N-(2-Allyl-4-eth­oxy-2H-indazol-5-yl)-4-methyl­benzene­sulfonamide

Hakima Chicha; El Mostapha Rakib; Latifa Bouissane; Maurizio Viale; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536814009283

. 2014 Apr 30;70(Pt 5):o624. doi: 10.1107/S1600536814009283

N-(2-Allyl-4-ethoxy-2H-indazol-5-yl)-4-methylbenzenesulfonamide

Hakima Chicha ^a, El Mostapha Rakib ^a, Latifa Bouissane ^a,^*, Maurizio Viale ^b, Mohamed Saadi ^c, Lahcen El Ammari ^c

PMCID: PMC4011273 PMID: 24860413

Abstract

The indazole ring system of the title compound, C₁₉H₂₁N₃O₃S, is almost planar (r.m.s. deviation = 0.0192 Å) and forms dihedral angles of 77.99 (15) and 83.9 (3)° with the benzene ring and allyl group, respectively. In the crystal, centrosymmetrically related molecules are connected by pairs of N—H⋯O hydrogen bonds into dimers, which are further linked by C—H⋯O hydrogen bonds, forming columns parallel to the b axis.

Related literature

For the biological activity of sulfonamides, see: Drews (2000 ▶); Supuran & Scozzafava (2001 ▶); Abbate et al. (2004 ▶); Rostom (2006 ▶); Ghorab et al. (2009 ▶). For similar compounds, see: Bouissane et al. (2006 ▶); Abbassi et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C₁₉H₂₁N₃O₃S
M _r = 371.45
Monoclinic,
a = 26.0808 (5) Å
b = 7.9335 (2) Å
c = 21.1573 (4) Å
β = 122.839 (1)°
V = 3678.13 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.42 × 0.35 × 0.30 mm

Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.693, T _max = 0.747
37135 measured reflections
4059 independent reflections
3100 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.134
S = 1.07
4059 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814009283/rz5122sup1.cif

e-70-0o624-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009283/rz5122Isup2.hkl

e-70-0o624-Isup2.hkl^{(199.1KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814009283/rz5122Isup3.cml

CCDC reference: 999285

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3ⁱ	0.84	2.14	2.960 (2)	164
C17—H17⋯O2ⁱⁱ	0.93	2.54	3.333 (3)	144

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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

1. Comment

Sulfonamides possess many types of biological activities and representatives of this class of pharmacological agents are widely used in clinic as antibacterial, hypoglycemic, diuretic and anti-carbonic anhydrase agents (Drews, 2000; Supuran & Scozzafava, 2001). Previously, a host of structurally novel sulfonamide derivatives have been reported to show substantial antitumor activity in vitro and/or in vivo (Abbate et al., 2004; Rostom, 2006; Ghorab et al., 2009). Recently, some N-[7(6)-indazolyl]arylsulfonamides prepared by our research group showed important antiproliferative activity against some human and murine cell lines ((Abbassi et al., 2012; Abbassi et al., 2013; Bouissane et al., 2006).

The molecule of the title compound is built up from two fused almost coplanar five- and six-membered rings (N1/N2/C4-C10), with a maximum deviation of 0.029 (3) Å for atom C9 (Fig. 1). The indazole ring system is nearly perpendicular to the planes through the allyl group (C1–C3) and benzene ring (C13–C18) as indicated by the dihedral angles between them of 83.9 (3) and 77.99 (15)°, respectively. An intramolecular C—H···O hydrogen bond (Table 1) stabilizes the molecular comformation. The cohesion of the crystal structure is ensured by N3–H3N···O3 hydrogen bonds between centrosymmetrically related molecules forming dimers, which are further connected into columns parallel to the b axis by C17–H17···O2 hydrogen bonds (Fig. 2, Table 1).

2. Experimental

A mixture of 2-allyl-5-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 6 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 (1.25 mmol) at room temperature for 24 h. The reaction mixture was then concentrated in vacuo and the resulting residue was purified by flash chromatography (eluted with ethyl acetate:hexane 2:8 v/v). The title compound was recrystallized from ethanol (yield = 78%, m. p. = 388 K).