Crystal structure of N-(1-allyl-3-chloro-4-eth­oxy-1H-indazol-5-yl)-4-meth­oxybenzene­sulfonamide

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

doi:10.1107/S1600536814018492

. 2014 Aug 20;70(Pt 9):o1029–o1030. doi: 10.1107/S1600536814018492

Crystal structure of N-(1-allyl-3-chloro-4-ethoxy-1H-indazol-5-yl)-4-methoxybenzenesulfonamide

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

PMCID: PMC4186176 PMID: 25309208

Abstract

In the title compound, C₁₉H₂₀ClN₃O₄S, the benzene ring is inclined to the indazole ring system (r.m.s. deviation = 0.014 Å) by 65.07 (8)°. The allyl and ethoxy groups are almost normal to the indazole ring, as indicated by the respective torsion angles [N—N—C—C = 111.6 (2) and C—C—O—C = −88.1 (2)°]. In the crystal, molecules are connected by N—H⋯N hydrogen bonds, forming helical chains propagating along [010]. The chains are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure, indazole, benzenesulfonamide, hydrogen bonds

Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶); Bouissane et al. (2006 ▶); Ghorab et al. (2009 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2014 ▶).

Experimental

Crystal data

C₁₉H₂₀ClN₃O₄S
M _r = 421.89
Monoclinic,
a = 8.2699 (7) Å
b = 13.1235 (12) Å
c = 10.0026 (9) Å
β = 110.379 (5)°
V = 1017.64 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.42 × 0.32 × 0.28 mm

Data collection

Bruker X8 APEX Diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.670, T _max = 0.746
12792 measured reflections
5605 independent reflections
4754 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.088
S = 1.03
5605 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ▶)
Absolute structure parameter: −0.04 (4)

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/S1600536814018492/su2771sup1.cif

e-70-o1029-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018492/su2771Isup2.hkl

e-70-o1029-Isup2.hkl^{(274.4KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814018492/su2771Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S1600536814018492/su2771fig1.tif

A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(2.3MB, tif)}

. DOI: 10.1107/S1600536814018492/su2771fig2.tif

A partial view of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1019238

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—H1N⋯N2ⁱ	0.84	2.11	2.931 (2)	166
C19—H19A⋯O3ⁱⁱ	0.96	2.37	3.285 (2)	159
C3—H3B⋯O2ⁱⁱⁱ	0.97	2.47	3.418 (3)	165

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for financial support.

supplementary crystallographic information

S1. Experimental

A mixture of 1-allyl-3-chloro-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. 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). Crystals of the title compound were obtained by recrystallization from ethanol (yield = 43%; m.p. = 397 K).