Crystal structure of di-μ-benzato-κ4O:O′-bis­[aqua­(benzato-κO)(benzato-κ2O,O′)(2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)europium(III)]–benzoic acid (1/2)

White, F.; Sykora, R.E.

doi:10.1107/S1600536814018182

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages m328-m329

doi:10.1107/S1600536814018182

Open

access

Crystal structure of di-μ-benzato-κ⁴O:O′-bis[aqua(benzato-κO)(benzato-κ²O,O′)(2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)europium(III)]–benzoic acid (1/2)

Frankie White ^a and Richard E. Sykora ^a ^*

^aUniversity of South Alabama, Department of Chemistry, Mobile, AL 36688-0002, USA
^*Correspondence e-mail: rsykora@southalabama.edu

Edited by T. J. Prior, University of Hull, England (Received 29 July 2014; accepted 7 August 2014; online 13 August 2014)

The title compound, [Eu₂(C₇H₅O₂)₆(C₁₅H₁₁N₃)₂(H₂O)₂]·2C₇H₆O₂, is a co-crystalline compound containing a dinuclear Eu^III coordination complex with inversion symmetry co-crystallized with benzoic acid in a 1:2 ratio. The Eu³⁺ ions within the dimer are nine-coordinate, containing one tridentate terpyridine, one water, and four benzoate ions, two of which bridge the Eu³⁺ ions. Of the four benzoate ligands coordinating to each Eu³⁺ position, three distinct coordination modes [monodentate, bidentate–chelating, and bidentate–bridging (twice)] are observed. Within the crystal, there are two additional uncoordinating benzoic acid molecules per dinuclear complex. Within the dimer, the water bound to each Eu³⁺ ion participates in intramolecular hydrogen bonding with a coordinating benzoate. Additionally, the carboxylic acid group on the benzoic acid participates in intermolecular hydrogen bonding with a benzoate ligand bound to the dimer complex.

Keywords: crystal structure; dinuclear europium(III) complex; 2,2′:6′,2′′-terpyridine; benzoate; hydrogen bonding.

CCDC reference: 1018455

1. Related literature

Coordination of lanthanide ions by organic ligands has many uses including solvent extractions from nuclear waste and light emitting diodes in electronics (Dul et al., 2013 ; Romero et al., 2012 ). Organic ligands are also capable of increasing the intensity of lanthanide emissions (Romero et al., 2012). The title compound, and similar derivatives, are of interest because of the effect these organic ligands can have on increasing the emission intensity from lanthanide ions in white-light-emitting phosphors. For lanthanide–terpyridine complex chemistry, see: Frost et al. (1969 ). For synthesis, structural, and spectroscopic properties of related lanthanide complexes containing both terpyridine and bridging benzoate ligands, see: Messimeri et al. (2007 ); Fiedler et al. (2007 ).

2. Experimental

2.1. Crystal data

[Eu₂(C₇H₅O₂)₆(C₁₅H₁₁N₃)₂(H₂O)₂]·2C₇H₆O₂
M_r = 1777.38
Triclinic, $[P \overline 1]$
a = 11.8435 (5) Å
b = 13.9470 (7) Å
c = 14.0090 (7) Å
α = 102.568 (4)°
β = 111.400 (5)°
γ = 108.583 (5)°
V = 1890.40 (16) Å³
Z = 1
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 180 K
0.05 × 0.04 × 0.03 mm

2.2. Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ) T_min = 0.988, T_max = 1.000
12682 measured reflections
6921 independent reflections
5919 reflections with I > 2σ(I)
R_int = 0.037

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.070
S = 1.03
6921 reflections
507 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O8ⁱ	0.82	1.76	2.582 (4)	178
O5—H5A⋯O8	0.87	1.98	2.796 (4)	155
O5—H5B⋯O4ⁱⁱ	0.87	1.95	2.768 (4)	155
Symmetry codes: (i) x, y-1, z-1; (ii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1018455

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018182/pj2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018182/pj2014Isup2.hkl

checkCIF report

Synthesis and crystallization top

Methanol solutions consisting of 0.1 M EuCl₃ (1mL), 0.1 M benzoic acid (1 mL), and 0.1 M 2,2':6',2"-terpyridine (1 mL) were mixed in a test tube. The resultant solution was left to evaporate under normal atmospheric conditions which resulted in the formation of colorless crystals. The single crystals were gathered and isolated for studies.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H-atoms were placed in calculated positions using the hadd command in Olex2 (Dolomanov et al., 2009) and allowed to ride during subsequent refinement, with U_iso(H) = 1.2U_eq(C) and C—H distances of 0.93 Å for ring hydrogens, with U_iso(H) = 1.5U_eq(O) and O—H distances of 0.875 Å for water hydrogens, and with U_iso(H) = 1.5U_eq(O) and an O—H distance of 0.82 Å for the carboxylic acid hydrogen. Free refinement of O—H hydrogen atoms resulted in reasonable geometries, but unexpectedly short O—H bond distances.

Related literature top

Coordination of lanthanide ions by organic ligands has many uses including solvent extractions from nuclear waste and light emitting diodes in electronics (Dul et al., 2013; Romero et al., 2012). Organic ligands are also capable of increasing the intensity of lanthanide emissions (Romero et al., 2012). The title compound, and similar derivatives, are of interest because of the effect these organic ligands can have on increasing the emission intensity from lanthanide ions in white-light-emitting phosphors. For lanthanide–terpyridine complex chemistry, see: Frost et al. (1969). For synthesis, structural, and spectroscopic properties of related lanthanide complexes containing both terpyridine and bridging benzoate ligands, see: Messimeri et al. (2007); Fiedler et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top

Fig. 1. A ball-and-stick representaion of the molecular structure of I. Hydrogen atoms on the aromatic rings have been removed for clarity.

Di-µ-benzato-κ⁴O:O'-bis[aqua(benzato-κO)(benzato-κ²O,O')(2,2':6',2''-terpyridine-κ³N,N',N'')europium(III)]–benzoic acid (1/2) top

Crystal data top

[Eu₂(C₇H₅O₂)₆(C₁₅H₁₁N₃)₂(H₂O)₂]·2C₇H₆O₂	Z = 1
M_r = 1777.38	F(000) = 896
Triclinic, P1	D_x = 1.561 Mg m⁻³
a = 11.8435 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.9470 (7) Å	Cell parameters from 5349 reflections
c = 14.0090 (7) Å	θ = 3.3–26.4°
α = 102.568 (4)°	µ = 1.72 mm⁻¹
β = 111.400 (5)°	T = 180 K
γ = 108.583 (5)°	Prism, clear colourless
V = 1890.40 (16) Å³	0.05 × 0.04 × 0.03 mm

Data collection top

Agilent Xcalibur Eos diffractometer	6921 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5919 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 16.0514 pixels mm^-1	θ_max = 25.4°, θ_min = 3.0°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −16→16
T_min = 0.988, T_max = 1.000	l = −16→15
12682 measured reflections

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0205P)²] where P = (F_o² + 2F_c²)/3
6921 reflections	(Δ/σ)_max = 0.001
507 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Eu₂(C₇H₅O₂)₆(C₁₅H₁₁N₃)₂(H₂O)₂]·2C₇H₆O₂	γ = 108.583 (5)°
M_r = 1777.38	V = 1890.40 (16) Å³
Triclinic, P1	Z = 1
a = 11.8435 (5) Å	Mo Kα radiation
b = 13.9470 (7) Å	µ = 1.72 mm⁻¹
c = 14.0090 (7) Å	T = 180 K
α = 102.568 (4)°	0.05 × 0.04 × 0.03 mm
β = 111.400 (5)°

Data collection top

Agilent Xcalibur Eos diffractometer	6921 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	5919 reflections with I > 2σ(I)
T_min = 0.988, T_max = 1.000	R_int = 0.037
12682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
6921 reflections	Δρ_min = −0.53 e Å⁻³
507 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 > 2σ(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
Eu1	0.60725 (2)	0.901818 (18)	0.607785 (17)	0.01686 (7)
N3	0.4478 (3)	0.7011 (3)	0.5632 (3)	0.0206 (8)
O3	0.6498 (3)	0.7737 (2)	0.4829 (2)	0.0231 (7)
O9	0.5811 (3)	0.9085 (2)	0.7688 (2)	0.0237 (7)
O4	0.4730 (3)	0.8045 (2)	0.4030 (2)	0.0231 (7)
O1	0.7127 (3)	1.0054 (2)	0.5254 (2)	0.0289 (7)
O8	0.7071 (3)	1.0699 (3)	0.9073 (2)	0.0356 (8)
N1	0.8631 (3)	0.9976 (3)	0.7433 (3)	0.0241 (8)
O7	0.8924 (4)	0.3302 (3)	−0.0132 (3)	0.0461 (9)
N2	0.7144 (3)	0.7916 (3)	0.7133 (2)	0.0186 (8)
C6	0.8428 (4)	0.8412 (4)	0.7946 (3)	0.0218 (10)
C25	0.3769 (4)	0.6313 (3)	0.2020 (3)	0.0246 (10)
H25	0.3164	0.6570	0.2107	0.030*
C17	0.7978 (4)	1.1095 (3)	0.4350 (3)	0.0211 (10)
C24	0.5068 (4)	0.6743 (3)	0.2884 (3)	0.0205 (9)
C23	0.5477 (4)	0.7567 (3)	0.3978 (3)	0.0187 (9)
C16	0.6934 (4)	1.0641 (3)	0.4701 (3)	0.0196 (9)
C10	0.6377 (4)	0.6881 (4)	0.6939 (3)	0.0212 (10)
C1	0.9367 (4)	1.0985 (4)	0.7559 (4)	0.0330 (11)
H1	0.8960	1.1277	0.7075	0.040*
C31	0.9065 (4)	0.4374 (4)	0.1515 (3)	0.0254 (10)
C38	0.5944 (4)	0.9156 (3)	0.9417 (3)	0.0202 (9)
C43	0.5257 (4)	0.8029 (4)	0.9017 (3)	0.0255 (10)
H43	0.4975	0.7619	0.8285	0.031*
C37	0.6298 (4)	0.9697 (4)	0.8685 (3)	0.0237 (10)
C29	0.5979 (4)	0.6380 (4)	0.2737 (3)	0.0267 (11)
H29	0.6857	0.6673	0.3305	0.032*
C3	1.1281 (5)	1.1201 (4)	0.9069 (4)	0.0408 (13)
H3	1.2166	1.1616	0.9628	0.049*
C42	0.4985 (4)	0.7505 (4)	0.9696 (4)	0.0330 (11)
H42	0.4526	0.6747	0.9420	0.040*
C15	0.3195 (4)	0.6563 (4)	0.4855 (4)	0.0293 (11)
H15	0.2864	0.7014	0.4568	0.035*
C11	0.4957 (4)	0.6357 (3)	0.6054 (3)	0.0219 (10)
C39	0.6353 (5)	0.9755 (4)	1.0512 (3)	0.0304 (11)
H39	0.6821	1.0512	1.0795	0.036*
C41	0.5395 (5)	0.8111 (4)	1.0781 (4)	0.0386 (13)
H41	0.5217	0.7761	1.1239	0.046*
C26	0.3368 (5)	0.5508 (4)	0.1032 (3)	0.0300 (11)
H26	0.2493	0.5213	0.0459	0.036*
C40	0.6065 (5)	0.9228 (4)	1.1184 (4)	0.0402 (13)
H40	0.6329	0.9634	1.1913	0.048*
C4	1.0557 (5)	1.0153 (4)	0.8952 (4)	0.0350 (12)
H4	1.0955	0.9850	0.9427	0.042*
C13	0.2820 (5)	0.4796 (4)	0.4873 (4)	0.0411 (13)
H13	0.2268	0.4054	0.4622	0.049*
C2	1.0678 (5)	1.1624 (4)	0.8350 (4)	0.0378 (12)
H2	1.1147	1.2324	0.8398	0.045*
C7	0.8972 (5)	0.7876 (4)	0.8584 (4)	0.0298 (11)
H7	0.9861	0.8232	0.9145	0.036*
C5	0.9242 (4)	0.9556 (4)	0.8130 (3)	0.0213 (10)
C14	0.2330 (5)	0.5469 (4)	0.4451 (4)	0.0330 (11)
H14	0.1441	0.5192	0.3908	0.040*
C12	0.4144 (5)	0.5249 (4)	0.5675 (4)	0.0320 (11)
H12	0.4495	0.4808	0.5965	0.038*
C28	0.5573 (5)	0.5576 (4)	0.1736 (4)	0.0376 (13)
H28	0.6180	0.5332	0.1632	0.045*
C32	0.8532 (5)	0.4409 (4)	0.2239 (4)	0.0373 (12)
H32	0.7912	0.3768	0.2192	0.045*
C18	0.9132 (5)	1.0938 (4)	0.4702 (4)	0.0382 (13)
H18	0.9255	1.0536	0.5148	0.046*
C9	0.6876 (5)	0.6307 (4)	0.7557 (4)	0.0314 (11)
H9	0.6329	0.5590	0.7414	0.038*
C36	0.9973 (5)	0.5325 (4)	0.1575 (4)	0.0413 (13)
H36	1.0320	0.5300	0.1077	0.050*
C8	0.8181 (5)	0.6823 (4)	0.8371 (4)	0.0351 (12)
H8	0.8533	0.6454	0.8784	0.042*
C27	0.4275 (5)	0.5144 (4)	0.0903 (4)	0.0370 (12)
H27	0.4004	0.4597	0.0240	0.044*
C35	1.0371 (6)	0.6320 (5)	0.2375 (5)	0.0530 (15)
H35	1.0995	0.6961	0.2425	0.064*
C22	0.7788 (5)	1.1673 (4)	0.3664 (4)	0.0374 (12)
H22	0.7011	1.1780	0.3416	0.045*
C30	0.8641 (4)	0.3329 (4)	0.0611 (4)	0.0272 (11)
C33	0.8922 (5)	0.5406 (5)	0.3042 (4)	0.0482 (15)
H33	0.8570	0.5434	0.3536	0.058*
C21	0.8756 (7)	1.2088 (4)	0.3351 (5)	0.0632 (19)
H21	0.8627	1.2476	0.2891	0.076*
C19	1.0107 (5)	1.1375 (5)	0.4396 (5)	0.0595 (18)
H19	1.0897	1.1288	0.4654	0.071*
C20	0.9896 (7)	1.1939 (5)	0.3702 (6)	0.072 (2)
H20	1.0534	1.2218	0.3476	0.087*
C34	0.9832 (6)	0.6347 (5)	0.3095 (5)	0.0561 (17)
H34	1.0088	0.7014	0.3626	0.067*
O6	0.7974 (3)	0.2460 (2)	0.0747 (2)	0.0333 (8)
H6	0.7697	0.1911	0.0207	0.050*
O5	0.6709 (3)	1.0977 (2)	0.7081 (2)	0.0263 (7)
H5A	0.6854	1.1097	0.7764	0.040*
H5B	0.6061	1.1148	0.6754	0.040*
O2	0.5972 (3)	1.0882 (2)	0.4455 (2)	0.0302 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.01700 (12)	0.01815 (12)	0.01788 (12)	0.00895 (9)	0.00798 (10)	0.00955 (9)
N3	0.021 (2)	0.019 (2)	0.0224 (19)	0.0092 (18)	0.0100 (18)	0.0103 (16)
O3	0.0210 (17)	0.0307 (19)	0.0190 (15)	0.0155 (15)	0.0060 (14)	0.0113 (14)
O9	0.0325 (19)	0.0246 (18)	0.0174 (15)	0.0147 (16)	0.0128 (15)	0.0088 (14)
O4	0.0252 (17)	0.0274 (18)	0.0242 (16)	0.0180 (15)	0.0124 (15)	0.0120 (14)
O1	0.0322 (19)	0.032 (2)	0.0327 (18)	0.0157 (17)	0.0195 (16)	0.0200 (16)
O8	0.050 (2)	0.021 (2)	0.0271 (18)	0.0048 (18)	0.0208 (18)	0.0072 (15)
N1	0.019 (2)	0.021 (2)	0.028 (2)	0.0067 (18)	0.0062 (18)	0.0122 (17)
O7	0.063 (3)	0.040 (2)	0.040 (2)	0.016 (2)	0.032 (2)	0.0177 (18)
N2	0.020 (2)	0.022 (2)	0.0185 (19)	0.0127 (18)	0.0107 (18)	0.0089 (16)
C6	0.024 (3)	0.028 (3)	0.021 (2)	0.016 (2)	0.012 (2)	0.013 (2)
C25	0.032 (3)	0.024 (3)	0.028 (2)	0.015 (2)	0.017 (2)	0.017 (2)
C17	0.028 (3)	0.019 (2)	0.022 (2)	0.010 (2)	0.017 (2)	0.0066 (19)
C24	0.026 (3)	0.019 (2)	0.021 (2)	0.010 (2)	0.012 (2)	0.013 (2)
C23	0.023 (2)	0.018 (2)	0.020 (2)	0.007 (2)	0.013 (2)	0.0112 (19)
C16	0.018 (2)	0.017 (2)	0.016 (2)	0.006 (2)	0.005 (2)	0.0009 (19)
C10	0.025 (3)	0.024 (3)	0.024 (2)	0.014 (2)	0.016 (2)	0.012 (2)
C1	0.023 (3)	0.027 (3)	0.044 (3)	0.011 (2)	0.007 (2)	0.021 (2)
C31	0.023 (3)	0.024 (3)	0.022 (2)	0.011 (2)	0.002 (2)	0.010 (2)
C38	0.023 (3)	0.023 (3)	0.020 (2)	0.013 (2)	0.011 (2)	0.011 (2)
C43	0.024 (3)	0.029 (3)	0.020 (2)	0.012 (2)	0.008 (2)	0.007 (2)
C37	0.027 (3)	0.024 (3)	0.027 (3)	0.017 (2)	0.014 (2)	0.012 (2)
C29	0.029 (3)	0.033 (3)	0.021 (2)	0.016 (2)	0.014 (2)	0.011 (2)
C3	0.018 (3)	0.038 (3)	0.042 (3)	0.004 (3)	0.000 (2)	0.011 (3)
C42	0.027 (3)	0.028 (3)	0.037 (3)	0.006 (2)	0.010 (2)	0.016 (2)
C15	0.027 (3)	0.029 (3)	0.033 (3)	0.013 (2)	0.012 (2)	0.014 (2)
C11	0.028 (3)	0.022 (3)	0.022 (2)	0.012 (2)	0.016 (2)	0.011 (2)
C39	0.043 (3)	0.021 (3)	0.026 (3)	0.012 (2)	0.017 (2)	0.008 (2)
C41	0.047 (3)	0.046 (4)	0.029 (3)	0.018 (3)	0.022 (3)	0.023 (3)
C26	0.032 (3)	0.024 (3)	0.021 (2)	0.006 (2)	0.005 (2)	0.008 (2)
C40	0.058 (4)	0.039 (4)	0.022 (3)	0.017 (3)	0.020 (3)	0.013 (2)
C4	0.024 (3)	0.038 (3)	0.037 (3)	0.011 (3)	0.005 (2)	0.023 (3)
C13	0.043 (3)	0.026 (3)	0.045 (3)	0.004 (3)	0.018 (3)	0.017 (3)
C2	0.027 (3)	0.033 (3)	0.045 (3)	0.011 (3)	0.007 (3)	0.020 (3)
C7	0.025 (3)	0.031 (3)	0.034 (3)	0.013 (2)	0.011 (2)	0.018 (2)
C5	0.020 (2)	0.027 (3)	0.022 (2)	0.014 (2)	0.012 (2)	0.012 (2)
C14	0.023 (3)	0.029 (3)	0.034 (3)	0.005 (2)	0.007 (2)	0.010 (2)
C12	0.033 (3)	0.023 (3)	0.034 (3)	0.010 (2)	0.010 (3)	0.013 (2)
C28	0.055 (4)	0.047 (3)	0.035 (3)	0.035 (3)	0.031 (3)	0.019 (3)
C32	0.030 (3)	0.035 (3)	0.033 (3)	0.015 (3)	0.005 (3)	0.006 (2)
C18	0.030 (3)	0.038 (3)	0.054 (3)	0.017 (3)	0.026 (3)	0.015 (3)
C9	0.034 (3)	0.025 (3)	0.039 (3)	0.014 (2)	0.016 (3)	0.018 (2)
C36	0.040 (3)	0.034 (3)	0.042 (3)	0.015 (3)	0.010 (3)	0.019 (3)
C8	0.035 (3)	0.038 (3)	0.039 (3)	0.023 (3)	0.012 (3)	0.025 (3)
C27	0.053 (4)	0.036 (3)	0.022 (3)	0.021 (3)	0.019 (3)	0.008 (2)
C35	0.046 (4)	0.032 (4)	0.061 (4)	0.017 (3)	0.005 (3)	0.019 (3)
C22	0.056 (4)	0.026 (3)	0.037 (3)	0.016 (3)	0.030 (3)	0.013 (2)
C30	0.026 (3)	0.022 (3)	0.030 (3)	0.012 (2)	0.007 (2)	0.011 (2)
C33	0.042 (4)	0.049 (4)	0.038 (3)	0.029 (3)	0.005 (3)	0.000 (3)
C21	0.119 (6)	0.035 (4)	0.060 (4)	0.024 (4)	0.071 (5)	0.025 (3)
C19	0.037 (4)	0.056 (4)	0.077 (4)	0.008 (3)	0.042 (4)	0.001 (4)
C20	0.093 (5)	0.032 (4)	0.095 (5)	−0.004 (4)	0.086 (5)	0.003 (3)
C34	0.046 (4)	0.030 (4)	0.053 (4)	0.022 (3)	−0.007 (3)	−0.007 (3)
O6	0.041 (2)	0.0217 (19)	0.0297 (18)	0.0075 (17)	0.0176 (18)	0.0054 (15)
O5	0.0337 (19)	0.0275 (19)	0.0233 (16)	0.0183 (16)	0.0118 (16)	0.0143 (14)
O2	0.0243 (18)	0.036 (2)	0.0354 (18)	0.0183 (17)	0.0139 (16)	0.0135 (16)

Geometric parameters (Å, º) top

Eu1—N3	2.608 (3)	C42—C41	1.378 (6)
Eu1—O3	2.523 (2)	C15—H15	0.9300
Eu1—O9	2.372 (2)	C15—C14	1.379 (6)
Eu1—O4	2.491 (3)	C11—C12	1.386 (6)
Eu1—O1	2.368 (3)	C39—H39	0.9300
Eu1—N1	2.587 (3)	C39—C40	1.385 (6)
Eu1—N2	2.650 (3)	C41—H41	0.9300
Eu1—C23	2.869 (4)	C41—C40	1.371 (7)
Eu1—O5	2.500 (3)	C26—H26	0.9300
Eu1—O2ⁱ	2.320 (3)	C26—C27	1.376 (6)
N3—C15	1.333 (5)	C40—H40	0.9300
N3—C11	1.349 (5)	C4—H4	0.9300
O3—C23	1.258 (4)	C4—C5	1.376 (6)
O9—C37	1.262 (5)	C13—H13	0.9300
O4—C23	1.278 (4)	C13—C14	1.381 (6)
O1—C16	1.260 (5)	C13—C12	1.376 (6)
O8—C37	1.256 (5)	C2—H2	0.9300
N1—C1	1.330 (5)	C7—H7	0.9300
N1—C5	1.350 (5)	C7—C8	1.360 (6)
O7—C30	1.201 (5)	C14—H14	0.9300
N2—C6	1.346 (5)	C12—H12	0.9300
N2—C10	1.340 (5)	C28—H28	0.9300
C6—C7	1.397 (5)	C28—C27	1.373 (6)
C6—C5	1.484 (6)	C32—H32	0.9300
C25—H25	0.9300	C32—C33	1.394 (6)
C25—C24	1.389 (5)	C18—H18	0.9300
C25—C26	1.381 (5)	C18—C19	1.384 (7)
C17—C16	1.500 (5)	C9—H9	0.9300
C17—C18	1.380 (5)	C9—C8	1.361 (6)
C17—C22	1.385 (6)	C36—H36	0.9300
C24—C23	1.497 (5)	C36—C35	1.387 (7)
C24—C29	1.390 (5)	C8—H8	0.9300
C16—O2	1.241 (4)	C27—H27	0.9300
C10—C11	1.484 (6)	C35—H35	0.9300
C10—C9	1.405 (5)	C35—C34	1.376 (7)
C1—H1	0.9300	C22—H22	0.9300
C1—C2	1.366 (6)	C22—C21	1.377 (7)
C31—C32	1.376 (6)	C30—O6	1.316 (5)
C31—C36	1.378 (6)	C33—H33	0.9300
C31—C30	1.499 (6)	C33—C34	1.373 (8)
C38—C43	1.384 (6)	C21—H21	0.9300
C38—C37	1.498 (5)	C21—C20	1.358 (8)
C38—C39	1.389 (5)	C19—H19	0.9300
C43—H43	0.9300	C19—C20	1.381 (8)
C43—C42	1.384 (6)	C20—H20	0.9300
C29—H29	0.9300	C34—H34	0.9300
C29—C28	1.390 (6)	O6—H6	0.8200
C3—H3	0.9300	O5—H5A	0.8741
C3—C4	1.375 (6)	O5—H5B	0.8737
C3—C2	1.369 (6)	O2—Eu1ⁱ	2.319 (3)
C42—H42	0.9300

N3—Eu1—N2	62.51 (10)	C24—C29—C28	119.7 (4)
N3—Eu1—C23	68.56 (10)	C28—C29—H29	120.2
O3—Eu1—N3	71.20 (9)	C4—C3—H3	120.5
O3—Eu1—N1	88.58 (9)	C2—C3—H3	120.5
O3—Eu1—N2	69.88 (8)	C2—C3—C4	119.0 (5)
O3—Eu1—C23	25.99 (9)	C43—C42—H42	120.1
O9—Eu1—N3	75.36 (10)	C41—C42—C43	119.8 (5)
O9—Eu1—O3	134.03 (9)	C41—C42—H42	120.1
O9—Eu1—O4	139.35 (10)	N3—C15—H15	118.1
O9—Eu1—N1	84.98 (10)	N3—C15—C14	123.9 (4)
O9—Eu1—N2	67.02 (8)	C14—C15—H15	118.1
O9—Eu1—C23	143.66 (11)	N3—C11—C10	117.0 (4)
O9—Eu1—O5	74.26 (9)	N3—C11—C12	120.9 (4)
O4—Eu1—N3	71.24 (10)	C12—C11—C10	122.1 (4)
O4—Eu1—O3	52.37 (8)	C38—C39—H39	119.9
O4—Eu1—N1	133.36 (9)	C40—C39—C38	120.2 (4)
O4—Eu1—N2	114.51 (9)	C40—C39—H39	119.9
O4—Eu1—C23	26.39 (9)	C42—C41—H41	120.0
O4—Eu1—O5	124.26 (9)	C40—C41—C42	120.0 (4)
O1—Eu1—N3	139.77 (10)	C40—C41—H41	120.0
O1—Eu1—O3	73.91 (9)	C25—C26—H26	120.3
O1—Eu1—O9	144.85 (10)	C27—C26—C25	119.4 (4)
O1—Eu1—O4	71.87 (10)	C27—C26—H26	120.3
O1—Eu1—N1	73.44 (10)	C39—C40—H40	119.8
O1—Eu1—N2	121.78 (9)	C41—C40—C39	120.4 (4)
O1—Eu1—C23	71.28 (10)	C41—C40—H40	119.8
O1—Eu1—O5	72.78 (9)	C3—C4—H4	120.1
N1—Eu1—N3	124.32 (10)	C3—C4—C5	119.8 (4)
N1—Eu1—N2	61.84 (10)	C5—C4—H4	120.1
N1—Eu1—C23	111.67 (11)	C14—C13—H13	120.8
N2—Eu1—C23	91.88 (10)	C12—C13—H13	120.8
O5—Eu1—N3	143.86 (9)	C12—C13—C14	118.4 (5)
O5—Eu1—O3	144.93 (9)	C1—C2—C3	117.9 (5)
O5—Eu1—N1	71.70 (10)	C1—C2—H2	121.0
O5—Eu1—N2	120.54 (9)	C3—C2—H2	121.0
O5—Eu1—C23	140.78 (10)	C6—C7—H7	120.6
O2ⁱ—Eu1—N3	79.81 (10)	C8—C7—C6	118.8 (4)
O2ⁱ—Eu1—O3	123.25 (9)	C8—C7—H7	120.6
O2ⁱ—Eu1—O9	79.32 (9)	N1—C5—C6	116.4 (4)
O2ⁱ—Eu1—O4	72.62 (9)	N1—C5—C4	121.6 (4)
O2ⁱ—Eu1—O1	103.81 (10)	C4—C5—C6	122.0 (4)
O2ⁱ—Eu1—N1	146.64 (10)	C15—C14—C13	118.2 (4)
O2ⁱ—Eu1—N2	134.08 (10)	C15—C14—H14	120.9
O2ⁱ—Eu1—C23	98.09 (11)	C13—C14—H14	120.9
O2ⁱ—Eu1—O5	75.75 (10)	C11—C12—H12	119.8
C15—N3—Eu1	119.7 (3)	C13—C12—C11	120.5 (4)
C15—N3—C11	118.1 (4)	C13—C12—H12	119.8
C11—N3—Eu1	121.6 (3)	C29—C28—H28	120.1
C23—O3—Eu1	92.5 (2)	C27—C28—C29	119.9 (4)
C37—O9—Eu1	141.9 (3)	C27—C28—H28	120.1
C23—O4—Eu1	93.6 (2)	C31—C32—H32	120.0
C16—O1—Eu1	139.7 (3)	C31—C32—C33	120.0 (5)
C1—N1—Eu1	119.5 (3)	C33—C32—H32	120.0
C1—N1—C5	117.1 (4)	C17—C18—H18	119.7
C5—N1—Eu1	122.9 (3)	C17—C18—C19	120.5 (5)
C6—N2—Eu1	120.8 (3)	C19—C18—H18	119.7
C10—N2—Eu1	120.3 (3)	C10—C9—H9	120.8
C10—N2—C6	118.6 (3)	C8—C9—C10	118.4 (4)
N2—C6—C7	121.8 (4)	C8—C9—H9	120.8
N2—C6—C5	116.7 (3)	C31—C36—H36	119.9
C7—C6—C5	121.5 (4)	C31—C36—C35	120.3 (5)
C24—C25—H25	119.7	C35—C36—H36	119.9
C26—C25—H25	119.7	C7—C8—C9	120.5 (4)
C26—C25—C24	120.6 (4)	C7—C8—H8	119.7
C18—C17—C16	120.5 (4)	C9—C8—H8	119.7
C18—C17—C22	119.3 (4)	C26—C27—H27	119.5
C22—C17—C16	120.2 (4)	C28—C27—C26	121.0 (4)
C25—C24—C23	120.6 (3)	C28—C27—H27	119.5
C25—C24—C29	119.4 (4)	C36—C35—H35	120.4
C29—C24—C23	120.0 (4)	C34—C35—C36	119.2 (6)
O3—C23—Eu1	61.47 (19)	C34—C35—H35	120.4
O3—C23—O4	121.5 (3)	C17—C22—H22	120.2
O3—C23—C24	120.0 (3)	C21—C22—C17	119.5 (5)
O4—C23—Eu1	60.06 (19)	C21—C22—H22	120.2
O4—C23—C24	118.4 (4)	O7—C30—C31	122.9 (4)
C24—C23—Eu1	175.2 (3)	O7—C30—O6	124.5 (4)
O1—C16—C17	116.5 (3)	O6—C30—C31	112.6 (4)
O2—C16—O1	124.8 (4)	C32—C33—H33	120.4
O2—C16—C17	118.7 (4)	C34—C33—C32	119.3 (5)
N2—C10—C11	117.7 (3)	C34—C33—H33	120.4
N2—C10—C9	121.9 (4)	C22—C21—H21	119.4
C9—C10—C11	120.4 (4)	C20—C21—C22	121.2 (5)
N1—C1—H1	117.7	C20—C21—H21	119.4
N1—C1—C2	124.7 (4)	C18—C19—H19	120.3
C2—C1—H1	117.7	C20—C19—C18	119.4 (5)
C32—C31—C36	120.0 (4)	C20—C19—H19	120.3
C32—C31—C30	122.1 (4)	C21—C20—C19	120.0 (5)
C36—C31—C30	117.8 (4)	C21—C20—H20	120.0
C43—C38—C37	119.6 (4)	C19—C20—H20	120.0
C43—C38—C39	118.8 (4)	C35—C34—H34	119.4
C39—C38—C37	121.5 (4)	C33—C34—C35	121.1 (5)
C38—C43—H43	119.6	C33—C34—H34	119.4
C38—C43—C42	120.8 (4)	C30—O6—H6	109.5
C42—C43—H43	119.6	Eu1—O5—H5A	110.7
O9—C37—C38	116.3 (4)	Eu1—O5—H5B	110.3
O8—C37—O9	123.1 (4)	H5A—O5—H5B	108.3
O8—C37—C38	120.6 (4)	C16—O2—Eu1ⁱ	168.9 (3)
C24—C29—H29	120.2

Eu1—N3—C15—C14	170.4 (3)	C25—C24—C23—O3	161.1 (4)
Eu1—N3—C11—C10	10.9 (4)	C25—C24—C23—O4	−15.5 (6)
Eu1—N3—C11—C12	−169.6 (3)	C25—C24—C29—C28	−1.3 (6)
Eu1—O3—C23—O4	1.7 (4)	C25—C26—C27—C28	−0.6 (7)
Eu1—O3—C23—C24	−174.8 (3)	C17—C16—O2—Eu1ⁱ	138.9 (12)
Eu1—O9—C37—O8	14.9 (7)	C17—C18—C19—C20	−2.2 (8)
Eu1—O9—C37—C38	−163.1 (3)	C17—C22—C21—C20	0.1 (8)
Eu1—O4—C23—O3	−1.7 (4)	C24—C25—C26—C27	−1.0 (6)
Eu1—O4—C23—C24	174.8 (3)	C24—C29—C28—C27	−0.3 (7)
Eu1—O1—C16—C17	−178.2 (3)	C23—Eu1—N3—C15	−72.4 (3)
Eu1—O1—C16—O2	3.6 (7)	C23—Eu1—N3—C11	98.2 (3)
Eu1—N1—C1—C2	170.9 (3)	C23—Eu1—O9—C37	160.1 (4)
Eu1—N1—C5—C6	11.0 (4)	C23—Eu1—O1—C16	98.5 (4)
Eu1—N1—C5—C4	−170.2 (3)	C23—Eu1—N1—C1	98.4 (3)
Eu1—N2—C6—C7	173.7 (3)	C23—Eu1—N1—C5	−90.0 (3)
Eu1—N2—C6—C5	−6.5 (4)	C23—Eu1—N2—C6	121.9 (3)
Eu1—N2—C10—C11	5.1 (4)	C23—Eu1—N2—C10	−64.5 (3)
Eu1—N2—C10—C9	−173.7 (3)	C23—C24—C29—C28	176.9 (4)
N3—Eu1—O3—C23	79.5 (2)	C16—C17—C18—C19	−178.8 (4)
N3—Eu1—O9—C37	167.1 (4)	C16—C17—C22—C21	179.8 (4)
N3—Eu1—O4—C23	−79.4 (2)	C10—N2—C6—C7	0.1 (5)
N3—Eu1—O1—C16	95.0 (4)	C10—N2—C6—C5	179.8 (3)
N3—Eu1—N1—C1	176.6 (3)	C10—C11—C12—C13	178.2 (4)
N3—Eu1—N1—C5	−11.9 (3)	C10—C9—C8—C7	0.7 (6)
N3—Eu1—N2—C6	−173.5 (3)	C1—N1—C5—C6	−177.3 (3)
N3—Eu1—N2—C10	0.1 (2)	C1—N1—C5—C4	1.5 (6)
N3—Eu1—C23—O3	−90.9 (2)	C31—C32—C33—C34	0.5 (7)
N3—Eu1—C23—O4	90.8 (2)	C31—C36—C35—C34	−1.1 (7)
N3—C15—C14—C13	−0.1 (7)	C38—C43—C42—C41	0.3 (6)
N3—C11—C12—C13	−1.3 (6)	C38—C39—C40—C41	1.1 (7)
O3—Eu1—N3—C15	−100.0 (3)	C43—C38—C37—O9	7.5 (5)
O3—Eu1—N3—C11	70.6 (3)	C43—C38—C37—O8	−170.6 (4)
O3—Eu1—O9—C37	122.8 (4)	C43—C38—C39—C40	−0.5 (6)
O3—Eu1—O4—C23	0.9 (2)	C43—C42—C41—C40	0.3 (7)
O3—Eu1—O1—C16	125.6 (4)	C37—C38—C43—C42	176.3 (4)
O3—Eu1—N1—C1	110.6 (3)	C37—C38—C39—C40	−176.9 (4)
O3—Eu1—N1—C5	−77.8 (3)	C29—C24—C23—O3	−17.0 (6)
O3—Eu1—N2—C6	107.8 (3)	C29—C24—C23—O4	166.4 (4)
O3—Eu1—N2—C10	−78.6 (3)	C29—C28—C27—C26	1.2 (7)
O3—Eu1—C23—O4	−178.3 (4)	C3—C4—C5—N1	−0.5 (6)
O9—Eu1—N3—C15	112.1 (3)	C3—C4—C5—C6	178.2 (4)
O9—Eu1—N3—C11	−77.4 (3)	C42—C41—C40—C39	−1.0 (7)
O9—Eu1—O3—C23	125.0 (2)	C15—N3—C11—C10	−178.4 (3)
O9—Eu1—O4—C23	−115.8 (2)	C15—N3—C11—C12	1.1 (5)
O9—Eu1—O1—C16	−86.5 (4)	C11—N3—C15—C14	−0.5 (6)
O9—Eu1—N1—C1	−115.0 (3)	C11—C10—C9—C8	−179.2 (4)
O9—Eu1—N1—C5	56.6 (3)	C39—C38—C43—C42	−0.2 (6)
O9—Eu1—N2—C6	−88.6 (3)	C39—C38—C37—O9	−176.1 (4)
O9—Eu1—N2—C10	85.0 (3)	C39—C38—C37—O8	5.9 (6)
O9—Eu1—C23—O3	−83.6 (3)	C26—C25—C24—C23	−176.2 (4)
O9—Eu1—C23—O4	98.1 (3)	C26—C25—C24—C29	1.9 (6)
O4—Eu1—N3—C15	−44.4 (3)	C4—C3—C2—C1	1.3 (7)
O4—Eu1—N3—C11	126.2 (3)	C2—C3—C4—C5	−0.9 (7)
O4—Eu1—O3—C23	−0.9 (2)	C7—C6—C5—N1	177.2 (3)
O4—Eu1—O9—C37	−157.4 (4)	C7—C6—C5—C4	−1.6 (6)
O4—Eu1—O1—C16	70.6 (4)	C5—N1—C1—C2	−1.1 (6)
O4—Eu1—N1—C1	80.3 (3)	C5—C6—C7—C8	−179.4 (4)
O4—Eu1—N1—C5	−108.1 (3)	C14—C13—C12—C11	0.7 (7)
O4—Eu1—N2—C6	136.0 (2)	C12—C13—C14—C15	0.0 (6)
O4—Eu1—N2—C10	−50.5 (3)	C32—C31—C36—C35	1.1 (7)
O4—Eu1—C23—O3	178.3 (4)	C32—C31—C30—O7	167.6 (4)
O1—Eu1—N3—C15	−68.8 (3)	C32—C31—C30—O6	−14.4 (6)
O1—Eu1—N3—C11	101.7 (3)	C32—C33—C34—C35	−0.5 (8)
O1—Eu1—O3—C23	−80.2 (2)	C18—C17—C16—O1	−5.0 (6)
O1—Eu1—O9—C37	−11.9 (5)	C18—C17—C16—O2	173.4 (4)
O1—Eu1—O4—C23	84.3 (2)	C18—C17—C22—C21	−0.5 (7)
O1—Eu1—N1—C1	37.0 (3)	C18—C19—C20—C21	1.7 (9)
O1—Eu1—N1—C5	−151.5 (3)	C9—C10—C11—N3	168.4 (3)
O1—Eu1—N2—C6	52.9 (3)	C9—C10—C11—C12	−11.1 (6)
O1—Eu1—N2—C10	−133.6 (3)	C36—C31—C32—C33	−0.7 (6)
O1—Eu1—C23—O3	91.6 (2)	C36—C31—C30—O7	−9.4 (6)
O1—Eu1—C23—O4	−86.8 (2)	C36—C31—C30—O6	168.5 (4)
O1—C16—O2—Eu1ⁱ	−42.9 (16)	C36—C35—C34—C33	0.8 (8)
N1—Eu1—N3—C15	−174.6 (3)	C22—C17—C16—O1	174.7 (4)
N1—Eu1—N3—C11	−4.1 (3)	C22—C17—C16—O2	−7.0 (6)
N1—Eu1—O3—C23	−153.3 (2)	C22—C17—C18—C19	1.5 (7)
N1—Eu1—O9—C37	39.7 (4)	C22—C21—C20—C19	−0.7 (9)
N1—Eu1—O4—C23	40.5 (3)	C30—C31—C32—C33	−177.7 (4)
N1—Eu1—O1—C16	−141.0 (4)	C30—C31—C36—C35	178.2 (4)
N1—Eu1—N2—C6	8.3 (2)	O5—Eu1—N3—C15	78.5 (3)
N1—Eu1—N2—C10	−178.2 (3)	O5—Eu1—N3—C11	−111.0 (3)
N1—Eu1—C23—O3	28.9 (3)	O5—Eu1—O3—C23	−98.9 (3)
N1—Eu1—C23—O4	−149.5 (2)	O5—Eu1—O9—C37	−32.7 (4)
N1—C1—C2—C3	−0.3 (7)	O5—Eu1—O4—C23	137.4 (2)
N2—Eu1—N3—C15	−176.5 (3)	O5—Eu1—O1—C16	−65.5 (4)
N2—Eu1—N3—C11	−6.0 (2)	O5—Eu1—N1—C1	−39.9 (3)
N2—Eu1—O3—C23	146.2 (3)	O5—Eu1—N1—C5	131.7 (3)
N2—Eu1—O9—C37	101.2 (4)	O5—Eu1—N2—C6	−34.9 (3)
N2—Eu1—O4—C23	−33.1 (3)	O5—Eu1—N2—C10	138.6 (2)
N2—Eu1—O1—C16	178.7 (4)	O5—Eu1—C23—O3	116.1 (2)
N2—Eu1—N1—C1	178.5 (3)	O5—Eu1—C23—O4	−62.2 (3)
N2—Eu1—N1—C5	−10.0 (3)	O2ⁱ—Eu1—N3—C15	30.6 (3)
N2—Eu1—C23—O3	−31.5 (2)	O2ⁱ—Eu1—N3—C11	−158.9 (3)
N2—Eu1—C23—O4	150.2 (2)	O2ⁱ—Eu1—O3—C23	16.0 (3)
N2—C6—C7—C8	0.3 (6)	O2ⁱ—Eu1—O9—C37	−110.7 (4)
N2—C6—C5—N1	−2.6 (5)	O2ⁱ—Eu1—O4—C23	−164.3 (2)
N2—C6—C5—C4	178.6 (3)	O2ⁱ—Eu1—O1—C16	4.5 (4)
N2—C10—C11—N3	−10.4 (5)	O2ⁱ—Eu1—N1—C1	−53.1 (4)
N2—C10—C11—C12	170.0 (3)	O2ⁱ—Eu1—N1—C5	118.5 (3)
N2—C10—C9—C8	−0.3 (6)	O2ⁱ—Eu1—N2—C6	−134.9 (2)
C6—N2—C10—C11	178.8 (3)	O2ⁱ—Eu1—N2—C10	38.6 (3)
C6—N2—C10—C9	0.0 (5)	O2ⁱ—Eu1—C23—O3	−166.5 (2)
C6—C7—C8—C9	−0.7 (6)	O2ⁱ—Eu1—C23—O4	15.1 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O8ⁱⁱ	0.82	1.76	2.582 (4)	178
O5—H5A···O8	0.87	1.98	2.796 (4)	155
O5—H5B···O4ⁱ	0.87	1.95	2.768 (4)	155

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O8ⁱ	0.82	1.76	2.582 (4)	177.6
O5—H5A···O8	0.87	1.98	2.796 (4)	154.7
O5—H5B···O4ⁱⁱ	0.87	1.95	2.768 (4)	154.8

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

Acknowledgements

The authors acknowledge the National Science Foundation for their generous support (NSF-CAREER grant to RES, CHE-0846680).

References

Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dul, M.-C., Bourgeois, D., Maynadie, J. & Meyer, D. (2013). Tetrahedron Lett. 54, 6271–6274. Web of Science CrossRef CAS Google Scholar
Fiedler, T., Hilder, M., Junk, P. C., Kynast, U. H., Lezhnina, M. M. & Warzala, M. (2007). Eur. J. Inorg, Chem. pp. 291–301. Google Scholar
Frost, G. H., Hart, F. A., Heath, C. & Hursthouse, M. B. (1969). J. Chem. Soc. D, 23, 1421–1422. CSD CrossRef Web of Science Google Scholar
Messimeri, A., Papadimitriou, C., Raptopoulou, C. P., Escuer, A., Perlepes, S. P. & Boudalis, A. K. (2007). Inorg. Chem. Commun. 10, 800–804. Web of Science CSD CrossRef CAS Google Scholar
Romero, V. H., De la Rosa, E., Salas, P. & Velazquez-Salazar, J. J. (2012). J. Solid State Chem. 196, 243–248. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages m328-m329

doi:10.1107/S1600536814018182

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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