Ethyl 1-[2-(1H-benzotriazol-1-yl)acet­yl]-4-hy­droxy-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

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

doi:10.1107/S1600536811020241

. 2011 Jun 4;67(Pt 7):o1574. doi: 10.1107/S1600536811020241

Ethyl 1-[2-(1H-benzotriazol-1-yl)acetyl]-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: PMC3151759 PMID: 21836985

Abstract

In the title compound, C₂₈H₂₆N₄O₄, the tetrahydropyridine ring adopts a boat conformation. The two phenyl rings form dihedral angles of 88.64 (8) and 59.28 (10)° with the best plane through the tetrahydropyridine ring. The dihedral angle between the two phenyl rings is 82.55 (10)°. The benzotriazole ring system is essentially planar, with a maximum deviation of 0.009 (1) Å from the least-squares plane. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) motif.

Related literature

For the synthesis and medicinal properties of piperidin-4-one-based amides, see: Aridoss et al. (2010a ▶). For related structures see: Aridoss et al. (2010a ▶, 2010b ▶, 2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₂₈H₂₆N₄O₄
M _r = 482.53
Monoclinic,
a = 7.9214 (2) Å
b = 21.9667 (6) Å
c = 14.5621 (4) Å
β = 95.722 (2)°
V = 2521.28 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.978, T _max = 0.981
24470 measured reflections
6280 independent reflections
4096 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.128
S = 1.04
6280 reflections
326 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 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 datablock(s) global, I. DOI: 10.1107/S1600536811020241/bt5557sup1.cif

e-67-o1574-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020241/bt5557Isup2.hkl

e-67-o1574-Isup2.hkl^{(301.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020241/bt5557Isup3.cml

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
O2—H2⋯O3	0.82	1.90	2.605 (2)	143

Open in a new tab

Acknowledgments

This research work was supported by the second stage of the BK-21 program. 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

In continuation of our interest on the conformation and crystal studies of piperidin-4-one based amides (Aridoss et al. 2010a, 2010b, 2011), we are reporting herewith the crystal structure of the title compound.

The molecular structure of compound (I) is illustrated in Fig.1. The sum of the bond angles around the atom N1 [358.77 (32)°] of the tetrahydropyridine ring in the molecule is in accordance with sp² hybridization. The two phenyl rings form dihedral angles of 88.64 (8) and 59.28 (10)° with the best plane through the tetrahydropyridine ring. The benzotriazole ring system is essentially planar with a maximum deviation of 0.009 (1)Å from the least squares plane. The ethyl acetate group shows an extended conformation [C26—O4—C27—C28 = 82.2 (2)°].

In the present structure tetrahydropyridine ring adopts a boat conformation with atoms C2 and C5 deviating by -0.316 (2) and -0.315 (1) Å, respectively from the least squares plane defined by the remaining atoms N1/C1/C3/C4 in the ring. The puckering parameters (Cremer & Pople, 1975) are Q = 0.5478 (16) Å; Θ = 90.33 (16) and Φ = 123.49 (16)°. The molecular structure is stabilized by a strong O—H···O hydrogen bond, wherein, atom O2 acts as a donor to O3, generating an S (6) motif.

Experimental

The title compound was prepared from N-bromoacetyl-3-carboxyethyl -2,6-diphenyl-4-hydroxy-Δ³-tetrahydropyridine and benzotriazole according to the literature method (Aridoss et al., 2010a). Slow evaporation of the ethanolic solution of the target compound at room temperature gave fine white crystals suitable for X-ray studies.