N,N′-Bis(2-chloro­benz­yl)-N′′-(2,2,2-trichloro­acet­yl)phospho­ric triamide

Pourayoubi, M.; Fadaei, H.; Parvez, M.

doi:10.1107/S1600536811027681

Volume 67
Part 8
Page o2046
August 2011

Received 24 June 2011
Accepted 11 July 2011
Online 16 July 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.053
wR = 0.129
Data-to-parameter ratio = 18.9
Details

N,N'-Bis(2-chlorobenzyl)-N''-(2,2,2-trichloroacetyl)phosphoric triamide

Mehrdad Pourayoubi,^a ^* Hassan Fadaei ^a and Masood Parvez ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

The P atom in the title compound, C₁₆H₁₅Cl₅N₃O₂P, exhibits a tetrahedral coordination geometry and the phosphoryl and carbonyl groups are anti with respect to one another. The dihedral angle between the benzene rings is 44.90 (15)°. One of the 2-chlorobenzylamido fragments is disordered over two sets of sites with occupancies of 0.8823 (17) and 0.1177 (17). In the crystal, adjacent molecules are linked via N-HO(P) and N-HO(C) hydrogen bonds into an extended chain running parallel to the a axis.

Related literature

For details of compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011). For bond lengths in related structures, see: Pourayoubi et al. (2011); Rudd et al. (1996).

Experimental

Crystal data

C₁₆H₁₅Cl₅N₃O₂P
M_r = 489.53
Triclinic, $[P \overline 1]$
a = 9.9789 (2) Å
b = 10.6058 (3) Å
c = 10.8386 (3) Å
= 75.8920 (13)°
= 72.2250 (15)°
= 69.6050 (15)°
V = 1011.66 (4) Å³
Z = 2
Mo K radiation
= 0.81 mm^-1
T = 173 K
0.18 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer with APEXII CCD detector
Absorption correction: multi-scan (SORTAV; Blessing, 1997) T_min = 0.867, T_max = 0.909
8947 measured reflections
4638 independent reflections
4083 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.129
S = 1.05
4638 reflections
245 parameters
H-atom parameters constrained
_max = 1.42 e Å^-3
_min = -0.68 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.88	1.94	2.804 (3)	168
N2-H2O1ⁱⁱ	0.88	2.38	3.106 (3)	141
N2'-H2'O1	0.88	2.42	3.025 (3)	126
N3-H3O1ⁱⁱ	0.88	2.34	3.129 (3)	149
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+2, -y, -z+2.

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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: SJ5176 ).

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.
Hooft, R. (1998). COLLECT. Nonius BV, Delft. The Netherlands.
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.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.
Rudd, M. D., Lindeman, S. V. & Husebye, S. (1996). Acta Chem. Scand. 50, 759-774.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Toghraee, M., Pourayoubi, M. & Divjakovic, V. (2011). Polyhedron, 30, 1680-1690.

organic compounds