Samaderin B and C from Samadera indica

Samaderin B, or (1R,2S,5R,5aR,7aS,11S,11aS,11bR,14S)-1,7,7a,11,11a,11b-hexa­hydro-1,11-di­hydroxy-8,11a,14-tri­methyl-2H-5a,2,5-(methan­oxy­metheno)­naphth­[1,2-d]­oxepine-4,6,10(5H)-trione, C₁₉H₂₂O₇, and samaderin C, or (1R,2S,5R,5aR,7aS,10S,11S,11aS,11bR,14S)-7,7a,10,11,11a,11b-hexa­hydro-1,10,11-tri­hydroxy-8,11a,14-tri­methyl-2H-5a,2,5-(methan­oxy­metheno)­naphth­[1,2-d]­oxepine-4,6(1H,5H)-dione, C₁₉H₂₄O₇, were isolated from the seed kernels of Samadera indica and were shown to exhibit antifeedant activity against Spodoptera litura third-instar larvae. The replacement of the carbonyl group in samaderin B by a hydroxy group in samaderin C causes conformational changes at the substitution site, but the overall conformation is not affected; however, the compounds pack differently in the crystal lattice.

S1. Comment

The title compounds, samaderine-B and C, (I) and (II), respectively, were extracted from the seed kernels of Samadera indica. Compounds (I) and (II) belong to the quassinoid class (Polonsky, 1973, 1985), a diverse group of structurally complex and highly oxygenated lactones (δ-lactones in the C20- and γ-lactones in the C19-compounds) that generally exhibit antifeedant and insecticidal (Leskinen et al., 1984) activities similar to those of limonoids from neem. Compounds (I) and (II) exhibit antifeedant activity against Spodoptera litura third instar larvae (Govindachari et al., 2001). We have taken up the crystallographic study of these compounds as part of our work on the structural studies of ecofriendly bioinsecticides. Chemically, (I) and (II) differ in the substitution at the C2-atom position, viz. a carbonyl group on atom C2 in samaderine-B and a hydroxyl group in samaderine-C. The compounds both crystallize in space group P2₁2₁2₁ but have different unit-cell parameters.

The present study shows that the bond lengths and angles in both structures are close to those observed for other quassinoids (Onan et al., 1978; Suong et al., 1982; Chan et al., 1992; Zukerman-Schpector et al., 1994; Kabaleeswaran et al., 2000). In (II), the hydroxyl groups at atoms C1 and C2 are staggered with respect to one another, as described by the O1—C1—C2—O2 dihedral angle of 77.3 (2)°. The hydroxyl group at atom C1 is in a (-)-antiperiplanar conformation (Klyne & Prelog, 1960) with respect to the C2—C3 bond [C3—C2—C1—O1 = −156.5 (2)°], while the hydroxyl group at atom C2 is (+)-anticlinal with respect to the C3—C4 bond [C4—C3—C2—O2 = 131.9 (3)°]. In (I), the hydroxyl and carbonyl groups attached to atoms C1 and C2, respectively, are nearly in an eclipsed conformation [O1—C1—C2—O2 = 12.0 (9)°]. The hydroxyl group on atom C1 assumes a (-)-antiperiplanar conformation with respect to the C2—C3 bond [C3—C2—C1—O1 = −166.4 (6)°]. The hydroxyl groups on atoms C1 and C11 of both molecules are in the β orientation, and the hydroxyl group on atom C2 of (II) is in the α orientation. In both molecules?, the C19 methyl group is in a β orientation, while atom C17 is in an α orientation. The γ lactone ring, E, and the oxymethylene bridge attached to ring C are in α and β orientations, respectively. However, when both molecules are superimposed, the other parts of the molecules show negligible conformational differences.

Ring A of both molecules are in a sofa conformation [Cremer & Pople, 1975; Q_T = 0.495 (7) Å, θ = 46.5 (9)° and ϕ₂ = −43 (1)° in (I), and Q_T = 0.491 (2) Å, θ = 46.6 (3)° and ϕ₂= −54.5 (4)° in (II)]. Ring B is in a highly distorted chair conformation in both molecules [Q_T = 0.541 (7) Å, θ = 18.9 (8)° and ϕ₂ = −32 (2)° in (I), and Q_T = 0.536 (2) Å, θ = 20.4 (2)° and ϕ₂ = −47.2 (7)° in (II)]. Ring C assumes a distorted chair conformation in both molecules [Q_T = 0.733 (7) Å, θ = 22.5 (5)° and ϕ₂ = −84 (1) ° in (I), and Q_T= 0.718 (2) Å, θ = 28.1 (2)° and ϕ₂ = −80.8 (4)° in (II)]. The five-membered ring, D, takes up a half-chair conformation [q₂ = 0.452 (7) Å and ϕ₂ = −51.9 (8)° in (I), and q₂ = 0.439 (2) Å and ϕ₂ = 164.0 (3)° in (II)], with atoms C8 and C14 deviating from the least-squares plane of atoms C13, O13 and C16. The γ lactone ring, E, takes up a conformation intermediate between a half-chair and an envelope in both compounds [q₂ = 0.434 (6) Å and ϕ₂ = 149.7 (7) ° in (I), and q₂ = 0.443 (2) Å and ϕ₂ = 153.7 (3) ° in (II)]. In both molecules, the A/B, B/C and C/D rings are trans-fused.

The crystal packing is stabilized both by inter- and intramolecular hydrogen bonds. An intramolecular O11—H11···O13 hydrogen bond in (I) forms a ring graph-set motif (Berstein et al., 1995) of S(6), while an intramolecular O11—H11···O1 interaction in (II) forms a ring with the S(7) motif. In (I), an intermolecular O1—H1···O15(1/2 + x, 3/2 − y, 1 − z) hydrogen bond links the molecules into C(9) chains, which run along [100] and are generated by the 2₁ screw axis along (x, 3/4, 1/2). In addition, there are C—H···O hydrogen bonds involving methine atom H12 and methylene atom H17A, which interact with a common acceptor, namely atom O7 at (−1/2 − x, 1 − y, z − 1/2). This three-centered hydrogen bond generates a graph-set motif of R₂¹(6). Compound (II) is similar to (I) in that an intermolecular O1—H1···O15(-x, y − 1/2, 1/2 − z) hydrogen bond links the molecules into chains, but these run along [010] and are generated by a 2₁ screw axis along (−1/2, y, 1/4). Another O2—H2···O11(x − 1, y, z) hydrogen bond links the molecules into chains that run along the [100] direction, with a graph-set motif of C(8). These two intermolecular O—H···O hydrogen bonds in combination generate a two-dimensional network in (II), in which the ring graph-set motif of R₅⁵(27) can be detected (Figs. 2a and 2 b).

S2. Experimental

Compounds (I) and (II) were isolated from the seed kernels of Samadera indica according to the procedure described by Govindachari et al. (2001).

S3. Refinement

In the absence of suitable anomalous scatters, Friedel equivalents could not be used to determine the absolute structure. Refinement of the Flack (1983) parameter led to inconclusive values (Flack & Bernadinelli, 2000) for this parameter [0.9 (8) for (I) and −0.2 (3) for (II)]. The enantiomer employed in the refined model was chosen to agree with the accepted configuration of quassinoids (Polonsky, 1985). The methyl and hydroxyl H atoms were constrained to an ideal geometry [C—H = 0.96 and O—H = 0.82 Å, with U_iso(H) = 1.5U_eq(parent atom)] but were allowed to rotate freely about the C—C and C—O bonds, respectively. All remaining H atoms were placed in idealized positions (C—H = 0.97–0.98 Å) and constrained to ride on their parent atoms with U_iso(H) values equal to 1.2U_eq(C).

Computing details

For both compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

Fig 1a ORTEP diagram of (I), showing displacement ellipsoids at the 30% probability level and the atomic numbering scheme. Fig 1 b ORTEP diagram of (II), showing displacement ellipsoids at the 30% probability level and the atomic numbering scheme. Fig 2a The packing of (I) in the crystal lattice. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), dollar sign ($) or hash (#) are at the symmetry positions (1 + x, y, z), (1/2 − x, 1 − y, z − 1/2) and (3/2 + x, 3/2 − y, 1 − z), respectively. Fig 2 b The packing of (II) in crystal lattice. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*), hash (#) or plus sign (+) are at the symmetry positions (-x, y − 1/2, 1/2 − z), (x − 1, y, z) and (-x + 1, y − 1/2, 1/2 − z), respectively.

(I)

Crystal data

C19H22O7	F(000) = 768
Mr = 362.37	Dx = 1.460 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.342 (4) Å	θ = 15–30°
b = 13.328 (7) Å	µ = 0.94 mm^−1
c = 11.956 (9) Å	T = 293 K
V = 1648.0 (16) Å^3	Rod shaped, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection

Enraf Nonius CAD4 diffractometer	Rint = 0.060
Radiation source: fine-focus sealed tube	θmax = 72.0°, θmin = 5.4°
Graphite monochromator	h = −12→12
non–profiled ω/2θ scans	k = 0→16
1807 measured reflections	l = 0→14
1741 independent reflections	3 standard reflections every 200 reflections
1203 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1269P)^2 + 0.1667P] where P = (Fo^2 + 2Fc^2)/3
1741 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1276 (5)	0.6090 (5)	0.4430 (4)	0.0507 (14)
H1	0.1621	0.6359	0.3891	0.076*
O2	0.3732 (5)	0.6576 (5)	0.4484 (4)	0.0539 (15)
O7	−0.0455 (6)	0.6100 (6)	0.9624 (5)	0.085 (2)
O11	−0.0691 (5)	0.4558 (4)	0.5223 (4)	0.0519 (14)
H11	−0.0966	0.4130	0.5654	0.078*
O12	−0.2826 (4)	0.6563 (4)	0.6204 (5)	0.0441 (13)
O13	−0.1924 (4)	0.4116 (3)	0.7216 (4)	0.0429 (12)
O15	−0.2725 (5)	0.7577 (4)	0.7677 (5)	0.0638 (16)
C1	0.1712 (6)	0.6544 (5)	0.5418 (6)	0.0367 (15)
H1A	0.1311	0.7209	0.5468	0.044*
C2	0.3205 (7)	0.6694 (5)	0.5369 (6)	0.0423 (17)
C3	0.3821 (7)	0.6936 (5)	0.6399 (6)	0.0414 (16)
H3	0.4668	0.7168	0.6371	0.050*
C4	0.3266 (7)	0.6853 (5)	0.7397 (6)	0.0427 (17)
C5	0.1846 (7)	0.6565 (5)	0.7482 (6)	0.0364 (15)
H5	0.1368	0.7200	0.7466	0.044*
C6	0.1507 (7)	0.6073 (6)	0.8611 (6)	0.0424 (17)
H6A	0.1929	0.5425	0.8659	0.051*
H6B	0.1836	0.6489	0.9214	0.051*
C7	0.0071 (7)	0.5937 (6)	0.8756 (5)	0.0428 (17)
C8	−0.0682 (7)	0.5538 (5)	0.7748 (6)	0.0352 (14)
C9	−0.0187 (6)	0.5945 (5)	0.6608 (6)	0.0322 (14)
H9	−0.0417	0.6658	0.6630	0.039*
C10	0.1344 (6)	0.5957 (5)	0.6472 (6)	0.0321 (13)
C11	−0.1018 (7)	0.5526 (6)	0.5633 (5)	0.0375 (16)
H11A	−0.0924	0.5994	0.5006	0.045*
C12	−0.2456 (6)	0.5538 (5)	0.5971 (6)	0.0357 (15)
H12	−0.2993	0.5257	0.5373	0.043*
C13	−0.2714 (6)	0.4996 (5)	0.7083 (5)	0.0356 (15)
C14	−0.2157 (6)	0.5786 (5)	0.7861 (6)	0.0362 (16)
H14	−0.2474	0.5722	0.8630	0.043*
C15	−0.2586 (6)	0.6751 (5)	0.7305 (7)	0.0430 (17)
C16	−0.0777 (6)	0.4399 (5)	0.7815 (6)	0.0406 (16)
H16A	−0.0021	0.4092	0.7479	0.049*
H16B	−0.0834	0.4185	0.8589	0.049*
C17	−0.4116 (7)	0.4726 (6)	0.7257 (7)	0.0463 (18)
H17A	−0.4367	0.4226	0.6721	0.070*
H17B	−0.4642	0.5313	0.7161	0.070*
H17C	−0.4232	0.4466	0.7999	0.070*
C19	0.1961 (6)	0.4899 (5)	0.6419 (6)	0.0410 (16)
H19A	0.1733	0.4528	0.7078	0.062*
H19B	0.2884	0.4961	0.6375	0.062*
H19C	0.1647	0.4552	0.5769	0.062*
C20	0.3979 (7)	0.7058 (7)	0.8466 (7)	0.055 (2)
H20A	0.4110	0.6440	0.8862	0.082*
H20B	0.3482	0.7509	0.8920	0.082*
H20C	0.4801	0.7356	0.8298	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.042 (3)	0.078 (4)	0.032 (2)	−0.002 (3)	0.004 (2)	0.005 (3)
O2	0.036 (3)	0.083 (4)	0.043 (3)	0.005 (3)	0.012 (2)	0.008 (3)
O7	0.061 (4)	0.158 (7)	0.037 (3)	−0.032 (4)	0.011 (3)	−0.027 (4)
O11	0.041 (3)	0.064 (3)	0.050 (3)	−0.002 (3)	0.006 (3)	−0.020 (3)
O12	0.028 (3)	0.047 (3)	0.058 (3)	−0.003 (2)	0.004 (2)	0.017 (2)
O13	0.035 (2)	0.039 (2)	0.055 (3)	−0.004 (2)	−0.007 (2)	0.005 (2)
O15	0.050 (3)	0.045 (3)	0.096 (4)	0.002 (3)	0.025 (3)	−0.007 (3)
C1	0.035 (4)	0.040 (3)	0.035 (3)	0.007 (3)	0.001 (3)	0.005 (3)
C2	0.037 (4)	0.044 (4)	0.047 (4)	0.006 (3)	0.006 (3)	0.009 (3)
C3	0.026 (3)	0.046 (4)	0.052 (4)	0.001 (3)	0.001 (3)	0.001 (4)
C4	0.037 (4)	0.048 (4)	0.043 (4)	0.006 (3)	0.002 (3)	0.009 (3)
C5	0.031 (3)	0.038 (3)	0.041 (4)	0.004 (3)	−0.001 (3)	−0.002 (3)
C6	0.035 (4)	0.059 (4)	0.033 (3)	−0.010 (3)	−0.008 (3)	0.002 (3)
C7	0.048 (4)	0.061 (4)	0.019 (3)	−0.007 (4)	−0.001 (3)	−0.005 (3)
C8	0.031 (3)	0.044 (3)	0.030 (3)	−0.005 (3)	−0.002 (3)	−0.005 (3)
C9	0.025 (3)	0.031 (3)	0.040 (3)	−0.001 (3)	0.007 (3)	−0.002 (3)
C10	0.024 (3)	0.036 (3)	0.036 (3)	0.003 (3)	0.000 (3)	−0.001 (3)
C11	0.026 (3)	0.055 (4)	0.031 (3)	0.005 (3)	−0.007 (3)	0.004 (3)
C12	0.023 (3)	0.044 (4)	0.040 (4)	−0.002 (3)	−0.003 (3)	0.006 (3)
C13	0.033 (4)	0.036 (3)	0.038 (3)	−0.004 (3)	0.000 (3)	−0.002 (3)
C14	0.028 (3)	0.046 (4)	0.034 (3)	−0.009 (3)	0.000 (3)	−0.001 (3)
C15	0.022 (3)	0.046 (4)	0.061 (4)	0.001 (3)	0.017 (4)	−0.001 (4)
C16	0.030 (3)	0.044 (4)	0.048 (4)	−0.003 (3)	−0.010 (3)	0.015 (3)
C17	0.030 (4)	0.060 (5)	0.049 (4)	−0.004 (3)	0.008 (4)	0.006 (4)
C19	0.026 (3)	0.040 (3)	0.058 (4)	0.005 (3)	0.004 (3)	−0.002 (3)
C20	0.034 (4)	0.074 (5)	0.057 (5)	−0.005 (4)	−0.005 (4)	0.001 (4)

Geometric parameters (Å, º)

O1—C1	1.401 (8)	C8—C16	1.523 (9)
O1—H1	0.8200	C8—C9	1.554 (9)
O2—C2	1.200 (8)	C8—C14	1.567 (10)
O7—C7	1.192 (8)	C9—C11	1.552 (9)
O11—C11	1.421 (9)	C9—C10	1.591 (9)
O11—H11	0.8200	C9—H9	0.9800
O12—C15	1.363 (10)	C10—C19	1.549 (8)
O12—C12	1.446 (8)	C11—C12	1.540 (9)
O13—C16	1.436 (8)	C11—H11A	0.9800
O13—C13	1.438 (8)	C12—C13	1.537 (9)
O15—C15	1.196 (8)	C12—H12	0.9800
C1—C10	1.532 (9)	C13—C17	1.509 (9)
C1—C2	1.558 (10)	C13—C14	1.518 (9)
C1—H1A	0.9800	C14—C15	1.514 (10)
C2—C3	1.423 (10)	C14—H14	0.9800
C3—C4	1.329 (10)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C20	1.501 (10)	C17—H17A	0.9600
C4—C5	1.521 (10)	C17—H17B	0.9600
C5—C6	1.542 (9)	C17—H17C	0.9600
C5—C10	1.544 (9)	C19—H19A	0.9600
C5—H5	0.9800	C19—H19B	0.9600
C6—C7	1.507 (10)	C19—H19C	0.9600
C6—H6A	0.9700	C20—H20A	0.9600
C6—H6B	0.9700	C20—H20B	0.9600
C7—C8	1.530 (9)	C20—H20C	0.9600
C1—O1—H1	109.5	O11—C11—C12	109.2 (6)
C11—O11—H11	109.5	O11—C11—C9	117.0 (6)
C15—O12—C12	108.2 (5)	C12—C11—C9	109.5 (5)
C16—O13—C13	108.0 (5)	O11—C11—H11A	106.9
O1—C1—C10	113.1 (5)	C12—C11—H11A	106.9
O1—C1—C2	110.1 (6)	C9—C11—H11A	106.9
C10—C1—C2	110.1 (5)	O12—C12—C13	103.3 (5)
O1—C1—H1A	107.8	O12—C12—C11	108.4 (5)
C10—C1—H1A	107.8	C13—C12—C11	112.9 (5)
C2—C1—H1A	107.8	O12—C12—H12	110.6
O2—C2—C3	126.1 (7)	C13—C12—H12	110.6
O2—C2—C1	117.8 (7)	C11—C12—H12	110.6
C3—C2—C1	116.1 (6)	O13—C13—C17	109.6 (6)
C4—C3—C2	124.4 (6)	O13—C13—C14	106.4 (5)
C4—C3—H3	117.8	C17—C13—C14	116.5 (6)
C2—C3—H3	117.8	O13—C13—C12	112.4 (5)
C3—C4—C20	122.5 (6)	C17—C13—C12	113.5 (6)
C3—C4—C5	119.9 (7)	C14—C13—C12	98.0 (5)
C20—C4—C5	117.6 (6)	C15—C14—C13	102.0 (6)
C4—C5—C6	112.6 (6)	C15—C14—C8	115.2 (5)
C4—C5—C10	113.9 (6)	C13—C14—C8	99.8 (5)
C6—C5—C10	112.7 (5)	C15—C14—H14	112.8
C4—C5—H5	105.6	C13—C14—H14	112.8
C6—C5—H5	105.6	C8—C14—H14	112.8
C10—C5—H5	105.6	O15—C15—O12	120.4 (7)
C7—C6—C5	112.1 (6)	O15—C15—C14	130.9 (8)
C7—C6—H6A	109.2	O12—C15—C14	108.7 (6)
C5—C6—H6A	109.2	O13—C16—C8	106.8 (5)
C7—C6—H6B	109.2	O13—C16—H16A	110.4
C5—C6—H6B	109.2	C8—C16—H16A	110.4
H6A—C6—H6B	107.9	O13—C16—H16B	110.4
O7—C7—C6	121.9 (7)	C8—C16—H16B	110.4
O7—C7—C8	121.2 (7)	H16A—C16—H16B	108.6
C6—C7—C8	116.9 (6)	C13—C17—H17A	109.5
C16—C8—C7	109.7 (6)	C13—C17—H17B	109.5
C16—C8—C9	114.5 (6)	H17A—C17—H17B	109.5
C7—C8—C9	113.7 (5)	C13—C17—H17C	109.5
C16—C8—C14	98.2 (5)	H17A—C17—H17C	109.5
C7—C8—C14	110.8 (6)	H17B—C17—H17C	109.5
C9—C8—C14	108.9 (5)	C10—C19—H19A	109.5
C8—C9—C11	110.5 (5)	C10—C19—H19B	109.5
C8—C9—C10	114.9 (6)	H19A—C19—H19B	109.5
C11—C9—C10	118.6 (6)	C10—C19—H19C	109.5
C8—C9—H9	103.6	H19A—C19—H19C	109.5
C11—C9—H9	103.6	H19B—C19—H19C	109.5
C10—C9—H9	103.6	C4—C20—H20A	109.5
C1—C10—C5	106.9 (5)	C4—C20—H20B	109.5
C1—C10—C19	109.2 (5)	H20A—C20—H20B	109.5
C5—C10—C19	111.8 (5)	C4—C20—H20C	109.5
C1—C10—C9	109.7 (5)	H20A—C20—H20C	109.5
C5—C10—C9	105.1 (5)	H20B—C20—H20C	109.5
C19—C10—C9	113.9 (5)
O1—C1—C2—O2	12.0 (9)	C8—C9—C10—C19	67.6 (8)
C10—C1—C2—O2	137.3 (7)	C11—C9—C10—C19	−66.2 (8)
O1—C1—C2—C3	−166.4 (6)	C8—C9—C11—O11	−83.5 (7)
C10—C1—C2—C3	−41.1 (8)	C10—C9—C11—O11	52.2 (8)
O2—C2—C3—C4	−164.9 (8)	C8—C9—C11—C12	41.4 (7)
C1—C2—C3—C4	13.4 (10)	C10—C9—C11—C12	177.1 (5)
C2—C3—C4—C20	176.2 (7)	C15—O12—C12—C13	31.3 (6)
C2—C3—C4—C5	−5.3 (11)	C15—O12—C12—C11	−88.8 (6)
C3—C4—C5—C6	155.6 (7)	O11—C11—C12—O12	−170.5 (5)
C20—C4—C5—C6	−25.9 (9)	C9—C11—C12—O12	60.3 (7)
C3—C4—C5—C10	25.7 (9)	O11—C11—C12—C13	75.7 (7)
C20—C4—C5—C10	−155.8 (6)	C9—C11—C12—C13	−53.6 (8)
C4—C5—C6—C7	171.3 (6)	C16—O13—C13—C17	−139.8 (6)
C10—C5—C6—C7	−58.2 (8)	C16—O13—C13—C14	−13.1 (7)
C5—C6—C7—O7	−138.6 (8)	C16—O13—C13—C12	93.0 (6)
C5—C6—C7—C8	43.7 (10)	O12—C12—C13—O13	−154.4 (5)
O7—C7—C8—C16	−85.2 (10)	C11—C12—C13—O13	−37.5 (8)
C6—C7—C8—C16	92.6 (8)	O12—C12—C13—C17	80.5 (7)
O7—C7—C8—C9	145.1 (8)	C11—C12—C13—C17	−162.6 (6)
C6—C7—C8—C9	−37.2 (9)	O12—C12—C13—C14	−43.0 (6)
O7—C7—C8—C14	22.1 (11)	C11—C12—C13—C14	73.9 (7)
C6—C7—C8—C14	−160.1 (6)	O13—C13—C14—C15	154.8 (5)
C16—C8—C9—C11	54.1 (7)	C17—C13—C14—C15	−82.7 (7)
C7—C8—C9—C11	−178.7 (6)	C12—C13—C14—C15	38.6 (6)
C14—C8—C9—C11	−54.7 (7)	O13—C13—C14—C8	36.2 (6)
C16—C8—C9—C10	−83.4 (7)	C17—C13—C14—C8	158.7 (6)
C7—C8—C9—C10	43.9 (8)	C12—C13—C14—C8	−80.0 (6)
C14—C8—C9—C10	167.9 (5)	C16—C8—C14—C15	−151.9 (6)
O1—C1—C10—C5	−178.1 (6)	C7—C8—C14—C15	93.3 (7)
C2—C1—C10—C5	58.4 (6)	C9—C8—C14—C15	−32.4 (8)
O1—C1—C10—C19	60.7 (7)	C16—C8—C14—C13	−43.5 (6)
C2—C1—C10—C19	−62.8 (7)	C7—C8—C14—C13	−158.3 (6)
O1—C1—C10—C9	−64.7 (7)	C9—C8—C14—C13	76.0 (6)
C2—C1—C10—C9	171.8 (6)	C12—O12—C15—O15	174.4 (6)
C4—C5—C10—C1	−51.7 (7)	C12—O12—C15—C14	−5.6 (7)
C6—C5—C10—C1	178.4 (6)	C13—C14—C15—O15	157.5 (8)
C4—C5—C10—C19	67.7 (7)	C8—C14—C15—O15	−95.4 (9)
C6—C5—C10—C19	−62.1 (7)	C13—C14—C15—O12	−22.5 (7)
C4—C5—C10—C9	−168.2 (6)	C8—C14—C15—O12	84.5 (7)
C6—C5—C10—C9	61.9 (7)	C13—O13—C16—C8	−16.8 (7)
C8—C9—C10—C1	−169.7 (5)	C7—C8—C16—O13	153.5 (6)
C11—C9—C10—C1	56.4 (8)	C9—C8—C16—O13	−77.2 (7)
C8—C9—C10—C5	−55.1 (7)	C14—C8—C16—O13	38.0 (7)
C11—C9—C10—C5	171.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O13	0.82	2.11	2.766 (8)	136
O1—H1···O15^i	0.82	2.45	3.252 (8)	168
C12—H12···O7^ii	0.98	2.58	3.468 (10)	151
C17—H17A···O7^ii	0.96	2.55	3.364 (11)	143

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x−1/2, −y+1, z−1/2.

(II)

Crystal data

C19H24O7	F(000) = 776
Mr = 364.38	Dx = 1.435 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.5278 (16) Å	θ = 15–30°
b = 12.418 (3) Å	µ = 0.91 mm^−1
c = 18.037 (4) Å	T = 293 K
V = 1686.2 (7) Å^3	Rod shaped, colourless
Z = 4	0.25 × 0.15 × 0.15 mm

Data collection

Enraf Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 71.8°, θmin = 4.3°
Graphite monochromator	h = 0→9
non–profiled ω/2θ scans	k = 0→14
1846 measured reflections	l = 0→22
1846 independent reflections	3 standard reflections every 200 reflections
1660 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.2417P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1846 reflections	Δρmax = 0.18 e Å^−3
240 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0358 (3)	0.74913 (15)	0.12065 (12)	0.0476 (5)
H1	−0.0288	0.6969	0.1140	0.071*
O2	−0.3420 (3)	0.77060 (17)	0.07249 (11)	0.0505 (5)
H2	−0.3984	0.7960	0.1072	0.076*
O7	0.1916 (3)	1.23757 (15)	0.21800 (11)	0.0606 (6)
O12	0.2523 (3)	0.89710 (14)	0.34958 (9)	0.0433 (5)
O11	0.3663 (2)	0.79653 (15)	0.16733 (11)	0.0448 (4)
H11	0.3028	0.7632	0.1384	0.067*
O13	0.5629 (2)	0.98607 (16)	0.21140 (10)	0.0463 (5)
O15	0.1031 (3)	1.04339 (16)	0.38421 (9)	0.0480 (5)
C1	−0.0686 (3)	0.84514 (19)	0.12011 (13)	0.0346 (5)
H1A	−0.1381	0.8478	0.1660	0.041*
C2	−0.1973 (3)	0.8406 (2)	0.05457 (13)	0.0410 (6)
H2A	−0.1331	0.8076	0.0131	0.049*
C3	−0.2599 (4)	0.9492 (2)	0.02883 (13)	0.0454 (6)
H3	−0.3486	0.9512	−0.0070	0.055*
C4	−0.1978 (3)	1.0422 (2)	0.05350 (12)	0.0422 (6)
C5	−0.0632 (3)	1.0448 (2)	0.11609 (12)	0.0354 (5)
H5	−0.1334	1.0423	0.1618	0.042*
C6	0.0449 (4)	1.1485 (2)	0.12090 (14)	0.0441 (6)
H6A	0.1147	1.1559	0.0760	0.053*
H6B	−0.0364	1.2091	0.1231	0.053*
C7	0.1664 (4)	1.15376 (19)	0.18596 (12)	0.0361 (5)
C8	0.2667 (3)	1.05236 (19)	0.20735 (11)	0.0320 (5)
C9	0.1557 (3)	0.94828 (19)	0.19535 (11)	0.0290 (4)
H9	0.0588	0.9550	0.2314	0.035*
C10	0.0574 (3)	0.94349 (19)	0.11860 (11)	0.0311 (5)
C11	0.2590 (3)	0.84709 (19)	0.22193 (13)	0.0354 (5)
H11A	0.1703	0.7941	0.2377	0.043*
C12	0.3752 (4)	0.8715 (2)	0.28933 (13)	0.0392 (6)
H12	0.4495	0.8094	0.3021	0.047*
C13	0.4869 (3)	0.9741 (2)	0.28349 (14)	0.0410 (6)
C14	0.3357 (3)	1.0556 (2)	0.28895 (12)	0.0353 (5)
H14	0.3764	1.1273	0.3040	0.042*
C15	0.2156 (3)	1.0044 (2)	0.34504 (12)	0.0362 (5)
C16	0.4476 (3)	1.0501 (2)	0.16772 (14)	0.0421 (6)
H16A	0.4352	1.0194	0.1186	0.050*
H16B	0.4945	1.1225	0.1629	0.050*
C17	0.6331 (4)	0.9823 (3)	0.34056 (18)	0.0587 (8)
H17A	0.6975	1.0482	0.3334	0.088*
H17B	0.7126	0.9223	0.3352	0.088*
H17C	0.5822	0.9816	0.3894	0.088*
C19	0.1746 (3)	0.9384 (2)	0.04852 (12)	0.0397 (6)
H19A	0.2500	0.8762	0.0510	0.060*
H19B	0.2464	1.0022	0.0456	0.060*
H19C	0.1003	0.9337	0.0054	0.060*
C20	−0.2672 (4)	1.1469 (3)	0.02315 (16)	0.0584 (8)
H20A	−0.3640	1.1328	−0.0101	0.088*
H20B	−0.1739	1.1834	−0.0030	0.088*
H20C	−0.3080	1.1914	0.0632	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0401 (10)	0.0338 (9)	0.0689 (12)	−0.0033 (8)	−0.0053 (10)	−0.0079 (9)
O2	0.0384 (9)	0.0578 (12)	0.0553 (10)	−0.0110 (9)	−0.0008 (9)	−0.0147 (9)
O7	0.0849 (16)	0.0357 (10)	0.0612 (11)	0.0045 (11)	−0.0190 (13)	−0.0097 (9)
O12	0.0528 (11)	0.0390 (10)	0.0381 (8)	0.0069 (9)	0.0029 (9)	0.0033 (7)
O11	0.0359 (8)	0.0437 (10)	0.0547 (10)	0.0057 (8)	0.0008 (9)	−0.0151 (8)
O13	0.0299 (8)	0.0570 (12)	0.0518 (10)	0.0030 (8)	0.0048 (8)	−0.0042 (9)
O15	0.0525 (11)	0.0487 (11)	0.0428 (8)	0.0097 (10)	0.0092 (9)	0.0000 (8)
C1	0.0297 (11)	0.0368 (13)	0.0372 (11)	−0.0033 (10)	0.0027 (10)	−0.0041 (9)
C2	0.0328 (12)	0.0535 (15)	0.0366 (11)	−0.0042 (12)	0.0001 (10)	−0.0104 (11)
C3	0.0370 (12)	0.0672 (17)	0.0321 (10)	0.0000 (15)	−0.0035 (10)	−0.0027 (12)
C4	0.0385 (12)	0.0551 (15)	0.0330 (10)	0.0078 (13)	0.0016 (10)	0.0053 (11)
C5	0.0355 (11)	0.0377 (13)	0.0328 (10)	0.0013 (11)	0.0010 (10)	0.0016 (9)
C6	0.0526 (15)	0.0348 (14)	0.0448 (13)	0.0038 (13)	−0.0060 (13)	0.0037 (10)
C7	0.0391 (12)	0.0334 (13)	0.0358 (10)	−0.0026 (11)	0.0072 (10)	0.0013 (9)
C8	0.0309 (10)	0.0324 (11)	0.0328 (9)	−0.0032 (10)	0.0026 (9)	−0.0014 (9)
C9	0.0270 (10)	0.0298 (11)	0.0304 (9)	−0.0009 (10)	0.0030 (8)	−0.0011 (8)
C10	0.0313 (10)	0.0316 (12)	0.0303 (10)	−0.0017 (11)	0.0029 (9)	−0.0015 (9)
C11	0.0311 (11)	0.0339 (13)	0.0413 (11)	0.0030 (10)	0.0026 (11)	−0.0015 (9)
C12	0.0375 (12)	0.0402 (14)	0.0399 (11)	0.0105 (11)	−0.0020 (11)	−0.0008 (10)
C13	0.0309 (11)	0.0476 (15)	0.0446 (12)	0.0013 (11)	−0.0029 (11)	−0.0083 (11)
C14	0.0346 (11)	0.0335 (12)	0.0377 (10)	−0.0013 (11)	−0.0032 (10)	−0.0037 (10)
C15	0.0378 (13)	0.0382 (13)	0.0326 (10)	0.0055 (11)	−0.0028 (10)	−0.0002 (10)
C16	0.0325 (11)	0.0464 (14)	0.0473 (13)	−0.0083 (12)	0.0063 (11)	−0.0044 (12)
C17	0.0463 (15)	0.066 (2)	0.0633 (16)	0.0063 (15)	−0.0193 (15)	−0.0135 (15)
C19	0.0384 (13)	0.0452 (14)	0.0354 (10)	−0.0019 (12)	0.0063 (10)	−0.0045 (10)
C20	0.0584 (18)	0.0652 (19)	0.0515 (15)	0.0128 (17)	−0.0095 (15)	0.0131 (14)

Geometric parameters (Å, º)

O1—C1	1.428 (3)	C7—C8	1.518 (3)
O1—H1	0.8200	C8—C16	1.538 (3)
O2—C2	1.431 (3)	C8—C9	1.554 (3)
O2—H2	0.8200	C8—C14	1.561 (3)
O7—C7	1.205 (3)	C9—C11	1.554 (3)
O12—C15	1.363 (3)	C9—C10	1.571 (3)
O12—C12	1.462 (3)	C9—H9	0.9800
O11—C11	1.420 (3)	C10—C19	1.543 (3)
O11—H11	0.8200	C11—C12	1.528 (3)
O13—C16	1.417 (3)	C11—H11A	0.9800
O13—C13	1.429 (3)	C12—C13	1.529 (4)
O15—C15	1.204 (3)	C12—H12	0.9800
C1—C2	1.529 (3)	C13—C17	1.510 (3)
C1—C10	1.547 (3)	C13—C14	1.527 (3)
C1—H1A	0.9800	C14—C15	1.499 (3)
C2—C3	1.503 (4)	C14—H14	0.9800
C2—H2A	0.9800	C16—H16A	0.9700
C3—C4	1.323 (4)	C16—H16B	0.9700
C3—H3	0.9300	C17—H17A	0.9600
C4—C20	1.504 (4)	C17—H17B	0.9600
C4—C5	1.517 (3)	C17—H17C	0.9600
C5—C6	1.526 (4)	C19—H19A	0.9600
C5—C10	1.552 (3)	C19—H19B	0.9600
C5—H5	0.9800	C19—H19C	0.9600
C6—C7	1.490 (4)	C20—H20A	0.9600
C6—H6A	0.9700	C20—H20B	0.9600
C6—H6B	0.9700	C20—H20C	0.9600
C1—O1—H1	109.5	C1—C10—C9	107.65 (17)
C2—O2—H2	109.5	C5—C10—C9	105.71 (17)
C15—O12—C12	107.22 (18)	O11—C11—C12	108.30 (19)
C11—O11—H11	109.5	O11—C11—C9	115.36 (18)
C16—O13—C13	108.61 (18)	C12—C11—C9	111.8 (2)
O1—C1—C2	108.84 (19)	O11—C11—H11A	107.0
O1—C1—C10	108.79 (18)	C12—C11—H11A	107.0
C2—C1—C10	113.82 (19)	C9—C11—H11A	107.0
O1—C1—H1A	108.4	O12—C12—C11	105.8 (2)
C2—C1—H1A	108.4	O12—C12—C13	102.60 (19)
C10—C1—H1A	108.4	C11—C12—C13	115.2 (2)
O2—C2—C3	112.1 (2)	O12—C12—H12	110.9
O2—C2—C1	109.3 (2)	C11—C12—H12	110.9
C3—C2—C1	113.8 (2)	C13—C12—H12	110.9
O2—C2—H2A	107.1	O13—C13—C17	108.7 (2)
C3—C2—H2A	107.1	O13—C13—C14	106.7 (2)
C1—C2—H2A	107.1	C17—C13—C14	117.0 (2)
C4—C3—C2	124.7 (2)	O13—C13—C12	111.7 (2)
C4—C3—H3	117.6	C17—C13—C12	114.2 (2)
C2—C3—H3	117.6	C14—C13—C12	97.95 (19)
C3—C4—C20	120.6 (2)	C15—C14—C13	102.23 (19)
C3—C4—C5	120.3 (2)	C15—C14—C8	115.1 (2)
C20—C4—C5	119.0 (2)	C13—C14—C8	99.79 (18)
C4—C5—C6	114.6 (2)	C15—C14—H14	112.8
C4—C5—C10	113.3 (2)	C13—C14—H14	112.8
C6—C5—C10	111.7 (2)	C8—C14—H14	112.8
C4—C5—H5	105.4	O15—C15—O12	120.0 (2)
C6—C5—H5	105.4	O15—C15—C14	130.5 (2)
C10—C5—H5	105.4	O12—C15—C14	109.5 (2)
C7—C6—C5	114.2 (2)	O13—C16—C8	107.13 (19)
C7—C6—H6A	108.7	O13—C16—H16A	110.3
C5—C6—H6A	108.7	C8—C16—H16A	110.3
C7—C6—H6B	108.7	O13—C16—H16B	110.3
C5—C6—H6B	108.7	C8—C16—H16B	110.3
H6A—C6—H6B	107.6	H16A—C16—H16B	108.5
O7—C7—C6	120.8 (2)	C13—C17—H17A	109.5
O7—C7—C8	121.1 (2)	C13—C17—H17B	109.5
C6—C7—C8	118.0 (2)	H17A—C17—H17B	109.5
C7—C8—C16	109.7 (2)	C13—C17—H17C	109.5
C7—C8—C9	112.78 (19)	H17A—C17—H17C	109.5
C16—C8—C9	113.33 (19)	H17B—C17—H17C	109.5
C7—C8—C14	112.55 (19)	C10—C19—H19A	109.5
C16—C8—C14	98.27 (19)	C10—C19—H19B	109.5
C9—C8—C14	109.38 (18)	H19A—C19—H19B	109.5
C11—C9—C8	111.14 (18)	C10—C19—H19C	109.5
C11—C9—C10	118.50 (18)	H19A—C19—H19C	109.5
C8—C9—C10	114.04 (17)	H19B—C19—H19C	109.5
C11—C9—H9	103.7	C4—C20—H20A	109.5
C8—C9—H9	103.7	C4—C20—H20B	109.5
C10—C9—H9	103.7	H20A—C20—H20B	109.5
C19—C10—C1	109.44 (18)	C4—C20—H20C	109.5
C19—C10—C5	110.11 (19)	H20A—C20—H20C	109.5
C1—C10—C5	106.37 (19)	H20B—C20—H20C	109.5
C19—C10—C9	117.02 (18)
O1—C1—C2—O2	77.3 (2)	C11—C9—C10—C5	168.23 (19)
C10—C1—C2—O2	−161.17 (19)	C8—C9—C10—C5	−58.0 (2)
O1—C1—C2—C3	−156.5 (2)	C8—C9—C11—O11	−90.3 (2)
C10—C1—C2—C3	−35.0 (3)	C10—C9—C11—O11	44.7 (3)
O2—C2—C3—C4	131.9 (3)	C8—C9—C11—C12	34.0 (2)
C1—C2—C3—C4	7.2 (3)	C10—C9—C11—C12	169.03 (19)
C2—C3—C4—C20	178.9 (3)	C15—O12—C12—C11	−86.9 (2)
C2—C3—C4—C5	−4.7 (4)	C15—O12—C12—C13	34.2 (2)
C3—C4—C5—C6	159.3 (2)	O11—C11—C12—O12	−165.88 (18)
C20—C4—C5—C6	−24.2 (3)	C9—C11—C12—O12	65.9 (2)
C3—C4—C5—C10	29.4 (3)	O11—C11—C12—C13	81.6 (3)
C20—C4—C5—C10	−154.1 (2)	C9—C11—C12—C13	−46.6 (3)
C4—C5—C6—C7	175.4 (2)	C16—O13—C13—C17	−139.8 (2)
C10—C5—C6—C7	−54.0 (3)	C16—O13—C13—C14	−12.7 (3)
C5—C6—C7—O7	−143.5 (3)	C16—O13—C13—C12	93.3 (2)
C5—C6—C7—C8	40.5 (3)	O12—C12—C13—O13	−155.75 (19)
O7—C7—C8—C16	−84.7 (3)	C11—C12—C13—O13	−41.3 (3)
C6—C7—C8—C16	91.3 (3)	O12—C12—C13—C17	80.3 (2)
O7—C7—C8—C9	148.0 (2)	C11—C12—C13—C17	−165.3 (2)
C6—C7—C8—C9	−36.1 (3)	O12—C12—C13—C14	−44.1 (2)
O7—C7—C8—C14	23.6 (3)	C11—C12—C13—C14	70.3 (2)
C6—C7—C8—C14	−160.4 (2)	O13—C13—C14—C15	153.77 (19)
C7—C8—C9—C11	−176.87 (18)	C17—C13—C14—C15	−84.2 (3)
C16—C8—C9—C11	57.7 (2)	C12—C13—C14—C15	38.2 (2)
C14—C8—C9—C11	−50.8 (2)	O13—C13—C14—C8	35.2 (2)
C7—C8—C9—C10	46.0 (2)	C17—C13—C14—C8	157.2 (2)
C16—C8—C9—C10	−79.4 (2)	C12—C13—C14—C8	−80.4 (2)
C14—C8—C9—C10	172.10 (17)	C7—C8—C14—C15	94.2 (2)
O1—C1—C10—C19	59.7 (2)	C16—C8—C14—C15	−150.4 (2)
C2—C1—C10—C19	−61.8 (3)	C9—C8—C14—C15	−32.0 (3)
O1—C1—C10—C5	178.62 (19)	C7—C8—C14—C13	−157.3 (2)
C2—C1—C10—C5	57.1 (2)	C16—C8—C14—C13	−41.9 (2)
O1—C1—C10—C9	−68.5 (2)	C9—C8—C14—C13	76.5 (2)
C2—C1—C10—C9	170.00 (19)	C12—O12—C15—O15	172.6 (2)
C4—C5—C10—C19	65.0 (3)	C12—O12—C15—C14	−8.9 (3)
C6—C5—C10—C19	−66.3 (2)	C13—C14—C15—O15	158.4 (3)
C4—C5—C10—C1	−53.5 (2)	C8—C14—C15—O15	−94.5 (3)
C6—C5—C10—C1	175.25 (19)	C13—C14—C15—O12	−19.9 (2)
C4—C5—C10—C9	−167.75 (18)	C8—C14—C15—O12	87.1 (2)
C6—C5—C10—C9	61.0 (2)	C13—O13—C16—C8	−16.2 (3)
C11—C9—C10—C19	−68.8 (3)	C7—C8—C16—O13	154.6 (2)
C8—C9—C10—C19	65.0 (3)	C9—C8—C16—O13	−78.4 (2)
C11—C9—C10—C1	54.9 (2)	C14—C8—C16—O13	36.9 (2)
C8—C9—C10—C1	−171.39 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O1	0.82	2.04	2.692 (3)	136
O1—H1···O15^i	0.82	1.99	2.762 (3)	158
O2—H2···O11^ii	0.82	2.08	2.802 (3)	147

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−1, y, z.