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Volume 69 
Part 4 
Page o505  
April 2013  

Received 29 January 2013
Accepted 1 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.051
wR = 0.149
Data-to-parameter ratio = 19.0
Details
Open access

2-(2-Chlorophenyl)-N-cyclohexyl-2-oxoacetamide

aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
Correspondence e-mail: wyz@zju.edu.cn

In the title compound, C14H16ClNO2, the cyclohexyl ring has a chair conformation. The dihedral angle between the benzene ring and the mean plane of the four planar C atoms of the cyclohexyl ring is 45.2 (3)°. The two carbonyl groups are trans to one another, with an O=C-C=O torsion angle of -137.1 (3)°. In the crystal, molecules are linked by N-H...O hydrogen bonds forming chains propagating along [001]. A region of disordered electron density, situated near the unit-cell corners, was treated using the SQUEEZE routine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. It gave a solvent-accessible void of ca 400 Å3 for only 21 electrons. It is probably due to traces of the solvent of crystallization and was not taken into account during structure refinement.

Related literature

For the crystal structures of substituted phenylglyoxamides, see: Boryczka et al. (1998[Boryczka, S., Suwinska, K., Le Guillanton, G., Do, Q. T. & Elothmani, D. (1998). J. Chem. Crystallogr. 28, 555-560.]); Dai & Wu (2011[Dai, J. & Wu, J.-L. (2011). Acta Cryst. E67, o3152.]); Jia & Wu (2012[Jia, Z.-J. & Wu, J.-L. (2012). Acta Cryst. E68, o1948.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16ClNO2

  • Mr = 265.73

  • Hexagonal, P 61

  • a = 17.075 (3) Å

  • c = 9.4536 (13) Å

  • V = 2387.0 (7) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 293 K

  • 0.48 × 0.26 × 0.20 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO CCD and CrysAlis PRO RED. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.896, Tmax = 0.955

  • 15794 measured reflections

  • 3101 independent reflections

  • 2344 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.149

  • S = 1.01

  • 3101 reflections

  • 163 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1422 Friedel pairs

  • Flack parameter: -0.05 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.86 2.07 2.864 (3) 153
Symmetry code: (i) [-x+1, -y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO CCD and CrysAlis PRO RED. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2558 ).


Acknowledgements

The authors gratefully acknowledge Mr Jiyong Liu and Jianming Gu of Zhejiang University for their assistance with the crystal structure analysis and useful dicussions.

References

Agilent (2011). CrysAlis PRO CCD and CrysAlis PRO RED. Agilent Technologies Ltd, Yarnton, England.
Boryczka, S., Suwinska, K., Le Guillanton, G., Do, Q. T. & Elothmani, D. (1998). J. Chem. Crystallogr. 28, 555-560.  [ISI] [CSD] [CrossRef] [ChemPort]
Dai, J. & Wu, J.-L. (2011). Acta Cryst. E67, o3152.  [CSD] [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Jia, Z.-J. & Wu, J.-L. (2012). Acta Cryst. E68, o1948.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o505  [ doi:10.1107/S1600536813005904 ]

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