3,3,6,6-Tetra­methyl-9-(1-methyl-1H-indol-2-yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

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

doi:10.1107/S1600536812045722

Volume 68
Part 12
Pages o3365-o3366
December 2012

Received 2 November 2012
Accepted 5 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 13.5
Details

3,3,6,6-Tetramethyl-9-(1-methyl-1H-indol-2-yl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

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

In the acridine system of the title molecule, C₂₆H₃₀N₂O₂, both cyclohex-2-enone rings adopt sofa conformations. The indole ring system is essentially planar, with a maximum deviation of 0.017 (2) Å for a bridgehead C atom. An intramolecular C-HO hydrogen bond occurs. The molecules assemble into C(6) chains in the crystal by way of N-HO hydrogen bonds.

Related literature

For potassium channel modulator activity for bicyclo (quinoline) and tricyclo (acridine) analogs, see: Horiuchi et al. (2001); Crestanello et al. (2000); Frank et al. (1993); Berkan et al. (2002); Simsek et al. (2004); Fincan et al. (2012); Gündüz et al. (2009); Li et al. (2011). For a description of the Cambridge Structural Database, see: Allen (2002). For a similar structure, see: El-Khouly et al. (2012). For geometric analysis, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Etter et al. (1990).

Experimental

Crystal data

C₂₆H₃₀N₂O₂
M_r = 402.54
Orthorhombic, P n a 2₁
a = 14.09072 (13) Å
b = 15.04800 (15) Å
c = 10.39178 (12) Å
V = 2203.44 (4) Å³
Z = 4
Cu K radiation
= 0.60 mm^-1
T = 123 K
0.50 × 0.45 × 0.40 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)] T_min = 0.753, T_max = 0.795
10170 measured reflections
3713 independent reflections
3682 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.096
S = 1.02
3713 reflections
276 parameters
1 restraint
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C22-H22CO2	0.98	2.54	3.314 (2)	136
N1-H1AO1ⁱ	0.88	1.87	2.7437 (15)	170
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

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: JJ2157 ).

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.
Berkan, O., Saraç, B., Simsek, R., Yildirim, A., Sarioglu, Y. & Safak, C. (2002). Eur. J. Med. Chem. 37, 519-523.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Crestanello, J. A., Doliba, N. M., Babsky, A. M., Debliba, N. M., Niiobori, K., Osbakken, M. & Whitman, G. J. (2000). J. Surg. Res. 94, 116-123.
El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Fincan, G. S. Ö., Gündüz, M., Vural, I. M., Simsek, R., Sarioglu, Y. & Safak, C. (2012). Med. Chem. Res. 21, 1817-1824.
Frank, C. A., Forst, J. M., Grant, T., Harris, R. J., Kau, S. T., Li, J. H., Ohnmacht, C. J., Smith, R. W., Trainor, D. A. & Trivedi, S. (1993). Bioorg. Med. Chem. Lett. 3, 2725-2726.
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, G. D. (2001). Stroke, 32, 218-224.
Li, T., Feng, X., Yao, C., Yu, C., Jiang, B. & Tu, S. (2011). Bioorg. Med. Chem. Lett. 21, 453-455.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Simsek, R., Özkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.

organic compounds