N,N,N′,N′-Tetra­benzyl-N′′-(2,6-difluoro­benzo­yl)phospho­ric triamide

Raissi Shabari, A.; Pourayoubi, M.; Tarahhomi, A.; Rheingold, A.L.; Golen, J.A.

doi:10.1107/S1600536812042481

Volume 68
Part 11
Page o3186
November 2012

Received 1 October 2012
Accepted 10 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 15.9
Details

N,N,N',N'-Tetrabenzyl-N''-(2,6-difluorobenzoyl)phosphoric triamide

Akbar Raissi Shabari,^a ^* Mehrdad Pourayoubi,^b Atekeh Tarahhomi,^b Arnold L. Rheingold ^c and James A. Golen ^c

^aFaculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran,^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^cDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
Correspondence e-mail: a.raissi_shabari@yahoo.com

In the C(O)NHP(O) fragment of the title compound, C₃₅H₃₂F₂N₃O₂P, the P-N bond is longer and the O-P-N angle is contracted compared with the other two P-N bonds and O-P-N angles. The P atom adopts a distorted tetrahedral environment and the phosphoryl and carbonyl groups are anti with respect to each other. The two tertiary N atoms of the dibenzylamido groups show sp² character with a slight deviation from planarity. In the crystal, pairs of N-HO(P) hydrogen bonds form inversion dimers.

Related literature

For related structures with a [C(O)NH]P(O)[N]₂ configuration, see: Sabbaghi et al. (2010); Pourayoubi et al. (2010). For the geometries of the tertiary N atoms in phosphoric triamides with a C(O)NHP(O)[N]₂ core, see: Pourayoubi et al. (2012).

Experimental

Crystal data

C₃₅H₃₂F₂N₃O₂P
M_r = 595.61
Monoclinic, P 2₁ /c
a = 12.3079 (7) Å
b = 19.5089 (12) Å
c = 13.0131 (6) Å
= 105.430 (3)°
V = 3012.0 (3) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 100 K
0.18 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.975, T_max = 0.986
23928 measured reflections
6199 independent reflections
4332 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.111
S = 1.01
6199 reflections
391 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.86 (2)	1.90 (2)	2.761 (2)	176 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5269 ).

Acknowledgements

Support of this investigation by the 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.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Pourayoubi, M., Jasinski, J. P., Shoghpour Bayraq, S., Eshghi, H., Keeley, A. C., Bruno, G. & Amiri Rudbari, H. (2012). Acta Cryst. C68, o399-o404.
Pourayoubi, M., Tarahhomi, A., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o2524.
Sabbaghi, F., Rostami Chaijan, M. & Pourayoubi, M. (2010). Acta Cryst. E66, o1754.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds