Methyl 2,6-diphenyl-1-p-tolyl-4-(p-tolyl­amino)-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Venugopala, K.N.; Nayak, S.K.; Odhav, B.

doi:10.1107/S1600536812030309

Volume 68
Part 8
Pages o2392-o2393
August 2012

Received 28 June 2012
Accepted 3 July 2012
Online 7 July 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 15.4
Details

Methyl 2,6-diphenyl-1-p-tolyl-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

K. N. Venugopala,^a ^* Susanta K. Nayak ^b ^* and Bharti Odhav ^a

^aDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa, and ^bCenter for Nano Science and Technology at PoliMi, Istituto Italiano di Tecnologia, Via Pascoli 70/3, 20133 Milan, Italy
Correspondence e-mail: katharigattav@dut.ac.za, nksusa@gmail.com

In the title compound, C₃₃H₃₂N₂O₂, the tetrahydropyridine ring adopts a boat conformation with the carbonyl group in an s-cis conformation with respect to the C=C bond of the six-membered tetrahydropyridine ring. The molecular conformation is stabilized by intramolecular N-HO, C-HO and C-H [pi] interactions. Formation of centrosymmetric head-to-head dimers is observed through pairwise intermolecular N-HO hydrogen bonds. Additional weak C-HO and C-H [pi] interactions stabilize the three-dimensional molecular assembly.

Related literature

For background to the applications of piperidines, see: Pearson et al. (2005); Sakai et al. (1986); Nayak et al. (2011); Mishra & Ghosh (2011). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₃H₃₂N₂O₂
M_r = 488.61
Monoclinic, P 2₁ /c
a = 13.3701 (11) Å
b = 6.1744 (5) Å
c = 31.797 (2) Å
= 90.381 (2)°
V = 2624.8 (4) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 173 K
0.29 × 0.13 × 0.05 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) T_min = 0.978, T_max = 0.996
16243 measured reflections
5175 independent reflections
3513 reflections with I > 2(I)
R_int = 0.041
Standard reflections: 0

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.112
S = 1.03
5175 reflections
337 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C29-C34, C7-C12 and C22-C27 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.88	2.11	2.7343 (17)	128
C19-H19O2	0.95	2.47	3.213 (3)	135
N2-H2O1ⁱ	0.88	2.52	3.2471 (17)	140
C23-H23O1ⁱⁱ	0.95	2.40	3.236 (2)	147
C24-H24O1ⁱⁱⁱ	0.95	2.58	3.363 (2)	140
C27-H27Cg1	0.95	2.83	3.476 (2)	126
C13-H13BCg2^iv	0.98	2.81	3.679 (2)	148
C21-H21CCg3^v	0.98	2.97	3.487 (2)	114
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z; (iv) $[-x+1, y+{\script{5\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+1, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2490 ).

Acknowledgements

The authors thank Durban University of Technology for facilities. KNV thanks NRF South Africa for a DST/NRF Innovation Postdoctoral Fellowship 2012.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Mishra, S. & Ghosh, R. (2011). Tetrahedron Lett. 52, 2857-2861.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Nayak, S. K., Venugopala, K. N., Chopra, D. & Guru Row, T. N. (2011). CrystEngComm, 13, 591-605.
Pearson, M. S. M., Mathe-Allainmat, M., Fargeas, V. & Lebreton, J. (2005). Eur. J. Org. Chem. 36, 2159-2191.
Sakai, R., Higa, T., Jefford, C. W., Bernardinelli, G. & Manzamine, A. (1986). J. Am. Chem. Soc. 108, 6404-6405.
Sheldrick, G. M. (2008a). Acta Cryst. A64, 112-122.
Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds