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Volume 69 
Part 7 
Page o1101  
July 2013  

Received 29 May 2013
Accepted 9 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.131
Data-to-parameter ratio = 15.1
Details
Open access

(2S*,5R*)-2,5-Dimethyl-1,4-bis(pyridin-2-ylmethyl)piperazine

aDepartment of Chemistry, Williams College, Williamstown, MA 01267, USA, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

The title compound, C18H24N4, resides on a crystallographic inversion centre, so that the asymmetric unit comprises one half-molecule. The piperazine ring adopts a chair conformation, with the mean planes of the two equatorial pyridine rings parallel to each other and separated by 2.54 (3) Å. No classical hydrogen bonds are observed.

Related literature

For related work on the synthesis of tetradentate pyridine-piperazine ligands and for metal complexes of these ligands, see: Geiger et al. (2011[Geiger, R. A., Chattopadhyay, S., Day, V. W. & Jackson, T. A. (2011). Dalton Trans. 40, 1707-1715.]); Ostermeier et al. (2006[Ostermeier, M., Limberg, C. & Ziemer, B. (2006). Z. Anorg. Allg. Chem. 632, 1287-1292.], 2009[Ostermeier, M., Limberg, C., Herwig, C. & Ziemer, B. (2009). Z. Anorg. Allg. Chem. 635, 1823-1830.]); Nam (2007[Nam, W. (2007). Acc. Chem. Res. 40, 522-531.]); Huuskonen et al. (1995[Huuskonen, J., Schulz, J. & Rissanen, K. (1995). Liebigs Ann. pp. 1515-1519.]); Que & Tolman (2008[Que, L. & Tolman, W. B. (2008). Nature, 455, 333-339.]); Ratilainen et al. (1999[Ratilainen, J., Airola, K., Fröhlich, R., Nieger, M. & Rissanen, K. (1999). Polyhedron, 18, 2265-2273.]); Fuji et al. (1996[Fuji, K., Takasu, K., Miyamoto, H., Tanaka, K. & Taga, T. (1996). Tetrahedron Lett. 37, 7111-7114.]). For the synthesis, see: Halfen et al. (2000[Halfen, J. A., Uhan, J. M., Fox, D. C., Mehn, M. P. & Que, L. (2000). Inorg. Chem. 39, 4913-4920.]).

[Scheme 1]

Experimental

Crystal data
  • C18H24N4

  • Mr = 296.41

  • Orthorhombic, P b c a

  • a = 9.4097 (5) Å

  • b = 9.2191 (5) Å

  • c = 18.7473 (9) Å

  • V = 1626.29 (14) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.57 mm-1

  • T = 173 K

  • 0.22 × 0.18 × 0.04 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.817, Tmax = 1.000

  • 10101 measured reflections

  • 1545 independent reflections

  • 1392 reflections with I > 2[sigma](I)

  • Rint = 0.064

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

  • wR(F2) = 0.131

  • S = 1.07

  • 1545 reflections

  • 102 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2633 ).


Acknowledgements

CG acknowledges the Donors of the American Chemical Society Petroleum Research Fund for support of this research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fuji, K., Takasu, K., Miyamoto, H., Tanaka, K. & Taga, T. (1996). Tetrahedron Lett. 37, 7111-7114.  [CrossRef] [ChemPort] [Web of Science]
Geiger, R. A., Chattopadhyay, S., Day, V. W. & Jackson, T. A. (2011). Dalton Trans. 40, 1707-1715.  [CSD] [CrossRef] [ChemPort] [PubMed]
Halfen, J. A., Uhan, J. M., Fox, D. C., Mehn, M. P. & Que, L. (2000). Inorg. Chem. 39, 4913-4920.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Huuskonen, J., Schulz, J. & Rissanen, K. (1995). Liebigs Ann. pp. 1515-1519.  [CrossRef]
Nam, W. (2007). Acc. Chem. Res. 40, 522-531.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Ostermeier, M., Limberg, C., Herwig, C. & Ziemer, B. (2009). Z. Anorg. Allg. Chem. 635, 1823-1830.  [CSD] [CrossRef] [ChemPort]
Ostermeier, M., Limberg, C. & Ziemer, B. (2006). Z. Anorg. Allg. Chem. 632, 1287-1292.  [CSD] [CrossRef] [ChemPort]
Que, L. & Tolman, W. B. (2008). Nature, 455, 333-339.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Ratilainen, J., Airola, K., Fröhlich, R., Nieger, M. & Rissanen, K. (1999). Polyhedron, 18, 2265-2273.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1101  [ doi:10.1107/S160053681301605X ]

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