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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 [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.027
wR = 0.081
Data-to-parameter ratio = 29.9
Details
Open access

Diphenyl (isopropylamido)phosphate

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-H...O=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[Sabbaghi, F., Pourayoubi, M., Negari, M. & Necas, M. (2011). Acta Cryst. E67, o2512.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18NO3P

  • Mr = 291.27

  • Monoclinic, P n

  • a = 8.4432 (5) Å

  • b = 5.3030 (4) Å

  • c = 16.3443 (11) Å

  • [beta] = 90.453 (6)°

  • V = 731.78 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.918, Tmax = 0.926

  • 6226 measured reflections

  • 6226 independent reflections

  • 6040 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1229 Friedel pairs

  • Flack parameter: 0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O3i 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[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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) 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: 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.  [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.
Sabbaghi, F., Pourayoubi, M., Negari, M. & Necas, M. (2011). Acta Cryst. E67, o2512.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3459  [ doi:10.1107/S1600536812047940 ]

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