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

Hakima Chicha; El Mostapha Rakib; Detlef Geffken; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536813021624

. 2013 Aug 7;69(Pt 9):o1398. doi: 10.1107/S1600536813021624

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

Hakima Chicha ^a,^*, El Mostapha Rakib ^a, Detlef Geffken ^b, Mohamed Saadi ^c, Lahcen El Ammari ^c

PMCID: PMC3884501 PMID: 24427037

Abstract

The indazole ring system [maximum deviation = 0.013 (2) Å] of the title compound, C₁₅H₁₅N₃O₃S, makes a dihedral angle of 50.11 (7)° with the benzene ring. In the crystal, cohesion is provided by C—H⋯O and N—H⋯N hydrogen bonds, which link the molecules into chains propagating along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006 ▶); El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2013 ▶). graphic file with name e-69-o1398-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₅N₃O₃S
M _r = 317.36
Monoclinic,
a = 10.1069 (3) Å
b = 13.6178 (3) Å
c = 10.8530 (2) Å
β = 90.777 (2)°
V = 1493.60 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.39 × 0.33 × 0.23 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.651, T _max = 0.747
19007 measured reflections
4178 independent reflections
3232 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.125
S = 1.02
4178 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 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/S1600536813021624/bt6924sup1.cif

e-69-o1398-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021624/bt6924Isup2.hkl

e-69-o1398-Isup2.hkl^{(200.6KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813021624/bt6924Isup3.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	0.89	2.25	3.1335 (19)	176
C8—H8A⋯O1ⁱⁱ	0.96	2.49	3.391 (2)	157

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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 the most of the 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 (Abbassi et al., 2012; Bouissane et al., 2006; El-Sayed et al., 2011; Mustafa et al., 2012). The present work is a continuation of the investigation of the sulfonamide derivatives published recently by our team (Abbassi et al., 2013; Chicha et al., 2013).

The molecule of 4-Methoxy-N-(1-methyl-1H-indazol-5-yl)-benzenesulfonamide is built up from the fused five- and six-membered rings (N2 N3 C1—C7) linked to the benzenesulfonamide group as shown in Fig. 1. The fused rings system is planar, with the maximum deviation of -0.013 (2) Å for N2 atom. Moreover, the dihedral angle between the indazole system and the plan through the atoms forming the benzene ring (C9—C14) is of 50.11 (7)°.

In the crystal, the molecules are interconnected by C8–H8A···O1 and N1–H1···N2 hydrogen bonds forming a one-dimensional chain running along the b axis as shown in Fig.2 and Table 2.

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-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). The title compound was recrystallized from acetone.