P,P-Bis[4-(dimethyl­amino)­phen­yl]-N,N-bis­(propan-2-yl)phosphinic amide

Evans, S.J.; Renison, C.A.; Williams, D.B.G.; Muller, A.

doi:10.1107/S1600536812050398

Volume 69
Part 2
Page o195
February 2013

Received 23 November 2012
Accepted 11 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.110
Data-to-parameter ratio = 20.7
Details

P,P-Bis[4-(dimethylamino)phenyl]-N,N-bis(propan-2-yl)phosphinic amide

Stephen J. Evans,^a C. Alicia Renison,^a D. Bradley G. Williams ^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: bwilliams@uj.ac.za

The molecular structure of the title compound, C₂₂H₃₄N₃OP, adopts a distorted tetrahedral geometry at the P atom, with the most noticeable distortion being for the O-P-N angle [117.53 (10)°]. An effective cone angle of 187° was calculated for the compound. In the crystal, weak C-HO interactions create infinite chains along [100], whereas C-H [pi] interactions propagating in [001] generate a herringbone motif.

Related literature

For the synthesis of ligands derived from phosphinic amides, see: Williams et al. (2009). For background to DoM technology, see: Snieckus (1990). For cone angles, see: Tolman (1977); Otto (2001).

Experimental

Crystal data

C₂₂H₃₄N₃OP
M_r = 387.49
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2960 (4) Å
b = 16.6389 (8) Å
c = 19.9475 (11) Å
V = 2089.7 (2) Å³
Z = 4
Mo K radiation
= 0.15 mm^-1
T = 100 K
0.13 × 0.11 × 0.1 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.981, T_max = 0.985
18896 measured reflections
5212 independent reflections
3840 reflections with I > 2(I)
R_int = 0.074

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.110
S = 1.04
5212 reflections
252 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.35 e Å^-3
Absolute structure: Flack (1983), 2224 Friedel pairs
Flack parameter: 0.11 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11-C16 and C21-C26 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C12-H12O1ⁱ	0.95	2.59	3.493 (3)	159
C33-H33AO1ⁱ	0.98	2.58	3.501 (3)	158
C18-H18ACg1ⁱⁱ	0.98	2.96	3.821 (2)	148
C18-H18CCg2ⁱⁱ	0.98	2.97	3.915 (3)	162
C27-H27CCg1ⁱⁱⁱ	0.98	2.69	3.468 (3)	137
Symmetry codes: (i) x+1, y, z; (ii) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); 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) and WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6869 ).

Acknowledgements

The University of the Free State is thanked for the use of their diffractometer. Financial assistance from Sasol, THRIP and the Research Fund of the University of Johannesburg is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Otto, S. (2001). Acta Cryst. C57, 793-795.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Snieckus, V. (1990). Chem. Rev. 90, 879-933.
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Williams, D. B. G., Evans, S. J., De Bod, H., Mokhadinyana, M. S. & Hughes, T. (2009). Synthesis, 18, 3106-3112.

organic compounds