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Acta Cryst. (2009). E65, o1317    [ doi:10.1107/S1600536809015955 ]

Pinnatane A from the bark of Walsura pinnata Hassk

K. Mohamad, M. Yusoff, K. Awang, K. Ahmad and S. W. Ng

Abstract top

In the molecule of pinnatane A, C30H48O3, isolated from the bark of Walsura pinnata Hassk, the four cyclohexane rings adopt chair conformations; the carboxyl and hydroxy substituents occupy axial positions. The cyclohexene ring is envelope-shaped. Adjacent molecules are linked by O-H...O hydrogen bonds into a chain running along the c axis.

Comment top

Chemicals from Walsura pinnata Hassk have not hitherto been reported. We have recently reported the structure of 3-oxoolean-1-en-28-oic acid (Awang et al., 2009), which was obtained from one fraction of the crude extract of the bark of this plant. The last fraction yielded the title compound, which we have named pinnatane A. A related carbon skeleton, assigned from spectroscopic measurements, has been reported (Jiang et al., 1995).

In the molecule of pinnatane A (Fig. 1) the four cyclohexane rings adopt chair comformations, with axial carboxylic acid and hydroxy substituents. The cyclohexene ring is envelope-shaped. Adjacent molecules are linked by O—H···O hydrogen bonds into a chain running along the longest axis of the orthorhombic unit cell.

Related literature top

For related structures, see: Awang et al. (2009); Jiang et al. (1995).

Experimental top

The dried and ground bark of Walsura pinnata Hassk (2.3 kg) was extracted with n-hexane for 72 h at room temperature. The solvent was evaporated to give a crude extract, which was subjected to column chromatography on silica gel (60 GF254), using n-hexane with increasing amounts of ethyl acetate as eluent. Of the twenty-four fractions collected, the twenty-fourth fraction, eluted with ethyl acetate:n-hexane (14:86) gave 2 g of the product, which was further purified by column chromatography (n-hexane:acetone, 94:6) to give the title compound (5 mg). The formulation was established by satisfactory solution NMR spectroscopy.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The oxygen-bound H-atoms were located in a difference Fourier map, and were refined with a distance restraint of 0.84±0.01 Å; their displacement parameters were freely refined. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker,2007); 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, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(I) top
Crystal data top
C30H48O3F000 = 1008
Mr = 456.68Dx = 1.214 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3887 reflections
a = 7.3761 (2) Åθ = 2.3–28.0º
b = 16.3585 (4) ŵ = 0.08 mm−1
c = 20.7032 (5) ÅT = 100 K
V = 2498.1 (1) Å3Chip, colorless
Z = 40.40 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		2881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Monochromator: graphiteθmax = 27.5º
T = 100 Kθmin = 1.6º
ω scansh = −9→9
Absorption correction: Nonek = −21→21
17614 measured reflectionsl = −26→25
3268 independent reflections
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)] = 0.037H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.0608P)2 + 0.3281P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3268 reflectionsΔρmax = 0.27 e Å−3
313 parametersΔρmin = −0.17 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C30H48O3V = 2498.1 (1) Å3
Mr = 456.68Z = 4
Orthorhombic, P212121Mo Kα
a = 7.3761 (2) ŵ = 0.08 mm−1
b = 16.3585 (4) ÅT = 100 K
c = 20.7032 (5) Å0.40 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		3268 independent reflections
Absorption correction: None2881 reflections with I > 2σ(I)
17614 measured reflectionsRint = 0.045
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.097Δρmax = 0.27 e Å−3
S = 1.00Δρmin = −0.17 e Å−3
3268 reflectionsAbsolute structure: ?
313 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0192 (2)1.08616 (9)−0.04603 (8)0.0226 (3)
H10.022 (5)1.1379 (6)−0.0479 (15)0.054 (9)*
O20.2787 (2)1.10407 (8)0.00673 (6)0.0191 (3)
O30.5137 (2)0.74943 (9)0.43439 (7)0.0219 (3)
H30.590 (3)0.7286 (16)0.4595 (11)0.040 (8)*
C10.1662 (3)1.05839 (11)−0.01560 (9)0.0145 (4)
C20.1730 (3)0.96355 (11)−0.01453 (9)0.0131 (4)
C30.1421 (3)0.93705 (12)−0.08573 (9)0.0168 (4)
H3A0.14470.8766−0.08840.020*
H3B0.02080.9556−0.09990.020*
C40.2849 (3)0.97201 (13)−0.13099 (10)0.0209 (4)
H4A0.26951.0321−0.13330.025*
H4B0.26500.9497−0.17490.025*
C50.4827 (3)0.95261 (13)−0.10968 (9)0.0197 (4)
C60.4780 (3)0.90007 (12)−0.04821 (9)0.0181 (4)
H6A0.60420.8920−0.03320.022*
H6B0.42900.8456−0.05960.022*
C70.3656 (3)0.93451 (11)0.00866 (9)0.0129 (4)
H70.43060.98440.02420.015*
C80.5911 (3)1.03113 (14)−0.09846 (11)0.0267 (5)
H8A0.52941.0649−0.06610.040*
H8B0.60051.0616−0.13910.040*
H8C0.71291.0172−0.08300.040*
C90.5782 (4)0.90337 (16)−0.16263 (10)0.0323 (6)
H9A0.51270.8521−0.16990.049*
H9B0.70280.8913−0.14920.049*
H9C0.58020.9352−0.20270.049*
C100.3632 (3)0.87291 (11)0.06662 (9)0.0118 (4)
C110.3079 (3)0.78698 (11)0.04270 (9)0.0159 (4)
H11A0.41040.76160.02030.024*
H11B0.20510.79180.01290.024*
H11C0.27290.75310.07970.024*
C120.2315 (3)0.90314 (11)0.12067 (8)0.0116 (4)
C130.0361 (3)0.89617 (12)0.09446 (9)0.0148 (4)
H13A−0.04640.92500.12450.018*
H13B0.00090.83780.09430.018*
C140.0073 (3)0.93116 (12)0.02569 (9)0.0172 (4)
H14A−0.08050.97670.02940.021*
H14B−0.05200.8880−0.00030.021*
C150.2605 (3)0.99440 (11)0.13609 (9)0.0151 (4)
H15A0.21381.00630.17940.023*
H15B0.19581.02780.10430.023*
H15C0.39021.00710.13440.023*
C160.2508 (3)0.84795 (11)0.18263 (9)0.0116 (4)
H160.21220.79200.16880.014*
C170.4463 (3)0.83731 (11)0.20946 (9)0.0126 (4)
C180.5718 (3)0.81296 (12)0.15331 (9)0.0147 (4)
H18A0.69880.81350.16880.018*
H18B0.54270.75630.14000.018*
C190.5566 (3)0.86876 (12)0.09454 (9)0.0147 (4)
H19A0.64020.84890.06060.018*
H19B0.59550.92450.10690.018*
C200.5197 (3)0.91447 (11)0.24330 (10)0.0168 (4)
H20A0.45180.92390.28330.025*
H20B0.50570.96170.21460.025*
H20C0.64840.90680.25350.025*
C210.4437 (3)0.76507 (11)0.25864 (9)0.0136 (4)
H210.43140.71390.23250.016*
C220.2839 (3)0.76640 (11)0.30481 (9)0.0139 (4)
C230.1435 (3)0.81574 (12)0.29524 (9)0.0150 (4)
H230.05020.81610.32690.018*
C240.1219 (3)0.87123 (12)0.23765 (9)0.0151 (4)
H24A0.14610.92830.25090.018*
H24B−0.00470.86820.22200.018*
C250.6225 (3)0.75728 (12)0.29622 (10)0.0182 (4)
H25A0.72520.75430.26560.022*
H25B0.63970.80600.32390.022*
C260.6192 (3)0.68067 (12)0.33802 (10)0.0191 (4)
H26A0.59930.63210.31040.023*
H26B0.73770.67420.35990.023*
C270.4700 (3)0.68582 (11)0.38820 (9)0.0168 (4)
H270.46580.63250.41180.020*
C280.2819 (3)0.70122 (11)0.35883 (9)0.0156 (4)
C290.1487 (3)0.72131 (13)0.41332 (9)0.0199 (4)
H29A0.17240.77660.42940.030*
H29B0.16410.68200.44860.030*
H29C0.02430.71820.39690.030*
C300.2190 (3)0.62008 (12)0.32797 (10)0.0215 (4)
H30A0.30000.60590.29220.032*
H30B0.09500.62630.31170.032*
H30C0.22210.57660.36050.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0198 (8)0.0148 (7)0.0332 (8)0.0020 (6)−0.0087 (7)0.0031 (6)
O20.0224 (8)0.0151 (6)0.0198 (7)−0.0031 (6)−0.0050 (6)0.0014 (5)
O30.0293 (9)0.0174 (7)0.0190 (7)0.0024 (7)−0.0108 (7)−0.0029 (6)
C10.0152 (10)0.0161 (9)0.0121 (8)0.0021 (8)0.0016 (8)0.0006 (7)
C20.0123 (9)0.0140 (8)0.0130 (9)0.0006 (7)−0.0012 (8)0.0005 (7)
C30.0186 (10)0.0184 (9)0.0134 (9)0.0001 (8)−0.0033 (8)−0.0014 (7)
C40.0216 (11)0.0284 (11)0.0126 (9)0.0043 (9)−0.0013 (9)0.0004 (8)
C50.0208 (11)0.0254 (10)0.0128 (9)0.0072 (9)0.0044 (9)0.0035 (8)
C60.0184 (10)0.0223 (10)0.0136 (9)0.0065 (9)0.0025 (8)0.0030 (8)
C70.0119 (9)0.0146 (9)0.0121 (8)0.0012 (7)0.0002 (7)0.0005 (7)
C80.0181 (11)0.0348 (12)0.0273 (11)−0.0002 (10)0.0018 (9)0.0123 (10)
C90.0379 (15)0.0426 (14)0.0165 (10)0.0175 (12)0.0082 (10)0.0050 (10)
C100.0106 (9)0.0128 (8)0.0119 (8)0.0012 (7)0.0012 (7)0.0009 (7)
C110.0175 (10)0.0141 (9)0.0160 (9)0.0010 (8)0.0010 (8)−0.0008 (7)
C120.0111 (9)0.0126 (8)0.0112 (8)0.0006 (7)−0.0005 (7)0.0001 (6)
C130.0120 (9)0.0170 (9)0.0155 (9)0.0012 (8)0.0008 (8)0.0034 (7)
C140.0131 (10)0.0195 (9)0.0190 (9)−0.0007 (8)−0.0017 (8)0.0045 (8)
C150.0166 (10)0.0142 (9)0.0144 (8)0.0014 (8)−0.0006 (8)0.0004 (7)
C160.0114 (9)0.0105 (8)0.0129 (8)−0.0003 (7)0.0009 (7)0.0016 (6)
C170.0115 (9)0.0135 (9)0.0128 (9)0.0009 (7)0.0001 (7)0.0018 (7)
C180.0116 (10)0.0172 (9)0.0151 (9)0.0023 (8)0.0009 (7)0.0031 (7)
C190.0128 (10)0.0167 (9)0.0146 (9)0.0005 (8)0.0008 (8)0.0014 (7)
C200.0169 (10)0.0160 (9)0.0175 (9)−0.0023 (8)−0.0021 (8)0.0013 (7)
C210.0147 (10)0.0128 (9)0.0134 (9)0.0008 (7)−0.0001 (7)0.0007 (7)
C220.0168 (10)0.0136 (8)0.0114 (8)−0.0035 (7)−0.0014 (8)−0.0003 (7)
C230.0141 (10)0.0187 (9)0.0122 (8)−0.0008 (8)0.0021 (8)−0.0002 (7)
C240.0121 (10)0.0184 (9)0.0150 (9)0.0025 (8)0.0015 (8)0.0025 (7)
C250.0152 (10)0.0188 (10)0.0205 (10)0.0013 (8)−0.0003 (8)0.0053 (8)
C260.0206 (11)0.0184 (10)0.0183 (9)0.0033 (9)−0.0030 (9)0.0032 (8)
C270.0245 (11)0.0126 (9)0.0133 (9)0.0000 (8)−0.0028 (8)0.0001 (7)
C280.0198 (10)0.0137 (9)0.0131 (9)−0.0019 (8)−0.0007 (8)−0.0002 (7)
C290.0225 (11)0.0236 (10)0.0136 (9)−0.0015 (9)0.0011 (8)0.0038 (8)
C300.0281 (12)0.0192 (10)0.0172 (9)−0.0063 (9)−0.0039 (9)0.0020 (8)
Geometric parameters (Å, °) top
O1—C11.334 (2)C15—H15A0.9800
O1—H10.85 (1)C15—H15B0.9800
O2—C11.208 (2)C15—H15C0.9800
O3—C271.450 (2)C16—C241.532 (3)
O3—H30.84 (1)C16—C171.555 (3)
C1—C21.552 (3)C16—H161.0000
C2—C31.553 (3)C17—C181.538 (3)
C2—C141.571 (3)C17—C201.542 (3)
C2—C71.573 (3)C17—C211.560 (2)
C3—C41.521 (3)C18—C191.525 (2)
C3—H3A0.9900C18—H18A0.9900
C3—H3B0.9900C18—H18B0.9900
C4—C51.557 (3)C19—H19A0.9900
C4—H4A0.9900C19—H19B0.9900
C4—H4B0.9900C20—H20A0.9800
C5—C91.532 (3)C20—H20B0.9800
C5—C81.531 (3)C20—H20C0.9800
C5—C61.536 (3)C21—C221.518 (3)
C6—C71.546 (3)C21—C251.536 (3)
C6—H6A0.9900C21—H211.0000
C6—H6B0.9900C22—C231.328 (3)
C7—C101.567 (2)C22—C281.545 (2)
C7—H71.0000C23—C241.507 (2)
C8—H8A0.9800C23—H230.9500
C8—H8B0.9800C24—H24A0.9900
C8—H8C0.9800C24—H24B0.9900
C9—H9A0.9800C25—C261.523 (3)
C9—H9B0.9800C25—H25A0.9900
C9—H9C0.9800C25—H25B0.9900
C10—C191.541 (3)C26—C271.516 (3)
C10—C111.545 (3)C26—H26A0.9900
C10—C121.562 (3)C26—H26B0.9900
C11—H11A0.9800C27—C281.535 (3)
C11—H11B0.9800C27—H271.0000
C11—H11C0.9800C28—C291.532 (3)
C12—C151.542 (3)C28—C301.544 (3)
C12—C131.544 (3)C29—H29A0.9800
C12—C161.575 (2)C29—H29B0.9800
C13—C141.549 (3)C29—H29C0.9800
C13—H13A0.9900C30—H30A0.9800
C13—H13B0.9900C30—H30B0.9800
C14—H14A0.9900C30—H30C0.9800
C14—H14B0.9900
C1—O1—H1110 (2)H15A—C15—H15C109.5
C27—O3—H3105.5 (19)H15B—C15—H15C109.5
O2—C1—O1121.87 (17)C24—C16—C17109.75 (15)
O2—C1—C2126.19 (18)C24—C16—C12114.01 (15)
O1—C1—C2111.93 (17)C17—C16—C12116.04 (15)
C1—C2—C3105.10 (15)C24—C16—H16105.3
C1—C2—C14108.63 (16)C17—C16—H16105.3
C3—C2—C14107.14 (16)C12—C16—H16105.3
C1—C2—C7109.60 (16)C18—C17—C20110.12 (16)
C3—C2—C7109.74 (16)C18—C17—C16108.48 (15)
C14—C2—C7116.04 (15)C20—C17—C16113.35 (16)
C4—C3—C2112.22 (16)C18—C17—C21107.73 (15)
C4—C3—H3A109.2C20—C17—C21109.15 (15)
C2—C3—H3A109.2C16—C17—C21107.84 (15)
C4—C3—H3B109.2C19—C18—C17113.81 (15)
C2—C3—H3B109.2C19—C18—H18A108.8
H3A—C3—H3B107.9C17—C18—H18A108.8
C3—C4—C5113.42 (16)C19—C18—H18B108.8
C3—C4—H4A108.9C17—C18—H18B108.8
C5—C4—H4A108.9H18A—C18—H18B107.7
C3—C4—H4B108.9C18—C19—C10113.18 (16)
C5—C4—H4B108.9C18—C19—H19A108.9
H4A—C4—H4B107.7C10—C19—H19A108.9
C9—C5—C8108.03 (19)C18—C19—H19B108.9
C9—C5—C6108.00 (16)C10—C19—H19B108.9
C8—C5—C6110.83 (17)H19A—C19—H19B107.8
C9—C5—C4109.59 (18)C17—C20—H20A109.5
C8—C5—C4111.19 (17)C17—C20—H20B109.5
C6—C5—C4109.13 (17)H20A—C20—H20B109.5
C5—C6—C7116.03 (16)C17—C20—H20C109.5
C5—C6—H6A108.3H20A—C20—H20C109.5
C7—C6—H6A108.3H20B—C20—H20C109.5
C5—C6—H6B108.3C22—C21—C25110.42 (15)
C7—C6—H6B108.3C22—C21—C17114.20 (15)
H6A—C6—H6B107.4C25—C21—C17112.50 (16)
C6—C7—C10110.77 (15)C22—C21—H21106.4
C6—C7—C2111.23 (15)C25—C21—H21106.4
C10—C7—C2114.71 (15)C17—C21—H21106.4
C6—C7—H7106.5C23—C22—C21121.36 (16)
C10—C7—H7106.5C23—C22—C28121.35 (18)
C2—C7—H7106.5C21—C22—C28116.93 (16)
C5—C8—H8A109.5C22—C23—C24124.52 (18)
C5—C8—H8B109.5C22—C23—H23117.7
H8A—C8—H8B109.5C24—C23—H23117.7
C5—C8—H8C109.5C23—C24—C16111.90 (16)
H8A—C8—H8C109.5C23—C24—H24A109.2
H8B—C8—H8C109.5C16—C24—H24A109.2
C5—C9—H9A109.5C23—C24—H24B109.2
C5—C9—H9B109.5C16—C24—H24B109.2
H9A—C9—H9B109.5H24A—C24—H24B107.9
C5—C9—H9C109.5C26—C25—C21110.02 (17)
H9A—C9—H9C109.5C26—C25—H25A109.7
H9B—C9—H9C109.5C21—C25—H25A109.7
C19—C10—C11108.97 (16)C26—C25—H25B109.7
C19—C10—C12108.72 (14)C21—C25—H25B109.7
C11—C10—C12110.67 (16)H25A—C25—H25B108.2
C19—C10—C7107.78 (15)C27—C26—C25110.80 (17)
C11—C10—C7110.03 (15)C27—C26—H26A109.5
C12—C10—C7110.60 (14)C25—C26—H26A109.5
C10—C11—H11A109.5C27—C26—H26B109.5
C10—C11—H11B109.5C25—C26—H26B109.5
H11A—C11—H11B109.5H26A—C26—H26B108.1
C10—C11—H11C109.5O3—C27—C26109.29 (17)
H11A—C11—H11C109.5O3—C27—C28110.14 (16)
H11B—C11—H11C109.5C26—C27—C28113.18 (16)
C15—C12—C13105.88 (16)O3—C27—H27108.0
C15—C12—C10111.64 (15)C26—C27—H27108.0
C13—C12—C10107.79 (14)C28—C27—H27108.0
C15—C12—C16111.95 (14)C29—C28—C27108.85 (15)
C13—C12—C16109.17 (15)C29—C28—C30107.23 (17)
C10—C12—C16110.22 (14)C27—C28—C30107.11 (16)
C12—C13—C14115.06 (16)C29—C28—C22113.01 (16)
C12—C13—H13A108.5C27—C28—C22113.06 (16)
C14—C13—H13A108.5C30—C28—C22107.25 (15)
C12—C13—H13B108.5C28—C29—H29A109.5
C14—C13—H13B108.5C28—C29—H29B109.5
H13A—C13—H13B107.5H29A—C29—H29B109.5
C13—C14—C2120.34 (17)C28—C29—H29C109.5
C13—C14—H14A107.2H29A—C29—H29C109.5
C2—C14—H14A107.2H29B—C29—H29C109.5
C13—C14—H14B107.2C28—C30—H30A109.5
C2—C14—H14B107.2C28—C30—H30B109.5
H14A—C14—H14B106.9H30A—C30—H30B109.5
C12—C15—H15A109.5C28—C30—H30C109.5
C12—C15—H15B109.5H30A—C30—H30C109.5
H15A—C15—H15B109.5H30B—C30—H30C109.5
C12—C15—H15C109.5
O2—C1—C2—C3−128.3 (2)C15—C12—C16—C17−72.0 (2)
O1—C1—C2—C350.5 (2)C13—C12—C16—C17171.15 (15)
O2—C1—C2—C14117.3 (2)C10—C12—C16—C1752.9 (2)
O1—C1—C2—C14−63.9 (2)C24—C16—C17—C18179.31 (15)
O2—C1—C2—C7−10.4 (3)C12—C16—C17—C18−49.6 (2)
O1—C1—C2—C7168.37 (15)C24—C16—C17—C20−58.05 (19)
C1—C2—C3—C459.0 (2)C12—C16—C17—C2072.99 (19)
C14—C2—C3—C4174.41 (16)C24—C16—C17—C2162.89 (19)
C7—C2—C3—C4−58.8 (2)C12—C16—C17—C21−166.06 (14)
C2—C3—C4—C554.0 (2)C20—C17—C18—C19−73.7 (2)
C3—C4—C5—C9119.69 (19)C16—C17—C18—C1950.8 (2)
C3—C4—C5—C8−120.95 (19)C21—C17—C18—C19167.33 (16)
C3—C4—C5—C61.6 (2)C17—C18—C19—C10−58.2 (2)
C9—C5—C6—C7−172.55 (19)C11—C10—C19—C18−62.8 (2)
C8—C5—C6—C769.3 (2)C12—C10—C19—C1857.9 (2)
C4—C5—C6—C7−53.5 (2)C7—C10—C19—C18177.82 (15)
C5—C6—C7—C10176.81 (17)C18—C17—C21—C22−161.11 (16)
C5—C6—C7—C248.0 (2)C20—C17—C21—C2279.3 (2)
C1—C2—C7—C6−106.48 (18)C16—C17—C21—C22−44.2 (2)
C3—C2—C7—C68.5 (2)C18—C17—C21—C2572.02 (19)
C14—C2—C7—C6130.06 (17)C20—C17—C21—C25−47.5 (2)
C1—C2—C7—C10126.83 (16)C16—C17—C21—C25−171.08 (15)
C3—C2—C7—C10−118.23 (16)C25—C21—C22—C23140.08 (18)
C14—C2—C7—C103.4 (2)C17—C21—C22—C2312.1 (2)
C6—C7—C10—C1967.88 (19)C25—C21—C22—C28−46.6 (2)
C2—C7—C10—C19−165.19 (16)C17—C21—C22—C28−174.56 (16)
C6—C7—C10—C11−50.8 (2)C21—C22—C23—C243.2 (3)
C2—C7—C10—C1176.1 (2)C28—C22—C23—C24−169.77 (18)
C6—C7—C10—C12−173.40 (16)C22—C23—C24—C1615.8 (3)
C2—C7—C10—C12−46.5 (2)C17—C16—C24—C23−48.9 (2)
C19—C10—C12—C1571.33 (18)C12—C16—C24—C23178.98 (15)
C11—C10—C12—C15−169.02 (15)C22—C21—C25—C2657.1 (2)
C7—C10—C12—C15−46.8 (2)C17—C21—C25—C26−173.99 (16)
C19—C10—C12—C13−172.80 (15)C21—C25—C26—C27−62.7 (2)
C11—C10—C12—C13−53.15 (19)C25—C26—C27—O3−67.6 (2)
C7—C10—C12—C1369.05 (18)C25—C26—C27—C2855.6 (2)
C19—C10—C12—C16−53.74 (19)O3—C27—C28—C29−46.8 (2)
C11—C10—C12—C1665.91 (19)C26—C27—C28—C29−169.46 (16)
C7—C10—C12—C16−171.90 (15)O3—C27—C28—C30−162.41 (16)
C15—C12—C13—C1472.33 (19)C26—C27—C28—C3074.91 (19)
C10—C12—C13—C14−47.3 (2)O3—C27—C28—C2279.67 (19)
C16—C12—C13—C14−166.99 (15)C26—C27—C28—C22−43.0 (2)
C12—C13—C14—C25.1 (3)C23—C22—C28—C29−22.9 (3)
C1—C2—C14—C13−106.01 (19)C21—C22—C28—C29163.82 (16)
C3—C2—C14—C13140.93 (18)C23—C22—C28—C27−147.09 (18)
C7—C2—C14—C1318.0 (2)C21—C22—C28—C2739.6 (2)
C15—C12—C16—C2457.0 (2)C23—C22—C28—C3095.1 (2)
C13—C12—C16—C24−59.8 (2)C21—C22—C28—C30−78.2 (2)
C10—C12—C16—C24−178.05 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.85 (1)1.90 (1)2.731 (2)167 (3)
O3—H3···O2ii0.84 (1)2.36 (2)3.080 (2)144 (2)
Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.85 (1)1.90 (1)2.731 (2)167 (3)
O3—H3···O2ii0.84 (1)2.36 (2)3.080 (2)144 (2)
Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x+1, y−1/2, −z+1/2.
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
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