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The title compound, 2-[1,2,3,4,4a,4b,5,6,7,8,8a,9-dodeca­hydro-7-hydroxy-4b,8,8-tri­methyl­phenanthren-2-yl]­propenoic acid, C20H30O3, is a naturally occurring diterpenoid which was isolated from Rabdosia macrocalyx. The hydroxy and carboxy groups, which are located at the two ends of the mol­ecule, both serve as simultaneous hydrogen-bond donors and acceptors. Two intermolecular O-H...O hydrogen bonds are present and link each mol­ecule to four neighbours, thus forming an extensive hydrogen-bond network within the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101018625/ta1347sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101018625/ta1347Isup2.hkl
Contains datablock I

CCDC reference: 180175

Comment top

Rabdosia macrocalyx is widely distributed in Anhui, Jiangsu,Zhejiang, Jiangxi, Fujian, Hunan, Guangdong, Guangxi and Taiwan provinces, China. It has been used as a folk medicine in China. Its decoctions are used as antibiotics and for antitumor treatment. Macrocalyxins A, B (Cheng et al., 1984), C (Wang et al., 1984), D (Wang et al., 1985), E (Wang et al., 1986), F, G and H (Wang et al., 1995) have been isolated previously from this plant. In order to isolate more bioactive constituents from this plant, we investigated the whole herb of Rabdosia macrocalyx, which led to the isolation of the title compound, the natural diterpenoid Macrocalyxin I, (1), which was isolated from Rabdosia macrocalyx Hara for the first time. Its structure was established from spectral evidence and was confirmed by this X-ray diffraction study.

The molecule of (1) (Fig. 1) is composed of three six-membered rings. Rings A (C1–C5/C10) and C (C8/C9/C12–C14) adopt a chair conformation, with mean torsion angles of 51.4 and 52.4°, respectively. Ring B (C5–C9/C10) adopts a half-chair conformation owing to the double bond between C7 and C8. The stereochemistry of the A/B ring junction is trans, and the dihedral angle between rings A and B is 17.6°; the dihedral angle between rings B and C is 14.9°. The configurations at the other chiral centers are as follows: C3—OH, C10—Me, C9—H and C13—H are axial and the 1-carboxylethenyl group is equatorial at C13.

The C17—C15—C16—O2 torsion angle has a vlaue of 172.4 (3)° because of the conjugated double bound. The best least-squares plane formed by atoms C17/C15/C16/O2/O3 has a maximum deviation of 0.0592 Å, and the dihedral angle between this plane and ring C is 114.2°. The hydroxyl group located at C3 and the carboxyl group located at C15 participate in hydrogen bonding. Both groups serve as simultaneous hydrogen-bond donors and acceptors. Two intermolecular O—H···O hydrogen bonds (Table 2) are present and link each molecule to four adjacent neighbours (Fig. 2). The overall result is an extended hydrogen-bonding network throughout the structure (Fig. 3).

Experimental top

Dried powder (7.5 kg) of the whole herb of Rabdosia macrocalyx were soaked three times with 95% EtOH at room temperature. The solvent was removed by evaporation at reduced pressure, the residue was successively fractioned with petroleum ether, EtOAc and n-BuOH. The residue of the EtOAc fraction was subjected to column chromatography over silica gel. The column was eluted with a petroleum ether–EtOAc mixture. The crude compound was purified by column chromatography on silica gel with an acetone–chloroform mixture, producing 210 mg of macrocalyxin A and 60 mg of the pure title compound, (1) [m.p.: 490.5–492.5 K (CHCl3/CH3COCH3)]. 13C NMR (125 MHz, pyridine): δ (p.p.m.) 169.8 (C16), 147.5 (C15), 137.2 (C8), 121.7 (C17), 121.2 (C7), 75.1 (C3), 52.4 (C9), 44.3 (C5), 41.7 (C6), 39.7 (C13), 37.5 (C4), 35.3 (C10), 32.3 (C14), 32.2 (C12), 29.3 (C19), 26.4 (C11), 25.7 (C1), 23.3 (C2), 23.1 (C18), 15.3 (C20). Crystals suitable for X-ray structure analysis were obtained by slow evaporation from an aqueous solution solution in chloroform and methanol (1:1) at room temperature.

Refinement top

H atoms were placed in the geometrically calculated positions and included in the final refinement as riding, with Uiso values equal to 1.2Ueq of the carrier atom. An attempt to establish the absolute configuration failed. The Flack (1983) parameter obtained was -0.9 (16). The Friedel pairs were merged before the final refinement and only the relative stereochemistry is shown in the Scheme and Figures.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Siemens, 1991); software used to prepare material for publication: SHELXTL/PC.

Figures top
[Figure 1] Fig. 1. View of the title molecule showing the atomic numbering scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The intermoleculer hydrogen bonding in (1) viewed normal to the (001) plane. H atoms have been omitted for clarity, except for those involved in hydrogen bonds, which are drawn as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The crystal-packing diagram for the title compound viewed down the c axis. H atoms have been omitted for clarity, except for these involved in hydrogen bonds.
2-[1,2,3,4,4a,4 b,5,6,7,8,8a,9-dodecahydro-7-hydroxy-4 b,8,8-trimethylphenanthren- 2-yl]propenoic acid top
Crystal data top
C20H30O3Dx = 1.176 Mg m3
Mr = 318.44Melting point: 490.5-492.5K K
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 24.066 (2) ÅCell parameters from 25 reflections
b = 10.017 (1) Åθ = 3.3–12.3°
c = 7.608 (1) ŵ = 0.08 mm1
β = 101.35 (1)°T = 295 K
V = 1798.2 (3) Å3Prism, colorless
Z = 40.50 × 0.50 × 0.40 mm
F(000) = 696
Data collection top
Siemens P4
diffractometer
Rint = 0.016
Radiation source: normal-focus sealed tubeθmax = 27.5°, θmin = 1.7°
Graphite monochromatorh = 031
ω scansk = 013
2311 measured reflectionsl = 99
2178 independent reflections3 standard reflections every 97 reflections
1605 reflections with I > 2σ(I) intensity decay: 1.3%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0509P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.15 e Å3
2178 reflectionsΔρmin = 0.12 e Å3
214 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.035 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: see text
Secondary atom site location: difference Fourier map
Crystal data top
C20H30O3V = 1798.2 (3) Å3
Mr = 318.44Z = 4
Monoclinic, C2Mo Kα radiation
a = 24.066 (2) ŵ = 0.08 mm1
b = 10.017 (1) ÅT = 295 K
c = 7.608 (1) Å0.50 × 0.50 × 0.40 mm
β = 101.35 (1)°
Data collection top
Siemens P4
diffractometer
Rint = 0.016
2311 measured reflections3 standard reflections every 97 reflections
2178 independent reflections intensity decay: 1.3%
1605 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0401 restraint
wR(F2) = 0.097H-atom parameters constrained
S = 0.98Δρmax = 0.15 e Å3
2178 reflectionsΔρmin = 0.12 e Å3
214 parametersAbsolute structure: see text
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. 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
O10.90473 (7)0.3283 (2)0.8642 (2)0.0532 (5)
H1O0.91800.31240.96990.064*
O20.53159 (7)0.75895 (18)0.8040 (3)0.0541 (5)
O30.45819 (7)0.62074 (19)0.7549 (3)0.0648 (6)
H3O0.44140.68850.77560.078*
C10.83633 (10)0.5363 (3)0.9824 (3)0.0532 (7)
H1A0.82780.59331.07670.064*
H1B0.82950.44471.01340.064*
C20.89867 (11)0.5522 (3)0.9736 (4)0.0579 (8)
H2A0.90630.64500.95080.070*
H2B0.92190.52751.08820.070*
C30.91440 (10)0.4655 (3)0.8268 (3)0.0488 (7)
H30.95470.47790.82590.059*
C40.87985 (10)0.4993 (3)0.6406 (3)0.0470 (6)
C50.81543 (9)0.4995 (2)0.6465 (3)0.0396 (5)
H50.80620.40540.66110.048*
C60.77756 (10)0.5410 (3)0.4699 (3)0.0531 (7)
H6A0.78570.63290.44340.064*
H6B0.78580.48540.37380.064*
C70.71645 (11)0.5280 (3)0.4782 (3)0.0534 (7)
H70.69000.53100.37120.064*
C80.69758 (10)0.5125 (3)0.6285 (3)0.0426 (6)
C90.73609 (9)0.5174 (3)0.8114 (3)0.0400 (5)
H90.74130.42470.85240.048*
C100.79625 (10)0.5718 (3)0.8048 (3)0.0407 (6)
C110.70718 (9)0.5897 (4)0.9470 (3)0.0616 (8)
H11A0.72970.57681.06640.074*
H11B0.70630.68470.92150.074*
C120.64725 (10)0.5421 (3)0.9445 (3)0.0592 (8)
H12A0.63110.59241.03130.071*
H12B0.64790.44860.97810.071*
C130.61058 (9)0.5600 (3)0.7583 (3)0.0432 (6)
H130.61310.65410.72560.052*
C140.63637 (10)0.4785 (3)0.6268 (3)0.0544 (7)
H14A0.63370.38460.65490.065*
H14B0.61450.49290.50690.065*
C150.54878 (10)0.5299 (3)0.7544 (3)0.0486 (6)
C160.51282 (10)0.6467 (3)0.7736 (3)0.0429 (6)
C170.52643 (13)0.4102 (3)0.7418 (5)0.0889 (13)
H17A0.48830.39920.74500.107*
H17B0.54870.33620.72970.107*
C180.90256 (13)0.6308 (3)0.5786 (5)0.0764 (10)
H18A0.94160.61980.57050.092*
H18B0.89940.70000.66330.092*
H18C0.88090.65470.46310.092*
C190.89093 (12)0.3919 (3)0.5080 (4)0.0627 (8)
H19A0.87380.30940.53360.075*
H19B0.93100.37950.51940.075*
H19C0.87490.41960.38800.075*
C200.79329 (13)0.7233 (3)0.7790 (4)0.0625 (8)
H20A0.82860.75510.75450.075*
H20B0.78620.76500.88600.075*
H20C0.76320.74500.68020.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0468 (10)0.0565 (11)0.0572 (11)0.0140 (8)0.0123 (9)0.0107 (9)
O20.0397 (10)0.0500 (11)0.0724 (12)0.0019 (8)0.0103 (8)0.0115 (10)
O30.0347 (9)0.0578 (13)0.1020 (16)0.0043 (9)0.0137 (10)0.0135 (11)
C10.0421 (14)0.073 (2)0.0420 (14)0.0109 (13)0.0028 (11)0.0117 (14)
C20.0450 (14)0.070 (2)0.0551 (16)0.0043 (13)0.0001 (12)0.0117 (15)
C30.0335 (12)0.0515 (16)0.0622 (17)0.0016 (11)0.0111 (11)0.0009 (13)
C40.0421 (13)0.0496 (15)0.0531 (15)0.0028 (11)0.0184 (11)0.0066 (12)
C50.0396 (12)0.0390 (14)0.0410 (12)0.0057 (10)0.0098 (10)0.0000 (11)
C60.0556 (15)0.0665 (19)0.0389 (13)0.0123 (14)0.0132 (11)0.0056 (13)
C70.0461 (14)0.0743 (19)0.0363 (13)0.0144 (14)0.0001 (11)0.0022 (14)
C80.0388 (12)0.0466 (14)0.0409 (12)0.0114 (11)0.0043 (10)0.0059 (11)
C90.0373 (12)0.0460 (13)0.0366 (12)0.0133 (11)0.0073 (9)0.0012 (11)
C100.0381 (12)0.0413 (13)0.0417 (13)0.0060 (10)0.0051 (10)0.0022 (11)
C110.0397 (13)0.103 (2)0.0408 (14)0.0161 (15)0.0036 (11)0.0162 (16)
C120.0452 (14)0.088 (2)0.0461 (15)0.0207 (15)0.0122 (11)0.0002 (15)
C130.0362 (12)0.0439 (14)0.0491 (14)0.0104 (11)0.0077 (10)0.0032 (12)
C140.0437 (14)0.0656 (19)0.0527 (15)0.0064 (13)0.0063 (11)0.0126 (13)
C150.0413 (13)0.0454 (15)0.0595 (15)0.0048 (12)0.0111 (11)0.0001 (13)
C160.0337 (12)0.0513 (16)0.0423 (14)0.0052 (11)0.0043 (10)0.0005 (12)
C170.060 (2)0.0477 (19)0.166 (4)0.0026 (16)0.038 (2)0.001 (2)
C180.0600 (18)0.073 (2)0.103 (3)0.0001 (17)0.0308 (17)0.024 (2)
C190.0587 (17)0.076 (2)0.0580 (17)0.0187 (16)0.0238 (13)0.0033 (16)
C200.0612 (18)0.0430 (16)0.084 (2)0.0073 (13)0.0164 (15)0.0148 (15)
Geometric parameters (Å, º) top
O1—C31.432 (3)C9—C101.557 (3)
O1—H1O0.8200C9—H90.9800
O2—C161.217 (3)C10—C201.530 (4)
O3—C161.320 (3)C11—C121.516 (4)
O3—H3O0.8200C11—H11A0.9700
C1—C21.523 (3)C11—H11B0.9700
C1—C101.539 (3)C12—C131.525 (3)
C1—H1A0.9700C12—H12A0.9700
C1—H1B0.9700C12—H12B0.9700
C2—C31.520 (4)C13—C151.512 (3)
C2—H2A0.9700C13—C141.516 (3)
C2—H2B0.9700C13—H130.9800
C3—C41.533 (4)C14—H14A0.9700
C3—H30.9800C14—H14B0.9700
C4—C191.534 (4)C15—C171.310 (4)
C4—C181.535 (4)C15—C161.479 (3)
C4—C51.560 (3)C17—H17A0.9300
C5—C61.526 (3)C17—H17B0.9300
C5—C101.552 (3)C18—H18A0.9600
C5—H50.9800C18—H18B0.9600
C6—C71.490 (3)C18—H18C0.9600
C6—H6A0.9700C19—H19A0.9600
C6—H6B0.9700C19—H19B0.9600
C7—C81.320 (3)C19—H19C0.9600
C7—H70.9300C20—H20A0.9600
C8—C141.510 (3)C20—H20B0.9600
C8—C91.513 (3)C20—H20C0.9600
C9—C111.535 (3)
C3—O1—H1O109.5C1—C10—C9108.47 (19)
C16—O3—H3O109.5C5—C10—C9106.37 (18)
C2—C1—C10113.0 (2)C12—C11—C9113.5 (2)
C2—C1—H1A109.0C12—C11—H11A108.9
C10—C1—H1A109.0C9—C11—H11A108.9
C2—C1—H1B109.0C12—C11—H11B108.9
C10—C1—H1B109.0C9—C11—H11B108.9
H1A—C1—H1B107.8H11A—C11—H11B107.7
C3—C2—C1111.2 (2)C11—C12—C13110.5 (2)
C3—C2—H2A109.4C11—C12—H12A109.6
C1—C2—H2A109.4C13—C12—H12A109.6
C3—C2—H2B109.4C11—C12—H12B109.6
C1—C2—H2B109.4C13—C12—H12B109.6
H2A—C2—H2B108.0H12A—C12—H12B108.1
O1—C3—C2109.2 (2)C15—C13—C14114.1 (2)
O1—C3—C4108.4 (2)C15—C13—C12112.5 (2)
C2—C3—C4112.6 (2)C14—C13—C12108.22 (19)
O1—C3—H3108.9C15—C13—H13107.2
C2—C3—H3108.9C14—C13—H13107.2
C4—C3—H3108.9C12—C13—H13107.2
C3—C4—C19108.7 (2)C8—C14—C13113.5 (2)
C3—C4—C18108.2 (2)C8—C14—H14A108.9
C19—C4—C18106.3 (2)C13—C14—H14A108.9
C3—C4—C5109.60 (18)C8—C14—H14B108.9
C19—C4—C5108.8 (2)C13—C14—H14B108.9
C18—C4—C5115.1 (2)H14A—C14—H14B107.7
C6—C5—C10109.80 (19)C17—C15—C16119.4 (2)
C6—C5—C4113.58 (19)C17—C15—C13124.9 (2)
C10—C5—C4118.2 (2)C16—C15—C13115.6 (2)
C6—C5—H5104.6O2—C16—O3121.8 (2)
C10—C5—H5104.6O2—C16—C15123.2 (2)
C4—C5—H5104.6O3—C16—C15115.0 (2)
C7—C6—C5111.2 (2)C15—C17—H17A120.0
C7—C6—H6A109.4C15—C17—H17B120.0
C5—C6—H6A109.4H17A—C17—H17B120.0
C7—C6—H6B109.4C4—C18—H18A109.5
C5—C6—H6B109.4C4—C18—H18B109.5
H6A—C6—H6B108.0H18A—C18—H18B109.5
C8—C7—C6123.9 (2)C4—C18—H18C109.5
C8—C7—H7118.0H18A—C18—H18C109.5
C6—C7—H7118.0H18B—C18—H18C109.5
C7—C8—C14121.4 (2)C4—C19—H19A109.5
C7—C8—C9122.7 (2)C4—C19—H19B109.5
C14—C8—C9115.8 (2)H19A—C19—H19B109.5
C8—C9—C11110.90 (18)C4—C19—H19C109.5
C8—C9—C10112.76 (19)H19A—C19—H19C109.5
C11—C9—C10113.8 (2)H19B—C19—H19C109.5
C8—C9—H9106.3C10—C20—H20A109.5
C11—C9—H9106.3C10—C20—H20B109.5
C10—C9—H9106.3H20A—C20—H20B109.5
C20—C10—C1110.3 (2)C10—C20—H20C109.5
C20—C10—C5112.2 (2)H20A—C20—H20C109.5
C1—C10—C5110.02 (19)H20B—C20—H20C109.5
C20—C10—C9109.4 (2)
C10—C1—C2—C358.3 (3)C4—C5—C10—C2078.8 (3)
C1—C2—C3—O160.9 (3)C6—C5—C10—C1176.9 (2)
C1—C2—C3—C459.6 (3)C4—C5—C10—C144.4 (3)
O1—C3—C4—C1949.2 (3)C6—C5—C10—C965.8 (2)
C2—C3—C4—C19170.1 (2)C4—C5—C10—C9161.74 (19)
O1—C3—C4—C18164.2 (2)C8—C9—C10—C2075.4 (3)
C2—C3—C4—C1874.9 (3)C11—C9—C10—C2052.0 (3)
O1—C3—C4—C569.6 (2)C8—C9—C10—C1164.2 (2)
C2—C3—C4—C551.4 (3)C11—C9—C10—C168.4 (3)
C3—C4—C5—C6176.3 (2)C8—C9—C10—C545.9 (3)
C19—C4—C5—C665.1 (3)C11—C9—C10—C5173.3 (2)
C18—C4—C5—C654.0 (3)C8—C9—C11—C1248.0 (3)
C3—C4—C5—C1045.5 (3)C10—C9—C11—C12176.4 (2)
C19—C4—C5—C10164.2 (2)C9—C11—C12—C1358.2 (3)
C18—C4—C5—C1076.7 (3)C11—C12—C13—C15172.9 (2)
C10—C5—C6—C750.2 (3)C11—C12—C13—C1460.1 (3)
C4—C5—C6—C7175.1 (2)C7—C8—C14—C13135.3 (3)
C5—C6—C7—C814.4 (4)C9—C8—C14—C1349.0 (3)
C6—C7—C8—C14170.3 (3)C15—C13—C14—C8178.3 (2)
C6—C7—C8—C95.1 (4)C12—C13—C14—C855.7 (3)
C7—C8—C9—C11141.2 (3)C14—C13—C15—C1741.7 (4)
C14—C8—C9—C1143.2 (3)C12—C13—C15—C1782.1 (4)
C7—C8—C9—C1012.3 (3)C14—C13—C15—C16140.8 (2)
C14—C8—C9—C10172.1 (2)C12—C13—C15—C1695.4 (3)
C2—C1—C10—C2075.0 (3)C17—C15—C16—O2172.4 (3)
C2—C1—C10—C549.2 (3)C13—C15—C16—O25.3 (4)
C2—C1—C10—C9165.2 (2)C17—C15—C16—O37.8 (4)
C6—C5—C10—C2053.7 (3)C13—C15—C16—O3174.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O1i0.821.852.662 (3)169
O1—H1O···O2ii0.821.972.771 (3)164
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+3/2, y1/2, z+2.

Experimental details

Crystal data
Chemical formulaC20H30O3
Mr318.44
Crystal system, space groupMonoclinic, C2
Temperature (K)295
a, b, c (Å)24.066 (2), 10.017 (1), 7.608 (1)
β (°) 101.35 (1)
V3)1798.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.50 × 0.40
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2311, 2178, 1605
Rint0.016
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.097, 0.98
No. of reflections2178
No. of parameters214
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.12
Absolute structureSee text

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Siemens, 1991), SHELXTL/PC.

Selected geometric parameters (Å, º) top
O1—C31.432 (3)C13—C151.512 (3)
O2—C161.217 (3)C15—C171.310 (4)
O3—C161.320 (3)C15—C161.479 (3)
C7—C81.320 (3)
O1—C3—C2109.2 (2)O2—C16—O3121.8 (2)
O1—C3—C4108.4 (2)O2—C16—C15123.2 (2)
C17—C15—C16119.4 (2)O3—C16—C15115.0 (2)
C17—C15—C13124.9 (2)
C17—C15—C16—O2172.4 (3)C17—C15—C16—O37.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O1i0.821.852.662 (3)169.4
O1—H1O···O2ii0.821.972.771 (3)163.9
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+3/2, y1/2, z+2.
 

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