[Journal logo]

Volume 68 
Part 12 
Pages o3491-o3492  
December 2012  

Received 6 November 2012
Accepted 26 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.042
wR = 0.107
Data-to-parameter ratio = 19.8
Details
Open access

N,N-Bis(diphenylthiophosphinoyl)-4-ethylaniline

aDepartment of Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa, and bSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
Correspondence e-mail: owaga@ukzn.ac.za

The title compound, C32H29NP2S2, has two molecules in the asymmetric unit, with an r.m.s. difference of 0.218 Å in their best-fit overlay. Both molecules have a slightly distorted trigonal-planar N atom, bonded to two PV atoms and a C atom of the 4-ethylphenyl unit. The P-N-P angles of 126.34 (11) and 125.98 (11)° are larger than the four C-N-P bond angles. The two S atoms are trans to one another with respect to the P-N-P angle. The crystal structure features C-H...[pi] interactions. The methyl group in one of the molecules is disordered over two sets of sites, with occupancies of 0.518 (6) and 0.482 (6).

Related literature

For background to the chemistry of coordination compounds containing P-N bonds and for their applications, see: Hartley (1990[Hartley, F. R. (1990). The Chemistry of Organophosphorus Compounds, p. 1. Manchester: Wiley.]); Greenwood & Earnshaw (1984[Greenwood, N. N. & Earnshaw, A. (1984). Chemistry of Elements, p. 619. Oxford: Pergamon Press.]); Balakrishna et al. (2000[Balakrishna, M. S., Panda, R., Smith, D. C. Jr, Kalamn, A. & Nolan, S. P. (2000). J. Organomet. Chem. 599, 159-165.]). For the ability of bis(diphenylphosphino)alkylaniline derivatives to form chelates with transition metal ions, see: Biricik et al. (2007)[Biricik, N., Durap, F., Gümgüm, B., Fei, Z. & Scopelliti, R. (2007). Transition Met. Chem. 32, 877-883.]; Fei & Dyson (2005[Fei, Z. & Dyson, P. J. (2005). Coord. Chem. Rev. 249, 2056-2074.]). For the synthesis of the title and related compounds, see: Fernández et al. (2005[Fernández, I., Breher, F., Pregosin, P. S., Fei, Z. & Dyson, P. J. (2005). Inorg. Chem. 44, 7616-7623.]); Gaw et al. (2002[Gaw, K. G., Smith, M. B. & Steed, J. W. (2002). J. Organomet. Chem. 664, 294-297.]); Fei et al. (2004[Fei, Z., Zhao, D., Biricik, N., Scopelliti, R. & Dyson, P. J. (2004). Inorg. Chem. 44, 2228-2230.]); Slawin et al. (2005[Slawin, A. M. Z., Wheatley, J. & Woollins, J. D. (2005). Eur. J. Inorg. Chem. pp. 713-720.]).

[Scheme 1]

Experimental

Crystal data
  • C32H29NP2S2

  • Mr = 553.62

  • Triclinic, [P \overline 1]

  • a = 9.6305 (11) Å

  • b = 13.8027 (14) Å

  • c = 21.360 (2) Å

  • [alpha] = 82.484 (2)°

  • [beta] = 84.635 (2)°

  • [gamma] = 79.975 (2)°

  • V = 2764.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 173 K

  • 0.17 × 0.08 × 0.08 mm

Data collection
  • Bruker X8 APEXII 4K KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.974

  • 56725 measured reflections

  • 13522 independent reflections

  • 9271 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.107

  • S = 1.00

  • 13522 reflections

  • 684 parameters

  • 9 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.82 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19-C24 and C57-C62 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C17-H17...Cg2i 0.95 2.97 3.759 (3) 141
C64-H64A...Cg1ii 0.98 2.88 3.767 (3) 151
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2607 ).


Acknowledgements

The authors gratefully acknowledge the financial support of GMRDC, University of Fort Hare, South Africa.

References

Balakrishna, M. S., Panda, R., Smith, D. C. Jr, Kalamn, A. & Nolan, S. P. (2000). J. Organomet. Chem. 599, 159-165.  [ChemPort]
Biricik, N., Durap, F., Gümgüm, B., Fei, Z. & Scopelliti, R. (2007). Transition Met. Chem. 32, 877-883.  [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fei, Z. & Dyson, P. J. (2005). Coord. Chem. Rev. 249, 2056-2074.  [CrossRef] [ChemPort]
Fei, Z., Zhao, D., Biricik, N., Scopelliti, R. & Dyson, P. J. (2004). Inorg. Chem. 44, 2228-2230.  [CrossRef]
Fernández, I., Breher, F., Pregosin, P. S., Fei, Z. & Dyson, P. J. (2005). Inorg. Chem. 44, 7616-7623.  [PubMed]
Gaw, K. G., Smith, M. B. & Steed, J. W. (2002). J. Organomet. Chem. 664, 294-297.  [CSD] [CrossRef] [ChemPort]
Greenwood, N. N. & Earnshaw, A. (1984). Chemistry of Elements, p. 619. Oxford: Pergamon Press.
Hartley, F. R. (1990). The Chemistry of Organophosphorus Compounds, p. 1. Manchester: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Slawin, A. M. Z., Wheatley, J. & Woollins, J. D. (2005). Eur. J. Inorg. Chem. pp. 713-720.  [CrossRef]


Acta Cryst (2012). E68, o3491-o3492   [ doi:10.1107/S1600536812048416 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.