Received 30 March 2013
The asymmetric unit of the title compound, C21H21Cl2NO2, contains two independent molecules that show similar geometrical features. The piperidine ring adopts a distorted boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring are oriented at angles of 65.4 (1) [64.7 (2)°] and 89.2 (1)° [86.3 (2)°] with respect to the least-squares plane of the piperidine ring. In the crystal, adjacent molecules are linked by a network of C-HO interactions, forming a C(6) chain along the c-axis direction.
For the biological activity of piperidine derivatives, see: Aridoss et al. (2009); Nalanishi et al. (1974); Michael (2001); Pinder (1992); Rubiralta et al. (1991). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5321 ).
PS thanks the UGC, New Delhi, for financial support in the form of a Research Fellowship in Science for Meritorious Students. SP thanks the UGC, New Delhi, for financial assistance in the form of a major research project.
Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577-592.
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Michael, J. P. (2001). The Alkaloids. Chemistry and Biology, edited by G. A. Cordell, Vol. 55, pp. 91-258. New York: Academic Press.
Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Jpn Patent No. 74-3987.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.
Rubiralta, M., Giralt, E. & Diez, A. (1991). Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives. pp. 225-312. Amsterdam: Elsevier.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.