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

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

doi:10.1107/S1600536814017747

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o983-o984

doi:10.1107/S1600536814017747

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

Hakima Chicha,^a El Mostapha Rakib,^a Ahmed Gamouh,^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: a_gamouh@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 July 2014; accepted 1 August 2014; online 9 August 2014)

In the title compound, C₁₅H₁₄ClN₃O₃S, the dihedral angle between the planes of the indazole ring system (r.m.s. deviation = 0.007 Å) and the benzene ring is 89.05 (7)°. The methoxy C atom deviates from its attached ring by 0.196 (3) Å. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops. The dimers are connected into [010] chains by C—H⋯O interactions.

Keywords: crystal structure; benzenesulfonamides; hydrogen bonding.

CCDC reference: 1017531

1. Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ); Mustafa et al. (2012 ); Scozzafava et al. (2003 ). For similar compounds, see: Abbassi et al. (2012 , 2013 ); Chicha et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₄ClN₃O₃S
M_r = 351.80
Triclinic, $[P \overline 1]$
a = 8.2023 (1) Å
b = 10.6312 (2) Å
c = 10.8957 (2) Å
α = 117.523 (1)°
β = 93.095 (1)°
γ = 103.166 (1)°
V = 806.36 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 K
0.40 × 0.36 × 0.31 mm

2.2. Data collection

Bruker X8 APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.693, T_max = 0.747
20115 measured reflections
4526 independent reflections
3707 reflections with I > 2σ(I)
R_int = 0.028

2.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.116
S = 1.03
4526 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2ⁱ	0.89	2.04	2.9286 (17)	175
C5—H5⋯O3ⁱⁱ	0.93	2.56	3.426 (2)	156
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x, y-1, 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: 1017531

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814017747/hb7261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017747/hb7261Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814017747/hb7261Isup3.cml

checkCIF report

Comment top

The sulfonamide functional group is a structure with broad importance, as it is found in numerous medicinal agents (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 0.010 (2) Å for C5 atom (Fig.1). The dihedral angle between the indazol system and the plane through the benzene ring (C9 to C14) is of 89.05 (7)°.

The cohesion of the crystal structure is ensured by N3–H3N···O2 hydrogen bonds between molecules forming dimers, which are linked together by C5–H5···O3 interaction and forming [010] chains as shown in Fig.2 and Table 1.

Related literature top

For the biological activity of sulfonamides, see: El-Sayed et al. (2011); Mustafa et al. (2012); Scozzafava et al. (2003). For similar compounds, see: Abbassi et al. (2012, 2013); Chicha et al. (2014).

Experimental top

A mixture of 1-methyl-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 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-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). The title compound was recrystallized from ethanol solution. Yield: 56%, PF: 140–142°C.

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 displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal structure of the title compound, showing molecules linked by N3–H3N···O2 hydrogen bond and forming dimers linked by C5–H5···O3 interaction.

N-(3-Chloro-1-methyl-1H-indazol-5-yl)-4-methoxybenzenesulfonamide top

Crystal data top

C₁₅H₁₄ClN₃O₃S	Z = 2
M_r = 351.80	F(000) = 364
Triclinic, P1	D_x = 1.449 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2023 (1) Å	Cell parameters from 4526 reflections
b = 10.6312 (2) Å	θ = 2.6–29.6°
c = 10.8957 (2) Å	µ = 0.38 mm⁻¹
α = 117.523 (1)°	T = 296 K
β = 93.095 (1)°	Block, colourless
γ = 103.166 (1)°	0.40 × 0.36 × 0.31 mm
V = 806.36 (2) Å³

Data collection top

Bruker X8 APEX CCD diffractometer	4526 independent reflections
Radiation source: fine-focus sealed tube	3707 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; Bruker, 2009)	h = −11→11
T_min = 0.693, T_max = 0.747	k = −14→14
20115 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.062P)² + 0.1878P] where P = (F_o² + 2F_c²)/3
4526 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₅H₁₄ClN₃O₃S	γ = 103.166 (1)°
M_r = 351.80	V = 806.36 (2) Å³
Triclinic, P1	Z = 2
a = 8.2023 (1) Å	Mo Kα radiation
b = 10.6312 (2) Å	µ = 0.38 mm⁻¹
c = 10.8957 (2) Å	T = 296 K
α = 117.523 (1)°	0.40 × 0.36 × 0.31 mm
β = 93.095 (1)°

Data collection top

Bruker X8 APEX CCD diffractometer	4526 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3707 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.747	R_int = 0.028
20115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
4526 reflections	Δρ_min = −0.37 e Å⁻³
209 parameters

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	0.5360 (3)	0.1820 (2)	−0.2354 (2)	0.0641 (5)
H1A	0.5166	0.1185	−0.3355	0.096*
H1B	0.4305	0.1986	−0.2072	0.096*
H1C	0.5801	0.1361	−0.1885	0.096*
C2	0.8383 (2)	0.47591 (16)	−0.23208 (15)	0.0391 (3)
C3	0.84060 (18)	0.54753 (16)	−0.08554 (14)	0.0352 (3)
C4	0.72093 (19)	0.44264 (17)	−0.06796 (16)	0.0397 (3)
C5	0.6874 (2)	0.4716 (2)	0.06598 (18)	0.0493 (4)
H5	0.6097	0.4017	0.0787	0.059*
C6	0.7734 (2)	0.60633 (19)	0.17665 (17)	0.0476 (4)
H6	0.7515	0.6289	0.2662	0.057*
C7	0.8951 (2)	0.71369 (17)	0.16058 (14)	0.0385 (3)
C8	0.93096 (19)	0.68456 (16)	0.02938 (14)	0.0375 (3)
H8	1.0120	0.7532	0.0177	0.045*
C9	0.88896 (18)	1.06974 (16)	0.26748 (13)	0.0364 (3)
C10	0.83288 (19)	1.04012 (17)	0.13088 (14)	0.0407 (3)
H10	0.8815	0.9839	0.0568	0.049*
C11	0.7053 (2)	1.09469 (18)	0.10689 (15)	0.0441 (3)
H11	0.6677	1.0754	0.0162	0.053*
C12	0.6321 (2)	1.17864 (17)	0.21742 (16)	0.0413 (3)
C13	0.6836 (2)	1.20357 (17)	0.35215 (16)	0.0435 (3)
H13	0.6319	1.2566	0.4254	0.052*
C14	0.8118 (2)	1.14935 (17)	0.37674 (14)	0.0413 (3)
H14	0.8469	1.1661	0.4670	0.050*
C15	0.4427 (3)	1.3276 (3)	0.2942 (3)	0.0797 (7)
H15A	0.3597	1.3573	0.2564	0.120*
H15B	0.5324	1.4136	0.3600	0.120*
H15C	0.3895	1.2767	0.3414	0.120*
N1	0.65760 (18)	0.32210 (15)	−0.19782 (15)	0.0478 (3)
N2	0.72912 (18)	0.34244 (15)	−0.29918 (14)	0.0456 (3)
N3	0.98123 (19)	0.84656 (15)	0.28741 (13)	0.0459 (3)
H3N	0.9455	0.8563	0.3661	0.057 (5)*
O1	1.16088 (15)	0.99481 (14)	0.19715 (12)	0.0520 (3)
O2	1.13503 (15)	1.10282 (14)	0.44851 (11)	0.0535 (3)
O3	0.51174 (17)	1.23162 (16)	0.18293 (14)	0.0575 (3)
S1	1.05777 (5)	1.00891 (4)	0.30176 (3)	0.04069 (12)
Cl1	0.95605 (6)	0.54559 (5)	−0.32303 (4)	0.05614 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0617 (11)	0.0421 (9)	0.0786 (13)	0.0032 (8)	0.0160 (10)	0.0262 (9)
C2	0.0482 (8)	0.0355 (7)	0.0327 (6)	0.0140 (6)	0.0112 (6)	0.0147 (6)
C3	0.0424 (7)	0.0354 (7)	0.0325 (6)	0.0176 (6)	0.0115 (5)	0.0170 (5)
C4	0.0443 (7)	0.0386 (8)	0.0420 (7)	0.0166 (6)	0.0133 (6)	0.0215 (6)
C5	0.0585 (10)	0.0506 (9)	0.0507 (9)	0.0187 (8)	0.0230 (7)	0.0315 (8)
C6	0.0631 (10)	0.0545 (10)	0.0396 (7)	0.0273 (8)	0.0224 (7)	0.0285 (7)
C7	0.0492 (8)	0.0416 (8)	0.0314 (6)	0.0243 (6)	0.0126 (6)	0.0174 (6)
C8	0.0468 (7)	0.0363 (7)	0.0308 (6)	0.0157 (6)	0.0108 (5)	0.0154 (5)
C9	0.0443 (7)	0.0328 (7)	0.0264 (6)	0.0081 (5)	0.0090 (5)	0.0110 (5)
C10	0.0462 (8)	0.0430 (8)	0.0263 (6)	0.0092 (6)	0.0109 (5)	0.0128 (6)
C11	0.0498 (8)	0.0489 (9)	0.0311 (6)	0.0088 (7)	0.0072 (6)	0.0197 (6)
C12	0.0446 (8)	0.0372 (7)	0.0413 (7)	0.0073 (6)	0.0085 (6)	0.0203 (6)
C13	0.0540 (9)	0.0394 (8)	0.0344 (7)	0.0165 (7)	0.0153 (6)	0.0137 (6)
C14	0.0535 (8)	0.0406 (8)	0.0256 (6)	0.0146 (6)	0.0103 (6)	0.0120 (5)
C15	0.0883 (16)	0.0877 (17)	0.0909 (17)	0.0560 (14)	0.0333 (14)	0.0502 (14)
N1	0.0523 (8)	0.0374 (7)	0.0485 (7)	0.0079 (6)	0.0134 (6)	0.0187 (6)
N2	0.0536 (8)	0.0367 (7)	0.0393 (6)	0.0111 (6)	0.0103 (6)	0.0134 (5)
N3	0.0649 (8)	0.0476 (8)	0.0272 (5)	0.0231 (6)	0.0116 (5)	0.0165 (5)
O1	0.0485 (6)	0.0604 (8)	0.0370 (5)	0.0149 (5)	0.0163 (5)	0.0151 (5)
O2	0.0533 (7)	0.0610 (8)	0.0281 (5)	0.0122 (6)	0.0018 (4)	0.0097 (5)
O3	0.0610 (7)	0.0654 (8)	0.0594 (7)	0.0281 (6)	0.0141 (6)	0.0362 (7)
S1	0.0437 (2)	0.0454 (2)	0.02480 (16)	0.01330 (15)	0.00761 (13)	0.01019 (14)
Cl1	0.0743 (3)	0.0487 (2)	0.0361 (2)	0.0060 (2)	0.01902 (18)	0.01758 (17)

Geometric parameters (Å, º) top

C1—N1	1.448 (2)	C9—S1	1.7465 (16)
C1—H1A	0.9600	C10—C11	1.374 (2)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—C12	1.392 (2)
C2—N2	1.320 (2)	C11—H11	0.9300
C2—C3	1.4129 (18)	C12—O3	1.357 (2)
C2—Cl1	1.7085 (15)	C12—C13	1.388 (2)
C3—C8	1.401 (2)	C13—C14	1.378 (2)
C3—C4	1.401 (2)	C13—H13	0.9300
C4—N1	1.362 (2)	C14—H14	0.9300
C4—C5	1.403 (2)	C15—O3	1.423 (3)
C5—C6	1.362 (2)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.419 (2)	C15—H15C	0.9600
C6—H6	0.9300	N1—N2	1.3577 (19)
C7—C8	1.3796 (19)	N3—S1	1.6260 (15)
C7—N3	1.4283 (19)	N3—H3N	0.8897
C8—H8	0.9300	O1—S1	1.4286 (11)
C9—C14	1.3884 (19)	O2—S1	1.4429 (11)
C9—C10	1.3974 (18)

N1—C1—H1A	109.5	C10—C11—C12	120.42 (13)
N1—C1—H1B	109.5	C10—C11—H11	119.8
H1A—C1—H1B	109.5	C12—C11—H11	119.8
N1—C1—H1C	109.5	O3—C12—C13	124.39 (14)
H1A—C1—H1C	109.5	O3—C12—C11	115.54 (14)
H1B—C1—H1C	109.5	C13—C12—C11	120.08 (15)
N2—C2—C3	112.74 (13)	C14—C13—C12	119.65 (14)
N2—C2—Cl1	120.30 (11)	C14—C13—H13	120.2
C3—C2—Cl1	126.95 (12)	C12—C13—H13	120.2
C8—C3—C4	121.43 (13)	C13—C14—C9	120.33 (13)
C8—C3—C2	135.32 (14)	C13—C14—H14	119.8
C4—C3—C2	103.24 (13)	C9—C14—H14	119.8
N1—C4—C3	107.20 (13)	O3—C15—H15A	109.5
N1—C4—C5	131.85 (15)	O3—C15—H15B	109.5
C3—C4—C5	120.95 (14)	H15A—C15—H15B	109.5
C6—C5—C4	117.13 (15)	O3—C15—H15C	109.5
C6—C5—H5	121.4	H15A—C15—H15C	109.5
C4—C5—H5	121.4	H15B—C15—H15C	109.5
C5—C6—C7	122.58 (14)	N2—N1—C4	111.53 (13)
C5—C6—H6	118.7	N2—N1—C1	119.65 (15)
C7—C6—H6	118.7	C4—N1—C1	128.76 (15)
C8—C7—C6	120.47 (14)	C2—N2—N1	105.29 (12)
C8—C7—N3	123.47 (14)	C7—N3—S1	125.87 (10)
C6—C7—N3	115.98 (13)	C7—N3—H3N	116.4
C7—C8—C3	117.42 (14)	S1—N3—H3N	109.8
C7—C8—H8	121.3	C12—O3—C15	117.58 (15)
C3—C8—H8	121.3	O1—S1—O2	119.16 (7)
C14—C9—C10	120.00 (14)	O1—S1—N3	108.43 (7)
C14—C9—S1	119.80 (11)	O2—S1—N3	104.11 (7)
C10—C9—S1	120.20 (11)	O1—S1—C9	107.91 (7)
C11—C10—C9	119.45 (13)	O2—S1—C9	108.05 (7)
C11—C10—H10	120.3	N3—S1—C9	108.82 (7)
C9—C10—H10	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.89	2.04	2.9286 (17)	175
C5—H5···O3ⁱⁱ	0.93	2.56	3.426 (2)	156

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.89	2.04	2.9286 (17)	175
C5—H5···O3ⁱⁱ	0.93	2.56	3.426 (2)	156

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS and CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for the financial support.

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o983-o984

doi:10.1107/S1600536814017747

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

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