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

Öztürk Yildirim, S.; Butcher, R.J.; Şimsek, R.; El-Khouly, A.; Şafak, C.

doi:10.1107/S1600536812048957

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.122
Data-to-parameter ratio = 15.4
Details

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

Sema Öztürk Yildirim,^a,^b Ray J. Butcher,^a ^* Rahime Simsek,^c Ahmed El-Khouly ^c and Cihat Safak ^c

^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-HO 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); Crestanello et al. (2000). For biological properties of 1,4-dihydropyridines (DHP), see: Simsek et al. (2004); Fincan et al. (2012); Gündüz et al. (2009); Pyrko (2008); Li et al. (2010). For geometric analysis, see: Cremer & Pople (1975). For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For similar structures, see: El-Khouly et al. (2012); Öztürk Yildirim et al. (2012, 2013); Gündüz et al. (2012).

Experimental

Crystal data

C₁₇H₂₁NO₂
M_r = 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 radiation
= 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), based on expressions derived by Clark & Reid (1995)] T_min = 0.740, T_max = 0.856
3055 measured reflections
1452 independent reflections
1349 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.122
S = 1.09
1452 reflections
94 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2BO1ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
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Simsek, R., Ozkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.

organic compounds