Ethyl 2-(3,4-dimethoxy­benz­yl)-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

B Gunasekaran; Radhakrishnan Sureshbabu; A K Mohanakrishnan; G Chakkaravarthi; V Manivannan

doi:10.1107/S1600536809026506

. 2009 Jul 15;65(Pt 8):o1856. doi: 10.1107/S1600536809026506

Ethyl 2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indole-3-carboxylate

B Gunasekaran ^a, Radhakrishnan Sureshbabu ^b, A K Mohanakrishnan ^b, G Chakkaravarthi ^c, V Manivannan ^d,^*

PMCID: PMC2977166 PMID: 21583554

Abstract

In the title compound, C₂₆H₂₅NO₆S, the phenyl ring forms a dihedral angle of 82.5 (1)° with the indole ring system. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal structure is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For the biological activity of indoles see: Macor et al. (1992 ▶); Williams et al. (1993 ▶); For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶). For graph set notation see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₂₅NO₆S
M _r = 479.53
Triclinic,
a = 9.2914 (3) Å
b = 9.3008 (3) Å
c = 14.1561 (5) Å
α = 87.367 (2)°
β = 76.158 (2)°
γ = 87.877 (2)°
V = 1186.13 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.958, T _max = 0.972
26965 measured reflections
5046 independent reflections
3632 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.124
S = 1.03
5046 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.18 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026506/bt2993sup1.cif

e-65-o1856-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026506/bt2993Isup2.hkl

e-65-o1856-Isup2.hkl^{(242.1KB, 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
C6—H6⋯O1	0.93	2.56	2.911 (3)	103
C8—H8⋯O2	0.93	2.31	2.894 (3)	121
C11—H11⋯O4	0.93	2.36	2.885 (2)	115
C18—H18A⋯O1	0.97	2.23	2.855 (3)	122
C18—H18B⋯O3	0.97	2.33	2.930 (3)	119
C25—H25B⋯O1ⁱ	0.96	2.38	3.231 (3)	147
C9—H9⋯O2ⁱⁱ	0.93	2.58	3.503 (3)	174

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

Acknowledgments

Author thanks AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

The chemistry of indole has been of increasing interest, since several compounds of this type possess diverse biological activities (Macor et al., 1992). In addition, phenylsulfonyl indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993).

The geometric parameters of the title compound, (I), (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl ring makes a dihedral angle of 82.5 (1)° with the indole ring system. The two aromatic rings C1—C6 and C19—C24 are inclined at an angle of 44.2 (1)° with respect to each other. The sum of the bond angles around N1 [358.8 (5)°] indicate the sp² hybridized state. The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [27.8 (2) ° and -37.1 (2) °, respectively] indicate the syn conformation of the sulfonyl moiety.

A distorted tetrahedral geometry [O1—S1—O2 = 120.4 (1) ° and O1—S1—N1 = 106.9 (1) °] around S1 is observed. The widening of the angles may be due to repulsive interactions between the two short S=O bonds.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions. The C6—H6···O1 interaction generate an S(5) graph set motif and C8—H8···O2 and C11—H11···O4 interactions generate S(6) graph set motifs (Bernstein et al., 1995).

Experimental

Ethyl 2-(acetoxymethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (0.39 g, 0.97 mmol) was dissolved in dry 1,2-dichloroethane (15 ml). To this, anhydrous Ferric chloride (0.02 g, 0.09 mmoL) and 1,2-dimethoxy benzene (0.15 ml, 1.16 mmoL) were added under nitrogen atmosphere. It was refluxed for 5 hr and cooled to room temperature. Ferric chloride was carefully filtered off and the filtrate was poured to water (50 ml) and extracted with chloroform (30 ml). The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the product. It was recrystallized from methanol. Yield: 0.28 g (61%), M.Pt: 134–136°C.