Diethyl 2-{[3-(2,4,6-trimethyl­benz­yl)-1-phenyl­sulfonyl-1H-indol-2-yl]methyl­idene}propane­dioate

B Saravanan; V Dhayalan; A K Mohanakrishnan; G Chakkaravarthi; V Manivannan

doi:10.1107/S1600536810019690

. 2010 May 29;66(Pt 6):o1509. doi: 10.1107/S1600536810019690

Diethyl 2-{[3-(2,4,6-trimethylbenzyl)-1-phenylsulfonyl-1H-indol-2-yl]methylidene}propanedioate

B Saravanan ^a, V Dhayalan ^b, A K Mohanakrishnan ^b, G Chakkaravarthi ^c, V Manivannan ^d,^*

PMCID: PMC2979489 PMID: 21579568

Abstract

In the title compound, C₃₂H₃₃NO₆S, the indole ring system makes dihedral angles of 62.78 (10) and 80.53 (8)°, respectively, with the phenyl and benzene rings. In the crystal, the molecules are linked through intermolecular C—H⋯O hydrogen bonds, forming a chain along the a axis. Between the chains, a weak aromatic π–π stacking interaction [centroid–centroid distance = 3.831 (2) Å] is observed.

Related literature

For the biological activity of indole derivatives, see: Ma et al. (2001 ▶); Zhao et al. (2002 ▶); Zhou et al. (2006 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C₃₂H₃₃NO₆S
M _r = 559.65
Triclinic,
a = 8.5103 (4) Å
b = 8.9540 (4) Å
c = 19.6546 (10) Å
α = 78.456 (3)°
β = 87.236 (4)°
γ = 86.736 (3)°
V = 1463.99 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.976
26660 measured reflections
7349 independent reflections
4328 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.211
S = 1.03
7349 reflections
370 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019690/is2550sup1.cif

e-66-o1509-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019690/is2550Isup2.hkl

e-66-o1509-Isup2.hkl^{(352.3KB, hkl)}

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
C10—H10⋯O4ⁱ	0.93	2.43	3.179 (4)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors wish to acknowledge DV University of Madras for the data collection.

supplementary crystallographic information

Comment

Indole derivatives are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001; Zhou et al., 2006; Zhao et al., 2002). In continuation of our studies in indole derivatives, we report the crystal structure of the title compound, (I). The geometric parameters of (I) (Fig. 1) agree with those in the reported structures (Chakkaravarthi et al., 2007, 2008).

The nine-membered indole ring system forms dihedral angles of 62.78 (10) and 80.53 (8)° with the phenyl ring (C1–C6) and benzene ring (C24–C29), respectively. The torsion angles O2—S1—N1—C7 and O1—S1—N1—C14 [-37.8 (2)° and 62.87 (18)°, respectively] indicate the syn-conformation of the sulfonyl moiety. The sum of the bond angles around N1 [342.1 (2)°] indicates that N1 is sp³-hybridized.

The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing of (I) (Fig. 2) exhibits weak intermolecular C—H···O (Table 1) and π–π interactions [Cg···Cg (-x, -y, 1-z) distance of 3.831 (2) Å]; Cg is the centroid of the C1–C6 ring.

Experimental

To a solution of diethyl-2-((3-(bromomethyl)-1-(phenylsulfonyl) -1H-indol-2-yl)methylene)malonate (0.3 g, 0.57 mmol) in dry 1,2-dichloroethane (15 ml), anhydrous ZnBr₂ (0.25 g, 1.11 mmol) and mesitylene (0.19 ml, 1.41 mmol) were added. It was then refluxed for 4 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by flash column chromatographic purification (n-hexane/ethyl acetate 98:2) led to the isolation of product as a colourless crystal.