Ethyl 2-(bromo­meth­yl)-5-meth­oxy-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

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

doi:10.1107/S1600536808007319

. 2008 Mar 20;64(Pt 4):o732. doi: 10.1107/S1600536808007319

Ethyl 2-(bromomethyl)-5-methoxy-1-phenylsulfonyl-1H-indole-3-carboxylate

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

PMCID: PMC2960959 PMID: 21202122

Abstract

In the title compound, C₁₉H₁₈BrNO₅S, the plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The Br atom is disordered over two positions, with site-occupancy factors of 0.833 (14) and 0.167 (14). 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.

Related literature

For biological activity, see: Nieto et al. (2005 ▶); Yang et al. (2002 ▶). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C₁₉H₁₈BrNO₅S
M _r = 452.31
Triclinic,
a = 8.9988 (3) Å
b = 9.2343 (2) Å
c = 11.6068 (3) Å
α = 82.524 (1)°
β = 87.666 (2)°
γ = 84.942 (3)°
V = 952.16 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 295 (2) K
0.20 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.593, T _max = 0.692
25160 measured reflections
6169 independent reflections
4163 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.127
S = 1.03
6169 reflections
254 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.89 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/S1600536808007319/rk2082sup1.cif

e-64-0o732-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007319/rk2082Isup2.hkl

e-64-0o732-Isup2.hkl^{(295.8KB, 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
C12—H12⋯O1ⁱ	0.93	2.56	3.472 (3)	165
C2—H2⋯O5ⁱⁱ	0.93	2.60	3.235 (3)	126
C6—H6⋯O2	0.93	2.54	2.908 (4)	104
C10—H10⋯O4	0.93	2.37	2.892 (3)	116
C13—H13⋯O1	0.93	2.28	2.863 (3)	120
C15—H15A⋯O5	0.97	2.31	2.911 (4)	119
C15—H15D⋯O2	0.97	2.16	2.895 (4)	131

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

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 anti–bacterial (Nieto et al., 2005) anti–tumour (Yang et al., 2002) activities, we report the crystal structure of the title compound (I). The geometric parameters of the molecule of I (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008).

The plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The N1—S1—C1 plane is orthogonal to indole ring (dihedral angle 88.70 (7)°) and makes 75.97 (9)° with the phenyl ring. The plane of indole ring is almost coplanar (dihedral angle 2.66 (7)°) with the ester group and makes 6.33 (18)° with the methoxy group.

The torsion angles O2–S1–N1–C7 and O1–S1–N1–C14 [-30.0 (2)° and 27.3 (2)°, respectively] indicate syn–conformation of the sulfonyl moiety. The Br1 atom is disordered over two positions with the site occupancy factors of 0.833 (14) and 0.167 (14). The molecular packing is stabilized by weak intramolecular C—H···O interactions and the crystal packing of I (Fig. 2) is stabilized by weak intermolecular C—H···O interactions (see Table).

Experimental

Ethyl 2-(methyl)-5-methoxy-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1g, 2.2 mmol), N–bromo succinimide (0.4 g, 2.3 mmol), azo–bis–isobutyronitrile (50 mg) were dissolved in 50 ml of carbon tetrachloride. Refluxed on a waterbath for 2hr. Cooled to room temperature. Succinimide was filtered off over sodium sulfate. Filtrate was evaporated under reduced pressure. Product was recrystallized from methanol. Yield: 78%.