(E)-3-Methyl-2,6-di­phenyl­piperidin-4-one O-(3-methyl­benzo­yl)oxime

V Kathiravan; K Gokula Krishnan; T Mohandas; V Thanikachalam; P Sakthivel

doi:10.1107/S1600536814016638

. 2014 Jul 31;70(Pt 8):o883. doi: 10.1107/S1600536814016638

(E)-3-Methyl-2,6-diphenylpiperidin-4-one O-(3-methylbenzoyl)oxime

V Kathiravan ^a, K Gokula Krishnan ^b, T Mohandas ^c, V Thanikachalam ^b, P Sakthivel ^d,^*

PMCID: PMC4158521 PMID: 25249925

Abstract

In the title compound, C₂₆H₂₆N₂O₂, the piperidine ring exhibits a chair conformation. The phenyl rings are attached to the central heterocycle in an equatorial position. The dihedral angle between the planes of the phenyl rings is 57.58 (8)°. In the crystal, C—H⋯O interactions connect the molecules into zigzag chains along [001].

Keywords: crystal structure, piperidinone, oxime, hydrogen bonding

Related literature

For the biological activity of oxime esters, see: Crichlow et al. (2007 ▶); Hwu et al. (2008 ▶); Neely et al. (2013 ▶); Liu et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For comparable structures, see: Park et al. (2012a ▶,b ▶).

Experimental

Crystal data

C₂₆H₂₆N₂O₂
M _r = 398.49
Monoclinic,
a = 10.6265 (6) Å
b = 12.7146 (7) Å
c = 16.4031 (8) Å
β = 99.524 (2)°
V = 2185.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.977, T _max = 0.985
37978 measured reflections
5367 independent reflections
3097 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.175
S = 1.04
5367 reflections
275 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT (Bruker, 2008 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016638/bt6984sup1.cif

e-70-0o883-sup1.cif^{(30.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016638/bt6984Isup2.hkl

e-70-0o883-Isup2.hkl^{(257.5KB, hkl)}

Click here for additional data file.^{(8.1KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814016638/bt6984Isup3.cml

CCDC reference: 1005453

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.59	3.485 (3)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Babu Varghese, Senior Scientific Officer SAIF, IIT Madras, India, for carrying out the data collection.

supplementary crystallographic information

S1. Comment

The chemistry of oxime esters are serving as important synthetic intermediate, and have been employed as starting materials for both synthetic and medicinal chemistry (Crichlow et al. 2007; Hwu et al.2008; Neely et al.2013). Oxime esters have received great potential in biologically active molecules such as agrochemical industries (Liu et al., 2011).

The central ring (N1/C7/C8/C9/C10/C11) adopts a chair conformation with the puckering parameters Q=0.5398 Å, θ=8.88° and φ=30.1509° (Cremer & Pople, 1975).

The bond distances and bond angles in the title compound agree very well with the corresponding values reported in closely related compounds (Park et al., 2012a,b).

This stucture was stabilized by C—H···O intramolecular interactions linking the molecules to zigzag chains running parallel to [001] axis.

S2. Experimental

A mixture of 3-methyl-2,6-diphenylpiperidin-4-one oxime (0.73 g, 2.5 mmol) and m-methylbenzoic acid (0.37 g, 2.75 mmol) in dry pyridine (7 ml) was stirred at ambient temperature. POCl₃ (0.25 ml, 2.75 mmol) was added drop wise to the reaction mixture and stirring is continued for 20 to 30 min. The progress of the reaction was monitored by TLC. After completion of the reaction, a saturated solution of NaHCO3 was added portion wise to the reaction mixture and the crude product was thrown out as a precipitate. The crude product was then recrystallized from absolute ethanol to get the pure 3-methyl-2,6-diphenylpiperidin-4-one-O-(3-methylbenzoyl) oxime. Yield 0.76 g (78%).