Ethyl 1-benzoyl-4-hy­droxy-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

G Aridoss; S Sundaramoorthy; D Velmurugan; Y T Jeong

doi:10.1107/S1600536811003266

. 2011 Feb 2;67(Pt 3):o540. doi: 10.1107/S1600536811003266

Ethyl 1-benzoyl-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

G Aridoss ^a, S Sundaramoorthy ^b, D Velmurugan ^b, Y T Jeong ^a,^*

PMCID: PMC3052159 PMID: 21522308

Abstract

In the title compound, C₂₇H₂₅NO₄, the tetrahydropyridine ring adopts a half-chair conformation. The three phenyl rings form dihedral angles of 66.33 (7), 87.36 (8) and 36.90 (7)° with the least-squares plane through the tetrahydropyridine ring. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) motif.

Related literature

For related structures, see: Subha Nandhini et al. (2003 ▶); Nithya et al. (2009 ▶); Aravindhan et al. (2009 ▶); Aridoss et al. (2009 ▶, 2010 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₂₇H₂₅NO₄
M _r = 427.48
Triclinic,
a = 8.2784 (7) Å
b = 10.6116 (9) Å
c = 12.7572 (11) Å
α = 85.681 (4)°
β = 89.963 (4)°
γ = 82.508 (5)°
V = 1107.91 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.979, T _max = 0.983
20295 measured reflections
5526 independent reflections
4179 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.120
S = 1.04
5526 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003266/is2669sup1.cif

e-67-0o540-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003266/is2669Isup2.hkl

e-67-0o540-Isup2.hkl^{(265.1KB, 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
O1—H1A⋯O2	0.82	1.85	2.570 (2)	146

Open in a new tab

Acknowledgments

This research was supported by the Industrial Technology Development Program, which was conducted by the Ministry of Knowledge Economy of the Korean Government. SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

supplementary crystallographic information

Comment

Owing to the relevance of piperidine-containing bioactive compounds, the development of new piperidine based derivatives continues to be a subject of considerable interest. The pharmacological effects of potential new drugs depend entirely on the stereochemistry and ring conformations of the compounds and hence the crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig. 1. The tetrahydropyridine ring adopts a half-chair conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for this ring are q₂ = 0.344 (1) Å, q₃ = -0.288 (1) Å; Q_T = 0.4485 Å and θ = 130.02 (2)°, φ₂ = 205.6 (2)°, respectively. The three phenyl rings are twisted away from the best plane of the tetrahydropyridine ring by 66.33 (7), 87.36 (8) and 36.90 (7)°, respectively. The sum of the bond angles around the atom N1 [360.09 (10)°] of the tetrahydropyridine ring in the molecule is in accordance with sp² hybridization. The ethyl acetate group shows an extended conformation [C18—O3—C19—C20 = 90.67 (2)°]. The molecular structure is stabilized by a strong O—H···O hydrogen bond, wherein, atom O1 acts as a donor to O2, generating an S(6) motif.

Experimental

To a mixture of 3-carboxyethyl-2,6-diphenylpiperidin-4-one (1 equiv.) and triethylamine (1.5 equiv.) in benzene, freshly distilled benzoyl chloride in benzene was added dropwise and stirred well at room temperature until completion. The crude mass obtained by the base work upon purification and recrystallization in distilled ethanol gave fine white crystals suitable for X-ray study.