Tetra­ethyl­ammonium tetra­kis­(1,1,1,5,5,5-hexa­fluoro­acetyl­acetonato)terbate(III)

Van Deun, R.; Van Der Voort, P.; Van Driessche, I.; Van Hecke, K.

doi:10.1107/S1600536811055437

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m111-m112

doi:10.1107/S1600536811055437

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Tetraethylammonium tetrakis(1,1,1,5,5,5-hexafluoroacetylacetonato)terbate(III)

Rik Van Deun,^a Pascal Van Der Voort,^a Isabel Van Driessche ^a and Kristof Van Hecke ^a ^*

^aDepartment of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281–S3, B-9000 Ghent, Belgium
^*Correspondence e-mail: Kristof.VanHecke@UGent.be

(Received 14 December 2011; accepted 23 December 2011; online 7 January 2012)

The title compound, (C₈H₂₀N)[Tb(C₅HF₆O₂)₄], is a tetrakis β-diketonate complex of hexafluoroacetylacetone with terbium(III), and tetraethylammonium as the counter-ion. This compound shows typical green terbium(III) luminescence upon excitation at about 335 nm. The coordination geometry around the Tb^III atom is a slightly distorted square antiprism. One hexafluoroacetylacetone ligand has a disordered CF₃ group [occupancies of 0.575 (4) and 0.425 (4)]. A three-dimensional network is built up by linkage of Tb^III complexes via C—H⋯F interactions.

Related literature

For a review on rare-earth β-diketonate complexes, their crystal structures and applications, see: Binnemans (2005 ). We have widely studied rare-earth β-diketonate complexes for their luminescence properties (Mech et al., 2008 ; Van Deun et al., 2007 ), either as pure materials, doped in liquid crystals (Van Deun et al., 2003 ; Nockemann et al., 2005 ), or processed into thin films (Lenaerts et al., 2005 , O'Riordan et al., 2005 ). For related structures, see: Tang & Mudring (2009 ); Danford et al. (1970 ); Lunstroot et al. (2009 ); Mehdi et al. (2010 ). For general procedues for the synthesis of rare-earth β-diketonate complexes, see: Melby et al. (1964 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

(C₈H₂₀N)[Tb(C₅HF₆O₂)₄]
M_r = 1117.41
Monoclinic, P 2₁ /n
a = 12.7113 (9) Å
b = 16.9355 (13) Å
c = 18.3540 (11) Å
β = 94.657 (6)°
V = 3938.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 100 K
0.4 × 0.1 × 0.1 mm

Data collection

Agilent SuperNova Dual Cu at zero Atlas diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.531, T_max = 0.820
14178 measured reflections
6876 independent reflections
4772 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.123
S = 0.98
6876 reflections
591 parameters
90 restraints
H-atom parameters constrained
Δρ_max = 1.51 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Selected bond lengths (Å)

Tb1—O1	2.373 (3)
Tb1—O2	2.351 (4)
Tb1—O3	2.345 (3)
Tb1—O4	2.369 (4)
Tb1—O5	2.372 (3)
Tb1—O6	2.351 (3)
Tb1—O7	2.359 (4)
Tb1—O8	2.365 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯F20ⁱ	0.95	2.51	3.430 (6)	164
C21—H21A⋯F10ⁱⁱ	0.99	2.47	3.279 (7)	139
C26—H26C⋯F14ⁱⁱⁱ	0.98	2.49	3.451 (7)	169
C27—H27B⋯F2Aⁱⁱⁱ	0.99	2.48	3.371 (9)	149
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); 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: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055437/pk2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055437/pk2378Isup2.hkl

checkCIF report

Comment top

β-diketones (1,3-diketones) are able to coordinate, as conjugate bases, to rare-earth ions, forming the corresponding β-diketonate complexes. Because of the accessibility to different commercially available β-diketones and the fact that the derived rare-earth complexes are relatively easy to synthesize, these β-diketonates have become the most scientifically studied and the most popular rare-earth coordination compounds.

For instance, rare-earth β-diketonates have been investigated as extractants in solvent-solvent extraction processes, as NMR shift reagents, as active materials in liquid lasers and novel types of organic light-emitting diodes (OLEDs), as active compounds in electroluminescent devices (e.g. flat-panel displays), as luminescent probes in bioassays, as precursors for chemical vapor deposition and as catalysts in organic reactions. These rare-earth β-diketonate complexes can be grouped into three main types: tris complexes, Lewis base adducts of the tris complexes (or ternary rare-earth β-diketonates) and tetrakis complexes.

An overiew of the different types of rare-earth β-diketonate complexes, their crystal structures and applications, is given by Binnemans, 2005.

We have widely studied rare-earth β-diketonate complexes for their luminescence properties (Mech et al., 2008; Van Deun et al., 2007), either as pure materials, doped in liquid crystals (Van Deun et al., 2003; Nockemann et al., 2005), or processed into thin films (Lenaerts et al., 2005, O'Riordan et al., 2005) and have recently determined other tetrakis rare-earth β-diketonate complexes with hexafluoroacetylacetone ligands (Lunstroot et al., 2009; Mehdi et al., 2010).

Here, we describe the crystal structure of a tetrakis complex of hexafluoroacetylacetone (hfac) with the terbium cation, Tb(III), and tetraethylammonium (Et₄N) as the counter ion, which shows typical green Tb(III) luminescence upon excitation at about 335 nm.

The title compound crystallizes in the monoclinic space group P2₁/n, with four formula units in the unit cell. The asymmetric unit consists of one Tb(III) cation, four hfac anions and one Et₄N cation, which in total equals one formula unit. Each Tb(III) ion is eight-coordinated by oxygen atoms from four chelating hfac ligands. The coordination polyhedron around Tb(III) can be best described as a slightly distorted square antiprism (Figure 1). There are no solvent molecules coordinating to the Tb(III) ion. One of the CF₃ groups of one of the hfac ligands is found disordered. The Tb–O distances range from 2.345 (3) to 2.373 (3) Å, which are comparable to those reported for other tetrakis(acetylacetonato)-Tb(III) complexes (Tang & Mudring, 2009) (Table 1). The O–Tb–O angles range from 73.81 (12)° to 75.19 (12)°. The only other tetrakis(acetylacetonato)-Tb(III) complex, found in the Cambridge Structural Database (CSD) has a Cs⁺ counterion (Danford et al., 1970). However, no coordinates are available for the latter structure (reference code QQQBZM, CSD (Version 5.32) (Allen, 2002)).

No classic hydrogen bonds are found. However, C–H···F potential hydrogen bonds can be observed within the [Tb(hfac)₄]^- anion itself (intraanion), between the [Tb(hfac)₄]^- anion and [Et₄N]⁺ cations (interanion-cation), as well as between different [Tb(hfac)₄]^- anions (interanion-anion). The acidic hydrogen atom in each hfac ligand forms at least one intraanion hydrogen bond with a fluorine atom of one of its adjacent CF₃ groups (C(–H)···F distances ranging from 2.713 (7) to 2.743 (6) Å). Several interanion-cation hydrogen bonds are observed between the [Tb(hfac)₄]^- anion and the [Et₄N]⁺ cations ((C(–H)···F distances ranging from 3.279 (7) to 3.451 (7) Å). Furthermore, one acidic hfac proton forms a C–H···F intermolecular interanion-anion hydrogen bond with a symmetry-equivalent hfac fluorine atom (C(13)(–H)···F(20) [2 - x,1 - y,-z] distance of 3.430 (6) Å) (Figure 2). Through the linkage of these intra- and intermolecular C–H···F interactions, a two-dimensional layer is formed in the (010)-plane. These layers are further building up a three-dimensional network, with the hfac CF₃ groups at the interfaces of the layers, as has been already noticed for other Tb(hfac)₄ complexes, although with different C₄mim and C₄mpyr counterions (Tang & Mudring, 2009) (Figure 3).

Related literature top

For a review on rare-earth β-diketonate complexes, their crystal structures and applications, see: Binnemans (2005). We have widely studied rare-earth β-diketonate complexes for their luminescence properties (Mech et al., 2008; Van Deun et al., 2007), either as pure materials, doped in liquid crystals (Van Deun et al., 2003; Nockemann et al., 2005), or processed into thin films (Lenaerts et al., 2005, O'Riordan et al., 2005). For related structures, see: Tang & Mudring (2009); Danford et al. (1970); Lunstroot et al. (2009); Mehdi et al. (2010). For general procedues for the synthesis of rare-earth β-diketonate complexes, see: Melby et al. (1964). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

General synthetic procedues for the synthesis of rare-earth β-diketonate complexes are given in Melby et al., 1964.

The title compound was synthesized by mixing 3.6 ml of a 1 N sodium hydroxide solution with 9 ml of an ethanol (95%(v/v)) solution of hexafluoroacetylacetone (0.505 ml, 3.6 mmol) in a 50 ml Erlenmeyer flask at 60 °C. Subsequently, under stirring, 9 ml of aqueous Tb(NO₃)₃.5H₂O solution (0.3906 g, 0.9 mmol) was added dropwise and finally 1.8 ml of aqueous tetraethylammonium chloride solution (0.0705 g, 0.426 mmol) was added dropwise. The mixture was concentrated by heating until the onset of crystallization. Finally, the solution was filtered and kept overnight to stand at room temperature, to allow the formation of single crystals.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Coordination geometry of the title compound, showing 50% probability displacement ellipsoids. The disorder of one of the CF₃ groups is not shown.
	Fig. 2. Intraanion, interanion-cation and interanion-anion C–H···F interactions (dashed lines), observed in the crystal structure of the title compound.
	Fig. 3. Packing diagram of the title compound along the b-axis, showing the two-dimensional layer formed in the (010)-plane (left) and along the c-axis, showing the three-dimensional network, with the hfac CF₃ groups at the interfaces of the layers (right). The interanion-cation and interanion-anion C–H···F interactions are indicated. H-atoms were omitted to enhance clarity.

Tetraethylammonium tetrakis(1,1,1,5,5,5-hexafluoroacetylacetonato)terbate(III) top

Crystal data top

(C₈H₂₀N)[Tb(C₅HF₆O₂)₄]	F(000) = 2176
M_r = 1117.41	D_x = 1.885 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3060 reflections
a = 12.7113 (9) Å	θ = 2.4–28.4°
b = 16.9355 (13) Å	µ = 1.96 mm⁻¹
c = 18.3540 (11) Å	T = 100 K
β = 94.657 (6)°	Needle, colourless
V = 3938.1 (5) Å³	0.4 × 0.1 × 0.1 mm
Z = 4

Data collection top

Agilent SuperNova Dual Cu at zero Atlas diffractometer	6876 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4772 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.064
Detector resolution: 10.35 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω scans	h = −10→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→19
T_min = 0.531, T_max = 0.820	l = −21→21
14178 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0477P)²] where P = (F_o² + 2F_c²)/3
6876 reflections	(Δ/σ)_max = 0.001
591 parameters	Δρ_max = 1.51 e Å⁻³
90 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

(C₈H₂₀N)[Tb(C₅HF₆O₂)₄]	V = 3938.1 (5) Å³
M_r = 1117.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7113 (9) Å	µ = 1.96 mm⁻¹
b = 16.9355 (13) Å	T = 100 K
c = 18.3540 (11) Å	0.4 × 0.1 × 0.1 mm
β = 94.657 (6)°

Data collection top

Agilent SuperNova Dual Cu at zero Atlas diffractometer	6876 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4772 reflections with I > 2σ(I)
T_min = 0.531, T_max = 0.820	R_int = 0.064
14178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	90 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 0.98	Δρ_max = 1.51 e Å⁻³
6876 reflections	Δρ_min = −1.24 e Å⁻³
591 parameters

Special details top

Experimental. CrysAlisPro. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Agilent Technologies, 2010)

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	Occ. (<1)
C1	0.8770 (4)	−0.0312 (3)	0.0638 (2)	0.0408 (18)
C2	0.8119 (5)	0.0356 (3)	0.0246 (3)	0.0269 (14)
C3	0.7175 (5)	0.0124 (3)	−0.0131 (3)	0.0344 (16)
H3	0.6992	−0.0420	−0.0135	0.041*
C4	0.6495 (4)	0.0647 (3)	−0.0499 (3)	0.0262 (14)
C5	0.5548 (5)	0.0315 (4)	−0.0952 (3)	0.0397 (17)
C6	0.6132 (4)	0.1453 (3)	0.2003 (3)	0.0259 (14)
C7	0.6239 (5)	0.1927 (3)	0.1298 (2)	0.0251 (14)
C8	0.5408 (4)	0.2398 (3)	0.1044 (3)	0.0206 (13)
H8	0.4770	0.2379	0.1280	0.025*
C9	0.5479 (5)	0.2907 (3)	0.0443 (3)	0.0240 (14)
C10	0.4618 (5)	0.3541 (3)	0.0308 (3)	0.0299 (15)
C11	0.8151 (6)	0.4535 (3)	0.1453 (3)	0.0407 (18)
C12	0.8176 (5)	0.4065 (3)	0.0732 (3)	0.0314 (15)
C13	0.8257 (5)	0.4492 (3)	0.0096 (3)	0.0414 (18)
H13	0.8368	0.5046	0.0127	0.050*
C14	0.8179 (5)	0.4129 (3)	−0.0592 (3)	0.0292 (15)
C15	0.8325 (5)	0.4656 (3)	−0.1259 (3)	0.0400 (18)
C16	1.1411 (5)	0.2831 (3)	−0.0144 (3)	0.0295 (15)
C17	1.0321 (4)	0.2525 (3)	−0.0428 (3)	0.0227 (14)
C18	1.0187 (4)	0.2291 (3)	−0.1155 (3)	0.0240 (14)
H18	1.0745	0.2370	−0.1462	0.029*
C19	0.9261 (4)	0.1948 (3)	−0.1440 (3)	0.0204 (13)
C20	0.9233 (5)	0.1624 (3)	−0.2223 (3)	0.0301 (15)
C21	0.0392 (5)	0.1360 (3)	0.3084 (3)	0.0389 (17)
H21A	0.0257	0.1631	0.3546	0.047*
H21B	0.1117	0.1143	0.3145	0.047*
C22	−0.0386 (6)	0.0668 (4)	0.2971 (3)	0.053 (2)
H22A	−0.1111	0.0870	0.2946	0.080*
H22B	−0.0276	0.0298	0.3380	0.080*
H22C	−0.0268	0.0396	0.2513	0.080*
C23	−0.0751 (5)	0.2336 (4)	0.2359 (3)	0.0406 (17)
H23A	−0.0736	0.2741	0.1970	0.049*
H23B	−0.1255	0.1921	0.2179	0.049*
C24	−0.1160 (6)	0.2718 (4)	0.3030 (4)	0.058 (2)
H24A	−0.1166	0.2327	0.3423	0.086*
H24B	−0.1878	0.2914	0.2908	0.086*
H24C	−0.0700	0.3159	0.3191	0.086*
C25	0.1164 (5)	0.2586 (3)	0.2736 (3)	0.0367 (17)
H25A	0.1862	0.2328	0.2823	0.044*
H25B	0.0976	0.2809	0.3207	0.044*
C27	0.0568 (5)	0.1617 (4)	0.1757 (3)	0.0431 (18)
H27A	0.0536	0.2041	0.1385	0.052*
H27B	0.0007	0.1230	0.1609	0.052*
C28	0.1652 (5)	0.1201 (4)	0.1762 (3)	0.049 (2)
H28A	0.2211	0.1569	0.1940	0.074*
H28B	0.1772	0.1031	0.1265	0.074*
H28C	0.1662	0.0740	0.2085	0.074*
C26	0.1247 (5)	0.3262 (3)	0.2183 (3)	0.050 (2)
H26A	0.1509	0.3053	0.1734	0.076*
H26B	0.1737	0.3664	0.2393	0.076*
H26C	0.0550	0.3498	0.2071	0.076*
N1	0.0347 (3)	0.1967 (2)	0.2478 (2)	0.0238 (11)
O1	0.8526 (3)	0.1026 (2)	0.03109 (17)	0.0249 (9)
O2	0.6578 (3)	0.1386 (2)	−0.05394 (18)	0.0276 (10)
O3	0.7119 (3)	0.1847 (2)	0.10428 (17)	0.0260 (9)
O4	0.6180 (3)	0.2930 (2)	0.00045 (17)	0.0266 (10)
O5	0.8142 (3)	0.3344 (2)	0.08163 (17)	0.0271 (10)
O6	0.7992 (3)	0.34237 (19)	−0.07428 (17)	0.0243 (9)
O7	0.9674 (3)	0.24911 (18)	0.00547 (17)	0.0221 (9)
O8	0.8409 (3)	0.18631 (19)	−0.11522 (17)	0.0233 (9)
F1B	0.8437 (7)	−0.0451 (6)	0.1273 (3)	0.069 (3)	0.425 (4)
F2B	0.9779 (5)	−0.0073 (4)	0.0802 (4)	0.044 (2)	0.425 (4)
F3B	0.8865 (8)	−0.0927 (4)	0.0223 (4)	0.060 (3)	0.425 (4)
F1A	0.8147 (5)	−0.0854 (3)	0.0929 (3)	0.0524 (18)	0.575 (4)
F2A	0.9494 (6)	−0.0096 (4)	0.1126 (3)	0.069 (2)	0.575 (4)
F3A	0.9235 (5)	−0.0736 (3)	0.0135 (3)	0.0427 (18)	0.575 (4)
F4	0.5671 (3)	0.0363 (2)	−0.16613 (18)	0.0701 (13)
F5	0.5332 (3)	−0.0435 (2)	−0.07899 (19)	0.0610 (12)
F6	0.4669 (3)	0.0730 (2)	−0.0848 (2)	0.0661 (13)
F7	0.6745 (3)	0.17776 (19)	0.25596 (15)	0.0388 (9)
F8	0.6463 (3)	0.07081 (17)	0.19320 (15)	0.0371 (9)
F9	0.5163 (3)	0.14256 (19)	0.22091 (16)	0.0390 (9)
F10	0.4251 (3)	0.3581 (2)	−0.03773 (16)	0.0535 (11)
F11	0.5033 (3)	0.4249 (2)	0.0478 (2)	0.0693 (14)
F12	0.3802 (3)	0.3450 (2)	0.07027 (17)	0.0517 (11)
F13	0.8205 (4)	0.5301 (2)	0.13763 (19)	0.0816 (15)
F14	0.8916 (3)	0.4309 (2)	0.19396 (16)	0.0477 (11)
F15	0.7254 (3)	0.4379 (3)	0.17600 (19)	0.0700 (13)
F16	0.9110 (3)	0.5157 (2)	−0.11361 (19)	0.0645 (12)
F17	0.8480 (4)	0.4257 (2)	−0.18469 (18)	0.0783 (15)
F18	0.7465 (4)	0.5087 (2)	−0.1421 (2)	0.0771 (14)
F19	1.1866 (3)	0.2368 (2)	0.03637 (18)	0.0454 (10)
F20	1.1322 (3)	0.3534 (2)	0.0180 (2)	0.0636 (13)
F21	1.2065 (3)	0.2928 (3)	−0.06505 (18)	0.0653 (13)
F22	0.8784 (3)	0.09067 (18)	−0.22706 (16)	0.0432 (10)
F23	1.0188 (3)	0.1542 (2)	−0.24729 (15)	0.0422 (10)
F24	0.8672 (3)	0.20959 (19)	−0.26958 (14)	0.0343 (9)
Tb1	0.78328 (2)	0.228824 (14)	−0.002340 (13)	0.02031 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (5)	0.020 (3)	0.040 (3)	0.002 (3)	0.000 (3)	−0.007 (3)
C2	0.037 (4)	0.024 (3)	0.021 (3)	0.008 (3)	0.008 (2)	0.003 (2)
C3	0.051 (4)	0.020 (3)	0.029 (3)	0.002 (3)	−0.011 (3)	−0.009 (2)
C4	0.032 (3)	0.015 (3)	0.033 (3)	−0.001 (2)	0.013 (3)	0.003 (2)
C5	0.046 (4)	0.037 (3)	0.035 (3)	−0.020 (3)	−0.010 (3)	0.009 (3)
C6	0.024 (3)	0.026 (3)	0.030 (3)	−0.002 (3)	0.010 (2)	0.003 (2)
C7	0.036 (4)	0.025 (3)	0.014 (2)	−0.007 (3)	0.001 (2)	−0.007 (2)
C8	0.018 (3)	0.022 (3)	0.022 (3)	−0.003 (2)	0.006 (2)	−0.005 (2)
C9	0.035 (3)	0.017 (3)	0.020 (3)	0.002 (2)	0.001 (2)	−0.004 (2)
C10	0.036 (4)	0.029 (3)	0.025 (3)	0.003 (3)	0.003 (3)	−0.002 (3)
C11	0.075 (5)	0.023 (3)	0.023 (3)	0.012 (3)	−0.002 (3)	−0.003 (3)
C12	0.039 (4)	0.028 (3)	0.028 (3)	0.003 (3)	0.004 (3)	−0.004 (3)
C13	0.077 (5)	0.021 (3)	0.027 (3)	0.001 (3)	0.008 (3)	−0.005 (3)
C14	0.042 (4)	0.012 (3)	0.034 (3)	0.005 (3)	0.004 (3)	0.009 (2)
C15	0.052 (4)	0.026 (3)	0.042 (3)	0.001 (3)	0.004 (3)	0.007 (3)
C16	0.028 (3)	0.029 (3)	0.033 (3)	−0.012 (3)	0.007 (3)	0.002 (3)
C17	0.032 (3)	0.012 (2)	0.025 (3)	−0.001 (2)	0.005 (2)	0.001 (2)
C18	0.027 (3)	0.024 (3)	0.021 (3)	−0.005 (3)	0.008 (2)	0.009 (2)
C19	0.030 (3)	0.010 (2)	0.021 (3)	0.001 (2)	0.003 (2)	0.002 (2)
C20	0.038 (4)	0.031 (3)	0.023 (3)	0.002 (3)	0.012 (3)	−0.001 (2)
C21	0.051 (4)	0.027 (3)	0.041 (3)	0.008 (3)	0.015 (3)	0.011 (3)
C22	0.074 (5)	0.030 (3)	0.057 (4)	−0.022 (3)	0.011 (4)	0.005 (3)
C23	0.039 (4)	0.038 (3)	0.045 (3)	−0.003 (3)	0.000 (3)	0.006 (3)
C24	0.059 (5)	0.049 (4)	0.069 (4)	−0.008 (4)	0.032 (4)	−0.022 (4)
C25	0.041 (4)	0.036 (3)	0.033 (3)	−0.007 (3)	0.002 (3)	−0.005 (3)
C27	0.054 (4)	0.041 (4)	0.034 (3)	−0.012 (3)	0.005 (3)	−0.007 (3)
C28	0.066 (5)	0.036 (4)	0.048 (4)	−0.001 (3)	0.022 (3)	−0.013 (3)
C26	0.052 (4)	0.025 (3)	0.077 (4)	−0.004 (3)	0.023 (4)	0.014 (3)
N1	0.027 (3)	0.026 (2)	0.019 (2)	−0.006 (2)	0.0032 (19)	−0.0013 (19)
O1	0.029 (2)	0.0205 (19)	0.0264 (18)	0.0043 (17)	0.0078 (16)	0.0028 (16)
O2	0.026 (2)	0.032 (2)	0.0256 (18)	−0.0020 (18)	0.0034 (16)	0.0074 (17)
O3	0.029 (2)	0.0207 (18)	0.0304 (19)	0.0034 (17)	0.0129 (17)	0.0044 (16)
O4	0.032 (2)	0.0250 (19)	0.0242 (18)	0.0027 (17)	0.0092 (17)	0.0089 (16)
O5	0.034 (2)	0.023 (2)	0.0253 (19)	0.0037 (18)	0.0094 (17)	−0.0015 (16)
O6	0.025 (2)	0.0208 (18)	0.0280 (19)	−0.0021 (17)	0.0061 (16)	0.0069 (16)
O7	0.030 (2)	0.0121 (17)	0.0242 (18)	−0.0036 (16)	0.0042 (17)	−0.0036 (15)
O8	0.028 (2)	0.0177 (18)	0.0242 (18)	−0.0004 (17)	0.0051 (16)	−0.0004 (16)
F1B	0.070 (5)	0.081 (5)	0.056 (4)	0.013 (4)	0.012 (4)	0.028 (4)
F2B	0.055 (5)	0.038 (4)	0.038 (4)	0.014 (4)	−0.009 (4)	0.004 (3)
F3B	0.068 (5)	0.033 (4)	0.077 (5)	0.005 (4)	−0.010 (4)	−0.003 (4)
F1A	0.053 (4)	0.044 (3)	0.062 (3)	0.010 (3)	0.019 (3)	0.037 (3)
F2A	0.094 (5)	0.045 (4)	0.060 (4)	0.008 (4)	−0.046 (4)	0.003 (3)
F3A	0.047 (4)	0.033 (3)	0.051 (3)	0.014 (3)	0.022 (3)	0.008 (3)
F4	0.097 (3)	0.080 (3)	0.0300 (19)	−0.047 (2)	−0.013 (2)	0.0041 (19)
F5	0.084 (3)	0.0315 (19)	0.062 (2)	−0.023 (2)	−0.031 (2)	0.0131 (18)
F6	0.045 (3)	0.066 (3)	0.083 (3)	−0.020 (2)	−0.019 (2)	0.014 (2)
F7	0.046 (2)	0.049 (2)	0.0212 (15)	−0.0158 (18)	0.0030 (15)	0.0005 (15)
F8	0.056 (2)	0.0237 (16)	0.0318 (16)	0.0019 (16)	0.0073 (16)	0.0088 (14)
F9	0.034 (2)	0.047 (2)	0.0382 (17)	−0.0094 (17)	0.0149 (15)	0.0119 (15)
F10	0.047 (2)	0.086 (3)	0.0270 (17)	0.032 (2)	0.0002 (16)	0.0033 (18)
F11	0.054 (3)	0.0249 (19)	0.126 (3)	0.0111 (19)	−0.011 (2)	−0.012 (2)
F12	0.046 (2)	0.069 (3)	0.0436 (18)	0.0258 (19)	0.0239 (17)	0.0135 (18)
F13	0.172 (4)	0.030 (2)	0.040 (2)	0.017 (2)	−0.006 (2)	−0.0085 (17)
F14	0.064 (3)	0.045 (2)	0.0326 (18)	0.0107 (19)	−0.0061 (18)	−0.0105 (16)
F15	0.056 (3)	0.105 (3)	0.050 (2)	0.018 (2)	0.0146 (19)	−0.040 (2)
F16	0.081 (3)	0.058 (2)	0.053 (2)	−0.036 (2)	0.004 (2)	0.021 (2)
F17	0.171 (4)	0.035 (2)	0.0339 (19)	−0.021 (3)	0.036 (2)	0.0034 (17)
F18	0.085 (3)	0.070 (3)	0.077 (3)	0.018 (3)	0.013 (2)	0.051 (2)
F19	0.041 (2)	0.047 (2)	0.0453 (19)	−0.0115 (18)	−0.0128 (17)	0.0125 (17)
F20	0.053 (3)	0.033 (2)	0.102 (3)	−0.0132 (19)	−0.005 (2)	−0.020 (2)
F21	0.036 (2)	0.124 (4)	0.0367 (19)	−0.038 (2)	0.0125 (17)	0.001 (2)
F22	0.067 (3)	0.0304 (18)	0.0317 (17)	−0.0021 (18)	0.0037 (17)	−0.0135 (15)
F23	0.041 (2)	0.059 (2)	0.0284 (17)	0.0141 (18)	0.0105 (15)	−0.0070 (16)
F24	0.036 (2)	0.049 (2)	0.0180 (15)	0.0086 (16)	0.0026 (14)	0.0032 (15)
Tb1	0.02640 (15)	0.01570 (12)	0.01963 (12)	0.00014 (12)	0.00668 (10)	0.00082 (11)

Geometric parameters (Å, º) top

C1—F2A	1.284 (6)	C17—O7	1.258 (6)
C1—F1B	1.293 (7)	C17—C18	1.390 (7)
C1—F3B	1.300 (7)	C18—C19	1.376 (7)
C1—F3A	1.344 (6)	C18—H18	0.9500
C1—F1A	1.350 (6)	C19—O8	1.251 (6)
C1—F2B	1.356 (7)	C19—C20	1.538 (7)
C1—C2	1.545 (7)	C20—F23	1.339 (6)
C2—O1	1.249 (6)	C20—F22	1.341 (6)
C2—C3	1.393 (8)	C20—F24	1.341 (6)
C3—C4	1.375 (8)	C21—N1	1.513 (7)
C3—H3	0.9500	C21—C22	1.536 (8)
C4—O2	1.259 (6)	C21—H21A	0.9900
C4—C5	1.514 (8)	C21—H21B	0.9900
C5—F4	1.326 (6)	C22—H22A	0.9800
C5—F5	1.338 (6)	C22—H22B	0.9800
C5—F6	1.348 (7)	C22—H22C	0.9800
C6—F9	1.318 (6)	C23—C24	1.520 (8)
C6—F8	1.340 (6)	C23—N1	1.528 (7)
C6—F7	1.350 (6)	C23—H23A	0.9900
C6—C7	1.537 (7)	C23—H23B	0.9900
C7—O3	1.255 (6)	C24—H24A	0.9800
C7—C8	1.375 (7)	C24—H24B	0.9800
C8—C9	1.410 (7)	C24—H24C	0.9800
C8—H8	0.9500	C25—N1	1.524 (7)
C9—O4	1.249 (6)	C25—C26	1.539 (8)
C9—C10	1.539 (8)	C25—H25A	0.9900
C10—F10	1.307 (6)	C25—H25B	0.9900
C10—F12	1.322 (6)	C27—N1	1.498 (7)
C10—F11	1.336 (6)	C27—C28	1.547 (9)
C11—F13	1.307 (6)	C27—H27A	0.9900
C11—F14	1.322 (7)	C27—H27B	0.9900
C11—F15	1.337 (8)	C28—H28A	0.9800
C11—C12	1.547 (7)	C28—H28B	0.9800
C12—O5	1.233 (6)	C28—H28C	0.9800
C12—C13	1.384 (7)	C26—H26A	0.9800
C13—C14	1.401 (7)	C26—H26B	0.9800
C13—H13	0.9500	C26—H26C	0.9800
C14—O6	1.244 (6)	Tb1—O1	2.373 (3)
C14—C15	1.538 (8)	Tb1—O2	2.351 (4)
C15—F17	1.302 (7)	Tb1—O3	2.345 (3)
C15—F16	1.315 (7)	Tb1—O4	2.369 (4)
C15—F18	1.328 (7)	Tb1—O5	2.372 (3)
C16—F21	1.307 (6)	Tb1—O6	2.351 (3)
C16—F19	1.315 (6)	Tb1—O7	2.359 (4)
C16—F20	1.340 (6)	Tb1—O8	2.365 (3)
C16—C17	1.531 (8)

F2A—C1—F1B	72.1 (5)	F23—C20—C19	113.8 (5)
F2A—C1—F3B	122.7 (6)	F22—C20—C19	111.2 (4)
F1B—C1—F3B	115.8 (6)	F24—C20—C19	111.3 (4)
F2A—C1—F3A	107.5 (5)	N1—C21—C22	115.7 (5)
F1B—C1—F3A	135.8 (6)	N1—C21—H21A	108.4
F2A—C1—F1A	109.2 (5)	C22—C21—H21A	108.4
F3B—C1—F1A	76.9 (5)	N1—C21—H21B	108.4
F3A—C1—F1A	102.4 (5)	C22—C21—H21B	108.4
F1B—C1—F2B	103.2 (6)	H21A—C21—H21B	107.4
F3B—C1—F2B	103.7 (6)	C21—C22—H22A	109.5
F3A—C1—F2B	81.4 (5)	C21—C22—H22B	109.5
F1A—C1—F2B	133.7 (5)	H22A—C22—H22B	109.5
F2A—C1—C2	116.2 (5)	C21—C22—H22C	109.5
F1B—C1—C2	110.5 (5)	H22A—C22—H22C	109.5
F3B—C1—C2	112.7 (5)	H22B—C22—H22C	109.5
F3A—C1—C2	108.6 (4)	C24—C23—N1	115.2 (5)
F1A—C1—C2	111.9 (4)	C24—C23—H23A	108.5
F2B—C1—C2	110.2 (5)	N1—C23—H23A	108.5
O1—C2—C3	129.5 (5)	C24—C23—H23B	108.5
O1—C2—C1	114.9 (5)	N1—C23—H23B	108.5
C3—C2—C1	115.6 (5)	H23A—C23—H23B	107.5
C4—C3—C2	123.0 (5)	C23—C24—H24A	109.5
C4—C3—H3	118.5	C23—C24—H24B	109.5
C2—C3—H3	118.5	H24A—C24—H24B	109.5
O2—C4—C3	128.0 (5)	C23—C24—H24C	109.5
O2—C4—C5	113.8 (5)	H24A—C24—H24C	109.5
C3—C4—C5	118.1 (5)	H24B—C24—H24C	109.5
F4—C5—F5	108.6 (5)	N1—C25—C26	112.8 (5)
F4—C5—F6	105.9 (5)	N1—C25—H25A	109.0
F5—C5—F6	106.0 (5)	C26—C25—H25A	109.0
F4—C5—C4	111.4 (5)	N1—C25—H25B	109.0
F5—C5—C4	113.5 (5)	C26—C25—H25B	109.0
F6—C5—C4	111.1 (5)	H25A—C25—H25B	107.8
F9—C6—F8	107.6 (4)	N1—C27—C28	113.9 (5)
F9—C6—F7	107.0 (4)	N1—C27—H27A	108.8
F8—C6—F7	106.8 (4)	C28—C27—H27A	108.8
F9—C6—C7	114.1 (4)	N1—C27—H27B	108.8
F8—C6—C7	111.1 (4)	C28—C27—H27B	108.8
F7—C6—C7	109.8 (4)	H27A—C27—H27B	107.7
O3—C7—C8	128.3 (5)	C27—C28—H28A	109.5
O3—C7—C6	113.7 (5)	C27—C28—H28B	109.5
C8—C7—C6	118.0 (5)	H28A—C28—H28B	109.5
C7—C8—C9	121.7 (5)	C27—C28—H28C	109.5
C7—C8—H8	119.2	H28A—C28—H28C	109.5
C9—C8—H8	119.2	H28B—C28—H28C	109.5
O4—C9—C8	128.1 (5)	C25—C26—H26A	109.5
O4—C9—C10	114.2 (4)	C25—C26—H26B	109.5
C8—C9—C10	117.6 (5)	H26A—C26—H26B	109.5
F10—C10—F12	107.4 (5)	C25—C26—H26C	109.5
F10—C10—F11	106.4 (5)	H26A—C26—H26C	109.5
F12—C10—F11	106.8 (4)	H26B—C26—H26C	109.5
F10—C10—C9	112.6 (4)	C27—N1—C21	112.4 (4)
F12—C10—C9	114.2 (4)	C27—N1—C25	112.0 (4)
F11—C10—C9	109.1 (5)	C21—N1—C25	104.8 (4)
F13—C11—F14	108.5 (5)	C27—N1—C23	105.6 (4)
F13—C11—F15	107.2 (5)	C21—N1—C23	111.3 (4)
F14—C11—F15	105.3 (4)	C25—N1—C23	110.8 (4)
F13—C11—C12	114.4 (5)	C2—O1—Tb1	130.7 (3)
F14—C11—C12	111.3 (5)	C4—O2—Tb1	132.8 (3)
F15—C11—C12	109.7 (5)	C7—O3—Tb1	134.0 (3)
O5—C12—C13	129.0 (5)	C9—O4—Tb1	132.9 (3)
O5—C12—C11	113.5 (4)	C12—O5—Tb1	132.2 (3)
C13—C12—C11	117.5 (5)	C14—O6—Tb1	133.1 (3)
C12—C13—C14	121.8 (5)	C17—O7—Tb1	131.8 (3)
C12—C13—H13	119.1	C19—O8—Tb1	132.4 (3)
C14—C13—H13	119.1	O3—Tb1—O6	141.84 (12)
O6—C14—C13	128.3 (5)	O3—Tb1—O2	80.42 (12)
O6—C14—C15	114.4 (5)	O6—Tb1—O2	113.06 (12)
C13—C14—C15	117.2 (5)	O3—Tb1—O7	116.42 (12)
F17—C15—F16	108.3 (5)	O6—Tb1—O7	77.57 (11)
F17—C15—F18	106.0 (5)	O2—Tb1—O7	139.15 (12)
F16—C15—F18	106.4 (5)	O3—Tb1—O8	143.35 (12)
F17—C15—C14	113.2 (5)	O6—Tb1—O8	73.15 (11)
F16—C15—C14	112.2 (5)	O2—Tb1—O8	72.40 (12)
F18—C15—C14	110.3 (5)	O7—Tb1—O8	73.80 (12)
F21—C16—F19	108.1 (5)	O3—Tb1—O4	74.01 (12)
F21—C16—F20	106.6 (5)	O6—Tb1—O4	75.75 (12)
F19—C16—F20	105.3 (4)	O2—Tb1—O4	74.53 (12)
F21—C16—C17	114.3 (4)	O7—Tb1—O4	144.01 (11)
F19—C16—C17	111.9 (4)	O8—Tb1—O4	119.80 (12)
F20—C16—C17	110.1 (5)	O3—Tb1—O5	75.68 (12)
O7—C17—C18	128.9 (5)	O6—Tb1—O5	74.41 (11)
O7—C17—C16	113.6 (4)	O2—Tb1—O5	145.33 (12)
C18—C17—C16	117.4 (5)	O7—Tb1—O5	74.91 (12)
C19—C18—C17	121.3 (5)	O8—Tb1—O5	138.75 (12)
C19—C18—H18	119.4	O4—Tb1—O5	74.97 (12)
C17—C18—H18	119.4	O3—Tb1—O1	69.99 (11)
O8—C19—C18	129.2 (5)	O6—Tb1—O1	146.60 (12)
O8—C19—C20	113.5 (4)	O2—Tb1—O1	75.19 (12)
C18—C19—C20	117.4 (5)	O7—Tb1—O1	76.69 (12)
F23—C20—F22	106.1 (4)	O8—Tb1—O1	79.48 (11)
F23—C20—F24	106.8 (4)	O4—Tb1—O1	135.94 (12)
F22—C20—F24	107.3 (4)	O5—Tb1—O1	118.18 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F5	0.95	2.34	2.718 (7)	103
C8—H8···F9	0.95	2.37	2.737 (6)	102
C8—H8···F12	0.95	2.39	2.743 (6)	102
C13—H13···F13	0.95	2.36	2.726 (6)	102
C13—H13···F20ⁱ	0.95	2.51	3.430 (6)	164
C18—H18···F21	0.95	2.35	2.713 (7)	102
C18—H18···F23	0.95	2.39	2.731 (6)	101
C21—H21A···F10ⁱⁱ	0.99	2.47	3.279 (7)	139
C26—H26C···F14ⁱⁱⁱ	0.98	2.49	3.451 (7)	169
C27—H27B···F2Aⁱⁱⁱ	0.99	2.48	3.371 (9)	149

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

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N)[Tb(C₅HF₆O₂)₄]
M_r	1117.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.7113 (9), 16.9355 (13), 18.3540 (11)
β (°)	94.657 (6)
V (Å³)	3938.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.4 × 0.1 × 0.1

Data collection
Diffractometer	Agilent SuperNova Dual Cu at zero Atlas diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.531, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	14178, 6876, 4772
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.123, 0.98
No. of reflections	6876
No. of parameters	591
No. of restraints	90
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.51, −1.24

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Tb1—O1	2.373 (3)	Tb1—O5	2.372 (3)
Tb1—O2	2.351 (4)	Tb1—O6	2.351 (3)
Tb1—O3	2.345 (3)	Tb1—O7	2.359 (4)
Tb1—O4	2.369 (4)	Tb1—O8	2.365 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F5	0.95	2.34	2.718 (7)	103
C8—H8···F9	0.95	2.37	2.737 (6)	102
C8—H8···F12	0.95	2.39	2.743 (6)	102
C13—H13···F13	0.95	2.36	2.726 (6)	102
C13—H13···F20ⁱ	0.95	2.51	3.430 (6)	164
C18—H18···F21	0.95	2.35	2.713 (7)	102
C18—H18···F23	0.95	2.39	2.731 (6)	101
C21—H21A···F10ⁱⁱ	0.99	2.47	3.279 (7)	139
C26—H26C···F14ⁱⁱⁱ	0.98	2.49	3.451 (7)	169
C27—H27B···F2Aⁱⁱⁱ	0.99	2.48	3.371 (9)	149

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

Acknowledgements

This research was co-funded by Ghent University, GOA grant No. 01 G00710.

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Volume 68| Part 2| February 2012| Pages m111-m112

doi:10.1107/S1600536811055437

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

Tetra­ethyl­ammonium tetra­kis­(1,1,1,5,5,5-hexa­fluoro­acetyl­acetonato)terbate(III)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Tetraethylammonium tetrakis(1,1,1,5,5,5-hexafluoroacetylacetonato)terbate(III)