Aqua-bis-(1,1,1,5,5,5-hexa-fluoro-acetyl-acetonato)[4'-(4-pyrid-yl)-2,2':6',2''-terpyridine]-ytterbium(III) chloride methanol monosolvate monohydrate.

The title compound, [Yb(C(5)HF(6)O(2))(2)(C(20)H(14)N(4))(H(2)O)]Cl·CH(3)OH·H(2)O, adopts an eight-coordinated geometry around the Yb(III) atom consisting of a 4'-(4-pyrid-yl)-2,2':6',2''-terpyridine (pytpy) ligand, two 1,1,1,5,5,5-hexa-fluoro-acetyl-acetonate (hfac) anions and an aqua ligand. In the solid state, the compound forms supra-molecular chains running along the b-axis via inter-molecular hydrogen bonds between the Yb-OH(2) unit and the N-atom donor of the 4-pyridyl pendant of pytpy, with an O⋯N distance of 2.686 (4) Å. A chloride counter-anion and lattice methanol and water solvent mol-ecules occupy a hydro-philic columnar space along the coordination chains. O-H⋯Cl hydrogen bonds occur. The two water molecules and the four trifluoromethyl groups are disordered over two sets of sites, each with different occupancy ratios.

Related literature

For general background to pytpy, see: Constable & Thompson (1992 ▶, 1994 ▶). For pytpy complexes, see: Sun et al. (2000 ▶); Sun & Lees (2001 ▶). For related Yb complexes, see: Fukuda et al. (2002 ▶); Hayashi et al. (1998 ▶); Przychodzen et al. (2007 ▶); Stojanovic et al. (2010 ▶); Li et al. (2007 ▶); Xu et al. (2009 ▶); Ahrens et al. (2002 ▶); Zhang et al. (2007a ▶). For potential applications of compounds with infinite one-dimensional to three-dimensional structures, see: Hayami et al. (2004 ▶); Hou et al. (2005 ▶); Feng et al. (2006 ▶); Beves et al. (2007a ▶); Zhang et al. (2007b ▶); Gou et al. (2008 ▶); Leong & Vittal (2011 ▶); Moulton & Zaworotko (2001 ▶). For the binding mode of pytpy involving hydrogen-bonding, see: Beves et al. (2007b ▶, 2008 ▶).

Experimental

Crystal data

[Yb(C5HF6O2)2(C20H14N4)(H2O)]Cl·CH4O·H2O

M = 1001.03

Triclinic,

a = 9.7559 (6) Å

b = 12.4035 (7) Å

c = 16.5543 (10) Å

α = 98.870 (1)°

β = 104.717 (1)°

γ = 93.559 (1)°

V = 1903.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.63 mm−1

T = 223 K

0.46 × 0.33 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.53, T max = 0.68

13523 measured reflections

9671 independent reflections

8205 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.081

S = 1.08

9671 reflections

587 parameters

34 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.02 e Å−3

Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker, 2010 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052378/mw2026sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052378/mw2026Isup2.hkl

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

[Yb(C5HF6O2)2(C20H14N4)(H2O)]Cl·CH4O·H2O	Z = 2
Mr = 1001.03	F(000) = 978
Triclinic, P1	Dx = 1.747 Mg m−3
a = 9.7559 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4035 (7) Å	Cell parameters from 4823 reflections
c = 16.5543 (10) Å	θ = 2.6–28.9°
α = 98.870 (1)°	µ = 2.63 mm−1
β = 104.717 (1)°	T = 223 K
γ = 93.559 (1)°	Prism, colourless
V = 1903.5 (2) Å3	0.46 × 0.33 × 0.16 mm

Bruker SMART APEX CCD diffractometer	9671 independent reflections
Radiation source: fine focus sealed tube	8205 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 8.3333 pixels mm-1	θmax = 28.7°, θmin = 1.7°
phi and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −13→16
Tmin = 0.53, Tmax = 0.68	l = −22→20
13523 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.030P)2 + 1.1P] where P = (Fo2 + 2Fc2)/3
9671 reflections	(Δ/σ)max = 0.001
587 parameters	Δρmax = 1.02 e Å−3
34 restraints	Δρmin = −0.88 e Å−3

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)
O7A	0.4270 (10)	0.9463 (10)	0.5369 (8)	0.135 (6)	0.584 (19)
H7A	0.4377	0.9366	0.489	0.203*	0.58
H7B	0.4045	0.9042	0.5548	0.203*	0.58
O7B	0.4211 (17)	0.9784 (8)	0.5886 (11)	0.101 (6)	0.416 (19)
H7C	0.4744	0.9843	0.633	0.151*	0.42
H7D	0.3432	0.9793	0.5672	0.151*	0.42
F1A	0.5633 (6)	0.4015 (4)	0.0987 (6)	0.132 (3)	0.809 (7)
F2A	0.7562 (8)	0.3375 (4)	0.1479 (3)	0.115 (2)	0.809 (7)
F3A	0.6812 (8)	0.3306 (5)	0.0145 (3)	0.106 (2)	0.809 (7)
C21A	0.6903 (11)	0.3909 (7)	0.0894 (4)	0.078 (2)	0.809 (7)
F4A	0.9969 (9)	0.7609 (6)	−0.0307 (5)	0.095 (2)	0.760 (10)
F5A	0.9299 (10)	0.5959 (5)	−0.0973 (3)	0.104 (2)	0.760 (10)
F6A	0.7780 (7)	0.7104 (9)	−0.0868 (5)	0.127 (3)	0.760 (10)
C25A	0.8965 (10)	0.6797 (7)	−0.0462 (5)	0.072 (2)	0.760 (10)
F7A	0.6123 (6)	1.0312 (4)	0.1179 (4)	0.136 (3)	0.901 (7)
F8A	0.5579 (6)	0.9439 (5)	0.2082 (4)	0.133 (2)	0.901 (7)
F9A	0.5449 (5)	0.8597 (4)	0.0849 (4)	0.126 (2)	0.901 (7)
C26A	0.6202 (8)	0.9367 (7)	0.1460 (6)	0.088 (2)	0.901 (7)
F10A	1.2675 (6)	1.0106 (4)	0.2103 (4)	0.1137 (19)	0.861 (6)
F11A	1.1197 (5)	1.1250 (3)	0.1800 (3)	0.0930 (14)	0.861 (6)
F12A	1.1272 (7)	0.9944 (5)	0.0843 (3)	0.136 (3)	0.861 (6)
C30A	1.1366 (8)	1.0194 (5)	0.1657 (5)	0.0693 (18)	0.861 (6)
F1B	0.547 (2)	0.4106 (19)	0.0297 (19)	0.132 (3)	0.191 (7)
F2B	0.654 (4)	0.3824 (19)	0.1497 (14)	0.115 (2)	0.191 (7)
F3B	0.724 (3)	0.328 (3)	0.0454 (16)	0.106 (2)	0.191 (7)
C21B	0.672 (3)	0.413 (3)	0.0808 (18)	0.078 (2)	0.191 (7)
F4B	1.023 (3)	0.727 (2)	−0.0193 (17)	0.095 (2)	0.240 (10)
F5B	0.844 (3)	0.627 (2)	−0.1050 (12)	0.104 (2)	0.240 (10)
F6B	0.808 (2)	0.774 (2)	−0.0447 (14)	0.127 (3)	0.240 (10)
C25B	0.889 (3)	0.697 (2)	−0.0299 (18)	0.072 (2)	0.240 (10)
F7B	0.643 (6)	1.055 (4)	0.168 (3)	0.136 (3)	0.099 (7)
F8B	0.548 (6)	0.892 (4)	0.153 (4)	0.133 (2)	0.099 (7)
F9B	0.615 (4)	0.944 (4)	0.054 (3)	0.126 (2)	0.099 (7)
C26B	0.650 (6)	0.951 (4)	0.137 (3)	0.088 (2)	0.099 (7)
F10B	1.237 (4)	1.053 (3)	0.215 (2)	0.1137 (19)	0.139 (6)
F11B	1.095 (3)	1.080 (2)	0.109 (2)	0.0930 (14)	0.139 (6)
F12B	1.203 (4)	0.931 (3)	0.102 (2)	0.136 (3)	0.139 (6)
C30B	1.142 (5)	0.998 (3)	0.147 (2)	0.0693 (18)	0.139 (6)
C1	1.2599 (5)	0.6952 (3)	0.1920 (3)	0.0523 (10)
H1	1.2293	0.7561	0.1676	0.063*
C2	1.3902 (5)	0.6611 (3)	0.1860 (3)	0.0537 (10)
H2	1.4462	0.6976	0.1579	0.064*
C3	1.4353 (5)	0.5733 (4)	0.2220 (3)	0.0537 (10)
H3	1.5237	0.5489	0.2195	0.064*
C4	1.3497 (4)	0.5204 (3)	0.2621 (3)	0.0468 (9)
H4	1.3795	0.4598	0.2872	0.056*
C5	1.2205 (4)	0.5574 (3)	0.2650 (2)	0.0361 (8)
C6	1.1229 (4)	0.5037 (3)	0.3055 (2)	0.0342 (7)
C7	1.1385 (4)	0.3992 (3)	0.3247 (2)	0.0388 (8)
H7	1.213	0.3609	0.3123	0.047*
C8	1.0437 (4)	0.3513 (3)	0.3624 (2)	0.0383 (8)
C9	0.9384 (4)	0.4127 (3)	0.3816 (2)	0.0369 (8)
H9	0.8752	0.3845	0.4095	0.044*
C10	0.9266 (4)	0.5166 (3)	0.3593 (2)	0.0338 (7)
C11	0.8142 (4)	0.5847 (3)	0.3771 (2)	0.0347 (7)
C12	0.7307 (4)	0.5584 (3)	0.4284 (2)	0.0417 (8)
H12	0.7421	0.4944	0.4522	0.05*
C13	0.6296 (5)	0.6267 (3)	0.4449 (3)	0.0501 (10)
H13	0.5704	0.6092	0.4788	0.06*
C14	0.6188 (5)	0.7210 (3)	0.4099 (3)	0.0519 (10)
H14	0.5534	0.77	0.4208	0.062*
C15	0.7043 (5)	0.7420 (3)	0.3593 (3)	0.0474 (10)
H15	0.6955	0.8066	0.336	0.057*
C16	1.1819 (5)	0.0805 (3)	0.3982 (3)	0.0571 (12)
H16	1.2672	0.0481	0.401	0.068*
C17	1.1783 (5)	0.1875 (3)	0.3838 (3)	0.0505 (10)
H17	1.2592	0.2262	0.3768	0.061*
C18	1.0535 (4)	0.2369 (3)	0.3799 (2)	0.0399 (8)
C19	0.9383 (5)	0.1753 (3)	0.3908 (3)	0.0519 (10)
H19	0.8517	0.2055	0.3887	0.062*
C20	0.9520 (6)	0.0688 (3)	0.4049 (3)	0.0594 (12)
H20	0.8731	0.0281	0.4126	0.071*
C22	0.7704 (5)	0.5083 (3)	0.0997 (3)	0.0523 (10)
C23	0.8004 (6)	0.5427 (4)	0.0297 (3)	0.0718 (15)
H23	0.7685	0.4974	−0.0239	0.086*
C24	0.8767 (5)	0.6429 (4)	0.0383 (3)	0.0515 (10)
C27	0.7744 (5)	0.9089 (3)	0.1768 (3)	0.0569 (11)
C28	0.8842 (5)	0.9693 (4)	0.1609 (3)	0.0655 (13)
H28	0.8637	1.0278	0.1314	0.079*
C29	1.0244 (5)	0.9468 (3)	0.1870 (3)	0.0534 (11)
C31	0.4832 (7)	0.7478 (6)	0.7308 (4)	0.0958 (19)
H31A	0.5547	0.7518	0.7843	0.144*
H31B	0.397	0.7054	0.7319	0.144*
H31C	0.4623	0.8213	0.7223	0.144*
Cl1	0.30493 (11)	0.69937 (8)	0.49683 (7)	0.0517 (2)
N1	1.1748 (3)	0.6454 (2)	0.23092 (19)	0.0405 (7)
N2	1.0163 (3)	0.5603 (2)	0.32052 (17)	0.0329 (6)
N3	0.8006 (3)	0.6758 (2)	0.34053 (18)	0.0376 (7)
N4	1.0714 (5)	0.0212 (3)	0.4082 (2)	0.0552 (9)
O1	0.8032 (3)	0.5596 (2)	0.17364 (16)	0.0442 (6)
O2	0.9332 (3)	0.7075 (2)	0.10503 (16)	0.0512 (7)
O3	1.0696 (3)	0.8734 (2)	0.22719 (16)	0.0476 (7)
O4	0.7822 (3)	0.8267 (2)	0.21397 (18)	0.0505 (7)
O5	1.0781 (3)	0.8027 (2)	0.37801 (17)	0.0458 (7)
H5A	1.087 (5)	0.867 (3)	0.392 (3)	0.069*
H5B	1.134 (5)	0.775 (4)	0.405 (3)	0.069*
O6	0.5339 (4)	0.6980 (3)	0.6653 (2)	0.0727 (10)
H6	0.4737	0.6963	0.6195	0.109*
Yb1	0.953387 (18)	0.714155 (11)	0.248364 (9)	0.03543 (6)

	U11	U22	U33	U12	U13	U23
O7A	0.129 (9)	0.068 (7)	0.177 (13)	−0.022 (6)	−0.026 (8)	0.055 (8)
O7B	0.163 (13)	0.047 (6)	0.130 (12)	0.040 (7)	0.101 (11)	0.015 (6)
F1A	0.100 (4)	0.105 (4)	0.186 (8)	−0.051 (3)	0.076 (5)	−0.023 (5)
F2A	0.190 (7)	0.054 (3)	0.094 (3)	−0.032 (3)	0.029 (4)	0.021 (2)
F3A	0.169 (6)	0.074 (2)	0.057 (3)	−0.061 (3)	0.035 (3)	−0.024 (3)
C21A	0.109 (6)	0.064 (5)	0.052 (4)	−0.040 (4)	0.028 (3)	−0.009 (3)
F4A	0.121 (4)	0.105 (5)	0.055 (3)	−0.038 (4)	0.016 (3)	0.036 (3)
F5A	0.146 (7)	0.118 (4)	0.054 (2)	−0.003 (4)	0.048 (4)	0.003 (2)
F6A	0.104 (4)	0.196 (9)	0.085 (5)	−0.001 (5)	−0.009 (4)	0.098 (5)
C25A	0.099 (5)	0.081 (5)	0.025 (4)	−0.027 (4)	0.008 (3)	0.004 (3)
F7A	0.094 (4)	0.102 (4)	0.228 (8)	0.039 (3)	0.012 (4)	0.117 (5)
F8A	0.110 (4)	0.158 (5)	0.180 (6)	0.089 (3)	0.073 (4)	0.092 (4)
F9A	0.080 (3)	0.119 (4)	0.152 (5)	0.005 (3)	−0.029 (3)	0.044 (3)
C26A	0.072 (5)	0.078 (4)	0.133 (6)	0.026 (4)	0.025 (4)	0.075 (5)
F10A	0.069 (3)	0.105 (4)	0.187 (5)	0.001 (3)	0.032 (3)	0.092 (4)
F11A	0.126 (3)	0.047 (2)	0.105 (3)	−0.020 (2)	0.024 (3)	0.032 (2)
F12A	0.196 (7)	0.123 (6)	0.095 (4)	−0.066 (4)	0.086 (4)	−0.010 (3)
C30A	0.078 (4)	0.058 (4)	0.073 (5)	−0.010 (3)	0.015 (3)	0.031 (3)
F1B	0.100 (4)	0.105 (4)	0.186 (8)	−0.051 (3)	0.076 (5)	−0.023 (5)
F2B	0.190 (7)	0.054 (3)	0.094 (3)	−0.032 (3)	0.029 (4)	0.021 (2)
F3B	0.169 (6)	0.074 (2)	0.057 (3)	−0.061 (3)	0.035 (3)	−0.024 (3)
C21B	0.109 (6)	0.064 (5)	0.052 (4)	−0.040 (4)	0.028 (3)	−0.009 (3)
F4B	0.121 (4)	0.105 (5)	0.055 (3)	−0.038 (4)	0.016 (3)	0.036 (3)
F5B	0.146 (7)	0.118 (4)	0.054 (2)	−0.003 (4)	0.048 (4)	0.003 (2)
F6B	0.104 (4)	0.196 (9)	0.085 (5)	−0.001 (5)	−0.009 (4)	0.098 (5)
C25B	0.099 (5)	0.081 (5)	0.025 (4)	−0.027 (4)	0.008 (3)	0.004 (3)
F7B	0.094 (4)	0.102 (4)	0.228 (8)	0.039 (3)	0.012 (4)	0.117 (5)
F8B	0.110 (4)	0.158 (5)	0.180 (6)	0.089 (3)	0.073 (4)	0.092 (4)
F9B	0.080 (3)	0.119 (4)	0.152 (5)	0.005 (3)	−0.029 (3)	0.044 (3)
C26B	0.072 (5)	0.078 (4)	0.133 (6)	0.026 (4)	0.025 (4)	0.075 (5)
F10B	0.069 (3)	0.105 (4)	0.187 (5)	0.001 (3)	0.032 (3)	0.092 (4)
F11B	0.126 (3)	0.047 (2)	0.105 (3)	−0.020 (2)	0.024 (3)	0.032 (2)
F12B	0.196 (7)	0.123 (6)	0.095 (4)	−0.066 (4)	0.086 (4)	−0.010 (3)
C30B	0.078 (4)	0.058 (4)	0.073 (5)	−0.010 (3)	0.015 (3)	0.031 (3)
C1	0.066 (3)	0.045 (2)	0.054 (3)	0.006 (2)	0.025 (2)	0.0186 (19)
C2	0.062 (3)	0.052 (2)	0.052 (3)	−0.002 (2)	0.024 (2)	0.0137 (19)
C3	0.047 (2)	0.053 (2)	0.060 (3)	0.0008 (19)	0.015 (2)	0.008 (2)
C4	0.045 (2)	0.038 (2)	0.055 (2)	0.0025 (17)	0.0080 (18)	0.0101 (17)
C5	0.045 (2)	0.0238 (16)	0.0355 (18)	0.0010 (14)	0.0053 (15)	0.0042 (13)
C6	0.043 (2)	0.0243 (15)	0.0320 (17)	0.0026 (14)	0.0032 (14)	0.0056 (13)
C7	0.048 (2)	0.0264 (16)	0.042 (2)	0.0099 (15)	0.0103 (16)	0.0068 (14)
C8	0.054 (2)	0.0234 (16)	0.0355 (18)	0.0083 (15)	0.0053 (16)	0.0079 (13)
C9	0.050 (2)	0.0264 (16)	0.0368 (19)	0.0054 (15)	0.0126 (16)	0.0111 (13)
C10	0.046 (2)	0.0237 (15)	0.0304 (17)	0.0030 (14)	0.0075 (15)	0.0067 (12)
C11	0.046 (2)	0.0241 (15)	0.0325 (17)	0.0049 (14)	0.0059 (15)	0.0069 (13)
C12	0.057 (2)	0.0332 (18)	0.0369 (19)	0.0049 (16)	0.0122 (17)	0.0110 (15)
C13	0.057 (3)	0.049 (2)	0.051 (2)	0.0112 (19)	0.023 (2)	0.0108 (18)
C14	0.060 (3)	0.047 (2)	0.054 (2)	0.023 (2)	0.019 (2)	0.0112 (19)
C15	0.063 (3)	0.0336 (19)	0.049 (2)	0.0200 (18)	0.014 (2)	0.0127 (16)
C16	0.071 (3)	0.0290 (19)	0.067 (3)	0.018 (2)	0.005 (2)	0.0147 (18)
C17	0.062 (3)	0.0288 (18)	0.058 (3)	0.0116 (18)	0.008 (2)	0.0122 (17)
C18	0.061 (2)	0.0241 (16)	0.0354 (19)	0.0094 (16)	0.0108 (17)	0.0090 (13)
C19	0.072 (3)	0.0307 (19)	0.062 (3)	0.0158 (19)	0.026 (2)	0.0194 (18)
C20	0.088 (4)	0.031 (2)	0.069 (3)	0.012 (2)	0.031 (3)	0.0190 (19)
C22	0.056 (3)	0.050 (2)	0.044 (2)	−0.009 (2)	0.0093 (19)	0.0007 (18)
C23	0.095 (4)	0.071 (3)	0.037 (2)	−0.030 (3)	0.013 (2)	−0.005 (2)
C24	0.059 (3)	0.056 (3)	0.037 (2)	−0.001 (2)	0.0057 (18)	0.0138 (18)
C27	0.067 (3)	0.043 (2)	0.067 (3)	0.017 (2)	0.013 (2)	0.029 (2)
C28	0.075 (3)	0.044 (2)	0.081 (3)	0.008 (2)	0.010 (3)	0.041 (2)
C29	0.072 (3)	0.034 (2)	0.051 (2)	−0.0040 (19)	0.006 (2)	0.0188 (17)
C31	0.079 (4)	0.129 (5)	0.077 (4)	0.018 (4)	0.014 (3)	0.024 (4)
Cl1	0.0523 (6)	0.0507 (6)	0.0543 (6)	0.0140 (5)	0.0087 (5)	0.0223 (4)
N1	0.053 (2)	0.0318 (15)	0.0399 (17)	0.0038 (14)	0.0136 (14)	0.0126 (12)
N2	0.0403 (16)	0.0218 (13)	0.0337 (15)	0.0062 (11)	0.0027 (12)	0.0068 (11)
N3	0.0490 (18)	0.0259 (14)	0.0387 (16)	0.0081 (13)	0.0097 (14)	0.0095 (12)
N4	0.090 (3)	0.0249 (15)	0.050 (2)	0.0142 (17)	0.0127 (19)	0.0116 (14)
O1	0.0527 (17)	0.0392 (14)	0.0368 (14)	−0.0025 (12)	0.0065 (12)	0.0065 (11)
O2	0.071 (2)	0.0422 (15)	0.0349 (14)	−0.0060 (13)	0.0037 (13)	0.0133 (11)
O3	0.0636 (18)	0.0328 (13)	0.0442 (15)	0.0035 (12)	0.0046 (13)	0.0174 (11)
O4	0.0563 (18)	0.0412 (15)	0.0595 (18)	0.0145 (13)	0.0115 (14)	0.0283 (13)
O5	0.0644 (19)	0.0223 (12)	0.0413 (15)	0.0080 (12)	−0.0051 (13)	0.0077 (10)
O6	0.059 (2)	0.087 (2)	0.070 (2)	0.0292 (19)	0.0039 (17)	0.0225 (19)
Yb1	0.04699 (10)	0.02374 (8)	0.03358 (9)	0.00377 (6)	0.00364 (6)	0.01108 (5)

O7A—H7A	0.818 (12)	C8—C9	1.387 (5)
O7A—H7B	0.689 (6)	C8—C18	1.496 (4)
O7B—H7C	0.775 (19)	C9—C10	1.397 (4)
O7B—H7D	0.754 (17)	C9—H9	0.94
F1A—C21A	1.299 (10)	C10—N2	1.344 (4)
F2A—C21A	1.313 (9)	C10—C11	1.485 (5)
F3A—C21A	1.325 (7)	C11—N3	1.359 (4)
C21A—C22	1.573 (9)	C11—C12	1.376 (5)
F4A—C25A	1.307 (8)	C12—C13	1.391 (5)
F5A—C25A	1.348 (8)	C12—H12	0.94
F6A—C25A	1.293 (9)	C13—C14	1.381 (6)
C25A—C24	1.589 (10)	C13—H13	0.94
F7A—C26A	1.327 (7)	C14—C15	1.364 (6)
F8A—C26A	1.317 (9)	C14—H14	0.94
F9A—C26A	1.309 (10)	C15—N3	1.349 (5)
C26A—C27	1.540 (8)	C15—H15	0.94
F10A—C30A	1.323 (7)	C16—N4	1.327 (6)
F11A—C30A	1.323 (7)	C16—C17	1.386 (5)
F12A—C30A	1.313 (8)	C16—H16	0.94
C30A—C29	1.518 (8)	C17—C18	1.388 (6)
F1B—C21B	1.30 (2)	C17—H17	0.94
F2B—C21B	1.31 (2)	C18—C19	1.385 (6)
F3B—C21B	1.324 (19)	C19—C20	1.385 (5)
C21B—C22	1.41 (3)	C19—H19	0.94
F4B—C25B	1.306 (17)	C20—N4	1.331 (6)
F5B—C25B	1.352 (19)	C20—H20	0.94
F6B—C25B	1.296 (19)	C22—O1	1.242 (5)
C25B—C24	1.42 (3)	C22—C23	1.385 (6)
F7B—C26B	1.33 (2)	C23—C24	1.376 (6)
F8B—C26B	1.30 (2)	C23—H23	0.94
F9B—C26B	1.31 (2)	C24—O2	1.238 (5)
C26B—C27	1.40 (5)	C27—O4	1.266 (4)
F10B—C30B	1.32 (2)	C27—C28	1.371 (6)
F11B—C30B	1.31 (2)	C28—C29	1.386 (7)
F12B—C30B	1.30 (2)	C28—H28	0.94
C30B—C29	1.61 (4)	C29—O3	1.246 (4)
C1—N1	1.347 (5)	C31—O6	1.380 (6)
C1—C2	1.387 (6)	C31—H31A	0.97
C1—H1	0.94	C31—H31B	0.97
C2—C3	1.363 (6)	C31—H31C	0.97
C2—H2	0.94	N1—Yb1	2.438 (3)
C3—C4	1.385 (6)	N2—Yb1	2.434 (3)
C3—H3	0.94	N3—Yb1	2.464 (3)
C4—C5	1.378 (5)	O1—Yb1	2.313 (2)
C4—H4	0.94	O2—Yb1	2.319 (3)
C5—N1	1.353 (4)	O3—Yb1	2.334 (3)
C5—C6	1.478 (5)	O4—Yb1	2.262 (3)
C6—N2	1.343 (4)	O5—Yb1	2.252 (3)
C6—C7	1.390 (4)	O5—H5A	0.78 (4)
C7—C8	1.391 (5)	O5—H5B	0.75 (4)
C7—H7	0.94	O6—H6	0.83
H7A—O7A—H7B	123.(2)	C14—C15—H15	118.0
H7C—O7B—H7D	142.0 (16)	N4—C16—C17	123.5 (4)
F1A—C21A—F2A	107.6 (7)	N4—C16—H16	118.3
F1A—C21A—F3A	109.7 (8)	C17—C16—H16	118.3
F2A—C21A—F3A	107.6 (8)	C16—C17—C18	119.1 (4)
F1A—C21A—C22	108.9 (7)	C16—C17—H17	120.5
F2A—C21A—C22	111.1 (6)	C18—C17—H17	120.5
F3A—C21A—C22	111.9 (6)	C19—C18—C17	117.5 (3)
F6A—C25A—F4A	108.7 (8)	C19—C18—C8	121.7 (4)
F6A—C25A—F5A	107.9 (6)	C17—C18—C8	120.9 (4)
F4A—C25A—F5A	107.8 (7)	C18—C19—C20	119.4 (4)
F6A—C25A—C24	109.1 (7)	C18—C19—H19	120.3
F4A—C25A—C24	112.3 (6)	C20—C19—H19	120.3
F5A—C25A—C24	111.0 (7)	N4—C20—C19	123.2 (5)
F9A—C26A—F8A	107.3 (7)	N4—C20—H20	118.4
F9A—C26A—F7A	108.0 (7)	C19—C20—H20	118.4
F8A—C26A—F7A	107.1 (7)	O1—C22—C23	127.1 (4)
F9A—C26A—C27	110.8 (7)	O1—C22—C21B	117.2 (12)
F8A—C26A—C27	110.5 (6)	C23—C22—C21B	114.8 (12)
F7A—C26A—C27	113.0 (6)	O1—C22—C21A	113.4 (4)
F12A—C30A—F11A	105.7 (5)	C23—C22—C21A	119.5 (4)
F12A—C30A—F10A	109.7 (7)	C24—C23—C22	120.3 (4)
F11A—C30A—F10A	105.7 (6)	C24—C23—H23	119.9
F12A—C30A—C29	109.3 (5)	C22—C23—H23	119.9
F11A—C30A—C29	113.3 (6)	O2—C24—C23	127.1 (4)
F10A—C30A—C29	112.8 (5)	O2—C24—C25B	107.4 (11)
F1B—C21B—F2B	107.(3)	C23—C24—C25B	125.1 (11)
F1B—C21B—F3B	103.(2)	O2—C24—C25A	115.9 (4)
F2B—C21B—F3B	103.(3)	C23—C24—C25A	117.0 (4)
F1B—C21B—C22	120.(2)	O4—C27—C28	127.4 (4)
F2B—C21B—C22	112.(2)	O4—C27—C26B	127.(2)
F3B—C21B—C22	111.(3)	C28—C27—C26B	106.(2)
F6B—C25B—F4B	113.(3)	O4—C27—C26A	112.4 (4)
F6B—C25B—F5B	101.(2)	C28—C27—C26A	120.2 (4)
F4B—C25B—F5B	107.(2)	C27—C28—C29	122.1 (4)
F6B—C25B—C24	117.(2)	C27—C28—H28	118.9
F4B—C25B—C24	108.(2)	C29—C28—H28	118.9
F5B—C25B—C24	111.(2)	O3—C29—C28	127.0 (4)
F8B—C26B—F9B	105.(3)	O3—C29—C30A	115.7 (5)
F8B—C26B—F7B	108.(3)	C28—C29—C30A	117.2 (4)
F9B—C26B—F7B	105.(3)	O3—C29—C30B	111.8 (11)
F8B—C26B—C27	104.(4)	C28—C29—C30B	119.7 (11)
F9B—C26B—C27	120.(4)	O6—C31—H31A	109.5
F7B—C26B—C27	114.(4)	O6—C31—H31B	109.5
F12B—C30B—F11B	113.(3)	H31A—C31—H31B	109.5
F12B—C30B—F10B	111.(3)	O6—C31—H31C	109.5
F11B—C30B—F10B	100.(3)	H31A—C31—H31C	109.5
F12B—C30B—C29	118.(3)	H31B—C31—H31C	109.5
F11B—C30B—C29	111.(3)	C1—N1—C5	117.3 (3)
F10B—C30B—C29	102.(3)	C1—N1—Yb1	122.6 (3)
N1—C1—C2	123.4 (4)	C5—N1—Yb1	120.0 (2)
N1—C1—H1	118.3	C6—N2—C10	118.8 (3)
C2—C1—H1	118.3	C6—N2—Yb1	119.5 (2)
C3—C2—C1	118.4 (4)	C10—N2—Yb1	120.0 (2)
C3—C2—H2	120.8	C15—N3—C11	116.8 (3)
C1—C2—H2	120.8	C15—N3—Yb1	123.7 (2)
C2—C3—C4	119.5 (4)	C11—N3—Yb1	119.5 (2)
C2—C3—H3	120.3	C16—N4—C20	117.4 (3)
C4—C3—H3	120.3	C22—O1—Yb1	136.0 (3)
C5—C4—C3	119.3 (4)	C24—O2—Yb1	136.7 (3)
C5—C4—H4	120.3	C29—O3—Yb1	131.4 (3)
C3—C4—H4	120.3	C27—O4—Yb1	133.3 (3)
N1—C5—C4	122.1 (3)	Yb1—O5—H5A	125.(4)
N1—C5—C6	115.7 (3)	Yb1—O5—H5B	120.(4)
C4—C5—C6	122.2 (3)	H5A—O5—H5B	113.(5)
N2—C6—C7	122.0 (3)	C31—O6—H6	109.5
N2—C6—C5	116.3 (3)	O5—Yb1—O4	101.21 (10)
C7—C6—C5	121.7 (3)	O5—Yb1—O1	145.11 (10)
C6—C7—C8	119.9 (3)	O4—Yb1—O1	92.58 (10)
C6—C7—H7	120.1	O5—Yb1—O2	142.31 (11)
C8—C7—H7	120.1	O4—Yb1—O2	78.53 (10)
C9—C8—C7	117.6 (3)	O1—Yb1—O2	71.66 (9)
C9—C8—C18	121.3 (3)	O5—Yb1—O3	73.80 (10)
C7—C8—C18	121.1 (3)	O4—Yb1—O3	74.24 (10)
C8—C9—C10	119.9 (3)	O1—Yb1—O3	141.08 (9)
C8—C9—H9	120.1	O2—Yb1—O3	69.89 (9)
C10—C9—H9	120.1	O5—Yb1—N2	79.05 (9)
N2—C10—C9	121.8 (3)	O4—Yb1—N2	143.97 (10)
N2—C10—C11	116.3 (3)	O1—Yb1—N2	71.28 (9)
C9—C10—C11	121.9 (3)	O2—Yb1—N2	122.99 (9)
N3—C11—C12	122.1 (3)	O3—Yb1—N2	137.52 (10)
N3—C11—C10	115.7 (3)	O5—Yb1—N1	87.59 (11)
C12—C11—C10	122.2 (3)	O4—Yb1—N1	149.10 (10)
C11—C12—C13	119.9 (3)	O1—Yb1—N1	96.84 (10)
C11—C12—H12	120.1	O2—Yb1—N1	76.68 (10)
C13—C12—H12	120.1	O3—Yb1—N1	80.08 (10)
C14—C13—C12	118.0 (4)	N2—Yb1—N1	66.59 (10)
C14—C13—H13	121.0	O5—Yb1—N3	76.28 (11)
C12—C13—H13	121.0	O4—Yb1—N3	78.64 (10)
C15—C14—C13	119.2 (4)	O1—Yb1—N3	75.27 (9)
C15—C14—H14	120.4	O2—Yb1—N3	138.51 (10)
C13—C14—H14	120.4	O3—Yb1—N3	134.26 (9)
N3—C15—C14	124.0 (4)	N2—Yb1—N3	66.31 (9)
N3—C15—H15	118.0	N1—Yb1—N3	132.23 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···Cl1i	0.75 (4)	2.31 (4)	3.054 (3)	175.(5)
O6—H6···Cl1	0.83	2.27	3.102 (3)	177.
O5—H5A···N4ii	0.78 (4)	1.92 (4)	2.686 (4)	167.(5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯Cl1i	0.75 (4)	2.31 (4)	3.054 (3)	175 (5)
O6—H6⋯Cl1	0.83	2.27	3.102 (3)	177
O5—H5A⋯N4ii	0.78 (4)	1.92 (4)	2.686 (4)	167 (5)

Symmetry codes: (i) ; (ii) .