Poly[hexa-aqua-bis(μ(3)-naphthalene-2,6-dicarboxyl-ato)(μ(2)-naphthalene-2,6-dicarboxyl-ato)diholmium(III)].

The crystal structure of the title compound, [Ho(2)(C(12)H(6)O(4))(3)(H(2)O)(6)](n), contains binuclear centrosymmetric {Ho(2)O(2)(CO(2))(4)(H(2)O)(6)} cores inter-connected via the naphthalene-2,6-dicarboxyl-ate (NDC(2-)) bridging ligands into a two-dimensional neutral plane net, ∞(2)[Ho(2)(NDC)(3)(H(2)O)(6)], exhibiting a typical (4,4)-topology. Inter-actions between adjacent layers are assured by a series of C-H⋯π contacts and a number of strong and highly directional O-H⋯O hydrogen bonds involving the coordinated water mol-ecules and neighbouring coordinated carboxyl-ate groups. One NDC(2-) bridging ligand has its centroid located at a crystallographic centre of inversion.

Related literature

For related structures see: Zheng, Sun et al. (2004 ▶); Zheng, Wang et al. (2004 ▶); Paz & Klinowski (2003 ▶); Min & Lee (2002 ▶); Wang et al. (2002 ▶). For related literature, see: Cunha-Silva, Mafra et al. (2007 ▶); Cunha-Silva, Shi et al. (2007 ▶); Shi et al. (2007 ▶); Mafra et al. (2006 ▶); Shi et al. (2006 ▶); Paz, Rocha, Klinowski et al. (2005 ▶); Almeida Paz, Shi, Mafra et al. (2005 ▶); Almeida Paz, Shi, Trindade et al. (2005 ▶); Shi et al. (2005 ▶); Paz & Klinowski (2004 ▶); Almeida Paz et al. (2002a ▶,b ▶,c ▶); Allen (2002 ▶); Allen & Motherwell (2002 ▶); Altomare et al. (1994 ▶); Deluzet et al. (2003 ▶).

Experimental

Crystal data

[Ho2(C12H6O4)3(H2O)6]

M = 540.23

Triclinic,

a = 7.8856 (3) Å

b = 9.6537 (5) Å

c = 12.5438 (6) Å

α = 75.191 (2)°

β = 74.224 (2)°

γ = 75.352 (2)°

V = 870.98 (7) Å3

Z = 2

Mo Kα radiation

μ = 4.60 mm−1

T = 180 (2) K

0.10 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.730, T max = 0.796

11608 measured reflections

3987 independent reflections

3135 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.079

S = 1.00

3987 reflections

271 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.51 e Å−3

Δρmin = −1.50 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: HKL DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Bruker, 2001 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064483/hj2008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064483/hj2008Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ho2(C12H6O4)3(H2O)6]	Z = 2
Mr = 540.23	F(000) = 524
Triclinic, P1	Dx = 2.060 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8856 (3) Å	Cell parameters from 14333 reflections
b = 9.6537 (5) Å	θ = 1.0–27.5°
c = 12.5438 (6) Å	µ = 4.60 mm−1
α = 75.191 (2)°	T = 180 K
β = 74.224 (2)°	Block, white
γ = 75.352 (2)°	0.10 × 0.05 × 0.05 mm
V = 870.98 (7) Å3

Nonius Kappa CCD diffractometer	3135 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Thin slice ω and φ scans	θmax = 27.6°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −10→9
Tmin = 0.730, Tmax = 0.796	k = −9→12
11608 measured reflections	l = −15→16
3987 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0301P)2] where P = (Fo2 + 2Fc2)/3
3987 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 1.51 e Å−3
9 restraints	Δρmin = −1.49 e Å−3

Experimental. See dedicated section in the main paper

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.

	x	y	z	Uiso*/Ueq
Ho1	1.23306 (3)	0.20677 (3)	−0.001555 (19)	0.01786 (10)
O1W	1.1573 (5)	0.4195 (4)	0.0764 (3)	0.0232 (9)
H1A	1.207 (6)	0.504 (3)	0.039 (4)	0.035*
H1B	1.039 (3)	0.450 (5)	0.118 (4)	0.035*
O2W	1.4902 (5)	0.3308 (4)	−0.0586 (3)	0.0259 (10)
H2A	1.506 (8)	0.340 (5)	0.011 (2)	0.039*
H2B	1.466 (8)	0.425 (2)	−0.105 (3)	0.039*
O3W	1.2069 (5)	−0.0416 (4)	0.0556 (3)	0.0301 (10)
H3A	1.104 (4)	−0.083 (5)	0.073 (5)	0.045*
H3B	1.311 (4)	−0.116 (4)	0.057 (5)	0.045*
O1	0.9506 (5)	0.2157 (4)	0.1072 (3)	0.0280 (10)
O2	0.6931 (5)	0.3656 (4)	0.0793 (3)	0.0241 (9)
O3	0.6021 (5)	−0.1174 (4)	0.8691 (3)	0.0269 (10)
O4	0.4373 (5)	0.1075 (4)	0.8570 (3)	0.0251 (9)
O5	1.1644 (5)	0.3945 (4)	−0.1584 (3)	0.0236 (9)
O6	1.0619 (5)	0.1934 (5)	−0.1337 (3)	0.0264 (10)
C1	0.7893 (8)	0.2736 (6)	0.1411 (4)	0.0199 (13)
C2	0.7080 (7)	0.2329 (7)	0.2662 (4)	0.0228 (14)
C3	0.5563 (10)	0.3242 (9)	0.3151 (5)	0.064 (3)
H3	0.4986	0.4070	0.2690	0.076*
C4	0.4889 (11)	0.2952 (10)	0.4304 (5)	0.087 (4)
H4	0.3852	0.3585	0.4629	0.105*
C5	0.5711 (8)	0.1739 (7)	0.5001 (4)	0.0257 (14)
C6	0.5125 (8)	0.1470 (7)	0.6203 (4)	0.0317 (16)
H6	0.4139	0.2127	0.6549	0.038*
C7	0.5957 (8)	0.0288 (6)	0.6862 (4)	0.0219 (13)
C8	0.5390 (7)	0.0055 (6)	0.8131 (4)	0.0183 (12)
C9	0.7352 (12)	−0.0676 (9)	0.6357 (5)	0.068 (3)
H9	0.7895	−0.1530	0.6811	0.081*
C10	0.7972 (13)	−0.0426 (9)	0.5211 (5)	0.084 (4)
H10	0.8956	−0.1102	0.4886	0.101*
C11	0.7190 (8)	0.0806 (6)	0.4501 (4)	0.0250 (14)
C12	0.7875 (9)	0.1138 (7)	0.3314 (4)	0.0318 (15)
H12	0.8908	0.0512	0.2975	0.038*
C13	1.0862 (7)	0.3182 (7)	−0.1918 (4)	0.0217 (13)
C14	1.0289 (8)	0.3725 (7)	−0.3018 (4)	0.0242 (14)
C15	0.9115 (8)	0.3065 (7)	−0.3296 (4)	0.0286 (15)
H15	0.8619	0.2299	−0.2759	0.034*
C16	0.8682 (9)	0.3509 (7)	−0.4318 (4)	0.0307 (15)
H16	0.7879	0.3056	−0.4492	0.037*
C17	0.9428 (8)	0.4657 (7)	−0.5143 (4)	0.0241 (13)
C18	1.0982 (8)	0.4868 (6)	−0.3770 (4)	0.0264 (14)
H18	1.1732	0.5338	−0.3562	0.032*

	U11	U22	U33	U12	U13	U23
Ho1	0.01942 (16)	0.02085 (16)	0.01278 (13)	−0.00448 (11)	−0.00501 (9)	−0.00036 (9)
O1W	0.024 (2)	0.023 (2)	0.0200 (19)	−0.0050 (18)	−0.0003 (16)	−0.0053 (16)
O2W	0.027 (2)	0.030 (3)	0.023 (2)	−0.012 (2)	−0.0058 (18)	−0.0037 (17)
O3W	0.022 (2)	0.024 (2)	0.042 (2)	−0.0073 (19)	−0.006 (2)	−0.0011 (19)
O1	0.026 (2)	0.034 (3)	0.0193 (19)	−0.008 (2)	0.0008 (17)	−0.0019 (17)
O2	0.024 (2)	0.029 (2)	0.0183 (18)	−0.0072 (19)	−0.0085 (17)	0.0027 (17)
O3	0.034 (2)	0.024 (2)	0.0217 (19)	−0.004 (2)	−0.0144 (18)	0.0037 (17)
O4	0.027 (2)	0.026 (2)	0.0197 (19)	−0.004 (2)	−0.0015 (17)	−0.0053 (17)
O5	0.032 (2)	0.023 (2)	0.0164 (18)	−0.0026 (19)	−0.0130 (17)	0.0011 (16)
O6	0.026 (2)	0.037 (3)	0.0165 (18)	−0.013 (2)	−0.0058 (16)	0.0015 (17)
C1	0.023 (3)	0.026 (3)	0.016 (3)	−0.015 (3)	−0.002 (2)	−0.004 (2)
C2	0.016 (3)	0.035 (4)	0.015 (3)	−0.007 (3)	−0.005 (2)	0.002 (2)
C3	0.044 (5)	0.080 (6)	0.022 (3)	0.029 (4)	0.001 (3)	0.019 (3)
C4	0.055 (5)	0.111 (8)	0.026 (4)	0.061 (5)	0.008 (3)	0.013 (4)
C5	0.021 (3)	0.034 (4)	0.015 (3)	−0.004 (3)	−0.002 (2)	0.004 (2)
C6	0.023 (3)	0.042 (4)	0.021 (3)	0.000 (3)	−0.002 (2)	0.000 (3)
C7	0.025 (3)	0.023 (3)	0.016 (3)	−0.004 (3)	−0.003 (2)	−0.003 (2)
C8	0.017 (3)	0.026 (4)	0.018 (3)	−0.011 (3)	−0.009 (2)	−0.003 (2)
C9	0.088 (6)	0.055 (5)	0.019 (3)	0.033 (5)	−0.001 (4)	0.006 (3)
C10	0.113 (8)	0.058 (6)	0.022 (3)	0.059 (5)	0.003 (4)	0.001 (3)
C11	0.035 (4)	0.023 (3)	0.015 (3)	−0.004 (3)	−0.007 (2)	−0.002 (2)
C12	0.039 (4)	0.027 (4)	0.024 (3)	0.003 (3)	−0.004 (3)	−0.008 (3)
C13	0.013 (3)	0.027 (4)	0.024 (3)	0.002 (3)	−0.009 (2)	−0.004 (3)
C14	0.026 (3)	0.027 (4)	0.018 (3)	0.000 (3)	−0.010 (2)	−0.001 (2)
C15	0.039 (4)	0.026 (4)	0.023 (3)	−0.003 (3)	−0.015 (3)	−0.003 (2)
C16	0.042 (4)	0.028 (4)	0.027 (3)	−0.007 (3)	−0.016 (3)	−0.004 (3)
C17	0.030 (4)	0.024 (4)	0.019 (3)	0.002 (3)	−0.010 (2)	−0.008 (2)
C18	0.032 (4)	0.024 (4)	0.026 (3)	0.000 (3)	−0.015 (3)	−0.006 (3)

Ho1—O1	2.267 (4)	C3—H3	0.9500
Ho1—O3i	2.252 (3)	C4—C5	1.399 (8)
Ho1—O4ii	2.279 (4)	C4—H4	0.9500
Ho1—O5	2.389 (3)	C5—C11	1.387 (8)
Ho1—O6	2.450 (4)	C5—C6	1.428 (7)
Ho1—O1W	2.370 (4)	C6—C7	1.359 (7)
Ho1—O2W	2.461 (4)	C6—H6	0.9500
Ho1—O3W	2.366 (4)	C7—C9	1.372 (9)
Ho1—C13	2.784 (5)	C7—C8	1.504 (7)
O1W—H1A	0.95 (4)	C9—C10	1.365 (8)
O1W—H1B	0.95 (4)	C9—H9	0.9500
O2W—H2A	0.95 (4)	C10—C11	1.405 (8)
O2W—H2B	0.95 (4)	C10—H10	0.9500
O3W—H3A	0.95 (4)	C11—C12	1.420 (7)
O3W—H3B	0.95 (4)	C12—H12	0.9500
O1—C1	1.256 (6)	C13—C14	1.494 (7)
O2—C1	1.262 (6)	C14—C18	1.378 (8)
O3—C8	1.270 (6)	C14—C15	1.404 (8)
O3—Ho1i	2.252 (3)	C15—C16	1.352 (7)
O4—C8	1.247 (7)	C15—H15	0.9500
O4—Ho1iii	2.279 (4)	C16—C17	1.434 (8)
O5—C13	1.275 (7)	C16—H16	0.9500
O6—C13	1.268 (7)	C17—C17iv	1.407 (12)
C1—C2	1.514 (7)	C17—C18iv	1.421 (7)
C2—C12	1.349 (7)	C18—C17iv	1.421 (7)
C2—C3	1.389 (9)	C18—H18	0.9500
C3—C4	1.379 (8)
O1—Ho1—O4ii	144.69 (15)	C12—C2—C1	120.6 (5)
O1—Ho1—O5	98.23 (13)	C3—C2—C1	119.5 (5)
O1—Ho1—O6	77.54 (13)	C4—C3—C2	120.2 (6)
O1—Ho1—O1W	72.71 (14)	C4—C3—H3	119.9
O1—Ho1—O2W	142.57 (14)	C2—C3—H3	119.9
O1—Ho1—O3W	76.58 (14)	C3—C4—C5	121.0 (7)
O3i—Ho1—O1	101.02 (13)	C3—C4—H4	119.5
O3i—Ho1—O4ii	96.82 (14)	C5—C4—H4	119.5
O3i—Ho1—O5	147.95 (14)	C11—C5—C4	118.4 (5)
O3i—Ho1—O6	155.80 (14)	C11—C5—C6	119.3 (5)
O3i—Ho1—O1W	83.38 (14)	C4—C5—C6	122.2 (6)
O3i—Ho1—O2W	72.20 (13)	C7—C6—C5	121.0 (6)
O3i—Ho1—O3W	76.60 (14)	C7—C6—H6	119.5
O4ii—Ho1—O5	81.43 (13)	C5—C6—H6	119.5
O4ii—Ho1—O6	73.82 (13)	C6—C7—C9	119.2 (5)
O4ii—Ho1—O1W	140.01 (13)	C6—C7—C8	120.6 (5)
O4ii—Ho1—O2W	72.11 (13)	C9—C7—C8	120.2 (5)
O4ii—Ho1—O3W	78.31 (14)	O4—C8—O3	123.9 (5)
O5—Ho1—O6	54.22 (13)	O4—C8—C7	118.8 (5)
O5—Ho1—O2W	76.91 (13)	O3—C8—C7	117.3 (5)
O6—Ho1—O2W	123.35 (12)	C10—C9—C7	121.1 (6)
O1W—Ho1—O5	78.18 (13)	C10—C9—H9	119.5
O1W—Ho1—O6	118.31 (14)	C7—C9—H9	119.5
O1W—Ho1—O2W	69.97 (13)	C9—C10—C11	121.6 (7)
O3W—Ho1—O5	133.18 (14)	C9—C10—H10	119.2
O3W—Ho1—O6	79.62 (14)	C11—C10—H10	119.2
O3W—Ho1—O2W	133.39 (14)	C5—C11—C10	117.6 (5)
O3W—Ho1—O1W	139.08 (13)	C5—C11—C12	119.6 (5)
O3i—Ho1—C13	170.11 (14)	C10—C11—C12	122.7 (6)
O1—Ho1—C13	88.87 (14)	C2—C12—C11	120.9 (6)
O4ii—Ho1—C13	74.78 (15)	C2—C12—H12	119.6
O3W—Ho1—C13	106.20 (17)	C11—C12—H12	119.6
O1W—Ho1—C13	99.61 (15)	O6—C13—O5	120.3 (5)
O5—Ho1—C13	27.19 (15)	O6—C13—C14	119.5 (5)
O6—Ho1—C13	27.09 (15)	O5—C13—C14	120.2 (5)
O2W—Ho1—C13	99.84 (15)	O6—C13—Ho1	61.6 (3)
Ho1—O1W—H1A	122 (3)	O5—C13—Ho1	58.9 (2)
Ho1—O1W—H1B	121 (3)	C14—C13—Ho1	173.3 (4)
H1A—O1W—H1B	108 (4)	C18—C14—C15	120.6 (5)
Ho1—O2W—H2A	103 (3)	C18—C14—C13	118.3 (5)
Ho1—O2W—H2B	113 (4)	C15—C14—C13	121.1 (5)
H2A—O2W—H2B	110 (4)	C16—C15—C14	120.8 (6)
Ho1—O3W—H3A	129 (3)	C16—C15—H15	119.6
Ho1—O3W—H3B	120 (3)	C14—C15—H15	119.6
H3A—O3W—H3B	110 (4)	C15—C16—C17	120.4 (6)
C1—O1—Ho1	155.6 (4)	C15—C16—H16	119.8
C8—O3—Ho1i	138.9 (4)	C17—C16—H16	119.8
C8—O4—Ho1iii	154.8 (3)	C17iv—C17—C18iv	119.4 (6)
C13—O5—Ho1	93.9 (3)	C17iv—C17—C16	118.9 (6)
C13—O6—Ho1	91.3 (3)	C18iv—C17—C16	121.7 (6)
O1—C1—O2	124.8 (5)	C14—C18—C17iv	119.8 (6)
O1—C1—C2	117.0 (5)	C14—C18—H18	120.1
O2—C1—C2	118.2 (5)	C17iv—C18—H18	120.1
C12—C2—C3	119.8 (5)
O3i—Ho1—O1—C1	131.2 (9)	C6—C7—C8—O3	169.4 (5)
O4ii—Ho1—O1—C1	−109.8 (9)	C9—C7—C8—O3	−12.2 (9)
O3W—Ho1—O1—C1	−155.6 (9)	C6—C7—C9—C10	3.3 (13)
O1W—Ho1—O1—C1	51.8 (9)	C8—C7—C9—C10	−175.1 (8)
O5—Ho1—O1—C1	−23.0 (9)	C7—C9—C10—C11	−1.3 (16)
O6—Ho1—O1—C1	−73.4 (9)	C4—C5—C11—C10	−178.5 (9)
O2W—Ho1—O1—C1	56.2 (9)	C6—C5—C11—C10	4.2 (10)
C13—Ho1—O1—C1	−48.6 (9)	C4—C5—C11—C12	2.8 (10)
O3i—Ho1—O5—C13	162.5 (3)	C6—C5—C11—C12	−174.5 (6)
O1—Ho1—O5—C13	−71.0 (3)	C9—C10—C11—C5	−2.5 (14)
O4ii—Ho1—O5—C13	73.3 (3)	C9—C10—C11—C12	176.2 (9)
O3W—Ho1—O5—C13	8.3 (4)	C3—C2—C12—C11	−0.5 (10)
O1W—Ho1—O5—C13	−141.3 (3)	C1—C2—C12—C11	175.6 (6)
O6—Ho1—O5—C13	−2.9 (3)	C5—C11—C12—C2	−1.6 (10)
O2W—Ho1—O5—C13	146.8 (3)	C10—C11—C12—C2	179.7 (7)
O3i—Ho1—O6—C13	−158.0 (3)	Ho1—O6—C13—O5	−5.1 (5)
O1—Ho1—O6—C13	112.8 (3)	Ho1—O6—C13—C14	172.4 (4)
O4ii—Ho1—O6—C13	−88.1 (3)	Ho1—O5—C13—O6	5.3 (5)
O3W—Ho1—O6—C13	−168.8 (3)	Ho1—O5—C13—C14	−172.3 (4)
O1W—Ho1—O6—C13	50.5 (3)	O1—Ho1—C13—O6	−64.2 (3)
O5—Ho1—O6—C13	2.9 (3)	O4ii—Ho1—C13—O6	84.1 (3)
O2W—Ho1—O6—C13	−33.1 (4)	O3W—Ho1—C13—O6	11.5 (3)
Ho1—O1—C1—O2	32.9 (12)	O1W—Ho1—C13—O6	−136.5 (3)
Ho1—O1—C1—C2	−144.8 (7)	O5—Ho1—C13—O6	−174.8 (5)
O1—C1—C2—C12	−16.9 (8)	O2W—Ho1—C13—O6	152.4 (3)
O2—C1—C2—C12	165.2 (5)	O1—Ho1—C13—O5	110.6 (3)
O1—C1—C2—C3	159.2 (6)	O4ii—Ho1—C13—O5	−101.0 (3)
O2—C1—C2—C3	−18.7 (9)	O3W—Ho1—C13—O5	−173.7 (3)
C12—C2—C3—C4	1.3 (13)	O1W—Ho1—C13—O5	38.4 (3)
C1—C2—C3—C4	−174.8 (8)	O6—Ho1—C13—O5	174.8 (5)
C2—C3—C4—C5	−0.1 (15)	O2W—Ho1—C13—O5	−32.8 (3)
C3—C4—C5—C11	−2.0 (14)	O6—C13—C14—C18	−162.7 (5)
C3—C4—C5—C6	175.3 (8)	O5—C13—C14—C18	14.9 (8)
C11—C5—C6—C7	−2.3 (10)	O6—C13—C14—C15	15.6 (8)
C4—C5—C6—C7	−179.5 (8)	O5—C13—C14—C15	−166.9 (5)
C5—C6—C7—C9	−1.6 (10)	C18—C14—C15—C16	2.0 (9)
C5—C6—C7—C8	176.9 (5)	C13—C14—C15—C16	−176.2 (5)
Ho1iii—O4—C8—O3	−23.0 (12)	C14—C15—C16—C17	0.4 (9)
Ho1iii—O4—C8—C7	158.7 (6)	C15—C16—C17—C17iv	−1.9 (11)
Ho1i—O3—C8—O4	−57.1 (8)	C15—C16—C17—C18iv	179.1 (6)
Ho1i—O3—C8—C7	121.2 (5)	C15—C14—C18—C17iv	−2.9 (9)
C6—C7—C8—O4	−12.2 (8)	C13—C14—C18—C17iv	175.4 (5)
C9—C7—C8—O4	166.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2v	0.95 (4)	1.82 (2)	2.725 (5)	157 (5)
O1W—H1B···O5v	0.95 (4)	1.95 (3)	2.818 (5)	150 (4)
O2W—H2A···O2vi	0.95 (4)	1.98 (4)	2.782 (5)	140 (5)
O2W—H2B···O2v	0.95 (4)	2.14 (4)	2.901 (6)	136 (4)
O3W—H3A···O6vii	0.95 (4)	1.78 (4)	2.704 (5)	165 (5)
O3W—H3B···O2Wviii	0.95 (4)	2.26 (4)	3.181 (6)	165 (4)
O3W—H3B···O4i	0.95 (4)	2.53 (5)	3.145 (6)	123 (4)

Ho1—O1	2.267 (4)
Ho1—O3i	2.252 (3)
Ho1—O4ii	2.279 (4)
Ho1—O5	2.389 (3)
Ho1—O6	2.450 (4)
Ho1—O1W	2.370 (4)
Ho1—O2W	2.461 (4)
Ho1—O3W	2.366 (4)

O1—Ho1—O4ii	144.69 (15)
O1—Ho1—O5	98.23 (13)
O1—Ho1—O6	77.54 (13)
O1—Ho1—O1W	72.71 (14)
O1—Ho1—O2W	142.57 (14)
O1—Ho1—O3W	76.58 (14)
O3i—Ho1—O1	101.02 (13)
O3i—Ho1—O4ii	96.82 (14)
O3i—Ho1—O5	147.95 (14)
O3i—Ho1—O6	155.80 (14)
O3i—Ho1—O1W	83.38 (14)
O3i—Ho1—O2W	72.20 (13)
O3i—Ho1—O3W	76.60 (14)
O4ii—Ho1—O5	81.43 (13)
O4ii—Ho1—O6	73.82 (13)
O4ii—Ho1—O1W	140.01 (13)
O4ii—Ho1—O2W	72.11 (13)
O4ii—Ho1—O3W	78.31 (14)
O5—Ho1—O6	54.22 (13)
O5—Ho1—O2W	76.91 (13)
O6—Ho1—O2W	123.35 (12)
O1W—Ho1—O5	78.18 (13)
O1W—Ho1—O6	118.31 (14)
O1W—Ho1—O2W	69.97 (13)
O3W—Ho1—O5	133.18 (14)
O3W—Ho1—O6	79.62 (14)
O3W—Ho1—O2W	133.39 (14)
O3W—Ho1—O1W	139.08 (13)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2iii	0.95 (4)	1.82 (2)	2.725 (5)	157 (5)
O1W—H1B⋯O5iii	0.95 (4)	1.95 (3)	2.818 (5)	150 (4)
O2W—H2A⋯O2iv	0.95 (4)	1.98 (4)	2.782 (5)	140 (5)
O2W—H2B⋯O2iii	0.95 (4)	2.14 (4)	2.901 (6)	136 (4)
O3W—H3A⋯O6v	0.95 (4)	1.78 (4)	2.704 (5)	165 (5)
O3W—H3B⋯O2Wvi	0.95 (4)	2.26 (4)	3.181 (6)	165 (4)
O3W—H3B⋯O4i	0.95 (4)	2.53 (5)	3.145 (6)	123 (4)

Symmetry codes: (i) ; (iii) ; (iv) ; (v) ; (vi) .