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

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

doi:10.1107/S1600536812046326

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.051
wR = 0.140
Data-to-parameter ratio = 16.5
Details

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

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

^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-HO 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-HO(=P) and N-HO(=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); Raissi Shabari et al. (2012). For the preparation of the starting compound 4-F-C₆H₄C(O)NHP(O)Cl₂, see: Tarahhomi et al. (2011).

Experimental

Crystal data

C₁₃H₂₁FN₃O₂P
M_r = 301.30
Monoclinic, P 2₁ /c
a = 15.9974 (12) Å
b = 10.7474 (7) Å
c = 19.5478 (13) Å
= 111.461 (2)°
V = 3127.8 (4) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.959, T_max = 0.972
24038 measured reflections
6366 independent reflections
4979 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(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
_max = 1.28 e Å^-3
_min = -1.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO4ⁱ	0.87 (2)	1.97 (2)	2.832 (2)	172 (2)
N2-H2NO3ⁱⁱ	0.85 (2)	2.18 (2)	3.010 (2)	167 (2)
N3-H3NO1	0.83 (2)	2.51 (3)	2.990 (3)	118 (2)
N4-H4NO2ⁱⁱⁱ	0.85 (2)	1.96 (2)	2.802 (2)	171 (3)
N5-H5NO1ⁱⁱ	0.85 (2)	2.15 (2)	2.990 (2)	167 (2)
N6-H6NO3	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); 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: Mercury (Macrae et al., 2008) and 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: 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.
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.
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.
Raissi Shabari, A., Pourayoubi, M., Fadaei, H., Necas, M. & Babiak, M. (2012). Acta Cryst. E68, o1813.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tarahhomi, A., Pourayoubi, M., Rheingold, A. L. & Golen, J. A. (2011). Struct. Chem. 22, 201-210.

organic compounds