β-(3,6,9-Trimethyl-9-xanthen­yl)propionic acid

The title compound, C₁₉H₂₀O₃, was obtained, among other condensation products, from the reaction of meta-cresol and levulinic acid. The pyrane ring closure does not alter significantly the environment of the ethereal linkage in comparison with diaryl ethers. The deformations of the endocyclic valence angles in the benzene rings, centred on the C atoms substituted with alkyl groups, is greater than expected. The mol­ecular packing is influenced by O—H...O hydrogen bonds, leading to centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 85 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.105
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O25    -   C23     ..       5.75 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Condensation of phenol with levulinic acid or its ester, in the presence of an acidic catalyst, provides the corresponding bisphenolic acid (DPA) as the only product (Bader & Kontowicz, 1954; Yu & Day, 1958). Xanthene core of the (I) molecule is planar as in other 9,9–disubstituted xanthenes (Jacobs, et al., 2005). A roof–shaped structure, with the fold angle up to 14.2 (1)° was found in xanthene–9–carboxylic acid molecule (Blackburn, et al., 1996). The benzene rings of (I) are almost regular hexagons with the typical aromatic C — C bond lengths (1.395 (8) Å). The internal angles centred on C3, C6, C11 and C14 atoms i.e. those, which are bonded to tetrahedral carbons, have lower value (lowest 116.00 (10)° largest 117.99 (10)) than expected 120°. The deformation is greater than expected (Δα = - 1.9°) for any electron releasing substituent (Domenicano, 1992). The O10 and C9 atoms are situated almost exactly in the plane of neighbour benzene rings; the deviations from the plane of four angular atoms are 0.043Å (O10) and 0.029 Å (C9). The geometry of pyrane ring can be described as the flat boat conformation. The internal C11 — C9 — C14 angle (109.65 (9)°) corresponds to the tetrahedral hybridization of C9 atom. The oxygen atom is more flexible member of the ring, the angle centred on O10 (118.48 (8)°) makes the pyrane ring nearly regular. The C — O bond length (1.381 (1) Å) is the same as in open diaryl ethers (Allen et al., 1995). The C26 — C9 — C21 plane is perpendicular to the xanthene system. Four bonds, formed by C9 have the lengths typical for the Ar — C(sp³) (1.5268 (14) and 1.5290 (15) Å) and C(sp³) – C(sp³) (1.5504 (15) and 1.5416 (15) Å). The ethylene C21 — C22 group has transoid conformation in crystal network, in part, due to the molecular packing. In solution, rotation along C21 — C22 bond is restricted to some extent because of steric interaction within the molecule (I). It is observed in the proton NMR spectrum as two illegible multiplets, at 2.11 and 1.84 p.p.m., indicating that the environments of vicinal protons are not magnetically equivalent.

The (I) molecules are arranged in couples joined by the O — H···.O hydrogen bond as in the aforementioned xanthene–9–carboxylic acid (Blackburn, et al., 1996). Monomeric carboxylic acids absorb in IR, in diluted carbon tetrachloride solution, at 3500—3550 cm^-1 due to O — H bond stretching vibrations. In the spectra of (I), registered in the solid state and in solution, this band is shifted to the 2800–3100 cm^-1 region and overlapped with the C — H stretching vibrations. The absorption enhancement and the shift, exceeding 16% on the 1/ λ scale, indicate a strong character of the hydrogen bond. The interaction is observed in the crystal lattice as short (2.666 Å) distance between two oxygen atoms belonging to neighbour molecules. It is less than the sum of Van der Waals radii (2.80 Å) of atoms participating in the hydrogen bond.

Related literature

For related literature, see: Bader & Kontowicz (1954); Blackburn et al. (1996); Domenicano (1992); Jacobs et al. (2005); Yu & Day (1958).

S2. Experimental

A catalytic amount of dry hydrogen chloride was introduced into the melt of levulinic acid (17.42 g, 0.15 mole) and meta-cresol (32.45 g, 0.30 mole). A brownish red mixture was left for 15 days at room temperature and poured on ice. An oily product was collected with ethyl ether and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was distilled in vacuum to remove unreacted substrates. A mixture of non-volatile components was dissolved in benzene and chromatographed on the short column (Kieselgel 60) using the benzene – izooctane 1:1 mixture as the eluent. Compound (III) was eluted first (6.02 g, 19%); m.p. 366–368 K (ethyl ether – n-hexane). The next fraction provided (I) as colourless prisms, m.p. 468–470 K. Crystallization from ethyl ether – benzene mixture gave crystals (8.03 g, 18%) suitable for X-ray diffraction studies. MS, m/z (int.): 296 (1, M⁺), 281 (4), 223 (100), 208 (4). IR (KBr): 3030 (aromatic protons); 2969, 2869, 2926 (aliphatic C — H stretching); 1706 (carbonyl band in carboxylic acid dimer); 1595m 1565, 1501 (skeletal vibrations); 860, 818, 806 (deformations of aromatic protons). ¹H–NMR (CDCl₃): 7.12, d ³J = 8.0 Hz, 2H (H-1, H-8); 6.80, dd ³J = 8.0 Hz, ⁴J = 1.2 Hz, 2H (H-2, H-7); 6.75, d ⁴J = 1.2 Hz, 2H (H-4, H-9); 2.24, s, 6H (methyl groups bonded to benzene rings); 2.11, m, 2H and 1.84, m, 2H (ethylene group on C-9); 1.58, s, 3H (methyl group on C-9). ¹³C-NMR (CDCl₃): 180.0 (carboxyl group); 150.9 (C-12, C-13); 138.0 (C-3, C-6); 126.3 (C-1, C-8); 124.4 (C-2, C-7); 123.3 (C-11, C-14); 116.9 (C-4, C-5); 40.1 (C-6, methyl group); 36.8 (C-9); 32.5, 30.6 (C-1 and C-2, ethylene group); 21.1 (Ar – methyl groups).

From the last fraction small amounts of lactone (II) were isolated (m.p. 452–454 K) and traces of 4,4-bis-(4-hydroxy-2-methylphenyl)- valeric acid (m.p. 448–450 K).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I) with atom labels. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing diagram of (I).
	Fig. 3. Reaction scheme.

β-(3,6,9-Trimethyl-9-xanthenyl)propionic acid

Crystal data

C19H20O3	F(000) = 632
Mr = 296.35	Dx = 1.237 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4075 reflections
a = 10.5042 (9) Å	θ = 2.7–29.4°
b = 14.3969 (11) Å	µ = 0.08 mm^−1
c = 11.2404 (9) Å	T = 85 K
β = 110.645 (7)°	Irregular, colourless
V = 1590.7 (2) Å^3	0.25 × 0.23 × 0.22 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer	2929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 29.4°, θmin = 2.7°
ω–scan	h = −14→13
12735 measured reflections	k = −17→19
4411 independent reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0677P)^2] where P = (Fo^2 + 2Fc^2)/3
4075 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.23 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
C1	0.54653 (11)	0.27029 (8)	0.62341 (10)	0.0160 (2)
H1	0.6202 (14)	0.3115 (9)	0.6747 (13)	0.023 (3)*
C2	0.41988 (11)	0.27971 (8)	0.63464 (11)	0.0166 (2)
H2	0.4057 (13)	0.3257 (9)	0.6905 (13)	0.021 (3)*
C3	0.31129 (11)	0.22389 (7)	0.56366 (10)	0.0153 (2)
C4	0.33408 (11)	0.15899 (7)	0.48222 (11)	0.0159 (2)
H4	0.2591 (13)	0.1191 (9)	0.4271 (12)	0.019 (3)*
C5	0.58806 (12)	0.00426 (8)	0.27792 (10)	0.0160 (2)
H5	0.5021 (13)	−0.0277 (8)	0.2353 (12)	0.018 (3)*
C6	0.70170 (12)	−0.01383 (8)	0.24647 (11)	0.0174 (2)
C7	0.82073 (12)	0.03521 (8)	0.31188 (11)	0.0198 (3)
H7	0.9041 (14)	0.0249 (9)	0.2919 (13)	0.022 (3)*
C8	0.82337 (12)	0.10053 (8)	0.40325 (11)	0.0184 (2)
H8	0.9108 (15)	0.1358 (9)	0.4460 (13)	0.026 (4)*
C9	0.71229 (11)	0.19491 (7)	0.53293 (10)	0.0125 (2)
O10	0.47112 (8)	0.08046 (5)	0.39100 (7)	0.01616 (18)
C11	0.57152 (11)	0.20465 (7)	0.54259 (10)	0.0124 (2)
C12	0.46221 (11)	0.14936 (7)	0.47324 (10)	0.0131 (2)
C13	0.59229 (11)	0.06962 (7)	0.37053 (10)	0.0134 (2)
C14	0.70842 (11)	0.12055 (7)	0.43461 (10)	0.0132 (2)
C21	0.81734 (11)	0.16763 (7)	0.66432 (10)	0.0131 (2)
H21A	0.8232 (12)	0.2171 (9)	0.7274 (12)	0.016 (3)*
H21B	0.9093 (13)	0.1643 (9)	0.6583 (12)	0.020 (3)*
C22	0.78051 (12)	0.07679 (8)	0.71238 (11)	0.0176 (2)
H22A	0.6909 (15)	0.0772 (10)	0.7165 (14)	0.030 (4)*
H22B	0.7760 (15)	0.0259 (10)	0.6524 (15)	0.034 (4)*
C23	0.87758 (11)	0.04535 (7)	0.83856 (10)	0.0142 (2)
O24	0.82955 (9)	−0.02352 (6)	0.88773 (9)	0.0309 (2)
H24	0.8952 (18)	−0.0415 (12)	0.9649 (18)	0.051 (5)*
O25	0.98967 (8)	0.07885 (6)	0.89079 (8)	0.0206 (2)
C26	0.75498 (12)	0.28876 (8)	0.49252 (11)	0.0172 (2)
H26A	0.8466 (14)	0.2862 (9)	0.4846 (12)	0.023 (3)*
H26B	0.7580 (12)	0.3375 (9)	0.5566 (12)	0.019 (3)*
H26C	0.6906 (15)	0.3085 (9)	0.4072 (14)	0.025 (4)*
C27	0.17292 (12)	0.23341 (9)	0.57411 (13)	0.0213 (3)
H27A	0.1353 (14)	0.1730 (11)	0.5853 (13)	0.026 (4)*
H27B	0.1723 (16)	0.2743 (11)	0.6474 (15)	0.039 (4)*
H27C	0.1077 (17)	0.2583 (11)	0.4953 (16)	0.042 (4)*
C28	0.69469 (15)	−0.08295 (10)	0.14359 (13)	0.0252 (3)
H28A	0.6348 (17)	−0.1350 (12)	0.1440 (16)	0.049 (5)*
H28B	0.6580 (18)	−0.0541 (12)	0.0595 (18)	0.053 (5)*
H28C	0.7874 (17)	−0.1085 (11)	0.1545 (15)	0.042 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0167 (5)	0.0160 (5)	0.0134 (5)	−0.0013 (4)	0.0029 (4)	−0.0016 (4)
C2	0.0186 (6)	0.0163 (6)	0.0148 (5)	0.0017 (4)	0.0057 (5)	−0.0017 (4)
C3	0.0146 (5)	0.0143 (5)	0.0173 (5)	0.0016 (4)	0.0062 (4)	0.0032 (4)
C4	0.0150 (5)	0.0135 (5)	0.0179 (6)	−0.0024 (4)	0.0043 (4)	−0.0001 (4)
C5	0.0180 (6)	0.0147 (5)	0.0144 (5)	−0.0031 (4)	0.0047 (5)	−0.0005 (4)
C6	0.0210 (6)	0.0172 (6)	0.0150 (5)	0.0002 (4)	0.0074 (5)	−0.0002 (4)
C7	0.0171 (6)	0.0246 (6)	0.0194 (6)	0.0010 (5)	0.0086 (5)	−0.0027 (5)
C8	0.0143 (5)	0.0229 (6)	0.0167 (6)	−0.0013 (4)	0.0040 (5)	−0.0015 (5)
C9	0.0116 (5)	0.0139 (5)	0.0107 (5)	−0.0004 (4)	0.0023 (4)	0.0006 (4)
O10	0.0148 (4)	0.0163 (4)	0.0191 (4)	−0.0040 (3)	0.0080 (3)	−0.0060 (3)
C11	0.0128 (5)	0.0131 (5)	0.0099 (5)	0.0004 (4)	0.0023 (4)	0.0026 (4)
C12	0.0167 (5)	0.0112 (5)	0.0111 (5)	0.0000 (4)	0.0047 (4)	0.0001 (4)
C13	0.0141 (5)	0.0143 (5)	0.0124 (5)	0.0003 (4)	0.0054 (4)	0.0024 (4)
C14	0.0141 (5)	0.0144 (5)	0.0105 (5)	0.0004 (4)	0.0037 (4)	0.0019 (4)
C21	0.0126 (5)	0.0139 (5)	0.0114 (5)	−0.0014 (4)	0.0024 (4)	0.0000 (4)
C22	0.0173 (6)	0.0174 (6)	0.0140 (5)	−0.0044 (4)	0.0003 (5)	0.0017 (4)
C23	0.0170 (5)	0.0118 (5)	0.0142 (5)	0.0012 (4)	0.0059 (4)	−0.0005 (4)
O24	0.0235 (5)	0.0328 (5)	0.0244 (5)	−0.0119 (4)	−0.0062 (4)	0.0162 (4)
O25	0.0147 (4)	0.0245 (4)	0.0177 (4)	−0.0034 (3)	−0.0003 (3)	0.0067 (3)
C26	0.0198 (6)	0.0157 (6)	0.0165 (6)	−0.0024 (4)	0.0071 (5)	0.0018 (4)
C27	0.0161 (6)	0.0208 (6)	0.0282 (7)	0.0006 (5)	0.0092 (5)	−0.0022 (5)
C28	0.0283 (7)	0.0269 (7)	0.0239 (7)	−0.0040 (5)	0.0135 (6)	−0.0098 (5)

Geometric parameters (Å, º)

C1—C2	1.3865 (15)	O10—C13	1.3799 (13)
C1—C11	1.3984 (15)	O10—C12	1.3813 (12)
C1—H1	0.984 (14)	C11—C12	1.3887 (14)
C2—C3	1.3935 (15)	C13—C14	1.3874 (15)
C2—H2	0.960 (13)	C21—C22	1.5164 (15)
C3—C4	1.3867 (16)	C21—H21A	0.991 (12)
C3—C27	1.5052 (16)	C21—H21B	0.993 (13)
C4—C12	1.3916 (15)	C22—C23	1.4954 (15)
C4—H4	0.995 (13)	C22—H22A	0.958 (15)
C5—C6	1.3840 (16)	C22—H22B	0.986 (15)
C5—C13	1.3922 (15)	C23—O25	1.2150 (13)
C5—H5	0.976 (13)	C23—O24	1.3190 (14)
C6—C7	1.3978 (16)	O24—H24	0.935 (18)
C6—C28	1.5076 (16)	C26—H26A	0.998 (13)
C7—C8	1.3855 (16)	C26—H26B	0.998 (14)
C7—H7	0.989 (14)	C26—H26C	1.001 (14)
C8—C14	1.4020 (15)	C27—H27A	0.981 (15)
C8—H8	1.010 (14)	C27—H27B	1.015 (16)
C9—C11	1.5268 (14)	C27—H27C	0.977 (17)
C9—C14	1.5289 (15)	C28—H28A	0.979 (18)
C9—C26	1.5416 (15)	C28—H28B	0.978 (19)
C9—C21	1.5504 (15)	C28—H28C	1.007 (17)
C2—C1—C11	122.08 (10)	C14—C13—C5	122.40 (10)
C2—C1—H1	118.0 (8)	C13—C14—C8	116.00 (10)
C11—C1—H1	119.9 (8)	C13—C14—C9	122.67 (9)
C1—C2—C3	120.63 (10)	C8—C14—C9	121.33 (10)
C1—C2—H2	120.2 (8)	C22—C21—C9	111.88 (9)
C3—C2—H2	119.2 (8)	C22—C21—H21A	108.9 (7)
C4—C3—C2	118.01 (10)	C9—C21—H21A	110.1 (7)
C4—C3—C27	120.60 (10)	C22—C21—H21B	111.0 (7)
C2—C3—C27	121.39 (10)	C9—C21—H21B	109.3 (7)
C3—C4—C12	120.76 (10)	H21A—C21—H21B	105.5 (10)
C3—C4—H4	121.2 (7)	C23—C22—C21	115.13 (9)
C12—C4—H4	118.1 (7)	C23—C22—H22A	108.0 (9)
C6—C5—C13	121.01 (10)	C21—C22—H22A	113.0 (8)
C6—C5—H5	121.2 (7)	C23—C22—H22B	106.0 (9)
C13—C5—H5	117.8 (7)	C21—C22—H22B	110.8 (9)
C5—C6—C7	117.56 (10)	H22A—C22—H22B	103.1 (12)
C5—C6—C28	120.46 (11)	O25—C23—O24	122.99 (10)
C7—C6—C28	121.97 (11)	O25—C23—C22	123.97 (10)
C8—C7—C6	120.87 (11)	O24—C23—C22	113.04 (9)
C8—C7—H7	118.9 (8)	C23—O24—H24	109.4 (11)
C6—C7—H7	120.2 (8)	C9—C26—H26A	112.5 (8)
C7—C8—C14	122.13 (11)	C9—C26—H26B	110.0 (7)
C7—C8—H8	118.1 (8)	H26A—C26—H26B	107.7 (10)
C14—C8—H8	119.7 (8)	C9—C26—H26C	111.3 (8)
C11—C9—C14	109.64 (8)	H26A—C26—H26C	105.8 (10)
C11—C9—C26	109.27 (9)	H26B—C26—H26C	109.3 (10)
C14—C9—C26	109.70 (9)	C3—C27—H27A	111.9 (8)
C11—C9—C21	109.72 (8)	C3—C27—H27B	113.5 (9)
C14—C9—C21	109.86 (8)	H27A—C27—H27B	107.0 (12)
C26—C9—C21	108.63 (9)	C3—C27—H27C	110.5 (9)
C13—O10—C12	118.49 (8)	H27A—C27—H27C	104.8 (13)
C12—C11—C1	116.40 (10)	H27B—C27—H27C	108.7 (12)
C12—C11—C9	122.50 (9)	C6—C28—H28A	111.0 (10)
C1—C11—C9	121.11 (9)	C6—C28—H28B	110.9 (10)
O10—C12—C11	123.34 (9)	H28A—C28—H28B	107.1 (14)
O10—C12—C4	114.55 (9)	C6—C28—H28C	111.4 (9)
C11—C12—C4	122.11 (10)	H28A—C28—H28C	108.3 (13)
O10—C13—C14	123.20 (10)	H28B—C28—H28C	107.9 (13)
O10—C13—C5	114.39 (9)
C11—C1—C2—C3	−0.69 (17)	C3—C4—C12—O10	178.37 (9)
C1—C2—C3—C4	0.11 (16)	C3—C4—C12—C11	−1.23 (16)
C1—C2—C3—C27	−179.71 (11)	C12—O10—C13—C14	4.26 (15)
C2—C3—C4—C12	0.82 (16)	C12—O10—C13—C5	−174.54 (9)
C27—C3—C4—C12	−179.36 (10)	C6—C5—C13—O10	179.65 (9)
C13—C5—C6—C7	0.60 (16)	C6—C5—C13—C14	0.84 (17)
C13—C5—C6—C28	−178.39 (11)	O10—C13—C14—C8	179.55 (9)
C5—C6—C7—C8	−1.04 (17)	C5—C13—C14—C8	−1.75 (16)
C28—C6—C7—C8	177.93 (11)	O10—C13—C14—C9	−0.99 (16)
C6—C7—C8—C14	0.08 (18)	C5—C13—C14—C9	177.72 (10)
C2—C1—C11—C12	0.31 (16)	C7—C8—C14—C13	1.29 (16)
C2—C1—C11—C9	−179.34 (10)	C7—C8—C14—C9	−178.18 (10)
C14—C9—C11—C12	2.30 (13)	C11—C9—C14—C13	−2.18 (14)
C26—C9—C11—C12	122.56 (11)	C26—C9—C14—C13	−122.18 (11)
C21—C9—C11—C12	−118.44 (10)	C21—C9—C14—C13	118.47 (11)
C14—C9—C11—C1	−178.06 (9)	C11—C9—C14—C8	177.26 (9)
C26—C9—C11—C1	−57.80 (13)	C26—C9—C14—C8	57.25 (13)
C21—C9—C11—C1	61.20 (12)	C21—C9—C14—C8	−62.09 (13)
C13—O10—C12—C11	−4.13 (14)	C11—C9—C21—C22	59.23 (12)
C13—O10—C12—C4	176.28 (9)	C14—C9—C21—C22	−61.37 (12)
C1—C11—C12—O10	−178.93 (9)	C26—C9—C21—C22	178.62 (9)
C9—C11—C12—O10	0.72 (15)	C9—C21—C22—C23	179.65 (9)
C1—C11—C12—C4	0.64 (15)	C21—C22—C23—O25	−12.54 (17)
C9—C11—C12—C4	−179.71 (9)	C21—C22—C23—O24	167.94 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···O25^i	0.935 (18)	1.732 (19)	2.6654 (12)	176.9 (17)
C2—H2···O10^ii	0.960 (13)	2.507 (14)	3.3989 (14)	154.6 (10)

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