Ethyl 4-anilino-2,6-bis­(4-fluoro­phen­yl)-1-phenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Anthal, S.; Brahmachari, G.; Das, S.; Kant, R.; Gupta, V.K.

doi:10.1107/S1600536813002158

Volume 69
Part 2
Pages o299-o300
February 2013

Received 12 December 2012
Accepted 22 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.056
wR = 0.167
Data-to-parameter ratio = 16.0
Details

Ethyl 4-anilino-2,6-bis(4-fluorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Sumati Anthal,^a Goutam Brahmachari,^b Suvankar Das,^b Rajni Kant ^a and Vivek K. Gupta ^a ^*

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bLaboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati University, Santiniketan 731 235, West Bengal, India
Correspondence e-mail: vivek_gupta2k2@hotmail.com

In the title compound, C₃₂H₂₈F₂N₂O₂, the tetrahydropyridine ring adopts a distorted boat conformation. The two fluorophenyl groups are attached to the tetrahydropyridine ring in a trans orientation. The dihedral angle between the planes of the fluoro-substituted rings is 57.0 (1)°. The amino group and carbonyl O atom are involved in intramolecular hydrogen bonding. In the crystal, weak C-HO, C-HF and C-H [pi] interactions link the molecules into columns along [010].

Related literature

For the crystal structures of related densely functionalized piperidine derivatives, see: Sambyal et al. (2011); Brahmachari & Das (2012); Khan et al. (2008, 2010). For general background to functionalized piperidines, see: Desai et al. (1992). For applications of functionalized piperidines, see: Jaen et al. (1988); Schotte et al. (1996); Agrawal & Somani (2009). For bond-length data in organic compounds, see: Allen et al. (1987).

Experimental

Crystal data

C₃₂H₂₈F₂N₂O₂
M_r = 510.56
Triclinic, $[P \overline 1]$
a = 10.0432 (4) Å
b = 10.4646 (4) Å
c = 13.9932 (6) Å
= 105.422 (4)°
= 105.982 (4)°
= 96.407 (4)°
V = 1335.53 (9) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.846, T_max = 1.000
19971 measured reflections
5521 independent reflections
3372 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.167
S = 1.03
5521 reflections
344 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.86	2.01	2.672 (3)	133
C11-H11O1ⁱ	0.93	2.46	3.298 (3)	150
C9-H9AF1ⁱⁱ	0.96	2.55	3.412 (3)	148
C26-H26Cg1ⁱⁱ	0.93	2.66	3.470 (3)	146
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5374 ).

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. GB is thankful to the CSIR, New Delhi, for financial support [grant No. 02 (110)/12/EMR-II].

References

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Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.
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Jaen, J. C., Wise, L. D., Heffner, T. G., Pugsley, T. A. & Meltzer, L. T. (1988). J. Med. Chem. 31, 1621-1625.
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