organic compounds
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); 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
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell 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.
Supporting information
10.1107/S1600536812045886/hg5266sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045886/hg5266Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045886/hg5266Isup3.cml
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.
All disordered components were subjected to rigid bond and similarity restraints and all major and minor disordered components were refined anisotropically. Hydrogen atoms were positioned geometrically [C—H = 0.95–1.00 Å; N—H = 0.88 Å] and refined using a riding model, with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(Cmethyl). A rotating-group model was applied for methyl groups.
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Sheldrick, 2008).C21H19BrN2O2·C2H6OS | F(000) = 1008 |
Mr = 489.42 | Dx = 1.498 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 7435 reflections |
a = 9.1544 (4) Å | θ = 3.5–75.5° |
b = 18.9619 (8) Å | µ = 3.71 mm−1 |
c = 12.9790 (5) Å | T = 123 K |
β = 105.623 (4)° | Prism, light-yellow |
V = 2169.72 (16) Å3 | 0.51 × 0.23 × 0.12 mm |
Z = 4 |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 4444 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 4183 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 75.7°, θmin = 4.2° |
ω scans | h = −10→11 |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), using a multi-faceted crystal model (Clark & Reid, 1995)] | k = −20→23 |
Tmin = 0.272, Tmax = 0.721 | l = −15→16 |
14006 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0699P)2 + 3.3586P] where P = (Fo2 + 2Fc2)/3 |
4444 reflections | (Δ/σ)max = 0.001 |
290 parameters | Δρmax = 1.96 e Å−3 |
6 restraints | Δρmin = −1.35 e Å−3 |
C21H19BrN2O2·C2H6OS | V = 2169.72 (16) Å3 |
Mr = 489.42 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.1544 (4) Å | µ = 3.71 mm−1 |
b = 18.9619 (8) Å | T = 123 K |
c = 12.9790 (5) Å | 0.51 × 0.23 × 0.12 mm |
β = 105.623 (4)° |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 4444 independent reflections |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), using a multi-faceted crystal model (Clark & Reid, 1995)] | 4183 reflections with I > 2σ(I) |
Tmin = 0.272, Tmax = 0.721 | Rint = 0.041 |
14006 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 6 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.06 | Δρmax = 1.96 e Å−3 |
4444 reflections | Δρmin = −1.35 e Å−3 |
290 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S10A | −0.13796 (9) | 0.48345 (4) | 0.17928 (7) | 0.03482 (18) | 0.8153 (16) |
O100 | −0.0432 (3) | 0.51319 (16) | 0.1107 (2) | 0.0382 (7) | 0.8153 (16) |
C100 | −0.0885 (11) | 0.5268 (4) | 0.3027 (4) | 0.0648 (14) | 0.8153 (16) |
H10C | 0.0119 | 0.5110 | 0.3443 | 0.097* | 0.8153 (16) |
H10D | −0.1634 | 0.5160 | 0.3419 | 0.097* | 0.8153 (16) |
H10E | −0.0863 | 0.5778 | 0.2910 | 0.097* | 0.8153 (16) |
C200 | −0.3247 (4) | 0.5167 (3) | 0.1308 (6) | 0.0412 (9) | 0.8153 (16) |
H20A | −0.3729 | 0.4955 | 0.0611 | 0.062* | 0.8153 (16) |
H20B | −0.3210 | 0.5680 | 0.1231 | 0.062* | 0.8153 (16) |
H20C | −0.3835 | 0.5050 | 0.1814 | 0.062* | 0.8153 (16) |
S10B | −0.1368 (4) | 0.54694 (19) | 0.1798 (3) | 0.03482 (18) | 0.1847 (16) |
O101 | −0.0449 (18) | 0.4988 (9) | 0.1276 (13) | 0.0382 (7) | 0.1847 (16) |
C101 | −0.096 (5) | 0.517 (2) | 0.3127 (12) | 0.0648 (14) | 0.1847 (16) |
H10F | 0.0071 | 0.4981 | 0.3344 | 0.097* | 0.1847 (16) |
H10G | −0.1685 | 0.4803 | 0.3183 | 0.097* | 0.1847 (16) |
H10H | −0.1043 | 0.5567 | 0.3596 | 0.097* | 0.1847 (16) |
C201 | −0.3306 (14) | 0.5260 (18) | 0.132 (3) | 0.0412 (9) | 0.1847 (16) |
H20D | −0.3710 | 0.5458 | 0.0604 | 0.062* | 0.1847 (16) |
H20E | −0.3858 | 0.5458 | 0.1805 | 0.062* | 0.1847 (16) |
H20F | −0.3430 | 0.4746 | 0.1291 | 0.062* | 0.1847 (16) |
Br1 | 0.25418 (3) | 0.905937 (19) | 0.00832 (2) | 0.04525 (11) | |
O1 | 0.2313 (2) | 0.77721 (11) | 0.33651 (15) | 0.0352 (4) | |
O2 | 0.7181 (2) | 0.65871 (10) | 0.37707 (14) | 0.0340 (4) | |
N1 | 0.6163 (2) | 0.78876 (11) | 0.65949 (16) | 0.0260 (4) | |
H1A | 0.6514 | 0.8073 | 0.7235 | 0.031* | |
N2 | 0.7825 (2) | 0.92633 (11) | 0.39600 (17) | 0.0269 (4) | |
H2C | 0.8614 | 0.9546 | 0.4157 | 0.032* | |
C1 | 0.4715 (3) | 0.80553 (12) | 0.59876 (19) | 0.0243 (5) | |
C2 | 0.3651 (3) | 0.83425 (14) | 0.6587 (2) | 0.0296 (5) | |
H2A | 0.4191 | 0.8691 | 0.7123 | 0.036* | |
H2B | 0.3301 | 0.7954 | 0.6972 | 0.036* | |
C3 | 0.2284 (3) | 0.86936 (15) | 0.5820 (2) | 0.0365 (6) | |
H3A | 0.1516 | 0.8807 | 0.6205 | 0.044* | |
H3B | 0.2604 | 0.9140 | 0.5551 | 0.044* | |
C4 | 0.1589 (3) | 0.82086 (16) | 0.4883 (2) | 0.0364 (6) | |
H4A | 0.1152 | 0.7791 | 0.5149 | 0.044* | |
H4B | 0.0753 | 0.8460 | 0.4372 | 0.044* | |
C5 | 0.2730 (3) | 0.79654 (13) | 0.4305 (2) | 0.0275 (5) | |
C6 | 0.4318 (3) | 0.79381 (12) | 0.49155 (19) | 0.0239 (5) | |
C7 | 0.5513 (2) | 0.77218 (12) | 0.43652 (18) | 0.0225 (4) | |
H7A | 0.5026 | 0.7423 | 0.3730 | 0.027* | |
C8 | 0.6706 (3) | 0.72888 (12) | 0.51402 (18) | 0.0235 (5) | |
C9 | 0.7466 (3) | 0.67249 (13) | 0.4734 (2) | 0.0265 (5) | |
C10 | 0.8583 (3) | 0.62845 (14) | 0.5553 (2) | 0.0305 (5) | |
H10A | 0.9300 | 0.6052 | 0.5210 | 0.037* | |
H10B | 0.8032 | 0.5912 | 0.5830 | 0.037* | |
C11 | 0.9464 (3) | 0.67432 (14) | 0.6478 (2) | 0.0303 (5) | |
H11A | 1.0056 | 0.7101 | 0.6207 | 0.036* | |
H11B | 1.0183 | 0.6446 | 0.7008 | 0.036* | |
C12 | 0.8380 (3) | 0.71116 (13) | 0.70158 (19) | 0.0270 (5) | |
H12A | 0.8002 | 0.6766 | 0.7455 | 0.032* | |
H12B | 0.8934 | 0.7486 | 0.7498 | 0.032* | |
C13 | 0.7059 (3) | 0.74323 (12) | 0.62042 (19) | 0.0241 (5) | |
C14 | 0.6227 (3) | 0.83598 (12) | 0.39910 (18) | 0.0230 (4) | |
C15 | 0.5613 (3) | 0.87732 (12) | 0.30416 (18) | 0.0235 (4) | |
C16 | 0.4347 (3) | 0.86999 (13) | 0.21609 (19) | 0.0261 (5) | |
H16A | 0.3642 | 0.8327 | 0.2122 | 0.031* | |
C17 | 0.4162 (3) | 0.91920 (14) | 0.1349 (2) | 0.0296 (5) | |
C18 | 0.5129 (3) | 0.97717 (14) | 0.1398 (2) | 0.0300 (5) | |
H18A | 0.4911 | 1.0114 | 0.0843 | 0.036* | |
C19 | 0.6399 (3) | 0.98455 (13) | 0.2253 (2) | 0.0276 (5) | |
H19A | 0.7078 | 1.0229 | 0.2291 | 0.033* | |
C20 | 0.6650 (3) | 0.93375 (13) | 0.30590 (19) | 0.0253 (5) | |
C21 | 0.7575 (3) | 0.86762 (13) | 0.45088 (19) | 0.0253 (5) | |
H21A | 0.8242 | 0.8512 | 0.5157 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S10A | 0.0375 (4) | 0.0344 (4) | 0.0344 (4) | 0.0084 (3) | 0.0128 (3) | 0.0046 (3) |
O100 | 0.0318 (9) | 0.0508 (17) | 0.0359 (14) | 0.0114 (11) | 0.0159 (9) | 0.0126 (11) |
C100 | 0.058 (2) | 0.093 (4) | 0.0423 (19) | 0.008 (2) | 0.0118 (19) | −0.023 (2) |
C200 | 0.0305 (13) | 0.045 (2) | 0.0518 (17) | 0.0033 (13) | 0.0173 (13) | 0.0110 (16) |
S10B | 0.0375 (4) | 0.0344 (4) | 0.0344 (4) | 0.0084 (3) | 0.0128 (3) | 0.0046 (3) |
O101 | 0.0318 (9) | 0.0508 (17) | 0.0359 (14) | 0.0114 (11) | 0.0159 (9) | 0.0126 (11) |
C101 | 0.058 (2) | 0.093 (4) | 0.0423 (19) | 0.008 (2) | 0.0118 (19) | −0.023 (2) |
C201 | 0.0305 (13) | 0.045 (2) | 0.0518 (17) | 0.0033 (13) | 0.0173 (13) | 0.0110 (16) |
Br1 | 0.03879 (18) | 0.0606 (2) | 0.02995 (16) | −0.00943 (13) | −0.00175 (13) | 0.01575 (12) |
O1 | 0.0266 (8) | 0.0499 (11) | 0.0276 (9) | 0.0020 (8) | 0.0049 (7) | 0.0038 (8) |
O2 | 0.0406 (10) | 0.0372 (10) | 0.0242 (8) | 0.0118 (8) | 0.0085 (7) | −0.0004 (7) |
N1 | 0.0283 (9) | 0.0290 (10) | 0.0209 (9) | 0.0015 (8) | 0.0071 (8) | −0.0011 (7) |
N2 | 0.0255 (9) | 0.0284 (10) | 0.0278 (10) | −0.0025 (8) | 0.0089 (8) | −0.0006 (8) |
C1 | 0.0260 (10) | 0.0227 (10) | 0.0262 (11) | 0.0004 (8) | 0.0102 (9) | 0.0033 (8) |
C2 | 0.0329 (12) | 0.0307 (12) | 0.0293 (12) | 0.0062 (10) | 0.0153 (10) | 0.0024 (9) |
C3 | 0.0352 (13) | 0.0416 (14) | 0.0368 (13) | 0.0128 (11) | 0.0170 (11) | 0.0044 (11) |
C4 | 0.0254 (11) | 0.0499 (15) | 0.0364 (14) | 0.0071 (11) | 0.0126 (10) | 0.0076 (12) |
C5 | 0.0260 (11) | 0.0303 (12) | 0.0273 (11) | 0.0022 (9) | 0.0090 (9) | 0.0074 (9) |
C6 | 0.0233 (10) | 0.0252 (11) | 0.0250 (11) | 0.0019 (8) | 0.0096 (9) | 0.0042 (8) |
C7 | 0.0220 (10) | 0.0248 (10) | 0.0209 (10) | 0.0014 (8) | 0.0062 (8) | 0.0009 (8) |
C8 | 0.0214 (10) | 0.0255 (11) | 0.0239 (11) | 0.0001 (8) | 0.0065 (8) | 0.0028 (9) |
C9 | 0.0257 (11) | 0.0279 (11) | 0.0266 (11) | 0.0018 (9) | 0.0082 (9) | 0.0018 (9) |
C10 | 0.0297 (11) | 0.0318 (12) | 0.0298 (12) | 0.0095 (10) | 0.0077 (10) | 0.0017 (10) |
C11 | 0.0241 (11) | 0.0369 (13) | 0.0291 (12) | 0.0049 (10) | 0.0059 (9) | 0.0056 (10) |
C12 | 0.0267 (11) | 0.0321 (12) | 0.0213 (10) | 0.0016 (9) | 0.0048 (9) | 0.0042 (9) |
C13 | 0.0245 (10) | 0.0243 (10) | 0.0246 (11) | 0.0000 (9) | 0.0083 (9) | 0.0039 (8) |
C14 | 0.0242 (10) | 0.0252 (11) | 0.0210 (10) | 0.0034 (8) | 0.0086 (8) | −0.0006 (8) |
C15 | 0.0259 (10) | 0.0239 (10) | 0.0233 (10) | 0.0037 (9) | 0.0115 (9) | 0.0014 (8) |
C16 | 0.0268 (11) | 0.0272 (11) | 0.0246 (11) | 0.0003 (9) | 0.0077 (9) | 0.0028 (9) |
C17 | 0.0256 (11) | 0.0388 (13) | 0.0224 (11) | 0.0013 (10) | 0.0032 (9) | 0.0050 (10) |
C18 | 0.0348 (12) | 0.0311 (12) | 0.0267 (11) | 0.0038 (10) | 0.0129 (10) | 0.0065 (9) |
C19 | 0.0314 (11) | 0.0251 (11) | 0.0305 (12) | −0.0002 (9) | 0.0154 (10) | 0.0025 (9) |
C20 | 0.0259 (10) | 0.0254 (11) | 0.0272 (11) | 0.0015 (9) | 0.0113 (9) | −0.0022 (9) |
C21 | 0.0248 (10) | 0.0288 (11) | 0.0235 (10) | 0.0022 (9) | 0.0086 (9) | 0.0000 (9) |
S10A—O100 | 1.510 (3) | C3—H3B | 0.9900 |
S10A—C100 | 1.748 (6) | C4—C5 | 1.512 (4) |
S10A—C200 | 1.771 (4) | C4—H4A | 0.9900 |
C100—H10C | 0.9800 | C4—H4B | 0.9900 |
C100—H10D | 0.9800 | C5—C6 | 1.457 (3) |
C100—H10E | 0.9800 | C6—C7 | 1.515 (3) |
C200—H20A | 0.9800 | C7—C8 | 1.512 (3) |
C200—H20B | 0.9800 | C7—C14 | 1.515 (3) |
C200—H20C | 0.9800 | C7—H7A | 1.0000 |
S10B—O101 | 1.519 (11) | C8—C13 | 1.358 (3) |
S10B—C101 | 1.757 (11) | C8—C9 | 1.450 (3) |
S10B—C201 | 1.760 (10) | C9—C10 | 1.513 (3) |
C101—H10F | 0.9800 | C10—C11 | 1.525 (4) |
C101—H10G | 0.9800 | C10—H10A | 0.9900 |
C101—H10H | 0.9800 | C10—H10B | 0.9900 |
C201—H20D | 0.9800 | C11—C12 | 1.527 (3) |
C201—H20E | 0.9800 | C11—H11A | 0.9900 |
C201—H20F | 0.9800 | C11—H11B | 0.9900 |
Br1—C17 | 1.910 (3) | C12—C13 | 1.502 (3) |
O1—C5 | 1.232 (3) | C12—H12A | 0.9900 |
O2—C9 | 1.235 (3) | C12—H12B | 0.9900 |
N1—C13 | 1.378 (3) | C14—C21 | 1.374 (3) |
N1—C1 | 1.385 (3) | C14—C15 | 1.441 (3) |
N1—H1A | 0.8800 | C15—C16 | 1.398 (3) |
N2—C20 | 1.366 (3) | C15—C20 | 1.426 (3) |
N2—C21 | 1.374 (3) | C16—C17 | 1.383 (3) |
N2—H2C | 0.8800 | C16—H16A | 0.9500 |
C1—C6 | 1.358 (3) | C17—C18 | 1.402 (4) |
C1—C2 | 1.503 (3) | C18—C19 | 1.382 (4) |
C2—C3 | 1.526 (4) | C18—H18A | 0.9500 |
C2—H2A | 0.9900 | C19—C20 | 1.394 (3) |
C2—H2B | 0.9900 | C19—H19A | 0.9500 |
C3—C4 | 1.520 (4) | C21—H21A | 0.9500 |
C3—H3A | 0.9900 | ||
O100—S10A—C100 | 108.4 (3) | C8—C7—H7A | 108.8 |
O100—S10A—C200 | 108.1 (3) | C6—C7—H7A | 108.8 |
C100—S10A—C200 | 98.3 (4) | C14—C7—H7A | 108.8 |
O101—S10B—C101 | 104.4 (16) | C13—C8—C9 | 120.7 (2) |
O101—S10B—C201 | 109.5 (14) | C13—C8—C7 | 119.9 (2) |
C101—S10B—C201 | 101 (2) | C9—C8—C7 | 119.3 (2) |
S10B—C101—H10F | 109.5 | O2—C9—C8 | 122.2 (2) |
S10B—C101—H10G | 109.5 | O2—C9—C10 | 120.9 (2) |
H10F—C101—H10G | 109.5 | C8—C9—C10 | 116.8 (2) |
S10B—C101—H10H | 109.5 | C9—C10—C11 | 110.6 (2) |
H10F—C101—H10H | 109.5 | C9—C10—H10A | 109.5 |
H10G—C101—H10H | 109.5 | C11—C10—H10A | 109.5 |
S10B—C201—H20D | 109.5 | C9—C10—H10B | 109.5 |
S10B—C201—H20E | 109.5 | C11—C10—H10B | 109.5 |
H20D—C201—H20E | 109.5 | H10A—C10—H10B | 108.1 |
S10B—C201—H20F | 109.5 | C10—C11—C12 | 110.5 (2) |
H20D—C201—H20F | 109.5 | C10—C11—H11A | 109.6 |
H20E—C201—H20F | 109.5 | C12—C11—H11A | 109.6 |
C13—N1—C1 | 120.5 (2) | C10—C11—H11B | 109.6 |
C13—N1—H1A | 119.7 | C12—C11—H11B | 109.6 |
C1—N1—H1A | 119.7 | H11A—C11—H11B | 108.1 |
C20—N2—C21 | 108.9 (2) | C13—C12—C11 | 111.3 (2) |
C20—N2—H2C | 125.5 | C13—C12—H12A | 109.4 |
C21—N2—H2C | 125.5 | C11—C12—H12A | 109.4 |
C6—C1—N1 | 119.7 (2) | C13—C12—H12B | 109.4 |
C6—C1—C2 | 123.9 (2) | C11—C12—H12B | 109.4 |
N1—C1—C2 | 116.3 (2) | H12A—C12—H12B | 108.0 |
C1—C2—C3 | 110.6 (2) | C8—C13—N1 | 119.8 (2) |
C1—C2—H2A | 109.5 | C8—C13—C12 | 123.9 (2) |
C3—C2—H2A | 109.5 | N1—C13—C12 | 116.2 (2) |
C1—C2—H2B | 109.5 | C21—C14—C15 | 105.8 (2) |
C3—C2—H2B | 109.5 | C21—C14—C7 | 126.8 (2) |
H2A—C2—H2B | 108.1 | C15—C14—C7 | 127.3 (2) |
C4—C3—C2 | 110.5 (2) | C16—C15—C20 | 119.3 (2) |
C4—C3—H3A | 109.5 | C16—C15—C14 | 133.7 (2) |
C2—C3—H3A | 109.5 | C20—C15—C14 | 106.9 (2) |
C4—C3—H3B | 109.5 | C17—C16—C15 | 117.4 (2) |
C2—C3—H3B | 109.5 | C17—C16—H16A | 121.3 |
H3A—C3—H3B | 108.1 | C15—C16—H16A | 121.3 |
C5—C4—C3 | 112.7 (2) | C16—C17—C18 | 123.2 (2) |
C5—C4—H4A | 109.1 | C16—C17—Br1 | 118.29 (19) |
C3—C4—H4A | 109.1 | C18—C17—Br1 | 118.48 (19) |
C5—C4—H4B | 109.1 | C19—C18—C17 | 120.0 (2) |
C3—C4—H4B | 109.1 | C19—C18—H18A | 120.0 |
H4A—C4—H4B | 107.8 | C17—C18—H18A | 120.0 |
O1—C5—C6 | 121.7 (2) | C18—C19—C20 | 117.8 (2) |
O1—C5—C4 | 120.7 (2) | C18—C19—H19A | 121.1 |
C6—C5—C4 | 117.5 (2) | C20—C19—H19A | 121.1 |
C1—C6—C5 | 120.2 (2) | N2—C20—C19 | 130.2 (2) |
C1—C6—C7 | 120.0 (2) | N2—C20—C15 | 107.7 (2) |
C5—C6—C7 | 119.7 (2) | C19—C20—C15 | 122.1 (2) |
C8—C7—C6 | 108.48 (19) | N2—C21—C14 | 110.7 (2) |
C8—C7—C14 | 110.51 (19) | N2—C21—H21A | 124.6 |
C6—C7—C14 | 111.30 (19) | C14—C21—H21A | 124.6 |
C13—N1—C1—C6 | −18.3 (3) | C7—C8—C13—N1 | 10.9 (3) |
C13—N1—C1—C2 | 159.9 (2) | C9—C8—C13—C12 | 9.5 (4) |
C6—C1—C2—C3 | −17.9 (3) | C7—C8—C13—C12 | −170.2 (2) |
N1—C1—C2—C3 | 164.0 (2) | C1—N1—C13—C8 | 17.0 (3) |
C1—C2—C3—C4 | 49.7 (3) | C1—N1—C13—C12 | −161.9 (2) |
C2—C3—C4—C5 | −54.8 (3) | C11—C12—C13—C8 | 12.8 (3) |
C3—C4—C5—O1 | −156.3 (2) | C11—C12—C13—N1 | −168.3 (2) |
C3—C4—C5—C6 | 26.5 (3) | C8—C7—C14—C21 | −22.8 (3) |
N1—C1—C6—C5 | 166.7 (2) | C6—C7—C14—C21 | 97.8 (3) |
C2—C1—C6—C5 | −11.4 (4) | C8—C7—C14—C15 | 159.4 (2) |
N1—C1—C6—C7 | −8.5 (3) | C6—C7—C14—C15 | −80.0 (3) |
C2—C1—C6—C7 | 173.4 (2) | C21—C14—C15—C16 | 174.8 (3) |
O1—C5—C6—C1 | −170.3 (2) | C7—C14—C15—C16 | −7.1 (4) |
C4—C5—C6—C1 | 6.9 (3) | C21—C14—C15—C20 | −1.1 (3) |
O1—C5—C6—C7 | 4.9 (4) | C7—C14—C15—C20 | 177.1 (2) |
C4—C5—C6—C7 | −177.9 (2) | C20—C15—C16—C17 | −0.7 (3) |
C1—C6—C7—C8 | 32.0 (3) | C14—C15—C16—C17 | −176.1 (2) |
C5—C6—C7—C8 | −143.2 (2) | C15—C16—C17—C18 | −3.5 (4) |
C1—C6—C7—C14 | −89.8 (3) | C15—C16—C17—Br1 | 174.75 (18) |
C5—C6—C7—C14 | 95.0 (2) | C16—C17—C18—C19 | 4.6 (4) |
C6—C7—C8—C13 | −33.3 (3) | Br1—C17—C18—C19 | −173.56 (19) |
C14—C7—C8—C13 | 89.0 (3) | C17—C18—C19—C20 | −1.4 (4) |
C6—C7—C8—C9 | 147.0 (2) | C21—N2—C20—C19 | −179.6 (2) |
C14—C7—C8—C9 | −90.7 (3) | C21—N2—C20—C15 | 0.1 (3) |
C13—C8—C9—O2 | −179.2 (2) | C18—C19—C20—N2 | 177.0 (2) |
C7—C8—C9—O2 | 0.5 (4) | C18—C19—C20—C15 | −2.7 (4) |
C13—C8—C9—C10 | 3.6 (3) | C16—C15—C20—N2 | −176.0 (2) |
C7—C8—C9—C10 | −176.7 (2) | C14—C15—C20—N2 | 0.6 (3) |
O2—C9—C10—C11 | 145.2 (2) | C16—C15—C20—C19 | 3.8 (3) |
C8—C9—C10—C11 | −37.5 (3) | C14—C15—C20—C19 | −179.6 (2) |
C9—C10—C11—C12 | 58.8 (3) | C20—N2—C21—C14 | −0.9 (3) |
C10—C11—C12—C13 | −46.2 (3) | C15—C14—C21—N2 | 1.2 (3) |
C9—C8—C13—N1 | −169.4 (2) | C7—C14—C21—N2 | −177.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O1 | 1.00 | 2.49 | 2.869 (3) | 102 |
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+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H19BrN2O2·C2H6OS |
Mr | 489.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 123 |
a, b, c (Å) | 9.1544 (4), 18.9619 (8), 12.9790 (5) |
β (°) | 105.623 (4) |
V (Å3) | 2169.72 (16) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.71 |
Crystal size (mm) | 0.51 × 0.23 × 0.12 |
Data collection | |
Diffractometer | Agilent Xcalibur (Ruby, Gemini) diffractometer |
Absorption correction | Analytical [CrysAlis PRO (Agilent, 2011), using a multi-faceted crystal model (Clark & Reid, 1995)] |
Tmin, Tmax | 0.272, 0.721 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14006, 4444, 4183 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.629 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.137, 1.06 |
No. of reflections | 4444 |
No. of parameters | 290 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.96, −1.35 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1 | 0.95 | 2.50 | 3.252 (3) | 136.1 |
N1—H1A···O2i | 0.88 | 2.03 | 2.901 (3) | 173.3 |
N2—H2C···O100ii | 0.88 | 2.10 | 2.920 (3) | 153.8 |
N2—H2C···O100iii | 0.88 | 2.52 | 3.038 (3) | 118.3 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, −y+3/2, z+1/2. |
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. Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Berkan, Ö., Saraç, B., Şimşek, R., Yildirim, Ş., Sarioglu, Y. & Şafak, C. (2002). Eur. J. Med. Chem. 37, 519–523. Web of Science CrossRef PubMed CAS Google Scholar
Biwersi, J., Tulk, B. & Verkman, A. S. (1994). Anal. Biochem. 219, 139-43. CrossRef CAS PubMed Web of Science Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Denny, W. (2002). Curr. Med. Chem. 9, 1655–1665. CrossRef PubMed CAS Google Scholar
Guetzoyan, L., Ramiandrasoa, F., Dorizon, H., Desprez, C., Bridoux, A., Rogier, C., Pradines, B. & Perree-Fauvet, M. (2007). Bioorg. Med. Chem. 15, 3278–3289. Web of Science CrossRef PubMed CAS Google Scholar
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. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Şimşek, R., Özkan, M., Kısmetli, E., Uma, S. & Şafak, C. (2004). Il Farmaco, 59, 939–943. PubMed Google Scholar
Wainwright, M. J. (2001). J. Antimicrob. Chemother. 47, 1–13. Web of Science CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).