N-[7-Eth­oxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methyl­benzene­sulfonamide

Najat Abbassi; El Mostapha Rakib; Hafid Zouihri

doi:10.1107/S1600536811019465

. 2011 Jun 4;67(Pt 7):o1561. doi: 10.1107/S1600536811019465

N-[7-Ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide

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

PMCID: PMC3151999 PMID: 21836974

Abstract

In the title compound, C₁₉H₂₁N₃O₃S, the C—SO₂—NH—C torsion angle is 103.72 (11)°. The almost planar indazole ring [r.m.s. deviation = 0.0202 (14) Å] is twisted away from the methylbenzene ring by 76.87 (7)°. The vinyl group is disordered over two orientations with site occupancies of 0.622 (10) and 0.378 (10). The S atom has a distorted tetrahedral geometry [maximum deviation: O—S—O = 119.18 (11)°]. An intramolecular C—H⋯O hydrogen bond occurs. In the crystal, two molecules are linked about a center of inversion by pairs of N—H⋯O hydrogen bonds, generating a dimer. C—H⋯π interactions are also observed.

Related literature

For a related structure, see: Abbassi et al. (2011b ▶). For the biological activity of sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee (2002 ▶). For the synthesis of 7-ethoxy-N-alkylindazole derivatives, see: Abbassi et al. (2011a ▶).

Experimental

Crystal data

C₁₉H₂₁N₃O₃S
M _r = 371.45
Triclinic,
a = 8.2208 (3) Å
b = 10.4985 (4) Å
c = 11.9655 (5) Å
α = 108.814 (2)°
β = 92.346 (2)°
γ = 107.500 (2)°
V = 921.33 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.32 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD detector diffractometer
23139 measured reflections
3629 independent reflections
3281 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.118
S = 1.08
3629 reflections
259 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.32 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/S1600536811019465/ng5164sup1.cif

e-67-o1561-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019465/ng5164Isup2.hkl

e-67-o1561-Isup2.hkl^{(177.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019465/ng5164Isup3.cml

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

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

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3ⁱ	0.86 (2)	2.15 (2)	3.002 (2)	171 (2)
C14—H14B⋯O1	0.97	2.35	2.974 (2)	121
C19—H19C⋯Cg1ⁱⁱ	0.96	2.87	3.622 (2)	136

Open in a new tab

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

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 a former paper, we reported the crystal structure of N-(7-ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide [Abbassi et al., 2011b]. In this communication, the crystal structure of N-[7-ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide is reported.

The title heterocyclic compound, C₁₉H₂₁N₃O₃S, is a new synthetic molecule whish is bent at the S atom with an C—SO~2~—NH—C torsion angle of 103.72 (11)°. The indazol planar ring [r.m.s. deviation: 0.0202 (14) Å] is twisted away from the methylbenzene ring by 76.87 (7)°. The vinyl group is disordered over two positions with site occupancies of 0.622 (10) and 0.378 (10). The S atom has a distorted tetrahedral geometry [maximum deviation: O—S—O = 119.17 (10)°].

In the crystal structure, the molecules are linked by N—H···O hydrogen bonds together with weak C—H···O interactions. There also exist C—H···Cg contacts between the methyl groups of the methylbenzene and the indazol rings. The crystal structure is further stabilized by intermolecular π–π stacking interactions [centroid–centroid distances = 3.6673 (9)–3.8109 (10) A °].

Experimental

A mixture of 1-allyl-4-nitro-1H-indazole [Abbassi et al., 2011a] (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).