(E)-Methyl 3-(2-methyl-1-phenyl­sulfonyl-1H-indol-3-yl)but-2-enoate

T Kavitha; M Thenmozhi; G Gobi Rajeshwaran; A K Mohanakrishnan; M N Ponnuswamy

doi:10.1107/S1600536809002931

. 2009 Jan 31;65(Pt 2):o431. doi: 10.1107/S1600536809002931

(E)-Methyl 3-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)but-2-enoate

T Kavitha ^a, M Thenmozhi ^a, G Gobi Rajeshwaran ^b, A K Mohanakrishnan ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2968289 PMID: 21582017

Abstract

In the title compound, C₂₀H₁₉NO₄S, the indole ring system is planar [r.m.s. deviation = 0.023 (2) Å]. The sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 86.75 (7)°]. The ester group is almost planar (r.m.s. deviation = 0.030 Å) and is oriented at an angle of 62.53 (5)° with respect to the indole ring system. Molecules are linked into a two-dimensional network parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activities of indole and its derivatives, see: Chandrakantha et al. (1992 ▶); Rodriguez et al. (1985 ▶). For related literature For the configuration at the S atom, see: Bassindale (1984 ▶). For the N atom hybridization, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C₂₀H₁₉NO₄S
M _r = 369.42
Monoclinic,
a = 8.9498 (3) Å
b = 8.8427 (2) Å
c = 23.2836 (7) Å
β = 97.085 (1)°
V = 1828.60 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.957, T _max = 0.968
23203 measured reflections
5673 independent reflections
3833 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.137
S = 1.01
5673 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.30 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002931/ci2752sup1.cif

e-65-0o431-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002931/ci2752Isup2.hkl

e-65-0o431-Isup2.hkl^{(272.1KB, 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⋯O2ⁱ	0.93	2.58	3.391 (2)	146
C13—H13⋯O3ⁱⁱ	0.93	2.50	3.277 (2)	141

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

Acknowledgments

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

supplementary crystallographic information

Comment

Indole and its derivatives have long been known for their chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985).

Due to Thorpe–Ignold effect (Bassindale, 1984), bond angles around atom S1 show significant deviation from ideal tetrahedral value, with significant deviations in angles O1—S1—O2 [120.37 (9)°] and N1—S1—C10 [104.96 (6)°]. The indole ring system is essentially planar. The sum of the bond angles around atom N1 (355.9°) indicates sp² hybridization (Beddoes et al., 1986). The sulfonyl bound phenyl ring is oriented almost perpendicular to the indole ring system as can be seen from the dihedral angle of 86.75 (7)°. The ester group attached to the indole ring system adopts an extended conformation which is confirmed by the torsion angles C3—C17—C19—C20 = -177.59 (14)°, C17—C19—C20—O4 = -176.02 (15)° and C19—C20—O4—C21 = -178.62 (15)°.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network parallel to the ab plane (Fig. 2).

Experimental

To a stirred suspension of NaH (29 mg, 1.20 mmol, hexane washed) in THF (5 ml), a solution of vinyl indole (0.23 g, 1 mmol) in THF (5 ml) was added and stirred for 30 min at room temperature. To the reaction mixture, a solution of PhSO₂Cl (0.21 g, 1.20 mmol) was added and stirring was continued for further 6 h. After the indole was consumed (monitored by TLC), the reaction mixture was quenched with cold diluted HCl (25 ml), extracted with ethyl acetate (2 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by recrystallization (MeOH) afforded yellow crystals of the title compound.