(1-Acetyl-2,6-diphenyl­piperidin-4-yl­idene)(phen­yl)acetonitrile

A Manimekalai; A Balamurugan; S Balamurugan; A Thiruvalluvar; R J Butcher

doi:10.1107/S160053680800860X

. 2008 Apr 4;64(Pt 5):o797. doi: 10.1107/S160053680800860X

(1-Acetyl-2,6-diphenylpiperidin-4-ylidene)(phenyl)acetonitrile

A Manimekalai ^a, A Balamurugan ^a, S Balamurugan ^b, A Thiruvalluvar ^b,^*, R J Butcher ^c

PMCID: PMC2961162 PMID: 21202289

Abstract

In the title molecule, C₂₇H₂₄N₂O, the piperidine ring adopts a boat conformation. The acetyl group at position 1 has a bisectional orientation. The two phenyl rings attached to the piperidine ring at positions 2 and 6 have bisectional and axial orientations, respectively, and make a dihedral angle of 75.27 (10)°. The phenylacetonitrile group at position 4 has an equatorial orientation. Molecules are linked by C—H⋯N, C—H⋯O intermolecular and C—H⋯π interactions. A C—H⋯O intramolecular interaction is also found in the molecule.

Related literature

Thiruvalluvar et al. (2007 ▶) have reported the crystal structure of (2,6-diphenylpiperidin-4-ylidene)(phenyl)acetonitrile, in which the piperidine ring adopts a chair conformation.

Experimental

Crystal data

C₂₇H₂₄N₂O
M _r = 392.48
Triclinic,
a = 9.4034 (17) Å
b = 10.646 (6) Å
c = 10.8860 (18) Å
α = 90.45 (2)°
β = 99.957 (14)°
γ = 101.98 (3)°
V = 1048.9 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 200 (2) K
0.43 × 0.37 × 0.23 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: none
14102 measured reflections
6736 independent reflections
2238 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.150
S = 0.86
6736 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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/S160053680800860X/wn2248sup1.cif

e-64-0o797-sup1.cif^{(26.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800860X/wn2248Isup2.hkl

e-64-0o797-Isup2.hkl^{(323KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O11	1.00	2.21	2.723 (3)	110
C12—H12A⋯N16ⁱ	0.98	2.50	3.423 (3)	158
C42—H42⋯O11ⁱⁱ	0.95	2.58	3.398 (3)	145
C22—H22⋯Cg1	0.95	2.79	3.734 (3)	174
C26—H26⋯Cg2ⁱⁱⁱ	0.95	2.89	3.784 (3)	157

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C61–C66 and C41–C46 phenyl rings, respectively.

Acknowledgments

RJB acknowledges the NSF-MRI program for funding the purchase of the X-ray CCD diffractometer. 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 the title compound, (Fig. 1), the piperidine ring adopts a boat conformation. The acetyl group at position 1 has a bisectional orientation. The two phenyl rings attached to the piperidine ring at positions 2 and 6 have bisectional and axial orientations, respectively, and make a dihedral angle of 75.27 (10)°. The phenyl-acetonitrile group at position 4 has an equatorial orientation. Molecules are linked by intermolecular C12—H12A···N16, C42—H42···O11 and intramolecular C6—H6···O11 hydrogen bonds. There are C22—H22···π (x, y, z) interactions involving the phenyl ring at 6 and C26—H26···π (1 - x, -y, 2 - z) interactions involving the phenyl ring at C14.

Experimental

A mixture of (2,6-diphenylpiperidin-4-ylidene)(phenyl)acetonitrile (3.5 g, 0.01 mol), acetic anhydride (2.8 ml, 0.03 mol) and trimethylamine (4.2 ml, 0.03 mol) in benzene (50 ml) was refluxed for 8-10 h. The reaction mixture was cooled to room temperature and poured into ice-cold water. The solid mass was separated by filtration, dried and recrystallized from ethanol. The yield of the isolated product was 2.16 g (55%).