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Volume 69 
Part 3 
Pages m160-m161  
March 2013  

Received 13 February 2013
Accepted 15 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.115
Data-to-parameter ratio = 17.4
Details
Open access

(2,2'-Bipyridine-[kappa]2N,N')[bis(diphenylthiophosphinoyl)methyl]lithium(I) benzene monosolvate

aCollege of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China,bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
Correspondence e-mail: hkfun@usm.my

In the title benzene-solvated heteroleptic lithium complex, [Li(C25H21P2S2)(C10H8N2)]·C6H6, the LiI ion is four-coordinated in a distorted tetrahedral geometry by two S atoms and two N atoms of the two chelating ligands, viz. bis(diphenylthiophosphinoyl)methyl and 2,2'-bipyridine. The 2,2'-bipyridine molecule is slightly twisted with a dihedral angle between the pyridine rings of 7.35 (12)°. Intramolecular C-H...S hydrogen bonds are present. In the crystal, molecules are stacked along the c axis by [pi]-[pi] interactions, with centroid-centroid distances of 3.6021 (15) and 3.6401 (16) Å. The crystal structure also features weak C-H...[pi] interactions.

Related literature

For standard bond lengths, 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 background to and applications of thiophosphinoyl ligands and their complexes, see: Amir et al. (2013[Amir, A., Sayer, A. H., Zagalsky, R., Shimon, L. W. & Fischer, B. (2013). J. Org. Chem. 78, 270-277.]); Leung, Wan & Mak (2010[Leung, W.-P., Wan, C.-L. & Mak, T. C. W. (2010). Organometallics, 29, 1622-1628.]); Leung, Wan, Kan & Mak (2010[Leung, W.-P., Wan, C.-L., Kan, K.-W. & Mak, T. C. W. (2010). Organometallics, 29, 814-820.]); Ren et al. (2011[Ren, W., Deng, X., Zi, G. & Fang, D.-C. (2011). Dalton Trans. 40, 9662-9664.]). For related structures, see: Thirumoorthi & Chivers (2012[Thirumoorthi, R. & Chivers, T. (2012). Eur. J. Inorg. Chem. pp. 3061-3069.]).

[Scheme 1]

Experimental

Crystal data
  • [Li(C25H21P2S2)(C10H8N2)]·C6H6

  • Mr = 688.73

  • Triclinic, [P \overline 1]

  • a = 10.7654 (11) Å

  • b = 13.1295 (12) Å

  • c = 13.5498 (11) Å

  • [alpha] = 90.746 (2)°

  • [beta] = 101.902 (1)°

  • [gamma] = 109.257 (2)°

  • V = 1762.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 297 K

  • 0.44 × 0.28 × 0.20 mm

Data collection
  • Bruker APEXII CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.889, Tmax = 0.947

  • 10290 measured reflections

  • 7517 independent reflections

  • 5856 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.115

  • S = 1.04

  • 7517 reflections

  • 433 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg6 and Cg7 are the centroids of the C11-C16, C30-C35 and C36-C41 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C12-H12...S1 0.95 2.86 3.367 (2) 114
C25-H25...S2 0.95 2.82 3.332 (2) 115
C1-H1...Cg6 0.95 2.77 3.710 (3) 172
C21-H21...Cg6i 0.95 2.70 3.632 (3) 166
C28-H28...Cg7ii 0.95 2.93 3.654 (3) 134
C37-H37...Cg3iii 0.95 2.80 3.634 (3) 147
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5044 ).


Acknowledgements

We thank the Fundamental Research Funds for the Central Universities (XDJK2013C032) and the Doctoral Foundation of Southwest University for support and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. The authors also thank Universiti Sains Malaysia (USM) for the RUC grant (Structure Determination of 50 kDa Outer Membrane Proteins From S.typhi By X-ray Protein Crystallography, No. 1001/PSKBP/8630013).

References

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.
Amir, A., Sayer, A. H., Zagalsky, R., Shimon, L. W. & Fischer, B. (2013). J. Org. Chem. 78, 270-277.  [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Leung, W.-P., Wan, C.-L., Kan, K.-W. & Mak, T. C. W. (2010). Organometallics, 29, 814-820.  [CSD] [CrossRef] [ChemPort]
Leung, W.-P., Wan, C.-L. & Mak, T. C. W. (2010). Organometallics, 29, 1622-1628.  [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Ren, W., Deng, X., Zi, G. & Fang, D.-C. (2011). Dalton Trans. 40, 9662-9664.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thirumoorthi, R. & Chivers, T. (2012). Eur. J. Inorg. Chem. pp. 3061-3069.  [ISI] [CSD] [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m160-m161   [ doi:10.1107/S160053681300456X ]

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