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Volume 69 
Part 3 
Pages o408-o409  
March 2013  

Received 11 January 2013
Accepted 9 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.095
Data-to-parameter ratio = 7.9
Details
Open access

4-Hydroxy-1,1'-bis[(S)-1-phenylethyl]-5,5',6,6'-tetrahydro-3,4'-bipyridine-2,2'(1H,1'H)-dione

aUniversidad Juárez Autónoma de Tabasco, División Académica de Ciencias Básicas, Km. 1 carretera Cunduacán, Jalpa de Méndez AP 24, Cunduacán, Tabasco, Mexico,bCentro de Química, Benemerita Universidad Autónoma de Puebla, Edif. 103H Complejo de Ciencias, C.U., 72570 Puebla, Pue., Mexico, and cUniversidad Autónoma de Nuevo León, UANL, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, San Nicolás de los Garza, Nuevo León CP 66451, Mexico
Correspondence e-mail: sylvain_bernes@hotmail.com

The title bis-piperidine, C26H28N2O3, was unexpectedly obtained via a dimerization mechanism promoted by acetic acid when performing the Dieckmann cyclization of a chiral amido ester. The S,S configuration was assigned by reference to the enantiomerically pure starting material. In the molecule, two core heterocycles are linked by a [sigma] bond. One ring includes a keto-enol group, while the other presents an enone functionality. Both rings present a conformation intermediate between envelope and screw-boat, and the dihedral angle between the mean planes passing through the rings [48.9 (1)°] is large enough to avoid hindrance between ring substituents. The enol tautomeric form in one ring favors the formation of strong intermolecular O-H...O=C hydrogen bonds. The resulting one-dimensional supramolecular structure features single-stranded helices running along the 21 screw axis parallel to [100].

Related literature

For natural products having a bis-piperidine substructure, see: Gil et al. (1995[Gil, L., Baucherel, X., Martin, M.-T., Marazano, C. & Das, B. C. (1995). Tetrahedron Lett. 36, 6231-6234.]); Torres et al. (2000[Torres, Y. R., Berlinck, R. G. S., Magalhães, A., Schefer, A. B., Ferreira, A. G., Hajdu, E. & Muricy, G. (2000). J. Nat. Prod. 63, 1098-1105.]); Matsunaga et al. (2004[Matsunaga, S., Miyata, Y., van Soest, R. W. M. & Fusetani, N. (2004). J. Nat. Prod. 67, 1758-1760.]); Smith & Sulikowski (2010[Smith, B. J. & Sulikowski, G. A. (2010). Angew. Chem. Int. Ed. 49, 1599-1602.]). For related structures of monocyclic piperidines, see: Didierjean et al. (2004[Didierjean, C., Marin, J., Wenger, E., Briand, J.-P., Aubry, A. & Guichard, G. (2004). Acta Cryst. C60, o200-o203.]); Romero et al. (2005[Romero, N., Terán, J. L., Gnecco, D. & Bernès, S. (2005). Acta Cryst. E61, o2924-o2926.]). For the application of Dieckmann condensation in organic synthesis, see: Scheiber & Nemes (2008[Scheiber, P. & Nemes, P. (2008). Arkivoc, iii, 194-199.]). For an example of self-condensation of a dione similar to that used for the synthesis of the title compound, see: Sugasawa & Oka (1954[Sugasawa, S. & Oka, K. (1954). Chem. Pharm. Bull. 2, 85-88.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28N2O3

  • Mr = 416.50

  • Orthorhombic, P 21 21 21

  • a = 9.6647 (13) Å

  • b = 9.7281 (10) Å

  • c = 23.684 (3) Å

  • V = 2226.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.60 × 0.60 × 0.08 mm

Data collection
  • Bruker P4 diffractometer

  • 3173 measured reflections

  • 2250 independent reflections

  • 1843 reflections with I > 2[sigma](I)

  • Rint = 0.019

  • 3 standard reflections every 97 reflections intensity decay: 1.5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.095

  • S = 1.04

  • 2250 reflections

  • 286 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O2'i 0.97 (4) 1.67 (4) 2.637 (3) 177 (4)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NR2039 ).


Acknowledgements

The authors wish to acknowledge CONACyT-Gobierno del Estado Tabasco and the Universidad Juárez Autónoma de Tabasco for financial support via projects TAB-2009-C18-122141 and UJAT-2009-C05-02, respectively.

References

Didierjean, C., Marin, J., Wenger, E., Briand, J.-P., Aubry, A. & Guichard, G. (2004). Acta Cryst. C60, o200-o203.  [CSD] [CrossRef] [details]
Gil, L., Baucherel, X., Martin, M.-T., Marazano, C. & Das, B. C. (1995). Tetrahedron Lett. 36, 6231-6234.  [CrossRef] [ChemPort] [ISI]
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]
Matsunaga, S., Miyata, Y., van Soest, R. W. M. & Fusetani, N. (2004). J. Nat. Prod. 67, 1758-1760.  [ISI] [CrossRef] [PubMed] [ChemPort]
Romero, N., Terán, J. L., Gnecco, D. & Bernès, S. (2005). Acta Cryst. E61, o2924-o2926.  [CSD] [CrossRef] [details]
Scheiber, P. & Nemes, P. (2008). Arkivoc, iii, 194-199.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Smith, B. J. & Sulikowski, G. A. (2010). Angew. Chem. Int. Ed. 49, 1599-1602.  [ISI] [CSD] [CrossRef] [ChemPort]
Sugasawa, S. & Oka, K. (1954). Chem. Pharm. Bull. 2, 85-88.  [ChemPort]
Torres, Y. R., Berlinck, R. G. S., Magalhães, A., Schefer, A. B., Ferreira, A. G., Hajdu, E. & Muricy, G. (2000). J. Nat. Prod. 63, 1098-1105.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o408-o409   [ doi:10.1107/S1600536813004017 ]

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