organic compounds
A correction has been published for this article. To view the correction, click here.
N-(2-Allyl-4-ethoxy-2H-indazol-5-yl)-4-methylbenzenesulfonamide
aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, bIST Istituto Nazionale per la Ricerca sul Cancro, U.O.C. Terapia Immunologica, L. go R. Benzi 10, 16132 Genova, Italy, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: l_bouissane@yahoo.fr
The indazole ring system of the title compound, C19H21N3O3S, is almost planar (r.m.s. deviation = 0.0192 Å) and forms dihedral angles of 77.99 (15) and 83.9 (3)° with the benzene ring and allyl group, respectively. In the crystal, centrosymmetrically related molecules are connected by pairs of N—H⋯O hydrogen bonds into dimers, which are further linked by C—H⋯O hydrogen bonds, forming columns parallel to the b axis.
CCDC reference: 999285
Related literature
For the biological activity of ); Supuran & Scozzafava (2001); Abbate et al. (2004); Rostom (2006); Ghorab et al. (2009). For similar compounds, see: Bouissane et al. (2006); Abbassi et al. (2012, 2013).
see: Drews (2000Experimental
Crystal data
|
|
Data collection: APEX2 (Bruker, 2009); cell 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
CCDC reference: 999285
10.1107/S1600536814009283/rz5122sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814009283/rz5122Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814009283/rz5122Isup3.cml
A mixture of 2-allyl-5-nitroindazole (1.22 mmol) and anhydrous SnCl2 (1.1 g, 6.1 mmol) in 25 ml of absolute ethanol was heated at 60°C 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-methylbenzenesulfonyl chloride (1.25 mmol) at room temperature for 24 h. The reaction mixture was then concentrated in vacuo and the resulting residue was purified by flash
(eluted with ethyl acetate:hexane 2:8 v/v). The title compound was recrystallized from ethanol (yield = 78%, m. p. = 388 K).H atoms were located in a difference Fourier map and treated as riding with C–H = 0.93-0.97 Å, N–H = 0.84 Å, and with Uiso(H) = 1.2 Ueq (C, N) or 1.5 Ueq for methyl H atoms. Three outliers (2 0 0, -2 0 2, 1 1 1) were omitted in the last cycles of refinement.
Data collection: APEX2 (Bruker, 2009); cell
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).C19H21N3O3S | F(000) = 1568 |
Mr = 371.45 | Dx = 1.342 Mg m−3 |
Monoclinic, C2/c | Melting point: 388 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.0808 (5) Å | Cell parameters from 4059 reflections |
b = 7.9335 (2) Å | θ = 2.3–27.1° |
c = 21.1573 (4) Å | µ = 0.20 mm−1 |
β = 122.839 (1)° | T = 296 K |
V = 3678.13 (14) Å3 | Block, colourless |
Z = 8 | 0.42 × 0.35 × 0.30 mm |
Bruker X8 APEX diffractometer | 4059 independent reflections |
Radiation source: fine-focus sealed tube | 3100 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ϕ and ω scans | θmax = 27.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −33→33 |
Tmin = 0.693, Tmax = 0.747 | k = −10→10 |
37135 measured reflections | l = −27→27 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0616P)2 + 3.2227P] where P = (Fo2 + 2Fc2)/3 |
4059 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C19H21N3O3S | V = 3678.13 (14) Å3 |
Mr = 371.45 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 26.0808 (5) Å | µ = 0.20 mm−1 |
b = 7.9335 (2) Å | T = 296 K |
c = 21.1573 (4) Å | 0.42 × 0.35 × 0.30 mm |
β = 122.839 (1)° |
Bruker X8 APEX diffractometer | 4059 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3100 reflections with I > 2σ(I) |
Tmin = 0.693, Tmax = 0.747 | Rint = 0.048 |
37135 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.28 e Å−3 |
4059 reflections | Δρmin = −0.36 e Å−3 |
235 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.18654 (15) | 1.1635 (5) | 0.01834 (19) | 0.0893 (10) | |
H1A | 0.1582 | 1.1968 | 0.0297 | 0.107* | |
H1B | 0.2038 | 1.2431 | 0.0030 | 0.107* | |
C2 | 0.20182 (12) | 1.0079 (4) | 0.02385 (15) | 0.0683 (8) | |
H2 | 0.2302 | 0.9786 | 0.0121 | 0.082* | |
C3 | 0.17730 (12) | 0.8734 (4) | 0.04754 (16) | 0.0724 (8) | |
H3A | 0.1511 | 0.8016 | 0.0047 | 0.087* | |
H3B | 0.1524 | 0.9234 | 0.0638 | 0.087* | |
C4 | 0.26062 (10) | 0.8146 (3) | 0.18156 (14) | 0.0550 (6) | |
H4 | 0.2592 | 0.9161 | 0.2025 | 0.066* | |
C5 | 0.30029 (9) | 0.6795 (3) | 0.21932 (12) | 0.0414 (5) | |
C6 | 0.28267 (10) | 0.5576 (3) | 0.16164 (13) | 0.0483 (5) | |
C7 | 0.31134 (11) | 0.3998 (3) | 0.17722 (15) | 0.0596 (7) | |
H7 | 0.2990 | 0.3198 | 0.1395 | 0.071* | |
C8 | 0.35751 (10) | 0.3678 (3) | 0.24888 (13) | 0.0496 (6) | |
H9 | 0.3762 | 0.2625 | 0.2606 | 0.060* | |
C9 | 0.37814 (9) | 0.4902 (2) | 0.30660 (11) | 0.0356 (4) | |
C10 | 0.35000 (9) | 0.6438 (3) | 0.29332 (11) | 0.0363 (4) | |
C11 | 0.36304 (15) | 0.9237 (3) | 0.34341 (16) | 0.0712 (8) | |
H11B | 0.3205 | 0.9536 | 0.3207 | 0.085* | |
H11A | 0.3758 | 0.9615 | 0.3104 | 0.085* | |
C12 | 0.40124 (14) | 1.0063 (4) | 0.41880 (16) | 0.0715 (8) | |
H12B | 0.3969 | 1.1264 | 0.4130 | 0.107* | |
H12A | 0.4433 | 0.9761 | 0.4409 | 0.107* | |
H12C | 0.3880 | 0.9692 | 0.4509 | 0.107* | |
C13 | 0.52408 (8) | 0.5771 (2) | 0.37746 (10) | 0.0329 (4) | |
C14 | 0.55443 (10) | 0.5564 (3) | 0.34089 (12) | 0.0428 (5) | |
H14 | 0.5586 | 0.4500 | 0.3258 | 0.051* | |
C15 | 0.57834 (11) | 0.6960 (3) | 0.32728 (13) | 0.0494 (6) | |
H15 | 0.5995 | 0.6821 | 0.3036 | 0.059* | |
C16 | 0.57191 (10) | 0.8555 (3) | 0.34757 (13) | 0.0460 (5) | |
C17 | 0.54115 (11) | 0.8730 (3) | 0.38424 (13) | 0.0477 (5) | |
H17 | 0.5363 | 0.9797 | 0.3984 | 0.057* | |
C18 | 0.51797 (10) | 0.7357 (3) | 0.39973 (12) | 0.0421 (5) | |
H18 | 0.4982 | 0.7490 | 0.4251 | 0.050* | |
C19 | 0.59695 (14) | 1.0079 (4) | 0.33072 (18) | 0.0743 (8) | |
H19A | 0.6303 | 0.9746 | 0.3264 | 0.111* | |
H19B | 0.6110 | 1.0884 | 0.3707 | 0.111* | |
H19C | 0.5654 | 1.0579 | 0.2843 | 0.111* | |
N1 | 0.22511 (9) | 0.7686 (3) | 0.10913 (12) | 0.0592 (6) | |
N2 | 0.23653 (9) | 0.6139 (3) | 0.09414 (12) | 0.0616 (6) | |
N3 | 0.42783 (7) | 0.4479 (2) | 0.38105 (9) | 0.0368 (4) | |
H3N | 0.4322 | 0.5087 | 0.4163 | 0.044* | |
O1 | 0.37042 (8) | 0.7467 (2) | 0.35341 (9) | 0.0589 (5) | |
O2 | 0.48852 (7) | 0.26717 (19) | 0.34847 (9) | 0.0493 (4) | |
O3 | 0.53203 (7) | 0.3684 (2) | 0.47767 (8) | 0.0486 (4) | |
S1 | 0.49532 (2) | 0.39937 (6) | 0.39815 (3) | 0.03587 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0645 (19) | 0.080 (2) | 0.091 (2) | −0.0064 (17) | 0.0212 (18) | 0.005 (2) |
C2 | 0.0484 (14) | 0.096 (2) | 0.0516 (15) | 0.0093 (15) | 0.0215 (12) | 0.0095 (16) |
C3 | 0.0416 (13) | 0.081 (2) | 0.0604 (17) | 0.0034 (13) | 0.0054 (13) | 0.0161 (15) |
C4 | 0.0419 (12) | 0.0544 (15) | 0.0548 (15) | 0.0074 (11) | 0.0172 (11) | 0.0020 (12) |
C5 | 0.0333 (10) | 0.0438 (12) | 0.0446 (12) | 0.0008 (9) | 0.0195 (9) | 0.0008 (10) |
C6 | 0.0347 (10) | 0.0561 (14) | 0.0435 (12) | −0.0049 (10) | 0.0144 (10) | −0.0076 (11) |
C7 | 0.0518 (14) | 0.0542 (15) | 0.0531 (15) | −0.0049 (11) | 0.0156 (12) | −0.0207 (12) |
C8 | 0.0480 (12) | 0.0370 (12) | 0.0566 (14) | −0.0018 (9) | 0.0236 (12) | −0.0097 (10) |
C9 | 0.0352 (10) | 0.0320 (10) | 0.0392 (11) | −0.0016 (8) | 0.0200 (9) | 0.0006 (9) |
C10 | 0.0370 (10) | 0.0355 (11) | 0.0380 (11) | −0.0032 (8) | 0.0213 (9) | −0.0040 (9) |
C11 | 0.094 (2) | 0.0451 (16) | 0.0664 (18) | 0.0085 (14) | 0.0381 (17) | −0.0006 (13) |
C12 | 0.085 (2) | 0.0484 (16) | 0.080 (2) | −0.0012 (14) | 0.0440 (17) | −0.0163 (14) |
C13 | 0.0330 (9) | 0.0321 (10) | 0.0300 (9) | 0.0052 (8) | 0.0147 (8) | 0.0033 (8) |
C14 | 0.0478 (12) | 0.0407 (12) | 0.0449 (12) | 0.0063 (9) | 0.0284 (10) | −0.0007 (10) |
C15 | 0.0514 (13) | 0.0562 (15) | 0.0532 (13) | 0.0016 (11) | 0.0365 (12) | 0.0031 (11) |
C16 | 0.0424 (11) | 0.0458 (13) | 0.0473 (13) | −0.0005 (10) | 0.0227 (10) | 0.0087 (10) |
C17 | 0.0558 (13) | 0.0327 (12) | 0.0596 (14) | 0.0042 (10) | 0.0346 (12) | 0.0016 (10) |
C18 | 0.0509 (12) | 0.0338 (11) | 0.0524 (13) | 0.0047 (9) | 0.0352 (11) | 0.0014 (10) |
C19 | 0.0806 (19) | 0.0632 (19) | 0.095 (2) | −0.0091 (15) | 0.0580 (18) | 0.0138 (16) |
N1 | 0.0365 (10) | 0.0692 (15) | 0.0498 (12) | 0.0019 (9) | 0.0089 (9) | 0.0063 (11) |
N2 | 0.0434 (11) | 0.0702 (15) | 0.0492 (12) | −0.0022 (10) | 0.0109 (10) | −0.0057 (11) |
N3 | 0.0419 (9) | 0.0324 (9) | 0.0389 (9) | 0.0019 (7) | 0.0238 (8) | 0.0019 (7) |
O1 | 0.0722 (11) | 0.0430 (9) | 0.0508 (10) | 0.0097 (8) | 0.0264 (9) | −0.0026 (8) |
O2 | 0.0595 (10) | 0.0317 (8) | 0.0595 (10) | 0.0054 (7) | 0.0341 (8) | −0.0047 (7) |
O3 | 0.0523 (9) | 0.0491 (9) | 0.0398 (8) | 0.0167 (7) | 0.0221 (7) | 0.0171 (7) |
S1 | 0.0418 (3) | 0.0277 (3) | 0.0375 (3) | 0.0078 (2) | 0.0211 (2) | 0.0056 (2) |
C1—C2 | 1.284 (4) | C11—H11A | 0.9700 |
C1—H1A | 0.9300 | C12—H12B | 0.9600 |
C1—H1B | 0.9300 | C12—H12A | 0.9600 |
C2—C3 | 1.465 (4) | C12—H12C | 0.9600 |
C2—H2 | 0.9300 | C13—C18 | 1.382 (3) |
C3—N1 | 1.477 (3) | C13—C14 | 1.384 (3) |
C3—H3A | 0.9700 | C13—S1 | 1.760 (2) |
C3—H3B | 0.9700 | C14—C15 | 1.376 (3) |
C4—N1 | 1.342 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.400 (3) | C15—C16 | 1.375 (3) |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C5—C10 | 1.418 (3) | C16—C17 | 1.393 (3) |
C5—C6 | 1.424 (3) | C16—C19 | 1.506 (3) |
C6—N2 | 1.350 (3) | C17—C18 | 1.369 (3) |
C6—C7 | 1.402 (3) | C17—H17 | 0.9300 |
C7—C8 | 1.354 (3) | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | C19—H19A | 0.9600 |
C8—C9 | 1.418 (3) | C19—H19B | 0.9600 |
C8—H9 | 0.9300 | C19—H19C | 0.9600 |
C9—C10 | 1.370 (3) | N1—N2 | 1.341 (3) |
C9—N3 | 1.435 (3) | N3—S1 | 1.6389 (16) |
C10—O1 | 1.354 (3) | N3—H3N | 0.8417 |
C11—O1 | 1.418 (3) | O2—S1 | 1.4261 (15) |
C11—C12 | 1.497 (4) | O3—S1 | 1.4357 (15) |
C11—H11B | 0.9700 | ||
C2—C1—H1A | 120.0 | C11—C12—H12C | 109.5 |
C2—C1—H1B | 120.0 | H12B—C12—H12C | 109.5 |
H1A—C1—H1B | 120.0 | H12A—C12—H12C | 109.5 |
C1—C2—C3 | 124.1 (3) | C18—C13—C14 | 120.33 (19) |
C1—C2—H2 | 118.0 | C18—C13—S1 | 120.05 (15) |
C3—C2—H2 | 118.0 | C14—C13—S1 | 119.59 (16) |
C2—C3—N1 | 113.3 (2) | C15—C14—C13 | 118.9 (2) |
C2—C3—H3A | 108.9 | C15—C14—H14 | 120.6 |
N1—C3—H3A | 108.9 | C13—C14—H14 | 120.6 |
C2—C3—H3B | 108.9 | C16—C15—C14 | 122.0 (2) |
N1—C3—H3B | 108.9 | C16—C15—H15 | 119.0 |
H3A—C3—H3B | 107.7 | C14—C15—H15 | 119.0 |
N1—C4—C5 | 106.4 (2) | C15—C16—C17 | 118.1 (2) |
N1—C4—H4 | 126.8 | C15—C16—C19 | 121.5 (2) |
C5—C4—H4 | 126.8 | C17—C16—C19 | 120.4 (2) |
C4—C5—C10 | 137.2 (2) | C18—C17—C16 | 121.1 (2) |
C4—C5—C6 | 103.6 (2) | C18—C17—H17 | 119.5 |
C10—C5—C6 | 119.2 (2) | C16—C17—H17 | 119.5 |
N2—C6—C7 | 126.8 (2) | C17—C18—C13 | 119.67 (19) |
N2—C6—C5 | 111.7 (2) | C17—C18—H18 | 120.2 |
C7—C6—C5 | 121.4 (2) | C13—C18—H18 | 120.2 |
C8—C7—C6 | 117.9 (2) | C16—C19—H19A | 109.5 |
C8—C7—H7 | 121.0 | C16—C19—H19B | 109.5 |
C6—C7—H7 | 121.0 | H19A—C19—H19B | 109.5 |
C7—C8—C9 | 121.8 (2) | C16—C19—H19C | 109.5 |
C7—C8—H9 | 119.1 | H19A—C19—H19C | 109.5 |
C9—C8—H9 | 119.1 | H19B—C19—H19C | 109.5 |
C10—C9—C8 | 121.43 (19) | N2—N1—C4 | 114.5 (2) |
C10—C9—N3 | 119.84 (17) | N2—N1—C3 | 119.7 (2) |
C8—C9—N3 | 118.68 (18) | C4—N1—C3 | 125.8 (2) |
O1—C10—C9 | 116.71 (18) | N1—N2—C6 | 103.7 (2) |
O1—C10—C5 | 125.09 (19) | C9—N3—S1 | 121.32 (13) |
C9—C10—C5 | 118.13 (18) | C9—N3—H3N | 116.5 |
O1—C11—C12 | 108.4 (2) | S1—N3—H3N | 108.9 |
O1—C11—H11B | 110.0 | C10—O1—C11 | 120.3 (2) |
C12—C11—H11B | 110.0 | O2—S1—O3 | 118.36 (10) |
O1—C11—H11A | 110.0 | O2—S1—N3 | 108.69 (9) |
C12—C11—H11A | 110.0 | O3—S1—N3 | 104.65 (9) |
H11B—C11—H11A | 108.4 | O2—S1—C13 | 107.78 (9) |
C11—C12—H12B | 109.5 | O3—S1—C13 | 108.99 (10) |
C11—C12—H12A | 109.5 | N3—S1—C13 | 107.96 (9) |
H12B—C12—H12A | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H9···O2 | 0.93 | 2.48 | 2.991 (3) | 115 |
N3—H3N···O3i | 0.84 | 2.14 | 2.960 (2) | 164 |
C17—H17···O2ii | 0.93 | 2.54 | 3.333 (3) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H9···O2 | 0.93 | 2.48 | 2.991 (3) | 115 |
N3—H3N···O3i | 0.84 | 2.14 | 2.960 (2) | 164 |
C17—H17···O2ii | 0.93 | 2.54 | 3.333 (3) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, 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
Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190–o191. CSD CrossRef CAS IUCr Journals Google Scholar
Abbate, F., Casini, A., Owa, T., Scozzafava, A. & Supuran, C. T. (2004). Bioorg. Med. Chem. Lett. 14, 217–223. Web of Science CrossRef PubMed CAS Google Scholar
Bouissane, L., El Kazzouli, S., Leonce, 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
Drews, J. (2000). Science, 287, 1960–1964. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ghorab, M. M., Ragab, F. A. & Hamed, M. M. (2009). Eur. J. Med. Chem. 44, 4211–4217. Web of Science CrossRef PubMed CAS Google Scholar
Rostom, S. A. (2006). Bioorg. Med. Chem. 14, 6475–6485. 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
Supuran, C. T. & Scozzafava, A. (2001). Immun. Endoc. Metab. Agents Med. Chem. 1, 61–97. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Sulfonamides possess many types of biological activities and representatives of this class of pharmacological agents are widely used in clinic as antibacterial, hypoglycemic, diuretic and anti-carbonic anhydrase agents (Drews, 2000; Supuran & Scozzafava, 2001). Previously, a host of structurally novel sulfonamide derivatives have been reported to show substantial antitumor activity in vitro and/or in vivo (Abbate et al., 2004; Rostom, 2006; Ghorab et al., 2009). Recently, some N-[7(6)-indazolyl]arylsulfonamides prepared by our research group showed important antiproliferative activity against some human and murine cell lines ((Abbassi et al., 2012; Abbassi et al., 2013; Bouissane et al., 2006).
The molecule of the title compound is built up from two fused almost coplanar five- and six-membered rings (N1/N2/C4-C10), with a maximum deviation of 0.029 (3) Å for atom C9 (Fig. 1). The indazole ring system is nearly perpendicular to the planes through the allyl group (C1–C3) and benzene ring (C13–C18) as indicated by the dihedral angles between them of 83.9 (3) and 77.99 (15)°, respectively. An intramolecular C—H···O hydrogen bond (Table 1) stabilizes the molecular comformation. The cohesion of the crystal structure is ensured by N3–H3N···O3 hydrogen bonds between centrosymmetrically related molecules forming dimers, which are further connected into columns parallel to the b axis by C17–H17···O2 hydrogen bonds (Fig. 2, Table 1).