Poly[diaqua­tris­(μ₄-1,3-phenyl­enediacetato)­dineodymium(III)]

Abstract

In the title coordination polymer, [Nd₂(C₁₀H₈O₄)₃(H₂O)₂]_n, each of the two Nd^III ions is nine-coordinated by eight O atoms from six different 2,2′-(m-phenyl­ene)diacetate (pda) bivalent anions and by one O atom from a water mol­ecule, forming a distorted tricapped trigonal–prismatic coordination geometry. Eight Nd^III ions and 12 pda ligands form a large [Nd₈(pda)₁₂] ring, and four Nd^III ions and six pda ligands form a small [Nd₄(pda)₆] ring. These rings are further connected by the coordination inter­actions of pda ligands and Nd^III, generating a three-dimensional supra­molecular framework.

Related literature

For the isotypic Ce analogue, see: Gao et al. (2011 ▶). For the structures and properties of lanthanide coordination compounds, see: Xiao et al. (2008 ▶); Lv et al. (2010 ▶). For bond lengths and angles in other complexes with nine-coordinate Nd^III, see: Xiao et al. (2008 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

• [Nd₂(C₁₀H₈O₄)₃(H₂O)₂]

• M _r = 901.00

• Triclinic,

• a = 10.4846 (13) Å

• b = 11.9660 (16) Å

• c = 12.3514 (16) Å

• α = 105.619 (5)°

• β = 97.202 (5)°

• γ = 92.625 (6)°

• V = 1475.5 (3) ų

• Z = 2

• Mo Kα radiation

• μ = 3.55 mm⁻¹

• T = 296 K

• 0.24 × 0.22 × 0.20 mm

Data collection

• Bruker SMART CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.516, T _max = 0.580

• 7865 measured reflections

• 5315 independent reflections

• 4806 reflections with I > 2σ(I)

• R _int = 0.013

Refinement

• R[F ² > 2σ(F ²)] = 0.021

• wR(F ²) = 0.054

• S = 1.03

• 5315 reflections

• 415 parameters

• 3 restraints

• H-atom parameters constrained

• Δρ_max = 0.64 e Å⁻³

• Δρ_min = −0.76 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H1W⋯O12i	0.88	2.39	2.838 (3)	112
O14—H4W⋯O7ii	0.86	2.26	2.829 (3)	124
O14—H4W⋯O2iii	0.86	2.41	3.177 (4)	148
O14—H3W⋯O7	0.87	2.25	3.024 (3)	149
O14—H3W⋯O14ii	0.87	2.53	3.100 (5)	123

Symmetry codes: (i) ; (ii) ; (iii) .

supplementary crystallographic information

Comment

Lanthanide coordination polymers have shown versatile structural architectures, accompanied with desirable properties, like luminescence, magnetism, catalysis, gas adsorption and separation (Xiao et al., 2008; Lv et al., 2010). In order to extend our investigations in this field, we chose 1,3-phenylendiacetic acid (pda) as a functional ligand and synthesized the lanthanide coordination polymer [Nd₂(pda)₃(H₂O)₂]_n, the structure of which is reported here.

The title compound is isotypic with its Ce analogue (Gao et al., 2011). The asymmetric unit of the title complex (Fig. 1) contains two crystallographically unique Nd^III ions, three pda ligands, and two coordinated water molecules. Both Nd1 and Nd2 are nine-coordinated within a distorted tricapped trigonal-prismatic geometry. The nine coordination sites are occupied by one O atom from a water molecule and eight O atoms from six different pda anions. The Nd—O bond lengths in the title complex are in the range 2.377 (2)–2.749 (2) Å, which is comparable to those reported for other Nd complexes with oxygen environment around the central metal (Xiao et al., 2008; Wang et al., 2009). The pda ligands adopt two coordination modes, viz. µ₄-hexadentate and µ₄-pentadentate. Eight Nd^III ions and twelve pda ligands form a large [Nd₈(pda)₁₂] ring, whereas four Nd^III ions and six pda ligands form a small [Nd₄(pda)₆] ring (Fig. 2). These rings are further connected by the coordination interactions of pda ligands and Nd^III to generate a three-dimensional supramolecular framework (Fig. 2).

Experimental

To a solution of neodymium nitrate hexahydrate (0.088 g, 0.2 mmol) in water (5 ml) was added an aqueous solution (5 ml) of the ligand (0.058 g, 0.3 mmol) and a drop of triethylamine. The reactants were sealed in a 25-ml Teflon-lined stainless-steel Parr bomb. The bomb was heated at 433 K for 3 d. Upon cooling, the solution yielded single crystals of the title complex in ca 75% yield. Anal./calc. for C₃₀H₂₈Nd₂O₁₄: C, 39.99; H, 3.13; found: C, 40.43; H, 3.47.

Refinement

The H atoms of the water molecules were located in a difference Fourier map and were refined with distance constraints of O–H = 0.83 (5) Å. The C-bound H atoms were placed in geometrically idealized positions, with C–H = 0.93 and 0.97 Å for aryl and methylene H-atoms, respectively, and constrained to ride on their respective parent atoms, with U_iso(H) = 1.2 U_eq(C).

Figures

Fig. 1.

A drawing of the asymmetric unit in the structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

Unit cell packing of the title complex showing the three-dimensional framework formed by a large [Nd8(pda)12] ring and a small [Nd4(pda)6] ring.

Crystal data

[Nd2(C10H8O4)3(H2O)2]	Z = 2
Mr = 901.00	F(000) = 880
Triclinic, P1	Dx = 2.028 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4846 (13) Å	Cell parameters from 5315 reflections
b = 11.9660 (16) Å	θ = 1.7–25.3°
c = 12.3514 (16) Å	µ = 3.55 mm−1
α = 105.619 (5)°	T = 296 K
β = 97.202 (5)°	Block, colorless
γ = 92.625 (6)°	0.24 × 0.22 × 0.20 mm
V = 1475.5 (3) Å3

Data collection

Bruker SMART CCD diffractometer	5315 independent reflections
Radiation source: fine-focus sealed tube	4806 reflections with I > 2σ(I)
graphite	Rint = 0.013
Detector resolution: 0 pixels mm-1	θmax = 25.3°, θmin = 1.7°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 1997)	k = −12→14
Tmin = 0.516, Tmax = 0.580	l = −14→14
7865 measured reflections

Refinement

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0265P)2 + 1.487P] where P = (Fo2 + 2Fc2)/3
5315 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.64 e Å−3
3 restraints	Δρmin = −0.76 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
Nd1	0.029517 (16)	0.026539 (14)	0.183517 (13)	0.01602 (6)
Nd2	0.306439 (16)	0.036922 (15)	0.455279 (14)	0.01818 (6)
C1	0.0706 (3)	0.8190 (3)	0.2608 (3)	0.0194 (7)
C2	0.1023 (4)	0.7042 (3)	0.2819 (3)	0.0314 (9)
H2A	0.1766	0.6787	0.2453	0.038*
H2B	0.1270	0.7169	0.3629	0.038*
C3	−0.0041 (4)	0.6073 (3)	0.2411 (3)	0.0244 (8)
C4	−0.1173 (4)	0.6146 (3)	0.2887 (3)	0.0340 (9)
H4	−0.1275	0.6802	0.3468	0.041*
C5	−0.2149 (4)	0.5267 (3)	0.2516 (4)	0.0368 (9)
H5	−0.2897	0.5324	0.2853	0.044*
C6	−0.2021 (4)	0.4299 (3)	0.1643 (3)	0.0330 (9)
H6	−0.2691	0.3714	0.1383	0.040*
C7	−0.0910 (4)	0.4192 (3)	0.1154 (3)	0.0265 (8)
C8	0.0082 (4)	0.5078 (3)	0.1549 (3)	0.0252 (8)
H8	0.0843	0.5002	0.1230	0.030*
C9	−0.0755 (4)	0.3102 (3)	0.0240 (3)	0.0326 (9)
H9A	−0.1557	0.2884	−0.0279	0.039*
H9B	−0.0092	0.3272	−0.0188	0.039*
C10	−0.0404 (3)	0.2088 (3)	0.0679 (3)	0.0220 (7)
C11	−0.2153 (3)	0.7492 (3)	0.5878 (3)	0.0243 (7)
C12	−0.1546 (4)	0.6428 (3)	0.6052 (4)	0.0475 (12)
H12A	−0.0771	0.6353	0.5692	0.057*
H12B	−0.1280	0.6558	0.6860	0.057*
C13	−0.2359 (4)	0.5289 (3)	0.5614 (3)	0.0322 (9)
C14	−0.3482 (4)	0.5093 (3)	0.6035 (3)	0.0393 (10)
H14	−0.3755	0.5681	0.6597	0.047*
C15	−0.4198 (4)	0.4044 (3)	0.5636 (3)	0.0334 (9)
H15	−0.4955	0.3927	0.5924	0.040*
C16	−0.3801 (3)	0.3155 (3)	0.4805 (3)	0.0280 (8)
H16	−0.4301	0.2449	0.4526	0.034*
C17	−0.2661 (3)	0.3315 (3)	0.4388 (3)	0.0232 (7)
C18	−0.1952 (3)	0.4387 (3)	0.4794 (3)	0.0258 (8)
H18	−0.1190	0.4506	0.4512	0.031*
C19	−0.2165 (3)	0.2365 (3)	0.3508 (3)	0.0257 (8)
H19A	−0.1419	0.2690	0.3271	0.031*
H19B	−0.2825	0.2110	0.2848	0.031*
C20	−0.1792 (3)	0.1314 (3)	0.3893 (3)	0.0194 (7)
C21	0.4696 (3)	0.1360 (3)	−0.3232 (3)	0.0249 (8)
C22	0.5520 (3)	0.2052 (3)	−0.2133 (3)	0.0289 (8)
H22A	0.6237	0.1609	−0.1973	0.035*
H22B	0.5873	0.2772	−0.2238	0.035*
C23	0.4804 (3)	0.2339 (3)	−0.1121 (3)	0.0272 (8)
C24	0.3884 (5)	0.3138 (4)	−0.1054 (4)	0.0496 (12)
H24	0.3733	0.3507	−0.1626	0.060*
H1W	−0.2406	0.0218	0.0635	0.060*
H2W	−0.2406	−0.0802	0.1125	0.060*
H4W	0.1094	0.0990	0.6110	0.060*
H3W	0.0294	0.0896	0.5035	0.060*
C25	0.3193 (5)	0.3397 (4)	−0.0164 (4)	0.0574 (14)
H25	0.2561	0.3919	−0.0146	0.069*
C26	0.3432 (4)	0.2885 (4)	0.0707 (3)	0.0409 (10)
H26	0.2972	0.3075	0.1319	0.049*
C27	0.4349 (3)	0.2093 (3)	0.0676 (3)	0.0270 (8)
C28	0.5025 (3)	0.1825 (3)	−0.0248 (3)	0.0261 (8)
H28	0.5641	0.1286	−0.0278	0.031*
C29	0.4652 (4)	0.1561 (4)	0.1644 (3)	0.0348 (9)
H29A	0.5015	0.2183	0.2310	0.042*
H29B	0.5324	0.1040	0.1459	0.042*
C30	0.3579 (3)	0.0892 (3)	0.1978 (3)	0.0242 (7)
O1	0.1566 (2)	0.9053 (2)	0.2968 (2)	0.0274 (5)
O2	−0.0342 (2)	0.8302 (2)	0.2080 (2)	0.0284 (6)
O3	−0.0371 (3)	0.10987 (19)	−0.0009 (2)	0.0300 (6)
O4	−0.0146 (3)	0.2218 (2)	0.1716 (2)	0.0346 (6)
O5	−0.1595 (2)	0.84733 (19)	0.64899 (19)	0.0252 (5)
O6	−0.3093 (2)	0.7452 (2)	0.5148 (2)	0.0312 (6)
O7	−0.0998 (2)	0.0686 (2)	0.3388 (2)	0.0274 (5)
O8	−0.2271 (3)	0.1114 (2)	0.4695 (2)	0.0365 (6)
O9	0.5273 (2)	0.1006 (2)	−0.41110 (18)	0.0243 (5)
O10	0.3524 (3)	0.1179 (3)	−0.3299 (2)	0.0445 (7)
O11	0.3881 (2)	0.0619 (2)	0.2879 (2)	0.0300 (6)
O12	0.2492 (2)	0.0633 (2)	0.1359 (2)	0.0308 (6)
O13	−0.2057 (2)	−0.0221 (2)	0.1036 (2)	0.0355 (6)
O14	0.1067 (2)	0.1022 (2)	0.5416 (2)	0.0334 (6)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Nd1	0.02272 (10)	0.01120 (9)	0.01384 (9)	0.00192 (7)	0.00258 (7)	0.00292 (7)
Nd2	0.02183 (10)	0.01863 (10)	0.01494 (10)	0.00167 (7)	0.00283 (7)	0.00602 (7)
C1	0.0306 (18)	0.0139 (16)	0.0136 (15)	0.0028 (14)	0.0065 (14)	0.0017 (13)
C2	0.043 (2)	0.0156 (18)	0.037 (2)	0.0046 (15)	−0.0013 (17)	0.0105 (16)
C3	0.038 (2)	0.0119 (16)	0.0242 (18)	0.0036 (14)	0.0010 (15)	0.0084 (14)
C4	0.060 (3)	0.0161 (18)	0.029 (2)	0.0100 (17)	0.0159 (19)	0.0066 (15)
C5	0.044 (2)	0.030 (2)	0.046 (2)	0.0107 (18)	0.0183 (19)	0.0189 (19)
C6	0.041 (2)	0.0188 (19)	0.040 (2)	−0.0011 (16)	−0.0013 (18)	0.0131 (17)
C7	0.045 (2)	0.0113 (17)	0.0229 (18)	0.0071 (15)	−0.0007 (16)	0.0063 (14)
C8	0.037 (2)	0.0177 (17)	0.0242 (17)	0.0095 (15)	0.0074 (15)	0.0093 (14)
C9	0.057 (3)	0.0178 (18)	0.0218 (18)	0.0051 (17)	0.0011 (17)	0.0055 (15)
C10	0.0297 (18)	0.0129 (17)	0.0227 (18)	0.0016 (13)	0.0054 (14)	0.0032 (14)
C11	0.0265 (18)	0.0175 (18)	0.0254 (18)	−0.0028 (14)	0.0044 (15)	0.0005 (14)
C12	0.039 (2)	0.016 (2)	0.073 (3)	0.0030 (17)	−0.018 (2)	−0.0002 (19)
C13	0.034 (2)	0.0155 (18)	0.041 (2)	0.0040 (15)	−0.0102 (17)	0.0048 (16)
C14	0.048 (3)	0.029 (2)	0.036 (2)	0.0154 (19)	0.0028 (19)	−0.0006 (17)
C15	0.032 (2)	0.030 (2)	0.039 (2)	0.0066 (16)	0.0131 (17)	0.0079 (17)
C16	0.0314 (19)	0.0191 (18)	0.033 (2)	0.0000 (15)	0.0033 (16)	0.0077 (15)
C17	0.0307 (19)	0.0192 (17)	0.0210 (17)	0.0042 (14)	0.0007 (14)	0.0087 (14)
C18	0.0224 (17)	0.0199 (18)	0.035 (2)	0.0017 (14)	−0.0010 (15)	0.0103 (15)
C19	0.0315 (19)	0.0219 (18)	0.0252 (18)	0.0034 (15)	0.0049 (15)	0.0082 (15)
C20	0.0236 (17)	0.0151 (16)	0.0167 (16)	−0.0015 (13)	0.0018 (13)	0.0007 (13)
C21	0.0294 (19)	0.030 (2)	0.0158 (17)	0.0037 (15)	0.0031 (14)	0.0064 (15)
C22	0.0305 (19)	0.035 (2)	0.0192 (18)	0.0000 (16)	0.0027 (15)	0.0038 (16)
C23	0.033 (2)	0.030 (2)	0.0161 (17)	−0.0001 (15)	0.0021 (15)	0.0036 (15)
C24	0.069 (3)	0.055 (3)	0.039 (2)	0.029 (2)	0.026 (2)	0.026 (2)
C25	0.077 (3)	0.063 (3)	0.050 (3)	0.043 (3)	0.037 (3)	0.027 (2)
C26	0.056 (3)	0.040 (2)	0.030 (2)	0.010 (2)	0.0212 (19)	0.0081 (18)
C27	0.0319 (19)	0.0269 (19)	0.0227 (18)	−0.0050 (15)	0.0032 (15)	0.0094 (15)
C28	0.0246 (18)	0.0267 (19)	0.0253 (18)	−0.0011 (14)	0.0007 (15)	0.0060 (15)
C29	0.030 (2)	0.047 (2)	0.030 (2)	−0.0072 (17)	0.0004 (16)	0.0188 (18)
C30	0.0282 (19)	0.0257 (19)	0.0193 (17)	0.0035 (15)	0.0082 (15)	0.0046 (15)
O1	0.0361 (14)	0.0165 (12)	0.0282 (13)	−0.0012 (10)	−0.0038 (11)	0.0079 (10)
O2	0.0297 (13)	0.0205 (13)	0.0363 (14)	0.0001 (10)	−0.0006 (11)	0.0126 (11)
O3	0.0495 (16)	0.0138 (12)	0.0258 (13)	0.0040 (11)	0.0117 (12)	0.0010 (10)
O4	0.0642 (19)	0.0190 (13)	0.0199 (13)	0.0106 (12)	−0.0007 (12)	0.0060 (10)
O5	0.0326 (13)	0.0158 (12)	0.0228 (12)	0.0005 (10)	−0.0011 (10)	0.0001 (10)
O6	0.0322 (14)	0.0198 (13)	0.0356 (14)	−0.0023 (10)	−0.0064 (12)	0.0035 (11)
O7	0.0340 (14)	0.0250 (13)	0.0264 (13)	0.0103 (11)	0.0121 (11)	0.0080 (11)
O8	0.0593 (18)	0.0261 (14)	0.0353 (15)	0.0142 (13)	0.0287 (14)	0.0160 (12)
O9	0.0316 (13)	0.0260 (13)	0.0162 (11)	0.0074 (10)	0.0064 (10)	0.0050 (10)
O10	0.0263 (15)	0.073 (2)	0.0265 (14)	−0.0010 (14)	0.0021 (12)	0.0016 (14)
O11	0.0310 (14)	0.0403 (15)	0.0247 (13)	0.0063 (11)	0.0083 (11)	0.0165 (12)
O12	0.0262 (13)	0.0424 (16)	0.0236 (13)	−0.0044 (11)	0.0031 (11)	0.0100 (12)
O13	0.0298 (14)	0.0386 (16)	0.0362 (15)	−0.0043 (12)	−0.0032 (12)	0.0119 (12)
O14	0.0334 (14)	0.0384 (16)	0.0316 (14)	0.0090 (12)	0.0078 (11)	0.0129 (12)

Geometric parameters (Å, °)

Nd1—O3i	2.415 (2)	C15—C16	1.384 (5)
Nd1—O5ii	2.416 (2)	C15—H15	0.9300
Nd1—O4	2.441 (2)	C16—C17	1.384 (5)
Nd1—O7	2.442 (2)	C16—H16	0.9300
Nd1—O12	2.496 (2)	C17—C18	1.387 (5)
Nd1—O13	2.519 (2)	C17—C19	1.508 (5)
Nd1—O2iii	2.520 (2)	C18—H18	0.9300
Nd1—O1iii	2.576 (2)	C19—C20	1.510 (5)
Nd1—O3	2.749 (2)	C19—H19A	0.9700
Nd2—O8iv	2.377 (2)	C19—H19B	0.9700
Nd2—O11	2.418 (2)	C20—O8	1.239 (4)
Nd2—O9v	2.462 (2)	C20—O7	1.257 (4)
Nd2—O1iii	2.475 (2)	C21—O10	1.227 (4)
Nd2—O14	2.529 (3)	C21—O9	1.290 (4)
Nd2—O6ii	2.531 (2)	C21—C22	1.519 (5)
Nd2—O10vi	2.542 (3)	C21—Nd2vii	2.952 (3)
Nd2—O5ii	2.571 (2)	C22—C23	1.506 (5)
Nd2—O9vi	2.621 (2)	C22—H22A	0.9700
C1—O2	1.237 (4)	C22—H22B	0.9700
C1—O1	1.282 (4)	C23—C28	1.380 (5)
C1—C2	1.510 (4)	C23—C24	1.383 (5)
C2—C3	1.506 (5)	C24—C25	1.366 (6)
C2—H2A	0.9700	C24—H24	0.9300
C2—H2B	0.9700	C25—C26	1.377 (6)
C3—C4	1.385 (5)	C25—H25	0.9300
C3—C8	1.392 (5)	C26—C27	1.377 (5)
C4—C5	1.374 (6)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.391 (5)
C5—C6	1.378 (5)	C27—C29	1.507 (5)
C5—H5	0.9300	C28—H28	0.9300
C6—C7	1.373 (5)	C29—C30	1.512 (5)
C6—H6	0.9300	C29—H29A	0.9700
C7—C8	1.392 (5)	C29—H29B	0.9700
C7—C9	1.508 (5)	C30—O11	1.251 (4)
C8—H8	0.9300	C30—O12	1.266 (4)
C9—C10	1.499 (5)	O1—Nd2viii	2.475 (2)
C9—H9A	0.9700	O1—Nd1viii	2.576 (2)
C9—H9B	0.9700	O2—Nd1viii	2.520 (2)
C10—O4	1.241 (4)	O3—Nd1i	2.415 (2)
C10—O3	1.263 (4)	O5—Nd1ii	2.416 (2)
C11—O6	1.239 (4)	O5—Nd2ii	2.571 (2)
C11—O5	1.281 (4)	O6—Nd2ii	2.531 (2)
C11—C12	1.503 (5)	O8—Nd2iv	2.377 (2)
C12—C13	1.502 (5)	O9—Nd2v	2.462 (2)
C12—H12A	0.9700	O9—Nd2vii	2.621 (2)
C12—H12B	0.9700	O10—Nd2vii	2.542 (3)
C13—C14	1.381 (6)	O13—H1W	0.8758
C13—C18	1.391 (5)	O13—H2W	0.8110
C14—C15	1.367 (6)	O14—H4W	0.8644
C14—H14	0.9300	O14—H3W	0.8693
O3i—Nd1—O5ii	144.23 (9)	C7—C9—H9B	108.7
O3i—Nd1—O4	113.33 (8)	H9A—C9—H9B	107.6
O5ii—Nd1—O4	76.46 (8)	O4—C10—O3	119.9 (3)
O3i—Nd1—O7	141.44 (8)	O4—C10—C9	120.3 (3)
O5ii—Nd1—O7	71.16 (8)	O3—C10—C9	119.9 (3)
O4—Nd1—O7	84.45 (8)	O6—C11—O5	120.5 (3)
O3i—Nd1—O12	74.32 (8)	O6—C11—C12	123.3 (3)
O5ii—Nd1—O12	71.68 (8)	O5—C11—C12	116.0 (3)
O4—Nd1—O12	88.05 (9)	C13—C12—C11	117.0 (3)
O7—Nd1—O12	142.83 (8)	C13—C12—H12A	108.0
O3i—Nd1—O13	77.43 (9)	C11—C12—H12A	108.0
O5ii—Nd1—O13	138.26 (8)	C13—C12—H12B	108.0
O4—Nd1—O13	83.71 (9)	C11—C12—H12B	108.0
O7—Nd1—O13	70.65 (8)	H12A—C12—H12B	107.3
O12—Nd1—O13	144.46 (8)	C14—C13—C18	118.6 (3)
O3i—Nd1—O2iii	75.03 (8)	C14—C13—C12	121.8 (4)
O5ii—Nd1—O2iii	112.51 (8)	C18—C13—C12	119.6 (4)
O4—Nd1—O2iii	153.02 (9)	C15—C14—C13	120.8 (4)
O7—Nd1—O2iii	75.35 (8)	C15—C14—H14	119.6
O12—Nd1—O2iii	118.83 (8)	C13—C14—H14	119.6
O13—Nd1—O2iii	72.90 (8)	C14—C15—C16	120.4 (4)
O3i—Nd1—O1iii	94.43 (8)	C14—C15—H15	119.8
O5ii—Nd1—O1iii	69.57 (8)	C16—C15—H15	119.8
O4—Nd1—O1iii	146.02 (8)	C15—C16—C17	120.1 (3)
O7—Nd1—O1iii	85.44 (8)	C15—C16—H16	119.9
O12—Nd1—O1iii	80.76 (8)	C17—C16—H16	119.9
O13—Nd1—O1iii	122.85 (8)	C16—C17—C18	118.8 (3)
O2iii—Nd1—O1iii	50.71 (7)	C16—C17—C19	122.3 (3)
O3i—Nd1—O3	64.78 (9)	C18—C17—C19	118.9 (3)
O5ii—Nd1—O3	119.11 (7)	C17—C18—C13	121.2 (3)
O4—Nd1—O3	48.91 (7)	C17—C18—H18	119.4
O7—Nd1—O3	119.10 (8)	C13—C18—H18	119.4
O12—Nd1—O3	80.67 (8)	C17—C19—C20	115.1 (3)
O13—Nd1—O3	67.92 (8)	C17—C19—H19A	108.5
O2iii—Nd1—O3	128.34 (7)	C20—C19—H19A	108.5
O1iii—Nd1—O3	155.25 (8)	C17—C19—H19B	108.5
O8iv—Nd2—O11	140.87 (9)	C20—C19—H19B	108.5
O8iv—Nd2—O9v	80.82 (8)	H19A—C19—H19B	107.5
O11—Nd2—O9v	72.33 (8)	O8—C20—O7	123.0 (3)
O8iv—Nd2—O1iii	74.90 (9)	O8—C20—C19	118.7 (3)
O11—Nd2—O1iii	76.48 (8)	O7—C20—C19	118.3 (3)
O9v—Nd2—O1iii	88.60 (8)	O10—C21—O9	120.9 (3)
O8iv—Nd2—O14	71.83 (9)	O10—C21—C22	121.8 (3)
O11—Nd2—O14	131.77 (8)	O9—C21—C22	117.3 (3)
O9v—Nd2—O14	152.59 (8)	C23—C22—C21	114.1 (3)
O1iii—Nd2—O14	85.98 (8)	C23—C22—H22A	108.7
O8iv—Nd2—O6ii	140.58 (9)	C21—C22—H22A	108.7
O11—Nd2—O6ii	77.47 (9)	C23—C22—H22B	108.7
O9v—Nd2—O6ii	132.09 (8)	C21—C22—H22B	108.7
O1iii—Nd2—O6ii	119.41 (8)	H22A—C22—H22B	107.6
O14—Nd2—O6ii	72.89 (9)	C28—C23—C24	118.0 (3)
O8iv—Nd2—O10vi	73.99 (10)	C28—C23—C22	122.3 (3)
O11—Nd2—O10vi	139.31 (9)	C24—C23—C22	119.7 (3)
O9v—Nd2—O10vi	103.61 (8)	C25—C24—C23	121.3 (4)
O1iii—Nd2—O10vi	144.10 (9)	C25—C24—H24	119.4
O14—Nd2—O10vi	67.60 (8)	C23—C24—H24	119.4
O6ii—Nd2—O10vi	76.78 (9)	C24—C25—C26	120.1 (4)
O8iv—Nd2—O5ii	123.39 (9)	C24—C25—H25	120.0
O11—Nd2—O5ii	67.91 (8)	C26—C25—H25	120.0
O9v—Nd2—O5ii	137.67 (7)	C25—C26—C27	120.4 (4)
O1iii—Nd2—O5ii	68.79 (7)	C25—C26—H26	119.8
O14—Nd2—O5ii	63.87 (8)	C27—C26—H26	119.8
O6ii—Nd2—O5ii	50.79 (7)	C26—C27—C28	118.7 (3)
O10vi—Nd2—O5ii	115.78 (9)	C26—C27—C29	120.8 (3)
O8iv—Nd2—O9vi	99.49 (9)	C28—C27—C29	120.5 (3)
O11—Nd2—O9vi	94.98 (8)	C23—C28—C27	121.6 (3)
O9v—Nd2—O9vi	65.88 (9)	C23—C28—H28	119.2
O1iii—Nd2—O9vi	154.47 (8)	C27—C28—H28	119.2
O14—Nd2—O9vi	116.39 (8)	C27—C29—C30	119.0 (3)
O6ii—Nd2—O9vi	80.98 (7)	C27—C29—H29A	107.6
O10vi—Nd2—O9vi	50.17 (8)	C30—C29—H29A	107.6
O5ii—Nd2—O9vi	130.65 (7)	C27—C29—H29B	107.6
O2—C1—O1	120.1 (3)	C30—C29—H29B	107.6
O2—C1—C2	121.6 (3)	H29A—C29—H29B	107.0
O1—C1—C2	118.3 (3)	O11—C30—O12	125.0 (3)
C3—C2—C1	115.8 (3)	O11—C30—C29	114.2 (3)
C3—C2—H2A	108.3	O12—C30—C29	120.8 (3)
C1—C2—H2A	108.3	C1—O1—Nd2viii	149.4 (2)
C3—C2—H2B	108.3	C1—O1—Nd1viii	92.21 (19)
C1—C2—H2B	108.3	Nd2viii—O1—Nd1viii	109.46 (8)
H2A—C2—H2B	107.4	C1—O2—Nd1viii	96.0 (2)
C4—C3—C8	118.0 (3)	C10—O3—Nd1i	155.9 (2)
C4—C3—C2	120.9 (3)	C10—O3—Nd1	87.89 (19)
C8—C3—C2	121.1 (3)	Nd1i—O3—Nd1	115.22 (9)
C5—C4—C3	121.1 (4)	C10—O4—Nd1	103.32 (19)
C5—C4—H4	119.4	C11—O5—Nd1ii	153.8 (2)
C3—C4—H4	119.4	C11—O5—Nd2ii	92.8 (2)
C4—C5—C6	120.1 (4)	Nd1ii—O5—Nd2ii	111.55 (9)
C4—C5—H5	120.0	C11—O6—Nd2ii	95.8 (2)
C6—C5—H5	120.0	C20—O7—Nd1	147.9 (2)
C7—C6—C5	120.5 (4)	C20—O8—Nd2iv	144.9 (2)
C7—C6—H6	119.7	C21—O9—Nd2v	132.8 (2)
C5—C6—H6	119.7	C21—O9—Nd2vii	91.54 (19)
C6—C7—C8	119.0 (3)	Nd2v—O9—Nd2vii	114.12 (8)
C6—C7—C9	120.0 (3)	C21—O10—Nd2vii	96.9 (2)
C8—C7—C9	120.9 (3)	C30—O11—Nd2	143.5 (2)
C7—C8—C3	121.3 (3)	C30—O12—Nd1	131.1 (2)
C7—C8—H8	119.4	Nd1—O13—H1W	116.9
C3—C8—H8	119.4	Nd1—O13—H2W	117.1
C10—C9—C7	114.1 (3)	H1W—O13—H2W	125.7
C10—C9—H9A	108.7	Nd2—O14—H4W	113.5
C7—C9—H9A	108.7	Nd2—O14—H3W	123.7
C10—C9—H9B	108.7	H4W—O14—H3W	113.8
O2—C1—C2—C3	−3.6 (5)	O1iii—Nd1—O3—C10	−137.8 (2)
O1—C1—C2—C3	178.0 (3)	C1iii—Nd1—O3—C10	171.40 (19)
C1—C2—C3—C4	−65.1 (5)	O3i—Nd1—O3—Nd1i	0.0
C1—C2—C3—C8	115.0 (4)	O5ii—Nd1—O3—Nd1i	139.84 (10)
C8—C3—C4—C5	−0.4 (5)	O4—Nd1—O3—Nd1i	172.57 (17)
C2—C3—C4—C5	179.8 (3)	O7—Nd1—O3—Nd1i	−136.64 (10)
C3—C4—C5—C6	−1.1 (6)	O12—Nd1—O3—Nd1i	76.98 (11)
C4—C5—C6—C7	1.4 (6)	O13—Nd1—O3—Nd1i	−86.07 (11)
C5—C6—C7—C8	−0.2 (5)	O2iii—Nd1—O3—Nd1i	−42.57 (15)
C5—C6—C7—C9	176.9 (3)	O1iii—Nd1—O3—Nd1i	35.2 (2)
C6—C7—C8—C3	−1.3 (5)	C1iii—Nd1—O3—Nd1i	−15.6 (2)
C9—C7—C8—C3	−178.4 (3)	O3—C10—O4—Nd1	−0.8 (4)
C4—C3—C8—C7	1.6 (5)	C9—C10—O4—Nd1	179.2 (3)
C2—C3—C8—C7	−178.6 (3)	O3i—Nd1—O4—C10	7.8 (3)
C6—C7—C9—C10	−78.4 (4)	O5ii—Nd1—O4—C10	151.4 (2)
C8—C7—C9—C10	98.7 (4)	O7—Nd1—O4—C10	−136.7 (2)
C7—C9—C10—O4	−6.9 (5)	O12—Nd1—O4—C10	79.8 (2)
C7—C9—C10—O3	173.1 (3)	O13—Nd1—O4—C10	−65.6 (2)
O6—C11—C12—C13	−21.0 (6)	O2iii—Nd1—O4—C10	−95.4 (3)
O5—C11—C12—C13	162.9 (4)	O1iii—Nd1—O4—C10	150.0 (2)
C11—C12—C13—C14	−62.9 (6)	O3—Nd1—O4—C10	0.4 (2)
C11—C12—C13—C18	119.6 (4)	C1iii—Nd1—O4—C10	−162.0 (3)
C18—C13—C14—C15	−1.6 (6)	O6—C11—O5—Nd1ii	156.4 (4)
C12—C13—C14—C15	−179.1 (4)	C12—C11—O5—Nd1ii	−27.5 (7)
C13—C14—C15—C16	0.5 (6)	O6—C11—O5—Nd2ii	−2.8 (3)
C14—C15—C16—C17	1.3 (6)	C12—C11—O5—Nd2ii	173.3 (3)
C15—C16—C17—C18	−1.9 (5)	O5—C11—O6—Nd2ii	2.9 (4)
C15—C16—C17—C19	178.2 (3)	C12—C11—O6—Nd2ii	−173.0 (4)
C16—C17—C18—C13	0.8 (5)	O8—C20—O7—Nd1	175.1 (3)
C19—C17—C18—C13	−179.3 (3)	C19—C20—O7—Nd1	−5.4 (6)
C14—C13—C18—C17	0.9 (5)	O3i—Nd1—O7—C20	−105.2 (4)
C12—C13—C18—C17	178.5 (3)	O5ii—Nd1—O7—C20	93.5 (4)
C16—C17—C19—C20	−65.2 (4)	O4—Nd1—O7—C20	15.9 (4)
C18—C17—C19—C20	114.9 (4)	O12—Nd1—O7—C20	95.2 (4)
C17—C19—C20—O8	22.9 (5)	O13—Nd1—O7—C20	−69.4 (4)
C17—C19—C20—O7	−156.6 (3)	O2iii—Nd1—O7—C20	−146.1 (4)
O10—C21—C22—C23	8.0 (5)	O1iii—Nd1—O7—C20	163.4 (4)
O9—C21—C22—C23	−174.6 (3)	O3—Nd1—O7—C20	−20.0 (4)
C21—C22—C23—C28	109.6 (4)	C1iii—Nd1—O7—C20	−170.7 (4)
C21—C22—C23—C24	−70.0 (5)	O7—C20—O8—Nd2iv	−36.4 (6)
C28—C23—C24—C25	−1.3 (7)	C19—C20—O8—Nd2iv	144.1 (3)
C22—C23—C24—C25	178.3 (4)	O10—C21—O9—Nd2v	−118.1 (3)
C23—C24—C25—C26	2.0 (8)	C22—C21—O9—Nd2v	64.4 (4)
C24—C25—C26—C27	−1.3 (8)	O10—C21—O9—Nd2vii	7.5 (4)
C25—C26—C27—C28	0.1 (6)	C22—C21—O9—Nd2vii	−170.0 (3)
C25—C26—C27—C29	177.8 (4)	O9—C21—O10—Nd2vii	−7.8 (4)
C24—C23—C28—C27	0.1 (6)	C22—C21—O10—Nd2vii	169.6 (3)
C22—C23—C28—C27	−179.5 (3)	O12—C30—O11—Nd2	−36.9 (6)
C26—C27—C28—C23	0.5 (5)	C29—C30—O11—Nd2	144.4 (3)
C29—C27—C28—C23	−177.2 (3)	O8iv—Nd2—O11—C30	100.6 (4)
C26—C27—C29—C30	58.1 (5)	O9v—Nd2—O11—C30	149.5 (4)
C28—C27—C29—C30	−124.2 (4)	O1iii—Nd2—O11—C30	56.7 (4)
C27—C29—C30—O11	−170.9 (3)	O14—Nd2—O11—C30	−15.2 (4)
C27—C29—C30—O12	10.4 (5)	O6ii—Nd2—O11—C30	−68.1 (4)
O2—C1—O1—Nd2viii	126.3 (4)	O10vi—Nd2—O11—C30	−120.0 (4)
C2—C1—O1—Nd2viii	−55.3 (6)	O5ii—Nd2—O11—C30	−15.6 (4)
O2—C1—O1—Nd1viii	−9.9 (3)	O9vi—Nd2—O11—C30	−147.7 (4)
C2—C1—O1—Nd1viii	168.6 (3)	C11ii—Nd2—O11—C30	−43.0 (4)
O1—C1—O2—Nd1viii	10.1 (3)	C21vi—Nd2—O11—C30	−134.6 (4)
C2—C1—O2—Nd1viii	−168.2 (3)	O11—C30—O12—Nd1	27.9 (5)
O4—C10—O3—Nd1i	−163.6 (4)	C29—C30—O12—Nd1	−153.5 (3)
C9—C10—O3—Nd1i	16.4 (8)	O3i—Nd1—O12—C30	−142.6 (3)
O4—C10—O3—Nd1	0.7 (3)	O5ii—Nd1—O12—C30	26.1 (3)
C9—C10—O3—Nd1	−179.3 (3)	O4—Nd1—O12—C30	102.4 (3)
O3i—Nd1—O3—C10	−173.0 (3)	O7—Nd1—O12—C30	24.3 (4)
O5ii—Nd1—O3—C10	−33.2 (2)	O13—Nd1—O12—C30	178.8 (3)
O4—Nd1—O3—C10	−0.43 (19)	O2iii—Nd1—O12—C30	−80.1 (3)
O7—Nd1—O3—C10	50.4 (2)	O1iii—Nd1—O12—C30	−45.4 (3)
O12—Nd1—O3—C10	−96.0 (2)	O3—Nd1—O12—C30	151.1 (3)
O13—Nd1—O3—C10	100.9 (2)	C1iii—Nd1—O12—C30	−63.8 (3)
O2iii—Nd1—O3—C10	144.43 (19)

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

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O13—H1W···O12i	0.88	2.39	2.838 (3)	112
O14—H4W···O7iv	0.86	2.26	2.829 (3)	124
O14—H4W···O2ii	0.86	2.41	3.177 (4)	148
O14—H3W···O7	0.87	2.25	3.024 (3)	149
O14—H3W···O14iv	0.87	2.53	3.100 (5)	123

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