Dichloro­phosphinic bis­(2-chloro­eth­yl)amide

Song, E.; Song, Y.

doi:10.1107/S1600536812049586

Volume 69
Part 1
Page o33
January 2013

Received 29 October 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.029
wR = 0.090
Data-to-parameter ratio = 32.2
Details

Dichlorophosphinic bis(2-chloroethyl)amide

Erqun Song ^a and Yang Song ^a ^*

^aKey Laboratory of Luminescence and Real-Time Analysis, Ministry of Education, College of Pharmaceutical Sciences, Southwest University, Chong Qing 400716, People's Republic of China
Correspondence e-mail: ysong@swu.edu.cn

In the title compound, C₄H₈Cl₄NOP, the two chloroethyl groups are not related by crystallographic symmetry. The difference in the conformation of the two groups is shown by their N-C-C-Cl torsion angles of 64.57 (15) and 175.62 (10)°.

Related literature

The title compound is a precursor used in the synthesis of the antitumor drug cyclophosphamide and its analogues. For information on organophosphorus heterocyclic compounds, see: Surendra Babu et al. (2009); Srinivasulu et al. (2008); Krishna et al. (2006). For the crystal structures of cyclophosphamide analogues, see: Camerman & Camerman (1973); Jones et al. (1996); Himes et al. (1982); Camerman et al. (1983); Perales & García-Blanco (1977a,b); Galdecki & Glowka (1981); Boyd et al. (1980); Shih et al. (1986). For the pharmacological activity of cyclophosphamide analogues, see: Lin et al. (1980); Borch & Canute (1991).

Experimental

Crystal data

C₄H₈Cl₄NOP
M_r = 258.88
Monoclinic, P 2₁ /c
a = 9.0723 (15) Å
b = 8.4810 (14) Å
c = 13.135 (2) Å
= 101.221 (2)°
V = 991.4 (3) Å³
Z = 4
Mo K radiation
= 1.30 mm^-1
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.819, T_max = 0.881
9480 measured reflections
3255 independent reflections
2725 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.090
S = 1.05
3255 reflections
101 parameters
H-atom parameters constrained
_max = 0.57 e Å^-3
_min = -0.46 e Å^-3

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and local procedures.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2076 ).

Acknowledgements

This work was supported by the Program for New Century Excellent Talents in Universities (NCET-10-0660), the National Scientific & Technological Special Project - Major Creation of New Drugs (Nos. 2010ZX09401-306-1-4 and 2010ZX09401-306-2-19) and the 211 Project of Southwest University (the Third Term).

References

Borch, R. F. & Canute, G. W. (1991). J. Med. Chem. 34, 3044-3052.
Boyd, V. L., Zon, G. & Himes, V. L. (1980). J. Med. Chem. 23, 372-375.
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Camerman, N. & Camerman, A. (1973). J. Am. Chem. Soc. 95, 5038-5041.
Camerman, A., Smith, H. W. & Camerman, N. (1983). J. Med. Chem. 26, 679-683.
Galdecki, Z. & Glowka, M. L. (1981). Acta Cryst. B37, 1136-1138.
Himes, V. L., Mighell, A. D., Stalick, J. K. & Zon, G. (1982). Acta Cryst. B38, 1009-1012.
Jones, P. G., Thönnessen, H., Fischer, A., Neda, I., Schmutzler, R., Engel, J., Kutscher, B. & Niemeyer, U. (1996). Acta Cryst. C52, 2359-2363.
Krishna, J. R., Krishnaiah, M., Stephen Babu, M., Suresh Reddy, C. & Puranik, V. G. (2006). Acta Cryst. E62, o249-o250.
Lin, T. S., Fischer, P. H. & Prusoff, W. H. (1980). J. Med. Chem. 23, 1235-1237.
Perales, A. & García-Blanco, S. (1977a). Acta Cryst. B33, 1935-1939.
Perales, A. & García-Blanco, S. (1977b). Acta Cryst. B33, 1939-1943.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shih, Y. E. & Wang, J. S. (1986). Heterocycles, 24, 1599-1603.
Srinivasulu, K., Babu, B. H., Kumar, K. S., Reddy, C. B., Raju, C. N. & Rooba, D. (2008). J. Heterocycl. Chem. 45, 751-757.
Surendra Babu, V. H. H., Krishnaiah, M., Srinivasulu, K., Raju, C. N. & Sreedhar, B. (2009). Acta Cryst. E65, o2700-o2701.

organic compounds