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Volume 69 
Part 5 
Page o773  
May 2013  

Received 21 March 2013
Accepted 11 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.063
wR = 0.152
Data-to-parameter ratio = 15.5
Details
Open access

2-Methyl-2-phenyl-1-(pyrrolidin-1-yl)propan-1-one

aSecurity and Environment Engineering College, Capital University of Economics and Business, Beijing 10070, People's Republic of China
Correspondence e-mail: nanoren@126.com

In the title compound, C14H19NO, the dihedral angle between the benzene ring and the plane of the amide group is 80.6 (1)°. In the crystal, molecules are connected via weak C-H...O hydrogen bonds, forming chains along the c-axis direction. The conformation of the five-memebred ring is an envelope, with one of the ring C atoms adjacent to the ring N atom as the flap atom.

Related literature

For background to the applications of the title compound as an intermediate in organic synthesis, an important organic synthesis intermediate, see: Richard et al. (2001[Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (1995). WO Patent No. 9500480.]). For the synthetic procedure, see: Richard et al. (1995[Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (2001). US Patent No. 6242606.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H19NO

  • Mr = 217.30

  • Monoclinic, P 21 /c

  • a = 8.2330 (16) Å

  • b = 12.534 (3) Å

  • c = 12.192 (2) Å

  • [beta] = 97.96 (3)°

  • V = 1246.0 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 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 = 0.979, Tmax = 0.993

  • 2283 measured reflections

  • 2283 independent reflections

  • 1316 reflections with I > 2[sigma](I)

  • Rint = 0.000

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.152

  • S = 1.00

  • 2283 reflections

  • 147 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...O1i 0.97 2.58 3.510 (4) 160
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2384 ).


Acknowledgements

This study was financially supported by Scientific Research Project of Beijing Education Commission and the Scientific Research Level Project of Beijing Education Commission Foundation. The authors thank the Center of Testing and Analysis, Beijing University of Science and Technology.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (1995). WO Patent No. 9500480.
Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (2001). US Patent No. 6242606.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o773  [ doi:10.1107/S1600536813009975 ]

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