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Volume 68 
Part 12 
Pages o3406-o3407  
December 2012  

Received 6 November 2012
Accepted 9 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.051
wR = 0.140
Data-to-parameter ratio = 16.5
Details
Open access

N-(4-Fluorobenzoyl)-N',N''-diisopropylphosphoric triamide

aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
Correspondence e-mail: pourayoubi@um.ac.ir

The asymmetric unit of the title phosphoric triamide, C13H21FN3O2P, consists of two independent molecules. In each molecule, the P=O group and the N-H unit belonging to the C(O)NHP(O) fragment are in a syn conformation with respect to each other. An intramolecular N-H...O hydrogen bond occurs in each molecule. The P atom adopts a distorted tetrahedral environment. The methyl groups of an isopropyl fragment are disordered over two sets of sites with refined occupancies of 0.458 (5) and 0.542 (5). In the crystal, molecules are linked through N-H...O(=P) and N-H...O(=C) hydrogen bonds into chains along [001].

Related literature

For related structures with a [C(O)NH]P(O)[NHC]2 moiety, see: Pourayoubi et al. (2011[Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.]); Raissi Shabari et al. (2012[Raissi Shabari, A., Pourayoubi, M., Fadaei, H., Necas, M. & Babiak, M. (2012). Acta Cryst. E68, o1813.]). For the preparation of the starting compound 4-F-C6H4C(O)NHP(O)Cl2, see: Tarahhomi et al. (2011[Tarahhomi, A., Pourayoubi, M., Rheingold, A. L. & Golen, J. A. (2011). Struct. Chem. 22, 201-210.]).

[Scheme 1]

Experimental

Crystal data
  • C13H21FN3O2P

  • Mr = 301.30

  • Monoclinic, P 21 /c

  • a = 15.9974 (12) Å

  • b = 10.7474 (7) Å

  • c = 19.5478 (13) Å

  • [beta] = 111.461 (2)°

  • V = 3127.8 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 100 K

  • 0.22 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.959, Tmax = 0.972

  • 24038 measured reflections

  • 6366 independent reflections

  • 4979 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.140

  • S = 1.08

  • 6366 reflections

  • 385 parameters

  • 11 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 1.28 e Å-3

  • [Delta][rho]min = -1.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O4i 0.87 (2) 1.97 (2) 2.832 (2) 172 (2)
N2-H2N...O3ii 0.85 (2) 2.18 (2) 3.010 (2) 167 (2)
N3-H3N...O1 0.83 (2) 2.51 (3) 2.990 (3) 118 (2)
N4-H4N...O2iii 0.85 (2) 1.96 (2) 2.802 (2) 171 (3)
N5-H5N...O1ii 0.85 (2) 2.15 (2) 2.990 (2) 167 (2)
N6-H6N...O3 0.83 (2) 2.51 (3) 3.055 (3) 124 (2)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and 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: FF2089 ).


Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad 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.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.  [CSD] [CrossRef] [details]
Raissi Shabari, A., Pourayoubi, M., Fadaei, H., Necas, M. & Babiak, M. (2012). Acta Cryst. E68, o1813.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tarahhomi, A., Pourayoubi, M., Rheingold, A. L. & Golen, J. A. (2011). Struct. Chem. 22, 201-210.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3406-o3407   [ doi:10.1107/S1600536812046326 ]

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