(2-Methyl-1-phenyl­sulfonyl-1H-indol-3-yl)methanol

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

doi:10.1107/S1600536808003024

. 2008 Jan 30;64(Pt 2):o542. doi: 10.1107/S1600536808003024

(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)methanol

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

PMCID: PMC2960400 PMID: 21201561

Abstract

In the title compound, C₁₆H₁₅NO₃S, the plane of the phenyl ring forms a dihedral angle of 80.37 (8)° with the indole ring system. The crystal packing is stabilized by weak O—H⋯O hydrogen bonds which link the molecules into infinite chains along the a axis of the crystal.

Related literature

For biological activity, see: Nieto et al. (2005 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶). For the structure of closely related compounds, see: Chakkaravarthi et al. (2007 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₅NO₃S
M _r = 301.35
Triclinic,
a = 8.3780 (4) Å
b = 9.6969 (5) Å
c = 9.9630 (4) Å
α = 78.718 (2)°
β = 65.347 (3)°
γ = 78.884 (2)°
V = 715.77 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 (2) K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.920, T _max = 0.963
14857 measured reflections
4088 independent reflections
3267 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.241
S = 1.05
4088 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003024/ya2066sup1.cif

e-64-0o542-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003024/ya2066Isup2.hkl

e-64-0o542-Isup2.hkl^{(196.2KB, 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
O3—H3⋯O2ⁱ	0.82	2.59	3.276 (5)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

supplementary crystallographic information

Comment

In continuation of our studies of benzenesulfonamide derivatives, which are known to exhibit antibacterial (Nieto et al., 2005), anticancer and anti - HIV (Pomarnacka & Kozlarska-Kedra, 2003) activities, we determined the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with those reported for similar structures (Chakkaravarthi et al., 2007; Liu et al., 2007).

The plane of the phenyl ring forms the dihedral angle of 80.37 (8)° with the indole ring system. The N1—S1—C1 plane is also approximately orthogonal to indole (dihedral angle 79.21 (6)°) and makes an angle of 57.86 (11)° with the phenyl plane.

The crystal packing of (I) is stabilized by a rather weak O—H···O bonds which link the molecules into the infinite chains along the x-axis of the crystal (Fig. 2, Table 2).

Experimental

Benzenesulfonyl chloride (7.75 ml, 43.9 mmol), 60% NaOH solution (60 g in 100 ml), along with tetrabutylammonium hydrogensulfate (1.5 g) were added to the solution of 2-methylindole-3-carboxaldehyde (8.0 g, 50.3 mmol) in distilled benzene (200 ml). The two-phase system thus formed was stirred at room temperature for 2 h. It was then diluted with water (200 ml) and the organic layer was separated. The aqueous layer was extracted with benzene (two times by 30 ml). The combined organic layer was dried (Na₂SO₄). The benzene was then completely removed and the crude product was recrystallized from methanol to get 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde.

NaBH₄ (2.97 g, 78.60 mmol) was added slowly to a solution of 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde (3 g, 13.10 mmol) in THF (30 ml). The reaction mixture was stirred at room temperature for 3 hrs. Dilute HCl (10%) was cautiously added until the solution became acidic. After most of the THF was removed in vacuo, the solution was extracted with dichloromethane and dried (MgSO₄); the solvent was then removed under vacuo. The crude product thus obtained was recrystallized from 10% ethyl acetate/n-hexane.