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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 [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.064
Data-to-parameter ratio = 15.7
Details
Open access

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

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[Sabbaghi, F., Pourayoubi, M. & Necas, M. (2012). Acta Cryst. E68, o2891.]). For structures with a P-N(CH2C6H5)2 fragment, 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
  • C16H20NO2PS

  • Mr = 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[alpha] radiation

  • [mu] = 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.] Tmin = 0.802, Tmax = 0.927

  • 4397 measured reflections

  • 3010 independent reflections

  • 2747 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.064

  • S = 1.03

  • 3010 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 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[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.]); software used to prepare material for publication: 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: 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.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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]
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.  [CrossRef] [details]
Sabbaghi, F., Pourayoubi, M. & Necas, M. (2012). Acta Cryst. E68, o2891.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3074  [ doi:10.1107/S1600536812041220 ]

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