organic compounds
16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene-5,13,14-tricarboxylic acid dimethylformamide disolvate
aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
*Correspondence e-mail: songzq@hotmail.com
The title compound, C24H34O6·2C3H7NO, which was isolated from fumaric-modified rosin, has four asymmetrically fused six-membered rings and three carboxylic acid substituents. It contains two fused and unbridged cyclohexane rings, which form a trans ring junction with a chair conformation. The includes one fumaropimaric acid and two dimethylformamide molecules. The is stabilized through intermolecular O—H⋯O hydrogen bonds between dimethylformamide and fumaropimaric acid.
Related literature
For various applications of rosin, see: Halbrook & Lawrence (1958). For the separation of the title compound, see: Aldrich (1971); Halbrook & Lawrence (1959); Song et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
https://doi.org/10.1107/S1600536810016594/bq2203sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016594/bq2203Isup2.hkl
The fumaric 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 DMF solution. The crystal data were collected on an Enraf–Nonius CAD-4 diffractometer. Data collection and cell
were performed using Enraf–Nonius CAD-4 Software.All H atoms bonded to the C atoms and O atoms were placed geometrically at the distances of 0.93-0.98 Å and 0.82 Å respectively, and included in the
in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the 2466 Friedel pairs were averaged before the final as the could not be determined unambiguously.As an abundant and renewable material, rosin is mainly known as additives and modifiers for various applications (Halbrook et al., 1958). Fumaric modified rosin is one of modified products of rosin. The title compound has been isolated by solvent extracting (Aldrich et al., 1971) and solvent washing (Halbrook et al., 1959) from fumaric modified rosin, but there are some problems such as complicated operation and large amounts of toxic organic solvents. Therefore, a new method has been used to separate the title compound (Song et al., 2009). In this work, we describe the
of the title compound (I). The molecular structure is shown in Fig. 1 and the crystal packing in Fig. 2.For various applications of rosin, see: Halbrook & Lawrence (1958). For the separation of the title compound, see: Aldrich (1971); Halbrook & Lawrence (1959); Song et al. (2009).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 25% probability level. | |
Fig. 2. A view of the packing of the title compound. |
C24H34O6·2C3H7NO | F(000) = 1224 |
Mr = 564.70 | Dx = 1.172 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P2ac2ab | Cell parameters from 25 reflections |
a = 7.1260 (14) Å | θ = 9–12° |
b = 11.342 (2) Å | µ = 0.08 mm−1 |
c = 39.610 (8) Å | T = 296 K |
V = 3201.4 (11) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 2039 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 25.3°, θmin = 1.0° |
ω/2θ scans | h = −8→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.975, Tmax = 0.992 | l = 0→47 |
5821 measured reflections | 3 standard reflections every 200 reflections |
3355 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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1012P)2] where P = (Fo2 + 2Fc2)/3 |
3355 reflections | (Δ/σ)max < 0.001 |
355 parameters | Δρmax = 0.38 e Å−3 |
1 restraint | Δρmin = −0.37 e Å−3 |
C24H34O6·2C3H7NO | V = 3201.4 (11) Å3 |
Mr = 564.70 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1260 (14) Å | µ = 0.08 mm−1 |
b = 11.342 (2) Å | T = 296 K |
c = 39.610 (8) Å | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 2039 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.056 |
Tmin = 0.975, Tmax = 0.992 | 3 standard reflections every 200 reflections |
5821 measured reflections | intensity decay: 1% |
3355 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 1 restraint |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.38 e Å−3 |
3355 reflections | Δρmin = −0.37 e Å−3 |
355 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 1.0202 (7) | −0.3704 (5) | 0.10397 (15) | 0.0998 (17) | |
O2 | 0.7495 (8) | −0.3154 (4) | 0.08207 (11) | 0.0955 (16) | |
H2A | 0.8053 | −0.3257 | 0.0642 | 0.143* | |
O3 | 0.8126 (5) | 0.3478 (3) | 0.11878 (9) | 0.0512 (9) | |
O4 | 0.7388 (7) | 0.2389 (3) | 0.07384 (9) | 0.0740 (12) | |
H4B | 0.8281 | 0.2735 | 0.0653 | 0.111* | |
O5 | 0.1597 (5) | 0.3461 (4) | 0.15090 (11) | 0.0789 (13) | |
H5A | 0.0552 | 0.3488 | 0.1423 | 0.118* | |
O6 | 0.2060 (6) | 0.2170 (4) | 0.10993 (11) | 0.0724 (12) | |
C1 | 0.6924 (6) | 0.0877 (4) | 0.14378 (11) | 0.0376 (10) | |
C2 | 0.8335 (7) | 0.0249 (4) | 0.12060 (12) | 0.0446 (12) | |
H2B | 0.7764 | 0.0130 | 0.0986 | 0.053* | |
H2C | 0.9425 | 0.0750 | 0.1176 | 0.053* | |
C3 | 0.8951 (7) | −0.0909 (4) | 0.13419 (13) | 0.0462 (12) | |
H3A | 0.9605 | −0.0792 | 0.1554 | 0.055* | |
H3B | 0.9814 | −0.1277 | 0.1185 | 0.055* | |
C4 | 0.7256 (7) | −0.1714 (4) | 0.13976 (12) | 0.0416 (11) | |
H4A | 0.6524 | −0.1637 | 0.1189 | 0.050* | |
C5 | 0.7738 (7) | −0.3056 (4) | 0.14164 (13) | 0.0497 (13) | |
C6 | 0.5870 (8) | −0.3741 (5) | 0.14560 (15) | 0.0602 (15) | |
H6A | 0.5148 | −0.3663 | 0.1249 | 0.072* | |
H6B | 0.6147 | −0.4571 | 0.1488 | 0.072* | |
C7 | 0.4702 (8) | −0.3317 (4) | 0.17471 (16) | 0.0579 (15) | |
H7A | 0.5385 | −0.3438 | 0.1956 | 0.069* | |
H7B | 0.3552 | −0.3773 | 0.1758 | 0.069* | |
C8 | 0.4223 (7) | −0.2011 (4) | 0.17099 (14) | 0.0482 (13) | |
H8A | 0.3506 | −0.1762 | 0.1905 | 0.058* | |
H8B | 0.3434 | −0.1910 | 0.1512 | 0.058* | |
C9 | 0.5950 (7) | −0.1214 (4) | 0.16751 (12) | 0.0405 (11) | |
C10 | 0.5277 (6) | 0.0027 (4) | 0.15488 (11) | 0.0372 (11) | |
H10A | 0.4542 | −0.0122 | 0.1344 | 0.045* | |
C11 | 0.3962 (7) | 0.0695 (4) | 0.17891 (13) | 0.0455 (12) | |
H11A | 0.3951 | 0.0309 | 0.2008 | 0.055* | |
H11B | 0.2694 | 0.0683 | 0.1700 | 0.055* | |
C12 | 0.4619 (7) | 0.1977 (4) | 0.18299 (13) | 0.0445 (12) | |
H12A | 0.3805 | 0.2399 | 0.1989 | 0.053* | |
C13 | 0.4592 (7) | 0.2585 (4) | 0.14818 (12) | 0.0456 (12) | |
H13A | 0.5121 | 0.3377 | 0.1509 | 0.055* | |
C14 | 0.5889 (7) | 0.1887 (4) | 0.12420 (12) | 0.0401 (11) | |
H14A | 0.5091 | 0.1514 | 0.1071 | 0.048* | |
C15 | 0.7754 (7) | 0.1409 (4) | 0.17497 (12) | 0.0396 (11) | |
H15A | 0.9027 | 0.1341 | 0.1797 | 0.048* | |
C16 | 0.6604 (7) | 0.1978 (4) | 0.19544 (12) | 0.0463 (12) | |
C17 | 0.7100 (11) | 0.2617 (6) | 0.22769 (16) | 0.0840 (15) | |
H17A | 0.6214 | 0.2370 | 0.2452 | 0.101* | |
C18 | 0.6869 (14) | 0.3950 (5) | 0.22221 (16) | 0.094 (2) | |
H18A | 0.5622 | 0.4111 | 0.2143 | 0.140* | |
H18B | 0.7764 | 0.4215 | 0.2058 | 0.140* | |
H18C | 0.7075 | 0.4356 | 0.2431 | 0.140* | |
C19 | 0.9084 (10) | 0.2325 (6) | 0.23979 (15) | 0.0840 (15) | |
H19A | 0.9205 | 0.1488 | 0.2427 | 0.126* | |
H19B | 0.9315 | 0.2712 | 0.2609 | 0.126* | |
H19C | 0.9979 | 0.2593 | 0.2234 | 0.126* | |
C20 | 0.9122 (8) | −0.3388 (5) | 0.16926 (16) | 0.0671 (16) | |
H20A | 1.0260 | −0.2946 | 0.1664 | 0.101* | |
H20B | 0.9396 | −0.4216 | 0.1679 | 0.101* | |
H20C | 0.8586 | −0.3214 | 0.1909 | 0.101* | |
C21 | 0.8668 (10) | −0.3355 (5) | 0.10798 (18) | 0.0660 (17) | |
C22 | 0.6957 (8) | −0.1143 (4) | 0.20269 (12) | 0.0499 (13) | |
H22A | 0.7342 | −0.1918 | 0.2095 | 0.075* | |
H22B | 0.6107 | −0.0824 | 0.2191 | 0.075* | |
H22C | 0.8039 | −0.0642 | 0.2009 | 0.075* | |
C23 | 0.7250 (7) | 0.2684 (5) | 0.10591 (12) | 0.0437 (12) | |
C24 | 0.2656 (7) | 0.2712 (4) | 0.13405 (13) | 0.0468 (12) | |
N1 | 0.3130 (14) | 0.9174 (8) | 0.03150 (17) | 0.120 (3) | |
O7 | 0.3811 (15) | 0.8410 (9) | −0.01985 (18) | 0.187 (4) | |
C25 | 0.310 (2) | 0.8890 (15) | 0.0001 (3) | 0.195 (6) | |
H25A | 0.2045 | 0.9239 | −0.0094 | 0.234* | |
C26 | 0.244 (2) | 0.8464 (12) | 0.0571 (4) | 0.206 (6) | |
H26A | 0.2250 | 0.7680 | 0.0486 | 0.309* | |
H26B | 0.1266 | 0.8776 | 0.0650 | 0.309* | |
H26C | 0.3322 | 0.8444 | 0.0754 | 0.309* | |
C27 | 0.343 (3) | 1.0316 (11) | 0.0438 (3) | 0.216 (7) | |
H27A | 0.3759 | 1.0827 | 0.0254 | 0.325* | |
H27B | 0.4431 | 1.0304 | 0.0600 | 0.325* | |
H27C | 0.2305 | 1.0598 | 0.0543 | 0.325* | |
O8 | 0.0025 (8) | 0.3316 (5) | 0.03938 (11) | 0.0894 (15) | |
N2 | 0.2801 (9) | 0.4273 (5) | 0.04118 (14) | 0.0842 (17) | |
C28 | 0.1104 (10) | 0.4000 (5) | 0.05282 (15) | 0.0647 (16) | |
H28A | 0.0714 | 0.4360 | 0.0727 | 0.078* | |
C29 | 0.3562 (15) | 0.3693 (11) | 0.0120 (3) | 0.181 (6) | |
H29A | 0.2611 | 0.3211 | 0.0018 | 0.271* | |
H29B | 0.4600 | 0.3206 | 0.0187 | 0.271* | |
H29C | 0.3983 | 0.4273 | −0.0039 | 0.271* | |
C30 | 0.3990 (13) | 0.5018 (7) | 0.0597 (2) | 0.123 (3) | |
H30A | 0.3318 | 0.5335 | 0.0787 | 0.185* | |
H30B | 0.4412 | 0.5651 | 0.0456 | 0.185* | |
H30C | 0.5052 | 0.4577 | 0.0676 | 0.185* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.075 (3) | 0.099 (4) | 0.126 (4) | 0.022 (3) | 0.030 (3) | −0.025 (3) |
O2 | 0.109 (4) | 0.117 (4) | 0.061 (3) | −0.005 (4) | 0.008 (3) | −0.027 (3) |
O3 | 0.0382 (18) | 0.0476 (19) | 0.068 (2) | −0.0019 (18) | −0.0004 (18) | −0.0041 (18) |
O4 | 0.092 (3) | 0.075 (3) | 0.054 (2) | −0.025 (3) | 0.014 (2) | 0.001 (2) |
O5 | 0.045 (2) | 0.092 (3) | 0.099 (3) | 0.023 (2) | −0.019 (2) | −0.032 (3) |
O6 | 0.048 (2) | 0.083 (3) | 0.086 (3) | 0.005 (2) | −0.014 (2) | −0.025 (3) |
C1 | 0.031 (2) | 0.041 (2) | 0.042 (2) | −0.003 (2) | 0.006 (2) | 0.001 (2) |
C2 | 0.044 (3) | 0.045 (3) | 0.045 (3) | −0.002 (2) | 0.012 (2) | −0.007 (2) |
C3 | 0.038 (2) | 0.047 (3) | 0.054 (3) | −0.005 (2) | 0.006 (2) | −0.013 (2) |
C4 | 0.039 (2) | 0.041 (2) | 0.045 (3) | 0.004 (2) | −0.001 (2) | −0.004 (2) |
C5 | 0.046 (3) | 0.047 (3) | 0.057 (3) | 0.005 (3) | −0.002 (3) | −0.007 (2) |
C6 | 0.059 (3) | 0.042 (3) | 0.080 (4) | 0.002 (3) | −0.003 (3) | −0.011 (3) |
C7 | 0.049 (3) | 0.043 (3) | 0.081 (4) | −0.013 (3) | 0.004 (3) | 0.010 (3) |
C8 | 0.039 (3) | 0.041 (3) | 0.065 (3) | −0.001 (2) | −0.002 (3) | −0.004 (2) |
C9 | 0.032 (2) | 0.042 (2) | 0.047 (3) | −0.001 (2) | 0.003 (2) | −0.001 (2) |
C10 | 0.035 (2) | 0.036 (2) | 0.041 (3) | −0.002 (2) | −0.001 (2) | 0.002 (2) |
C11 | 0.034 (2) | 0.048 (3) | 0.054 (3) | 0.004 (2) | 0.006 (2) | 0.003 (2) |
C12 | 0.040 (3) | 0.047 (3) | 0.046 (3) | 0.008 (2) | 0.009 (2) | 0.002 (2) |
C13 | 0.040 (3) | 0.037 (2) | 0.060 (3) | 0.001 (2) | −0.003 (3) | −0.004 (2) |
C14 | 0.037 (2) | 0.041 (2) | 0.042 (3) | −0.003 (2) | −0.003 (2) | −0.002 (2) |
C15 | 0.033 (2) | 0.038 (2) | 0.048 (3) | 0.005 (2) | −0.006 (2) | 0.001 (2) |
C16 | 0.051 (3) | 0.042 (3) | 0.046 (3) | −0.001 (3) | −0.009 (2) | 0.003 (2) |
C17 | 0.093 (3) | 0.094 (3) | 0.065 (3) | 0.007 (3) | −0.025 (3) | −0.023 (3) |
C18 | 0.145 (7) | 0.065 (4) | 0.071 (4) | −0.015 (5) | 0.018 (5) | −0.027 (3) |
C19 | 0.093 (3) | 0.094 (3) | 0.065 (3) | 0.007 (3) | −0.025 (3) | −0.023 (3) |
C20 | 0.056 (3) | 0.059 (4) | 0.085 (4) | 0.014 (3) | −0.014 (3) | −0.001 (3) |
C21 | 0.073 (4) | 0.050 (3) | 0.074 (4) | −0.002 (3) | 0.009 (4) | −0.015 (3) |
C22 | 0.049 (3) | 0.051 (3) | 0.050 (3) | 0.004 (3) | −0.008 (3) | −0.001 (2) |
C23 | 0.039 (3) | 0.051 (3) | 0.042 (3) | 0.008 (3) | 0.004 (2) | 0.008 (2) |
C24 | 0.041 (3) | 0.043 (3) | 0.056 (3) | −0.002 (3) | −0.003 (3) | 0.002 (2) |
N1 | 0.162 (7) | 0.141 (6) | 0.057 (4) | −0.015 (6) | −0.022 (5) | −0.017 (4) |
O7 | 0.226 (10) | 0.244 (9) | 0.091 (5) | 0.046 (9) | −0.020 (6) | −0.070 (5) |
C25 | 0.176 (13) | 0.296 (19) | 0.114 (9) | 0.005 (14) | −0.001 (10) | −0.042 (12) |
C26 | 0.197 (14) | 0.228 (15) | 0.192 (13) | −0.035 (14) | −0.023 (13) | 0.053 (11) |
C27 | 0.31 (2) | 0.160 (11) | 0.183 (12) | −0.016 (15) | −0.052 (14) | −0.039 (9) |
O8 | 0.101 (4) | 0.105 (4) | 0.061 (3) | −0.035 (3) | 0.016 (3) | −0.008 (2) |
N2 | 0.085 (4) | 0.087 (4) | 0.081 (4) | −0.016 (4) | 0.010 (4) | −0.025 (3) |
C28 | 0.075 (4) | 0.063 (4) | 0.056 (4) | −0.002 (4) | 0.004 (3) | −0.004 (3) |
C29 | 0.144 (10) | 0.231 (12) | 0.168 (10) | −0.063 (10) | 0.086 (8) | −0.114 (9) |
C30 | 0.104 (6) | 0.121 (6) | 0.143 (7) | −0.025 (6) | −0.018 (6) | −0.043 (6) |
O1—C21 | 1.174 (7) | C13—C14 | 1.543 (7) |
O2—C21 | 1.343 (8) | C13—H13A | 0.9800 |
O2—H2A | 0.8200 | C14—C23 | 1.511 (7) |
O3—C23 | 1.209 (6) | C14—H14A | 0.9800 |
O4—C23 | 1.317 (6) | C15—C16 | 1.321 (7) |
O4—H4B | 0.8200 | C15—H15A | 0.9300 |
O5—C24 | 1.317 (6) | C16—C17 | 1.511 (7) |
O5—H5A | 0.8200 | C17—C19 | 1.529 (9) |
O6—C24 | 1.213 (6) | C17—C18 | 1.536 (9) |
C1—C15 | 1.496 (6) | C17—H17A | 0.9800 |
C1—C2 | 1.537 (6) | C18—H18A | 0.9600 |
C1—C14 | 1.568 (6) | C18—H18B | 0.9600 |
C1—C10 | 1.581 (6) | C18—H18C | 0.9600 |
C2—C3 | 1.486 (7) | C19—H19A | 0.9600 |
C2—H2B | 0.9700 | C19—H19B | 0.9600 |
C2—H2C | 0.9700 | C19—H19C | 0.9600 |
C3—C4 | 1.531 (6) | C20—H20A | 0.9600 |
C3—H3A | 0.9700 | C20—H20B | 0.9600 |
C3—H3B | 0.9700 | C20—H20C | 0.9600 |
C4—C9 | 1.547 (6) | C22—H22A | 0.9600 |
C4—C5 | 1.562 (6) | C22—H22B | 0.9600 |
C4—H4A | 0.9800 | C22—H22C | 0.9600 |
C5—C20 | 1.520 (7) | N1—C25 | 1.284 (13) |
C5—C21 | 1.527 (8) | N1—C26 | 1.385 (13) |
C5—C6 | 1.549 (7) | N1—C27 | 1.399 (12) |
C6—C7 | 1.501 (8) | O7—C25 | 1.085 (14) |
C6—H6A | 0.9700 | C25—H25A | 0.9300 |
C6—H6B | 0.9700 | C26—H26A | 0.9600 |
C7—C8 | 1.527 (7) | C26—H26B | 0.9600 |
C7—H7A | 0.9700 | C26—H26C | 0.9600 |
C7—H7B | 0.9700 | C27—H27A | 0.9600 |
C8—C9 | 1.533 (6) | C27—H27B | 0.9600 |
C8—H8A | 0.9700 | C27—H27C | 0.9600 |
C8—H8B | 0.9700 | O8—C28 | 1.215 (7) |
C9—C22 | 1.569 (6) | N2—C28 | 1.331 (9) |
C9—C10 | 1.570 (6) | N2—C30 | 1.404 (9) |
C10—C11 | 1.535 (6) | N2—C29 | 1.436 (9) |
C10—H10A | 0.9800 | C28—H28A | 0.9300 |
C11—C12 | 1.537 (7) | C29—H29A | 0.9600 |
C11—H11A | 0.9700 | C29—H29B | 0.9600 |
C11—H11B | 0.9700 | C29—H29C | 0.9600 |
C12—C16 | 1.498 (7) | C30—H30A | 0.9600 |
C12—C13 | 1.542 (7) | C30—H30B | 0.9600 |
C12—H12A | 0.9800 | C30—H30C | 0.9600 |
C13—C24 | 1.496 (7) | ||
C21—O2—H2A | 109.5 | C23—C14—H14A | 107.4 |
C23—O4—H4B | 109.5 | C13—C14—H14A | 107.4 |
C24—O5—H5A | 109.5 | C1—C14—H14A | 107.4 |
C15—C1—C2 | 114.9 (4) | C16—C15—C1 | 117.3 (4) |
C15—C1—C14 | 107.4 (3) | C16—C15—H15A | 121.4 |
C2—C1—C14 | 110.6 (4) | C1—C15—H15A | 121.4 |
C15—C1—C10 | 108.0 (4) | C15—C16—C12 | 112.5 (4) |
C2—C1—C10 | 111.7 (4) | C15—C16—C17 | 127.5 (5) |
C14—C1—C10 | 103.5 (4) | C12—C16—C17 | 120.0 (5) |
C3—C2—C1 | 112.7 (4) | C16—C17—C19 | 112.2 (6) |
C3—C2—H2B | 109.0 | C16—C17—C18 | 109.1 (5) |
C1—C2—H2B | 109.0 | C19—C17—C18 | 110.9 (7) |
C3—C2—H2C | 109.0 | C16—C17—H17A | 108.2 |
C1—C2—H2C | 109.0 | C19—C17—H17A | 108.2 |
H2B—C2—H2C | 107.8 | C18—C17—H17A | 108.2 |
C2—C3—C4 | 110.3 (4) | C17—C18—H18A | 109.5 |
C2—C3—H3A | 109.6 | C17—C18—H18B | 109.5 |
C4—C3—H3A | 109.6 | H18A—C18—H18B | 109.5 |
C2—C3—H3B | 109.6 | C17—C18—H18C | 109.5 |
C4—C3—H3B | 109.6 | H18A—C18—H18C | 109.5 |
H3A—C3—H3B | 108.1 | H18B—C18—H18C | 109.5 |
C3—C4—C9 | 111.0 (4) | C17—C19—H19A | 109.5 |
C3—C4—C5 | 114.5 (4) | C17—C19—H19B | 109.5 |
C9—C4—C5 | 117.1 (4) | H19A—C19—H19B | 109.5 |
C3—C4—H4A | 104.2 | C17—C19—H19C | 109.5 |
C9—C4—H4A | 104.2 | H19A—C19—H19C | 109.5 |
C5—C4—H4A | 104.2 | H19B—C19—H19C | 109.5 |
C20—C5—C21 | 107.0 (5) | C5—C20—H20A | 109.5 |
C20—C5—C6 | 111.1 (5) | C5—C20—H20B | 109.5 |
C21—C5—C6 | 110.5 (4) | H20A—C20—H20B | 109.5 |
C20—C5—C4 | 114.8 (4) | C5—C20—H20C | 109.5 |
C21—C5—C4 | 105.7 (4) | H20A—C20—H20C | 109.5 |
C6—C5—C4 | 107.7 (4) | H20B—C20—H20C | 109.5 |
C7—C6—C5 | 113.2 (4) | O1—C21—O2 | 122.3 (7) |
C7—C6—H6A | 108.9 | O1—C21—C5 | 126.7 (7) |
C5—C6—H6A | 108.9 | O2—C21—C5 | 111.1 (5) |
C7—C6—H6B | 108.9 | C9—C22—H22A | 109.5 |
C5—C6—H6B | 108.9 | C9—C22—H22B | 109.5 |
H6A—C6—H6B | 107.8 | H22A—C22—H22B | 109.5 |
C6—C7—C8 | 111.1 (5) | C9—C22—H22C | 109.5 |
C6—C7—H7A | 109.4 | H22A—C22—H22C | 109.5 |
C8—C7—H7A | 109.4 | H22B—C22—H22C | 109.5 |
C6—C7—H7B | 109.4 | O3—C23—O4 | 123.9 (5) |
C8—C7—H7B | 109.4 | O3—C23—C14 | 125.1 (4) |
H7A—C7—H7B | 108.0 | O4—C23—C14 | 111.0 (5) |
C7—C8—C9 | 113.6 (4) | O6—C24—O5 | 121.7 (5) |
C7—C8—H8A | 108.8 | O6—C24—C13 | 124.7 (5) |
C9—C8—H8A | 108.8 | O5—C24—C13 | 113.6 (5) |
C7—C8—H8B | 108.8 | C25—N1—C26 | 123.9 (12) |
C9—C8—H8B | 108.8 | C25—N1—C27 | 124.7 (12) |
H8A—C8—H8B | 107.7 | C26—N1—C27 | 109.8 (9) |
C8—C9—C4 | 109.3 (4) | O7—C25—N1 | 145.5 (18) |
C8—C9—C22 | 108.5 (4) | O7—C25—H25A | 107.2 |
C4—C9—C22 | 112.0 (4) | N1—C25—H25A | 107.2 |
C8—C9—C10 | 108.2 (4) | N1—C26—H26A | 109.5 |
C4—C9—C10 | 106.6 (4) | N1—C26—H26B | 109.5 |
C22—C9—C10 | 112.1 (4) | H26A—C26—H26B | 109.5 |
C11—C10—C9 | 115.6 (4) | N1—C26—H26C | 109.5 |
C11—C10—C1 | 108.9 (3) | H26A—C26—H26C | 109.5 |
C9—C10—C1 | 114.1 (4) | H26B—C26—H26C | 109.5 |
C11—C10—H10A | 105.8 | N1—C27—H27A | 109.5 |
C9—C10—H10A | 105.8 | N1—C27—H27B | 109.5 |
C1—C10—H10A | 105.8 | H27A—C27—H27B | 109.5 |
C10—C11—C12 | 110.2 (4) | N1—C27—H27C | 109.5 |
C10—C11—H11A | 109.6 | H27A—C27—H27C | 109.5 |
C12—C11—H11A | 109.6 | H27B—C27—H27C | 109.5 |
C10—C11—H11B | 109.6 | C28—N2—C30 | 120.5 (7) |
C12—C11—H11B | 109.6 | C28—N2—C29 | 121.0 (7) |
H11A—C11—H11B | 108.1 | C30—N2—C29 | 118.0 (7) |
C16—C12—C11 | 108.8 (4) | O8—C28—N2 | 124.9 (6) |
C16—C12—C13 | 107.8 (4) | O8—C28—H28A | 117.6 |
C11—C12—C13 | 109.0 (4) | N2—C28—H28A | 117.6 |
C16—C12—H12A | 110.4 | N2—C29—H29A | 109.5 |
C11—C12—H12A | 110.4 | N2—C29—H29B | 109.5 |
C13—C12—H12A | 110.4 | H29A—C29—H29B | 109.5 |
C24—C13—C12 | 112.9 (4) | N2—C29—H29C | 109.5 |
C24—C13—C14 | 111.8 (4) | H29A—C29—H29C | 109.5 |
C12—C13—C14 | 108.3 (4) | H29B—C29—H29C | 109.5 |
C24—C13—H13A | 107.9 | N2—C30—H30A | 109.5 |
C12—C13—H13A | 107.9 | N2—C30—H30B | 109.5 |
C14—C13—H13A | 107.9 | H30A—C30—H30B | 109.5 |
C23—C14—C13 | 111.9 (4) | N2—C30—H30C | 109.5 |
C23—C14—C1 | 111.8 (4) | H30A—C30—H30C | 109.5 |
C13—C14—C1 | 110.6 (4) | H30B—C30—H30C | 109.5 |
C15—C1—C2—C3 | 74.5 (5) | C16—C12—C13—C14 | 59.5 (5) |
C14—C1—C2—C3 | −163.6 (4) | C11—C12—C13—C14 | −58.5 (5) |
C10—C1—C2—C3 | −49.0 (5) | C24—C13—C14—C23 | 104.6 (5) |
C1—C2—C3—C4 | 57.9 (5) | C12—C13—C14—C23 | −130.4 (4) |
C2—C3—C4—C9 | −65.1 (5) | C24—C13—C14—C1 | −130.0 (4) |
C2—C3—C4—C5 | 159.6 (4) | C12—C13—C14—C1 | −5.0 (5) |
C3—C4—C5—C20 | 58.3 (6) | C15—C1—C14—C23 | 76.2 (5) |
C9—C4—C5—C20 | −74.1 (6) | C2—C1—C14—C23 | −49.9 (5) |
C3—C4—C5—C21 | −59.3 (6) | C10—C1—C14—C23 | −169.6 (4) |
C9—C4—C5—C21 | 168.3 (4) | C15—C1—C14—C13 | −49.2 (5) |
C3—C4—C5—C6 | −177.4 (4) | C2—C1—C14—C13 | −175.3 (4) |
C9—C4—C5—C6 | 50.2 (6) | C10—C1—C14—C13 | 65.0 (4) |
C20—C5—C6—C7 | 72.7 (6) | C2—C1—C15—C16 | 178.8 (4) |
C21—C5—C6—C7 | −168.8 (5) | C14—C1—C15—C16 | 55.3 (5) |
C4—C5—C6—C7 | −53.8 (6) | C10—C1—C15—C16 | −55.8 (5) |
C5—C6—C7—C8 | 58.7 (6) | C1—C15—C16—C12 | 0.1 (6) |
C6—C7—C8—C9 | −56.7 (6) | C1—C15—C16—C17 | −178.0 (5) |
C7—C8—C9—C4 | 50.2 (6) | C11—C12—C16—C15 | 58.1 (5) |
C7—C8—C9—C22 | −72.2 (5) | C13—C12—C16—C15 | −59.9 (6) |
C7—C8—C9—C10 | 165.9 (4) | C11—C12—C16—C17 | −123.6 (5) |
C3—C4—C9—C8 | 177.1 (4) | C13—C12—C16—C17 | 118.4 (5) |
C5—C4—C9—C8 | −48.9 (5) | C15—C16—C17—C19 | −12.9 (9) |
C3—C4—C9—C22 | −62.6 (5) | C12—C16—C17—C19 | 169.1 (6) |
C5—C4—C9—C22 | 71.4 (5) | C15—C16—C17—C18 | 110.4 (7) |
C3—C4—C9—C10 | 60.3 (5) | C12—C16—C17—C18 | −67.6 (8) |
C5—C4—C9—C10 | −165.6 (4) | C20—C5—C21—O1 | −4.4 (8) |
C8—C9—C10—C11 | 63.0 (5) | C6—C5—C21—O1 | −125.5 (7) |
C4—C9—C10—C11 | −179.6 (4) | C4—C5—C21—O1 | 118.3 (7) |
C22—C9—C10—C11 | −56.7 (5) | C20—C5—C21—O2 | 176.4 (5) |
C8—C9—C10—C1 | −169.6 (4) | C6—C5—C21—O2 | 55.3 (6) |
C4—C9—C10—C1 | −52.1 (5) | C4—C5—C21—O2 | −60.9 (6) |
C22—C9—C10—C1 | 70.8 (5) | C13—C14—C23—O3 | 43.9 (6) |
C15—C1—C10—C11 | 50.7 (5) | C1—C14—C23—O3 | −80.8 (6) |
C2—C1—C10—C11 | 178.0 (4) | C13—C14—C23—O4 | −137.1 (4) |
C14—C1—C10—C11 | −63.1 (5) | C1—C14—C23—O4 | 98.2 (5) |
C15—C1—C10—C9 | −80.1 (5) | C12—C13—C24—O6 | −110.1 (6) |
C2—C1—C10—C9 | 47.2 (5) | C14—C13—C24—O6 | 12.2 (7) |
C14—C1—C10—C9 | 166.1 (4) | C12—C13—C24—O5 | 68.2 (6) |
C9—C10—C11—C12 | 132.6 (4) | C14—C13—C24—O5 | −169.5 (4) |
C1—C10—C11—C12 | 2.6 (5) | C26—N1—C25—O7 | −84 (3) |
C10—C11—C12—C16 | −57.0 (5) | C27—N1—C25—O7 | 112 (3) |
C10—C11—C12—C13 | 60.4 (5) | C30—N2—C28—O8 | −175.9 (7) |
C16—C12—C13—C24 | −176.1 (4) | C29—N2—C28—O8 | −4.6 (12) |
C11—C12—C13—C24 | 65.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O7i | 0.82 | 1.85 | 2.653 (8) | 168 |
O4—H4B···O8ii | 0.82 | 1.74 | 2.549 (6) | 168 |
O5—H5A···O3iii | 0.82 | 1.96 | 2.781 (5) | 176 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C24H34O6·2C3H7NO |
Mr | 564.70 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 7.1260 (14), 11.342 (2), 39.610 (8) |
V (Å3) | 3201.4 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.975, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5821, 3355, 2039 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.182, 0.99 |
No. of reflections | 3355 |
No. of parameters | 355 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.37 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O7i | 0.82 | 1.85 | 2.653 (8) | 167.5 |
O4—H4B···O8ii | 0.82 | 1.74 | 2.549 (6) | 167.7 |
O5—H5A···O3iii | 0.82 | 1.96 | 2.781 (5) | 175.6 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z; (iii) x−1, y, z. |
Acknowledgements
This work was supported by the `948' program granted by the State Forestry Administration under grant No. 2006-4-C03.
References
Aldrich, P. H. (1971). US Patent No. 3 562 243. Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Halbrook, N. J. & Lawrence, R. V. (1958). J. Am. Chem. Soc. 80, 368–370. CrossRef CAS Web of Science Google Scholar
Halbrook, N. J. & Lawrence, R. V. (1959). US Patent No. 2 889 362. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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Song, Z. Q., Xu, X., Shang, S. B., Wang, H. X. & Rao, X. P (2009). Chinese Patent CN 101591239. 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.
As an abundant and renewable material, rosin is mainly known as additives and modifiers for various applications (Halbrook et al., 1958). Fumaric modified rosin is one of modified products of rosin. The title compound has been isolated by solvent extracting (Aldrich et al., 1971) and solvent washing (Halbrook et al., 1959) from fumaric modified rosin, but there are some problems such as complicated operation and large amounts of toxic organic solvents. Therefore, a new method has been used to separate the title compound (Song et al., 2009). In this work, we describe the crystal structure of the title compound (I). The molecular structure is shown in Fig. 1 and the crystal packing in Fig. 2.