (15)−0.0025 (13)0.0029 (13)
C6A0.0330 (19)0.046 (2)0.0333 (19)0.0085 (17)−0.0058 (16)−0.0012 (16)
C7A0.056 (2)0.041 (2)0.035 (2)0.017 (2)−0.008 (2)0.0055 (16)
C8A0.051 (2)0.0385 (19)0.0351 (19)−0.0003 (19)−0.0012 (18)0.0026 (16)
C9A0.0313 (18)0.047 (2)0.0237 (16)−0.0014 (16)0.0008 (14)0.0013 (14)
C10A0.0313 (17)0.0421 (18)0.0180 (14)0.0030 (15)−0.0028 (13)0.0004 (13)
C11A0.038 (2)0.067 (3)0.033 (2)−0.003 (2)−0.0047 (18)−0.0005 (18)
C12A0.055 (3)0.091 (4)0.038 (2)−0.031 (3)−0.005 (2)0.002 (2)
C13A0.081 (4)0.065 (3)0.034 (2)−0.027 (3)−0.005 (2)−0.003 (2)
C14A0.061 (3)0.056 (2)0.039 (2)−0.003 (2)0.005 (2)−0.0095 (19)
C15A0.052 (2)0.045 (2)0.049 (2)0.008 (2)0.003 (2)−0.0054 (19)
C16A0.134 (6)0.070 (4)0.061 (3)−0.041 (4)−0.006 (4)−0.007 (3)
C17A0.087 (4)0.050 (3)0.056 (3)−0.013 (3)−0.007 (3)0.016 (2)
C18A0.098 (4)0.050 (3)0.088 (4)−0.019 (3)−0.019 (4)0.000 (3)
C19A0.054 (3)0.076 (3)0.068 (3)−0.008 (3)−0.020 (3)−0.010 (3)
C20A0.0375 (19)0.0413 (18)0.0223 (15)0.0019 (16)0.0004 (14)0.0029 (14)

Geometric parameters (Å, °)

O1—C201.218 (5)O1A—C20A1.220 (5)
O2—C201.298 (5)O2A—C20A1.301 (4)
O2—H20.82O2A—H2AA0.82
O3—C111.442 (5)O3A—C11A1.438 (5)
O3—O41.468 (4)O3A—O4A1.465 (5)
O4—C141.435 (6)O4A—C14A1.437 (6)
C1—C21.530 (6)C1A—C2A1.529 (6)
C1—C101.537 (5)C1A—C10A1.532 (5)
C1—H1A0.97C1A—H1A10.97
C1—H1B0.97C1A—H1A20.97
C2—C31.542 (6)C2A—C3A1.546 (6)
C2—H2A0.97C2A—H2A10.97
C2—H2B0.97C2A—H2A20.97
C3—C41.535 (5)C3A—C4A1.527 (5)
C3—C51.562 (5)C3A—C5A1.574 (5)
C3—H30.98C3A—H3A0.98
C4—C191.515 (6)C4A—C19A1.522 (7)
C4—C181.531 (7)C4A—C18A1.530 (6)
C4—H40.98C4A—H4A0.98
C5—C201.527 (5)C5A—C20A1.522 (5)
C5—C61.536 (5)C5A—C6A1.522 (5)
C5—C101.546 (5)C5A—C10A1.547 (4)
C6—C71.517 (6)C6A—C7A1.521 (6)
C6—H6A0.97C6A—H6A10.97
C6—H6B0.97C6A—H6A20.97
C7—C81.555 (6)C7A—C8A1.565 (6)
C7—H7A0.97C7A—H7A10.97
C7—H7B0.97C7A—H7A20.97
C8—C151.543 (6)C8A—C17A1.548 (6)
C8—C171.545 (6)C8A—C15A1.549 (6)
C8—C91.565 (5)C8A—C9A1.561 (5)
C9—C101.534 (5)C9A—C10A1.531 (5)
C9—C111.558 (5)C9A—C11A1.562 (5)
C9—H90.98C9A—H9A0.98
C10—H100.98C10A—H10A0.98
C11—C121.491 (6)C11A—C12A1.493 (7)
C11—H110.98C11A—H11A0.98
C12—C131.310 (7)C12A—C13A1.312 (8)
C12—H120.93C12A—H12A0.93
C13—C161.488 (6)C13A—C16A1.502 (7)
C13—C141.519 (7)C13A—C14A1.507 (8)
C14—C151.531 (6)C14A—C15A1.532 (7)
C14—H140.98C14A—H14A0.98
C15—H15A0.97C15A—H15C0.97
C15—H15B0.97C15A—H15D0.97
C16—H16A0.96C16A—H16D0.96
C16—H16B0.96C16A—H16E0.96
C16—H16C0.96C16A—H16F0.96
C17—H17A0.96C17A—H17D0.96
C17—H17B0.96C17A—H17E0.96
C17—H17C0.96C17A—H17F0.96
C18—H18A0.96C18A—H18D0.96
C18—H18B0.96C18A—H18E0.96
C18—H18C0.96C18A—H18F0.96
C19—H19A0.96C19A—H19D0.96
C19—H19B0.96C19A—H19E0.96
C19—H19C0.96C19A—H19F0.96
C20—O2—H2109.5C20A—O2A—H2AA109.5
C11—O3—O4113.0 (3)C11A—O3A—O4A113.5 (3)
C14—O4—O3113.8 (3)C14A—O4A—O3A113.3 (3)
C2—C1—C10104.8 (3)C2A—C1A—C10A104.8 (3)
C2—C1—H1A110.8C2A—C1A—H1A1110.8
C10—C1—H1A110.8C10A—C1A—H1A1110.8
C2—C1—H1B110.8C2A—C1A—H1A2110.8
C10—C1—H1B110.8C10A—C1A—H1A2110.8
H1A—C1—H1B108.9H1A1—C1A—H1A2108.9
C1—C2—C3107.2 (3)C1A—C2A—C3A107.5 (3)
C1—C2—H2A110.3C1A—C2A—H2A1110.2
C3—C2—H2A110.3C3A—C2A—H2A1110.2
C1—C2—H2B110.3C1A—C2A—H2A2110.2
C3—C2—H2B110.3C3A—C2A—H2A2110.2
H2A—C2—H2B108.5H2A1—C2A—H2A2108.5
C4—C3—C2113.1 (3)C4A—C3A—C2A114.1 (3)
C4—C3—C5119.4 (3)C4A—C3A—C5A118.9 (3)
C2—C3—C5102.8 (3)C2A—C3A—C5A102.4 (3)
C4—C3—H3106.9C4A—C3A—H3A106.9
C2—C3—H3106.9C2A—C3A—H3A106.9
C5—C3—H3106.9C5A—C3A—H3A106.9
C19—C4—C18108.7 (4)C19A—C4A—C3A113.3 (4)
C19—C4—C3113.7 (4)C19A—C4A—C18A108.2 (4)
C18—C4—C3110.0 (4)C3A—C4A—C18A111.6 (4)
C19—C4—H4108.1C19A—C4A—H4A107.8
C18—C4—H4108.1C3A—C4A—H4A107.8
C3—C4—H4108.1C18A—C4A—H4A107.8
C20—C5—C6110.6 (3)C20A—C5A—C6A111.1 (3)
C20—C5—C10112.7 (3)C20A—C5A—C10A113.4 (3)
C6—C5—C10105.8 (3)C6A—C5A—C10A106.3 (3)
C20—C5—C3109.2 (3)C20A—C5A—C3A107.8 (3)
C6—C5—C3118.1 (3)C6A—C5A—C3A117.9 (3)
C10—C5—C3100.0 (3)C10A—C5A—C3A99.8 (3)
C7—C6—C5109.3 (3)C7A—C6A—C5A108.8 (3)
C7—C6—H6A109.8C7A—C6A—H6A1109.9
C5—C6—H6A109.8C5A—C6A—H6A1109.9
C7—C6—H6B109.8C7A—C6A—H6A2109.9
C5—C6—H6B109.8C5A—C6A—H6A2109.9
H6A—C6—H6B108.3H6A1—C6A—H6A2108.3
C6—C7—C8118.6 (3)C6A—C7A—C8A118.0 (3)
C6—C7—H7A107.7C6A—C7A—H7A1107.8
C8—C7—H7A107.7C8A—C7A—H7A1107.8
C6—C7—H7B107.7C6A—C7A—H7A2107.8
C8—C7—H7B107.7C8A—C7A—H7A2107.8
H7A—C7—H7B107.1H7A1—C7A—H7A2107.1
C15—C8—C17111.2 (4)C17A—C8A—C15A110.6 (4)
C15—C8—C7108.0 (4)C17A—C8A—C9A111.2 (4)
C17—C8—C7103.4 (4)C15A—C8A—C9A111.7 (3)
C15—C8—C9111.3 (3)C17A—C8A—C7A104.1 (3)
C17—C8—C9111.4 (4)C15A—C8A—C7A107.7 (4)
C7—C8—C9111.1 (3)C9A—C8A—C7A111.3 (3)
C10—C9—C11108.5 (3)C10A—C9A—C8A112.1 (3)
C10—C9—C8111.6 (3)C10A—C9A—C11A108.2 (3)
C11—C9—C8115.8 (3)C8A—C9A—C11A115.8 (3)
C10—C9—H9106.8C10A—C9A—H9A106.8
C11—C9—H9106.8C8A—C9A—H9A106.8
C8—C9—H9106.8C11A—C9A—H9A106.8
C9—C10—C1118.0 (3)C9A—C10A—C1A117.6 (3)
C9—C10—C5115.2 (3)C9A—C10A—C5A115.0 (3)
C1—C10—C5105.7 (3)C1A—C10A—C5A105.8 (3)
C9—C10—H10105.6C9A—C10A—H10A105.8
C1—C10—H10105.6C1A—C10A—H10A105.8
C5—C10—H10105.6C5A—C10A—H10A105.8
O3—C11—C12108.8 (3)O3A—C11A—C12A108.8 (4)
O3—C11—C9112.4 (3)O3A—C11A—C9A112.1 (3)
C12—C11—C9115.4 (4)C12A—C11A—C9A115.4 (4)
O3—C11—H11106.6O3A—C11A—H11A106.7
C12—C11—H11106.6C12A—C11A—H11A106.7
C9—C11—H11106.6C9A—C11A—H11A106.7
C13—C12—C11117.0 (4)C13A—C12A—C11A117.2 (5)
C13—C12—H12121.5C13A—C12A—H12A121.4
C11—C12—H12121.5C11A—C12A—H12A121.4
C12—C13—C16126.5 (5)C12A—C13A—C16A126.2 (6)
C12—C13—C14114.2 (4)C12A—C13A—C14A113.9 (4)
C16—C13—C14119.2 (5)C16A—C13A—C14A119.8 (6)
O4—C14—C13109.5 (4)O4A—C14A—C13A109.6 (4)
O4—C14—C15111.3 (4)O4A—C14A—C15A110.9 (4)
C13—C14—C15114.7 (4)C13A—C14A—C15A116.0 (4)
O4—C14—H14107O4A—C14A—H14A106.6
C13—C14—H14107C13A—C14A—H14A106.6
C15—C14—H14107C15A—C14A—H14A106.6
C14—C15—C8118.4 (4)C14A—C15A—C8A118.1 (4)
C14—C15—H15A107.7C14A—C15A—H15C107.8
C8—C15—H15A107.7C8A—C15A—H15C107.8
C14—C15—H15B107.7C14A—C15A—H15D107.8
C8—C15—H15B107.7C8A—C15A—H15D107.8
H15A—C15—H15B107.1H15C—C15A—H15D107.1
C13—C16—H16A109.5C13A—C16A—H16D109.5
C13—C16—H16B109.5C13A—C16A—H16E109.5
H16A—C16—H16B109.5H16D—C16A—H16E109.5
C13—C16—H16C109.5C13A—C16A—H16F109.5
H16A—C16—H16C109.5H16D—C16A—H16F109.5
H16B—C16—H16C109.5H16E—C16A—H16F109.5
C8—C17—H17A109.5C8A—C17A—H17D109.5
C8—C17—H17B109.5C8A—C17A—H17E109.5
H17A—C17—H17B109.5H17D—C17A—H17E109.5
C8—C17—H17C109.5C8A—C17A—H17F109.5
H17A—C17—H17C109.5H17D—C17A—H17F109.5
H17B—C17—H17C109.5H17E—C17A—H17F109.5
C4—C18—H18A109.5C4A—C18A—H18D109.5
C4—C18—H18B109.5C4A—C18A—H18E109.5
H18A—C18—H18B109.5H18D—C18A—H18E109.5
C4—C18—H18C109.5C4A—C18A—H18F109.5
H18A—C18—H18C109.5H18D—C18A—H18F109.5
H18B—C18—H18C109.5H18E—C18A—H18F109.5
C4—C19—H19A109.5C4A—C19A—H19D109.5
C4—C19—H19B109.5C4A—C19A—H19E109.5
H19A—C19—H19B109.5H19D—C19A—H19E109.5
C4—C19—H19C109.5C4A—C19A—H19F109.5
H19A—C19—H19C109.5H19D—C19A—H19F109.5
H19B—C19—H19C109.5H19E—C19A—H19F109.5
O1—C20—O2122.1 (3)O1A—C20A—O2A122.3 (3)
O1—C20—C5123.1 (3)O1A—C20A—C5A123.4 (3)
O2—C20—C5114.8 (3)O2A—C20A—C5A114.3 (3)
C11—O3—O4—C14−1.5 (4)C11A—O3A—O4A—C14A−1.1 (5)
C10—C1—C2—C3−3.2 (4)C10A—C1A—C2A—C3A−2.6 (4)
C1—C2—C3—C4158.9 (3)C1A—C2A—C3A—C4A158.1 (3)
C1—C2—C3—C528.7 (4)C1A—C2A—C3A—C5A28.3 (4)
C2—C3—C4—C19179.1 (4)C2A—C3A—C4A—C19A173.4 (4)
C5—C3—C4—C19−59.6 (5)C5A—C3A—C4A—C19A−65.6 (5)
C2—C3—C4—C1857.0 (5)C2A—C3A—C4A—C18A50.9 (5)
C5—C3—C4—C18178.2 (4)C5A—C3A—C4A—C18A171.9 (4)
C4—C3—C5—C20−49.9 (4)C4A—C3A—C5A—C20A−50.0 (4)
C2—C3—C5—C2076.4 (3)C2A—C3A—C5A—C20A76.7 (3)
C4—C3—C5—C677.6 (4)C4A—C3A—C5A—C6A76.8 (4)
C2—C3—C5—C6−156.2 (3)C2A—C3A—C5A—C6A−156.5 (3)
C4—C3—C5—C10−168.3 (3)C4A—C3A—C5A—C10A−168.7 (3)
C2—C3—C5—C10−42.1 (3)C2A—C3A—C5A—C10A−42.0 (3)
C20—C5—C6—C7−62.5 (4)C20A—C5A—C6A—C7A−62.8 (4)
C10—C5—C6—C759.8 (4)C10A—C5A—C6A—C7A61.1 (4)
C3—C5—C6—C7170.7 (3)C3A—C5A—C6A—C7A172.0 (3)
C5—C6—C7—C8−54.2 (5)C5A—C6A—C7A—C8A−55.1 (5)
C6—C7—C8—C15−79.9 (4)C6A—C7A—C8A—C17A162.2 (4)
C6—C7—C8—C17162.2 (4)C6A—C7A—C8A—C15A−80.3 (4)
C6—C7—C8—C942.5 (5)C6A—C7A—C8A—C9A42.3 (5)
C15—C8—C9—C1081.2 (4)C17A—C8A—C9A—C10A−153.8 (3)
C17—C8—C9—C10−154.0 (3)C15A—C8A—C9A—C10A82.1 (4)
C7—C8—C9—C10−39.2 (4)C7A—C8A—C9A—C10A−38.2 (4)
C15—C8—C9—C11−43.6 (5)C17A—C8A—C9A—C11A81.4 (4)
C17—C8—C9—C1181.2 (4)C15A—C8A—C9A—C11A−42.7 (5)
C7—C8—C9—C11−164.0 (3)C7A—C8A—C9A—C11A−163.0 (3)
C11—C9—C10—C1−51.6 (4)C8A—C9A—C10A—C1A177.9 (3)
C8—C9—C10—C1179.7 (3)C11A—C9A—C10A—C1A−53.2 (4)
C11—C9—C10—C5−177.6 (3)C8A—C9A—C10A—C5A52.1 (4)
C8—C9—C10—C553.6 (4)C11A—C9A—C10A—C5A−179.0 (3)
C2—C1—C10—C9−154.6 (3)C2A—C1A—C10A—C9A−155.0 (3)
C2—C1—C10—C5−24.0 (4)C2A—C1A—C10A—C5A−24.9 (4)
C20—C5—C10—C957.5 (4)C20A—C5A—C10A—C9A58.9 (4)
C6—C5—C10—C9−63.6 (4)C6A—C5A—C10A—C9A−63.6 (4)
C3—C5—C10—C9173.3 (3)C3A—C5A—C10A—C9A173.3 (3)
C20—C5—C10—C1−74.7 (4)C20A—C5A—C10A—C1A−72.8 (4)
C6—C5—C10—C1164.3 (3)C6A—C5A—C10A—C1A164.8 (3)
C3—C5—C10—C141.1 (3)C3A—C5A—C10A—C1A41.7 (3)
O4—O3—C11—C1250.5 (4)O4A—O3A—C11A—C12A49.7 (4)
O4—O3—C11—C9−78.6 (4)O4A—O3A—C11A—C9A−79.1 (4)
C10—C9—C11—O3−39.1 (4)C10A—C9A—C11A—O3A−40.1 (4)
C8—C9—C11—O387.3 (4)C8A—C9A—C11A—O3A86.7 (4)
C10—C9—C11—C12−164.7 (3)C10A—C9A—C11A—C12A−165.4 (4)
C8—C9—C11—C12−38.2 (5)C8A—C9A—C11A—C12A−38.6 (5)
O3—C11—C12—C13−51.0 (5)O3A—C11A—C12A—C13A−49.8 (6)
C9—C11—C12—C1376.3 (5)C9A—C11A—C12A—C13A77.1 (5)
C11—C12—C13—C16−176.6 (5)C11A—C12A—C13A—C16A−178.9 (5)
C11—C12—C13—C140.1 (6)C11A—C12A—C13A—C14A−1.2 (6)
O3—O4—C14—C13−48.5 (4)O3A—O4A—C14A—C13A−49.5 (5)
O3—O4—C14—C1579.4 (4)O3A—O4A—C14A—C15A79.8 (5)
C12—C13—C14—O450.4 (5)C12A—C13A—C14A—O4A51.7 (5)
C16—C13—C14—O4−132.7 (4)C16A—C13A—C14A—O4A−130.5 (5)
C12—C13—C14—C15−75.6 (5)C12A—C13A—C14A—C15A−74.8 (6)
C16—C13—C14—C15101.3 (5)C16A—C13A—C14A—C15A102.9 (5)
O4—C14—C15—C8−87.5 (5)O4A—C14A—C15A—C8A−87.7 (5)
C13—C14—C15—C837.5 (6)C13A—C14A—C15A—C8A38.2 (6)
C17—C8—C15—C14−80.3 (5)C17A—C8A—C15A—C14A−80.4 (5)
C7—C8—C15—C14166.9 (4)C9A—C8A—C15A—C14A44.0 (5)
C9—C8—C15—C1444.6 (5)C7A—C8A—C15A—C14A166.5 (4)
C6—C5—C20—O1137.6 (4)C6A—C5A—C20A—O1A139.5 (4)
C10—C5—C20—O119.4 (5)C10A—C5A—C20A—O1A19.8 (6)
C3—C5—C20—O1−90.8 (5)C3A—C5A—C20A—O1A−89.8 (5)
C6—C5—C20—O2−42.9 (5)C6A—C5A—C20A—O2A−42.1 (4)
C10—C5—C20—O2−161.2 (3)C10A—C5A—C20A—O2A−161.9 (3)
C3—C5—C20—O288.6 (4)C3A—C5A—C20A—O2A88.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2A—H2AA···O1i0.821.862.681 (4)177
O2—H2···O1Aii0.821.892.702 (4)175

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2310).

References

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