p-Tolyl bis­(cyclo­hexyl­amido)­phosphinate

Raissi Shabari, A.; Pourayoubi, M.; Taghizadeh, A.; Ghoreishi, F.; Vahdani, B.

doi:10.1107/S1600536811029722

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 (C-C) = 0.004 Å
R = 0.052
wR = 0.090
Data-to-parameter ratio = 24.3
Details

p-Tolyl bis(cyclohexylamido)phosphinate

Akbar Raissi Shabari,^a ^* Mehrdad Pourayoubi,^b Afsaneh Taghizadeh,^a Farnaz Ghoreishi ^a and Banafsheh Vahdani ^a

^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-HO(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). For bond lengths in related structures, see: Sabbaghi et al. (2011); Rudd et al. (1996). For double hydrogen-bond acceptors, see: Steiner (2002).

Experimental

Crystal data

C₁₉H₃₁N₂O₂P
M_r = 350.43
Monoclinic, P 2₁ /a
a = 9.131 (5) Å
b = 19.333 (5) Å
c = 11.291 (5) Å
= 99.247 (5)°
V = 1967.3 (15) Å³
Z = 4
Mo K radiation
= 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) in PLATON (Spek, 2009)] T_min = 0.992, T_max = 1.000
14835 measured reflections
5296 independent reflections
1925 reflections with I > 2(I)
R_int = 0.091

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.090
S = 0.76
5296 reflections
218 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.76	2.23	2.969 (3)	163
N2-H2O1ⁱ	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); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).

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.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.
Rudd, M. D., Lindeman, S. V. & Husebye, S. (1996). Acta Chem. Scand. 50, 759-774.
Sabbaghi, F., Pourayoubi, M., Karimi Ahmadabad, F. & Parvez, M. (2011). Acta Cryst. E67, o1502.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.

organic compounds