metal-organic compounds

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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Poly[ethanolbis(l 3-2-thioxo-1,2-dihydropyridin-1-olato)dilithium(I)] Jens Hartung, a Nina Schneiders, a Ingrid Svoboda b and Hartmut Fuess b * a Fachbereich Chemie, Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, D Kaiserslautern, Germany, and b Struktur- Strukturforschung, FB 11, Material- und Geowissenschaften, Technische Universität Darmstadt, Petersenstrasse 23, D Darmstadt, Germany Correspondence hartung@chemie.uni-kl.de Received 13 December 2007; accepted 1 February 2008 Key indicators: single-crystal X-ray study; T = 300 K; mean (C C) = Å; R factor = 0.045; wr factor = 0.100; data-to-parameter ratio = Experimental Crystal data [Li 2 (C 5 H 4 NOS) 2 (C 2 H 6 O)] M r = Monoclinic, P2 1 =c a = (7) Å b = (2) Å c = (7) Å = (4) Data collection Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2006); analytical numeric absorption correction using a multifaceted crystal model based Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = (19) Å 3 Z =8 Mo K radiation = 0.38 mm 1 T = 300 (2) K mm on expressions derived by Clark & Reid (1995)] T min = 0.835, T max = measured reflections 5597 independent reflections 1539 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.44 e Å 3 min = 0.32 e Å 3 The title compound, [Li 2 (C 5 H 4 NOS) 2 (C 2 H 6 O)] n, having two formula units in the asymmetric unit, forms infinite chains of Li 2 O 2 rhombi along b, consisting of four independent Li and O atoms. Metal binding to 2-thiooxo-1,2-dihydropyridin-1-olate occurs in a bidentate fashion via O and S, and in a monodentate manner via the N-oxide O atom. Interactions between polymeric chains are evident from centroidto-centroid distances of pyridinethione fragments of (6) (6) Å. The N O and C S bond lengths are distinctively different from those in hitherto investigated Ni II, Zn II and (H 3 C) 2 Tl III complexes of 2-thiooxo-1,2-dihydropyridin-1-olate, but correlate with those reported for 1-hydroxy- and 1-alkoxypyridine-2(1H)-thiones in the solid state. Related literature For related literature, see: Barnett et al. (1977); Castaño et al. (1988); Chen et al. (1991); Hartung, Hiller et al. (1996); Hartung, Svoboda et al. (1996); Hartung et al. (1999, 2007). Table 1 Selected interatomic distances (Å). Cg1, Cg2, Cg3 and Cg4 are the centroids of atoms N4,C16 C20, N1,C1 C5, N3,C11 C15 and N2,C6 C10, respectively. Cg1Cg (6) Cg1Cg2 i (6) Symmetry code: (i) x; y þ 1; z. Table 2 Hydrogen-bond geometry (Å, ). Cg3Cg (6) Cg3Cg4 i (6) D HA D H HA DA D HA O5 H5AS1 i (3) 174 O6 H6AS3 ii (4) 172 Symmetry codes: (i) x; y þ 1; z; (ii) x; y 1; z. Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2377). References Barnett, B. L., Kretschmar, H. C. & Hartmann, F. A. (1977). Inorg. Chem. 16, Castaño, M. V., Sánchez, A., Casas, J. S., Sordo, J., Briansó, J. L., Piniella, J. F., Solans, X., Germain, G. & Debaerdemaeker, T. (1988). Organometallics, 7, m462 Hartung et al. doi: /s

2 metal-organic compounds Chen, X., Hu, Y., Wu, D., Weng, L. & Kang, B. (1991). Polyhedron, 10, Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Hartung, J., Hiller, M., Schwarz, M., Svoboda, I. & Fuess, H. (1996). Liebigs Ann. Chem. pp Hartung, J., Kneuer, R., Schwarz, M., Svoboda, I. & Fuess, H. (1999). Eur. J. Org. Chem. pp Hartung, J., Svoboda, I. & Fuess, H. (1996). Acta Cryst. C52, Hartung, J., Svoboda, I. & Fuess, H. (2007). Unpublished results. Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Sheldrick, G. M. (2008). Acta Cryst. A64, Hartung et al. [Li 2 (C 5 H 4 NOS) 2 (C 2 H 6 O)] m463

3 supporting information [doi: /s ] Poly[ethanolbis(µ 3-2-thioxo-1,2-dihydropyridin-1-olato)dilithium(I)] Jens Hartung, Nina Schneiders, Ingrid Svoboda and Hartmut Fuess S1. Comment 2-Thiooxo-1,2-dihydropyridine-1-olate is an ambident nucleophile that is preferentially alkylated at sulfur in the presence of hard countercations, such as Na+ (Hartung et al., 1999). The reactivity of the title compound, however, does not fit into this general scheme. Its inherent low reactivity toward strong electrophiles in association with a slight preference for the O-alkylation prompted us to explore its solid state geometry at 300 K. Diffraction experiments performed at 100 K and 150 K surprisingly did not afford data sets of an improved quality. The results of the structure investigation are summarized in the following section. Formula 1, Figure 1 The title compound, (I), crystallizes in monoclinic space group P2 1 /c (Z = 4). Its structure is composed of infinite chains of Li 2 O 2 rhombi along y consisting of four independent Li and O atoms (Figure 1). Neighbouring segments are tilted by approximately 90 in an accordion-like manner. π π Interactions between polymeric chains are evident from centroidto-centroid distances of pyridinethione fragments (Table 1). Metal binding to 2-thiooxo-1,2-dihydropyridine-1-olate occurs in two different ways. Li1 and Li2 are chelated via S and O to two molecules of 2-thiooxo-1,2-dihydropyridine-1- olate. In both instances, one of the ligands places the metal closer toward the heterocyclic plane [Li1 O2 N2 C6 = 13.6 (6), Li2 O4 N4 C16 = (6) ] than in the other [Li1 S1 C1 N1 = (4), Li2 S3 C11 N3 = 29.9 (4) ]. A fifth contact to Li1 and Li2 occurs via N-oxide binding of O2 and O4, giving rise to irregularly shaped polyhedra. Li3 and Li4 are located in distorted tetrahedral coordination polyedra that are composed of three N-oxide O- atoms [O1, O2, and O3 for Li3 and O1, O3, and O4 for Li4] and one O-atom from an ethanol solvate molecule [O5 for Li3 and O6 for Li4]. The observed parameters, in particular those of the central thiohydroxamate functionality of independent 2-thiooxo-1,2- dihydropyridine-1-olato entities in (I) [N1 O1 = (5) Å, N2 O2 = (4) Å, N3 O3 = (4) Å, N4 O4 = Å, C1 S1 = (5) Å, C6 S2 = (5), C11 S3 = (5) Å, C16 S4 = (5) Å] are distinctively different from those reported for the corresponding subunits 2-alkylsulfanyl pyridine-1-oxides [N O = Å, C S = (3) Å] (Hartung, Svoboda et al., 1996), bis[2-thiooxo-1,2-dihydropyridine-1-olato]nickel [N O = (3) Å and (4) Å, C S = (3) Å and (3) Å] (Chen et al., 1991, Hartung et al., 2007), the corresponding Zn(II) compound [N O = 1.34 (1) Å and 1.37 (1) Å, C S = (9) Å and (9) Å] (Barnett et al., 1977), and the derived dimethylthallium(iii) complex [N O = (9) Å, C S = (9) Å] (Castaño et al., 1988). A reasonable correlation, on the other hand, is seen with distances reported for 1-hydroxypyridine-2(1H)-thione [N O = (3) Å, C S = (2) Å] (Hartung et al., 1999) and 1-[trans-(4-tert-butylcyclohexyl-1-oxy)]pyridine-2(1H)-thione [N O = (4) Å, C S = (4) Å] (Hartung, Hiller et al., 1996). These findings point to a significant statistical weight of the thione formula for representing major structural aspects of the title compound (I) in the solid state. A hypothesis that is evident from the current results suggests that comparatively strong ligand to metal interactions occur in (2-thiooxo-1,2- dihydropyridine-1-olato)lithium(i). These attractions are likely to reduce its reactivity toward alkyl halides or tosylates sup-1

4 even in strong donor solvents such as dimethyl sulfoxide or dimethyl formamide (Hartung et al., 1999), thus providing an explanation of its unusual reactivity. S2. Experimental Crystals suitable for X-ray diffraction were grown by slow concentrating a saturated solution of (2-thiooxo-1,2-dihydropyridine-1-olato)lithium(I) (Hartung et al., 1999) in EtOH at 293 K. S3. Refinement All H atoms were positioned geometrically (C H = Å, O H = 0.82 Å), and treated as riding atoms, with U iso (H)=1.2 or 1.5 times U eq (parent atom). Figure 1 Molecular structure of (I). Displacement ellipsoids are plotted at the 50% probability level (O atoms are depicted in red, N in blue, C in yellow and Li in purple). C-bound H atoms omitted for clarity. Poly[ethanolbis(µ 3-2-thioxo-1,2-dihydropyridine-1-olato)dilithium(I)] Crystal data [Li 2 (C 5 H 4 NOS) 2 (C 2 H 6 O)] M r = Monoclinic, P2 1 /c Hall symbol: -P2ybc a = (7) Å b = (2) Å c = (7) Å β = (4) V = (19) Å 3 Z = 8 F(000) = 1296 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 1033 reflections θ = µ = 0.38 mm 1 sup-2

5 T = 300 K Needle, colourless Data collection Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector Radiation source: Enhance (Mo) X-ray Source Graphite monochromator Detector resolution: pixels mm -1 rotation method data acquisition using ω and φ scans Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 383 parameters 0 restraints Primary atom site location: structure-invariant direct methods mm Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2006); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] T min = 0.835, T max = measured reflections 5597 independent reflections 1539 reflections with I > 2σ(I) R int = θ max = 26.4, θ min = 4.1 h = k = 8 4 l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.039P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.44 e Å 3 Δρ min = 0.32 e Å 3 Special details 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq C (2) (6) (2) (12) C (2) (6) (3) (14) H * C (3) (7) (3) (14) H * C (3) (7) (3) (15) H * C (2) (6) (3) (14) H * sup-3

6 C (2) (6) (3) (12) C (3) (7) (3) (14) H * C (3) (6) (3) (15) H * C (3) (6) (3) (14) H * C (3) (6) (3) (14) H * C (2) (6) (2) (13) C (2) (6) (3) (13) H * C (3) (7) (3) (15) H * C (3) (7) (3) (15) H * C (2) (6) (3) (13) H * C (2) (6) (3) (12) C (3) (6) (2) (13) H * C (3) (6) (3) (14) H * C (2) (6) (3) (14) H * C (2) (6) (2) (14) H * C (3) (9) (3) (2) H21A * H21B * C (4) (10) (4) (4) H22A * H22B * H22C * C (4) (12) (4) (3) H23A * H23B * C (4) (11) (6) (6) H24A * H24B * H24C * Li (4) (11) (4) (2) Li (4) (11) (4) (2) N (2) (5) (2) (10) N (2) (5) (2) (10) N (2) (5) (2) (10) N (2) (5) (2) (10) O (15) (4) (16) (9) sup-4

7 O (14) (4) (15) (9) O (14) (4) (15) (9) O (15) (4) (15) (9) O (15) (5) (16) (12) H5A * O (16) (5) (19) (15) H6A * Li (4) (13) (5) (3) Li (5) (15) (5) (4) S (5) (16) (6) (3) S (6) (19) (6) (4) S (5) (16) (6) (4) S (6) (19) (6) (4) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 C (3) (3) (3) (3) (2) (2) C (3) (4) (3) (3) (3) (3) C (4) (3) (4) (3) (3) (3) C (4) (3) (3) (3) (3) (3) C (3) (3) (3) (3) (3) (3) C (3) (3) (3) (2) (2) (2) C (3) (3) (3) (3) (3) (3) C (4) (4) (4) (3) (3) (3) C (3) (3) (4) (3) (3) (3) C (4) (3) (3) (3) (3) (3) C (3) (3) (3) (3) (2) (3) C (3) (3) (3) (3) (3) (3) C (4) (3) (4) (3) (3) (3) C (4) (3) (3) (3) (3) (3) C (3) (3) (3) (3) (3) (3) C (3) (3) (3) (2) (2) (3) C (3) (3) (3) (3) (2) (3) C (4) (4) (3) (3) (3) (3) C (3) (4) (4) (3) (3) (3) C (3) (3) (3) (3) (2) (2) C (5) (6) (4) (5) (4) (4) C (5) (8) (9) (6) (6) (7) C (7) (8) (7) (7) (7) (6) C (7) (8) (13) (7) (8) (8) Li (5) (6) (5) (4) (4) (4) Li (5) (5) (6) (4) (4) (4) N (3) (3) (3) (2) (2) (2) N (3) (3) (2) (2) (2) (2) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) O (2) (3) (2) (17) (16) (18) sup-5

8 O (2) (2) (18) (17) (15) (16) O (2) (2) (19) (17) (16) (17) O (2) (2) (19) (18) (16) (17) O (2) (3) (2) (2) (18) (2) O (3) (3) (2) (2) (2) (2) Li (6) (7) (6) (5) (5) (6) Li (6) (10) (7) (6) (5) (7) S (7) (9) (7) (7) (5) (7) S (7) (11) (7) (8) (6) (8) S (7) (9) (8) (7) (6) (7) S (7) (11) (7) (8) (6) (8) Geometric parameters (Å, º) C1 N (5) C21 H21A C1 C (6) C21 H21B C1 S (5) C22 H22A C2 C (6) C22 H22B C2 H C22 H22C C3 C (6) C23 C (8) C3 H C23 O (7) C4 C (6) C23 H23A C4 H C23 H23B C5 N (5) C24 H24A C5 H C24 H24B C6 N (5) C24 H24C C6 C (6) Li1 O (8) C6 S (5) Li1 O (8) C7 C (6) Li1 O (8) C7 H Li1 S (8) C8 C (6) Li1 S (8) C8 H Li1 Li (9) C9 C (6) Li1 Li (8) C9 H Li1 Li (12) C10 N (5) Li2 O (8) C10 H Li2 O (8) C11 N (5) Li2 O (8) C11 C (6) Li2 S (8) C11 S (5) Li2 S (8) C12 C (5) Li2 Li (11) C12 H Li2 Li (10) C13 C (6) N1 O (5) C13 H N2 O (4) C14 C (6) N3 O (4) C14 H N4 O (4) C15 N (5) O1 Li (9) C15 H O1 Li4 i (11) C16 N (5) O2 Li (9) sup-6

9 C16 C (6) O3 Li (10) C16 S (5) O3 Li3 ii (10) C17 C (5) O4 Li (10) C17 H O5 Li (9) C18 C (5) O5 H5A C18 H O6 Li (8) C19 C (6) O6 H6A C19 H Li3 O3 i (10) C20 N (5) Li3 Li4 i (11) C20 H Li4 O1 ii (11) C21 O (5) Li4 Li3 ii (11) C21 C (7) Cg1 Cg (6) Cg3 Cg (6) Cg1 Cg2 ii (6) Cg3 Cg4 ii (6) Cg2 Cg1 i (6) Cg4 Cg3 i (6) N1 C1 C (4) O2 Li1 S (4) N1 C1 S (4) O4 Li1 S (3) C2 C1 S (4) O1 Li1 S (2) N1 C1 C (3) S2 Li1 S (3) C2 C1 C (3) O2 Li1 Li (2) S1 C1 C (17) O4 Li1 Li (3) C3 C2 C (5) O1 Li1 Li (2) C3 C2 C (3) S2 Li1 Li (3) C1 C2 C (3) S1 Li1 Li (3) C3 C2 H O2 Li1 Li (2) C1 C2 H O4 Li1 Li (2) C19 C2 H O1 Li1 Li (3) C2 C3 C (5) S2 Li1 Li (3) C2 C3 C (3) S1 Li1 Li (3) C4 C3 C (3) Li3 Li1 Li (2) C2 C3 H O2 Li1 Li (3) C4 C3 H O4 Li1 Li (2) C18 C3 H O1 Li1 Li (3) C3 C4 C (5) S2 Li1 Li (2) C3 C4 C (3) S1 Li1 Li (2) C5 C4 C (3) Li3 Li1 Li (3) C3 C4 H Li2 Li1 Li (2) C5 C4 H O4 Li2 O (3) C17 C4 H O4 Li2 O (3) N1 C5 C (5) O2 Li2 O (4) N1 C5 C (3) O4 Li2 S (3) C4 C5 C (3) O2 Li2 S (3) N1 C5 H O3 Li2 S (4) C4 C5 H O4 Li2 S (4) C16 C5 H O2 Li2 S (3) N2 C6 C (5) O3 Li2 S (2) sup-7

10 N2 C6 S (4) S4 Li2 S (3) C7 C6 S (4) O4 Li2 Li (3) N2 C6 C (3) O2 Li2 Li (3) C7 C6 C (3) O3 Li2 Li (3) S2 C6 C (18) S4 Li2 Li (3) C8 C7 C (5) S3 Li2 Li (3) C8 C7 C (3) O4 Li2 Li (2) C6 C7 C (3) O2 Li2 Li (2) C8 C7 H O3 Li2 Li (3) C6 C7 H S4 Li2 Li (2) C14 C7 H S3 Li2 Li (3) C7 C8 C (5) Li4 Li2 Li (3) C7 C8 C (3) O4 Li2 Li (3) C9 C8 C (3) O2 Li2 Li (2) C7 C8 H O3 Li2 Li (3) C9 C8 H S4 Li2 Li (2) C13 C8 H S3 Li2 Li (2) C8 C9 C (5) Li4 Li2 Li (3) C8 C9 C (3) Li1 Li2 Li (19) C10 C9 C (3) C5 N1 C (4) C8 C9 H C5 N1 O (4) C10 C9 H C1 N1 O (4) C12 C9 H C5 N1 N (3) N2 C10 C (5) C1 N1 N (2) N2 C10 C (3) O1 N1 N (2) C9 C10 C (3) C6 N2 C (4) N2 C10 H C6 N2 O (4) C9 C10 H C10 N2 O (4) C11 C10 H C6 N2 N (3) N3 C11 C (4) C10 N2 N (3) N3 C11 S (4) O2 N2 N (2) C12 C11 S (4) C15 N3 C (4) N3 C11 C (3) C15 N3 O (4) C12 C11 C (3) C11 N3 O (4) S3 C11 C (17) C15 N3 N (3) C13 C12 C (5) C11 N3 N (3) C13 C12 C (3) O3 N3 N (2) C11 C12 C (3) C16 N4 C (4) C13 C12 H C16 N4 O (4) C11 C12 H C20 N4 O (4) C9 C12 H C16 N4 N (3) C12 C13 C (5) C20 N4 N (3) C12 C13 C (3) O4 N4 N (2) C14 C13 C (3) N1 O1 Li (4) C12 C13 H N1 O1 Li (3) C14 C13 H Li3 O1 Li (3) C8 C13 H N1 O1 Li4 i (4) C13 C14 C (5) Li3 O1 Li4 i 86.6 (4) sup-8

11 C13 C14 C (3) Li1 O1 Li4 i (4) C15 C14 C (3) N2 O2 Li (4) C13 C14 H N2 O2 Li (3) C15 C14 H Li3 O2 Li (4) C7 C14 H N2 O2 Li (3) N3 C15 C (5) Li3 O2 Li (4) N3 C15 C (3) Li1 O2 Li (3) C14 C15 C (3) N3 O3 Li (4) N3 C15 H N3 O3 Li (3) C14 C15 H Li4 O3 Li (4) C6 C15 H N3 O3 Li3 ii (3) N4 C16 C (4) Li4 O3 Li3 ii 88.1 (4) N4 C16 S (4) Li2 O3 Li3 ii (3) C17 C16 S (4) N4 O4 Li (4) N4 C16 C (3) N4 O4 Li (3) C17 C16 C (3) Li4 O4 Li (4) S4 C16 C (18) N4 O4 Li (3) C18 C17 C (5) Li4 O4 Li (4) C18 C17 C (3) Li2 O4 Li (3) C16 C17 C (3) C21 O5 Li (5) C18 C17 H C21 O5 H5A C16 C17 H Li4 O5 H5A C4 C17 H C23 O6 Li (5) C19 C18 C (5) C23 O6 H6A C19 C18 C (3) Li3 O6 H6A C17 C18 C (3) O6 Li3 O (5) C19 C18 H O6 Li3 O (5) C17 C18 H O1 Li3 O (4) C3 C18 H O6 Li3 O3 i 94.0 (4) C18 C19 C (5) O1 Li3 O3 i 92.9 (4) C18 C19 C (3) O2 Li3 O3 i (4) C20 C19 C (3) O6 Li3 Li (5) C18 C19 H O1 Li3 Li (3) C20 C19 H O2 Li3 Li (3) C2 C19 H O3 i Li3 Li (3) N4 C20 C (4) O6 Li3 Li4 i (4) N4 C20 C (3) O1 Li3 Li4 i 51.0 (3) C19 C20 C (3) O2 Li3 Li4 i (4) N4 C20 H O3 i Li3 Li4 i 41.9 (3) C19 C20 H Li1 Li3 Li4 i 83.2 (3) C1 C20 H O6 Li3 Li (4) O5 C21 C (6) O1 Li3 Li (3) O5 C21 H21A O2 Li3 Li (2) C22 C21 H21A O3 i Li3 Li (3) O5 C21 H21B Li1 Li3 Li (19) C22 C21 H21B Li4 i Li3 Li (3) H21A C21 H21B O5 Li4 O (6) C21 C22 H22A O5 Li4 O (5) sup-9

12 C21 C22 H22B O3 Li4 O (4) H22A C22 H22B O5 Li4 O1 ii 93.3 (5) C21 C22 H22C O3 Li4 O1 ii 92.4 (4) H22A C22 H22C O4 Li4 O1 ii (5) H22B C22 H22C O5 Li4 Li (6) C24 C23 O (8) O3 Li4 Li (3) C24 C23 H23A O4 Li4 Li (3) O6 C23 H23A O1 ii Li4 Li (4) C24 C23 H23B O5 Li4 Li3 ii (5) O6 C23 H23B O3 Li4 Li3 ii 50.1 (3) H23A C23 H23B O4 Li4 Li3 ii (4) C23 C24 H24A O1 ii Li4 Li3 ii 42.4 (3) C23 C24 H24B Li2 Li4 Li3 ii 83.0 (3) H24A C24 H24B O5 Li4 Li (4) C23 C24 H24C O3 Li4 Li (4) H24A C24 H24C O4 Li4 Li (3) H24B C24 H24C O1 ii Li4 Li (4) O2 Li1 O (3) Li2 Li4 Li (2) O2 Li1 O (3) Li3 ii Li4 Li (3) O4 Li1 O (4) C1 S1 Li (2) O2 Li1 S (3) C6 S2 Li (2) O4 Li1 S (3) C11 S3 Li (2) O1 Li1 S (4) C16 S4 Li (2) N1 C1 C2 C3 0.6 (7) O2 Li2 O3 Li (5) S1 C1 C2 C (4) S4 Li2 O3 Li (6) C20 C1 C2 C (5) S3 Li2 O3 Li (3) N1 C1 C2 C (4) Li1 Li2 O3 Li (4) S1 C1 C2 C (4) Li3 Li2 O3 Li (6) C20 C1 C2 C (14) O4 Li2 O3 Li3 ii 84.9 (4) C1 C2 C3 C4 0.1 (8) O2 Li2 O3 Li3 ii (3) C19 C2 C3 C (4) S4 Li2 O3 Li3 ii 15.9 (7) C1 C2 C3 C (5) S3 Li2 O3 Li3 ii 93.5 (4) C19 C2 C3 C (16) Li4 Li2 O3 Li3 ii 85.7 (5) C2 C3 C4 C5 0.4 (7) Li1 Li2 O3 Li3 ii (4) C18 C3 C4 C (5) Li3 Li2 O3 Li3 ii (5) C2 C3 C4 C (4) C16 N4 O4 Li (5) C18 C3 C4 C (16) C20 N4 O4 Li (6) C3 C4 C5 N1 0.4 (8) N1 N4 O4 Li (3) C17 C4 C5 N (5) C16 N4 O4 Li (6) C3 C4 C5 C (5) C20 N4 O4 Li (4) C17 C4 C5 C (14) N1 N4 O4 Li (4) N2 C6 C7 C8 0.2 (8) C16 N4 O4 Li (5) S2 C6 C7 C (4) C20 N4 O4 Li (5) C15 C6 C7 C (5) N1 N4 O4 Li (3) N2 C6 C7 C (4) O2 Li2 O4 N (4) S2 C6 C7 C (4) O3 Li2 O4 N (3) C15 C6 C7 C (14) S4 Li2 O4 N (4) sup-10

13 C6 C7 C8 C9 1.7 (8) S3 Li2 O4 N (10) C14 C7 C8 C (4) Li4 Li2 O4 N (5) C6 C7 C8 C (5) Li1 Li2 O4 N (4) C14 C7 C8 C (16) Li3 Li2 O4 N (4) C7 C8 C9 C (7) O2 Li2 O4 Li (4) C13 C8 C9 C (5) O3 Li2 O4 Li4 0.7 (4) C7 C8 C9 C (4) S4 Li2 O4 Li (3) C13 C8 C9 C (15) S3 Li2 O4 Li4 5.0 (12) C8 C9 C10 N2 0.2 (8) Li1 Li2 O4 Li (4) C12 C9 C10 N (5) Li3 Li2 O4 Li (4) C8 C9 C10 C (4) O2 Li2 O4 Li1 0.6 (4) C12 C9 C10 C (14) O3 Li2 O4 Li (3) N2 C10 C11 N3 7.8 (3) S4 Li2 O4 Li (2) C9 C10 C11 N (4) S3 Li2 O4 Li (11) N2 C10 C11 C (4) Li4 Li2 O4 Li (4) C9 C10 C11 C (3) Li3 Li2 O4 Li (3) N2 C10 C11 S (3) O2 Li1 O4 N (3) C9 C10 C11 S (4) O1 Li1 O4 N (5) N3 C11 C12 C (7) S2 Li1 O4 N (3) S3 C11 C12 C (4) S1 Li1 O4 N (4) C10 C11 C12 C (5) Li3 Li1 O4 N (4) N3 C11 C12 C (4) Li2 Li1 O4 N (4) S3 C11 C12 C (4) Li4 Li1 O4 N (5) C10 C11 C12 C (14) O2 Li1 O4 Li (4) C8 C9 C12 C (4) O1 Li1 O4 Li (3) C10 C9 C12 C (5) S2 Li1 O4 Li4 7.6 (6) C8 C9 C12 C (5) S1 Li1 O4 Li (4) C10 C9 C12 C (3) Li3 Li1 O4 Li (4) C11 C12 C13 C (8) Li2 Li1 O4 Li (5) C9 C12 C13 C (4) O2 Li1 O4 Li2 0.7 (4) C11 C12 C13 C (5) O1 Li1 O4 Li (4) C9 C12 C13 C (16) S2 Li1 O4 Li (3) C7 C8 C13 C (5) S1 Li1 O4 Li (2) C9 C8 C13 C (4) Li3 Li1 O4 Li (4) C7 C8 C13 C (4) Li4 Li1 O4 Li (5) C9 C8 C13 C (5) C22 C21 O5 Li (9) C12 C13 C14 C (8) C24 C23 O6 Li (9) C8 C13 C14 C (5) C23 O6 Li3 O (12) C12 C13 C14 C (4) C23 O6 Li3 O (11) C8 C13 C14 C (16) C23 O6 Li3 O3 i (8) C8 C7 C14 C (4) C23 O6 Li3 Li (16) C6 C7 C14 C (5) C23 O6 Li3 Li4 i (9) C8 C7 C14 C (5) C23 O6 Li3 Li (10) C6 C7 C14 C (4) N1 O1 Li3 O (11) C13 C14 C15 N3 1.8 (8) Li1 O1 Li3 O (7) C7 C14 C15 N (5) Li4 i O1 Li3 O (7) C13 C14 C15 C (5) N1 O1 Li3 O (5) C7 C14 C15 C (14) Li1 O1 Li3 O2 1.2 (4) sup-11

14 N2 C6 C15 N3 8.0 (3) Li4 i O1 Li3 O (4) C7 C6 C15 N (4) N1 O1 Li3 O3 i (5) S2 C6 C15 N (4) Li1 O1 Li3 O3 i (3) N2 C6 C15 C (4) Li4 i O1 Li3 O3 i 0.6 (4) C7 C6 C15 C (4) N1 O1 Li3 Li (6) S2 C6 C15 C (4) Li4 i O1 Li3 Li (3) N1 C5 C16 N4 9.9 (4) N1 O1 Li3 Li4 i (6) C4 C5 C16 N (4) Li1 O1 Li3 Li4 i (3) N1 C5 C16 C (4) N1 O1 Li3 Li (5) C4 C5 C16 C (3) Li1 O1 Li3 Li (3) N1 C5 C16 S (4) Li4 i O1 Li3 Li (3) C4 C5 C16 S (4) N2 O2 Li3 O (7) N4 C16 C17 C (8) Li1 O2 Li3 O (5) S4 C16 C17 C (4) Li2 O2 Li3 O (7) C5 C16 C17 C (5) N2 O2 Li3 O (4) N4 C16 C17 C (4) Li1 O2 Li3 O1 1.3 (5) S4 C16 C17 C (4) Li2 O2 Li3 O (5) C5 C16 C17 C (14) N2 O2 Li3 O3 i 30.8 (6) C3 C4 C17 C (4) Li1 O2 Li3 O3 i 98.2 (4) C5 C4 C17 C (4) Li2 O2 Li3 O3 i (3) C3 C4 C17 C (5) N2 O2 Li3 Li (4) C5 C4 C17 C (3) Li2 O2 Li3 Li (4) C16 C17 C18 C (8) N2 O2 Li3 Li4 i 77.3 (4) C4 C17 C18 C (4) Li1 O2 Li3 Li4 i 51.7 (4) C16 C17 C18 C (5) Li2 O2 Li3 Li4 i (4) C4 C17 C18 C (16) N2 O2 Li3 Li (5) C2 C3 C18 C (4) Li1 O2 Li3 Li (4) C4 C3 C18 C (5) O2 Li1 Li3 O (9) C2 C3 C18 C (5) O4 Li1 Li3 O6 1.5 (10) C4 C3 C18 C (4) O1 Li1 Li3 O (10) C17 C18 C19 C (7) S2 Li1 Li3 O (9) C3 C18 C19 C (5) S1 Li1 Li3 O (9) C17 C18 C19 C (4) Li2 Li1 Li3 O (9) C3 C18 C19 C (15) Li4 Li1 Li3 O (11) C3 C2 C19 C (4) O2 Li1 Li3 O (6) C1 C2 C19 C (5) O4 Li1 Li3 O (4) C3 C2 C19 C (5) S2 Li1 Li3 O (4) C1 C2 C19 C (3) S1 Li1 Li3 O1 3.2 (3) C18 C19 C20 N4 0.4 (8) Li2 Li1 Li3 O (4) C2 C19 C20 N (4) Li4 Li1 Li3 O (4) C18 C19 C20 C (5) O4 Li1 Li3 O (4) C2 C19 C20 C (14) O1 Li1 Li3 O (6) N1 C1 C20 N4 8.8 (3) S2 Li1 Li3 O (3) C2 C1 C20 N (4) S1 Li1 Li3 O (5) S1 C1 C20 N (3) Li2 Li1 Li3 O (3) N1 C1 C20 C (4) Li4 Li1 Li3 O (4) C2 C1 C20 C (3) O2 Li1 Li3 O3 i (5) S1 C1 C20 C (4) O4 Li1 Li3 O3 i (4) sup-12

15 O2 Li1 Li2 O (5) O1 Li1 Li3 O3 i 74.2 (4) O1 Li1 Li2 O (4) S2 Li1 Li3 O3 i 60.1 (4) S2 Li1 Li2 O (4) S1 Li1 Li3 O3 i 71.0 (4) S1 Li1 Li2 O (4) Li2 Li1 Li3 O3 i (4) Li3 Li1 Li2 O (3) Li4 Li1 Li3 O3 i (3) Li4 Li1 Li2 O (3) O2 Li1 Li3 Li4 i (4) O4 Li1 Li2 O (5) O4 Li1 Li3 Li4 i (3) O1 Li1 Li2 O (3) O1 Li1 Li3 Li4 i 44.3 (3) S2 Li1 Li2 O (3) S2 Li1 Li3 Li4 i 90.0 (3) S1 Li1 Li2 O (6) S1 Li1 Li3 Li4 i 41.1 (3) Li3 Li1 Li2 O (3) Li2 Li1 Li3 Li4 i (3) Li4 Li1 Li2 O (3) Li4 Li1 Li3 Li4 i (4) O2 Li1 Li2 O (4) O2 Li1 Li3 Li (3) O4 Li1 Li2 O (3) O4 Li1 Li3 Li (3) O1 Li1 Li2 O (4) O1 Li1 Li3 Li (4) S2 Li1 Li2 O (3) S2 Li1 Li3 Li (3) S1 Li1 Li2 O (5) S1 Li1 Li3 Li (3) Li3 Li1 Li2 O (3) Li4 Li1 Li3 Li2 0.1 (3) Li4 Li1 Li2 O (3) O4 Li2 Li3 O (5) O2 Li1 Li2 S (3) O2 Li2 Li3 O (6) O4 Li1 Li2 S (3) O3 Li2 Li3 O (7) O1 Li1 Li2 S (3) S4 Li2 Li3 O (3) S2 Li1 Li2 S (3) S3 Li2 Li3 O (4) S1 Li1 Li2 S (5) Li4 Li2 Li3 O (4) Li3 Li1 Li2 S (2) Li1 Li2 Li3 O (4) Li4 Li1 Li2 S (3) O4 Li2 Li3 O1 3.5 (3) O2 Li1 Li2 S (4) O2 Li2 Li3 O (5) O4 Li1 Li2 S (6) O3 Li2 Li3 O (6) O1 Li1 Li2 S (5) S4 Li2 Li3 O (3) S2 Li1 Li2 S (5) S3 Li2 Li3 O (4) S1 Li1 Li2 S (4) Li4 Li2 Li3 O (5) Li3 Li1 Li2 S (5) Li1 Li2 Li3 O (3) Li4 Li1 Li2 S (5) O4 Li2 Li3 O (4) O2 Li1 Li2 Li (3) O3 Li2 Li3 O2 6.2 (5) O4 Li1 Li2 Li (3) S4 Li2 Li3 O (5) O1 Li1 Li2 Li (3) S3 Li2 Li3 O (4) S2 Li1 Li2 Li (3) Li4 Li2 Li3 O (5) S1 Li1 Li2 Li (5) Li1 Li2 Li3 O (4) Li3 Li1 Li2 Li (3) O4 Li2 Li3 O3 i 98.0 (6) O2 Li1 Li2 Li (3) O2 Li2 Li3 O3 i 3.1 (5) O4 Li1 Li2 Li (3) O3 Li2 Li3 O3 i 9.2 (9) O1 Li1 Li2 Li (3) S4 Li2 Li3 O3 i (7) S2 Li1 Li2 Li (3) S3 Li2 Li3 O3 i 72.6 (7) S1 Li1 Li2 Li (5) Li4 Li2 Li3 O3 i 69.7 (8) Li4 Li1 Li2 Li (3) Li1 Li2 Li3 O3 i 69.6 (6) C4 C5 N1 C1 0.1 (7) O4 Li2 Li3 Li (3) C16 C5 N1 C (4) O2 Li2 Li3 Li (4) C4 C5 N1 O (4) O3 Li2 Li3 Li (6) sup-13

16 C16 C5 N1 O (4) S4 Li2 Li3 Li (3) C4 C5 N1 N (5) S3 Li2 Li3 Li (3) C16 C5 N1 N (13) Li4 Li2 Li3 Li1 0.1 (4) C2 C1 N1 C5 0.6 (6) O4 Li2 Li3 Li4 i 30.8 (5) S1 C1 N1 C (3) O2 Li2 Li3 Li4 i 64.2 (5) C20 C1 N1 C (4) O3 Li2 Li3 Li4 i 58.0 (7) C2 C1 N1 O (4) S4 Li2 Li3 Li4 i (4) S1 C1 N1 O1 3.0 (6) S3 Li2 Li3 Li4 i (4) C20 C1 N1 O (4) Li4 Li2 Li3 Li4 i 2.5 (5) C2 C1 N1 N (4) Li1 Li2 Li3 Li4 i 2.4 (4) S1 C1 N1 N (3) C21 O5 Li4 O (13) C20 C1 N1 N (13) C21 O5 Li4 O (11) C7 C6 N2 C (7) C21 O5 Li4 O1 ii (7) S2 C6 N2 C (3) C21 O5 Li4 Li (17) C15 C6 N2 C (4) C21 O5 Li4 Li3 ii (8) C7 C6 N2 O (4) C21 O5 Li4 Li (9) S2 C6 N2 O2 3.4 (6) N3 O3 Li4 O (11) C15 C6 N2 O (4) Li2 O3 Li4 O (8) C7 C6 N2 N (4) Li3 ii O3 Li4 O (8) S2 C6 N2 N (3) N3 O3 Li4 O (5) C15 C6 N2 N (12) Li2 O3 Li4 O4 0.8 (5) C9 C10 N2 C6 1.4 (7) Li3 ii O3 Li4 O (4) C11 C10 N2 C (4) N3 O3 Li4 O1 ii (4) C9 C10 N2 O (4) Li2 O3 Li4 O1 ii (3) C11 C10 N2 O (4) Li3 ii O3 Li4 O1 ii 0.6 (4) C9 C10 N2 N (5) N3 O3 Li4 Li (6) C11 C10 N2 N (12) Li3 ii O3 Li4 Li (3) C14 C15 N3 C (7) N3 O3 Li4 Li3 ii (6) C6 C15 N3 C (4) Li2 O3 Li4 Li3 ii (3) C14 C15 N3 O (4) N3 O3 Li4 Li (5) C6 C15 N3 O (4) Li2 O3 Li4 Li (3) C14 C15 N3 N (5) Li3 ii O3 Li4 Li (3) C6 C15 N3 N (13) N4 O4 Li4 O (8) C12 C11 N3 C (7) Li2 O4 Li4 O (6) S3 C11 N3 C (3) Li1 O4 Li4 O (8) C10 C11 N3 C (4) N4 O4 Li4 O (4) C12 C11 N3 O (4) Li2 O4 Li4 O3 0.8 (5) S3 C11 N3 O3 2.9 (6) Li1 O4 Li4 O (5) C10 C11 N3 O (4) N4 O4 Li4 O1 ii 30.0 (6) C12 C11 N3 N (4) Li2 O4 Li4 O1 ii 97.5 (5) S3 C11 N3 N (3) Li1 O4 Li4 O1 ii (3) C10 C11 N3 N (13) N4 O4 Li4 Li (4) C6 N2 N3 C (3) Li1 O4 Li4 Li (4) C10 N2 N3 C (4) N4 O4 Li4 Li3 ii 77.5 (5) O2 N2 N3 C (4) Li2 O4 Li4 Li3 ii 50.0 (4) C6 N2 N3 C (4) Li1 O4 Li4 Li3 ii (4) C10 N2 N3 C (3) N4 O4 Li4 Li (5) O2 N2 N3 C (4) Li2 O4 Li4 Li (4) sup-14

17 C6 N2 N3 O (4) O4 Li2 Li4 O (11) C10 N2 N3 O (4) O2 Li2 Li4 O5 7.0 (11) O2 N2 N3 O3 8.6 (2) O3 Li2 Li4 O (12) C17 C16 N4 C (6) S4 Li2 Li4 O (11) S4 C16 N4 C (3) S3 Li2 Li4 O (11) C5 C16 N4 C (4) Li1 Li2 Li4 O (11) C17 C16 N4 O (4) Li3 Li2 Li4 O (12) S4 C16 N4 O4 2.3 (6) O4 Li2 Li4 O (6) C5 C16 N4 O (4) O2 Li2 Li4 O (5) C17 C16 N4 N (4) S4 Li2 Li4 O (4) S4 C16 N4 N (3) S3 Li2 Li4 O3 0.8 (3) C5 C16 N4 N (13) Li1 Li2 Li4 O (4) C19 C20 N4 C (7) Li3 Li2 Li4 O (4) C1 C20 N4 C (4) O2 Li2 Li4 O (4) C19 C20 N4 O (4) O3 Li2 Li4 O (6) C1 C20 N4 O (4) S4 Li2 Li4 O (3) C19 C20 N4 N (5) S3 Li2 Li4 O (5) C1 C20 N4 N (12) Li1 Li2 Li4 O (3) C5 N1 N4 C (4) Li3 Li2 Li4 O (5) C1 N1 N4 C (4) O4 Li2 Li4 O1 ii (5) O1 N1 N4 C (4) O2 Li2 Li4 O1 ii (4) C5 N1 N4 C (4) O3 Li2 Li4 O1 ii 73.6 (4) C1 N1 N4 C (3) S4 Li2 Li4 O1 ii 60.6 (4) O1 N1 N4 C (4) S3 Li2 Li4 O1 ii 72.7 (4) C5 N1 N4 O (4) Li1 Li2 Li4 O1 ii (4) C1 N1 N4 O (4) Li3 Li2 Li4 O1 ii (3) O1 N1 N4 O4 8.7 (2) O4 Li2 Li4 Li3 ii (4) C5 N1 O1 Li (8) O2 Li2 Li4 Li3 ii (3) C1 N1 O1 Li (5) O3 Li2 Li4 Li3 ii 42.8 (3) N4 N1 O1 Li (5) S4 Li2 Li4 Li3 ii 91.3 (3) C5 N1 O1 Li (4) S3 Li2 Li4 Li3 ii 42.0 (3) C1 N1 O1 Li (5) Li1 Li2 Li4 Li3 ii (3) N4 N1 O1 Li (3) Li3 Li2 Li4 Li3 ii (4) C5 N1 O1 Li4 i 88.3 (5) O4 Li2 Li4 Li (3) C1 N1 O1 Li4 i 91.6 (5) O2 Li2 Li4 Li (3) N4 N1 O1 Li4 i (3) O3 Li2 Li4 Li (4) O2 Li1 O1 N (3) S4 Li2 Li4 Li (3) O4 Li1 O1 N (5) S3 Li2 Li4 Li (3) S2 Li1 O1 N (4) Li3 Li2 Li4 Li1 0.1 (3) S1 Li1 O1 N (3) O2 Li1 Li4 O (5) Li3 Li1 O1 N (4) O4 Li1 Li4 O (7) Li2 Li1 O1 N (3) O1 Li1 Li4 O (7) Li4 Li1 O1 N (6) S2 Li1 Li4 O (4) O2 Li1 O1 Li3 1.1 (4) S1 Li1 Li4 O (4) O4 Li1 O1 Li (5) Li3 Li1 Li4 O (4) S2 Li1 O1 Li (5) Li2 Li1 Li4 O (5) S1 Li1 O1 Li (3) O2 Li1 Li4 O3 1.1 (3) Li2 Li1 O1 Li (4) O4 Li1 Li4 O (5) sup-15

18 Li4 Li1 O1 Li (6) O1 Li1 Li4 O (6) O2 Li1 O1 Li4 i 82.8 (4) S2 Li1 Li4 O (4) O4 Li1 O1 Li4 i (3) S1 Li1 Li4 O (4) S2 Li1 O1 Li4 i 13.8 (7) Li3 Li1 Li4 O (5) S1 Li1 O1 Li4 i 92.9 (4) Li2 Li1 Li4 O (3) Li3 Li1 O1 Li4 i 84.0 (4) O2 Li1 Li4 O (5) Li2 Li1 O1 Li4 i (4) O1 Li1 Li4 O4 6.8 (5) Li4 Li1 O1 Li4 i (6) S2 Li1 Li4 O (6) C6 N2 O2 Li (5) S1 Li1 Li4 O (4) C10 N2 O2 Li (6) Li3 Li1 Li4 O (5) N3 N2 O2 Li (3) Li2 Li1 Li4 O (4) C6 N2 O2 Li (6) O2 Li1 Li4 O1 ii (7) C10 N2 O2 Li (4) O4 Li1 Li4 O1 ii 3.3 (5) N3 N2 O2 Li (4) O1 Li1 Li4 O1 ii 10.1 (9) C6 N2 O2 Li (5) S2 Li1 Li4 O1 ii (7) C10 N2 O2 Li (5) S1 Li1 Li4 O1 ii 71.9 (7) N3 N2 O2 Li (3) Li3 Li1 Li4 O1 ii 70.6 (8) O4 Li1 O2 N (4) Li2 Li1 Li4 O1 ii 70.7 (7) O1 Li1 O2 N (3) O2 Li1 Li4 Li (3) S2 Li1 O2 N (4) O4 Li1 Li4 Li (4) S1 Li1 O2 N (10) O1 Li1 Li4 Li (6) Li3 Li1 O2 N (5) S2 Li1 Li4 Li (3) Li2 Li1 O2 N (4) S1 Li1 Li4 Li (3) Li4 Li1 O2 N (4) Li3 Li1 Li4 Li2 0.1 (4) O4 Li1 O2 Li (3) O2 Li1 Li4 Li3 ii 32.0 (5) O1 Li1 O2 Li3 1.1 (4) O4 Li1 Li4 Li3 ii 65.1 (5) S2 Li1 O2 Li (3) O1 Li1 Li4 Li3 ii 58.2 (8) S1 Li1 O2 Li (11) S2 Li1 Li4 Li3 ii (4) Li2 Li1 O2 Li (4) S1 Li1 Li4 Li3 ii (4) Li4 Li1 O2 Li (3) Li3 Li1 Li4 Li3 ii 2.3 (6) O4 Li1 O2 Li2 0.6 (4) Li2 Li1 Li4 Li3 ii 2.4 (4) O1 Li1 O2 Li (3) N1 C1 S1 Li (4) S2 Li1 O2 Li (2) C2 C1 S1 Li (4) S1 Li1 O2 Li (10) C20 C1 S1 Li (19) Li3 Li1 O2 Li (4) O2 Li1 S1 C (10) Li4 Li1 O2 Li (3) O4 Li1 S1 C (3) O4 Li2 O2 N (3) O1 Li1 S1 C (2) O3 Li2 O2 N (5) S2 Li1 S1 C (3) S4 Li2 O2 N (3) Li3 Li1 S1 C (3) S3 Li2 O2 N (4) Li2 Li1 S1 C (5) Li4 Li2 O2 N (4) Li4 Li1 S1 C (3) Li1 Li2 O2 N (4) N2 C6 S2 Li1 5.1 (4) Li3 Li2 O2 N (5) C7 C6 S2 Li (5) O4 Li2 O2 Li (4) C15 C6 S2 Li (2) O3 Li2 O2 Li (3) O2 Li1 S2 C6 8.3 (3) S4 Li2 O2 Li3 9.6 (5) O4 Li1 S2 C (3) S3 Li2 O2 Li (4) O1 Li1 S2 C (5) Li4 Li2 O2 Li (4) S1 Li1 S2 C (3) sup-16

19 Li1 Li2 O2 Li (4) Li3 Li1 S2 C (3) O4 Li2 O2 Li1 0.7 (4) Li2 Li1 S2 C (3) O3 Li2 O2 Li (4) Li4 Li1 S2 C (2) S4 Li2 O2 Li (3) N3 C11 S3 Li (4) S3 Li2 O2 Li (3) C12 C11 S3 Li (4) Li4 Li2 O2 Li (4) C10 C11 S3 Li (19) Li3 Li2 O2 Li (4) O4 Li2 S3 C (11) C15 N3 O3 Li (8) O2 Li2 S3 C (3) C11 N3 O3 Li (6) O3 Li2 S3 C (2) N2 N3 O3 Li (6) S4 Li2 S3 C (3) C15 N3 O3 Li (4) Li4 Li2 S3 C (3) C11 N3 O3 Li (5) Li1 Li2 S3 C (5) N2 N3 O3 Li (3) Li3 Li2 S3 C (2) C15 N3 O3 Li3 ii 88.3 (5) N4 C16 S4 Li2 7.4 (4) C11 N3 O3 Li3 ii 93.3 (5) C17 C16 S4 Li (5) N2 N3 O3 Li3 ii (3) C5 C16 S4 Li (2) O4 Li2 O3 N (3) O4 Li2 S4 C (3) O2 Li2 O3 N (5) O2 Li2 S4 C (3) S4 Li2 O3 N (4) O3 Li2 S4 C (5) S3 Li2 O3 N (3) S3 Li2 S4 C (3) Li4 Li2 O3 N (4) Li4 Li2 S4 C (3) Li1 Li2 O3 N (3) Li1 Li2 S4 C (2) Li3 Li2 O3 N (6) Li3 Li2 S4 C (2) O4 Li2 O3 Li4 0.7 (4) Symmetry codes: (i) x, y 1, z; (ii) x, y+1, z. Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O5 H5A S1 ii (3) 174 O6 H6A S3 i (4) 172 Symmetry codes: (i) x, y 1, z; (ii) x, y+1, z. sup-17