organic compounds
N-(3-Chloro-1-methyl-1H-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, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: ouafa_amiri@yahoo.fr
The 15H14ClN3O2S, contains two independent molecules showing different conformations: in one molecule, the indazole ring system makes a dihedral angle of 51.5 (1)° with the benzene ring whereas in the other, the indazole unit is almost perpendicular to the benzene ring [dihedral angle 77.7 (1)°]. In the crystal, the molecules are linked by N—H⋯N and N—H⋯O hydrogen bonds, forming a set of four molecules linked in pairs about an inversion centre.
of the title compound, CCCDC reference: 985013
Related literature
For the biological activity of et al. (2011); Mustafa et al. (2012); Scozzafava et al. (2003); Abbassi et al. (2012); Bouissane et al. (2006). For similar compounds see: Abbassi et al. (2013); Chicha et al. (2013).
see: El-SayedExperimental
Crystal data
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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: 985013
10.1107/S1600536814001184/rz5102sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001184/rz5102Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001184/rz5102Isup3.cml
A mixture of 3-chloro-1-methyl-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 5 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. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash
(eluted with ethyl acetate/hexane 2:8 v/). The title compound was recrystallized from ethanol, at room temperature, giving colourless crystals (m.p. 397 K, yield: 56%).All H atoms were located in a difference Fourier map and treated as riding with N—H = 0.89 Å, C–H = 0.93–0.96 Å, and with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C) for methyl H atoms. Two outliers (0 1 1, 0 2 1) were omitted in the last cycles of refinement.
Sulfonamides are an important class of compounds which are widely used in the design of diverse classes of drug candidates (El-Sayed et al., 2011; Mustafa et al., 2012; Scozzafava et al., 2003). 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; Bouissane et al., 2006). The present work is a continuation of the investigation of the
derivatives published recently by our team (Abbassi et al., 2013; Chicha et al., 2013).Each of the two independent molecules of the title compound is built up from fused five- and six-membered rings linked to a methylbenzenesulfonamide group as shown in Fig. 1. The molecules show different conformations. In the first molecule, the indazole ring system (N1/N2/C1–C7) makes a dihedral angle of 51.5 (1)° with the plane through the atoms forming the benzene ring (C9–C14). On the other hand, in the second molecule, the fused five- and six-membered ring system (N4/N5/C16–C22) is almost perpendicular to the benzene plane (C24–C29), as indicated by the dihedral angle of 77.7 (1)°. In the crystal, the molecules are interconnected by N3–H3N···N5 and N6–H6N···O3 hydrogen bonds (Table 1) in the way to form a set of four molecules linked in pairs by the inversion centre as shown in Fig. 2.
For the biological activity of
see: El-Sayed et al. (2011); Mustafa et al. (2012); Scozzafava et al. (2003); Abbassi et al. (2012); Bouissane et al. (2006). For similar compounds see: Abbassi et al. (2013); Chicha et al. (2013).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).C15H14ClN3O2S | F(000) = 1392 |
Mr = 335.80 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7548 reflections |
a = 8.4580 (13) Å | θ = 1.2–27.9° |
b = 34.920 (6) Å | µ = 0.38 mm−1 |
c = 10.8333 (17) Å | T = 296 K |
β = 97.226 (7)° | Block, colourless |
V = 3174.2 (9) Å3 | 0.43 × 0.34 × 0.29 mm |
Z = 8 |
Bruker X8 APEX Diffractometer | 7548 independent reflections |
Radiation source: fine-focus sealed tube | 5730 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.9°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→11 |
Tmin = 0.693, Tmax = 0.747 | k = −45→45 |
24523 measured reflections | l = −14→14 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.066P)2 + 1.0641P] where P = (Fo2 + 2Fc2)/3 |
7548 reflections | (Δ/σ)max = 0.001 |
398 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C15H14ClN3O2S | V = 3174.2 (9) Å3 |
Mr = 335.80 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.4580 (13) Å | µ = 0.38 mm−1 |
b = 34.920 (6) Å | T = 296 K |
c = 10.8333 (17) Å | 0.43 × 0.34 × 0.29 mm |
β = 97.226 (7)° |
Bruker X8 APEX Diffractometer | 7548 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5730 reflections with I > 2σ(I) |
Tmin = 0.693, Tmax = 0.747 | Rint = 0.029 |
24523 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.36 e Å−3 |
7548 reflections | Δρmin = −0.31 e Å−3 |
398 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 > σ(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 | 1.0746 (3) | 0.91347 (6) | 0.79881 (19) | 0.0504 (5) | |
C2 | 1.0407 (2) | 0.87989 (6) | 0.72723 (17) | 0.0419 (4) | |
C3 | 0.9081 (2) | 0.85660 (6) | 0.69368 (18) | 0.0434 (4) | |
H3 | 0.8109 | 0.8619 | 0.7216 | 0.052* | |
C4 | 0.9252 (2) | 0.82564 (6) | 0.61843 (18) | 0.0423 (4) | |
C5 | 1.0743 (3) | 0.81730 (6) | 0.57778 (19) | 0.0486 (5) | |
H5 | 1.0831 | 0.7959 | 0.5278 | 0.058* | |
C6 | 1.2054 (3) | 0.83968 (6) | 0.60973 (19) | 0.0495 (5) | |
H6 | 1.3029 | 0.8339 | 0.5830 | 0.059* | |
C7 | 1.1868 (2) | 0.87174 (6) | 0.68471 (17) | 0.0420 (4) | |
C8 | 1.4506 (3) | 0.90628 (9) | 0.7010 (3) | 0.0770 (8) | |
H8A | 1.4792 | 0.8864 | 0.6466 | 0.115* | |
H8B | 1.5234 | 0.9061 | 0.7765 | 0.115* | |
H8C | 1.4556 | 0.9307 | 0.6608 | 0.115* | |
C9 | 0.7224 (2) | 0.81651 (6) | 0.3369 (2) | 0.0480 (5) | |
C10 | 0.7436 (3) | 0.78368 (7) | 0.2700 (2) | 0.0555 (5) | |
H10 | 0.7121 | 0.7601 | 0.2983 | 0.067* | |
C11 | 0.8113 (3) | 0.78596 (8) | 0.1618 (2) | 0.0630 (6) | |
H11 | 0.8253 | 0.7637 | 0.1170 | 0.076* | |
C12 | 0.8592 (3) | 0.82078 (9) | 0.1178 (2) | 0.0647 (7) | |
C13 | 0.8353 (3) | 0.85328 (8) | 0.1854 (3) | 0.0699 (7) | |
H13 | 0.8658 | 0.8769 | 0.1565 | 0.084* | |
C14 | 0.7677 (3) | 0.85179 (7) | 0.2943 (2) | 0.0631 (6) | |
H14 | 0.7526 | 0.8740 | 0.3386 | 0.076* | |
C15 | 0.9348 (4) | 0.82282 (12) | −0.0009 (3) | 0.0958 (11) | |
H15A | 0.9758 | 0.8481 | −0.0105 | 0.144* | |
H15B | 0.8564 | 0.8170 | −0.0704 | 0.144* | |
H15C | 1.0203 | 0.8046 | 0.0026 | 0.144* | |
C16 | −0.0868 (3) | 0.68888 (6) | 0.5237 (2) | 0.0461 (5) | |
C17 | −0.1129 (2) | 0.65302 (6) | 0.57713 (18) | 0.0400 (4) | |
C18 | −0.0879 (2) | 0.61439 (6) | 0.54823 (17) | 0.0409 (4) | |
H18 | −0.0357 | 0.6077 | 0.4807 | 0.049* | |
C19 | −0.1426 (2) | 0.58688 (6) | 0.62205 (18) | 0.0424 (4) | |
C20 | −0.2169 (3) | 0.59712 (7) | 0.7270 (2) | 0.0550 (6) | |
H20 | −0.2535 | 0.5779 | 0.7755 | 0.066* | |
C21 | −0.2365 (3) | 0.63448 (7) | 0.7594 (2) | 0.0558 (6) | |
H21 | −0.2825 | 0.6409 | 0.8302 | 0.067* | |
C22 | −0.1853 (2) | 0.66258 (6) | 0.68257 (19) | 0.0439 (4) | |
C23 | −0.2682 (3) | 0.72545 (7) | 0.7723 (2) | 0.0621 (6) | |
H23A | −0.3477 | 0.7416 | 0.7275 | 0.093* | |
H23B | −0.1879 | 0.7411 | 0.8181 | 0.093* | |
H23C | −0.3170 | 0.7095 | 0.8289 | 0.093* | |
C24 | 0.1019 (2) | 0.52481 (6) | 0.76926 (18) | 0.0426 (4) | |
C25 | 0.2386 (3) | 0.52368 (7) | 0.7115 (2) | 0.0555 (6) | |
H25 | 0.2331 | 0.5167 | 0.6282 | 0.067* | |
C26 | 0.3831 (3) | 0.53297 (7) | 0.7785 (2) | 0.0590 (6) | |
H26 | 0.4748 | 0.5321 | 0.7393 | 0.071* | |
C27 | 0.3950 (3) | 0.54353 (6) | 0.9019 (2) | 0.0512 (5) | |
C28 | 0.2566 (3) | 0.54467 (8) | 0.9573 (2) | 0.0630 (6) | |
H28 | 0.2620 | 0.5518 | 1.0405 | 0.076* | |
C29 | 0.1113 (3) | 0.53550 (7) | 0.8926 (2) | 0.0581 (6) | |
H29 | 0.0196 | 0.5365 | 0.9318 | 0.070* | |
C30 | 0.5535 (3) | 0.55361 (9) | 0.9739 (2) | 0.0703 (7) | |
H30A | 0.5504 | 0.5487 | 1.0607 | 0.105* | |
H30B | 0.5756 | 0.5802 | 0.9622 | 0.105* | |
H30C | 0.6356 | 0.5383 | 0.9447 | 0.105* | |
N1 | 1.2903 (2) | 0.89975 (5) | 0.72974 (16) | 0.0508 (4) | |
N2 | 1.2212 (2) | 0.92559 (5) | 0.79962 (17) | 0.0536 (5) | |
N3 | 0.7936 (2) | 0.80055 (5) | 0.58368 (17) | 0.0510 (4) | |
H3N | 0.8174 | 0.7786 | 0.5734 | 0.061* | |
N4 | −0.1959 (2) | 0.70164 (5) | 0.68515 (17) | 0.0507 (4) | |
N5 | −0.1351 (2) | 0.71778 (5) | 0.58704 (18) | 0.0511 (4) | |
N6 | −0.1321 (2) | 0.54756 (5) | 0.58771 (16) | 0.0481 (4) | |
H6N | −0.1053 | 0.5437 | 0.5194 | 0.048 (6)* | |
O1 | 0.5382 (2) | 0.78159 (7) | 0.47439 (19) | 0.0876 (7) | |
O2 | 0.5960 (2) | 0.85057 (6) | 0.51171 (18) | 0.0796 (6) | |
O3 | −0.06493 (19) | 0.48003 (4) | 0.60889 (14) | 0.0518 (4) | |
O4 | −0.19633 (19) | 0.51112 (5) | 0.77251 (15) | 0.0572 (4) | |
S1 | 0.64646 (7) | 0.81318 (2) | 0.47990 (6) | 0.05832 (17) | |
S2 | −0.08315 (6) | 0.512747 (14) | 0.68561 (5) | 0.04431 (14) | |
Cl1 | 0.94290 (10) | 0.93782 (2) | 0.87784 (8) | 0.0867 (3) | |
Cl2 | −0.00273 (9) | 0.697034 (19) | 0.39037 (6) | 0.06916 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0641 (14) | 0.0440 (11) | 0.0436 (11) | 0.0153 (10) | 0.0092 (10) | −0.0055 (9) |
C2 | 0.0534 (11) | 0.0389 (10) | 0.0338 (9) | 0.0118 (9) | 0.0069 (8) | 0.0006 (8) |
C3 | 0.0489 (11) | 0.0449 (11) | 0.0380 (10) | 0.0096 (9) | 0.0113 (8) | 0.0027 (8) |
C4 | 0.0500 (11) | 0.0416 (10) | 0.0357 (9) | 0.0032 (9) | 0.0071 (8) | 0.0031 (8) |
C5 | 0.0575 (12) | 0.0465 (12) | 0.0435 (11) | 0.0050 (10) | 0.0131 (9) | −0.0104 (9) |
C6 | 0.0505 (11) | 0.0533 (13) | 0.0468 (11) | 0.0059 (10) | 0.0145 (9) | −0.0097 (10) |
C7 | 0.0495 (11) | 0.0432 (11) | 0.0334 (9) | 0.0062 (9) | 0.0050 (8) | −0.0019 (8) |
C8 | 0.0678 (16) | 0.0822 (19) | 0.0854 (19) | −0.0212 (14) | 0.0272 (14) | −0.0310 (16) |
C9 | 0.0411 (10) | 0.0535 (13) | 0.0486 (12) | −0.0007 (9) | 0.0028 (9) | 0.0009 (10) |
C10 | 0.0622 (13) | 0.0516 (13) | 0.0525 (13) | −0.0028 (11) | 0.0058 (10) | 0.0013 (10) |
C11 | 0.0679 (15) | 0.0713 (17) | 0.0494 (13) | 0.0015 (13) | 0.0058 (11) | −0.0075 (12) |
C12 | 0.0559 (13) | 0.092 (2) | 0.0455 (12) | −0.0060 (13) | 0.0021 (10) | 0.0076 (13) |
C13 | 0.0734 (17) | 0.0663 (17) | 0.0688 (16) | −0.0111 (14) | 0.0046 (13) | 0.0183 (14) |
C14 | 0.0682 (15) | 0.0523 (14) | 0.0684 (16) | −0.0010 (12) | 0.0066 (12) | −0.0025 (12) |
C15 | 0.084 (2) | 0.152 (3) | 0.0528 (15) | −0.015 (2) | 0.0146 (14) | 0.0132 (19) |
C16 | 0.0468 (11) | 0.0431 (11) | 0.0490 (11) | −0.0042 (9) | 0.0083 (9) | 0.0018 (9) |
C17 | 0.0390 (9) | 0.0407 (10) | 0.0398 (10) | −0.0011 (8) | 0.0036 (8) | 0.0007 (8) |
C18 | 0.0430 (10) | 0.0432 (11) | 0.0369 (9) | 0.0013 (8) | 0.0071 (8) | −0.0018 (8) |
C19 | 0.0483 (11) | 0.0366 (10) | 0.0425 (10) | 0.0043 (8) | 0.0060 (8) | 0.0009 (8) |
C20 | 0.0732 (15) | 0.0443 (12) | 0.0520 (12) | 0.0069 (11) | 0.0256 (11) | 0.0078 (10) |
C21 | 0.0726 (15) | 0.0502 (13) | 0.0488 (12) | 0.0104 (11) | 0.0241 (11) | 0.0028 (10) |
C22 | 0.0454 (10) | 0.0399 (11) | 0.0462 (11) | 0.0052 (8) | 0.0051 (8) | −0.0023 (8) |
C23 | 0.0732 (16) | 0.0530 (14) | 0.0616 (14) | 0.0132 (12) | 0.0150 (12) | −0.0079 (11) |
C24 | 0.0545 (11) | 0.0334 (10) | 0.0416 (10) | 0.0005 (9) | 0.0123 (9) | 0.0024 (8) |
C25 | 0.0614 (13) | 0.0672 (15) | 0.0401 (11) | −0.0117 (11) | 0.0156 (10) | −0.0138 (10) |
C26 | 0.0577 (13) | 0.0688 (16) | 0.0536 (13) | −0.0105 (12) | 0.0191 (10) | −0.0163 (11) |
C27 | 0.0633 (13) | 0.0449 (12) | 0.0459 (11) | −0.0046 (10) | 0.0091 (10) | −0.0046 (9) |
C28 | 0.0758 (16) | 0.0758 (17) | 0.0386 (11) | 0.0001 (13) | 0.0127 (11) | −0.0094 (11) |
C29 | 0.0641 (14) | 0.0699 (16) | 0.0439 (12) | 0.0031 (12) | 0.0214 (11) | −0.0026 (11) |
C30 | 0.0760 (17) | 0.0789 (18) | 0.0556 (14) | −0.0116 (14) | 0.0068 (12) | −0.0109 (13) |
N1 | 0.0536 (10) | 0.0516 (11) | 0.0473 (10) | 0.0013 (8) | 0.0073 (8) | −0.0106 (8) |
N2 | 0.0667 (12) | 0.0454 (10) | 0.0483 (10) | 0.0062 (9) | 0.0057 (9) | −0.0097 (8) |
N3 | 0.0577 (11) | 0.0457 (10) | 0.0506 (10) | −0.0035 (8) | 0.0112 (8) | −0.0002 (8) |
N4 | 0.0585 (11) | 0.0412 (10) | 0.0533 (10) | 0.0038 (8) | 0.0107 (8) | −0.0025 (8) |
N5 | 0.0547 (10) | 0.0414 (10) | 0.0574 (11) | −0.0030 (8) | 0.0083 (8) | −0.0002 (8) |
N6 | 0.0656 (11) | 0.0393 (9) | 0.0410 (9) | 0.0040 (8) | 0.0126 (8) | 0.0009 (7) |
O1 | 0.0602 (11) | 0.1231 (18) | 0.0819 (13) | −0.0364 (11) | 0.0190 (9) | −0.0040 (12) |
O2 | 0.0652 (11) | 0.0982 (15) | 0.0771 (12) | 0.0316 (10) | 0.0148 (9) | −0.0131 (11) |
O3 | 0.0635 (9) | 0.0352 (7) | 0.0582 (9) | −0.0032 (7) | 0.0131 (7) | −0.0004 (6) |
O4 | 0.0609 (9) | 0.0524 (9) | 0.0629 (10) | −0.0027 (7) | 0.0257 (8) | 0.0083 (7) |
S1 | 0.0431 (3) | 0.0763 (4) | 0.0573 (3) | −0.0024 (3) | 0.0130 (2) | −0.0057 (3) |
S2 | 0.0526 (3) | 0.0346 (3) | 0.0478 (3) | −0.0019 (2) | 0.0143 (2) | 0.0037 (2) |
Cl1 | 0.0885 (5) | 0.0726 (5) | 0.1041 (6) | 0.0191 (4) | 0.0319 (4) | −0.0360 (4) |
Cl2 | 0.0874 (5) | 0.0592 (4) | 0.0663 (4) | −0.0082 (3) | 0.0308 (3) | 0.0107 (3) |
C1—N2 | 1.309 (3) | C18—C19 | 1.367 (3) |
C1—C2 | 1.415 (3) | C18—H18 | 0.9300 |
C1—Cl1 | 1.713 (2) | C19—C20 | 1.413 (3) |
C2—C3 | 1.396 (3) | C19—N6 | 1.428 (3) |
C2—C7 | 1.401 (3) | C20—C21 | 1.366 (3) |
C3—C4 | 1.373 (3) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.390 (3) |
C4—C5 | 1.418 (3) | C21—H21 | 0.9300 |
C4—N3 | 1.429 (3) | C22—N4 | 1.367 (3) |
C5—C6 | 1.365 (3) | C23—N4 | 1.450 (3) |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C7 | 1.404 (3) | C23—H23B | 0.9600 |
C6—H6 | 0.9300 | C23—H23C | 0.9600 |
C7—N1 | 1.361 (3) | C24—C29 | 1.380 (3) |
C8—N1 | 1.447 (3) | C24—C25 | 1.383 (3) |
C8—H8A | 0.9600 | C24—S2 | 1.758 (2) |
C8—H8B | 0.9600 | C25—C26 | 1.379 (3) |
C8—H8C | 0.9600 | C25—H25 | 0.9300 |
C9—C10 | 1.380 (3) | C26—C27 | 1.379 (3) |
C9—C14 | 1.386 (3) | C26—H26 | 0.9300 |
C9—S1 | 1.754 (2) | C27—C28 | 1.382 (3) |
C10—C11 | 1.370 (3) | C27—C30 | 1.505 (3) |
C10—H10 | 0.9300 | C28—C29 | 1.374 (4) |
C11—C12 | 1.385 (4) | C28—H28 | 0.9300 |
C11—H11 | 0.9300 | C29—H29 | 0.9300 |
C12—C13 | 1.379 (4) | C30—H30A | 0.9600 |
C12—C15 | 1.509 (4) | C30—H30B | 0.9600 |
C13—C14 | 1.376 (4) | C30—H30C | 0.9600 |
C13—H13 | 0.9300 | N1—N2 | 1.356 (2) |
C14—H14 | 0.9300 | N3—S1 | 1.630 (2) |
C15—H15A | 0.9600 | N3—H3N | 0.8039 |
C15—H15B | 0.9600 | N4—N5 | 1.360 (3) |
C15—H15C | 0.9600 | N6—S2 | 1.6321 (17) |
C16—N5 | 1.314 (3) | N6—H6N | 0.8114 |
C16—C17 | 1.409 (3) | O1—S1 | 1.430 (2) |
C16—Cl2 | 1.712 (2) | O2—S1 | 1.429 (2) |
C17—C22 | 1.403 (3) | O3—S2 | 1.4325 (15) |
C17—C18 | 1.407 (3) | O4—S2 | 1.4256 (15) |
N2—C1—C2 | 113.42 (18) | C21—C20—H20 | 119.0 |
N2—C1—Cl1 | 120.72 (17) | C19—C20—H20 | 119.0 |
C2—C1—Cl1 | 125.85 (18) | C20—C21—C22 | 117.6 (2) |
C3—C2—C7 | 120.60 (18) | C20—C21—H21 | 121.2 |
C3—C2—C1 | 136.53 (19) | C22—C21—H21 | 121.2 |
C7—C2—C1 | 102.86 (19) | N4—C22—C21 | 131.7 (2) |
C4—C3—C2 | 118.20 (18) | N4—C22—C17 | 106.89 (18) |
C4—C3—H3 | 120.9 | C21—C22—C17 | 121.34 (19) |
C2—C3—H3 | 120.9 | N4—C23—H23A | 109.5 |
C3—C4—C5 | 120.68 (19) | N4—C23—H23B | 109.5 |
C3—C4—N3 | 120.20 (18) | H23A—C23—H23B | 109.5 |
C5—C4—N3 | 119.08 (18) | N4—C23—H23C | 109.5 |
C6—C5—C4 | 122.01 (19) | H23A—C23—H23C | 109.5 |
C6—C5—H5 | 119.0 | H23B—C23—H23C | 109.5 |
C4—C5—H5 | 119.0 | C29—C24—C25 | 119.7 (2) |
C5—C6—C7 | 117.16 (19) | C29—C24—S2 | 120.19 (17) |
C5—C6—H6 | 121.4 | C25—C24—S2 | 120.06 (16) |
C7—C6—H6 | 121.4 | C26—C25—C24 | 119.5 (2) |
N1—C7—C2 | 106.86 (17) | C26—C25—H25 | 120.3 |
N1—C7—C6 | 131.81 (19) | C24—C25—H25 | 120.3 |
C2—C7—C6 | 121.33 (19) | C27—C26—C25 | 121.6 (2) |
N1—C8—H8A | 109.5 | C27—C26—H26 | 119.2 |
N1—C8—H8B | 109.5 | C25—C26—H26 | 119.2 |
H8A—C8—H8B | 109.5 | C26—C27—C28 | 117.8 (2) |
N1—C8—H8C | 109.5 | C26—C27—C30 | 121.1 (2) |
H8A—C8—H8C | 109.5 | C28—C27—C30 | 121.1 (2) |
H8B—C8—H8C | 109.5 | C29—C28—C27 | 121.6 (2) |
C10—C9—C14 | 120.3 (2) | C29—C28—H28 | 119.2 |
C10—C9—S1 | 119.66 (18) | C27—C28—H28 | 119.2 |
C14—C9—S1 | 120.01 (19) | C28—C29—C24 | 119.7 (2) |
C11—C10—C9 | 119.8 (2) | C28—C29—H29 | 120.1 |
C11—C10—H10 | 120.1 | C24—C29—H29 | 120.1 |
C9—C10—H10 | 120.1 | C27—C30—H30A | 109.5 |
C10—C11—C12 | 121.1 (2) | C27—C30—H30B | 109.5 |
C10—C11—H11 | 119.4 | H30A—C30—H30B | 109.5 |
C12—C11—H11 | 119.4 | C27—C30—H30C | 109.5 |
C13—C12—C11 | 118.2 (2) | H30A—C30—H30C | 109.5 |
C13—C12—C15 | 121.3 (3) | H30B—C30—H30C | 109.5 |
C11—C12—C15 | 120.5 (3) | N2—N1—C7 | 112.03 (17) |
C14—C13—C12 | 121.9 (3) | N2—N1—C8 | 119.78 (19) |
C14—C13—H13 | 119.0 | C7—N1—C8 | 127.85 (19) |
C12—C13—H13 | 119.0 | C1—N2—N1 | 104.81 (17) |
C13—C14—C9 | 118.8 (2) | C4—N3—S1 | 121.17 (15) |
C13—C14—H14 | 120.6 | C4—N3—H3N | 114.9 |
C9—C14—H14 | 120.6 | S1—N3—H3N | 110.2 |
C12—C15—H15A | 109.5 | N5—N4—C22 | 111.42 (17) |
C12—C15—H15B | 109.5 | N5—N4—C23 | 120.21 (18) |
H15A—C15—H15B | 109.5 | C22—N4—C23 | 128.28 (19) |
C12—C15—H15C | 109.5 | C16—N5—N4 | 105.25 (17) |
H15A—C15—H15C | 109.5 | C19—N6—S2 | 124.46 (14) |
H15B—C15—H15C | 109.5 | C19—N6—H6N | 115.4 |
N5—C16—C17 | 113.14 (19) | S2—N6—H6N | 113.2 |
N5—C16—Cl2 | 120.16 (16) | O2—S1—O1 | 120.36 (13) |
C17—C16—Cl2 | 126.69 (16) | O2—S1—N3 | 107.83 (11) |
C22—C17—C18 | 120.18 (18) | O1—S1—N3 | 104.45 (12) |
C22—C17—C16 | 103.29 (18) | O2—S1—C9 | 107.82 (12) |
C18—C17—C16 | 136.51 (19) | O1—S1—C9 | 108.55 (11) |
C19—C18—C17 | 118.18 (18) | N3—S1—C9 | 107.12 (10) |
C19—C18—H18 | 120.9 | O4—S2—O3 | 118.79 (10) |
C17—C18—H18 | 120.9 | O4—S2—N6 | 108.81 (10) |
C18—C19—C20 | 120.70 (19) | O3—S2—N6 | 104.71 (9) |
C18—C19—N6 | 119.09 (18) | O4—S2—C24 | 107.30 (10) |
C20—C19—N6 | 120.11 (18) | O3—S2—C24 | 109.65 (10) |
C21—C20—C19 | 121.9 (2) | N6—S2—C24 | 107.03 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···N5i | 0.80 | 2.16 | 2.952 (3) | 167 |
N6—H6N···O3ii | 0.81 | 2.28 | 3.022 (2) | 152 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···N5i | 0.80 | 2.16 | 2.952 (3) | 167.0 |
N6—H6N···O3ii | 0.81 | 2.28 | 3.022 (2) | 152.3 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z+1. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
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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 are an important class of compounds which are widely used in the design of diverse classes of drug candidates (El-Sayed et al., 2011; Mustafa et al., 2012; Scozzafava et al., 2003). 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; Bouissane et al., 2006). The present work is a continuation of the investigation of the sulfonamides derivatives published recently by our team (Abbassi et al., 2013; Chicha et al., 2013).
Each of the two independent molecules of the title compound is built up from fused five- and six-membered rings linked to a methylbenzenesulfonamide group as shown in Fig. 1. The molecules show different conformations. In the first molecule, the indazole ring system (N1/N2/C1–C7) makes a dihedral angle of 51.5 (1)° with the plane through the atoms forming the benzene ring (C9–C14). On the other hand, in the second molecule, the fused five- and six-membered ring system (N4/N5/C16–C22) is almost perpendicular to the benzene plane (C24–C29), as indicated by the dihedral angle of 77.7 (1)°. In the crystal, the molecules are interconnected by N3–H3N···N5 and N6–H6N···O3 hydrogen bonds (Table 1) in the way to form a set of four molecules linked in pairs by the inversion centre as shown in Fig. 2.