N-(7-Eth­oxy-1H-indazol-4-yl)-4-methyl­benzene­sulfonamide

Najat Abbassi; El Mostapha Rakib; Hafid Zouihri

doi:10.1107/S1600536811016576

. 2011 May 7;67(Pt 6):o1354. doi: 10.1107/S1600536811016576

N-(7-Ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide

Najat Abbassi ^a, El Mostapha Rakib ^a,^*, Hafid Zouihri ^b

PMCID: PMC3120551 PMID: 21754748

Abstract

The molecule of the title heterocyclic compound, C₁₆H₁₇N₃O₃S, is bent at the S atom with an C—SO₂—NH—C torsion angle of 80.17 (8)°. The phenyl substituent at the S atom is rotated out of the plane of the 1H-indazole ring [interplanar angle = 46.24 (8)°]. In the crystal, intermolecular N—H⋯N and N—H⋯O hydrogen bonds build up a ribbon developing parallel to the b-axis direction. C—H⋯O hydrogen bonds link these ribbons, forming a layer parallel to the bc plane.

Related literature

For related structures, see: Shakuntala et al. (2011a ▶,b ▶); Khan et al. (2010 ▶); Gowda et al. (2010 ▶). For the biological activity of similar sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee, (2002 ▶).

Experimental

Crystal data

C₁₆H₁₇N₃O₃S
M _r = 331.39
Monoclinic,
a = 16.2579 (4) Å
b = 5.0291 (1) Å
c = 20.4551 (5) Å
β = 97.269 (1)°
V = 1659.02 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.23 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD detector diffractometer
31243 measured reflections
6745 independent reflections
5062 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.158
S = 1.07
6745 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016576/dn2681sup1.cif

e-67-o1354-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016576/dn2681Isup2.hkl

e-67-o1354-Isup2.hkl^{(330.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016576/dn2681Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811016576/dn2681Isup4.cml

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
C14—H14B⋯O1ⁱ	0.97	2.54	3.373 (3)	144
N1—H14⋯O2ⁱⁱ	0.85	2.07	2.9159 (15)	172
N2—H2A⋯N3ⁱⁱⁱ	0.86	2.21	2.8974 (15)	136

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

Similar sulfonamides have been studied in various previously works [Shakuntala et al. 2011a and 2011b; Khan et al. 2010; Gowda et al. 2010] and have proved important functionalities for biological and anti-hypertensive activities [Soledade et al., 2006; Lee & Lee, 2002].

In the title compound, C₁₆H₁₇N₃O₃S, the molecule is bent at the S atom with an C—SO₂—NH—C torsion angle of 80.17 (8)° (Fig. 1). In the crystal structure, intermolecular N—H···N and N—H···O hydrogen bonds build up a ribbon developping parallel to the b direction and the C—H···O link these reibons to form a two D layer parallel to the bc plane (Fig. 2, Table 1).

The S atom has a distorted tetrahedral geometry [maximum deviation: O—S—O = 119.87 (9)°]. The phenyl substituent at S1 atom is rotated out of the plane of the 1H-indazol ring (the interplanar angles is 46.24 (8)°).

Experimental

A mixture of 4-nitroindazole (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was heated at 60 °C for 2 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was made slightly basic (pH 7–8) by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methylbenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with Ethyl acetate: Hexane 1:9).

Yield: 45%; mp: 443–445 °K; IR (KBr, cm^-1): 3340, 3235 (NH), 1595 (CN), 1335, 1160 (SO₂); ¹H NMR (DMSO-d₆): 2.27 (s, 3H, CH3), 6.92 (dd, 1H, J=2.1 Hz and 6.1 Hz), 7.16 (d, 2H, J=6.2 Hz), 7.28 (d, 2H, J=8.3 Hz), 7.68 (d, 2H, J=8.3 Hz), 8.22 (s, 1H),10.51 (s, 1H, NH), 13.05 (s, 1H, NH); ¹³C NMR (DMSO-d₆): 21.3 (CH3), 106.7,111.0, 126.9, 127.2, 130.1, 132.4 (6 CH), 117.3, 130.5, 137.3, 141.4, 143.7 (5 C); MS m/z=288 [M+1].