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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 [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.110
Data-to-parameter ratio = 20.7
Details
Open access

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

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-H...O 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[Williams, D. B. G., Evans, S. J., De Bod, H., Mokhadinyana, M. S. & Hughes, T. (2009). Synthesis, 18, 3106-3112.]). For background to DoM technology, see: Snieckus (1990[Snieckus, V. (1990). Chem. Rev. 90, 879-933.]). For cone angles, see: Tolman (1977[Tolman, C. A. (1977). Chem. Rev. 77, 313-348.]); Otto (2001[Otto, S. (2001). Acta Cryst. C57, 793-795.]).

[Scheme 1]

Experimental

Crystal data
  • C22H34N3OP

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2004). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.985

  • 18896 measured reflections

  • 5212 independent reflections

  • 3840 reflections with I > 2[sigma](I)

  • Rint = 0.074

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

  • wR(F2) = 0.110

  • S = 1.04

  • 5212 reflections

  • 252 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 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-H...A D-H H...A D...A D-H...A
C12-H12...O1i 0.95 2.59 3.493 (3) 159
C33-H33A...O1i 0.98 2.58 3.501 (3) 158
C18-H18A...Cg1ii 0.98 2.96 3.821 (2) 148
C18-H18C...Cg2ii 0.98 2.97 3.915 (3) 162
C27-H27C...Cg1iii 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[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and 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: 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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Otto, S. (2001). Acta Cryst. C57, 793-795.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Snieckus, V. (1990). Chem. Rev. 90, 879-933.  [CrossRef] [ChemPort] [ISI]
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.  [CrossRef] [ChemPort] [ISI]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Williams, D. B. G., Evans, S. J., De Bod, H., Mokhadinyana, M. S. & Hughes, T. (2009). Synthesis, 18, 3106-3112.  [ISI] [CrossRef]


Acta Cryst (2013). E69, o195  [ doi:10.1107/S1600536812050398 ]

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