Diphenyl (isopropyl­amido)­phosphate

Sabbaghi, F.; Pourayoubi, M.; Nečas, M.; Babiak, M.

doi:10.1107/S1600536812047940

Volume 68
Part 12
Page o3459
December 2012

Received 14 November 2012
Accepted 21 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.027
wR = 0.081
Data-to-parameter ratio = 29.9
Details

Diphenyl (isopropylamido)phosphate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi,^b Marek Necas ^c and Michal Babiak ^c

^aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran,^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^cDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

The P atom in the title compound, C₁₅H₁₈NO₃P, is in a distorted tetrahedral P(O)(O)₂N environment; the bond angles at P are in the range 98.16 (6)-115.82 (6)°. In the crystal, adjacent molecules are linked via N-HO=P hydrogen bonds into a chain running parallel to the b axis. The methyl groups are disordered over two sets of sites in a 0.677 (14):0.323 (14) ratio. The crystal studied was a non-merohedral twin with a refined minor component of 22.31 (4)%.

Related literature

For bond lengths and angles in a related structure, see: Sabbaghi et al. (2011).

Experimental

Crystal data

C₁₅H₁₈NO₃P
M_r = 291.27
Monoclinic, P n
a = 8.4432 (5) Å
b = 5.3030 (4) Å
c = 16.3443 (11) Å
= 90.453 (6)°
V = 731.78 (9) Å³
Z = 2
Mo K radiation
= 0.19 mm^-1
T = 120 K
0.45 × 0.42 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.918, T_max = 0.926
6226 measured reflections
6226 independent reflections
6040 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.081
S = 1.06
6226 reflections
208 parameters
28 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.18 e Å^-3
Absolute structure: Flack (1983), 1229 Friedel pairs
Flack parameter: 0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.81 (1)	2.23 (1)	3.0065 (17)	161 (2)
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2090 ).

Acknowledgements

Support of this investigation by Zanjan 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sabbaghi, F., Pourayoubi, M., Negari, M. & Necas, M. (2011). Acta Cryst. E67, o2512.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds