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

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

doi:10.1107/S160053681302744X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1632

doi:10.1107/S160053681302744X

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N-(3-Chloro-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

(Received 1 October 2013; accepted 7 October 2013; online 12 October 2013)

In the title compound, C₁₄H₁₂ClN₃O₃S, the fused five- and six-membered rings are folded slightly along the common edge, forming a dihedral angle of 3.2 (1)°. The mean plane through the indazole system makes a dihedral angle of 30.75 (7)° with the distant benzene ring. In the crystal, N—H⋯O hydrogen bonds link the molecules, forming a two-dimensional network parallel to (001).

CCDC reference: 965151

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006 ); El-Sayed et al. (2011 ); Mustafa et al. (2012 ). For similar compounds, see: Abbassi et al. (2012 , 2013 ); Chicha et al. (2013 ).

Experimental

Crystal data

C₁₄H₁₂ClN₃O₃S
M_r = 337.78
Monoclinic, P 2₁ /c
a = 16.1229 (5) Å
b = 10.0562 (3) Å
c = 9.7955 (2) Å
β = 105.388 (1)°
V = 1531.26 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.42 × 0.35 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.693, T_max = 0.747
19939 measured reflections
4666 independent reflections
3973 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.117
S = 1.03
4666 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.82	2.26	3.046 (2)	161
N2—H2⋯O1ⁱⁱ	0.88	1.99	2.862 (2)	174
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (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: 965151

Crystal structure: contains datablock I. DOI: 10.1107/S160053681302744X/im2442sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302744X/im2442Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302744X/im2442Isup3.cml

checkCIF report

Comment top

Sulfonamide derivatives are well known pharmaceutical agents since this group has been the main functional part in a vast number of drug structures due to stability and tolerance in human beings. These compounds exhibit a wide range of biological activities such as anticancer, anti-inflammatory, and antiviral functions (Abbassi et al., 2012; Bouissane et al., 2006; El-Sayed et al., 2011; Mustafa et al., 2012). The present work is a continuation of the investigation of sulfonamide derivatives published recently by our team (Abbassi et al., 2013; Chicha et al., 2013).

The molecule of N-(3-chloro-1H-indazol-5-yl)-4-methoxybenzenesulfonamide is built up from the 3-chloro-1H-indazol system (N2, N3, C1—C7, Cl) linked to the 4-methoxybenzenesulfonamide group as shown in Fig.1. The fused rings are slightly folded along the common edge and form a dihedral angle of 3.2 (1) °. Moreover, the dihedral angle between the mean plane through the indazole system and the plane through the atoms forming the benzene ring (C9—C14) is 30.75 (7)°.

In the crystal, molecules are interconnected by N1–H1···O2 and N2–H2···O1 hydrogen bonds forming a two-dimensional network parallel to (0 0 1) plane as shown in Fig.2 and Table 1.

Related literature top

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006); El-Sayed et al. (2011); Mustafa et al. (2012). For similar compounds, see: Abbassi et al. (2012, 2013); Chicha et al. (2013).

Experimental top

A mixture of 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-methoxybenzenesulfonyl chloride (1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuum, the resulting residue was purified by flash chromatography (eluted with ethyl acetate: hexane 1:9, yield: 67%, mp: 445 K). The title compound was recrystallized from ethanol.

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. H atoms are represented as small circles.
	Fig. 2. Partial crystal packing for the title compound showing N2—H2···O1 and N1—H1···O2 hydrogen bonds as dashed lines.

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

Crystal data top

C₁₄H₁₂ClN₃O₃S	F(000) = 696
M_r = 337.78	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4666 reflections
a = 16.1229 (5) Å	θ = 2.4–30.5°
b = 10.0562 (3) Å	µ = 0.40 mm⁻¹
c = 9.7955 (2) Å	T = 296 K
β = 105.388 (1)°	Block, colourless
V = 1531.26 (7) Å³	0.42 × 0.35 × 0.28 mm
Z = 4

Data collection top

Bruker X8 APEX diffractometer	4666 independent reflections
Radiation source: fine-focus sealed tube	3973 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 30.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→20
T_min = 0.693, T_max = 0.747	k = −14→14
19939 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0626P)² + 0.5266P] where P = (F_o² + 2F_c²)/3
4666 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₄H₁₂ClN₃O₃S	V = 1531.26 (7) Å³
M_r = 337.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1229 (5) Å	µ = 0.40 mm⁻¹
b = 10.0562 (3) Å	T = 296 K
c = 9.7955 (2) Å	0.42 × 0.35 × 0.28 mm
β = 105.388 (1)°

Data collection top

Bruker X8 APEX diffractometer	4666 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3973 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.747	R_int = 0.022
19939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
4666 reflections	Δρ_min = −0.49 e Å⁻³
199 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

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

	x	y	z	U_iso*/U_eq
C4	0.60822 (8)	0.97963 (12)	−0.02865 (13)	0.0268 (2)
C5	0.56209 (8)	1.06572 (14)	−0.13562 (15)	0.0336 (3)
H5	0.5231	1.0301	−0.2147	0.040*
C6	0.57361 (10)	1.20157 (14)	−0.12547 (17)	0.0386 (3)
H6	0.5432	1.2585	−0.1960	0.046*
C7	0.63294 (9)	1.24992 (12)	−0.00465 (16)	0.0347 (3)
C2	0.67936 (9)	1.16423 (13)	0.10154 (14)	0.0306 (3)
C3	0.66674 (8)	1.02644 (12)	0.09022 (13)	0.0286 (2)
H3	0.6968	0.9690	0.1604	0.034*
C1	0.73489 (11)	1.25131 (14)	0.19788 (17)	0.0400 (3)
C8	0.76161 (9)	0.78982 (13)	−0.03973 (14)	0.0305 (2)
C9	0.80235 (10)	0.71057 (16)	0.07419 (17)	0.0427 (3)
H9	0.7756	0.6340	0.0946	0.051*
C10	0.88322 (11)	0.7460 (2)	0.1577 (2)	0.0533 (5)
H10	0.9112	0.6926	0.2334	0.064*
C11	0.92203 (10)	0.8613 (2)	0.12745 (18)	0.0497 (4)
C12	0.88199 (10)	0.93915 (17)	0.01121 (17)	0.0436 (3)
H12	0.9094	1.0146	−0.0105	0.052*
C13	0.80182 (9)	0.90444 (14)	−0.07167 (15)	0.0348 (3)
H13	0.7745	0.9570	−0.1486	0.042*
C14	1.03882 (16)	0.8432 (4)	0.3356 (3)	0.1044 (12)
H14A	1.0928	0.8853	0.3792	0.157*
H14B	1.0484	0.7512	0.3185	0.157*
H14C	1.0017	0.8498	0.3974	0.157*
N1	0.59374 (7)	0.83818 (10)	−0.04781 (12)	0.0298 (2)
H1	0.5932	0.7982	0.0253	0.036*
N2	0.66110 (10)	1.37511 (12)	0.03591 (17)	0.0486 (3)
H2	0.6490	1.4494	−0.0128	0.058*
N3	0.72483 (10)	1.37633 (13)	0.15800 (16)	0.0497 (3)
O1	0.63534 (8)	0.62011 (10)	−0.11826 (12)	0.0436 (3)
O2	0.63874 (7)	0.81515 (10)	−0.26973 (10)	0.0378 (2)
O3	0.99969 (9)	0.9074 (2)	0.20519 (17)	0.0789 (5)
S1	0.65443 (2)	0.75832 (3)	−0.13090 (3)	0.02874 (9)
Cl1	0.80966 (4)	1.20719 (5)	0.34939 (5)	0.06387 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.0299 (5)	0.0219 (5)	0.0284 (5)	−0.0007 (4)	0.0075 (4)	−0.0003 (4)
C5	0.0305 (6)	0.0314 (6)	0.0339 (6)	0.0016 (5)	−0.0001 (5)	0.0017 (5)
C6	0.0366 (7)	0.0296 (6)	0.0441 (8)	0.0063 (5)	0.0011 (6)	0.0087 (5)
C7	0.0370 (7)	0.0217 (5)	0.0443 (7)	0.0024 (5)	0.0087 (6)	0.0009 (5)
C2	0.0354 (6)	0.0242 (5)	0.0311 (6)	−0.0014 (5)	0.0067 (5)	−0.0032 (4)
C3	0.0358 (6)	0.0228 (5)	0.0259 (5)	0.0005 (4)	0.0058 (5)	0.0017 (4)
C1	0.0471 (8)	0.0322 (7)	0.0372 (7)	−0.0059 (6)	0.0049 (6)	−0.0085 (5)
C8	0.0352 (6)	0.0283 (6)	0.0269 (6)	0.0033 (5)	0.0065 (5)	0.0024 (4)
C9	0.0423 (8)	0.0406 (7)	0.0428 (8)	0.0026 (6)	0.0068 (6)	0.0160 (6)
C10	0.0381 (8)	0.0683 (12)	0.0478 (9)	0.0044 (7)	0.0011 (7)	0.0286 (8)
C11	0.0311 (7)	0.0727 (12)	0.0421 (8)	−0.0022 (7)	0.0040 (6)	0.0134 (8)
C12	0.0372 (7)	0.0485 (8)	0.0436 (8)	−0.0060 (6)	0.0080 (6)	0.0109 (7)
C13	0.0381 (7)	0.0336 (6)	0.0313 (6)	0.0015 (5)	0.0066 (5)	0.0073 (5)
C14	0.0523 (12)	0.175 (3)	0.0664 (15)	−0.0201 (16)	−0.0193 (11)	0.0445 (18)
N1	0.0363 (5)	0.0232 (5)	0.0295 (5)	−0.0051 (4)	0.0081 (4)	−0.0004 (4)
N2	0.0575 (8)	0.0211 (5)	0.0617 (9)	0.0005 (5)	0.0065 (7)	0.0009 (5)
N3	0.0595 (9)	0.0294 (6)	0.0568 (9)	−0.0080 (6)	0.0091 (7)	−0.0109 (6)
O1	0.0615 (7)	0.0206 (4)	0.0443 (6)	−0.0064 (4)	0.0063 (5)	−0.0047 (4)
O2	0.0491 (6)	0.0382 (5)	0.0226 (4)	−0.0019 (4)	0.0033 (4)	0.0000 (4)
O3	0.0394 (6)	0.1184 (14)	0.0647 (9)	−0.0214 (8)	−0.0107 (6)	0.0322 (9)
S1	0.03872 (17)	0.02109 (14)	0.02355 (15)	−0.00219 (11)	0.00327 (12)	−0.00259 (10)
Cl1	0.0721 (3)	0.0615 (3)	0.0427 (2)	−0.0113 (2)	−0.0115 (2)	−0.00649 (19)

Geometric parameters (Å, º) top

C4—C3	1.3728 (17)	C9—H9	0.9300
C4—C5	1.4096 (17)	C10—C11	1.387 (3)
C4—N1	1.4456 (15)	C10—H10	0.9300
C5—C6	1.3787 (19)	C11—O3	1.362 (2)
C5—H5	0.9300	C11—C12	1.391 (2)
C6—C7	1.397 (2)	C12—C13	1.377 (2)
C6—H6	0.9300	C12—H12	0.9300
C7—N2	1.3613 (17)	C13—H13	0.9300
C7—C2	1.4041 (19)	C14—O3	1.421 (3)
C2—C3	1.4006 (16)	C14—H14A	0.9600
C2—C1	1.4180 (18)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C1—N3	1.314 (2)	N1—S1	1.6393 (12)
C1—Cl1	1.7038 (17)	N1—H1	0.8235
C8—C9	1.3866 (19)	N2—N3	1.354 (2)
C8—C13	1.3980 (19)	N2—H2	0.8799
C8—S1	1.7507 (14)	O1—S1	1.4359 (10)
C9—C10	1.389 (2)	O2—S1	1.4344 (10)

C3—C4—C5	121.88 (11)	O3—C11—C10	124.39 (15)
C3—C4—N1	119.90 (11)	O3—C11—C12	115.10 (16)
C5—C4—N1	118.21 (11)	C10—C11—C12	120.50 (15)
C6—C5—C4	121.37 (12)	C13—C12—C11	119.94 (14)
C6—C5—H5	119.3	C13—C12—H12	120.0
C4—C5—H5	119.3	C11—C12—H12	120.0
C5—C6—C7	117.05 (12)	C12—C13—C8	119.72 (13)
C5—C6—H6	121.5	C12—C13—H13	120.1
C7—C6—H6	121.5	C8—C13—H13	120.1
N2—C7—C6	132.03 (13)	O3—C14—H14A	109.5
N2—C7—C2	106.28 (13)	O3—C14—H14B	109.5
C6—C7—C2	121.64 (12)	H14A—C14—H14B	109.5
C3—C2—C7	120.72 (12)	O3—C14—H14C	109.5
C3—C2—C1	135.76 (13)	H14A—C14—H14C	109.5
C7—C2—C1	103.44 (12)	H14B—C14—H14C	109.5
C4—C3—C2	117.33 (11)	C4—N1—S1	116.71 (9)
C4—C3—H3	121.3	C4—N1—H1	113.9
C2—C3—H3	121.3	S1—N1—H1	109.7
N3—C1—C2	112.75 (14)	N3—N2—C7	112.47 (13)
N3—C1—Cl1	120.74 (12)	N3—N2—H2	118.6
C2—C1—Cl1	126.50 (12)	C7—N2—H2	128.2
C9—C8—C13	120.34 (13)	C1—N3—N2	105.00 (12)
C9—C8—S1	119.95 (11)	C11—O3—C14	118.12 (18)
C13—C8—S1	119.25 (10)	O2—S1—O1	118.65 (6)
C8—C9—C10	119.78 (15)	O2—S1—N1	107.29 (6)
C8—C9—H9	120.1	O1—S1—N1	105.16 (6)
C10—C9—H9	120.1	O2—S1—C8	108.27 (6)
C11—C10—C9	119.68 (14)	O1—S1—C8	109.65 (7)
C11—C10—H10	120.2	N1—S1—C8	107.25 (6)
C9—C10—H10	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.82	2.26	3.046 (2)	161
N2—H2···O1ⁱⁱ	0.88	1.99	2.862 (2)	174

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.82	2.26	3.046 (2)	160.9
N2—H2···O1ⁱⁱ	0.88	1.99	2.862 (2)	173.8

Symmetry codes: (i) x, −y+3/2, z+1/2; (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

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