organic compounds
3β-Hydroxyfriedelan-17β-carboxylic acid
aCollege of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China, bDepartment of Chemistry, Hainan Normal University, Haikou 571158, People's Republic of China, and cDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, People's Republic of China
*Correspondence e-mail: lincuiwu@gxu.edu.cn
The title compound, C30H50O3, which was isolated from a marine endophytic fungus, is a new friedelan derivative. The molecule contains five six-membered rings, which exhibit boat (ring A), distorted boat (ring B) and chair (rings C–E) conformations. The is stabilized by intermolecular O—H⋯O hydrogen bonds, which link neighbouring molecules into 12-membered rings.
Related literature
For general background, see: Chen et al. (2003, 2005, 2006a,b); Lin et al. (2001a,b, 2002). For related structures, see: Dhaneshwar et al. (1987); Fun et al. (2007); Mo (1977); Mo et al. (1989); Sun et al. (2004).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808010295/xu2405sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010295/xu2405Isup2.hkl
Starter cultures were maintained on cornmeal seawater agar. Plugs of agar supporting mycelial growth were cut and transferred aseptically to a 250 ml Erlenmeyer flask containing 100 ml of liquid medium GYP (glucose 5 g/l, yeast extract 0.5 g/l, peptone 1 g/l, beef extract 0.5 g/l, NaCl 3 g/l). The flask was incubated at 30°C on a rotary shaker for 5 d, and the mycelium was aseptically transferred to a 500 ml Erlenmeyer flask containing culture liquid (200 ml). The flask was then incubated at 30°C for 4 weeks. The cultures (80 l) were filtered through cheesecloth. The filtrate was concentrated to 5 l in vacuo below 50°C and extracted three times by shaking with an equal volume of ethyl acetate. The combined organic extracts were applied to a silica gel column, eluting with a gradient of petroleum ether to ethyl acetate to offer title compound (30 mg). The single crystals of the title compound were obtained by recrystallizing from an ethyl acetate/petroleum ether solution (V/V 1:1).
The H atoms placed in calculated positions with O—H = 0.84 Å and C–H = 0.98–1.00 Å, and refined in riding mode with Uiso(H) = 1.5Ueq(O,C) for hydroxyl groups and methyl groups, or Uiso(H)= 1.2Ueq(C) for others. As no significant
effect, Friedel pairs were merged.Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).C30H50O3 | F(000) = 1016 |
Mr = 458.70 | Dx = 1.092 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 999 reflections |
a = 13.238 (3) Å | θ = 3.0–26.8° |
b = 24.141 (5) Å | µ = 0.07 mm−1 |
c = 8.7349 (17) Å | T = 153 K |
V = 2791.5 (10) Å3 | Block, colourless |
Z = 4 | 0.51 × 0.48 × 0.46 mm |
Bruker SMART CCD area-detector diffractometer | 3010 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 27.1°, θmin = 2.3° |
ω scans | h = −16→16 |
18448 measured reflections | k = −23→30 |
3466 independent reflections | l = −9→11 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0609P)2 + 0.5096P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3457 reflections | Δρmax = 0.20 e Å−3 |
308 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0119 (15) |
C30H50O3 | V = 2791.5 (10) Å3 |
Mr = 458.70 | Z = 4 |
Orthorhombic, P21212 | Mo Kα radiation |
a = 13.238 (3) Å | µ = 0.07 mm−1 |
b = 24.141 (5) Å | T = 153 K |
c = 8.7349 (17) Å | 0.51 × 0.48 × 0.46 mm |
Bruker SMART CCD area-detector diffractometer | 3010 reflections with I > 2σ(I) |
18448 measured reflections | Rint = 0.029 |
3466 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
3457 reflections | Δρmin = −0.15 e Å−3 |
308 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. In absence of significant anomalous dispersion effects, Friedel-pair reflections were merged prior to 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 | ||
C1 | 0.81598 (18) | 0.35284 (10) | −0.0686 (3) | 0.0481 (6) | |
H1A | 0.8073 | 0.3249 | −0.1506 | 0.058* | |
H1B | 0.8849 | 0.3483 | −0.0266 | 0.058* | |
C2 | 0.8082 (2) | 0.41090 (11) | −0.1410 (3) | 0.0556 (6) | |
C3 | 0.6970 (2) | 0.42285 (12) | −0.1844 (3) | 0.0613 (7) | |
H3A | 0.6717 | 0.4537 | −0.1203 | 0.074* | |
H3B | 0.6942 | 0.4350 | −0.2926 | 0.074* | |
C4 | 0.6285 (2) | 0.37339 (11) | −0.1639 (3) | 0.0529 (6) | |
H4A | 0.6502 | 0.3438 | −0.2351 | 0.063* | |
H4B | 0.5588 | 0.3842 | −0.1920 | 0.063* | |
C5 | 0.62811 (16) | 0.34982 (9) | 0.0025 (2) | 0.0373 (4) | |
C6 | 0.56513 (16) | 0.29657 (9) | 0.0022 (3) | 0.0421 (5) | |
H6A | 0.5873 | 0.2735 | −0.0853 | 0.051* | |
H6B | 0.4937 | 0.3067 | −0.0161 | 0.051* | |
C7 | 0.57009 (16) | 0.26112 (9) | 0.1476 (3) | 0.0427 (5) | |
H7A | 0.5629 | 0.2217 | 0.1180 | 0.051* | |
H7B | 0.5117 | 0.2707 | 0.2132 | 0.051* | |
C8 | 0.66815 (14) | 0.26743 (8) | 0.2439 (2) | 0.0321 (4) | |
C9 | 0.69014 (13) | 0.21204 (8) | 0.3279 (2) | 0.0319 (4) | |
H9 | 0.6958 | 0.1841 | 0.2439 | 0.038* | |
C10 | 0.60437 (15) | 0.19038 (9) | 0.4292 (3) | 0.0425 (5) | |
H10A | 0.6020 | 0.2120 | 0.5254 | 0.051* | |
H10B | 0.5391 | 0.1952 | 0.3756 | 0.051* | |
C11 | 0.62009 (16) | 0.12897 (9) | 0.4665 (3) | 0.0440 (5) | |
H11A | 0.6162 | 0.1073 | 0.3704 | 0.053* | |
H11B | 0.5645 | 0.1164 | 0.5338 | 0.053* | |
C12 | 0.72162 (15) | 0.11659 (9) | 0.5455 (2) | 0.0367 (5) | |
C13 | 0.74102 (18) | 0.05269 (9) | 0.5379 (3) | 0.0447 (5) | |
H13 | 0.7356 | 0.0428 | 0.4270 | 0.054* | |
C14 | 0.84770 (19) | 0.03498 (10) | 0.5858 (3) | 0.0508 (6) | |
H14 | 0.8565 | −0.0048 | 0.5568 | 0.061* | |
C15 | 0.92836 (19) | 0.06796 (11) | 0.5046 (4) | 0.0587 (7) | |
H15A | 0.9301 | 0.0569 | 0.3954 | 0.070* | |
H15B | 0.9949 | 0.0590 | 0.5499 | 0.070* | |
C16 | 0.91100 (16) | 0.13007 (10) | 0.5149 (3) | 0.0452 (5) | |
H16A | 0.9638 | 0.1497 | 0.4557 | 0.054* | |
H16B | 0.9160 | 0.1421 | 0.6230 | 0.054* | |
C17 | 0.80690 (15) | 0.14506 (9) | 0.4519 (2) | 0.0346 (4) | |
H17 | 0.8043 | 0.1265 | 0.3497 | 0.042* | |
C18 | 0.79289 (14) | 0.20805 (8) | 0.4146 (2) | 0.0321 (4) | |
C19 | 0.87692 (15) | 0.22646 (9) | 0.3048 (3) | 0.0396 (5) | |
H19A | 0.9408 | 0.2297 | 0.3632 | 0.048* | |
H19B | 0.8866 | 0.1973 | 0.2265 | 0.048* | |
C20 | 0.85661 (15) | 0.28143 (9) | 0.2237 (3) | 0.0382 (5) | |
H20A | 0.9133 | 0.2895 | 0.1533 | 0.046* | |
H20B | 0.8540 | 0.3114 | 0.3009 | 0.046* | |
C21 | 0.75695 (14) | 0.28132 (8) | 0.1319 (2) | 0.0323 (4) | |
C22 | 0.73960 (15) | 0.34027 (8) | 0.0593 (2) | 0.0357 (4) | |
H22 | 0.7521 | 0.3679 | 0.1424 | 0.043* | |
C31 | 0.8474 (3) | 0.45484 (13) | −0.0312 (4) | 0.0836 (10) | |
H31A | 0.9188 | 0.4477 | −0.0086 | 0.125* | |
H31B | 0.8083 | 0.4536 | 0.0640 | 0.125* | |
H31C | 0.8405 | 0.4915 | −0.0782 | 0.125* | |
C32 | 0.8739 (3) | 0.41075 (15) | −0.2853 (4) | 0.0878 (11) | |
H32A | 0.8739 | 0.4478 | −0.3311 | 0.132* | |
H32B | 0.8466 | 0.3840 | −0.3590 | 0.132* | |
H32C | 0.9432 | 0.4003 | −0.2583 | 0.132* | |
C33 | 0.57641 (18) | 0.39522 (9) | 0.0954 (3) | 0.0428 (5) | |
O34 | 0.61970 (15) | 0.43196 (7) | 0.1613 (2) | 0.0584 (5) | |
O35 | 0.47665 (13) | 0.39178 (8) | 0.0915 (2) | 0.0593 (5) | |
H35 | 0.4516 | 0.4172 | 0.1452 | 0.089* | |
C36 | 0.65061 (17) | 0.31401 (9) | 0.3614 (3) | 0.0424 (5) | |
H36A | 0.6119 | 0.2995 | 0.4482 | 0.064* | |
H36B | 0.6129 | 0.3442 | 0.3130 | 0.064* | |
H36C | 0.7159 | 0.3279 | 0.3977 | 0.064* | |
C37 | 0.76840 (19) | 0.23692 (9) | 0.0047 (3) | 0.0436 (5) | |
H37A | 0.8360 | 0.2395 | −0.0404 | 0.065* | |
H37B | 0.7175 | 0.2432 | −0.0748 | 0.065* | |
H37C | 0.7590 | 0.2000 | 0.0490 | 0.065* | |
C38 | 0.80133 (19) | 0.24406 (9) | 0.5599 (2) | 0.0439 (5) | |
H38A | 0.8499 | 0.2273 | 0.6307 | 0.066* | |
H38B | 0.7351 | 0.2465 | 0.6095 | 0.066* | |
H38C | 0.8244 | 0.2813 | 0.5319 | 0.066* | |
C39 | 0.7150 (2) | 0.13555 (10) | 0.7141 (3) | 0.0489 (6) | |
H39A | 0.6849 | 0.1726 | 0.7188 | 0.073* | |
H39B | 0.7829 | 0.1366 | 0.7585 | 0.073* | |
H39C | 0.6730 | 0.1095 | 0.7719 | 0.073* | |
C40 | 0.6620 (2) | 0.01711 (11) | 0.6185 (4) | 0.0617 (7) | |
H40A | 0.6789 | −0.0221 | 0.6050 | 0.093* | |
H40B | 0.5954 | 0.0245 | 0.5743 | 0.093* | |
H40C | 0.6612 | 0.0261 | 0.7279 | 0.093* | |
O41 | 0.86248 (15) | 0.03944 (7) | 0.7487 (2) | 0.0578 (5) | |
H41 | 0.8633 | 0.0076 | 0.7876 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0469 (12) | 0.0492 (13) | 0.0481 (13) | 0.0055 (10) | 0.0085 (11) | 0.0088 (11) |
C2 | 0.0647 (15) | 0.0510 (14) | 0.0512 (14) | 0.0024 (12) | 0.0137 (13) | 0.0141 (12) |
C3 | 0.0745 (17) | 0.0560 (15) | 0.0536 (15) | 0.0137 (13) | 0.0084 (14) | 0.0184 (13) |
C4 | 0.0593 (14) | 0.0600 (15) | 0.0392 (12) | 0.0123 (12) | −0.0052 (11) | 0.0072 (11) |
C5 | 0.0429 (10) | 0.0359 (10) | 0.0330 (10) | 0.0082 (9) | −0.0016 (9) | 0.0002 (8) |
C6 | 0.0422 (10) | 0.0395 (11) | 0.0447 (12) | 0.0055 (9) | −0.0151 (10) | −0.0021 (10) |
C7 | 0.0342 (10) | 0.0398 (11) | 0.0542 (13) | 0.0007 (9) | −0.0101 (10) | 0.0071 (11) |
C8 | 0.0291 (9) | 0.0343 (10) | 0.0329 (10) | 0.0038 (7) | −0.0019 (8) | 0.0002 (8) |
C9 | 0.0285 (8) | 0.0340 (10) | 0.0331 (10) | 0.0019 (8) | −0.0017 (8) | −0.0014 (8) |
C10 | 0.0308 (9) | 0.0475 (12) | 0.0493 (12) | 0.0026 (9) | 0.0001 (10) | 0.0090 (10) |
C11 | 0.0334 (9) | 0.0456 (12) | 0.0529 (13) | −0.0042 (9) | −0.0048 (10) | 0.0085 (10) |
C12 | 0.0369 (10) | 0.0346 (10) | 0.0388 (11) | −0.0008 (8) | −0.0062 (9) | 0.0025 (9) |
C13 | 0.0524 (12) | 0.0369 (11) | 0.0448 (13) | −0.0013 (10) | −0.0144 (11) | −0.0028 (10) |
C14 | 0.0594 (14) | 0.0329 (11) | 0.0600 (15) | 0.0073 (10) | −0.0166 (13) | 0.0007 (10) |
C15 | 0.0491 (13) | 0.0558 (15) | 0.0712 (17) | 0.0179 (12) | −0.0058 (13) | 0.0107 (14) |
C16 | 0.0352 (10) | 0.0495 (13) | 0.0510 (13) | 0.0043 (9) | −0.0082 (10) | 0.0091 (11) |
C17 | 0.0332 (9) | 0.0382 (10) | 0.0326 (10) | 0.0043 (8) | −0.0049 (8) | −0.0025 (8) |
C18 | 0.0297 (8) | 0.0350 (10) | 0.0317 (9) | 0.0014 (8) | −0.0019 (8) | 0.0002 (8) |
C19 | 0.0285 (9) | 0.0495 (12) | 0.0409 (11) | 0.0032 (8) | −0.0015 (9) | 0.0053 (9) |
C20 | 0.0312 (9) | 0.0452 (12) | 0.0383 (11) | −0.0017 (8) | 0.0002 (9) | 0.0048 (9) |
C21 | 0.0326 (9) | 0.0338 (10) | 0.0305 (9) | 0.0036 (8) | 0.0001 (8) | −0.0020 (8) |
C22 | 0.0389 (10) | 0.0348 (10) | 0.0333 (10) | 0.0029 (8) | −0.0004 (9) | −0.0010 (8) |
C31 | 0.101 (3) | 0.0595 (18) | 0.090 (2) | −0.0205 (18) | −0.002 (2) | 0.0065 (18) |
C32 | 0.101 (2) | 0.083 (2) | 0.079 (2) | 0.018 (2) | 0.043 (2) | 0.0334 (19) |
C33 | 0.0512 (12) | 0.0364 (11) | 0.0408 (11) | 0.0091 (10) | 0.0038 (10) | 0.0049 (9) |
O34 | 0.0668 (11) | 0.0356 (8) | 0.0727 (12) | 0.0049 (8) | 0.0050 (10) | −0.0131 (9) |
O35 | 0.0503 (9) | 0.0573 (11) | 0.0702 (12) | 0.0155 (8) | 0.0074 (9) | −0.0078 (9) |
C36 | 0.0477 (11) | 0.0399 (11) | 0.0397 (11) | 0.0092 (9) | 0.0083 (10) | −0.0004 (9) |
C37 | 0.0546 (13) | 0.0407 (12) | 0.0353 (10) | 0.0095 (10) | 0.0019 (10) | −0.0049 (10) |
C38 | 0.0547 (13) | 0.0410 (11) | 0.0359 (11) | −0.0025 (10) | −0.0086 (11) | −0.0019 (9) |
C39 | 0.0626 (14) | 0.0422 (12) | 0.0419 (12) | −0.0001 (11) | 0.0034 (11) | 0.0026 (10) |
C40 | 0.0683 (16) | 0.0443 (13) | 0.0725 (18) | −0.0146 (12) | −0.0183 (15) | 0.0096 (13) |
O41 | 0.0721 (11) | 0.0384 (9) | 0.0628 (11) | −0.0092 (8) | −0.0293 (10) | 0.0121 (8) |
C1—C22 | 1.537 (3) | C15—H15A | 0.9900 |
C1—C2 | 1.541 (3) | C15—H15B | 0.9900 |
C1—H1A | 0.9900 | C16—C17 | 1.528 (3) |
C1—H1B | 0.9900 | C16—H16A | 0.9900 |
C2—C31 | 1.522 (4) | C16—H16B | 0.9900 |
C2—C32 | 1.531 (4) | C17—C18 | 1.566 (3) |
C2—C3 | 1.547 (4) | C17—H17 | 1.0000 |
C3—C4 | 1.510 (4) | C18—C19 | 1.535 (3) |
C3—H3A | 0.9900 | C18—C38 | 1.542 (3) |
C3—H3B | 0.9900 | C19—C20 | 1.528 (3) |
C4—C5 | 1.561 (3) | C19—H19A | 0.9900 |
C4—H4A | 0.9900 | C19—H19B | 0.9900 |
C4—H4B | 0.9900 | C20—C21 | 1.544 (3) |
C5—C33 | 1.526 (3) | C20—H20A | 0.9900 |
C5—C6 | 1.532 (3) | C20—H20B | 0.9900 |
C5—C22 | 1.574 (3) | C21—C37 | 1.551 (3) |
C6—C7 | 1.533 (3) | C21—C22 | 1.575 (3) |
C6—H6A | 0.9900 | C22—H22 | 1.0000 |
C6—H6B | 0.9900 | C31—H31A | 0.9800 |
C7—C8 | 1.555 (3) | C31—H31B | 0.9800 |
C7—H7A | 0.9900 | C31—H31C | 0.9800 |
C7—H7B | 0.9900 | C32—H32A | 0.9800 |
C8—C36 | 1.540 (3) | C32—H32B | 0.9800 |
C8—C9 | 1.553 (3) | C32—H32C | 0.9800 |
C8—C21 | 1.566 (3) | C33—O34 | 1.203 (3) |
C9—C10 | 1.531 (3) | C33—O35 | 1.324 (3) |
C9—C18 | 1.560 (3) | O35—H35 | 0.8400 |
C9—H9 | 1.0000 | C36—H36A | 0.9800 |
C10—C11 | 1.532 (3) | C36—H36B | 0.9800 |
C10—H10A | 0.9900 | C36—H36C | 0.9800 |
C10—H10B | 0.9900 | C37—H37A | 0.9800 |
C11—C12 | 1.540 (3) | C37—H37B | 0.9800 |
C11—H11A | 0.9900 | C37—H37C | 0.9800 |
C11—H11B | 0.9900 | C38—H38A | 0.9800 |
C12—C39 | 1.544 (3) | C38—H38B | 0.9800 |
C12—C17 | 1.554 (3) | C38—H38C | 0.9800 |
C12—C13 | 1.565 (3) | C39—H39A | 0.9800 |
C13—C40 | 1.525 (4) | C39—H39B | 0.9800 |
C13—C14 | 1.534 (3) | C39—H39C | 0.9800 |
C13—H13 | 1.0000 | C40—H40A | 0.9800 |
C14—O41 | 1.440 (3) | C40—H40B | 0.9800 |
C14—C15 | 1.509 (4) | C40—H40C | 0.9800 |
C14—H14 | 1.0000 | O41—H41 | 0.8400 |
C15—C16 | 1.520 (3) | ||
C22—C1—C2 | 115.72 (19) | C15—C16—C17 | 110.41 (19) |
C22—C1—H1A | 108.4 | C15—C16—H16A | 109.6 |
C2—C1—H1A | 108.4 | C17—C16—H16A | 109.6 |
C22—C1—H1B | 108.4 | C15—C16—H16B | 109.6 |
C2—C1—H1B | 108.4 | C17—C16—H16B | 109.6 |
H1A—C1—H1B | 107.4 | H16A—C16—H16B | 108.1 |
C31—C2—C32 | 109.1 (3) | C16—C17—C12 | 111.15 (17) |
C31—C2—C1 | 110.6 (2) | C16—C17—C18 | 114.32 (17) |
C32—C2—C1 | 107.3 (2) | C12—C17—C18 | 116.92 (16) |
C31—C2—C3 | 110.4 (3) | C16—C17—H17 | 104.3 |
C32—C2—C3 | 109.8 (3) | C12—C17—H17 | 104.3 |
C1—C2—C3 | 109.5 (2) | C18—C17—H17 | 104.3 |
C4—C3—C2 | 113.3 (2) | C19—C18—C38 | 107.38 (17) |
C4—C3—H3A | 108.9 | C19—C18—C9 | 108.09 (15) |
C2—C3—H3A | 108.9 | C38—C18—C9 | 115.35 (17) |
C4—C3—H3B | 108.9 | C19—C18—C17 | 108.98 (16) |
C2—C3—H3B | 108.9 | C38—C18—C17 | 111.58 (17) |
H3A—C3—H3B | 107.7 | C9—C18—C17 | 105.31 (15) |
C3—C4—C5 | 113.6 (2) | C20—C19—C18 | 114.44 (17) |
C3—C4—H4A | 108.8 | C20—C19—H19A | 108.7 |
C5—C4—H4A | 108.8 | C18—C19—H19A | 108.7 |
C3—C4—H4B | 108.8 | C20—C19—H19B | 108.7 |
C5—C4—H4B | 108.8 | C18—C19—H19B | 108.7 |
H4A—C4—H4B | 107.7 | H19A—C19—H19B | 107.6 |
C33—C5—C6 | 111.08 (18) | C19—C20—C21 | 112.93 (17) |
C33—C5—C4 | 103.59 (17) | C19—C20—H20A | 109.0 |
C6—C5—C4 | 107.80 (18) | C21—C20—H20A | 109.0 |
C33—C5—C22 | 111.00 (17) | C19—C20—H20B | 109.0 |
C6—C5—C22 | 112.84 (16) | C21—C20—H20B | 109.0 |
C4—C5—C22 | 110.08 (18) | H20A—C20—H20B | 107.8 |
C5—C6—C7 | 116.32 (18) | C20—C21—C37 | 106.84 (16) |
C5—C6—H6A | 108.2 | C20—C21—C8 | 108.48 (15) |
C7—C6—H6A | 108.2 | C37—C21—C8 | 111.90 (17) |
C5—C6—H6B | 108.2 | C20—C21—C22 | 109.41 (16) |
C7—C6—H6B | 108.2 | C37—C21—C22 | 110.52 (16) |
H6A—C6—H6B | 107.4 | C8—C21—C22 | 109.61 (15) |
C6—C7—C8 | 115.44 (18) | C1—C22—C5 | 111.04 (18) |
C6—C7—H7A | 108.4 | C1—C22—C21 | 112.03 (17) |
C8—C7—H7A | 108.4 | C5—C22—C21 | 113.32 (16) |
C6—C7—H7B | 108.4 | C1—C22—H22 | 106.7 |
C8—C7—H7B | 108.4 | C5—C22—H22 | 106.7 |
H7A—C7—H7B | 107.5 | C21—C22—H22 | 106.7 |
C36—C8—C9 | 110.03 (16) | C2—C31—H31A | 109.5 |
C36—C8—C7 | 107.84 (16) | C2—C31—H31B | 109.5 |
C9—C8—C7 | 109.14 (16) | H31A—C31—H31B | 109.5 |
C36—C8—C21 | 111.92 (16) | C2—C31—H31C | 109.5 |
C9—C8—C21 | 109.81 (15) | H31A—C31—H31C | 109.5 |
C7—C8—C21 | 108.02 (16) | H31B—C31—H31C | 109.5 |
C10—C9—C8 | 115.34 (16) | C2—C32—H32A | 109.5 |
C10—C9—C18 | 110.17 (16) | C2—C32—H32B | 109.5 |
C8—C9—C18 | 116.49 (15) | H32A—C32—H32B | 109.5 |
C10—C9—H9 | 104.4 | C2—C32—H32C | 109.5 |
C8—C9—H9 | 104.4 | H32A—C32—H32C | 109.5 |
C18—C9—H9 | 104.4 | H32B—C32—H32C | 109.5 |
C11—C10—C9 | 110.65 (17) | O34—C33—O35 | 122.3 (2) |
C11—C10—H10A | 109.5 | O34—C33—C5 | 124.8 (2) |
C9—C10—H10A | 109.5 | O35—C33—C5 | 112.9 (2) |
C11—C10—H10B | 109.5 | C33—O35—H35 | 109.5 |
C9—C10—H10B | 109.5 | C8—C36—H36A | 109.5 |
H10A—C10—H10B | 108.1 | C8—C36—H36B | 109.5 |
C10—C11—C12 | 113.68 (18) | H36A—C36—H36B | 109.5 |
C10—C11—H11A | 108.8 | C8—C36—H36C | 109.5 |
C12—C11—H11A | 108.8 | H36A—C36—H36C | 109.5 |
C10—C11—H11B | 108.8 | H36B—C36—H36C | 109.5 |
C12—C11—H11B | 108.8 | C21—C37—H37A | 109.5 |
H11A—C11—H11B | 107.7 | C21—C37—H37B | 109.5 |
C11—C12—C39 | 108.68 (19) | H37A—C37—H37B | 109.5 |
C11—C12—C17 | 108.18 (17) | C21—C37—H37C | 109.5 |
C39—C12—C17 | 114.32 (18) | H37A—C37—H37C | 109.5 |
C11—C12—C13 | 108.38 (17) | H37B—C37—H37C | 109.5 |
C39—C12—C13 | 109.99 (18) | C18—C38—H38A | 109.5 |
C17—C12—C13 | 107.12 (17) | C18—C38—H38B | 109.5 |
C40—C13—C14 | 110.4 (2) | H38A—C38—H38B | 109.5 |
C40—C13—C12 | 115.0 (2) | C18—C38—H38C | 109.5 |
C14—C13—C12 | 114.48 (18) | H38A—C38—H38C | 109.5 |
C40—C13—H13 | 105.3 | H38B—C38—H38C | 109.5 |
C14—C13—H13 | 105.3 | C12—C39—H39A | 109.5 |
C12—C13—H13 | 105.3 | C12—C39—H39B | 109.5 |
O41—C14—C15 | 109.2 (2) | H39A—C39—H39B | 109.5 |
O41—C14—C13 | 111.9 (2) | C12—C39—H39C | 109.5 |
C15—C14—C13 | 112.1 (2) | H39A—C39—H39C | 109.5 |
O41—C14—H14 | 107.8 | H39B—C39—H39C | 109.5 |
C15—C14—H14 | 107.8 | C13—C40—H40A | 109.5 |
C13—C14—H14 | 107.8 | C13—C40—H40B | 109.5 |
C14—C15—C16 | 112.7 (2) | H40A—C40—H40B | 109.5 |
C14—C15—H15A | 109.1 | C13—C40—H40C | 109.5 |
C16—C15—H15A | 109.1 | H40A—C40—H40C | 109.5 |
C14—C15—H15B | 109.1 | H40B—C40—H40C | 109.5 |
C16—C15—H15B | 109.1 | C14—O41—H41 | 109.5 |
H15A—C15—H15B | 107.8 | ||
C22—C1—C2—C31 | 72.8 (3) | C13—C12—C17—C18 | 168.25 (17) |
C22—C1—C2—C32 | −168.3 (3) | C10—C9—C18—C19 | 176.21 (18) |
C22—C1—C2—C3 | −49.1 (3) | C8—C9—C18—C19 | −50.0 (2) |
C31—C2—C3—C4 | −129.2 (3) | C10—C9—C18—C38 | −63.6 (2) |
C32—C2—C3—C4 | 110.5 (3) | C8—C9—C18—C38 | 70.2 (2) |
C1—C2—C3—C4 | −7.1 (3) | C10—C9—C18—C17 | 59.8 (2) |
C2—C3—C4—C5 | 57.6 (3) | C8—C9—C18—C17 | −166.34 (16) |
C3—C4—C5—C33 | 68.3 (3) | C16—C17—C18—C19 | 55.0 (2) |
C3—C4—C5—C6 | −174.0 (2) | C12—C17—C18—C19 | −172.64 (16) |
C3—C4—C5—C22 | −50.5 (3) | C16—C17—C18—C38 | −63.4 (2) |
C33—C5—C6—C7 | −77.6 (2) | C12—C17—C18—C38 | 69.0 (2) |
C4—C5—C6—C7 | 169.56 (19) | C16—C17—C18—C9 | 170.78 (17) |
C22—C5—C6—C7 | 47.8 (3) | C12—C17—C18—C9 | −56.9 (2) |
C5—C6—C7—C8 | −25.9 (3) | C38—C18—C19—C20 | −75.4 (2) |
C6—C7—C8—C36 | 90.4 (2) | C9—C18—C19—C20 | 49.6 (2) |
C6—C7—C8—C9 | −150.07 (18) | C17—C18—C19—C20 | 163.59 (17) |
C6—C7—C8—C21 | −30.7 (2) | C18—C19—C20—C21 | −57.0 (2) |
C36—C8—C9—C10 | 62.4 (2) | C19—C20—C21—C37 | −63.1 (2) |
C7—C8—C9—C10 | −55.8 (2) | C19—C20—C21—C8 | 57.7 (2) |
C21—C8—C9—C10 | −174.02 (17) | C19—C20—C21—C22 | 177.21 (17) |
C36—C8—C9—C18 | −69.1 (2) | C36—C8—C21—C20 | 67.5 (2) |
C7—C8—C9—C18 | 172.75 (17) | C9—C8—C21—C20 | −55.0 (2) |
C21—C8—C9—C18 | 54.5 (2) | C7—C8—C21—C20 | −173.94 (16) |
C8—C9—C10—C11 | 162.92 (18) | C36—C8—C21—C37 | −174.90 (17) |
C18—C9—C10—C11 | −62.7 (2) | C9—C8—C21—C37 | 62.6 (2) |
C9—C10—C11—C12 | 57.3 (3) | C7—C8—C21—C37 | −56.3 (2) |
C10—C11—C12—C39 | 75.3 (2) | C36—C8—C21—C22 | −51.9 (2) |
C10—C11—C12—C17 | −49.4 (2) | C9—C8—C21—C22 | −174.43 (16) |
C10—C11—C12—C13 | −165.2 (2) | C7—C8—C21—C22 | 66.6 (2) |
C11—C12—C13—C40 | −61.1 (3) | C2—C1—C22—C5 | 55.1 (3) |
C39—C12—C13—C40 | 57.6 (3) | C2—C1—C22—C21 | −177.0 (2) |
C17—C12—C13—C40 | −177.61 (19) | C33—C5—C22—C1 | −118.2 (2) |
C11—C12—C13—C14 | 169.5 (2) | C6—C5—C22—C1 | 116.4 (2) |
C39—C12—C13—C14 | −71.8 (3) | C4—C5—C22—C1 | −4.1 (2) |
C17—C12—C13—C14 | 52.9 (3) | C33—C5—C22—C21 | 114.73 (19) |
C40—C13—C14—O41 | −58.8 (3) | C6—C5—C22—C21 | −10.7 (2) |
C12—C13—C14—O41 | 72.9 (3) | C4—C5—C22—C21 | −131.17 (18) |
C40—C13—C14—C15 | 178.1 (2) | C20—C21—C22—C1 | 69.3 (2) |
C12—C13—C14—C15 | −50.2 (3) | C37—C21—C22—C1 | −48.1 (2) |
O41—C14—C15—C16 | −74.1 (3) | C8—C21—C22—C1 | −171.89 (18) |
C13—C14—C15—C16 | 50.5 (3) | C20—C21—C22—C5 | −164.12 (17) |
C14—C15—C16—C17 | −56.4 (3) | C37—C21—C22—C5 | 78.5 (2) |
C15—C16—C17—C12 | 61.2 (3) | C8—C21—C22—C5 | −45.3 (2) |
C15—C16—C17—C18 | −163.8 (2) | C6—C5—C33—O34 | 151.5 (2) |
C11—C12—C17—C16 | −174.64 (19) | C4—C5—C33—O34 | −93.0 (3) |
C39—C12—C17—C16 | 64.1 (2) | C22—C5—C33—O34 | 25.1 (3) |
C13—C12—C17—C16 | −58.0 (2) | C6—C5—C33—O35 | −31.2 (3) |
C11—C12—C17—C18 | 51.6 (2) | C4—C5—C33—O35 | 84.3 (2) |
C39—C12—C17—C18 | −69.6 (2) | C22—C5—C33—O35 | −157.59 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O35—H35···O41i | 0.84 | 1.83 | 2.644 (2) | 163 |
O41—H41···O34ii | 0.84 | 1.89 | 2.721 (2) | 168 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C30H50O3 |
Mr | 458.70 |
Crystal system, space group | Orthorhombic, P21212 |
Temperature (K) | 153 |
a, b, c (Å) | 13.238 (3), 24.141 (5), 8.7349 (17) |
V (Å3) | 2791.5 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.51 × 0.48 × 0.46 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18448, 3466, 3010 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.640 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.112, 1.04 |
No. of reflections | 3457 |
No. of parameters | 308 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.15 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O35—H35···O41i | 0.84 | 1.83 | 2.644 (2) | 162.7 |
O41—H41···O34ii | 0.84 | 1.89 | 2.721 (2) | 168.1 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y−1/2, −z+1. |
Acknowledgements
The project was supported by Guangxi Science Foundation (Guikezi0728257, Guikeji0144002) and the National Natural Science Foundation of China (20562004). The X-ray data were collected at the Instrumentation Analysis and Research Center of Sun Yat-sen (Zhongshan) University; the authors thank the staff for all their help and advice. We acknowledge Dr S. Parkin at the University of Kentucky (Lexington) and Dr Z. Ma at the University of Guangxi (Nanning) for their advice.
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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.
In the course of our ongoing research on the bioactive secondary metabolites from marine mangrove fungi (Chen et al., 2003, 2005, 2006a, 2006b; Lin et al., 2001a,b, 2002), the title compound was recently isolated from an unidentified species mangrove endophytic fungus No. H2K. It is a new friedelan analogue (Dhaneshwar et al., 1987; Fun et al., 2007; Mo, 1977; Mo et al., 1989; Sun et al., 2004). We report here the structure of the title compound. Further studies on properties are in progress.
The molecular structure is shown in Fig. 1. The molecule contains five six-membered rins, they exhibit boat (ring A), distorted boat (ring B) and chair conformations (rings C–E ), respectively. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds, which link neighbouring molecules into 12-membered rings (Table 1 and Fig. 2).