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

Niedziałkowski, P.; Wnuk, E.; Wcisło, A.; Trzybiński, D.

doi:10.1107/S1600536812050313

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 (C-C) = 0.002 Å
R = 0.041
wR = 0.102
Data-to-parameter ratio = 13.4
Details

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

Pawel Niedzialkowski,^a Elzbieta Wnuk,^a Anna Wcislo ^a and Damian Trzybinski ^a ^*

^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); El-Najjar et al. (2011); Czupryniak et al. (2012); Krohn (2008); Wannalerse et al. (2008). For related structures, see: Niedzialkowski et al. (2010, 2011); Wnuk et al. (2012); Yatsenko et al. (2000).

Experimental

Crystal data

C₂₄H₂₆N₂O₂
M_r = 374.47
Monoclinic, P 2₁ /c
a = 10.9115 (4) Å
b = 7.0127 (2) Å
c = 12.5984 (5) Å
= 97.819 (4)°
V = 955.05 (6) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.909, T_max = 1.000
12625 measured reflections
1699 independent reflections
1274 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.102
S = 1.04
1699 reflections
127 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C2-H2Cg2ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Czupryniak, J., Niedzialkowski, P., Karbarz, M., Ossowski, T. & Stojek, Z. (2012). Electroanalysis, 24, 975-982.
El-Najjar, N., Gali-Muhtasib, H. A., Ketola, R., Vuorela, P., Urtti, A. & Vuorela, H. (2011). Phytochem. Rev. 10, 353-370.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Niedzialkowski, P., Trzybinski, D., Sikorski, A. & Ossowski, T. (2010). Acta Cryst. E66, o33-o34.
Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wannalerse, B., Tuntulani, T. & Tomapatanaget, B. (2008). Tetrahedron, 64, 10619-10624.
Wnuk, E., Niedzialkowski, P., Trzybinski, D. & Ossowski, T. (2012). Acta Cryst. E68, o2879.
Yatsenko, A. V., Paseshnichenko, K. A. & Popov, S. I. (2000). Z. Kristallogr. 215, 542-546.

organic compounds