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; Sema Öztürk Yildirim; Ray J Butcher; Rahime Şimsek; Cihat Şafak

doi:10.1107/S1600536812045886

. 2012 Nov 10;68(Pt 12):o3337. doi: 10.1107/S1600536812045886

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 Şimsek ^a, Cihat Şafak ^a

PMCID: PMC3588939 PMID: 23476175

Abstract

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 ▶); 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: Şimşek 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,
a = 9.1544 (4) Å
b = 18.9619 (8) Å
c = 12.9790 (5) Å
β = 105.623 (4)°
V = 2169.72 (16) Å³
Z = 4
Cu Kα radiation
μ = 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 > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.137
S = 1.06
4444 reflections
290 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.96 e Å⁻³
Δρ_min = −1.35 e Å⁻³

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 Material

Click here for additional data file.^{(34.1KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045886/hg5266sup1.cif

e-68-o3337-sup1.cif^{(34.1KB, cif)}

Click here for additional data file.^{(217.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045886/hg5266Isup2.hkl

e-68-o3337-Isup2.hkl^{(217.7KB, hkl)}

Click here for additional data file.^{(9.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812045886/hg5266Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Acridines display abroad range of biological properties including antibacterial, anti-parasitic, and antitumor activities (Biwersi et al., 1994; Wainwright, 2001;Guetzoyan et al., 2007; Denny, 2002; Luan et al., 2011). Furthermore, the indole moiety also has a wide range of biological activities which may enhance the acridine ring properties. Recent studies show that some acridine analogs having aryl and heteroaryl substituents on their ten position on the ring exert potassium channel modulating activities (Şimşek et al., 2004; Berkan et al., 2002).

The title acridine compound contains (Fig. 1), 5-bromo-3-methyl-1H-indole connected to the 3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione system and the disordered dimethyl sulfoxide solvent molecule. The Br—C bond distance [1.910 (3) Å] is in the normal range (Allen, 2002). The 1-H indole ring system is essentially planar with a maximum deviation of -0.050 (3) Å for atom C21. The 1H-indol ring system forms a dihedral angle of 22.40 (12) ° with the 1,4-dihydro-pyridine ring (N1/C1/C6—C8/C13). The two cyclohex-2-enone rings (C1—C6 and C8—C13) adopt half chair conformations with C3 atom 0.345 (3) Å and C11 atom 0.335 (3) Å out of the mean-plane formed by the remaining ring atoms. The solvent molecule exhibits minor disorder of its S atom [site occupancies = 0.8153 (16) and 0.1847 (18)]. In the crystal, molecules are linked by C—H···O and N—H···O hydrogen bonds (Tab. 1 & Fig. 2).

Experimental

A mixture of 5-bromoindole-3-carbaldehyde (1.0 mmol), 1,3-cyclohexanedione (2.0 mmol), ammonium acetate (5.0 mmol) was dissolved in 5 ml of methanol and refluxed until the reaction was completed (monitored by TLC). The forming precipitate was filtered off and crystallized from ethanol. Crystals were grown by slow evaporation of an dimethyl sulfoxide/methanol mixed solution.