Ethyl 3-[6-(4-meth­oxy­benzene­sulfon­amido)-2H-indazol-2-yl]propano­ate monohydrate

Najat Abbassi; El Mostapha Rakib; Abdellah Hannioui; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536812051975

. 2013 Jan 9;69(Pt 2):o190–o191. doi: 10.1107/S1600536812051975

Ethyl 3-[6-(4-methoxybenzenesulfonamido)-2H-indazol-2-yl]propanoate monohydrate

Najat Abbassi ^a,^*, El Mostapha Rakib ^a, Abdellah Hannioui ^a, Mohamed Saadi ^b, Lahcen El Ammari ^b

PMCID: PMC3569252 PMID: 23424475

Abstract

In the title compound, C₁₉H₂₁N₃O₅S·H₂O, the central indazole system is essentially planar (r.m.s. deviation = 0.012 Å), while both the benzene ring and the mean plane defined by the non-H atoms of the ethyl propionic ester unit (r.m.s. deviation = 0.087 Å) are nearly perpendicular to the indazole plane, as indicated by the dihedral angles of 82.45 (8) and 75.62 (8)°, respectively. Consequently, the molecule adopts a U-shaped geometry. In the crystal, the water molecule, which is linked to the indazole system by a strong O—H⋯N hydrogen bond, is also involved in two additional N—H⋯O and O—H⋯O interactions, which link the organic molecules into chains along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamides, see: Gadad et al. (2000 ▶); Brzozowski et al. (2010 ▶); Drew (2000 ▶); Garaj et al. (2005 ▶). For their antiproliferative activity see: Abbassi et al. (2012 ▶); Bouissane et al. (2006 ▶).

Experimental

Crystal data

C₁₉H₂₁N₃O₅S·H₂O
M _r = 421.46
Monoclinic,
a = 9.0248 (3) Å
b = 8.7602 (3) Å
c = 13.1792 (4) Å
β = 101.062 (2)°
V = 1022.58 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.42 × 0.37 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer
10050 measured reflections
4021 independent reflections
3887 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.077
S = 1.05
4021 reflections
262 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1779 Friedel pairs
Flack parameter: 0.03 (6)

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

Click here for additional data file.^{(28.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051975/lr2095sup1.cif

e-69-0o190-sup1.cif^{(28.5KB, cif)}

Click here for additional data file.^{(197.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051975/lr2095Isup2.hkl

e-69-0o190-Isup2.hkl^{(197.1KB, hkl)}

Click here for additional data file.^{(7.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812051975/lr2095Isup3.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
O6—H6A⋯N2	0.86	1.94	2.8029 (19)	176
N1—H1⋯O6ⁱ	0.81	1.95	2.7575 (19)	177
O6—H6B⋯O1ⁱⁱ	0.86	2.10	2.9094 (17)	156

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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

Comment

Sulfonamides constitute an important class of drugs. They possess various types of pharmacological activities such as antibacterial (Gadad et al., 2000), anti-carbonic anhydrase (Brzozowski et al., 2010), hypoglycemic (Drew, 2000), and anticancer activity (Garaj et al., 2005). Recently, our research group has reported the synthesis of some new N-(6(4)-indazolyl)aylsulfonamide derivatives. Some of these compounds showed an important antiproliferative activity against some human and murine cell lines (Abbassi et al., 2012; Bouissane et al., 2006).

The crystal structure of the Ethyl-3-[6-(4-methoxybenzenesulfonamido)-2H- indazol-2-yl]-propanoate monohydrate is built up from two fused five- and six-membered rings (N2 N3 C1 to C7) virtually coplanar, with a maximum deviation of 0.021 (2) A Å for C2 atom as shown in Fig.1. Moreover, the two cycles are nearly perpendicular to the plan through the atoms forming the propionic acid ester group (O3O4 C9 to C11) and to benzene ring (C13 to C18) as indicated by the dihedral angles between them of 75.62 (8)° and 82.45 (8)° respectively. As a matter of fact, the molecule has a U shaped geometry.

The cohesion of the crystal structure is ensured by three classic strong hydrogen bonds between the water and the organic molecules: O6–H6A···N2, N1–H1···O6 and O6–H6B···O1, as shown in Fig.2 and Table 2.

Experimental

A mixture of ethyl 3-(6-nitro-2H-indazol-2-yl)propanoate 1 (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 ml of absolute ethanol was heated at 333 K for 3 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).