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

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

doi:10.1107/S1600536808016449

. 2008 Jun 7;64(Pt 7):o1211. doi: 10.1107/S1600536808016449

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

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

PMCID: PMC2961741 PMID: 21202850

Abstract

In the title molecule, C₂₆H₂₈N₂O₃, 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 80.72 (15)°. The benzyl group at position 3 has an equatorial orientation. The oxime group at position 4 has a bisectional orientation. The ring of the benzyl group makes dihedral angles of 64.71 (16) and 84.79 (17)° with the two benzene rings. Molecules are linked by intermolecular N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, and C—H⋯π interactions. There is also a C—H⋯O intramolecular interaction.

Related literature

For related literature, see: Jayabharathi et al. (2007 ▶); Thiruvalluvar et al. (2007 ▶).

Experimental

Crystal data

C₂₆H₂₈N₂O₃
M _r = 416.50
Orthorhombic,
a = 10.2472 (4) Å
b = 11.2723 (4) Å
c = 38.4188 (15) Å
V = 4437.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 160 (1) K
0.25 × 0.13 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
36542 measured reflections
3910 independent reflections
2305 reflections with I > 2σ(I)
R _int = 0.092

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.211
S = 1.08
3910 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.75 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016449/wn2266sup1.cif

e-64-o1211-sup1.cif^{(29.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016449/wn2266Isup2.hkl

e-64-o1211-Isup2.hkl^{(187.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of rings C31–C36 and C21–C26, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6ⁱ	0.97 (3)	2.52 (3)	3.348 (3)	144 (2)
O4—H4⋯N1ⁱⁱ	0.84	2.01	2.818 (3)	160
C5—H5A⋯O4	0.99	2.27	2.705 (4)	105
C65—H65⋯O4ⁱⁱⁱ	0.95	2.43	3.334 (4)	158
C12—H12B⋯Cg1^iv	0.98	2.89	3.314 (4)	107
C16—H16A⋯Cg2ⁱ	0.98	2.65	3.598 (4)	162

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

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].

supplementary crystallographic information

Comment

In a wide research program toward new and efficient antimicrobial agents, a series of t3-benzyl-r2,c6-diarylpiperidin-4-ones have been synthesized and tested for their in vitro antibacterial and antifungal activities (Jayabharathi et al., 2007). Thiruvalluvar et al. (2007) have reported the crystal structure of t3-benzyl-1-formyl-r2,c-6-diphenylpiperidin-4-one, in which the piperidine ring is in a distorted boat form.

In the title compound, (Fig. 1), 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 80.72 (15)°. The benzyl group at position 3 has an equatorial orientation. The oxime group at position 4 has a bisectional orientation. The phenyl ring of the benzyl group makes a dihedral angle of 64.71 (16)° with the benzene ring at C2, and 84.79 (17)° with the benzene ring at C6. Molecules are linked by intermolecular N1—H1···O6, O4—H4···N1 and C65—H65···O4 hydrogen bonds (Fig. 2). There are C12—H12B···π (-1 + x, y, z) interactions involving the phenyl ring at C13 and C16—H16A···π (1 - x, 1 - y, -z) interactions involving the benzene ring at C2. There is also a C5—H5A···O4 intramolecular interaction.

Experimental

The title compound was prepared according to the literature procedure (Jayabharathi et al., 2007). t3-Benzyl-r2,c6-bis(p-methoxyphenyl)piperidin-4-one (ca 0.05 mol, 20 g) and sodium acetate trihydrate (0.15 mol, 20.41 g) were dissolved in boiling ethanol and hydroxylamine hydrochloride (0.06 mol, 4.17 g) was added. The mixture was heated to 313 K and stirred for 3-4 h. It was allowed to stand overnight and then poured into crushed ice. The separated solid was filtered off and recrystallized from ethanol. The yield of the isolated pure product was 16 g (80%).