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

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ISSN: 2056-9890
Volume 64| Part 3| March 2008| Pages m462-m463

Poly[ethano­lbis(μ3-2-thio­xo-1,2-di­hydro­pyridin-1-olato)dilithium(I)]

aFachbereich Chemie, Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, D-67663 Kaiserslautern, Germany, and bStrukturforschung, FB 11, Material- und Geowissenschaften, Technische Universität Darmstadt, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: hartung@chemie.uni-kl.de

(Received 13 December 2007; accepted 1 February 2008; online 8 February 2008)

The title compound, [Li2(C5H4NOS)2(C2H6O)]n, having two formula units in the asymmetric unit, forms infinite chains of Li2O2 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. ππ Inter­actions between polymeric chains are evident from centroid-to-centroid distances of pyridine­thione fragments of 3.461 (6)–3.607 (6) Å. The N—O and C—S bond lengths are distinctively different from those in hitherto investigated NiII, ZnII and (H3C)2TlIII 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[Barnett, B. L., Kretschmar, H. C. & Hartmann, F. A. (1977). Inorg. Chem. 16, 1834-1838.]); Castaño et al. (1988[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, 1897-1904.]); Chen et al. (1991[Chen, X., Hu, Y., Wu, D., Weng, L. & Kang, B. (1991). Polyhedron, 10, 2651-2657.]); Hartung, Hiller et al. (1996[Hartung, J., Hiller, M., Schwarz, M., Svoboda, I. & Fuess, H. (1996). Liebigs Ann. Chem. pp. 2091-2097.]); Hartung, Svoboda et al. (1996[Hartung, J., Svoboda, I. & Fuess, H. (1996). Acta Cryst. C52, 2841-2844.]); Hartung et al. (1999[Hartung, J., Kneuer, R., Schwarz, M., Svoboda, I. & Fuess, H. (1999). Eur. J. Org. Chem. pp. 97-106.], 2007[Hartung, J., Svoboda, I. & Fuess, H. (2007). Unpublished results.]).

[Scheme 1]

Experimental

Crystal data
  • [Li2(C5H4NOS)2(C2H6O)]

  • Mr = 312.25

  • Monoclinic, P 21 /c

  • a = 22.492 (7) Å

  • b = 7.047 (2) Å

  • c = 20.881 (7) Å

  • β = 119.31 (4)°

  • V = 2886.0 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 300 (2) K

  • 0.50 × 0.12 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction , 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.835, Tmax = 0.971

  • 16998 measured reflections

  • 5597 independent reflections

  • 1539 reflections with I > 2σ(I)

  • Rint = 0.086

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.100

  • S = 0.71

  • 5597 reflections

  • 383 parameters

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.32 e Å−3

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.

Cg1⋯Cg2 3.470 (6)
Cg1⋯Cg2i 3.596 (6)
Cg3⋯Cg4 3.461 (6)
Cg3⋯Cg4i 3.607 (6)
Symmetry code: (i) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5A⋯S1i 0.82 2.39 3.205 (3) 174
O6—H6A⋯S3ii 0.82 2.41 3.226 (4) 172
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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 P21/c (Z = 4). Its structure is composed of infinite chains of Li2O2 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 centroid-to-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 = -15.0 (6)°] than in the other [Li1—S1—C1—N1 = -34.5 (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 = 1.389 (5) Å, N2—O2 = 1.383 (4) Å, N3—O3 = 1.383 (4) Å, N4—O4 = 1.390 Å, C1—S1 = 1.654 (5) Å, C6—S2 = °1.671 (5), C11—S3 = 1.647 (5) Å, C16—S4 = 1.655 (5) Å] are distinctively different from those reported for the corresponding subunits 2-alkylsulfanyl pyridine-1-oxides [N—O = 1.308 Å, C—S = 1.739 (3) Å] (Hartung, Svoboda et al., 1996), bis[2-thiooxo-1,2-dihydropyridine-1-olato]nickel [N—O = 1.343 (3) Å and 1.344 (4) Å, C—S = 1.710 (3) Å and 1.712 (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 = 1.716 (9) Å and 1.719 (9) Å] (Barnett et al., 1977), and the derived dimethylthallium(III) complex [N—O = 1.338 (9) Å, C—S = 1.736 (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 = 1.367 (3) Å, C—S = 1.684 (2) Å] (Hartung et al., 1999) and 1-[trans-(4-tert-butylcyclohexyl-1-oxy)]pyridine-2(1H)-thione [N—O = 1.384 (4) Å, C—S = 1.666 (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 even in strong donor solvents such as dimethyl sulfoxide or dimethyl formamide (Hartung et al., 1999), thus providing an explanation of its unusual reactivity.

Related literature top

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).

Experimental top

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.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93–0.96 Å, O—H = 0.82 Å), and treated as riding atoms, with Uiso(H)=1.2 or 1.5 times Ueq(parent atom).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 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(µ3-2-thioxo-1,2-dihydropyridine-1-olato)dilithium(I)] top
Crystal data top
[Li2(C5H4NOS)2(C2H6O)]F(000) = 1296
Mr = 312.25Dx = 1.437 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 1033 reflections
a = 22.492 (7) Åθ = 2.2–20.6°
b = 7.047 (2) ŵ = 0.38 mm1
c = 20.881 (7) ÅT = 300 K
β = 119.31 (4)°Needle, colourless
V = 2886.0 (19) Å30.50 × 0.12 × 0.08 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
5597 independent reflections
Radiation source: Enhance (Mo) X-ray Source1539 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
Detector resolution: 8.4012 pixels mm-1θmax = 26.4°, θmin = 4.1°
rotation method data acquisition using ω and ϕ scansh = 2827
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)]
k = 84
Tmin = 0.835, Tmax = 0.971l = 2626
16998 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 0.71 w = 1/[σ2(Fo2) + (0.039P)2]
where P = (Fo2 + 2Fc2)/3
5597 reflections(Δ/σ)max = 0.073
383 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
[Li2(C5H4NOS)2(C2H6O)]V = 2886.0 (19) Å3
Mr = 312.25Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.492 (7) ŵ = 0.38 mm1
b = 7.047 (2) ÅT = 300 K
c = 20.881 (7) Å0.50 × 0.12 × 0.08 mm
β = 119.31 (4)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
5597 independent reflections
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)]
1539 reflections with I > 2σ(I)
Tmin = 0.835, Tmax = 0.971Rint = 0.087
16998 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.71Δρmax = 0.44 e Å3
5597 reflectionsΔρmin = 0.32 e Å3
383 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3919 (2)0.1763 (6)0.4763 (2)0.0295 (12)
C20.4254 (2)0.1700 (6)0.4334 (3)0.0386 (14)
H20.46990.12450.45580.046*
C30.3978 (3)0.2239 (7)0.3642 (3)0.0458 (14)
H30.42140.21750.33810.055*
C40.3336 (3)0.2888 (7)0.3338 (3)0.0447 (15)
H40.31130.32820.28510.054*
C50.3001 (2)0.2975 (6)0.3752 (3)0.0402 (14)
H50.25570.34380.35290.048*
C60.2170 (2)0.0318 (6)0.6268 (3)0.0319 (12)
C70.1856 (3)0.0303 (7)0.6722 (3)0.0438 (14)
H70.21220.06460.72120.053*
C80.1214 (3)0.0163 (6)0.6493 (3)0.0486 (15)
H80.10280.01200.68050.058*
C90.0846 (3)0.0697 (6)0.5797 (3)0.0407 (14)
H90.03950.10730.56090.049*
C100.1149 (3)0.0686 (6)0.5349 (3)0.0409 (14)
H100.08870.10590.48610.049*
C110.1076 (2)0.4132 (6)0.5198 (2)0.0330 (13)
C120.0749 (2)0.4095 (6)0.5644 (3)0.0365 (13)
H120.03010.36650.54320.044*
C130.1047 (3)0.4630 (7)0.6326 (3)0.0492 (15)
H130.08240.45850.66020.059*
C140.1692 (3)0.5252 (7)0.6615 (3)0.0461 (15)
H140.19290.56170.71050.055*
C150.2008 (2)0.5354 (6)0.6187 (3)0.0383 (13)
H150.24500.58240.63960.046*
C160.2826 (2)0.2062 (6)0.3712 (3)0.0328 (12)
C170.3156 (3)0.2097 (6)0.3269 (2)0.0377 (13)
H170.28970.17300.27810.045*
C180.3795 (3)0.2606 (6)0.3499 (3)0.0430 (14)
H180.39820.26260.31890.052*
C190.4145 (2)0.3083 (6)0.4196 (3)0.0422 (14)
H190.45980.34550.43900.051*
C200.3856 (2)0.3042 (6)0.4644 (2)0.0361 (14)
H200.41220.33810.51340.043*
C210.4071 (3)0.5216 (9)0.6919 (3)0.104 (2)
H21A0.38260.44090.70880.125*
H21B0.41720.64050.71860.125*
C220.4667 (4)0.4349 (10)0.7052 (4)0.189 (4)
H22A0.45650.32450.67470.227*
H22B0.49180.39810.75590.227*
H22C0.49350.52160.69440.227*
C230.0849 (4)0.2585 (12)0.3053 (4)0.145 (3)
H23A0.10820.17070.28930.174*
H23B0.07150.36950.27380.174*
C240.0319 (4)0.1783 (11)0.3032 (6)0.220 (6)
H24A0.04630.07110.33580.264*
H24B0.00900.26790.31840.264*
H24C0.00130.13670.25410.264*
Li10.3025 (4)0.0014 (11)0.5407 (4)0.041 (2)
Li20.1956 (4)0.2363 (11)0.4551 (4)0.038 (2)
N10.3283 (2)0.2435 (5)0.4436 (2)0.0319 (10)
N20.1786 (2)0.0174 (5)0.5582 (2)0.0278 (10)
N30.1707 (2)0.4819 (5)0.5507 (2)0.0324 (10)
N40.3213 (2)0.2539 (5)0.4404 (2)0.0297 (10)
O10.29231 (15)0.2565 (4)0.48172 (16)0.0402 (9)
O20.20416 (14)0.0166 (4)0.51000 (15)0.0331 (9)
O30.20569 (14)0.4927 (4)0.51171 (15)0.0340 (9)
O40.29464 (15)0.2503 (4)0.48815 (15)0.0363 (9)
O50.36826 (15)0.5544 (5)0.61947 (16)0.0843 (12)
H5A0.38350.64550.60780.101*
O60.12663 (16)0.3096 (5)0.37800 (19)0.1027 (15)
H6A0.11020.40160.38780.123*
Li30.1999 (4)0.2468 (13)0.4565 (5)0.060 (3)
Li40.2976 (5)0.4811 (15)0.5386 (5)0.082 (4)
S10.42243 (5)0.10135 (16)0.56162 (6)0.0439 (3)
S20.29818 (6)0.08162 (19)0.65231 (6)0.0561 (4)
S30.07545 (5)0.33344 (16)0.43499 (6)0.0461 (4)
S40.20225 (6)0.15195 (19)0.34460 (6)0.0591 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.023 (3)0.025 (3)0.041 (3)0.004 (3)0.017 (2)0.003 (2)
C20.037 (3)0.035 (4)0.045 (3)0.006 (3)0.021 (3)0.005 (3)
C30.053 (4)0.044 (3)0.053 (4)0.006 (3)0.035 (3)0.008 (3)
C40.061 (4)0.044 (3)0.038 (3)0.011 (3)0.032 (3)0.004 (3)
C50.036 (3)0.031 (3)0.034 (3)0.005 (3)0.003 (3)0.006 (3)
C60.043 (3)0.028 (3)0.031 (3)0.001 (2)0.023 (2)0.003 (2)
C70.049 (3)0.043 (3)0.041 (3)0.006 (3)0.022 (3)0.003 (3)
C80.059 (4)0.043 (4)0.068 (4)0.003 (3)0.049 (3)0.006 (3)
C90.037 (3)0.027 (3)0.061 (4)0.001 (3)0.026 (3)0.001 (3)
C100.033 (4)0.042 (3)0.048 (3)0.008 (3)0.020 (3)0.001 (3)
C110.021 (3)0.035 (3)0.044 (3)0.002 (3)0.017 (2)0.001 (3)
C120.033 (3)0.038 (3)0.046 (3)0.004 (3)0.025 (3)0.009 (3)
C130.069 (4)0.036 (3)0.065 (4)0.009 (3)0.050 (3)0.014 (3)
C140.059 (4)0.040 (3)0.035 (3)0.003 (3)0.019 (3)0.003 (3)
C150.033 (3)0.043 (3)0.033 (3)0.008 (3)0.012 (3)0.008 (3)
C160.031 (3)0.038 (3)0.027 (3)0.004 (2)0.012 (2)0.001 (3)
C170.041 (3)0.039 (3)0.031 (3)0.004 (3)0.017 (2)0.002 (3)
C180.050 (4)0.050 (4)0.040 (3)0.009 (3)0.031 (3)0.009 (3)
C190.035 (3)0.048 (4)0.051 (4)0.005 (3)0.027 (3)0.013 (3)
C200.023 (3)0.036 (3)0.037 (3)0.001 (3)0.005 (2)0.003 (2)
C210.104 (5)0.116 (6)0.048 (4)0.041 (5)0.004 (4)0.025 (4)
C220.080 (5)0.165 (8)0.234 (9)0.066 (6)0.008 (6)0.051 (7)
C230.143 (7)0.152 (8)0.130 (7)0.060 (7)0.059 (7)0.011 (6)
C240.118 (7)0.145 (8)0.334 (13)0.062 (7)0.062 (8)0.052 (8)
Li10.028 (5)0.049 (6)0.040 (5)0.002 (4)0.012 (4)0.003 (4)
Li20.033 (5)0.035 (5)0.051 (6)0.004 (4)0.024 (4)0.001 (4)
N10.027 (3)0.028 (3)0.040 (3)0.001 (2)0.016 (2)0.003 (2)
N20.025 (3)0.029 (3)0.028 (2)0.001 (2)0.011 (2)0.002 (2)
N30.028 (3)0.038 (3)0.031 (3)0.005 (2)0.014 (2)0.001 (2)
N40.031 (3)0.023 (3)0.035 (3)0.002 (2)0.016 (2)0.002 (2)
O10.024 (2)0.059 (3)0.040 (2)0.0005 (17)0.0177 (16)0.0005 (18)
O20.029 (2)0.046 (2)0.0271 (18)0.0026 (17)0.0156 (15)0.0028 (16)
O30.023 (2)0.046 (2)0.0343 (19)0.0024 (17)0.0147 (16)0.0004 (17)
O40.031 (2)0.055 (2)0.0269 (19)0.0015 (18)0.0175 (16)0.0025 (17)
O50.078 (2)0.087 (3)0.043 (2)0.029 (2)0.0056 (18)0.015 (2)
O60.092 (3)0.091 (3)0.061 (2)0.029 (2)0.013 (2)0.015 (2)
Li30.039 (6)0.078 (7)0.061 (6)0.006 (5)0.023 (5)0.029 (6)
Li40.039 (6)0.123 (10)0.070 (7)0.001 (6)0.017 (5)0.031 (7)
S10.0304 (7)0.0557 (9)0.0404 (7)0.0041 (7)0.0132 (5)0.0001 (7)
S20.0376 (7)0.0886 (11)0.0381 (7)0.0099 (8)0.0155 (6)0.0115 (8)
S30.0316 (7)0.0543 (9)0.0453 (8)0.0038 (7)0.0133 (6)0.0025 (7)
S40.0385 (7)0.0946 (11)0.0391 (7)0.0120 (8)0.0150 (6)0.0158 (8)
Geometric parameters (Å, º) top
C1—N11.335 (5)C21—H21A0.9700
C1—C21.427 (6)C21—H21B0.9700
C1—S11.651 (5)C22—H22A0.9600
C2—C31.318 (6)C22—H22B0.9600
C2—H20.9300C22—H22C0.9600
C3—C41.342 (6)C23—C241.301 (8)
C3—H30.9300C23—O61.386 (7)
C4—C51.399 (6)C23—H23A0.9700
C4—H40.9300C23—H23B0.9700
C5—N11.304 (5)C24—H24A0.9600
C5—H50.9300C24—H24B0.9600
C6—N21.306 (5)C24—H24C0.9600
C6—C71.433 (6)Li1—O21.982 (8)
C6—S21.670 (5)Li1—O42.030 (8)
C7—C81.321 (6)Li1—O12.144 (8)
C7—H70.9300Li1—S22.446 (8)
C8—C91.328 (6)Li1—S12.616 (8)
C8—H80.9300Li1—Li32.740 (9)
C9—C101.401 (6)Li1—Li22.740 (8)
C9—H90.9300Li1—Li43.382 (12)
C10—N21.318 (5)Li2—O41.986 (8)
C10—H100.9300Li2—O22.077 (8)
C11—N31.331 (5)Li2—O32.110 (8)
C11—C121.441 (6)Li2—S42.457 (8)
C11—S31.649 (5)Li2—S32.615 (8)
C12—C131.299 (5)Li2—Li42.713 (11)
C12—H120.9300Li2—Li33.406 (10)
C13—C141.343 (6)N1—O11.389 (5)
C13—H130.9300N2—O21.382 (4)
C14—C151.389 (6)N3—O31.384 (4)
C14—H140.9300N4—O41.392 (4)
C15—N31.293 (5)O1—Li31.880 (9)
C15—H150.9300O1—Li4i2.170 (11)
C16—N41.314 (5)O2—Li31.945 (9)
C16—C171.439 (6)O3—Li41.860 (10)
C16—S41.656 (5)O3—Li3ii2.137 (10)
C17—C181.323 (5)O4—Li41.921 (10)
C17—H170.9300O5—Li41.737 (9)
C18—C191.315 (5)O5—H5A0.8200
C18—H180.9300O6—Li31.718 (8)
C19—C201.377 (6)O6—H6A0.8200
C19—H190.9300Li3—O3i2.137 (10)
C20—N41.326 (5)Li3—Li4i2.785 (11)
C20—H200.9300Li4—O1ii2.170 (11)
C21—O51.346 (5)Li4—Li3ii2.785 (11)
C21—C221.372 (7)
Cg1···Cg23.470 (6)Cg3···Cg43.461 (6)
Cg1···Cg2ii3.596 (6)Cg3···Cg4ii3.607 (6)
Cg2···Cg1i3.596 (6)Cg4···Cg3i3.607 (6)
N1—C1—C2116.9 (4)O2—Li1—S1158.8 (4)
N1—C1—S1116.2 (4)O4—Li1—S198.0 (3)
C2—C1—S1126.9 (4)O1—Li1—S170.9 (2)
N1—C1—C20108.7 (3)S2—Li1—S1115.1 (3)
C2—C1—C2086.5 (3)O2—Li1—Li345.2 (2)
S1—C1—C2074.97 (17)O4—Li1—Li3112.4 (3)
C3—C2—C1124.7 (5)O1—Li1—Li343.2 (2)
C3—C2—C19102.6 (3)S2—Li1—Li3110.2 (3)
C1—C2—C1992.6 (3)S1—Li1—Li3114.0 (3)
C3—C2—H2117.6O2—Li1—Li249.0 (2)
C1—C2—H2117.6O4—Li1—Li246.3 (2)
C19—C2—H273.4O1—Li1—Li2109.0 (3)
C2—C3—C4115.9 (5)S2—Li1—Li292.9 (3)
C2—C3—C1877.3 (3)S1—Li1—Li2141.3 (3)
C4—C3—C18104.0 (3)Li3—Li1—Li276.9 (2)
C2—C3—H3122.0O2—Li1—Li492.1 (3)
C4—C3—H3122.0O4—Li1—Li430.2 (2)
C18—C3—H388.8O1—Li1—Li4147.8 (3)
C3—C4—C5120.3 (5)S2—Li1—Li476.4 (2)
C3—C4—C1775.9 (3)S1—Li1—Li4107.7 (2)
C5—C4—C1789.0 (3)Li3—Li1—Li4128.2 (3)
C3—C4—H4119.9Li2—Li1—Li451.3 (2)
C5—C4—H4119.9O4—Li2—O293.8 (3)
C17—C4—H4105.2O4—Li2—O388.2 (3)
N1—C5—C4122.9 (5)O2—Li2—O3118.1 (4)
N1—C5—C1674.0 (3)O4—Li2—S476.4 (3)
C4—C5—C1691.6 (3)O2—Li2—S4106.2 (3)
N1—C5—H5118.6O3—Li2—S4134.0 (4)
C4—C5—H5118.6O4—Li2—S3159.8 (4)
C16—C5—H5105.0O2—Li2—S397.0 (3)
N2—C6—C7116.6 (5)O3—Li2—S371.6 (2)
N2—C6—S2116.0 (4)S4—Li2—S3116.5 (3)
C7—C6—S2127.4 (4)O4—Li2—Li445.0 (3)
N2—C6—C15102.4 (3)O2—Li2—Li4111.7 (3)
C7—C6—C1588.1 (3)O3—Li2—Li443.1 (3)
S2—C6—C1582.90 (18)S4—Li2—Li4109.7 (3)
C8—C7—C6124.6 (5)S3—Li2—Li4114.8 (3)
C8—C7—C1499.4 (3)O4—Li2—Li147.7 (2)
C6—C7—C1491.2 (3)O2—Li2—Li146.1 (2)
C8—C7—H7117.7O3—Li2—Li1109.4 (3)
C6—C7—H7117.7S4—Li2—Li191.7 (2)
C14—C7—H778.6S3—Li2—Li1140.4 (3)
C7—C8—C9116.8 (5)Li4—Li2—Li176.7 (3)
C7—C8—C1380.6 (3)O4—Li2—Li391.4 (3)
C9—C8—C13101.0 (3)O2—Li2—Li331.0 (2)
C7—C8—H8121.6O3—Li2—Li3148.9 (3)
C9—C8—H8121.6S4—Li2—Li375.6 (2)
C13—C8—H888.5S3—Li2—Li3106.6 (2)
C8—C9—C10118.9 (5)Li4—Li2—Li3128.2 (3)
C8—C9—C1278.3 (3)Li1—Li2—Li351.57 (19)
C10—C9—C1287.8 (3)C5—N1—C1119.3 (4)
C8—C9—H9120.5C5—N1—O1120.0 (4)
C10—C9—H9120.5C1—N1—O1120.6 (4)
C12—C9—H9103.7C5—N1—N4106.1 (3)
N2—C10—C9123.4 (5)C1—N1—N471.5 (2)
N2—C10—C1175.9 (3)O1—N1—N492.5 (2)
C9—C10—C1192.9 (3)C6—N2—C10119.5 (4)
N2—C10—H10118.3C6—N2—O2120.7 (4)
C9—C10—H10118.3C10—N2—O2119.7 (4)
C11—C10—H10101.8C6—N2—N377.0 (3)
N3—C11—C12117.0 (4)C10—N2—N3103.6 (3)
N3—C11—S3116.6 (4)O2—N2—N389.6 (2)
C12—C11—S3126.4 (4)C15—N3—C11119.9 (4)
N3—C11—C10109.0 (3)C15—N3—O3119.2 (4)
C12—C11—C1086.5 (3)C11—N3—O3120.9 (4)
S3—C11—C1074.68 (17)C15—N3—N2104.8 (3)
C13—C12—C11123.5 (5)C11—N3—N271.1 (3)
C13—C12—C9102.2 (3)O3—N3—N292.9 (2)
C11—C12—C992.8 (3)C16—N4—C20119.6 (4)
C13—C12—H12118.3C16—N4—O4119.9 (4)
C11—C12—H12118.3C20—N4—O4120.5 (4)
C9—C12—H1274.0C16—N4—N176.4 (3)
C12—C13—C14116.8 (5)C20—N4—N1103.2 (3)
C12—C13—C878.2 (3)O4—N4—N190.0 (2)
C14—C13—C8103.7 (3)N1—O1—Li3135.4 (4)
C12—C13—H13121.6N1—O1—Li1110.2 (3)
C14—C13—H13121.6Li3—O1—Li185.6 (3)
C8—C13—H1388.2N1—O1—Li4i118.6 (4)
C13—C14—C15120.6 (5)Li3—O1—Li4i86.6 (4)
C13—C14—C776.2 (3)Li1—O1—Li4i116.5 (4)
C15—C14—C791.3 (3)N2—O2—Li3119.6 (4)
C13—C14—H14119.7N2—O2—Li1124.1 (3)
C15—C14—H14119.7Li3—O2—Li188.5 (4)
C7—C14—H14102.7N2—O2—Li2116.5 (3)
N3—C15—C14122.3 (5)Li3—O2—Li2115.7 (4)
N3—C15—C675.4 (3)Li1—O2—Li284.9 (3)
C14—C15—C689.4 (3)N3—O3—Li4133.4 (4)
N3—C15—H15118.9N3—O3—Li2110.3 (3)
C14—C15—H15118.9Li4—O3—Li286.0 (4)
C6—C15—H15105.7N3—O3—Li3ii117.6 (3)
N4—C16—C17115.5 (4)Li4—O3—Li3ii88.1 (4)
N4—C16—S4116.9 (4)Li2—O3—Li3ii118.1 (3)
C17—C16—S4127.5 (4)N4—O4—Li4117.8 (4)
N4—C16—C5102.9 (3)N4—O4—Li2123.7 (3)
C17—C16—C587.0 (3)Li4—O4—Li288.0 (4)
S4—C16—C582.39 (18)N4—O4—Li1116.6 (3)
C18—C17—C16125.5 (5)Li4—O4—Li1117.7 (4)
C18—C17—C499.9 (3)Li2—O4—Li186.0 (3)
C16—C17—C492.4 (3)C21—O5—Li4145.4 (5)
C18—C17—H17117.2C21—O5—H5A109.5
C16—C17—H17117.2Li4—O5—H5A105.1
C4—C17—H1776.4C23—O6—Li3142.8 (5)
C19—C18—C17115.3 (5)C23—O6—H6A109.5
C19—C18—C3100.1 (3)Li3—O6—H6A107.7
C17—C18—C379.9 (3)O6—Li3—O1132.1 (5)
C19—C18—H18122.4O6—Li3—O2121.2 (5)
C17—C18—H18122.4O1—Li3—O297.6 (4)
C3—C18—H1890.0O6—Li3—O3i94.0 (4)
C18—C19—C20121.3 (5)O1—Li3—O3i92.9 (4)
C18—C19—C279.6 (3)O2—Li3—O3i115.7 (4)
C20—C19—C287.7 (3)O6—Li3—Li1152.8 (5)
C18—C19—H19119.4O1—Li3—Li151.3 (3)
C20—C19—H19119.4O2—Li3—Li146.3 (3)
C2—C19—H19103.0O3i—Li3—Li1113.1 (3)
N4—C20—C19122.7 (4)O6—Li3—Li4i120.6 (4)
N4—C20—C176.1 (3)O1—Li3—Li4i51.0 (3)
C19—C20—C193.1 (3)O2—Li3—Li4i114.7 (4)
N4—C20—H20118.6O3i—Li3—Li4i41.9 (3)
C19—C20—H20118.6Li1—Li3—Li4i83.2 (3)
C1—C20—H20101.2O6—Li3—Li2103.9 (4)
O5—C21—C22109.6 (6)O1—Li3—Li293.5 (3)
O5—C21—H21A109.7O2—Li3—Li233.3 (2)
C22—C21—H21A109.7O3i—Li3—Li2149.0 (3)
O5—C21—H21B109.7Li1—Li3—Li251.57 (19)
C22—C21—H21B109.7Li4i—Li3—Li2134.7 (3)
H21A—C21—H21B108.2O5—Li4—O3129.3 (6)
C21—C22—H22A109.5O5—Li4—O4123.7 (5)
C21—C22—H22B109.5O3—Li4—O497.9 (4)
H22A—C22—H22B109.5O5—Li4—O1ii93.3 (5)
C21—C22—H22C109.5O3—Li4—O1ii92.4 (4)
H22A—C22—H22C109.5O4—Li4—O1ii116.3 (5)
H22B—C22—H22C109.5O5—Li4—Li2153.8 (6)
C24—C23—O6105.5 (8)O3—Li4—Li250.9 (3)
C24—C23—H23A110.7O4—Li4—Li247.0 (3)
O6—C23—H23A110.7O1ii—Li4—Li2112.8 (4)
C24—C23—H23B110.6O5—Li4—Li3ii117.7 (5)
O6—C23—H23B110.6O3—Li4—Li3ii50.1 (3)
H23A—C23—H23B108.8O4—Li4—Li3ii116.1 (4)
C23—C24—H24A109.4O1ii—Li4—Li3ii42.4 (3)
C23—C24—H24B109.5Li2—Li4—Li3ii83.0 (3)
H24A—C24—H24B109.5O5—Li4—Li1106.0 (4)
C23—C24—H24C109.5O3—Li4—Li194.1 (4)
H24A—C24—H24C109.5O4—Li4—Li132.1 (3)
H24B—C24—H24C109.5O1ii—Li4—Li1148.4 (4)
O2—Li1—O495.3 (3)Li2—Li4—Li152.0 (2)
O2—Li1—O188.4 (3)Li3ii—Li4—Li1135.0 (3)
O4—Li1—O1117.7 (4)C1—S1—Li193.3 (2)
O2—Li1—S276.4 (3)C6—S2—Li1101.2 (2)
O4—Li1—S2106.4 (3)C11—S3—Li292.4 (2)
O1—Li1—S2134.5 (4)C16—S4—Li2100.8 (2)
N1—C1—C2—C30.6 (7)O2—Li2—O3—Li492.6 (5)
S1—C1—C2—C3176.9 (4)S4—Li2—O3—Li469.8 (6)
C20—C1—C2—C3108.6 (5)S3—Li2—O3—Li4179.2 (3)
N1—C1—C2—C19108.0 (4)Li1—Li2—O3—Li442.7 (4)
S1—C1—C2—C1969.5 (4)Li3—Li2—O3—Li489.0 (6)
C20—C1—C2—C191.25 (14)O4—Li2—O3—Li3ii84.9 (4)
C1—C2—C3—C40.1 (8)O2—Li2—O3—Li3ii178.2 (3)
C19—C2—C3—C4102.3 (4)S4—Li2—O3—Li3ii15.9 (7)
C1—C2—C3—C1899.5 (5)S3—Li2—O3—Li3ii93.5 (4)
C19—C2—C3—C182.76 (16)Li4—Li2—O3—Li3ii85.7 (5)
C2—C3—C4—C50.4 (7)Li1—Li2—O3—Li3ii128.4 (4)
C18—C3—C4—C583.0 (5)Li3—Li2—O3—Li3ii174.6 (5)
C2—C3—C4—C1779.9 (4)C16—N4—O4—Li4122.7 (5)
C18—C3—C4—C172.60 (16)C20—N4—O4—Li457.7 (6)
C3—C4—C5—N10.4 (8)N1—N4—O4—Li4163.1 (3)
C17—C4—C5—N172.6 (5)C16—N4—O4—Li215.0 (6)
C3—C4—C5—C1672.4 (5)C20—N4—O4—Li2165.3 (4)
C17—C4—C5—C160.62 (14)N1—N4—O4—Li289.3 (4)
N2—C6—C7—C80.2 (8)C16—N4—O4—Li188.9 (5)
S2—C6—C7—C8177.7 (4)C20—N4—O4—Li190.7 (5)
C15—C6—C7—C8102.7 (5)N1—N4—O4—Li114.7 (3)
N2—C6—C7—C14102.4 (4)O2—Li2—O4—N4120.2 (4)
S2—C6—C7—C1480.1 (4)O3—Li2—O4—N4121.8 (3)
C15—C6—C7—C140.49 (14)S4—Li2—O4—N414.5 (4)
C6—C7—C8—C91.7 (8)S3—Li2—O4—N4117.5 (10)
C14—C7—C8—C999.8 (4)Li4—Li2—O4—N4122.5 (5)
C6—C7—C8—C1395.9 (5)Li1—Li2—O4—N4119.6 (4)
C14—C7—C8—C132.11 (16)Li3—Li2—O4—N489.3 (4)
C7—C8—C9—C101.7 (7)O2—Li2—O4—Li4117.3 (4)
C13—C8—C9—C1083.2 (5)O3—Li2—O4—Li40.7 (4)
C7—C8—C9—C1282.5 (4)S4—Li2—O4—Li4137.0 (3)
C13—C8—C9—C122.41 (15)S3—Li2—O4—Li45.0 (12)
C8—C9—C10—N20.2 (8)Li1—Li2—O4—Li4117.9 (4)
C12—C9—C10—N275.5 (5)Li3—Li2—O4—Li4148.2 (4)
C8—C9—C10—C1174.8 (4)O2—Li2—O4—Li10.6 (4)
C12—C9—C10—C110.57 (14)O3—Li2—O4—Li1118.6 (3)
N2—C10—C11—N37.8 (3)S4—Li2—O4—Li1105.1 (2)
C9—C10—C11—N3116.0 (4)S3—Li2—O4—Li1122.9 (11)
N2—C10—C11—C12125.1 (4)Li4—Li2—O4—Li1117.9 (4)
C9—C10—C11—C121.3 (3)Li3—Li2—O4—Li130.3 (3)
N2—C10—C11—S3105.6 (3)O2—Li1—O4—N4126.6 (3)
C9—C10—C11—S3130.6 (4)O1—Li1—O4—N435.7 (5)
N3—C11—C12—C132.4 (7)S2—Li1—O4—N4156.0 (3)
S3—C11—C12—C13175.2 (4)S1—Li1—O4—N436.9 (4)
C10—C11—C12—C13107.2 (5)Li3—Li1—O4—N483.3 (4)
N3—C11—C12—C9109.0 (4)Li2—Li1—O4—N4126.0 (4)
S3—C11—C12—C968.6 (4)Li4—Li1—O4—N4148.4 (5)
C10—C11—C12—C90.55 (14)O2—Li1—O4—Li484.9 (4)
C8—C9—C12—C136.4 (4)O1—Li1—O4—Li4175.9 (3)
C10—C9—C12—C13126.5 (5)S2—Li1—O4—Li47.6 (6)
C8—C9—C12—C11118.8 (5)S1—Li1—O4—Li4111.6 (4)
C10—C9—C12—C111.3 (3)Li3—Li1—O4—Li4128.3 (4)
C11—C12—C13—C140.3 (8)Li2—Li1—O4—Li485.6 (5)
C9—C12—C13—C14102.0 (4)O2—Li1—O4—Li20.7 (4)
C11—C12—C13—C899.2 (5)O1—Li1—O4—Li290.3 (4)
C9—C12—C13—C82.48 (16)S2—Li1—O4—Li278.0 (3)
C7—C8—C13—C12109.4 (5)S1—Li1—O4—Li2162.8 (2)
C9—C8—C13—C126.3 (4)Li3—Li1—O4—Li242.7 (4)
C7—C8—C13—C145.6 (4)Li4—Li1—O4—Li285.6 (5)
C9—C8—C13—C14121.3 (5)C22—C21—O5—Li4103.7 (9)
C12—C13—C14—C151.8 (8)C24—C23—O6—Li3104.1 (9)
C8—C13—C14—C1585.3 (5)C23—O6—Li3—O169.8 (12)
C12—C13—C14—C781.4 (4)C23—O6—Li3—O269.2 (11)
C8—C13—C14—C72.15 (16)C23—O6—Li3—O3i167.4 (8)
C8—C7—C14—C135.4 (4)C23—O6—Li3—Li115.3 (16)
C6—C7—C14—C13120.0 (5)C23—O6—Li3—Li4i133.0 (9)
C8—C7—C14—C15126.7 (5)C23—O6—Li3—Li238.2 (10)
C6—C7—C14—C151.2 (4)N1—O1—Li3—O629.8 (11)
C13—C14—C15—N31.8 (8)Li1—O1—Li3—O6144.3 (7)
C7—C14—C15—N372.8 (5)Li4i—O1—Li3—O698.7 (7)
C13—C14—C15—C674.1 (5)N1—O1—Li3—O2115.7 (5)
C7—C14—C15—C60.50 (14)Li1—O1—Li3—O21.2 (4)
N2—C6—C15—N38.0 (3)Li4i—O1—Li3—O2115.8 (4)
C7—C6—C15—N3124.9 (4)N1—O1—Li3—O3i127.9 (5)
S2—C6—C15—N3107.1 (4)Li1—O1—Li3—O3i117.6 (3)
N2—C6—C15—C14115.6 (4)Li4i—O1—Li3—O3i0.6 (4)
C7—C6—C15—C141.2 (4)N1—O1—Li3—Li1114.5 (6)
S2—C6—C15—C14129.3 (4)Li4i—O1—Li3—Li1116.9 (3)
N1—C5—C16—N49.9 (4)N1—O1—Li3—Li4i128.6 (6)
C4—C5—C16—N4114.0 (4)Li1—O1—Li3—Li4i116.9 (3)
N1—C5—C16—C17125.4 (4)N1—O1—Li3—Li282.4 (5)
C4—C5—C16—C171.5 (3)Li1—O1—Li3—Li232.1 (3)
N1—C5—C16—S4106.1 (4)Li4i—O1—Li3—Li2149.0 (3)
C4—C5—C16—S4130.0 (4)N2—O2—Li3—O681.6 (7)
N4—C16—C17—C181.8 (8)Li1—O2—Li3—O6149.3 (5)
S4—C16—C17—C18177.4 (4)Li2—O2—Li3—O665.8 (7)
C5—C16—C17—C18104.6 (5)N2—O2—Li3—O1127.8 (4)
N4—C16—C17—C4102.2 (4)Li1—O2—Li3—O11.3 (5)
S4—C16—C17—C478.6 (4)Li2—O2—Li3—O184.8 (5)
C5—C16—C17—C40.60 (14)N2—O2—Li3—O3i30.8 (6)
C3—C4—C17—C186.7 (4)Li1—O2—Li3—O3i98.2 (4)
C5—C4—C17—C18128.3 (4)Li2—O2—Li3—O3i178.2 (3)
C3—C4—C17—C16120.1 (5)N2—O2—Li3—Li1129.0 (4)
C5—C4—C17—C161.5 (3)Li2—O2—Li3—Li183.6 (4)
C16—C17—C18—C191.1 (8)N2—O2—Li3—Li4i77.3 (4)
C4—C17—C18—C1999.1 (4)Li1—O2—Li3—Li4i51.7 (4)
C16—C17—C18—C397.7 (5)Li2—O2—Li3—Li4i135.3 (4)
C4—C17—C18—C32.56 (16)N2—O2—Li3—Li2147.4 (5)
C2—C3—C18—C197.1 (4)Li1—O2—Li3—Li283.6 (4)
C4—C3—C18—C19121.0 (5)O2—Li1—Li3—O672.9 (9)
C2—C3—C18—C17107.1 (5)O4—Li1—Li3—O61.5 (10)
C4—C3—C18—C176.8 (4)O1—Li1—Li3—O6108.7 (10)
C17—C18—C19—C200.0 (7)S2—Li1—Li3—O6117.0 (9)
C3—C18—C19—C2083.5 (5)S1—Li1—Li3—O6111.9 (9)
C17—C18—C19—C280.8 (4)Li2—Li1—Li3—O628.8 (9)
C3—C18—C19—C22.72 (15)Li4—Li1—Li3—O628.7 (11)
C3—C2—C19—C187.2 (4)O2—Li1—Li3—O1178.4 (6)
C1—C2—C19—C18119.3 (5)O4—Li1—Li3—O1107.2 (4)
C3—C2—C19—C20129.6 (5)S2—Li1—Li3—O1134.3 (4)
C1—C2—C19—C203.1 (3)S1—Li1—Li3—O13.2 (3)
C18—C19—C20—N40.4 (8)Li2—Li1—Li3—O1137.4 (4)
C2—C19—C20—N476.8 (4)Li4—Li1—Li3—O1137.3 (4)
C18—C19—C20—C175.0 (5)O4—Li1—Li3—O274.4 (4)
C2—C19—C20—C11.30 (14)O1—Li1—Li3—O2178.4 (6)
N1—C1—C20—N48.8 (3)S2—Li1—Li3—O244.1 (3)
C2—C1—C20—N4126.1 (4)S1—Li1—Li3—O2175.2 (5)
S1—C1—C20—N4104.2 (3)Li2—Li1—Li3—O244.2 (3)
N1—C1—C20—C19114.2 (4)Li4—Li1—Li3—O244.3 (4)
C2—C1—C20—C193.1 (3)O2—Li1—Li3—O3i104.1 (5)
S1—C1—C20—C19132.8 (4)O4—Li1—Li3—O3i178.6 (4)
O2—Li1—Li2—O4179.1 (5)O1—Li1—Li3—O3i74.2 (4)
O1—Li1—Li2—O4110.6 (4)S2—Li1—Li3—O3i60.1 (4)
S2—Li1—Li2—O4110.0 (4)S1—Li1—Li3—O3i71.0 (4)
S1—Li1—Li2—O427.8 (4)Li2—Li1—Li3—O3i148.3 (4)
Li3—Li1—Li2—O4139.9 (3)Li4—Li1—Li3—O3i148.4 (3)
Li4—Li1—Li2—O440.0 (3)O2—Li1—Li3—Li4i134.1 (4)
O4—Li1—Li2—O2179.1 (5)O4—Li1—Li3—Li4i151.5 (3)
O1—Li1—Li2—O270.2 (3)O1—Li1—Li3—Li4i44.3 (3)
S2—Li1—Li2—O269.1 (3)S2—Li1—Li3—Li4i90.0 (3)
S1—Li1—Li2—O2153.0 (6)S1—Li1—Li3—Li4i41.1 (3)
Li3—Li1—Li2—O240.9 (3)Li2—Li1—Li3—Li4i178.3 (3)
Li4—Li1—Li2—O2139.1 (3)Li4—Li1—Li3—Li4i178.4 (4)
O2—Li1—Li2—O3110.7 (4)O2—Li1—Li3—Li244.2 (3)
O4—Li1—Li2—O368.5 (3)O4—Li1—Li3—Li230.2 (3)
O1—Li1—Li2—O3179.1 (4)O1—Li1—Li3—Li2137.4 (4)
S2—Li1—Li2—O341.5 (3)S2—Li1—Li3—Li288.3 (3)
S1—Li1—Li2—O396.3 (5)S1—Li1—Li3—Li2140.6 (3)
Li3—Li1—Li2—O3151.6 (3)Li4—Li1—Li3—Li20.1 (3)
Li4—Li1—Li2—O328.5 (3)O4—Li2—Li3—O6138.5 (5)
O2—Li1—Li2—S4111.0 (3)O2—Li2—Li3—O6126.5 (6)
O4—Li1—Li2—S469.8 (3)O3—Li2—Li3—O6132.7 (7)
O1—Li1—Li2—S440.8 (3)S4—Li2—Li3—O662.9 (3)
S2—Li1—Li2—S4179.8 (3)S3—Li2—Li3—O650.9 (4)
S1—Li1—Li2—S442.0 (5)Li4—Li2—Li3—O6166.8 (4)
Li3—Li1—Li2—S470.1 (2)Li1—Li2—Li3—O6166.9 (4)
Li4—Li1—Li2—S4109.8 (3)O4—Li2—Li3—O13.5 (3)
O2—Li1—Li2—S326.3 (4)O2—Li2—Li3—O198.5 (5)
O4—Li1—Li2—S3152.9 (6)O3—Li2—Li3—O192.3 (6)
O1—Li1—Li2—S396.5 (5)S4—Li2—Li3—O172.1 (3)
S2—Li1—Li2—S342.9 (5)S3—Li2—Li3—O1174.1 (4)
S1—Li1—Li2—S3179.3 (4)Li4—Li2—Li3—O131.8 (5)
Li3—Li1—Li2—S367.2 (5)Li1—Li2—Li3—O131.9 (3)
Li4—Li1—Li2—S3112.9 (5)O4—Li2—Li3—O295.0 (4)
O2—Li1—Li2—Li4139.1 (3)O3—Li2—Li3—O26.2 (5)
O4—Li1—Li2—Li440.0 (3)S4—Li2—Li3—O2170.5 (5)
O1—Li1—Li2—Li4150.6 (3)S3—Li2—Li3—O275.7 (4)
S2—Li1—Li2—Li470.0 (3)Li4—Li2—Li3—O266.6 (5)
S1—Li1—Li2—Li467.8 (5)Li1—Li2—Li3—O266.5 (4)
Li3—Li1—Li2—Li4179.9 (3)O4—Li2—Li3—O3i98.0 (6)
O2—Li1—Li2—Li340.9 (3)O2—Li2—Li3—O3i3.1 (5)
O4—Li1—Li2—Li3139.9 (3)O3—Li2—Li3—O3i9.2 (9)
O1—Li1—Li2—Li329.3 (3)S4—Li2—Li3—O3i173.6 (7)
S2—Li1—Li2—Li3110.1 (3)S3—Li2—Li3—O3i72.6 (7)
S1—Li1—Li2—Li3112.1 (5)Li4—Li2—Li3—O3i69.7 (8)
Li4—Li1—Li2—Li3179.9 (3)Li1—Li2—Li3—O3i69.6 (6)
C4—C5—N1—C10.1 (7)O4—Li2—Li3—Li128.4 (3)
C16—C5—N1—C181.2 (4)O2—Li2—Li3—Li166.5 (4)
C4—C5—N1—O1179.8 (4)O3—Li2—Li3—Li160.4 (6)
C16—C5—N1—O198.9 (4)S4—Li2—Li3—Li1104.0 (3)
C4—C5—N1—N477.6 (5)S3—Li2—Li3—Li1142.2 (3)
C16—C5—N1—N43.73 (13)Li4—Li2—Li3—Li10.1 (4)
C2—C1—N1—C50.6 (6)O4—Li2—Li3—Li4i30.8 (5)
S1—C1—N1—C5177.1 (3)O2—Li2—Li3—Li4i64.2 (5)
C20—C1—N1—C595.1 (4)O3—Li2—Li3—Li4i58.0 (7)
C2—C1—N1—O1179.3 (4)S4—Li2—Li3—Li4i106.4 (4)
S1—C1—N1—O13.0 (6)S3—Li2—Li3—Li4i139.8 (4)
C20—C1—N1—O185.0 (4)Li4—Li2—Li3—Li4i2.5 (5)
C2—C1—N1—N499.1 (4)Li1—Li2—Li3—Li4i2.4 (4)
S1—C1—N1—N478.6 (3)C21—O5—Li4—O368.5 (13)
C20—C1—N1—N43.40 (13)C21—O5—Li4—O470.7 (11)
C7—C6—N2—C101.4 (7)C21—O5—Li4—O1ii164.4 (7)
S2—C6—N2—C10176.4 (3)C21—O5—Li4—Li210.9 (17)
C15—C6—N2—C1095.5 (4)C21—O5—Li4—Li3ii128.1 (8)
C7—C6—N2—O2178.8 (4)C21—O5—Li4—Li140.9 (9)
S2—C6—N2—O23.4 (6)N3—O3—Li4—O531.6 (11)
C15—C6—N2—O284.6 (4)Li2—O3—Li4—O5146.0 (8)
C7—C6—N2—N397.1 (4)Li3ii—O3—Li4—O595.6 (8)
S2—C6—N2—N385.1 (3)N3—O3—Li4—O4115.1 (5)
C15—C6—N2—N32.92 (12)Li2—O3—Li4—O40.8 (5)
C9—C10—N2—C61.4 (7)Li3ii—O3—Li4—O4117.6 (4)
C11—C10—N2—C685.5 (4)N3—O3—Li4—O1ii127.9 (4)
C9—C10—N2—O2178.7 (4)Li2—O3—Li4—O1ii117.8 (3)
C11—C10—N2—O294.7 (4)Li3ii—O3—Li4—O1ii0.6 (4)
C9—C10—N2—N381.2 (5)N3—O3—Li4—Li2114.3 (6)
C11—C10—N2—N32.85 (12)Li3ii—O3—Li4—Li2118.4 (3)
C14—C15—N3—C110.4 (7)N3—O3—Li4—Li3ii127.3 (6)
C6—C15—N3—C1179.5 (4)Li2—O3—Li4—Li3ii118.4 (3)
C14—C15—N3—O3178.8 (4)N3—O3—Li4—Li183.0 (5)
C6—C15—N3—O399.0 (4)Li2—O3—Li4—Li131.3 (3)
C14—C15—N3—N276.8 (5)Li3ii—O3—Li4—Li1149.7 (3)
C6—C15—N3—N23.00 (13)N4—O4—Li4—O584.0 (8)
C12—C11—N3—C152.3 (7)Li2—O4—Li4—O5148.5 (6)
S3—C11—N3—C15175.5 (3)Li1—O4—Li4—O564.1 (8)
C10—C11—N3—C1593.6 (4)N4—O4—Li4—O3126.7 (4)
C12—C11—N3—O3179.3 (4)Li2—O4—Li4—O30.8 (5)
S3—C11—N3—O32.9 (6)Li1—O4—Li4—O385.2 (5)
C10—C11—N3—O384.8 (4)N4—O4—Li4—O1ii30.0 (6)
C12—C11—N3—N298.9 (4)Li2—O4—Li4—O1ii97.5 (5)
S3—C11—N3—N279.0 (3)Li1—O4—Li4—O1ii178.1 (3)
C10—C11—N3—N22.98 (13)N4—O4—Li4—Li2127.5 (4)
C6—N2—N3—C158.2 (3)Li1—O4—Li4—Li284.4 (4)
C10—N2—N3—C15109.5 (4)N4—O4—Li4—Li3ii77.5 (5)
O2—N2—N3—C15129.9 (4)Li2—O4—Li4—Li3ii50.0 (4)
C6—N2—N3—C11125.2 (4)Li1—O4—Li4—Li3ii134.4 (4)
C10—N2—N3—C117.5 (3)N4—O4—Li4—Li1148.1 (5)
O2—N2—N3—C11113.1 (4)Li2—O4—Li4—Li184.4 (4)
C6—N2—N3—O3113.1 (4)O4—Li2—Li4—O579.7 (11)
C10—N2—N3—O3129.2 (4)O2—Li2—Li4—O57.0 (11)
O2—N2—N3—O38.6 (2)O3—Li2—Li4—O5101.3 (12)
C17—C16—N4—C201.3 (6)S4—Li2—Li4—O5124.5 (11)
S4—C16—N4—C20178.0 (3)S3—Li2—Li4—O5102.2 (11)
C5—C16—N4—C2094.1 (4)Li1—Li2—Li4—O537.5 (11)
C17—C16—N4—O4178.4 (4)Li3—Li2—Li4—O537.6 (12)
S4—C16—N4—O42.3 (6)O4—Li2—Li4—O3179.0 (6)
C5—C16—N4—O485.6 (4)O2—Li2—Li4—O3108.4 (5)
C17—C16—N4—N196.4 (4)S4—Li2—Li4—O3134.2 (4)
S4—C16—N4—N184.3 (3)S3—Li2—Li4—O30.8 (3)
C5—C16—N4—N13.61 (13)Li1—Li2—Li4—O3138.9 (4)
C19—C20—N4—C160.3 (7)Li3—Li2—Li4—O3139.0 (4)
C1—C20—N4—C1685.0 (4)O2—Li2—Li4—O472.7 (4)
C19—C20—N4—O4179.4 (4)O3—Li2—Li4—O4179.0 (6)
C1—C20—N4—O494.7 (4)S4—Li2—Li4—O444.8 (3)
C19—C20—N4—N181.4 (5)S3—Li2—Li4—O4178.1 (5)
C1—C20—N4—N13.25 (12)Li1—Li2—Li4—O442.2 (3)
C5—N1—N4—C1610.1 (4)Li3—Li2—Li4—O442.1 (5)
C1—N1—N4—C16126.2 (4)O4—Li2—Li4—O1ii105.4 (5)
O1—N1—N4—C16112.2 (4)O2—Li2—Li4—O1ii178.1 (4)
C5—N1—N4—C20107.7 (4)O3—Li2—Li4—O1ii73.6 (4)
C1—N1—N4—C208.5 (3)S4—Li2—Li4—O1ii60.6 (4)
O1—N1—N4—C20130.1 (4)S3—Li2—Li4—O1ii72.7 (4)
C5—N1—N4—O4130.9 (4)Li1—Li2—Li4—O1ii147.6 (4)
C1—N1—N4—O4112.9 (4)Li3—Li2—Li4—O1ii147.5 (3)
O1—N1—N4—O48.7 (2)O4—Li2—Li4—Li3ii136.1 (4)
C5—N1—O1—Li328.9 (8)O2—Li2—Li4—Li3ii151.2 (3)
C1—N1—O1—Li3151.2 (5)O3—Li2—Li4—Li3ii42.8 (3)
N4—N1—O1—Li381.3 (5)S4—Li2—Li4—Li3ii91.3 (3)
C5—N1—O1—Li1133.7 (4)S3—Li2—Li4—Li3ii42.0 (3)
C1—N1—O1—Li146.4 (5)Li1—Li2—Li4—Li3ii178.3 (3)
N4—N1—O1—Li123.5 (3)Li3—Li2—Li4—Li3ii178.2 (4)
C5—N1—O1—Li4i88.3 (5)O4—Li2—Li4—Li142.2 (3)
C1—N1—O1—Li4i91.6 (5)O2—Li2—Li4—Li130.5 (3)
N4—N1—O1—Li4i161.4 (3)O3—Li2—Li4—Li1138.9 (4)
O2—Li1—O1—N1138.3 (3)S4—Li2—Li4—Li187.0 (3)
O4—Li1—O1—N143.1 (5)S3—Li2—Li4—Li1139.7 (3)
S2—Li1—O1—N1152.7 (4)Li3—Li2—Li4—Li10.1 (3)
S1—Li1—O1—N146.0 (3)O2—Li1—Li4—O5134.1 (5)
Li3—Li1—O1—N1137.1 (4)O4—Li1—Li4—O5128.8 (7)
Li2—Li1—O1—N193.0 (3)O1—Li1—Li4—O5135.7 (7)
Li4—Li1—O1—N147.0 (6)S2—Li1—Li4—O558.7 (4)
O2—Li1—O1—Li31.1 (4)S1—Li1—Li4—O553.7 (4)
O4—Li1—O1—Li394.0 (5)Li3—Li1—Li4—O5163.8 (4)
S2—Li1—O1—Li370.2 (5)Li2—Li1—Li4—O5163.7 (5)
S1—Li1—O1—Li3176.9 (3)O2—Li1—Li4—O31.1 (3)
Li2—Li1—O1—Li344.2 (4)O4—Li1—Li4—O398.2 (5)
Li4—Li1—O1—Li390.1 (6)O1—Li1—Li4—O391.4 (6)
O2—Li1—O1—Li4i82.8 (4)S2—Li1—Li4—O374.3 (4)
O4—Li1—O1—Li4i178.0 (3)S1—Li1—Li4—O3173.3 (4)
S2—Li1—O1—Li4i13.8 (7)Li3—Li1—Li4—O330.9 (5)
S1—Li1—O1—Li4i92.9 (4)Li2—Li1—Li4—O330.8 (3)
Li3—Li1—O1—Li4i84.0 (4)O2—Li1—Li4—O497.1 (5)
Li2—Li1—O1—Li4i128.1 (4)O1—Li1—Li4—O46.8 (5)
Li4—Li1—O1—Li4i174.1 (6)S2—Li1—Li4—O4172.5 (6)
C6—N2—O2—Li3124.1 (5)S1—Li1—Li4—O475.1 (4)
C10—N2—O2—Li355.7 (6)Li3—Li1—Li4—O467.3 (5)
N3—N2—O2—Li3161.2 (3)Li2—Li1—Li4—O467.4 (4)
C6—N2—O2—Li113.8 (6)O2—Li1—Li4—O1ii100.3 (7)
C10—N2—O2—Li1166.0 (4)O4—Li1—Li4—O1ii3.3 (5)
N3—N2—O2—Li188.5 (4)O1—Li1—Li4—O1ii10.1 (9)
C6—N2—O2—Li288.7 (5)S2—Li1—Li4—O1ii175.8 (7)
C10—N2—O2—Li291.4 (5)S1—Li1—Li4—O1ii71.9 (7)
N3—N2—O2—Li214.1 (3)Li3—Li1—Li4—O1ii70.6 (8)
O4—Li1—O2—N2118.1 (4)Li2—Li1—Li4—O1ii70.7 (7)
O1—Li1—O2—N2124.2 (3)O2—Li1—Li4—Li229.6 (3)
S2—Li1—O2—N212.5 (4)O4—Li1—Li4—Li267.4 (4)
S1—Li1—O2—N2113.1 (10)O1—Li1—Li4—Li260.6 (6)
Li3—Li1—O2—N2125.3 (5)S2—Li1—Li4—Li2105.1 (3)
Li2—Li1—O2—N2118.7 (4)S1—Li1—Li4—Li2142.6 (3)
Li4—Li1—O2—N288.0 (4)Li3—Li1—Li4—Li20.1 (4)
O4—Li1—O2—Li3116.6 (3)O2—Li1—Li4—Li3ii32.0 (5)
O1—Li1—O2—Li31.1 (4)O4—Li1—Li4—Li3ii65.1 (5)
S2—Li1—O2—Li3137.8 (3)O1—Li1—Li4—Li3ii58.2 (8)
S1—Li1—O2—Li312.2 (11)S2—Li1—Li4—Li3ii107.5 (4)
Li2—Li1—O2—Li3116.0 (4)S1—Li1—Li4—Li3ii140.2 (4)
Li4—Li1—O2—Li3146.7 (3)Li3—Li1—Li4—Li3ii2.3 (6)
O4—Li1—O2—Li20.6 (4)Li2—Li1—Li4—Li3ii2.4 (4)
O1—Li1—O2—Li2117.1 (3)N1—C1—S1—Li130.4 (4)
S2—Li1—O2—Li2106.2 (2)C2—C1—S1—Li1147.1 (4)
S1—Li1—O2—Li2128.2 (10)C20—C1—S1—Li173.35 (19)
Li3—Li1—O2—Li2116.0 (4)O2—Li1—S1—C149.8 (10)
Li4—Li1—O2—Li230.7 (3)O4—Li1—S1—C178.6 (3)
O4—Li2—O2—N2125.1 (3)O1—Li1—S1—C138.0 (2)
O3—Li2—O2—N235.2 (5)S2—Li1—S1—C1169.1 (3)
S4—Li2—O2—N2158.0 (3)Li3—Li1—S1—C140.4 (3)
S3—Li2—O2—N237.8 (4)Li2—Li1—S1—C158.7 (5)
Li4—Li2—O2—N282.5 (4)Li4—Li1—S1—C1108.0 (3)
Li1—Li2—O2—N2125.7 (4)N2—C6—S2—Li15.1 (4)
Li3—Li2—O2—N2148.4 (5)C7—C6—S2—Li1172.4 (5)
O4—Li2—O2—Li386.5 (4)C15—C6—S2—Li1105.5 (2)
O3—Li2—O2—Li3176.4 (3)O2—Li1—S2—C68.3 (3)
S4—Li2—O2—Li39.6 (5)O4—Li1—S2—C699.9 (3)
S3—Li2—O2—Li3110.7 (4)O1—Li1—S2—C665.5 (5)
Li4—Li2—O2—Li3129.1 (4)S1—Li1—S2—C6152.8 (3)
Li1—Li2—O2—Li385.8 (4)Li3—Li1—S2—C622.2 (3)
O4—Li2—O2—Li10.7 (4)Li2—Li1—S2—C654.8 (3)
O3—Li2—O2—Li190.6 (4)Li4—Li1—S2—C6103.8 (2)
S4—Li2—O2—Li176.3 (3)N3—C11—S3—Li229.8 (4)
S3—Li2—O2—Li1163.5 (3)C12—C11—S3—Li2147.8 (4)
Li4—Li2—O2—Li143.3 (4)C10—C11—S3—Li274.09 (19)
Li3—Li2—O2—Li185.8 (4)O4—Li2—S3—C1142.1 (11)
C15—N3—O3—Li427.9 (8)O2—Li2—S3—C1179.6 (3)
C11—N3—O3—Li4150.5 (6)O3—Li2—S3—C1137.7 (2)
N2—N3—O3—Li480.8 (6)S4—Li2—S3—C11168.3 (3)
C15—N3—O3—Li2132.2 (4)Li4—Li2—S3—C1138.3 (3)
C11—N3—O3—Li246.2 (5)Li1—Li2—S3—C1160.9 (5)
N2—N3—O3—Li223.6 (3)Li3—Li2—S3—C11109.8 (2)
C15—N3—O3—Li3ii88.3 (5)N4—C16—S4—Li27.4 (4)
C11—N3—O3—Li3ii93.3 (5)C17—C16—S4—Li2171.9 (5)
N2—N3—O3—Li3ii163.0 (3)C5—C16—S4—Li2108.0 (2)
O4—Li2—O3—N3135.9 (3)O4—Li2—S4—C1610.4 (3)
O2—Li2—O3—N342.6 (5)O2—Li2—S4—C16100.4 (3)
S4—Li2—O3—N3155.1 (4)O3—Li2—S4—C1663.4 (5)
S3—Li2—O3—N345.7 (3)S3—Li2—S4—C16152.9 (3)
Li4—Li2—O3—N3135.1 (4)Li4—Li2—S4—C1620.5 (3)
Li1—Li2—O3—N392.4 (3)Li1—Li2—S4—C1655.9 (2)
Li3—Li2—O3—N346.2 (6)Li3—Li2—S4—C16105.4 (2)
O4—Li2—O3—Li40.7 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···S1ii0.822.393.205 (3)174
O6—H6A···S3i0.822.413.226 (4)172
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Li2(C5H4NOS)2(C2H6O)]
Mr312.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)300
a, b, c (Å)22.492 (7), 7.047 (2), 20.881 (7)
β (°) 119.31 (4)
V3)2886.0 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.50 × 0.12 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
[CrysAlis RED (Oxford Diffraction , 2006); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.835, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
16998, 5597, 1539
Rint0.087
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.100, 0.71
No. of reflections5597
No. of parameters383
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Selected interatomic distances (Å) top
Cg1···Cg23.470 (6)Cg3···Cg43.461 (6)
Cg1···Cg2i3.596 (6)Cg3···Cg4i3.607 (6)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···S1i0.822.393.205 (3)174.3
O6—H6A···S3ii0.822.413.226 (4)171.6
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

References

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 3| March 2008| Pages m462-m463
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