Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035155/lh2461sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035155/lh2461Isup2.hkl |
CCDC reference: 659099
Seeds of C. siamensis (600 g) were extracted with hexane-acetone (1:1 V/V) over the period of 3 days at room temperature. The mixture was filtered and concentrated under reduced pressure to provide the crude extract (62.21 g). This crude extract was subjected to quick column chromatography (QCC) over silica gel and eluted with a gradient of EtOAc-hexane to afford 13 factions (A1—A13). Fraction A8 (1.01 g) was subjected to repeated column chromatography using 25% EtOAc-hexane to give compound (I) (17.2 mg). Colorless plate shaped single crystals of the title compound were recrystallization from EtOAc-hexane (1:2 V/V) solution, Mp 493 K decomposition.
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with the C—H distances in the range 0.93–0.98 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. A total of 2006 Friedel pairs were merged before final refinement as there is no large anomalous dispersion for the determination of the absolute configuration. The absolute configuration of the title compound was selected arbitrarily.
Meliaceae plants are known to be rich sources of limonoids. Some of these limonoids posses significant pharmocological effects such as antimalarial (Bickii et al., 2000; Saewan et al., 2006), cytotoxic (Takeya et al., 1996), antiprotozoal (Khalid et al., 1998) and antifeedant activities (Koul et al., 2003; Nihei et al., 2002). Chisocheton siamensis or "Ta Sua" in a local Thai name, is one of the Meliaceae plants, which is found in the northern part of Thailand. As part of our study of chemical constituents and bioactive compounds from C. siamensis, we herein report the crystal structure of the title compound which was isolated for the first time from the seed of C. siamensis collected from Chiang Mai province in the northern part of Thailand. The title compound was found to posses anti-allergic (Penido, Costa et al., (2006) and antiinflammatory (Penido, Conte et al., (2006) activities.
The title molecule (Fig. 1) contains a four trans-fused rings, the cyclohexene ring adopts a screw boat conformation with the puckering parameters (Cremer & Pople, 1975) Q = 0.552 (4) Å, θ = 70.6 (5)° and φ = 276.7 (5)°, the two cyclohexane rings are in standard chair and boat conformations and the cyclopentane adopts an envelope conformation, with atom C17 displaced from the C13/C14/C15/C16 plane by 0.238 (4) Å. The oxirane moiety (C14/C15/O3) makes the dihedral angle of 78.0 (4)° with the mean plane of C13/C14/C15/C16. The furan ring is planar and attached to the cyclopentane ring at atom C17, the dihedral angle between the furan ring and the C13/C14/C15/C16 mean plane is 56.7 (3)°. The two acetate groups are planar and in cis-configuration with respect to the C6—C7 bond, the dihedral angle between the mean plane of these two acetate moieties is 44.4 (3)°(Fig.1). The bond lengths and angles are within normal ranges (Allen et al., 1987). In the structure, the weak C5—H5A···O7, C7—H7A···O8 and C9—H9A···O7 intramolecular interactions generate S(5) ring motifs, the C28—H28D···O5 and C29—H28D···O5 generate S(6) ring motifs (Bernstein et al.,1995), whereas the intermolecular C27—H27A···O2(-x, -y, z) interaction connects the molecules into dimers (Fig. 2).
For hydrogen-bond motifs, see Bernstein et al. (1995). For values of bond lengths and angles, see Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For limonoid compounds and activities, see for example, Bickii et al. (2000); Khalid et al. (1998); Koul et al. (2003); Nihei et al. (2002); Penido, Conte et al. (2006); Penido, Costa et al. (2006); Saewan et al. (2006); Takeya et al. (1996).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C30H36O8 | Dx = 1.299 Mg m−3 |
Mr = 524.59 | Melting point: 493 K, decomposition K |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 2724 reflections |
a = 12.189 (3) Å | θ = 1.8–25.0° |
b = 29.983 (5) Å | µ = 0.09 mm−1 |
c = 7.3372 (11) Å | T = 297 K |
V = 2681.5 (9) Å3 | Plate, colourless |
Z = 4 | 0.39 × 0.10 × 0.07 mm |
F(000) = 1120 |
Bruker SMART APEXII CCD area-detector diffractometer | 2724 independent reflections |
Radiation source: fine-focus sealed tube | 1782 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −14→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −35→32 |
Tmin = 0.965, Tmax = 0.994 | l = −8→8 |
20575 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.359P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2724 reflections | Δρmax = 0.16 e Å−3 |
351 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0128 (16) |
C30H36O8 | V = 2681.5 (9) Å3 |
Mr = 524.59 | Z = 4 |
Orthorhombic, P21212 | Mo Kα radiation |
a = 12.189 (3) Å | µ = 0.09 mm−1 |
b = 29.983 (5) Å | T = 297 K |
c = 7.3372 (11) Å | 0.39 × 0.10 × 0.07 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2724 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1782 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.994 | Rint = 0.100 |
20575 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.16 e Å−3 |
2724 reflections | Δρmin = −0.14 e Å−3 |
351 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 | 0.7277 (3) | 0.20923 (12) | 0.2888 (6) | 0.0843 (11) | |
O2 | −0.0801 (3) | 0.04653 (14) | 0.1717 (6) | 0.0975 (13) | |
O3 | −0.1807 (4) | 0.1049 (2) | 0.7665 (6) | 0.1104 (15) | |
O4 | 0.0294 (3) | 0.14448 (14) | 0.0196 (5) | 0.0819 (11) | |
O5 | 0.4887 (2) | 0.10007 (9) | −0.1064 (4) | 0.0495 (7) | |
O6 | 0.4156 (3) | 0.11150 (12) | −0.3842 (5) | 0.0733 (10) | |
O7 | 0.3165 (2) | 0.08053 (8) | 0.1306 (4) | 0.0486 (7) | |
O8 | 0.2993 (4) | 0.02858 (12) | −0.0864 (6) | 0.1002 (13) | |
C1 | 0.4516 (4) | 0.20161 (14) | 0.4065 (6) | 0.0577 (12) | |
H1A | 0.4052 | 0.2069 | 0.5048 | 0.069* | |
C2 | 0.5586 (4) | 0.20273 (15) | 0.4328 (7) | 0.0631 (13) | |
H2A | 0.5858 | 0.2091 | 0.5484 | 0.076* | |
C3 | 0.6344 (4) | 0.19424 (15) | 0.2850 (7) | 0.0586 (13) | |
C4 | 0.5981 (3) | 0.16439 (13) | 0.1284 (6) | 0.0479 (11) | |
C5 | 0.4730 (3) | 0.15332 (13) | 0.1422 (5) | 0.0412 (9) | |
H5A | 0.4674 | 0.1289 | 0.2305 | 0.049* | |
C6 | 0.4207 (3) | 0.13562 (13) | −0.0334 (6) | 0.0425 (10) | |
H6A | 0.4157 | 0.1598 | −0.1228 | 0.051* | |
C7 | 0.3065 (3) | 0.11623 (13) | 0.0000 (6) | 0.0454 (10) | |
H7A | 0.2764 | 0.1047 | −0.1145 | 0.054* | |
C8 | 0.2303 (3) | 0.15175 (13) | 0.0774 (6) | 0.0453 (11) | |
C9 | 0.2831 (3) | 0.17297 (13) | 0.2505 (6) | 0.0488 (11) | |
H9A | 0.2926 | 0.1480 | 0.3353 | 0.059* | |
C10 | 0.4017 (3) | 0.19194 (12) | 0.2214 (6) | 0.0438 (10) | |
C11 | 0.2019 (4) | 0.20428 (15) | 0.3457 (7) | 0.0661 (13) | |
H11A | 0.2360 | 0.2158 | 0.4555 | 0.079* | |
H11B | 0.1872 | 0.2294 | 0.2661 | 0.079* | |
C12 | 0.0927 (4) | 0.18242 (15) | 0.3972 (7) | 0.0664 (13) | |
H12A | 0.0838 | 0.1841 | 0.5284 | 0.080* | |
H12B | 0.0335 | 0.1994 | 0.3423 | 0.080* | |
C13 | 0.0817 (3) | 0.13369 (15) | 0.3387 (6) | 0.0509 (11) | |
C14 | 0.1178 (3) | 0.13163 (15) | 0.1389 (6) | 0.0525 (11) | |
C15 | 0.0509 (4) | 0.0982 (2) | 0.0452 (8) | 0.0765 (16) | |
H15A | 0.0804 | 0.0794 | −0.0523 | 0.092* | |
C16 | −0.0310 (4) | 0.08116 (19) | 0.1807 (7) | 0.0706 (14) | |
C17 | −0.0398 (3) | 0.11626 (16) | 0.3268 (6) | 0.0574 (12) | |
H17A | −0.0844 | 0.1406 | 0.2773 | 0.069* | |
C18 | 0.1430 (4) | 0.10127 (17) | 0.4612 (7) | 0.0669 (14) | |
H18A | 0.2196 | 0.1087 | 0.4621 | 0.100* | |
H18B | 0.1338 | 0.0715 | 0.4160 | 0.100* | |
H18C | 0.1144 | 0.1031 | 0.5828 | 0.100* | |
C19 | 0.4068 (4) | 0.23638 (13) | 0.1148 (7) | 0.0655 (14) | |
H19A | 0.4793 | 0.2487 | 0.1237 | 0.098* | |
H19B | 0.3549 | 0.2570 | 0.1655 | 0.098* | |
H19C | 0.3893 | 0.2310 | −0.0109 | 0.098* | |
C20 | −0.0921 (4) | 0.10193 (18) | 0.5024 (7) | 0.0623 (13) | |
C21 | −0.0981 (4) | 0.0586 (2) | 0.5791 (8) | 0.0827 (16) | |
H21A | −0.0702 | 0.0326 | 0.5279 | 0.099* | |
C22 | −0.1507 (5) | 0.0618 (3) | 0.7375 (10) | 0.100 (2) | |
H22A | −0.1647 | 0.0382 | 0.8163 | 0.119* | |
C23 | −0.1448 (5) | 0.1283 (2) | 0.6193 (9) | 0.0912 (18) | |
H23A | −0.1557 | 0.1587 | 0.6025 | 0.109* | |
C24 | 0.4794 (4) | 0.09201 (16) | −0.2885 (7) | 0.0582 (12) | |
C25 | 0.5585 (4) | 0.05754 (19) | −0.3489 (8) | 0.0854 (17) | |
H25A | 0.5334 | 0.0444 | −0.4606 | 0.128* | |
H25B | 0.5645 | 0.0349 | −0.2570 | 0.128* | |
H25C | 0.6290 | 0.0710 | −0.3680 | 0.128* | |
C26 | 0.3122 (4) | 0.03785 (17) | 0.0706 (9) | 0.0687 (14) | |
C27 | 0.3269 (5) | 0.00620 (17) | 0.2258 (8) | 0.0891 (17) | |
H27A | 0.2609 | −0.0108 | 0.2424 | 0.134* | |
H27B | 0.3425 | 0.0227 | 0.3350 | 0.134* | |
H27C | 0.3868 | −0.0136 | 0.1999 | 0.134* | |
C28 | 0.6329 (4) | 0.18517 (16) | −0.0557 (7) | 0.0642 (14) | |
H28A | 0.7092 | 0.1930 | −0.0510 | 0.096* | |
H28B | 0.5900 | 0.2114 | −0.0785 | 0.096* | |
H28D | 0.6211 | 0.1640 | −0.1517 | 0.096* | |
C29 | 0.6656 (3) | 0.12137 (14) | 0.1587 (7) | 0.0639 (14) | |
H29A | 0.7420 | 0.1276 | 0.1397 | 0.096* | |
H29D | 0.6420 | 0.0989 | 0.0741 | 0.096* | |
H29B | 0.6548 | 0.1109 | 0.2810 | 0.096* | |
C30 | 0.2062 (4) | 0.18580 (15) | −0.0755 (7) | 0.0623 (13) | |
H30D | 0.2742 | 0.1970 | −0.1234 | 0.093* | |
H30A | 0.1640 | 0.2101 | −0.0270 | 0.093* | |
H30B | 0.1657 | 0.1715 | −0.1712 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.060 (2) | 0.090 (2) | 0.103 (3) | −0.0292 (19) | −0.007 (2) | −0.020 (2) |
O2 | 0.083 (2) | 0.112 (3) | 0.098 (3) | −0.040 (2) | 0.014 (2) | −0.026 (3) |
O3 | 0.102 (3) | 0.148 (4) | 0.081 (3) | −0.035 (3) | 0.029 (3) | −0.017 (3) |
O4 | 0.0501 (18) | 0.126 (3) | 0.069 (2) | −0.006 (2) | −0.0200 (18) | 0.018 (2) |
O5 | 0.0452 (16) | 0.0519 (16) | 0.0514 (18) | −0.0011 (13) | 0.0003 (14) | −0.0054 (15) |
O6 | 0.078 (2) | 0.089 (2) | 0.052 (2) | −0.001 (2) | −0.0079 (19) | −0.0021 (19) |
O7 | 0.0501 (15) | 0.0375 (16) | 0.0581 (18) | −0.0025 (13) | −0.0017 (15) | 0.0014 (15) |
O8 | 0.137 (4) | 0.066 (2) | 0.098 (3) | −0.015 (2) | −0.007 (3) | −0.027 (2) |
C1 | 0.065 (3) | 0.052 (3) | 0.056 (3) | −0.011 (2) | 0.001 (2) | −0.011 (2) |
C2 | 0.072 (3) | 0.063 (3) | 0.054 (3) | −0.021 (3) | −0.012 (3) | −0.004 (3) |
C3 | 0.058 (3) | 0.051 (3) | 0.067 (3) | −0.014 (2) | −0.013 (3) | 0.000 (3) |
C4 | 0.043 (2) | 0.046 (2) | 0.054 (3) | −0.007 (2) | 0.001 (2) | 0.002 (2) |
C5 | 0.041 (2) | 0.039 (2) | 0.044 (2) | −0.0046 (18) | −0.003 (2) | 0.000 (2) |
C6 | 0.046 (2) | 0.037 (2) | 0.045 (2) | 0.0048 (19) | 0.0000 (19) | −0.002 (2) |
C7 | 0.040 (2) | 0.048 (2) | 0.048 (3) | −0.0015 (19) | −0.003 (2) | 0.004 (2) |
C8 | 0.043 (2) | 0.047 (2) | 0.046 (2) | 0.004 (2) | −0.005 (2) | 0.003 (2) |
C9 | 0.049 (2) | 0.045 (2) | 0.052 (3) | 0.001 (2) | 0.000 (2) | −0.004 (2) |
C10 | 0.047 (2) | 0.038 (2) | 0.047 (3) | −0.0009 (19) | −0.005 (2) | −0.004 (2) |
C11 | 0.065 (3) | 0.058 (3) | 0.075 (3) | 0.001 (2) | 0.009 (3) | −0.016 (3) |
C12 | 0.059 (3) | 0.068 (3) | 0.072 (3) | 0.004 (2) | 0.006 (3) | −0.008 (3) |
C13 | 0.040 (2) | 0.058 (3) | 0.055 (3) | 0.002 (2) | −0.005 (2) | −0.003 (2) |
C14 | 0.043 (2) | 0.064 (3) | 0.051 (3) | 0.002 (2) | −0.006 (2) | 0.001 (2) |
C15 | 0.059 (3) | 0.105 (5) | 0.065 (3) | −0.023 (3) | 0.001 (3) | −0.028 (3) |
C16 | 0.049 (3) | 0.093 (4) | 0.069 (3) | −0.018 (3) | 0.005 (3) | −0.014 (3) |
C17 | 0.037 (2) | 0.073 (3) | 0.062 (3) | 0.002 (2) | −0.001 (2) | 0.000 (3) |
C18 | 0.050 (3) | 0.089 (4) | 0.062 (3) | −0.005 (3) | −0.006 (2) | 0.018 (3) |
C19 | 0.066 (3) | 0.037 (2) | 0.093 (4) | −0.003 (2) | 0.001 (3) | 0.006 (3) |
C20 | 0.042 (2) | 0.078 (4) | 0.067 (3) | −0.003 (3) | 0.000 (2) | −0.005 (3) |
C21 | 0.066 (3) | 0.098 (4) | 0.084 (4) | −0.003 (3) | 0.003 (3) | 0.015 (4) |
C22 | 0.078 (4) | 0.130 (6) | 0.091 (5) | −0.033 (4) | −0.004 (4) | 0.028 (5) |
C23 | 0.088 (4) | 0.101 (4) | 0.085 (4) | −0.019 (3) | 0.037 (4) | −0.013 (4) |
C24 | 0.052 (3) | 0.064 (3) | 0.058 (3) | −0.010 (2) | 0.002 (3) | −0.010 (3) |
C25 | 0.086 (4) | 0.088 (4) | 0.082 (4) | 0.005 (3) | 0.010 (3) | −0.030 (3) |
C26 | 0.065 (3) | 0.051 (3) | 0.090 (4) | −0.007 (2) | −0.007 (3) | −0.010 (3) |
C27 | 0.092 (4) | 0.054 (3) | 0.122 (4) | −0.004 (3) | −0.009 (4) | 0.020 (4) |
C28 | 0.055 (3) | 0.069 (3) | 0.069 (3) | −0.013 (2) | −0.001 (2) | 0.013 (3) |
C29 | 0.048 (2) | 0.057 (3) | 0.086 (4) | 0.001 (2) | −0.013 (3) | −0.001 (3) |
C30 | 0.058 (3) | 0.060 (3) | 0.069 (3) | 0.010 (2) | −0.003 (2) | 0.006 (3) |
O1—C3 | 1.224 (5) | C12—H12B | 0.9700 |
O2—C16 | 1.200 (6) | C13—C18 | 1.520 (6) |
O3—C22 | 1.359 (8) | C13—C14 | 1.532 (6) |
O3—C23 | 1.360 (7) | C13—C17 | 1.573 (6) |
O4—C15 | 1.424 (7) | C14—C15 | 1.464 (6) |
O4—C14 | 1.440 (5) | C15—C16 | 1.499 (7) |
O5—C24 | 1.362 (5) | C15—H15A | 0.9800 |
O5—C6 | 1.453 (5) | C16—C17 | 1.506 (7) |
O6—C24 | 1.199 (5) | C17—C20 | 1.500 (7) |
O7—C26 | 1.354 (6) | C17—H17A | 0.9800 |
O7—C7 | 1.442 (5) | C18—H18A | 0.9600 |
O8—C26 | 1.195 (6) | C18—H18B | 0.9600 |
C1—C2 | 1.319 (6) | C18—H18C | 0.9600 |
C1—C10 | 1.516 (6) | C19—H19A | 0.9600 |
C1—H1A | 0.9300 | C19—H19B | 0.9600 |
C2—C3 | 1.447 (7) | C19—H19C | 0.9600 |
C2—H2A | 0.9300 | C20—C23 | 1.331 (7) |
C3—C4 | 1.522 (6) | C20—C21 | 1.419 (7) |
C4—C29 | 1.546 (6) | C21—C22 | 1.331 (8) |
C4—C28 | 1.547 (6) | C21—H21A | 0.9300 |
C4—C5 | 1.564 (5) | C22—H22A | 0.9300 |
C5—C6 | 1.532 (5) | C23—H23A | 0.9300 |
C5—C10 | 1.560 (5) | C24—C25 | 1.482 (7) |
C5—H5A | 0.9800 | C25—H25A | 0.9600 |
C6—C7 | 1.528 (5) | C25—H25B | 0.9600 |
C6—H6A | 0.9800 | C25—H25C | 0.9600 |
C7—C8 | 1.523 (6) | C26—C27 | 1.493 (7) |
C7—H7A | 0.9800 | C27—H27A | 0.9600 |
C8—C30 | 1.545 (6) | C27—H27B | 0.9600 |
C8—C9 | 1.559 (6) | C27—H27C | 0.9600 |
C8—C14 | 1.564 (6) | C28—H28A | 0.9600 |
C9—C11 | 1.532 (6) | C28—H28B | 0.9600 |
C9—C10 | 1.568 (6) | C28—H28D | 0.9600 |
C9—H9A | 0.9800 | C29—H29A | 0.9600 |
C10—C19 | 1.546 (6) | C29—H29D | 0.9600 |
C11—C12 | 1.531 (6) | C29—H29B | 0.9600 |
C11—H11A | 0.9700 | C30—H30D | 0.9600 |
C11—H11B | 0.9700 | C30—H30A | 0.9600 |
C12—C13 | 1.529 (6) | C30—H30B | 0.9600 |
C12—H12A | 0.9700 | ||
C22—O3—C23 | 106.2 (5) | C15—C14—C8 | 128.1 (4) |
C15—O4—C14 | 61.5 (3) | C13—C14—C8 | 120.8 (3) |
C24—O5—C6 | 116.4 (3) | O4—C15—C14 | 59.8 (3) |
C26—O7—C7 | 118.8 (4) | O4—C15—C16 | 107.3 (5) |
C2—C1—C10 | 122.2 (4) | C14—C15—C16 | 107.0 (4) |
C2—C1—H1A | 118.9 | O4—C15—H15A | 122.2 |
C10—C1—H1A | 118.9 | C14—C15—H15A | 122.2 |
C1—C2—C3 | 121.1 (5) | C16—C15—H15A | 122.2 |
C1—C2—H2A | 119.4 | O2—C16—C15 | 126.2 (5) |
C3—C2—H2A | 119.4 | O2—C16—C17 | 127.5 (5) |
O1—C3—C2 | 120.8 (5) | C15—C16—C17 | 106.3 (4) |
O1—C3—C4 | 120.2 (5) | C20—C17—C16 | 116.2 (4) |
C2—C3—C4 | 118.9 (4) | C20—C17—C13 | 116.6 (4) |
C3—C4—C29 | 103.2 (4) | C16—C17—C13 | 101.8 (3) |
C3—C4—C28 | 110.0 (3) | C20—C17—H17A | 107.2 |
C29—C4—C28 | 108.4 (4) | C16—C17—H17A | 107.2 |
C3—C4—C5 | 111.1 (4) | C13—C17—H17A | 107.2 |
C29—C4—C5 | 109.4 (3) | C13—C18—H18A | 109.5 |
C28—C4—C5 | 114.1 (4) | C13—C18—H18B | 109.5 |
C6—C5—C10 | 109.8 (3) | H18A—C18—H18B | 109.5 |
C6—C5—C4 | 115.2 (3) | C13—C18—H18C | 109.5 |
C10—C5—C4 | 114.2 (3) | H18A—C18—H18C | 109.5 |
C6—C5—H5A | 105.6 | H18B—C18—H18C | 109.5 |
C10—C5—H5A | 105.6 | C10—C19—H19A | 109.5 |
C4—C5—H5A | 105.6 | C10—C19—H19B | 109.5 |
O5—C6—C7 | 107.4 (3) | H19A—C19—H19B | 109.5 |
O5—C6—C5 | 109.1 (3) | C10—C19—H19C | 109.5 |
C7—C6—C5 | 112.1 (3) | H19A—C19—H19C | 109.5 |
O5—C6—H6A | 109.4 | H19B—C19—H19C | 109.5 |
C7—C6—H6A | 109.4 | C23—C20—C21 | 105.3 (5) |
C5—C6—H6A | 109.4 | C23—C20—C17 | 126.1 (5) |
O7—C7—C8 | 108.8 (3) | C21—C20—C17 | 128.7 (5) |
O7—C7—C6 | 108.2 (3) | C22—C21—C20 | 107.7 (6) |
C8—C7—C6 | 110.5 (3) | C22—C21—H21A | 126.1 |
O7—C7—H7A | 109.8 | C20—C21—H21A | 126.1 |
C8—C7—H7A | 109.8 | C21—C22—O3 | 109.6 (6) |
C6—C7—H7A | 109.8 | C21—C22—H22A | 125.2 |
C7—C8—C30 | 107.9 (3) | O3—C22—H22A | 125.2 |
C7—C8—C9 | 109.7 (3) | C20—C23—O3 | 111.1 (6) |
C30—C8—C9 | 113.6 (3) | C20—C23—H23A | 124.4 |
C7—C8—C14 | 111.9 (3) | O3—C23—H23A | 124.4 |
C30—C8—C14 | 107.3 (3) | O6—C24—O5 | 122.8 (4) |
C9—C8—C14 | 106.5 (3) | O6—C24—C25 | 125.9 (5) |
C11—C9—C8 | 110.8 (3) | O5—C24—C25 | 111.3 (5) |
C11—C9—C10 | 115.8 (3) | C24—C25—H25A | 109.5 |
C8—C9—C10 | 114.7 (3) | C24—C25—H25B | 109.5 |
C11—C9—H9A | 104.7 | H25A—C25—H25B | 109.5 |
C8—C9—H9A | 104.7 | C24—C25—H25C | 109.5 |
C10—C9—H9A | 104.7 | H25A—C25—H25C | 109.5 |
C1—C10—C19 | 105.8 (3) | H25B—C25—H25C | 109.5 |
C1—C10—C5 | 104.6 (3) | O8—C26—O7 | 122.5 (5) |
C19—C10—C5 | 115.4 (4) | O8—C26—C27 | 127.1 (5) |
C1—C10—C9 | 108.5 (3) | O7—C26—C27 | 110.4 (5) |
C19—C10—C9 | 114.7 (3) | C26—C27—H27A | 109.5 |
C5—C10—C9 | 107.2 (3) | C26—C27—H27B | 109.5 |
C12—C11—C9 | 114.3 (4) | H27A—C27—H27B | 109.5 |
C12—C11—H11A | 108.7 | C26—C27—H27C | 109.5 |
C9—C11—H11A | 108.7 | H27A—C27—H27C | 109.5 |
C12—C11—H11B | 108.7 | H27B—C27—H27C | 109.5 |
C9—C11—H11B | 108.7 | C4—C28—H28A | 109.5 |
H11A—C11—H11B | 107.6 | C4—C28—H28B | 109.5 |
C13—C12—C11 | 114.6 (4) | H28A—C28—H28B | 109.5 |
C13—C12—H12A | 108.6 | C4—C28—H28D | 109.5 |
C11—C12—H12A | 108.6 | H28A—C28—H28D | 109.5 |
C13—C12—H12B | 108.6 | H28B—C28—H28D | 109.5 |
C11—C12—H12B | 108.6 | C4—C29—H29A | 109.5 |
H12A—C12—H12B | 107.6 | C4—C29—H29D | 109.5 |
C18—C13—C12 | 113.7 (4) | H29A—C29—H29D | 109.5 |
C18—C13—C14 | 113.5 (4) | C4—C29—H29B | 109.5 |
C12—C13—C14 | 106.4 (4) | H29A—C29—H29B | 109.5 |
C18—C13—C17 | 106.4 (4) | H29D—C29—H29B | 109.5 |
C12—C13—C17 | 114.6 (4) | C8—C30—H30D | 109.5 |
C14—C13—C17 | 101.8 (3) | C8—C30—H30A | 109.5 |
O4—C14—C15 | 58.7 (3) | H30D—C30—H30A | 109.5 |
O4—C14—C13 | 110.9 (3) | C8—C30—H30B | 109.5 |
C15—C14—C13 | 108.5 (4) | H30D—C30—H30B | 109.5 |
O4—C14—C8 | 112.2 (3) | H30A—C30—H30B | 109.5 |
C10—C1—C2—C3 | −0.6 (7) | C11—C12—C13—C14 | −47.8 (5) |
C1—C2—C3—O1 | 155.2 (5) | C11—C12—C13—C17 | −159.4 (4) |
C1—C2—C3—C4 | −27.8 (7) | C15—O4—C14—C13 | −99.5 (4) |
O1—C3—C4—C29 | 68.6 (5) | C15—O4—C14—C8 | 122.1 (4) |
C2—C3—C4—C29 | −108.4 (4) | C18—C13—C14—O4 | 151.9 (4) |
O1—C3—C4—C28 | −46.8 (6) | C12—C13—C14—O4 | −82.3 (4) |
C2—C3—C4—C28 | 136.1 (4) | C17—C13—C14—O4 | 37.9 (5) |
O1—C3—C4—C5 | −174.2 (4) | C18—C13—C14—C15 | 89.2 (4) |
C2—C3—C4—C5 | 8.8 (6) | C12—C13—C14—C15 | −145.0 (4) |
C3—C4—C5—C6 | 162.7 (3) | C17—C13—C14—C15 | −24.8 (5) |
C29—C4—C5—C6 | −84.1 (4) | C18—C13—C14—C8 | −73.9 (5) |
C28—C4—C5—C6 | 37.6 (5) | C12—C13—C14—C8 | 51.9 (5) |
C3—C4—C5—C10 | 34.3 (5) | C17—C13—C14—C8 | 172.1 (4) |
C29—C4—C5—C10 | 147.6 (4) | C7—C8—C14—O4 | −108.7 (4) |
C28—C4—C5—C10 | −90.8 (4) | C30—C8—C14—O4 | 9.4 (5) |
C24—O5—C6—C7 | 82.0 (4) | C9—C8—C14—O4 | 131.4 (4) |
C24—O5—C6—C5 | −156.3 (3) | C7—C8—C14—C15 | −41.9 (6) |
C10—C5—C6—O5 | 179.4 (3) | C30—C8—C14—C15 | 76.3 (6) |
C4—C5—C6—O5 | 48.8 (4) | C9—C8—C14—C15 | −161.8 (5) |
C10—C5—C6—C7 | −61.8 (4) | C7—C8—C14—C13 | 117.6 (4) |
C4—C5—C6—C7 | 167.7 (3) | C30—C8—C14—C13 | −124.2 (4) |
C26—O7—C7—C8 | 136.6 (4) | C9—C8—C14—C13 | −2.3 (5) |
C26—O7—C7—C6 | −103.4 (4) | C14—O4—C15—C16 | 100.0 (4) |
O5—C6—C7—O7 | 60.8 (4) | C13—C14—C15—O4 | 103.7 (4) |
C5—C6—C7—O7 | −59.0 (4) | C8—C14—C15—O4 | −94.8 (5) |
O5—C6—C7—C8 | 179.8 (3) | O4—C14—C15—C16 | −100.5 (5) |
C5—C6—C7—C8 | 60.1 (4) | C13—C14—C15—C16 | 3.2 (6) |
O7—C7—C8—C30 | −171.2 (3) | C8—C14—C15—C16 | 164.7 (4) |
C6—C7—C8—C30 | 70.2 (4) | O4—C15—C16—O2 | 137.6 (6) |
O7—C7—C8—C9 | 64.6 (4) | C14—C15—C16—O2 | −159.5 (5) |
C6—C7—C8—C9 | −54.0 (4) | O4—C15—C16—C17 | −41.7 (5) |
O7—C7—C8—C14 | −53.4 (4) | C14—C15—C16—C17 | 21.2 (6) |
C6—C7—C8—C14 | −172.0 (3) | O2—C16—C17—C20 | 17.0 (8) |
C7—C8—C9—C11 | −172.5 (3) | C15—C16—C17—C20 | −163.7 (4) |
C30—C8—C9—C11 | 66.8 (5) | O2—C16—C17—C13 | 144.8 (5) |
C14—C8—C9—C11 | −51.2 (4) | C15—C16—C17—C13 | −35.9 (5) |
C7—C8—C9—C10 | 54.2 (4) | C18—C13—C17—C20 | 44.8 (5) |
C30—C8—C9—C10 | −66.6 (5) | C12—C13—C17—C20 | −81.8 (5) |
C14—C8—C9—C10 | 175.5 (3) | C14—C13—C17—C20 | 163.9 (4) |
C2—C1—C10—C19 | −80.6 (5) | C18—C13—C17—C16 | −82.7 (5) |
C2—C1—C10—C5 | 41.7 (5) | C12—C13—C17—C16 | 150.7 (4) |
C2—C1—C10—C9 | 155.8 (4) | C14—C13—C17—C16 | 36.4 (5) |
C6—C5—C10—C1 | 171.7 (3) | C16—C17—C20—C23 | −153.2 (5) |
C4—C5—C10—C1 | −57.3 (4) | C13—C17—C20—C23 | 86.7 (6) |
C6—C5—C10—C19 | −72.5 (4) | C16—C17—C20—C21 | 25.9 (7) |
C4—C5—C10—C19 | 58.5 (5) | C13—C17—C20—C21 | −94.2 (6) |
C6—C5—C10—C9 | 56.6 (4) | C23—C20—C21—C22 | −1.6 (6) |
C4—C5—C10—C9 | −172.3 (3) | C17—C20—C21—C22 | 179.0 (5) |
C11—C9—C10—C1 | 61.7 (5) | C20—C21—C22—O3 | 0.9 (6) |
C8—C9—C10—C1 | −167.3 (3) | C23—O3—C22—C21 | 0.2 (7) |
C11—C9—C10—C19 | −56.3 (5) | C21—C20—C23—O3 | 1.8 (6) |
C8—C9—C10—C19 | 74.7 (4) | C17—C20—C23—O3 | −178.9 (4) |
C11—C9—C10—C5 | 174.2 (4) | C22—O3—C23—C20 | −1.3 (7) |
C8—C9—C10—C5 | −54.8 (4) | C6—O5—C24—O6 | −3.1 (6) |
C8—C9—C11—C12 | 55.8 (5) | C6—O5—C24—C25 | 175.7 (3) |
C10—C9—C11—C12 | −171.4 (4) | C7—O7—C26—O8 | −0.7 (7) |
C9—C11—C12—C13 | −2.1 (6) | C7—O7—C26—C27 | 178.6 (4) |
C11—C12—C13—C18 | 77.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O7 | 0.98 | 2.45 | 2.900 (5) | 107 |
C7—H7A···O8 | 0.98 | 2.31 | 2.705 (5) | 103 |
C9—H9A···O7 | 0.98 | 2.54 | 2.936 (5) | 104 |
C27—H27A···O2i | 0.96 | 2.51 | 3.422 (7) | 160 |
C28—H28D···O5 | 0.96 | 2.53 | 3.121 (6) | 120 |
C29—H29D···O5 | 0.96 | 2.29 | 2.973 (5) | 127 |
Symmetry code: (i) −x, −y, z. |
Experimental details
Crystal data | |
Chemical formula | C30H36O8 |
Mr | 524.59 |
Crystal system, space group | Orthorhombic, P21212 |
Temperature (K) | 297 |
a, b, c (Å) | 12.189 (3), 29.983 (5), 7.3372 (11) |
V (Å3) | 2681.5 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.39 × 0.10 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.965, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20575, 2724, 1782 |
Rint | 0.100 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.125, 1.02 |
No. of reflections | 2724 |
No. of parameters | 351 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O7 | 0.98 | 2.4543 | 2.900 (5) | 107 |
C7—H7A···O8 | 0.98 | 2.3085 | 2.705 (5) | 103 |
C9—H9A···O7 | 0.98 | 2.5363 | 2.936 (5) | 104 |
C27—H27A···O2i | 0.96 | 2.5047 | 3.422 (7) | 160 |
C28—H28D···O5 | 0.96 | 2.5277 | 3.121 (6) | 120 |
C29—H29D···O5 | 0.96 | 2.2906 | 2.973 (5) | 127 |
Symmetry code: (i) −x, −y, z. |
Meliaceae plants are known to be rich sources of limonoids. Some of these limonoids posses significant pharmocological effects such as antimalarial (Bickii et al., 2000; Saewan et al., 2006), cytotoxic (Takeya et al., 1996), antiprotozoal (Khalid et al., 1998) and antifeedant activities (Koul et al., 2003; Nihei et al., 2002). Chisocheton siamensis or "Ta Sua" in a local Thai name, is one of the Meliaceae plants, which is found in the northern part of Thailand. As part of our study of chemical constituents and bioactive compounds from C. siamensis, we herein report the crystal structure of the title compound which was isolated for the first time from the seed of C. siamensis collected from Chiang Mai province in the northern part of Thailand. The title compound was found to posses anti-allergic (Penido, Costa et al., (2006) and antiinflammatory (Penido, Conte et al., (2006) activities.
The title molecule (Fig. 1) contains a four trans-fused rings, the cyclohexene ring adopts a screw boat conformation with the puckering parameters (Cremer & Pople, 1975) Q = 0.552 (4) Å, θ = 70.6 (5)° and φ = 276.7 (5)°, the two cyclohexane rings are in standard chair and boat conformations and the cyclopentane adopts an envelope conformation, with atom C17 displaced from the C13/C14/C15/C16 plane by 0.238 (4) Å. The oxirane moiety (C14/C15/O3) makes the dihedral angle of 78.0 (4)° with the mean plane of C13/C14/C15/C16. The furan ring is planar and attached to the cyclopentane ring at atom C17, the dihedral angle between the furan ring and the C13/C14/C15/C16 mean plane is 56.7 (3)°. The two acetate groups are planar and in cis-configuration with respect to the C6—C7 bond, the dihedral angle between the mean plane of these two acetate moieties is 44.4 (3)°(Fig.1). The bond lengths and angles are within normal ranges (Allen et al., 1987). In the structure, the weak C5—H5A···O7, C7—H7A···O8 and C9—H9A···O7 intramolecular interactions generate S(5) ring motifs, the C28—H28D···O5 and C29—H28D···O5 generate S(6) ring motifs (Bernstein et al.,1995), whereas the intermolecular C27—H27A···O2(-x, -y, z) interaction connects the molecules into dimers (Fig. 2).