3-(4-Methoxy­benz­yl)-2-methyl-1-phenyl­sulfonyl-1H-indole

T Kavitha; M Thenmozhi; V Dhayalan; A K Mohanakrishnan; M N Ponnuswamy

doi:10.1107/S1600536809010046

. 2009 Mar 25;65(Pt 4):o847. doi: 10.1107/S1600536809010046

3-(4-Methoxybenzyl)-2-methyl-1-phenylsulfonyl-1H-indole

T Kavitha ^a, M Thenmozhi ^a, V Dhayalan ^b, A K Mohanakrishnan ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2968905 PMID: 21582566

Abstract

There are two crystallographically independent molecules in the asymmetric unit of the title compound, C₂₃H₂₁NO₃S. The indole ring system is approximately perpendicular to the sulfonyl phenyl ring in both molecules [dihedral angles = 85.42 (8) and 88.30 (9)°]. C—H⋯O interactions between molecules stabilize the crystal structure.

Related literature

For the Thorpe–Ingold effect, see: Bassindale (1984 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the biological activity of sulfur-containing compounds, see: De-Benedetti et al, (1985 ▶); Krishnaiah et al. (1995 ▶).

Experimental

Crystal data

C₂₃H₂₁NO₃S
M _r = 391.47
Triclinic,
a = 11.4366 (4) Å
b = 13.6021 (5) Å
c = 14.0001 (5) Å
α = 74.154 (1)°
β = 67.773 (2)°
γ = 88.848 (2)°
V = 1930.96 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.963, T _max = 0.970
45568 measured reflections
10459 independent reflections
7561 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.140
S = 1.07
10459 reflections
509 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.29 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010046/bt2902sup1.cif

e-65-0o847-sup1.cif^{(34.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010046/bt2902Isup2.hkl

e-65-0o847-Isup2.hkl^{(501.1KB, 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
C11A—H11A⋯O1Bⁱ	0.93	2.52	3.397 (2)	157
C11B—H11B⋯O1Aⁱⁱ	0.93	2.49	3.337 (2)	151
C15A—H15A⋯O3Bⁱⁱⁱ	0.93	2.53	3.398 (2)	155

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

Acknowledgments

TK thanks Dr Babu Varghese, SAIF, IIT– Madras, Chennai, India, for his help with the data collection.

supplementary crystallographic information

Comment

Many sulfur-containing compounds, such as sulfates, sulfones and sulfonamides, exhibit insecticidal, germicidal, antimicrobial and antibacterial activities (De-Benedetti et al., 1985; Krishnaiah et al., 1995).

The asymmetric unit contains two crystallographically independent molecules, A and B (Fig. 1). As a result of the electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1—C2 [1.4268 (24) Å and 1.4315 (25) Å] and N1—C5 [1.4180 (23) Å and 1.4160 (24) Å] in molecules A and B are longer than the mean value of 1.355 (14) Å (Allen et al., 1987). Atom S has a tetrahedral geometry, with the O—S—O and N—S—C angles deviating significantly from ideal value, and this may be attributed to the Thorpe-Ingold effect (Bassindale, 1984). The mean plane of the planar indole ring system and the sulfonyl bound phenyl ring are approximately perpendicular to each other in both the molecules A [85.41 (8)°] and B [88.30 (9)°]. The benzylphenyl rings are oriented at angles of 66.73 (8)° and 71.93 (8)° in molecules A & B, respectively.

In the crystal structure, C—H···O interactions (Table 2) link the molecules into linear chain extending along the a axis.

Experimental

1-Phenylsulfonyl-2-methyl-3-bromomethylindole (2 g, 5.49 mmol) was dissolved in dry CH₃CN (20 ml). To this anisole (0.89 ml, 8.23 mmol), ZnBr₂ (2.47 g, 10.96 mmol) were added and refluxed for 12 h. The reaction mixture was quenched with ice containing few drops of conc. HCl, extracted with CHCl₃ (3 × 5 ml) and dried Na₂SO₄. The solvent was removed under vacuo. Then crude was recrystallized from CDCl₃ to get the diffraction quality crystals.