4-Methyl-N-(1-methyl-1H-indazol-5-yl)benzene­sulfonamide

Hakima Chicha; Bassou Oulemda; El Mostapha Rakib; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536813023398

. 2013 Aug 23;69(Pt 9):o1471. doi: 10.1107/S1600536813023398

4-Methyl-N-(1-methyl-1H-indazol-5-yl)benzenesulfonamide

Hakima Chicha ^a,^*, Bassou Oulemda ^a, El Mostapha Rakib ^a, Mohamed Saadi ^b, Lahcen El Ammari ^b

PMCID: PMC3884404 PMID: 24427093

Abstract

In the title compound, C₁₅H₁₅N₃O₂S, the fused ring system is close to planar, the largest deviation from the mean plane being 0.030 (2) Å, and makes a dihedral angle of 48.84 (9)° with the benzene ring belonging to the methylbenzenesulfonamide moiety. In the crystal, molecules are connected through N—H⋯N hydrogen bonds and weak C—H⋯O contacts, forming a two-dimensional network parallel to (001).

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006 ▶); Mustafa et al. (2012 ▶); Lopez et al. (2010 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶). graphic file with name e-69-o1471-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₅N₃O₂S
M _r = 301.36
Monoclinic,
a = 8.0026 (3) Å
b = 12.8195 (4) Å
c = 14.1321 (4) Å
β = 91.602 (2)°
V = 1449.24 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.43 × 0.36 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.992
17896 measured reflections
4048 independent reflections
2703 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.134
S = 1.02
4048 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.25 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/S1600536813023398/bh2482sup1.cif

e-69-o1471-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023398/bh2482Isup2.hkl

e-69-o1471-Isup2.hkl^{(194.4KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813023398/bh2482Isup3.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—H1⋯N2ⁱ	0.88	2.21	3.065 (2)	166
C3—H3⋯O2ⁱⁱ	0.93	2.53	3.277 (2)	137

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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

Sulfonamide derivatives are well known pharmaceutical agents since this group has been the main functional part of many drug structures, due to stability and tolerance in human beings. These compounds exhibit a wide range of biological activities, such as anticancer, anti-inflammatory, and antiviral functions (Bouissane et al., 2006; Mustafa et al., 2012; Lopez et al., 2010). The present work is a continuation of the investigation on sulfonamide derivatives published recently by our team (Abbassi et al., 2012, 2013).

The molecule of 4-methyl-N-(1-methyl-1H-indazol-5-yl)-benzenesulfonamide is built up from two fused five- and six-membered rings (N2/N3/C1 to C7) linked to the benzenesulfonamide group, as shown in Fig. 1. The fused rings system is almost planar, with the maximum deviation of 0.030 (2) Å arising from atom C1. Moreover, the dihedral angle between the indazole system and the plan through the atoms forming the benzene ring (C9 to C14) is 48.84 (9)°.

In the crystal, the molecules are interconnected through C3—H3···O2ⁱⁱ weak contacts and N1—H1···N2ⁱ hydrogen bonds, forming a two-dimensional network (Fig. 2 and Table 2; symmetry codes: (i) -x + 1, y + 1/2, -z + 1/2; (ii) x + 1, y, z).

2. Experimental

A mixture of 1-methyl-5-nitroindazole (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-methylbenzenesulfonyl 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). The title compound was recrystallized from acetone.