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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Pages m917-m918

catena-Poly[[(ethanol-κO)[3-(1-phenyl-1H-pyrazol-3-yl)benzoic acid-κO]lithium]-μ-3-(1-phenyl-1H-pyrazol-3-yl)benzoato-κ2O:O′]

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 Universiti Sains Malaysia, Penang, Malaysia, bSyngene International Ltd, Biocon Park, Plot Nos. 2 & 3, Bommasandra 4th Phase, Jigani Link Rd, Bangalore 560 100, India, cDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and dDepartment of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India
*Correspondence e-mail: hkfun@usm.my

(Received 2 July 2009; accepted 7 July 2009; online 15 July 2009)

The asymmetric unit of the title polymeric compound, [Li2(C16H11N2O2)2(C16H12N2O2)2(CH3CH2OH)2]n, contains two LiI ions, two 3-(1-phenyl-1H-pyrazol-3-yl)benzoate ions, two 3-(1-phenyl-1H-pyrazol-3-yl)benzoic acid mol­ecules and two ethanol mol­ecules. In the crystal structure, each of the two LiI ions has a distorted tetra­hedral geometry, coordinated by two carboxyl­ate O atoms, one carboxyl O atom and one ethanol O atom. The carboxyl­ate group bridges the LiI ions, forming a one-dimensional polymeric chain along [100]. The crystal structure is further stabilized by O—H⋯O and C—H⋯N hydrogen bonding, and ππ inter­actions with centroid–centroid distances in the range 3.6534 (13)–3.8374 (13) Å.

Related literature

For pyrazole derivatives, see: Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44. In the press. ]); Skoutakis et al. (1988[Skoutakis, V. A., Carter, C. A., Micklee, T. R., Smith, V. H., Arkin, C. R., Allissantros, J. & Petty, D. (1988). Drug Intell. Clin. Pharm. 3, 850-859.]); Di Marzo et al. (2004[Di Marzo, V., Bifulco, M. & De Petrocellis, L. (2004). Nat. Rev. Drug Discov. 3, 771-784.]); Kalluraya et al. (2004[Kalluraya, B., Jagadeesha, R. L. & Isloor, A. M. (2004). Indian J. Heterocycl. Chem. 13, 245-248.]); Hanamoto et al. (2008[Hanamoto, T., Hashimoto, E., Miura, M., Furuno, H. & Inanaga, J. (2008). J. Org. Chem. 73, 4736-4739.]). For a similar coordination geometry, see: Fischer (2005[Fischer, A. (2005). Acta Cryst. E61, m320-m322.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • [Li2(C16H11N2O2)2(C16H12N2O2)2(C2H6O)2]

  • Mr = 1161.10

  • Triclinic, [P \overline 1]

  • a = 7.9607 (1) Å

  • b = 14.9527 (2) Å

  • c = 26.5320 (4) Å

  • α = 103.471 (1)°

  • β = 90.348 (1)°

  • γ = 105.429 (1)°

  • V = 2952.82 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.47 × 0.18 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.987

  • 66644 measured reflections

  • 17230 independent reflections

  • 11897 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.168

  • S = 1.04

  • 17230 reflections

  • 811 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Selected bond lengths (Å)

Li1—O1A 1.912 (4)
Li1—O2D 1.931 (4)
Li1—O4 1.953 (4)
Li1—O1Ci 1.954 (4)
Li2—O2C 1.912 (4)
Li2—O1B 1.931 (4)
Li2—O1D 1.940 (4)
Li2—O3 1.960 (4)
Symmetry code: (i) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2A—H1OA⋯O2Ci 0.91 (3) 1.70 (3) 2.594 (2) 167 (3)
O2B—H1OB⋯O2D 0.92 (3) 1.68 (3) 2.584 (2) 165 (3)
O3—H1O3⋯O1Ci 0.85 (3) 1.92 (3) 2.761 (2) 171 (3)
O4—H1O4⋯O1Di 0.85 (3) 1.94 (3) 2.780 (2) 170 (2)
C7A—H7AA⋯N2D 0.93 2.58 3.306 (3) 136
C5C—H5CA⋯N2Bii 0.93 2.60 3.501 (3) 163
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Natural antibiotic compounds have become indispensable to the current health care system, assisting and complementing the natural immune system against microbial pathogens. However, because conventional antibiotics are often overused to treat microbial infections, some microorganisms have developed resistance to many of these antibiotics. Pyrazole chemistry has been a focus of medical research for more than five decades due to the versatile biological and pharmacological activities of pyrazole derivatives, including effects as antimicrobial (Isloor et al., 2009), antiviral (Skoutakis et al., 1988), antitumor (Di Marzo et al., 2004), anti-inflammatory (Kalluraya et al., 2004), antihistaminic, antifungal, anti-rheumatoid-arthritic, anticonvulsant and antipyretic (Hanamoto et al., 2008) agents. We report here a lithium salt of the pyrazole derivative.

The asymmetric unit of (I) (Fig. 1), contains two Li ions, two 3-(1-phenyl-1H-pyrazol-3-yl)benzoate ions, two 3-(1-phenyl-1H-pyrazol-3-yl)benzoic acid and two ethanol molecules. The bond lengths (Allen et al., 1987) and angles are normal. The torsion angles of C6A—N1A—C7A—C8A, C4A—C5A—C6A—N1A, C2A—C1A—C6A—N1A, C10A—C11A—C12A—C16A, C16A—C12A—C13A—C14A, C13A—C12A—C16A—O1A, C11A—C12A—C16A—O2A, C6B—N1B—C7B—C8B, C4B—C5B—C6B—N1B, C2B—C1B—C6B—N1B, C10B—C11B—C12B—C16B, C16B—C12B—C13B—C14B, C13B—C12B—C16B—O1B, C11B—C12B—C16B—O2B, C6C—N1C—C7C—C8C, C4C—C5C—C6C—N1C, C2C—C1C—C6C—N1C, C10C—C11C—C12C—C16C, C16C—C12C—C13C—C14C, C13C—C12C—C16C—O1C, C11C—C12C—C16C—O2C, C6D—N1D—C7D—C8D, C4D—C5D—C6D—N1D, C2D—C1D—C6D—N1D, C10D—C11D—C12D—C16D, C16D—C12D—C13D—C14D, C13D—C12D—C16D—O1D and C11D—C12D—C16D—O2D are -178.7 (2), 178.8 (2), -178.3 (2), 177.4 (2), -177.9 (2), -176.8 (2), -174.7 (2), -179.1 (2), -179.4 (2), -179.9 (2), 177.1 (2), -176.6 (2), 171.3 (2), 176.2 (2), 178.7 (2), 178.3 (2), -179.5 (2), 178.2 (2), -178.3 (2), 172.0 (2), 173.8 (2), -180.0 (2), 177.9 (2), -178.8 (2), 177.7 (2), -177.7 (2), 172.0 (2) and 174.2 (2)°, respectively. The environments of both Li ions adopt a distorted tetrahedral geometry, with each Li atom coordinated by two carboxylate oxygen atoms, one carboxyl oxygen atom and an ethanol oxygen atom (Table 1). This coordination is similar to that observed in the crystal structure of lithium hydrogen (RS)-phenylsuccinate (Fischer, 2005). In the crystal packing (Fig. 2), the molecules form one-dimensional polymeric chains along the [100] direction. In each chain, the ethanol hydrogen atom is hydrogen-bonded to the carboxylate oxygen atoms through O—H···O hydrogen bonding. The carboxyl hydrogen atom is also hydrogen-bonded to the carboxylate oxygen atoms via O—H···O hydrogen bonding. The crystal structure is further stabilized by C—H···N hydrogen-bonding (Table 2) and ππ interactions. The ππ interaction between the five-membered rings, N1A—N2A/C9A—C7A and N1B—N2B/C9B—C7B, has centroid-to-centroid distance of 3.6534 (13) Å. The ππ interactions between the six-membered rings, C1A—C6A/C10A—C15A and C1B—C6B/C10B—C15B, have centroid-to-centroid distances of between 3.7099 (14) and 3.7589 (14) Å. The ππ interaction between the five-membered and six-membered rings, N1C—N2C/C9C—C7C and C10B—C15B, has centroid-to-centroid distance of 3.8374 (13) Å.

Related literature top

For pyrazole derivatives, see: Isloor et al. (2009); Skoutakis et al. (1988); Di Marzo et al. (2004); Kalluraya et al. (2004); Hanamoto et al. (2008). For a similar coordination geometry, see: Fischer (2005). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound is obtained by adding 3-bromo-1-phenyl pyrazole (500 mg, 2.2 mmol) into a stirred solution of benzene boronic acid (369 mg, 2.2 mmol) in toluene (10 ml) and water (10 ml). Sodium carbonate (370 mg, 4.4 mmol), and tetrakis(triphenylphosphine)palladium(0) (258 mg, 0.2 mmol) were then added. The reaction mixture was heated to 100°C for 12 hr when TLC showed completion of reaction. Reaction mixture was diluted with water, acidified to pH 3, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, concentrated and the residue purified by column chromatography using 5% methanol in chloroform to get pure product as colorless crystals, Yield: 510 mg (84%), Melting point: 435–438 K. The lithium is an impurity with silica gel. The NMR data is consistent with the structure of the title compound (I).

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C). A rotating–group model was used for the methyl groups. The oxygen H atoms were located from the difference Fourier map [O–H = 0.85 (3)–0.91 (3) Å] and allowed to refine freely.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. The polymeric network of (I) along the [100] direction. Dashed lines indicate the hydrogen bonding.
catena-Poly[[(ethanol-κO)[3-(1-phenyl-1H-pyrazol- 3-yl)benzoic acid-κO]lithium(I)]-µ-3-(1-phenyl-1H-pyrazol-3-yl)benzoato- κ2O:O'] top
Crystal data top
[Li2(C16H11N2O2)2(C16H12N2O2)2(C2H6O)2]Z = 2
Mr = 1161.10F(000) = 1216
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9607 (1) ÅCell parameters from 9941 reflections
b = 14.9527 (2) Åθ = 2.4–30.1°
c = 26.5320 (4) ŵ = 0.09 mm1
α = 103.471 (1)°T = 100 K
β = 90.348 (1)°Block, colorless
γ = 105.429 (1)°0.47 × 0.18 × 0.15 mm
V = 2952.82 (7) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
17230 independent reflections
Radiation source: fine-focus sealed tube11897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 30.2°, θmin = 0.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1111
Tmin = 0.960, Tmax = 0.987k = 2021
66644 measured reflectionsl = 3537
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0531P)2 + 3.024P]
where P = (Fo2 + 2Fc2)/3
17230 reflections(Δ/σ)max < 0.001
811 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Li2(C16H11N2O2)2(C16H12N2O2)2(C2H6O)2]γ = 105.429 (1)°
Mr = 1161.10V = 2952.82 (7) Å3
Triclinic, P1Z = 2
a = 7.9607 (1) ÅMo Kα radiation
b = 14.9527 (2) ŵ = 0.09 mm1
c = 26.5320 (4) ÅT = 100 K
α = 103.471 (1)°0.47 × 0.18 × 0.15 mm
β = 90.348 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
17230 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
11897 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.987Rint = 0.046
66644 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.41 e Å3
17230 reflectionsΔρmin = 0.31 e Å3
811 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Li11.4484 (4)0.4845 (2)0.21870 (13)0.0220 (7)
Li20.9517 (4)0.5029 (3)0.27808 (13)0.0224 (7)
O1A1.4132 (2)0.35616 (11)0.17852 (6)0.0327 (4)
O2A1.6215 (2)0.30183 (12)0.20755 (6)0.0293 (3)
N1A1.0252 (2)0.06256 (12)0.06878 (7)0.0243 (4)
N2A1.1522 (2)0.05002 (12)0.03866 (6)0.0230 (4)
C1A1.0440 (3)0.07475 (16)0.13585 (8)0.0289 (5)
H1AA1.11240.09060.11260.035*
C2A1.0046 (3)0.13031 (18)0.18655 (9)0.0347 (5)
H2AA1.04750.18330.19720.042*
C3A0.9028 (3)0.10783 (19)0.22109 (9)0.0399 (6)
H3AA0.87800.14490.25510.048*
C4A0.8374 (4)0.0297 (2)0.20491 (10)0.0426 (6)
H4AA0.76660.01510.22800.051*
C5A0.8762 (3)0.02741 (18)0.15462 (9)0.0359 (5)
H5AA0.83290.08030.14410.043*
C6A0.9805 (3)0.00437 (15)0.12024 (8)0.0258 (4)
C7A0.9607 (3)0.13500 (15)0.04342 (9)0.0309 (5)
H7AA0.87400.15630.05650.037*
C8A1.0462 (3)0.17068 (15)0.00468 (9)0.0298 (5)
H8AA1.03010.22040.03090.036*
C9A1.1647 (3)0.11558 (14)0.00604 (8)0.0226 (4)
C10A1.2922 (3)0.12322 (15)0.04811 (8)0.0235 (4)
C11A1.3292 (3)0.20125 (14)0.09116 (8)0.0225 (4)
H11A1.27110.24830.09370.027*
C12A1.4534 (3)0.20890 (15)0.13040 (8)0.0240 (4)
C13A1.5398 (3)0.13848 (17)0.12752 (9)0.0303 (5)
H13A1.62200.14380.15390.036*
C14A1.5021 (3)0.06018 (17)0.08493 (9)0.0331 (5)
H14A1.55930.01280.08270.040*
C15A1.3794 (3)0.05260 (16)0.04567 (8)0.0283 (5)
H15A1.35470.00010.01730.034*
C16A1.4931 (3)0.29600 (15)0.17435 (8)0.0236 (4)
O1B1.0385 (2)0.63497 (11)0.31587 (6)0.0289 (3)
O2B1.3177 (2)0.67241 (11)0.29641 (6)0.0277 (3)
N1B0.9371 (2)0.93770 (12)0.56028 (7)0.0229 (4)
N2B1.0854 (2)0.93899 (12)0.53531 (6)0.0216 (3)
C1B1.1010 (3)1.06570 (16)0.63134 (8)0.0267 (4)
H1BA1.20141.06700.61350.032*
C2B1.1088 (3)1.12830 (17)0.67979 (8)0.0308 (5)
H2BA1.21481.17090.69450.037*
C3B0.9589 (3)1.12698 (18)0.70596 (9)0.0362 (6)
H3BA0.96401.16870.73830.043*
C4B0.8006 (3)1.06335 (18)0.68384 (9)0.0361 (5)
H4BA0.69971.06330.70130.043*
C5B0.7918 (3)0.99997 (16)0.63590 (9)0.0311 (5)
H5BA0.68580.95700.62140.037*
C6B0.9428 (3)1.00136 (15)0.60980 (8)0.0243 (4)
C7B0.7971 (3)0.87027 (16)0.53268 (9)0.0339 (5)
H7BA0.68280.85670.54240.041*
C8B0.8557 (3)0.82614 (16)0.48798 (9)0.0317 (5)
H8BA0.79030.77690.46120.038*
C9B1.0358 (3)0.87105 (14)0.49110 (8)0.0207 (4)
C10B1.1659 (3)0.84961 (14)0.45499 (8)0.0227 (4)
C11B1.1187 (3)0.78132 (14)0.40765 (7)0.0210 (4)
H11B1.00140.75000.39800.025*
C12B1.2456 (3)0.75986 (14)0.37487 (8)0.0234 (4)
C13B1.4212 (3)0.80507 (17)0.38890 (9)0.0318 (5)
H13B1.50580.79040.36700.038*
C14B1.4695 (3)0.87257 (18)0.43609 (9)0.0374 (6)
H14B1.58690.90330.44580.045*
C15B1.3434 (3)0.89403 (16)0.46862 (9)0.0322 (5)
H15B1.37730.93890.50020.039*
C16B1.1898 (3)0.68338 (14)0.32605 (7)0.0215 (4)
O1C0.45630 (18)0.48572 (11)0.29247 (5)0.0240 (3)
O2C0.70998 (17)0.44937 (10)0.28620 (5)0.0206 (3)
N1C0.3491 (2)0.71485 (12)0.55515 (6)0.0203 (3)
N2C0.4858 (2)0.68099 (12)0.53726 (6)0.0206 (3)
C1C0.4597 (3)0.75143 (15)0.64512 (8)0.0239 (4)
H1CA0.51940.70500.63620.029*
C2C0.4694 (3)0.80360 (16)0.69617 (8)0.0290 (5)
H2CA0.53790.79290.72150.035*
C3C0.3778 (3)0.87166 (16)0.70978 (8)0.0321 (5)
H3CA0.38280.90540.74420.039*
C4C0.2791 (3)0.88917 (17)0.67205 (9)0.0337 (5)
H4CA0.21800.93490.68120.040*
C5C0.2709 (3)0.83868 (16)0.62051 (8)0.0282 (5)
H5CA0.20630.85140.59500.034*
C6C0.3598 (3)0.76925 (14)0.60752 (7)0.0214 (4)
C7C0.2168 (3)0.69150 (15)0.51775 (8)0.0236 (4)
H7CA0.11130.70720.52140.028*
C8C0.2681 (3)0.64053 (15)0.47366 (8)0.0229 (4)
H8CA0.20550.61450.44150.027*
C9C0.4369 (3)0.63602 (14)0.48750 (7)0.0192 (4)
C10C0.5541 (2)0.58987 (14)0.45517 (7)0.0185 (4)
C11C0.5233 (3)0.56048 (14)0.40109 (7)0.0187 (4)
H11C0.42790.57090.38530.022*
C12C0.6337 (2)0.51578 (13)0.37057 (7)0.0178 (4)
C13C0.7780 (3)0.50106 (14)0.39425 (7)0.0197 (4)
H13C0.85300.47190.37420.024*
C14C0.8087 (3)0.53019 (14)0.44790 (8)0.0217 (4)
H14C0.90460.52020.46370.026*
C15C0.6984 (3)0.57396 (14)0.47825 (7)0.0206 (4)
H15C0.72030.59290.51420.025*
C16C0.5968 (2)0.48180 (14)0.31252 (7)0.0184 (4)
O1D0.96510 (18)0.49718 (11)0.20445 (5)0.0230 (3)
O2D1.25582 (18)0.53777 (10)0.21192 (5)0.0205 (3)
N1D0.6220 (2)0.27979 (12)0.05822 (6)0.0206 (3)
N2D0.7938 (2)0.31606 (12)0.04095 (6)0.0200 (3)
C1D0.6886 (3)0.25619 (15)0.14861 (8)0.0242 (4)
H1DA0.79430.30300.13890.029*
C2D0.6411 (3)0.20990 (16)0.20067 (8)0.0276 (5)
H2DA0.71640.22570.22590.033*
C3D0.4833 (3)0.14069 (16)0.21533 (8)0.0292 (5)
H3DA0.45210.11070.25020.035*
C4D0.3723 (3)0.11638 (16)0.17781 (9)0.0309 (5)
H4DA0.26600.07000.18760.037*
C5D0.4182 (3)0.16084 (15)0.12542 (8)0.0267 (4)
H5DA0.34460.14360.10020.032*
C6D0.5760 (3)0.23139 (14)0.11147 (7)0.0206 (4)
C7D0.5147 (3)0.29660 (16)0.01962 (8)0.0246 (4)
H7DA0.39320.27830.02270.030*
C8D0.6191 (3)0.34543 (15)0.02464 (8)0.0245 (4)
H8DA0.58380.36730.05750.029*
C9D0.7913 (3)0.35560 (14)0.00984 (7)0.0194 (4)
C10D0.9570 (3)0.40278 (13)0.04207 (7)0.0189 (4)
C11D0.9577 (3)0.42900 (14)0.09619 (7)0.0195 (4)
H11D0.85270.41640.11190.023*
C12D1.1138 (3)0.47380 (13)0.12698 (7)0.0180 (4)
C13D1.2705 (3)0.49167 (14)0.10350 (7)0.0196 (4)
H13D1.37500.52090.12380.024*
C14D1.2716 (3)0.46595 (14)0.04972 (8)0.0221 (4)
H14D1.37690.47790.03410.027*
C15D1.1159 (3)0.42249 (14)0.01917 (7)0.0204 (4)
H15D1.11750.40640.01680.025*
C16D1.1096 (3)0.50458 (14)0.18509 (7)0.0189 (4)
O31.1049 (2)0.44372 (11)0.30900 (6)0.0254 (3)
C171.0641 (3)0.34913 (16)0.31647 (10)0.0338 (5)
H17A1.12060.31080.29120.041*
H17B0.93890.32040.31060.041*
C181.1228 (3)0.34828 (19)0.37057 (11)0.0384 (6)
H18A1.09930.28340.37350.058*
H18B1.06060.38210.39550.058*
H18C1.24600.37880.37700.058*
O41.6609 (2)0.54954 (11)0.19115 (6)0.0267 (3)
C191.7212 (3)0.64612 (18)0.18609 (11)0.0407 (6)
H19A1.81510.68180.21250.049*
H19B1.62660.67610.19180.049*
C201.7857 (4)0.6501 (2)0.13303 (13)0.0532 (8)
H20A1.82690.71560.13110.080*
H20B1.69190.61680.10690.080*
H20C1.87950.62050.12730.080*
H1OA1.642 (4)0.357 (2)0.2328 (11)0.044 (8)*
H1OB1.276 (4)0.623 (2)0.2673 (12)0.052 (9)*
H1O31.215 (4)0.460 (2)0.3076 (11)0.043 (8)*
H1O41.750 (4)0.5287 (19)0.1914 (10)0.036 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.0187 (17)0.0279 (17)0.0179 (15)0.0079 (14)0.0006 (13)0.0011 (13)
Li20.0185 (17)0.0281 (17)0.0166 (15)0.0050 (14)0.0007 (13)0.0006 (13)
O1A0.0382 (9)0.0259 (8)0.0301 (8)0.0127 (7)0.0098 (7)0.0050 (6)
O2A0.0300 (8)0.0321 (8)0.0224 (7)0.0123 (7)0.0044 (6)0.0044 (6)
N1A0.0245 (9)0.0213 (8)0.0246 (9)0.0058 (7)0.0021 (7)0.0017 (7)
N2A0.0220 (9)0.0242 (8)0.0211 (8)0.0056 (7)0.0005 (7)0.0030 (7)
C1A0.0267 (11)0.0301 (11)0.0251 (10)0.0061 (9)0.0023 (9)0.0007 (8)
C2A0.0316 (13)0.0357 (12)0.0303 (12)0.0098 (10)0.0009 (10)0.0051 (10)
C3A0.0395 (14)0.0464 (15)0.0256 (11)0.0085 (12)0.0054 (10)0.0034 (10)
C4A0.0431 (15)0.0504 (16)0.0320 (13)0.0112 (12)0.0103 (11)0.0076 (11)
C5A0.0381 (14)0.0358 (12)0.0332 (12)0.0129 (11)0.0050 (10)0.0045 (10)
C6A0.0246 (11)0.0262 (10)0.0229 (10)0.0038 (8)0.0013 (8)0.0026 (8)
C7A0.0307 (12)0.0232 (10)0.0357 (12)0.0102 (9)0.0069 (9)0.0018 (9)
C8A0.0321 (12)0.0216 (10)0.0326 (11)0.0101 (9)0.0036 (9)0.0022 (8)
C9A0.0234 (10)0.0187 (9)0.0233 (10)0.0035 (8)0.0016 (8)0.0030 (7)
C10A0.0225 (10)0.0231 (9)0.0213 (9)0.0037 (8)0.0021 (8)0.0016 (8)
C11A0.0230 (10)0.0204 (9)0.0228 (10)0.0053 (8)0.0028 (8)0.0035 (7)
C12A0.0261 (11)0.0242 (10)0.0195 (9)0.0066 (8)0.0034 (8)0.0012 (8)
C13A0.0321 (12)0.0346 (12)0.0241 (10)0.0140 (10)0.0011 (9)0.0014 (9)
C14A0.0380 (13)0.0318 (11)0.0304 (11)0.0181 (10)0.0006 (10)0.0002 (9)
C15A0.0320 (12)0.0280 (11)0.0221 (10)0.0104 (9)0.0017 (9)0.0019 (8)
C16A0.0233 (10)0.0242 (10)0.0196 (9)0.0041 (8)0.0014 (8)0.0010 (8)
O1B0.0251 (8)0.0263 (7)0.0276 (8)0.0035 (6)0.0030 (6)0.0043 (6)
O2B0.0231 (8)0.0327 (8)0.0204 (7)0.0054 (6)0.0029 (6)0.0048 (6)
N1B0.0251 (9)0.0195 (8)0.0227 (8)0.0053 (7)0.0074 (7)0.0029 (6)
N2B0.0222 (9)0.0241 (8)0.0192 (8)0.0095 (7)0.0041 (6)0.0032 (6)
C1B0.0275 (11)0.0304 (11)0.0211 (10)0.0098 (9)0.0046 (8)0.0016 (8)
C2B0.0313 (12)0.0313 (11)0.0255 (11)0.0081 (9)0.0004 (9)0.0009 (9)
C3B0.0437 (15)0.0368 (13)0.0235 (11)0.0119 (11)0.0053 (10)0.0024 (9)
C4B0.0372 (14)0.0394 (13)0.0286 (12)0.0092 (11)0.0128 (10)0.0034 (10)
C5B0.0303 (12)0.0289 (11)0.0296 (11)0.0041 (9)0.0070 (9)0.0031 (9)
C6B0.0311 (11)0.0231 (10)0.0194 (9)0.0102 (8)0.0064 (8)0.0034 (8)
C7B0.0254 (12)0.0266 (11)0.0382 (13)0.0021 (9)0.0107 (10)0.0038 (9)
C8B0.0275 (12)0.0229 (10)0.0341 (12)0.0007 (9)0.0057 (9)0.0047 (9)
C9B0.0226 (10)0.0184 (9)0.0210 (9)0.0071 (8)0.0019 (8)0.0030 (7)
C10B0.0243 (10)0.0228 (9)0.0194 (9)0.0069 (8)0.0019 (8)0.0014 (7)
C11B0.0214 (10)0.0199 (9)0.0197 (9)0.0047 (7)0.0008 (7)0.0024 (7)
C12B0.0239 (10)0.0223 (9)0.0207 (9)0.0061 (8)0.0001 (8)0.0008 (7)
C13B0.0254 (11)0.0345 (12)0.0290 (11)0.0076 (9)0.0045 (9)0.0039 (9)
C14B0.0215 (11)0.0407 (13)0.0360 (13)0.0020 (10)0.0008 (9)0.0102 (10)
C15B0.0282 (12)0.0311 (11)0.0266 (11)0.0041 (9)0.0008 (9)0.0093 (9)
C16B0.0241 (10)0.0214 (9)0.0185 (9)0.0084 (8)0.0001 (8)0.0014 (7)
O1C0.0165 (7)0.0393 (8)0.0175 (7)0.0114 (6)0.0007 (5)0.0052 (6)
O2C0.0157 (7)0.0264 (7)0.0176 (6)0.0064 (6)0.0009 (5)0.0007 (5)
N1C0.0202 (8)0.0228 (8)0.0174 (8)0.0067 (7)0.0020 (6)0.0031 (6)
N2C0.0193 (8)0.0210 (8)0.0199 (8)0.0051 (6)0.0015 (6)0.0024 (6)
C1C0.0256 (11)0.0228 (9)0.0217 (10)0.0061 (8)0.0021 (8)0.0027 (8)
C2C0.0322 (12)0.0306 (11)0.0204 (10)0.0044 (9)0.0014 (9)0.0039 (8)
C3C0.0423 (14)0.0295 (11)0.0196 (10)0.0091 (10)0.0031 (9)0.0029 (8)
C4C0.0437 (14)0.0286 (11)0.0289 (11)0.0163 (10)0.0039 (10)0.0002 (9)
C5C0.0353 (12)0.0278 (11)0.0228 (10)0.0126 (9)0.0016 (9)0.0038 (8)
C6C0.0227 (10)0.0210 (9)0.0169 (9)0.0032 (8)0.0029 (7)0.0011 (7)
C7C0.0232 (10)0.0280 (10)0.0217 (9)0.0104 (8)0.0012 (8)0.0063 (8)
C8C0.0230 (10)0.0276 (10)0.0183 (9)0.0090 (8)0.0004 (8)0.0037 (8)
C9C0.0204 (10)0.0195 (9)0.0167 (8)0.0039 (7)0.0012 (7)0.0040 (7)
C10C0.0163 (9)0.0211 (9)0.0168 (8)0.0031 (7)0.0013 (7)0.0045 (7)
C11C0.0159 (9)0.0220 (9)0.0176 (9)0.0047 (7)0.0006 (7)0.0042 (7)
C12C0.0167 (9)0.0194 (8)0.0158 (8)0.0034 (7)0.0003 (7)0.0036 (7)
C13C0.0175 (9)0.0227 (9)0.0183 (9)0.0055 (7)0.0017 (7)0.0039 (7)
C14C0.0181 (10)0.0259 (10)0.0217 (9)0.0061 (8)0.0029 (7)0.0068 (8)
C15C0.0199 (10)0.0239 (9)0.0159 (8)0.0033 (8)0.0012 (7)0.0041 (7)
C16C0.0152 (9)0.0217 (9)0.0173 (9)0.0037 (7)0.0009 (7)0.0045 (7)
O1D0.0169 (7)0.0365 (8)0.0163 (6)0.0113 (6)0.0010 (5)0.0033 (6)
O2D0.0168 (7)0.0282 (7)0.0159 (6)0.0095 (6)0.0008 (5)0.0003 (5)
N1D0.0192 (8)0.0234 (8)0.0171 (8)0.0048 (7)0.0004 (6)0.0021 (6)
N2D0.0189 (8)0.0212 (8)0.0185 (8)0.0065 (6)0.0015 (6)0.0014 (6)
C1D0.0240 (10)0.0238 (10)0.0221 (10)0.0058 (8)0.0006 (8)0.0008 (8)
C2D0.0335 (12)0.0306 (11)0.0188 (9)0.0116 (9)0.0049 (8)0.0026 (8)
C3D0.0334 (12)0.0318 (11)0.0185 (9)0.0116 (9)0.0038 (8)0.0044 (8)
C4D0.0288 (12)0.0283 (11)0.0270 (11)0.0015 (9)0.0039 (9)0.0023 (9)
C5D0.0267 (11)0.0262 (10)0.0232 (10)0.0033 (9)0.0003 (8)0.0029 (8)
C6D0.0229 (10)0.0220 (9)0.0164 (9)0.0076 (8)0.0018 (7)0.0019 (7)
C7D0.0191 (10)0.0329 (11)0.0202 (9)0.0063 (8)0.0022 (8)0.0041 (8)
C8D0.0228 (10)0.0299 (10)0.0189 (9)0.0067 (8)0.0019 (8)0.0032 (8)
C9D0.0225 (10)0.0202 (9)0.0158 (8)0.0076 (7)0.0003 (7)0.0028 (7)
C10D0.0205 (10)0.0196 (9)0.0160 (8)0.0074 (7)0.0009 (7)0.0012 (7)
C11D0.0181 (9)0.0227 (9)0.0176 (9)0.0071 (7)0.0010 (7)0.0030 (7)
C12D0.0193 (9)0.0196 (9)0.0155 (8)0.0081 (7)0.0004 (7)0.0020 (7)
C13D0.0174 (9)0.0227 (9)0.0178 (9)0.0062 (7)0.0007 (7)0.0023 (7)
C14D0.0194 (10)0.0263 (10)0.0206 (9)0.0075 (8)0.0052 (7)0.0043 (8)
C15D0.0233 (10)0.0235 (9)0.0151 (8)0.0092 (8)0.0026 (7)0.0026 (7)
C16D0.0189 (9)0.0223 (9)0.0165 (8)0.0090 (7)0.0007 (7)0.0028 (7)
O30.0161 (7)0.0327 (8)0.0292 (8)0.0069 (6)0.0020 (6)0.0104 (6)
C170.0301 (12)0.0253 (11)0.0423 (13)0.0059 (9)0.0002 (10)0.0032 (10)
C180.0286 (12)0.0413 (14)0.0541 (16)0.0120 (10)0.0023 (11)0.0261 (12)
O40.0189 (8)0.0343 (8)0.0309 (8)0.0116 (6)0.0037 (6)0.0104 (6)
C190.0317 (13)0.0292 (12)0.0580 (17)0.0092 (10)0.0030 (12)0.0033 (11)
C200.0403 (16)0.0542 (17)0.085 (2)0.0220 (14)0.0269 (15)0.0441 (17)
Geometric parameters (Å, º) top
Li1—O1A1.912 (4)N1C—N2C1.361 (2)
Li1—O2D1.931 (4)N1C—C6C1.427 (2)
Li1—O41.953 (4)N2C—C9C1.337 (2)
Li1—O1Ci1.954 (4)C1C—C2C1.387 (3)
Li2—O2C1.912 (4)C1C—C6C1.388 (3)
Li2—O1B1.931 (4)C1C—H1CA0.9300
Li2—O1D1.940 (4)C2C—C3C1.387 (3)
Li2—O31.960 (4)C2C—H2CA0.9300
O1A—C16A1.218 (3)C3C—C4C1.382 (3)
O2A—C16A1.317 (3)C3C—H3CA0.9300
O2A—H1OA0.91 (3)C4C—C5C1.391 (3)
N1A—C7A1.360 (3)C4C—H4CA0.9300
N1A—N2A1.363 (2)C5C—C6C1.387 (3)
N1A—C6A1.423 (3)C5C—H5CA0.9300
N2A—C9A1.335 (2)C7C—C8C1.368 (3)
C1A—C6A1.385 (3)C7C—H7CA0.9300
C1A—C2A1.390 (3)C8C—C9C1.414 (3)
C1A—H1AA0.9300C8C—H8CA0.9300
C2A—C3A1.375 (4)C9C—C10C1.469 (3)
C2A—H2AA0.9300C10C—C15C1.398 (3)
C3A—C4A1.383 (4)C10C—C11C1.399 (3)
C3A—H3AA0.9300C11C—C12C1.394 (3)
C4A—C5A1.389 (3)C11C—H11C0.9300
C4A—H4AA0.9300C12C—C13C1.398 (3)
C5A—C6A1.389 (3)C12C—C16C1.506 (3)
C5A—H5AA0.9300C13C—C14C1.388 (3)
C7A—C8A1.362 (3)C13C—H13C0.9300
C7A—H7AA0.9300C14C—C15C1.385 (3)
C8A—C9A1.413 (3)C14C—H14C0.9300
C8A—H8AA0.9300C15C—H15C0.9300
C9A—C10A1.468 (3)O1D—C16D1.251 (2)
C10A—C11A1.395 (3)O2D—C16D1.275 (2)
C10A—C15A1.400 (3)N1D—C7D1.359 (3)
C11A—C12A1.395 (3)N1D—N2D1.363 (2)
C11A—H11A0.9300N1D—C6D1.425 (2)
C12A—C13A1.391 (3)N2D—C9D1.342 (2)
C12A—C16A1.492 (3)C1D—C6D1.384 (3)
C13A—C14A1.389 (3)C1D—C2D1.392 (3)
C13A—H13A0.9300C1D—H1DA0.9300
C14A—C15A1.388 (3)C2D—C3D1.384 (3)
C14A—H14A0.9300C2D—H2DA0.9300
C15A—H15A0.9300C3D—C4D1.383 (3)
O1B—C16B1.220 (3)C3D—H3DA0.9300
O2B—C16B1.312 (2)C4D—C5D1.394 (3)
O2B—H1OB0.92 (3)C4D—H4DA0.9300
N1B—N2B1.356 (2)C5D—C6D1.391 (3)
N1B—C7B1.357 (3)C5D—H5DA0.9300
N1B—C6B1.424 (2)C7D—C8D1.367 (3)
N2B—C9B1.338 (2)C7D—H7DA0.9300
C1B—C6B1.388 (3)C8D—C9D1.408 (3)
C1B—C2B1.393 (3)C8D—H8DA0.9300
C1B—H1BA0.9300C9D—C10D1.475 (3)
C2B—C3B1.382 (3)C10D—C15D1.397 (3)
C2B—H2BA0.9300C10D—C11D1.397 (3)
C3B—C4B1.390 (4)C11D—C12D1.397 (3)
C3B—H3BA0.9300C11D—H11D0.9300
C4B—C5B1.387 (3)C12D—C13D1.388 (3)
C4B—H4BA0.9300C12D—C16D1.506 (3)
C5B—C6B1.389 (3)C13D—C14D1.389 (3)
C5B—H5BA0.9300C13D—H13D0.9300
C7B—C8B1.366 (3)C14D—C15D1.389 (3)
C7B—H7BA0.9300C14D—H14D0.9300
C8B—C9B1.405 (3)C15D—H15D0.9300
C8B—H8BA0.9300O3—C171.426 (3)
C9B—C10B1.463 (3)O3—H1O30.85 (3)
C10B—C15B1.396 (3)C17—C181.511 (3)
C10B—C11B1.398 (3)C17—H17A0.9700
C11B—C12B1.390 (3)C17—H17B0.9700
C11B—H11B0.9300C18—H18A0.9600
C12B—C13B1.387 (3)C18—H18B0.9600
C12B—C16B1.488 (3)C18—H18C0.9600
C13B—C14B1.390 (3)O4—C191.434 (3)
C13B—H13B0.9300O4—H1O40.85 (3)
C14B—C15B1.381 (3)C19—C201.510 (4)
C14B—H14B0.9300C19—H19A0.9700
C15B—H15B0.9300C19—H19B0.9700
O1C—C16C1.257 (2)C20—H20A0.9600
O1C—Li1ii1.954 (4)C20—H20B0.9600
O2C—C16C1.272 (2)C20—H20C0.9600
N1C—C7C1.359 (3)
O1A—Li1—O2D114.37 (17)C1C—C2C—C3C120.5 (2)
O1A—Li1—O4100.80 (17)C1C—C2C—H2CA119.8
O2D—Li1—O4113.07 (19)C3C—C2C—H2CA119.8
O1A—Li1—O1Ci109.10 (19)C4C—C3C—C2C119.8 (2)
O2D—Li1—O1Ci102.01 (16)C4C—C3C—H3CA120.1
O4—Li1—O1Ci118.00 (17)C2C—C3C—H3CA120.1
O2C—Li2—O1B112.91 (18)C3C—C4C—C5C120.3 (2)
O2C—Li2—O1D105.03 (16)C3C—C4C—H4CA119.8
O1B—Li2—O1D108.16 (19)C5C—C4C—H4CA119.8
O2C—Li2—O3112.76 (19)C6C—C5C—C4C119.4 (2)
O1B—Li2—O3101.30 (16)C6C—C5C—H5CA120.3
O1D—Li2—O3116.84 (18)C4C—C5C—H5CA120.3
C16A—O2A—H1OA110.3 (18)C5C—C6C—C1C120.70 (18)
C7A—N1A—N2A111.37 (17)C5C—C6C—N1C120.26 (18)
C7A—N1A—C6A128.98 (18)C1C—C6C—N1C119.04 (18)
N2A—N1A—C6A119.62 (17)N1C—C7C—C8C107.01 (18)
C9A—N2A—N1A104.87 (16)N1C—C7C—H7CA126.5
C6A—C1A—C2A119.4 (2)C8C—C7C—H7CA126.5
C6A—C1A—H1AA120.3C7C—C8C—C9C105.17 (17)
C2A—C1A—H1AA120.3C7C—C8C—H8CA127.4
C3A—C2A—C1A120.7 (2)C9C—C8C—H8CA127.4
C3A—C2A—H2AA119.6N2C—C9C—C8C111.09 (17)
C1A—C2A—H2AA119.6N2C—C9C—C10C120.22 (17)
C2A—C3A—C4A119.4 (2)C8C—C9C—C10C128.69 (17)
C2A—C3A—H3AA120.3C15C—C10C—C11C118.81 (18)
C4A—C3A—H3AA120.3C15C—C10C—C9C120.20 (17)
C3A—C4A—C5A120.9 (2)C11C—C10C—C9C120.99 (17)
C3A—C4A—H4AA119.5C12C—C11C—C10C120.83 (18)
C5A—C4A—H4AA119.5C12C—C11C—H11C119.6
C4A—C5A—C6A119.0 (2)C10C—C11C—H11C119.6
C4A—C5A—H5AA120.5C11C—C12C—C13C119.60 (17)
C6A—C5A—H5AA120.5C11C—C12C—C16C120.53 (17)
C1A—C6A—C5A120.4 (2)C13C—C12C—C16C119.87 (17)
C1A—C6A—N1A119.27 (19)C14C—C13C—C12C119.65 (18)
C5A—C6A—N1A120.3 (2)C14C—C13C—H13C120.2
N1A—C7A—C8A107.58 (19)C12C—C13C—H13C120.2
N1A—C7A—H7AA126.2C15C—C14C—C13C120.75 (18)
C8A—C7A—H7AA126.2C15C—C14C—H14C119.6
C7A—C8A—C9A104.95 (19)C13C—C14C—H14C119.6
C7A—C8A—H8AA127.5C14C—C15C—C10C120.37 (18)
C9A—C8A—H8AA127.5C14C—C15C—H15C119.8
N2A—C9A—C8A111.22 (18)C10C—C15C—H15C119.8
N2A—C9A—C10A119.82 (18)O1C—C16C—O2C123.21 (17)
C8A—C9A—C10A128.95 (18)O1C—C16C—C12C119.02 (17)
C11A—C10A—C15A118.78 (19)O2C—C16C—C12C117.76 (16)
C11A—C10A—C9A120.57 (19)C7D—N1D—N2D111.97 (15)
C15A—C10A—C9A120.65 (18)C7D—N1D—C6D128.50 (17)
C10A—C11A—C12A120.12 (19)N2D—N1D—C6D119.53 (16)
C10A—C11A—H11A119.9C9D—N2D—N1D104.39 (16)
C12A—C11A—H11A119.9C6D—C1D—C2D119.0 (2)
C13A—C12A—C11A120.64 (19)C6D—C1D—H1DA120.5
C13A—C12A—C16A121.64 (19)C2D—C1D—H1DA120.5
C11A—C12A—C16A117.70 (19)C3D—C2D—C1D120.8 (2)
C14A—C13A—C12A119.4 (2)C3D—C2D—H2DA119.6
C14A—C13A—H13A120.3C1D—C2D—H2DA119.6
C12A—C13A—H13A120.3C4D—C3D—C2D119.66 (19)
C15A—C14A—C13A120.1 (2)C4D—C3D—H3DA120.2
C15A—C14A—H14A120.0C2D—C3D—H3DA120.2
C13A—C14A—H14A120.0C3D—C4D—C5D120.5 (2)
C14A—C15A—C10A120.93 (19)C3D—C4D—H4DA119.7
C14A—C15A—H15A119.5C5D—C4D—H4DA119.7
C10A—C15A—H15A119.5C6D—C5D—C4D119.0 (2)
O1A—C16A—O2A123.60 (18)C6D—C5D—H5DA120.5
O1A—C16A—C12A122.29 (19)C4D—C5D—H5DA120.5
O2A—C16A—C12A114.10 (18)C1D—C6D—C5D121.04 (18)
C16B—O2B—H1OB109.8 (19)C1D—C6D—N1D119.29 (18)
N2B—N1B—C7B111.66 (17)C5D—C6D—N1D119.67 (19)
N2B—N1B—C6B120.00 (17)N1D—C7D—C8D107.07 (18)
C7B—N1B—C6B128.33 (19)N1D—C7D—H7DA126.5
C9B—N2B—N1B104.95 (16)C8D—C7D—H7DA126.5
C6B—C1B—C2B119.8 (2)C7D—C8D—C9D105.26 (18)
C6B—C1B—H1BA120.1C7D—C8D—H8DA127.4
C2B—C1B—H1BA120.1C9D—C8D—H8DA127.4
C3B—C2B—C1B119.9 (2)N2D—C9D—C8D111.31 (17)
C3B—C2B—H2BA120.0N2D—C9D—C10D119.98 (18)
C1B—C2B—H2BA120.0C8D—C9D—C10D128.71 (17)
C2B—C3B—C4B120.0 (2)C15D—C10D—C11D118.67 (17)
C2B—C3B—H3BA120.0C15D—C10D—C9D120.79 (17)
C4B—C3B—H3BA120.0C11D—C10D—C9D120.54 (18)
C5B—C4B—C3B120.5 (2)C12D—C11D—C10D120.91 (18)
C5B—C4B—H4BA119.7C12D—C11D—H11D119.5
C3B—C4B—H4BA119.7C10D—C11D—H11D119.5
C4B—C5B—C6B119.3 (2)C13D—C12D—C11D119.53 (17)
C4B—C5B—H5BA120.3C13D—C12D—C16D120.82 (17)
C6B—C5B—H5BA120.3C11D—C12D—C16D119.63 (17)
C1B—C6B—C5B120.43 (19)C12D—C13D—C14D120.13 (18)
C1B—C6B—N1B119.14 (19)C12D—C13D—H13D119.9
C5B—C6B—N1B120.42 (19)C14D—C13D—H13D119.9
N1B—C7B—C8B107.2 (2)C15D—C14D—C13D120.21 (19)
N1B—C7B—H7BA126.4C15D—C14D—H14D119.9
C8B—C7B—H7BA126.4C13D—C14D—H14D119.9
C7B—C8B—C9B105.23 (19)C14D—C15D—C10D120.55 (18)
C7B—C8B—H8BA127.4C14D—C15D—H15D119.7
C9B—C8B—H8BA127.4C10D—C15D—H15D119.7
N2B—C9B—C8B111.01 (18)O1D—C16D—O2D123.56 (17)
N2B—C9B—C10B119.97 (18)O1D—C16D—C12D119.06 (17)
C8B—C9B—C10B128.95 (18)O2D—C16D—C12D117.38 (17)
C15B—C10B—C11B118.17 (19)C17—O3—H1O3105 (2)
C15B—C10B—C9B120.05 (18)Li2—O3—H1O3123 (2)
C11B—C10B—C9B121.70 (19)O3—C17—C18111.84 (19)
C12B—C11B—C10B120.53 (19)O3—C17—H17A109.2
C12B—C11B—H11B119.7C18—C17—H17A109.2
C10B—C11B—H11B119.7O3—C17—H17B109.2
C13B—C12B—C11B120.52 (18)C18—C17—H17B109.2
C13B—C12B—C16B120.77 (19)H17A—C17—H17B107.9
C11B—C12B—C16B118.61 (18)C17—C18—H18A109.5
C12B—C13B—C14B119.3 (2)C17—C18—H18B109.5
C12B—C13B—H13B120.3H18A—C18—H18B109.5
C14B—C13B—H13B120.3C17—C18—H18C109.5
C15B—C14B—C13B120.1 (2)H18A—C18—H18C109.5
C15B—C14B—H14B119.9H18B—C18—H18C109.5
C13B—C14B—H14B119.9C19—O4—H1O4106.9 (19)
C14B—C15B—C10B121.29 (19)Li1—O4—H1O4118.8 (19)
C14B—C15B—H15B119.4O4—C19—C20111.6 (2)
C10B—C15B—H15B119.4O4—C19—H19A109.3
O1B—C16B—O2B124.17 (18)C20—C19—H19A109.3
O1B—C16B—C12B121.93 (19)O4—C19—H19B109.3
O2B—C16B—C12B113.89 (18)C20—C19—H19B109.3
C7C—N1C—N2C111.96 (16)H19A—C19—H19B108.0
C7C—N1C—C6C128.46 (17)C19—C20—H20A109.5
N2C—N1C—C6C119.58 (16)C19—C20—H20B109.5
C9C—N2C—N1C104.77 (16)H20A—C20—H20B109.5
C2C—C1C—C6C119.3 (2)C19—C20—H20C109.5
C2C—C1C—H1CA120.4H20A—C20—H20C109.5
C6C—C1C—H1CA120.4H20B—C20—H20C109.5
O2D—Li1—O1A—C16A174.1 (2)N2C—N1C—C6C—C1C29.7 (3)
O4—Li1—O1A—C16A64.3 (3)N2C—N1C—C7C—C8C0.1 (2)
O1Ci—Li1—O1A—C16A60.6 (3)C6C—N1C—C7C—C8C178.71 (19)
C16Ci—Li1—O1A—C16A36.5 (3)N1C—C7C—C8C—C9C0.2 (2)
C7A—N1A—N2A—C9A0.4 (2)N1C—N2C—C9C—C8C0.4 (2)
C6A—N1A—N2A—C9A178.84 (18)N1C—N2C—C9C—C10C179.91 (17)
C6A—C1A—C2A—C3A0.4 (4)C7C—C8C—C9C—N2C0.4 (2)
C1A—C2A—C3A—C4A0.8 (4)C7C—C8C—C9C—C10C180.0 (2)
C2A—C3A—C4A—C5A1.3 (4)N2C—C9C—C10C—C15C14.1 (3)
C3A—C4A—C5A—C6A0.7 (4)C8C—C9C—C10C—C15C165.4 (2)
C2A—C1A—C6A—C5A0.9 (4)N2C—C9C—C10C—C11C166.31 (19)
C2A—C1A—C6A—N1A178.3 (2)C8C—C9C—C10C—C11C14.1 (3)
C4A—C5A—C6A—C1A0.4 (4)C15C—C10C—C11C—C12C0.2 (3)
C4A—C5A—C6A—N1A178.8 (2)C9C—C10C—C11C—C12C179.32 (18)
C7A—N1A—C6A—C1A170.6 (2)C10C—C11C—C12C—C13C0.7 (3)
N2A—N1A—C6A—C1A11.3 (3)C10C—C11C—C12C—C16C178.23 (18)
C7A—N1A—C6A—C5A10.1 (4)C11C—C12C—C13C—C14C0.7 (3)
N2A—N1A—C6A—C5A168.0 (2)C16C—C12C—C13C—C14C178.26 (18)
N2A—N1A—C7A—C8A0.4 (3)C12C—C13C—C14C—C15C0.2 (3)
C6A—N1A—C7A—C8A178.7 (2)C13C—C14C—C15C—C10C0.2 (3)
N1A—C7A—C8A—C9A0.3 (3)C11C—C10C—C15C—C14C0.2 (3)
N1A—N2A—C9A—C8A0.2 (2)C9C—C10C—C15C—C14C179.79 (18)
N1A—N2A—C9A—C10A179.50 (18)Li1ii—O1C—C16C—O2C21.6 (3)
C7A—C8A—C9A—N2A0.0 (3)Li1ii—O1C—C16C—C12C159.17 (18)
C7A—C8A—C9A—C10A179.2 (2)Li2—O2C—C16C—O1C121.9 (2)
N2A—C9A—C10A—C11A168.5 (2)Li2—O2C—C16C—C12C58.9 (3)
C8A—C9A—C10A—C11A10.6 (4)Li2—O2C—C16C—Li1ii108.4 (2)
N2A—C9A—C10A—C15A11.2 (3)C11C—C12C—C16C—O1C6.9 (3)
C8A—C9A—C10A—C15A169.7 (2)C13C—C12C—C16C—O1C172.00 (19)
C15A—C10A—C11A—C12A1.1 (3)C11C—C12C—C16C—O2C173.83 (18)
C9A—C10A—C11A—C12A178.6 (2)C13C—C12C—C16C—O2C7.3 (3)
C10A—C11A—C12A—C13A0.9 (3)C11C—C12C—C16C—Li1ii22.7 (4)
C10A—C11A—C12A—C16A177.42 (19)C13C—C12C—C16C—Li1ii158.4 (3)
C11A—C12A—C13A—C14A0.3 (4)O2C—Li2—O1D—C16D162.18 (17)
C16A—C12A—C13A—C14A177.9 (2)O1B—Li2—O1D—C16D77.0 (2)
C12A—C13A—C14A—C15A0.0 (4)O3—Li2—O1D—C16D36.4 (3)
C13A—C14A—C15A—C10A0.2 (4)O1A—Li1—O2D—C16D1.3 (3)
C11A—C10A—C15A—C14A0.8 (3)O4—Li1—O2D—C16D113.3 (2)
C9A—C10A—C15A—C14A178.9 (2)O1Ci—Li1—O2D—C16D118.9 (2)
Li1—O1A—C16A—O2A14.2 (4)C16Ci—Li1—O2D—C16D128.7 (2)
Li1—O1A—C16A—C12A165.4 (2)C7D—N1D—N2D—C9D0.4 (2)
C13A—C12A—C16A—O1A176.8 (2)C6D—N1D—N2D—C9D179.65 (17)
C11A—C12A—C16A—O1A4.9 (3)C6D—C1D—C2D—C3D0.5 (3)
C13A—C12A—C16A—O2A3.6 (3)C1D—C2D—C3D—C4D0.8 (3)
C11A—C12A—C16A—O2A174.68 (19)C2D—C3D—C4D—C5D0.2 (4)
O2C—Li2—O1B—C16B165.81 (19)C3D—C4D—C5D—C6D1.3 (3)
O1D—Li2—O1B—C16B78.4 (3)C2D—C1D—C6D—C5D0.6 (3)
O3—Li2—O1B—C16B45.0 (3)C2D—C1D—C6D—N1D178.75 (19)
C16D—Li2—O1B—C16B55.5 (2)C4D—C5D—C6D—C1D1.5 (3)
C7B—N1B—N2B—C9B0.3 (2)C4D—C5D—C6D—N1D177.85 (19)
C6B—N1B—N2B—C9B179.24 (18)C7D—N1D—C6D—C1D151.3 (2)
C6B—C1B—C2B—C3B0.8 (4)N2D—N1D—C6D—C1D28.6 (3)
C1B—C2B—C3B—C4B0.1 (4)C7D—N1D—C6D—C5D28.1 (3)
C2B—C3B—C4B—C5B0.9 (4)N2D—N1D—C6D—C5D152.06 (19)
C3B—C4B—C5B—C6B0.7 (4)N2D—N1D—C7D—C8D0.1 (2)
C2B—C1B—C6B—C5B1.0 (3)C6D—N1D—C7D—C8D179.99 (19)
C2B—C1B—C6B—N1B179.9 (2)N1D—C7D—C8D—C9D0.3 (2)
C4B—C5B—C6B—C1B0.2 (4)N1D—N2D—C9D—C8D0.6 (2)
C4B—C5B—C6B—N1B179.4 (2)N1D—N2D—C9D—C10D180.00 (17)
N2B—N1B—C6B—C1B1.4 (3)C7D—C8D—C9D—N2D0.6 (2)
C7B—N1B—C6B—C1B179.8 (2)C7D—C8D—C9D—C10D179.9 (2)
N2B—N1B—C6B—C5B179.4 (2)N2D—C9D—C10D—C15D11.7 (3)
C7B—N1B—C6B—C5B0.7 (3)C8D—C9D—C10D—C15D167.5 (2)
N2B—N1B—C7B—C8B0.3 (3)N2D—C9D—C10D—C11D168.53 (18)
C6B—N1B—C7B—C8B179.1 (2)C8D—C9D—C10D—C11D12.2 (3)
N1B—C7B—C8B—C9B0.1 (3)C15D—C10D—C11D—C12D0.2 (3)
N1B—N2B—C9B—C8B0.2 (2)C9D—C10D—C11D—C12D179.91 (18)
N1B—N2B—C9B—C10B177.43 (18)C10D—C11D—C12D—C13D0.6 (3)
C7B—C8B—C9B—N2B0.1 (3)C10D—C11D—C12D—C16D177.67 (18)
C7B—C8B—C9B—C10B177.0 (2)C11D—C12D—C13D—C14D0.6 (3)
N2B—C9B—C10B—C15B5.5 (3)C16D—C12D—C13D—C14D177.66 (18)
C8B—C9B—C10B—C15B171.1 (2)C12D—C13D—C14D—C15D0.2 (3)
N2B—C9B—C10B—C11B177.91 (19)C13D—C14D—C15D—C10D1.0 (3)
C8B—C9B—C10B—C11B5.4 (3)C11D—C10D—C15D—C14D1.0 (3)
C15B—C10B—C11B—C12B1.1 (3)C9D—C10D—C15D—C14D179.27 (18)
C9B—C10B—C11B—C12B177.69 (19)Li2—O1D—C16D—O2D17.1 (3)
C10B—C11B—C12B—C13B0.7 (3)Li2—O1D—C16D—C12D163.43 (18)
C10B—C11B—C12B—C16B177.13 (19)Li1—O2D—C16D—O1D121.8 (2)
C11B—C12B—C13B—C14B0.3 (4)Li1—O2D—C16D—C12D58.7 (3)
C16B—C12B—C13B—C14B176.6 (2)Li1—O2D—C16D—Li2111.5 (2)
C12B—C13B—C14B—C15B0.1 (4)C13D—C12D—C16D—O1D171.96 (18)
C13B—C14B—C15B—C10B0.5 (4)C11D—C12D—C16D—O1D6.3 (3)
C11B—C10B—C15B—C14B1.0 (4)C13D—C12D—C16D—O2D7.5 (3)
C9B—C10B—C15B—C14B177.6 (2)C11D—C12D—C16D—O2D174.21 (18)
Li2—O1B—C16B—O2B31.3 (3)C13D—C12D—C16D—Li2165.2 (3)
Li2—O1B—C16B—C12B147.2 (2)C11D—C12D—C16D—Li216.6 (4)
C13B—C12B—C16B—O1B171.3 (2)O2C—Li2—C16D—O1D21.7 (2)
C11B—C12B—C16B—O1B5.1 (3)O1B—Li2—C16D—O1D109.0 (2)
C13B—C12B—C16B—O2B7.4 (3)O3—Li2—C16D—O1D147.7 (2)
C11B—C12B—C16B—O2B176.24 (19)O2C—Li2—C16D—O2D172.6 (2)
O1B—Li2—O2C—C16C2.6 (3)O1B—Li2—C16D—O2D56.79 (17)
O1D—Li2—O2C—C16C120.3 (2)O1D—Li2—C16D—O2D165.8 (2)
O3—Li2—O2C—C16C111.5 (2)O3—Li2—C16D—O2D46.51 (16)
C16D—Li2—O2C—C16C128.9 (2)O2C—Li2—C16D—C12D12.3 (5)
C7C—N1C—N2C—C9C0.3 (2)O1B—Li2—C16D—C12D143.0 (3)
C6C—N1C—N2C—C9C178.58 (17)O1D—Li2—C16D—C12D34.0 (4)
C6C—C1C—C2C—C3C1.2 (3)O3—Li2—C16D—C12D113.7 (3)
C1C—C2C—C3C—C4C1.5 (4)O2C—Li2—O3—C1727.5 (3)
C2C—C3C—C4C—C5C0.2 (4)O1B—Li2—O3—C17148.46 (19)
C3C—C4C—C5C—C6C1.3 (4)O1D—Li2—O3—C1794.3 (3)
C4C—C5C—C6C—C1C1.5 (3)C16D—Li2—O3—C17107.9 (2)
C4C—C5C—C6C—N1C178.3 (2)Li2—O3—C17—C18133.1 (2)
C2C—C1C—C6C—C5C0.3 (3)O1A—Li1—O4—C19150.1 (2)
C2C—C1C—C6C—N1C179.53 (19)O2D—Li1—O4—C1927.6 (3)
C7C—N1C—C6C—C5C28.2 (3)O1Ci—Li1—O4—C1991.3 (3)
N2C—N1C—C6C—C5C150.5 (2)C16Ci—Li1—O4—C19104.9 (2)
C7C—N1C—C6C—C1C151.6 (2)Li1—O4—C19—C20133.6 (2)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H1OA···O2Ci0.91 (3)1.70 (3)2.594 (2)167 (3)
O2B—H1OB···O2D0.92 (3)1.68 (3)2.584 (2)165 (3)
O3—H1O3···O1Ci0.85 (3)1.92 (3)2.761 (2)171 (3)
O4—H1O4···O1Di0.85 (3)1.94 (3)2.780 (2)170 (2)
C7A—H7AA···N2D0.932.583.306 (3)136
C5C—H5CA···N2Bii0.932.603.501 (3)163
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formula[Li2(C16H11N2O2)2(C16H12N2O2)2(C2H6O)2]
Mr1161.10
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.9607 (1), 14.9527 (2), 26.5320 (4)
α, β, γ (°)103.471 (1), 90.348 (1), 105.429 (1)
V3)2952.82 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.47 × 0.18 × 0.15
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.960, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
66644, 17230, 11897
Rint0.046
(sin θ/λ)max1)0.707
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.168, 1.04
No. of reflections17230
No. of parameters811
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Li1—O1A1.912 (4)Li2—O2C1.912 (4)
Li1—O2D1.931 (4)Li2—O1B1.931 (4)
Li1—O41.953 (4)Li2—O1D1.940 (4)
Li1—O1Ci1.954 (4)Li2—O31.960 (4)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H1OA···O2Ci0.91 (3)1.70 (3)2.594 (2)167 (3)
O2B—H1OB···O2D0.92 (3)1.68 (3)2.584 (2)165 (3)
O3—H1O3···O1Ci0.85 (3)1.92 (3)2.761 (2)171 (3)
O4—H1O4···O1Di0.85 (3)1.94 (3)2.780 (2)170 (2)
C7A—H7AA···N2D0.932.583.306 (3)136
C5C—H5CA···N2Bii0.932.603.501 (3)163
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and KBS thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. KBS thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. AMI is grateful to the Director, NITK, Surathkal, India, for providing research facilities. SR thanks Dr Gautam Das & Raghvendra G.M, Syngene International Ltd, Bangalore, India, for allocation of research resources.

References

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Volume 65| Part 8| August 2009| Pages m917-m918
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