[4-(Dimethyl­amino)­phen­yl]diphenyl­phosphine selenide

Davis, W.L.; Muller, A.

doi:10.1107/S1600536812042602

Volume 68
Part 11
Pages o3153-o3154
November 2012

Received 27 September 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 21.7
Details

[4-(Dimethylamino)phenyl]diphenylphosphine selenide

Wade L. Davis ^a and Alfred Muller ^a ^*

^aResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: mullera@uj.ac.za

In the title compound, C₂₀H₂₀NPSe, the P atom lies in a distorted tetrahedral environment. The Tolman cone angle is 157° indicating steric crowding at this atom. In the crystal, weak C-HSe interactions create linked dimeric units and C-H [pi] interactions are also observed.

Related literature

For investigations into the steric and electronic properties of phosphorus containing ligands, see: Roodt et al. (2003); Otto & Roodt (2004); Muller et al. (2008); Cowley & Damasco (1971); Allen & Taylor (1982); Allen et al. (1985). For the free phosphine related to the title compound, see: Dreissig & Plieth (1972). For the oxide analogue of the title compound, see: Lynch et al. (2003). For the related phosphine selenide, see: Phasha et al. (2012). For cone angles, see: Tolman (1977); Otto (2001). For details on the conformational fit of molecules using Mercury, see: Macrae et al. (2006); Weng et al. (2008a,b). For a description of the Cambridge Structural Database, see: Allen (2002). For background on Bent's rule, see: Bent (1961).

Experimental

Crystal data

C₂₀H₂₀NPSe
M_r = 384.3
Monoclinic, P 2₁ /c
a = 12.1757 (13) Å
b = 10.6173 (11) Å
c = 17.5211 (14) Å
= 128.098 (5)°
V = 1782.5 (3) Å³
Z = 4
Mo K radiation
= 2.20 mm^-1
T = 100 K
0.22 × 0.11 × 0.09 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.643, T_max = 0.827
31924 measured reflections
4553 independent reflections
3798 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.097
S = 1.06
4553 reflections
210 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.72 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 refer to the centroids of the C7-C12 and C13-C18 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C20-H20ASe1ⁱ	0.98	3.25	3.833 (3)	120
C20-H20CSe1ⁱⁱ	0.98	3.07	3.707 (3)	124
C4-H4Cg1ⁱⁱⁱ	0.95	2.66	3.476 (4)	145
C15-H15Cg1^iv	0.95	2.90	3.699 (3)	142
C19-H19BCg2^v	0.98	2.79	3.627 (3)	144
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x, -y, -z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) & WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2075 ).

Acknowledgements

Financial assistance from the Research Fund of the University of Johannesburg is gratefully acknowledged.

References

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organic compounds