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

Abbassi, N.; Rakib, E.M.; Hannioui, A.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536812051975

Volume 69
Part 2
Pages o190-o191
February 2013

Received 6 December 2012
Accepted 27 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.077
Data-to-parameter ratio = 15.3
Details

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

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

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: najat_abbassi@hotmail.com

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-HN hydrogen bond, is also involved in two additional N-HO and O-HO 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, P 2₁
a = 9.0248 (3) Å
b = 8.7602 (3) Å
c = 13.1792 (4) Å
= 101.062 (2)°
V = 1022.58 (6) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.077
S = 1.05
4021 reflections
262 parameters
1 restraint
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.28 e Å^-3
Absolute structure: Flack (1983), 1779 Friedel pairs
Flack parameter: 0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O6-H6AN2	0.86	1.94	2.8029 (19)	176
N1-H1O6ⁱ	0.81	1.95	2.7575 (19)	177
O6-H6BO1ⁱⁱ	0.86	2.10	2.9094 (17)	156
Symmetry codes: (i) x, y+1, z; (ii) $[-x+2, y-{\script{1\over 2}}, -z]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: LR2095 ).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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organic compounds