organic compounds
N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methylbenzenesulfonamide
ofaLaboratoire 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: m_chigr@yahoo.fr
The 3-chloro-1H-indazole system in the title molecule, C17H16ClN3O2S, is almost planar, with the largest deviation from the mean plane being 0.029 (2) Å for one of the N atoms. This system is nearly perpendicular to the allyl chain, as indicated by the C—C—N—N torsion angle of −90.1 (6)° between them. The allyl group is split into two fragments, the major component has a site occupancy of 0.579 (7). The indazole system makes a dihedral angle of 47.53 (10)° with the plane through the benzene ring. In the crystal, molecules are connected by N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network.
CCDC reference: 1018456
1. Related literature
For the biological activity of et al. (2011); Mustafa et al. (2012); Scozzafava et al. (2003). For similar compounds, see: Abbassi et al. (2012, 2013); Chicha et al. (2014).
see: El-Sayed,2. Experimental
2.1. Crystal data
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2.3. Refinement
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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: 1018456
10.1107/S1600536814018194/tk5336sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018194/tk5336Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018194/tk5336Isup3.cml
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). Previously, we identified a series of indazoles bearing a sulfonamide moiety with good antiproliferative activities (Abbassi et al., 2012; Abbassi, et al. 2013; Chicha et al., 2014).
The molecule of the title compound is built up from two fused five- and six-membered rings (N1 N2 C2 to C8) almost coplanar, with a maximum deviation of 0.029 (2) Å for N1 atom (Fig. 1). The dihedral angle between the indazol system and the plane through the benzene ring (C9 to C14) is of 47.53 (10)°. The allyl chain is perpendicular to the fused rings system as indicated by the C(16A)—C(15)—N(1)—N(2) torsion angle of -90.1 (6)°.
The cohesion of the
is ensured by N3–H3N···O1, C5–H5···O1 and C4–H4···O2 hydrogen bonds between molecules to form a three-dimensional network as shown in Fig. 2 and Table 1.A mixture of 1-allyl-3-chloro-5-nitroindazole (1.22 mmol) and anhydrous SnCl2 (1.1 g, 6.1 mmol) in 25 ml of absolute ethanol 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-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). The title compound was recrystallized from its ethanol solution. Yield: 65%, M.pt: 394 K.The reflections (002), (110), (021) and (020), probably affected by the beam stop, were removed from the final
The of the model, i.e. disordered allyl group, required constraints on the distance C15—C16—C17 and atomic displacements of allyl group. The H atoms were located in a difference map and treated as riding with C—H = 0.96 Å, C—H = 0.97 Å, C—H = 0.93 Å, and N—H = 0.81 Å for methyl, methylene, aromatic CH and NH, respectively, and with Uiso(H) = 1.2 Ueq (methylene, aromatic, NH) and Uiso(H) = 1.5 Ueq for methyl.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).C17H16ClN3O2S | Dx = 1.355 Mg m−3 |
Mr = 361.84 | Melting point: 394 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 3621 reflections |
a = 8.1736 (12) Å | θ = 2.8–26.4° |
b = 22.504 (4) Å | µ = 0.35 mm−1 |
c = 19.279 (3) Å | T = 296 K |
V = 3546.2 (10) Å3 | Block, colourless |
Z = 8 | 0.40 × 0.36 × 0.31 mm |
F(000) = 1504 |
Bruker X8 APEX diffractometer | 3621 independent reflections |
Radiation source: fine-focus sealed tube | 2327 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −9→10 |
Tmin = 0.693, Tmax = 0.747 | k = −28→26 |
18362 measured reflections | l = −22→24 |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0557P)2 + 0.7269P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3621 reflections | Δρmax = 0.26 e Å−3 |
225 parameters | Δρmin = −0.26 e Å−3 |
4 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0026 (4) |
C17H16ClN3O2S | V = 3546.2 (10) Å3 |
Mr = 361.84 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 8.1736 (12) Å | µ = 0.35 mm−1 |
b = 22.504 (4) Å | T = 296 K |
c = 19.279 (3) Å | 0.40 × 0.36 × 0.31 mm |
Bruker X8 APEX diffractometer | 3621 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | 2327 reflections with I > 2σ(I) |
Tmin = 0.693, Tmax = 0.747 | Rint = 0.051 |
18362 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 4 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.26 e Å−3 |
3621 reflections | Δρmin = −0.26 e Å−3 |
225 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 | Occ. (<1) | |
C1 | 0.8260 (3) | −0.03622 (11) | 0.08181 (12) | 0.0516 (6) | |
C2 | 0.8328 (3) | 0.02554 (10) | 0.06992 (11) | 0.0427 (5) | |
C3 | 0.9964 (3) | 0.04008 (11) | 0.08496 (12) | 0.0481 (6) | |
C4 | 1.0542 (3) | 0.09849 (12) | 0.07951 (13) | 0.0570 (7) | |
H4 | 1.1624 | 0.1081 | 0.0892 | 0.068* | |
C5 | 0.9446 (3) | 0.14053 (11) | 0.05939 (13) | 0.0532 (6) | |
H5 | 0.9793 | 0.1798 | 0.0558 | 0.064* | |
C6 | 0.7806 (3) | 0.12692 (10) | 0.04380 (11) | 0.0444 (5) | |
C7 | 0.7233 (3) | 0.06945 (10) | 0.04817 (11) | 0.0445 (6) | |
H7 | 0.6156 | 0.0602 | 0.0370 | 0.053* | |
C8 | 0.6222 (3) | 0.22836 (11) | 0.14802 (13) | 0.0503 (6) | |
C9 | 0.6865 (3) | 0.19241 (12) | 0.19974 (14) | 0.0628 (7) | |
H9 | 0.6795 | 0.1513 | 0.1961 | 0.075* | |
C10 | 0.7609 (4) | 0.21805 (15) | 0.25663 (15) | 0.0741 (8) | |
H10 | 0.8063 | 0.1939 | 0.2907 | 0.089* | |
C11 | 0.7691 (4) | 0.27915 (16) | 0.26378 (16) | 0.0756 (9) | |
C12 | 0.7046 (4) | 0.31338 (14) | 0.21193 (19) | 0.0830 (10) | |
H12 | 0.7097 | 0.3545 | 0.2162 | 0.100* | |
C13 | 0.6321 (3) | 0.28965 (12) | 0.15350 (16) | 0.0669 (8) | |
H13 | 0.5911 | 0.3141 | 0.1187 | 0.080* | |
C14 | 0.8448 (5) | 0.3061 (2) | 0.32849 (19) | 0.1179 (15) | |
H14A | 0.8818 | 0.2750 | 0.3586 | 0.177* | |
H14B | 0.7645 | 0.3298 | 0.3521 | 0.177* | |
H14C | 0.9358 | 0.3307 | 0.3156 | 0.177* | |
C15 | 1.2392 (3) | −0.01960 (14) | 0.12649 (15) | 0.0755 (9) | |
H15A | 1.3111 | 0.0081 | 0.1029 | 0.091* | |
H15B | 1.2767 | −0.0597 | 0.1172 | 0.091* | |
C16A | 1.2386 (8) | −0.0080 (6) | 0.2012 (2) | 0.0902 (19) | 0.579 (7) |
H16A | 1.1739 | −0.0334 | 0.2276 | 0.108* | 0.579 (7) |
C17A | 1.3154 (12) | 0.0324 (4) | 0.2354 (5) | 0.120 (2) | 0.579 (7) |
H17A | 1.3823 | 0.0593 | 0.2122 | 0.144* | 0.579 (7) |
H17B | 1.3039 | 0.0348 | 0.2833 | 0.144* | 0.579 (7) |
C16B | 1.2961 (13) | −0.0101 (9) | 0.1975 (3) | 0.0902 (19) | 0.421 (7) |
H16B | 1.3979 | −0.0238 | 0.2119 | 0.108* | 0.421 (7) |
C17B | 1.2008 (15) | 0.0178 (6) | 0.2393 (6) | 0.120 (2) | 0.421 (7) |
H17C | 1.0994 | 0.0312 | 0.2241 | 0.144* | 0.421 (7) |
H17D | 1.2333 | 0.0246 | 0.2849 | 0.144* | 0.421 (7) |
N1 | 1.0722 (2) | −0.01207 (10) | 0.10293 (11) | 0.0576 (6) | |
N2 | 0.9665 (3) | −0.05905 (9) | 0.10217 (11) | 0.0593 (6) | |
N3 | 0.6711 (2) | 0.17352 (9) | 0.02206 (10) | 0.0510 (5) | |
H3N | 0.7140 | 0.2027 | 0.0059 | 0.061* | |
O1 | 0.4373 (2) | 0.24036 (8) | 0.03876 (10) | 0.0743 (6) | |
O2 | 0.44423 (19) | 0.14312 (8) | 0.09892 (10) | 0.0613 (5) | |
S1 | 0.52632 (7) | 0.19552 (3) | 0.07563 (3) | 0.0508 (2) | |
Cl1 | 0.65782 (9) | −0.08137 (3) | 0.07145 (5) | 0.0776 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0444 (14) | 0.0511 (15) | 0.0591 (16) | 0.0037 (11) | −0.0066 (12) | −0.0015 (11) |
C2 | 0.0360 (12) | 0.0497 (14) | 0.0424 (12) | 0.0002 (10) | −0.0015 (10) | −0.0025 (10) |
C3 | 0.0361 (13) | 0.0595 (15) | 0.0486 (14) | 0.0021 (11) | −0.0009 (10) | −0.0027 (11) |
C4 | 0.0324 (13) | 0.0728 (18) | 0.0659 (17) | −0.0071 (12) | −0.0022 (12) | −0.0017 (13) |
C5 | 0.0449 (14) | 0.0543 (15) | 0.0605 (15) | −0.0097 (12) | 0.0030 (12) | 0.0020 (11) |
C6 | 0.0380 (13) | 0.0514 (14) | 0.0437 (13) | −0.0018 (11) | 0.0008 (10) | 0.0035 (10) |
C7 | 0.0326 (12) | 0.0537 (15) | 0.0471 (13) | −0.0013 (10) | −0.0013 (10) | −0.0012 (10) |
C8 | 0.0372 (13) | 0.0534 (16) | 0.0603 (16) | −0.0031 (11) | 0.0080 (11) | 0.0041 (11) |
C9 | 0.0652 (18) | 0.0606 (17) | 0.0625 (17) | −0.0024 (14) | 0.0008 (14) | 0.0087 (13) |
C10 | 0.0681 (19) | 0.099 (2) | 0.0556 (17) | −0.0019 (18) | 0.0005 (15) | 0.0061 (16) |
C11 | 0.0620 (18) | 0.102 (3) | 0.0632 (19) | −0.0170 (18) | 0.0130 (16) | −0.0167 (17) |
C12 | 0.094 (2) | 0.064 (2) | 0.090 (2) | −0.0176 (18) | 0.006 (2) | −0.0170 (17) |
C13 | 0.0691 (18) | 0.0497 (16) | 0.082 (2) | −0.0021 (14) | 0.0029 (16) | 0.0027 (13) |
C14 | 0.113 (3) | 0.162 (4) | 0.078 (2) | −0.028 (3) | 0.007 (2) | −0.041 (2) |
C15 | 0.0471 (15) | 0.094 (2) | 0.086 (2) | 0.0195 (15) | −0.0203 (15) | −0.0028 (16) |
C16A | 0.051 (5) | 0.108 (3) | 0.112 (3) | 0.026 (6) | −0.053 (3) | −0.003 (3) |
C17A | 0.125 (7) | 0.150 (6) | 0.085 (4) | −0.008 (6) | −0.019 (5) | −0.002 (4) |
C16B | 0.051 (5) | 0.108 (3) | 0.112 (3) | 0.026 (6) | −0.053 (3) | −0.003 (3) |
C17B | 0.125 (7) | 0.150 (6) | 0.085 (4) | −0.008 (6) | −0.019 (5) | −0.002 (4) |
N1 | 0.0400 (11) | 0.0674 (15) | 0.0655 (14) | 0.0090 (11) | −0.0081 (10) | −0.0028 (11) |
N2 | 0.0556 (13) | 0.0575 (13) | 0.0649 (14) | 0.0090 (12) | −0.0079 (11) | −0.0014 (10) |
N3 | 0.0487 (12) | 0.0504 (12) | 0.0540 (12) | −0.0004 (9) | 0.0008 (10) | 0.0125 (9) |
O1 | 0.0602 (12) | 0.0682 (12) | 0.0945 (14) | 0.0180 (10) | −0.0207 (11) | 0.0137 (10) |
O2 | 0.0408 (9) | 0.0583 (11) | 0.0848 (12) | −0.0107 (8) | 0.0069 (9) | 0.0003 (9) |
S1 | 0.0372 (3) | 0.0478 (4) | 0.0673 (4) | 0.0015 (3) | −0.0050 (3) | 0.0078 (3) |
Cl1 | 0.0639 (5) | 0.0553 (4) | 0.1137 (7) | −0.0094 (3) | −0.0186 (4) | 0.0066 (4) |
C1—N2 | 1.318 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.410 (3) | C13—H13 | 0.9300 |
C1—Cl1 | 1.721 (3) | C14—H14A | 0.9600 |
C2—C7 | 1.398 (3) | C14—H14B | 0.9600 |
C2—C3 | 1.407 (3) | C14—H14C | 0.9600 |
C3—N1 | 1.371 (3) | C15—N1 | 1.448 (3) |
C3—C4 | 1.400 (3) | C15—C16B | 1.461 (2) |
C4—C5 | 1.359 (3) | C15—C16A | 1.464 (2) |
C4—H4 | 0.9300 | C15—H15A | 0.9700 |
C5—C6 | 1.407 (3) | C15—H15B | 0.9700 |
C5—H5 | 0.9300 | C16A—C17A | 1.286 (2) |
C6—C7 | 1.378 (3) | C16A—H16A | 0.9300 |
C6—N3 | 1.441 (3) | C17A—H17A | 0.9300 |
C7—H7 | 0.9300 | C17A—H17B | 0.9300 |
C8—C13 | 1.386 (3) | C16B—C17B | 1.286 (2) |
C8—C9 | 1.387 (3) | C16B—H16B | 0.9300 |
C8—S1 | 1.763 (3) | C17B—H17C | 0.9300 |
C9—C10 | 1.381 (4) | C17B—H17D | 0.9300 |
C9—H9 | 0.9300 | N1—N2 | 1.366 (3) |
C10—C11 | 1.384 (4) | N3—S1 | 1.647 (2) |
C10—H10 | 0.9300 | N3—H3N | 0.8060 |
C11—C12 | 1.368 (5) | O1—S1 | 1.4329 (18) |
C11—C14 | 1.519 (4) | O2—S1 | 1.4291 (17) |
C12—C13 | 1.380 (4) | ||
N2—C1—C2 | 113.4 (2) | C11—C14—H14B | 109.5 |
N2—C1—Cl1 | 120.0 (2) | H14A—C14—H14B | 109.5 |
C2—C1—Cl1 | 126.52 (19) | C11—C14—H14C | 109.5 |
C7—C2—C3 | 120.4 (2) | H14A—C14—H14C | 109.5 |
C7—C2—C1 | 136.1 (2) | H14B—C14—H14C | 109.5 |
C3—C2—C1 | 103.5 (2) | N1—C15—C16B | 125.2 (5) |
N1—C3—C4 | 132.1 (2) | N1—C15—C16A | 106.5 (3) |
N1—C3—C2 | 106.4 (2) | C16B—C15—C16A | 18.8 (5) |
C4—C3—C2 | 121.5 (2) | N1—C15—H15A | 110.4 |
C5—C4—C3 | 116.9 (2) | C16B—C15—H15A | 98.8 |
C5—C4—H4 | 121.5 | C16A—C15—H15A | 110.4 |
C3—C4—H4 | 121.5 | N1—C15—H15B | 110.4 |
C4—C5—C6 | 122.5 (2) | C16B—C15—H15B | 102.0 |
C4—C5—H5 | 118.8 | C16A—C15—H15B | 110.4 |
C6—C5—H5 | 118.8 | H15A—C15—H15B | 108.6 |
C7—C6—C5 | 121.0 (2) | C17A—C16A—C15 | 128.9 (8) |
C7—C6—N3 | 119.3 (2) | C17A—C16A—H16A | 115.5 |
C5—C6—N3 | 119.7 (2) | C15—C16A—H16A | 115.5 |
C6—C7—C2 | 117.6 (2) | C16A—C17A—H17A | 120.0 |
C6—C7—H7 | 121.2 | C16A—C17A—H17B | 120.0 |
C2—C7—H7 | 121.2 | H17A—C17A—H17B | 120.0 |
C13—C8—C9 | 120.2 (3) | C17B—C16B—C15 | 117.8 (10) |
C13—C8—S1 | 120.3 (2) | C17B—C16B—H16B | 121.1 |
C9—C8—S1 | 119.5 (2) | C15—C16B—H16B | 121.1 |
C10—C9—C8 | 119.6 (3) | C16B—C17B—H17C | 120.0 |
C10—C9—H9 | 120.2 | C16B—C17B—H17D | 120.0 |
C8—C9—H9 | 120.2 | H17C—C17B—H17D | 120.0 |
C9—C10—C11 | 121.1 (3) | N2—N1—C3 | 111.97 (18) |
C9—C10—H10 | 119.5 | N2—N1—C15 | 120.6 (2) |
C11—C10—H10 | 119.5 | C3—N1—C15 | 127.2 (2) |
C12—C11—C10 | 117.9 (3) | C1—N2—N1 | 104.6 (2) |
C12—C11—C14 | 122.2 (3) | C6—N3—S1 | 118.87 (15) |
C10—C11—C14 | 119.9 (3) | C6—N3—H3N | 115.8 |
C11—C12—C13 | 123.0 (3) | S1—N3—H3N | 108.1 |
C11—C12—H12 | 118.5 | O2—S1—O1 | 119.90 (11) |
C13—C12—H12 | 118.5 | O2—S1—N3 | 106.65 (10) |
C12—C13—C8 | 118.2 (3) | O1—S1—N3 | 105.41 (11) |
C12—C13—H13 | 120.9 | O2—S1—C8 | 107.81 (11) |
C8—C13—H13 | 120.9 | O1—S1—C8 | 108.85 (12) |
C11—C14—H14A | 109.5 | N3—S1—C8 | 107.64 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1i | 0.81 | 2.39 | 3.140 (3) | 155 |
C4—H4···O2ii | 0.93 | 2.44 | 3.364 (3) | 171 |
C5—H5···O1i | 0.93 | 2.58 | 3.282 (3) | 132 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1i | 0.81 | 2.39 | 3.140 (3) | 155.1 |
C4—H4···O2ii | 0.93 | 2.44 | 3.364 (3) | 171.1 |
C5—H5···O1i | 0.93 | 2.58 | 3.282 (3) | 132.3 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements, and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for financial support.
References
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