Ethyl 1-(2-bromo­propano­yl)-4-hydr­oxy-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxylate

Aridoss, G.; Gayathri, D.; Velmurugan, D.; Kim, M.S.; Jeong, Y.T.

doi:10.1107/S1600536809023836

Volume 65
Part 7
Pages o1708-o1709
July 2009

Received 16 June 2009
Accepted 22 June 2009
Online 27 June 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R = 0.044
wR = 0.138
Data-to-parameter ratio = 13.8
Details

Ethyl 1-(2-bromopropanoyl)-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

G. Aridoss,^a D. Gayathri,^b ⁺ D. Velmurugan,^b M. S. Kim ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: ytjeong@pknu.ac.kr

The title compound, C₂₃H₂₄BrNO₄, crystallizes with two independent molecules per asymmetric unit. The methyl group of the ethoxycarbonyl unit is disordered over two positions, with occupancies of 0.715 (12) and 0.285 (12) in one of the independent molecules, and 0.529 (11) and 0.471 (11) in the other molecule. In one of the independent molecules, the tetrahydropyridine ring adopts a half-chair conformation, while in the other it is in a distorted envelope conformation. In each independent molecule, an intramolecular O-HO hydrogen bond generates an S(6) ring motif. The two independent molecules are linked via C-HO hydrogen bonds, forming a chain along the c axis.

Related literature

For general background to the synthesis and properties of 2,6-diarylpiperidin-4-one derivatives, see: Aridoss et al. (2007, 2008b); Krishnakumar & Krishnapillay (1996); Krishnapillay et al. (2000); Rubiralta et al. (1991). For the biological activity of pyridine derivatives, see: Aridoss et al. (2008a); Dewick (1997); Gwaltney et al. (2003); Michael (1997, 2001); Pinder (1992); Yeung et al. (1982). For a related structure, see: Subha Nandhini et al. (2003). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₂₃H₂₄BrNO₄
M_r = 458.34
Triclinic, $[P \overline 1]$
a = 10.3970 (4) Å
b = 14.4874 (6) Å
c = 15.8580 (7) Å
= 65.457 (2)°
= 89.556 (3)°
= 80.597 (3)°
V = 2138.80 (15) Å³
Z = 4
Mo K radiation
= 1.95 mm^-1
T = 293 K
0.30 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999) T_min = 0.600, T_max = 0.749
39210 measured reflections
7523 independent reflections
5075 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.138
S = 1.04
7523 reflections
545 parameters
28 restraints
H-atom parameters constrained
_max = 0.67 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1OO3	0.82	1.83	2.547 (6)	146
O5-H5OO7	0.82	1.90	2.582 (6)	140
C7-H7O6ⁱ	0.93	2.58	3.349 (4)	141
C30-H30O2ⁱⁱ	0.93	2.56	3.349 (5)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2830 ).

Acknowledgements

GA and YTJ acknowledge support provided by the second stage of BK21 program, Republic of Korea. Financial support from the University Grants Commission (UGC-SAP) and the Department of Science & Technology (DST-FIST), Government of India, are acknowledged by DV for providing facilities to the department.

References

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