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Volume 65 
Part 1 
Page o162  
January 2009  

Received 12 December 2008
Accepted 13 December 2008
Online 20 December 2008

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.147
Data-to-parameter ratio = 19.0
Details
Open access

N-(4-Chlorophenyl)-4-(2-oxocyclopentyl)butyramide

Lin-Tao Yu,a Jiang-Tao Weia and Xiang-Ge Zhoua*

aInstitute of Homogeneous Catalysis, Department of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
Correspondence e-mail: scuzhou106@yahoo.com.cn

In the title compound, C15H18ClNO2, the amide group is coplanar with the chlorophenyl group, making a dihedral angle of 1.71 (12)°. The cyclopentanone ring adopts a twist conformation. A weak intramolecular C-H...O hydrogen bond is observed. Molecules are linked into cyclic centrosymmetric dimers by paired N-H...O hydrogen bonds.

Related literature

For the synthesis of cyathin terpenoids, see: Drège et al. (2006[Drège, E., Tominiaux, C., Morgant, G. & Desmaële, D. (2006). Eur. J. Org. Chem. pp. 4825-4840.]).

[Scheme 1]

Experimental

Crystal data

  • C15H18ClNO2

  • Mr = 279.75

  • Triclinic, [P \overline 1]

  • a = 5.5897 (2) Å

  • b = 8.8847 (3) Å

  • c = 14.6480 (4) Å

  • [alpha] = 80.906 (2)°

  • [beta] = 86.436 (2)°

  • [gamma] = 85.351 (2)°

  • V = 715.05 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 296 (2) K

  • 0.42 × 0.40 × 0.20 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.895, Tmax = 0.948

  • 8899 measured reflections

  • 3273 independent reflections

  • 1648 reflections with I > 2[sigma](I)

  • Rint = 0.047
Refinement

  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.147

  • S = 1.01

  • 3273 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.86 2.17 2.980 (2) 158
C15-H15...O2 0.93 2.29 2.889 (2) 121
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2743 ).

Acknowledgements

The authors thank the NSFC (grant Nos. 20672075 and 20771076) and Sichuan University for financial support.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Drège, E., Tominiaux, C., Morgant, G. & Desmaële, D. (2006). Eur. J. Org. Chem. pp. 4825-4840.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2009). E65, o162  [ doi:10.1107/S1600536808042505 ]

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