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

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o190-o191

doi:10.1107/S1600536812051975

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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

(Received 6 December 2012; accepted 27 December 2012; online 9 January 2013)

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, P 2₁
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[F² > 2σ(F²)] = 0.031
wR(F²) = 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)

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
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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051975/lr2095sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812051975/lr2095Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. A view of crystal packing showing the water units linking the organic molecules in chains along the b axis.

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

Crystal data top

C₁₉H₂₁N₃O₅S·H₂O	F(000) = 444
M_r = 421.46	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2yb	Cell parameters from 4021 reflections
a = 9.0248 (3) Å	θ = 2.3–26.4°
b = 8.7602 (3) Å	µ = 0.20 mm⁻¹
c = 13.1792 (4) Å	T = 296 K
β = 101.062 (2)°	Block, colourless
V = 1022.58 (6) Å³	0.42 × 0.37 × 0.28 mm
Z = 2

Data collection top

Bruker X8 APEX diffractometer	3887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 26.4°, θ_min = 2.3°
ϕ and ω scans	h = −11→11
10050 measured reflections	k = −10→10
4021 independent reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.037P)² + 0.2529P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4021 reflections	Δρ_max = 0.28 e Å⁻³
262 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1779 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (6)

Crystal data top

C₁₉H₂₁N₃O₅S·H₂O	V = 1022.58 (6) Å³
M_r = 421.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.0248 (3) Å	µ = 0.20 mm⁻¹
b = 8.7602 (3) Å	T = 296 K
c = 13.1792 (4) Å	0.42 × 0.37 × 0.28 mm
β = 101.062 (2)°

Data collection top

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

Refinement top

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

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against all reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.75199 (19)	0.7888 (2)	0.11333 (12)	0.0197 (4)
C2	0.61152 (18)	0.8667 (2)	0.10899 (12)	0.0216 (3)
H2	0.6095	0.9726	0.1039	0.026*
C3	0.4816 (2)	0.7914 (2)	0.11201 (13)	0.0223 (4)
H3	0.3909	0.8438	0.1071	0.027*
C4	0.48733 (19)	0.6302 (2)	0.12290 (12)	0.0202 (3)
C5	0.62772 (18)	0.5536 (2)	0.12955 (12)	0.0191 (3)
C6	0.76182 (19)	0.6328 (2)	0.12325 (13)	0.0214 (4)
H6	0.8528	0.5817	0.1257	0.026*
C7	0.3845 (2)	0.5150 (2)	0.13056 (13)	0.0215 (4)
H7	0.2815	0.5268	0.1283	0.026*
C8	0.4016 (2)	0.2317 (2)	0.15290 (14)	0.0241 (4)
H8A	0.4322	0.1643	0.1022	0.029*
H8B	0.2921	0.2363	0.1386	0.029*
C9	0.4548 (2)	0.1655 (2)	0.25982 (14)	0.0273 (4)
H9A	0.4299	0.0577	0.2586	0.033*
H9B	0.5638	0.1746	0.2782	0.033*
C10	0.3852 (2)	0.2433 (2)	0.34120 (15)	0.0316 (4)
C11	0.3662 (4)	0.2412 (4)	0.5169 (2)	0.0783 (11)
H11A	0.4110	0.3401	0.5363	0.094*
H11B	0.2581	0.2546	0.4950	0.094*
C12	0.3972 (3)	0.1377 (5)	0.6044 (2)	0.0764 (10)
H12A	0.3521	0.1767	0.6594	0.115*
H12B	0.5043	0.1290	0.6277	0.115*
H12C	0.3556	0.0391	0.5839	0.115*
C13	1.07596 (19)	0.8265 (2)	0.27877 (13)	0.0236 (4)
C14	1.1631 (2)	0.7069 (2)	0.32717 (15)	0.0309 (4)
H14	1.2039	0.6351	0.2884	0.037*
C15	1.1882 (2)	0.6960 (3)	0.43361 (15)	0.0355 (5)
H15	1.2487	0.6179	0.4668	0.043*
C16	1.1239 (2)	0.8006 (2)	0.49155 (15)	0.0304 (4)
C17	1.0371 (3)	0.9201 (3)	0.44266 (16)	0.0367 (5)
H17	0.9944	0.9908	0.4812	0.044*
C18	1.0144 (2)	0.9330 (2)	0.33620 (16)	0.0342 (5)
H18	0.9577	1.0136	0.3031	0.041*
C19	1.0760 (3)	0.8738 (3)	0.65678 (15)	0.0430 (6)
H19A	1.0906	0.8351	0.7261	0.065*
H19B	0.9700	0.8764	0.6276	0.065*
H19C	1.1167	0.9751	0.6576	0.065*
N1	0.87396 (16)	0.88540 (16)	0.10220 (11)	0.0222 (3)
H1	0.8609	0.9762	0.1044	0.027*
N2	0.61166 (17)	0.40098 (17)	0.14153 (11)	0.0224 (3)
N3	0.46167 (16)	0.38390 (16)	0.14178 (10)	0.0202 (3)
O1	1.08832 (15)	0.70535 (16)	0.10224 (10)	0.0269 (3)
O2	1.13045 (15)	0.98256 (17)	0.12154 (11)	0.0315 (3)
O3	0.29906 (17)	0.3482 (2)	0.32659 (11)	0.0450 (4)
O4	0.4297 (2)	0.1772 (2)	0.43247 (11)	0.0520 (5)
O5	1.15167 (18)	0.77637 (19)	0.59538 (11)	0.0411 (4)
O6	0.83323 (15)	0.19739 (15)	0.10176 (10)	0.0297 (3)
H6A	0.7633	0.2565	0.1151	0.036*
H6B	0.8488	0.2280	0.0427	0.036*
S1	1.05094 (4)	0.84904 (5)	0.14406 (3)	0.02171 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0167 (9)	0.0247 (8)	0.0181 (8)	0.0017 (7)	0.0040 (7)	−0.0004 (6)
C2	0.0208 (8)	0.0207 (8)	0.0237 (8)	0.0050 (7)	0.0055 (6)	0.0004 (7)
C3	0.0171 (9)	0.0250 (8)	0.0257 (9)	0.0078 (7)	0.0061 (7)	0.0006 (7)
C4	0.0192 (9)	0.0241 (9)	0.0173 (8)	0.0040 (7)	0.0038 (7)	0.0000 (6)
C5	0.0181 (8)	0.0219 (8)	0.0166 (8)	0.0047 (7)	0.0015 (6)	0.0002 (6)
C6	0.0157 (8)	0.0243 (9)	0.0243 (9)	0.0078 (7)	0.0044 (7)	0.0019 (7)
C7	0.0192 (9)	0.0253 (9)	0.0202 (8)	0.0051 (7)	0.0044 (7)	−0.0011 (7)
C8	0.0209 (9)	0.0225 (9)	0.0287 (9)	−0.0006 (7)	0.0043 (7)	−0.0027 (7)
C9	0.0273 (10)	0.0234 (9)	0.0319 (10)	0.0020 (7)	0.0073 (8)	0.0031 (7)
C10	0.0330 (11)	0.0330 (10)	0.0309 (10)	0.0010 (9)	0.0112 (8)	0.0053 (8)
C11	0.110 (3)	0.097 (2)	0.0363 (14)	0.036 (2)	0.0350 (16)	0.0102 (15)
C12	0.0642 (19)	0.129 (3)	0.0388 (14)	−0.015 (2)	0.0174 (13)	0.0096 (17)
C13	0.0187 (8)	0.0259 (9)	0.0256 (8)	−0.0004 (7)	0.0026 (7)	−0.0019 (7)
C14	0.0290 (11)	0.0319 (10)	0.0319 (10)	0.0091 (8)	0.0062 (8)	0.0010 (8)
C15	0.0344 (11)	0.0375 (11)	0.0334 (10)	0.0094 (9)	0.0033 (9)	0.0082 (9)
C16	0.0251 (10)	0.0354 (10)	0.0289 (10)	−0.0046 (7)	0.0010 (8)	0.0003 (7)
C17	0.0404 (12)	0.0377 (11)	0.0321 (10)	0.0088 (9)	0.0072 (9)	−0.0068 (8)
C18	0.0362 (12)	0.0331 (10)	0.0319 (10)	0.0124 (9)	0.0028 (9)	−0.0011 (8)
C19	0.0374 (12)	0.0635 (17)	0.0277 (10)	−0.0016 (11)	0.0051 (8)	−0.0046 (10)
N1	0.0180 (8)	0.0188 (7)	0.0298 (7)	0.0047 (5)	0.0047 (6)	0.0040 (6)
N2	0.0190 (8)	0.0228 (7)	0.0259 (7)	0.0033 (6)	0.0053 (6)	0.0013 (6)
N3	0.0178 (7)	0.0217 (8)	0.0209 (7)	0.0018 (6)	0.0033 (5)	0.0001 (5)
O1	0.0208 (7)	0.0314 (7)	0.0300 (7)	0.0056 (6)	0.0084 (5)	−0.0007 (6)
O2	0.0203 (7)	0.0324 (7)	0.0438 (8)	−0.0005 (6)	0.0114 (6)	0.0073 (6)
O3	0.0536 (9)	0.0433 (8)	0.0434 (8)	0.0182 (9)	0.0227 (7)	0.0073 (8)
O4	0.0646 (11)	0.0640 (11)	0.0303 (8)	0.0236 (9)	0.0165 (8)	0.0126 (7)
O5	0.0444 (9)	0.0506 (9)	0.0262 (8)	0.0047 (7)	0.0020 (6)	0.0013 (6)
O6	0.0334 (8)	0.0249 (7)	0.0335 (7)	0.0082 (6)	0.0133 (6)	0.0030 (5)
S1	0.0152 (2)	0.0246 (2)	0.0263 (2)	0.00303 (17)	0.00648 (15)	0.00187 (18)

Geometric parameters (Å, º) top

C1—C6	1.374 (2)	C12—H12A	0.9600
C1—N1	1.418 (2)	C12—H12B	0.9600
C1—C2	1.431 (2)	C12—H12C	0.9600
C2—C3	1.353 (3)	C13—C18	1.383 (2)
C2—H2	0.9300	C13—C14	1.390 (3)
C3—C4	1.419 (2)	C13—S1	1.7572 (17)
C3—H3	0.9300	C14—C15	1.381 (3)
C4—C7	1.387 (2)	C14—H14	0.9300
C4—C5	1.422 (2)	C15—C16	1.389 (3)
C5—N2	1.357 (2)	C15—H15	0.9300
C5—C6	1.411 (2)	C16—O5	1.360 (2)
C6—H6	0.9300	C16—C17	1.390 (3)
C7—N3	1.337 (2)	C17—C18	1.383 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—N3	1.458 (2)	C18—H18	0.9300
C8—C9	1.514 (3)	C19—O5	1.436 (3)
C8—H8A	0.9700	C19—H19A	0.9600
C8—H8B	0.9700	C19—H19B	0.9600
C9—C10	1.506 (3)	C19—H19C	0.9600
C9—H9A	0.9700	N1—S1	1.6183 (14)
C9—H9B	0.9700	N1—H1	0.8050
C10—O3	1.196 (3)	N2—N3	1.363 (2)
C10—O4	1.326 (2)	O1—S1	1.4399 (14)
C11—C12	1.451 (4)	O2—S1	1.4327 (14)
C11—O4	1.458 (3)	O6—H6A	0.8601
C11—H11A	0.9700	O6—H6B	0.8600
C11—H11B	0.9700

C6—C1—N1	124.49 (16)	H12A—C12—H12B	109.5
C6—C1—C2	121.23 (17)	C11—C12—H12C	109.5
N1—C1—C2	114.23 (15)	H12A—C12—H12C	109.5
C3—C2—C1	122.16 (17)	H12B—C12—H12C	109.5
C3—C2—H2	118.9	C18—C13—C14	120.58 (17)
C1—C2—H2	118.9	C18—C13—S1	119.33 (14)
C2—C3—C4	118.27 (17)	C14—C13—S1	120.01 (14)
C2—C3—H3	120.9	C15—C14—C13	119.13 (18)
C4—C3—H3	120.9	C15—C14—H14	120.4
C7—C4—C3	135.97 (17)	C13—C14—H14	120.4
C7—C4—C5	104.64 (15)	C14—C15—C16	120.55 (19)
C3—C4—C5	119.38 (16)	C14—C15—H15	119.7
N2—C5—C6	127.09 (15)	C16—C15—H15	119.7
N2—C5—C4	111.00 (15)	O5—C16—C15	115.76 (18)
C6—C5—C4	121.91 (16)	O5—C16—C17	124.24 (18)
C1—C6—C5	117.01 (16)	C15—C16—C17	120.01 (18)
C1—C6—H6	121.5	C18—C17—C16	119.51 (18)
C5—C6—H6	121.5	C18—C17—H17	120.2
N3—C7—C4	106.95 (15)	C16—C17—H17	120.2
N3—C7—H7	126.5	C17—C18—C13	120.20 (18)
C4—C7—H7	126.5	C17—C18—H18	119.9
N3—C8—C9	112.72 (15)	C13—C18—H18	119.9
N3—C8—H8A	109.0	O5—C19—H19A	109.5
C9—C8—H8A	109.0	O5—C19—H19B	109.5
N3—C8—H8B	109.0	H19A—C19—H19B	109.5
C9—C8—H8B	109.0	O5—C19—H19C	109.5
H8A—C8—H8B	107.8	H19A—C19—H19C	109.5
C10—C9—C8	112.84 (16)	H19B—C19—H19C	109.5
C10—C9—H9A	109.0	C1—N1—S1	125.60 (12)
C8—C9—H9A	109.0	C1—N1—H1	117.6
C10—C9—H9B	109.0	S1—N1—H1	108.9
C8—C9—H9B	109.0	C5—N2—N3	103.70 (13)
H9A—C9—H9B	107.8	C7—N3—N2	113.70 (14)
O3—C10—O4	123.80 (19)	C7—N3—C8	126.97 (15)
O3—C10—C9	125.49 (18)	N2—N3—C8	119.33 (14)
O4—C10—C9	110.70 (17)	C10—O4—C11	115.4 (2)
C12—C11—O4	108.8 (3)	C16—O5—C19	117.30 (17)
C12—C11—H11A	109.9	H6A—O6—H6B	104.5
O4—C11—H11A	109.9	O2—S1—O1	118.09 (7)
C12—C11—H11B	109.9	O2—S1—N1	105.63 (8)
O4—C11—H11B	109.9	O1—S1—N1	109.27 (8)
H11A—C11—H11B	108.3	O2—S1—C13	109.18 (9)
C11—C12—H12A	109.5	O1—S1—C13	107.13 (8)
C11—C12—H12B	109.5	N1—S1—C13	107.07 (8)

C6—C1—C2—C3	−1.5 (3)	C14—C13—C18—C17	−1.1 (3)
N1—C1—C2—C3	175.96 (15)	S1—C13—C18—C17	−177.88 (17)
C1—C2—C3—C4	1.9 (3)	C6—C1—N1—S1	−26.6 (2)
C2—C3—C4—C7	178.80 (18)	C2—C1—N1—S1	155.99 (12)
C2—C3—C4—C5	−0.4 (3)	C6—C5—N2—N3	−179.35 (15)
C7—C4—C5—N2	−0.54 (19)	C4—C5—N2—N3	0.25 (18)
C3—C4—C5—N2	178.89 (15)	C4—C7—N3—N2	−0.50 (19)
C7—C4—C5—C6	179.08 (15)	C4—C7—N3—C8	179.99 (15)
C3—C4—C5—C6	−1.5 (2)	C5—N2—N3—C7	0.16 (18)
N1—C1—C6—C5	−177.59 (14)	C5—N2—N3—C8	179.70 (14)
C2—C1—C6—C5	−0.4 (2)	C9—C8—N3—C7	−111.10 (19)
N2—C5—C6—C1	−178.61 (17)	C9—C8—N3—N2	69.41 (19)
C4—C5—C6—C1	1.8 (2)	O3—C10—O4—C11	0.0 (4)
C3—C4—C7—N3	−178.7 (2)	C9—C10—O4—C11	−178.6 (2)
C5—C4—C7—N3	0.61 (18)	C12—C11—O4—C10	167.3 (3)
N3—C8—C9—C10	70.9 (2)	C15—C16—O5—C19	−174.48 (19)
C8—C9—C10—O3	−1.3 (3)	C17—C16—O5—C19	5.2 (3)
C8—C9—C10—O4	177.17 (17)	C1—N1—S1—O2	−176.12 (14)
C18—C13—C14—C15	−0.3 (3)	C1—N1—S1—O1	55.87 (16)
S1—C13—C14—C15	176.48 (16)	C1—N1—S1—C13	−59.84 (16)
C13—C14—C15—C16	1.8 (3)	C18—C13—S1—O2	66.47 (17)
C14—C15—C16—O5	177.83 (19)	C14—C13—S1—O2	−110.37 (16)
C14—C15—C16—C17	−1.9 (3)	C18—C13—S1—O1	−164.56 (15)
O5—C16—C17—C18	−179.2 (2)	C14—C13—S1—O1	18.60 (18)
C15—C16—C17—C18	0.5 (3)	C18—C13—S1—N1	−47.44 (18)
C16—C17—C18—C13	1.0 (3)	C14—C13—S1—N1	135.72 (15)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁N₃O₅S·H₂O
M_r	421.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.0248 (3), 8.7602 (3), 13.1792 (4)
β (°)	101.062 (2)
V (Å³)	1022.58 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.42 × 0.37 × 0.28

Data collection
Diffractometer	Bruker X8 APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10050, 4021, 3887
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.077, 1.05
No. of reflections	4021
No. of parameters	262
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.28
Absolute structure	Flack (1983), 1779 Friedel pairs
Absolute structure parameter	0.03 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···N2	0.86	1.94	2.8029 (19)	176.3
N1—H1···O6ⁱ	0.81	1.95	2.7575 (19)	176.5
O6—H6B···O1ⁱⁱ	0.86	2.10	2.9094 (17)	155.7

Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z.

Acknowledgements

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

References

Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240–249. Web of Science CrossRef CAS PubMed Google Scholar
Bouissane, L., El Kazzouli, S., Léonce, S., Pffeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078–1088. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Brzozowski, Z., S1awinski, J., Saczewski, F., Innocenti, A. & Supuran, C. T. (2010). Eur. J. Med. Chem. 45, 2396–2404. Google Scholar
Drew, J. (2000). Science, 287, 1960–964. Web of Science PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gadad, A. K., Mahajanshetti, C. S., Nimbalkar, S. & Raichurkar, A. (2000). Eur. J. Med. Chem. 35, 853–857. Web of Science CrossRef PubMed CAS Google Scholar
Garaj, V., Puccetti, L., Fasolis, G., Winum, J. Y., Montero, J. L., Scozzafava, A., Vullo, D., Innocenti, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3102–3108. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 2| February 2013| Pages o190-o191

doi:10.1107/S1600536812051975

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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