catena-Poly[[[triaqua­zinc(II)]-μ-2-nitro­terephthalato-κO¹:κ²O⁴,O^4′] monohydrate]

The title complex, {[Zn(C₈H₃NO₆)(H₂O)₃]·H₂O}_n, has a one-dimensional chain structure. The two carboxyl­ate groups of the dianionic 2-nitro­terephthalate ligand adopt mono- and bidentate chelating modes. The Zn atom shows distorted octa­hedral coordination, bonded to three O atoms from two carboxyl­ate groups and three O atoms of three non-equivalent coordinated water mol­ecules. The one-dimensional chains are aggregated into two-dimensional layers through inter-chain hydrogen bonding. The whole three-dimensional structure is further stabilized by inter-layer hydrogen bonds.

S1. Comment

Metal–organic networks or coordination polymers have attracted much attention recently in the area of topology design and for their potential applications in adsorption, catalysis, luminescence, magnetism etc. (Blatov et al., 2004; James, 2003; Janiak, 2003). The use of dicarboxylate ligands as small building blocks to generate metal–organic frameworks of different dimensionalities may lead to interesting network architectures (Rodríguez-Martín et al., 2002; Guo & Zhao, 2006). In particular, aromatic dicarboxylate ligands such as terephthalate (benzene-1,4-dicarboxylate, bdc) have been used in the architecture of polymeric metal complexes because they can adopt bis-monodentate, bis-bidentate and combined modes of coordination to form short bridges via one carboxylate end, or long bridges via the aromatic ring, and this can lead to a great variety of structures. For example, as a bis-monodentate ligand, the terephthalate dianion is known to bond to metals to give one-dimensional chain complexes, e.g. in [Cu(bdc)(N-MeIm)₂]_n (where N-MeIm is N-methylimidazole) (Liu et al., 2005), [Zn(bdc)(H₂O)₂]_n (Ding et al., 2003) and [[Co(bdc)(4-picoline)₂(H₂O)₂](4-picoline)]_n (Groeneman et al., 1999). On the other hand, in its bis-bidentate and combined modes of coordination, the terephthalate dianion can be found to chelate through the two carboxylate O atoms, as in [Cr(OH)(bdc)]_4n[HO₂C—C₆H₄—CO₂H]_3n (Millange et al., 2002), [Cu(L)(bdc)]_n [L is N-(2-aminoethyl)-3-amino-1-propanol] (Mukherjee et al., 2004) and [Ni(bdc)(2,2'-bipy)(H₂O)₂]_n (2,2'-bipy is 2,2'-bipyridine) (Go et al., 2004). However, in spite of this wealth of possibilities, only a few complexes of metal–nitroterephthalate systems have been reported to date. We have used the 2-nitroterephthalate dianion as a ligand, and have obtained the title novel six-coordinate 2-nitroterephthalato–zinc complex, (I). We describe here the structure of this one-dimensional metal–nitroterephthalate coordination polymer, with strong O—H···O interchain bonding leading to a three-dimensional supramolecular network.

The asymmetric unit in the structure of (I) comprises one Zn atom, one complete 2-nitroterephthalate dianion and four non-equivalent water molecules, and is shown in Fig. 1 in a symmetry-expanded view, which displays the full coordination of the Zn atom. Selected geometric parameters are given in Table 1.

The Zn atom of (I) is surrounded by an O₆ donor set with octahedral geometry. The four equatorial sites are occupied by three O atoms from a monodentate carboxylate group (O1) and a bidentate carboxylate group [O3ⁱ and O4ⁱ; symmetry code: (i) -x, y + 1/2, -z + 1/2], and by one coordinated water molecule, O9. Atoms O7 and O8 from two other water molecules occupy two of the opposing apices of the octahedron. The Zn—O_water distances range from 2.051 (2) to 2.090 (2) Å and the Zn—O_{2-nitroterephthalate} distances are in the range 1.987 (2)–2.253 (2) Å. Of these Zn—O distances, Zn—O3ⁱ and Zn—O4ⁱ are the longest. The cis O—Zn—O bond angles range from 85.32 (8) to 105.49 (9)°, except for O3ⁱ—Zn1—O4ⁱ, which is 58.80 (8)°. The trans O—Zn—O bond angles cover the range 156.60 (9)–172.19 (8)°. Thus, the coordination octahedron around the Zn atom is significantly distorted.

In the present structure, the versatility of the dianionic 2-nitroterephthalate ligand can be clearly seen. Mono- and bidentate chelating and bridging bonding modes are present. Atom O1 of the O1/C1/O2 carboxylate group has a monodentate mode, while atoms O3 and O4 of the O3/C8/O4 carboxylate group adopt a bidentate 1,2-chelating mode to the Zn atom. These adopt a bridging mode via the aromatic ring to connect two Zn atoms. The O—C—O angle for the monodentate carboxylate group (O1/C1/O2) is 127.5 (3)°, notably larger than the value of 120.8 (3)° for the chelating carboxylate group. The two C—O bond distances (O1—C1 and O2—C1) of the monodentate carboxylate group are 1.267 (4) and 1.232 (4) Å, respectively, while the two C—O bond distances (O3—C8 and O4—C8) of the chelating carboxylate group are 1.262 (4) and 1.259 (4) Å, respectively. This indicates that the mesomeric effect for the chelating carboxylate group is greater than that of the monodentate carboxylate group.

In the crystallographic c direction, perpendicular to the direction of chain propagation, neighbouring chains are linked together via O8—H8B···O3ⁱⁱ (part of a bifurcated hydrogen bond) and O7—H7A···O3ⁱⁱⁱ hydrogen-bonded interactions (symmetry codes and geometric details in Table 2). This results in the Zn atoms stacking in a zigzag fashion along the c direction and the aryl rings of the 2-nitroterephthalate ligands stacking along the c direction, ca 3.93 Å apart. In this way, a two-dimensional layer is formed parallel to the bc plane (Fig. 2). Supramolecular connectivity within this layer is further enhanced by hydrogen bonds involving the uncoordinated water molecules (Table 2).

The three coordinated water molecules, a disordered water molecule and the nitro group (O5/N1/O6) also engage in hydrogen bonds (Table 2), which influence the conformation of the polymer. The strong hydrogen bond O8—H8A···O2^v plays an important role (Brown, 1976) in the aggregation of the one-dimensional polymer through the formation of a 12-membered hydrogen-bonded R₂²(12) ring (Bernstein et al., 1995) between chains (Fig. 3a). Furthermore, the hydrogen bond O9—H9A···O4^vi links each chain to its neighbour via an R₂²(8) grouping (Fig. 3a). The resulting supramolecular aggregation yields a zigzag stacking of the Zn atoms along the a direction. Also in the a direction, perpendicular to the direction of chain propagation, O9—H9B···O2^iv hydrogen bonds link neighbouring chains together and complete a two-dimensional layer parallel to the crystallographic ab plane (Fig. 3b). Other hydrogen bonds, such as O8—H8B···O5, O10—H10B···O6, O10—H10A···O4^iv and O10'—H11A···O4^iv, involving free water molecules, further enhance the aggregation in this layer. Full details of all these hydrogen bonds, and their associated symmetry codes, are given in Table 2.

Related literature

For related literature, see: Bernstein et al. (1995); Blatov et al. (2004); Brown (1976); Ding et al. (2003); Go et al. (2004); Groeneman et al. (1999); Guo & Zhao (2006); James (2003); Janiak (2003); Liu et al. (2005); Millange et al. (2002); Mukherjee et al. (2004); Rodríguez-Martín, Hernández-Molina, Delgado, Pasán, Ruiz-Pérez, Sanchiz, Lloret & Julve (2002).

S2. Experimental

The addition of anhydrous sodium carbonate (0.43 g, 4 mmol) to a stirred solution of zinc nitrate hexahydrate (1.2 g, 4 mmol) in water (30 ml) produced a white precipitate, which was filtered off and washed with distilled water. The precipitate was subsequently added to a stirred solution of 2-nitroterephthalic acid (0.53 g, 2.5 mmol) in boiling water (20.0 ml) over a period of 5 min. After filtration, slow evaporation over a period of two weeks at room temperature provided colourless needle-like crystals of (I).

S3. Refinement

All water H atoms were found in difference Fourier maps and were fixed during refinement at O—H distances of 0.85 Å, with U_iso(H) = 1.2U_eq(O). The noncoordinated water molecule is disordered over at least two sites; the refined occupancy factors for atoms O10 and O10' were 0.740 (2):0.260 (2). The H atoms of the CH groups were treated as riding, with C—-H = 0.93 Å and U_iso (H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of (I), showing the atom-numbering scheme and the coordination polyhedra for the Zn atoms. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbirtrary radii. A disordered water molecule is shown. [Symmetry code: (i) -x, y + 1/2, -z + 1/2].
	Fig. 2. The packing of (I), showing hydrogen-bond interactions (dashed lines) in the direction of the bc plane, viewed down the a axis. The minor disorder component has been omitted.
	Fig. 3. Packing diagrams for (I), viewed down the c axis, showing the hydrogen-bonding interactions (dashed lines) in the direction of the ab plane. (a) The O8—H8A···O2 and O9—H9A···O4 hydrogen bonds. (b) The hydrogen bonds involving O9—H9B and O2 etc. [Not clear - please describe more fully]. The minor disorder component has been omitted.

catena-Poly[[[triaquazinc(II)]-µ-2-nitroterephthalato- κO¹:κ²O⁴:O^4'] monohydrate]

Crystal data

[Zn(C8H3NO6)(H2O)3]·H2O	F(000) = 704
Mr = 346.55	Dx = 1.892 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3987 reflections
a = 7.8862 (12) Å	θ = 2.7–26.4°
b = 20.501 (5) Å	µ = 2.07 mm^−1
c = 7.7119 (13) Å	T = 294 K
β = 102.633 (16)°	Needle, colourless
V = 1216.6 (4) Å^3	0.20 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2489 independent reflections
Radiation source: fine-focus sealed tube	2153 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.743, Tmax = 0.845	k = −25→25
6933 measured reflections	l = −9→7

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 1.2254P] where P = (Fo^2 + 2Fc^2)/3
2489 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.47 e Å^−3
36 restraints	Δρmin = −0.59 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	Occ. (<1)
Zn1	0.22101 (4)	0.467979 (15)	0.28529 (4)	0.02152 (12)
O1	0.0652 (3)	0.39115 (10)	0.2286 (3)	0.0309 (5)
O2	−0.1723 (3)	0.40738 (11)	0.3381 (4)	0.0447 (6)
O3	−0.0487 (3)	0.05413 (10)	0.2672 (3)	0.0269 (5)
O4	−0.3295 (3)	0.07002 (9)	0.1823 (3)	0.0253 (4)
O5	0.2112 (3)	0.32597 (11)	0.5516 (3)	0.0390 (6)
O6	0.3313 (4)	0.24550 (15)	0.4486 (5)	0.0745 (10)
O7	0.2489 (3)	0.47581 (10)	0.0228 (3)	0.0341 (5)
H7A	0.1476	0.4708	−0.0428	0.041*
H7B	0.3275	0.4513	−0.0016	0.041*
O8	0.2161 (3)	0.47102 (9)	0.5550 (3)	0.0275 (5)
H8A	0.2056	0.5100	0.5900	0.033*
H8B	0.1522	0.4428	0.5903	0.033*
O9	0.4523 (3)	0.41850 (11)	0.3481 (3)	0.0345 (5)
H9A	0.5102	0.4196	0.4553	0.041*
H9B	0.5115	0.4139	0.2692	0.041*
N1	0.2041 (4)	0.27768 (13)	0.4582 (4)	0.0337 (6)
C1	−0.0659 (4)	0.37277 (13)	0.2858 (4)	0.0241 (6)
C2	−0.0942 (4)	0.29950 (13)	0.2839 (4)	0.0215 (6)
C3	0.0347 (4)	0.25498 (13)	0.3568 (4)	0.0226 (6)
C4	0.0096 (4)	0.18809 (13)	0.3430 (4)	0.0233 (6)
H4	0.0987	0.1597	0.3932	0.028*
C5	−0.1496 (4)	0.16416 (13)	0.2534 (4)	0.0197 (6)
C6	−0.2820 (4)	0.20755 (13)	0.1810 (4)	0.0254 (6)
H6	−0.3897	0.1917	0.1220	0.030*
C7	−0.2542 (4)	0.27463 (14)	0.1966 (4)	0.0280 (7)
H7	−0.3437	0.3031	0.1480	0.034*
C8	−0.1777 (4)	0.09209 (13)	0.2331 (4)	0.0216 (6)
O10	0.4654 (9)	0.1118 (4)	0.4247 (10)	0.0486 (17)	0.74 (2)
H10A	0.5747	0.1067	0.4381	0.058*	0.74 (2)
H10B	0.4192	0.1426	0.3569	0.058*	0.74 (2)
O10'	0.520 (3)	0.0882 (11)	0.484 (2)	0.042 (4)	0.26 (2)
H11A	0.4983	0.0969	0.3728	0.051*	0.26 (2)
H11B	0.6271	0.0841	0.5343	0.051*	0.26 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0253 (2)	0.01378 (17)	0.02494 (19)	−0.00018 (14)	0.00439 (13)	0.00049 (13)
O1	0.0386 (13)	0.0196 (10)	0.0370 (13)	−0.0119 (9)	0.0137 (10)	−0.0055 (9)
O2	0.0514 (16)	0.0201 (11)	0.0701 (18)	−0.0018 (11)	0.0300 (14)	−0.0123 (11)
O3	0.0283 (12)	0.0169 (9)	0.0338 (12)	0.0037 (9)	0.0030 (9)	−0.0011 (8)
O4	0.0257 (11)	0.0174 (9)	0.0314 (11)	−0.0055 (9)	0.0028 (9)	−0.0007 (8)
O5	0.0504 (15)	0.0296 (12)	0.0315 (12)	−0.0116 (11)	−0.0030 (10)	−0.0086 (10)
O6	0.0327 (15)	0.0563 (17)	0.123 (3)	0.0034 (14)	−0.0091 (16)	−0.0356 (18)
O7	0.0362 (13)	0.0399 (13)	0.0260 (11)	0.0002 (11)	0.0063 (9)	−0.0012 (9)
O8	0.0393 (13)	0.0169 (9)	0.0275 (11)	−0.0028 (9)	0.0101 (9)	−0.0021 (8)
O9	0.0295 (12)	0.0420 (13)	0.0308 (12)	0.0098 (10)	0.0038 (9)	−0.0015 (10)
N1	0.0288 (15)	0.0234 (13)	0.0449 (16)	−0.0034 (11)	−0.0009 (12)	−0.0042 (11)
C1	0.0324 (17)	0.0160 (14)	0.0232 (15)	−0.0034 (12)	0.0044 (12)	−0.0042 (11)
C2	0.0290 (16)	0.0144 (13)	0.0234 (14)	−0.0018 (12)	0.0104 (12)	−0.0036 (11)
C3	0.0230 (15)	0.0190 (13)	0.0254 (14)	−0.0053 (11)	0.0045 (11)	−0.0050 (11)
C4	0.0266 (16)	0.0168 (13)	0.0258 (15)	0.0012 (12)	0.0040 (12)	−0.0015 (11)
C5	0.0233 (15)	0.0135 (12)	0.0231 (14)	−0.0027 (11)	0.0067 (11)	−0.0009 (10)
C6	0.0227 (15)	0.0162 (13)	0.0347 (17)	−0.0023 (12)	0.0007 (12)	−0.0030 (12)
C7	0.0272 (17)	0.0163 (14)	0.0386 (18)	0.0022 (12)	0.0032 (13)	0.0018 (12)
C8	0.0271 (16)	0.0160 (13)	0.0218 (14)	0.0004 (12)	0.0053 (12)	−0.0010 (11)
O10	0.046 (3)	0.043 (3)	0.062 (3)	0.000 (2)	0.023 (2)	−0.002 (2)
O10'	0.039 (6)	0.051 (6)	0.042 (6)	−0.009 (4)	0.021 (4)	0.000 (4)

Geometric parameters (Å, º)

Zn1—O3^i	2.211 (2)	N1—C3	1.469 (4)
Zn1—O4^i	2.253 (2)	C1—C2	1.518 (4)
Zn1—O1	1.987 (2)	C2—C3	1.390 (4)
Zn1—O9	2.051 (2)	C2—C7	1.390 (4)
Zn1—O8	2.089 (2)	C3—C4	1.386 (4)
Zn1—O7	2.090 (2)	C4—C5	1.384 (4)
O1—C1	1.267 (4)	C4—H4	0.9300
O2—C1	1.232 (4)	C5—C6	1.392 (4)
O3—C8	1.262 (4)	C5—C8	1.497 (4)
O4—C8	1.259 (4)	C6—C7	1.394 (4)
O5—N1	1.218 (3)	C6—H6	0.9300
O6—N1	1.216 (4)	C7—H7	0.9300
O7—H7A	0.8526	O10—H10A	0.8515
O7—H7B	0.8504	O10—H10B	0.8486
O8—H8A	0.8536	O10—H11A	0.6061
O8—H8B	0.8503	O10'—H10A	0.7188
O9—H9A	0.8530	O10'—H11A	0.8535
O9—H9B	0.8492	O10'—H11B	0.8516
O1—Zn1—O9	97.77 (9)	O2—C1—C2	117.6 (3)
O1—Zn1—O8	95.59 (8)	O1—C1—C2	114.9 (3)
O9—Zn1—O8	89.37 (9)	C3—C2—C7	117.4 (3)
O1—Zn1—O7	92.22 (9)	C3—C2—C1	123.5 (3)
O9—Zn1—O7	89.44 (9)	C7—C2—C1	118.9 (3)
O1—Zn1—O3^i	105.49 (9)	C4—C3—C2	122.6 (3)
O8—Zn1—O3^i	90.80 (8)	C4—C3—N1	116.9 (3)
O7—Zn1—O3^i	87.24 (8)	C2—C3—N1	120.5 (2)
O9—Zn1—O4^i	97.85 (8)	C5—C4—C3	119.2 (3)
O8—Zn1—O4^i	87.20 (7)	C5—C4—H4	120.4
O7—Zn1—O4^i	85.32 (8)	C3—C4—H4	120.4
O3^i—Zn1—O4^i	58.80 (8)	C4—C5—C6	119.5 (3)
O8—Zn1—O7	172.19 (8)	C4—C5—C8	120.0 (3)
O9—Zn1—O3^i	156.60 (9)	C6—C5—C8	120.5 (3)
O1—Zn1—O4^i	164.16 (9)	C5—C6—C7	120.4 (3)
C1—O1—Zn1	132.19 (19)	C5—C6—H6	119.8
C8—O3—Zn1^ii	91.10 (17)	C7—C6—H6	119.8
C8—O4—Zn1^ii	89.26 (17)	C2—C7—C6	120.9 (3)
Zn1—O7—H7A	106.4	C2—C7—H7	119.6
Zn1—O7—H7B	113.9	C6—C7—H7	119.6
H7A—O7—H7B	115.6	O4—C8—O3	120.8 (3)
Zn1—O8—H8A	111.6	O4—C8—C5	119.7 (3)
Zn1—O8—H8B	116.1	O3—C8—C5	119.5 (3)
H8A—O8—H8B	115.6	O4—C8—Zn1^ii	61.36 (14)
Zn1—O9—H9A	118.4	C5—C8—Zn1^ii	177.2 (2)
Zn1—O9—H9B	119.1	H10A—O10—H10B	117.0
H9A—O9—H9B	115.9	H10A—O10—H11A	56.6
O6—N1—O5	123.0 (3)	H10B—O10—H11A	99.0
O6—N1—C3	117.5 (3)	H10A—O10'—H11A	54.0
O5—N1—C3	119.4 (3)	H10A—O10'—H11B	68.9
O2—C1—O1	127.5 (3)	H11A—O10'—H11B	116.4
O9—Zn1—O1—C1	126.0 (3)	O5—N1—C3—C2	35.9 (4)
O8—Zn1—O1—C1	35.9 (3)	C2—C3—C4—C5	−0.1 (4)
O7—Zn1—O1—C1	−144.3 (3)	N1—C3—C4—C5	178.0 (3)
O3^i—Zn1—O1—C1	−56.5 (3)	C3—C4—C5—C6	−0.8 (4)
O4^i—Zn1—O1—C1	−63.6 (4)	C3—C4—C5—C8	178.5 (3)
C8^i—Zn1—O1—C1	−59.3 (3)	C4—C5—C6—C7	0.7 (4)
Zn1—O1—C1—O2	30.8 (5)	C8—C5—C6—C7	−178.5 (3)
Zn1—O1—C1—C2	−150.8 (2)	C3—C2—C7—C6	−1.0 (4)
O2—C1—C2—C3	−130.5 (3)	C1—C2—C7—C6	175.6 (3)
O1—C1—C2—C3	51.0 (4)	C5—C6—C7—C2	0.2 (5)
O2—C1—C2—C7	53.1 (4)	Zn1^ii—O4—C8—O3	2.9 (3)
O1—C1—C2—C7	−125.4 (3)	Zn1^ii—O4—C8—C5	−177.1 (2)
C7—C2—C3—C4	1.0 (4)	Zn1^ii—O3—C8—O4	−3.0 (3)
C1—C2—C3—C4	−175.4 (3)	Zn1^ii—O3—C8—C5	177.0 (2)
C7—C2—C3—N1	−177.1 (3)	C4—C5—C8—O4	166.7 (3)
C1—C2—C3—N1	6.5 (4)	C6—C5—C8—O4	−14.1 (4)
O6—N1—C3—C4	35.4 (4)	C4—C5—C8—O3	−13.3 (4)
O5—N1—C3—C4	−142.3 (3)	C6—C5—C8—O3	165.9 (3)
O6—N1—C3—C2	−146.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8B···O3^iii	0.85	2.31	2.966 (3)	135
O7—H7A···O3^iv	0.85	1.95	2.783 (3)	164
O7—H7B···O10^iv	0.85	1.86	2.699 (5)	169
O9—H9B···O10′^iv	0.85	2.22	2.977 (14)	149
O7—H7B···O10′^iv	0.85	1.75	2.584 (11)	167
O10—H10B···O6	0.85	2.38	2.957 (9)	126
O8—H8B···O5	0.85	2.47	2.974 (3)	119
O9—H9B···O2^v	0.85	2.44	2.987 (3)	123
O10—H10A···O4^v	0.85	2.38	2.858 (5)	116
O10′—H11A···O4^v	0.85	2.28	2.855 (11)	125
O8—H8A···O2^vi	0.85	1.82	2.672 (3)	177
O9—H9A···O4^vii	0.85	1.93	2.778 (3)	170
O10′—H11B···O7^viii	0.85	2.50	2.94 (3)	113

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