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

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3337

doi:10.1107/S1600536812045886

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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 and Cihat Şafak ^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

(Received 31 October 2012; accepted 6 November 2012; online 10 November 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 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

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); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045886/hg5266sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812045886/hg5266Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability ellipsoids for non-H atoms. Only major disordered component for the solvent molecule is shown.
	Fig. 2. The packing of (I), viewed down a axis, showing molecules are linked into plane parallel to bc plane. Only major disordered component for the solvent molecule is shown and hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₁H₁₉BrN₂O₂·C₂H₆OS	F(000) = 1008
M_r = 489.42	D_x = 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

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	4444 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.7°, θ_min = 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
T_min = 0.272, T_max = 0.721	l = −15→16
14006 measured reflections

Refinement top

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(F_o²) + (0.0699P)² + 3.3586P] where P = (F_o² + 2F_c²)/3
4444 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 1.96 e Å⁻³
6 restraints	Δρ_min = −1.35 e Å⁻³

Crystal data top

C₂₁H₁₉BrN₂O₂·C₂H₆OS	V = 2169.72 (16) Å³
M_r = 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)°

Data collection top

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)
T_min = 0.272, T_max = 0.721	R_int = 0.041
14006 measured reflections

Refinement top

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

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)]
T_min, T_max	0.272, 0.721
No. of measured, independent and observed [I > 2σ(I)] reflections	14006, 4444, 4183
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	1.96, −1.35

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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
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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
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Volume 68| Part 12| December 2012| Page o3337

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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