Crystal structure of N-(1-allyl-3-chloro-4-eth­oxy-1H-indazol-5-yl)-4-meth­oxybenzene­sulfonamide

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

doi:10.1107/S1600536814018492

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1029-o1030

doi:10.1107/S1600536814018492

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Crystal structure of N-(1-allyl-3-chloro-4-ethoxy-1H-indazol-5-yl)-4-methoxybenzenesulfonamide

Hakima Chicha,^a El Mostapha Rakib,^a Latifa Bouissane,^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: l_bouissane@yahoo.fr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 12 August 2014; accepted 13 August 2014; online 20 August 2014)

In the title compound, C₁₉H₂₀ClN₃O₄S, the benzene ring is inclined to the indazole ring system (r.m.s. deviation = 0.014 Å) by 65.07 (8)°. The allyl and ethoxy groups are almost normal to the indazole ring, as indicated by the respective torsion angles [N—N—C—C = 111.6 (2) and C—C—O—C = −88.1 (2)°]. In the crystal, molecules are connected by N—H⋯N hydrogen bonds, forming helical chains propagating along [010]. The chains are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure; indazole; benzenesulfonamide; hydrogen bonds.

CCDC reference: 1019238

1. Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ); Mustafa et al. (2012 ); Bouissane et al. (2006 ); Ghorab et al. (2009 ). For similar compounds, see: Abbassi et al. (2012 , 2013 ); Chicha et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₉H₂₀ClN₃O₄S
M_r = 421.89
Monoclinic, P 2₁
a = 8.2699 (7) Å
b = 13.1235 (12) Å
c = 10.0026 (9) Å
β = 110.379 (5)°
V = 1017.64 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.42 × 0.32 × 0.28 mm

2.2. Data collection

Bruker X8 APEX Diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.670, T_max = 0.746
12792 measured reflections
5605 independent reflections
4754 reflections with I > 2σ(I)
R_int = 0.028

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.03
5605 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 )
Absolute structure parameter: −0.04 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N⋯N2ⁱ	0.84	2.11	2.931 (2)	166
C19—H19A⋯O3ⁱⁱ	0.96	2.37	3.285 (2)	159
C3—H3B⋯O2ⁱⁱⁱ	0.97	2.47	3.418 (3)	165
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z+1; (iii) x+1, y, 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

CCDC reference: 1019238

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018492/su2771sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018492/su2771Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018492/su2771Isup3.cml

checkCIF report

Related literature top

For the biological activity of sulfonamides, see: El-Sayed et al. (2011); Mustafa et al. (2012); Bouissane et al. (2006); Ghorab et al. (2009). For similar compounds, see: Abbassi et al. (2012, 2013); Chicha et al. (2014).

Experimental top

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. 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 2:8). Crystals of the title compound were obtained by recrystallization from ethanol (yield = 43%; m.p. = 397 K).

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. A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

N-(1-Allyl-3-chloro-4-ethoxy-1H-indazol-5-yl)-4-methoxybenzenesulfonamide top

Crystal data top

C₁₉H₂₀ClN₃O₄S	F(000) = 440
M_r = 421.89	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁	Melting point: 397 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.2699 (7) Å	Cell parameters from 5605 reflections
b = 13.1235 (12) Å	θ = 2.6–29.6°
c = 10.0026 (9) Å	µ = 0.32 mm⁻¹
β = 110.379 (5)°	T = 296 K
V = 1017.64 (16) Å³	Prism, colourless
Z = 2	0.42 × 0.32 × 0.28 mm

Data collection top

Bruker X8 APEX Diffractometer	5605 independent reflections
Radiation source: fine-focus sealed tube	4754 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 29.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −11→11
T_min = 0.670, T_max = 0.746	k = −18→18
12792 measured reflections	l = −12→13

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0435P)² + 0.0481P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5605 reflections	Δρ_max = 0.18 e Å⁻³
253 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack & Bernardinelli (2000)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (4)

Crystal data top

C₁₉H₂₀ClN₃O₄S	V = 1017.64 (16) Å³
M_r = 421.89	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.2699 (7) Å	µ = 0.32 mm⁻¹
b = 13.1235 (12) Å	T = 296 K
c = 10.0026 (9) Å	0.42 × 0.32 × 0.28 mm
β = 110.379 (5)°

Data collection top

Bruker X8 APEX Diffractometer	5605 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	4754 reflections with I > 2σ(I)
T_min = 0.670, T_max = 0.746	R_int = 0.028
12792 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.18 e Å⁻³
S = 1.03	Δρ_min = −0.20 e Å⁻³
5605 reflections	Absolute structure: Flack & Bernardinelli (2000)
253 parameters	Absolute structure parameter: −0.04 (4)
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 > 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.

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

	x	y	z	U_iso*/U_eq
C1	0.5375 (4)	0.8680 (4)	0.9417 (3)	0.1124 (13)
H1A	0.6182	0.8159	0.9577	0.135*
H1B	0.5344	0.9084	1.0173	0.135*
C2	0.4301 (3)	0.8844 (2)	0.8151 (3)	0.0706 (7)
H2	0.3506	0.9370	0.8018	0.085*
C3	0.4268 (2)	0.82350 (16)	0.6893 (2)	0.0519 (4)
H3A	0.4629	0.8663	0.6257	0.062*
H3B	0.5089	0.7680	0.7206	0.062*
C4	0.0173 (2)	0.76621 (13)	0.43723 (18)	0.0438 (4)
C5	0.0066 (2)	0.69652 (13)	0.54239 (16)	0.0396 (3)
C6	0.1670 (2)	0.70913 (13)	0.65413 (18)	0.0411 (4)
C7	0.2124 (2)	0.65003 (15)	0.77993 (19)	0.0472 (4)
H7	0.3187	0.6575	0.8526	0.057*
C8	0.0936 (2)	0.58180 (14)	0.78968 (19)	0.0455 (4)
H8	0.1200	0.5420	0.8714	0.055*
C9	−0.0697 (2)	0.56870 (13)	0.68005 (17)	0.0387 (3)
C10	−0.1141 (2)	0.62525 (13)	0.55548 (17)	0.0389 (3)
C11	−0.4058 (3)	0.67175 (17)	0.4348 (2)	0.0595 (5)
H11A	−0.3680	0.7422	0.4467	0.071*
H11B	−0.4498	0.6548	0.5102	0.071*
C12	−0.5450 (3)	0.6575 (2)	0.2914 (3)	0.0826 (8)
H12A	−0.6410	0.7009	0.2846	0.124*
H12B	−0.5821	0.5877	0.2807	0.124*
H12C	−0.5006	0.6748	0.2176	0.124*
C13	−0.1432 (2)	0.47263 (13)	0.97527 (17)	0.0372 (3)
C14	−0.0709 (2)	0.37584 (14)	1.00480 (19)	0.0445 (4)
H14	−0.0998	0.3261	0.9342	0.053*
C15	0.0440 (2)	0.35386 (14)	1.1395 (2)	0.0472 (4)
H15	0.0936	0.2895	1.1594	0.057*
C16	0.0854 (2)	0.42823 (14)	1.24556 (18)	0.0412 (4)
C17	0.0108 (3)	0.52403 (15)	1.21696 (19)	0.0509 (5)
H17	0.0365	0.5732	1.2882	0.061*
C18	−0.1031 (2)	0.54584 (15)	1.08055 (19)	0.0472 (4)
H18	−0.1525	0.6103	1.0603	0.057*
C19	0.2358 (3)	0.4703 (2)	1.4897 (2)	0.0654 (6)
H19A	0.3188	0.4414	1.5739	0.098*
H19B	0.1310	0.4845	1.5071	0.098*
H19C	0.2808	0.5323	1.4656	0.098*
N1	0.25612 (19)	0.78146 (13)	0.61078 (16)	0.0475 (3)
H1N	−0.1966	0.4399	0.6454	0.057*
N2	0.1641 (2)	0.81619 (12)	0.47747 (17)	0.0487 (4)
N3	−0.18652 (19)	0.49314 (12)	0.69400 (14)	0.0450 (3)
O1	−0.26451 (16)	0.60654 (10)	0.44257 (13)	0.0492 (3)
O2	−0.3468 (2)	0.60356 (12)	0.80661 (15)	0.0631 (4)
O3	−0.41372 (18)	0.41918 (13)	0.76263 (15)	0.0663 (4)
O4	0.20127 (17)	0.39973 (12)	1.37445 (14)	0.0575 (4)
S1	−0.29029 (5)	0.50045 (3)	0.80328 (4)	0.04255 (11)
Cl1	−0.13391 (7)	0.78969 (4)	0.27168 (5)	0.06011 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0692 (16)	0.197 (4)	0.0710 (18)	−0.008 (2)	0.0241 (14)	−0.035 (2)
C2	0.0470 (11)	0.0776 (16)	0.0869 (16)	−0.0028 (11)	0.0230 (11)	−0.0236 (13)
C3	0.0415 (9)	0.0562 (11)	0.0615 (11)	−0.0034 (8)	0.0223 (8)	0.0045 (9)
C4	0.0545 (10)	0.0401 (10)	0.0375 (8)	0.0026 (8)	0.0168 (7)	0.0043 (7)
C5	0.0474 (9)	0.0380 (8)	0.0345 (7)	0.0047 (7)	0.0155 (6)	0.0034 (6)
C6	0.0436 (8)	0.0399 (9)	0.0415 (8)	0.0019 (7)	0.0169 (7)	0.0041 (7)
C7	0.0441 (9)	0.0529 (11)	0.0404 (8)	0.0016 (8)	0.0096 (7)	0.0075 (7)
C8	0.0517 (10)	0.0480 (10)	0.0367 (8)	0.0037 (8)	0.0154 (7)	0.0096 (7)
C9	0.0471 (9)	0.0340 (8)	0.0377 (8)	−0.0011 (7)	0.0184 (7)	−0.0012 (6)
C10	0.0460 (8)	0.0355 (8)	0.0343 (7)	0.0020 (7)	0.0129 (6)	−0.0020 (6)
C11	0.0527 (10)	0.0579 (12)	0.0599 (11)	0.0003 (10)	0.0097 (9)	−0.0046 (10)
C12	0.0651 (14)	0.0873 (19)	0.0745 (15)	−0.0002 (13)	−0.0023 (12)	0.0097 (14)
C13	0.0374 (7)	0.0407 (9)	0.0341 (7)	0.0006 (6)	0.0129 (6)	0.0056 (6)
C14	0.0526 (9)	0.0398 (9)	0.0398 (8)	0.0039 (8)	0.0145 (7)	−0.0014 (7)
C15	0.0530 (10)	0.0396 (9)	0.0487 (9)	0.0108 (8)	0.0171 (8)	0.0061 (7)
C16	0.0353 (7)	0.0475 (10)	0.0390 (8)	0.0030 (7)	0.0108 (6)	0.0053 (7)
C17	0.0548 (10)	0.0466 (11)	0.0424 (9)	0.0043 (8)	0.0057 (7)	−0.0067 (7)
C18	0.0532 (10)	0.0382 (9)	0.0447 (9)	0.0072 (7)	0.0100 (8)	0.0024 (7)
C19	0.0630 (12)	0.0784 (16)	0.0416 (10)	−0.0014 (11)	0.0013 (8)	0.0019 (10)
N1	0.0483 (7)	0.0480 (8)	0.0464 (8)	−0.0015 (7)	0.0169 (6)	0.0078 (7)
N2	0.0601 (9)	0.0433 (8)	0.0465 (8)	0.0024 (7)	0.0234 (7)	0.0091 (6)
N3	0.0608 (8)	0.0372 (7)	0.0419 (7)	−0.0087 (7)	0.0241 (6)	−0.0053 (6)
O1	0.0551 (7)	0.0475 (7)	0.0390 (6)	−0.0016 (6)	0.0089 (5)	−0.0066 (5)
O2	0.0731 (9)	0.0687 (10)	0.0497 (8)	0.0340 (8)	0.0242 (7)	0.0146 (7)
O3	0.0477 (7)	0.0917 (12)	0.0499 (8)	−0.0213 (8)	0.0049 (6)	0.0132 (8)
O4	0.0520 (7)	0.0689 (9)	0.0419 (6)	0.0142 (7)	0.0041 (5)	0.0047 (6)
S1	0.03950 (19)	0.0505 (2)	0.03584 (18)	0.00353 (19)	0.01090 (14)	0.00789 (17)
Cl1	0.0752 (3)	0.0580 (3)	0.0390 (2)	−0.0010 (2)	0.0097 (2)	0.0121 (2)

Geometric parameters (Å, º) top

C1—C2	1.287 (4)	C11—H11B	0.9700
C1—H1A	0.9300	C12—H12A	0.9600
C1—H1B	0.9300	C12—H12B	0.9600
C2—C3	1.483 (3)	C12—H12C	0.9600
C2—H2	0.9300	C13—C18	1.378 (3)
C3—N1	1.463 (2)	C13—C14	1.391 (2)
C3—H3A	0.9700	C13—S1	1.7650 (16)
C3—H3B	0.9700	C14—C15	1.382 (2)
C4—N2	1.313 (2)	C14—H14	0.9300
C4—C5	1.420 (2)	C15—C16	1.393 (3)
C4—Cl1	1.7201 (17)	C15—H15	0.9300
C5—C10	1.407 (2)	C16—O4	1.3636 (19)
C5—C6	1.416 (2)	C16—C17	1.386 (3)
C6—N1	1.362 (2)	C17—C18	1.391 (2)
C6—C7	1.413 (2)	C17—H17	0.9300
C7—C8	1.358 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—O4	1.428 (3)
C8—C9	1.423 (2)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—C10	1.385 (2)	C19—H19C	0.9600
C9—N3	1.425 (2)	N1—N2	1.363 (2)
C10—O1	1.3801 (19)	N3—S1	1.6106 (14)
C11—O1	1.428 (2)	N3—H1N	0.8390
C11—C12	1.506 (3)	O2—S1	1.4358 (15)
C11—H11A	0.9700	O3—S1	1.4338 (15)

C2—C1—H1A	120.0	C11—C12—H12C	109.5
C2—C1—H1B	120.0	H12A—C12—H12C	109.5
H1A—C1—H1B	120.0	H12B—C12—H12C	109.5
C1—C2—C3	123.2 (3)	C18—C13—C14	120.21 (15)
C1—C2—H2	118.4	C18—C13—S1	120.10 (13)
C3—C2—H2	118.4	C14—C13—S1	119.68 (13)
N1—C3—C2	112.82 (16)	C15—C14—C13	119.75 (16)
N1—C3—H3A	109.0	C15—C14—H14	120.1
C2—C3—H3A	109.0	C13—C14—H14	120.1
N1—C3—H3B	109.0	C14—C15—C16	119.95 (16)
C2—C3—H3B	109.0	C14—C15—H15	120.0
H3A—C3—H3B	107.8	C16—C15—H15	120.0
N2—C4—C5	112.59 (15)	O4—C16—C17	124.04 (16)
N2—C4—Cl1	119.34 (13)	O4—C16—C15	115.67 (16)
C5—C4—Cl1	128.07 (14)	C17—C16—C15	120.29 (15)
C10—C5—C6	120.30 (15)	C16—C17—C18	119.33 (17)
C10—C5—C4	136.61 (15)	C16—C17—H17	120.3
C6—C5—C4	103.08 (15)	C18—C17—H17	120.3
N1—C6—C7	131.36 (16)	C13—C18—C17	120.43 (17)
N1—C6—C5	107.00 (15)	C13—C18—H18	119.8
C7—C6—C5	121.61 (16)	C17—C18—H18	119.8
C8—C7—C6	116.83 (15)	O4—C19—H19A	109.5
C8—C7—H7	121.6	O4—C19—H19B	109.5
C6—C7—H7	121.6	H19A—C19—H19B	109.5
C7—C8—C9	122.74 (16)	O4—C19—H19C	109.5
C7—C8—H8	118.6	H19A—C19—H19C	109.5
C9—C8—H8	118.6	H19B—C19—H19C	109.5
C10—C9—C8	120.76 (16)	C6—N1—N2	111.39 (14)
C10—C9—N3	119.00 (15)	C6—N1—C3	128.29 (16)
C8—C9—N3	120.16 (14)	N2—N1—C3	120.30 (16)
O1—C10—C9	121.44 (16)	C4—N2—N1	105.93 (14)
O1—C10—C5	120.56 (15)	C9—N3—S1	124.38 (12)
C9—C10—C5	117.75 (15)	C9—N3—H1N	117.2
O1—C11—C12	108.46 (19)	S1—N3—H1N	118.3
O1—C11—H11A	110.0	C10—O1—C11	115.14 (13)
C12—C11—H11A	110.0	C16—O4—C19	117.56 (16)
O1—C11—H11B	110.0	O3—S1—O2	120.14 (10)
C12—C11—H11B	110.0	O3—S1—N3	104.96 (9)
H11A—C11—H11B	108.4	O2—S1—N3	109.07 (8)
C11—C12—H12A	109.5	O3—S1—C13	107.67 (8)
C11—C12—H12B	109.5	O2—S1—C13	106.96 (8)
H12A—C12—H12B	109.5	N3—S1—C13	107.45 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···N2ⁱ	0.84	2.11	2.931 (2)	166
C19—H19A···O3ⁱⁱ	0.96	2.37	3.285 (2)	159
C3—H3B···O2ⁱⁱⁱ	0.97	2.47	3.418 (3)	165

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···N2ⁱ	0.84	2.11	2.931 (2)	166
C19—H19A···O3ⁱⁱ	0.96	2.37	3.285 (2)	159
C3—H3B···O2ⁱⁱⁱ	0.97	2.47	3.418 (3)	165

Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x+1, y, z+1; (iii) 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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Volume 70| Part 9| September 2014| Pages o1029-o1030

doi:10.1107/S1600536814018492

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

Crystal structure of N-(1-allyl-3-chloro-4-eth­­oxy-1H-indazol-5-yl)-4-meth­oxybenzene­sulfonamide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of N-(1-allyl-3-chloro-4-ethoxy-1H-indazol-5-yl)-4-methoxybenzenesulfonamide