[Journal logo]

Volume 67 
Part 8 
Page o2167  
August 2011  

Received 13 July 2011
Accepted 22 July 2011
Online 30 July 2011

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.090
Data-to-parameter ratio = 24.3
Details
Open access

p-Tolyl bis(cyclohexylamido)phosphinate

aFaculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
Correspondence e-mail: a.raissi_shabari@yahoo.com

The P atom in the title molecule, C19H31N2O2P, is in a distorted tetrahedral configuration with the bond angles in the range 101.48 (10)-118.58 (9)°. The N-H units have a syn orientation with respect to one another. In the crystal, molecules are connected via two different intermolecular N-H...O(P) hydrogen bonds into chains along the a axis in which the O atom of the P=O group acts as a double acceptor.

Related literature

For background to phosphoramidate compounds, see: Pourayoubi et al. (2011[Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.]). For bond lengths in related structures, see: Sabbaghi et al. (2011[Sabbaghi, F., Pourayoubi, M., Karimi Ahmadabad, F. & Parvez, M. (2011). Acta Cryst. E67, o1502.]); Rudd et al. (1996[Rudd, M. D., Lindeman, S. V. & Husebye, S. (1996). Acta Chem. Scand. 50, 759-774.]). For double hydrogen-bond acceptors, see: Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]).

[Scheme 1]

Experimental

Crystal data
  • C19H31N2O2P

  • Mr = 350.43

  • Monoclinic, P 21 /a

  • a = 9.131 (5) Å

  • b = 19.333 (5) Å

  • c = 11.291 (5) Å

  • [beta] = 99.247 (5)°

  • V = 1967.3 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 291 K

  • 0.38 × 0.12 × 0.08 mm

Data collection
  • Stoe IPDS II image plate diffractometer

  • Absorption correction: multi-scan [MULABS (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.])] Tmin = 0.992, Tmax = 1.000

  • 14835 measured reflections

  • 5296 independent reflections

  • 1925 reflections with I > 2[sigma](I)

  • Rint = 0.091

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.090

  • S = 0.76

  • 5296 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.76 2.23 2.969 (3) 163
N2-H2...O1i 0.75 2.25 2.975 (3) 162
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5287 ).


Acknowledgements

Support of this investigation by North Tehran Branch, Islamic Azad University, is gratefully acknowledged.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.  [CSD] [CrossRef] [details]
Rudd, M. D., Lindeman, S. V. & Husebye, S. (1996). Acta Chem. Scand. 50, 759-774.  [CrossRef] [ChemPort]
Sabbaghi, F., Pourayoubi, M., Karimi Ahmadabad, F. & Parvez, M. (2011). Acta Cryst. E67, o1502.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2011). E67, o2167  [ doi:10.1107/S1600536811029722 ]

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.