Tetra-ethyl-ammonium tetra-kis-(1,1,1,5,5,5-hexa-fluoro-acetyl-acetonato)terbate(III).

The title compound, (C(8)H(20)N)[Tb(C(5)HF(6)O(2))(4)], is a tetrakis β-diketonate complex of hexa-fluoro-acetyl-acetone with terbium(III), and tetra-ethyl-ammonium 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 anti-prism. One hexa-fluoro-acetyl-acetone ligand has a disordered CF(3) 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 inter-actions.

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 = 1117.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.123

S = 0.98

6876 reflections

591 parameters

90 restraints

H-atom parameters constrained

Δρmax = 1.51 e Å−3

Δρmin = −1.24 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055437/pk2378sup1.cif

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

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

(C8H20N)[Tb(C5HF6O2)4]	F(000) = 2176
Mr = 1117.41	Dx = 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

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	Rint = 0.064
Detector resolution: 10.35 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω scans	h = −10→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→19
Tmin = 0.531, Tmax = 0.820	l = −21→21
14178 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3
6876 reflections	(Δ/σ)max = 0.001
591 parameters	Δρmax = 1.51 e Å−3
90 restraints	Δρmin = −1.24 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) ; (ii) ; (iii) .