N-(1H-Indazol-5-yl)-4-meth­oxy­benzene­sulfonamide

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

doi:10.1107/S1600536813028912

. 2013 Oct 26;69(Pt 11):o1702. doi: 10.1107/S1600536813028912

N-(1H-Indazol-5-yl)-4-methoxybenzenesulfonamide

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

PMCID: PMC3884352 PMID: 24454128

Abstract

In the title compound, C₁₄H₁₃N₃O₃S, the fused ring system is almost planar, the largest deviation from the mean plane being 0.023 (2) Å, and makes a dihedral angle of 47.92 (10)° with the benzene ring of the benzenesulfonamide moiety. In the crystal, molecules are connected through N—H⋯O hydrogen bonds and weak C—H⋯O contacts, forming a two-dimensional network which is parallel to (010).

Related literature

For the pharmacological activity of selected sulfonamide derivatives, see: El-Sayed et al. (2011 ▶); Smith & Jones (2008 ▶); Scozzafava et al. (2003 ▶). For similar compounds, see: Bouissane et al. (2006 ▶); Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2013 ▶). graphic file with name e-69-o1702-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₃N₃O₃S
M _r = 303.33
Monoclinic,
a = 8.9996 (4) Å
b = 7.1999 (3) Å
c = 21.3728 (10) Å
β = 91.794 (3)°
V = 1384.20 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.41 × 0.36 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.912, T _max = 0.954
14415 measured reflections
3059 independent reflections
2234 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.119
S = 1.05
3059 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 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/S1600536813028912/im2443sup1.cif

e-69-o1702-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028912/im2443Isup2.hkl

e-69-o1702-Isup2.hkl^{(147.1KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813028912/im2443Isup3.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
N1—H1N⋯O1ⁱ	0.90	2.07	2.956 (2)	168
N3—H3N⋯O2ⁱⁱ	0.77	2.23	2.998 (2)	172
C6—H6⋯O2ⁱ	0.93	2.52	3.381 (2)	155

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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 are an important class of compounds which are widely used in the design of diverse classes of drug candidates (El-Sayed et al., 2011; Smith & Jones, 2008; Scozzafava et al., 2003). 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, 2013; Bouissane et al., 2006; Chicha et al., 2013).

The molecule of the title compound is built up from two fused five- and six-membered rings (N1/N2/C1 to C7) linked to the 4-methoxybenzenesulfonamide group, as shown in Fig. 1. The fused ring system is almost planar, with the maximum deviation of -0.023 (2) Å arising from atom C1. Moreover, the dihedral angle between the indazole system and the plan through the atoms forming the benzene ring (C8 to C13) is 47.92 (10)°.

In the crystal, molecules are connected through N—H···O hydrogen bonds and weak C—H···O contacts, forming a two-dimensional network nearly parallel to (0 1 0) as shown in Fig.2 and Table 1.

2. Experimental

A mixture of 5-nitroindazole (216 mg, 1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 ml of absolute ethanol was heated at 333 K 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-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 2:8, yield: 54%, m.p.: 437 K). The title compound was recrystallized from ethanol.