N,N-Dibenzyl-O,O′-dimethyl thio­phosphate

Raissi Shabari, A.; Sabbaghi, F.; Pourayoubi, M.; Nečas, M.; Babiak, M.

doi:10.1107/S1600536812041220

Volume 68
Part 11
Page o3074
November 2012

Received 23 September 2012
Accepted 1 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.064
Data-to-parameter ratio = 15.7
Details

N,N-Dibenzyl-O,O'-dimethyl thiophosphate

Akbar Raissi Shabari,^a ^* Fahimeh Sabbaghi,^b Mehrdad Pourayoubi,^c Marek Necas ^d and Michal Babiak ^d

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

The P atom in the title compound, C₁₆H₂₀NO₂PS, is bonded in a distorted tetrahedral P(S)(O)₂N environment with the bond angles at the P atom in the range 99.37 (7) to 115.68 (5)°. The angles at the amido N atom (with bond-angle sum of 357.8°) confirm its sp² character. The C-O-P bond angles are 119.78 (11) and 119.39 (12)°.

Related literature

For a related phosphoramidothioate structure, see: Sabbaghi et al. (2012). For structures with a P-N(CH₂C₆H₅)₂ fragment, see: Pourayoubi et al. (2012).

Experimental

Crystal data

C₁₆H₂₀NO₂PS
M_r = 321.36
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.8377 (3) Å
b = 8.1115 (4) Å
c = 28.6187 (16) Å
V = 1587.31 (14) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 120 K
0.75 × 0.55 × 0.25 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 = 0.802, T_max = 0.927
4397 measured reflections
3010 independent reflections
2747 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.064
S = 1.03
3010 reflections
192 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.31 e Å^-3
Absolute structure: Flack (1983), 982 Friedel pairs
Flack parameter: -0.04 (7)

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: enCIFer (Allen et al., 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5538 ).

Acknowledgements

Support of this investigation by the Islamic Azad University, North Tehran Branch, 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.
Pourayoubi, M., Jasinski, J. P., Shoghpour Bayraq, S., Eshghi, H., Keeley, A. C., Bruno, G. & Amiri Rudbari, H. (2012). Acta Cryst. C68, o399-o404.
Sabbaghi, F., Pourayoubi, M. & Necas, M. (2012). Acta Cryst. E68, o2891.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds