N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-meth­oxy­benzene­sulfonamide hemi­hydrate

Chicha, H.; Kouakou, A.; Rakib, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536813020606

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1353

doi:10.1107/S1600536813020606

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N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-methoxybenzenesulfonamide hemihydrate

Hakima Chicha,^a ^* Assoman Kouakou,^a El Mostapha Rakib,^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: hakima_chicha@yahoo.fr

(Received 23 July 2013; accepted 24 July 2013; online 31 July 2013)

The fused five- and six-membered rings in the title compound, C₁₇H₁₆ClN₃O₃S·0.5H₂O, are practically coplanar, with the maximum deviation from the mean plane being 0.057 (3) Å for the C atom bound to the exocyclic N atom. The indazole system makes a dihedral angle of 66.18 (12)° with the plane through the benzene ring, and it is nearly perpendicular to the allyl group, as indicated by the N—N—C—C torsion angle of 79.2 (3)°. In the crystal, the water molecule, lying on a twofold axis, forms O—H⋯N and accepts N—H⋯O hydrogen bonds. Additional C—H⋯O hydrogen bonds contribute to the formation of a chain along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010 ); Drew (2000 ); Garaj et al. (2005 ); Lopez et al. (2010 ). For similar compounds, see: Abbassi et al. (2012 , 2013 ).

Experimental

Crystal data

C₁₇H₁₆ClN₃O₃S·0.5H₂O
M_r = 386.86
Monoclinic, C 2/c
a = 23.5515 (9) Å
b = 8.9081 (3) Å
c = 20.8278 (8) Å
β = 122.628 (2)°
V = 3680.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.41 × 0.38 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer
20391 measured reflections
4389 independent reflections
2740 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.122
S = 1.02
4389 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.83	2.04	2.875 (2)	174
O4—H4⋯N2	0.87	2.00	2.822 (2)	158
C7—H7⋯O3ⁱⁱ	0.93	2.37	3.288 (3)	170
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 datablock I. DOI: 10.1107/S1600536813020606/tk5244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020606/tk5244Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020606/tk5244Isup3.cml

checkCIF report

Comment top

Research on sulfonamides are justified by the medical interest of these compounds. Indeed, these drugs possess different types of pharmacological activities such as anti-bacterial, hypoglycemic, anti-inflammatory agents and anti-tumour (Lopez, et al., 2010), anti-carbonic anhydrase (Brzozowski et al., 2010), hypoglycemia (Drew, 2000) and anti-cancer activity (Garaj et al., 2005). This work is part of research on the synthesis of some new N-(6 (4)-indazolyl derivatives)aylsulfonamide recently reported by our group (Abbassi et al., 2012, Abbassi et al., 2013).

The molecule of the N-(2-allyl-5-chloro-2H-indazol-5-yl)-4-methoxybenzenesulfonamide is built up from fused five- and six-membered rings which are almost co-planar, with a maximum deviation of -0.057 (3) Å for C1 atom as shown in Fig. 1. Moreover, the fused rings system is nearly perpendicular to the plane through the atoms forming the allyl group (C8-C10) and to benzene ring (C11-C16) as indicated by the dihedral angles between them of 66.4 (5) and 66.18 (12)°, respectively.

The cohesion of the crystal structure is ensured by O4–H4···N2, N1–H1···O4 and C7–H7···O3 hydrogen bonds formed between the water and the organic molecules forming a one-dimensional chain along the b axis (Table 2).

Related literature top

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010); Drew (2000); Garaj et al. (2005); Lopez et al. (2010). For similar compounds, see: Abbassi et al. (2012, 2013).

Experimental top

A mixture of 2-allyl-5-nitroindazole (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in absolute ethanol (25 ml) 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 its ethanol solution.

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 with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-methoxybenzenesulfonamide hemihydrate top

Crystal data top

C₁₇H₁₆ClN₃O₃S·0.5H₂O	F(000) = 1608
M_r = 386.86	D_x = 1.396 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4389 reflections
a = 23.5515 (9) Å	θ = 2.5–27.9°
b = 8.9081 (3) Å	µ = 0.35 mm⁻¹
c = 20.8278 (8) Å	T = 296 K
β = 122.628 (2)°	Block, colourless
V = 3680.1 (2) Å³	0.41 × 0.38 × 0.27 mm
Z = 8

Data collection top

Bruker X8 APEX diffractometer	2740 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 27.9°, θ_min = 2.5°
ϕ and ω scans	h = −30→29
20391 measured reflections	k = −11→11
4389 independent reflections	l = −25→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0457P)² + 2.416P] where P = (F_o² + 2F_c²)/3
4389 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₇H₁₆ClN₃O₃S·0.5H₂O	V = 3680.1 (2) Å³
M_r = 386.86	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.5515 (9) Å	µ = 0.35 mm⁻¹
b = 8.9081 (3) Å	T = 296 K
c = 20.8278 (8) Å	0.41 × 0.38 × 0.27 mm
β = 122.628 (2)°

Data collection top

Bruker X8 APEX diffractometer	2740 reflections with I > 2σ(I)
20391 measured reflections	R_int = 0.057
4389 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
4389 reflections	Δρ_min = −0.33 e Å⁻³
231 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.07686 (11)	0.1101 (2)	0.24133 (13)	0.0363 (5)
C2	0.06759 (12)	−0.0223 (3)	0.19808 (14)	0.0434 (6)
H2	0.0569	−0.0121	0.1483	0.052*
C3	0.07383 (13)	−0.1630 (3)	0.22687 (14)	0.0457 (6)
H3	0.0688	−0.2476	0.1981	0.055*
C4	0.08816 (12)	−0.1761 (3)	0.30157 (13)	0.0402 (5)
C5	0.09891 (11)	−0.0468 (2)	0.34607 (13)	0.0369 (5)
C6	0.09541 (11)	0.0968 (2)	0.31577 (13)	0.0361 (5)
C7	0.10847 (12)	−0.1007 (3)	0.41405 (14)	0.0458 (6)
H7	0.1169	−0.0441	0.4558	0.055*
C8	0.11049 (16)	−0.3571 (3)	0.46422 (16)	0.0612 (8)
H8A	0.0770	−0.4358	0.4394	0.073*
H8B	0.1028	−0.3065	0.5001	0.073*
C9	0.1797 (2)	−0.4252 (4)	0.5063 (2)	0.0854 (11)
H9	0.1947	−0.4679	0.4773	0.103*
C10	0.2188 (2)	−0.4290 (6)	0.5770 (3)	0.1285 (17)
H10A	0.2056	−0.3874	0.6080	0.154*
H10B	0.2610	−0.4734	0.5987	0.154*
C11	0.19083 (12)	0.3430 (3)	0.25760 (13)	0.0404 (5)
C12	0.23937 (14)	0.2387 (3)	0.27121 (15)	0.0517 (7)
H12	0.2288	0.1607	0.2369	0.062*
C13	0.30364 (14)	0.2495 (3)	0.33557 (15)	0.0521 (7)
H13	0.3364	0.1796	0.3443	0.062*
C14	0.31891 (13)	0.3638 (3)	0.38665 (14)	0.0448 (6)
C15	0.26970 (14)	0.4682 (3)	0.37284 (15)	0.0555 (7)
H15	0.2802	0.5461	0.4072	0.067*
C16	0.20606 (13)	0.4575 (3)	0.30924 (15)	0.0514 (7)
H16	0.1732	0.5269	0.3008	0.062*
C17	0.43186 (15)	0.2760 (4)	0.47218 (17)	0.0706 (9)
H17A	0.4722	0.3057	0.5189	0.106*
H17B	0.4409	0.2688	0.4325	0.106*
H17C	0.4171	0.1802	0.4790	0.106*
N1	0.06279 (10)	0.2526 (2)	0.20483 (11)	0.0415 (5)
H1	0.0473	0.3177	0.2200	0.050*
N2	0.09126 (11)	−0.3021 (2)	0.33985 (12)	0.0491 (5)
N3	0.10311 (11)	−0.2499 (2)	0.40710 (12)	0.0481 (5)
O1	0.08137 (9)	0.47240 (19)	0.14958 (10)	0.0602 (5)
O2	0.11154 (9)	0.2212 (2)	0.12606 (10)	0.0550 (5)
O3	0.38047 (10)	0.3849 (2)	0.45159 (10)	0.0651 (6)
O4	0.0000	−0.5316 (2)	0.2500	0.0455 (6)
H4	0.0324	−0.4800	0.2868	0.055*
S1	0.10886 (3)	0.32522 (7)	0.17658 (3)	0.04380 (18)
Cl1	0.11387 (4)	0.25023 (7)	0.37487 (4)	0.0539 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0325 (12)	0.0362 (11)	0.0432 (14)	−0.0015 (9)	0.0224 (10)	−0.0012 (10)
C2	0.0502 (15)	0.0461 (13)	0.0395 (14)	−0.0016 (11)	0.0279 (12)	−0.0045 (11)
C3	0.0548 (15)	0.0385 (13)	0.0473 (15)	−0.0058 (11)	0.0299 (13)	−0.0112 (11)
C4	0.0418 (13)	0.0355 (12)	0.0426 (13)	−0.0036 (10)	0.0223 (11)	−0.0035 (10)
C5	0.0334 (12)	0.0374 (12)	0.0354 (12)	−0.0021 (10)	0.0156 (10)	−0.0031 (10)
C6	0.0328 (12)	0.0341 (11)	0.0399 (13)	−0.0014 (9)	0.0186 (10)	−0.0063 (10)
C7	0.0488 (15)	0.0420 (13)	0.0425 (14)	−0.0026 (11)	0.0220 (12)	−0.0046 (11)
C8	0.078 (2)	0.0522 (15)	0.0503 (16)	−0.0095 (15)	0.0324 (15)	0.0060 (13)
C9	0.113 (3)	0.069 (2)	0.060 (2)	0.022 (2)	0.038 (2)	0.0236 (18)
C10	0.090 (3)	0.168 (5)	0.130 (4)	0.029 (3)	0.061 (3)	0.046 (4)
C11	0.0413 (13)	0.0437 (13)	0.0389 (13)	−0.0031 (11)	0.0233 (11)	0.0003 (11)
C12	0.0509 (16)	0.0530 (15)	0.0490 (16)	−0.0001 (12)	0.0255 (13)	−0.0111 (12)
C13	0.0469 (15)	0.0546 (15)	0.0521 (16)	0.0088 (12)	0.0250 (13)	−0.0044 (13)
C14	0.0446 (14)	0.0488 (14)	0.0360 (13)	−0.0008 (11)	0.0185 (11)	0.0006 (11)
C15	0.0555 (17)	0.0510 (15)	0.0479 (16)	0.0041 (13)	0.0200 (13)	−0.0123 (12)
C16	0.0516 (16)	0.0462 (14)	0.0530 (16)	0.0083 (12)	0.0259 (13)	−0.0020 (12)
C17	0.0550 (18)	0.085 (2)	0.0531 (18)	0.0131 (16)	0.0170 (15)	0.0047 (16)
N1	0.0426 (11)	0.0384 (10)	0.0480 (12)	0.0044 (9)	0.0272 (10)	0.0030 (9)
N2	0.0621 (14)	0.0374 (10)	0.0467 (13)	−0.0070 (10)	0.0285 (11)	−0.0033 (10)
N3	0.0580 (14)	0.0422 (11)	0.0400 (12)	−0.0039 (10)	0.0238 (11)	0.0007 (10)
O1	0.0570 (11)	0.0533 (11)	0.0583 (12)	0.0038 (9)	0.0232 (10)	0.0218 (9)
O2	0.0580 (12)	0.0709 (12)	0.0423 (10)	−0.0083 (9)	0.0311 (9)	−0.0085 (9)
O3	0.0547 (12)	0.0710 (12)	0.0449 (11)	0.0067 (10)	0.0106 (9)	−0.0085 (9)
O4	0.0490 (14)	0.0278 (11)	0.0537 (15)	0.000	0.0238 (12)	0.000
S1	0.0435 (3)	0.0467 (3)	0.0391 (3)	−0.0030 (3)	0.0210 (3)	0.0045 (3)
Cl1	0.0702 (5)	0.0371 (3)	0.0480 (4)	0.0009 (3)	0.0275 (3)	−0.0084 (3)

Geometric parameters (Å, º) top

C1—C6	1.371 (3)	C11—C12	1.379 (3)
C1—N1	1.423 (3)	C11—C16	1.382 (3)
C1—C2	1.428 (3)	C11—S1	1.757 (2)
C2—C3	1.363 (3)	C12—C13	1.382 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.408 (3)	C13—C14	1.373 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—N2	1.356 (3)	C14—O3	1.361 (3)
C4—C5	1.413 (3)	C14—C15	1.390 (4)
C5—C7	1.393 (3)	C15—C16	1.367 (3)
C5—C6	1.409 (3)	C15—H15	0.9300
C6—Cl1	1.731 (2)	C16—H16	0.9300
C7—N3	1.336 (3)	C17—O3	1.425 (3)
C7—H7	0.9300	C17—H17A	0.9600
C8—N3	1.461 (3)	C17—H17B	0.9600
C8—C9	1.501 (5)	C17—H17C	0.9600
C8—H8A	0.9700	N1—S1	1.622 (2)
C8—H8B	0.9700	N1—H1	0.8338
C9—C10	1.247 (5)	N2—N3	1.355 (3)
C9—H9	0.9300	O1—S1	1.4359 (18)
C10—H10A	0.9300	O2—S1	1.4286 (18)
C10—H10B	0.9300	O4—H4	0.8662

C6—C1—N1	121.5 (2)	C11—C12—C13	120.4 (2)
C6—C1—C2	119.3 (2)	C11—C12—H12	119.8
N1—C1—C2	119.2 (2)	C13—C12—H12	119.8
C3—C2—C1	122.6 (2)	C14—C13—C12	119.7 (2)
C3—C2—H2	118.7	C14—C13—H13	120.2
C1—C2—H2	118.7	C12—C13—H13	120.2
C2—C3—C4	117.9 (2)	O3—C14—C13	124.5 (2)
C2—C3—H3	121.1	O3—C14—C15	115.9 (2)
C4—C3—H3	121.1	C13—C14—C15	119.7 (2)
N2—C4—C3	128.5 (2)	C16—C15—C14	120.7 (2)
N2—C4—C5	110.8 (2)	C16—C15—H15	119.7
C3—C4—C5	120.6 (2)	C14—C15—H15	119.7
C7—C5—C6	134.9 (2)	C15—C16—C11	119.6 (2)
C7—C5—C4	105.0 (2)	C15—C16—H16	120.2
C6—C5—C4	120.0 (2)	C11—C16—H16	120.2
C1—C6—C5	119.4 (2)	O3—C17—H17A	109.5
C1—C6—Cl1	122.73 (17)	O3—C17—H17B	109.5
C5—C6—Cl1	117.83 (18)	H17A—C17—H17B	109.5
N3—C7—C5	106.2 (2)	O3—C17—H17C	109.5
N3—C7—H7	126.9	H17A—C17—H17C	109.5
C5—C7—H7	126.9	H17B—C17—H17C	109.5
N3—C8—C9	110.7 (3)	C1—N1—S1	122.73 (16)
N3—C8—H8A	109.5	C1—N1—H1	116.2
C9—C8—H8A	109.5	S1—N1—H1	112.1
N3—C8—H8B	109.5	N3—N2—C4	103.84 (18)
C9—C8—H8B	109.5	C7—N3—N2	114.1 (2)
H8A—C8—H8B	108.1	C7—N3—C8	126.8 (2)
C10—C9—C8	125.3 (4)	N2—N3—C8	119.0 (2)
C10—C9—H9	117.4	C14—O3—C17	118.8 (2)
C8—C9—H9	117.4	O2—S1—O1	119.55 (12)
C9—C10—H10A	120.0	O2—S1—N1	108.20 (11)
C9—C10—H10B	120.0	O1—S1—N1	104.94 (11)
H10A—C10—H10B	120.0	O2—S1—C11	107.69 (12)
C12—C11—C16	119.9 (2)	O1—S1—C11	108.89 (11)
C12—C11—S1	119.78 (19)	N1—S1—C11	106.92 (11)
C16—C11—S1	120.25 (19)

C6—C1—C2—C3	2.7 (4)	C13—C14—C15—C16	0.6 (4)
N1—C1—C2—C3	−173.7 (2)	C14—C15—C16—C11	−1.0 (4)
C1—C2—C3—C4	1.8 (4)	C12—C11—C16—C15	1.3 (4)
C2—C3—C4—N2	174.2 (2)	S1—C11—C16—C15	178.7 (2)
C2—C3—C4—C5	−3.0 (4)	C6—C1—N1—S1	114.3 (2)
N2—C4—C5—C7	−0.3 (3)	C2—C1—N1—S1	−69.4 (3)
C3—C4—C5—C7	177.4 (2)	C3—C4—N2—N3	−176.8 (2)
N2—C4—C5—C6	−177.8 (2)	C5—C4—N2—N3	0.6 (3)
C3—C4—C5—C6	−0.1 (3)	C5—C7—N3—N2	0.6 (3)
N1—C1—C6—C5	170.4 (2)	C5—C7—N3—C8	178.8 (2)
C2—C1—C6—C5	−5.8 (3)	C4—N2—N3—C7	−0.8 (3)
N1—C1—C6—Cl1	−8.6 (3)	C4—N2—N3—C8	−179.2 (2)
C2—C1—C6—Cl1	175.13 (17)	C9—C8—N3—C7	−99.0 (3)
C7—C5—C6—C1	−171.9 (3)	C9—C8—N3—N2	79.2 (3)
C4—C5—C6—C1	4.6 (3)	C13—C14—O3—C17	−5.1 (4)
C7—C5—C6—Cl1	7.2 (4)	C15—C14—O3—C17	175.5 (3)
C4—C5—C6—Cl1	−176.30 (18)	C1—N1—S1—O2	56.3 (2)
C6—C5—C7—N3	176.7 (3)	C1—N1—S1—O1	−175.03 (18)
C4—C5—C7—N3	−0.2 (3)	C1—N1—S1—C11	−59.5 (2)
N3—C8—C9—C10	127.3 (4)	C12—C11—S1—O2	−15.3 (2)
C16—C11—C12—C13	−1.2 (4)	C16—C11—S1—O2	167.2 (2)
S1—C11—C12—C13	−178.6 (2)	C12—C11—S1—O1	−146.4 (2)
C11—C12—C13—C14	0.7 (4)	C16—C11—S1—O1	36.2 (2)
C12—C13—C14—O3	−179.9 (3)	C12—C11—S1—N1	100.7 (2)
C12—C13—C14—C15	−0.4 (4)	C16—C11—S1—N1	−76.7 (2)
O3—C14—C15—C16	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.83	2.04	2.875 (2)	174
O4—H4···N2	0.87	2.00	2.822 (2)	158
C7—H7···O3ⁱⁱ	0.93	2.37	3.288 (3)	170

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.83	2.04	2.875 (2)	174
O4—H4···N2	0.87	2.00	2.822 (2)	158
C7—H7···O3ⁱⁱ	0.93	2.37	3.288 (3)	170

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

Acknowledgements

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

References

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Volume 69| Part 8| August 2013| Page o1353

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

N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-meth­­oxy­benzene­sulfonamide hemi­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-methoxybenzenesulfonamide hemihydrate