organic compounds
16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene-5,14-dicarboxylic acid ethanol hemisolvate
aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
*Correspondence e-mail: shangsb@hotmail.com
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) and solvent washing (Bicu & Munstata, 2007) from acrylic modified rosin.
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809021059/at2806sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809021059/at2806Isup2.hkl
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.
All H atoms were placed geometrically with C—H = 0.93–0.98 Å, O—H = 0.82 Å and included in the
in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the In the absence of significant effects Friedel pairs were averaged using MERG 3 in SHELXL-97.Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell
CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H34O4·0.5C2H6O | F(000) = 868 |
Mr = 397.54 | Dx = 1.141 Mg m−3 |
Monoclinic, P21 | Melting point: 474 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 12.682 (3) Å | Cell parameters from 25 reflections |
b = 12.476 (3) Å | θ = 9–12° |
c = 14.629 (3) Å | µ = 0.08 mm−1 |
β = 90.12 (3)° | T = 293 K |
V = 2314.6 (9) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 2780 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.3°, θmin = 1.4° |
ω/2θ scans | h = 0→15 |
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995) | k = 0→14 |
Tmin = 0.977, Tmax = 0.985 | l = −17→17 |
4620 measured reflections | 3 standard reflections every 200 reflections |
4413 independent reflections | intensity decay: 1% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.07P)2 + 2P] where P = (Fo2 + 2Fc2)/3 |
4413 reflections | (Δ/σ)max < 0.001 |
480 parameters | Δρmax = 0.41 e Å−3 |
24 restraints | Δρmin = −0.47 e Å−3 |
C23H34O4·0.5C2H6O | V = 2314.6 (9) Å3 |
Mr = 397.54 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.682 (3) Å | µ = 0.08 mm−1 |
b = 12.476 (3) Å | T = 293 K |
c = 14.629 (3) Å | 0.30 × 0.20 × 0.20 mm |
β = 90.12 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2780 reflections with I > 2σ(I) |
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995) | Rint = 0.033 |
Tmin = 0.977, Tmax = 0.985 | 3 standard reflections every 200 reflections |
4620 measured reflections | intensity decay: 1% |
4413 independent reflections |
R[F2 > 2σ(F2)] = 0.077 | 24 restraints |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.41 e Å−3 |
4413 reflections | Δρmin = −0.47 e Å−3 |
480 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4273 (5) | 0.0876 (5) | −0.8077 (3) | 0.102 (2) | |
H1D | 0.4194 | 0.0560 | −0.7591 | 0.153* | |
O2 | 0.5275 (4) | −0.0529 (5) | −0.8341 (3) | 0.0851 (16) | |
O3 | 0.9581 (5) | 0.4395 (7) | −0.8591 (4) | 0.126 (2) | |
O4 | 0.7895 (5) | 0.4697 (6) | −0.8765 (4) | 0.120 (2) | |
H4A | 0.7994 | 0.5018 | −0.8284 | 0.180* | |
C1 | 0.7264 (7) | −0.2280 (8) | −1.0584 (6) | 0.107 | |
H1A | 0.7431 | −0.2911 | −1.0929 | 0.161* | |
H1B | 0.6911 | −0.2481 | −1.0030 | 0.161* | |
H1C | 0.7903 | −0.1903 | −1.0436 | 0.161* | |
C2 | 0.7017 (7) | −0.1389 (9) | −1.2089 (6) | 0.106 | |
H2A | 0.6525 | −0.0958 | −1.2426 | 0.159* | |
H2B | 0.7115 | −0.2061 | −1.2397 | 0.159* | |
H2C | 0.7681 | −0.1021 | −1.2048 | 0.159* | |
C3 | 0.6586 (7) | −0.1594 (8) | −1.1118 (7) | 0.103 (3) | |
H3A | 0.5918 | −0.1980 | −1.1194 | 0.123* | |
C4 | 0.6320 (5) | −0.0537 (6) | −1.0688 (5) | 0.072 (2) | |
C5 | 0.6772 (5) | −0.0079 (5) | −0.9964 (4) | 0.0544 (15) | |
H5A | 0.7320 | −0.0405 | −0.9645 | 0.065* | |
C6 | 0.6333 (4) | 0.1013 (5) | −0.9689 (4) | 0.0520 (15) | |
C7 | 0.6353 (4) | 0.1774 (5) | −1.0529 (4) | 0.0518 (15) | |
H7A | 0.5896 | 0.2378 | −1.0366 | 0.062* | |
C8 | 0.5802 (5) | 0.1215 (7) | −1.1353 (4) | 0.070 (2) | |
H8A | 0.5220 | 0.1653 | −1.1566 | 0.084* | |
H8B | 0.6300 | 0.1137 | −1.1852 | 0.084* | |
C9 | 0.5399 (5) | 0.0127 (6) | −1.1076 (4) | 0.0651 (18) | |
H9A | 0.5074 | −0.0240 | −1.1598 | 0.078* | |
C10 | 0.4610 (5) | 0.0217 (7) | −1.0277 (4) | 0.073 (2) | |
H10A | 0.3977 | 0.0586 | −1.0479 | 0.088* | |
H10B | 0.4411 | −0.0493 | −1.0069 | 0.088* | |
C11 | 0.5125 (5) | 0.0839 (6) | −0.9494 (4) | 0.0606 (17) | |
H11A | 0.4799 | 0.1551 | −0.9487 | 0.073* | |
C12 | 0.4906 (5) | 0.0343 (6) | −0.8588 (5) | 0.0656 (19) | |
C13 | 0.6874 (5) | 0.1508 (6) | −0.8859 (4) | 0.0612 (17) | |
H13A | 0.6414 | 0.2051 | −0.8602 | 0.073* | |
H13B | 0.6973 | 0.0956 | −0.8399 | 0.073* | |
C14 | 0.7930 (5) | 0.2011 (6) | −0.9069 (4) | 0.0654 (18) | |
H14A | 0.8429 | 0.1460 | −0.9247 | 0.078* | |
H14B | 0.8202 | 0.2368 | −0.8528 | 0.078* | |
C15 | 0.7804 (5) | 0.2815 (6) | −0.9837 (4) | 0.0555 (15) | |
H15A | 0.7203 | 0.3259 | −0.9653 | 0.067* | |
C16 | 0.7447 (5) | 0.2279 (5) | −1.0760 (4) | 0.0579 (16) | |
C17 | 0.8741 (5) | 0.3615 (7) | −0.9916 (4) | 0.0689 (19) | |
C18 | 0.8501 (6) | 0.4431 (7) | −1.0690 (4) | 0.081 (2) | |
H18A | 0.7924 | 0.4891 | −1.0502 | 0.098* | |
H18B | 0.9115 | 0.4880 | −1.0786 | 0.098* | |
C19 | 0.8213 (6) | 0.3891 (7) | −1.1580 (5) | 0.078 (2) | |
H19A | 0.8048 | 0.4434 | −1.2033 | 0.094* | |
H19B | 0.8815 | 0.3487 | −1.1799 | 0.094* | |
C20 | 0.7285 (5) | 0.3148 (6) | −1.1481 (4) | 0.0656 (18) | |
H20A | 0.7147 | 0.2809 | −1.2065 | 0.079* | |
H20B | 0.6668 | 0.3567 | −1.1320 | 0.079* | |
C21 | 0.8229 (5) | 0.1451 (6) | −1.1122 (5) | 0.073 (2) | |
H21A | 0.7967 | 0.1155 | −1.1684 | 0.110* | |
H21B | 0.8313 | 0.0889 | −1.0680 | 0.110* | |
H21C | 0.8897 | 0.1789 | −1.1229 | 0.110* | |
C22 | 0.9823 (5) | 0.3088 (9) | −1.0076 (6) | 0.094 (3) | |
H22A | 1.0371 | 0.3606 | −0.9972 | 0.141* | |
H22B | 0.9862 | 0.2831 | −1.0693 | 0.141* | |
H22C | 0.9911 | 0.2498 | −0.9661 | 0.141* | |
C23 | 0.8768 (6) | 0.4258 (7) | −0.9028 (5) | 0.076 (2) | |
O5 | 1.0495 (5) | 0.0182 (7) | −0.3837 (4) | 0.1285 (17) | |
O6 | 0.9276 (5) | −0.0140 (8) | −0.2842 (4) | 0.1285 (17) | |
H6A | 0.9796 | −0.0252 | −0.2522 | 0.193* | |
O7 | 0.6143 (5) | 0.5069 (5) | −0.3528 (3) | 0.0916 (16) | |
O8 | 0.5194 (5) | 0.3646 (5) | −0.3324 (4) | 0.0977 (18) | |
H8C | 0.5094 | 0.3950 | −0.2835 | 0.147* | |
C24 | 1.0176 (8) | 0.1264 (10) | −0.7555 (5) | 0.115 (3) | |
H24A | 1.0768 | 0.1292 | −0.7963 | 0.172* | |
H24B | 0.9850 | 0.1957 | −0.7526 | 0.172* | |
H24C | 0.9675 | 0.0748 | −0.7776 | 0.172* | |
C25 | 1.1456 (7) | 0.1660 (10) | −0.6261 (6) | 0.113 (3) | |
H25A | 1.1699 | 0.1391 | −0.5683 | 0.170* | |
H25B | 1.1207 | 0.2381 | −0.6188 | 0.170* | |
H25C | 1.2026 | 0.1651 | −0.6692 | 0.170* | |
C26 | 1.0545 (6) | 0.0943 (7) | −0.6619 (4) | 0.079 (2) | |
H26A | 1.0824 | 0.0213 | −0.6669 | 0.095* | |
C27 | 0.9606 (5) | 0.0895 (6) | −0.5969 (4) | 0.0626 (17) | |
C28 | 0.9403 (5) | 0.1554 (5) | −0.5295 (4) | 0.0570 (16) | |
H28A | 0.9808 | 0.2163 | −0.5192 | 0.068* | |
C29 | 0.8485 (5) | 0.1274 (5) | −0.4700 (4) | 0.0511 (14) | |
C30 | 0.7487 (5) | 0.1144 (6) | −0.5314 (4) | 0.0608 (16) | |
H30A | 0.6967 | 0.0774 | −0.4932 | 0.073* | |
C31 | 0.7718 (6) | 0.0385 (6) | −0.6096 (5) | 0.078 (2) | |
H31A | 0.7617 | 0.0753 | −0.6674 | 0.094* | |
H31B | 0.7235 | −0.0217 | −0.6075 | 0.094* | |
C32 | 0.8852 (6) | −0.0019 (6) | −0.6026 (5) | 0.0741 (19) | |
H32A | 0.9022 | −0.0479 | −0.6548 | 0.089* | |
C33 | 0.8950 (7) | −0.0638 (7) | −0.5143 (6) | 0.093 (3) | |
H33A | 0.9661 | −0.0915 | −0.5080 | 0.112* | |
H33B | 0.8466 | −0.1240 | −0.5148 | 0.112* | |
C34 | 0.8698 (6) | 0.0093 (6) | −0.4343 (4) | 0.072 (2) | |
H34A | 0.8051 | −0.0169 | −0.4054 | 0.087* | |
C35 | 0.9563 (8) | 0.0079 (12) | −0.3638 (6) | 0.1285 (17) | |
C36 | 0.8312 (5) | 0.2043 (6) | −0.3913 (4) | 0.0625 (17) | |
H36A | 0.8985 | 0.2201 | −0.3627 | 0.075* | |
H36B | 0.7868 | 0.1702 | −0.3459 | 0.075* | |
C37 | 0.7799 (5) | 0.3086 (6) | −0.4215 (4) | 0.0610 (17) | |
H37A | 0.8271 | 0.3468 | −0.4622 | 0.073* | |
H37B | 0.7670 | 0.3536 | −0.3686 | 0.073* | |
C38 | 0.6737 (5) | 0.2857 (5) | −0.4717 (4) | 0.0555 (15) | |
H38A | 0.6364 | 0.2351 | −0.4320 | 0.067* | |
C39 | 0.6950 (5) | 0.2234 (6) | −0.5600 (4) | 0.0616 (17) | |
C40 | 0.5989 (6) | 0.3845 (6) | −0.4794 (4) | 0.0693 (19) | |
C41 | 0.4955 (7) | 0.3485 (8) | −0.5246 (5) | 0.093 (3) | |
H41A | 0.4581 | 0.3018 | −0.4827 | 0.112* | |
H41B | 0.4517 | 0.4111 | −0.5352 | 0.112* | |
C42 | 0.5107 (7) | 0.2896 (9) | −0.6151 (5) | 0.108 (3) | |
H42A | 0.5399 | 0.3383 | −0.6602 | 0.130* | |
H42B | 0.4431 | 0.2644 | −0.6376 | 0.130* | |
C43 | 0.5853 (6) | 0.1943 (8) | −0.6017 (5) | 0.088 (2) | |
H43A | 0.5964 | 0.1601 | −0.6604 | 0.106* | |
H43B | 0.5513 | 0.1425 | −0.5621 | 0.106* | |
C44 | 0.7602 (6) | 0.2839 (6) | −0.6303 (4) | 0.077 (2) | |
H44A | 0.8272 | 0.3026 | −0.6042 | 0.115* | |
H44B | 0.7235 | 0.3479 | −0.6481 | 0.115* | |
H44C | 0.7709 | 0.2393 | −0.6830 | 0.115* | |
C45 | 0.6462 (8) | 0.4816 (7) | −0.5321 (5) | 0.098 (3) | |
H45A | 0.5980 | 0.5408 | −0.5297 | 0.147* | |
H45B | 0.6579 | 0.4619 | −0.5947 | 0.147* | |
H45C | 0.7120 | 0.5020 | −0.5045 | 0.147* | |
C46 | 0.5767 (6) | 0.4226 (7) | −0.3827 (5) | 0.0652 (18) | |
O9 | 0.7956 (6) | 0.5787 (6) | −0.7267 (4) | 0.122 (2) | |
H9B | 0.7924 | 0.5357 | −0.6818 | 0.147* | |
C48 | 0.7586 (9) | 0.7631 (10) | −0.7751 (8) | 0.143 | |
H48A | 0.7287 | 0.8246 | −0.7454 | 0.215* | |
H48B | 0.7155 | 0.7434 | −0.8264 | 0.215* | |
H48C | 0.8284 | 0.7801 | −0.7959 | 0.215* | |
C47 | 0.7636 (10) | 0.6740 (10) | −0.7108 (8) | 0.149 | |
H47A | 0.8064 | 0.6994 | −0.6602 | 0.179* | |
H47B | 0.6927 | 0.6663 | −0.6871 | 0.179* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.136 (5) | 0.096 (4) | 0.074 (3) | 0.045 (4) | 0.051 (3) | 0.029 (3) |
O2 | 0.094 (4) | 0.084 (4) | 0.078 (3) | 0.026 (3) | 0.024 (3) | 0.028 (3) |
O3 | 0.118 (4) | 0.157 (6) | 0.102 (4) | −0.028 (4) | −0.035 (3) | −0.022 (4) |
O4 | 0.121 (4) | 0.140 (5) | 0.098 (4) | −0.001 (4) | −0.026 (3) | −0.052 (4) |
C1 | 0.098 | 0.108 | 0.114 | 0.023 | −0.071 | −0.065 |
C2 | 0.106 | 0.106 | 0.106 | 0.000 | 0.000 | 0.000 |
C3 | 0.076 (5) | 0.096 (7) | 0.136 (8) | −0.023 (5) | 0.016 (5) | −0.043 (6) |
C4 | 0.066 (4) | 0.070 (5) | 0.081 (5) | −0.013 (4) | 0.017 (4) | −0.019 (4) |
C5 | 0.054 (3) | 0.054 (4) | 0.055 (3) | −0.004 (3) | −0.002 (3) | 0.005 (3) |
C6 | 0.049 (3) | 0.069 (4) | 0.038 (3) | −0.002 (3) | 0.003 (2) | 0.010 (3) |
C7 | 0.053 (3) | 0.064 (4) | 0.039 (3) | −0.001 (3) | 0.000 (2) | 0.002 (3) |
C8 | 0.069 (4) | 0.100 (6) | 0.041 (3) | −0.015 (4) | −0.009 (3) | −0.006 (4) |
C9 | 0.057 (4) | 0.079 (5) | 0.059 (4) | −0.012 (4) | 0.002 (3) | −0.012 (4) |
C10 | 0.056 (4) | 0.097 (6) | 0.067 (4) | −0.011 (4) | 0.002 (3) | 0.003 (4) |
C11 | 0.058 (4) | 0.076 (5) | 0.048 (3) | 0.004 (4) | 0.009 (3) | 0.008 (3) |
C12 | 0.059 (4) | 0.079 (5) | 0.059 (4) | −0.008 (4) | 0.014 (3) | 0.005 (4) |
C13 | 0.080 (4) | 0.069 (4) | 0.034 (3) | 0.000 (4) | 0.000 (3) | 0.009 (3) |
C14 | 0.073 (4) | 0.084 (5) | 0.039 (3) | −0.002 (4) | −0.009 (3) | −0.002 (3) |
C15 | 0.057 (3) | 0.065 (4) | 0.044 (3) | −0.003 (3) | 0.002 (3) | 0.000 (3) |
C16 | 0.067 (4) | 0.064 (4) | 0.043 (3) | −0.011 (3) | 0.009 (3) | 0.006 (3) |
C17 | 0.068 (4) | 0.084 (5) | 0.055 (4) | −0.014 (4) | −0.003 (3) | 0.006 (4) |
C18 | 0.097 (5) | 0.092 (6) | 0.055 (4) | −0.038 (5) | −0.009 (4) | 0.011 (4) |
C19 | 0.092 (5) | 0.085 (5) | 0.056 (4) | −0.018 (5) | 0.001 (4) | 0.015 (4) |
C20 | 0.073 (4) | 0.089 (5) | 0.035 (3) | 0.000 (4) | −0.007 (3) | 0.007 (3) |
C21 | 0.070 (4) | 0.084 (5) | 0.066 (4) | −0.011 (4) | 0.029 (3) | −0.010 (4) |
C22 | 0.054 (4) | 0.131 (8) | 0.097 (5) | −0.010 (5) | −0.007 (4) | −0.002 (6) |
C23 | 0.083 (4) | 0.086 (5) | 0.058 (4) | −0.015 (4) | −0.019 (3) | 0.004 (4) |
O5 | 0.106 (3) | 0.208 (5) | 0.071 (2) | 0.011 (4) | 0.000 (2) | 0.044 (3) |
O6 | 0.106 (3) | 0.208 (5) | 0.071 (2) | 0.011 (4) | 0.000 (2) | 0.044 (3) |
O7 | 0.124 (4) | 0.083 (4) | 0.068 (3) | −0.001 (4) | 0.026 (3) | −0.007 (3) |
O8 | 0.112 (4) | 0.112 (5) | 0.070 (3) | −0.011 (4) | 0.026 (3) | −0.017 (3) |
C24 | 0.139 (8) | 0.146 (9) | 0.058 (4) | 0.037 (7) | 0.027 (5) | 0.015 (6) |
C25 | 0.095 (6) | 0.149 (10) | 0.096 (6) | 0.010 (7) | 0.036 (5) | 0.009 (7) |
C26 | 0.105 (6) | 0.079 (5) | 0.054 (4) | 0.021 (5) | 0.028 (4) | −0.001 (4) |
C27 | 0.076 (4) | 0.062 (4) | 0.050 (3) | 0.012 (4) | 0.010 (3) | −0.008 (3) |
C28 | 0.061 (4) | 0.060 (4) | 0.049 (3) | 0.001 (3) | 0.006 (3) | −0.003 (3) |
C29 | 0.061 (4) | 0.051 (4) | 0.041 (3) | 0.006 (3) | 0.004 (3) | −0.001 (3) |
C30 | 0.068 (4) | 0.065 (4) | 0.049 (3) | 0.002 (3) | 0.000 (3) | −0.005 (3) |
C31 | 0.092 (5) | 0.069 (5) | 0.074 (5) | −0.005 (4) | −0.008 (4) | −0.020 (4) |
C32 | 0.098 (5) | 0.052 (4) | 0.072 (4) | 0.013 (4) | 0.006 (4) | −0.013 (4) |
C33 | 0.107 (6) | 0.070 (5) | 0.103 (6) | 0.019 (5) | 0.001 (5) | 0.009 (5) |
C34 | 0.091 (5) | 0.070 (5) | 0.057 (4) | 0.005 (4) | 0.010 (3) | 0.023 (4) |
C35 | 0.106 (3) | 0.208 (5) | 0.071 (2) | 0.011 (4) | 0.000 (2) | 0.044 (3) |
C36 | 0.070 (4) | 0.076 (5) | 0.042 (3) | −0.001 (4) | 0.000 (3) | −0.005 (3) |
C37 | 0.069 (4) | 0.073 (5) | 0.041 (3) | −0.010 (4) | 0.004 (3) | −0.022 (3) |
C38 | 0.065 (4) | 0.061 (4) | 0.040 (3) | 0.004 (3) | 0.001 (3) | 0.001 (3) |
C39 | 0.072 (4) | 0.072 (4) | 0.041 (3) | 0.001 (4) | −0.002 (3) | −0.005 (3) |
C40 | 0.080 (5) | 0.082 (5) | 0.046 (3) | 0.020 (4) | 0.003 (3) | −0.006 (4) |
C41 | 0.097 (5) | 0.118 (7) | 0.064 (5) | 0.033 (5) | −0.016 (4) | −0.018 (5) |
C42 | 0.096 (6) | 0.151 (9) | 0.078 (5) | 0.042 (7) | −0.030 (4) | −0.012 (6) |
C43 | 0.091 (5) | 0.112 (7) | 0.061 (4) | 0.015 (5) | −0.021 (4) | −0.022 (5) |
C44 | 0.106 (5) | 0.080 (5) | 0.045 (3) | 0.029 (5) | 0.014 (3) | 0.003 (4) |
C45 | 0.158 (8) | 0.077 (6) | 0.060 (4) | 0.038 (6) | 0.021 (5) | 0.009 (4) |
C46 | 0.069 (4) | 0.074 (5) | 0.053 (4) | 0.006 (4) | 0.006 (3) | −0.001 (4) |
O9 | 0.172 (6) | 0.099 (5) | 0.096 (4) | 0.034 (5) | −0.003 (4) | −0.020 (4) |
C48 | 0.143 | 0.143 | 0.143 | 0.000 | 0.000 | 0.000 |
C47 | 0.149 | 0.149 | 0.149 | 0.000 | 0.000 | 0.000 |
O1—C12 | 1.284 (8) | O8—C46 | 1.262 (9) |
O1—H1D | 0.8200 | O8—H8C | 0.8200 |
O2—C12 | 1.237 (9) | C24—C26 | 1.501 (10) |
O3—C23 | 1.224 (8) | C24—H24A | 0.9600 |
O4—C23 | 1.293 (9) | C24—H24B | 0.9600 |
O4—H4A | 0.8200 | C24—H24C | 0.9600 |
C1—C3 | 1.442 (12) | C25—C26 | 1.551 (12) |
C1—H1A | 0.9600 | C25—H25A | 0.9600 |
C1—H1B | 0.9600 | C25—H25B | 0.9600 |
C1—H1C | 0.9600 | C25—H25C | 0.9600 |
C2—C3 | 1.545 (12) | C26—C27 | 1.527 (9) |
C2—H2A | 0.9600 | C26—H26A | 0.9800 |
C2—H2B | 0.9600 | C27—C28 | 1.309 (8) |
C2—H2C | 0.9600 | C27—C32 | 1.490 (10) |
C3—C4 | 1.499 (11) | C28—C29 | 1.496 (8) |
C3—H3A | 0.9800 | C28—H28A | 0.9300 |
C4—C5 | 1.333 (9) | C29—C36 | 1.516 (8) |
C4—C9 | 1.540 (10) | C29—C30 | 1.558 (8) |
C5—C6 | 1.526 (9) | C29—C34 | 1.586 (9) |
C5—H5A | 0.9300 | C30—C31 | 1.514 (9) |
C6—C13 | 1.525 (8) | C30—C39 | 1.576 (10) |
C6—C7 | 1.552 (8) | C30—H30A | 0.9800 |
C6—C11 | 1.574 (8) | C31—C32 | 1.527 (10) |
C7—C8 | 1.558 (8) | C31—H31A | 0.9700 |
C7—C16 | 1.562 (8) | C31—H31B | 0.9700 |
C7—H7A | 0.9800 | C32—C33 | 1.510 (10) |
C8—C9 | 1.507 (10) | C32—H32A | 0.9800 |
C8—H8A | 0.9700 | C33—C34 | 1.518 (11) |
C8—H8B | 0.9700 | C33—H33A | 0.9700 |
C9—C10 | 1.544 (9) | C33—H33B | 0.9700 |
C9—H9A | 0.9800 | C34—C35 | 1.504 (12) |
C10—C11 | 1.528 (9) | C34—H34A | 0.9800 |
C10—H10A | 0.9700 | C36—C37 | 1.520 (10) |
C10—H10B | 0.9700 | C36—H36A | 0.9700 |
C11—C12 | 1.490 (9) | C36—H36B | 0.9700 |
C11—H11A | 0.9800 | C37—C38 | 1.559 (8) |
C13—C14 | 1.512 (9) | C37—H37A | 0.9700 |
C13—H13A | 0.9700 | C37—H37B | 0.9700 |
C13—H13B | 0.9700 | C38—C39 | 1.532 (8) |
C14—C15 | 1.514 (9) | C38—C40 | 1.560 (9) |
C14—H14A | 0.9700 | C38—H38A | 0.9800 |
C14—H14B | 0.9700 | C39—C44 | 1.522 (10) |
C15—C17 | 1.556 (9) | C39—C43 | 1.561 (10) |
C15—C16 | 1.573 (8) | C40—C46 | 1.520 (9) |
C15—H15A | 0.9800 | C40—C41 | 1.534 (11) |
C16—C20 | 1.526 (9) | C40—C45 | 1.557 (11) |
C16—C21 | 1.527 (9) | C41—C42 | 1.527 (11) |
C17—C23 | 1.527 (10) | C41—H41A | 0.9700 |
C17—C22 | 1.540 (10) | C41—H41B | 0.9700 |
C17—C18 | 1.553 (10) | C42—C43 | 1.532 (12) |
C18—C19 | 1.510 (9) | C42—H42A | 0.9700 |
C18—H18A | 0.9700 | C42—H42B | 0.9700 |
C18—H18B | 0.9700 | C43—H43A | 0.9700 |
C19—C20 | 1.505 (10) | C43—H43B | 0.9700 |
C19—H19A | 0.9700 | C44—H44A | 0.9600 |
C19—H19B | 0.9700 | C44—H44B | 0.9600 |
C20—H20A | 0.9700 | C44—H44C | 0.9600 |
C20—H20B | 0.9700 | C45—H45A | 0.9600 |
C21—H21A | 0.9600 | C45—H45B | 0.9600 |
C21—H21B | 0.9600 | C45—H45C | 0.9600 |
C21—H21C | 0.9600 | O9—C47 | 1.278 (11) |
C22—H22A | 0.9600 | O9—H9B | 0.8499 |
C22—H22B | 0.9600 | C48—C47 | 1.458 (9) |
C22—H22C | 0.9600 | C48—H48A | 0.9600 |
O5—C35 | 1.224 (10) | C48—H48B | 0.9600 |
O6—C35 | 1.252 (10) | C48—H48C | 0.9600 |
O6—H6A | 0.8200 | C47—H47A | 0.9700 |
O7—C46 | 1.234 (9) | C47—H47B | 0.9700 |
C12—O1—H1D | 109.5 | H24B—C24—H24C | 109.5 |
C23—O4—H4A | 109.5 | C26—C25—H25A | 109.5 |
C3—C1—H1A | 109.5 | C26—C25—H25B | 109.5 |
C3—C1—H1B | 109.5 | H25A—C25—H25B | 109.5 |
H1A—C1—H1B | 109.5 | C26—C25—H25C | 109.5 |
C3—C1—H1C | 109.5 | H25A—C25—H25C | 109.5 |
H1A—C1—H1C | 109.5 | H25B—C25—H25C | 109.5 |
H1B—C1—H1C | 109.5 | C24—C26—C27 | 109.7 (7) |
C3—C2—H2A | 109.5 | C24—C26—C25 | 112.6 (8) |
C3—C2—H2B | 109.5 | C27—C26—C25 | 113.2 (6) |
H2A—C2—H2B | 109.5 | C24—C26—H26A | 107.0 |
C3—C2—H2C | 109.5 | C27—C26—H26A | 107.0 |
H2A—C2—H2C | 109.5 | C25—C26—H26A | 107.0 |
H2B—C2—H2C | 109.5 | C28—C27—C32 | 113.3 (6) |
C1—C3—C4 | 115.4 (8) | C28—C27—C26 | 126.8 (7) |
C1—C3—C2 | 112.6 (8) | C32—C27—C26 | 119.8 (6) |
C4—C3—C2 | 108.7 (8) | C27—C28—C29 | 116.5 (6) |
C1—C3—H3A | 106.5 | C27—C28—H28A | 121.8 |
C4—C3—H3A | 106.5 | C29—C28—H28A | 121.8 |
C2—C3—H3A | 106.5 | C28—C29—C36 | 114.1 (5) |
C5—C4—C3 | 127.9 (8) | C28—C29—C30 | 108.7 (5) |
C5—C4—C9 | 112.7 (6) | C36—C29—C30 | 112.6 (5) |
C3—C4—C9 | 119.3 (7) | C28—C29—C34 | 106.0 (5) |
C4—C5—C6 | 115.8 (6) | C36—C29—C34 | 111.2 (5) |
C4—C5—H5A | 122.1 | C30—C29—C34 | 103.3 (5) |
C6—C5—H5A | 122.1 | C31—C30—C29 | 110.0 (5) |
C13—C6—C5 | 114.1 (5) | C31—C30—C39 | 115.0 (5) |
C13—C6—C7 | 112.0 (5) | C29—C30—C39 | 114.4 (5) |
C5—C6—C7 | 109.4 (4) | C31—C30—H30A | 105.5 |
C13—C6—C11 | 110.3 (5) | C29—C30—H30A | 105.5 |
C5—C6—C11 | 106.3 (5) | C39—C30—H30A | 105.5 |
C7—C6—C11 | 104.2 (5) | C30—C31—C32 | 109.8 (6) |
C6—C7—C8 | 109.3 (5) | C30—C31—H31A | 109.7 |
C6—C7—C16 | 115.7 (5) | C32—C31—H31A | 109.7 |
C8—C7—C16 | 114.2 (5) | C30—C31—H31B | 109.7 |
C6—C7—H7A | 105.6 | C32—C31—H31B | 109.7 |
C8—C7—H7A | 105.6 | H31A—C31—H31B | 108.2 |
C16—C7—H7A | 105.6 | C27—C32—C33 | 107.0 (6) |
C9—C8—C7 | 110.3 (5) | C27—C32—C31 | 110.8 (6) |
C9—C8—H8A | 109.6 | C33—C32—C31 | 107.6 (6) |
C7—C8—H8A | 109.6 | C27—C32—H32A | 110.5 |
C9—C8—H8B | 109.6 | C33—C32—H32A | 110.5 |
C7—C8—H8B | 109.6 | C31—C32—H32A | 110.5 |
H8A—C8—H8B | 108.1 | C32—C33—C34 | 109.6 (6) |
C8—C9—C4 | 109.0 (5) | C32—C33—H33A | 109.8 |
C8—C9—C10 | 111.1 (6) | C34—C33—H33A | 109.8 |
C4—C9—C10 | 104.7 (6) | C32—C33—H33B | 109.8 |
C8—C9—H9A | 110.6 | C34—C33—H33B | 109.8 |
C4—C9—H9A | 110.6 | H33A—C33—H33B | 108.2 |
C10—C9—H9A | 110.6 | C35—C34—C33 | 111.5 (8) |
C11—C10—C9 | 109.1 (5) | C35—C34—C29 | 111.1 (8) |
C11—C10—H10A | 109.9 | C33—C34—C29 | 109.9 (5) |
C9—C10—H10A | 109.9 | C35—C34—H34A | 108.1 |
C11—C10—H10B | 109.9 | C33—C34—H34A | 108.1 |
C9—C10—H10B | 109.9 | C29—C34—H34A | 108.1 |
H10A—C10—H10B | 108.3 | O5—C35—O6 | 121.8 (9) |
C12—C11—C10 | 112.1 (6) | O5—C35—C34 | 122.6 (8) |
C12—C11—C6 | 113.7 (5) | O6—C35—C34 | 115.3 (9) |
C10—C11—C6 | 110.4 (5) | C29—C36—C37 | 112.5 (5) |
C12—C11—H11A | 106.7 | C29—C36—H36A | 109.1 |
C10—C11—H11A | 106.7 | C37—C36—H36A | 109.1 |
C6—C11—H11A | 106.7 | C29—C36—H36B | 109.1 |
O2—C12—O1 | 121.5 (6) | C37—C36—H36B | 109.1 |
O2—C12—C11 | 123.6 (7) | H36A—C36—H36B | 107.8 |
O1—C12—C11 | 114.8 (7) | C36—C37—C38 | 110.4 (5) |
C14—C13—C6 | 113.8 (5) | C36—C37—H37A | 109.6 |
C14—C13—H13A | 108.8 | C38—C37—H37A | 109.6 |
C6—C13—H13A | 108.8 | C36—C37—H37B | 109.6 |
C14—C13—H13B | 108.8 | C38—C37—H37B | 109.6 |
C6—C13—H13B | 108.8 | H37A—C37—H37B | 108.1 |
H13A—C13—H13B | 107.7 | C39—C38—C37 | 109.6 (5) |
C13—C14—C15 | 109.5 (5) | C39—C38—C40 | 116.6 (5) |
C13—C14—H14A | 109.8 | C37—C38—C40 | 114.5 (6) |
C15—C14—H14A | 109.8 | C39—C38—H38A | 104.9 |
C13—C14—H14B | 109.8 | C37—C38—H38A | 104.9 |
C15—C14—H14B | 109.8 | C40—C38—H38A | 104.9 |
H14A—C14—H14B | 108.2 | C44—C39—C38 | 114.5 (6) |
C14—C15—C17 | 113.6 (5) | C44—C39—C43 | 109.6 (6) |
C14—C15—C16 | 112.7 (5) | C38—C39—C43 | 106.8 (5) |
C17—C15—C16 | 115.3 (5) | C44—C39—C30 | 111.9 (6) |
C14—C15—H15A | 104.6 | C38—C39—C30 | 106.9 (5) |
C17—C15—H15A | 104.6 | C43—C39—C30 | 106.7 (6) |
C16—C15—H15A | 104.6 | C46—C40—C41 | 109.5 (6) |
C20—C16—C21 | 109.1 (5) | C46—C40—C45 | 106.9 (6) |
C20—C16—C7 | 108.6 (5) | C41—C40—C45 | 110.1 (6) |
C21—C16—C7 | 112.3 (6) | C46—C40—C38 | 107.0 (5) |
C20—C16—C15 | 109.2 (5) | C41—C40—C38 | 108.6 (6) |
C21—C16—C15 | 113.5 (5) | C45—C40—C38 | 114.6 (6) |
C7—C16—C15 | 103.9 (4) | C42—C41—C40 | 113.9 (7) |
C23—C17—C22 | 109.6 (6) | C42—C41—H41A | 108.8 |
C23—C17—C18 | 106.3 (6) | C40—C41—H41A | 108.8 |
C22—C17—C18 | 110.0 (6) | C42—C41—H41B | 108.8 |
C23—C17—C15 | 106.8 (5) | C40—C41—H41B | 108.8 |
C22—C17—C15 | 114.7 (7) | H41A—C41—H41B | 107.7 |
C18—C17—C15 | 109.0 (5) | C41—C42—C43 | 110.0 (6) |
C19—C18—C17 | 112.5 (7) | C41—C42—H42A | 109.7 |
C19—C18—H18A | 109.1 | C43—C42—H42A | 109.7 |
C17—C18—H18A | 109.1 | C41—C42—H42B | 109.7 |
C19—C18—H18B | 109.1 | C43—C42—H42B | 109.7 |
C17—C18—H18B | 109.1 | H42A—C42—H42B | 108.2 |
H18A—C18—H18B | 107.8 | C42—C43—C39 | 114.8 (7) |
C20—C19—C18 | 112.3 (6) | C42—C43—H43A | 108.6 |
C20—C19—H19A | 109.1 | C39—C43—H43A | 108.6 |
C18—C19—H19A | 109.1 | C42—C43—H43B | 108.6 |
C20—C19—H19B | 109.1 | C39—C43—H43B | 108.6 |
C18—C19—H19B | 109.1 | H43A—C43—H43B | 107.5 |
H19A—C19—H19B | 107.9 | C39—C44—H44A | 109.5 |
C19—C20—C16 | 113.6 (5) | C39—C44—H44B | 109.5 |
C19—C20—H20A | 108.8 | H44A—C44—H44B | 109.5 |
C16—C20—H20A | 108.8 | C39—C44—H44C | 109.5 |
C19—C20—H20B | 108.8 | H44A—C44—H44C | 109.5 |
C16—C20—H20B | 108.8 | H44B—C44—H44C | 109.5 |
H20A—C20—H20B | 107.7 | C40—C45—H45A | 109.5 |
C16—C21—H21A | 109.5 | C40—C45—H45B | 109.5 |
C16—C21—H21B | 109.5 | H45A—C45—H45B | 109.5 |
H21A—C21—H21B | 109.5 | C40—C45—H45C | 109.5 |
C16—C21—H21C | 109.5 | H45A—C45—H45C | 109.5 |
H21A—C21—H21C | 109.5 | H45B—C45—H45C | 109.5 |
H21B—C21—H21C | 109.5 | O7—C46—O8 | 120.4 (7) |
C17—C22—H22A | 109.5 | O7—C46—C40 | 121.6 (7) |
C17—C22—H22B | 109.5 | O8—C46—C40 | 118.1 (7) |
H22A—C22—H22B | 109.5 | C47—O9—H9B | 115.5 |
C17—C22—H22C | 109.5 | C47—C48—H48A | 109.5 |
H22A—C22—H22C | 109.5 | C47—C48—H48B | 109.5 |
H22B—C22—H22C | 109.5 | H48A—C48—H48B | 109.5 |
O3—C23—O4 | 120.4 (8) | C47—C48—H48C | 109.5 |
O3—C23—C17 | 122.3 (8) | H48A—C48—H48C | 109.5 |
O4—C23—C17 | 117.2 (6) | H48B—C48—H48C | 109.5 |
C35—O6—H6A | 109.5 | O9—C47—C48 | 127.2 (12) |
C46—O8—H8C | 109.5 | O9—C47—H47A | 105.5 |
C26—C24—H24A | 109.5 | C48—C47—H47A | 105.5 |
C26—C24—H24B | 109.5 | O9—C47—H47B | 105.5 |
H24A—C24—H24B | 109.5 | C48—C47—H47B | 105.5 |
C26—C24—H24C | 109.5 | H47A—C47—H47B | 106.1 |
H24A—C24—H24C | 109.5 | ||
C1—C3—C4—C5 | 12.9 (12) | C24—C26—C27—C28 | −109.9 (9) |
C2—C3—C4—C5 | −114.6 (9) | C25—C26—C27—C28 | 16.8 (11) |
C1—C3—C4—C9 | −164.8 (7) | C24—C26—C27—C32 | 74.9 (9) |
C2—C3—C4—C9 | 67.6 (9) | C25—C26—C27—C32 | −158.4 (7) |
C3—C4—C5—C6 | 179.5 (7) | C32—C27—C28—C29 | 1.1 (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—C36 | 177.9 (6) |
C4—C5—C6—C7 | −53.6 (7) | C27—C28—C29—C30 | −55.4 (7) |
C4—C5—C6—C11 | 58.3 (6) | C27—C28—C29—C34 | 55.1 (7) |
C13—C6—C7—C8 | 179.3 (5) | C28—C29—C30—C31 | 51.4 (7) |
C5—C6—C7—C8 | 51.8 (6) | C36—C29—C30—C31 | 178.9 (6) |
C11—C6—C7—C8 | −61.5 (6) | C34—C29—C30—C31 | −61.0 (7) |
C13—C6—C7—C16 | 48.7 (7) | C28—C29—C30—C39 | −79.9 (6) |
C5—C6—C7—C16 | −78.8 (6) | C36—C29—C30—C39 | 47.6 (7) |
C11—C6—C7—C16 | 168.0 (5) | C34—C29—C30—C39 | 167.8 (5) |
C6—C7—C8—C9 | 1.5 (7) | C29—C30—C31—C32 | 0.6 (8) |
C16—C7—C8—C9 | 132.9 (6) | C39—C30—C31—C32 | 131.5 (6) |
C7—C8—C9—C4 | −56.1 (7) | C28—C27—C32—C33 | −61.3 (8) |
C7—C8—C9—C10 | 58.8 (7) | C26—C27—C32—C33 | 114.6 (7) |
C5—C4—C9—C8 | 59.5 (7) | C28—C27—C32—C31 | 55.7 (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—C10 | 118.6 (7) | C30—C31—C32—C33 | 62.5 (8) |
C8—C9—C10—C11 | −54.0 (8) | C27—C32—C33—C34 | 59.0 (8) |
C4—C9—C10—C11 | 63.5 (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—C35 | 72.8 (7) |
C5—C6—C11—C12 | 78.1 (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—C10 | 66.7 (7) | C30—C29—C34—C33 | 63.2 (7) |
C10—C11—C12—O2 | 69.1 (9) | C33—C34—C35—O5 | 48.2 (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—O1 | 124.9 (7) | C29—C34—C35—O6 | 111.3 (12) |
C5—C6—C13—C14 | 78.2 (7) | C28—C29—C36—C37 | 76.8 (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—C15 | 54.2 (8) | C29—C36—C37—C38 | 56.3 (7) |
C13—C14—C15—C17 | 162.8 (6) | C36—C37—C38—C39 | −64.4 (6) |
C13—C14—C15—C16 | −63.8 (7) | C36—C37—C38—C40 | 162.4 (5) |
C6—C7—C16—C20 | −169.8 (5) | C37—C38—C39—C44 | −63.5 (7) |
C8—C7—C16—C20 | 62.0 (7) | C40—C38—C39—C44 | 68.6 (7) |
C6—C7—C16—C21 | 69.4 (7) | C37—C38—C39—C43 | 175.0 (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—C30 | 61.0 (7) |
C8—C7—C16—C15 | 178.1 (6) | C40—C38—C39—C30 | −166.8 (5) |
C14—C15—C16—C20 | 177.2 (5) | C31—C30—C39—C44 | −56.5 (8) |
C17—C15—C16—C20 | −50.2 (7) | C29—C30—C39—C44 | 72.3 (7) |
C14—C15—C16—C21 | −60.8 (7) | C31—C30—C39—C38 | 177.4 (6) |
C17—C15—C16—C21 | 71.8 (7) | C29—C30—C39—C38 | −53.9 (7) |
C14—C15—C16—C7 | 61.5 (6) | C31—C30—C39—C43 | 63.4 (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—C46 | 171.7 (6) |
C16—C15—C17—C23 | 165.0 (6) | C37—C38—C40—C46 | −58.4 (7) |
C14—C15—C17—C22 | 58.9 (8) | C39—C38—C40—C41 | 53.6 (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—C18 | 50.6 (8) | C37—C38—C40—C45 | 59.9 (7) |
C23—C17—C18—C19 | −167.4 (6) | C46—C40—C41—C42 | −169.3 (8) |
C22—C17—C18—C19 | 74.0 (8) | C45—C40—C41—C42 | 73.5 (9) |
C15—C17—C18—C19 | −52.6 (8) | C38—C40—C41—C42 | −52.7 (9) |
C17—C18—C19—C20 | 56.9 (9) | C40—C41—C42—C43 | 55.0 (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—C19 | 164.5 (6) | C38—C39—C43—C42 | 53.5 (8) |
C15—C16—C20—C19 | 51.9 (7) | C30—C39—C43—C42 | 167.6 (6) |
C22—C17—C23—O3 | 6.9 (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—O3 | 131.7 (8) | C38—C40—C46—O7 | 108.6 (8) |
C22—C17—C23—O4 | −175.7 (8) | C41—C40—C46—O8 | 47.1 (9) |
C18—C17—C23—O4 | 65.5 (9) | C45—C40—C46—O8 | 166.4 (7) |
C15—C17—C23—O4 | −50.9 (9) | C38—C40—C46—O8 | −70.5 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O4 | 0.98 | 2.38 | 2.824 (10) | 107 |
C18—H18A···O4 | 0.97 | 2.55 | 2.939 (8) | 104 |
C33—H33A···O5 | 0.97 | 2.51 | 2.919 (11) | 105 |
C41—H41A···O8 | 0.97 | 2.46 | 2.834 (9) | 103 |
O1—H1D···O7i | 0.82 | 1.80 | 2.610 (7) | 169 |
O4—H4A···O9 | 0.82 | 1.77 | 2.589 (9) | 169 |
O6—H6A···O3ii | 0.82 | 1.86 | 2.611 (9) | 152 |
O8—H8C···O2iii | 0.82 | 1.90 | 2.712 (8) | 171 |
O9—H9B···O5iv | 0.85 | 2.23 | 2.651 (9) | 111 |
C2—H2C···O6v | 0.96 | 2.58 | 3.443 (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. |
Experimental details
Crystal data | |
Chemical formula | C23H34O4·0.5C2H6O |
Mr | 397.54 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 12.682 (3), 12.476 (3), 14.629 (3) |
β (°) | 90.12 (3) |
V (Å3) | 2314.6 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (XCAD4; Harms & Wocadlo, 1995) |
Tmin, Tmax | 0.977, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4620, 4413, 2780 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.194, 1.02 |
No. of reflections | 4413 |
No. of parameters | 480 |
No. of restraints | 24 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.47 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O4 | 0.98 | 2.38 | 2.824 (10) | 107 |
C18—H18A···O4 | 0.97 | 2.55 | 2.939 (8) | 104 |
C33—H33A···O5 | 0.97 | 2.51 | 2.919 (11) | 105 |
C41—H41A···O8 | 0.97 | 2.46 | 2.834 (9) | 103 |
O1—H1D···O7i | 0.82 | 1.80 | 2.610 (7) | 169 |
O4—H4A···O9 | 0.82 | 1.77 | 2.589 (9) | 169 |
O6—H6A···O3ii | 0.82 | 1.86 | 2.611 (9) | 152 |
O8—H8C···O2iii | 0.82 | 1.90 | 2.712 (8) | 171 |
O9—H9B···O5iv | 0.85 | 2.23 | 2.651 (9) | 111 |
C2—H2C···O6v | 0.96 | 2.58 | 3.443 (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. |
Acknowledgements
This work was supported by the `948′ program of the State Forestry Administration under grant No. 2006–4-C03.
References
Aldrich, P. H. (1971). US Patent No. 3 562 243. Google Scholar
Bicu, I. & Munstata, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 5979–5990. Web of Science CrossRef CAS Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).