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

Mehr-un-Nisa; Munawar, M.A.; Hall, G.B.; Roberts, S.A.; Hruby, V.J.

doi:10.1107/S1600536812051896

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 (C-C) = 0.001 Å
R = 0.034
wR = 0.079
Data-to-parameter ratio = 65.3
Details

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

Mehr-un-Nisa,^a Munawar Ali Munawar,^a Gabriel B. Hall,^b Sue A. Roberts ^b ^* and Victor J. Hruby ^b

^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-HO and C-HO 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); Joergen et al. (1997); Peter et al. (2009). For the synthesis of the title compound, see: Vardanyan et al. (2009).

Experimental

Crystal data

C₁₆H₂₂Cl₂N₂O₂
M_r = 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 radiation
= 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) T_min = 0.662, T_max = 0.749
34136 measured reflections
13197 independent reflections
11079 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.079
S = 1.00
13197 reflections
202 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.19 e Å^-3
Absolute structure: Flack (1983), 6110 Friedel pairs
Flack parameter: -0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.88	2.12	2.9740 (8)	163
C3-H3O2ⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds