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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1521.
Published online 2009 June 6. doi:  10.1107/S1600536809021059
PMCID: PMC2969219

16-Isopropyl-5,9-dimethyltetra­cyclo­[10.2.2.01,10.04,9]hexa­dec-15-ene-5,14-dicarboxylic acid ethanol hemisolvate

Abstract

In the title compound, C23H34O4·0.5C2H6O, which was isolated from acrylic modified rosin, the endocyclic compound adopts a tetra­cyclo­[10.2.2.01,10.04,9]hexa­decane structure. In the crystal, the components are linked by O—H(...)O and C—H(...) hydrogen bonds.

Related literature

The title compound has previously been isolated by solvent extracting (Aldrich, 1971 [triangle]) and solvent washing (Bicu & Munstata, 2007 [triangle]) from acrylic modified rosin.

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Object name is e-65-o1521-scheme1.jpg

Experimental

Crystal data

  • C23H34O4·0.5C2H6O
  • M r = 397.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1521-efi1.jpg
  • a = 12.682 (3) Å
  • b = 12.476 (3) Å
  • c = 14.629 (3) Å
  • β = 90.12 (3)°
  • V = 2314.6 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 [triangle]) T min = 0.977, T max = 0.985
  • 4620 measured reflections
  • 4413 independent reflections
  • 2780 reflections with I > 2σ(I)
  • R int = 0.033
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.194
  • S = 1.02
  • 4413 reflections
  • 480 parameters
  • 24 restraints
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 EXPRESS; 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/S1600536809021059/at2806sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021059/at2806Isup2.hkl

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

Acknowledgments

This work was supported by the ‘948′ program of the State Forestry Administration under grant No. 2006–4-C03.

supplementary crystallographic information

Comment

Rosin is an abundant and renewable material composed of a series of diterpenic resin acids. It is widely used in production and daily lives in a modified form. Acrylic modified rosin is one of modified products of rosin. Although the title compound has been isolated by solvent extracting (Aldrich, 1971) and solvent washing (Bicu & Munstata, 2007) from acrylic modified rosin, its crystal has not been reported. In this work, we describe the crystal structure of the title compound. The molecular structure is shown in Fig. 1 and the crystal packing in Fig. 2, where the dash lines indicate hydrogen bondsing interactions (Table 1).

Experimental

The modified rosin (10 g) was dissolved in ethyl alcohol, then 5% sodium hydroxide solution (30 mL) and 2% aqueous sodium chloride solution (500 ml) was added dropwise successively with constant stirring. After dropping the mixture was stirred for another 15 minutes and then filtered. The filtrate was adjusted pH to 3 using 5% hydrochloric acid solution. The title compound was precipitated from the solution. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement

All H atoms were placed geometrically with C—H = 0.93–0.98 Å, O—H = 0.82 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom. In the absence of significant anomalous dispersion effects Friedel pairs were averaged using MERG 3 in SHELXL-97.

Figures

Fig. 1.
A view of the molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
Fig. 2.
The crystal packing of the title compound. The dash lines indicate hydrogen bonding interactions.

Crystal data

C23H34O4·0.5C2H6OF(000) = 868
Mr = 397.54Dx = 1.141 Mg m3
Monoclinic, P21Melting point: 474 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.682 (3) ÅCell parameters from 25 reflections
b = 12.476 (3) Åθ = 9–12°
c = 14.629 (3) ŵ = 0.08 mm1
β = 90.12 (3)°T = 293 K
V = 2314.6 (9) Å3Block, colourless
Z = 40.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2780 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
graphiteθmax = 25.3°, θmin = 1.4°
ω/2θ scansh = 0→15
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)k = 0→14
Tmin = 0.977, Tmax = 0.985l = −17→17
4620 measured reflections3 standard reflections every 200 reflections
4413 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) = 0.194H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.07P)2 + 2P] where P = (Fo2 + 2Fc2)/3
4413 reflections(Δ/σ)max < 0.001
480 parametersΔρmax = 0.41 e Å3
24 restraintsΔρmin = −0.46 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
O10.4273 (5)0.0876 (5)−0.8077 (3)0.102 (2)
H1D0.41940.0560−0.75910.153*
O20.5275 (4)−0.0529 (5)−0.8341 (3)0.0851 (16)
O30.9581 (5)0.4395 (7)−0.8591 (4)0.126 (2)
O40.7895 (5)0.4697 (6)−0.8765 (4)0.120 (2)
H4A0.79940.5018−0.82840.180*
C10.7264 (7)−0.2280 (8)−1.0584 (6)0.107
H1A0.7431−0.2911−1.09290.161*
H1B0.6911−0.2481−1.00300.161*
H1C0.7903−0.1903−1.04360.161*
C20.7017 (7)−0.1389 (9)−1.2089 (6)0.106
H2A0.6525−0.0958−1.24260.159*
H2B0.7115−0.2061−1.23970.159*
H2C0.7681−0.1021−1.20480.159*
C30.6586 (7)−0.1594 (8)−1.1118 (7)0.103 (3)
H3A0.5918−0.1980−1.11940.123*
C40.6320 (5)−0.0537 (6)−1.0688 (5)0.072 (2)
C50.6772 (5)−0.0079 (5)−0.9964 (4)0.0544 (15)
H5A0.7320−0.0405−0.96450.065*
C60.6333 (4)0.1013 (5)−0.9689 (4)0.0520 (15)
C70.6353 (4)0.1774 (5)−1.0529 (4)0.0518 (15)
H7A0.58960.2378−1.03660.062*
C80.5802 (5)0.1215 (7)−1.1353 (4)0.070 (2)
H8A0.52200.1653−1.15660.084*
H8B0.63000.1137−1.18520.084*
C90.5399 (5)0.0127 (6)−1.1076 (4)0.0651 (18)
H9A0.5074−0.0240−1.15980.078*
C100.4610 (5)0.0217 (7)−1.0277 (4)0.073 (2)
H10A0.39770.0586−1.04790.088*
H10B0.4411−0.0493−1.00690.088*
C110.5125 (5)0.0839 (6)−0.9494 (4)0.0606 (17)
H11A0.47990.1551−0.94870.073*
C120.4906 (5)0.0343 (6)−0.8588 (5)0.0656 (19)
C130.6874 (5)0.1508 (6)−0.8859 (4)0.0612 (17)
H13A0.64140.2051−0.86020.073*
H13B0.69730.0956−0.83990.073*
C140.7930 (5)0.2011 (6)−0.9069 (4)0.0654 (18)
H14A0.84290.1460−0.92470.078*
H14B0.82020.2368−0.85280.078*
C150.7804 (5)0.2815 (6)−0.9837 (4)0.0555 (15)
H15A0.72030.3259−0.96530.067*
C160.7447 (5)0.2279 (5)−1.0760 (4)0.0579 (16)
C170.8741 (5)0.3615 (7)−0.9916 (4)0.0689 (19)
C180.8501 (6)0.4431 (7)−1.0690 (4)0.081 (2)
H18A0.79240.4891−1.05020.098*
H18B0.91150.4880−1.07860.098*
C190.8213 (6)0.3891 (7)−1.1580 (5)0.078 (2)
H19A0.80480.4434−1.20330.094*
H19B0.88150.3487−1.17990.094*
C200.7285 (5)0.3148 (6)−1.1481 (4)0.0656 (18)
H20A0.71470.2809−1.20650.079*
H20B0.66680.3567−1.13200.079*
C210.8229 (5)0.1451 (6)−1.1122 (5)0.073 (2)
H21A0.79670.1155−1.16840.110*
H21B0.83130.0889−1.06800.110*
H21C0.88970.1789−1.12290.110*
C220.9823 (5)0.3088 (9)−1.0076 (6)0.094 (3)
H22A1.03710.3606−0.99720.141*
H22B0.98620.2831−1.06930.141*
H22C0.99110.2498−0.96610.141*
C230.8768 (6)0.4258 (7)−0.9028 (5)0.076 (2)
O51.0495 (5)0.0182 (7)−0.3837 (4)0.1285 (17)
O60.9276 (5)−0.0140 (8)−0.2842 (4)0.1285 (17)
H6A0.9796−0.0252−0.25220.193*
O70.6143 (5)0.5069 (5)−0.3528 (3)0.0916 (16)
O80.5194 (5)0.3646 (5)−0.3324 (4)0.0977 (18)
H8C0.50940.3950−0.28350.147*
C241.0176 (8)0.1264 (10)−0.7555 (5)0.115 (3)
H24A1.07680.1292−0.79630.172*
H24B0.98500.1957−0.75260.172*
H24C0.96750.0748−0.77760.172*
C251.1456 (7)0.1660 (10)−0.6261 (6)0.113 (3)
H25A1.16990.1391−0.56830.170*
H25B1.12070.2381−0.61880.170*
H25C1.20260.1651−0.66920.170*
C261.0545 (6)0.0943 (7)−0.6619 (4)0.079 (2)
H26A1.08240.0213−0.66690.095*
C270.9606 (5)0.0895 (6)−0.5969 (4)0.0626 (17)
C280.9403 (5)0.1554 (5)−0.5295 (4)0.0570 (16)
H28A0.98080.2163−0.51920.068*
C290.8485 (5)0.1274 (5)−0.4700 (4)0.0511 (14)
C300.7487 (5)0.1144 (6)−0.5314 (4)0.0608 (16)
H30A0.69670.0774−0.49320.073*
C310.7718 (6)0.0385 (6)−0.6096 (5)0.078 (2)
H31A0.76170.0753−0.66740.094*
H31B0.7235−0.0217−0.60750.094*
C320.8852 (6)−0.0019 (6)−0.6026 (5)0.0741 (19)
H32A0.9022−0.0479−0.65480.089*
C330.8950 (7)−0.0638 (7)−0.5143 (6)0.093 (3)
H33A0.9661−0.0915−0.50800.112*
H33B0.8466−0.1240−0.51480.112*
C340.8698 (6)0.0093 (6)−0.4343 (4)0.072 (2)
H34A0.8051−0.0169−0.40540.087*
C350.9563 (8)0.0079 (12)−0.3638 (6)0.1285 (17)
C360.8312 (5)0.2043 (6)−0.3913 (4)0.0625 (17)
H36A0.89850.2201−0.36270.075*
H36B0.78680.1702−0.34590.075*
C370.7799 (5)0.3086 (6)−0.4215 (4)0.0610 (17)
H37A0.82710.3468−0.46220.073*
H37B0.76700.3536−0.36860.073*
C380.6737 (5)0.2857 (5)−0.4717 (4)0.0555 (15)
H38A0.63640.2351−0.43200.067*
C390.6950 (5)0.2234 (6)−0.5600 (4)0.0616 (17)
C400.5989 (6)0.3845 (6)−0.4794 (4)0.0693 (19)
C410.4955 (7)0.3485 (8)−0.5246 (5)0.093 (3)
H41A0.45810.3018−0.48270.112*
H41B0.45170.4111−0.53520.112*
C420.5107 (7)0.2896 (9)−0.6151 (5)0.108 (3)
H42A0.53990.3383−0.66020.130*
H42B0.44310.2644−0.63760.130*
C430.5853 (6)0.1943 (8)−0.6017 (5)0.088 (2)
H43A0.59640.1601−0.66040.106*
H43B0.55130.1425−0.56210.106*
C440.7602 (6)0.2839 (6)−0.6303 (4)0.077 (2)
H44A0.82720.3026−0.60420.115*
H44B0.72350.3479−0.64810.115*
H44C0.77090.2393−0.68300.115*
C450.6462 (8)0.4816 (7)−0.5321 (5)0.098 (3)
H45A0.59800.5408−0.52970.147*
H45B0.65790.4619−0.59470.147*
H45C0.71200.5020−0.50450.147*
C460.5767 (6)0.4226 (7)−0.3827 (5)0.0652 (18)
O90.7956 (6)0.5787 (6)−0.7267 (4)0.122 (2)
H9B0.79240.5357−0.68180.147*
C480.7586 (9)0.7631 (10)−0.7751 (8)0.143
H48A0.72870.8246−0.74540.215*
H48B0.71550.7434−0.82640.215*
H48C0.82840.7801−0.79590.215*
C470.7636 (10)0.6740 (10)−0.7108 (8)0.149
H47A0.80640.6994−0.66020.179*
H47B0.69270.6663−0.68710.179*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.136 (5)0.096 (4)0.074 (3)0.045 (4)0.051 (3)0.029 (3)
O20.094 (4)0.084 (4)0.078 (3)0.026 (3)0.024 (3)0.028 (3)
O30.118 (4)0.157 (6)0.102 (4)−0.028 (4)−0.035 (3)−0.022 (4)
O40.121 (4)0.140 (5)0.098 (4)−0.001 (4)−0.026 (3)−0.052 (4)
C10.0980.1080.1140.023−0.071−0.065
C20.1060.1060.1060.0000.0000.000
C30.076 (5)0.096 (7)0.136 (8)−0.023 (5)0.016 (5)−0.043 (6)
C40.066 (4)0.070 (5)0.081 (5)−0.013 (4)0.017 (4)−0.019 (4)
C50.054 (3)0.054 (4)0.055 (3)−0.004 (3)−0.002 (3)0.005 (3)
C60.049 (3)0.069 (4)0.038 (3)−0.002 (3)0.003 (2)0.010 (3)
C70.053 (3)0.064 (4)0.039 (3)−0.001 (3)0.000 (2)0.002 (3)
C80.069 (4)0.100 (6)0.041 (3)−0.015 (4)−0.009 (3)−0.006 (4)
C90.057 (4)0.079 (5)0.059 (4)−0.012 (4)0.002 (3)−0.012 (4)
C100.056 (4)0.097 (6)0.067 (4)−0.011 (4)0.002 (3)0.003 (4)
C110.058 (4)0.076 (5)0.048 (3)0.004 (4)0.009 (3)0.008 (3)
C120.059 (4)0.079 (5)0.059 (4)−0.008 (4)0.014 (3)0.005 (4)
C130.080 (4)0.069 (4)0.034 (3)0.000 (4)0.000 (3)0.009 (3)
C140.073 (4)0.084 (5)0.039 (3)−0.002 (4)−0.009 (3)−0.002 (3)
C150.057 (3)0.065 (4)0.044 (3)−0.003 (3)0.002 (3)0.000 (3)
C160.067 (4)0.064 (4)0.043 (3)−0.011 (3)0.009 (3)0.006 (3)
C170.068 (4)0.084 (5)0.055 (4)−0.014 (4)−0.003 (3)0.006 (4)
C180.097 (5)0.092 (6)0.055 (4)−0.038 (5)−0.009 (4)0.011 (4)
C190.092 (5)0.085 (5)0.056 (4)−0.018 (5)0.001 (4)0.015 (4)
C200.073 (4)0.089 (5)0.035 (3)0.000 (4)−0.007 (3)0.007 (3)
C210.070 (4)0.084 (5)0.066 (4)−0.011 (4)0.029 (3)−0.010 (4)
C220.054 (4)0.131 (8)0.097 (5)−0.010 (5)−0.007 (4)−0.002 (6)
C230.083 (4)0.086 (5)0.058 (4)−0.015 (4)−0.019 (3)0.004 (4)
O50.106 (3)0.208 (5)0.071 (2)0.011 (4)0.000 (2)0.044 (3)
O60.106 (3)0.208 (5)0.071 (2)0.011 (4)0.000 (2)0.044 (3)
O70.124 (4)0.083 (4)0.068 (3)−0.001 (4)0.026 (3)−0.007 (3)
O80.112 (4)0.112 (5)0.070 (3)−0.011 (4)0.026 (3)−0.017 (3)
C240.139 (8)0.146 (9)0.058 (4)0.037 (7)0.027 (5)0.015 (6)
C250.095 (6)0.149 (10)0.096 (6)0.010 (7)0.036 (5)0.009 (7)
C260.105 (6)0.079 (5)0.054 (4)0.021 (5)0.028 (4)−0.001 (4)
C270.076 (4)0.062 (4)0.050 (3)0.012 (4)0.010 (3)−0.008 (3)
C280.061 (4)0.060 (4)0.049 (3)0.001 (3)0.006 (3)−0.003 (3)
C290.061 (4)0.051 (4)0.041 (3)0.006 (3)0.004 (3)−0.001 (3)
C300.068 (4)0.065 (4)0.049 (3)0.002 (3)0.000 (3)−0.005 (3)
C310.092 (5)0.069 (5)0.074 (5)−0.005 (4)−0.008 (4)−0.020 (4)
C320.098 (5)0.052 (4)0.072 (4)0.013 (4)0.006 (4)−0.013 (4)
C330.107 (6)0.070 (5)0.103 (6)0.019 (5)0.001 (5)0.009 (5)
C340.091 (5)0.070 (5)0.057 (4)0.005 (4)0.010 (3)0.023 (4)
C350.106 (3)0.208 (5)0.071 (2)0.011 (4)0.000 (2)0.044 (3)
C360.070 (4)0.076 (5)0.042 (3)−0.001 (4)0.000 (3)−0.005 (3)
C370.069 (4)0.073 (5)0.041 (3)−0.010 (4)0.004 (3)−0.022 (3)
C380.065 (4)0.061 (4)0.040 (3)0.004 (3)0.001 (3)0.001 (3)
C390.072 (4)0.072 (4)0.041 (3)0.001 (4)−0.002 (3)−0.005 (3)
C400.080 (5)0.082 (5)0.046 (3)0.020 (4)0.003 (3)−0.006 (4)
C410.097 (5)0.118 (7)0.064 (5)0.033 (5)−0.016 (4)−0.018 (5)
C420.096 (6)0.151 (9)0.078 (5)0.042 (7)−0.030 (4)−0.012 (6)
C430.091 (5)0.112 (7)0.061 (4)0.015 (5)−0.021 (4)−0.022 (5)
C440.106 (5)0.080 (5)0.045 (3)0.029 (5)0.014 (3)0.003 (4)
C450.158 (8)0.077 (6)0.060 (4)0.038 (6)0.021 (5)0.009 (4)
C460.069 (4)0.074 (5)0.053 (4)0.006 (4)0.006 (3)−0.001 (4)
O90.172 (6)0.099 (5)0.096 (4)0.034 (5)−0.003 (4)−0.020 (4)
C480.1430.1430.1430.0000.0000.000
C470.1490.1490.1490.0000.0000.000

Geometric parameters (Å, °)

O1—C121.284 (8)O8—C461.262 (9)
O1—H1D0.8200O8—H8C0.8200
O2—C121.237 (9)C24—C261.501 (10)
O3—C231.224 (8)C24—H24A0.9600
O4—C231.293 (9)C24—H24B0.9600
O4—H4A0.8200C24—H24C0.9600
C1—C31.442 (12)C25—C261.551 (12)
C1—H1A0.9600C25—H25A0.9600
C1—H1B0.9600C25—H25B0.9600
C1—H1C0.9600C25—H25C0.9600
C2—C31.545 (12)C26—C271.527 (9)
C2—H2A0.9600C26—H26A0.9800
C2—H2B0.9600C27—C281.309 (8)
C2—H2C0.9600C27—C321.490 (10)
C3—C41.499 (11)C28—C291.496 (8)
C3—H3A0.9800C28—H28A0.9300
C4—C51.333 (9)C29—C361.516 (8)
C4—C91.540 (10)C29—C301.558 (8)
C5—C61.526 (9)C29—C341.586 (9)
C5—H5A0.9300C30—C311.514 (9)
C6—C131.525 (8)C30—C391.576 (10)
C6—C71.552 (8)C30—H30A0.9800
C6—C111.574 (8)C31—C321.527 (10)
C7—C81.558 (8)C31—H31A0.9700
C7—C161.562 (8)C31—H31B0.9700
C7—H7A0.9800C32—C331.510 (10)
C8—C91.507 (10)C32—H32A0.9800
C8—H8A0.9700C33—C341.518 (11)
C8—H8B0.9700C33—H33A0.9700
C9—C101.544 (9)C33—H33B0.9700
C9—H9A0.9800C34—C351.504 (12)
C10—C111.528 (9)C34—H34A0.9800
C10—H10A0.9700C36—C371.520 (10)
C10—H10B0.9700C36—H36A0.9700
C11—C121.490 (9)C36—H36B0.9700
C11—H11A0.9800C37—C381.559 (8)
C13—C141.512 (9)C37—H37A0.9700
C13—H13A0.9700C37—H37B0.9700
C13—H13B0.9700C38—C391.532 (8)
C14—C151.514 (9)C38—C401.560 (9)
C14—H14A0.9700C38—H38A0.9800
C14—H14B0.9700C39—C441.522 (10)
C15—C171.556 (9)C39—C431.561 (10)
C15—C161.573 (8)C40—C461.520 (9)
C15—H15A0.9800C40—C411.534 (11)
C16—C201.526 (9)C40—C451.557 (11)
C16—C211.527 (9)C41—C421.527 (11)
C17—C231.527 (10)C41—H41A0.9700
C17—C221.540 (10)C41—H41B0.9700
C17—C181.553 (10)C42—C431.532 (12)
C18—C191.510 (9)C42—H42A0.9700
C18—H18A0.9700C42—H42B0.9700
C18—H18B0.9700C43—H43A0.9700
C19—C201.505 (10)C43—H43B0.9700
C19—H19A0.9700C44—H44A0.9600
C19—H19B0.9700C44—H44B0.9600
C20—H20A0.9700C44—H44C0.9600
C20—H20B0.9700C45—H45A0.9600
C21—H21A0.9600C45—H45B0.9600
C21—H21B0.9600C45—H45C0.9600
C21—H21C0.9600O9—C471.278 (11)
C22—H22A0.9600O9—H9B0.8499
C22—H22B0.9600C48—C471.458 (9)
C22—H22C0.9600C48—H48A0.9600
O5—C351.224 (10)C48—H48B0.9600
O6—C351.252 (10)C48—H48C0.9600
O6—H6A0.8200C47—H47A0.9700
O7—C461.234 (9)C47—H47B0.9700
C12—O1—H1D109.5H24B—C24—H24C109.5
C23—O4—H4A109.5C26—C25—H25A109.5
C3—C1—H1A109.5C26—C25—H25B109.5
C3—C1—H1B109.5H25A—C25—H25B109.5
H1A—C1—H1B109.5C26—C25—H25C109.5
C3—C1—H1C109.5H25A—C25—H25C109.5
H1A—C1—H1C109.5H25B—C25—H25C109.5
H1B—C1—H1C109.5C24—C26—C27109.7 (7)
C3—C2—H2A109.5C24—C26—C25112.6 (8)
C3—C2—H2B109.5C27—C26—C25113.2 (6)
H2A—C2—H2B109.5C24—C26—H26A107.0
C3—C2—H2C109.5C27—C26—H26A107.0
H2A—C2—H2C109.5C25—C26—H26A107.0
H2B—C2—H2C109.5C28—C27—C32113.3 (6)
C1—C3—C4115.4 (8)C28—C27—C26126.8 (7)
C1—C3—C2112.6 (8)C32—C27—C26119.8 (6)
C4—C3—C2108.7 (8)C27—C28—C29116.5 (6)
C1—C3—H3A106.5C27—C28—H28A121.8
C4—C3—H3A106.5C29—C28—H28A121.8
C2—C3—H3A106.5C28—C29—C36114.1 (5)
C5—C4—C3127.9 (8)C28—C29—C30108.7 (5)
C5—C4—C9112.7 (6)C36—C29—C30112.6 (5)
C3—C4—C9119.3 (7)C28—C29—C34106.0 (5)
C4—C5—C6115.8 (6)C36—C29—C34111.2 (5)
C4—C5—H5A122.1C30—C29—C34103.3 (5)
C6—C5—H5A122.1C31—C30—C29110.0 (5)
C13—C6—C5114.1 (5)C31—C30—C39115.0 (5)
C13—C6—C7112.0 (5)C29—C30—C39114.4 (5)
C5—C6—C7109.4 (4)C31—C30—H30A105.5
C13—C6—C11110.3 (5)C29—C30—H30A105.5
C5—C6—C11106.3 (5)C39—C30—H30A105.5
C7—C6—C11104.2 (5)C30—C31—C32109.8 (6)
C6—C7—C8109.3 (5)C30—C31—H31A109.7
C6—C7—C16115.7 (5)C32—C31—H31A109.7
C8—C7—C16114.2 (5)C30—C31—H31B109.7
C6—C7—H7A105.6C32—C31—H31B109.7
C8—C7—H7A105.6H31A—C31—H31B108.2
C16—C7—H7A105.6C27—C32—C33107.0 (6)
C9—C8—C7110.3 (5)C27—C32—C31110.8 (6)
C9—C8—H8A109.6C33—C32—C31107.6 (6)
C7—C8—H8A109.6C27—C32—H32A110.5
C9—C8—H8B109.6C33—C32—H32A110.5
C7—C8—H8B109.6C31—C32—H32A110.5
H8A—C8—H8B108.1C32—C33—C34109.6 (6)
C8—C9—C4109.0 (5)C32—C33—H33A109.8
C8—C9—C10111.1 (6)C34—C33—H33A109.8
C4—C9—C10104.7 (6)C32—C33—H33B109.8
C8—C9—H9A110.6C34—C33—H33B109.8
C4—C9—H9A110.6H33A—C33—H33B108.2
C10—C9—H9A110.6C35—C34—C33111.5 (8)
C11—C10—C9109.1 (5)C35—C34—C29111.1 (8)
C11—C10—H10A109.9C33—C34—C29109.9 (5)
C9—C10—H10A109.9C35—C34—H34A108.1
C11—C10—H10B109.9C33—C34—H34A108.1
C9—C10—H10B109.9C29—C34—H34A108.1
H10A—C10—H10B108.3O5—C35—O6121.8 (9)
C12—C11—C10112.1 (6)O5—C35—C34122.6 (8)
C12—C11—C6113.7 (5)O6—C35—C34115.3 (9)
C10—C11—C6110.4 (5)C29—C36—C37112.5 (5)
C12—C11—H11A106.7C29—C36—H36A109.1
C10—C11—H11A106.7C37—C36—H36A109.1
C6—C11—H11A106.7C29—C36—H36B109.1
O2—C12—O1121.5 (6)C37—C36—H36B109.1
O2—C12—C11123.6 (7)H36A—C36—H36B107.8
O1—C12—C11114.8 (7)C36—C37—C38110.4 (5)
C14—C13—C6113.8 (5)C36—C37—H37A109.6
C14—C13—H13A108.8C38—C37—H37A109.6
C6—C13—H13A108.8C36—C37—H37B109.6
C14—C13—H13B108.8C38—C37—H37B109.6
C6—C13—H13B108.8H37A—C37—H37B108.1
H13A—C13—H13B107.7C39—C38—C37109.6 (5)
C13—C14—C15109.5 (5)C39—C38—C40116.6 (5)
C13—C14—H14A109.8C37—C38—C40114.5 (6)
C15—C14—H14A109.8C39—C38—H38A104.9
C13—C14—H14B109.8C37—C38—H38A104.9
C15—C14—H14B109.8C40—C38—H38A104.9
H14A—C14—H14B108.2C44—C39—C38114.5 (6)
C14—C15—C17113.6 (5)C44—C39—C43109.6 (6)
C14—C15—C16112.7 (5)C38—C39—C43106.8 (5)
C17—C15—C16115.3 (5)C44—C39—C30111.9 (6)
C14—C15—H15A104.6C38—C39—C30106.9 (5)
C17—C15—H15A104.6C43—C39—C30106.7 (6)
C16—C15—H15A104.6C46—C40—C41109.5 (6)
C20—C16—C21109.1 (5)C46—C40—C45106.9 (6)
C20—C16—C7108.6 (5)C41—C40—C45110.1 (6)
C21—C16—C7112.3 (6)C46—C40—C38107.0 (5)
C20—C16—C15109.2 (5)C41—C40—C38108.6 (6)
C21—C16—C15113.5 (5)C45—C40—C38114.6 (6)
C7—C16—C15103.9 (4)C42—C41—C40113.9 (7)
C23—C17—C22109.6 (6)C42—C41—H41A108.8
C23—C17—C18106.3 (6)C40—C41—H41A108.8
C22—C17—C18110.0 (6)C42—C41—H41B108.8
C23—C17—C15106.8 (5)C40—C41—H41B108.8
C22—C17—C15114.7 (7)H41A—C41—H41B107.7
C18—C17—C15109.0 (5)C41—C42—C43110.0 (6)
C19—C18—C17112.5 (7)C41—C42—H42A109.7
C19—C18—H18A109.1C43—C42—H42A109.7
C17—C18—H18A109.1C41—C42—H42B109.7
C19—C18—H18B109.1C43—C42—H42B109.7
C17—C18—H18B109.1H42A—C42—H42B108.2
H18A—C18—H18B107.8C42—C43—C39114.8 (7)
C20—C19—C18112.3 (6)C42—C43—H43A108.6
C20—C19—H19A109.1C39—C43—H43A108.6
C18—C19—H19A109.1C42—C43—H43B108.6
C20—C19—H19B109.1C39—C43—H43B108.6
C18—C19—H19B109.1H43A—C43—H43B107.5
H19A—C19—H19B107.9C39—C44—H44A109.5
C19—C20—C16113.6 (5)C39—C44—H44B109.5
C19—C20—H20A108.8H44A—C44—H44B109.5
C16—C20—H20A108.8C39—C44—H44C109.5
C19—C20—H20B108.8H44A—C44—H44C109.5
C16—C20—H20B108.8H44B—C44—H44C109.5
H20A—C20—H20B107.7C40—C45—H45A109.5
C16—C21—H21A109.5C40—C45—H45B109.5
C16—C21—H21B109.5H45A—C45—H45B109.5
H21A—C21—H21B109.5C40—C45—H45C109.5
C16—C21—H21C109.5H45A—C45—H45C109.5
H21A—C21—H21C109.5H45B—C45—H45C109.5
H21B—C21—H21C109.5O7—C46—O8120.4 (7)
C17—C22—H22A109.5O7—C46—C40121.6 (7)
C17—C22—H22B109.5O8—C46—C40118.1 (7)
H22A—C22—H22B109.5C47—O9—H9B115.5
C17—C22—H22C109.5C47—C48—H48A109.5
H22A—C22—H22C109.5C47—C48—H48B109.5
H22B—C22—H22C109.5H48A—C48—H48B109.5
O3—C23—O4120.4 (8)C47—C48—H48C109.5
O3—C23—C17122.3 (8)H48A—C48—H48C109.5
O4—C23—C17117.2 (6)H48B—C48—H48C109.5
C35—O6—H6A109.5O9—C47—C48127.2 (12)
C46—O8—H8C109.5O9—C47—H47A105.5
C26—C24—H24A109.5C48—C47—H47A105.5
C26—C24—H24B109.5O9—C47—H47B105.5
H24A—C24—H24B109.5C48—C47—H47B105.5
C26—C24—H24C109.5H47A—C47—H47B106.1
H24A—C24—H24C109.5
C1—C3—C4—C512.9 (12)C24—C26—C27—C28−109.9 (9)
C2—C3—C4—C5−114.6 (9)C25—C26—C27—C2816.8 (11)
C1—C3—C4—C9−164.8 (7)C24—C26—C27—C3274.9 (9)
C2—C3—C4—C967.6 (9)C25—C26—C27—C32−158.4 (7)
C3—C4—C5—C6179.5 (7)C32—C27—C28—C291.1 (9)
C9—C4—C5—C6−2.7 (8)C26—C27—C28—C29−174.4 (6)
C4—C5—C6—C13−179.9 (6)C27—C28—C29—C36177.9 (6)
C4—C5—C6—C7−53.6 (7)C27—C28—C29—C30−55.4 (7)
C4—C5—C6—C1158.3 (6)C27—C28—C29—C3455.1 (7)
C13—C6—C7—C8179.3 (5)C28—C29—C30—C3151.4 (7)
C5—C6—C7—C851.8 (6)C36—C29—C30—C31178.9 (6)
C11—C6—C7—C8−61.5 (6)C34—C29—C30—C31−61.0 (7)
C13—C6—C7—C1648.7 (7)C28—C29—C30—C39−79.9 (6)
C5—C6—C7—C16−78.8 (6)C36—C29—C30—C3947.6 (7)
C11—C6—C7—C16168.0 (5)C34—C29—C30—C39167.8 (5)
C6—C7—C8—C91.5 (7)C29—C30—C31—C320.6 (8)
C16—C7—C8—C9132.9 (6)C39—C30—C31—C32131.5 (6)
C7—C8—C9—C4−56.1 (7)C28—C27—C32—C33−61.3 (8)
C7—C8—C9—C1058.8 (7)C26—C27—C32—C33114.6 (7)
C5—C4—C9—C859.5 (7)C28—C27—C32—C3155.7 (8)
C3—C4—C9—C8−122.5 (7)C26—C27—C32—C31−128.4 (7)
C5—C4—C9—C10−59.5 (7)C30—C31—C32—C27−54.1 (8)
C3—C4—C9—C10118.6 (7)C30—C31—C32—C3362.5 (8)
C8—C9—C10—C11−54.0 (8)C27—C32—C33—C3459.0 (8)
C4—C9—C10—C1163.5 (7)C31—C32—C33—C34−60.1 (8)
C9—C10—C11—C12−137.2 (6)C32—C33—C34—C35−127.1 (8)
C9—C10—C11—C6−9.3 (8)C32—C33—C34—C29−3.4 (9)
C13—C6—C11—C12−46.0 (8)C28—C29—C34—C3572.8 (7)
C5—C6—C11—C1278.1 (7)C36—C29—C34—C35−51.8 (8)
C7—C6—C11—C12−166.4 (6)C30—C29—C34—C35−172.9 (6)
C13—C6—C11—C10−172.9 (6)C28—C29—C34—C33−51.1 (7)
C5—C6—C11—C10−48.8 (7)C36—C29—C34—C33−175.7 (6)
C7—C6—C11—C1066.7 (7)C30—C29—C34—C3363.2 (7)
C10—C11—C12—O269.1 (9)C33—C34—C35—O548.2 (16)
C6—C11—C12—O2−57.0 (9)C29—C34—C35—O5−74.8 (15)
C10—C11—C12—O1−109.0 (7)C33—C34—C35—O6−125.7 (11)
C6—C11—C12—O1124.9 (7)C29—C34—C35—O6111.3 (12)
C5—C6—C13—C1478.2 (7)C28—C29—C36—C3776.8 (7)
C7—C6—C13—C14−46.7 (8)C30—C29—C36—C37−47.8 (7)
C11—C6—C13—C14−162.3 (6)C34—C29—C36—C37−163.3 (5)
C6—C13—C14—C1554.2 (8)C29—C36—C37—C3856.3 (7)
C13—C14—C15—C17162.8 (6)C36—C37—C38—C39−64.4 (6)
C13—C14—C15—C16−63.8 (7)C36—C37—C38—C40162.4 (5)
C6—C7—C16—C20−169.8 (5)C37—C38—C39—C44−63.5 (7)
C8—C7—C16—C2062.0 (7)C40—C38—C39—C4468.6 (7)
C6—C7—C16—C2169.4 (7)C37—C38—C39—C43175.0 (6)
C8—C7—C16—C21−58.8 (7)C40—C38—C39—C43−52.9 (8)
C6—C7—C16—C15−53.7 (7)C37—C38—C39—C3061.0 (7)
C8—C7—C16—C15178.1 (6)C40—C38—C39—C30−166.8 (5)
C14—C15—C16—C20177.2 (5)C31—C30—C39—C44−56.5 (8)
C17—C15—C16—C20−50.2 (7)C29—C30—C39—C4472.3 (7)
C14—C15—C16—C21−60.8 (7)C31—C30—C39—C38177.4 (6)
C17—C15—C16—C2171.8 (7)C29—C30—C39—C38−53.9 (7)
C14—C15—C16—C761.5 (6)C31—C30—C39—C4363.4 (7)
C17—C15—C16—C7−165.9 (6)C29—C30—C39—C43−167.9 (5)
C14—C15—C17—C23−62.8 (8)C39—C38—C40—C46171.7 (6)
C16—C15—C17—C23165.0 (6)C37—C38—C40—C46−58.4 (7)
C14—C15—C17—C2258.9 (8)C39—C38—C40—C4153.6 (8)
C16—C15—C17—C22−73.3 (7)C37—C38—C40—C41−176.5 (5)
C14—C15—C17—C18−177.3 (6)C39—C38—C40—C45−70.0 (8)
C16—C15—C17—C1850.6 (8)C37—C38—C40—C4559.9 (7)
C23—C17—C18—C19−167.4 (6)C46—C40—C41—C42−169.3 (8)
C22—C17—C18—C1974.0 (8)C45—C40—C41—C4273.5 (9)
C15—C17—C18—C19−52.6 (8)C38—C40—C41—C42−52.7 (9)
C17—C18—C19—C2056.9 (9)C40—C41—C42—C4355.0 (11)
C18—C19—C20—C16−57.0 (9)C41—C42—C43—C39−55.8 (10)
C21—C16—C20—C19−72.7 (7)C44—C39—C43—C42−71.1 (8)
C7—C16—C20—C19164.5 (6)C38—C39—C43—C4253.5 (8)
C15—C16—C20—C1951.9 (7)C30—C39—C43—C42167.6 (6)
C22—C17—C23—O36.9 (11)C41—C40—C46—O7−133.9 (8)
C18—C17—C23—O3−112.0 (9)C45—C40—C46—O7−14.6 (9)
C15—C17—C23—O3131.7 (8)C38—C40—C46—O7108.6 (8)
C22—C17—C23—O4−175.7 (8)C41—C40—C46—O847.1 (9)
C18—C17—C23—O465.5 (9)C45—C40—C46—O8166.4 (7)
C15—C17—C23—O4−50.9 (9)C38—C40—C46—O8−70.5 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15A···O40.982.382.824 (10)107
C18—H18A···O40.972.552.939 (8)104
C33—H33A···O50.972.512.919 (11)105
C41—H41A···O80.972.462.834 (9)103
O1—H1D···O7i0.821.802.610 (7)169
O4—H4A···O90.821.772.589 (9)169
O6—H6A···O3ii0.821.862.611 (9)152
O8—H8C···O2iii0.821.902.712 (8)171
O9—H9B···O5iv0.852.232.651 (9)111
C2—H2C···O6v0.962.583.443 (12)150

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2806).

References

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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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