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Volume 69 
Part 7 
Pages o1188-o1189  
July 2013  

Received 30 May 2013
Accepted 26 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](O-C) = 0.004 Å
R = 0.048
wR = 0.133
Data-to-parameter ratio = 14.0
Details
Open access

Methyl N-(dimethoxyphosphoryl)carbamate

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, CH3OC(O)NHP(O)(OCH3)2, the P atom has a slightly distorted tetrahedral configuration. The mixed imide moiety can be described as cisoid-transoid in which the two opposing dipoles (P=O and C=O) are oriented with a O=C...P=O torsion angle of 150.88(18)°. In the crystal, molecules are linked by pairs of N-H...O hydrogen bonds, forming inversion dimers.

Related literature

For the use of phosphorylated carbamides as potential new ligands, see: Safin et al. (2009[Safin, D. A., Bolte, M., Shakirova, E. R. & Babashkina, M. G. (2009). Polyhedron, 28, 501-501.]); 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.]); Sokolov et al. (2008[Sokolov, F. D., Brusko, V. V., Safin, D. A., Cherkasov, R. A. & Zabirov, N. G. (2008). Transition Metal Chemistry: New Research, edited by B. Varga & L. Kis, pp. 101-150. Hauppauge, NY: Nova Science Publishers Inc.]). 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.]); Tsibulskaya & Orlacheva (1956[Tsibulskaya, N. P. & Orlacheva, K. A. (1956). DAN UkrSSR, pp. 602-606.]). For P=O bond lengths, see: Mizrahi & Modro (1982[Mizrahi, V. & Modro, T. A. (1982). Cryst. Struct. Commun. 11, 627-631.]): Amirkhanov et al. (1997[Amirkhanov, V. M., Ovchynnikov, V. A., Glowiak, T. & Kozlowski, H. (1997). Z. Naturforsch. Teil B, 52, 1331-1336.]). For the synthesis of the title compound, see: Kirsanov & Marenetc (1959[Kirsanov, A. V. & Marenetc, M. C. (1959). Russ. J. Gen. Chem. 29, 2256-2262.]). For short O...O contacts see: Bianchi et al. (2000[Bianchi, R., Gervasio, G. & Marabello, D. (2000). Inorg. Chem. 39, 2360-2366.]); Zhurova et al. (2002[Zhurova, E. A., Tsirelson, V. G., Stash, A. I. & Pinkerton, A. A. (2002). J. Am. Chem. Soc. 124, 4574-4575.])

[Scheme 1]

Experimental

Crystal data
  • C4H10NO5P

  • Mr = 183.10

  • Triclinic, [P \overline 1]

  • a = 6.441 (1) Å

  • b = 7.018 (1) Å

  • c = 9.298 (2) Å

  • [alpha] = 99.05 (3)°

  • [beta] = 96.70 (3)°

  • [gamma] = 100.54 (3)°

  • V = 403.46 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.910, Tmax = 0.924

  • 1417 measured reflections

  • 1417 independent reflections

  • 1322 reflections with I > 2[sigma](I)

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.133

  • S = 1.04

  • 1417 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.74 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Selected geometric parameters (Å, °)

P1-O1 1.451 (2)
P1-O4 1.556 (2)
P1-O3 1.573 (2)
P1-O2 3.126 (2)
P1-N1 1.658 (2)
O2-O4 2.938 (3)
O1-P1-O4 117.63 (12)
O1-P1-O3 109.28 (13)
O4-P1-O3 101.56 (12)
O1-P1-N1 109.55 (12)
O4-P1-N1 108.84 (12)
O3-P1-N1 109.57 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.86 1.99 2.847 (3) 171
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). 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 (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: GG2115 ).


References

Amirkhanov, V. M., Ovchynnikov, V. A., 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]
Bianchi, R., Gervasio, G. & Marabello, D. (2000). Inorg. Chem. 39, 2360-2366.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Enraf-Nonius (1994). 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]
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
Kirsanov, A. V. & Marenetc, M. C. (1959). Russ. J. Gen. Chem. 29, 2256-2262.  [ChemPort]
Mizrahi, V. & Modro, T. A. (1982). Cryst. Struct. Commun. 11, 627-631.  [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
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]
Safin, D. A., Bolte, M., Shakirova, E. R. & Babashkina, M. G. (2009). Polyhedron, 28, 501-501.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sokolov, F. D., Brusko, V. V., Safin, D. A., Cherkasov, R. A. & Zabirov, N. G. (2008). Transition Metal Chemistry: New Research, edited by B. Varga & L. Kis, pp. 101-150. Hauppauge, NY: Nova Science Publishers Inc.
Tsibulskaya, N. P. & Orlacheva, K. A. (1956). DAN UkrSSR, pp. 602-606.
Zhurova, E. A., Tsirelson, V. G., Stash, A. I. & Pinkerton, A. A. (2002). J. Am. Chem. Soc. 124, 4574-4575.  [Web of Science] [CrossRef] [PubMed] [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, o1188-o1189   [ doi:10.1107/S1600536813017637 ]

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