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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2402.
Published online 2009 September 9. doi:  10.1107/S1600536809035600
PMCID: PMC2970241

Dehydro­abietic acid

Abstract

The title compound [systematic name: (1R,4aS,10aR)-7-iso­prop­yl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa­hydro­phen­anthrene-1-carboxylic acid], C20H28O2, has been isolated from disproportionated rosin which is obtained by isomerizing gum rosin with a Pd-C catalyst.. Two crystallographically independent mol­ecules exist in the asymmetric unit. In each mol­ecule, there are three six-membered rings, which adopt planar, half-chair and chair conformations. The two cyclo­hexane rings form a trans ring junction with the two methyl groups in axial positions. The crystal structure is stabilized by inter­molecular O—H(...)O hydrogen bonds.

Related literature

For the synthesis and uses of dehydro­abietic acid, see: Halbrook & Lawrence (1966 [triangle]); Jia et al. (2009 [triangle]); Piispanen et al. (2001 [triangle]); Rao et al. (2006 [triangle]); Rao, Song & He (2008 [triangle]); Rao, Song, He & Jia (2008 [triangle]); Sepulveda et al. (2005 [triangle]); Wada et al. (1985 [triangle]).

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Object name is e-65-o2402-scheme1.jpg

Experimental

Crystal data

  • C20H28O2
  • M r = 300.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2402-efi1.jpg
  • a = 11.738 (2) Å
  • b = 11.875 (2) Å
  • c = 13.654 (3) Å
  • β = 107.50 (3)°
  • V = 1815.1 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 K
  • 0.40 × 0.20 × 0.20 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 [triangle]) T min = 0.973, T max = 0.986
  • 3592 measured reflections
  • 3417 independent reflections
  • 2173 reflections with I > 2σ(I)
  • R int = 0.086
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.182
  • S = 1.00
  • 3417 reflections
  • 361 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.52 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035600/at2868sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035600/at2868Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 30800871) and the Fundamental Research Foundation of the Central Commonwealth Institute of the Chinese Academy of Forestry (grant No. CAFYBB2008021),

supplementary crystallographic information

Comment

Dehydroabietic acid is an abietane diterpenic resin acid which can be easily obtained from Pinus resin or commercial disproportionated rosin (Halbrook & Lawrence, 1966). The tri-cyclic hydrophenanthrene structure of dehydroabietic acid has strong hydrophobicity, so it can be used as raw material for the synthesis of surfactants (Piispanen et al., 2001; Jia et al., 2009). Dehydroabietic acid is also widely used as starting material for design and synthesis of biological compounds (Sepulveda et al., 2005; Rao, Song & He, 2008; Rao, Song He & Jia, 2008; Wada et al., 1985). In this work, we describe the crystal structure of the title compound.

The overall geometry of the title compound (Fig. 1) is comparable to that found for dehydroabietic N-methyl anilide (Rao et al., 2006) Two crystallorgraphic independent molecules exist in the asymmetric unit. In each molecule there are three six-membered rings, in which they form plannar, half-chair and chair conformations, respectively. The tricyclo phenanthrene structure of the title compound exhibited the same conformation with dehydroabietic N-methyl anilide. The two cyclohexane rings form a trans ring junction with two methyl groups in the same side of tricyclo phenanthrene structure. There are three chiral centers in each molecule, they exhibited R–, S– and R– configurations, respectively.

The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds.

Experimental

The title compound wasere isolated from disproportionated rosin by recrystallization 5 times from acetone. Single crystals were grown from acetone.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.97–0.98Å and Uiso(H) = 1.2Ueq(C) for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom labelling scheme. H atoms are represented by spheres of arbitrary radius and displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C20H28O2F(000) = 656
Mr = 300.42Dx = 1.099 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 11.738 (2) Åθ = 9–13°
b = 11.875 (2) ŵ = 0.07 mm1
c = 13.654 (3) ÅT = 293 K
β = 107.50 (3)°Block, white
V = 1815.1 (6) Å30.40 × 0.20 × 0.20 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer2173 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.086
graphiteθmax = 25.2°, θmin = 1.6°
ω/2θ scansh = 0→14
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)k = 0→14
Tmin = 0.973, Tmax = 0.986l = −16→15
3592 measured reflections3 standard reflections every 200 reflections
3417 independent reflections intensity decay: 1%

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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.06P)2 + 1.6P] where P = (Fo2 + 2Fc2)/3
3417 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.24 e Å3
3 restraintsΔρmin = −0.52 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
O10.7903 (4)0.0770 (5)0.5980 (5)0.111 (2)
O20.6194 (4)−0.0132 (5)0.5509 (4)0.0981 (18)
H2D0.6584−0.04870.52060.147*
C11.0216 (7)0.7319 (9)0.7227 (6)0.105
H1A1.04730.65920.70680.158*
H1B1.08790.78320.73850.158*
H1C0.95940.75940.66460.158*
C20.9229 (7)0.8140 (7)0.8668 (6)0.094
H2A0.89720.77960.92020.141*
H2B0.85590.84930.81800.141*
H2C0.98270.86970.89610.141*
C30.9762 (7)0.7223 (7)0.8115 (5)0.089
H3A1.04710.69760.86600.107*
C40.8968 (8)0.6219 (7)0.7975 (7)0.094 (2)
C50.9072 (8)0.5624 (8)0.8875 (7)0.104 (3)
H5A0.95430.59130.94990.125*
C60.8482 (6)0.4603 (7)0.8856 (5)0.079 (2)
H6A0.85960.42060.94650.095*
C70.7739 (5)0.4168 (5)0.7964 (4)0.0580 (15)
C80.7635 (6)0.4722 (6)0.7055 (5)0.0660 (16)
C90.8238 (7)0.5731 (6)0.7076 (6)0.085 (2)
H9A0.81510.61010.64570.102*
C100.7026 (5)0.3060 (5)0.7991 (4)0.0554 (15)
C110.6944 (4)0.2442 (5)0.6962 (4)0.0463 (13)
H11A0.77710.23840.69460.056*
C120.6319 (5)0.3137 (6)0.6046 (4)0.0636 (16)
H12A0.55010.32590.60420.076*
H12B0.62990.27220.54290.076*
C130.6904 (7)0.4267 (7)0.6020 (5)0.085 (2)
H13A0.62850.48100.57040.101*
H13B0.74190.42030.55850.101*
C140.7656 (6)0.2326 (6)0.8889 (4)0.0674 (17)
H14A0.76270.26880.95180.081*
H14B0.84890.22550.89170.081*
C150.7105 (7)0.1152 (6)0.8826 (5)0.084 (2)
H15A0.75480.07140.94180.101*
H15B0.62880.12170.88440.101*
C160.7117 (6)0.0560 (6)0.7883 (6)0.081 (2)
H16A0.6743−0.01700.78690.097*
H16B0.79400.04340.79030.097*
C170.6479 (4)0.1187 (6)0.6895 (4)0.0549 (15)
C190.5766 (5)0.3435 (7)0.8062 (6)0.085 (2)
H19A0.52930.27800.80800.128*
H19B0.53690.38840.74730.128*
H19C0.58670.38690.86750.128*
C180.6865 (5)0.0604 (5)0.6094 (5)0.0623 (16)
C200.5112 (5)0.1113 (6)0.6643 (6)0.082 (2)
H20A0.48740.03360.66090.123*
H20B0.47410.14680.59940.123*
H20C0.48660.14870.71690.123*
O30.2917 (4)0.3532 (5)0.5604 (4)0.0990 (19)
O40.1213 (4)0.4452 (5)0.5126 (4)0.0960 (18)
H4A0.15810.48090.48060.144*
C210.4859 (7)0.2433 (8)1.2965 (6)0.098
H21A0.54080.26281.36200.148*
H21B0.47500.16311.29260.148*
H21C0.41050.27931.28870.148*
C220.6600 (6)0.2601 (9)1.2160 (6)0.107
H22A0.71190.27701.28340.160*
H22B0.68060.30681.16640.160*
H22C0.66890.18241.20040.160*
C230.5353 (6)0.2817 (7)1.2122 (5)0.085
H23A0.53250.36401.21700.102*
C240.4502 (6)0.2576 (9)1.1044 (6)0.093 (2)
C250.4036 (8)0.1542 (8)1.0763 (7)0.112 (3)
H25A0.42190.09581.12390.134*
C260.3299 (7)0.1337 (7)0.9789 (7)0.108 (3)
H26A0.30760.05990.95970.129*
C270.2870 (5)0.2205 (6)0.9074 (5)0.0695 (19)
C280.3299 (6)0.3285 (6)0.9408 (5)0.0709 (18)
C290.4126 (6)0.3443 (6)1.0387 (5)0.0747 (19)
H29A0.44190.41621.05860.090*
C300.1924 (5)0.1988 (6)0.8056 (5)0.0650 (18)
C310.2050 (5)0.2939 (5)0.7340 (4)0.0540 (14)
H31A0.28880.29040.73520.065*
C320.1918 (7)0.4097 (6)0.7754 (5)0.079 (2)
H32A0.11630.41500.79050.095*
H32B0.19270.46650.72460.095*
C330.2942 (7)0.4292 (6)0.8722 (5)0.084 (2)
H33A0.36300.45450.85290.101*
H33B0.27220.48940.91100.101*
C340.2114 (6)0.0853 (6)0.7582 (5)0.0736 (19)
H34A0.29470.07960.76090.088*
H34B0.19530.02520.80040.088*
C350.1367 (6)0.0670 (7)0.6509 (5)0.087 (2)
H35A0.05340.06310.64860.105*
H35B0.1580−0.00430.62660.105*
C360.1528 (6)0.1607 (7)0.5810 (5)0.078 (2)
H36A0.09860.14770.51270.094*
H36B0.23360.15710.57630.094*
C370.1309 (5)0.2781 (6)0.6151 (5)0.0650 (17)
C39−0.0057 (5)0.3022 (8)0.5926 (5)0.087 (2)
H39A−0.04570.29130.52080.130*
H39B−0.01690.37840.61120.130*
H39C−0.03840.25160.63200.130*
C380.1848 (5)0.3630 (6)0.5582 (5)0.0688 (19)
C400.0688 (5)0.1971 (8)0.8262 (5)0.090 (3)
H40A0.05680.26720.85670.136*
H40B0.06680.13630.87190.136*
H40C0.00660.18680.76250.136*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.076 (3)0.120 (5)0.161 (5)−0.044 (3)0.070 (3)−0.075 (4)
O20.058 (3)0.116 (4)0.124 (4)−0.022 (3)0.032 (3)−0.060 (4)
C10.1050.1050.1050.0000.0320.000
C20.0940.0940.0940.0000.0280.000
C30.0890.0890.0890.0000.0270.000
C40.131 (7)0.069 (5)0.094 (6)−0.045 (5)0.052 (5)−0.031 (5)
C50.127 (7)0.088 (6)0.113 (7)−0.054 (5)0.060 (5)−0.055 (6)
C60.094 (5)0.094 (6)0.060 (4)−0.027 (4)0.037 (4)−0.015 (4)
C70.066 (4)0.055 (4)0.057 (4)−0.007 (3)0.026 (3)−0.008 (3)
C80.073 (4)0.057 (4)0.065 (4)0.003 (3)0.015 (3)0.005 (3)
C90.105 (5)0.070 (5)0.092 (5)−0.007 (4)0.051 (4)0.022 (4)
C100.048 (3)0.065 (4)0.059 (4)0.000 (3)0.024 (3)−0.008 (3)
C110.040 (3)0.056 (3)0.046 (3)0.002 (3)0.017 (2)−0.009 (3)
C120.065 (3)0.068 (4)0.053 (3)−0.008 (3)0.010 (3)−0.006 (3)
C130.084 (5)0.091 (5)0.075 (5)−0.004 (4)0.019 (4)0.020 (4)
C140.076 (4)0.075 (4)0.052 (3)−0.009 (4)0.020 (3)0.000 (3)
C150.105 (5)0.079 (5)0.070 (4)−0.018 (4)0.027 (4)0.005 (4)
C160.081 (5)0.058 (4)0.108 (6)−0.008 (4)0.036 (4)0.005 (4)
C170.031 (2)0.079 (4)0.058 (3)−0.006 (3)0.018 (2)−0.009 (3)
C190.068 (4)0.089 (5)0.115 (6)−0.003 (4)0.053 (4)−0.025 (5)
C180.050 (3)0.057 (4)0.083 (4)0.001 (3)0.025 (3)−0.008 (4)
C200.056 (3)0.086 (5)0.114 (6)−0.020 (4)0.041 (4)−0.036 (5)
O30.052 (2)0.135 (5)0.122 (4)0.028 (3)0.043 (3)0.071 (4)
O40.062 (3)0.112 (4)0.117 (4)0.016 (3)0.032 (3)0.066 (4)
C210.0980.0980.0980.0000.0300.000
C220.1070.1070.1070.0000.0320.000
C230.0850.0850.0850.0000.0260.000
C240.081 (5)0.107 (7)0.078 (5)−0.006 (5)0.006 (4)0.001 (5)
C250.139 (8)0.084 (6)0.081 (5)−0.014 (6)−0.015 (5)0.021 (5)
C260.102 (6)0.074 (5)0.113 (7)−0.022 (5)−0.017 (5)0.029 (5)
C270.058 (4)0.076 (5)0.076 (4)0.010 (3)0.023 (3)0.031 (4)
C280.076 (4)0.072 (5)0.067 (4)0.016 (4)0.024 (3)0.002 (4)
C290.091 (5)0.069 (5)0.067 (4)0.008 (4)0.028 (4)−0.009 (4)
C300.040 (3)0.088 (5)0.073 (4)0.002 (3)0.025 (3)0.017 (4)
C310.049 (3)0.058 (4)0.060 (3)0.014 (3)0.023 (3)0.010 (3)
C320.089 (5)0.077 (5)0.084 (5)0.020 (4)0.043 (4)0.018 (4)
C330.122 (6)0.055 (4)0.076 (5)0.017 (4)0.031 (4)0.000 (4)
C340.066 (4)0.061 (4)0.090 (5)−0.011 (3)0.018 (4)0.011 (4)
C350.079 (5)0.083 (5)0.087 (5)−0.027 (4)0.005 (4)0.013 (4)
C360.059 (4)0.094 (6)0.077 (4)−0.011 (4)0.015 (3)−0.005 (4)
C370.038 (3)0.084 (5)0.070 (4)0.005 (3)0.011 (3)0.019 (4)
C390.039 (3)0.125 (6)0.097 (5)0.010 (4)0.020 (3)0.032 (5)
C380.042 (3)0.099 (5)0.067 (4)0.007 (3)0.019 (3)0.029 (4)
C400.052 (3)0.138 (7)0.088 (4)−0.011 (4)0.032 (3)0.042 (5)

Geometric parameters (Å, °)

O1—C181.289 (7)O3—C381.252 (6)
O2—C181.281 (7)O4—C381.271 (8)
O2—H2D0.8200O4—H4A0.8200
C1—C31.469 (7)C21—C231.507 (10)
C1—H1A0.9600C21—H21A0.9600
C1—H1B0.9600C21—H21B0.9600
C1—H1C0.9600C21—H21C0.9600
C2—C31.559 (10)C22—C231.472 (7)
C2—H2A0.9600C22—H22A0.9600
C2—H2B0.9600C22—H22B0.9600
C2—H2C0.9600C22—H22C0.9600
C3—C41.490 (10)C23—C241.538 (10)
C3—H3A0.9800C23—H23A0.9800
C4—C51.391 (12)C24—C291.350 (10)
C4—C91.395 (10)C24—C251.352 (12)
C5—C61.393 (10)C25—C261.373 (11)
C5—H5A0.9300C25—H25A0.9300
C6—C71.368 (8)C26—C271.405 (9)
C6—H6A0.9300C26—H26A0.9300
C7—C81.377 (8)C27—C281.404 (10)
C7—C101.567 (9)C27—C301.518 (9)
C8—C91.388 (9)C28—C291.408 (9)
C8—C131.516 (9)C28—C331.498 (10)
C9—H9A0.9300C29—H29A0.9300
C10—C141.504 (9)C30—C311.530 (8)
C10—C111.562 (7)C30—C341.540 (10)
C10—C191.576 (7)C30—C401.558 (7)
C11—C121.494 (8)C31—C321.513 (9)
C11—C171.581 (8)C31—C371.605 (8)
C11—H11A0.9800C31—H31A0.9800
C12—C131.511 (10)C32—C331.514 (10)
C12—H12A0.9700C32—H32A0.9700
C12—H12B0.9700C32—H32B0.9700
C13—H13A0.9700C33—H33A0.9700
C13—H13B0.9700C33—H33B0.9700
C14—C151.529 (10)C34—C351.480 (9)
C14—H14A0.9700C34—H34A0.9700
C14—H14B0.9700C34—H34B0.9700
C15—C161.471 (10)C35—C361.515 (10)
C15—H15A0.9700C35—H35A0.9700
C15—H15B0.9700C35—H35B0.9700
C16—C171.524 (9)C36—C371.516 (10)
C16—H16A0.9700C36—H36A0.9700
C16—H16B0.9700C36—H36B0.9700
C17—C181.477 (8)C37—C381.522 (9)
C17—C201.540 (7)C37—C391.566 (7)
C19—H19A0.9600C39—H39A0.9600
C19—H19B0.9600C39—H39B0.9600
C19—H19C0.9600C39—H39C0.9600
C20—H20A0.9600C40—H40A0.9600
C20—H20B0.9600C40—H40B0.9600
C20—H20C0.9600C40—H40C0.9600
C18—O2—H2D109.5C38—O4—H4A109.5
C3—C1—H1A109.5C23—C21—H21A109.5
C3—C1—H1B109.5C23—C21—H21B109.5
H1A—C1—H1B109.5H21A—C21—H21B109.5
C3—C1—H1C109.5C23—C21—H21C109.5
H1A—C1—H1C109.5H21A—C21—H21C109.5
H1B—C1—H1C109.5H21B—C21—H21C109.5
C3—C2—H2A109.5C23—C22—H22A109.5
C3—C2—H2B109.5C23—C22—H22B109.5
H2A—C2—H2B109.5H22A—C22—H22B109.5
C3—C2—H2C109.5C23—C22—H22C109.5
H2A—C2—H2C109.5H22A—C22—H22C109.5
H2B—C2—H2C109.5H22B—C22—H22C109.5
C1—C3—C4108.9 (7)C22—C23—C21121.9 (7)
C1—C3—C2130.1 (7)C22—C23—C24110.7 (6)
C4—C3—C2107.1 (6)C21—C23—C24112.7 (6)
C1—C3—H3A102.4C22—C23—H23A102.9
C4—C3—H3A102.4C21—C23—H23A102.9
C2—C3—H3A102.4C24—C23—H23A102.9
C5—C4—C9115.8 (7)C29—C24—C25118.7 (7)
C5—C4—C3114.1 (7)C29—C24—C23118.8 (8)
C9—C4—C3129.8 (7)C25—C24—C23122.1 (8)
C4—C5—C6121.0 (7)C24—C25—C26121.3 (8)
C4—C5—H5A119.5C24—C25—H25A119.4
C6—C5—H5A119.5C26—C25—H25A119.4
C7—C6—C5121.7 (7)C25—C26—C27122.3 (8)
C7—C6—H6A119.2C25—C26—H26A118.9
C5—C6—H6A119.2C27—C26—H26A118.9
C6—C7—C8118.9 (6)C28—C27—C26115.2 (6)
C6—C7—C10119.9 (6)C28—C27—C30123.0 (6)
C8—C7—C10121.3 (5)C26—C27—C30121.5 (7)
C7—C8—C9119.2 (6)C27—C28—C29120.5 (6)
C7—C8—C13122.8 (6)C27—C28—C33121.4 (6)
C9—C8—C13118.0 (6)C29—C28—C33118.0 (7)
C8—C9—C4123.4 (7)C24—C29—C28121.6 (7)
C8—C9—H9A118.3C24—C29—H29A119.2
C4—C9—H9A118.3C28—C29—H29A119.2
C14—C10—C11110.1 (5)C27—C30—C31105.9 (5)
C14—C10—C7111.7 (5)C27—C30—C34112.0 (5)
C11—C10—C7105.2 (4)C31—C30—C34108.9 (5)
C14—C10—C19110.7 (5)C27—C30—C40107.6 (5)
C11—C10—C19112.5 (5)C31—C30—C40113.5 (5)
C7—C10—C19106.4 (5)C34—C30—C40108.9 (6)
C12—C11—C10112.0 (5)C32—C31—C30113.1 (5)
C12—C11—C17113.5 (4)C32—C31—C37113.5 (5)
C10—C11—C17114.9 (4)C30—C31—C37115.6 (5)
C12—C11—H11A105.1C32—C31—H31A104.4
C10—C11—H11A105.1C30—C31—H31A104.4
C17—C11—H11A105.1C37—C31—H31A104.4
C11—C12—C13113.5 (5)C31—C32—C33108.8 (6)
C11—C12—H12A108.9C31—C32—H32A109.9
C13—C12—H12A108.9C33—C32—H32A109.9
C11—C12—H12B108.9C31—C32—H32B109.9
C13—C12—H12B108.9C33—C32—H32B109.9
H12A—C12—H12B107.7H32A—C32—H32B108.3
C12—C13—C8115.4 (6)C28—C33—C32115.0 (7)
C12—C13—H13A108.4C28—C33—H33A108.5
C8—C13—H13A108.4C32—C33—H33A108.5
C12—C13—H13B108.4C28—C33—H33B108.5
C8—C13—H13B108.4C32—C33—H33B108.5
H13A—C13—H13B107.5H33A—C33—H33B107.5
C10—C14—C15112.8 (5)C35—C34—C30115.2 (6)
C10—C14—H14A109.0C35—C34—H34A108.5
C15—C14—H14A109.0C30—C34—H34A108.5
C10—C14—H14B109.0C35—C34—H34B108.5
C15—C14—H14B109.0C30—C34—H34B108.5
H14A—C14—H14B107.8H34A—C34—H34B107.5
C16—C15—C14111.7 (6)C34—C35—C36111.6 (6)
C16—C15—H15A109.3C34—C35—H35A109.3
C14—C15—H15A109.3C36—C35—H35A109.3
C16—C15—H15B109.3C34—C35—H35B109.3
C14—C15—H15B109.3C36—C35—H35B109.3
H15A—C15—H15B107.9H35A—C35—H35B108.0
C15—C16—C17114.2 (6)C35—C36—C37114.6 (6)
C15—C16—H16A108.7C35—C36—H36A108.6
C17—C16—H16A108.7C37—C36—H36A108.6
C15—C16—H16B108.7C35—C36—H36B108.6
C17—C16—H16B108.7C37—C36—H36B108.6
H16A—C16—H16B107.6H36A—C36—H36B107.6
C18—C17—C16104.4 (5)C36—C37—C38108.5 (5)
C18—C17—C20109.8 (5)C36—C37—C39111.5 (6)
C16—C17—C20111.8 (5)C38—C37—C39109.7 (5)
C18—C17—C11107.9 (4)C36—C37—C31109.2 (5)
C16—C17—C11109.9 (5)C38—C37—C31104.9 (5)
C20—C17—C11112.7 (5)C39—C37—C31112.9 (5)
C10—C19—H19A109.5C37—C39—H39A109.5
C10—C19—H19B109.5C37—C39—H39B109.5
H19A—C19—H19B109.5H39A—C39—H39B109.5
C10—C19—H19C109.5C37—C39—H39C109.5
H19A—C19—H19C109.5H39A—C39—H39C109.5
H19B—C19—H19C109.5H39B—C39—H39C109.5
O2—C18—O1117.1 (6)O3—C38—O4121.3 (6)
O2—C18—C17120.9 (5)O3—C38—C37119.6 (6)
O1—C18—C17121.9 (6)O4—C38—C37119.1 (5)
C17—C20—H20A109.5C30—C40—H40A109.5
C17—C20—H20B109.5C30—C40—H40B109.5
H20A—C20—H20B109.5H40A—C40—H40B109.5
C17—C20—H20C109.5C30—C40—H40C109.5
H20A—C20—H20C109.5H40A—C40—H40C109.5
H20B—C20—H20C109.5H40B—C40—H40C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2D···O3i0.821.822.621 (8)165
O4—H4A···O1ii0.821.792.598 (8)168
C11—H11A···O10.982.362.813 (8)108
C31—H31A···O30.982.512.933 (8)106
C36—H36B···O30.972.452.870 (10)105

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2868).

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