(2-Methyl-1-phenyl­sulfonyl-1H-indol-3-yl)phenyl­methyl acetate

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

doi:10.1107/S1600536809044365

. 2009 Oct 28;65(Pt 11):o2906. doi: 10.1107/S1600536809044365

(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)phenylmethyl acetate

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

PMCID: PMC2970969 PMID: 21578487

Abstract

In the title compound, C₂₄H₂₁NO₄S, the indole ring system makes dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the S- and C-bound phenyl rings. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond. In the crystal, a weak intermolecular C—H⋯O hydrogen bond and a C—H⋯π interaction are also observed.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006 ▶); Olgen & Coban (2003 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C₂₄H₂₁NO₄S
M _r = 419.48
Monoclinic,
a = 14.3655 (6) Å
b = 8.3432 (4) Å
c = 18.6261 (8) Å
β = 108.086 (2)°
V = 2122.12 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.951, T _max = 0.968
23327 measured reflections
4712 independent reflections
3030 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.146
S = 1.01
4712 reflections
273 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.35 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/S1600536809044365/is2478sup1.cif

e-65-o2906-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044365/is2478Isup2.hkl

e-65-o2906-Isup2.hkl^{(226.2KB, 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
C13—H13⋯O1	0.93	2.39	2.977 (4)	121
C24—H24B⋯O2ⁱ	0.96	2.58	3.429 (4)	147
C15—H15A⋯Cg1ⁱⁱ	0.96	2.97	3.590 (3)	124

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C17–C22 ring.

Acknowledgments

The authors acknowledge SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

In continuation of our studies of indole derivatives, which are known to exhibit antihepatitis B virus (Chai et al., 2006) and anti-oxidant activity (Olgen & Coban, 2003), we report the crystal structure of the title compound, (I). The bond lengths and bond angles of the title compound are agree with the reported similar structures (Chakkaravarthi et al., 2007,2008).

The phenyl rings C1—C6 and C17—C22 make dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the indole ring system. The two phenyl rings are inclined at an angle of 62.2 (1)° with respect to each other. The torsion angles C7—N1—S1—O2 and C14—N1—S1—O1 [-36.8 (2) and 51.1 (2)°, respectively] indicate a syn conformation of the sulfonyl moiety. The sum of the bond angles around N1 [351.2 (2)°] indicates that N1 is sp²-hybridized.

The molecular structure is controlled by a weak intramolecular C—H···O hydrogen bond and the crystal packing of (I) (Fig. 2) is through weak intermolecular C—H···O hydrogen bonds and C—H···π (Table 1) interactions.

Experimental

To a solution of 1-phenylsulfonyl-(2-methyl-1H-indol-3-yl) (phenyl)methanol (0.5 g, 1.32 mmol) in dry DCM (20 ml) acetic anhydride (0.27 g, 2.64 mmol) and pyridine (0.2 g, 2.52 mmol) were added. It was then stirred at room temperature for 7 h under N₂ atmosphere. The reaction mixture was poured over crushed ice (100 g) containing 2 ml of Conc. HCl, extracted with CHCl₃ (3 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by recrystallization from CDCl₃ afforded the compound as crystals.