(IUCr) 1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one

Volume 65
Part 8
Page o1975
August 2009

Received 30 June 2009
Accepted 16 July 2009
Online 25 July 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.050
wR = 0.152
Data-to-parameter ratio = 23.4
Details

1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one

S. Aravindhan,^a S. Ponnuswamy,^b J. Umamaheswari,^b P. Ramesh ^c and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C₂₆H₂₅NO₂, the piperidine ring adopts a distorted boat conformation. The three phenyl rings form dihedral angles of 67.58 (8), 59.82 (8) and 86.41 (8)° with the best plane through the piperidine ring. The crystal packing is governed by intermolecular C-HO interactions.

Related literature

For the biological activity of piperidine derivatives, see: Dimmock et al. (2001); Perumal et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₂₆H₂₅NO₂
M_r = 383.47
Monoclinic, P 2₁ /c
a = 10.8540 (9) Å
b = 17.8050 (17) Å
c = 10.8853 (10) Å
= 94.987 (3)°
V = 2095.7 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 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 = 0.977, T_max = 0.985
27356 measured reflections
6189 independent reflections
3897 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.152
S = 0.98
6189 reflections
265 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1	0.98	2.29	2.7346 (17)	106
C2-H2O1ⁱ	0.98	2.56	3.3784 (17)	141
C20-H20AO1ⁱ	0.96	2.47	3.1885 (19)	132
C20-H20BO2ⁱⁱ	0.96	2.52	3.470 (2)	170
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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 (Farrugia, 1997); 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: BT2990 ).

Acknowledgements

SA thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

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.
Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santos, C. L., Balsarini, J., Clercq, E. D. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586-593.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Perumal, R. V., Agiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156-159.
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds