The first structural characterization of a rare earth ethanesulfonate

The crystal structure of catena-poly[[triaqua­bis(ethane­sulfonato-κO)europium(III)]-μ-ethanesulfonato-κ²O:O′], [Eu(C₂H₅SO₃)₃(H₂O)₃]_n, is the first reported determination of a rare earth ethanesulfonate and also of any hydrated binary metal ethanesulfonate. Two of the three ethanesulfonate anions act as bidentate bridging ligands and connect the single [Eu(C₂H₅SO₃)₃(H₂O)₃] building blocks into infinite chains along the [010] direction. Hydrogen bonds between the water mol­ecules of one chain and sulfonate anions and water mol­ecules of adjacent chains associate the chains into a two-dimensional supra­molecular network. In the third direction, only van der Waals forces between the alkyl groups are observed.

S1. Comment

From the beginning of the 20th century, some alkanesulfonates of the rare earth elements, such as samarium and neodymium methane-, ethane-, propane- and isobutansulfonate, have been known and characterized by elemental analysis (James et al., 1912). Crystal structure analyses have only, thus far, been performed on methanesulfonates of the lanthanoids and their hydrates (Arico et al., 1997, 2001; Wickleder, 2001, 2002; Wickleder & Müller, 2004). The first crystallographically characterized rare earth ethanesulfonate is presented here. catena-poly[[triaquabis(ethanesulfonato-κO)europium(III)]-µ-ethanesulfonato-κ²O:O'], (I), is obtained from a solution of europium(III) oxide and ethanesulfonic acid in water after slow evaporation of the solvent at room temperature. After recrystallization of the raw product from a mixture of water and selected alcohols, thin colourless needles suitable for single-crystal diffraction experiments are isolated. [Eu(C₂H₅SO₃)₃(H₂O)₃] crystallizes in the monoclinic space group I2/a and in the chosen asymmetric unit the central Eu atom is surrounded by three sulfonate anions and three water molecules, all in general positions. The primary coordination is completed by two additional O atoms from two further ethanesulfonate anions (Fig. 1). In total the Eu atom is eightfold coordinated by O atoms. The coordination polyhedron is a bicapped trigonal prism. The Eu—O distances are in the range 2.354 (2) to 2.454 (3) Å. Bond lengths and angles of the sulfonate groups are as expected, with S—O distances of 1.449 (3)–1.479 (2) Å, S—C distances of 1.760 (3)–1.773 (3) Å and C—C distances of 1.513 (5)–1.515 (5) Å.

The ethanesulfonate anions containing atoms S1 and S2 operate as bidentate ligands; they link the metal atoms in a µ-κO:κO' mode and thus connect the building blocks into infinite chains along [010] (Fig. 2). In contrast, the anion containing S3 only acts as a monodentate ligand. Some µ-κO:κO'-bridging ethanesulfonate ligands are also found in dinuclear chloro–sulfonato–antimony(V) complexes (Burchardt et al., 1998; Lang et al., 1998) and in polymeric chains of the dioxouranium(VI) complex [(UO₂)(H₂O)(C₂H₅SO₃)₂] (Alcock et al., 1993) and the ethanesulfonato–hydrogenmethanephosphonato–diorganyltin(IV) compound [(C₄H₉)₂Sn{OP(O)(OH)CH₃}OS(O)₂C₂H₅] (Shankar et al., 2006). In contrast to this bridging mode, the ethanesulfonate group in the polymeric chain structure of [Cu(CO)C₂H₅SO₃] is 1κO:2κO',κO''-bridging (Doyle et al., 1983).

The structural assembly of (I) in the solid state is determined by a hierarchical system of supramolecular interactions with a pronounced gradation in bond strength with respect to each of the three dimensions. Firstly, strong Eu—O bonds are responsible for the formation of a one-dimensional chain structure. Secondly, hydrogen bonding occurs between water molecules of one chain and sulfonate anions and water molecules of adjacent chains, and thus provides an association of the one-dimensional supramolecular system in a second direction, resulting in a layered assembly of chains. Atoms H3 and H4 take part in hydrogen bonding to O atoms of the same chain exclusively. Although the bond strength can be classified as only weak to medium, proved by the O···O distances of 2.774 (3)–3.302 (4) Å, the contribution of hydrogen bonding to the composition of the solid is essential. In the third direction, van der Waals forces between ethyl groups are the only interactions of note. Fig. 3 shows the connection of the chains in the solid state packing.

Related literature

For related literature, see: Alcock et al. (1993); Arico et al. (1997, 2001); Burchardt et al. (1998); Doyle et al. (1983); James et al. (1912); Lang et al. (1998); Shankar et al. (2006); Wickleder (2001, 2002); Wickleder & Müller (2004).

S2. Experimental

A sample of Eu₂O₃ (0.354 g, 1 mmol) was suspended in water (10 ml), and ethanesulfonic acid (0.5 ml, 6 mmol) was added carefully to avoid uncontrolled local heating. The mixture was heated slowly to ca 343 K and stirred until dissolution of the rare earth oxide after a few minutes. Colourless needles of [Eu(C₂H₅SO₃)₃(H₂O)₃] were obtained by evaporation of the solvent at room temperature. To isolate crystals suitable for X-ray structure analysis and single-crystal attenuated total reflection IR recrystallization of the raw product from a mixture of ca 4 ml of water, 4 ml of methanol, 1 ml of ethanol and a few drops of glycerol proved to be necessary. IR (ν, cm^-1): 3387 (m, br), 2980 (m, sh), 2943 (m, sh), 2884 (w, sh), 1716 (w, br), 1660 (w), 1618 (w, sh), 1458 (w), 1429 (w, sh), 1421 (w), 1302 (w), 1254 (m), 1200 (m, sh), 1139 (vs), 1073 (s, sh), 1052 (s, sh), 1038 (vs), 983 (m, sh), 787 (w), 746 (m), 575 (m); CHN analysis (533.41), found: C 13.60, H 3.95%; calculated; C 13.51, H 3.97 %.

S3. Refinement

As the difference of atom displacement of Eu1 and O11 along the corresponding bond direction was somewhat too high, one `rigid bond' restraint was applied. All H-atom positions of the water molecules, including the partial occupancy positions H6 and H6A (Fig. 1), could be located in difference Fourier maps. The water molecules were treated as rigid groups with idealized geometry but with freedom of rotation and translation. Isotropic displacement parameters for their H atoms were refined, except for H5, H6 and H6A, for which the U_iso values were fixed at 150% of the U_eq value of the parent atom O12. As the partial occupancy positions of the disordered atoms H6 and H6A were not stable during refinement, their principal orientation found in the difference map was stabilized by restraining the intermolecular distances between H6 and H6A^v and H6A and H6^v [symmetry code: (v) -x + 1/2, y, -z] to 2.70 Å with an estimated standard deviation of 0.01 Å. The H atoms of the CH₂ groups were treated as riding on the C atoms with idealized bond lengths and angles. Those of the CH₃ groups were allowed to ride on the C atoms likewise, but were additionally free to rotate about the C—C bond. U_iso values were fixed at 120% of the U_eq value of the respective parent C atom, whereas the U_iso values of H atoms of the CH₃ groups were fixed at 150% of the U_eq value of the carrier atom. Three significant electron-density maxima (1.16 e Å^-3 at 0.90 Å, 1.04 e Å^-3 at 0.93 Å and 1.04 e Å^-3 at 0.90 Å from Eu1) were found in the final difference Fourier map.

Computing details

Data collection: IPDS Software (Stoe & Cie, 2000); cell refinement: IPDS Software (Stoe & Cie, 2000); data reduction: IPDS Software (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures

	Fig. 1. : The coordination environment about Eu in (I); displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn with an arbitrary radius. The disorder of one H atom at O12 is indicated by the use of solid and open bond types. Dashed lines indicate hydrogen bonds. [Symmetry codes: (ii) x, y + 1, z; (iii) x, y - 1, z.]
	Fig. 2. : Ethanesulfonate anions connect [Eu(C2H5SO3)3(H2O)3] units into chains in the [010] direction. Only one of the disordered H atoms is shown. Thin lines indicate extended bonds. H atoms of the alkyl groups have been omitted for clarity. [Symmetry codes: (ii) x, y + 1, z; (iii) x, y - 1, z.]
	Fig. 3. : The packing of (I). Hydrogen bonds and van der Waals interactions associate the chains into a supramolecular network. Dashed lines indicate hydrogen bonds. Only one of the disordered H atoms is shown. H atoms of the alkyl groups have been omitted for clarity.

catena-poly[[triaquabis(ethanesulfonato-κO)europium(III)]-µ-ethanesulfonato- κ²O:O']

Crystal data

[Eu(C2H5SO3)3(H2O)3]	F(000) = 2112
Mr = 533.41	Dx = 2.124 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2ya	Cell parameters from 7998 reflections
a = 24.323 (2) Å	θ = 2.8–26.1°
b = 5.4408 (4) Å	µ = 4.19 mm^−1
c = 27.066 (2) Å	T = 233 K
β = 111.328 (9)°	Needle, colourless
V = 3336.5 (5) Å^3	0.57 × 0.10 × 0.10 mm
Z = 8

Data collection

Stoe IPDS diffractometer	3282 independent reflections
Radiation source: fine-focus sealed tube	2788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
Detector resolution: 6.67 pixels mm^-1	θmax = 26.1°, θmin = 2.8°
ϕ scans	h = −29→29
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	k = −6→6
Tmin = 0.578, Tmax = 0.672	l = −33→33
22872 measured reflections

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.050	H-atom parameters constrained
S = 1.22	w = 1/[σ^2(Fo^2) + (0.0275P)^2] where P = (Fo^2 + 2Fc^2)/3
3282 reflections	(Δ/σ)max = 0.001
216 parameters	Δρmax = 1.16 e Å^−3
3 restraints	Δρmin = −1.19 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. The non-standard space group setting was preferred to the standard setting because of a significant smaller monoclinic angle of 111.33 ° compared to 119.87 °. It was necessary to refine one of the water molecules containing O(12) as disordered: otherwise the structure model is not plausible because neighbouring atoms are too close to each other. In spite of a careful search no superstructure reflections could be found, i. e. a split site for this aqua ligand is given or the related noncentrosymmetric space group Ia has to be chosen. Based on the distribution of E-values and arguments given by Marsh [Acta Cryst. (1986), B42, 193–198) concerning the choice of centrosymmetric and noncentrosymmetric space groups a statistic treatment in a centrosymmetric space group deemed more sensible than the use of the noncentrosymmetric subgroup.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Eu1	0.350369 (6)	0.37896 (3)	0.124278 (6)	0.01568 (6)
S1	0.28461 (3)	0.87040 (13)	0.17595 (3)	0.01754 (15)
S2	0.35168 (3)	−0.12394 (13)	0.02760 (3)	0.01897 (15)
S3	0.50656 (3)	0.19178 (14)	0.16842 (3)	0.02174 (16)
O1	0.29347 (11)	0.6213 (4)	0.15977 (11)	0.0314 (6)
O2	0.29488 (10)	1.0538 (4)	0.14085 (9)	0.0246 (5)
O3	0.31854 (10)	0.9206 (4)	0.23147 (9)	0.0296 (5)
O4	0.34044 (10)	0.0900 (4)	0.05461 (10)	0.0279 (5)
O5	0.30774 (11)	−0.1525 (5)	−0.02521 (10)	0.0385 (6)
O6	0.35952 (13)	−0.3469 (4)	0.05927 (10)	0.0358 (6)
O7	0.44884 (9)	0.2802 (4)	0.13132 (9)	0.0266 (5)
O8	0.51312 (11)	0.2367 (5)	0.22303 (10)	0.0376 (6)
O9	0.51577 (12)	−0.0621 (4)	0.15713 (12)	0.0380 (6)
O10	0.41375 (10)	0.7201 (4)	0.17091 (10)	0.0252 (5)
H1	0.4260	0.7184	0.2038	0.035 (11)*
H2	0.4436	0.7465	0.1637	0.032 (10)*
O11	0.39591 (10)	0.2747 (4)	0.21706 (9)	0.0261 (5)
H3	0.4318	0.2644	0.2349	0.038 (11)*
H4	0.3803	0.1735	0.2309	0.035 (11)*
O12	0.25025 (11)	0.4005 (5)	0.05719 (11)	0.0401 (6)
H5	0.2324	0.5318	0.0469	0.060*
H6	0.2390	0.3102	0.0307	0.060*	0.50
H6A	0.2238	0.2962	0.0519	0.060*	0.50
C1	0.20846 (14)	0.8823 (6)	0.16530 (14)	0.0262 (7)
H11	0.1860	0.8411	0.1286	0.031*
H12	0.1998	0.7595	0.1874	0.031*
C2	0.18868 (19)	1.1317 (7)	0.1775 (2)	0.0504 (11)
H21	0.1467	1.1309	0.1684	0.076*
H22	0.1990	1.2555	0.1571	0.076*
H23	0.2078	1.1666	0.2146	0.076*
C3	0.42025 (15)	−0.0709 (6)	0.02031 (14)	0.0259 (7)
H31	0.4511	−0.0565	0.0551	0.031*
H32	0.4297	−0.2098	0.0023	0.031*
C4	0.41839 (18)	0.1611 (6)	−0.01112 (17)	0.0380 (9)
H41	0.4552	0.1801	−0.0163	0.057*
H42	0.4121	0.3003	0.0080	0.057*
H43	0.3868	0.1500	−0.0450	0.057*
C5	0.56084 (15)	0.3712 (6)	0.15678 (14)	0.0276 (7)
H51	0.5558	0.5415	0.1648	0.033*
H52	0.5995	0.3183	0.1806	0.033*
C6	0.55857 (18)	0.3542 (8)	0.10026 (16)	0.0433 (10)
H61	0.5910	0.4444	0.0970	0.065*
H62	0.5220	0.4223	0.0767	0.065*
H63	0.5612	0.1850	0.0913	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Eu1	0.01554 (9)	0.01393 (8)	0.01771 (9)	0.00028 (6)	0.00620 (6)	0.00126 (6)
S1	0.0176 (4)	0.0167 (3)	0.0206 (4)	−0.0004 (3)	0.0096 (3)	−0.0001 (3)
S2	0.0234 (4)	0.0180 (3)	0.0155 (4)	−0.0045 (3)	0.0070 (3)	−0.0010 (3)
S3	0.0178 (4)	0.0228 (3)	0.0239 (4)	0.0025 (3)	0.0068 (3)	0.0005 (3)
O1	0.0294 (13)	0.0184 (10)	0.0538 (17)	−0.0011 (10)	0.0238 (12)	−0.0038 (11)
O2	0.0252 (12)	0.0261 (11)	0.0214 (12)	−0.0063 (9)	0.0071 (10)	0.0031 (9)
O3	0.0281 (12)	0.0387 (13)	0.0202 (12)	−0.0037 (10)	0.0068 (10)	0.0040 (10)
O4	0.0282 (12)	0.0262 (12)	0.0326 (13)	−0.0033 (10)	0.0150 (11)	−0.0077 (10)
O5	0.0326 (14)	0.0567 (16)	0.0209 (13)	−0.0128 (12)	0.0034 (10)	−0.0066 (12)
O6	0.0554 (17)	0.0224 (11)	0.0337 (14)	−0.0038 (11)	0.0210 (13)	0.0081 (10)
O7	0.0175 (11)	0.0372 (12)	0.0231 (12)	0.0051 (10)	0.0049 (9)	−0.0015 (10)
O8	0.0273 (13)	0.0621 (17)	0.0216 (13)	0.0094 (13)	0.0067 (10)	0.0003 (12)
O9	0.0366 (14)	0.0200 (11)	0.0603 (19)	0.0029 (10)	0.0212 (13)	0.0004 (11)
O10	0.0222 (11)	0.0271 (11)	0.0260 (13)	−0.0064 (10)	0.0084 (10)	−0.0037 (10)
O11	0.0231 (12)	0.0307 (12)	0.0219 (9)	−0.0057 (10)	0.0052 (9)	0.0043 (10)
O12	0.0266 (13)	0.0459 (15)	0.0390 (16)	0.0081 (12)	0.0014 (11)	0.0075 (12)
C1	0.0198 (16)	0.0283 (16)	0.0328 (18)	−0.0016 (14)	0.0126 (14)	0.0001 (15)
C2	0.032 (2)	0.043 (2)	0.078 (3)	0.0078 (18)	0.022 (2)	−0.017 (2)
C3	0.0251 (17)	0.0283 (16)	0.0275 (18)	0.0011 (14)	0.0133 (14)	−0.0017 (14)
C4	0.043 (2)	0.035 (2)	0.046 (2)	−0.0076 (17)	0.0276 (19)	0.0022 (17)
C5	0.0214 (16)	0.0238 (15)	0.0362 (19)	−0.0044 (14)	0.0087 (14)	−0.0023 (15)
C6	0.036 (2)	0.059 (2)	0.037 (2)	−0.008 (2)	0.0168 (18)	0.0086 (19)

Geometric parameters (Å, º)

Eu1—O1	2.354 (2)	O11—H3	0.8320
Eu1—O2^i	2.365 (2)	O11—H4	0.8311
Eu1—O4	2.399 (2)	O12—H5	0.8299
Eu1—O6^ii	2.378 (2)	O12—H6	0.8301
Eu1—O7	2.394 (2)	O12—H6A	0.8300
Eu1—O11	2.415 (2)	C1—C2	1.515 (5)
Eu1—O10	2.449 (2)	C1—H11	0.9700
Eu1—O12	2.454 (3)	C1—H12	0.9700
S1—O1	1.464 (2)	C2—H21	0.9600
S1—O2	1.460 (2)	C2—H22	0.9600
S1—O3	1.453 (2)	C2—H23	0.9600
S1—C1	1.769 (3)	C3—C4	1.514 (5)
S2—O4	1.452 (2)	C3—H31	0.9700
S2—O5	1.449 (3)	C3—H32	0.9700
S2—O6	1.457 (2)	C4—H41	0.9600
S2—C3	1.773 (3)	C4—H42	0.9600
S3—O7	1.479 (2)	C4—H43	0.9600
S3—O8	1.449 (3)	C5—C6	1.513 (5)
S3—O9	1.449 (2)	C5—H51	0.9700
S3—C5	1.760 (3)	C5—H52	0.9700
O2—Eu1^ii	2.365 (2)	C6—H61	0.9600
O6—Eu1^i	2.378 (2)	C6—H62	0.9600
O10—H1	0.8290	C6—H63	0.9600
O10—H2	0.8311
O1—Eu1—O2^i	83.16 (8)	S2—O6—Eu1^i	158.40 (16)
O1—Eu1—O6^ii	100.24 (8)	S3—O7—Eu1	143.38 (14)
O2^i—Eu1—O6^ii	145.38 (9)	Eu1—O10—H1	117.3
O1—Eu1—O7	144.37 (8)	Eu1—O10—H2	116.8
O2^i—Eu1—O7	116.14 (8)	H1—O10—H2	104.4
O6^ii—Eu1—O7	80.76 (9)	Eu1—O11—H3	127.4
O1—Eu1—O4	141.41 (9)	Eu1—O11—H4	120.8
O2^i—Eu1—O4	75.97 (8)	H3—O11—H4	104.4
O6^ii—Eu1—O4	80.74 (8)	Eu1—O12—H5	123.2
O7—Eu1—O4	74.17 (8)	Eu1—O12—H6	122.6
O1—Eu1—O11	79.79 (9)	H5—O12—H6	104.6
O2^i—Eu1—O11	72.82 (8)	Eu1—O12—H6A	126.4
O6^ii—Eu1—O11	141.80 (9)	H5—O12—H6A	104.6
O7—Eu1—O11	78.30 (8)	C2—C1—S1	113.2 (2)
O4—Eu1—O11	122.71 (8)	C2—C1—H11	108.9
O1—Eu1—O10	73.66 (8)	S1—C1—H11	108.9
O2^i—Eu1—O10	139.89 (8)	C2—C1—H12	108.9
O6^ii—Eu1—O10	72.26 (9)	S1—C1—H12	108.9
O7—Eu1—O10	72.84 (8)	H11—C1—H12	107.8
O4—Eu1—O10	140.02 (8)	C1—C2—H21	109.5
O11—Eu1—O10	71.18 (8)	C1—C2—H22	109.5
O1—Eu1—O12	72.71 (9)	H21—C2—H22	109.5
O2^i—Eu1—O12	72.24 (8)	C1—C2—H23	109.5
O6^ii—Eu1—O12	75.96 (10)	H21—C2—H23	109.5
O7—Eu1—O12	139.86 (9)	H22—C2—H23	109.5
O4—Eu1—O12	70.17 (9)	C4—C3—S2	111.2 (2)
O11—Eu1—O12	137.47 (9)	C4—C3—H31	109.4
O10—Eu1—O12	127.89 (8)	S2—C3—H31	109.4
O3—S1—O2	112.15 (13)	C4—C3—H32	109.4
O3—S1—O1	113.15 (15)	S2—C3—H32	109.4
O2—S1—O1	111.05 (13)	H31—C3—H32	108.0
O3—S1—C1	109.20 (15)	C3—C4—H41	109.5
O2—S1—C1	106.60 (15)	C3—C4—H42	109.5
O1—S1—C1	104.15 (14)	H41—C4—H42	109.5
O5—S2—O4	112.10 (15)	C3—C4—H43	109.5
O5—S2—O6	112.51 (16)	H41—C4—H43	109.5
O4—S2—O6	112.32 (14)	H42—C4—H43	109.5
O5—S2—C3	107.09 (16)	C6—C5—S3	113.2 (2)
O4—S2—C3	106.40 (14)	C6—C5—H51	108.9
O6—S2—C3	105.88 (16)	S3—C5—H51	108.9
O8—S3—O9	114.06 (17)	C6—C5—H52	108.9
O8—S3—O7	111.30 (14)	S3—C5—H52	108.9
O9—S3—O7	110.38 (15)	H51—C5—H52	107.8
O8—S3—C5	106.13 (16)	C5—C6—H61	109.5
O9—S3—C5	107.89 (15)	C5—C6—H62	109.5
O7—S3—C5	106.66 (15)	H61—C6—H62	109.5
S1—O1—Eu1	144.36 (13)	C5—C6—H63	109.5
S1—O2—Eu1^ii	151.51 (14)	H61—C6—H63	109.5
S2—O4—Eu1	159.61 (16)	H62—C6—H63	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H1···O8^iii	0.83	2.00	2.774 (3)	156
O10—H2···O9^ii	0.83	2.10	2.894 (3)	159
O11—H3···O8	0.83	2.12	2.804 (3)	139
O11—H4···O3^i	0.83	2.04	2.818 (3)	155
O12—H5···O5^iv	0.83	1.96	2.787 (4)	178
O12—H6···O12^v	0.83	2.53	3.092	126
O12—H6A···O5^v	0.83	2.58	3.302 (4)	146

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