t-3-Benzyl-r-2,c-6-bis­(4-methoxy­phen­yl)­piperidin-4-one

Jayabharathi, J.; Thangamani, A.; Balamurugan, S.; Thiruvalluvar, A.; Linden, A.

doi:10.1107/S1600536808015717

Volume 64
Part 7
Page o1181
July 2008

Received 22 May 2008
Accepted 25 May 2008
Online 7 June 2008

Key indicators
Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.003 Å
R = 0.054
wR = 0.177
Data-to-parameter ratio = 17.2
Details

t-3-Benzyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one

J. Jayabharathi,^a A. Thangamani,^a S. Balamurugan,^b A. Thiruvalluvar ^b ^* and A. Linden ^c

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India,^bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, and ^cInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
Correspondence e-mail: athiru@vsnl.net

In the title compound, C₂₆H₂₇NO₃, the piperidine ring adopts a chair conformation. The two methoxyphenyl groups attached to the piperidine ring at positions 2 and 6 have equatorial orientations and make a dihedral angle of 87.33 (8)°. The benzyl group at position 3 has an equatorial orientation. The phenyl ring of the benzyl group makes dihedral angles of 75.60 (9) and 73.69 (9)° with the two benzene rings. Molecules are linked by intermolecular N-HO and C-HO hydrogen bonds and by C-H [pi] interactions.

Related literature

For related literature, see: Jayabharathi et al. (2007); Thiruvalluvar et al. (2007); Noller & Baliah (1948).

Experimental

Crystal data

C₂₆H₂₇NO₃
M_r = 401.49
Triclinic, $[P \overline 1]$
a = 5.5612 (2) Å
b = 13.8097 (5) Å
c = 14.5119 (6) Å
= 71.629 (2)°
= 79.928 (2)°
= 82.526 (2)°
V = 1038.04 (7) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 160 (1) K
0.30 × 0.18 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
25390 measured reflections
4740 independent reflections
3325 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.177
S = 1.09
4740 reflections
275 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.92 (2)	2.56 (2)	3.420 (2)	154.9 (14)
C5-H5BO4ⁱⁱ	0.99	2.51	3.490 (2)	173
C16-H16BCg1ⁱⁱⁱ	0.98	2.85	3.659 (2)	140
C16-H16CCg2^iv	0.98	2.98	3.587 (2)	121
C34-H34Cg3^v	0.95	2.91	3.719 (2)	144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x+2, -y+1, -z; (v) -x, -y+1, -z+1. Cg1, Cg2 and Cg3 are the centroids of the C61-C66, C31-C36 and C21-26 rings, respectively.

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); 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: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2265 ).

Acknowledgements

AT thanks the UGC, India, for the award of a Minor Research Project [file No. MRP-2355/06(UGC-SERO), link No. 2355, 10/01/2007].

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Jayabharathi, J., Manimekalai, A., Consalata Vani, T. & Padmavathy, M. (2007). Eur. J. Med. Chem. 42, 593-605.
Noller, C. R. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853-3855.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. London: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Thiruvalluvar, A., Balamurugan, S., Butcher, R. J., Manimekalai, A. & Jayabharathi, J. (2007). Acta Cryst. E63, o4533.

organic compounds