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Volume 69 
Part 1 
Pages o88-o89  
January 2013  

Received 14 November 2012
Accepted 29 November 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.122
Data-to-parameter ratio = 15.4
Details
Open access

2,2,7,7-Tetramethyl-1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and cHacettepe University, Faculty of Pharmacy, Dept. of Pharmaceutical Chemistry, 06100 Sihhiye-Ankara, Turkey
Correspondence e-mail: rbutcher99@yahoo.com

The whole molecule of the title compound, C17H21NO2, is generated by twofold rotational symmetry. The N atom and the C and H atoms in position 4 of the pyridine ring lie on the twofold axis. The cyclohexene ring has a sofa conformation with the CH2 C atom adjacent to the dimethyl-substituted C atom displaced by 0.5949 (16) Å from the mean plane of the other five C atoms. In the crystal, weak C-H...O interactions link the molecules into chains parallel to the a axis. In addition, [pi]-[pi] stacking interactions [centroid-centroid distance = 3.8444 (7) Å] contribute to the stabilization of the crystal structure.

Related literature

For background to potassium channels and biological functions and physiological roles, see: Horiuchi et al. (2001[Horiuchi, T., Dietrich, H. H., Tsugane, S. & Dacey, R. G. Jr (2001). Stroke, 32, 218-224.]); Crestanello et al. (2000[Crestanello, J. A., Doliba, N. M., Babsky, A. M., Doliba, N. M., Niibori, K., Osbakken, M. D. & Whitman, G. J. (2000). J. Surg. Res. 94, 116-123.]). For biological properties of 1,4-dihydropyridines (DHP), see: Simsek et al. (2004[Simsek, R., Ozkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.]); Fincan et al. (2012[Fincan, G. S. Ö., Gündüz, M. G., Vural, I. M., Simsek, R., Sarioglu, Y. & Safak, C. (2012). Med. Chem. Res. 21, 1817-1824.]); Gündüz et al. (2009[Gündüz, M. G., Dogan, A. E., Simsek, R., Erol, K. & Safak, C. (2009). Med. Chem. Res. 18, 317-325.]); Pyrko (2008[Pyrko, A. N. (2008). Russ. J. Org. Chem. 44, 1215-1224.]); Li et al. (2010[Li, T., Feng, X., Yao, C., Yu, C., Jiang, B. & Tu, S. (2010). Bioorg. Med. Chem. Lett. 21, 453-455.]). For geometric analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For similar structures, see: El-Khouly et al. (2012[El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.]); Öztürk Yildirim et al. (2012[Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.], 2013[Öztürk Yildirim, S., Butcher, R. J., Gündüz, M. G., El-Khouly, A., Simsek, R. & Safak, C. (2013). Acta Cryst. E69, o40-o41.]); Gündüz et al. (2012[Gündüz, M. G., Butcher, R. J., Öztürk Yildirim, S., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3404-o3405.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21NO2

  • Mr = 271.35

  • Tetragonal, P 43 22

  • a = 9.99077 (19) Å

  • c = 14.5063 (4) Å

  • V = 1447.95 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.64 mm-1

  • T = 123 K

  • 0.50 × 0.30 × 0.25 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.740, Tmax = 0.856

  • 3055 measured reflections

  • 1452 independent reflections

  • 1349 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.122

  • S = 1.09

  • 1452 reflections

  • 94 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2B...O1i 0.99 2.52 3.415 (2) 151
Symmetry code: (i) [-y+1, x, z-{\script{1\over 4}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2098 ).


Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Crestanello, J. A., Doliba, N. M., Babsky, A. M., Doliba, N. M., Niibori, K., Osbakken, M. D. & Whitman, G. J. (2000). J. Surg. Res. 94, 116-123.  [CrossRef] [PubMed] [ChemPort]
El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.  [CSD] [CrossRef] [details]
Fincan, G. S. Ö., Gündüz, M. G., Vural, I. M., Simsek, R., Sarioglu, Y. & Safak, C. (2012). Med. Chem. Res. 21, 1817-1824.  [ISI] [CrossRef] [ChemPort]
Gündüz, M. G., Butcher, R. J., Öztürk Yildirim, S., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3404-o3405.  [CSD] [CrossRef] [details]
Gündüz, M. G., Dogan, A. E., Simsek, R., Erol, K. & Safak, C. (2009). Med. Chem. Res. 18, 317-325.
Horiuchi, T., Dietrich, H. H., Tsugane, S. & Dacey, R. G. Jr (2001). Stroke, 32, 218-224.  [CrossRef] [PubMed] [ChemPort]
Li, T., Feng, X., Yao, C., Yu, C., Jiang, B. & Tu, S. (2010). Bioorg. Med. Chem. Lett. 21, 453-455.  [CSD] [CrossRef] [PubMed]
Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.  [CSD] [CrossRef] [details]
Öztürk Yildirim, S., Butcher, R. J., Gündüz, M. G., El-Khouly, A., Simsek, R. & Safak, C. (2013). Acta Cryst. E69, o40-o41.  [CrossRef] [details]
Pyrko, A. N. (2008). Russ. J. Org. Chem. 44, 1215-1224.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Simsek, R., Ozkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.  [PubMed]


Acta Cryst (2013). E69, o88-o89   [ doi:10.1107/S1600536812048957 ]

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