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Volume 68 
Part 12 
Page o3337  
December 2012  

Received 31 October 2012
Accepted 6 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.052
wR = 0.137
Data-to-parameter ratio = 15.3
Details
Open access

9-(5-Bromo-1H-indol-3-yl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione dimethyl sulfoxide monosolvate

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

In the title compound, C21H19BrN2O2·C2H6OS, the indole ring system is essentially planar, with a maximum deviation of 0.050 (3) Å for the non-bridgehead C atom adjacent to the N atom. The two cyclohex-2-enone rings adopt half-chair conformations. An intramolecular C-H...O hydrogen bond occurs. The solvent molecule exhibits minor disorder of the S atom [site occupancies = 0.8153 (16) and 0.1847 (18)]. In the crystal, molecules are linked by N-H...O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For biological properties of acridines, including antibacterial, anti-parasitic, and antitumor activity, see: Biwersi et al. (1994[Biwersi, J., Tulk, B. & Verkman, A. S. (1994). Anal. Biochem. 219, 139-43.]); Wainwright (2001[Wainwright, M. J. (2001). J. Antimicrob. Chemother. 47, 1-13.]); Guetzoyan et al. (2007[Guetzoyan, L., Ramiandrasoa, F., Dorizon, H., Desprez, C., Bridoux, A., Rogier, C., Pradines, B. & Perree-Fauvet, M. (2007). Bioorg. Med. Chem. 15, 3278-3289.]); Denny (2002[Denny, W. (2002). Curr. Med. Chem. 9, 1655-1665.]); Luan et al. (2011[Luan, X., Gao, C., Zhang, N., Chen, Y., Sun, Q., Tan, C., Liu, H., Jin, Y. & Jiang, Y. (2011). Bioorg. Med. Chem. 19, 3312-3319.]). For recent studies showing that some acridine analogs having aryl and heteroaryl substituents at the ten position on the ring exert potassium-channel-modulating activiy, see: Simsek et al. (2004[Simsek, R., Özkan, M., Kismetli, E., Uma, S. & Safak, C. (2004). Il Farmaco, 59, 939-943.]), Berkan et al. (2002[Berkan, Ö., Saraç, B., Simsek, R., Yildirim, S., Sarioglu, Y. & Safak, C. (2002). Eur. J. Med. Chem. 37, 519-523.]). For a description of the Cambridge Structural Database, see: Allen, (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19BrN2O2·C2H6OS

  • Mr = 489.42

  • Monoclinic, P 21 /c

  • a = 9.1544 (4) Å

  • b = 18.9619 (8) Å

  • c = 12.9790 (5) Å

  • [beta] = 105.623 (4)°

  • V = 2169.72 (16) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 3.71 mm-1

  • T = 123 K

  • 0.51 × 0.23 × 0.12 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), using a multi-faceted crystal model (Clark & Reid, 1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.272, Tmax = 0.721

  • 14006 measured reflections

  • 4444 independent reflections

  • 4183 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.137

  • S = 1.06

  • 4444 reflections

  • 290 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 1.96 e Å-3

  • [Delta][rho]min = -1.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16A...O1 0.95 2.50 3.252 (3) 136
N1-H1A...O2i 0.88 2.03 2.901 (3) 173
N2-H2C...O100ii 0.88 2.10 2.920 (3) 154
N2-H2C...O100iii 0.88 2.52 3.038 (3) 118
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. 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: HG5266 ).


Acknowledgements

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

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Berkan, Ö., Saraç, B., Simsek, R., Yildirim, S., Sarioglu, Y. & Safak, C. (2002). Eur. J. Med. Chem. 37, 519-523.  [ISI] [CrossRef] [PubMed] [ChemPort]
Biwersi, J., Tulk, B. & Verkman, A. S. (1994). Anal. Biochem. 219, 139-43.  [CrossRef] [ChemPort] [PubMed] [ISI]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Denny, W. (2002). Curr. Med. Chem. 9, 1655-1665.  [CrossRef] [PubMed] [ChemPort]
Guetzoyan, L., Ramiandrasoa, F., Dorizon, H., Desprez, C., Bridoux, A., Rogier, C., Pradines, B. & Perree-Fauvet, M. (2007). Bioorg. Med. Chem. 15, 3278-3289.  [CrossRef] [PubMed] [ChemPort]
Luan, X., Gao, C., Zhang, N., Chen, Y., Sun, Q., Tan, C., Liu, H., Jin, Y. & Jiang, Y. (2011). Bioorg. Med. Chem. 19, 3312-3319.  [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]
Wainwright, M. J. (2001). J. Antimicrob. Chemother. 47, 1-13.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3337  [ doi:10.1107/S1600536812045886 ]

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