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Volume 69 
Part 1 
Page o110  
January 2013  

Received 5 December 2012
Accepted 10 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.102
Data-to-parameter ratio = 13.4
Details
Open access

1,5-Bis(piperidin-1-yl)-9,10-anthraquinone

aFaculty of Chemistry, University of Gdansk, J. Sobieskiego 18, 80-952 Gdansk, Poland
Correspondence e-mail: trzybinski@chem.univ.gda.pl

In the centrosymmetric title compound, C24H26N2O2, the piperidine ring adopts a chair conformation and is inclined at a dihedral angle of 37.5 (1)°to the anthracene ring system. In the crystal, adjacent molecules are linked through C-H...[pi] and [pi]-[pi] [centroid-centroid distances = 3.806 (1) Å] interactions, forming a layer parallel to the bc plane.

Related literature

For general background to quinone compounds, see: Alves et al. (2004[Alves, D. S., Perez-Fons, L., Estepa, A. & Micol, V. (2004). Biochem. Pharmacol. 68, 549-561.]); El-Najjar et al. (2011[El-Najjar, N., Gali-Muhtasib, H. A., Ketola, R., Vuorela, P., Urtti, A. & Vuorela, H. (2011). Phytochem. Rev. 10, 353-370.]); Czupryniak et al. (2012[Czupryniak, J., Niedzialkowski, P., Karbarz, M., Ossowski, T. & Stojek, Z. (2012). Electroanalysis, 24, 975-982.]); Krohn (2008[Krohn, K. (2008). Editor. Anthracycline Chemistry and Biology II, Topics in Current Chemistry, Vol. 283. Berlin Heidelberg: Springer-Verlag.]); Wannalerse et al. (2008[Wannalerse, B., Tuntulani, T. & Tomapatanaget, B. (2008). Tetrahedron, 64, 10619-10624.]). For related structures, see: Niedzialkowski et al. (2010[Niedzialkowski, P., Trzybinski, D., Sikorski, A. & Ossowski, T. (2010). Acta Cryst. E66, o33-o34.], 2011[Niedzialkowski, P., Narloch, J., Trzybinski, D. & Ossowski, T. (2011). Acta Cryst. E67, o723.]); Wnuk et al. (2012[Wnuk, E., Niedzialkowski, P., Trzybinski, D. & Ossowski, T. (2012). Acta Cryst. E68, o2879.]); Yatsenko et al. (2000[Yatsenko, A. V., Paseshnichenko, K. A. & Popov, S. I. (2000). Z. Kristallogr. 215, 542-546.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26N2O2

  • Mr = 374.47

  • Monoclinic, P 21 /c

  • a = 10.9115 (4) Å

  • b = 7.0127 (2) Å

  • c = 12.5984 (5) Å

  • [beta] = 97.819 (4)°

  • V = 955.05 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.45 × 0.22 × 0.05 mm

Data collection
  • Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.909, Tmax = 1.000

  • 12625 measured reflections

  • 1699 independent reflections

  • 1274 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.102

  • S = 1.04

  • 1699 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg2i 0.93 2.98 3.850 (2) 156
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5662 ).


Acknowledgements

This study was financed by the State Funds for Scientific Research through National Center for Science grant No. N N204 122 640 and by the University of Gdansk within the project supporting young scientists and PhD students (grant No. 538-8210-1029-12).

References

Alves, D. S., Perez-Fons, L., Estepa, A. & Micol, V. (2004). Biochem. Pharmacol. 68, 549-561.  [ISI] [CrossRef] [PubMed] [ChemPort]
Czupryniak, J., Niedzialkowski, P., Karbarz, M., Ossowski, T. & Stojek, Z. (2012). Electroanalysis, 24, 975-982.  [CrossRef] [ChemPort]
El-Najjar, N., Gali-Muhtasib, H. A., Ketola, R., Vuorela, P., Urtti, A. & Vuorela, H. (2011). Phytochem. Rev. 10, 353-370.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Krohn, K. (2008). Editor. Anthracycline Chemistry and Biology II, Topics in Current Chemistry, Vol. 283. Berlin Heidelberg: Springer-Verlag.
Niedzialkowski, P., Narloch, J., Trzybinski, D. & Ossowski, T. (2011). Acta Cryst. E67, o723.  [CSD] [CrossRef] [details]
Niedzialkowski, P., Trzybinski, D., Sikorski, A. & Ossowski, T. (2010). Acta Cryst. E66, o33-o34.  [CSD] [CrossRef] [details]
Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wannalerse, B., Tuntulani, T. & Tomapatanaget, B. (2008). Tetrahedron, 64, 10619-10624.  [ISI] [CrossRef] [ChemPort]
Wnuk, E., Niedzialkowski, P., Trzybinski, D. & Ossowski, T. (2012). Acta Cryst. E68, o2879.  [CSD] [CrossRef] [details]
Yatsenko, A. V., Paseshnichenko, K. A. & Popov, S. I. (2000). Z. Kristallogr. 215, 542-546.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o110  [ doi:10.1107/S1600536812050313 ]

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