Poly[[hexa­aqua­(μ₂-oxalato-κ⁴O¹,O²:O^1′,O^2′)bis­(μ₃-pyridine-2,4-dicarboxyl­ato-κ⁴N,O²:O^2′:O⁴)dilanthanum(III)] monohydrate]

In the polymeric title compound, {[La₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O}_n, the La³⁺ cation is nine-coordinated in a distorted LaNO₈ tricapped trigonal–prismatic geometry formed by three pyridinedicarboxylate anions, one oxalate anion and three water mol­ecules. The oxalate anion is located on an inversion center. The oxalate and pyridine­dicarboxyl­ate anions bridge the La³⁺ cations, forming a two-dimensional polymeric complex parallel to (010). Inter­molecular O—H...O hydrogen bonding and weak C—H...O hydrogen bonding is present in the crystal structure and π–π stacking [centroid–centroid distance = 3.571 (3) Å] is observed between parallel pyridine rings of adjacent mol­ecules. The uncoordinated water molecule shows an occupancy of 0.5.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in solvent or counterion
• R factor = 0.032
• wR factor = 0.093
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H7B    ..  H10B    ..       2.09 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H9B    ..  H10B    ..       2.07 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        La1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT314_ALERT_2_C Check Small Angle for H2O: Metal-O9     -H9A          86.62 Deg.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0081 Ang
PLAT417_ALERT_2_C Short Inter D-H..H-D       H9B    ..  H10A    ..       2.12 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          2
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       2.05 eA-3
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.11 eA-3

Alert level G
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  La1    --  O9      ..        8.3 su
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................        100 Perc.
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          78 Perc.
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          !

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

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

---

S1. Comment

The pyridine-2,4-dicarboxylic acid (pdcH2) has important coordination functions to metals by either carboxylate bridges between metal centers, to form dimeric complexes or tridentate (O, N, O') chelation to metal ions. Some pydc complexes have been reported (Li et al., 2007; Wang et al., 2009; Aghabozorg et al., 2011).

The symmetric unit of the title compound,{[(LaC₇H₃NO₄)(C₂O₄)_0.5(H₂O)₃]₂.(H₂O)}_n, contains two La^III atoms, two pyridine-2,4-dicarboxylate(pydc) ligands, one oxalate ligand and six coordinated water molecules. The oxalate ligand are both chelating and bridging, forming an oxalate-bridged dinuclear complex. The La^III is nine-coordinated in a distorted tricapped trigonal prismatic geometry by N,O atom from a pydc ligand, two O atoms from two pydc ligands, two O atoms from one oxalate ligand and three O atoms from coordinated water molecules (shown as Fig. 1, Table 1). The geometric center of the dimer lies on an inversion center.

The crystal structure contains weak O—H···O and non-classical C—H···O hydrogen bonds. The π-π stacking between two pyridine rings of (pydc) anion fragments with distances of 3.570 (3) Å (1 - x, 1 - y,1 - z) are observed (Fig. 3). The uncoordinated water molecule shows half-occupation.

Related literature

For related structures, see: Aghabozorg et al. (2011); Li et al. (2007); Wang et al. (2009).

S2. Experimental

La(NO₃)₃.6H2O (0.1096 g, 0.25 mmole), pydridine-2,4-dicarboxylic acid (0.0418 g, 0.25 mmol) and 4,4'-dipyridine (0.0464 g, 0.25 mmol) were mixed in 10 ml of deionized water. After stirring for 30 min, the mixture was placed in a 23 ml Teflon-lined reactor which was heated under autogenous pressure to 418 K for 48 h and then allowed to cool to room temperature. The brown transparent single crystals were obtained in 41.3% yield (based on La).

S3. Refinement

The site occupancy factor of the lattice water O10 was refined to 0.509 (16), and was set as 0.5 at the final cycles of refinement. Water H atoms were fixed in chemical sensible positions, thermal parameters were fixed as 0.08 Ų. Other H atoms were positioned geometrically with C—H = 0.93 Å (aromatic) and refined using a riding model with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. All H atoms have been omitted for clarity. [Symmetry code: (i) -1 + x, y, z; (ii) 1 - x, 1 - y, 1 - z; (iv)1+x, y, z.]
	Fig. 2. The molecular packing for the title compound. Hydrogen bonds are shown as dashed lines.
	Fig. 3. π-π Stacking between pyridine rings [symmetry code: (ii) 1 - x, 1 - y,1 - z.]

Poly[[hexaaqua(µ₂-oxalato- κ⁴O¹,O²:O^1',O^2')bis(µ₃-pyridine-2,4- dicarboxylato-κ⁴N,O²:O^2':O⁴) dilanthanum(III)] monohydrate]

Crystal data

[La2(C7H3NO4)2(C2O4)(H2O)6]·H2O	Z = 1
Mr = 822.16	F(000) = 396
Triclinic, P1	Dx = 2.355 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4614 (8) Å	Cell parameters from 3390 reflections
b = 6.6844 (8) Å	θ = 2.5–25.0°
c = 14.0796 (17) Å	µ = 3.73 mm^−1
α = 89.735 (2)°	T = 295 K
β = 85.266 (2)°	Columnar, brown
γ = 73.135 (2)°	0.30 × 0.10 × 0.10 mm
V = 579.85 (12) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2046 independent reflections
Radiation source: fine-focus sealed tube	1795 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 9 pixels mm^-1	θmax = 25.0°, θmin = 1.5°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −7→7
Tmin = 0.686, Tmax = 0.950	l = −16→16
5023 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0639P)^2] where P = (Fo^2 + 2Fc^2)/3
2046 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 2.14 e Å^−3
0 restraints	Δρmin = −2.13 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
La1	0.36051 (5)	0.32815 (5)	0.80389 (2)	0.0265 (1)
O1	0.7674 (8)	0.3427 (7)	0.2806 (3)	0.0392 (16)
O2	1.0913 (8)	0.2154 (8)	0.3384 (3)	0.0525 (19)
O3	1.0788 (7)	0.2730 (8)	0.6993 (3)	0.0396 (16)
O4	0.7592 (7)	0.3177 (9)	0.7799 (3)	0.0521 (18)
O5	0.5103 (8)	0.2478 (6)	0.9657 (3)	0.0423 (14)
O6	0.5841 (9)	0.3677 (7)	1.1030 (3)	0.0485 (18)
O7	−0.0071 (10)	0.5171 (10)	0.8990 (5)	0.0863 (19)
O8	0.5618 (9)	−0.0608 (7)	0.7835 (4)	0.0542 (19)
O9	0.1731 (10)	0.0871 (10)	0.9025 (5)	0.0863 (19)
N1	0.5725 (7)	0.2598 (7)	0.6261 (3)	0.0249 (14)
C1	0.7769 (9)	0.2729 (9)	0.6137 (4)	0.0257 (17)
C2	0.5722 (10)	0.2408 (9)	0.4559 (4)	0.0294 (17)
C3	0.7801 (9)	0.2612 (8)	0.4439 (4)	0.0260 (17)
C4	0.8843 (9)	0.2739 (9)	0.5250 (4)	0.0285 (17)
C5	0.4771 (9)	0.2395 (9)	0.5474 (4)	0.0291 (17)
C6	0.8914 (10)	0.2739 (9)	0.3464 (4)	0.0301 (17)
C7	0.8804 (10)	0.2893 (10)	0.7040 (4)	0.0341 (19)
C8	0.5274 (10)	0.3885 (9)	1.0197 (4)	0.0288 (17)
O10	−0.1015 (18)	−0.0885 (16)	0.9137 (11)	0.072 (5)	0.500
H2A	0.49810	0.22820	0.40340	0.0350*
H4A	1.02570	0.28300	0.51960	0.0340*
H5A	0.33850	0.22340	0.55470	0.0350*
H7A	−0.08470	0.47740	0.86270	0.0800*
H7B	−0.05250	0.64720	0.89900	0.0800*
H8A	0.67010	−0.11890	0.74700	0.0800*
H8B	0.55880	−0.18960	0.81340	0.0800*
H9A	0.29540	−0.01320	0.89080	0.0800*
H9B	0.07450	0.05280	0.87580	0.0800*
H10A	−0.22390	−0.01980	0.89910	0.0800*	0.500
H10B	−0.11240	−0.06870	0.97360	0.0800*	0.500

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
La1	0.0283 (2)	0.0378 (2)	0.0187 (2)	−0.0182 (2)	−0.0020 (1)	0.0042 (1)
O1	0.043 (3)	0.047 (3)	0.025 (2)	−0.009 (2)	−0.004 (2)	0.0078 (19)
O2	0.033 (3)	0.074 (4)	0.039 (3)	−0.001 (2)	0.009 (2)	0.014 (2)
O3	0.028 (2)	0.060 (3)	0.038 (3)	−0.022 (2)	−0.0100 (19)	0.002 (2)
O4	0.037 (3)	0.112 (4)	0.023 (2)	−0.046 (3)	−0.005 (2)	0.007 (2)
O5	0.067 (3)	0.029 (2)	0.032 (2)	−0.013 (2)	−0.015 (2)	0.0013 (19)
O6	0.079 (4)	0.038 (2)	0.036 (3)	−0.022 (2)	−0.030 (3)	0.013 (2)
O7	0.059 (3)	0.072 (3)	0.113 (4)	−0.008 (2)	0.037 (3)	0.026 (3)
O8	0.071 (4)	0.034 (3)	0.053 (3)	−0.016 (2)	0.023 (3)	0.001 (2)
O9	0.059 (3)	0.072 (3)	0.113 (4)	−0.008 (2)	0.037 (3)	0.026 (3)
N1	0.020 (2)	0.029 (2)	0.027 (3)	−0.0093 (19)	−0.0018 (19)	0.002 (2)
C1	0.018 (3)	0.029 (3)	0.031 (3)	−0.008 (2)	−0.003 (2)	0.006 (2)
C2	0.030 (3)	0.037 (3)	0.023 (3)	−0.011 (3)	−0.009 (2)	0.002 (2)
C3	0.025 (3)	0.027 (3)	0.024 (3)	−0.005 (2)	−0.001 (2)	0.004 (2)
C4	0.019 (3)	0.039 (3)	0.027 (3)	−0.008 (2)	−0.002 (2)	0.008 (3)
C5	0.023 (3)	0.036 (3)	0.030 (3)	−0.011 (2)	−0.004 (2)	0.003 (2)
C6	0.033 (3)	0.032 (3)	0.023 (3)	−0.007 (3)	0.001 (2)	0.000 (2)
C7	0.030 (3)	0.046 (4)	0.033 (3)	−0.021 (3)	−0.006 (3)	0.011 (3)
C8	0.032 (3)	0.030 (3)	0.022 (3)	−0.006 (2)	0.000 (2)	0.003 (2)
O10	0.044 (6)	0.044 (6)	0.135 (12)	−0.014 (5)	−0.036 (7)	0.007 (7)

Geometric parameters (Å, º)

La1—N1	2.726 (4)	O8—H8B	0.9600
La1—O1^i	2.454 (4)	O9—H9B	0.8500
La1—O3^ii	2.541 (5)	O9—H9A	0.8800
La1—O4	2.551 (5)	O10—H10A	0.8300
La1—O5	2.543 (4)	O10—H10B	0.8500
La1—O6^iii	2.550 (5)	N1—C5	1.338 (7)
La1—O7	2.604 (7)	N1—C1	1.346 (8)
La1—O8	2.553 (5)	C1—C4	1.379 (8)
La1—O9	2.612 (7)	C1—C7	1.503 (8)
O1—C6	1.271 (8)	C2—C3	1.386 (9)
O2—C6	1.232 (9)	C2—C5	1.382 (8)
O3—C7	1.251 (8)	C3—C6	1.510 (8)
O4—C7	1.253 (7)	C3—C4	1.388 (8)
O5—C8	1.247 (7)	C8—C8^iii	1.541 (8)
O6—C8	1.253 (7)	C2—H2A	0.9300
O7—H7B	0.8300	C4—H4A	0.9300
O7—H7A	0.8400	C5—H5A	0.9300
O8—H8A	0.8300
O4—La1—O5	73.91 (15)	La1—O5—C8	121.8 (4)
O4—La1—O7	143.20 (19)	La1^iii—O6—C8	121.6 (4)
O4—La1—O8	76.08 (19)	La1—O7—H7B	119.00
O4—La1—O9	130.46 (19)	H7A—O7—H7B	105.00
O4—La1—N1	60.09 (14)	La1—O7—H7A	96.00
O3^ii—La1—O4	136.05 (14)	La1—O8—H8A	129.00
O1^i—La1—O4	94.15 (17)	H8A—O8—H8B	93.00
O4—La1—O6^iii	71.03 (17)	La1—O8—H8B	138.00
O5—La1—O7	85.94 (19)	La1—O9—H9A	87.00
O5—La1—O8	78.78 (15)	H9A—O9—H9B	108.00
O5—La1—O9	68.31 (19)	La1—O9—H9B	116.00
O5—La1—N1	129.55 (15)	H10A—O10—H10B	102.00
O3^ii—La1—O5	143.58 (15)	La1—N1—C5	123.7 (4)
O1^i—La1—O5	131.93 (14)	La1—N1—C1	118.9 (3)
O5—La1—O6^iii	62.98 (13)	C1—N1—C5	116.8 (5)
O7—La1—O8	130.39 (19)	N1—C1—C4	122.9 (5)
O7—La1—O9	64.2 (2)	N1—C1—C7	115.1 (5)
O7—La1—N1	143.97 (18)	C4—C1—C7	121.9 (6)
O3^ii—La1—O7	76.45 (18)	C3—C2—C5	118.7 (5)
O1^i—La1—O7	76.62 (19)	C2—C3—C6	122.0 (5)
O6^iii—La1—O7	72.42 (19)	C4—C3—C6	120.1 (5)
O8—La1—O9	66.27 (19)	C2—C3—C4	117.9 (5)
O8—La1—N1	71.47 (16)	C1—C4—C3	119.6 (6)
O3^ii—La1—O8	88.67 (17)	N1—C5—C2	123.9 (6)
O1^i—La1—O8	144.45 (16)	O1—C6—O2	126.8 (6)
O6^iii—La1—O8	134.78 (18)	O2—C6—C3	117.2 (5)
O9—La1—N1	128.72 (18)	O1—C6—C3	116.1 (6)
O3^ii—La1—O9	75.33 (18)	O4—C7—C1	116.7 (6)
O1^i—La1—O9	135.03 (19)	O3—C7—C1	119.0 (5)
O6^iii—La1—O9	115.40 (18)	O3—C7—O4	124.3 (6)
O3^ii—La1—N1	76.02 (14)	O5—C8—O6	126.8 (5)
O1^i—La1—N1	74.06 (14)	O5—C8—C8^iii	116.9 (5)
O6^iii—La1—N1	114.76 (15)	O6—C8—C8^iii	116.4 (5)
O1^i—La1—O3^ii	74.77 (16)	C5—C2—H2A	121.00
O3^ii—La1—O6^iii	136.50 (17)	C3—C2—H2A	121.00
O1^i—La1—O6^iii	69.06 (15)	C1—C4—H4A	120.00
La1^i—O1—C6	137.1 (4)	C3—C4—H4A	120.00
La1^iv—O3—C7	139.6 (4)	N1—C5—H5A	118.00
La1—O4—C7	128.4 (4)	C2—C5—H5A	118.00
O5—La1—O4—C7	158.8 (6)	N1—La1—O1^i—C6^i	73.1 (6)
O7—La1—O4—C7	−141.7 (5)	O4—La1—O6^iii—C8^iii	−86.9 (5)
O8—La1—O4—C7	76.7 (6)	O5—La1—O6^iii—C8^iii	−5.7 (5)
O9—La1—O4—C7	117.6 (6)	O7—La1—O6^iii—C8^iii	88.8 (5)
N1—La1—O4—C7	0.3 (5)	O8—La1—O6^iii—C8^iii	−41.2 (6)
O3^ii—La1—O4—C7	3.7 (7)	O9—La1—O6^iii—C8^iii	39.8 (6)
O1^i—La1—O4—C7	−68.6 (6)	N1—La1—O6^iii—C8^iii	−129.2 (5)
O6^iii—La1—O4—C7	−134.8 (6)	La1^i—O1—C6—C3	102.3 (6)
O4—La1—O5—C8	82.1 (5)	La1^i—O1—C6—O2	−78.5 (8)
O7—La1—O5—C8	−66.7 (5)	La1^iv—O3—C7—O4	−11.4 (11)
O8—La1—O5—C8	160.7 (5)	La1^iv—O3—C7—C1	169.0 (4)
O9—La1—O5—C8	−130.5 (5)	La1—O4—C7—C1	4.4 (9)
N1—La1—O5—C8	106.5 (5)	La1—O4—C7—O3	−175.2 (5)
O3^ii—La1—O5—C8	−127.3 (5)	La1—O5—C8—O6	174.5 (5)
O1^i—La1—O5—C8	1.2 (6)	La1—O5—C8—C8^iii	−5.3 (8)
O6^iii—La1—O5—C8	5.6 (5)	La1^iii—O6—C8—O5	174.7 (5)
O4—La1—N1—C1	−5.7 (4)	La1^iii—O6—C8—C8^iii	−5.5 (8)
O4—La1—N1—C5	−177.0 (5)	C5—N1—C1—C4	2.4 (8)
O5—La1—N1—C1	−32.9 (5)	La1—N1—C1—C7	9.8 (6)
O5—La1—N1—C5	155.9 (4)	C1—N1—C5—C2	−3.0 (8)
O7—La1—N1—C1	135.5 (4)	C5—N1—C1—C7	−178.3 (5)
O7—La1—N1—C5	−35.7 (6)	La1—N1—C5—C2	168.4 (4)
O8—La1—N1—C1	−90.0 (4)	La1—N1—C1—C4	−169.4 (4)
O8—La1—N1—C5	98.8 (4)	N1—C1—C7—O3	170.2 (6)
O9—La1—N1—C1	−125.6 (4)	N1—C1—C7—O4	−9.4 (8)
O9—La1—N1—C5	63.2 (5)	C4—C1—C7—O3	−10.5 (9)
O3^ii—La1—N1—C1	176.7 (4)	C4—C1—C7—O4	169.9 (6)
O3^ii—La1—N1—C5	5.4 (4)	N1—C1—C4—C3	0.1 (9)
O1^i—La1—N1—C1	98.8 (4)	C7—C1—C4—C3	−179.1 (5)
O1^i—La1—N1—C5	−72.4 (4)	C5—C2—C3—C4	1.6 (8)
O6^iii—La1—N1—C1	41.6 (4)	C3—C2—C5—N1	1.0 (9)
O6^iii—La1—N1—C5	−129.7 (4)	C5—C2—C3—C6	−177.2 (5)
O4—La1—O3^ii—C7^ii	−173.4 (6)	C2—C3—C6—O1	25.5 (8)
O5—La1—O3^ii—C7^ii	49.4 (8)	C6—C3—C4—C1	176.7 (5)
O7—La1—O3^ii—C7^ii	−13.9 (7)	C4—C3—C6—O2	27.4 (8)
O8—La1—O3^ii—C7^ii	118.3 (7)	C2—C3—C6—O2	−153.9 (6)
O9—La1—O3^ii—C7^ii	52.5 (7)	C4—C3—C6—O1	−153.3 (5)
N1—La1—O3^ii—C7^ii	−170.5 (7)	C2—C3—C4—C1	−2.1 (8)
O4—La1—O1^i—C6^i	130.4 (6)	O5—C8—C8^iii—O5^iii	−180.0 (6)
O5—La1—O1^i—C6^i	−157.6 (6)	O5—C8—C8^iii—O6^iii	−0.2 (9)
O7—La1—O1^i—C6^i	−85.8 (6)	O6—C8—C8^iii—O5^iii	0.2 (9)
O8—La1—O1^i—C6^i	58.6 (7)	O6—C8—C8^iii—O6^iii	180.0 (6)
O9—La1—O1^i—C6^i	−56.3 (7)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4^ii	0.84	2.08	2.911 (8)	168
O7—H7B···O10^v	0.83	1.71	2.533 (12)	168
O8—H8A···O2^vi	0.83	1.83	2.660 (7)	173
O8—H8B···O6^vii	0.96	2.03	2.914 (7)	153
O9—H9A···O6^vii	0.88	2.27	2.987 (8)	138
O9—H9B···O10	0.85	1.73	2.390 (14)	133
O10—H10A···O5^ii	0.83	2.24	2.885 (12)	135
O10—H10A···O8^ii	0.83	2.29	2.924 (15)	133
O10—H10B···O9^viii	0.85	1.77	2.591 (17)	163
C5—H5A···O3^ii	0.93	2.49	3.164 (7)	130

Symmetry codes: (ii) x−1, y, z; (v) x, y+1, z; (vi) −x+2, −y, −z+1; (vii) −x+1, −y, −z+2; (viii) −x, −y, −z+2.