Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Two minor compounds were isolated from a sample of Harrisonia perforata leaves collected in central Vietnam, namely haperforin B1, C27H32O9, and haperforin D, C27H34O10. Biogenetically, haperforin D and haperforin B1 can be derived from each other by addition or elimination of water.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003565/gs1076sup1.cif
Contains datablocks B1, D, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003565/gs1076B1sup2.hkl
Contains datablock B1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003565/gs1076Dsup3.hkl
Contains datablock D

CCDC references: 146067; 146068

Computing details top

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NONIUS (Riche, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: R3M (Riche, 1983) and ORTEP (Johnson, 1965).

(B1) methyl 4-(3,6-dihydro-2,2-dimethyl-6-oxo-2H-pyran-3-ylideneacetyl)-8- furanoyl-5-(1-hydroxyethyl)-4,8-dimethyl-1-oxaspiro[2.5]octane-2-carboxylate top
Crystal data top
C27H32O9Dx = 1.301 Mg m3
Mr = 500.53Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 12.216 (4) Åθ = 14.0–22.1°
b = 12.463 (5) ŵ = 0.81 mm1
c = 16.781 (7) ÅT = 293 K
V = 2554.9 (17) Å3Prism, colorless
Z = 40.53 × 0.26 × 0.2 mm
F(000) = 1064
Data collection top
Nonius CAD4
diffractometer
Rint = 0.026
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 4.4°
Graphite monochromatorh = 1014
θ/2θ scansk = 014
3271 measured reflectionsl = 019
2327 independent reflections3 standard reflections every 120 min
2192 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.08Calculated w = 1/[σ2(Fo2) + (0.0859P)2 + 0.5597P]
where P = (Fo2 + 2Fc2)/3
2327 reflections(Δ/σ)max = 0.004
325 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.26 e Å3
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0596 (3)0.0522 (2)0.1814 (2)0.0393 (7)
C20.0238 (3)0.1355 (3)0.1232 (2)0.0448 (8)
H20.04860.20520.13100.054*
C30.0409 (3)0.1173 (3)0.0609 (2)0.0427 (7)
C40.0764 (3)0.2090 (3)0.0070 (2)0.0495 (8)
C50.2185 (4)0.0890 (4)0.0459 (2)0.0654 (11)
C60.1524 (4)0.0003 (4)0.0205 (3)0.0687 (12)
H60.16540.06770.04230.082*
C70.0732 (4)0.0107 (3)0.0334 (2)0.0567 (10)
H70.03820.04970.05370.068*
C80.1694 (2)0.0694 (2)0.2253 (2)0.0332 (6)
C90.2135 (3)0.0419 (2)0.2518 (2)0.0373 (7)
H90.15390.08000.27880.045*
C100.2522 (3)0.1117 (3)0.1818 (2)0.0555 (9)
H100.32750.08990.16970.067*
C110.3086 (3)0.0301 (2)0.3113 (2)0.0447 (8)
H11A0.32690.10060.33200.054*
H11B0.37220.00330.28300.054*
C120.2851 (3)0.0437 (2)0.3808 (2)0.0435 (8)
H12A0.35100.05080.41260.052*
H12B0.22940.01110.41410.052*
C130.2462 (3)0.1566 (2)0.3560 (2)0.0370 (7)
C140.1466 (2)0.1366 (2)0.3015 (2)0.0302 (6)
C150.0341 (3)0.1297 (2)0.3362 (2)0.0384 (7)
H150.01480.08120.30730.046*
C160.0005 (3)0.1508 (3)0.4200 (2)0.0447 (8)
C170.3415 (3)0.2205 (3)0.3173 (2)0.0406 (7)
C180.2210 (3)0.2221 (3)0.4325 (2)0.0469 (8)
H18A0.19660.29270.41790.056*
H18B0.28610.22760.46430.056*
H18C0.16470.18670.46250.056*
C190.2559 (5)0.2296 (3)0.2035 (3)0.089 (2)
H19A0.28030.27040.15830.107*
H19B0.18410.25310.21880.107*
H19C0.30570.24000.24710.107*
C200.3264 (3)0.3311 (3)0.2884 (2)0.0402 (7)
C210.2381 (3)0.3964 (3)0.2856 (3)0.0558 (10)
H210.16770.37590.30030.067*
C220.4146 (3)0.3953 (3)0.2594 (2)0.0517 (9)
H220.48690.37330.25330.062*
C230.3755 (4)0.4915 (3)0.2427 (3)0.0619 (11)
H230.41650.54840.22290.074*
C280.0912 (5)0.3139 (3)0.0502 (3)0.0765 (14)
H28A0.14100.30410.09390.092*
H28B0.12030.36650.01420.092*
H28C0.02180.33790.07020.092*
C290.0011 (4)0.2205 (4)0.0620 (2)0.0668 (11)
H29A0.00890.15250.08840.080*
H29B0.07120.24380.04290.080*
H29C0.02730.27240.09890.080*
C300.2491 (3)0.1279 (3)0.1690 (2)0.0421 (7)
H30A0.31770.13910.19560.051*
H30B0.21850.19600.15400.051*
H30C0.26070.08520.12210.051*
C310.0265 (4)0.0677 (4)0.5448 (2)0.0664 (11)
H31A0.01260.00050.57090.080*
H31B0.10380.08160.54460.080*
H31C0.01050.12430.57280.080*
O10.0010 (2)0.0229 (2)0.19693 (15)0.0531 (6)
O40.1860 (2)0.1882 (2)0.0261 (2)0.0660 (8)
O70.3039 (3)0.0793 (4)0.0824 (2)0.0964 (12)
O100.1900 (3)0.0965 (2)0.11050 (15)0.0639 (7)
HO100.13240.13000.113720.077*
O140.0676 (2)0.2218 (2)0.29068 (13)0.0397 (5)
O160.0422 (2)0.2327 (2)0.4432 (2)0.0601 (7)
O16'0.0131 (2)0.0629 (2)0.46411 (14)0.0504 (6)
O170.4332 (2)0.1828 (2)0.3173 (2)0.0582 (7)
O210.2651 (2)0.4948 (2)0.2589 (2)0.0685 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.041 (2)0.043 (2)0.034 (2)0.0027 (14)0.0045 (15)0.0004 (13)
C20.053 (2)0.041 (2)0.041 (2)0.0009 (15)0.008 (2)0.0019 (13)
C30.051 (2)0.046 (2)0.031 (2)0.0026 (15)0.004 (2)0.0019 (14)
C40.053 (2)0.047 (2)0.048 (2)0.007 (2)0.008 (2)0.002 (2)
C50.057 (2)0.086 (3)0.053 (2)0.009 (2)0.005 (2)0.011 (2)
C60.088 (3)0.062 (2)0.056 (2)0.020 (2)0.025 (2)0.002 (2)
C70.077 (3)0.049 (2)0.044 (2)0.002 (2)0.015 (2)0.002 (2)
C80.0352 (14)0.0333 (13)0.0313 (15)0.0009 (11)0.0008 (14)0.0013 (12)
C90.0359 (15)0.0344 (15)0.042 (2)0.0020 (12)0.0006 (14)0.0005 (13)
C100.055 (2)0.046 (2)0.065 (2)0.003 (2)0.004 (2)0.017 (2)
C110.039 (2)0.0404 (15)0.054 (2)0.0051 (13)0.008 (2)0.0029 (14)
C120.044 (2)0.040 (2)0.047 (2)0.0021 (14)0.008 (2)0.0057 (14)
C130.0366 (15)0.0377 (14)0.037 (2)0.0019 (13)0.0053 (14)0.0023 (13)
C140.0279 (12)0.0307 (12)0.032 (2)0.0005 (11)0.0004 (13)0.0008 (11)
C150.0350 (14)0.0383 (15)0.042 (2)0.0005 (12)0.0029 (14)0.0014 (13)
C160.042 (2)0.042 (2)0.050 (2)0.0033 (15)0.003 (2)0.0005 (14)
C170.0360 (15)0.044 (2)0.042 (2)0.0023 (13)0.0009 (15)0.0059 (14)
C180.050 (2)0.051 (2)0.039 (2)0.010 (2)0.004 (2)0.0059 (15)
C190.116 (4)0.048 (2)0.102 (4)0.026 (3)0.027 (4)0.023 (2)
C200.038 (2)0.043 (2)0.039 (2)0.0077 (13)0.0006 (14)0.0022 (14)
C210.050 (2)0.037 (2)0.081 (3)0.0021 (15)0.006 (2)0.006 (2)
C220.046 (2)0.057 (2)0.052 (2)0.012 (2)0.003 (2)0.001 (2)
C230.064 (2)0.055 (2)0.066 (3)0.018 (2)0.006 (2)0.008 (2)
C280.106 (4)0.051 (2)0.072 (3)0.024 (2)0.018 (3)0.004 (2)
C290.076 (3)0.074 (3)0.051 (2)0.003 (2)0.002 (2)0.018 (2)
C300.046 (2)0.047 (2)0.034 (2)0.0084 (14)0.006 (2)0.0021 (13)
C310.082 (3)0.073 (2)0.044 (2)0.006 (2)0.016 (2)0.007 (2)
O10.0506 (13)0.0567 (13)0.0521 (14)0.0171 (11)0.0092 (13)0.0090 (12)
O40.058 (2)0.069 (2)0.071 (2)0.0086 (14)0.0160 (15)0.0051 (15)
O70.067 (2)0.134 (3)0.088 (2)0.021 (2)0.030 (2)0.018 (2)
O100.085 (2)0.0597 (15)0.0475 (14)0.0137 (15)0.004 (2)0.0097 (12)
O140.0389 (11)0.0360 (10)0.0441 (12)0.0073 (9)0.0013 (10)0.0034 (9)
O160.069 (2)0.0582 (14)0.0536 (15)0.0233 (14)0.0154 (14)0.0015 (12)
O16'0.0587 (14)0.0461 (12)0.0463 (13)0.0029 (11)0.0134 (13)0.0031 (10)
O170.0327 (11)0.0545 (14)0.088 (2)0.0006 (10)0.0012 (13)0.0017 (14)
O210.067 (2)0.0425 (12)0.096 (2)0.0025 (12)0.007 (2)0.0121 (14)
Geometric parameters (Å, º) top
C1—O11.207 (4)C11—C121.513 (5)
C1—C21.490 (4)C12—C131.541 (4)
C1—C81.547 (4)C13—C141.543 (4)
C2—C31.330 (5)C13—C181.552 (5)
C3—C71.460 (5)C13—C171.554 (4)
C3—C41.521 (5)C14—O141.446 (3)
C4—O41.472 (5)C14—C151.494 (4)
C4—C291.503 (6)C15—O141.438 (4)
C4—C281.506 (5)C15—C161.492 (5)
C5—O71.216 (5)C16—O161.206 (4)
C5—O41.340 (5)C16—O16'1.332 (4)
C5—C61.440 (6)C17—O171.215 (4)
C6—C71.332 (6)C17—C201.473 (5)
C8—C301.540 (4)C20—C211.351 (5)
C8—C141.553 (4)C20—C221.429 (5)
C8—C91.553 (4)C21—O211.347 (4)
C9—C101.537 (5)C22—C231.320 (6)
C9—C111.538 (4)C23—O211.377 (5)
C10—O101.429 (5)C31—O16'1.439 (5)
C10—C191.515 (6)
O1—C1—C2120.5 (3)C12—C13—C14104.9 (2)
O1—C1—C8121.3 (3)C12—C13—C18108.6 (3)
C2—C1—C8118.1 (3)C14—C13—C18114.8 (3)
C3—C2—C1124.8 (3)C12—C13—C17110.4 (3)
C2—C3—C7124.3 (3)C14—C13—C17115.2 (3)
C2—C3—C4120.6 (3)C18—C13—C17103.0 (2)
C7—C3—C4114.8 (3)O14—C14—C1558.5 (2)
O4—C4—C29107.4 (3)O14—C14—C13118.9 (2)
O4—C4—C28103.0 (3)C15—C14—C13120.1 (3)
C29—C4—C28111.4 (4)O14—C14—C8114.4 (2)
O4—C4—C3110.5 (3)C15—C14—C8117.1 (2)
C29—C4—C3110.5 (3)C13—C14—C8115.7 (2)
C28—C4—C3113.6 (3)O14—C15—C16116.2 (3)
O7—C5—O4118.1 (4)O14—C15—C1459.0 (2)
O7—C5—C6123.6 (5)C16—C15—C14128.2 (3)
O4—C5—C6118.3 (4)O16—C16—O16'124.7 (3)
C7—C6—C5121.9 (4)O16—C16—C15124.9 (3)
C6—C7—C3120.3 (4)O16'—C16—C15110.1 (3)
C30—C8—C1108.7 (2)O17—C17—C20118.6 (3)
C30—C8—C14111.3 (2)O17—C17—C13119.5 (3)
C1—C8—C14108.1 (2)C20—C17—C13121.5 (3)
C30—C8—C9112.3 (2)C21—C20—C22104.6 (3)
C1—C8—C9108.3 (2)C21—C20—C17132.5 (3)
C14—C8—C9108.0 (2)C22—C20—C17122.8 (3)
C10—C9—C11108.6 (3)O21—C21—C20111.4 (3)
C10—C9—C8113.2 (3)C23—C22—C20108.0 (3)
C11—C9—C8111.3 (2)C22—C23—O21109.9 (3)
O10—C10—C19110.2 (3)C5—O4—C4121.7 (3)
O10—C10—C9113.7 (3)C15—O14—C1462.4 (2)
C19—C10—C9112.0 (4)C16—O16'—C31116.5 (3)
C12—C11—C9114.5 (3)C21—O21—C23106.1 (3)
C11—C12—C13114.0 (3)
O1—C1—C2—C331.3 (5)C18—C13—C14—C8179.0 (2)
C8—C1—C2—C3153.1 (3)C17—C13—C14—C861.7 (3)
C1—C2—C3—C79.7 (6)C30—C8—C14—O1479.6 (3)
C1—C2—C3—C4177.4 (3)C1—C8—C14—O1439.7 (3)
C7—C3—C4—O437.8 (4)C9—C8—C14—O14156.7 (2)
C3—C4—O4—C535.9 (5)C30—C8—C14—C15145.3 (3)
C4—O4—C5—C611.6 (6)C1—C8—C14—C1525.9 (3)
O4—C5—C6—C712.6 (7)C9—C8—C14—C1591.0 (3)
C5—C6—C7—C38.2 (7)C30—C8—C14—C1364.1 (3)
C6—C7—C3—C418.2 (6)C1—C8—C14—C13176.6 (2)
C8—C9—C10—O1033.8 (4)C9—C8—C14—C1359.6 (3)
C13—C14—C15—C166.8 (4)O14—C14—C15—O140.0
C14—C15—C16—O1699.9 (4)C13—C14—C15—O14107.4 (3)
C2—C3—C4—O4148.7 (3)C8—C14—C15—O14103.4 (3)
C2—C3—C4—C2992.6 (4)O14—C14—C15—C16100.6 (3)
C7—C3—C4—C2980.9 (4)C13—C14—C15—C166.8 (4)
C2—C3—C4—C2833.4 (5)C8—C14—C15—C16156.1 (3)
C7—C3—C4—C28153.0 (4)O14—C15—C16—O1630.0 (5)
O7—C5—C6—C7165.2 (5)C14—C15—C16—O1699.9 (4)
C2—C3—C7—C6168.6 (4)O14—C15—C16—O16'155.1 (3)
O1—C1—C8—C30151.0 (3)C14—C15—C16—O16'85.1 (4)
C2—C1—C8—C3033.4 (4)C12—C13—C17—O176.8 (4)
O1—C1—C8—C928.7 (4)C14—C13—C17—O17125.3 (3)
C2—C1—C8—C9155.7 (3)C18—C13—C17—O17109.0 (3)
O1—C1—C8—C1488.0 (3)C12—C13—C17—C20179.9 (3)
C2—C1—C8—C1487.6 (3)C14—C13—C17—C2061.6 (4)
C30—C8—C9—C1050.1 (3)C18—C13—C17—C2064.1 (4)
C1—C8—C9—C1069.9 (3)O17—C17—C20—C21175.3 (4)
C14—C8—C9—C10173.3 (3)C13—C17—C20—C212.1 (6)
C30—C8—C9—C1172.4 (3)O17—C17—C20—C220.8 (5)
C1—C8—C9—C11167.6 (3)C13—C17—C20—C22174.0 (3)
C14—C8—C9—C1150.7 (3)C22—C20—C21—O211.0 (5)
C11—C9—C10—O10157.8 (3)C17—C20—C21—O21175.6 (3)
C8—C9—C10—O1033.8 (4)C21—C20—C22—C230.7 (5)
C11—C9—C10—C1976.4 (4)C17—C20—C22—C23176.3 (3)
C8—C9—C10—C19159.5 (4)C20—C22—C23—O210.2 (5)
C10—C9—C11—C12175.7 (3)O7—C5—O4—C4170.5 (4)
C8—C9—C11—C1250.5 (4)C29—C4—O4—C584.8 (4)
C9—C11—C12—C1353.9 (4)C28—C4—O4—C5157.5 (4)
C11—C12—C13—C1454.7 (3)C16—C15—O14—C14120.6 (3)
C11—C12—C13—C18177.9 (3)C14—C15—O14—C140.0
C11—C12—C13—C1769.9 (3)C15—C14—O14—C150.0
C12—C13—C14—O14158.1 (3)C13—C14—O14—C15109.6 (3)
C18—C13—C14—O1439.0 (4)C8—C14—O14—C15108.0 (3)
C17—C13—C14—O1480.3 (3)O16—C16—O16'—C310.6 (6)
C12—C13—C14—C1589.8 (3)C15—C16—O16'—C31174.4 (3)
C18—C13—C14—C1529.3 (4)C20—C21—O21—C230.9 (5)
C17—C13—C14—C15148.6 (3)C22—C23—O21—C210.5 (5)
C12—C13—C14—C859.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—HO10···O16i0.822.252.933 (4)141
Symmetry code: (i) x, y1/2, z+1/2.
(D) methyl 6'-furanoyl-3-hydroxy-4,4,3',6',7a'-pentamethylperhydro-4H-furo[2,1-c]- pyran-2-spiro-1'-perhydroisobenzofuran-7'-spiro-2''-oxirane-3''-carboxylate top
Crystal data top
C27H34O10F(000) = 552
Mr = 518.54Dx = 1.350 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
a = 10.148 (5) ÅCell parameters from 25 reflections
b = 11.225 (7) Åθ = 15.2–21.0°
c = 11.356 (8) ŵ = 0.86 mm1
β = 99.44 (2)°T = 293 K
V = 1276.1 (14) Å3Prism, colourless
Z = 20.35 × 0.35 × 0.20 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.061
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 4.4°
Graphite monochromatorh = 1111
θ/2θ scansk = 013
3411 measured reflectionsl = 013
2389 independent reflections3 standard reflections every 120 min
2368 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.09Calculated w = 1/[σ2(Fo2) + (0.1223P)2 + 0.1273P]
where P = (Fo2 + 2Fc2)/3
2385 reflections(Δ/σ)max = 0.023
334 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.40 e Å3
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 on F2 for ALL reflections except for 4 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3417 (3)0.3796 (4)0.8838 (2)0.0413 (6)
C20.2893 (3)0.3384 (4)0.9969 (2)0.0435 (6)
H20.36090.30151.05350.052*
C30.2482 (3)0.4577 (4)1.0446 (3)0.0478 (7)
H30.32960.49601.08610.057*
C40.1472 (3)0.4560 (5)1.1306 (3)0.0557 (8)
C50.0262 (3)0.4443 (6)0.9550 (4)0.0698 (11)
C60.0488 (4)0.5422 (6)0.9025 (4)0.0761 (13)
H6A0.02360.61830.93260.091*
H6B0.02180.54260.81650.091*
C70.2003 (4)0.5298 (4)0.9308 (3)0.0552 (8)
H70.24150.60900.93800.066*
C80.3746 (3)0.2872 (4)0.7896 (2)0.0400 (6)
C90.4618 (3)0.3705 (4)0.7256 (3)0.0450 (7)
H90.40270.43210.68490.054*
C100.5506 (3)0.4301 (4)0.8297 (3)0.0496 (7)
H100.62630.37760.85820.060*
C110.5254 (4)0.3063 (4)0.6305 (3)0.0531 (8)
H11A0.57390.36290.58930.064*
H11B0.58800.24680.66780.064*
C120.4170 (4)0.2472 (4)0.5423 (3)0.0550 (8)
H12A0.45870.20420.48420.066*
H12B0.36120.30870.49990.066*
C130.3263 (3)0.1594 (4)0.5987 (3)0.0468 (7)
C140.2683 (3)0.2296 (4)0.6958 (2)0.0406 (6)
C150.1306 (3)0.2815 (4)0.6744 (3)0.0486 (7)
H150.12210.35190.72350.058*
C160.0269 (4)0.2765 (5)0.5647 (3)0.0589 (9)
C170.4072 (3)0.0464 (4)0.6414 (3)0.0482 (7)
C180.2206 (4)0.1108 (5)0.4972 (3)0.0618 (9)
H18A0.16370.17470.46350.093*
H18B0.16790.05120.52830.093*
H18C0.26420.07630.43650.093*
C190.6028 (5)0.5517 (5)0.8063 (5)0.0731 (11)
H19A0.65740.58090.87750.110*
H19B0.52910.60500.78310.110*
H19C0.65520.54670.74330.110*
C200.3526 (3)0.0513 (4)0.7058 (3)0.0492 (7)
C210.2329 (5)0.0688 (5)0.7469 (6)0.088 (2)
H210.16260.01470.73980.105*
C220.4252 (4)0.1539 (5)0.7385 (4)0.0608 (9)
H220.50970.17060.72110.073*
C230.3551 (4)0.2249 (5)0.7990 (4)0.0655 (10)
H230.38480.29640.83540.079*
C280.1360 (5)0.5813 (6)1.1824 (5)0.0831 (15)
H28A0.11450.63741.11840.125*
H28B0.21950.60281.23030.125*
H28C0.06690.58181.23090.125*
C290.1811 (4)0.3630 (7)1.2279 (3)0.0768 (13)
H29A0.11540.36491.27980.115*
H29B0.26760.37971.27320.115*
H29C0.18180.28541.19230.115*
C300.4587 (3)0.1895 (4)0.8634 (3)0.0440 (6)
H30A0.52520.22620.92210.066*
H30B0.50160.14100.81120.066*
H30C0.40130.14070.90260.066*
C310.1611 (6)0.1723 (9)0.4668 (5)0.108 (2)
H31A0.21220.10230.47730.162*
H31B0.12510.16570.39390.162*
H31C0.21770.24120.46300.162*
O10.2442 (2)0.4654 (3)0.8336 (2)0.0480 (5)
O20.1793 (2)0.2612 (4)0.9714 (2)0.0530 (6)
HO20.16500.24650.89970.051*
O40.0151 (2)0.4182 (4)1.0686 (2)0.0618 (7)
O70.1231 (4)0.3961 (7)0.9026 (4)0.110 (2)
O100.4660 (2)0.4386 (4)0.9212 (2)0.0546 (6)
O140.1587 (2)0.1745 (3)0.7438 (2)0.0473 (5)
O160.0167 (4)0.3540 (4)0.4901 (3)0.0815 (9)
O16'0.0534 (3)0.1840 (5)0.5658 (2)0.0725 (8)
O170.5166 (3)0.0316 (4)0.6119 (3)0.0641 (7)
O210.2348 (4)0.1762 (5)0.7988 (5)0.111 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0345 (13)0.0444 (14)0.0479 (13)0.0017 (11)0.0149 (10)0.0026 (12)
C20.0396 (14)0.052 (2)0.0413 (12)0.0005 (12)0.0128 (10)0.0000 (12)
C30.0373 (13)0.057 (2)0.0533 (15)0.0058 (12)0.0185 (11)0.0083 (13)
C40.041 (2)0.076 (2)0.054 (2)0.0005 (15)0.0198 (13)0.012 (2)
C50.035 (2)0.094 (3)0.081 (2)0.013 (2)0.0119 (15)0.009 (2)
C60.070 (2)0.086 (3)0.078 (2)0.038 (2)0.029 (2)0.018 (2)
C70.057 (2)0.048 (2)0.067 (2)0.006 (2)0.0290 (15)0.000 (2)
C80.0356 (12)0.0457 (15)0.0420 (13)0.0035 (11)0.0161 (10)0.0044 (12)
C90.0433 (14)0.0437 (15)0.0539 (15)0.0038 (12)0.0254 (12)0.0089 (13)
C100.0429 (15)0.045 (2)0.067 (2)0.0009 (13)0.0278 (13)0.0007 (14)
C110.055 (2)0.051 (2)0.063 (2)0.0017 (15)0.0357 (14)0.0058 (15)
C120.069 (2)0.056 (2)0.0468 (15)0.006 (2)0.0306 (14)0.0086 (14)
C130.049 (2)0.052 (2)0.0423 (13)0.0041 (14)0.0177 (11)0.0023 (13)
C140.0423 (14)0.0441 (14)0.0385 (12)0.0009 (11)0.0160 (10)0.0062 (11)
C150.0419 (14)0.057 (2)0.0481 (14)0.0055 (13)0.0114 (11)0.0031 (14)
C160.049 (2)0.074 (2)0.054 (2)0.009 (2)0.0080 (13)0.005 (2)
C170.049 (2)0.047 (2)0.0524 (15)0.0009 (13)0.0181 (12)0.0024 (13)
C180.064 (2)0.072 (2)0.050 (2)0.007 (2)0.0117 (14)0.008 (2)
C190.082 (3)0.050 (2)0.098 (3)0.014 (2)0.045 (2)0.004 (2)
C200.0431 (14)0.046 (2)0.060 (2)0.0001 (13)0.0148 (12)0.0014 (14)
C210.062 (2)0.053 (2)0.157 (5)0.003 (2)0.045 (3)0.031 (3)
C220.050 (2)0.063 (2)0.070 (2)0.002 (2)0.0126 (15)0.014 (2)
C230.049 (2)0.055 (2)0.097 (3)0.009 (2)0.024 (2)0.029 (2)
C280.068 (2)0.102 (4)0.087 (3)0.001 (3)0.033 (2)0.043 (3)
C290.069 (2)0.115 (4)0.054 (2)0.015 (3)0.030 (2)0.011 (2)
C300.0415 (13)0.0461 (15)0.0461 (13)0.0050 (13)0.0120 (10)0.0049 (13)
C310.080 (3)0.137 (6)0.093 (3)0.013 (4)0.028 (3)0.003 (4)
O10.0500 (11)0.0454 (12)0.0527 (11)0.0071 (9)0.0203 (9)0.0047 (9)
O20.0571 (13)0.0585 (13)0.0489 (11)0.0117 (11)0.0254 (9)0.0020 (10)
O40.0390 (11)0.082 (2)0.0696 (14)0.0042 (12)0.0225 (10)0.0036 (13)
O70.055 (2)0.163 (5)0.106 (2)0.002 (2)0.005 (2)0.023 (3)
O100.0418 (11)0.0639 (14)0.0635 (13)0.0094 (11)0.0245 (9)0.0145 (11)
O140.0415 (10)0.0606 (13)0.0420 (9)0.0036 (9)0.0140 (8)0.0074 (10)
O160.081 (2)0.083 (2)0.075 (2)0.011 (2)0.0023 (15)0.022 (2)
O16'0.0589 (14)0.094 (2)0.0613 (14)0.010 (2)0.0002 (11)0.007 (2)
O170.0602 (14)0.0558 (14)0.086 (2)0.0083 (12)0.0417 (13)0.0019 (13)
O210.090 (2)0.084 (3)0.175 (4)0.013 (2)0.069 (3)0.047 (3)
Geometric parameters (Å, º) top
C1—O101.426 (4)C10—O101.456 (3)
C1—O11.430 (4)C10—C191.502 (5)
C1—C21.540 (4)C11—C121.514 (6)
C1—C81.565 (4)C12—C131.556 (5)
C2—O21.405 (4)C13—C181.540 (5)
C2—C31.528 (5)C13—C171.546 (5)
C3—C41.528 (4)C13—C141.548 (4)
C3—C71.535 (5)C14—O141.455 (3)
C4—O41.471 (4)C14—C151.496 (4)
C4—C291.518 (6)C15—O141.439 (4)
C4—C281.535 (7)C15—C161.494 (5)
C5—O71.193 (6)C16—O161.207 (5)
C5—O41.322 (5)C16—O16'1.322 (6)
C5—C61.514 (8)C17—O171.223 (4)
C6—C71.524 (6)C17—C201.475 (5)
C7—O11.449 (4)C20—C221.385 (6)
C8—C141.530 (4)C20—C211.385 (6)
C8—C91.548 (4)C21—O211.341 (7)
C8—C301.549 (4)C22—C231.332 (6)
C9—C101.519 (5)C23—O211.337 (6)
C9—C111.526 (4)C31—O16'1.440 (5)
O10—C1—O1109.0 (3)C19—C10—C9116.3 (3)
O10—C1—C2107.5 (2)C12—C11—C9109.3 (3)
O1—C1—C2102.9 (2)C11—C12—C13114.9 (3)
O10—C1—C8103.5 (2)C18—C13—C17102.3 (3)
O1—C1—C8112.6 (2)C18—C13—C14114.4 (3)
C2—C1—C8120.9 (3)C17—C13—C14116.0 (2)
O2—C2—C3111.1 (2)C18—C13—C12107.7 (3)
O2—C2—C1112.7 (2)C17—C13—C12109.2 (3)
C3—C2—C1100.6 (3)C14—C13—C12106.9 (3)
C2—C3—C4117.8 (3)O14—C14—C1558.4 (2)
C2—C3—C7103.3 (2)O14—C14—C8114.4 (2)
C4—C3—C7113.1 (3)C15—C14—C8118.8 (3)
O4—C4—C29103.3 (3)O14—C14—C13117.0 (3)
O4—C4—C3110.6 (3)C15—C14—C13122.4 (3)
C29—C4—C3112.2 (3)C8—C14—C13113.8 (2)
O4—C4—C28109.2 (3)O14—C15—C16118.3 (3)
C29—C4—C28111.9 (4)O14—C15—C1459.4 (2)
C3—C4—C28109.5 (3)C16—C15—C14129.2 (3)
O7—C5—O4119.4 (5)O16—C16—O16'126.2 (4)
O7—C5—C6124.0 (5)O16—C16—C15121.7 (4)
O4—C5—C6116.4 (4)O16'—C16—C15111.9 (3)
C5—C6—C7113.9 (3)O17—C17—C20117.8 (3)
O1—C7—C6108.1 (3)O17—C17—C13119.0 (3)
O1—C7—C3106.5 (3)C20—C17—C13122.9 (3)
C6—C7—C3113.3 (3)C22—C20—C21104.4 (3)
C14—C8—C9108.7 (2)C22—C20—C17121.7 (3)
C14—C8—C30109.9 (3)C21—C20—C17133.9 (4)
C9—C8—C30112.1 (2)O21—C21—C20108.9 (4)
C14—C8—C1123.4 (2)C23—C22—C20109.3 (3)
C9—C8—C197.1 (2)C22—C23—O21108.6 (4)
C30—C8—C1105.1 (2)C1—O1—C7108.2 (2)
C10—C9—C11119.5 (3)C5—O4—C4121.4 (3)
C10—C9—C8102.3 (2)C1—O10—C10110.7 (2)
C11—C9—C8112.8 (3)C15—O14—C1462.3 (2)
O10—C10—C19109.4 (3)C16—O16'—C31117.0 (4)
O10—C10—C9103.9 (2)C23—O21—C21108.5 (4)
O10—C1—C2—O2169.6 (3)C30—C8—C14—O1472.5 (3)
O1—C1—C2—O275.4 (3)C1—C8—C14—O1452.3 (4)
C8—C1—C2—O251.3 (3)C9—C8—C14—C1598.6 (3)
O10—C1—C2—C372.0 (3)C30—C8—C14—C15138.4 (3)
O1—C1—C2—C343.0 (3)C1—C8—C14—C1513.7 (4)
C8—C1—C2—C3169.6 (2)C9—C8—C14—C1357.2 (3)
O2—C2—C3—C439.4 (4)C30—C8—C14—C1365.8 (3)
C1—C2—C3—C4158.9 (3)C1—C8—C14—C13169.5 (2)
O2—C2—C3—C786.0 (3)C18—C13—C14—O1448.3 (4)
C1—C2—C3—C733.4 (3)C17—C13—C14—O1470.5 (3)
C2—C3—C4—O468.3 (4)C12—C13—C14—O14167.4 (2)
C2—C3—C4—C2946.5 (4)C18—C13—C14—C1519.8 (4)
C7—C3—C4—C29167.0 (4)C17—C13—C14—C15138.6 (3)
C2—C3—C4—C28171.4 (3)C12—C13—C14—C1599.3 (3)
C7—C3—C4—C2868.1 (4)C18—C13—C14—C8174.6 (3)
O7—C5—C6—C7137.4 (5)C17—C13—C14—C866.6 (3)
C5—C6—C7—O193.2 (4)C12—C13—C14—C855.5 (3)
C2—C3—C7—O113.2 (3)O14—C14—C15—O140.000 (1)
C3—C7—O1—C114.6 (3)C8—C14—C15—O14102.5 (3)
C7—O1—C1—C236.3 (3)C13—C14—C15—O14103.9 (3)
C4—C3—C7—C623.0 (5)O14—C14—C15—C16103.2 (4)
C3—C7—C6—C524.5 (5)C8—C14—C15—C16154.3 (3)
C7—C6—C5—O447.5 (5)O14—C15—C16—O16165.0 (4)
C6—C5—O4—C417.0 (6)O14—C15—C16—O16'19.3 (4)
C5—O4—C4—C332.7 (5)C14—C15—C16—O16'91.4 (4)
O4—C4—C3—C752.3 (4)C18—C13—C17—O17103.3 (3)
O10—C1—C8—C942.2 (3)C14—C13—C17—O17131.5 (3)
C1—C8—C9—C1045.1 (3)C12—C13—C17—O1710.6 (4)
C8—C9—C10—O1032.9 (3)C18—C13—C17—C2070.0 (4)
C9—C10—O10—C15.5 (3)C14—C13—C17—C2055.3 (4)
C10—O10—C1—C823.9 (3)C12—C13—C17—C20176.1 (3)
C13—C14—C15—C160.7 (5)O17—C17—C20—C223.9 (5)
C14—C15—C16—O1692.8 (5)C13—C17—C20—C22177.2 (3)
C4—C3—C7—O1141.7 (3)O17—C17—C20—C21176.3 (5)
C2—C3—C7—C6105.5 (3)C13—C17—C20—C213.0 (7)
O10—C1—C8—C14160.1 (3)C22—C20—C21—O211.0 (7)
O1—C1—C8—C1442.5 (3)C17—C20—C21—O21179.1 (5)
C2—C1—C8—C1479.6 (3)C21—C20—C22—C232.2 (6)
O1—C1—C8—C975.5 (3)C17—C20—C22—C23177.6 (4)
C2—C1—C8—C9162.4 (2)C20—C22—C23—O214.7 (6)
O10—C1—C8—C3073.0 (3)O10—C1—O1—C777.6 (3)
O1—C1—C8—C30169.3 (2)C8—C1—O1—C7168.1 (2)
C2—C1—C8—C3047.3 (3)C6—C7—O1—C1136.6 (3)
C14—C8—C9—C10174.0 (2)O7—C5—O4—C4167.7 (5)
C30—C8—C9—C1064.3 (3)C29—C4—O4—C5153.0 (4)
C14—C8—C9—C1156.3 (3)C28—C4—O4—C587.8 (4)
C30—C8—C9—C1165.4 (3)O1—C1—O10—C1096.2 (3)
C1—C8—C9—C11174.8 (3)C2—C1—O10—C10152.9 (3)
C11—C9—C10—O10158.3 (3)C19—C10—O10—C1130.4 (3)
C11—C9—C10—C1981.4 (4)C16—C15—O14—C14121.1 (3)
C8—C9—C10—C19153.3 (3)C14—C15—O14—C140.000 (1)
C10—C9—C11—C12175.8 (3)C15—C14—O14—C150.000 (1)
C8—C9—C11—C1255.6 (4)C8—C14—O14—C15110.0 (3)
C9—C11—C12—C1356.1 (4)C13—C14—O14—C15113.2 (3)
C11—C12—C13—C18178.5 (3)O16—C16—O16'—C312.0 (7)
C11—C12—C13—C1771.1 (4)C15—C16—O16'—C31177.6 (5)
C11—C12—C13—C1455.1 (4)C22—C23—O21—C215.4 (7)
C9—C8—C14—O14164.6 (2)C20—C21—O21—C233.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HO2···O140.821.942.738 (3)165
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds