Ethyl 3-[7-eth­oxy-6-(4-meth­oxy­benzene­sulfonamido)-2H-indazol-2-yl]propano­ate

Najat Abbassi; Bassou Oulemda; El Mostapha Rakib; Detlef Geffken; Hafid Zouihri

doi:10.1107/S1600536812007519

. 2012 Mar 3;68(Pt 4):o931. doi: 10.1107/S1600536812007519

Ethyl 3-[7-ethoxy-6-(4-methoxybenzenesulfonamido)-2H-indazol-2-yl]propanoate

Najat Abbassi ^a,^*, Bassou Oulemda ^a, El Mostapha Rakib ^a, Detlef Geffken ^b, Hafid Zouihri ^c

PMCID: PMC3343913 PMID: 22589994

Abstract

In the title compound, C₂₁H₂₅N₃O₆S, the dihedral angle between the methoxybenzene and indazole rings is 74.96 (5)°. The crystal packing is stabilized by an N—H⋯O hydrogen bond into a two-dimensional network. In addition, C—H⋯π interactions and a π–π contact, with a centroid–centroid distance of 3.5333 (6) Å, are observed. The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₂₁H₂₅N₃O₆S
M _r = 447.50
Triclinic,
a = 9.1163 (4) Å
b = 10.9161 (5) Å
c = 11.2959 (5) Å
α = 77.259 (2)°
β = 77.364 (2)°
γ = 88.562 (2)°
V = 1069.55 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.32 × 0.31 × 0.19 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.940, T _max = 0.964
21582 measured reflections
4187 independent reflections
3834 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.084
S = 1.06
4187 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.41 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 datablock(s) I, global. DOI: 10.1107/S1600536812007519/fj2520sup1.cif

e-68-0o931-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007519/fj2520Isup2.hkl

e-68-0o931-Isup2.hkl^{(205.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812007519/fj2520Isup3.cml

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

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

Cg1 is the centroid of the pyrazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.88	2.12	2.9779 (15)	164
C3—H3⋯O5ⁱⁱ	0.93	2.41	3.3277 (17)	168
C21—H21B⋯Cg1ⁱⁱⁱ	0.93	2.98	3.6660 (18)	130

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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

Various sulfonamides are widely used as anti-hypertensive (Soledade et al., 2006; Lee & Lee, 2002). In former papers, we reported the crystal structures of N-(7-ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide (Abbassi et al., 2011a) and N-[7-ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide (Abbassi et al., 2011b). In this communication, the crystal structure of N-[7-ethoxy-2-(prop-2-en-1-yl)-2H-indazol-6-yl]-4-methylbenzenesulfonamide is reported.

In the title compound, C₂₁H₂₅N₃O₆S, the dihedral angle between the methoxyphenyl and the indazole rings is: 74.96 (5)° (Fig. 1).

Two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N—H···O interactions (Table 1 and Fig. 2).

The crystal packing is stabilized by intermolecular N—H···O and C—H···O H-bonds and C—H···π interactions (Fig. 3). Also, π–π contacts are observed with centroid-centroid distance of 3.5333 (6) Å.

Experimental

A mixture of ethyl 3-(6-nitro-2H-indazol-2-yl)propanoate (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was heated at 60 °C for 3 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-methoxybenzenesulfonyl chloride (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).