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

Ajibade, P.A.; Onwudiwe, D.C.; Omondi, B.

doi:10.1107/S1600536812048416

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.042
wR = 0.107
Data-to-parameter ratio = 19.8
Details

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

Peter A. Ajibade,^a Damian C. Onwudiwe ^a and Bernard Omondi ^b ^*

^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 P^V 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); Greenwood & Earnshaw (1984); Balakrishna et al. (2000). For the ability of bis(diphenylphosphino)alkylaniline derivatives to form chelates with transition metal ions, see: Biricik et al. (2007); Fei & Dyson (2005). For the synthesis of the title and related compounds, see: Fernández et al. (2005); Gaw et al. (2002); Fei et al. (2004); Slawin et al. (2005).

Experimental

Crystal data

C₃₂H₂₉NP₂S₂
M_r = 553.62
Triclinic, $[P \overline 1]$
a = 9.6305 (11) Å
b = 13.8027 (14) Å
c = 21.360 (2) Å
= 82.484 (2)°
= 84.635 (2)°
= 79.975 (2)°
V = 2764.7 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.946, T_max = 0.974
56725 measured reflections
13522 independent reflections
9271 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.107
S = 1.00
13522 reflections
684 parameters
9 restraints
H-atom parameters constrained
_max = 0.82 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C17-H17Cg2ⁱ	0.95	2.97	3.759 (3)	141
C64-H64ACg1ⁱⁱ	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); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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

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organic compounds