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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2804.
Published online 2009 October 23. doi:  10.1107/S1600536809042305
PMCID: PMC2971422

7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodeca­hydro­phenan­threne-1-carboxylic acid

Abstract

The title compound, C20H32O2, has been isolated from hydrogenated rosin. There are two independent mol­ecules in the asymmetric unit. In each mol­ecule, the cyclo­hexane ring assumes a chair conformation, while the two cyclo­hexene rings adopt half-chair and envelope conformations. Inter­molecular O—H(...)O hydrogen bonding between carboxyl groups links pairs of independent mol­ecules into dimers.

Related literature

For the applications of pine resin acids, see: Piispanen et al. (2001 [triangle]); Jia et al. (2009 [triangle]); Sepulveda et al. (2005 [triangle]); Rao, Song & He (2008 [triangle]); Rao, Song, He & Jia (2008 [triangle]); Bicu & Mustata (2000 [triangle]); Hoa et al. (1993 [triangle]).

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Object name is e-65-o2804-scheme1.jpg

Experimental

Crystal data

  • C20H32O2
  • M r = 304.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2804-efi1.jpg
  • a = 11.543 (2) Å
  • b = 13.580 (3) Å
  • c = 13.345 (3) Å
  • β = 114.93 (3)°
  • V = 1897.0 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: none
  • 3775 measured reflections
  • 3590 independent reflections
  • 2046 reflections with I > 2σ(I)
  • R int = 0.025
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.194
  • S = 1.00
  • 3590 reflections
  • 385 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.18 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: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S1600536809042305/xu2627sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042305/xu2627Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Jiangsu Province (BK2008088) and the Fundamental Research Foundation of the Central Commonwealth Institute of the Chinese Academy of Forestry (CAFYBB2008021).

supplementary crystallographic information

Comment

Pine resin acids are natural diterpenoid compounds, monocarboxylic acids of alkylated hydrophenanthrene acids constitutes the principal resin acid. Pine resin acids are widely used as starting material for design and synthesis of surfactants (Piispanen et al., 2001; Jia et al., 2009), biological compounds (Sepulveda et al., 2005; Rao et al., 2008a,b) and polymers (Bicu et al., 2000; Hoa et al., 1993). In this work we describe the crystal structure of the title compound.

Two crystallorgraphica independent molecules exist in the title structure, in each molecule there are three six-membered rings, in which they form half-chair, envelope and chair conformations, respectively (Fig. 1). The two methyl groups in the same side of tricyclo phenanthrene structure. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds (Table 1).

Experimental

The title compound was isolated from hydrogenated 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 = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.97 - 0.98 Å and Uiso(H) = 1.2Ueq(C) for the other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with atom labels. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C20H32O2F(000) = 672
Mr = 304.42Dx = 1.066 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 11.543 (2) Åθ = 10–13°
b = 13.580 (3) ŵ = 0.07 mm1
c = 13.345 (3) ÅT = 293 K
β = 114.93 (3)°Block, colorless
V = 1897.0 (7) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.025
Radiation source: fine-focus sealed tubeθmax = 25.3°, θmin = 1.7°
graphiteh = 0→13
ω/2θ scansk = 0→16
3775 measured reflectionsl = −16→14
3590 independent reflections3 standard reflections every 200 reflections
2046 reflections with I > 2σ(I) 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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.113P)2] where P = (Fo2 + 2Fc2)/3
3590 reflections(Δ/σ)max = 0.002
385 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = −0.18 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
O10.5995 (3)−0.3368 (3)0.9250 (4)0.0953 (14)
O20.7106 (3)−0.2421 (4)0.8667 (4)0.1058 (16)
H2D0.7689−0.27280.91450.159*
C10.5526 (10)0.4293 (8)0.7003 (9)0.162 (4)
H1A0.56980.49580.72680.242*
H1B0.46920.42580.64020.242*
H1C0.61550.40870.67520.242*
C20.6790 (9)0.3821 (7)0.8947 (8)0.151 (3)
H2A0.67440.34120.95150.226*
H2B0.68520.44990.91680.226*
H2C0.75300.36450.88300.226*
C30.5574 (8)0.3672 (6)0.7861 (8)0.117 (2)
H3A0.48660.38850.80310.140*
C40.5336 (5)0.2562 (5)0.7585 (6)0.0872 (17)
H4A0.59890.23500.73420.105*
C50.4077 (6)0.2351 (5)0.6649 (6)0.101 (2)
H5A0.39670.27760.60300.122*
H5B0.33990.24970.68730.122*
C60.3975 (5)0.1284 (4)0.6285 (5)0.0835 (17)
H6A0.30940.11460.57880.100*
H6B0.44880.11920.58740.100*
C70.4403 (4)0.0550 (4)0.7227 (5)0.0673 (14)
C80.5082 (5)0.0867 (4)0.8256 (5)0.0743 (15)
C90.5507 (6)0.1922 (5)0.8566 (6)0.0921 (19)
H9A0.50220.22050.89380.111*
H9B0.64010.19260.90830.111*
C100.4006 (4)−0.0506 (4)0.6951 (4)0.0667 (14)
C110.4961 (4)−0.1151 (4)0.7890 (4)0.0656 (14)
H11A0.5800−0.09820.79200.079*
C120.5025 (5)−0.0827 (5)0.9023 (5)0.0780 (16)
H12A0.4178−0.08490.90090.094*
H12B0.5573−0.12710.95960.094*
C130.5550 (6)0.0217 (5)0.9272 (5)0.0840 (17)
H13A0.53020.05080.98150.101*
H13B0.64760.01900.95900.101*
C140.4079 (5)−0.0832 (4)0.5888 (4)0.0774 (16)
H14A0.4900−0.06340.59180.093*
H14B0.3423−0.04870.52740.093*
C150.3914 (6)−0.1936 (5)0.5660 (5)0.0931 (19)
H15A0.3066−0.21350.55650.112*
H15B0.3994−0.20820.49810.112*
C160.4894 (6)−0.2508 (5)0.6590 (5)0.0857 (17)
H16A0.5736−0.23390.66480.103*
H16B0.4761−0.32060.64240.103*
C170.4845 (5)−0.2311 (4)0.7703 (5)0.0758 (16)
C180.2594 (4)−0.0591 (6)0.6788 (5)0.097 (2)
H18A0.2306−0.12570.66000.145*
H18B0.2069−0.01590.62030.145*
H18C0.2535−0.04090.74600.145*
C190.3683 (5)−0.2784 (5)0.7804 (6)0.113 (2)
H19A0.3678−0.34800.76740.169*
H19B0.2911−0.24960.72680.169*
H19C0.3737−0.26710.85330.169*
C200.6034 (5)−0.2739 (4)0.8604 (5)0.0715 (14)
O31.0841 (3)0.1724 (4)0.9849 (3)0.0991 (14)
O41.1955 (3)0.0884 (4)0.9141 (3)0.1037 (15)
H4B1.25510.11390.96610.156*
C211.0284 (11)−0.0278 (10)0.1895 (9)0.164 (2)
H21A1.0483−0.01130.12860.246*
H21B0.9479−0.06160.16250.246*
H21C1.0941−0.06960.24000.246*
C221.1466 (10)0.0976 (10)0.2801 (8)0.164 (2)
H22A1.16280.15770.32180.246*
H22B1.16020.10820.21470.246*
H22C1.20350.04720.32430.246*
C231.0201 (11)0.0682 (10)0.2501 (9)0.164 (2)
H23A0.95820.11530.20040.197*
C240.9939 (7)0.0429 (7)0.3525 (5)0.110 (3)
H24A1.06320.00000.40070.132*
C250.8671 (7)−0.0108 (6)0.3270 (5)0.110 (3)
H25A0.79600.03280.28660.132*
H25B0.8601−0.06800.28130.132*
C260.8618 (6)−0.0429 (5)0.4348 (5)0.0893 (18)
H26A0.7753−0.06310.41910.107*
H26B0.9171−0.09960.46390.107*
C270.9020 (5)0.0367 (4)0.5217 (4)0.0645 (13)
C280.9620 (5)0.1162 (4)0.5122 (4)0.0692 (14)
C290.9967 (6)0.1337 (6)0.4162 (5)0.0893 (19)
H29A0.93770.18130.36660.107*
H29B1.08170.16190.44420.107*
C300.8702 (4)0.0187 (4)0.6208 (4)0.0581 (12)
C310.9664 (4)0.0813 (4)0.7182 (4)0.0609 (13)
H31A1.05070.05990.72550.073*
C320.9591 (5)0.1894 (4)0.6862 (5)0.0763 (16)
H32A0.87240.21330.66260.092*
H32B1.01450.22810.74940.092*
C331.0000 (5)0.2002 (4)0.5941 (5)0.0804 (16)
H33A1.09230.20680.62590.097*
H33B0.96390.26060.55450.097*
C340.8919 (6)−0.0900 (4)0.6569 (5)0.0815 (16)
H34A0.8284−0.13040.60040.098*
H34B0.9755−0.11050.66370.098*
C350.8836 (6)−0.1070 (5)0.7676 (5)0.096 (2)
H35A0.7988−0.08940.75990.115*
H35B0.8969−0.17630.78670.115*
C360.9802 (6)−0.0478 (5)0.8582 (5)0.0916 (19)
H36A1.0648−0.06960.86960.110*
H36B0.9707−0.06020.92590.110*
C370.9695 (5)0.0636 (5)0.8356 (4)0.0731 (16)
C380.7292 (4)0.0467 (5)0.5848 (5)0.0867 (17)
H38A0.67620.00520.52480.130*
H38B0.71660.11430.56130.130*
H38C0.70680.03830.64590.130*
C390.8541 (5)0.1048 (6)0.8505 (5)0.101 (2)
H39A0.86260.09000.92360.152*
H39B0.77730.07530.79710.152*
H39C0.85020.17480.84000.152*
C401.0881 (4)0.1130 (5)0.9177 (4)0.0701 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.063 (2)0.101 (3)0.111 (3)−0.009 (2)0.026 (2)0.039 (3)
O20.054 (2)0.123 (4)0.131 (3)0.006 (2)0.031 (2)0.061 (3)
C10.158 (8)0.104 (7)0.171 (9)−0.017 (6)0.019 (7)0.025 (7)
C20.145 (7)0.095 (6)0.184 (9)−0.013 (6)0.041 (7)−0.028 (6)
C30.110 (5)0.073 (5)0.153 (7)0.002 (4)0.041 (5)−0.014 (5)
C40.071 (3)0.083 (5)0.104 (4)0.005 (3)0.033 (3)−0.004 (4)
C50.085 (4)0.077 (5)0.120 (5)0.017 (3)0.022 (4)0.013 (4)
C60.064 (3)0.073 (4)0.089 (4)0.005 (3)0.008 (3)0.009 (3)
C70.047 (2)0.072 (4)0.081 (4)0.013 (2)0.025 (3)0.008 (3)
C80.069 (3)0.071 (4)0.079 (4)0.015 (3)0.027 (3)0.003 (3)
C90.090 (4)0.083 (4)0.111 (5)0.001 (3)0.050 (4)−0.029 (4)
C100.045 (2)0.077 (4)0.075 (3)0.005 (3)0.022 (2)0.001 (3)
C110.047 (2)0.078 (4)0.068 (3)0.000 (3)0.022 (2)0.014 (3)
C120.071 (3)0.091 (4)0.080 (4)0.011 (3)0.039 (3)0.011 (3)
C130.092 (4)0.091 (5)0.075 (4)0.007 (3)0.042 (3)−0.007 (3)
C140.072 (3)0.069 (4)0.069 (3)−0.002 (3)0.008 (3)−0.005 (3)
C150.085 (4)0.083 (5)0.082 (4)−0.008 (3)0.007 (3)−0.005 (4)
C160.100 (4)0.062 (4)0.074 (4)−0.002 (3)0.016 (3)−0.003 (3)
C170.051 (3)0.070 (4)0.098 (4)−0.012 (3)0.023 (3)0.006 (3)
C180.042 (3)0.117 (5)0.120 (5)0.009 (3)0.023 (3)0.020 (4)
C190.063 (3)0.100 (5)0.146 (6)−0.028 (3)0.015 (4)0.027 (5)
C200.060 (3)0.072 (4)0.083 (4)−0.005 (3)0.030 (3)0.015 (3)
O30.072 (2)0.134 (4)0.094 (3)−0.010 (2)0.038 (2)−0.040 (3)
O40.054 (2)0.156 (4)0.092 (3)0.003 (2)0.0222 (18)−0.032 (3)
C210.170 (5)0.192 (6)0.159 (5)0.045 (5)0.098 (5)0.032 (5)
C220.170 (5)0.192 (6)0.159 (5)0.045 (5)0.098 (5)0.032 (5)
C230.170 (5)0.192 (6)0.159 (5)0.045 (5)0.098 (5)0.032 (5)
C240.107 (5)0.158 (8)0.075 (4)0.057 (5)0.048 (4)0.035 (5)
C250.118 (6)0.131 (6)0.064 (4)0.035 (5)0.022 (4)−0.020 (4)
C260.087 (4)0.092 (4)0.087 (4)−0.009 (3)0.034 (3)−0.025 (4)
C270.055 (3)0.065 (3)0.067 (3)0.008 (3)0.020 (2)−0.004 (3)
C280.060 (3)0.082 (4)0.070 (3)0.004 (3)0.032 (2)0.021 (3)
C290.083 (4)0.114 (5)0.075 (4)0.013 (4)0.037 (3)0.032 (4)
C300.052 (2)0.051 (3)0.070 (3)−0.007 (2)0.025 (2)0.000 (2)
C310.042 (2)0.076 (4)0.067 (3)0.000 (2)0.025 (2)0.003 (3)
C320.064 (3)0.055 (3)0.093 (4)−0.005 (3)0.017 (3)−0.004 (3)
C330.065 (3)0.074 (4)0.090 (4)−0.008 (3)0.020 (3)0.006 (3)
C340.081 (4)0.066 (4)0.096 (4)−0.026 (3)0.035 (3)−0.001 (3)
C350.099 (4)0.079 (5)0.111 (5)−0.018 (4)0.045 (4)0.014 (4)
C360.093 (4)0.097 (5)0.089 (4)−0.008 (4)0.043 (4)0.021 (4)
C370.061 (3)0.090 (5)0.073 (3)−0.004 (3)0.034 (3)−0.005 (3)
C380.054 (3)0.107 (5)0.091 (4)−0.013 (3)0.022 (3)−0.022 (4)
C390.054 (3)0.154 (7)0.102 (4)0.001 (4)0.039 (3)−0.022 (4)
C400.059 (3)0.092 (4)0.061 (3)−0.004 (3)0.027 (2)−0.008 (3)

Geometric parameters (Å, °)

O1—C201.228 (6)O3—C401.221 (6)
O2—C201.280 (6)O4—C401.304 (6)
O2—H2D0.8200O4—H4B0.8200
C1—C31.404 (12)C21—C231.559 (16)
C1—H1A0.9600C21—H21A0.9600
C1—H1B0.9600C21—H21B0.9600
C1—H1C0.9600C21—H21C0.9600
C2—C31.548 (11)C22—C231.400 (14)
C2—H2A0.9600C22—H22A0.9600
C2—H2B0.9600C22—H22B0.9600
C2—H2C0.9600C22—H22C0.9600
C3—C41.549 (10)C23—C241.557 (11)
C3—H3A0.9800C23—H23A0.9800
C4—C51.491 (9)C24—C291.490 (11)
C4—C91.513 (9)C24—C251.539 (11)
C4—H4A0.9800C24—H24A0.9800
C5—C61.517 (9)C25—C261.529 (9)
C5—H5A0.9700C25—H25A0.9700
C5—H5B0.9700C25—H25B0.9700
C6—C71.515 (8)C26—C271.508 (8)
C6—H6A0.9700C26—H26A0.9700
C6—H6B0.9700C26—H26B0.9700
C7—C81.333 (7)C27—C281.317 (7)
C7—C101.504 (8)C27—C301.534 (7)
C8—C131.514 (8)C28—C331.511 (8)
C8—C91.515 (9)C28—C291.513 (7)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C10—C141.521 (8)C30—C381.539 (7)
C10—C111.545 (7)C30—C341.539 (8)
C10—C181.556 (7)C30—C311.558 (7)
C11—C121.547 (8)C31—C321.521 (8)
C11—C171.591 (8)C31—C371.571 (7)
C11—H11A0.9800C31—H31A0.9800
C12—C131.522 (9)C32—C331.499 (8)
C12—H12A0.9700C32—H32A0.9700
C12—H12B0.9700C32—H32B0.9700
C13—H13A0.9700C33—H33A0.9700
C13—H13B0.9700C33—H33B0.9700
C14—C151.527 (9)C34—C351.539 (9)
C14—H14A0.9700C34—H34A0.9700
C14—H14B0.9700C34—H34B0.9700
C15—C161.496 (8)C35—C361.488 (9)
C15—H15A0.9700C35—H35A0.9700
C15—H15B0.9700C35—H35B0.9700
C16—C171.534 (8)C36—C371.538 (9)
C16—H16A0.9700C36—H36A0.9700
C16—H16B0.9700C36—H36B0.9700
C17—C201.508 (8)C37—C401.503 (7)
C17—C191.544 (8)C37—C391.532 (7)
C18—H18A0.9600C38—H38A0.9600
C18—H18B0.9600C38—H38B0.9600
C18—H18C0.9600C38—H38C0.9600
C19—H19A0.9600C39—H39A0.9600
C19—H19B0.9600C39—H39B0.9600
C19—H19C0.9600C39—H39C0.9600
C20—O2—H2D109.5C40—O4—H4B109.5
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—C2113.2 (8)C22—C23—C24112.2 (9)
C1—C3—C4116.6 (8)C22—C23—C2195.9 (9)
C2—C3—C4110.5 (7)C24—C23—C21110.4 (9)
C1—C3—H3A105.1C22—C23—H23A112.5
C2—C3—H3A105.1C24—C23—H23A112.5
C4—C3—H3A105.1C21—C23—H23A112.5
C5—C4—C9109.9 (6)C29—C24—C25107.9 (5)
C5—C4—C3113.5 (6)C29—C24—C23110.7 (8)
C9—C4—C3114.0 (6)C25—C24—C23115.4 (7)
C5—C4—H4A106.3C29—C24—H24A107.5
C9—C4—H4A106.3C25—C24—H24A107.5
C3—C4—H4A106.3C23—C24—H24A107.5
C4—C5—C6111.6 (5)C26—C25—C24109.8 (5)
C4—C5—H5A109.3C26—C25—H25A109.7
C6—C5—H5A109.3C24—C25—H25A109.7
C4—C5—H5B109.3C26—C25—H25B109.7
C6—C5—H5B109.3C24—C25—H25B109.7
H5A—C5—H5B108.0H25A—C25—H25B108.2
C7—C6—C5114.1 (5)C27—C26—C25113.5 (6)
C7—C6—H6A108.7C27—C26—H26A108.9
C5—C6—H6A108.7C25—C26—H26A108.9
C7—C6—H6B108.7C27—C26—H26B108.9
C5—C6—H6B108.7C25—C26—H26B108.9
H6A—C6—H6B107.6H26A—C26—H26B107.7
C8—C7—C10123.1 (5)C28—C27—C26121.1 (5)
C8—C7—C6119.2 (5)C28—C27—C30122.7 (5)
C10—C7—C6117.7 (5)C26—C27—C30116.2 (5)
C7—C8—C13124.5 (6)C27—C28—C33123.5 (5)
C7—C8—C9124.7 (6)C27—C28—C29123.2 (6)
C13—C8—C9110.8 (5)C33—C28—C29113.2 (5)
C4—C9—C8113.4 (5)C24—C29—C28113.8 (6)
C4—C9—H9A108.9C24—C29—H29A108.8
C8—C9—H9A108.9C28—C29—H29A108.8
C4—C9—H9B108.9C24—C29—H29B108.8
C8—C9—H9B108.9C28—C29—H29B108.8
H9A—C9—H9B107.7H29A—C29—H29B107.7
C7—C10—C14112.0 (5)C27—C30—C38107.3 (4)
C7—C10—C11107.6 (4)C27—C30—C34110.8 (4)
C14—C10—C11106.9 (4)C38—C30—C34110.3 (4)
C7—C10—C18107.3 (5)C27—C30—C31106.6 (4)
C14—C10—C18108.3 (5)C38—C30—C31114.4 (4)
C11—C10—C18114.7 (5)C34—C30—C31107.3 (4)
C10—C11—C12110.8 (4)C32—C31—C30111.0 (4)
C10—C11—C17116.8 (4)C32—C31—C37113.7 (4)
C12—C11—C17113.7 (5)C30—C31—C37117.2 (4)
C10—C11—H11A104.8C32—C31—H31A104.5
C12—C11—H11A104.8C30—C31—H31A104.5
C17—C11—H11A104.8C37—C31—H31A104.5
C13—C12—C11109.2 (5)C33—C32—C31108.9 (5)
C13—C12—H12A109.8C33—C32—H32A109.9
C11—C12—H12A109.8C31—C32—H32A109.9
C13—C12—H12B109.8C33—C32—H32B109.9
C11—C12—H12B109.8C31—C32—H32B109.9
H12A—C12—H12B108.3H32A—C32—H32B108.3
C8—C13—C12112.9 (5)C32—C33—C28115.1 (4)
C8—C13—H13A109.0C32—C33—H33A108.5
C12—C13—H13A109.0C28—C33—H33A108.5
C8—C13—H13B109.0C32—C33—H33B108.5
C12—C13—H13B109.0C28—C33—H33B108.5
H13A—C13—H13B107.8H33A—C33—H33B107.5
C10—C14—C15114.8 (5)C35—C34—C30112.1 (5)
C10—C14—H14A108.6C35—C34—H34A109.2
C15—C14—H14A108.6C30—C34—H34A109.2
C10—C14—H14B108.6C35—C34—H34B109.2
C15—C14—H14B108.6C30—C34—H34B109.2
H14A—C14—H14B107.5H34A—C34—H34B107.9
C16—C15—C14111.0 (5)C36—C35—C34111.7 (5)
C16—C15—H15A109.4C36—C35—H35A109.3
C14—C15—H15A109.4C34—C35—H35A109.3
C16—C15—H15B109.4C36—C35—H35B109.3
C14—C15—H15B109.4C34—C35—H35B109.3
H15A—C15—H15B108.0H35A—C35—H35B107.9
C15—C16—C17112.9 (5)C35—C36—C37113.7 (5)
C15—C16—H16A109.0C35—C36—H36A108.8
C17—C16—H16A109.0C37—C36—H36A108.8
C15—C16—H16B109.0C35—C36—H36B108.8
C17—C16—H16B109.0C37—C36—H36B108.8
H16A—C16—H16B107.8H36A—C36—H36B107.7
C20—C17—C16108.2 (5)C40—C37—C39108.5 (5)
C20—C17—C19107.6 (5)C40—C37—C36108.9 (5)
C16—C17—C19113.5 (5)C39—C37—C36109.6 (5)
C20—C17—C11105.6 (4)C40—C37—C31106.9 (4)
C16—C17—C11106.8 (5)C39—C37—C31114.7 (5)
C19—C17—C11114.7 (5)C36—C37—C31108.2 (5)
C10—C18—H18A109.5C30—C38—H38A109.5
C10—C18—H18B109.5C30—C38—H38B109.5
H18A—C18—H18B109.5H38A—C38—H38B109.5
C10—C18—H18C109.5C30—C38—H38C109.5
H18A—C18—H18C109.5H38A—C38—H38C109.5
H18B—C18—H18C109.5H38B—C38—H38C109.5
C17—C19—H19A109.5C37—C39—H39A109.5
C17—C19—H19B109.5C37—C39—H39B109.5
H19A—C19—H19B109.5H39A—C39—H39B109.5
C17—C19—H19C109.5C37—C39—H39C109.5
H19A—C19—H19C109.5H39A—C39—H39C109.5
H19B—C19—H19C109.5H39B—C39—H39C109.5
O1—C20—O2120.6 (5)O3—C40—O4121.8 (5)
O1—C20—C17122.6 (5)O3—C40—C37121.7 (5)
O2—C20—C17116.8 (5)O4—C40—C37116.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2D···O3i0.821.822.632 (6)170
O4—H4B···O1ii0.821.822.638 (6)173

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2627).

References

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