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Volume 69 
Part 12 
Page o1759  
December 2013  

Received 22 October 2013
Accepted 6 November 2013
Online 9 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.077
wR = 0.195
Data-to-parameter ratio = 12.2
Details
Open access

N,N'-Dimethyl-N''-(trichloroacet­yl)phospho­ramide

aDepartment of Inorganic Chemistry, Kiev National Taras Shevchenko University, Vladimirskaya St. 64/13, Kiev 01601, Ukraine
Correspondence e-mail: ovchynnikov@univ.kiev.ua

In the title compound, C4H9Cl3N3O2P or CCl3C(O)NHP(O)(NHCH3)2, the P atom has a strongly distorted tetra­hedral geometry due to the formation of intermolecular strong hydrogen bonds involving the N atoms. In the crystal, N-H...O=P and N-H...O=C hydrogen bonds connect the mol­ecules into a two-dimensional array parallel to (100). An intra­molecular P...O contact [P...O = 2.975 (3) Å] is observed. The CCl3 group is rotationally disordered, with occupancies of 0.60 (3) and 0.40 (3)

Related literature

For the use of carbacyl­amido­phosphates as potential new ligands for metal ions, see: Skopenko et al. (2004[Skopenko, V., Amirkhanov, V., Silva, T., Vasilchenko, I., Anpilova, E. & Garnovskii, A. (2004). Usp. Khim. 73, 797-814.]); Znovjyak et al. (2009[Znovjyak, K. O., Moroz, O. V., Ovchynnikov, V. A., Sliva, T. Yu., Shishkina, S. V. & Amirkhanov, V. M. (2009). Polyhedron, 28, 3731-3738.]); Yizhak et al. (2013[Yizhak, R., Znovjyak, K., Ovchynnikov, V., Sliva, T., Konovalova, I., Medviediev, V., Shishkin, O. & Amirkhanov, V. (2013). Polyhedron, 62, 293-299.]); Gubina et al. (2009[Gubina, K., Maslov, O., Trush, E., Trush, V., Ovchynnikov, V., Shishkina, S. & Amirkhanov, V. (2009). Polyhedron, 28, 2661-2666.]). For their biological activity, see: Amirkhanov et al. (1996[Amirkhanov, V., Ovchynnikov, V., Legendziewicz, J., Graczyk, A., Hanuza, J. & Masalik, L. (1996). Acta Phys. Pol. A, 90, 455-460.]); Rebrova et al. (1984[Rebrova, O. H., Biyushkin, V. N., Malinovskiy, T. I., Procenko, L. D. & Dneprova, T. N. (1984). Dokl. Akad. Nauk SSSR, 274, 328-332.]). For P=O and C=O bond lengths, see: Mizrahi & Modro (1982[Mizrahi, V. & Modro, T. (1982). Cryst. Struct. Commun. 11, 627-631.]); Amirkhanov et al. (1997[Amirkhanov, V., Ovchynnikov, V., Glowiak, T. & Kozlowski, H. (1997). Z. Naturforsch. Teil B, 52, 1331-1336.]); Gubina & Amirkhanov (2000[Gubina, K. & Amirkhanov, V. (2000). Z. Naturforsch. Teil B, 55, 1015-1019.]). For the preparation of tri­chloro­acetyl­amido­phospho­ric acid dichloranhydride, see: Kirsanov & Derkach (1956[Kirsanov, A. & Derkach, G. (1956). Zh. Obshch. Khim. 26, 2009-2014.]).

[Scheme 1]

Experimental

Crystal data
  • C4H9Cl3N3O2P

  • Mr = 268.46

  • Monoclinic, P 21 /c

  • a = 10.231 (2) Å

  • b = 8.754 (2) Å

  • c = 12.826 (3) Å

  • [beta] = 101.27 (3)°

  • V = 1126.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.93 mm-1

  • T = 293 K

  • 0.4 × 0.3 × 0.3 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 3806 measured reflections

  • 1908 independent reflections

  • 1419 reflections with I > 2[sigma](I)

  • Rint = 0.060

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.195

  • S = 1.08

  • 1908 reflections

  • 157 parameters

  • 33 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.82 e Å-3

  • [Delta][rho]min = -0.77 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.81 (3) 2.00 (4) 2.782 (5) 164 (5)
N3-H3...O1i 0.81 (3) 2.21 (4) 2.953 (4) 153 (4)
N2-H2...O2ii 0.81 (3) 2.38 (4) 3.077 (5) 146 (6)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y, -z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1995[Enraf-Nonius (1995). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2520 ).


References

Amirkhanov, V., Ovchynnikov, V., Glowiak, T. & Kozlowski, H. (1997). Z. Naturforsch. Teil B, 52, 1331-1336.  [ChemPort]
Amirkhanov, V., Ovchynnikov, V., Legendziewicz, J., Graczyk, A., Hanuza, J. & Masalik, L. (1996). Acta Phys. Pol. A, 90, 455-460.  [ChemPort]
Enraf-Nonius (1995). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gubina, K. & Amirkhanov, V. (2000). Z. Naturforsch. Teil B, 55, 1015-1019.  [ChemPort]
Gubina, K., Maslov, O., Trush, E., Trush, V., Ovchynnikov, V., Shishkina, S. & Amirkhanov, V. (2009). Polyhedron, 28, 2661-2666.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
Kirsanov, A. & Derkach, G. (1956). Zh. Obshch. Khim. 26, 2009-2014.  [ChemPort]
Mizrahi, V. & Modro, T. (1982). Cryst. Struct. Commun. 11, 627-631.  [ChemPort]
Rebrova, O. H., Biyushkin, V. N., Malinovskiy, T. I., Procenko, L. D. & Dneprova, T. N. (1984). Dokl. Akad. Nauk SSSR, 274, 328-332.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Skopenko, V., Amirkhanov, V., Silva, T., Vasilchenko, I., Anpilova, E. & Garnovskii, A. (2004). Usp. Khim. 73, 797-814.
Yizhak, R., Znovjyak, K., Ovchynnikov, V., Sliva, T., Konovalova, I., Medviediev, V., Shishkin, O. & Amirkhanov, V. (2013). Polyhedron, 62, 293-299.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Znovjyak, K. O., Moroz, O. V., Ovchynnikov, V. A., Sliva, T. Yu., Shishkina, S. V. & Amirkhanov, V. M. (2009). Polyhedron, 28, 3731-3738.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1759  [ doi:10.1107/S1600536813030389 ]

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