organic compounds
(20S)-Dammar-24-ene-3β,20-diol monohydrate from the bark of Aglaia exima (Meliaceae)
aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my
In the title compound {systematic name: (1R,2R,5R,7R,10R,11R,14S,15R)-14-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol monohydrate}, C30H52O2·H2O, the three fused cyclohexane rings adopt chair conformations and the hydroxy substituent of one of these occupies an axial position. The fused cyclopentane ring adopts an (with the flap atom being the C atom bearing the methyl group) and the 3-methylbut-2-enyl portion of its substituent is disordered over three sets of sites in a 0.413 (7):0.250 (7):0.337 (7) ratio. The O atoms of both water molecules occupy special positions of 2 In the crystal, Os—H⋯Ow and Ow—H⋯Os (s = steroid and w = water) hydrogen bonds link hydroxy groups and water molecules, forming a three-dimensional network. The crystal studied was found to be a non-merohedral twin with a 0.518 (1):0.482 (1) component ratio.
Related literature
For the isolation of 20S-dammar-24-ene-3β,20-diol from other plants, see: Anjaneyulu et al. (1985); Bianchini et al. (1988); Huang et al. (2010); Leonti et al. (2004); Pakhathirathien et al. (2005); Ukiya et al. (2010).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812034976/hb6931sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034976/hb6931Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034976/hb6931Isup3.cml
Aglaia exima was collected from the Bogor Botanical Garden, West Java, Indonesia in July 2006. The plant was identified by Herbarium Bogoriense of Bogor city. The dried and milled bark (3 kg) was extracted succesively 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) to give a colorless solid (63 mg). Colourless prisms were obtained by recrystallization from ethyl acetate solution. The chemical structure was established by NMR spectroscopic analysis; however, the analysis did not note the presence of water.Carbon- and oxygen-bound H-atoms were placed in calculated positions [C–H 0.98 to 1.00 Å, O–H 0.84 Å, Uiso(H) 1.2 to 1.5Ueq(C,O)] and were included in the
in the riding model approximation.The 3-methylbut-2-enyl chain is disordered over three sites in a 0.413 (7): 0.250: 0.337 ratio. The temperature factors of the singly-primed and doubly-primed atoms were set to those of the unprimed ones; the anisotropic temperature factors were restrained to be nearly isotropic. The 1,2-related distances were restrained to within 0.01 Å.
The final difference Fourier map had a peak at 3.64 Å from H1c. The peak, which is close to a special position, could not be refined as a half oxygen atom.
The
was calculated from 2574 Friedel pairs. The few oxygen atoms together with and disorder precluded a more accurate The is that expected from spectroscopic assignments. and disorder probably contributed to the large weighting scheme.The structure is a non-merohedral twin [twin law: -0.9998 - 0.0165 - 0.0977, 0.0160 - 0.9976 - 0.0931, -0.0130 - 0.0127) with a minor component of 48.2 (1)%.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).The molecular structure of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the 3-methylbut-2-enyl chain is not shown. |
C30H52O2·H2O | Dx = 1.056 Mg m−3 |
Mr = 462.73 | Cu Kα radiation, λ = 1.54184 Å |
Tetragonal, P42 | Cell parameters from 37417 reflections |
Hall symbol: P 4c | θ = 3.1–76.4° |
a = 19.9229 (1) Å | µ = 0.50 mm−1 |
c = 7.3302 (1) Å | T = 100 K |
V = 2909.52 (4) Å3 | Prism, colorless |
Z = 4 | 0.30 × 0.10 × 0.05 mm |
F(000) = 1032 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 15153 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 14049 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.068 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 76.9°, θmin = 3.1° |
ω scan | h = −25→25 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −25→24 |
Tmin = 0.864, Tmax = 0.975 | l = −9→7 |
11893 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)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.266 | w = 1/[σ2(Fo2) + (0.1593P)2 + 2.3284P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
15153 reflections | Δρmax = 1.15 e Å−3 |
341 parameters | Δρmin = −0.36 e Å−3 |
45 restraints | Absolute structure: Flack (1983), 2575 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (3) |
C30H52O2·H2O | Z = 4 |
Mr = 462.73 | Cu Kα radiation |
Tetragonal, P42 | µ = 0.50 mm−1 |
a = 19.9229 (1) Å | T = 100 K |
c = 7.3302 (1) Å | 0.30 × 0.10 × 0.05 mm |
V = 2909.52 (4) Å3 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 15153 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 14049 reflections with I > 2σ(I) |
Tmin = 0.864, Tmax = 0.975 | Rint = 0.068 |
11893 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.266 | Δρmax = 1.15 e Å−3 |
S = 1.15 | Δρmin = −0.36 e Å−3 |
15153 reflections | Absolute structure: Flack (1983), 2575 Friedel pairs |
341 parameters | Absolute structure parameter: 0.1 (3) |
45 restraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.40677 (8) | 0.95002 (8) | 0.4154 (3) | 0.0199 (3) | |
H1 | 0.4242 | 0.9693 | 0.3251 | 0.030* | |
O2 | 0.08964 (8) | 0.54803 (8) | 0.4294 (3) | 0.0208 (4) | |
H2 | 0.0743 | 0.5323 | 0.3316 | 0.031* | |
O1W | 0.5000 | 1.0000 | 0.1754 (4) | 0.0197 (5) | |
H1W | 0.4837 | 1.0303 | 0.1093 | 0.030* | |
O2W | 0.0000 | 0.5000 | 0.1640 (4) | 0.0203 (5) | |
H2W | 0.0164 | 0.4694 | 0.0987 | 0.031* | |
C1 | 0.23302 (12) | 1.02383 (11) | 0.3489 (4) | 0.0233 (5) | |
H1A | 0.2503 | 1.0699 | 0.3528 | 0.035* | |
H1B | 0.2121 | 1.0129 | 0.4662 | 0.035* | |
H1C | 0.1996 | 1.0200 | 0.2513 | 0.035* | |
C2 | 0.32326 (12) | 0.99569 (11) | 0.1298 (4) | 0.0204 (5) | |
H2A | 0.3368 | 1.0429 | 0.1364 | 0.031* | |
H2B | 0.2905 | 0.9899 | 0.0314 | 0.031* | |
H2C | 0.3627 | 0.9677 | 0.1056 | 0.031* | |
C3 | 0.29148 (12) | 0.97463 (11) | 0.3120 (3) | 0.0177 (5) | |
C4 | 0.34506 (11) | 0.98337 (11) | 0.4633 (4) | 0.0184 (5) | |
H4 | 0.3543 | 1.0323 | 0.4797 | 0.022* | |
C5 | 0.32263 (12) | 0.95406 (11) | 0.6451 (3) | 0.0195 (5) | |
H5A | 0.2830 | 0.9792 | 0.6899 | 0.023* | |
H5B | 0.3591 | 0.9594 | 0.7356 | 0.023* | |
C6 | 0.30465 (11) | 0.87956 (11) | 0.6280 (3) | 0.0179 (5) | |
H6A | 0.2899 | 0.8627 | 0.7486 | 0.022* | |
H6B | 0.3454 | 0.8542 | 0.5925 | 0.022* | |
C7 | 0.18212 (12) | 0.89138 (12) | 0.5695 (4) | 0.0201 (5) | |
H7A | 0.1854 | 0.9397 | 0.5926 | 0.030* | |
H7B | 0.1732 | 0.8679 | 0.6844 | 0.030* | |
H7C | 0.1455 | 0.8827 | 0.4835 | 0.030* | |
C8 | 0.24895 (10) | 0.86580 (11) | 0.4874 (3) | 0.0151 (4) | |
C9 | 0.26992 (11) | 0.89986 (11) | 0.3032 (3) | 0.0148 (4) | |
H9 | 0.3115 | 0.8755 | 0.2656 | 0.018* | |
C10 | 0.21932 (11) | 0.88426 (11) | 0.1525 (3) | 0.0182 (5) | |
H10A | 0.2318 | 0.9088 | 0.0401 | 0.022* | |
H10B | 0.1741 | 0.8994 | 0.1904 | 0.022* | |
C11 | 0.21803 (11) | 0.80866 (11) | 0.1139 (3) | 0.0173 (4) | |
H11A | 0.2623 | 0.7950 | 0.0649 | 0.021* | |
H11B | 0.1839 | 0.7995 | 0.0188 | 0.021* | |
C12 | 0.12674 (11) | 0.77502 (12) | 0.3267 (4) | 0.0189 (5) | |
H12A | 0.0998 | 0.7600 | 0.2224 | 0.028* | |
H12B | 0.1176 | 0.8225 | 0.3508 | 0.028* | |
H12C | 0.1150 | 0.7484 | 0.4345 | 0.028* | |
C13 | 0.20209 (11) | 0.76580 (11) | 0.2830 (3) | 0.0149 (4) | |
C14 | 0.24821 (11) | 0.78826 (10) | 0.4463 (3) | 0.0151 (4) | |
H14 | 0.2948 | 0.7782 | 0.4037 | 0.018* | |
C15 | 0.23867 (12) | 0.74306 (11) | 0.6142 (4) | 0.0196 (5) | |
H15A | 0.2701 | 0.7574 | 0.7112 | 0.024* | |
H15B | 0.1924 | 0.7487 | 0.6612 | 0.024* | |
C16 | 0.25069 (11) | 0.66882 (11) | 0.5715 (3) | 0.0181 (5) | |
H16A | 0.2981 | 0.6619 | 0.5357 | 0.022* | |
H16B | 0.2416 | 0.6414 | 0.6814 | 0.022* | |
C17 | 0.20446 (11) | 0.64684 (10) | 0.4162 (3) | 0.0166 (4) | |
H17 | 0.1575 | 0.6572 | 0.4555 | 0.020* | |
C18 | 0.29079 (11) | 0.67911 (11) | 0.1759 (4) | 0.0197 (5) | |
H18A | 0.2984 | 0.6313 | 0.1526 | 0.030* | |
H18B | 0.3224 | 0.6949 | 0.2690 | 0.030* | |
H18C | 0.2976 | 0.7045 | 0.0630 | 0.030* | |
C19 | 0.21845 (11) | 0.68953 (11) | 0.2437 (3) | 0.0166 (4) | |
C20 | 0.17282 (12) | 0.65349 (11) | 0.1054 (4) | 0.0201 (5) | |
H20A | 0.1850 | 0.6657 | −0.0213 | 0.024* | |
H20B | 0.1251 | 0.6648 | 0.1265 | 0.024* | |
C21 | 0.18623 (12) | 0.57823 (11) | 0.1420 (4) | 0.0212 (5) | |
H21A | 0.2237 | 0.5618 | 0.0653 | 0.025* | |
H21B | 0.1457 | 0.5512 | 0.1151 | 0.025* | |
C22 | 0.20476 (11) | 0.57331 (11) | 0.3489 (3) | 0.0172 (5) | |
H22 | 0.2517 | 0.5559 | 0.3585 | 0.021* | |
C23 | 0.15811 (11) | 0.52502 (11) | 0.4544 (4) | 0.0199 (5) | |
C24 | 0.17163 (13) | 0.52639 (12) | 0.6588 (4) | 0.0247 (5) | |
H24A | 0.1409 | 0.4955 | 0.7207 | 0.037* | |
H24B | 0.1646 | 0.5720 | 0.7053 | 0.037* | |
H24C | 0.2181 | 0.5126 | 0.6821 | 0.037* | |
C25 | 0.16250 (12) | 0.45282 (11) | 0.3808 (4) | 0.0230 (5) | |
H25A | 0.1454 | 0.4528 | 0.2540 | 0.028* | 0.413 (3) |
H25B | 0.1319 | 0.4244 | 0.4540 | 0.028* | 0.413 (3) |
H25C | 0.1358 | 0.4504 | 0.2671 | 0.028* | 0.250 (7) |
H25D | 0.1408 | 0.4227 | 0.4707 | 0.028* | 0.250 (7) |
H25E | 0.1559 | 0.4542 | 0.2470 | 0.028* | 0.337 (7) |
H25F | 0.1249 | 0.4266 | 0.4332 | 0.028* | 0.337 (7) |
C26 | 0.2328 (3) | 0.4192 (5) | 0.3806 (13) | 0.0196 (19) | 0.413 (3) |
H26A | 0.2592 | 0.4366 | 0.4850 | 0.024* | 0.413 (3) |
H26B | 0.2274 | 0.3702 | 0.3973 | 0.024* | 0.413 (3) |
C27 | 0.2701 (7) | 0.4317 (7) | 0.2113 (18) | 0.036 (2) | 0.413 (3) |
H27 | 0.2415 | 0.4194 | 0.1131 | 0.043* | 0.413 (3) |
C28 | 0.3265 (4) | 0.4528 (5) | 0.1393 (15) | 0.0416 (18) | 0.413 (3) |
C29 | 0.3498 (5) | 0.4646 (7) | −0.0560 (17) | 0.059 (2) | 0.413 (3) |
H29A | 0.3927 | 0.4417 | −0.0759 | 0.089* | 0.413 (3) |
H29B | 0.3554 | 0.5128 | −0.0769 | 0.089* | 0.413 (3) |
H29C | 0.3162 | 0.4468 | −0.1409 | 0.089* | 0.413 (3) |
C30 | 0.3800 (6) | 0.4710 (7) | 0.277 (2) | 0.074 (3) | 0.413 (3) |
H30A | 0.3631 | 0.4623 | 0.4003 | 0.112* | 0.413 (3) |
H30B | 0.3913 | 0.5186 | 0.2646 | 0.112* | 0.413 (3) |
H30C | 0.4201 | 0.4437 | 0.2550 | 0.112* | 0.413 (3) |
C26' | 0.2338 (6) | 0.4245 (11) | 0.340 (2) | 0.0196 (19) | 0.250 (7) |
H26C | 0.2632 | 0.4408 | 0.4395 | 0.024* | 0.250 (7) |
H26D | 0.2305 | 0.3752 | 0.3550 | 0.024* | 0.250 (7) |
C27' | 0.2706 (9) | 0.4359 (15) | 0.170 (2) | 0.036 (2) | 0.250 (7) |
H27' | 0.2516 | 0.4353 | 0.0509 | 0.043* | 0.250 (7) |
C28' | 0.3390 (7) | 0.4479 (8) | 0.211 (3) | 0.0416 (18) | 0.250 (7) |
C29' | 0.3714 (9) | 0.4563 (11) | 0.024 (3) | 0.059 (2) | 0.250 (7) |
H29D | 0.3364 | 0.4576 | −0.0696 | 0.089* | 0.250 (7) |
H29E | 0.4016 | 0.4185 | 0.0007 | 0.089* | 0.250 (7) |
H29F | 0.3970 | 0.4983 | 0.0215 | 0.089* | 0.250 (7) |
C30' | 0.3828 (10) | 0.4522 (13) | 0.380 (4) | 0.074 (3) | 0.250 (7) |
H30D | 0.3546 | 0.4492 | 0.4889 | 0.112* | 0.250 (7) |
H30E | 0.4068 | 0.4951 | 0.3799 | 0.112* | 0.250 (7) |
H30F | 0.4152 | 0.4152 | 0.3792 | 0.112* | 0.250 (7) |
C26" | 0.2285 (6) | 0.4150 (10) | 0.423 (2) | 0.0196 (19) | 0.337 (7) |
H26E | 0.2461 | 0.4296 | 0.5426 | 0.024* | 0.337 (7) |
H26F | 0.2194 | 0.3662 | 0.4293 | 0.024* | 0.337 (7) |
C27" | 0.2785 (6) | 0.4279 (7) | 0.2825 (19) | 0.036 (2) | 0.337 (7) |
H27" | 0.2648 | 0.4187 | 0.1609 | 0.043* | 0.337 (7) |
C28" | 0.3442 (5) | 0.4520 (5) | 0.3021 (19) | 0.0416 (18) | 0.337 (7) |
C29" | 0.3880 (6) | 0.4653 (7) | 0.136 (2) | 0.059 (2) | 0.337 (7) |
H29G | 0.3598 | 0.4674 | 0.0270 | 0.089* | 0.337 (7) |
H29H | 0.4208 | 0.4290 | 0.1234 | 0.089* | 0.337 (7) |
H29I | 0.4116 | 0.5081 | 0.1522 | 0.089* | 0.337 (7) |
C30" | 0.3691 (7) | 0.4694 (9) | 0.493 (2) | 0.074 (3) | 0.337 (7) |
H30G | 0.3606 | 0.5170 | 0.5174 | 0.112* | 0.337 (7) |
H30H | 0.4174 | 0.4606 | 0.5005 | 0.112* | 0.337 (7) |
H30I | 0.3454 | 0.4418 | 0.5827 | 0.112* | 0.337 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0214 (8) | 0.0221 (8) | 0.0162 (9) | −0.0034 (6) | 0.0000 (7) | −0.0006 (7) |
O2 | 0.0198 (8) | 0.0223 (8) | 0.0202 (10) | −0.0020 (6) | 0.0014 (7) | −0.0015 (7) |
O1W | 0.0230 (11) | 0.0194 (11) | 0.0168 (13) | 0.0029 (8) | 0.000 | 0.000 |
O2W | 0.0254 (11) | 0.0196 (11) | 0.0161 (13) | 0.0054 (8) | 0.000 | 0.000 |
C1 | 0.0280 (12) | 0.0164 (10) | 0.0255 (14) | 0.0030 (8) | −0.0015 (10) | −0.0008 (9) |
C2 | 0.0240 (11) | 0.0194 (10) | 0.0179 (13) | −0.0032 (8) | 0.0001 (9) | 0.0031 (9) |
C3 | 0.0223 (11) | 0.0163 (10) | 0.0145 (12) | −0.0017 (8) | 0.0011 (9) | 0.0016 (9) |
C4 | 0.0227 (11) | 0.0160 (10) | 0.0164 (13) | −0.0021 (8) | −0.0011 (9) | −0.0029 (9) |
C5 | 0.0273 (11) | 0.0195 (10) | 0.0116 (13) | −0.0055 (8) | −0.0018 (9) | −0.0019 (9) |
C6 | 0.0234 (11) | 0.0191 (10) | 0.0113 (12) | −0.0031 (8) | −0.0019 (9) | 0.0002 (9) |
C7 | 0.0225 (11) | 0.0215 (11) | 0.0162 (13) | −0.0019 (8) | 0.0048 (9) | −0.0021 (9) |
C8 | 0.0170 (10) | 0.0138 (10) | 0.0145 (12) | 0.0001 (7) | 0.0002 (8) | −0.0013 (8) |
C9 | 0.0181 (10) | 0.0146 (9) | 0.0118 (12) | −0.0011 (7) | 0.0012 (8) | 0.0009 (8) |
C10 | 0.0231 (11) | 0.0176 (10) | 0.0140 (13) | 0.0008 (8) | −0.0025 (9) | 0.0018 (9) |
C11 | 0.0230 (10) | 0.0195 (10) | 0.0093 (11) | −0.0023 (8) | −0.0023 (9) | 0.0001 (9) |
C12 | 0.0173 (10) | 0.0219 (11) | 0.0175 (13) | −0.0020 (8) | −0.0016 (9) | −0.0029 (9) |
C13 | 0.0156 (10) | 0.0179 (10) | 0.0110 (11) | −0.0023 (7) | 0.0000 (8) | −0.0007 (8) |
C14 | 0.0162 (10) | 0.0178 (10) | 0.0112 (12) | 0.0002 (7) | −0.0016 (8) | −0.0014 (9) |
C15 | 0.0244 (11) | 0.0200 (11) | 0.0144 (13) | −0.0052 (8) | −0.0022 (9) | −0.0010 (9) |
C16 | 0.0209 (11) | 0.0187 (10) | 0.0148 (12) | −0.0022 (8) | −0.0024 (9) | 0.0025 (9) |
C17 | 0.0191 (10) | 0.0159 (10) | 0.0149 (12) | −0.0034 (7) | 0.0019 (9) | −0.0015 (9) |
C18 | 0.0205 (10) | 0.0170 (10) | 0.0218 (13) | −0.0022 (8) | 0.0035 (9) | −0.0019 (9) |
C19 | 0.0175 (10) | 0.0184 (11) | 0.0140 (12) | −0.0026 (8) | 0.0013 (9) | −0.0002 (9) |
C20 | 0.0261 (11) | 0.0200 (10) | 0.0142 (12) | −0.0034 (8) | −0.0011 (9) | −0.0015 (9) |
C21 | 0.0280 (12) | 0.0197 (11) | 0.0158 (13) | −0.0045 (8) | 0.0011 (10) | −0.0030 (9) |
C22 | 0.0194 (10) | 0.0156 (10) | 0.0167 (13) | 0.0001 (7) | 0.0004 (9) | −0.0020 (9) |
C23 | 0.0203 (11) | 0.0193 (11) | 0.0200 (14) | −0.0015 (8) | −0.0002 (9) | 0.0016 (9) |
C24 | 0.0303 (12) | 0.0227 (11) | 0.0210 (14) | −0.0059 (9) | −0.0026 (11) | 0.0041 (10) |
C25 | 0.0251 (11) | 0.0187 (11) | 0.0253 (15) | −0.0039 (8) | −0.0015 (10) | 0.0028 (10) |
C26 | 0.0337 (17) | 0.014 (3) | 0.012 (6) | 0.0011 (16) | −0.004 (3) | 0.009 (4) |
C27 | 0.034 (2) | 0.021 (2) | 0.053 (6) | 0.0028 (16) | 0.018 (3) | 0.000 (5) |
C28 | 0.028 (3) | 0.041 (2) | 0.057 (5) | −0.0006 (19) | 0.002 (3) | −0.007 (4) |
C29 | 0.029 (3) | 0.075 (4) | 0.073 (6) | −0.002 (3) | 0.010 (3) | −0.002 (4) |
C30 | 0.038 (3) | 0.093 (5) | 0.091 (7) | −0.014 (3) | −0.020 (5) | 0.019 (5) |
C26' | 0.0337 (17) | 0.014 (3) | 0.012 (6) | 0.0011 (16) | −0.004 (3) | 0.009 (4) |
C27' | 0.034 (2) | 0.021 (2) | 0.053 (6) | 0.0028 (16) | 0.018 (3) | 0.000 (5) |
C28' | 0.028 (3) | 0.041 (2) | 0.057 (5) | −0.0006 (19) | 0.002 (3) | −0.007 (4) |
C29' | 0.029 (3) | 0.075 (4) | 0.073 (6) | −0.002 (3) | 0.010 (3) | −0.002 (4) |
C30' | 0.038 (3) | 0.093 (5) | 0.091 (7) | −0.014 (3) | −0.020 (5) | 0.019 (5) |
C26" | 0.0337 (17) | 0.014 (3) | 0.012 (6) | 0.0011 (16) | −0.004 (3) | 0.009 (4) |
C27" | 0.034 (2) | 0.021 (2) | 0.053 (6) | 0.0028 (16) | 0.018 (3) | 0.000 (5) |
C28" | 0.028 (3) | 0.041 (2) | 0.057 (5) | −0.0006 (19) | 0.002 (3) | −0.007 (4) |
C29" | 0.029 (3) | 0.075 (4) | 0.073 (6) | −0.002 (3) | 0.010 (3) | −0.002 (4) |
C30" | 0.038 (3) | 0.093 (5) | 0.091 (7) | −0.014 (3) | −0.020 (5) | 0.019 (5) |
O1—C4 | 1.441 (3) | C20—H20A | 0.9900 |
O1—H1 | 0.8400 | C20—H20B | 0.9900 |
O2—C23 | 1.451 (3) | C21—C22 | 1.564 (4) |
O2—H2 | 0.8400 | C21—H21A | 0.9900 |
O1W—H1W | 0.8400 | C21—H21B | 0.9900 |
O2W—H2W | 0.8400 | C22—C23 | 1.545 (3) |
C1—C3 | 1.546 (3) | C22—H22 | 1.0000 |
C1—H1A | 0.9800 | C23—C24 | 1.523 (4) |
C1—H1B | 0.9800 | C23—C25 | 1.539 (3) |
C1—H1C | 0.9800 | C24—H24A | 0.9800 |
C2—C3 | 1.536 (3) | C24—H24B | 0.9800 |
C2—H2A | 0.9800 | C24—H24C | 0.9800 |
C2—H2B | 0.9800 | C25—C26" | 1.547 (7) |
C2—H2C | 0.9800 | C25—C26 | 1.553 (6) |
C3—C4 | 1.549 (3) | C25—C26' | 1.557 (8) |
C3—C9 | 1.552 (3) | C25—H25A | 0.9900 |
C4—C5 | 1.522 (3) | C25—H25B | 0.9900 |
C4—H4 | 1.0000 | C25—H25C | 0.9900 |
C5—C6 | 1.532 (3) | C25—H25D | 0.9902 |
C5—H5A | 0.9900 | C25—H25E | 0.9900 |
C5—H5B | 0.9900 | C25—H25F | 0.9901 |
C6—C8 | 1.539 (3) | C26—C27 | 1.467 (8) |
C6—H6A | 0.9900 | C26—H26A | 0.9900 |
C6—H6B | 0.9900 | C26—H26B | 0.9900 |
C7—C8 | 1.547 (3) | C27—C28 | 1.311 (13) |
C7—H7A | 0.9800 | C27—H27 | 0.9500 |
C7—H7B | 0.9800 | C28—C30 | 1.510 (14) |
C7—H7C | 0.9800 | C28—C29 | 1.523 (13) |
C8—C9 | 1.567 (3) | C29—H29A | 0.9800 |
C8—C14 | 1.574 (3) | C29—H29B | 0.9800 |
C9—C10 | 1.528 (3) | C29—H29C | 0.9800 |
C9—H9 | 1.0000 | C30—H30A | 0.9800 |
C10—C11 | 1.533 (3) | C30—H30B | 0.9800 |
C10—H10A | 0.9900 | C30—H30C | 0.9800 |
C10—H10B | 0.9900 | C26'—C27' | 1.465 (10) |
C11—C13 | 1.539 (3) | C26'—H26C | 0.9900 |
C11—H11A | 0.9900 | C26'—H26D | 0.9900 |
C11—H11B | 0.9900 | C27'—C28' | 1.417 (16) |
C12—C13 | 1.546 (3) | C27'—H27' | 0.9500 |
C12—H12A | 0.9800 | C28'—C30' | 1.514 (16) |
C12—H12B | 0.9800 | C28'—C29' | 1.523 (14) |
C12—H12C | 0.9800 | C29'—H29D | 0.9800 |
C13—C14 | 1.574 (3) | C29'—H29E | 0.9800 |
C13—C19 | 1.581 (3) | C29'—H29F | 0.9800 |
C14—C15 | 1.537 (3) | C30'—H30D | 0.9800 |
C14—H14 | 1.0000 | C30'—H30E | 0.9800 |
C15—C16 | 1.531 (3) | C30'—H30F | 0.9800 |
C15—H15A | 0.9900 | C26"—C27" | 1.454 (9) |
C15—H15B | 0.9900 | C26"—H26E | 0.9900 |
C16—C17 | 1.528 (3) | C26"—H26F | 0.9900 |
C16—H16A | 0.9900 | C27"—C28" | 1.401 (14) |
C16—H16B | 0.9900 | C27"—H27" | 0.9500 |
C17—C22 | 1.546 (3) | C28"—C29" | 1.518 (14) |
C17—C19 | 1.549 (3) | C28"—C30" | 1.522 (15) |
C17—H17 | 1.0000 | C29"—H29G | 0.9800 |
C18—C19 | 1.538 (3) | C29"—H29H | 0.9800 |
C18—H18A | 0.9800 | C29"—H29I | 0.9800 |
C18—H18B | 0.9800 | C30"—H30G | 0.9800 |
C18—H18C | 0.9800 | C30"—H30H | 0.9800 |
C19—C20 | 1.540 (3) | C30"—H30I | 0.9800 |
C20—C21 | 1.547 (3) | ||
C4—O1—H1 | 109.5 | H18A—C18—H18B | 109.5 |
C23—O2—H2 | 109.5 | C19—C18—H18C | 109.5 |
C3—C1—H1A | 109.5 | H18A—C18—H18C | 109.5 |
C3—C1—H1B | 109.5 | H18B—C18—H18C | 109.5 |
H1A—C1—H1B | 109.5 | C18—C19—C20 | 106.1 (2) |
C3—C1—H1C | 109.5 | C18—C19—C17 | 110.99 (19) |
H1A—C1—H1C | 109.5 | C20—C19—C17 | 100.09 (18) |
H1B—C1—H1C | 109.5 | C18—C19—C13 | 112.45 (17) |
C3—C2—H2A | 109.5 | C20—C19—C13 | 116.53 (19) |
C3—C2—H2B | 109.5 | C17—C19—C13 | 109.99 (19) |
H2A—C2—H2B | 109.5 | C19—C20—C21 | 103.65 (19) |
C3—C2—H2C | 109.5 | C19—C20—H20A | 111.0 |
H2A—C2—H2C | 109.5 | C21—C20—H20A | 111.0 |
H2B—C2—H2C | 109.5 | C19—C20—H20B | 111.0 |
C2—C3—C1 | 106.84 (19) | C21—C20—H20B | 111.0 |
C2—C3—C4 | 107.92 (19) | H20A—C20—H20B | 109.0 |
C1—C3—C4 | 108.8 (2) | C20—C21—C22 | 105.65 (19) |
C2—C3—C9 | 109.91 (19) | C20—C21—H21A | 110.6 |
C1—C3—C9 | 114.03 (19) | C22—C21—H21A | 110.6 |
C4—C3—C9 | 109.15 (18) | C20—C21—H21B | 110.6 |
O1—C4—C5 | 106.67 (19) | C22—C21—H21B | 110.6 |
O1—C4—C3 | 111.20 (19) | H21A—C21—H21B | 108.7 |
C5—C4—C3 | 112.43 (18) | C23—C22—C17 | 115.33 (19) |
O1—C4—H4 | 108.8 | C23—C22—C21 | 112.48 (19) |
C5—C4—H4 | 108.8 | C17—C22—C21 | 104.44 (18) |
C3—C4—H4 | 108.8 | C23—C22—H22 | 108.1 |
C4—C5—C6 | 111.6 (2) | C17—C22—H22 | 108.1 |
C4—C5—H5A | 109.3 | C21—C22—H22 | 108.1 |
C6—C5—H5A | 109.3 | O2—C23—C24 | 106.6 (2) |
C4—C5—H5B | 109.3 | O2—C23—C25 | 107.73 (18) |
C6—C5—H5B | 109.3 | C24—C23—C25 | 110.6 (2) |
H5A—C5—H5B | 108.0 | O2—C23—C22 | 107.80 (18) |
C5—C6—C8 | 113.33 (19) | C24—C23—C22 | 112.02 (19) |
C5—C6—H6A | 108.9 | C25—C23—C22 | 111.9 (2) |
C8—C6—H6A | 108.9 | C23—C24—H24A | 109.5 |
C5—C6—H6B | 108.9 | C23—C24—H24B | 109.5 |
C8—C6—H6B | 108.9 | H24A—C24—H24B | 109.5 |
H6A—C6—H6B | 107.7 | C23—C24—H24C | 109.5 |
C8—C7—H7A | 109.5 | H24A—C24—H24C | 109.5 |
C8—C7—H7B | 109.5 | H24B—C24—H24C | 109.5 |
H7A—C7—H7B | 109.5 | C23—C25—C26" | 115.7 (9) |
C8—C7—H7C | 109.5 | C23—C25—C26 | 117.0 (5) |
H7A—C7—H7C | 109.5 | C23—C25—C26' | 117.3 (10) |
H7B—C7—H7C | 109.5 | C23—C25—H25A | 108.0 |
C6—C8—C7 | 107.5 (2) | C26—C25—H25A | 108.0 |
C6—C8—C9 | 107.90 (17) | C23—C25—H25B | 108.0 |
C7—C8—C9 | 114.95 (18) | C26—C25—H25B | 108.0 |
C6—C8—C14 | 108.04 (17) | H25A—C25—H25B | 107.3 |
C7—C8—C14 | 112.92 (17) | C23—C25—H25C | 108.1 |
C9—C8—C14 | 105.23 (18) | C26—C25—H25C | 117.6 |
C10—C9—C3 | 114.06 (18) | C26'—C25—H25C | 108.1 |
C10—C9—C8 | 111.03 (18) | C23—C25—H25D | 107.9 |
C3—C9—C8 | 117.00 (19) | C23—C25—H25E | 108.4 |
C10—C9—H9 | 104.4 | C26"—C25—H25E | 108.8 |
C3—C9—H9 | 104.4 | C23—C25—H25F | 108.3 |
C8—C9—H9 | 104.4 | C26"—C25—H25F | 108.0 |
C9—C10—C11 | 110.16 (18) | H25E—C25—H25F | 107.4 |
C9—C10—H10A | 109.6 | C27—C26—C25 | 112.6 (7) |
C11—C10—H10A | 109.6 | C27—C26—H26A | 109.1 |
C9—C10—H10B | 109.6 | C25—C26—H26A | 109.1 |
C11—C10—H10B | 109.6 | C27—C26—H26B | 109.1 |
H10A—C10—H10B | 108.1 | C25—C26—H26B | 109.1 |
C10—C11—C13 | 113.6 (2) | H26A—C26—H26B | 107.8 |
C10—C11—H11A | 108.9 | C28—C27—C26 | 145.9 (14) |
C13—C11—H11A | 108.9 | C28—C27—H27 | 107.0 |
C10—C11—H11B | 108.9 | C26—C27—H27 | 107.0 |
C13—C11—H11B | 108.9 | C27—C28—C30 | 114.4 (12) |
H11A—C11—H11B | 107.7 | C27—C28—C29 | 133.5 (11) |
C13—C12—H12A | 109.5 | C30—C28—C29 | 112.1 (9) |
C13—C12—H12B | 109.5 | C27'—C26'—C25 | 124.3 (14) |
H12A—C12—H12B | 109.5 | C27'—C26'—H26C | 106.2 |
C13—C12—H12C | 109.5 | C25—C26'—H26C | 106.2 |
H12A—C12—H12C | 109.5 | C27'—C26'—H26D | 106.2 |
H12B—C12—H12C | 109.5 | C25—C26'—H26D | 106.2 |
C11—C13—C12 | 107.53 (19) | H26C—C26'—H26D | 106.4 |
C11—C13—C14 | 109.55 (17) | C28'—C27'—C26' | 109.0 (16) |
C12—C13—C14 | 112.08 (19) | C28'—C27'—H27' | 125.5 |
C11—C13—C19 | 110.12 (19) | C26'—C27'—H27' | 125.5 |
C12—C13—C19 | 110.62 (17) | C27'—C28'—C30' | 137.5 (17) |
C14—C13—C19 | 106.95 (17) | C27'—C28'—C29' | 103.5 (14) |
C15—C14—C13 | 111.72 (17) | C30'—C28'—C29' | 118.9 (15) |
C15—C14—C8 | 115.04 (19) | C28'—C29'—H29D | 109.5 |
C13—C14—C8 | 115.47 (18) | C28'—C29'—H29E | 109.5 |
C15—C14—H14 | 104.3 | H29D—C29'—H29E | 109.5 |
C13—C14—H14 | 104.3 | C28'—C29'—H29F | 109.5 |
C8—C14—H14 | 104.3 | H29D—C29'—H29F | 109.5 |
C16—C15—C14 | 112.5 (2) | H29E—C29'—H29F | 109.5 |
C16—C15—H15A | 109.1 | C28'—C30'—H30D | 109.5 |
C14—C15—H15A | 109.1 | C28'—C30'—H30E | 109.5 |
C16—C15—H15B | 109.1 | H30D—C30'—H30E | 109.5 |
C14—C15—H15B | 109.1 | C28'—C30'—H30F | 109.5 |
H15A—C15—H15B | 107.8 | H30D—C30'—H30F | 109.5 |
C17—C16—C15 | 109.57 (18) | H30E—C30'—H30F | 109.5 |
C17—C16—H16A | 109.8 | C27"—C26"—C25 | 110.9 (9) |
C15—C16—H16A | 109.8 | C27"—C26"—H26E | 109.5 |
C17—C16—H16B | 109.8 | C25—C26"—H26E | 109.5 |
C15—C16—H16B | 109.8 | C27"—C26"—H26F | 109.5 |
H16A—C16—H16B | 108.2 | C25—C26"—H26F | 109.5 |
C16—C17—C22 | 120.46 (19) | H26E—C26"—H26F | 108.1 |
C16—C17—C19 | 110.00 (17) | C28"—C27"—C26" | 128.9 (14) |
C22—C17—C19 | 105.02 (19) | C28"—C27"—H27" | 115.5 |
C16—C17—H17 | 106.9 | C26"—C27"—H27" | 115.5 |
C22—C17—H17 | 106.9 | C27"—C28"—C29" | 121.0 (11) |
C19—C17—H17 | 106.9 | C27"—C28"—C30" | 118.5 (11) |
C19—C18—H18A | 109.5 | C29"—C28"—C30" | 120.4 (11) |
C19—C18—H18B | 109.5 | ||
C2—C3—C4—O1 | −51.8 (2) | C11—C13—C19—C18 | 54.0 (3) |
C1—C3—C4—O1 | −167.36 (18) | C12—C13—C19—C18 | 172.7 (2) |
C9—C3—C4—O1 | 67.6 (2) | C14—C13—C19—C18 | −65.0 (2) |
C2—C3—C4—C5 | −171.33 (18) | C11—C13—C19—C20 | −68.8 (2) |
C1—C3—C4—C5 | 73.1 (2) | C12—C13—C19—C20 | 49.9 (3) |
C9—C3—C4—C5 | −51.9 (2) | C14—C13—C19—C20 | 172.23 (19) |
O1—C4—C5—C6 | −65.2 (2) | C11—C13—C19—C17 | 178.24 (18) |
C3—C4—C5—C6 | 56.9 (3) | C12—C13—C19—C17 | −63.0 (2) |
C4—C5—C6—C8 | −58.0 (3) | C14—C13—C19—C17 | 59.3 (2) |
C5—C6—C8—C7 | −72.1 (2) | C18—C19—C20—C21 | 71.1 (2) |
C5—C6—C8—C9 | 52.4 (2) | C17—C19—C20—C21 | −44.3 (2) |
C5—C6—C8—C14 | 165.72 (19) | C13—C19—C20—C21 | −162.83 (19) |
C2—C3—C9—C10 | −59.2 (2) | C19—C20—C21—C22 | 29.7 (2) |
C1—C3—C9—C10 | 60.8 (3) | C16—C17—C22—C23 | 86.4 (3) |
C4—C3—C9—C10 | −177.36 (19) | C19—C17—C22—C23 | −148.94 (19) |
C2—C3—C9—C8 | 168.87 (18) | C16—C17—C22—C21 | −149.6 (2) |
C1—C3—C9—C8 | −71.2 (3) | C19—C17—C22—C21 | −25.0 (2) |
C4—C3—C9—C8 | 50.7 (2) | C20—C21—C22—C23 | 122.9 (2) |
C6—C8—C9—C10 | 176.04 (17) | C20—C21—C22—C17 | −2.9 (2) |
C7—C8—C9—C10 | −64.0 (2) | C17—C22—C23—O2 | 62.8 (3) |
C14—C8—C9—C10 | 60.9 (2) | C21—C22—C23—O2 | −56.9 (2) |
C6—C8—C9—C3 | −50.6 (2) | C17—C22—C23—C24 | −54.1 (3) |
C7—C8—C9—C3 | 69.3 (2) | C21—C22—C23—C24 | −173.8 (2) |
C14—C8—C9—C3 | −165.81 (18) | C17—C22—C23—C25 | −179.0 (2) |
C3—C9—C10—C11 | 161.98 (19) | C21—C22—C23—C25 | 61.4 (2) |
C8—C9—C10—C11 | −63.3 (2) | O2—C23—C25—C26" | −170.6 (5) |
C9—C10—C11—C13 | 56.8 (2) | C24—C23—C25—C26" | −54.5 (6) |
C10—C11—C13—C12 | 72.8 (2) | C22—C23—C25—C26" | 71.1 (6) |
C10—C11—C13—C14 | −49.3 (2) | O2—C23—C25—C26 | 175.8 (4) |
C10—C11—C13—C19 | −166.64 (17) | C24—C23—C25—C26 | −68.1 (4) |
C11—C13—C14—C15 | −175.11 (18) | C22—C23—C25—C26 | 57.5 (5) |
C12—C13—C14—C15 | 65.6 (2) | O2—C23—C25—C26' | 162.7 (7) |
C19—C13—C14—C15 | −55.8 (2) | C24—C23—C25—C26' | −81.2 (7) |
C11—C13—C14—C8 | 50.9 (2) | C22—C23—C25—C26' | 44.4 (7) |
C12—C13—C14—C8 | −68.4 (2) | C23—C25—C26—C27 | −89.5 (10) |
C19—C13—C14—C8 | 170.25 (18) | C26"—C25—C26—C27 | −176 (6) |
C6—C8—C14—C15 | 56.6 (2) | C26'—C25—C26—C27 | 5 (5) |
C7—C8—C14—C15 | −62.2 (3) | C25—C26—C27—C28 | 127.9 (19) |
C9—C8—C14—C15 | 171.71 (18) | C26—C27—C28—C30 | 3 (3) |
C6—C8—C14—C13 | −170.91 (19) | C26—C27—C28—C29 | −175.1 (16) |
C7—C8—C14—C13 | 70.3 (3) | C23—C25—C26'—C27' | −84 (2) |
C9—C8—C14—C13 | −55.8 (2) | C26"—C25—C26'—C27' | −177 (6) |
C13—C14—C15—C16 | 55.9 (2) | C26—C25—C26'—C27' | −176 (7) |
C8—C14—C15—C16 | −169.89 (17) | C25—C26'—C27'—C28' | 139 (2) |
C14—C15—C16—C17 | −56.4 (2) | C26'—C27'—C28'—C30' | 0 (4) |
C15—C16—C17—C22 | −178.3 (2) | C26'—C27'—C28'—C29' | 178.1 (19) |
C15—C16—C17—C19 | 59.5 (2) | C23—C25—C26"—C27" | −87.7 (15) |
C16—C17—C19—C18 | 62.3 (2) | C26—C25—C26"—C27" | 11 (4) |
C22—C17—C19—C18 | −68.7 (2) | C26'—C25—C26"—C27" | 12 (3) |
C16—C17—C19—C20 | 174.03 (18) | C25—C26"—C27"—C28" | 125.6 (15) |
C22—C17—C19—C20 | 43.0 (2) | C26"—C27"—C28"—C29" | −177.1 (14) |
C16—C17—C19—C13 | −62.8 (2) | C26"—C27"—C28"—C30" | −1 (2) |
C22—C17—C19—C13 | 166.21 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1w | 0.84 | 1.96 | 2.745 (2) | 154 |
O2—H2···O2w | 0.84 | 2.03 | 2.809 (2) | 154 |
O1w—H1w···O2i | 0.84 | 1.88 | 2.712 (2) | 171 |
O2w—H2w···O1ii | 0.84 | 1.95 | 2.786 (2) | 171 |
Symmetry codes: (i) −y+1, x+1, z−1/2; (ii) −y+1, x, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C30H52O2·H2O |
Mr | 462.73 |
Crystal system, space group | Tetragonal, P42 |
Temperature (K) | 100 |
a, c (Å) | 19.9229 (1), 7.3302 (1) |
V (Å3) | 2909.52 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.30 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.864, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11893, 15153, 14049 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.632 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.266, 1.15 |
No. of reflections | 15153 |
No. of parameters | 341 |
No. of restraints | 45 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.15, −0.36 |
Absolute structure | Flack (1983), 2575 Friedel pairs |
Absolute structure parameter | 0.1 (3) |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1w | 0.84 | 1.96 | 2.745 (2) | 154 |
O2—H2···O2w | 0.84 | 2.03 | 2.809 (2) | 154 |
O1w—H1w···O2i | 0.84 | 1.88 | 2.712 (2) | 171 |
O2w—H2w···O1ii | 0.84 | 1.95 | 2.786 (2) | 171 |
Symmetry codes: (i) −y+1, x+1, z−1/2; (ii) −y+1, x, z−1/2. |
Acknowledgements
We thank Padjadjaran University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.
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The genus of Aglaia (Meliaceae family) comprises more than a hundred woody plant species, most of which are found in Indonesia. In this part of the world, the genus provides fruit and they are also used in traditional medicines. 20S-Dammar-24-ene-3β,20-diol has been isolated from several plants, e.g., Ceriops tagal (Pakhathirathien et al., 2005), Ligustrum lucidum (Huang et al., 2010), Olea madagascariensis (Bianchini et al., 1988), Mangifera indica (Anjaneyulu et al. (1985), Mosquitoxylum jamaicense (Anacardiaceae) (Leonti et al., 2004) and Shoreajavanica (Dipterocarpaceae) (Ukiya et al., 2010). The compound is also available commercially.
14-[(2S)-2-Hydroxy-6-methylhept-5-en-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.02,7.011,15]heptadecan-5-olcrystallizes as a monohydrate (Scheme I). The Flack parameter, calculated from 2574 Friedel pairs, is sufficiently well refined despite the somewhat large standard deviation. The few oxygen atoms together with twinning and disorder precluded a more accurate refinement; nevertheless, the absolute configuration is that expected from spectroscopic assignments.
The three cyclohexane rings that are fused together adopt chair conformations; the cyclopentane ring that is fused with a cyclohexane ring adopts an envelope conformation. The 3-methylbut-2-enyl portion of its substituent is disordered over three positions in an approximate 1:1:1 ratio. The O atoms of both water molecules lie on special positions of 2 site symmetry. Both hydroxy groups are hydrogen-bond donors to water molecules; the water molecules themselves are hydrogen-bond donors to hydroxy groups to generate a three-dimensional hydrogen-bonded network (Table 1).