Diphenyl (o-tolyl­amido)­phospho­nate

Sabbaghi, F.; Pourayoubi, M.; Zargaran, P.

doi:10.1107/S1600536811013924

Volume 67
Part 5
Page o1170
May 2011

Received 31 March 2011
Accepted 13 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 18.4
Details

Diphenyl (o-tolylamido)phosphonate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi ^b and Poorya Zargaran ^b

^aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, PO Box 49195-467, Zanjan, Iran, and ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran
Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

The asymmetric unit of the title compound, C₁₉H₁₈NO₃P, contains two independent molecules in which the P atoms are found in slightly distorted tetrahedral environments. In the crystal, pairs of intermolecular N-HO(P) hydrogen bonds form two independent centrosymmetric dimers.

Related literature

For a related structure, see: Pourayoubi et al. (2010).

Experimental

Crystal data

C₁₉H₁₈NO₃P
M_r = 339.31
Triclinic, $[P \overline 1]$
a = 10.2986 (13) Å
b = 10.3540 (12) Å
c = 17.993 (2) Å
= 86.650 (2)°
= 84.036 (2)°
= 62.429 (2)°
V = 1691.4 (4) Å³
Z = 4
Mo K radiation
= 0.18 mm^-1
T = 120 K
0.50 × 0.40 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.918, T_max = 0.956
17593 measured reflections
8135 independent reflections
6772 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.104
S = 1.00
8135 reflections
441 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.85 (2)	2.09 (2)	2.903 (1)	162 (1)
N1'-H1'NO1'ⁱⁱ	0.86 (2)	2.02 (2)	2.867 (1)	167 (1)
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 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: LH5229 ).

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.
Bruker (1998). SAINT-Plus and SMART. 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., Zargaran, P., Ghammamy, S. & Eshtiagh-Hosseini, H. (2010). Acta Cryst. E66, o3357.
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds