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Volume 69 
Part 8 
Page o1326  
August 2013  

Received 30 June 2013
Accepted 22 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.009 Å
R = 0.060
wR = 0.069
Data-to-parameter ratio = 8.4
Details
Open access

2-[4-(2-Chloroacetyl)phenyl]-2-methyl-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

The asymmetric unit of the title compound, C16H20ClNO2, contains two molecules in which the dihedral angles between the benzene ring and the plane of the amide unit are 77.4 (1) and 81.1 (1)°. In both molecules, the five-membered ring adopts an envelope conformation with one of the [beta]-C atoms as the flap. In the crystal, molecules are connected via C-H...O hydrogen bonds, forming chains along the b-axis direction. These chains are further linked by C-H...[pi] interactions, forming a three-dimensional network.

Related literature

For background to applications of the title compound, see: Krauss et al. (2001[Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (2001). US Patent No. 6242606.]). For the synthetic procedure of the title compound, see: Krauss et al. (1995[Krauss, R. C., Strom, R. M., Scortichini, C. L., Kruper, W. J. & Wolf, R. A. (1995). WO Patent No. 9500480.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20ClNO2

  • Mr = 293.78

  • Monoclinic, P c

  • a = 8.7380 (17) Å

  • b = 6.1660 (12) Å

  • c = 28.670 (6) Å

  • [beta] = 95.95 (3)°

  • V = 1536.4 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 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 = 0.929, Tmax = 0.976

  • 5766 measured reflections

  • 3048 independent reflections

  • 1538 reflections with I > 2[sigma](I)

  • Rint = 0.093

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.069

  • S = 0.92

  • 3048 reflections

  • 361 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 200 Friedel pairs

  • Absolute structure parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C9-C14 and C25-C30 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C4-H4A...O1i 0.97 2.53 3.427 (9) 153
C32-H32B...O1i 0.97 2.35 3.136 (8) 138
C18-H18B...Cg4ii 0.97 2.73 3.448 (7) 131
C4-H4B...Cg2 0.97 2.89 3.728 (9) 145
C23-H23B...Cg2iii 0.96 2.98 3.932 (6) 171
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) [x, -y+1, 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: SHELXS97 (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: VM2196 ).


Acknowledgements

This study was supported financially by the Scientific Research Project of Beijing Education Commission and the Scientific Research Level Project of Beijing Education Commission Foundation. The author thanks the Center of Testing and Analysis, Beijing University of Science and Technology, for the data collection.

References

Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
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.
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]


Acta Cryst (2013). E69, o1326  [ doi:10.1107/S1600536813020175 ]

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