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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 [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.090
Data-to-parameter ratio = 32.2
Details
Open access

Dichlorophosphinic bis(2-chloroethyl)amide

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

[Scheme 1]

Experimental

Crystal data
  • C4H8Cl4NOP

  • Mr = 258.88

  • Monoclinic, P 21 /c

  • a = 9.0723 (15) Å

  • b = 8.4810 (14) Å

  • c = 13.135 (2) Å

  • [beta] = 101.221 (2)°

  • V = 991.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.819, Tmax = 0.881

  • 9480 measured reflections

  • 3255 independent reflections

  • 2725 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.090

  • S = 1.05

  • 3255 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.57 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

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


Acta Cryst (2013). E69, o33  [ doi:10.1107/S1600536812049586 ]

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