Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfan­yl)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/S1600536811022744

. 2011 Jun 18;67(Pt 7):o1731. doi: 10.1107/S1600536811022744

Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfanyl)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: PMC3151913 PMID: 21837120

Abstract

In the title compound, C₂₉H₂₆N₂O₅S, the piperidine ring adopts a half-chair conformation. The phenyl rings are oriented at dihedral angles of 75.76 (12) and 86.64 (9)° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 30.81 (13)°. The benzoxazole ring system is approximately planar [maximum deviation = 0.016 (4) Å]. The atoms of the ethyl side chain are disordered over two sets of sites [site occupancies = 0.376 (9) and 0.624 (9)]. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) motif. The crystal packing is stabilized by intermolecular C—H⋯O interactions, generating a chain running along the a axis.

Related literature

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

Experimental

Crystal data

C₂₉H₂₆N₂O₅S
M _r = 514.58
Monoclinic,
a = 12.4630 (2) Å
b = 24.3243 (5) Å
c = 9.2350 (2) Å
β = 109.608 (1)°
V = 2637.28 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.23 × 0.2 × 0.18 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.963, T _max = 0.971
25589 measured reflections
6571 independent reflections
4020 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.128
S = 1.05
6571 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 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/S1600536811022744/lw2065sup1.cif

e-67-o1731-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022744/lw2065Isup2.hkl

e-67-o1731-Isup2.hkl^{(315.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811022744/lw2065Isup3.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
O1—H1A⋯O2	0.82	1.84	2.558 (2)	145
C13—H13⋯O2ⁱ	0.93	2.59	3.263 (2)	130

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Symmetry code: (i) Inline graphic .

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

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 = 0.3543 (18) Å, q3 = 0.2996 (18) Å, Q_T = 0.4639 (17)Å and θ = 49.8 (2)°, respectively. The phenyl rings are oriented at dihedral angles of 75.76 (12) and 86.64 (9)° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 30.81 (13)°. The sum of the bond angles around the atom N1 [359.49 (4)°] of the tetrahydropyridine ring in the molecule is in accordance with sp² hybridization.

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. The crystal packing is stabilized by C—H···O intermolecular interaction which links the molecules into chain running along the a axis.

Experimental

The title compound was prepared from N-bromoacetyl-3-carboxyethyl -2,6-diphenyl-4-hydroxy-Δ³-tetrahydropyridine and benzoxazol -2-thiol according to the literature method (Aridoss et al., 2010a). Single crystals of the target molecule were obtained by the slow evaporation of its ethanolic solution at room temperature.