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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 [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 15.9
Details
Open access

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

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-H...O(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[Sabbaghi, F., Rostami Chaijan, M. & Pourayoubi, M. (2010). Acta Cryst. E66, o1754.]); Pourayoubi et al. (2010[Pourayoubi, M., Tarahhomi, A., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o2524.]). 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[Pourayoubi, M., Jasinski, J. P., Shoghpour Bayraq, S., Eshghi, H., Keeley, A. C., Bruno, G. & Amiri Rudbari, H. (2012). Acta Cryst. C68, o399-o404.]).

[Scheme 1]

Experimental

Crystal data
  • C35H32F2N3O2P

  • Mr = 595.61

  • Monoclinic, P 21 /c

  • a = 12.3079 (7) Å

  • b = 19.5089 (12) Å

  • c = 13.0131 (6) Å

  • [beta] = 105.430 (3)°

  • V = 3012.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.986

  • 23928 measured reflections

  • 6199 independent reflections

  • 4332 reflections with I > 2[sigma](I)

  • Rint = 0.062

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.86 (2) 1.90 (2) 2.761 (2) 176 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL 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: 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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [details]
Pourayoubi, M., Tarahhomi, A., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o2524.  [CSD] [CrossRef] [details]
Sabbaghi, F., Rostami Chaijan, M. & Pourayoubi, M. (2010). Acta Cryst. E66, o1754.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3186  [ doi:10.1107/S1600536812042481 ]

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