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Volume 69 
Part 10 
Page o1529  
October 2013  

Received 4 September 2013
Accepted 6 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.068
wR = 0.231
Data-to-parameter ratio = 16.8
Details
Open access

Ethyl N-(2-acetyl-3-oxo-1-phenylbutyl)carbamate

aA. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Leninsky prospect 31, Moscow 119071, Russian Federation
Correspondence e-mail: alex123.87@mail.ru

In the title compound, C15H19NO4, all three carbonyl groups are syn-oriented with respect to the methine group attached to the phenyl ring. The mean planes of the phenyl ring and ethyl carbamate moiety form a dihedral angle of 65.2 (1)°. In the crystal, molecules related by translation in [100] are linked into chains via N-H...O hydrogen bonds.

Related literature

For details of the synthesis, see: Kuzmina et al. (2013[Kuzmina, O. M., Volov, A. N., Albov, D. V., Fitch, A. N., Chernyshev, V. V., Shutalev, A. D., Tsivadze, A. Yu., Savinkina, E. V. & Zamilatskov, I. A. (2013). Tetrahedron Lett. Submitted.]). For the crystal structures of related compounds, see: Hatano et al. (2008[Hatano, M., Maki, T., Moriyama, M., Arinobe, M. & Ishihara, K. (2008). J. Am. Chem. Soc. 130, 16858-16860.]).

[Scheme 1]

Experimental

Crystal data
  • C15H19NO4

  • Mr = 277.31

  • Triclinic, [P \overline 1]

  • a = 5.392 (2) Å

  • b = 9.204 (2) Å

  • c = 15.841 (6) Å

  • [alpha] = 81.58 (2)°

  • [beta] = 81.98 (2)°

  • [gamma] = 89.13 (3)°

  • V = 770.1 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.71 mm-1

  • T = 295 K

  • 0.50 × 0.21 × 0.10 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 = 0.76, Tmax = 0.92

  • 4976 measured reflections

  • 3176 independent reflections

  • 2057 reflections with I > 2[sigma](I)

  • Rint = 0.022

  • 2 standard reflections every 150 reflections intensity decay: 3%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.231

  • S = 1.04

  • 3176 reflections

  • 189 parameters

  • 15 restraints

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.97 (3) 2.26 (3) 3.180 (4) 158 (2)
Symmetry code: (i) x+1, y, z.

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, 1995[Harms, K. & Wocadlo, S. (1995). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2414 ).


References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Hatano, M., Maki, T., Moriyama, M., Arinobe, M. & Ishihara, K. (2008). J. Am. Chem. Soc. 130, 16858-16860.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Kuzmina, O. M., Volov, A. N., Albov, D. V., Fitch, A. N., Chernyshev, V. V., Shutalev, A. D., Tsivadze, A. Yu., Savinkina, E. V. & Zamilatskov, I. A. (2013). Tetrahedron Lett. Submitted.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1529  [ doi:10.1107/S1600536813024884 ]

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