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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 [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 15.4
Details
Open access

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

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-H...O, C-H...O and C-H...[pi] interactions. Formation of centrosymmetric head-to-head dimers is observed through pairwise intermolecular N-H...O hydrogen bonds. Additional weak C-H...O 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[Pearson, M. S. M., Mathe-Allainmat, M., Fargeas, V. & Lebreton, J. (2005). Eur. J. Org. Chem. 36, 2159-2191.]); Sakai et al. (1986[Sakai, R., Higa, T., Jefford, C. W., Bernardinelli, G. & Manzamine, A. (1986). J. Am. Chem. Soc. 108, 6404-6405.]); Nayak et al. (2011[Nayak, S. K., Venugopala, K. N., Chopra, D. & Guru Row, T. N. (2011). CrystEngComm, 13, 591-605.]); Mishra & Ghosh (2011[Mishra, S. & Ghosh, R. (2011). Tetrahedron Lett. 52, 2857-2861.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C33H32N2O2

  • Mr = 488.61

  • Monoclinic, P 21 /c

  • a = 13.3701 (11) Å

  • b = 6.1744 (5) Å

  • c = 31.797 (2) Å

  • [beta] = 90.381 (2)°

  • V = 2624.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany.]) Tmin = 0.978, Tmax = 0.996

  • 16243 measured reflections

  • 5175 independent reflections

  • 3513 reflections with I > 2[sigma](I)

  • Rint = 0.041

  • Standard reflections: 0

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.112

  • S = 1.03

  • 5175 reflections

  • 337 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
N2-H2...O1 0.88 2.11 2.7343 (17) 128
C19-H19...O2 0.95 2.47 3.213 (3) 135
N2-H2...O1i 0.88 2.52 3.2471 (17) 140
C23-H23...O1ii 0.95 2.40 3.236 (2) 147
C24-H24...O1iii 0.95 2.58 3.363 (2) 140
C27-H27...Cg1 0.95 2.83 3.476 (2) 126
C13-H13B...Cg2iv 0.98 2.81 3.679 (2) 148
C21-H21C...Cg3v 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a[Sheldrick, G. M. (2008a). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a[Sheldrick, G. M. (2008a). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


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.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Mishra, S. & Ghosh, R. (2011). Tetrahedron Lett. 52, 2857-2861.  [ISI] [CSD] [CrossRef] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nayak, S. K., Venugopala, K. N., Chopra, D. & Guru Row, T. N. (2011). CrystEngComm, 13, 591-605.  [ISI] [CSD] [CrossRef] [ChemPort]
Pearson, M. S. M., Mathe-Allainmat, M., Fargeas, V. & Lebreton, J. (2005). Eur. J. Org. Chem. 36, 2159-2191.  [CrossRef]
Sakai, R., Higa, T., Jefford, C. W., Bernardinelli, G. & Manzamine, A. (1986). J. Am. Chem. Soc. 108, 6404-6405.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008a). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o2392-o2393   [ doi:10.1107/S1600536812030309 ]

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