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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 [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O hydrogen bond occurs. The molecules assemble into C(6) chains in the crystal by way of N-H...O hydrogen bonds.

Related literature

For potassium channel modulator activity for bicyclo (quinoline) and tricyclo (acridine) analogs, see: Horiuchi et al. (2001[Horiuchi, T., Dietrich, H. H., Tsugane, S. & Dacey, G. D. (2001). Stroke, 32, 218-224.]); Crestanello et al. (2000[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.]); Frank et al. (1993[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.]); Berkan et al. (2002[Berkan, O., Saraç, B., Simsek, R., Yildirim, A., Sarioglu, Y. & Safak, C. (2002). Eur. J. Med. Chem. 37, 519-523.]); Simsek et al. (2004[Simsek, R., Özkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.]); Fincan et al. (2012[Fincan, G. S. Ö., Gündüz, M., 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.]); Li et al. (2011[Li, T., Feng, X., Yao, C., Yu, C., Jiang, B. & Tu, S. (2011). Bioorg. Med. Chem. Lett. 21, 453-455.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For a similar structure, see: El-Khouly et al. (2012[El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.]). For geometric analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C26H30N2O2

  • Mr = 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[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]), based on expressions derived from Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.753, Tmax = 0.795

  • 10170 measured reflections

  • 3713 independent reflections

  • 3682 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.02

  • 3713 reflections

  • 276 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 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
C22-H22C...O2 0.98 2.54 3.314 (2) 136
N1-H1A...O1i 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[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: 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.  [ISI] [CrossRef] [details]
Berkan, O., Saraç, B., Simsek, R., Yildirim, A., Sarioglu, Y. & Safak, C. (2002). Eur. J. Med. Chem. 37, 519-523.  [ISI] [CrossRef] [PubMed] [ChemPort]
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., Debliba, N. M., Niiobori, K., Osbakken, M. & 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.  [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Fincan, G. S. Ö., Gündüz, M., Vural, I. M., Simsek, R., Sarioglu, Y. & Safak, C. (2012). Med. Chem. Res. 21, 1817-1824.  [ISI] [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
Li, T., Feng, X., Yao, C., Yu, C., Jiang, B. & Tu, S. (2011). Bioorg. Med. Chem. Lett. 21, 453-455.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Simsek, R., Özkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.  [PubMed]


Acta Cryst (2012). E68, o3365-o3366   [ doi:10.1107/S1600536812045722 ]

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