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

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

doi:10.1107/S1600536812045886

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 (C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.052
wR = 0.137
Data-to-parameter ratio = 15.3
Details

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

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

^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-HO 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-HO 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); Wainwright (2001); Guetzoyan et al. (2007); Denny (2002); Luan et al. (2011). 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), Berkan et al. (2002). For a description of the Cambridge Structural Database, see: Allen, (2002).

Experimental

Crystal data

C₂₁H₁₉BrN₂O₂·C₂H₆OS
M_r = 489.42
Monoclinic, P 2₁ /c
a = 9.1544 (4) Å
b = 18.9619 (8) Å
c = 12.9790 (5) Å
= 105.623 (4)°
V = 2169.72 (16) Å³
Z = 4
Cu K radiation
= 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), using a multi-faceted crystal model (Clark & Reid, 1995)] T_min = 0.272, T_max = 0.721
14006 measured reflections
4444 independent reflections
4183 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.137
S = 1.06
4444 reflections
290 parameters
6 restraints
H-atom parameters constrained
_max = 1.96 e Å^-3
_min = -1.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16AO1	0.95	2.50	3.252 (3)	136
N1-H1AO2ⁱ	0.88	2.03	2.901 (3)	173
N2-H2CO100ⁱⁱ	0.88	2.10	2.920 (3)	154
N2-H2CO100ⁱⁱⁱ	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); 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: 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.
Berkan, Ö., Saraç, B., Simsek, R., Yildirim, S., Sarioglu, Y. & Safak, C. (2002). Eur. J. Med. Chem. 37, 519-523.
Biwersi, J., Tulk, B. & Verkman, A. S. (1994). Anal. Biochem. 219, 139-43.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Denny, W. (2002). Curr. Med. Chem. 9, 1655-1665.
Guetzoyan, L., Ramiandrasoa, F., Dorizon, H., Desprez, C., Bridoux, A., Rogier, C., Pradines, B. & Perree-Fauvet, M. (2007). Bioorg. Med. Chem. 15, 3278-3289.
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.
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.
Wainwright, M. J. (2001). J. Antimicrob. Chemother. 47, 1-13.

organic compounds