metal-organic compounds

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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Di-l-hydroxido-j 4 O:O-l-trifluoromethanesulfonato-j 2 O:O 0 -bis[(5,5 0 - dimethyl-2,2-bipyridine-j 2 N,N 0 )- (g 5 -pentamethylcyclopentadienyl)- ytterbium(iii)] tetraphenylborate 5,5 0 -dimethyl-2,2-bipyridine Daniel Kazhdan Chemistry Department and Chemical Sciences Division of Lawrence Berkeley National Laboratory, University of California, Berkeley, CA 94720, USA Correspondence kazhdan@berkeley.edu Received 4 January 2008; accepted 24 January 2008 Key indicators: single-crystal X-ray study; T = 130 K; mean (C C) = Å; R factor = 0.040; wr factor = 0.040; data-to-parameter ratio = The title compound, [Yb 2 (CF 3 O 3 S)(C 10 H 15 ) 2 (OH) 2 - (C 12 H 12 N 2 ) 2 ](C 24 H 20 B)C 12 H 12 N 2, crystallizes as a half-sandwich complex with a bridging trifluoromethanesulfonate as well as two bridging hydroxide groups. The bound bipyridine ligands have N C C N torsion angles of 13.1 (9) and 12.1 (8). The structure also contains an uncoordinated 5,5 0 - dimethyl-2,2 0 -bipyridine molecule with an N C C N torsion angle of (7). The triply bridged Yb centers are (4) Å apart. The Yb N bond lengths are in the range (6) (5) Å. Related literature For related literature, see: Allen (2002); van Albada et al. (2005); Schultz et al. (2002). Experimental Crystal data [Yb 2 (CF 3 O 3 S)(C 10 H 15 ) 2 (OH) 2 - (C 12 H 12 N 2 ) 2 ](C 24 H 20 B)C 12 H 12 N 2 M r = Triclinic, P1 a = (8) Å b = (9) Å c = (15) Å = (1) Data collection Bruker APEX diffractometer Absorption correction: multi-scan (using intensity measurements; Blessing, 1995) T min = 0.691, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Selected geometric parameters (Å, ). = (1) = (1) V = (4) Å 3 Z =2 Mo K radiation = 2.49 mm 1 T = 130 (1) K mm measured reflections independent reflections 9459 reflections with F 2 >3(F 2 ) R int = parameters H-atom parameters constrained max = 1.59 e Å 3 min = 2.03 e Å 3 Cg1 and Cg2 are the centroids of the C1 C5 and C6 C10 rings, respectively. Yb1 Yb (4) Yb1 O (4) Yb1 O (4) Yb1 O (4) Yb1 N (5) Yb1 N (5) Yb1 Cg (3) Yb2 O (5) Yb2 O (4) Yb2 O (5) Yb2 N (6) Yb2 N (6) Yb2 Cg (3) Yb1 O1 Yb (2) Yb1 O2 Yb (2) Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (MSC/Rigaku, 1998); molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN. This work was supported by the Director, Office of Energy Research, Office of Basic Energy Sciences, Chemical Sciences Division, US Department of Energy, under contract No. DE- AC03-76SF0098. I thank Professor Richard A. Andersen (UC Berkeley) and Dr Fred Hollander (CHEXRAY, the UC Berkeley X-ray facility). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2065). References Albada, G. A. van, Mutikainen, I., Turpeinen, U. & Reedijk, J. (2005). Acta Cryst. E61, m1411 m1412. Allen, F. H. (2002). Acta Cryst. B58, Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, Blessing, R. H. (1995). Acta Cryst. A51, Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. MSC/Rigaku (1998). TEXSAN. Version MSC/Rigaku, The Woodlands, Texas, USA. Schultz, M., Boncella, J. M., Berg, D. J., Tilley, T. D. & Andersen, R. A. (2002). Organometallics, 21, doi: /s Daniel Kazhdan m435

2 supporting information [doi: /s ] Di-µ-hydroxido-κ 4 O:O-µ-trifluoromethanesulfonato-κ 2 O:O -bis[(5,5 -dimethyl-2,2-bipyridine-κ 2 N,N )(η 5 -pentamethylcyclopentadienyl)ytterbium(iii)] tetraphenylborate 5,5 -dimethyl-2,2-bipyridine Daniel Kazhdan S1. Comment The title compound, (I), is presented in Fig. 1, wherein, the cyclopentadienyl ligands represented by Cg1 and Cg2, are the centroids of the rings defined by C1 C5 and C6 C10, respectively. The two pyridine rings of the bipyridine (bpy) ligands are not coplanar; the torsion angles N C C N are The Yb(III)-N distances of (6) (5) Å in (I) are not uncommon for neutral bpy bound to a Ytterbium center (Schultz et al., 2002). The trifluoromethanesulfonate anion is bridging. The uncoordinated 5,5 -dimethyl-2,2 -bipyridine is the second structure (van Albada et al., 2005) of uncoordinated 5,5 -dimethyl-2,2 -bipyridine in the Cambridge Structural Database (Allen, 2002). S2. Experimental Impure NaBPh 4 (1.00 g, 3.13 mmol) purchased from Aldrich was added to ([Cp* 2 Yb(5,5 -dimethyl-2,2 -bipyridine)] [OTf] (1.16 g, 1.49 mmol) in the presence of 5,5 -dimethyl-2,2 -bipyridine (0.50 g, 2.71 mmol) in ether. The solution was stirred overnight and the ether was filtered off. The yellow residue was dissolved in dichloromethane, filtered, and then layered with pentane. After 3 days dark yellow crystals were obtained. Yield 0.86 g (77%). S3. Refinement All non-hydrogen atoms were refined anisotropically. Hydrogen atoms bonded to C-atoms were included in the refinements at geometrically idealized positions with C H = 0.95 Å and U iso = 1.2 times U eq of the parent atoms. The hydrxyl H-atoms were located from a difference map and included in the refinements at those positions with U iso = 1.2 times U eq of the O-atoms. The final difference map showed residual electron denities in the close proximity of Yb atoms. sup-1

3 Figure 1 A view of the title compound with displacement ellipsoids drawn at the 50% probability level; hydrogen atoms have been omitted for clarity. Di-µ-hydroxido-κ 4 O:O-µ-trifluoromethanesulfonato-κ 2 O:O -bis[(5,5 - dimethyl-2,2-bipyridine-κ 2 N,N )(η 5 pentamethylcyclopentadienyl)ytterbium(iii)] tetraphenylborate 5,5 -dimethyl-2,2-bipyridine Crystal data [Yb 2 (CF 3 O 3 S)(C 10 H 15 ) 2 (OH) 2 (C 12 H 12 N 2 ) 2 ] (C 24 H 20 B) C 12 H 12 N 2 M r = Triclinic, P1 Hall symbol: -P 1 a = (8) Å b = (9) Å c = (15) Å α = (1) β = (1) γ = (1) V = (4) Å 3 Z = 2 F(000) = D x = Mg m 3 Melting point: 518 (with decomposition) K Mo Kα radiation, λ = Å Cell parameters from 4695 reflections θ = µ = 2.49 mm 1 T = 130 K Block, yellow mm sup-2

4 Data collection Bruker APEX diffractometer ω scans Absorption correction: multi-scan (Blessing, 1995) T min = 0.691, T max = measured reflections independent reflections 9459 reflections with F 2 > 3σ(F 2 ) R int = θ max = 26.4 h = 0 16 k = l = Refinement Refinement on F R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 892 parameters H-atom parameters constrained w = 1/[σ 2 (F o ) F o 2 ] (Δ/σ) max = Δρ max = 1.59 e Å 3 Δρ min = 2.03 e Å 3 Special details Refinement. Refinement using reflections with F 2 > 3.0 σ(f 2 ). The weighted R-factor (wr), goodness of fit (S) and R- factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F 2 > 3.0 σ(f 2 ) is used only for calculating R-factor (gt). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Yb (2) (2) (1) (1) Yb (2) (2) (1) (9) S (1) (2) (7) (5) F (4) (4) (2) (2) F (4) (4) (2) (2) F (4) (4) (2) (2) O (3) (4) (2) (1) O (3) (3) (2) (1) O (4) (4) (2) (1) O (4) (4) (2) (1) O (4) (4) (2) (2) N (4) (4) (2) (2) N (4) (4) (2) (2) N (4) (4) (2) (2) N (4) (4) (2) (2) N (5) (5) (3) (2) N (5) (6) (3) (3) C (6) (6) (3) (2) C (6) (6) (4) (2) C (7) (6) (4) (3) C (8) (6) (3) (3) C (7) (7) (4) (3) C (5) (5) (3) (2) C (5) (5) (3) (2) C (5) (6) (3) (2) sup-3

5 C (5) (6) (4) (2) C (5) (6) (3) (2) C (7) (7) (4) (3) C (7) (7) (4) (3) C (8) (8) (6) (4) C (10) (9) (4) (5) C (10) (8) (5) (5) C (5) (7) (3) (3) C (6) (7) (4) (3) C (7) (9) (4) (4) C (7) (7) (5) (4) C (6) (8) (4) (3) C (5) (6) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (5) (5) (3) (2) C (5) (5) (3) (2) C (6) (6) (3) (2) C (6) (6) (4) (3) C (6) (6) (3) (2) C (6) (6) (3) (2) C (7) (6) (3) (3) C (6) (7) (4) (3) C (5) (5) (3) (2) C (5) (6) (3) (2) C (6) (6) (3) (2) C (5) (6) (3) (2) C (5) (5) (3) (2) C (5) (5) (3) (2) C (6) (6) (3) (2) C (6) (6) (4) (2) C (6) (6) (3) (2) C (5) (5) (3) (2) C (6) (6) (3) (2) C (7) (6) (4) (3) C (6) (6) (4) (3) C (6) (6) (3) (3) C (8) (8) (4) (3) C (7) (7) (4) (3) C (6) (6) (4) (2) C (6) (6) (4) (3) C (7) (7) (4) (3) C (8) (8) (4) (4) C (8) (7) (4) (3) C (7) (7) (5) (3) C (7) (7) (4) (3) C (9) (8) (5) (4) sup-4

6 C (5) (6) (3) (2) C (5) (5) (3) (2) C (6) (7) (3) (2) C (6) (7) (3) (3) C (6) (6) (3) (3) C (5) (6) (3) (2) C (5) (5) (3) (2) C (5) (5) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (5) (6) (3) (2) C (5) (5) (3) (2) C (5) (5) (3) (2) C (5) (6) (3) (2) C (5) (5) (3) (2) C (6) (6) (3) (2) C (5) (5) (3) (2) C (5) (5) (3) (2) C (5) (5) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (6) (6) (3) (2) C (7) (8) (3) (3) B (6) (6) (3) (2) H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * sup-5

7 H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * sup-6

8 H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Yb (2) (2) (2) (2) (1) (2) Yb (2) (2) (2) (1) (1) (1) S (1) (1) (10) (9) (8) (9) F (4) (5) (3) (4) (3) (3) F (3) (4) (3) (3) (2) (3) F (5) (4) (3) (4) (3) (3) O (3) (3) (3) (3) (2) (2) O (2) (3) (3) (2) (2) (2) O (3) (3) (3) (3) (2) (2) O (3) (3) (3) (2) (2) (2) O (3) (4) (4) (3) (3) (3) N (3) (3) (3) (3) (2) (3) N (3) (4) (4) (3) (3) (3) N (3) (3) (3) (3) (2) (3) N (3) (4) (3) (3) (2) (3) N (4) (4) (5) (3) (3) (4) N (4) (5) (6) (4) (4) (4) C (4) (5) (4) (4) (3) (3) C (5) (5) (5) (4) (4) (4) C (6) (5) (6) (5) (5) (4) C (7) (5) (5) (5) (4) (4) C (5) (6) (6) (5) (4) (4) C (4) (4) (4) (3) (3) (3) C (3) (4) (4) (3) (3) (3) C (4) (5) (5) (4) (3) (4) C (4) (4) (7) (3) (4) (4) sup-7

9 C (4) (5) (5) (4) (3) (4) C (6) (6) (7) (5) (5) (5) C (6) (6) (8) (5) (5) (5) C (6) (7) 0.18 (1) (6) (7) (7) C (1) (8) (7) (9) (8) (6) C (1) (8) (9) (7) (7) (6) C (4) (6) (5) (4) (4) (5) C (5) (6) (6) (5) (4) (5) C (5) (10) (6) (6) (4) (6) C (6) (6) 0.18 (1) (5) (7) (7) C (5) (8) (7) (5) (5) (6) C (4) (4) (5) (3) (3) (4) C (5) (5) (4) (4) (3) (3) C (5) (5) (4) (4) (4) (3) C (4) (5) (4) (4) (3) (3) C (4) (4) (4) (3) (3) (3) C (4) (4) (4) (3) (3) (3) C (4) (5) (4) (4) (3) (4) C (4) (5) (6) (4) (4) (4) C (4) (5) (5) (4) (4) (4) C (4) (5) (4) (4) (3) (4) C (6) (6) (5) (5) (4) (4) C (5) (6) (7) (5) (5) (5) C (4) (4) (4) (3) (3) (3) C (4) (5) (4) (4) (3) (4) C (4) (5) (4) (4) (3) (4) C (4) (5) (4) (4) (3) (4) C (3) (4) (4) (3) (3) (3) C (4) (4) (5) (3) (3) (3) C (4) (5) (5) (4) (4) (4) C (4) (4) (5) (4) (4) (4) C (4) (4) (5) (3) (4) (4) C (4) (4) (4) (3) (3) (3) C (5) (5) (4) (4) (4) (4) C (5) (5) (6) (4) (4) (4) C (4) (5) (6) (4) (4) (4) C (5) (5) (5) (4) (4) (4) C (6) (7) (7) (5) (5) (5) C (5) (6) (7) (4) (5) (5) C (4) (5) (6) (4) (4) (4) C (4) (5) (6) (4) (4) (4) C (5) (6) (7) (5) (5) (5) C (6) (7) (8) (5) (5) (6) C (7) (6) (7) (5) (6) (5) C (5) (6) (9) (5) (6) (6) C (6) (7) (6) (6) (5) (5) C (9) (7) (9) (7) (7) (6) C (4) (4) (4) (3) (3) (3) sup-8

10 C (4) (4) (4) (3) (3) (3) C (4) (6) (5) (4) (3) (4) C (5) (6) (5) (5) (4) (4) C (5) (5) (5) (4) (4) (4) C (4) (5) (4) (3) (3) (4) C (4) (4) (4) (3) (3) (3) C (4) (4) (4) (3) (3) (3) C (4) (5) (4) (4) (3) (4) C (4) (4) (5) (4) (4) (4) C (4) (5) (4) (4) (3) (4) C (4) (4) (4) (3) (3) (3) C (4) (4) (4) (3) (3) (3) C (4) (4) (4) (3) (3) (3) C (4) (5) (5) (4) (3) (4) C (4) (4) (5) (3) (3) (3) C (4) (5) (4) (4) (3) (4) C (4) (4) (4) (3) (3) (3) C (3) (4) (4) (3) (3) (3) C (4) (4) (4) (3) (3) (3) C (4) (5) (4) (3) (3) (3) C (4) (5) (4) (4) (3) (4) C (5) (5) (5) (4) (4) (4) C (4) (5) (4) (4) (3) (4) C (6) (7) (5) (6) (4) (5) B (4) (5) (4) (4) (3) (3) Geometric parameters (Å, º) Yb1 Yb (4) C61 C (10) Yb1 O (4) C63 C (9) Yb1 O (4) C63 C (9) Yb1 O (4) C63 B (1) Yb1 N (5) C64 C (10) Yb1 N (5) C65 C (10) Yb1 C (7) C66 C (1) Yb1 C (8) C67 C (1) Yb1 C (8) C69 C (9) Yb1 C (8) C69 C (9) Yb1 C (8) C69 B (10) Yb1 Cg (3) C70 C (9) Yb2 O (5) C71 C (10) Yb2 O (4) C72 C (10) Yb2 O (5) C73 C (9) Yb2 N (6) C75 C (9) Yb2 N (6) C75 C (10) Yb2 C (6) C75 B (10) Yb2 C (6) C76 C (10) Yb2 C (7) C77 C (11) sup-9

11 Yb2 C (7) C78 C (1) Yb2 C (7) C79 C (10) Yb2 Cg (3) O1 H S1 O (5) O2 H S1 O (5) C11 H S1 O (5) C11 H S1 C (8) C11 H F1 C (9) C12 H F2 C (10) C12 H F3 C (10) C12 H N1 C (8) C13 H N1 C (8) C13 H N2 C (8) C13 H N2 C (9) C14 H N3 C (8) C14 H N3 C (8) C14 H N4 C (9) C15 H N4 C (8) C15 H N5 C (10) C15 H N5 C (9) C16 H N6 C (9) C16 H N6 C (1) C16 H C1 C (1) C17 H C1 C (1) C17 H C1 C (1) C17 H C1 Cg (7) C18 H C2 C (1) C18 H C2 C (1) C18 H C2 Cg (9) C19 H C3 C (1) C19 H C3 C (1) C19 H C3 Cg (8) C20 H C4 C (1) C20 H C4 C (1) C20 H C4 Cg (8) C21 H C5 C (1) C23 H C5 Cg (8) C24 H C6 C (9) C27 H C6 C (10) C28 H C6 C (10) C30 H C6 Cg (7) C31 H C7 C (10) C31 H C7 C (1) C31 H C7 Cg (7) C32 H C8 C (1) C32 H C8 C (1) C32 H C8 Cg (8) C33 H C9 C (1) C35 H sup-10

12 C9 C (1) C36 H C9 Cg (8) C39 H C10 C (1) C40 H C10 Cg (8) C42 H C21 C (9) C43 H C22 C (1) C43 H C22 C (1) C43 H C23 C (10) C44 H C24 C (9) C44 H C25 C (9) C44 H C26 C (9) C45 H C27 C (1) C47 H C28 C (1) C48 H C29 C (10) C51 H C29 C (1) C52 H C33 C (10) C54 H C34 C (1) C55 H C34 C (1) C55 H C35 C (10) C55 H C36 C (9) C56 H C37 C (9) C56 H C38 C (10) C56 H C39 C (1) C58 H C40 C (1) C59 H C41 C (10) C60 H C41 C (1) C61 H C45 C (1) C62 H C46 C (1) C64 H C46 C (1) C65 H C47 C (1) C66 H C48 C (1) C67 H C49 C (1) C68 H C50 C (1) C70 H C51 C (1) C71 H C52 C (1) C72 H C53 C (1) C73 H C53 C (1) C74 H C57 C (9) C76 H C57 C (10) C77 H C57 B (10) C78 H C58 C (10) C79 H C59 C (1) C80 H C60 C (1) Yb1 Yb (4) C16 C77 iv 3.54 (1) Yb1 C (7) C18 C56 iii 3.57 (1) Yb1 C (8) C23 C (1) Yb1 C (8) C23 C (1) sup-11

13 Yb1 C (8) C23 C (1) Yb1 C (8) C24 C (9) Yb2 C (6) C25 C (1) Yb2 C (6) C26 C (1) Yb2 C (7) C27 C (1) Yb2 C (7) C27 C (1) Yb2 C (7) C28 C (1) F1 C15 i 3.43 (1) C28 C (1) F2 C17 ii (9) C29 C (1) F3 C56 iii 3.57 (1) C29 C (1) O2 N (8) C32 C (1) O2 C (10) C32 C (1) O5 C (1) C32 C (1) O5 C (1) C36 C (1) N2 N (9) C37 C (9) N3 C (9) C38 C (10) N5 C (9) C39 C70 v 3.34 (1) N5 C (9) C39 C71 v 3.52 (1) N5 C (10) C41 C (1) N5 C (1) C42 C (1) C6 C28 iv (9) C43 C58 vi 3.59 (1) C7 C32 iv (10) C44 C78 v 3.56 (1) C16 C28 iv 3.49 (1) Yb2 Yb1 O (1) N3 C37 C (6) Yb2 Yb1 O (1) N3 C37 C (6) Yb2 Yb1 O (1) C36 C37 C (7) Yb2 Yb1 N (1) N4 C38 C (6) Yb2 Yb1 N (1) N4 C38 C (7) Yb2 Yb1 C (2) C37 C38 C (7) Yb2 Yb1 C (2) C38 C39 C (7) Yb2 Yb1 C (2) C39 C40 C (7) Yb2 Yb1 C (2) C40 C41 C (7) Yb2 Yb1 C (2) C40 C41 C (7) Yb2 Yb1 Cg (1) C42 C41 C (8) O1 Yb1 O (2) N4 C42 C (7) O1 Yb1 O (2) N5 C45 C (8) O1 Yb1 N (2) C45 C46 C (8) O1 Yb1 N (2) C45 C46 C (8) O1 Yb1 C (2) C47 C46 C (8) O1 Yb1 C (2) C46 C47 C (8) O1 Yb1 C (2) C47 C48 C (8) O1 Yb1 C (2) N5 C49 C (8) O1 Yb1 C (2) N5 C49 C (7) O1 Yb1 Cg (1) C48 C49 C (8) O2 Yb1 O (2) N6 C50 C (8) O2 Yb1 N (2) N6 C50 C (8) O2 Yb1 N (2) C49 C50 C (7) sup-12

14 O2 Yb1 C (2) C50 C51 C (8) O2 Yb1 C (2) C51 C52 C (9) O2 Yb1 C (2) C52 C53 C (9) O2 Yb1 C (2) C52 C53 C (1) O2 Yb1 C (2) C54 C53 C (10) O2 Yb1 Cg (1) N6 C54 C (9) O3 Yb1 N (2) C58 C57 C (6) O3 Yb1 N (2) C58 C57 B (6) O3 Yb1 C (2) C62 C57 B (6) O3 Yb1 C (2) C57 C58 C (7) O3 Yb1 C (2) C58 C59 C (7) O3 Yb1 C (2) C59 C60 C (7) O3 Yb1 C (2) C60 C61 C (8) O3 Yb1 Cg (1) C57 C62 C (7) N1 Yb1 N (2) C64 C63 C (6) N1 Yb1 C (2) C64 C63 B (6) N1 Yb1 C (2) C68 C63 B (6) N1 Yb1 C (2) C63 C64 C (6) N1 Yb1 C (2) C64 C65 C (7) N1 Yb1 C (2) C65 C66 C (7) N1 Yb1 Cg (1) C66 C67 C (7) N2 Yb1 C (2) C63 C68 C (7) N2 Yb1 C (2) C70 C69 C (6) N2 Yb1 C (2) C70 C69 B (6) N2 Yb1 C (3) C74 C69 B (6) N2 Yb1 C (2) C69 C70 C (6) N2 Yb1 Cg (1) C70 C71 C (6) C1 Yb1 C (2) C71 C72 C (6) C1 Yb1 C (2) C72 C73 C (6) C1 Yb1 C (2) C69 C74 C (6) C1 Yb1 C (2) C76 C75 C (6) C1 Yb1 Cg (1) C76 C75 B (6) C2 Yb1 C (2) C80 C75 B (6) C2 Yb1 C (3) C75 C76 C (7) C2 Yb1 C (3) C76 C77 C (7) C2 Yb1 Cg (2) C77 C78 C (7) C3 Yb1 C (3) C78 C79 C (7) C3 Yb1 C (3) C75 C80 C (7) C3 Yb1 Cg (2) S1 C81 F (6) C4 Yb1 C (3) S1 C81 F (5) C4 Yb1 Cg (2) S1 C81 F (7) C5 Yb1 Cg (2) F1 C81 F (8) Yb1 Yb2 O (1) F1 C81 F (7) Yb1 Yb2 O (1) F2 C81 F (7) Yb1 Yb2 O (1) Yb1 Cg1 C (3) Yb1 Yb2 N (1) Yb1 Cg1 C (4) Yb1 Yb2 N (1) Yb1 Cg1 C (4) Yb1 Yb2 C (2) Yb1 Cg1 C (4) sup-13

15 Yb1 Yb2 C (2) Yb1 Cg1 C (4) Yb1 Yb2 C (2) C1 Cg1 C (5) Yb1 Yb2 C (2) C1 Cg1 C (6) Yb1 Yb2 C (2) C1 Cg1 C (6) Yb1 Yb2 Cg (1) C1 Cg1 C (5) O1 Yb2 O (2) C2 Cg1 C (6) O1 Yb2 O (2) C2 Cg1 C (6) O1 Yb2 N (2) C2 Cg1 C (6) O1 Yb2 N (2) C3 Cg1 C (6) O1 Yb2 C (2) C3 Cg1 C (6) O1 Yb2 C (2) C4 Cg1 C (6) O1 Yb2 C (2) Yb2 Cg2 C (3) O1 Yb2 C (2) Yb2 Cg2 C (3) O1 Yb2 C (2) Yb2 Cg2 C (3) O1 Yb2 Cg (1) Yb2 Cg2 C (3) O2 Yb2 O (1) Yb2 Cg2 C (3) O2 Yb2 N (2) C6 Cg2 C (5) O2 Yb2 N (2) C6 Cg2 C (5) O2 Yb2 C (2) C6 Cg2 C (6) O2 Yb2 C (2) C6 Cg2 C (5) O2 Yb2 C (2) C7 Cg2 C (5) O2 Yb2 C (2) C7 Cg2 C (6) O2 Yb2 C (2) C7 Cg2 C (5) O2 Yb2 Cg (1) C8 Cg2 C (5) O4 Yb2 N (2) C8 Cg2 C (6) O4 Yb2 N (2) C9 Cg2 C (5) O4 Yb2 C (2) C57 B1 C (5) O4 Yb2 C (2) C57 B1 C (5) O4 Yb2 C (2) C57 B1 C (6) O4 Yb2 C (2) C63 B1 C (5) O4 Yb2 C (2) C63 B1 C (5) O4 Yb2 Cg (1) C69 B1 C (5) N3 Yb2 N (2) Yb1 O1 H N3 Yb2 C (2) Yb2 O1 H N3 Yb2 C (2) Yb1 O2 H N3 Yb2 C (2) Yb2 O2 H N3 Yb2 C (2) C1 C11 H N3 Yb2 C (2) C1 C11 H N3 Yb2 Cg (1) C1 C11 H N4 Yb2 C (2) H3 C11 H N4 Yb2 C (2) H3 C11 H N4 Yb2 C (2) H4 C11 H N4 Yb2 C (2) C2 C12 H N4 Yb2 C (2) C2 C12 H N4 Yb2 Cg (1) C2 C12 H C6 Yb2 C (2) H6 C12 H C6 Yb2 C (2) H6 C12 H C6 Yb2 C (2) H7 C12 H sup-14

16 C6 Yb2 C (2) C3 C13 H C6 Yb2 Cg (1) C3 C13 H C7 Yb2 C (2) C3 C13 H C7 Yb2 C (2) H9 C13 H C7 Yb2 C (2) H9 C13 H C7 Yb2 Cg (2) H10 C13 H C8 Yb2 C (2) C4 C14 H C8 Yb2 C (2) C4 C14 H C8 Yb2 Cg (2) C4 C14 H C9 Yb2 C (2) H12 C14 H C9 Yb2 Cg (2) H12 C14 H C10 Yb2 Cg (2) H13 C14 H O3 S1 O (3) C5 C15 H O3 S1 O (3) C5 C15 H O3 S1 C (4) C5 C15 H O4 S1 O (3) H15 C15 H O4 S1 C (3) H15 C15 H O5 S1 C (4) H16 C15 H Yb1 O1 Yb (2) C6 C16 H Yb1 O2 Yb (2) C6 C16 H Yb1 O3 S (3) C6 C16 H Yb2 O4 S (3) H18 C16 H Yb1 N1 C (4) H18 C16 H Yb1 N1 C (4) H19 C16 H C21 N1 C (6) C7 C17 H Yb1 N2 C (4) C7 C17 H Yb1 N2 C (4) C7 C17 H C26 N2 C (6) H21 C17 H Yb2 N3 C (5) H21 C17 H Yb2 N3 C (4) H22 C17 H C33 N3 C (6) C8 C18 H Yb2 N4 C (5) C8 C18 H Yb2 N4 C (5) C8 C18 H C38 N4 C (6) H24 C18 H C45 N5 C (7) H24 C18 H C50 N6 C (8) H25 C18 H Yb1 C1 C (4) C9 C19 H Yb1 C1 C (4) C9 C19 H Yb1 C1 C (5) C9 C19 H Yb1 C1 Cg (3) H27 C19 H C2 C1 C (7) H27 C19 H C2 C1 C (7) H28 C19 H C2 C1 Cg (4) C10 C20 H C5 C1 C (8) C10 C20 H C5 C1 Cg (5) C10 C20 H C11 C1 Cg (7) H30 C20 H Yb1 C2 C (4) H30 C20 H Yb1 C2 C (5) H31 C20 H sup-15

17 Yb1 C2 C (6) N1 C21 H Yb1 C2 Cg (3) C22 C21 H C1 C2 C (7) C22 C23 H C1 C2 C (8) C24 C23 H C1 C2 Cg (4) C23 C24 H C3 C2 C (8) C25 C24 H C3 C2 Cg (5) C26 C27 H C12 C2 Cg (8) C28 C27 H Yb1 C3 C (5) C27 C28 H Yb1 C3 C (5) C29 C28 H Yb1 C3 C (5) N2 C30 H Yb1 C3 Cg (3) C29 C30 H C2 C3 C (7) C22 C31 H C2 C3 C (9) C22 C31 H C2 C3 Cg (5) C22 C31 H C4 C3 C (9) H39 C31 H C4 C3 Cg (5) H39 C31 H C13 C3 Cg (8) H40 C31 H Yb1 C4 C (5) C29 C32 H Yb1 C4 C (4) C29 C32 H Yb1 C4 C (6) C29 C32 H Yb1 C4 Cg (3) H42 C32 H C3 C4 C (7) H42 C32 H C3 C4 C (10) H43 C32 H C3 C4 Cg (5) N3 C33 H C5 C4 C (9) C34 C33 H C5 C4 Cg (5) C34 C35 H C14 C4 Cg (8) C36 C35 H Yb1 C5 C (4) C35 C36 H Yb1 C5 C (5) C37 C36 H Yb1 C5 C (6) C38 C39 H Yb1 C5 Cg (3) C40 C39 H C1 C5 C (7) C39 C40 H C1 C5 C (9) C41 C40 H C1 C5 Cg (5) N4 C42 H C4 C5 C (9) C41 C42 H C4 C5 Cg (5) C34 C43 H C15 C5 Cg (8) C34 C43 H Yb2 C6 C (4) C34 C43 H Yb2 C6 C (4) H51 C43 H Yb2 C6 C (4) H51 C43 H Yb2 C6 Cg (3) H52 C43 H C7 C6 C (6) C41 C44 H C7 C6 C (7) C41 C44 H C7 C6 Cg (4) C41 C44 H C10 C6 C (7) H54 C44 H C10 C6 Cg (4) H54 C44 H C16 C6 Cg (6) H55 C44 H sup-16

18 Yb2 C7 C (4) N5 C45 H Yb2 C7 C (4) C46 C45 H Yb2 C7 C (4) C46 C47 H Yb2 C7 Cg (3) C48 C47 H C6 C7 C (6) C47 C48 H C6 C7 C (7) C49 C48 H C6 C7 Cg (4) C50 C51 H C8 C7 C (7) C52 C51 H C8 C7 Cg (4) C51 C52 H C17 C7 Cg (6) C53 C52 H Yb2 C8 C (4) N6 C54 H Yb2 C8 C (4) C53 C54 H Yb2 C8 C (5) C46 C55 H Yb2 C8 Cg (3) C46 C55 H C7 C8 C (7) C46 C55 H C7 C8 C (8) H63 C55 H C7 C8 Cg (4) H63 C55 H C9 C8 C (8) H64 C55 H C9 C8 Cg (5) C53 C56 H C18 C8 Cg (6) C53 C56 H Yb2 C9 C (4) C53 C56 H Yb2 C9 C (4) H66 C56 H Yb2 C9 C (5) H66 C56 H Yb2 C9 Cg (3) H67 C56 H C8 C9 C (7) C57 C58 H C8 C9 C (9) C59 C58 H C8 C9 Cg (4) C58 C59 H C10 C9 C (9) C60 C59 H C10 C9 Cg (4) C59 C60 H C19 C9 Cg (7) C61 C60 H Yb2 C10 C (4) C60 C61 H Yb2 C10 C (4) C62 C61 H Yb2 C10 C (5) C57 C62 H Yb2 C10 Cg (3) C61 C62 H C6 C10 C (7) C63 C64 H C6 C10 C (8) C65 C64 H C6 C10 Cg (4) C64 C65 H C9 C10 C (8) C66 C65 H C9 C10 Cg (5) C65 C66 H C20 C10 Cg (7) C67 C66 H N1 C21 C (6) C66 C67 H C21 C22 C (7) C68 C67 H C21 C22 C (7) C63 C68 H C23 C22 C (7) C67 C68 H C22 C23 C (7) C69 C70 H C23 C24 C (6) C71 C70 H N1 C25 C (6) C70 C71 H N1 C25 C (6) C72 C71 H sup-17

19 C24 C25 C (6) C71 C72 H N2 C26 C (6) C73 C72 H N2 C26 C (6) C72 C73 H C25 C26 C (6) C74 C73 H C26 C27 C (7) C69 C74 H C27 C28 C (7) C73 C74 H C28 C29 C (7) C75 C76 H C28 C29 C (7) C77 C76 H C30 C29 C (7) C76 C77 H N2 C30 C (7) C78 C77 H N3 C33 C (7) C77 C78 H C33 C34 C (7) C79 C78 H C33 C34 C (7) C78 C79 H C35 C34 C (7) C80 C79 H C34 C35 C (7) C75 C80 H C35 C36 C (7) C79 C80 H N1 C25 C26 N (9) N5 C49 C50 N (7) N3 C37 C38 N (8) Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+2, z+1; (iv) x+1, y, z; (v) x, y+1, z; (vi) x+1, y+1, z+2. sup-18