1-Dichloro­acetyl-r-2,c-6-bis­(4-methoxy­phen­yl)-c-3,t-3-dimethyl­piperidin-4-one

Thenmozhi, M.; Ponnuswamy, S.; Mohanraj, V.; Vijayalakshmi, R.; Ponnuswamy, M.N.

doi:10.1107/S1600536808040063

Volume 65
Part 1
Page o11
January 2009

Received 15 November 2008
Accepted 27 November 2008
Online 3 December 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.056
wR = 0.184
Data-to-parameter ratio = 25.1
Details

1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-c-3,t-3-dimethylpiperidin-4-one

M. Thenmozhi,^a S. Ponnuswamy,^b V. Mohanraj,^b R. Vijayalakshmi ^c and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India,^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India, and ^cDepartment of Chemistry, Queen Mary's College (Autonomous), Chennai 600 004, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C₂₃H₂₅Cl₂NO₄, the piperidine ring adopts a distorted boat conformation. Inversion-related molecules are linked into centrosymmetric R₂²(16) dimers by paired C-HO hydrogen bonds, and the dimers are connected via C-HO hydrogen bonds into a chain running along [101].

Related literature

For general background, see: Eller et al.(2002); Ribeiro da Silva et al. (2007). For hybridization, see: Beddoes et al. (1986) For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₂₃H₂₅Cl₂NO₄
M_r = 450.34
Monoclinic, C 2/c
a = 23.6295 (9) Å
b = 10.3999 (4) Å
c = 19.2617 (9) Å
= 107.734 (1)°
V = 4508.5 (3) Å³
Z = 8
Mo K radiation
= 0.32 mm^-1
T = 293 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.911, T_max = 0.939
29354 measured reflections
6905 independent reflections
4138 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.184
S = 1.00
6905 reflections
275 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.63 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.98	2.30	3.216 (2)	155
C13-H13O3ⁱⁱ	0.93	2.58	3.453 (3)	155
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2726 ).

Acknowledgements

SP thanks the UGC, India, for financial support.

References

Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Eller, K., Henkes, E., Rossbacher, R. & Hoke, H. (2002). Amines, Aliphatic, in Ullmann's Encyclopedia of Industrial Chemistry, Vol. 1, p. 379. Weinheim: Wiley-VCH Verlag.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Ribeiro da Silva, M. A. V. & Cabral, J. I. T. A. (2007). J. Therm. Anal. Calorim. 90, 865-871.
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds