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Volume 69 
Part 2 
Page o205  
February 2013  

Received 20 December 2012
Accepted 26 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.034
wR = 0.079
Data-to-parameter ratio = 65.3
Details
Open access

tert-Butyl 4-(3,4-dichloroanilino)piperidine-1-carboxylate

aInstitute of Chemistry, University of The Punjab, Qaid-i-Azam Campus, Lahore 54590, Pakistan, and bDepartment of Chemistry and Biochemistry, 1306 E University Boulevard, The University of Arizona, Tucson, AZ 85721, USA
Correspondence e-mail: suer@email.arizona.edu

In the title compound, C16H22Cl2N2O2, the substituted piperidine ring adopts a chair conformation with both substituents in equatorial positions. In the crystal, N-H...O and C-H...O hydrogen bonds connect molecules into ribbons along the a-axis direction.

Related literature

For the biological activity of piperazine derivatives, see: Hamed et al. (2012[Hamed, A., Christoph, B., Olivier, C., Bibia, H. & Romain, S. (2012). US Patent Appl. 2012316178.]); Joergen et al. (1997[Joergen, S.-K., Peter, M. & Frank, W. (1997). World Patent WO9730997.]); Peter et al. (2009[Peter, D., Eriksen, B. L., Munro, G. & Nielsen, E. (2009). World Patent WO 2009/077585.]). For the synthesis of the title compound, see: Vardanyan et al. (2009[Vardanyan, R., Vijay, G., Nichol, G. S., Liu, L., Kumarasinghe, I., Davis, P., Vanderah, T., Porreca, F., Lai, J. & Hruby, V. J. (2009). Bioorg. Med. Chem. 14, 5044-5053.]).

[Scheme 1]

Experimental

Crystal data
  • C16H22Cl2N2O2

  • Mr = 345.25

  • Orthorhombic, P 21 21 21

  • a = 9.7825 (6) Å

  • b = 10.6075 (6) Å

  • c = 16.8215 (10) Å

  • V = 1745.53 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 100 K

  • 0.40 × 0.40 × 0.30 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.662, Tmax = 0.749

  • 34136 measured reflections

  • 13197 independent reflections

  • 11079 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.079

  • S = 1.00

  • 13197 reflections

  • 202 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 6110 Friedel pairs

  • Flack parameter: -0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.88 2.12 2.9740 (8) 163
C3-H3...O2i 0.95 2.58 3.3486 (9) 138
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, 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: 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2529 ).


Acknowledgements

We gratefully acknowledge a grant from the Higher Education Commission of Pakistan under the IRSIP programme to support PhD students. The Bruker Kappa APEXII DUO was purchased with funding from NSF grant CHE-0741837. The work was supported in part by grants from the US Public Health Service and National Institutes of Health (DA06284 and DA13449).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Hamed, A., Christoph, B., Olivier, C., Bibia, H. & Romain, S. (2012). US Patent Appl. 2012316178.
Joergen, S.-K., Peter, M. & Frank, W. (1997). World Patent WO9730997.
Peter, D., Eriksen, B. L., Munro, G. & Nielsen, E. (2009). World Patent WO 2009/077585.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vardanyan, R., Vijay, G., Nichol, G. S., Liu, L., Kumarasinghe, I., Davis, P., Vanderah, T., Porreca, F., Lai, J. & Hruby, V. J. (2009). Bioorg. Med. Chem. 14, 5044-5053.  [CSD] [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o205  [ doi:10.1107/S1600536812051896 ]

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