3-Iodo-2-methyl-1-phenyl­sulfonyl-1H-indole

C Ramathilagam; Velu Saravanan; A K Mohanakrishnan; G Chakkaravarthi; P R Umarani; V Manivannan

doi:10.1107/S1600536811004685

. 2011 Feb 12;67(Pt 3):o632. doi: 10.1107/S1600536811004685

3-Iodo-2-methyl-1-phenylsulfonyl-1H-indole

C Ramathilagam ^a, Velu Saravanan ^b, A K Mohanakrishnan ^b, G Chakkaravarthi ^c, P R Umarani ^d, V Manivannan ^e,^*

PMCID: PMC3051985 PMID: 21522386

Abstract

In the title compound, C₁₅H₁₂INO₂S, the sulfonyl-bound phenyl ring forms a dihedral angle 82.84 (9)° with the indole ring system. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond. The crystal structure exhibits weak intermolecular C—H⋯π interactions and π–π interactions between the indole groups [centroid–centroid distance between the five-membered and six-membered rings of the indole group = 3.7617 (18) Å].

Related literature

For the biological properties of indole derivatives, see: Chai et al. (2006 ▶); Nieto et al. (2005 ▶). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C₁₅H₁₂INO₂S
M _r = 397.22
Monoclinic,
a = 10.7068 (3) Å
b = 16.2670 (4) Å
c = 8.5147 (2) Å
β = 104.540 (1)°
V = 1435.49 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 295 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.536, T _max = 0.648
21249 measured reflections
5276 independent reflections
3696 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.144
S = 1.06
5276 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −1.56 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 I, global. DOI: 10.1107/S1600536811004685/gk2346sup1.cif

e-67-0o632-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004685/gk2346Isup2.hkl

e-67-0o632-Isup2.hkl^{(253.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.29	2.871 (4)	120
C4—H4⋯Cg3ⁱ	0.93	2.65	3.517 (5)	156

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

CR wishes to acknowledge AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Indole derivatives exhibit antihepatitis B virus (Chai et al., 2006) and antibacterial (Nieto et al., 2005) activities. The geometric parameters of the title molecule (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al. 2007, 2008).

The phenyl ring makes the dihedral angle of 82.84 (9)° with the indole ring system. The sum of the bond angles around N1 [359.4 (2)°] indicates that N1 atom is sp² hybridized. The molecular structure is stabilized by weak intramolecular C—H···O hydrogen bond. The crystal structure exhibits weak intermolecular C—H···π (Table 1) and π–π interactions [Cg1···Cg3 (1 - x,-y,1 - z) 3.7617 (18) Å; Cg1 and Cg3 are the centroids of the rings N1/C7/C8/C9/C14 and C9—C14, respectively].

Experimental

3-Iodo-2-methylindole (5 g,0.02 mmole) was dissolved in distilled benzene (100 ml).To this, benzenesulfonyl chloride(3.23 ml,0.025 mmol) and 60% aqueous NaOH solution (40 g in 67.0 ml) were added along with tetrabutyl ammonium hydrogensulfate (1.0 g). This two phase system 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 (2x20 ml). The combined organic layer was dried(Na₂SO₄).The benzene was then removed completely and the crude product was recrystallized from methanol (m.p. 395–397 K).