organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

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

(Received 2 March 2008; accepted 15 April 2008; online 23 April 2008)

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 CE) conformations. The crystal structure 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[Chen, G. Y., Lin, Y. C., Wen, L., Vrijmoed, L. L. P. & Gareth, E. B. J. (2003). Tetrahedron, 59, 4907-4909.], 2005[Chen, H. Y., Qi, P., Lin, Y. C., Chen, G. Y., Wang, L. & Vrijmoed, L. L. P. (2005). Zhongshan Daxue Xuebao (Ziran Kexueban), 44, 122-123.], 2006a[Chen, H. Y., Lin, Y. C., Chen, G. Y., Hu, G. P., Wang, L. & Vrijmoed, L. L. P. (2006a). Chem. Nat. Compd. 42, 407-409.],b[Chen, H.-Y., Lin, Y.-C., Vrijmoed, L. L. P. & Jones, E. B. G. (2006b). Acta Cryst. E62, o836-o837.]); Lin et al. (2001a[Lin, Y. C., Wu, X. Y., Feng, S., Jiang, G. C., Luo, J. H., Zhou, S. N., Vrijmoed, L. L. P., Gareth, E. B. J., Krohn, K., Steingrover, K. & Zsila, F. (2001a). J. Org. Chem. 66, 6252-6256.],b[Lin, Y. C., Wu, X. Y., Feng, S., Jiang, G. C., Zhou, S. N., Vrijmoed, L. L. P. & Gareth, E. B. J. (2001b). Tetrahedron Lett. 42, 449-451.], 2002[Lin, Y. C., Wu, X. Y., Deng, Z. J., Wang, J., Zhou, S. N., Vrijmoed, L. L. P. & Gareth, E. B. J. (2002). Phytochemistry, 59, 469-471.]). For related structures, see: Dhaneshwar et al. (1987[Dhaneshwar, N. N., Sawaikar, D. D., Narayanan, C. R., Tavale, S. S. & Guru Row, T. N. (1987). Acta Cryst. C43, 66-68.]); Fun et al. (2007[Fun, H.-K., Boonnak, N. & Chantrapromma, S. (2007). Acta Cryst. E63, o2014-o2016.]); Mo (1977[Mo, F. (1977). Acta Cryst. B33, 641-649.]); Mo et al. (1989[Mo, F., Winther, S. & Scrimgeour, S. N. (1989). Acta Cryst. B45, 261-270.]); Sun et al. (2004[Sun, J., Zhang, H. G., Zhang, J. M., Zhang, T. B., Guo, B. & Zhang, H. Q. (2004). J. Chin. Pharm. Sci. 13, 291-292.]).

[Scheme 1]

Experimental

Crystal data
  • C30H50O3

  • Mr = 458.70

  • Orthorhombic, P 21 21 2

  • a = 13.238 (3) Å

  • b = 24.141 (5) Å

  • c = 8.7349 (17) Å

  • V = 2791.5 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 153 (2) K

  • 0.51 × 0.48 × 0.46 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 18448 measured reflections

  • 3466 independent reflections

  • 3010 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.112

  • S = 1.04

  • 3466 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+1].

Data collection: SMART (Bruker, 1998[Bruker, (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker, (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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 top

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).

Refinement top

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 anomalous scattering effect, Friedel pairs were merged.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. View of the title compound without the hydrogen atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The unit cell packing of the title compound, showing the intermolecular hydrogen bonding completing a 12-membered ring.
3β-Hydroxyfriedelan-17β-carboxylic acid top
Crystal data top
C30H50O3F(000) = 1016
Mr = 458.70Dx = 1.092 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 999 reflections
a = 13.238 (3) Åθ = 3.0–26.8°
b = 24.141 (5) ŵ = 0.07 mm1
c = 8.7349 (17) ÅT = 153 K
V = 2791.5 (10) Å3Block, colourless
Z = 40.51 × 0.48 × 0.46 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3010 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 27.1°, θmin = 2.3°
ω scansh = 1616
18448 measured reflectionsk = 2330
3466 independent reflectionsl = 911
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.20 e Å3
308 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0119 (15)
Crystal data top
C30H50O3V = 2791.5 (10) Å3
Mr = 458.70Z = 4
Orthorhombic, P21212Mo Kα radiation
a = 13.238 (3) ŵ = 0.07 mm1
b = 24.141 (5) ÅT = 153 K
c = 8.7349 (17) Å0.51 × 0.48 × 0.46 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3010 reflections with I > 2σ(I)
18448 measured reflectionsRint = 0.029
3466 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.04Δρmax = 0.20 e Å3
3457 reflectionsΔρmin = 0.15 e Å3
308 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.81598 (18)0.35284 (10)0.0686 (3)0.0481 (6)
H1A0.80730.32490.15060.058*
H1B0.88490.34830.02660.058*
C20.8082 (2)0.41090 (11)0.1410 (3)0.0556 (6)
C30.6970 (2)0.42285 (12)0.1844 (3)0.0613 (7)
H3A0.67170.45370.12030.074*
H3B0.69420.43500.29260.074*
C40.6285 (2)0.37339 (11)0.1639 (3)0.0529 (6)
H4A0.65020.34380.23510.063*
H4B0.55880.38420.19200.063*
C50.62811 (16)0.34982 (9)0.0025 (2)0.0373 (4)
C60.56513 (16)0.29657 (9)0.0022 (3)0.0421 (5)
H6A0.58730.27350.08530.051*
H6B0.49370.30670.01610.051*
C70.57009 (16)0.26112 (9)0.1476 (3)0.0427 (5)
H7A0.56290.22170.11800.051*
H7B0.51170.27070.21320.051*
C80.66815 (14)0.26743 (8)0.2439 (2)0.0321 (4)
C90.69014 (13)0.21204 (8)0.3279 (2)0.0319 (4)
H90.69580.18410.24390.038*
C100.60437 (15)0.19038 (9)0.4292 (3)0.0425 (5)
H10A0.60200.21200.52540.051*
H10B0.53910.19520.37560.051*
C110.62009 (16)0.12897 (9)0.4665 (3)0.0440 (5)
H11A0.61620.10730.37040.053*
H11B0.56450.11640.53380.053*
C120.72162 (15)0.11659 (9)0.5455 (2)0.0367 (5)
C130.74102 (18)0.05269 (9)0.5379 (3)0.0447 (5)
H130.73560.04280.42700.054*
C140.84770 (19)0.03498 (10)0.5858 (3)0.0508 (6)
H140.85650.00480.55680.061*
C150.92836 (19)0.06796 (11)0.5046 (4)0.0587 (7)
H15A0.93010.05690.39540.070*
H15B0.99490.05900.54990.070*
C160.91100 (16)0.13007 (10)0.5149 (3)0.0452 (5)
H16A0.96380.14970.45570.054*
H16B0.91600.14210.62300.054*
C170.80690 (15)0.14506 (9)0.4519 (2)0.0346 (4)
H170.80430.12650.34970.042*
C180.79289 (14)0.20805 (8)0.4146 (2)0.0321 (4)
C190.87692 (15)0.22646 (9)0.3048 (3)0.0396 (5)
H19A0.94080.22970.36320.048*
H19B0.88660.19730.22650.048*
C200.85661 (15)0.28143 (9)0.2237 (3)0.0382 (5)
H20A0.91330.28950.15330.046*
H20B0.85400.31140.30090.046*
C210.75695 (14)0.28132 (8)0.1319 (2)0.0323 (4)
C220.73960 (15)0.34027 (8)0.0593 (2)0.0357 (4)
H220.75210.36790.14240.043*
C310.8474 (3)0.45484 (13)0.0312 (4)0.0836 (10)
H31A0.91880.44770.00860.125*
H31B0.80830.45360.06400.125*
H31C0.84050.49150.07820.125*
C320.8739 (3)0.41075 (15)0.2853 (4)0.0878 (11)
H32A0.87390.44780.33110.132*
H32B0.84660.38400.35900.132*
H32C0.94320.40030.25830.132*
C330.57641 (18)0.39522 (9)0.0954 (3)0.0428 (5)
O340.61970 (15)0.43196 (7)0.1613 (2)0.0584 (5)
O350.47665 (13)0.39178 (8)0.0915 (2)0.0593 (5)
H350.45160.41720.14520.089*
C360.65061 (17)0.31401 (9)0.3614 (3)0.0424 (5)
H36A0.61190.29950.44820.064*
H36B0.61290.34420.31300.064*
H36C0.71590.32790.39770.064*
C370.76840 (19)0.23692 (9)0.0047 (3)0.0436 (5)
H37A0.83600.23950.04040.065*
H37B0.71750.24320.07480.065*
H37C0.75900.20000.04900.065*
C380.80133 (19)0.24406 (9)0.5599 (2)0.0439 (5)
H38A0.84990.22730.63070.066*
H38B0.73510.24650.60950.066*
H38C0.82440.28130.53190.066*
C390.7150 (2)0.13555 (10)0.7141 (3)0.0489 (6)
H39A0.68490.17260.71880.073*
H39B0.78290.13660.75850.073*
H39C0.67300.10950.77190.073*
C400.6620 (2)0.01711 (11)0.6185 (4)0.0617 (7)
H40A0.67890.02210.60500.093*
H40B0.59540.02450.57430.093*
H40C0.66120.02610.72790.093*
O410.86248 (15)0.03944 (7)0.7487 (2)0.0578 (5)
H410.86330.00760.78760.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0469 (12)0.0492 (13)0.0481 (13)0.0055 (10)0.0085 (11)0.0088 (11)
C20.0647 (15)0.0510 (14)0.0512 (14)0.0024 (12)0.0137 (13)0.0141 (12)
C30.0745 (17)0.0560 (15)0.0536 (15)0.0137 (13)0.0084 (14)0.0184 (13)
C40.0593 (14)0.0600 (15)0.0392 (12)0.0123 (12)0.0052 (11)0.0072 (11)
C50.0429 (10)0.0359 (10)0.0330 (10)0.0082 (9)0.0016 (9)0.0002 (8)
C60.0422 (10)0.0395 (11)0.0447 (12)0.0055 (9)0.0151 (10)0.0021 (10)
C70.0342 (10)0.0398 (11)0.0542 (13)0.0007 (9)0.0101 (10)0.0071 (11)
C80.0291 (9)0.0343 (10)0.0329 (10)0.0038 (7)0.0019 (8)0.0002 (8)
C90.0285 (8)0.0340 (10)0.0331 (10)0.0019 (8)0.0017 (8)0.0014 (8)
C100.0308 (9)0.0475 (12)0.0493 (12)0.0026 (9)0.0001 (10)0.0090 (10)
C110.0334 (9)0.0456 (12)0.0529 (13)0.0042 (9)0.0048 (10)0.0085 (10)
C120.0369 (10)0.0346 (10)0.0388 (11)0.0008 (8)0.0062 (9)0.0025 (9)
C130.0524 (12)0.0369 (11)0.0448 (13)0.0013 (10)0.0144 (11)0.0028 (10)
C140.0594 (14)0.0329 (11)0.0600 (15)0.0073 (10)0.0166 (13)0.0007 (10)
C150.0491 (13)0.0558 (15)0.0712 (17)0.0179 (12)0.0058 (13)0.0107 (14)
C160.0352 (10)0.0495 (13)0.0510 (13)0.0043 (9)0.0082 (10)0.0091 (11)
C170.0332 (9)0.0382 (10)0.0326 (10)0.0043 (8)0.0049 (8)0.0025 (8)
C180.0297 (8)0.0350 (10)0.0317 (9)0.0014 (8)0.0019 (8)0.0002 (8)
C190.0285 (9)0.0495 (12)0.0409 (11)0.0032 (8)0.0015 (9)0.0053 (9)
C200.0312 (9)0.0452 (12)0.0383 (11)0.0017 (8)0.0002 (9)0.0048 (9)
C210.0326 (9)0.0338 (10)0.0305 (9)0.0036 (8)0.0001 (8)0.0020 (8)
C220.0389 (10)0.0348 (10)0.0333 (10)0.0029 (8)0.0004 (9)0.0010 (8)
C310.101 (3)0.0595 (18)0.090 (2)0.0205 (18)0.002 (2)0.0065 (18)
C320.101 (2)0.083 (2)0.079 (2)0.018 (2)0.043 (2)0.0334 (19)
C330.0512 (12)0.0364 (11)0.0408 (11)0.0091 (10)0.0038 (10)0.0049 (9)
O340.0668 (11)0.0356 (8)0.0727 (12)0.0049 (8)0.0050 (10)0.0131 (9)
O350.0503 (9)0.0573 (11)0.0702 (12)0.0155 (8)0.0074 (9)0.0078 (9)
C360.0477 (11)0.0399 (11)0.0397 (11)0.0092 (9)0.0083 (10)0.0004 (9)
C370.0546 (13)0.0407 (12)0.0353 (10)0.0095 (10)0.0019 (10)0.0049 (10)
C380.0547 (13)0.0410 (11)0.0359 (11)0.0025 (10)0.0086 (11)0.0019 (9)
C390.0626 (14)0.0422 (12)0.0419 (12)0.0001 (11)0.0034 (11)0.0026 (10)
C400.0683 (16)0.0443 (13)0.0725 (18)0.0146 (12)0.0183 (15)0.0096 (13)
O410.0721 (11)0.0384 (9)0.0628 (11)0.0092 (8)0.0293 (10)0.0121 (8)
Geometric parameters (Å, º) top
C1—C221.537 (3)C15—H15A0.9900
C1—C21.541 (3)C15—H15B0.9900
C1—H1A0.9900C16—C171.528 (3)
C1—H1B0.9900C16—H16A0.9900
C2—C311.522 (4)C16—H16B0.9900
C2—C321.531 (4)C17—C181.566 (3)
C2—C31.547 (4)C17—H171.0000
C3—C41.510 (4)C18—C191.535 (3)
C3—H3A0.9900C18—C381.542 (3)
C3—H3B0.9900C19—C201.528 (3)
C4—C51.561 (3)C19—H19A0.9900
C4—H4A0.9900C19—H19B0.9900
C4—H4B0.9900C20—C211.544 (3)
C5—C331.526 (3)C20—H20A0.9900
C5—C61.532 (3)C20—H20B0.9900
C5—C221.574 (3)C21—C371.551 (3)
C6—C71.533 (3)C21—C221.575 (3)
C6—H6A0.9900C22—H221.0000
C6—H6B0.9900C31—H31A0.9800
C7—C81.555 (3)C31—H31B0.9800
C7—H7A0.9900C31—H31C0.9800
C7—H7B0.9900C32—H32A0.9800
C8—C361.540 (3)C32—H32B0.9800
C8—C91.553 (3)C32—H32C0.9800
C8—C211.566 (3)C33—O341.203 (3)
C9—C101.531 (3)C33—O351.324 (3)
C9—C181.560 (3)O35—H350.8400
C9—H91.0000C36—H36A0.9800
C10—C111.532 (3)C36—H36B0.9800
C10—H10A0.9900C36—H36C0.9800
C10—H10B0.9900C37—H37A0.9800
C11—C121.540 (3)C37—H37B0.9800
C11—H11A0.9900C37—H37C0.9800
C11—H11B0.9900C38—H38A0.9800
C12—C391.544 (3)C38—H38B0.9800
C12—C171.554 (3)C38—H38C0.9800
C12—C131.565 (3)C39—H39A0.9800
C13—C401.525 (4)C39—H39B0.9800
C13—C141.534 (3)C39—H39C0.9800
C13—H131.0000C40—H40A0.9800
C14—O411.440 (3)C40—H40B0.9800
C14—C151.509 (4)C40—H40C0.9800
C14—H141.0000O41—H410.8400
C15—C161.520 (3)
C22—C1—C2115.72 (19)C15—C16—C17110.41 (19)
C22—C1—H1A108.4C15—C16—H16A109.6
C2—C1—H1A108.4C17—C16—H16A109.6
C22—C1—H1B108.4C15—C16—H16B109.6
C2—C1—H1B108.4C17—C16—H16B109.6
H1A—C1—H1B107.4H16A—C16—H16B108.1
C31—C2—C32109.1 (3)C16—C17—C12111.15 (17)
C31—C2—C1110.6 (2)C16—C17—C18114.32 (17)
C32—C2—C1107.3 (2)C12—C17—C18116.92 (16)
C31—C2—C3110.4 (3)C16—C17—H17104.3
C32—C2—C3109.8 (3)C12—C17—H17104.3
C1—C2—C3109.5 (2)C18—C17—H17104.3
C4—C3—C2113.3 (2)C19—C18—C38107.38 (17)
C4—C3—H3A108.9C19—C18—C9108.09 (15)
C2—C3—H3A108.9C38—C18—C9115.35 (17)
C4—C3—H3B108.9C19—C18—C17108.98 (16)
C2—C3—H3B108.9C38—C18—C17111.58 (17)
H3A—C3—H3B107.7C9—C18—C17105.31 (15)
C3—C4—C5113.6 (2)C20—C19—C18114.44 (17)
C3—C4—H4A108.8C20—C19—H19A108.7
C5—C4—H4A108.8C18—C19—H19A108.7
C3—C4—H4B108.8C20—C19—H19B108.7
C5—C4—H4B108.8C18—C19—H19B108.7
H4A—C4—H4B107.7H19A—C19—H19B107.6
C33—C5—C6111.08 (18)C19—C20—C21112.93 (17)
C33—C5—C4103.59 (17)C19—C20—H20A109.0
C6—C5—C4107.80 (18)C21—C20—H20A109.0
C33—C5—C22111.00 (17)C19—C20—H20B109.0
C6—C5—C22112.84 (16)C21—C20—H20B109.0
C4—C5—C22110.08 (18)H20A—C20—H20B107.8
C5—C6—C7116.32 (18)C20—C21—C37106.84 (16)
C5—C6—H6A108.2C20—C21—C8108.48 (15)
C7—C6—H6A108.2C37—C21—C8111.90 (17)
C5—C6—H6B108.2C20—C21—C22109.41 (16)
C7—C6—H6B108.2C37—C21—C22110.52 (16)
H6A—C6—H6B107.4C8—C21—C22109.61 (15)
C6—C7—C8115.44 (18)C1—C22—C5111.04 (18)
C6—C7—H7A108.4C1—C22—C21112.03 (17)
C8—C7—H7A108.4C5—C22—C21113.32 (16)
C6—C7—H7B108.4C1—C22—H22106.7
C8—C7—H7B108.4C5—C22—H22106.7
H7A—C7—H7B107.5C21—C22—H22106.7
C36—C8—C9110.03 (16)C2—C31—H31A109.5
C36—C8—C7107.84 (16)C2—C31—H31B109.5
C9—C8—C7109.14 (16)H31A—C31—H31B109.5
C36—C8—C21111.92 (16)C2—C31—H31C109.5
C9—C8—C21109.81 (15)H31A—C31—H31C109.5
C7—C8—C21108.02 (16)H31B—C31—H31C109.5
C10—C9—C8115.34 (16)C2—C32—H32A109.5
C10—C9—C18110.17 (16)C2—C32—H32B109.5
C8—C9—C18116.49 (15)H32A—C32—H32B109.5
C10—C9—H9104.4C2—C32—H32C109.5
C8—C9—H9104.4H32A—C32—H32C109.5
C18—C9—H9104.4H32B—C32—H32C109.5
C11—C10—C9110.65 (17)O34—C33—O35122.3 (2)
C11—C10—H10A109.5O34—C33—C5124.8 (2)
C9—C10—H10A109.5O35—C33—C5112.9 (2)
C11—C10—H10B109.5C33—O35—H35109.5
C9—C10—H10B109.5C8—C36—H36A109.5
H10A—C10—H10B108.1C8—C36—H36B109.5
C10—C11—C12113.68 (18)H36A—C36—H36B109.5
C10—C11—H11A108.8C8—C36—H36C109.5
C12—C11—H11A108.8H36A—C36—H36C109.5
C10—C11—H11B108.8H36B—C36—H36C109.5
C12—C11—H11B108.8C21—C37—H37A109.5
H11A—C11—H11B107.7C21—C37—H37B109.5
C11—C12—C39108.68 (19)H37A—C37—H37B109.5
C11—C12—C17108.18 (17)C21—C37—H37C109.5
C39—C12—C17114.32 (18)H37A—C37—H37C109.5
C11—C12—C13108.38 (17)H37B—C37—H37C109.5
C39—C12—C13109.99 (18)C18—C38—H38A109.5
C17—C12—C13107.12 (17)C18—C38—H38B109.5
C40—C13—C14110.4 (2)H38A—C38—H38B109.5
C40—C13—C12115.0 (2)C18—C38—H38C109.5
C14—C13—C12114.48 (18)H38A—C38—H38C109.5
C40—C13—H13105.3H38B—C38—H38C109.5
C14—C13—H13105.3C12—C39—H39A109.5
C12—C13—H13105.3C12—C39—H39B109.5
O41—C14—C15109.2 (2)H39A—C39—H39B109.5
O41—C14—C13111.9 (2)C12—C39—H39C109.5
C15—C14—C13112.1 (2)H39A—C39—H39C109.5
O41—C14—H14107.8H39B—C39—H39C109.5
C15—C14—H14107.8C13—C40—H40A109.5
C13—C14—H14107.8C13—C40—H40B109.5
C14—C15—C16112.7 (2)H40A—C40—H40B109.5
C14—C15—H15A109.1C13—C40—H40C109.5
C16—C15—H15A109.1H40A—C40—H40C109.5
C14—C15—H15B109.1H40B—C40—H40C109.5
C16—C15—H15B109.1C14—O41—H41109.5
H15A—C15—H15B107.8
C22—C1—C2—C3172.8 (3)C13—C12—C17—C18168.25 (17)
C22—C1—C2—C32168.3 (3)C10—C9—C18—C19176.21 (18)
C22—C1—C2—C349.1 (3)C8—C9—C18—C1950.0 (2)
C31—C2—C3—C4129.2 (3)C10—C9—C18—C3863.6 (2)
C32—C2—C3—C4110.5 (3)C8—C9—C18—C3870.2 (2)
C1—C2—C3—C47.1 (3)C10—C9—C18—C1759.8 (2)
C2—C3—C4—C557.6 (3)C8—C9—C18—C17166.34 (16)
C3—C4—C5—C3368.3 (3)C16—C17—C18—C1955.0 (2)
C3—C4—C5—C6174.0 (2)C12—C17—C18—C19172.64 (16)
C3—C4—C5—C2250.5 (3)C16—C17—C18—C3863.4 (2)
C33—C5—C6—C777.6 (2)C12—C17—C18—C3869.0 (2)
C4—C5—C6—C7169.56 (19)C16—C17—C18—C9170.78 (17)
C22—C5—C6—C747.8 (3)C12—C17—C18—C956.9 (2)
C5—C6—C7—C825.9 (3)C38—C18—C19—C2075.4 (2)
C6—C7—C8—C3690.4 (2)C9—C18—C19—C2049.6 (2)
C6—C7—C8—C9150.07 (18)C17—C18—C19—C20163.59 (17)
C6—C7—C8—C2130.7 (2)C18—C19—C20—C2157.0 (2)
C36—C8—C9—C1062.4 (2)C19—C20—C21—C3763.1 (2)
C7—C8—C9—C1055.8 (2)C19—C20—C21—C857.7 (2)
C21—C8—C9—C10174.02 (17)C19—C20—C21—C22177.21 (17)
C36—C8—C9—C1869.1 (2)C36—C8—C21—C2067.5 (2)
C7—C8—C9—C18172.75 (17)C9—C8—C21—C2055.0 (2)
C21—C8—C9—C1854.5 (2)C7—C8—C21—C20173.94 (16)
C8—C9—C10—C11162.92 (18)C36—C8—C21—C37174.90 (17)
C18—C9—C10—C1162.7 (2)C9—C8—C21—C3762.6 (2)
C9—C10—C11—C1257.3 (3)C7—C8—C21—C3756.3 (2)
C10—C11—C12—C3975.3 (2)C36—C8—C21—C2251.9 (2)
C10—C11—C12—C1749.4 (2)C9—C8—C21—C22174.43 (16)
C10—C11—C12—C13165.2 (2)C7—C8—C21—C2266.6 (2)
C11—C12—C13—C4061.1 (3)C2—C1—C22—C555.1 (3)
C39—C12—C13—C4057.6 (3)C2—C1—C22—C21177.0 (2)
C17—C12—C13—C40177.61 (19)C33—C5—C22—C1118.2 (2)
C11—C12—C13—C14169.5 (2)C6—C5—C22—C1116.4 (2)
C39—C12—C13—C1471.8 (3)C4—C5—C22—C14.1 (2)
C17—C12—C13—C1452.9 (3)C33—C5—C22—C21114.73 (19)
C40—C13—C14—O4158.8 (3)C6—C5—C22—C2110.7 (2)
C12—C13—C14—O4172.9 (3)C4—C5—C22—C21131.17 (18)
C40—C13—C14—C15178.1 (2)C20—C21—C22—C169.3 (2)
C12—C13—C14—C1550.2 (3)C37—C21—C22—C148.1 (2)
O41—C14—C15—C1674.1 (3)C8—C21—C22—C1171.89 (18)
C13—C14—C15—C1650.5 (3)C20—C21—C22—C5164.12 (17)
C14—C15—C16—C1756.4 (3)C37—C21—C22—C578.5 (2)
C15—C16—C17—C1261.2 (3)C8—C21—C22—C545.3 (2)
C15—C16—C17—C18163.8 (2)C6—C5—C33—O34151.5 (2)
C11—C12—C17—C16174.64 (19)C4—C5—C33—O3493.0 (3)
C39—C12—C17—C1664.1 (2)C22—C5—C33—O3425.1 (3)
C13—C12—C17—C1658.0 (2)C6—C5—C33—O3531.2 (3)
C11—C12—C17—C1851.6 (2)C4—C5—C33—O3584.3 (2)
C39—C12—C17—C1869.6 (2)C22—C5—C33—O35157.59 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O35—H35···O41i0.841.832.644 (2)163
O41—H41···O34ii0.841.892.721 (2)168
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+3/2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC30H50O3
Mr458.70
Crystal system, space groupOrthorhombic, P21212
Temperature (K)153
a, b, c (Å)13.238 (3), 24.141 (5), 8.7349 (17)
V3)2791.5 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.51 × 0.48 × 0.46
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18448, 3466, 3010
Rint0.029
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.112, 1.04
No. of reflections3457
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.15

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O35—H35···O41i0.841.832.644 (2)162.7
O41—H41···O34ii0.841.892.721 (2)168.1
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+3/2, y1/2, 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.

References

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