organic compounds
3-epi-Dammarenediol II 1.075 hydrate: a dammarane triterpene from the bark of Aglaia eximia
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and dDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia
*Correspondence e-mail: hkfun@usm.my
The title dammarane tritepene, 3α,20(S)-dihydroxydammar-24-ene, which crystallized out in a hydrated form, C30H52O2.1.075H2O, was isolated from the Aglaia eximia bark. The three cyclohexane rings adopt chair conformations. The cyclopentane has an with the quaternary C at position 14 as the flap atom with the maximum deviation of 0.288 (2) Å. The methylheptene side chain is disordered over two positions with 0.505 (1):0.495 (1) site occupancies and is axially attached with an (+)-syn-clinal conformation. The hydroxyl group at position 3 of dammarane is in a different conformation to the corresponding hydroxyl in Dammarenediol II. In the crystal, the dammarane and water molecules are linked by ODammarane—H⋯Owater and Owater—H⋯ODammarane hydrogen bonds into a three-dimensional network.
Related literature
For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For background to Aglaia plants, and their biological activity, see: Asakawa et al. (1977); Chairgulprasert et al. (2006); Greger et al. (2001); Grosvenor et al. (1995); Lima et al. (2004); Qiu et al. (2001); Roux et al. (1998); Yodsaoue et al. (2012); Zhang et al. (2010). For related structures, see: Qiu et al. (2001). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Supporting information
The dried and milled bark of A. eximia (3 kg) which was collected from Bogor Botanical Garden, West Java, Indonesia, was extracted successively by n-hexane, ethyl acetate and methanol at room temperature. The ethyl acetate extract (300 g) was subjected to vacuum
on silica gel G 60 by using a step gradient of n-hexane-ethyl acetate methanol. The fraction eluted by n-hexane/ethyl acetate (3:2) was further separated by on silica gel (chloroform: methanol; 9.5:0.5 v/v) to give a colorless solid (63 mg) of the title compound. Colorless needle-shaped single crystals of the title compound suitable for X-ray were recrystallized from ethyl acetate at room temperature after several days.One of the water molecules, O3W, was refined isotropically. H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(O—H) = 0.83-0.84 Å, d(C—H) = 1.00 Å for cyclic CH, 0.95 for CH, 0.99 for CH2 and 0.98 Å for CH3 atoms. The Uiso values were constrained to be 1.2Ueq of the
for all H atoms. A rotating group model was used for the methyl groups. A total of 3923 Friedel pairs were merged before final The methylheptene side chain is disordered over two sites with refined site occupancies of 0.505 (1) and 0.495 (1). The same Uij parameters were used for atom pairs C23/C24, C26/C27 and C26A/C27A. A number of reflections were omitted from the final owing to poor agreement.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C30H52O2·1.075H2O | Dx = 1.055 Mg m−3 |
Mr = 463.99 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P42 | Cell parameters from 4543 reflections |
Hall symbol: P 4c | θ = 2.0–30.0° |
a = 19.9481 (13) Å | µ = 0.07 mm−1 |
c = 7.3410 (7) Å | T = 100 K |
V = 2921.2 (5) Å3 | Needle, colourless |
Z = 4 | 0.39 × 0.11 × 0.10 mm |
F(000) = 1035 |
Bruker APEX Duo CCD area-detector diffractometer | 4543 independent reflections |
Radiation source: sealed tube | 3887 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ϕ and ω scans | θmax = 30.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −28→27 |
Tmin = 0.975, Tmax = 0.994 | k = −22→28 |
24864 measured reflections | l = −10→10 |
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)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.1014P)2 + 0.4141P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4543 reflections | Δρmax = 0.72 e Å−3 |
332 parameters | Δρmin = −0.48 e Å−3 |
1 restraint | Absolute structure: nd |
Primary atom site location: structure-invariant direct methods |
C30H52O2·1.075H2O | Z = 4 |
Mr = 463.99 | Mo Kα radiation |
Tetragonal, P42 | µ = 0.07 mm−1 |
a = 19.9481 (13) Å | T = 100 K |
c = 7.3410 (7) Å | 0.39 × 0.11 × 0.10 mm |
V = 2921.2 (5) Å3 |
Bruker APEX Duo CCD area-detector diffractometer | 4543 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3887 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.994 | Rint = 0.064 |
24864 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 1 restraint |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.72 e Å−3 |
4543 reflections | Δρmin = −0.48 e Å−3 |
332 parameters | Absolute structure: nd |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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 > 2sigma(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 | Occ. (<1) | |
O1 | 0.40685 (8) | 0.04934 (8) | 0.2210 (3) | 0.0194 (4) | |
H1O1 | 0.3988 | 0.0883 | 0.2587 | 0.023* | |
O2 | 0.09002 (8) | 0.45212 (8) | 0.2073 (3) | 0.0202 (4) | |
H1O2 | 0.0731 | 0.4721 | 0.2969 | 0.024* | |
C1 | 0.30479 (11) | 0.12044 (11) | 0.0082 (4) | 0.0158 (4) | |
H1A | 0.2901 | 0.1373 | −0.1122 | 0.019* | |
H1B | 0.3454 | 0.1457 | 0.0439 | 0.019* | |
C2 | 0.32266 (12) | 0.04584 (12) | −0.0089 (3) | 0.0175 (5) | |
H2A | 0.2832 | 0.0208 | −0.0543 | 0.021* | |
H2B | 0.3593 | 0.0404 | −0.0987 | 0.021* | |
C3 | 0.34456 (12) | 0.01670 (11) | 0.1731 (4) | 0.0160 (4) | |
H3A | 0.3534 | −0.0323 | 0.1566 | 0.019* | |
C4 | 0.29152 (12) | 0.02521 (11) | 0.3236 (4) | 0.0155 (4) | |
C5 | 0.27016 (11) | 0.10018 (11) | 0.3325 (3) | 0.0133 (4) | |
H5A | 0.3118 | 0.1245 | 0.3697 | 0.016* | |
C6 | 0.21933 (12) | 0.11581 (11) | 0.4842 (4) | 0.0164 (4) | |
H6A | 0.1741 | 0.1007 | 0.4466 | 0.020* | |
H6B | 0.2319 | 0.0914 | 0.5965 | 0.020* | |
C7 | 0.21811 (12) | 0.19144 (11) | 0.5223 (4) | 0.0164 (4) | |
H7A | 0.2623 | 0.2051 | 0.5715 | 0.020* | |
H7B | 0.1840 | 0.2007 | 0.6170 | 0.020* | |
C8 | 0.20235 (11) | 0.23448 (11) | 0.3524 (3) | 0.0135 (4) | |
C9 | 0.24808 (11) | 0.21167 (10) | 0.1905 (3) | 0.0132 (4) | |
H9A | 0.2946 | 0.2217 | 0.2330 | 0.016* | |
C10 | 0.24882 (11) | 0.13407 (11) | 0.1492 (3) | 0.0137 (4) | |
C11 | 0.23870 (12) | 0.25678 (11) | 0.0224 (4) | 0.0164 (4) | |
H11A | 0.1925 | 0.2511 | −0.0247 | 0.020* | |
H11B | 0.2702 | 0.2423 | −0.0742 | 0.020* | |
C12 | 0.25087 (12) | 0.33151 (11) | 0.0648 (4) | 0.0167 (4) | |
H12A | 0.2982 | 0.3385 | 0.1008 | 0.020* | |
H12B | 0.2418 | 0.3589 | −0.0450 | 0.020* | |
C13 | 0.20444 (11) | 0.35310 (11) | 0.2196 (3) | 0.0142 (4) | |
H13A | 0.1576 | 0.3429 | 0.1800 | 0.017* | |
C14 | 0.21829 (11) | 0.31048 (11) | 0.3922 (3) | 0.0136 (4) | |
C15 | 0.17269 (12) | 0.34658 (12) | 0.5301 (4) | 0.0185 (5) | |
H15A | 0.1845 | 0.3342 | 0.6567 | 0.022* | |
H15B | 0.1249 | 0.3357 | 0.5083 | 0.022* | |
C16 | 0.18674 (13) | 0.42168 (11) | 0.4941 (4) | 0.0183 (5) | |
H16A | 0.2245 | 0.4376 | 0.5703 | 0.022* | |
H16B | 0.1466 | 0.4490 | 0.5218 | 0.022* | |
C17 | 0.20495 (12) | 0.42675 (11) | 0.2870 (4) | 0.0156 (4) | |
H17A | 0.2518 | 0.4442 | 0.2769 | 0.019* | |
C18 | 0.12704 (11) | 0.22514 (12) | 0.3090 (4) | 0.0183 (5) | |
H18A | 0.1002 | 0.2512 | 0.3956 | 0.022* | |
H18B | 0.1153 | 0.1776 | 0.3190 | 0.022* | |
H18C | 0.1179 | 0.2408 | 0.1849 | 0.022* | |
C19 | 0.18212 (12) | 0.10878 (12) | 0.0669 (4) | 0.0185 (5) | |
H19A | 0.1909 | 0.0699 | −0.0113 | 0.022* | |
H19B | 0.1616 | 0.1446 | −0.0054 | 0.022* | |
H19C | 0.1516 | 0.0958 | 0.1654 | 0.022* | |
C20 | 0.15827 (12) | 0.47476 (11) | 0.1821 (4) | 0.0166 (5) | |
C21 | 0.17162 (13) | 0.47347 (13) | −0.0233 (4) | 0.0217 (5) | |
H21A | 0.1578 | 0.4300 | −0.0731 | 0.026* | |
H21B | 0.2196 | 0.4803 | −0.0458 | 0.026* | |
H21C | 0.1460 | 0.5093 | −0.0824 | 0.026* | |
C22 | 0.16225 (13) | 0.54729 (12) | 0.2552 (4) | 0.0219 (5) | |
H22A | 0.1308 | 0.5752 | 0.1838 | 0.026* | |
H22B | 0.1462 | 0.5472 | 0.3828 | 0.026* | |
C23 | 0.23106 (15) | 0.58110 (14) | 0.2509 (7) | 0.0405 (9) | |
H23A | 0.2262 | 0.6298 | 0.2290 | 0.049* | 0.505 (14) |
H23B | 0.2590 | 0.5618 | 0.1526 | 0.049* | 0.505 (14) |
H23C | 0.2503 | 0.5715 | 0.1294 | 0.049* | 0.495 (14) |
H23D | 0.2227 | 0.6300 | 0.2552 | 0.049* | 0.495 (14) |
C24 | 0.2660 (5) | 0.5675 (4) | 0.4513 (17) | 0.0405 (9) | 0.505 (14) |
H24A | 0.2382 | 0.5748 | 0.5545 | 0.049* | 0.505 (14) |
C25 | 0.3285 (5) | 0.5474 (5) | 0.486 (2) | 0.053 (3) | 0.505 (14) |
C26 | 0.3527 (5) | 0.5366 (8) | 0.680 (2) | 0.083 (4) | 0.505 (14) |
H26A | 0.3176 | 0.5503 | 0.7651 | 0.100* | 0.505 (14) |
H26B | 0.3931 | 0.5634 | 0.7008 | 0.100* | 0.505 (14) |
H26C | 0.3631 | 0.4890 | 0.6978 | 0.100* | 0.505 (14) |
C27 | 0.3782 (5) | 0.5330 (7) | 0.339 (2) | 0.083 (4) | 0.505 (14) |
H27A | 0.3692 | 0.4886 | 0.2867 | 0.100* | 0.505 (14) |
H27B | 0.4237 | 0.5339 | 0.3894 | 0.100* | 0.505 (14) |
H27C | 0.3744 | 0.5670 | 0.2429 | 0.100* | 0.505 (14) |
C24A | 0.2789 (4) | 0.5695 (4) | 0.3779 (19) | 0.041 (3) | 0.495 (14) |
H24B | 0.2655 | 0.5767 | 0.5006 | 0.050* | 0.495 (14) |
C25A | 0.3409 (4) | 0.5498 (5) | 0.355 (3) | 0.073 (5) | 0.495 (14) |
C26A | 0.3867 (5) | 0.5364 (7) | 0.512 (3) | 0.111 (6) | 0.495 (14) |
H26D | 0.3610 | 0.5374 | 0.6262 | 0.133* | 0.495 (14) |
H26E | 0.4217 | 0.5708 | 0.5165 | 0.133* | 0.495 (14) |
H26F | 0.4074 | 0.4922 | 0.4977 | 0.133* | 0.495 (14) |
C27A | 0.3696 (5) | 0.5328 (8) | 0.159 (3) | 0.111 (6) | 0.495 (14) |
H27D | 0.4145 | 0.5521 | 0.1466 | 0.133* | 0.495 (14) |
H27E | 0.3400 | 0.5517 | 0.0662 | 0.133* | 0.495 (14) |
H27F | 0.3720 | 0.4840 | 0.1444 | 0.133* | 0.495 (14) |
C28 | 0.32341 (12) | 0.00442 (12) | 0.5058 (4) | 0.0188 (5) | |
H28A | 0.3460 | −0.0389 | 0.4914 | 0.023* | |
H28B | 0.2884 | 0.0006 | 0.5990 | 0.023* | |
H28C | 0.3561 | 0.0384 | 0.5433 | 0.023* | |
C29 | 0.23313 (13) | −0.02388 (12) | 0.2882 (4) | 0.0212 (5) | |
H29A | 0.2497 | −0.0701 | 0.2956 | 0.025* | |
H29B | 0.2146 | −0.0157 | 0.1666 | 0.025* | |
H29C | 0.1981 | −0.0170 | 0.3800 | 0.025* | |
C30 | 0.29122 (12) | 0.32099 (12) | 0.4601 (4) | 0.0188 (5) | |
H30A | 0.3048 | 0.3675 | 0.4376 | 0.023* | |
H30B | 0.3213 | 0.2906 | 0.3945 | 0.023* | |
H30C | 0.2936 | 0.3115 | 0.5909 | 0.023* | |
O1W | 0.0000 | 0.5000 | 0.4726 (4) | 0.0189 (5) | |
H1W1 | 0.0159 | 0.5297 | 0.5419 | 0.023* | |
O2W | 0.0000 | 0.5000 | 0.9617 (4) | 0.0187 (5) | |
H1W2 | 0.0278 | 0.4839 | 1.0342 | 0.022* | |
O3W | 0.967 (2) | 0.016 (2) | 0.858 (7) | 0.069 (12)* | 0.07 |
H1W3 | 0.9518 | 0.0223 | 0.9645 | 0.083* | 0.07 |
H2W3 | 1.0084 | 0.0055 | 0.8469 | 0.083* | 0.07 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0211 (8) | 0.0185 (8) | 0.0188 (9) | 0.0018 (6) | −0.0003 (7) | −0.0031 (7) |
O2 | 0.0176 (8) | 0.0214 (8) | 0.0215 (10) | 0.0016 (6) | −0.0002 (7) | −0.0016 (8) |
C1 | 0.0201 (10) | 0.0153 (9) | 0.0119 (11) | 0.0026 (8) | 0.0011 (9) | 0.0000 (9) |
C2 | 0.0245 (11) | 0.0172 (10) | 0.0108 (11) | 0.0040 (8) | 0.0002 (9) | −0.0032 (9) |
C3 | 0.0209 (10) | 0.0133 (9) | 0.0139 (11) | 0.0034 (8) | −0.0001 (9) | −0.0017 (8) |
C4 | 0.0196 (10) | 0.0134 (9) | 0.0136 (11) | 0.0006 (8) | 0.0001 (9) | −0.0001 (9) |
C5 | 0.0160 (10) | 0.0150 (9) | 0.0089 (10) | 0.0004 (7) | −0.0002 (8) | −0.0010 (8) |
C6 | 0.0202 (10) | 0.0152 (9) | 0.0139 (12) | 0.0008 (8) | 0.0035 (9) | 0.0002 (9) |
C7 | 0.0219 (10) | 0.0170 (10) | 0.0103 (10) | 0.0013 (8) | 0.0028 (9) | 0.0012 (9) |
C8 | 0.0143 (9) | 0.0163 (10) | 0.0098 (10) | 0.0021 (7) | 0.0006 (8) | 0.0009 (8) |
C9 | 0.0155 (9) | 0.0135 (9) | 0.0106 (11) | 0.0013 (7) | −0.0004 (8) | −0.0006 (8) |
C10 | 0.0157 (10) | 0.0145 (9) | 0.0109 (11) | 0.0007 (7) | 0.0000 (8) | −0.0009 (8) |
C11 | 0.0220 (10) | 0.0162 (10) | 0.0109 (11) | 0.0038 (8) | 0.0015 (9) | 0.0000 (9) |
C12 | 0.0210 (11) | 0.0164 (10) | 0.0127 (11) | 0.0025 (8) | 0.0024 (9) | 0.0022 (9) |
C13 | 0.0168 (9) | 0.0146 (9) | 0.0112 (11) | 0.0022 (7) | −0.0013 (9) | −0.0018 (9) |
C14 | 0.0166 (10) | 0.0139 (9) | 0.0101 (10) | 0.0032 (8) | −0.0011 (8) | −0.0015 (8) |
C15 | 0.0244 (11) | 0.0179 (10) | 0.0133 (11) | 0.0044 (8) | 0.0029 (9) | −0.0017 (9) |
C16 | 0.0264 (11) | 0.0153 (10) | 0.0131 (11) | 0.0045 (8) | −0.0025 (10) | −0.0025 (9) |
C17 | 0.0181 (10) | 0.0135 (9) | 0.0151 (11) | 0.0013 (7) | −0.0005 (9) | −0.0029 (9) |
C18 | 0.0156 (10) | 0.0197 (10) | 0.0197 (12) | −0.0001 (8) | 0.0013 (9) | −0.0025 (10) |
C19 | 0.0183 (10) | 0.0205 (10) | 0.0167 (12) | −0.0009 (8) | −0.0063 (9) | −0.0021 (9) |
C20 | 0.0185 (10) | 0.0153 (10) | 0.0161 (12) | 0.0019 (8) | 0.0001 (9) | 0.0010 (9) |
C21 | 0.0266 (12) | 0.0228 (11) | 0.0157 (12) | 0.0060 (9) | 0.0029 (10) | 0.0043 (10) |
C22 | 0.0238 (11) | 0.0149 (10) | 0.0272 (15) | 0.0023 (8) | 0.0022 (10) | 0.0007 (10) |
C23 | 0.0309 (14) | 0.0176 (11) | 0.073 (3) | −0.0046 (9) | 0.0144 (16) | −0.0107 (14) |
C24 | 0.0309 (14) | 0.0176 (11) | 0.073 (3) | −0.0046 (9) | 0.0144 (16) | −0.0107 (14) |
C25 | 0.024 (4) | 0.047 (4) | 0.090 (9) | −0.003 (3) | −0.013 (5) | −0.006 (5) |
C26 | 0.040 (4) | 0.102 (6) | 0.108 (9) | 0.019 (4) | −0.029 (4) | −0.032 (6) |
C27 | 0.040 (4) | 0.102 (6) | 0.108 (9) | 0.019 (4) | −0.029 (4) | −0.032 (6) |
C24A | 0.021 (3) | 0.022 (3) | 0.081 (8) | −0.006 (2) | −0.006 (4) | −0.007 (4) |
C25A | 0.017 (4) | 0.036 (4) | 0.166 (17) | −0.003 (3) | 0.001 (6) | 0.007 (7) |
C26A | 0.035 (4) | 0.091 (6) | 0.207 (18) | −0.008 (3) | −0.016 (6) | 0.018 (8) |
C27A | 0.035 (4) | 0.091 (6) | 0.207 (18) | −0.008 (3) | −0.016 (6) | 0.018 (8) |
C28 | 0.0238 (11) | 0.0178 (10) | 0.0149 (11) | 0.0024 (8) | 0.0000 (10) | 0.0012 (9) |
C29 | 0.0261 (12) | 0.0150 (10) | 0.0224 (13) | −0.0030 (9) | −0.0012 (10) | −0.0004 (10) |
C30 | 0.0198 (10) | 0.0167 (10) | 0.0197 (12) | 0.0005 (8) | −0.0056 (10) | −0.0016 (9) |
O1W | 0.0233 (12) | 0.0190 (11) | 0.0145 (12) | −0.0064 (9) | 0.000 | 0.000 |
O2W | 0.0190 (11) | 0.0212 (11) | 0.0158 (12) | 0.0021 (9) | 0.000 | 0.000 |
O1—C3 | 1.446 (3) | C18—H18C | 0.9800 |
O1—H1O1 | 0.8400 | C19—H19A | 0.9800 |
O2—C20 | 1.446 (3) | C19—H19B | 0.9800 |
O2—H1O2 | 0.8400 | C19—H19C | 0.9800 |
C1—C2 | 1.535 (3) | C20—C21 | 1.531 (4) |
C1—C10 | 1.547 (3) | C20—C22 | 1.545 (3) |
C1—H1A | 0.9900 | C21—H21A | 0.9800 |
C1—H1B | 0.9900 | C21—H21B | 0.9800 |
C2—C3 | 1.522 (3) | C21—H21C | 0.9800 |
C2—H2A | 0.9900 | C22—C23 | 1.530 (4) |
C2—H2B | 0.9900 | C22—H22A | 0.9900 |
C3—C4 | 1.539 (3) | C22—H22B | 0.9900 |
C3—H3A | 1.0000 | C23—C24A | 1.354 (11) |
C4—C28 | 1.538 (4) | C23—C24 | 1.650 (13) |
C4—C29 | 1.544 (3) | C23—H23A | 0.9900 |
C4—C5 | 1.557 (3) | C23—H23B | 0.9900 |
C5—C6 | 1.538 (3) | C23—H23C | 0.9900 |
C5—C10 | 1.565 (3) | C23—H23D | 0.9899 |
C5—H5A | 1.0000 | C24—C25 | 1.335 (13) |
C6—C7 | 1.535 (3) | C24—H24A | 0.9500 |
C6—H6A | 0.9900 | C25—C27 | 1.496 (19) |
C6—H6B | 0.9900 | C25—C26 | 1.516 (19) |
C7—C8 | 1.546 (3) | C26—H26A | 0.9800 |
C7—H7A | 0.9900 | C26—H26B | 0.9800 |
C7—H7B | 0.9900 | C26—H26C | 0.9800 |
C8—C18 | 1.547 (3) | C27—H27A | 0.9800 |
C8—C9 | 1.566 (3) | C27—H27B | 0.9800 |
C8—C14 | 1.577 (3) | C27—H27C | 0.9800 |
C9—C11 | 1.539 (3) | C24A—C25A | 1.309 (12) |
C9—C10 | 1.577 (3) | C24A—H24B | 0.9500 |
C9—H9A | 1.0000 | C25A—C26A | 1.50 (3) |
C10—C19 | 1.546 (3) | C25A—C27A | 1.58 (3) |
C11—C12 | 1.542 (3) | C26A—H26D | 0.9800 |
C11—H11A | 0.9900 | C26A—H26E | 0.9800 |
C11—H11B | 0.9900 | C26A—H26F | 0.9800 |
C12—C13 | 1.528 (3) | C27A—H27D | 0.9800 |
C12—H12A | 0.9900 | C27A—H27E | 0.9800 |
C12—H12B | 0.9900 | C27A—H27F | 0.9800 |
C13—C17 | 1.550 (3) | C28—H28A | 0.9800 |
C13—C14 | 1.551 (3) | C28—H28B | 0.9800 |
C13—H13A | 1.0000 | C28—H28C | 0.9800 |
C14—C15 | 1.540 (3) | C29—H29A | 0.9800 |
C14—C30 | 1.552 (3) | C29—H29B | 0.9800 |
C15—C16 | 1.547 (3) | C29—H29C | 0.9800 |
C15—H15A | 0.9900 | C30—H30A | 0.9800 |
C15—H15B | 0.9900 | C30—H30B | 0.9800 |
C16—C17 | 1.566 (4) | C30—H30C | 0.9800 |
C16—H16A | 0.9900 | O1W—H1W1 | 0.8422 |
C16—H16B | 0.9900 | O2W—H1W2 | 0.8324 |
C17—C20 | 1.542 (3) | O3W—O3Wi | 1.45 (9) |
C17—H17A | 1.0000 | O3W—H1W3 | 0.8496 |
C18—H18A | 0.9800 | O3W—H2W3 | 0.8504 |
C18—H18B | 0.9800 | ||
C3—O1—H1O1 | 109.4 | C20—C17—C13 | 115.2 (2) |
C20—O2—H1O2 | 109.3 | C20—C17—C16 | 112.63 (19) |
C2—C1—C10 | 113.14 (19) | C13—C17—C16 | 104.30 (19) |
C2—C1—H1A | 109.0 | C20—C17—H17A | 108.2 |
C10—C1—H1A | 109.0 | C13—C17—H17A | 108.2 |
C2—C1—H1B | 109.0 | C16—C17—H17A | 108.2 |
C10—C1—H1B | 109.0 | C8—C18—H18A | 109.5 |
H1A—C1—H1B | 107.8 | C8—C18—H18B | 109.5 |
C3—C2—C1 | 111.4 (2) | H18A—C18—H18B | 109.5 |
C3—C2—H2A | 109.3 | C8—C18—H18C | 109.5 |
C1—C2—H2A | 109.3 | H18A—C18—H18C | 109.5 |
C3—C2—H2B | 109.3 | H18B—C18—H18C | 109.5 |
C1—C2—H2B | 109.3 | C10—C19—H19A | 109.5 |
H2A—C2—H2B | 108.0 | C10—C19—H19B | 109.5 |
O1—C3—C2 | 106.76 (19) | H19A—C19—H19B | 109.5 |
O1—C3—C4 | 111.5 (2) | C10—C19—H19C | 109.5 |
C2—C3—C4 | 113.01 (19) | H19A—C19—H19C | 109.5 |
O1—C3—H3A | 108.5 | H19B—C19—H19C | 109.5 |
C2—C3—H3A | 108.5 | O2—C20—C21 | 106.5 (2) |
C4—C3—H3A | 108.5 | O2—C20—C17 | 108.10 (19) |
C28—C4—C3 | 108.07 (19) | C21—C20—C17 | 112.1 (2) |
C28—C4—C29 | 106.7 (2) | O2—C20—C22 | 107.25 (18) |
C3—C4—C29 | 109.2 (2) | C21—C20—C22 | 110.4 (2) |
C28—C4—C5 | 109.61 (19) | C17—C20—C22 | 112.2 (2) |
C3—C4—C5 | 108.92 (18) | C20—C21—H21A | 109.5 |
C29—C4—C5 | 114.21 (19) | C20—C21—H21B | 109.5 |
C6—C5—C4 | 113.93 (19) | H21A—C21—H21B | 109.5 |
C6—C5—C10 | 110.83 (18) | C20—C21—H21C | 109.5 |
C4—C5—C10 | 116.96 (19) | H21A—C21—H21C | 109.5 |
C6—C5—H5A | 104.5 | H21B—C21—H21C | 109.5 |
C4—C5—H5A | 104.5 | C23—C22—C20 | 116.9 (2) |
C10—C5—H5A | 104.5 | C23—C22—H22A | 108.1 |
C7—C6—C5 | 109.98 (19) | C20—C22—H22A | 108.1 |
C7—C6—H6A | 109.7 | C23—C22—H22B | 108.1 |
C5—C6—H6A | 109.7 | C20—C22—H22B | 108.1 |
C7—C6—H6B | 109.7 | H22A—C22—H22B | 107.3 |
C5—C6—H6B | 109.7 | C24A—C23—C22 | 122.9 (5) |
H6A—C6—H6B | 108.2 | C22—C23—C24 | 106.7 (4) |
C6—C7—C8 | 113.7 (2) | C24A—C23—H23A | 110.4 |
C6—C7—H7A | 108.8 | C22—C23—H23A | 110.4 |
C8—C7—H7A | 108.8 | C24—C23—H23A | 110.4 |
C6—C7—H7B | 108.8 | C24A—C23—H23B | 92.3 |
C8—C7—H7B | 108.8 | C22—C23—H23B | 110.4 |
H7A—C7—H7B | 107.7 | C24—C23—H23B | 110.4 |
C7—C8—C18 | 107.26 (19) | H23A—C23—H23B | 108.6 |
C7—C8—C9 | 109.42 (17) | C24A—C23—H23C | 108.3 |
C18—C8—C9 | 112.0 (2) | C22—C23—H23C | 106.4 |
C7—C8—C14 | 110.1 (2) | C24—C23—H23C | 127.4 |
C18—C8—C14 | 110.48 (18) | H23A—C23—H23C | 94.6 |
C9—C8—C14 | 107.62 (18) | C24A—C23—H23D | 105.4 |
C11—C9—C8 | 111.60 (17) | C22—C23—H23D | 106.4 |
C11—C9—C10 | 114.9 (2) | C24—C23—H23D | 101.8 |
C8—C9—C10 | 115.88 (18) | H23B—C23—H23D | 120.1 |
C11—C9—H9A | 104.3 | H23C—C23—H23D | 106.5 |
C8—C9—H9A | 104.3 | C25—C24—C23 | 127.9 (9) |
C10—C9—H9A | 104.3 | C25—C24—H24A | 116.1 |
C19—C10—C1 | 107.6 (2) | C23—C24—H24A | 116.1 |
C19—C10—C5 | 115.41 (19) | C24—C25—C27 | 122.6 (12) |
C1—C10—C5 | 107.65 (18) | C24—C25—C26 | 121.3 (12) |
C19—C10—C9 | 112.78 (18) | C27—C25—C26 | 116.1 (8) |
C1—C10—C9 | 107.94 (18) | C25A—C24A—C23 | 129.1 (13) |
C5—C10—C9 | 105.14 (19) | C25A—C24A—H24B | 115.5 |
C9—C11—C12 | 112.6 (2) | C23—C24A—H24B | 115.5 |
C9—C11—H11A | 109.1 | C24A—C25A—C26A | 122.3 (17) |
C12—C11—H11A | 109.1 | C24A—C25A—C27A | 121.4 (14) |
C9—C11—H11B | 109.1 | C26A—C25A—C27A | 116.1 (11) |
C12—C11—H11B | 109.1 | C25A—C26A—H26D | 109.5 |
H11A—C11—H11B | 107.8 | C25A—C26A—H26E | 109.5 |
C13—C12—C11 | 109.10 (19) | H26D—C26A—H26E | 109.5 |
C13—C12—H12A | 109.9 | C25A—C26A—H26F | 109.5 |
C11—C12—H12A | 109.9 | H26D—C26A—H26F | 109.5 |
C13—C12—H12B | 109.9 | H26E—C26A—H26F | 109.5 |
C11—C12—H12B | 109.9 | C25A—C27A—H27D | 109.5 |
H12A—C12—H12B | 108.3 | C25A—C27A—H27E | 109.5 |
C12—C13—C17 | 120.0 (2) | H27D—C27A—H27E | 109.5 |
C12—C13—C14 | 110.19 (18) | C25A—C27A—H27F | 109.5 |
C17—C13—C14 | 104.92 (19) | H27D—C27A—H27F | 109.5 |
C12—C13—H13A | 107.0 | H27E—C27A—H27F | 109.5 |
C17—C13—H13A | 107.0 | C4—C28—H28A | 109.5 |
C14—C13—H13A | 107.0 | C4—C28—H28B | 109.5 |
C15—C14—C13 | 100.11 (17) | H28A—C28—H28B | 109.5 |
C15—C14—C30 | 106.2 (2) | C4—C28—H28C | 109.5 |
C13—C14—C30 | 110.8 (2) | H28A—C28—H28C | 109.5 |
C15—C14—C8 | 116.91 (19) | H28B—C28—H28C | 109.5 |
C13—C14—C8 | 109.86 (19) | C4—C29—H29A | 109.5 |
C30—C14—C8 | 112.24 (17) | C4—C29—H29B | 109.5 |
C14—C15—C16 | 103.5 (2) | H29A—C29—H29B | 109.5 |
C14—C15—H15A | 111.1 | C4—C29—H29C | 109.5 |
C16—C15—H15A | 111.1 | H29A—C29—H29C | 109.5 |
C14—C15—H15B | 111.1 | H29B—C29—H29C | 109.5 |
C16—C15—H15B | 111.1 | C14—C30—H30A | 109.5 |
H15A—C15—H15B | 109.0 | C14—C30—H30B | 109.5 |
C15—C16—C17 | 105.70 (19) | H30A—C30—H30B | 109.5 |
C15—C16—H16A | 110.6 | C14—C30—H30C | 109.5 |
C17—C16—H16A | 110.6 | H30A—C30—H30C | 109.5 |
C15—C16—H16B | 110.6 | H30B—C30—H30C | 109.5 |
C17—C16—H16B | 110.6 | O3Wi—O3W—H1W3 | 113.1 |
H16A—C16—H16B | 108.7 | H1W3—O3W—H2W3 | 118.4 |
C10—C1—C2—C3 | −57.8 (3) | C11—C12—C13—C14 | 59.5 (2) |
C1—C2—C3—O1 | −66.0 (2) | C12—C13—C14—C15 | 173.65 (18) |
C1—C2—C3—C4 | 56.9 (3) | C17—C13—C14—C15 | 43.1 (2) |
O1—C3—C4—C28 | −50.8 (2) | C12—C13—C14—C30 | 61.8 (2) |
C2—C3—C4—C28 | −171.06 (19) | C17—C13—C14—C30 | −68.7 (2) |
O1—C3—C4—C29 | −166.47 (19) | C12—C13—C14—C8 | −62.8 (2) |
C2—C3—C4—C29 | 73.3 (2) | C17—C13—C14—C8 | 166.71 (17) |
O1—C3—C4—C5 | 68.2 (2) | C7—C8—C14—C15 | −68.6 (2) |
C2—C3—C4—C5 | −52.0 (3) | C18—C8—C14—C15 | 49.7 (3) |
C28—C4—C5—C6 | −59.4 (3) | C9—C8—C14—C15 | 172.24 (19) |
C3—C4—C5—C6 | −177.4 (2) | C7—C8—C14—C13 | 178.30 (18) |
C29—C4—C5—C6 | 60.3 (3) | C18—C8—C14—C13 | −63.4 (2) |
C28—C4—C5—C10 | 169.14 (19) | C9—C8—C14—C13 | 59.1 (2) |
C3—C4—C5—C10 | 51.1 (3) | C7—C8—C14—C30 | 54.5 (3) |
C29—C4—C5—C10 | −71.2 (3) | C18—C8—C14—C30 | 172.8 (2) |
C4—C5—C6—C7 | 162.2 (2) | C9—C8—C14—C30 | −64.6 (3) |
C10—C5—C6—C7 | −63.4 (2) | C13—C14—C15—C16 | −44.8 (2) |
C5—C6—C7—C8 | 56.5 (3) | C30—C14—C15—C16 | 70.5 (2) |
C6—C7—C8—C18 | 72.7 (2) | C8—C14—C15—C16 | −163.3 (2) |
C6—C7—C8—C9 | −49.0 (3) | C14—C15—C16—C17 | 30.3 (2) |
C6—C7—C8—C14 | −167.05 (18) | C12—C13—C17—C20 | 86.8 (3) |
C7—C8—C9—C11 | −175.21 (18) | C14—C13—C17—C20 | −148.6 (2) |
C18—C8—C9—C11 | 66.0 (2) | C12—C13—C17—C16 | −149.2 (2) |
C14—C8—C9—C11 | −55.6 (2) | C14—C13—C17—C16 | −24.7 (2) |
C7—C8—C9—C10 | 50.8 (3) | C15—C16—C17—C20 | 122.2 (2) |
C18—C8—C9—C10 | −68.0 (2) | C15—C16—C17—C13 | −3.4 (2) |
C14—C8—C9—C10 | 170.35 (18) | C13—C17—C20—O2 | 62.8 (3) |
C2—C1—C10—C19 | −72.2 (2) | C16—C17—C20—O2 | −56.7 (2) |
C2—C1—C10—C5 | 52.7 (2) | C13—C17—C20—C21 | −54.3 (3) |
C2—C1—C10—C9 | 165.77 (19) | C16—C17—C20—C21 | −173.8 (2) |
C6—C5—C10—C19 | −63.9 (3) | C13—C17—C20—C22 | −179.2 (2) |
C4—C5—C10—C19 | 69.0 (3) | C16—C17—C20—C22 | 61.4 (3) |
C6—C5—C10—C1 | 175.91 (17) | O2—C20—C22—C23 | 177.3 (3) |
C4—C5—C10—C1 | −51.2 (2) | C21—C20—C22—C23 | −67.0 (3) |
C6—C5—C10—C9 | 61.0 (2) | C17—C20—C22—C23 | 58.8 (3) |
C4—C5—C10—C9 | −166.10 (18) | C20—C22—C23—C24A | −80.0 (6) |
C11—C9—C10—C19 | −62.2 (3) | C20—C22—C23—C24 | −93.2 (4) |
C8—C9—C10—C19 | 70.3 (3) | C24A—C23—C24—C25 | −12.1 (11) |
C11—C9—C10—C1 | 56.5 (2) | C22—C23—C24—C25 | 134.1 (8) |
C8—C9—C10—C1 | −170.92 (19) | C23—C24—C25—C27 | −0.7 (15) |
C11—C9—C10—C5 | 171.24 (18) | C23—C24—C25—C26 | −179.4 (9) |
C8—C9—C10—C5 | −56.2 (2) | C22—C23—C24A—C25A | 125.3 (8) |
C8—C9—C11—C12 | 55.7 (3) | C24—C23—C24A—C25A | 165 (2) |
C10—C9—C11—C12 | −169.78 (18) | C23—C24A—C25A—C26A | −177.2 (9) |
C9—C11—C12—C13 | −56.3 (3) | C23—C24A—C25A—C27A | −2.7 (14) |
C11—C12—C13—C17 | −178.5 (2) |
Symmetry code: (i) −x+2, −y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···O1W | 0.84 | 2.02 | 2.816 (3) | 157 |
O1W—H1W1···O1ii | 0.84 | 1.94 | 2.783 (3) | 175 |
O2W—H1W2···O2iii | 0.83 | 1.89 | 2.718 (3) | 177 |
Symmetry codes: (ii) y, −x+1, z+1/2; (iii) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C30H52O2·1.075H2O |
Mr | 463.99 |
Crystal system, space group | Tetragonal, P42 |
Temperature (K) | 100 |
a, c (Å) | 19.9481 (13), 7.3410 (7) |
V (Å3) | 2921.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.39 × 0.11 × 0.10 |
Data collection | |
Diffractometer | Bruker APEX Duo CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.975, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24864, 4543, 3887 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.162, 1.07 |
No. of reflections | 4543 |
No. of parameters | 332 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.48 |
Absolute structure | Nd |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···O1W | 0.84 | 2.02 | 2.816 (3) | 157 |
O1W—H1W1···O1i | 0.84 | 1.94 | 2.783 (3) | 175 |
O2W—H1W2···O2ii | 0.83 | 1.89 | 2.718 (3) | 177 |
Symmetry codes: (i) y, −x+1, z+1/2; (ii) x, y, z+1. |
Acknowledgements
AS, DH and US thank Padjadjaran University for financial support. HKF and SC thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Asakawa, J., Kasai, R., Yamasaki, K. & Tanaka, O. (1977). Tetrahedron, 33, 1935–1939. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chairgulprasert, V., Krisornpornsan, B. & Hamad, A. (2006). Songklanakarin J. Sci. Technol. 28, 321–326. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Greger, H., Pacher, T., Bream, B., Bacher, M. & Hofer, O. (2001). Phytochemistry, 57, 57–64. Web of Science CrossRef PubMed CAS Google Scholar
Grosvenor, P. W., Supriono, A. & Gray, D. O. (1995). J. Ethnopharm. 45, 97–111. CrossRef CAS Web of Science Google Scholar
Lima, M. da P., Braga, P. A. de C., Macedo, M. L., Silva, M. F., da das, G. F., Ferreira, A. G., Fernandes, J. B. & Vierira, P. C. (2004). J. Braz. Chem. Soc. 15, 385–394. CrossRef CAS Google Scholar
Qiu, S.-X., van Hung, N., Xuan, L. T., Gu, J.-Q., Lobkovsky, E., Khanh, T. C., Soejarto, D. D., Clardy, J., Pezzuto, J. M., Dong, Y., Tri, M. V., Huong, L. M. & Fong, H. H. S. (2001). Phytochem. 56 775–780. Web of Science CSD CrossRef CAS Google Scholar
Roux, D., Martin, M.-T., Adeline, M.-T., Sevenet, T., Hadi, A. H. A. & Pais, M. (1998). Phytochemistry, 49, 1745–1748. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yodsaoue, O., Sonprasit, J., Karalai, C., Ponglimanont, C., Tewtrakul, S. & Chantrapromma, S. (2012). Phytochemistry, 76, 83–91. Web of Science CrossRef CAS PubMed Google Scholar
Zhang, F., Wang, J. S., Gu, J. S. & Kong, L. Y. (2010). J. Nat. Prod. 73, 2042–2046. Web of Science CrossRef CAS PubMed 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.
Aglaia genus plants belonging to the Mahogany family have been known as a good source of organic acids, sesquiterpenes, diterpenes and triterpenes (Chairgulprasert et al., 2006; Qiu et al., 2001; Roux et al., 1998; Yodsaoue et al., 2012). Many of the various terpenenoids from this genus possess interesting biological properties such as anti-inflammatory (Yodsaoue et al., 2012), cytotoxic (Zhang et al., 2010) and insecticidal (Greger et al., 2001) activities. The title compound (I), 3-epi-Dammarenediol II or 3α,20(S)-dihydroxydammar-24-ene, was previously isolated from Trattinnickia burserifolia (Lima et al., 2004). However it is now isolated for the first time from Aglaia eximia, a plant which was used as a traditional medicine for the treatment of malaria in Indonesia (Grosvenor et al., 1995). Herein the crystal structure of (I) is reported.
Compound (I) has a dammarane nucleus and crystallized in a hydrated form, C30H52O2.1.075(H2O) (Fig. 1). Two of the water molecules, O1W and O2W, have half occupancies and lie on two-fold axis, the other H of each water molecule was generated by a symmetry operation, -x, -y, z, whereas the third water molecule, O3W, has 0.075 occupancy. The molecule of dammarane has four fused rings and all rings are in trans-fused conformation. The three cyclohexane rings are in standard chair conformations. The cyclopentane (C13–C17) adopts an envelope conformation with the puckered C14 atom having the maximum deviation of 0.288 (2) Å, Q = 0.457 (3) Å and θ = 220.1 (3)° (Cremer & Pople, 1975). The hydroxyl group at atom C3 is axially attached which is different from the corresponding hydroxyl group in Dammarenediol II (Asakawa et al., 1977). The methylheptene side chain is disordered over two positions; the major component and the minor component A (Fig. 1), with the refined site-occupancy ratio of 0.505 (1)/0.495 (1) and is axially attached at atom C20 with the torsion angle of C17–C20–C22–C23 = 58.83 (3)°, indicating an (+)-syn-clinal conformation with respect to the cyclopentane ring (Fig. 1). The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to a related structure (Qiu et al., 2001).
The crystal packing of (I) is consolidated by intermolecular ODammarane—H···Owater and Owater—H···ODammarane hydrogen bonds (Table 1). The molecules of 3-epi-Dammarenediol II and water molecules are linked by O—H···O hydrogen bonds into a three dimensional network (Fig. 2).