Tetrakis[μ-3-(3-hy­droxy­phen­yl)propenoato]bis­{aqua­(2,2′-bipyridine)­[3-(3-hy­droxy­phen­yl)propenoato]neodymium(III)} 2,2′-bipyridine disolvate dihydrate

Guo, J.-K.; Wen, Y.-H.

doi:10.1107/S1600536811050707

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1907-m1908

https://doi.org/10.1107/S1600536811050707

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Tetrakis[μ-3-(3-hydroxyphenyl)propenoato]bis{aqua(2,2′-bipyridine)[3-(3-hydroxyphenyl)propenoato]neodymium(III)} 2,2′-bipyridine disolvate dihydrate

Jing-Ke Guo ^a and Yi-Hang Wen ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Life Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: wyh@zjnu.edu.cn

(Received 27 October 2011; accepted 25 November 2011; online 30 November 2011)

The dinuclear title compound, [Nd₂(C₉H₇O₃)₆(C₁₀H₈N₂)₂]·2C₁₀H₈N₂·2H₂O, was synthesized under hydrothermal conditions. The centrosymmetric complex consists of two nine-coordinated Nd³⁺ cations, six 3-hydroxycinnamate anions and two chelating 2,2′-bipyridine molecules. The coordination geometry around the cations can be best described as distorted tricapped trigonal-prismatic. The carboxylate groups show different coordination and bridging modes. Two of them chelate to one Nd³⁺ cation, two bridge the two cations in a bis-monodentate fashion, and two chelate to one and bridge monodentately to the symmetry-related Nd³⁺ cation. The dinuclear molecule is surrounded by two 2,2′-bipyridine solvent and two water molecules. Extensive O—H⋯O and O—H⋯N hydrogen-bonding interactions between the components lead to the formation of a three-dimensional network.

Related literature

For related structures, see: Casas et al. (2008 ); Crowther et al. (2008 ); Gossauer et al. (2004 ); Zhang et al. (2010 ).

Experimental

Crystal data

[Nd₂(C₉H₇O₃)₆(C₁₀H₈N₂)₂]·2C₁₀H₈N₂·2H₂O
M_r = 1928.12
Monoclinic, P 2₁ /c
a = 10.7333 (2) Å
b = 28.9077 (5) Å
c = 14.3276 (3) Å
β = 108.274 (1)°
V = 4221.30 (14) Å³
Z = 2
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 296 K
0.24 × 0.11 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.84, T_max = 0.91
36893 measured reflections
9735 independent reflections
6140 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.083
S = 1.00
9735 reflections
574 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯N4ⁱ	0.87 (5)	2.04 (5)	2.897 (6)	168 (5)
O3—H3⋯O1Wⁱⁱ	0.96 (4)	1.68 (2)	2.618 (5)	163 (5)
O6—H6⋯O1ⁱⁱⁱ	0.93 (4)	1.79 (2)	2.703 (4)	168 (4)
O9—H9⋯N3ⁱ	0.96 (4)	1.90 (2)	2.849 (5)	175 (5)
O1W—H1WA⋯O8	0.87 (4)	1.96 (4)	2.825 (4)	175 (5)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050707/wm2552sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050707/wm2552Isup2.hkl

checkCIF report

Comment top

Compounds containing metal ions with 3-hydroxycinnamate ligands (L) have been reported previously (e.g. Casas et al., 2008; Crowther et al., 2008; Gossauer et al., 2004; Zhang et al., 2010). Herein we report a new Nd³⁺ compound, Nd₂L₆(bipy)₂^.2(bipy)^.2(H₂O), derived from 3-hydroxycinnamic acid and 2,2'-bipyridine (bipy) ligands.

A perspective view of the molecular struture of the centrosymmetric binuclear compound is presented in Fig. 1. It contains two nine-coordinated Nd³⁺ cations, which are linked by four carboxylate groups from four 3-hydroxycinnamate anions, and are also coordinated by two N atoms from two chelating 2,2'-bipyridine molecules. The molecule is surrounded by two solvent 2,2'-bipyridine and two solvent H₂O molecules. The carboxylate groups adopt different coordination and bridging modes. Two groups are chelating; two are monodentate and bridging; two are both chelating and bridging. Corresponding Nd—O distances are in the range 2.380 (3) to 2.635 (2) Å, with an Nd···Nd separation of 3.9928 (2) Å. Two N atoms of 2,2'-bipyridine [Nd—N distances are 2.617 (3) and 2.646 (3) Å] complete the nine-coordinate configuration of Nd³⁺. Its coordination geometry can be best described as a distorted tricapped trigonal prism.

The dihedral angles between two pyridyl rings from the coordinating and the solvent 2,2'-bipyridine molecules are quite different (10.65 (13) and 48.61 (16) °, respectively). There are extensive intermolecular O—H···N and O—H···O hydrogen-bonding interactions involving the 3-hydroxycinnamate anions, the solvent 2,2'-bipyridine and water molecules (Table 1), resulting in the formation of three-dimensional network structure (Fig. 2).

Related literature top

For related structures, see: Casas et al. (2008); Crowther et al. (2008); Gossauer et al. (2004); Zhang et al. (2010).

Experimental top

A mixture of Nd(NO₃)₃ (0.3302 g, 0.5 mmol) ,3-hydroxycinnamic acid (0.2462 g, 1.5 mmol) and 2,2'-bipyridine (0.2343 g, 1.5 mmol) was dissolved in 16 mL EtOH/H₂O (v/v, 1:15) and then sealed in a 25 ml stainless steel reactor with a telflon liner and heated at 433 K for 72 h, and subsequently cooled to room temperature over 3 days. Then, the reactor was cooled to room temperature at a speed of 5 Kh^-1. Colourless single crystals of the title compound were obtained by slow evaporation of the filtrate over a few days.

Structure description top

For related structures, see: Casas et al. (2008); Crowther et al. (2008); Gossauer et al. (2004); Zhang et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x + 2,-y,-z + 1]
	Fig. 2. View of the supramolecular network defined by hydrogen bonding interactions.

Tetrakis[µ-3-(3-hydroxyphenyl)propenoato]bis{aqua(2,2'-bipyridine)[3-(3- hydroxyphenyl)propenoato]neodymium(III)} 2,2'-bipyridine disolvate dihydrate top

Crystal data top

[Nd₂(C₉H₇O₃)₆(C₁₀H₈N₂)₂]·2C₁₀H₈N₂·2H₂O	F(000) = 1956
M_r = 1928.12	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3747 reflections
a = 10.7333 (2) Å	θ = 1.4–27.6°
b = 28.9077 (5) Å	µ = 1.30 mm⁻¹
c = 14.3276 (3) Å	T = 296 K
β = 108.274 (1)°	Block, colorless
V = 4221.30 (14) Å³	0.24 × 0.11 × 0.07 mm
Z = 2

Data collection top

Bruker APEXII area-detector diffractometer	9735 independent reflections
Radiation source: fine-focus sealed tube	6140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scans	θ_max = 27.6°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.84, T_max = 0.91	k = −31→37
36893 measured reflections	l = −12→18

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0225P)²] where P = (F_o² + 2F_c²)/3
9735 reflections	(Δ/σ)_max = 0.001
574 parameters	Δρ_max = 1.13 e Å⁻³
7 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Nd₂(C₉H₇O₃)₆(C₁₀H₈N₂)₂]·2C₁₀H₈N₂·2H₂O	V = 4221.30 (14) Å³
M_r = 1928.12	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7333 (2) Å	µ = 1.30 mm⁻¹
b = 28.9077 (5) Å	T = 296 K
c = 14.3276 (3) Å	0.24 × 0.11 × 0.07 mm
β = 108.274 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	9735 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6140 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.91	R_int = 0.078
36893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	7 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 1.13 e Å⁻³
9735 reflections	Δρ_min = −0.65 e Å⁻³
574 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Nd1	0.831518 (18)	0.015918 (7)	0.397023 (15)	0.02703 (7)
N1	0.6264 (3)	0.07010 (11)	0.3784 (2)	0.0384 (8)
N2	0.7276 (3)	0.06032 (11)	0.2317 (2)	0.0341 (8)
N3	1.0336 (4)	0.19224 (15)	0.6936 (3)	0.0627 (11)
N4	0.9520 (4)	0.30801 (15)	0.6957 (3)	0.0653 (12)
O1	0.7649 (2)	−0.04827 (9)	0.27042 (19)	0.0390 (7)
O1W	0.8072 (4)	0.18385 (12)	0.3349 (3)	0.0835 (12)
H1WA	0.845 (5)	0.1579 (12)	0.358 (4)	0.125*
H1WB	0.841 (5)	0.1884 (19)	0.288 (3)	0.125*
O2	0.6300 (3)	−0.03295 (10)	0.3539 (2)	0.0475 (8)
O3	0.3636 (3)	−0.25709 (12)	0.1387 (3)	0.0891 (13)
H3	0.290 (3)	−0.2761 (15)	0.138 (4)	0.107*
O4	0.8074 (2)	0.01453 (9)	0.55653 (19)	0.0407 (7)
O5	0.9911 (2)	−0.00966 (9)	0.67152 (18)	0.0362 (7)
O6	0.8780 (3)	−0.06697 (11)	1.1306 (2)	0.0553 (9)
H6	0.837 (4)	−0.0650 (14)	1.179 (2)	0.066*
O7	1.0478 (2)	0.05061 (8)	0.52033 (18)	0.0313 (6)
O8	0.9189 (2)	0.09865 (8)	0.4161 (2)	0.0389 (7)
O9	1.2759 (3)	0.30599 (12)	0.3496 (3)	0.0791 (11)
H9	1.196 (3)	0.3049 (17)	0.296 (3)	0.095*
C1	1.2941 (5)	0.27173 (16)	0.4170 (4)	0.0547 (13)
C2	1.2018 (4)	0.23699 (13)	0.4114 (3)	0.0436 (11)
H2A	1.1224	0.2376	0.3608	0.052*
C3	1.2264 (4)	0.20148 (13)	0.4801 (3)	0.0376 (10)
C4	1.3427 (4)	0.20126 (15)	0.5574 (3)	0.0461 (11)
H4A	1.3602	0.1778	0.6041	0.055*
C5	1.4324 (5)	0.23641 (17)	0.5640 (4)	0.0648 (15)
H5A	1.5093	0.2370	0.6169	0.078*
C6	1.4101 (5)	0.27068 (17)	0.4937 (4)	0.0640 (15)
H6A	1.4737	0.2932	0.4980	0.077*
C7	1.1278 (4)	0.16482 (14)	0.4648 (3)	0.0395 (10)
H7A	1.0478	0.1713	0.4177	0.047*
C8	1.1346 (4)	0.12442 (13)	0.5070 (3)	0.0375 (10)
H8A	1.2111	0.1168	0.5568	0.045*
C9	1.0275 (4)	0.09037 (13)	0.4796 (3)	0.0322 (9)
C10	0.3132 (5)	−0.21370 (16)	0.1416 (4)	0.0548 (13)
C11	0.4023 (4)	−0.17935 (15)	0.1817 (3)	0.0472 (12)
H11A	0.4917	−0.1857	0.2021	0.057*
C12	0.3574 (4)	−0.13491 (15)	0.1914 (3)	0.0407 (10)
C13	0.2243 (4)	−0.12596 (16)	0.1601 (3)	0.0529 (12)
H13A	0.1942	−0.0965	0.1678	0.063*
C14	0.1352 (5)	−0.16042 (18)	0.1175 (4)	0.0609 (14)
H14A	0.0459	−0.1539	0.0947	0.073*
C15	0.1795 (4)	−0.20420 (18)	0.1091 (3)	0.0616 (14)
H15A	0.1199	−0.2276	0.0815	0.074*
C16	0.4520 (4)	−0.09847 (14)	0.2386 (3)	0.0440 (11)
H16A	0.4213	−0.0750	0.2701	0.053*
C17	0.5764 (4)	−0.09551 (13)	0.2408 (3)	0.0393 (10)
H17A	0.6112	−0.1183	0.2105	0.047*
C18	0.6605 (4)	−0.05660 (13)	0.2908 (3)	0.0337 (9)
C19	0.7990 (4)	−0.05164 (14)	1.0418 (3)	0.0391 (10)
C20	0.8559 (4)	−0.04089 (14)	0.9707 (3)	0.0385 (10)
H20A	0.9461	−0.0443	0.9849	0.046*
C21	0.7824 (4)	−0.02509 (13)	0.8783 (3)	0.0338 (10)
C22	0.6472 (4)	−0.01986 (14)	0.8582 (3)	0.0421 (11)
H22A	0.5954	−0.0096	0.7967	0.050*
C23	0.5911 (4)	−0.03002 (15)	0.9300 (3)	0.0500 (12)
H23A	0.5014	−0.0256	0.9171	0.060*
C24	0.6654 (4)	−0.04660 (15)	1.0208 (3)	0.0455 (11)
H24A	0.6253	−0.0543	1.0676	0.055*
C25	0.8479 (4)	−0.01611 (13)	0.8042 (3)	0.0358 (9)
H25A	0.9390	−0.0175	0.8263	0.043*
C26	0.7942 (4)	−0.00642 (13)	0.7111 (3)	0.0371 (10)
H26A	0.7035	−0.0034	0.6871	0.045*
C27	0.8703 (4)	0.00003 (13)	0.6416 (3)	0.0334 (10)
C28	0.7741 (4)	0.05261 (14)	0.1567 (3)	0.0401 (10)
H28A	0.8311	0.0279	0.1615	0.048*
C29	0.7424 (4)	0.07910 (16)	0.0735 (3)	0.0563 (13)
H29A	0.7740	0.0716	0.0219	0.068*
C30	0.6637 (5)	0.11667 (18)	0.0676 (4)	0.0704 (16)
H30A	0.6431	0.1361	0.0132	0.084*
C31	0.6153 (5)	0.12521 (16)	0.1442 (4)	0.0640 (15)
H31A	0.5615	0.1507	0.1416	0.077*
C32	0.6458 (4)	0.09633 (14)	0.2249 (3)	0.0393 (10)
C33	0.5880 (4)	0.10092 (15)	0.3063 (3)	0.0433 (11)
C34	0.4948 (5)	0.13386 (18)	0.3052 (4)	0.0732 (16)
H34A	0.4721	0.1562	0.2560	0.088*
C35	0.4354 (5)	0.1334 (2)	0.3779 (4)	0.088 (2)
H35A	0.3727	0.1555	0.3783	0.106*
C36	0.4694 (5)	0.10040 (19)	0.4486 (4)	0.0692 (15)
H36A	0.4280	0.0986	0.4966	0.083*
C37	0.5658 (4)	0.07005 (16)	0.4474 (3)	0.0507 (12)
H37A	0.5910	0.0480	0.4971	0.061*
C38	1.0081 (6)	0.3500 (2)	0.7036 (5)	0.0863 (19)
H38A	0.9706	0.3743	0.7280	0.104*
C39	1.1184 (7)	0.3586 (2)	0.6771 (5)	0.095 (2)
H39A	1.1532	0.3883	0.6820	0.114*
C40	1.1758 (6)	0.3233 (3)	0.6436 (5)	0.097 (2)
H40A	1.2495	0.3285	0.6241	0.117*
C41	1.1234 (5)	0.2798 (2)	0.6391 (4)	0.0735 (16)
H41A	1.1633	0.2548	0.6191	0.088*
C42	1.0109 (5)	0.27347 (16)	0.6644 (3)	0.0523 (12)
C43	0.9506 (5)	0.22716 (17)	0.6563 (3)	0.0536 (13)
C44	0.8195 (5)	0.22010 (18)	0.6091 (4)	0.0713 (16)
H44A	0.7640	0.2452	0.5868	0.086*
C45	0.7705 (6)	0.1761 (2)	0.5949 (5)	0.0888 (19)
H45A	0.6821	0.1710	0.5618	0.107*
C46	0.8526 (7)	0.1401 (2)	0.6297 (5)	0.0864 (19)
H46A	0.8219	0.1099	0.6197	0.104*
C47	0.9818 (7)	0.14907 (19)	0.6802 (4)	0.0776 (17)
H47A	1.0366	0.1242	0.7065	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.02956 (11)	0.02835 (12)	0.02408 (12)	−0.00029 (10)	0.00971 (9)	0.00308 (11)
N1	0.0387 (19)	0.041 (2)	0.037 (2)	0.0041 (15)	0.0140 (18)	0.0011 (18)
N2	0.0314 (17)	0.041 (2)	0.028 (2)	0.0013 (14)	0.0063 (16)	0.0028 (16)
N3	0.078 (3)	0.057 (3)	0.052 (3)	0.014 (2)	0.020 (2)	−0.004 (2)
N4	0.075 (3)	0.051 (3)	0.069 (3)	0.016 (2)	0.020 (3)	−0.002 (2)
O1	0.0421 (16)	0.0423 (17)	0.0365 (18)	−0.0090 (13)	0.0178 (14)	−0.0054 (14)
O1W	0.079 (3)	0.048 (2)	0.130 (4)	0.0187 (18)	0.042 (3)	0.019 (2)
O2	0.0482 (17)	0.0483 (19)	0.054 (2)	−0.0147 (13)	0.0275 (16)	−0.0184 (16)
O3	0.070 (2)	0.057 (3)	0.142 (4)	−0.0180 (18)	0.036 (3)	−0.022 (3)
O4	0.0400 (16)	0.0577 (19)	0.0272 (16)	0.0100 (14)	0.0144 (14)	0.0092 (15)
O5	0.0337 (15)	0.0500 (18)	0.0273 (16)	0.0039 (13)	0.0131 (13)	0.0050 (14)
O6	0.0544 (19)	0.086 (2)	0.0281 (18)	0.0196 (17)	0.0169 (16)	0.0153 (18)
O7	0.0415 (12)	0.0225 (15)	0.0278 (15)	−0.0023 (11)	0.0078 (10)	0.0015 (12)
O8	0.0383 (16)	0.0288 (16)	0.0443 (19)	0.0016 (12)	0.0052 (15)	0.0083 (14)
O9	0.081 (3)	0.062 (2)	0.081 (3)	−0.034 (2)	0.007 (2)	0.029 (2)
C1	0.059 (3)	0.048 (3)	0.058 (4)	−0.017 (2)	0.019 (3)	0.003 (3)
C2	0.046 (3)	0.037 (3)	0.045 (3)	−0.011 (2)	0.011 (2)	−0.001 (2)
C3	0.040 (2)	0.032 (2)	0.041 (3)	−0.0062 (18)	0.014 (2)	−0.003 (2)
C4	0.043 (3)	0.044 (3)	0.048 (3)	−0.007 (2)	0.010 (2)	0.001 (2)
C5	0.049 (3)	0.072 (4)	0.066 (4)	−0.013 (3)	0.008 (3)	0.000 (3)
C6	0.061 (3)	0.062 (4)	0.066 (4)	−0.032 (3)	0.014 (3)	−0.004 (3)
C7	0.035 (2)	0.042 (3)	0.038 (3)	−0.0013 (19)	0.007 (2)	0.003 (2)
C8	0.036 (2)	0.033 (3)	0.039 (3)	−0.0012 (18)	0.006 (2)	0.006 (2)
C9	0.039 (2)	0.027 (2)	0.033 (3)	0.0019 (18)	0.014 (2)	0.000 (2)
C10	0.058 (3)	0.041 (3)	0.069 (4)	−0.007 (2)	0.025 (3)	−0.008 (3)
C11	0.044 (3)	0.044 (3)	0.051 (3)	−0.012 (2)	0.011 (2)	−0.007 (2)
C12	0.044 (2)	0.045 (3)	0.033 (3)	−0.012 (2)	0.013 (2)	−0.002 (2)
C13	0.053 (3)	0.051 (3)	0.054 (3)	−0.006 (2)	0.016 (3)	−0.002 (3)
C14	0.051 (3)	0.066 (4)	0.061 (4)	−0.011 (3)	0.009 (3)	−0.003 (3)
C15	0.056 (3)	0.066 (4)	0.058 (4)	−0.026 (3)	0.012 (3)	−0.013 (3)
C16	0.047 (3)	0.043 (3)	0.041 (3)	−0.007 (2)	0.012 (2)	−0.005 (2)
C17	0.050 (3)	0.033 (3)	0.036 (3)	−0.0044 (19)	0.014 (2)	−0.003 (2)
C18	0.041 (2)	0.030 (2)	0.027 (2)	−0.0016 (18)	0.008 (2)	0.001 (2)
C19	0.041 (2)	0.048 (3)	0.029 (3)	0.002 (2)	0.012 (2)	−0.001 (2)
C20	0.034 (2)	0.048 (3)	0.036 (3)	0.0041 (19)	0.014 (2)	−0.002 (2)
C21	0.038 (2)	0.038 (3)	0.027 (2)	0.0010 (17)	0.013 (2)	−0.0041 (19)
C22	0.037 (2)	0.062 (3)	0.029 (2)	0.000 (2)	0.013 (2)	0.002 (2)
C23	0.035 (2)	0.076 (4)	0.041 (3)	−0.002 (2)	0.016 (2)	0.000 (3)
C24	0.044 (3)	0.068 (3)	0.034 (3)	−0.007 (2)	0.026 (2)	0.005 (2)
C25	0.033 (2)	0.046 (3)	0.032 (2)	0.0017 (19)	0.016 (2)	0.002 (2)
C26	0.034 (2)	0.050 (3)	0.030 (2)	0.0030 (18)	0.015 (2)	0.006 (2)
C27	0.042 (2)	0.031 (2)	0.028 (2)	0.0016 (17)	0.012 (2)	−0.0014 (19)
C28	0.038 (2)	0.048 (3)	0.035 (3)	0.0058 (19)	0.012 (2)	0.005 (2)
C29	0.062 (3)	0.069 (4)	0.042 (3)	0.002 (3)	0.022 (3)	0.012 (3)
C30	0.094 (4)	0.073 (4)	0.045 (3)	0.028 (3)	0.023 (3)	0.033 (3)
C31	0.082 (4)	0.053 (3)	0.057 (4)	0.030 (3)	0.022 (3)	0.024 (3)
C32	0.038 (2)	0.035 (3)	0.040 (3)	0.0043 (19)	0.007 (2)	0.006 (2)
C33	0.041 (2)	0.041 (3)	0.044 (3)	0.009 (2)	0.007 (2)	−0.001 (2)
C34	0.083 (4)	0.084 (4)	0.053 (4)	0.048 (3)	0.022 (3)	0.020 (3)
C35	0.087 (4)	0.110 (5)	0.073 (4)	0.061 (4)	0.033 (4)	0.008 (4)
C36	0.057 (3)	0.097 (4)	0.058 (4)	0.026 (3)	0.025 (3)	−0.001 (3)
C37	0.043 (3)	0.067 (3)	0.042 (3)	0.011 (2)	0.013 (2)	0.006 (3)
C38	0.108 (5)	0.049 (4)	0.097 (5)	0.016 (3)	0.025 (4)	0.007 (4)
C39	0.120 (6)	0.066 (5)	0.092 (5)	−0.013 (4)	0.023 (5)	0.011 (4)
C40	0.101 (5)	0.106 (6)	0.093 (5)	−0.040 (4)	0.043 (4)	−0.018 (4)
C41	0.074 (4)	0.078 (4)	0.074 (4)	−0.003 (3)	0.030 (3)	−0.026 (3)
C42	0.064 (3)	0.049 (3)	0.041 (3)	0.004 (2)	0.012 (3)	0.001 (2)
C43	0.068 (3)	0.050 (3)	0.045 (3)	0.000 (3)	0.020 (3)	−0.003 (3)
C44	0.065 (4)	0.062 (4)	0.076 (4)	−0.003 (3)	0.008 (3)	0.002 (3)
C45	0.082 (4)	0.085 (5)	0.090 (5)	−0.028 (4)	0.014 (4)	−0.006 (4)
C46	0.120 (6)	0.063 (4)	0.081 (5)	−0.021 (4)	0.038 (5)	−0.013 (4)
C47	0.121 (5)	0.053 (4)	0.064 (4)	0.019 (4)	0.037 (4)	0.004 (3)

Geometric parameters (Å, º) top

Nd1—O4	2.380 (3)	C14—C15	1.370 (6)
Nd1—O5ⁱ	2.407 (2)	C14—H14A	0.9300
Nd1—O7ⁱ	2.412 (2)	C15—H15A	0.9300
Nd1—O2	2.494 (2)	C16—C17	1.328 (5)
Nd1—O1	2.536 (3)	C16—H16A	0.9300
Nd1—O8	2.552 (2)	C17—C18	1.479 (5)
Nd1—N2	2.617 (3)	C17—H17A	0.9300
Nd1—O7	2.635 (2)	C19—C20	1.378 (5)
Nd1—N1	2.646 (3)	C19—C24	1.379 (5)
N1—C33	1.329 (5)	C20—C21	1.388 (5)
N1—C37	1.343 (5)	C20—H20A	0.9300
N2—C28	1.337 (5)	C21—C22	1.396 (5)
N2—C32	1.346 (4)	C21—C25	1.469 (5)
N3—C43	1.342 (5)	C22—C23	1.377 (5)
N3—C47	1.355 (6)	C22—H22A	0.9300
N4—C42	1.333 (5)	C23—C24	1.381 (5)
N4—C38	1.343 (6)	C23—H23A	0.9300
O1—C18	1.267 (4)	C24—H24A	0.9300
O1W—H1WA	0.87 (4)	C25—C26	1.307 (5)
O1W—H1WB	0.87 (19)	C25—H25A	0.9300
O2—C18	1.256 (4)	C26—C27	1.484 (5)
O3—C10	1.372 (5)	C26—H26A	0.9300
O3—H3	0.96 (4)	C28—C29	1.368 (5)
O4—C27	1.266 (4)	C28—H28A	0.9300
O5—C27	1.262 (4)	C29—C30	1.362 (6)
O5—Nd1ⁱ	2.407 (2)	C29—H29A	0.9300
O6—C19	1.363 (4)	C30—C31	1.376 (6)
O6—H6	0.93 (4)	C30—H30A	0.9300
O7—C9	1.277 (4)	C31—C32	1.379 (6)
O7—Nd1ⁱ	2.412 (2)	C31—H31A	0.9300
O8—C9	1.256 (4)	C32—C33	1.488 (6)
O9—C1	1.354 (5)	C33—C34	1.378 (5)
O9—H9	0.96 (4)	C34—C35	1.381 (7)
C1—C6	1.378 (6)	C34—H34A	0.9300
C1—C2	1.395 (5)	C35—C36	1.356 (7)
C2—C3	1.389 (5)	C35—H35A	0.9300
C2—H2A	0.9300	C36—C37	1.361 (5)
C3—C4	1.384 (5)	C36—H36A	0.9300
C3—C7	1.465 (5)	C37—H37A	0.9300
C4—C5	1.383 (5)	C38—C39	1.375 (8)
C4—H4A	0.9300	C38—H38A	0.9300
C5—C6	1.379 (6)	C39—C40	1.354 (7)
C5—H5A	0.9300	C39—H39A	0.9300
C6—H6A	0.9300	C40—C41	1.372 (7)
C7—C8	1.306 (5)	C40—H40A	0.9300
C7—H7A	0.9300	C41—C42	1.377 (6)
C8—C9	1.470 (5)	C41—H41A	0.9300
C8—H8A	0.9300	C42—C43	1.476 (6)
C10—C11	1.373 (5)	C43—C44	1.372 (6)
C10—C15	1.390 (6)	C44—C45	1.366 (6)
C11—C12	1.394 (5)	C44—H44A	0.9300
C11—H11A	0.9300	C45—C46	1.353 (7)
C12—C13	1.381 (5)	C45—H45A	0.9300
C12—C16	1.472 (5)	C46—C47	1.373 (7)
C13—C14	1.383 (6)	C46—H46A	0.9300
C13—H13A	0.9300	C47—H47A	0.9300

O4—Nd1—O5ⁱ	136.78 (8)	O3—C10—C15	123.1 (4)
O4—Nd1—O7ⁱ	73.65 (8)	C11—C10—C15	120.5 (4)
O5ⁱ—Nd1—O7ⁱ	76.62 (8)	C10—C11—C12	119.4 (4)
O4—Nd1—O2	83.19 (9)	C10—C11—H11A	120.3
O5ⁱ—Nd1—O2	126.29 (9)	C12—C11—H11A	120.3
O7ⁱ—Nd1—O2	87.75 (9)	C13—C12—C11	119.6 (4)
O4—Nd1—O1	125.69 (9)	C13—C12—C16	120.6 (4)
O5ⁱ—Nd1—O1	74.62 (8)	C11—C12—C16	119.7 (4)
O7ⁱ—Nd1—O1	75.84 (8)	C12—C13—C14	120.7 (4)
O2—Nd1—O1	51.69 (8)	C12—C13—H13A	119.7
O4—Nd1—O8	93.43 (9)	C14—C13—H13A	119.7
O5ⁱ—Nd1—O8	78.64 (8)	C15—C14—C13	119.5 (5)
O7ⁱ—Nd1—O8	124.88 (8)	C15—C14—H14A	120.2
O2—Nd1—O8	144.94 (9)	C13—C14—H14A	120.2
O1—Nd1—O8	140.72 (8)	C14—C15—C10	120.2 (4)
O4—Nd1—N2	137.21 (9)	C14—C15—H15A	119.9
O5ⁱ—Nd1—N2	80.48 (9)	C10—C15—H15A	119.9
O7ⁱ—Nd1—N2	147.84 (9)	C17—C16—C12	126.9 (4)
O2—Nd1—N2	87.88 (9)	C17—C16—H16A	116.5
O1—Nd1—N2	76.52 (9)	C12—C16—H16A	116.5
O8—Nd1—N2	71.06 (9)	C16—C17—C18	121.2 (4)
O4—Nd1—O7	72.59 (8)	C16—C17—H17A	119.4
O5ⁱ—Nd1—O7	70.06 (8)	C18—C17—H17A	119.4
O7ⁱ—Nd1—O7	75.50 (8)	O2—C18—O1	120.8 (4)
O2—Nd1—O7	153.53 (9)	O2—C18—C17	120.3 (4)
O1—Nd1—O7	138.55 (8)	O1—C18—C17	118.9 (4)
O8—Nd1—O7	49.80 (8)	O2—C18—Nd1	59.42 (19)
N2—Nd1—O7	117.13 (8)	O1—C18—Nd1	61.38 (19)
O4—Nd1—N1	76.64 (9)	C17—C18—Nd1	176.9 (3)
O5ⁱ—Nd1—N1	137.98 (9)	O6—C19—C20	118.3 (4)
O7ⁱ—Nd1—N1	145.40 (9)	O6—C19—C24	122.5 (4)
O2—Nd1—N1	71.38 (10)	C20—C19—C24	119.2 (4)
O1—Nd1—N1	108.79 (9)	C19—C20—C21	121.8 (4)
O8—Nd1—N1	73.88 (9)	C19—C20—H20A	119.1
N2—Nd1—N1	60.90 (10)	C21—C20—H20A	119.1
O7—Nd1—N1	111.86 (9)	C20—C21—C22	118.5 (4)
O4—Nd1—C18	104.56 (10)	C20—C21—C25	119.3 (3)
O5ⁱ—Nd1—C18	100.60 (10)	C22—C21—C25	122.2 (4)
O7ⁱ—Nd1—C18	80.48 (9)	C23—C22—C21	119.4 (4)
O2—Nd1—C18	25.69 (9)	C23—C22—H22A	120.3
O1—Nd1—C18	26.01 (9)	C21—C22—H22A	120.3
O8—Nd1—C18	152.73 (10)	C22—C23—C24	121.3 (4)
N2—Nd1—C18	81.88 (10)	C22—C23—H23A	119.3
O7—Nd1—C18	155.64 (9)	C24—C23—H23A	119.3
N1—Nd1—C18	90.31 (10)	C19—C24—C23	119.7 (4)
O4—Nd1—C9	84.66 (10)	C19—C24—H24A	120.1
O5ⁱ—Nd1—C9	70.51 (9)	C23—C24—H24A	120.1
O7ⁱ—Nd1—C9	100.21 (10)	C26—C25—C21	128.2 (4)
O2—Nd1—C9	162.98 (9)	C26—C25—H25A	115.9
O1—Nd1—C9	144.81 (9)	C21—C25—H25A	115.9
O8—Nd1—C9	24.69 (8)	C25—C26—C27	123.5 (4)
N2—Nd1—C9	93.00 (10)	C25—C26—H26A	118.2
O7—Nd1—C9	25.31 (8)	C27—C26—H26A	118.2
N1—Nd1—C9	94.23 (10)	O5—C27—O4	125.6 (4)
C18—Nd1—C9	170.47 (11)	O5—C27—C26	117.8 (4)
O4—Nd1—Nd1ⁱ	68.44 (6)	O4—C27—C26	116.6 (3)
O5ⁱ—Nd1—Nd1ⁱ	68.60 (6)	N2—C28—C29	123.6 (4)
O7ⁱ—Nd1—Nd1ⁱ	39.71 (6)	N2—C28—H28A	118.2
O2—Nd1—Nd1ⁱ	124.54 (7)	C29—C28—H28A	118.2
O1—Nd1—Nd1ⁱ	110.29 (6)	C30—C29—C28	118.7 (4)
O8—Nd1—Nd1ⁱ	85.38 (6)	C30—C29—H29A	120.7
N2—Nd1—Nd1ⁱ	144.33 (6)	C28—C29—H29A	120.7
O7—Nd1—Nd1ⁱ	35.79 (5)	C29—C30—C31	118.4 (5)
N1—Nd1—Nd1ⁱ	137.98 (7)	C29—C30—H30A	120.8
C18—Nd1—Nd1ⁱ	120.09 (8)	C31—C30—H30A	120.8
C9—Nd1—Nd1ⁱ	60.69 (8)	C30—C31—C32	120.7 (4)
C33—N1—C37	118.0 (4)	C30—C31—H31A	119.7
C33—N1—Nd1	121.3 (3)	C32—C31—H31A	119.7
C37—N1—Nd1	120.4 (3)	N2—C32—C31	120.4 (4)
C28—N2—C32	118.1 (4)	N2—C32—C33	115.8 (4)
C28—N2—Nd1	119.0 (3)	C31—C32—C33	123.7 (4)
C32—N2—Nd1	121.9 (3)	N1—C33—C34	121.3 (4)
C43—N3—C47	116.4 (5)	N1—C33—C32	116.5 (3)
C42—N4—C38	117.2 (5)	C34—C33—C32	122.2 (4)
C18—O1—Nd1	92.6 (2)	C33—C34—C35	119.4 (5)
H1WA—O1W—H1WB	100 (3)	C33—C34—H34A	120.3
C18—O2—Nd1	94.9 (2)	C35—C34—H34A	120.3
C10—O3—H3	101 (3)	C36—C35—C34	119.4 (5)
C27—O4—Nd1	138.1 (2)	C36—C35—H35A	120.3
C27—O5—Nd1ⁱ	137.5 (2)	C34—C35—H35A	120.3
C19—O6—H6	112 (3)	C35—C36—C37	118.1 (5)
C9—O7—Nd1ⁱ	158.6 (2)	C35—C36—H36A	120.9
C9—O7—Nd1	92.7 (2)	C37—C36—H36A	120.9
Nd1ⁱ—O7—Nd1	104.50 (8)	N1—C37—C36	123.7 (4)
C9—O8—Nd1	97.2 (2)	N1—C37—H37A	118.2
C1—O9—H9	116 (3)	C36—C37—H37A	118.2
O9—C1—C6	118.5 (4)	N4—C38—C39	122.8 (6)
O9—C1—C2	122.9 (4)	N4—C38—H38A	118.6
C6—C1—C2	118.6 (4)	C39—C38—H38A	118.6
C3—C2—C1	121.1 (4)	C40—C39—C38	119.3 (6)
C3—C2—H2A	119.4	C40—C39—H39A	120.4
C1—C2—H2A	119.4	C38—C39—H39A	120.4
C4—C3—C2	119.6 (4)	C39—C40—C41	118.8 (6)
C4—C3—C7	123.0 (4)	C39—C40—H40A	120.6
C2—C3—C7	117.4 (4)	C41—C40—H40A	120.6
C5—C4—C3	119.0 (4)	C40—C41—C42	119.3 (5)
C5—C4—H4A	120.5	C40—C41—H41A	120.3
C3—C4—H4A	120.5	C42—C41—H41A	120.3
C6—C5—C4	121.4 (5)	N4—C42—C41	122.5 (5)
C6—C5—H5A	119.3	N4—C42—C43	117.6 (4)
C4—C5—H5A	119.3	C41—C42—C43	119.9 (5)
C1—C6—C5	120.2 (4)	N3—C43—C44	122.3 (5)
C1—C6—H6A	119.9	N3—C43—C42	115.5 (5)
C5—C6—H6A	119.9	C44—C43—C42	122.0 (5)
C8—C7—C3	130.1 (4)	C45—C44—C43	119.9 (5)
C8—C7—H7A	114.9	C45—C44—H44A	120.0
C3—C7—H7A	114.9	C43—C44—H44A	120.0
C7—C8—C9	123.3 (4)	C46—C45—C44	119.0 (6)
C7—C8—H8A	118.3	C46—C45—H45A	120.5
C9—C8—H8A	118.3	C44—C45—H45A	120.5
O8—C9—O7	119.3 (3)	C45—C46—C47	118.9 (6)
O8—C9—C8	122.4 (4)	C45—C46—H46A	120.6
O7—C9—C8	118.3 (4)	C47—C46—H46A	120.6
O8—C9—Nd1	58.09 (19)	N3—C47—C46	123.4 (5)
O7—C9—Nd1	61.94 (19)	N3—C47—H47A	118.3
C8—C9—Nd1	169.8 (3)	C46—C47—H47A	118.3
O3—C10—C11	116.4 (4)

O4—Nd1—N1—C33	159.5 (3)	O5ⁱ—Nd1—C9—O8	105.6 (2)
O5ⁱ—Nd1—N1—C33	10.7 (4)	O7ⁱ—Nd1—C9—O8	177.4 (2)
O7ⁱ—Nd1—N1—C33	−169.1 (3)	O2—Nd1—C9—O8	−65.7 (4)
O2—Nd1—N1—C33	−113.3 (3)	O1—Nd1—C9—O8	97.5 (2)
O1—Nd1—N1—C33	−76.9 (3)	N2—Nd1—C9—O8	26.8 (2)
O8—Nd1—N1—C33	61.9 (3)	O7—Nd1—C9—O8	−170.0 (4)
N2—Nd1—N1—C33	−15.1 (3)	N1—Nd1—C9—O8	−34.2 (2)
O7—Nd1—N1—C33	94.8 (3)	Nd1ⁱ—Nd1—C9—O8	−178.6 (2)
C18—Nd1—N1—C33	−95.6 (3)	O4—Nd1—C9—O7	59.7 (2)
C9—Nd1—N1—C33	76.0 (3)	O5ⁱ—Nd1—C9—O7	−84.4 (2)
Nd1ⁱ—Nd1—N1—C33	125.4 (3)	O7ⁱ—Nd1—C9—O7	−12.6 (2)
O4—Nd1—N1—C37	−14.3 (3)	O2—Nd1—C9—O7	104.2 (4)
O5ⁱ—Nd1—N1—C37	−163.1 (3)	O1—Nd1—C9—O7	−92.5 (2)
O7ⁱ—Nd1—N1—C37	17.1 (4)	O8—Nd1—C9—O7	170.0 (4)
O2—Nd1—N1—C37	73.0 (3)	N2—Nd1—C9—O7	−163.2 (2)
O1—Nd1—N1—C37	109.3 (3)	N1—Nd1—C9—O7	135.8 (2)
O8—Nd1—N1—C37	−111.9 (3)	Nd1ⁱ—Nd1—C9—O7	−8.57 (17)
N2—Nd1—N1—C37	171.2 (3)	O4—Nd1—C9—C8	153.6 (16)
O7—Nd1—N1—C37	−79.0 (3)	O5ⁱ—Nd1—C9—C8	9.5 (16)
C18—Nd1—N1—C37	90.6 (3)	O7ⁱ—Nd1—C9—C8	81.3 (16)
C9—Nd1—N1—C37	−97.7 (3)	O2—Nd1—C9—C8	−161.8 (14)
Nd1ⁱ—Nd1—N1—C37	−48.4 (3)	O1—Nd1—C9—C8	1.4 (17)
O4—Nd1—N2—C28	176.6 (2)	O8—Nd1—C9—C8	−96.1 (16)
O5ⁱ—Nd1—N2—C28	21.6 (3)	N2—Nd1—C9—C8	−69.3 (16)
O7ⁱ—Nd1—N2—C28	−23.4 (4)	O7—Nd1—C9—C8	93.9 (16)
O2—Nd1—N2—C28	−105.8 (3)	N1—Nd1—C9—C8	−130.3 (16)
O1—Nd1—N2—C28	−54.7 (3)	Nd1ⁱ—Nd1—C9—C8	85.4 (16)
O8—Nd1—N2—C28	102.8 (3)	O3—C10—C11—C12	−176.8 (4)
O7—Nd1—N2—C28	83.3 (3)	C15—C10—C11—C12	1.3 (7)
N1—Nd1—N2—C28	−175.6 (3)	C10—C11—C12—C13	−0.4 (7)
C18—Nd1—N2—C28	−80.7 (3)	C10—C11—C12—C16	177.1 (4)
C9—Nd1—N2—C28	91.3 (3)	C11—C12—C13—C14	−1.3 (7)
Nd1ⁱ—Nd1—N2—C28	51.4 (3)	C16—C12—C13—C14	−178.8 (4)
O4—Nd1—N2—C32	8.6 (3)	C12—C13—C14—C15	2.0 (7)
O5ⁱ—Nd1—N2—C32	−146.4 (3)	C13—C14—C15—C10	−1.1 (8)
O7ⁱ—Nd1—N2—C32	168.6 (2)	O3—C10—C15—C14	177.4 (5)
O2—Nd1—N2—C32	86.2 (3)	C11—C10—C15—C14	−0.5 (8)
O1—Nd1—N2—C32	137.2 (3)	C13—C12—C16—C17	−154.3 (5)
O8—Nd1—N2—C32	−65.3 (3)	C11—C12—C16—C17	28.3 (7)
O7—Nd1—N2—C32	−84.8 (3)	C12—C16—C17—C18	179.7 (4)
N1—Nd1—N2—C32	16.4 (3)	Nd1—O2—C18—O1	−2.1 (4)
C18—Nd1—N2—C32	111.3 (3)	Nd1—O2—C18—C17	176.4 (3)
C9—Nd1—N2—C32	−76.8 (3)	Nd1—O1—C18—O2	2.0 (4)
Nd1ⁱ—Nd1—N2—C32	−116.6 (3)	Nd1—O1—C18—C17	−176.4 (3)
O4—Nd1—O1—C18	40.0 (3)	C16—C17—C18—O2	19.7 (6)
O5ⁱ—Nd1—O1—C18	177.1 (2)	C16—C17—C18—O1	−161.9 (4)
O7ⁱ—Nd1—O1—C18	97.4 (2)	O4—Nd1—C18—O2	34.7 (2)
O2—Nd1—O1—C18	−1.1 (2)	O5ⁱ—Nd1—C18—O2	179.2 (2)
O8—Nd1—O1—C18	−134.1 (2)	O7ⁱ—Nd1—C18—O2	104.9 (2)
N2—Nd1—O1—C18	−99.2 (2)	O1—Nd1—C18—O2	−178.0 (4)
O7—Nd1—O1—C18	144.9 (2)	O8—Nd1—C18—O2	−95.1 (3)
N1—Nd1—O1—C18	−46.8 (2)	N2—Nd1—C18—O2	−102.1 (2)
C9—Nd1—O1—C18	−175.0 (2)	O7—Nd1—C18—O2	114.5 (3)
Nd1ⁱ—Nd1—O1—C18	117.4 (2)	N1—Nd1—C18—O2	−41.6 (2)
O4—Nd1—O2—C18	−146.3 (2)	Nd1ⁱ—Nd1—C18—O2	107.9 (2)
O5ⁱ—Nd1—O2—C18	−1.0 (3)	O4—Nd1—C18—O1	−147.4 (2)
O7ⁱ—Nd1—O2—C18	−72.5 (2)	O5ⁱ—Nd1—C18—O1	−2.8 (2)
O1—Nd1—O2—C18	1.1 (2)	O7ⁱ—Nd1—C18—O1	−77.2 (2)
O8—Nd1—O2—C18	127.4 (2)	O2—Nd1—C18—O1	178.0 (4)
N2—Nd1—O2—C18	75.6 (2)	O8—Nd1—C18—O1	82.9 (3)
O7—Nd1—O2—C18	−122.7 (2)	N2—Nd1—C18—O1	75.8 (2)
N1—Nd1—O2—C18	135.5 (3)	O7—Nd1—C18—O1	−67.5 (3)
C9—Nd1—O2—C18	168.9 (3)	N1—Nd1—C18—O1	136.3 (2)
Nd1ⁱ—Nd1—O2—C18	−88.4 (2)	Nd1ⁱ—Nd1—C18—O1	−74.1 (2)
O5ⁱ—Nd1—O4—C27	−21.2 (4)	O6—C19—C20—C21	180.0 (4)
O7ⁱ—Nd1—O4—C27	27.2 (4)	C24—C19—C20—C21	0.0 (6)
O2—Nd1—O4—C27	116.8 (4)	C19—C20—C21—C22	0.4 (6)
O1—Nd1—O4—C27	85.5 (4)	C19—C20—C21—C25	−177.4 (4)
O8—Nd1—O4—C27	−98.2 (4)	C20—C21—C22—C23	0.6 (6)
N2—Nd1—O4—C27	−163.8 (3)	C25—C21—C22—C23	178.3 (4)
O7—Nd1—O4—C27	−52.4 (4)	C21—C22—C23—C24	−1.9 (7)
N1—Nd1—O4—C27	−170.8 (4)	O6—C19—C24—C23	178.7 (4)
C18—Nd1—O4—C27	102.5 (4)	C20—C19—C24—C23	−1.3 (7)
C9—Nd1—O4—C27	−75.1 (4)	C22—C23—C24—C19	2.3 (7)
Nd1ⁱ—Nd1—O4—C27	−14.6 (4)	C20—C21—C25—C26	171.4 (4)
O4—Nd1—O7—C9	−115.8 (2)	C22—C21—C25—C26	−6.3 (7)
O5ⁱ—Nd1—O7—C9	86.4 (2)	C21—C25—C26—C27	−177.2 (4)
O7ⁱ—Nd1—O7—C9	167.2 (2)	Nd1ⁱ—O5—C27—O4	−7.0 (6)
O2—Nd1—O7—C9	−140.5 (2)	Nd1ⁱ—O5—C27—C26	172.3 (2)
O1—Nd1—O7—C9	119.6 (2)	Nd1—O4—C27—O5	19.2 (6)
O8—Nd1—O7—C9	−5.5 (2)	Nd1—O4—C27—C26	−160.1 (3)
N2—Nd1—O7—C9	18.9 (2)	C25—C26—C27—O5	8.6 (6)
N1—Nd1—O7—C9	−48.5 (2)	C25—C26—C27—O4	−172.0 (4)
C18—Nd1—O7—C9	157.3 (3)	C32—N2—C28—C29	−0.4 (6)
Nd1ⁱ—Nd1—O7—C9	167.2 (2)	Nd1—N2—C28—C29	−168.9 (3)
O4—Nd1—O7—Nd1ⁱ	77.07 (10)	N2—C28—C29—C30	2.9 (7)
O5ⁱ—Nd1—O7—Nd1ⁱ	−80.77 (9)	C28—C29—C30—C31	−2.5 (8)
O7ⁱ—Nd1—O7—Nd1ⁱ	0.0	C29—C30—C31—C32	−0.1 (8)
O2—Nd1—O7—Nd1ⁱ	52.4 (2)	C28—N2—C32—C31	−2.3 (6)
O1—Nd1—O7—Nd1ⁱ	−47.59 (15)	Nd1—N2—C32—C31	165.8 (3)
O8—Nd1—O7—Nd1ⁱ	−172.62 (14)	C28—N2—C32—C33	174.9 (3)
N2—Nd1—O7—Nd1ⁱ	−148.21 (9)	Nd1—N2—C32—C33	−16.9 (5)
N1—Nd1—O7—Nd1ⁱ	144.32 (10)	C30—C31—C32—N2	2.6 (7)
C18—Nd1—O7—Nd1ⁱ	−9.9 (3)	C30—C31—C32—C33	−174.4 (5)
C9—Nd1—O7—Nd1ⁱ	−167.2 (2)	C37—N1—C33—C34	4.1 (7)
O4—Nd1—O8—C9	69.3 (2)	Nd1—N1—C33—C34	−169.8 (4)
O5ⁱ—Nd1—O8—C9	−67.8 (2)	C37—N1—C33—C32	−172.8 (4)
O7ⁱ—Nd1—O8—C9	−3.1 (3)	Nd1—N1—C33—C32	13.2 (5)
O2—Nd1—O8—C9	152.3 (2)	N2—C32—C33—N1	2.2 (6)
O1—Nd1—O8—C9	−115.5 (2)	C31—C32—C33—N1	179.4 (4)
N2—Nd1—O8—C9	−151.5 (2)	N2—C32—C33—C34	−174.8 (4)
O7—Nd1—O8—C9	5.6 (2)	C31—C32—C33—C34	2.4 (7)
N1—Nd1—O8—C9	144.3 (2)	N1—C33—C34—C35	−3.3 (8)
C18—Nd1—O8—C9	−158.9 (3)	C32—C33—C34—C35	173.5 (5)
Nd1ⁱ—Nd1—O8—C9	1.3 (2)	C33—C34—C35—C36	−0.3 (9)
O9—C1—C2—C3	177.6 (4)	C34—C35—C36—C37	2.8 (9)
C6—C1—C2—C3	−1.3 (7)	C33—N1—C37—C36	−1.5 (7)
C1—C2—C3—C4	2.1 (6)	Nd1—N1—C37—C36	172.5 (4)
C1—C2—C3—C7	−176.0 (4)	C35—C36—C37—N1	−2.0 (8)
C2—C3—C4—C5	−0.4 (6)	C42—N4—C38—C39	2.7 (9)
C7—C3—C4—C5	177.6 (4)	N4—C38—C39—C40	−1.6 (10)
C3—C4—C5—C6	−2.1 (7)	C38—C39—C40—C41	−1.3 (10)
O9—C1—C6—C5	179.9 (5)	C39—C40—C41—C42	2.8 (9)
C2—C1—C6—C5	−1.3 (7)	C38—N4—C42—C41	−1.1 (7)
C4—C5—C6—C1	3.0 (8)	C38—N4—C42—C43	179.5 (5)
C4—C3—C7—C8	−10.7 (7)	C40—C41—C42—N4	−1.7 (8)
C2—C3—C7—C8	167.3 (4)	C40—C41—C42—C43	177.7 (5)
C3—C7—C8—C9	−177.0 (4)	C47—N3—C43—C44	1.5 (7)
Nd1—O8—C9—O7	−10.1 (4)	C47—N3—C43—C42	−175.1 (4)
Nd1—O8—C9—C8	167.9 (3)	N4—C42—C43—N3	−134.0 (5)
Nd1ⁱ—O7—C9—O8	153.7 (5)	C41—C42—C43—N3	46.5 (6)
Nd1—O7—C9—O8	9.7 (4)	N4—C42—C43—C44	49.3 (7)
Nd1ⁱ—O7—C9—C8	−24.5 (9)	C41—C42—C43—C44	−130.1 (5)
Nd1—O7—C9—C8	−168.4 (3)	N3—C43—C44—C45	−2.9 (8)
Nd1ⁱ—O7—C9—Nd1	143.9 (7)	C42—C43—C44—C45	173.5 (5)
C7—C8—C9—O8	−3.1 (6)	C43—C44—C45—C46	1.3 (9)
C7—C8—C9—O7	174.9 (4)	C44—C45—C46—C47	1.4 (10)
C7—C8—C9—Nd1	86.5 (16)	C43—N3—C47—C46	1.4 (8)
O4—Nd1—C9—O8	−110.3 (2)	C45—C46—C47—N3	−2.9 (9)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···N4ⁱⁱ	0.87 (5)	2.04 (5)	2.897 (6)	168 (5)
O3—H3···O1Wⁱⁱⁱ	0.96 (4)	1.68 (2)	2.618 (5)	163 (5)
O6—H6···O1^iv	0.93 (4)	1.79 (2)	2.703 (4)	168 (4)
O9—H9···N3ⁱⁱ	0.96 (4)	1.90 (2)	2.849 (5)	175 (5)
O1W—H1WA···O8	0.87 (4)	1.96 (4)	2.825 (4)	175 (5)

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

Experimental details

Crystal data
Chemical formula	[Nd₂(C₉H₇O₃)₆(C₁₀H₈N₂)₂]·2C₁₀H₈N₂·2H₂O
M_r	1928.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.7333 (2), 28.9077 (5), 14.3276 (3)
β (°)	108.274 (1)
V (Å³)	4221.30 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.24 × 0.11 × 0.07

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.84, 0.91
No. of measured, independent and observed [I > 2σ(I)] reflections	36893, 9735, 6140
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.083, 1.00
No. of reflections	9735
No. of parameters	574
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.65

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···N4ⁱ	0.87 (5)	2.04 (5)	2.897 (6)	168 (5)
O3—H3···O1Wⁱⁱ	0.96 (4)	1.68 (2)	2.618 (5)	163 (5)
O6—H6···O1ⁱⁱⁱ	0.93 (4)	1.79 (2)	2.703 (4)	168 (4)
O9—H9···N3ⁱ	0.96 (4)	1.90 (2)	2.849 (5)	175 (5)
O1W—H1WA···O8	0.87 (4)	1.96 (4)	2.825 (4)	175 (5)

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

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J., Couse, M. D., Garcia-Vega, M., Rosende, M., Sanchez, A., Sordo, J., Varela, J. M. & Vazquez-Lopez, E. M. (2008). Polyhedron, 27, 2436–2446. Web of Science CSD CrossRef CAS Google Scholar
Crowther, D., Chowdhury, M. & Kariuki, B. M. (2008). J. Mol. Struct. 872, 64–74. Web of Science CSD CrossRef CAS Google Scholar
Gossauer, A., Nydegger, F., Kiss, T., Sleziak, R. & Stoeckli-Evans, H. (2004). J. Am. Chem. Soc. 126, 1764–1783. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göettingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, C.-Y., Fu, J.-D. & Wen, Y.-H. (2010). Acta Cryst. E66, m1519. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 67| Part 12| December 2011| Pages m1907-m1908

https://doi.org/10.1107/S1600536811050707

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tetra­kis­[μ-3-(3-hy­dr­oxy­phen­yl)propenoato]bis­­{aqua­(2,2′-bi­pyridine)­[3-(3-hy­dr­oxy­phen­yl)propenoato]neodymium(III)} 2,2′-bi­pyridine disolvate dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Tetrakis[μ-3-(3-hydroxyphenyl)propenoato]bis{aqua(2,2′-bipyridine)[3-(3-hydroxyphenyl)propenoato]neodymium(III)} 2,2′-bipyridine disolvate dihydrate